- A procedure for transforming indoles into indolequinones
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A procedure that converts a series of structurally diverse, readily available indole derivatives to their corresponding indolequinones is described. The three-step route commences with an iridium catalyzed C-H borylation to give a 7-borylindole that upon
- Eastabrook, Andrew S.,Wang, Christy,Davison, Emma K.,Sperry, Jonathan
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- Rational design of host materials for phosphorescent organic light-emitting diodes by modifying the 1-position of carbazole
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A novel carbazole moiety with bromine at the 1-position of carbazole was synthesized and four carbazole compounds derived from the 1-position modified carbazole were developed as the host materials for phosphorescent organic light-emitting diodes. The 1-p
- Kim, Sung Moo,Byeon, Sung Yong,Hwang, Seok-Ho,Lee, Jun Yeob
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- Color-Tunable Solid-State Fluorescence Emission from Carbazole-Based BODIPYs
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Several carbazole-based boron dipyrromethene (BODIPY) dyes were synthesized by organometallic approaches. Thiazole, benzothiazole, imidazole, benzimidazole, triazole, and indolone substituents were introduced at the 1-position of the carbazole moiety, and boron complexation of each dipyrrin generated the corresponding compounds 1, 2 a, and 3-6. The properties of these products were investigated by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, X-ray crystallography, and DFT calculations. These compounds exhibited large Stokes shifts, and compounds 1, 2 a, and 3-5 fluoresced both in solution and in the solid state. Complex 2 a showed the highest fluorescence quantum yield (ΦF) in the solid state, therefore boron complexes of the carbazole-benzothiazole hybrids 2 b-f, which had several different substituents, were prepared and the effects of the substituents on the photophysical properties of the compounds were examined. The fluorescence properties showed good correlation with the results of crystal-packing analyses, and the dyes exhibited color-tunable solid-state fluorescence.
- Maeda, Chihiro,Todaka, Takumi,Ueda, Tomomi,Ema, Tadashi
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- Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates
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Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.
- Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul
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supporting information
p. 5022 - 5037
(2021/05/04)
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- Method for the synthesis of 1-carbazole-boric acid pinacol ester by amide ortho-orthogonal directing borification
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The present invention discloses a method of synthesizing 1-carbazole - boronic acid pinacol ester by orthophoreinization of an amide orthostatic directional boronate, the steps comprising: (1) the carbazole and the amidation reagent under the action of a
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Paragraph 0047; 0049-0050; 0052
(2022/01/04)
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- HETEROCYCLIC COMPOUND AND AN ORGANIC ELECTROLUMINESCENCE DEVICE COMPRISING THE HETEROCYCLIC COMPOUND
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The present invention relates to specific heterocyclic compounds, a material, preferably an emitter material, for an organic electroluminescence device comprising said specific heterocyclic compounds, an organic electroluminescence device comprising said specific heterocyclic compounds, an electronic equipment comprising said organic electroluminescence device, a light emitting layer comprising at least one host and at least one dopant, wherein the dopant comprises at least one of said specific heterocyclic compounds, and the use of said heterocyclic compounds in an organic electroluminescence device.
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Page/Page column 98
(2022/01/04)
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- COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME
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The present specification relates to a compound of Formula 1 and an organic light emitting device including the same.
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Paragraph 0191-0194
(2021/11/24)
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- Nitrogen-containing compound, organic electroluminescent element, and electronic device
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The invention belongs to the technical field of organic materials, and provides a nitrogen-containing compound, an organic electroluminescent device and an electronic device. The structure of the nitrogen-containing compound is as shown in formula 1, and the nitrogen-containing compound can improve the performance of the organic electroluminescent device.
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Paragraph 0145-0149
(2021/08/06)
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- Novel compound applied to organic electroluminescent device
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The invention provides a novel compound applied to an organic electroluminescent device. The novel compound is represented by a general formula (I) which is described in the specification. In the general formula (I), L1 and L3 are the same or different and are independently selected from a single bond and C6-C30 aryl groups respectively; Ar, R1 and R2 are respectively and independently selected from hydrogen, halogen and substituted or unsubstituted C6-C30 aryl groups; R1 and R2 are the same or different; p is an integer in a range of 0 to 4; q is an integer in a range of 0 to 3; and n is an integer in a range of 0 to 6. A stable and efficient electron transport material prepared by the invention reduces the lighting and working voltage of the device, improves the efficiency of the device,prolongs the service life of the device, and has very important practical application value.
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Paragraph 0049-0051
(2020/09/16)
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- Novel organic compounds and organic light-emitting diode therewith
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The present invention relates to an organic compound represented by the chemical formula A or B, and to an organic light-emitting diode comprising the same, and in the chemical formula A and the chemical formula B, R1 to R12, L1, L2, Ar1 to Ar3, n and m are as described in the description of the invention. Accordingly, a first technical object of the present invention is to provide a specific structure of organic compound having high efficiency, low voltage and long life characteristics by using the compound in an emitting layer, an electron transporting layer or a hole transporting layer in the organic light emitting diode.COPYRIGHT KIPO 2018
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Paragraph 0422-0426
(2018/05/03)
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- Enantioselective Palladium-Catalyzed Carbene Insertion into the N?H Bonds of Aromatic Heterocycles
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C3-substituted indoles and carbazoles react with α-aryl-α-diazoesters under palladium catalysis to form α-(N-indolyl)-α-arylesters and α-(N-carbazolyl)-α-arylesters. The products result from insertion of a palladium-carbene ligand into the N?H bond of the aromatic N-heterocycles. Enantioselection was achieved using a chiral bis(oxazoline) ligand, in many cases with high enantioselectivity (up to 99 % ee). The method was applied to synthesize the core of a bioactive carbazole derivative in a concise manner.
- Arredondo, Vanessa,Hiew, Stanley C.,Gutman, Eugene S.,Premachandra, Ilandari Dewage Udara Anulal,Van Vranken, David L.
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supporting information
p. 4156 - 4159
(2017/04/03)
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- ORGANIC ELECTROLUMINESCENT COMPOUND, ORGANIC ELECTROLUMINESCENT MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
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The present disclosure relates to an organic electroluminescent compound, an organic electroluminescent material, and an organic electroluminescent device comprising the same. By using the organic electroluminescent compound of the present disclosure, it is possible to provide an organic electroluminescent device having low driving voltage, and/or excellent current and/or power efficiencies.
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Paragraph 137-139; 141; 142
(2017/07/05)
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- ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
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The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By using the organic electroluminescent compound of the present disclosure, an organic electroluminescent device having low driving voltage, high luminous efficiency, and/or excellent lifespan characteristic can be produced.
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Paragraph 189; 190; 193; 194
(2017/12/15)
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- Carbazole-Based Boron Dipyrromethenes (BODIPYs): Facile Synthesis, Structures, and Fine-Tunable Optical Properties
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Carbazole-based BODIPYs were synthesized in three steps using an organometallic approach consisting of sequential Ir-catalyzed borylation, Suzuki-Miyaura coupling, and boron complexation. Various substituents were introduced into the carbazole moiety, and
- Maeda, Chihiro,Todaka, Takumi,Ema, Tadashi
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supporting information
p. 3090 - 3093
(2015/06/30)
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- Iridium-catalyzed, silyl-directed borylation of nitrogen-containing heterocycles
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Chemical Figure Presented Selective methods for the functionalization of indoles and other nitrogen heterocycles would provide access to the core structures of many natural products and pharmaceuticals. Although there are many methods and strategies for the synthesis of substituted indoles or functionalization of the azole ring, strategies for the selective functionalization of the benzo-fused portion of the indole skeleton, particularly the 7-position, are less common. We report a one-pot, iridium-catalyzed, silyl-directed C-H borylation of indoles at the 7-position. This process occurs in high yield with a variety of substituted indoles, and conversions of the 7-borylindole products to 7-aryl-, 7-cinnamyl-, and 7-haloindoles are demonstrated. The lr-catalyzed, silyl-directed C-H borylation also occurs with several other nitrogen heterocycles, including carbazole, phenothiazines, and tetrahydroquinoline. The utility of this methodology is highlighted by the one-pot synthesis of a member of the pyrrolophenanthrldone class of alkaloid natural products. Copyright
- Robbins, Daniel W.,Boebel, Timothy A.,Hartwig, John F.
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supporting information; experimental part
p. 4068 - 4069
(2010/05/01)
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