- Three color random fluorene-based oligomers for fast micrometer-scale photopatterning
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In this contribution we show that random fluorene cooligomers with photo reactive acrylate units can be prepared in a simple 1-step Yamamoto synthesis. The acrylate functionalities are preserved quantitatively under Yamamoto conditions.NMRand Maldi-ToF measurements point to an almost statistical incorporation of the comonomers into the oligomer chain. Maldi-ToF analyses give a further insight into the chain compositions, and we found fluorene-only oligomers to be present in low quantities. Thin films of the aromatic amine containing cooligomer show a blue fluorescence, the benzothiadiazole oligomer shows yellow photoluminescence, and the bithiophene oligomer emits orange-red light upon excitation. Compared to pure fluorene oligomers with a HOMO of 5.7 eV the HOMOlevels of the TPD and bithiophene derivatives are increased to 5.25 and 5.31 eV, respectively, whereas theHOMO level of the benzothiadiazole oligomer is decrased to 5.85 eV. Photolithography experiments reveal that a careful optimization of the conditions, for example, the choice of the photoinitiator, temperature, and irradiation wavelength, leads to well-resolved micrometer sized patterns. A minimum feature size of 1 μm was obtained. Thus we showed that with a simple 1-step Yamamoto coupling oligomers with photo-cross-linkable acrylate groups are accessible. UV irradiation leads to densely cross-linked, insoluble networks. Thus these materials are ideal candidates for multilayer as well as patterned semiconducting devices.
- Scheler, Esther,Strohriegl, Peter
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Read Online
- Method for preparing biphenyl triarylated amine compound by taking carboxyl as guide group, intermediate and preparation method thereof
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The invention relates to a method for preparing a biphenyl triarylated amine compound by taking carboxyl as a guide group, an intermediate and a preparation method thereof. The intermediate has a structure as shown in the formula, (the formula is shown in the description), wherein R is selected from hydrogen, alkyl with a carbon atom number of 1-10, halogenated alkyl with a carbon atom number of 1-5, alkoxy with a carbon atom number of 1-5 and aryl. The intermediate is prepared from simple and easily available raw materials, and the biphenyl triarylated amine compound prepared by the intermediate is high in purity and yield, so that the production cost of the biphenyl triarylated amine compound can be remarkably reduced, and therefore, the method is very suitable for industrial productionof the biphenyl triarylated amine compound.
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Paragraph 0065; 0070; 0075; 0076
(2018/07/30)
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- Aromatic compounds and organic electronics material (by machine translation)
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[Problem] to reduce the halogen atom from the aromatic halide compound containing an aromatic compound is efficiently obtained, production of aromatic compounds. [Solution] aromatic halogen compound is a palladium catalyst, in the presence of a solvent comprises an aromatic compound as a hydrogen and a basic manufacturing method, wherein the catalyst is a palladium, a palladium complex compound ligand has preferably a phosphine, under an argon or nitrogen flow is the de-hydrogenation, reflux reaction is preferably heated at 50 a-°C 200. [Drawing] no (by machine translation)
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Paragraph 0056; 0057; 0058; 0059; 0060; 0061; 0062
(2018/04/13)
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- Metal-Free Oxidative C-C Coupling of Arylamines Using a Quinone-Based Organic Oxidant
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A variety of arylamines are shown to undergo oxidative C-C bond formation using quinone-based chloranil/H+ reagent as the recyclable organic (metal-free) oxidant system to afford benzidines/naphthidines. Arylamines (3°/2°) designed with various substituents were employed to understand the steric as well as electronic preferences of oxidative dimerization, and a mechanism involving amine radical cation has been proposed. The tetraphenylbenzidine derivative obtained via oxidative C-C coupling has been further converted to blue-emissive hole-transporting material via a simple chemical transformation. This study highlights the preparation of novel HTMs in a simple, economic, and efficient manner.
- Maddala, Sudhakar,Mallick, Sudesh,Venkatakrishnan, Parthasarathy
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p. 8958 - 8972
(2017/09/11)
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- Near UV-vis LED-excitable two-branched sensitizers for cationic, radical, and thiol-ene photopolymerizations
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Two novel branched sensitizers bearing biphenyl or fluorenyl groups as the linking skeleton and triphenylamine-stilbene-thiomethyl benzonitrile as peripheral branches were designed. Strong absorption of light in the UV-vis range (λmax = 389-397 nm, εmax = 60,200-90,300 M-1 cm-1) matched the emission of new light sources, i.e., UV-vis light-emitting diodes at 365-450 nm. The reactive species produced from the photoinitiating systems based on these chromophores themselves or combined with an iodonium salt, N-vinylcarbazole, or an amine were highly efficient for versatile photopolymerizations (radical, cationic, and thiol-ene polymerizations) upon soft exposure conditions (365-450 nm light-emitting diodes). The UV-vis spectra, theoretical calculation of molecular orbitals, electrochemistry, and fluorescence quenching measurements were studied to reveal the photochemical mechanism.
- Fang, Bingqing,Jin, Ming,Wu, Xingyu,Zhang, Yuan,Wan, Decheng
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- PRODUCTION METHOD OF AROMATIC COMPOUND, AND ORGANIC ELECTRONIC MATERIALS
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PROBLEM TO BE SOLVED: To provide a production method of an aromatic compound gaining the aromatic compound that halogen atom content is reduced from an aromatic halide efficiently. SOLUTION: A production method of an aromatic compound includes a step dehalogenating and hydrogenating an aromatic halide under a presence of a palladium catalyst, a base and solvent. the palladium catalyst is preferable to be a palladium complex which ligand is a phosphine compound, and the dehalogenation and hydrogenation is preferable to react under a nitrogen gas stream or an argon gas stream by heating at 50-200°C while flowing back. COPYRIGHT: (C)2015,JPO&INPIT
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Paragraph 0056-0059; 0061
(2016/10/07)
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- Cu(II)-mediated generation of triarylamine radical cations and their dimerization. An easy route to tetraarylbenzidines
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(Chemical Equation Presented) Triphenylamine (TPA) derivatives react with Cu2+ in acetonitrile to give TPA radical cations which undergo dimerization and deprotonation reactions to yield tetraphenylbenzidines (TPB). Synthetic utility of this reaction is demonstrated using several triphenylamine derivatives, and yields in excess of 80% are obtained in most cases. Involvement of the amine radical cations in these reactions was confirmed by ESR and absorption spectroscopic studies. A mechanism consistent with all observations is proposed. This study also revealed a very good correlation between the free energy change for radical cation formation and product yields.
- Sreenath, Kesavapillai,Suneesh, Chettiyam Veettil,Ratheesh Kumar, Venugopal K.,Gopidas, Karical R.
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p. 3245 - 3251
(2008/09/20)
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- TRIARYLAMINE DIMER DERIVATIVE HAVING AMORPHOUS PHASE AND METHOD FOR PRODUCING THE SAME
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PROBLEM TO BE SOLVED: To provide a triarylamine dimer derivative having amorphous phase, having high solubility to organic solvent without introducing any long-chain aliphatic substituent and capable of forming thin film by a simple method such as coating or spin coating one. SOLUTION: The triarylamine dimer derivative is represented by formula 1 [wherein, Ar1 to Ar4 are each a (substituted) aryl; R1 and R2 are each H, an alkyl, alkoxy or halogen atom; m and n are each 0-4; wherein Ar1 and Ar2 and Ar3 and Ar4 may be bound to each other to form a nitrogen atom-containing cyclic structure, respectively] and shows amorphous phase by its powder X-ray diffraction spectrum.
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Page/Page column 10-11
(2008/06/13)
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- Triarylamine dimer derivative having amorphous phase
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A triarylamine dimer derivative is represented by the following chemical formula [1] ???(in the chemical formula [1]: -Ar1, -Ar2, -Ar3 and -Ar4 are aryl groups being to have a substitutional group respectively, -R1 and -R2 are same or different to each other and one thereof is selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxyl group and a halogen atom; m and n are from 0 to 4; and with a proviso that -Ar1 and -Ar2, -Ar3 and -Ar4 are being to bind respectively to compose a cyclic structure group having a nitrogen atom) having an amorphous phase indicated by spectrum of powder X-ray diffractometry. The triarylamine dimer derivative is used for a charge transport material, an electrophotographic photosensitive conductor having thereof, an electroluminescence elemental device having a hole transport material thereof.
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Page/Page column 11
(2008/06/13)
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- Photo-crosslinkable polymers as hole-transport materials for organic light-emitting diodes
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A bis(diarylamino)biphenyl-functionalised methacrylate has been synthesised and polymerised to give a hole-transport polymer; copolymerisation with a chalcone- or cinnamate-functionalised methacrylate affords photocrosslinkable hole-transport polymers that become insoluble upon exposure to ultra-violet irradiation. Organic light-emitting diodes (OLEDs) were fabricated based on both crosslinked and non-crosslinked hole-transport polymers, and the performances of the devices were evaluated.
- Zhang, Ya-Dong,Hreha, Richard D.,Jabbour, Ghassan E.,Kippelen, Bernard,Peyghambarian,Marder, Seth R.
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p. 1703 - 1708
(2007/10/03)
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- Process for preparing triarylamine dimer
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The present invention intends to provide a simple process for preparing triarylamine dimer without using any expensive chemicals, the process being able to achieve high reaction yield and being advantageous to be carried out on an industrial scale. The present invention provides a process for preparing triarylamine dimer (I) using the Ullmann reaction represented by the scheme: wherein X represents a halogen atom, R1and R2represent independently a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, Ar represents a phenylene group, or a naphthylene group, characterized in that the reaction accelerator is polyethylene glycol or di- or monoalkyl ether of polyethylene glycol.
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- Oligomerization of aromatic tertiary amines
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The oligomerization of some tertiary aromatic amines was studied using ferric chloride in a variety of solvent. The predominant dimer formation of triphenylamine (TPA) was observed in chloroform at O °C where concentration of TPA was 0.125 mmol/l and the molar ratio of ferric chloride to TPA was 4. Except for N-methyldiphenylamine, high molecular weight oligomers were formed in a variety of solvents.
- Sato, Hisaya,Kanegae, Aiko,Yamaguchi, Ryoji,Ogino, Kenji,Kurjata, Jan
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