cas 57103-20-5, 3,6-Dibromo-9-phenylcarbazole

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Preparation method of N-arylcarbazole-3-boric acid
The invention discloses a preparation method of N-arylcarbazole-3-boric acid, and belongs to the field of liquid crystal intermediates. The preparation method comprises the following steps: coupling carbazole with aryl halide in the presence of alkali to generate N-arylcarbazole, enabling the N-arylcarbazole to react with a bromination reagent to generate Naryl-3, 6-dibromo carbazole, enabling theNaryl-3, 6-dibromo carbazole to react with borate and butyl lithium by a one-pot method, and carrying out hydrolyzing to obtain N-arylcarbazole-3-boric acid. According to the method, dibromides whichare easy to purify are generated during bromination, monosubstituted products are generated by controlling the using amount of the lithiation reagent and the boric acid ester during lithiation, the method is verified on the scale of dozens of kilograms, and the method has the prospect of industrial methods.
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Paragraph 0026; 0029-0030; 0033; 0036-0037; 0040; 0043-0044

(2021/02/06)

Synthesis of carbazole-based small organic molecule hole transport material and application of carbazole-based small organic molecule hole transport material in perovskite solar cell
The invention belongs to the field of perovskite solar cell materials, and discloses a carbazole-based small organic molecule hole transport material. According to the carbazole-based small organic molecule hole transport material, a carbazole intermediate core group fragment is synthesized by utilizing a low-temperature reaction and a bromination reaction; a target product OY1, a target product OY2 and a target product OY3 are obtained by means of synthesis from the carbazole intermediate core group fragment and peripheral triphenylamine micromolecules through an acylation reaction and a coupling reaction; the structures of the target product OY1, the target product OY2 and the target product OY3 are confirmed through a high-resolution mass spectrum characterization means, and the target product OY1, the target product OY2 and the target product OY3 are applied to a perovskite solar cell; the synthesized compound is subjected to photophysic, electrochemical, intrinsic hole mobility and thin film characteristic tests, and in addition, the photovoltaic performance of the perovskite solar cell is represented through tests of output current-voltage, incident monochromatic photon-electron conversion efficiency, long-term stability and the like of the cell device. Due to low cost, easy chemical synthesis and excellent performance, the carbazole-based small organic molecule hole transport material will become a powerful competitor.
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Paragraph 0024; 0038; 0049-0050

(2021/07/31)

Scope, Kinetics, and Mechanism of “On Water” Cu Catalysis in the C–N Cross-Coupling Reactions of Indole Derivatives
A simple and cost-effective protocol for the C–N cross coupling of indole derivatives with aryl iodides using CuI/phenanthroline catalytic system in aqueous and DME/H2O solvent mixture is described. The reactions were performed in the absence of phase-transfer catalyst, and afforded N-arylated products in moderate to excellent yields under mild reaction conditions. A systematic tuning of reaction conditions using DME as a co-solvent enables to improve product yields of N-arylation reactions. The broad substrate scope, easy performance, and low loading of catalyst as well as ligand render this approach appropriate for large scale processes. The mechanism of “on water” Cu-catalyzed N-arylation reaction is investigated using kinetic and computational studies, which reveal interesting mechanistic aspects of the reaction. A series of kinetic experiments showed significant rate enhancement for “on water” Cu-catalyzed N-arylation over the reaction performed in the organic solvent (DME). Computational studies corroborated “on water” rate acceleration by delineating the role of water in the reaction. The water induces rate acceleration by stabilizing the transition state of oxidative addition through hydrogen bonding interactions, presumably at the oil-water interface, and thus helps to reduce the free energy of activation of oxidative addition of iodobenzene to the Cu complex, which is identified as the rate-limiting step of reaction.
Malavade, Vrunda,Patil, Manish,Patil, Mahendra
supporting information
p. 561 - 569
(2020/02/05)

Monomer compounds comprising uracil group, Organic layers comprising the cross-linked of the monomer compounds, and Organic electronic device comprising the organic layers
The present invention provides a pyrimidine-based functional group-containing monomolecular compound represented by chemical formula 1 of Ar-(R_1-R_2-Py)_n as a material for an organic layer of an organic electronic device. The compound can form an organic layer within a short time through photo-curing at room temperature. In chemical formula 1, n is 2-10; Ar is a substituted or non-substituted C_6-C_60 aryl group, or a substituted or non-substituted C_3-C_60 heteroaryl group having an n-valent linking group; each of R_1 and R_2 independently represents a single bond, -O-, a substituted or non-substituted C_6-C_30 arylene group, a substituted or non-substituted C_3-C_30 heteroarylene group, a substituted or non-substituted C_1-C_10 alkylene group, a substituted or non-substituted C_1-C10 alkoxylene group, a substituted or non-substituted amide group, or a substituted or non-substituted amine group; and Py is a monovalent linking group derived from a pyrimidine-based functional group.COPYRIGHT KIPO 2020
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Paragraph 0166-0167; 0183-0187

(2020/08/01)

A OLED material and its application
The present invention relates to an OLED material and applications thereof, wherein the OLED material has a molecular structure represented by a formula (1), Ar1 is an aromatic group containing a substituent or a substituent-free aromatic group, Ar2 is a
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Paragraph 0039-0041

(2018/01/11)

An electronic transmission material and its preparation and device
The invention provides carbazole-imidazole electron transport materials. Based on triphenyl imidazole and carbazole, a kind of classic compounds is formed by connecting triphenyl imidazole and carbazole with benzene of different substituent groups. A preparation method is based on improvement of existing methods. Through repeated verification, the preparation method is simple in synthesis and purification processes and low in cost and can meet the industrial development requirements. A device prepared by using the substances has high light emitting efficiency.
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Paragraph 0035; 0038

(2017/10/14)

Symmetric fluorenylbenzimidazole derivative and preparation method therefor
The invention relates to a symmetric fluorenylbenzimidazole derivative and a preparation method therefor. The compound has a structural general formula represented by a formula shown in the description. The method is convenient, universal and economical. The compound has an extensive application prospect in the fields of organic photoelectric materials and fluorescence probing based analysis; in addition, the compound has a symmetrical structure, so that the molecular thermal stability of the compound is improved greatly, and the manufacturing of OLED (Organic Light Emitting Diode) light-emitting devices is better facilitated.
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Page/Page column 11

(2017/07/21)

Organic photoelectric material with carbazole and iminostilbene structure and application of organic photoelectric material
The invention relates to an organic photoelectric material with a carbazole and iminostilbene structure and application of the organic photoelectric material. A compound structural formula of the organic photoelectric material is as shown in the specifica
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Paragraph 0051; 0052

(2017/02/23)

Pigment additives, method of manufacturing the same and pigment dispersion compositions containing the same
The present invention refers to novel pigment additive, manufacturing method thereof and relates to a pigment dispersion composition including, using additives pigment of the present invention optical properties surface, dispersibility and excelling in dispersion stability and have a color property, a pigment dispersion composition provides. (by machine translation)
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Paragraph 0109-0112

(2017/01/26)

FLUORESCENT MOLECULAR ROTORS
The present invention relates to methods and compositions for detecting an interaction between a protein and a ligand, comprising: (i) binding at least one fluorescent molecular rotor to said ligand or protein; and (ii) detecting a change in fluorescence emitted by said fluorescent molecular rotor after contact of the bound fluorescent molecular rotor with the other of said ligand or protein, thereby detecting an interaction between the ligand and the protein, wherein the fluorescent molecular rotor comprises: a rotating ?-bond; an electron-donating moiety; an electron-accepting moiety; and a ?-conjugated linker.
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Paragraph 0310; 0311; 0312

(2016/08/07)

Aggregation-Induced Emission of Platinum(II) Metallacycles and Their Ability to Detect Nitroaromatics
Two new acceptors containing platinum-carbazole (1) and platinum-triphenylamine (2) backbones with bite angles of 90° and 120°, respectively, have been synthesised and characterised. Reactions of the rigid acceptor 1 with linear dipyridyl-based donors (3 and 4) generated [4+4] self-assembled molecular squares (5 and 6), and similar treatments with acceptor 2 instead of 1 yielded [6+6] self-assembled molecular hexagons (7 and 8). The metallacycles were characterised by multinuclear NMR spectroscopy (1H and 31P) and ESI-MS. The geometries of the metallacycles were optimised by using the PM6 method. When aggregates of the metallacycles were formed by adding hexane solutions in dichloromethane, aggregation-induced emission was observed for metallacycles 5 and 7, and aggregation-caused quenching was observed for metallacycles 6 and 8. The formation of aggregates was verified by dynamic light scattering and TEM analyses. Macrocycles 5 and 7 are white-light emitters in THF. Moreover, their high luminescence in both solution and the solid state was utilised for the recognition of nitroaromatic explosives.
Chowdhury, Aniket,Howlader, Prodip,Mukherjee, Partha Sarathi
p. 7468 - 7478
(2016/05/24)

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
The present invention provides a novel compound to improve light emission efficiency and reliability of an element and to extend the lifespan of the element, to an organic electronic element using the same, and to an electronic device thereof. The compound is represented by chemical formula 1, wherein n is a constant in the range of two and four.(110) Substrate(120) Positive electrode(130) Hole injection layer(140) Hole tranfer layer(141) Buffer layer(150) Light emitting layer(151) Light-emitting assisting layer(160) Electron transfer layer(170) Electron injection layer(180) Negative electrodeCOPYRIGHT KIPO 2015
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Paragraph 0149; 0153; 0182-0184

(2016/10/10)

Copper/β-diketone-catalysed N-arylation of carbazoles
A copper-catalysed C-N bond-forming reaction of carbazoles with aryl iodides is described. Several commercially available ligands such as β-diketone and diamine, are tested in the N-arylation of carbazoles. The catalytic system generated in situ from an inexpensive copper salt, simple β-diketone and inorganic base efficiently N-arylated the carbazoles. A wide range of aryl iodides and carbazoles can be coupled to generate N-arylcarbazoles in the presence of various functional groups. However, the sterically hindered effect of aryl iodides is evident in this catalytic system. The selectivity of two iodine atoms on the aromatic ring of diiodobenzene is evaluated in the developed catalytic system. Results showed that the selectivity of diiodobenzene can be tuned by the reaction temperature.
Chen, Fei,Liu, Ning,Ji, Enhui,Dai, Bin
p. 51512 - 51523
(2015/06/25)

Condensed compound and organic light emitting diode comprising the same
Provided are a condensed cyclic compound represented by chemical formula 1 and an organic electroluminescent device comprising the same. In the chemical formula 1, X, and R1 to R10 refer to the detailed description of the present invention. An organic light emitting device having an organic layer comprising the condensed cyclic compound has properties of low driving voltage, high light emitting efficiency and long lifespan.COPYRIGHT KIPO 2016
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Paragraph 0317; 0318; 0319

(2016/12/01)

ORGANIC COMPOUND, LIGHT-EMITTING ELEMENT, LIGHT-EMITTING DEVICE, ELECTRONIC DEVICE, AND LIGHTING DEVICE
PROBLEM TO BE SOLVED: To provide a useful novel phosphorescence organic compound that is used as a host material in which a light-emitting substance of a light-emitting layer is dispersed in a light-emitting element using an organic electroluminescence. S
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Paragraph 0253; 0254

(2016/10/10)

An electroluminescent compound and an electroluminescent device comprising the same
The present invention relates to an organic light emitting compound applied to an organic light emitting device. The organic light emitting compound: is represented by chemical formula 1; includes one or more substituted bodies represented by structural formula 1 or structural formula 2; and is capable of realizing an organic light emitting device having excellent luminous properties such as driving voltage, luminance, a long life and the like in the case of being applied as a phosphorescent host compound in a hole transporting functional layer or an emissive layer.COPYRIGHT KIPO 2016
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Paragraph 0246; 0247; 0297; 0298

(2016/10/07)

LIGHT-EMITTING MATERIAL FOR ORGANIC ELECTROLUMINESCENT DEVICE, ORGANIC ELECTROLUMINESCENT DEVICE USING SAME, AND MATERIAL FOR ORGANIC ELECTROLUMINESCENT DEVICE
Disclosed are a novel fused cyclic compound having excellent light emitting efficiency and thermal stability, a method for producing the same, and an organic electroluminescent device including the same compound. The fused cyclic compound is represented b
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Paragraph 0350-0353

(2016/10/08)

This polycarbazole-phosphine oxide compound and an organic electroluminescence element including (by machine translation)
The present invention relates to a carbazole-based phosphine oxide compound, and an organic electroluminescent device including the same. According to the present invention, provided are a compound for an organic electroluminescent device which can improve unstable thermal stability and low efficiency characteristics which are the problems of known compounds for an organic electroluminescent device, and particularly, can implement excellent efficiency characteristics in a pure blue phosphorescent device, by using the carbazole-based phosphine oxide compound of the compound for the organic electroluminescent device, and the organic electroluminescent device. According to one aspect of the present invention, the carbazole-based phosphine oxide compound of the compound for the organic electroluminescent device is provided, and the organic electroluminescent device containing the same which can implement thermal stability and high efficiency characteristics is also provided.
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Paragraph 0159

(2016/10/10)

High-efficiency deep blue fluorescent emitters based on phenanthro[9,10-d]imidazole substituted carbazole and their applications in organic light emitting diodes
A series of highly efficient deep blue emitters comprising of carbazole and phenanthro[9,10-d]imidazole moieties are designed and synthesized. These compounds present deep blue emission, narrow FWHM, high quantum yields, high thermal and morphological stabilities. Among them, the design strategy of 2:1 ratio of phenanthro[9,10-d]imidazole and carbazole unit affords M2 with more balanced carrier injection and transporting properties. OLEDs using M2 as emitting layer is observed to deliver a truly deep blue CIE of y 3is attained with a maximum current efficiency of 33.35 cd A-1, a power efficiency of 22.99 lm W-1and a maximum external quantum efficiency of 9.47%. When doped with an orange fluorescent material, upon careful tuning the doping proportion, the two-emitting-component white OLED is successfully fabricated with a maximum current efficiency of 5.53 cd A-1and CIE coordinates of (0.313, 0.305). Both the non-doped and doped devices exhibited high operational stability with negligible efficiency roll-off over the broad current density range.
Gao, Zhao,Wang, Zhiming,Shan, Tong,Liu, Yulong,Shen, Fangzhong,Pan, Yuyu,Zhang, Huanhuan,He, Xin,Lu, Ping,Yang, Bing,Ma, Yuguang
supporting information
p. 2667 - 2676
(2014/12/10)

The interplay of photophysical properties in carbazole fluorescent oligomers
The photophysical properties and the organic synthesis using effective palladium-catalyzed Suzuki coupling reactions from a series of carbazole derivatives are described and the relationships of the donor and acceptor groups are also investigated. The purification of the materials and its applications along with the corresponding photo-physical characterizations were presented. With the advantages gained from 2DCOSY spectra, which provide more correlated information between immediate atoms than 1H-NMR spectra and a series of further investigations were undertaken including powder X-ray diffraction analysis, Infrared and Raman spectroscopy, constructing the composition conformation and chemical structure of the materials is more easily to achieve. Additionally, the optimized structure of the minimized energy geometries and spatial distributions of carbazole derivatives was calculated using density functional theory (DFT), new materials can be developed and designed selectively based on the method proposed in this work.
Hsu, Chung-Yi,Hsieh, Mu-Tao,Chen, Yen-Fu,Hsu, Chun-Chia,Hung, Tzu-Lin,Chen, Chun-Shuo,Whang, Thou-Jen
p. 579 - 589
(2013/10/22)

Electrochemical and spectral characterizations of 9-phenylcarbazoles
A series of 9-phenylcarbazoles have been synthesized and characterized for their electrochemical as well as spectral properties. For 3,6-substituted carbazoles, the oxidation is reversible and the potential is affected by the substituents. For 3,6-unprotected carbazoles, on the other hand, the oxidized forms can undergo dimerization. Their corresponding dimers have been independently synthesized by chemical methods and have exhibited identical spectral properties. The para position of the 9-phenyl group is relatively insensitive for redox and chemical reactions. The amino derivatives are unstable in carbazole cation radical form compared with their triphenylamine counterparts.
Chiu, Ssu-Kai,Chung, Yi-Chun,Liou, Guey-Sheng,Su, Yuhlong Oliver
scheme or table
p. 331 - 337
(2012/07/03)

Using tetraphenylethene and carbazole to create efficient luminophores with aggregation-induced emission, high thermal stability, and good hole-transporting property
Tetraphenylethene (TPE) is an archetypal luminogen that exhibits a phenomenon of aggregation-induced emission (AIE), while carbazole is a conventional chromophore which shows the opposite effect of aggregation-caused quenching (ACQ) of light emission in the condensed phase. Melding the two units at the molecular level generates a group of new luminescent materials that suffer no ACQ effect but depict high solid-state fluorescence quantum yields up to unity, demonstrative of the uniqueness of the approach to solve the ACQ problem of traditional luminophores. All the TPE-carbazole adducts are thermally and morphologically stable, showing high glass-transition temperatures (up to 179 °C) and thermal-degradation temperatures (up to 554 °C). Multilayer electroluminescence devices with configurations of ITO/NPB/emitter/TPBi/Alq 3/LiF/Al are constructed, which exhibit sky blue light in high luminance (up to 13650 cd m-2) and high current and external quantum efficiencies (up to 3.8 cd A-1, and 1.8%, respectively). The devices of the luminogens fabricated in the absence of NPB or hole-transporting layer show even higher efficiencies up to 6.3 cd A-1 and 2.3%, thanks to the good hole-transporting property of the carbazole unit.
Zhao, Zujin,Chan, Carrie Y. K.,Chen, Shuming,Deng, Chunmei,Lam, Jacky W. Y.,Jim, Cathy K. W.,Hong, Yuning,Lu, Ping,Chang, Zhengfeng,Chen, Xiaopeng,Kwok, Hoi Sing,Qiu, Huayu,Tang, Ben Zhong
scheme or table
p. 4527 - 4534
(2012/08/08)

Efficient phosphorescent green and red organic light-emitting diodes based on the novel carbazole-type host material
We developed a novel carbazole-type material, 9-phenyl-3,6-bis(4-(1-phenyl- 1H-benzo[d]imidazol-2-yl)phenyl)-9H-carbazole (LPGH 153), and fabricated the green and red phosphorescent organic light-emitting diodes (OLEDs) using LPGH 153 as host. The red and green devices have the max. luminous efficiencies of 22.2 cd/A and 32.2 cd/A, respectively. Copyright
Seo, Ji Hyun,Kim, Hoe Min,Choi, Eun Young,Choi, Dae Hyuk,Park, Jung Hwan,Lee, Kum Hee,Yoon, Seung Soo,Kim, Young Kwan
experimental part
p. 1373 - 1376
(2012/05/20)

Highly efficient deep-blue emitting organic light emitting diode based on the multifunctional fluorescent molecule comprising covalently bonded carbazole and anthracene moieties
High performance deep-blue organic light-emitting diodes (OLEDs) have been investigated using new multifunctional blue emitting materials 3-(anthracen-9-yl)-9-ethyl-9H-carbazole (AC), 3,6-di(anthracen-9-yl)-9-ethyl-9H- carbazole (DAC), 3-(anthracen-9-yl-)-9-phenyl-9H-carbazole (P-AC), and 3,6-di(anthracen-9-yl)-9-phenyl-9H-carbazole (P-DAC) which comprise covalently bonded carbazole and anthracene moieties. We also have investigated the thermal, electrochemical, and morphological stability to find suitable molecular structure, consisting of carbazole and anthracene moieties. The non-doping deep-blue OLEDs using P-DAC, which showed the highest thermal, electrochemical, and morphological stability, proved the highest luminance efficiency and external quantum efficiency of 3.14 cd A-1 and 2.75%, with the Commission Internationale de l'Eclairage (CIE) chromaticity coordinates (0.162, 0.136) at 100 mA cm-2. Moreover, the doping devices using P-DAC as the host material showed blue emission, and the high luminance efficiencies and external quantum efficiencies of as high as 7.70 cd A-1 and 4.86% with CIE chromaticity coordinates (0.156, 0.136) and (0.156, 0.217) at 100 mA cm-2. Both the non-doping and doping devices using P-DAC uniquely exhibited high operational stability with virtually negligible efficiency roll-off over the broad current density range.
Kim, Se Hun,Cho, Illhun,Sim, Mun Ki,Park, Sanghyuk,Park, Soo Young
supporting information; experimental part
p. 9139 - 9148
(2012/01/15)

NOVEL COMPOUND AND ORGANIC ELECTRONIC DEVICE USING SAME
The present invention relates to a novel compound and an organic light emitting device using the compound, and the compound according to the present invention may largely improve a life span, efficiency, electrochemical stability and thermal stability of the organic light emitting device.
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(2011/08/03)

High-triplet-energy tri-carbazole derivatives as host materials for efficient solution-processed blue phosphorescent devices
A novel series of solution-processible carbazole-based host materials, 3,6-bis(N-carbazolyl)-N-phenylcarbazole (BCC-36), 3,6-bis(3,6-di-tert-butyl-9- carbazolyl)-N-phenylcarbazole (BTCC-36), 2,7-bis(N-carbazolyl)-N-phenylcarbazole (BCC-27), and 2,7-bis(3,6-di-tert-butyl-9-carbazolyl)-N-phenylcarbazole (BTCC-27), is designed and synthesized. Owing to the highly twisted configuration, these hosts exhibit high triplet energy levels (2.90-3.02 eV) and high glass transition temperatures (147-210°C). They also exhibit appropriate HOMO energy levels (-5.21 - 5.36 eV), resulting in an improved hole-injection property. These novel compounds are employed to fabricate phosphorescent organic lighting-emitting diodes (OLEDs) as the host materials doped with the guests of iridium(iii) bis(4,6-difluorophenylpyridinato)- picolinate (FIrpic) and iridium(iii) bis(4′,6′- difluorophenylpyridinato)tetrakis(1-pyrazolyl)borate (FIr6) by spin coating. The best device performance of FIrpic based blue-emitting devices has a rather low turn-on voltage of 3.9 V, a maximum efficiency of 27.2 cd A-1 (11.8 lm W-1), and a maximum external quantum efficiency of 14.0%. Moreover, the best device performance of FIr6 based deep-blue-emitting devices exhibits a turn-on voltage of 4.9 V, a maximum efficiency of 11.5 cd A -1 (4.9 lm W-1), and a maximum external quantum efficiency 6.8%. The performance data are outstanding for solution-processed blue phosphorescent OLEDs. The Royal Society of Chemistry 2011.
Jiang, Wei,Duan, Lian,Qiao, Juan,Dong, Guifang,Zhang, Deqiang,Wang, Liduo,Qiu, Yong
experimental part
p. 4918 - 4926
(2011/10/12)

Influence of donor moiety in ruthenium sensitizers on the properties of dye-sensitized solar cells
Heteroleptic ruthenium complexes c/s-[Ru(H2dcbpy)(L)(NCS) 2], where H2dcbpy is 4,4'-dicarboxylic acid-2,2'-bipyridine and L is 4-(4-(N,N-di-(p-hexyloxyphenyl)-amino)styryl)-4'- methyl-2,2'-bipyridine (Rut-A) or 4-(4'-(3,6-
Nguyen, Hong-Minh,Choi, Jongwan,Heo, Ji Hyun,Oh, Jin-Woo,Nguyen, Duc-Nghia,Kim, Nakjoong
body text
p. 6811 - 6814
(2011/10/13)

Silanylamine-based compound, method of preparing the same and organic light emitting device including organic layer comprising the silanylamine-based compound
Silanylamine-based compounds represented by Formula I are provided. Methods of preparing the compounds and organic light emitting devices including organic layers comprising the silanylamine-based compounds are also provided. The silanylamine-based compounds have excellent electrical stability and hole transporting capabilities. Thus, the silanylamine-based compounds may be effectively used for red, green, blue, and white fluorescent and phosphorescent materials used to form hole injection layers, hole transport layers, and emissive layers in organic light emitting devices. Organic light emitting devices using these compounds have high efficiency, low driving voltages, high luminance and long lifetimes.
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Page/Page column 35-36

(2008/12/05)

Synthesis and optical properties of novel compounds containing carbazole and 1,8-naphthalimide groups
A series of novel carbazole-naphthalimide compounds with moieties capable of carrier-balance and electroluminescence were synthesised and characterised, and theirs luminescent properties had been studied.
Feng, Guo-Liang,Ji, Shun-Jun,Geng, Li-Jun,Bian, Bing,Liu, Yu
scheme or table
p. 137 - 140
(2009/04/10)

Synthesis, characterization, and field-effect transistor properties of carbazolenevinylene oligomers: From linear to cyclic architectures
Two cyclic carbazolenevinylene dimers 1 and 2 were synthesized by McMurry coupling reactions. A linear compound 3 was also prepared for comparison. Compounds 1-3 were fully characterized by means of NMR spectroscopy, HRMS, elemental analysis, and UV/Vis absorption spectroscopy. Quantum chemical simulations showed that the cyclic compounds possessed smaller HOMO-LUMO gaps and more extended conjugation. The UV/Vis absorption spectra of the cyclic compounds showed blueshifts compared with that of the linear compound 3. Time-dependent DFT (TD-DFT) analysis revealed that this was due to the different selection rules for molecules with cyclic and linear architectures. The cyclic conformation also significantly affected the molecular ordering in the solid state. The X-ray crystal structure of 1 showed partial π-π over-lapping between the adjacent mole-cules. Thin films of 1-3 were fabricated by the vacuum-deposition method on Si/SiO, substrates. Multicrystalline thin films were obtained from compounds 1 and 2, but only amorphous thin films could be obtained for the linear compound 3. Another important difference between the cyclic and linear compounds was the reduced reorganization energy for the cyclic compounds. These two facts have resulted in improved field-effect transistor (FET) mobilities for the cyclic compounds compared with the linear compound. In addition, as the substrate temperature has a significant influence on the morphology and the degree of crystallinity of the thin films deposited, the device performance could be optimized by varying the substrate temperature. The FET devices based on 2 gave the highest mobility of 0.013 cm2V -1s-1. The results showed that carbazole derivatives with cyclic structures might make better FETs.
Song, Yabin,Di, Chong-An,Wei, Zhongming,Zhao, Tianyue,Xu, Wei,Liu, Yunqi,Zhang, Deqing,Zhu, Daoben
scheme or table
p. 4731 - 4740
(2009/05/07)

Synthesis and optical properties of starburst carbazoles based on 9-phenylcarbazole core
New well-defined starburst carbazole derivatives, which contain N-phenylcarbazole as the central core joining 9-hexylcarbazole or 9-phenylcarbazole as arms, are presented. All these compounds were obtained via Suzuki cross-coupling in moderate yields. Their structures were confirmed by 1H NMR, MALDI-TOF mass spectrometry and elementary analysis. Moreover, the fluorescence spectra showed that these compounds exhibited good blue fluorescence with the maximum wavelengths ranging from 410 nm to 430 nm. Georg Thieme Verlag Stuttgart.
Feng, Guo-Liang,Ji, Shun-Jun,Lai, Wen-Yong,Huang, Wei
p. 2841 - 2845
(2008/02/13)

New luminescent compositions and their uses
High quantum yield luminescent monomers, oligomers, and polymers, comprising benzotriazole repeating units and derivatives thereof have been discovered and utilized in optical devices and components therefor, including electroluminescent devices, light emitting devices, photoluminescent devices, organic light emitting diodes (OLEDs), OLED displays, sensors, and the like.
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(2008/06/13)

Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system
The preparation, isolation and characterization by elemental analysis and 1H-NMR, 13C-NMR, and MS data of the bromo derivatives of N-substituted carbazoles, i.e., of 9-methyl-9H-carbazole (1), 9-phenyl-9H-carbazole (2), 9-benzyl-9H-carbazole (3), 2-methoxy-9-methyl-9H- carbazole (4), and of C-substituted carbazoles, i.e., of 2-(acetyloxy)-9H- carbazole (5) and 3-nitro-9H-carbazole (6), are reported, in part for the first time. As brominating reagents, N-bromosuccinimide (NBS) or NBS/silica gel in CH2Cl2, NBS in AcOH, KBrO3/KBr in EtOH doped with a catalytic amount of H2SO4, or KBrO3/KBr in AcOH were employed, and their uses were compared. Semi-empirical PM3 calculations were performed to predict the reactivity of the N-substituted and C-substituted carbazoles and of their bromo derivatives and found to verify the experimental results. The UV-absorption and fluorescence and phosphorescence emission spectra of the bromocarbazole derivatives in MeCN solution at 298 K and in a solid matrix at 77 K were compared with those of the corresponding carbazoles 1-6. The dynamic properties of the lowest excited singlet and triplet states (τf, τp, φf, and φp) were measured under the same experimental conditions. The intramolecular spin-orbital-coupling effect of the Br-atom and NO2 group on the spectroscopic data, photophysical parameters, and on the photo reactivity were also briefly analyzed.
Ponce, Maria B.,Cabrerizo, Franco M.,Bonesi, Sergio M.,Erra-Balsells, Rosa
p. 1123 - 1139
(2007/10/03)

Synthesis and characterization of blue-light-emitting alternating copolymers of 9,9-dihexylfluorene and 9-arylcarbazole
Several soluble and well-defined copolymers of 9,9-dihexyl-2,7-fluorene and 9-aryl-3,6-carbazole (aryl = phenyl, p-methylphenyl, p-methoxyphenyl) were prepared in good yields by Suzuki-type coupling polymerization of fluorene-diboronic ester with some 9-a
Wong, Wai-Yeung,Liu, Li,Cui, Dongmui,Leung, Louis M.,Kwong, Chin-Fai,Lee, Tik-Ho,Ng, Ho-Fung
p. 4970 - 4976
(2007/10/03)

A convenient synthesis of 3,6-substituted carbazoles via nickel catalyzed cross-coupling
Alkyl, vinyl and aryl substitiuted carbazoles at the 3- and 6-positions are prepared in high yield from the corresponding 3,6-dibromocarbazole via nickel catalyzed coupling with Grignard reagents (Corriu-Kumada coupling).
Park, Minnie,Buck, Jason R.,Rizzo, Carmelo J.
p. 12707 - 12714
(2007/10/03)