- A thiadiazole compound, a compound for a light-emitting element, light-emitting element, the light emitting device, the authentication device and electronic device
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PROBLEM TO BE SOLVED: To provide a thiadiazole compound, a compound for light-emitting elements, and a light-emitting element capable of emitting light in the near-infrared region and having high efficiency and long life, and a light-emitting device, an authentication device, and an electronic device having the light-emitting element.SOLUTION: The thiadiazole compound is represented by the following formula (1), wherein Xs each independently represent a hydrogen atom or a functional group, and a ring may be formed by adjacent two or more Xs.
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Paragraph 0135
(2017/07/23)
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- High-yielding synthesis and full spectroscopic characterization of 5,6:11,12-di-o-phenylenetetracene and its synthesis intermediates
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Herein we present a synthetic gram-scale route to 5,6:11,12-di-o-phenylenetetracene (DOPT, 8), which is a member of the class of cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAHs). Full analytical characterization of the title compound was carried out by IR, Raman, UV/Vis, and high-field 1H NMR spectroscopy, as well as by mass spectrometry. A unique double-elimination of phenylide moieties, as the key reaction step, gave DOPT for the first time in high purity and in an isolated yield of >70 %. Re-aromatization of the annulated π-ring system occurred following the reductive elimination of the two phenyl groups from the DOPT precursor. Two alternative reaction pathways for this process are discussed. The synthetic method described herein may allow development of the chemistry of the title compound further, for example, to investigate the organometallic chemistry of DOPT as well as its semiconducting behavior in organic electronics. Diels-Alder chemistry has allowed the high-yielding synthesis of the carbon framework of the aromatic hydrocarbon 5,6:11,12-di-o-phenylenetetracene (DOPT). All the reaction intermediates have been fully characterized for the first time. A final unprecedented re-aromatization sequence employing a two-fold reductive dephenylation yielded crystalline, blue DOPT in gram-scale quantities.
- Wombacher, Tobias,Foro, Sabine,Schneider, J?rg J.
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p. 569 - 578
(2016/02/18)
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- Structural Polymorphism and Thin Film Transistor Behavior in the Fullerene Framework Molecule 5,6;11,12-di-o-Phenylenetetracene
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The molecular structure of the hydrocarbon 5,6;11,12-di-o-phenylenetetracene (DOPT), its material characterization and evaluation of electronic properties is reported for the first time. A single-crystal X-ray study reveals two different motifs of intramo
- Wombacher, Tobias,Gassmann, Andrea,Foro, Sabine,Von Seggern, Heinz,Schneider, J?rg J.
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supporting information
p. 6041 - 6046
(2016/05/19)
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- THIADIAZOLE COMPOUND, COMPOUND FOR LIGHT EMITTING ELEMENT, LIGHT EMITTING ELEMENT, LIGHT EMITTING DEVICE, AUTHENTICATION DEVICE AND ELECTRONIC APPARATUS
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PROBLEM TO BE SOLVED: To provide an efficient and long-life thiadiazole compound which emits light in the near-infrared region, and a light emitting element or the like prepared using the same. SOLUTION: A light emitting element 1 comprises an anode 3, a cathode 9, and a light emission layer 6 provided between the anode 3 and the cathode 9, wherein the light emission layer 6 comprises a thiadiazole compound represented by formula (1) and a compound of formula IRH-1. In the formula (1), A is H, an alkyl group or the like, and in the formula IRH-1, n is a natural number of 1-12 and R is H, alkyl or the like. COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0207-0208
(2016/10/08)
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- Electronic device
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PROBLEM TO BE SOLVED: To provide a thiadiazole compound, a compound for light-emitting elements, and a light-emitting element capable of emitting light in the near-infrared region and having high efficiency and long life, and a light-emitting device, an authentication device, and an electronic device having the light-emitting element. SOLUTION: A light-emitting element 1 comprises an anode 3, a cathode 9, and a light-emitting layer 6 provided between the anode 3 and the cathode 9. The light-emitting layer 6 is configured to contain a compound represented by formula (1) and a compound represented by formula IRH-1. In the formula (1), A and B each represent an aryl group, an arylamino group or triarylamine. In the formula IRH-1, n represents a natural number of 1 to 12; and each R is a substituent or a functional group, and represents an aryl group or an arylamino group which may have H, an alkyl group or a substituent. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0103; 0111; 0112; 0113
(2016/10/09)
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- Rubrene-based single-crystal organic semiconductors: Synthesis, electronic structure, and charge-transport properties
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Correlations among the molecular structure, crystal structure, electronic structure, and charge-carrier transport phenomena have been derived from six congeners (2-7) of rubrene (1). The congeners were synthesized via a three-step route from known 6,11-dichloro-5,12-tetracenedione. After crystallization, their packing structures were solved using single-crystal X-ray diffraction. Rubrenes 5-7 maintain the orthorhombic features of the parent rubrene (1) in their solid-state packing structures. Control of the packing structure in 5-7 provided the first series of systematically manipulated rubrenes that preserve the π-stacking motif of 1. Density functional theory calculations were performed at the B3LYP/6-31G(d,p) level of theory to evaluate the geometric and electronic structure of each derivative and reveal that key properties of rubrene (1) have been maintained. Intermolecular electronic couplings (transfer integrals) were calculated for each derivative to determine the propensity for charge-carrier transport. For rubrenes 5-7, evaluations of the transfer integrals and periodic electronic structures suggest these derivatives should exhibit transport characteristics equivalent to, or in some cases improved on, those of the parent rubrene (1), as well as the potential for ambipolar behavior. Single-crystal field-effect transistors were fabricated for 5-7, and these derivatives show ambipolar transport as predicted. Although device architecture has yet to be fully optimized, maximum hole (electron) mobilities of 1.54 (0.28) cm 2 V-1 s-1 were measured for rubrene 5. This work lays a foundation to improve our understanding of charge-carrier transport phenomena in organic single-crystal semiconductors through the correlation of designed molecular and crystallographic changes to electronic and transport properties.
- McGarry, Kathryn A.,Xie, Wei,Sutton, Christopher,Risko, Chad,Wu, Yanfei,Young, Victor G.,Bredas, Jean-Luc,Frisbie, C. Daniel,Douglas, Christopher J.
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p. 2254 - 2263
(2013/07/27)
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- THIADIAZOLE-BASED COMPOUND, LIGHT EMITTING ELEMENT COMPOUND, LIGHT EMITTING ELEMENT, LIGHT EMITTING DEVICE, AUTHENTICATION DEVICE, AND ELECTRONIC DEVICE
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Provided is a thiadiazole compound with high efficiency and long life which emits light in a near-infrared region and represented by Formula (I). [In the Formula (I), As each independently represent an aryl group which may have a substituent or a diarylamino group.]
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Page/Page column 47-48
(2012/11/07)
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- Bridged Organosilane and Production Method Thereof
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Provided is a bridged organosilane, which has a large complex organic group, and which is useful in the synthesis of a mesoporous silica and a light-emitting material, and a production method of the bridged organosilane. The bridged organosilane is expressed by the following general formula (1): [in the formula (1), q represents an integer in a range from 2 to 4, X1— represents a substituent selected from the group consisting of substituents expressed by the following general formulae (2) to (5): (in the formulae (2) to (5), R1 represents alkyl group having 1 to 5 carbon atoms, R2 represents an allyl group, and n represents an integer in a range from 0 to 3, and m represents an integer in a range from 0 to 6), and A1 represents an organic group expressed by, for example, the following general formula (6): (in the formula (6), Y1 represents a substituent expressed by, for example, O═C)].
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Page/Page column 40
(2009/04/24)
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- Rubrenes: Planar and twisted
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Surprisingly, despite its very high mobility in a single crystal, rubrene shows very low mobility in vacuum-sublimed or solution-processed organic thin-film transistors. We synthesized several rubrene analogues with electron-withdrawing and electron-donating substituents and found that most of the substituted rubrenes are not planar in the solid state. Moreover, we conclude (based on experimental and calculated data) that even parent rubrene is not planar in solution and in thin films. This discovery explains why high mobility is reported in rubrene single crystals, but rubreneshows very low field-effect mobility in thin films. The substituted rubrenes obtained in this work have significantly better solubility than parent rubrene and some even form films and not crystals after evaporation of the solvent. Thus, substituted rubrenes are promising materials for organic light-emitting diode (OLED) applications.
- Paraskar, Abhimanyu S.,Ravikumar Reddy,Patra, Asit,Wijsboom, Yair H.,Gidron, Ori,Shimon, Linda J.W.,Leitus, Gregory,Bendikov, Michael
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experimental part
p. 10639 - 10647
(2009/12/27)
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- Regioselective Synthesis of Substituted Rubrenes
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The development of two complementary synthetic routes to 5,6,11,12-tetraphenylnaphthacene (rubrene) derivatives is described.In one approach, selective nucleophilic addition of aryllithiums to diarylnaphthacenequinones (13, 14, 16), followed by HI aromatization of the corresponding diols, allows for the convenient preparation of a wide variety of selectively functionalized rubrenes.Symmetrically and unsymmetrically di- and tetrasubstituted rubrenes have been prepared, as well as several "end-capped" versions.In a second route, cycloaddition of 1,3-diphenylisobenzofuran with the naphthyne 7 (Ar= Ph) followed by Lewis acid mediated deoxygenation of the resultant oxo-bridged adduct gives rubrene in a particularly convergent manner.Elaboration through the use of substituted isobenzofurans (i.e. 9-11) allows for the analogous preparation of substituted rubrenes (45-47).
- Dodge, Jeffrey A.,Bain, J. D.,Chamberlin, A. Richard
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p. 4190 - 4198
(2007/10/02)
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