- Side chain modification on PDI-spirobifluorene-based molecular acceptors and its impact on organic solar cell performances
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N-Substitution in perylene diimide (PDI) n-type semiconductors is critical for their performance in organic bulk heterojunction solar cells. In this work we synthesized and compared three perylene diimide-spirobifluorene derivatives, N-substituted with different alkyl side groups. These molecular systems were obtained by cost-effective methods, using straightforward synthetic procedures and easy purification. These PDI derivatives were used as electron acceptor materials, blended with a benchmark quinoxaline-benzodithiophene based donor polymer, in bulk heterojunction solar cells. All devices were processed by blade coating in air, and also using non-chlorinated solvents. The three molecules presented identical HOMO/LUMO energy levels and very similar optical properties but different photovoltaic responses. These different performances were discussed through optical, electrical and morphological characterizations. The highest power conversion efficiency was achieved for the active layer based on the derivative with branched and longer alkyl groups in N-positions, which favored a morphology with reduced donor:acceptor phase segregation.
- Bolognesi, Margherita,Gedefaw, Desta,Cavazzini, Marco,Catellani, Marinella,Andersson, Mats R.,Muccini, Michele,Kozma, Erika,Seri, Mirko
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- Spirobifluorene/sulfone hybrid: Highly efficient solution-processable material for UV-violet electrofluorescence, blue and green phosphorescent OLEDs
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A high efficient UV-violet emission type material bis[4-(9,9′- spirobifluorene-2-yl)phenyl] sulfone (SF-DPSO) has been synthesized by incorporating electron deficient sulfone and morphologically stable spirobifluorene into one molecule. The steric and bulky compound SF-DPSO exhibits an excellent solid state photoluminescence quantum yield (ΦPL = 92%), high glass transition temperature (Tg = 211 °C) and high triplet energy (ET = 2.85 eV). In addition, the uniform amorphous thin film could be formed by spin-coating from its solution. These promising physical properties of the material made it suitable for using as UV-violet emitter in non-doped device and appropriate host in phosphorescent OLEDs. With SF-DPSO as an emitter, the non-doped solution processed device achieved an efficient UV-violet emission with the EL peak around 400 nm. By using SF-DPSO as a host, solution processed blue and green phosphorescent organic light emitting diodes showed a high luminous efficiency of 13.7 and 30.2 cd A-1, respectively.
- Ban, Xinxin,Xu, Huange,Yuan, Guolong,Jiang, Wei,Huang, Bin,Sun, Yueming
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- Poly(vinylspirobifluorene): Synthesis and properties of a novel styrenic polymer
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Synthesis and properties of a new class of styrenic polymer are reported. The radical polymerization of 2-vinyl-9,9′-spirobifluorene yielded high molecular weight poly(vinylspirobifluorene) with high thermal stability and high solubility, which gave a self-standing transparent film with high refractive index. Copyright
- Ishiwari, Fumitaka,Shinichi Kawasaki,Koyama, Asuhito,Takata, Toshikazu
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- Carbohydrate recognition: Enantioselective spirobifluorene diphosphonate receptors
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The mono- and bis-tetrabutylammonium salts of 2-ethyl-spirobifluorene monophosphonate and (±) 2,2'-diethyl-7,7'-didodecyloxy-spirobifluorene diphosphonate respectively, were synthesized and shown to bind strongly to a series of 1-O-octylglycosides in CD3CN.
- Das, Goutam,Hamilton, Andrew D.
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- Organic electroluminescent compound and organic electroluminescent device containing same
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The invention discloses an organic electroluminescent compound, which is formed by connecting a structural formula (1) and a structural formula (2), wherein * is a connecting site, the structural formula (1) and the structural formula (2) are defined in the specification, Y is O or S, X1-X8 are independently C-R5 or N, Z1-Z4 are independently C-R6 or N, the structural formula (1) can be connected with any non-N connecting site in Z1-Z4 on the A ring of the structural formula (2), and Ar is a substituted or unsubstituted C6-C60 aromatic hydrocarbon group or a substituted or unsubstituted C5-C60 heteroaromatic hydrocarbon group. When the organic electroluminescent compound is applied to the organic electroluminescent device, under the same current density, the luminous efficiency is greatly improved, the color purity is high, the starting voltage of the device is reduced, the power consumption of the device is relatively reduced, and the service life of the device is correspondingly prolonged.
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Paragraph 0149; 0150; 0151-0153
(2021/06/26)
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- COMPOUND FOR ORGANIC ELECTRIC ELEMENT, ORGANIC ELECTRIC ELEMENT COMPRISING THE SAME AND ELECTRONIC DEVICE THEREOF
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The present invention relates to: a compound for an organic electric element; the organic electric element using the same; and an electronic device thereof. According to the present invention, it is possible to achieve high luminous efficiency, low driving voltage, and high heat resistance of an element, and to improve color purity and lifespan of the element. By using the compound according to the present invention, it is possible to achieve high luminous efficiency, low driving voltage, and high heat resistance of the element, and to provide an effect of improving color purity and lifespan of the element.(110) Substrate(120) Positive electrode(130) Hole injection layer(140) Hole transfer layer(141) Buffer layer(150) Light emitting layer(151) Light emitting auxiliary layer(160) Electron transfer layer(170) Electron injection layer(180) Negative electrodeCOPYRIGHT KIPO 2020
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Paragraph 0263-0267; 0288-0289; 0291
(2020/04/30)
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- Method for synthesizing 9,9'-spirobifluorene derivative
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The invention relates to a method for synthesizing a 9,9'-spirobifluorene derivative, and belongs to the field of organic chemical synthesis. The method comprises the following steps: activating a C-Fbond in tetrahydrofuran under inert gas protection through reduction and lithiation reaction of raw materials of 2-fluorobiphenyl and a metal lithium sheet, thus establishing 2-biphenyl lithium; thenenabling the 2-biphenyl lithium to react with a fluorenone derivative, hydrolyzing, drying a solvent by distillation, and carrying out ring closing on solid in acetic acid, thus synthesizing the 9,9'-spirobifluorene derivative. According to the method disclosed by the invention, the 2-fluorobiphenyl in low cost is adopted as a raw material to replace 2-bromobiphenyl commonly adopted by a traditional method, the production cost is low, and reaction conditions are gentle; an applicable substrate range of the method is wide, and a new thought is provided for synthesis of the 9,9'-spirobifluorenederivative.
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- The compound for the electronic element
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The present invention relates to compounds for use in electronic devices, preferably organic electroluminescent devices. The invention furthermore relates to processes for the preparation of these compounds and to electronic devices comprising these compounds, preferably in a function as matrix materials and/or as electron-transport materials.
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Paragraph 0138; 0139
(2017/07/31)
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- A kind of 9, 9 the- [...] method for synthesis of derivatives of fluorene
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The invention discloses a synthesis method of a 9,9'-spirobifluorene derivative, and belongs to the field of organic chemical synthesis. The method comprises the steps that 2-bromochlorobenzene as a raw material acts with phenylmagnesium bromide and then reacts with bromofluorenone at 50-100 DEG C in a methyltetrahydrofuran solvent, hydrolysis and filtration are performed, solid performs closed-loop synthesis under acid catalysis to produce bromo-9,9'-spirobifluorene, and bromo-9,9'-spirobifluorene reacts with lithium diphenylphosphide to synthesize the 9,9'-spirobifluorene diphenylphosphine derivative. The synthesis method is simple in process; raw materials are low in price and easy to obtain; the production cost of series products is obviously lowered during synthesis; and the application of the fluorene derivative in design and synthesis of organic photoelectric materials as an intermediate is extended.
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Paragraph 0016; 0017; 0018
(2017/02/09)
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- MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES
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The present invention relates to compounds of the formula (1) which are suitable for use in electronic devices, in particular organic electroluminescent devices, and to electronic devices which comprise these compounds.
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Page/Page column 64; 65
(2016/06/15)
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- 2-Substituted vs 4-substituted-9,9'-spirobifluorene host materials for green and blue phosphorescent OLEDs: A structure-property relationship study
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Abstract We report a structure-property relationship study of four 9,9'-spirobifluorene (SBF) derivatives (4-5Pm-SBF, 2-5Pm-SBF, 4-Ph-SBF and 2-Ph-SBF), substituted with either phenyl or pyrimidine at the C2 or C4 position of the SBF core. Structural, thermal, electrochemical and photophysical properties have been examined and correlated to theoretical calculations in order to study the influence of the nature and the position of the substituent. The emission properties of 4- versus 2-substituted SBFs are noticeably different highlighting, in the excited state, the remarkable effect of substitution in ortho position of SBF. All compounds have been used as host material for green dopant in PhOLEDs with very high performances (2-5Pm-SBF: CE58 cd/A, PE35 lm/W, EQE14%). More importantly, the two 4-substituted SBFs have been used as host materials in blue PhOLEDs, displaying high performance and a decrease of VnfTH/inf for 4-5Pm-SBF due to the incorporation of the electron-withdrawing pyrimidine.
- Thiery, Sébastien,Declairieux, Céline,Tondelier, Denis,Seo, Gijun,Geffroy, Bernard,Jeannin, Olivier,Métivier, Rémi,Rault-Berthelot, Jo?lle,Poriel, Cyril
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p. 6337 - 6351
(2015/04/14)
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- Organic compounds for an organic electroluminescent device and an organic electroluminescent device comprising the same
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Provided are novel organic compounds for an organic electroluminescent device and an organic electroluminescent device comprising the same wherein the compounds are selected from a group of chemical formula 1.COPYRIGHT KIPO 2015
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- Novel spyrobifluorene type organic compounds and an organic electroluminescent device comprising the same
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The present invention provides a novel compound represented by the following Chemical Formula 1 and an organic electroluminescent device comprising the same.COPYRIGHT KIPO 2015
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- LIGHT-EMITTING ELEMENT, LIGHT-EMITTING DEVICE, AND ELECTRONIC DEVICE
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The present invention refers to and light emitting element using phosphorescent compounds to suitable provides device structure wherein the. Furthermore, the present invention refers to said by the use of having a high emission efficiency light-emitting device with high. In particular, the present invention refers to emits a long-life light-emitting device with high. Hole transport-magnetic host material and phosphorescent compound including number 1 luminescence layer and an electron-transporting host material and phosphorescent compound emitting layer including number 2, number 1 number 2 a luminescent layer number 1 light emitting layer and in contact with one another between electrode number 2 electrode and a light emitting element is is produced.
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- Novel tri-carbazole modified fluorene host material for highly efficient solution-processed blue and green electrophosphorescent devices
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A series of novel solution-processable small-molecule host materials: 2DPF-TCz, 2SBF-TCz, 27DPF-TCz, and 27SBF-TCz comprising a fluorene monomer as the rigid core and tri-carbazole as the periphery have been designed and synthesized, and their optical, electrochemical, and thermal properties have been fully characterized. The host materials exhibit high glass-transition temperatures (231-310 °C) and high triplet energy levels (2.61-2.73 eV). High-quality amorphous thin films can be obtained by spin-coating the host materials from solutions. It is found that the HOMO level of the host materials can be tuned by linking the tri-carbazole unit to the 2,7 positions of the fluorine core, resulting in appropriate HOMO energy levels (-5.36 to -5.23 eV) for improved hole-injection in the device. Solution-processed blue and green electrophosphorescent devices bases on the developed host materials exhibit high efficiencies of 21.2 and 34.8 cd A-1, respectively.
- Tang, Jinan,Chen, Yuanshen,Cong, Lei,Lin, Baoping,Sun, Yueming
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p. 3847 - 3853
(2014/06/09)
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- NOVEL COMPOUND AND ORGANIC ELECTRONIC DEVICE USING SAME
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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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- CARBAZOLE DERIVATIVE, AND LIGHT-EMITTING ELEMENT, LIGHT-EMITTING DEVICE, AND ELECTRONIC DEVICE USING CARBAZOLE DERIVATIVE
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To provide a light-emitting element having high luminous efficiency and to provide a light-emitting device and an electronic device which consumes low power and is driven at low voltage, a carbazole derivative represented by the general formula (1) is provided. In the formula, α1, α2, α3, and α4 each represent an arylene group having less than or equal to 13 carbon atoms; Ar1 and Ar2 each represent an aryl group having less than or equal to 13 carbon atoms; R1 represents any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted biphenyl group; and R2represents any of an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted biphenyl group. In addition, l, m, and n are each independenly 0 or 1.
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(2009/07/17)
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- Simple and efficient method for obtaining fluorene and spirobifluorene bromide derivatives
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A mild, simple, and efficient synthetic procedure for the preparation of 2-monobromo-, 2,7-dibromo-, and 2,2′,7,7′-tetrabromo-substituted spirobifluorene derivatives and their key intermediates, 2-monobromo- and 2,7-dibromo-substituted fluorene compounds, has been developed. The oxidative bromination of fluorene and spirobifluorene was achieved using NaBr/H2O2 as the bromine source. High conversion of the starting materials was achieved together with good selectivities under optimized reaction conditions. Copyright Taylor & Francis Group, LLC.
- Jiang, Wen-Feng,Wang, Hui-Long,Wang, An-Gang,Li, Zhe-Qi
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p. 1888 - 1895
(2008/09/20)
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- FLUORENE-BASED COMPOUND AND ORGANO-ELECTROLUMINESCENT DEVICE USING THE SAME
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Provided herein are fluorene-based compounds including a fluorene or a spirofluorene structure at both terminals and a spacer including one or more atoms between the both terminals. The invention further provides an organo-electroluminescent device having an organic layer in which the fluorene-based compound is introduced. The fluorene-based compound can be readily manufactured using dry and wet processes, and the organo-electroluminescent device using the same has excellent properties in color purity, internal and external efficiency, and thermal, optical and electrical stability.
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- Quinoxaline Derivative, And Light-Emitting Element And Light-Emitting Device Using Quinoxaline Derivative
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An object is to provide a novel organic compound capable of visible light emission. In particular, an object is to provide a novel organic compound that exhibits a broad emission spectrum when it is used for a light-emitting element. In addition, an object is to provide a light-emitting element and a light-emitting device that gives white light emission with an excellent color rendering property. The quinoxaline derivative represented by General Formula (1) is provided. Since the quinoxaline derivative represented by General Formula (1) is capable of emitting visible light, it can be favorably used for a light-emitting element. In particular, since the quinoxaline derivative represented by General Formula (1) exhibits a broad emission spectrum when it is used for a light-emitting element, by using it for a light-emitting element, a light-emitting element that gives white light emission with an excellent color rendering property can be obtained.
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Page/Page column 36-37
(2008/06/13)
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- Aromatic amine compound, and light emitting element, light emitting device, and electronic device using aromatic amine compound
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An object is to provide an aromatic amine compound with excellent heat resistance. Another object is to provide a light emitting element, a light emitting device, and an electronic device with excellent heat resistance. An aromatic amine compound represented by General Formula (1) is provided. The aromatic amine compound represented by General Formula (1) has a high glass transition point and excellent heat resistance. By using the aromatic amine compound represented by General Formula (1) for a light emitting element, a light emitting device, and an electronic device, a light emitting element, a light emitting device, and an electronic device with excellent heat resistance can be obtained.
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(2008/06/13)
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- SPIROFLUORENE DERIVATIVE, MATERIAL FOR LIGHT-EMITTING ELEMENT, LIGHT-EMITTING ELEMENT, LIGHT-EMITTING DEVICE, AND ELECTRONIC DEVICE
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It is an object of the present invention to provide a material having a high Tg and a wide energy gap. The present invention provides a spirofluorene derivative represented by General Formula 1. (In the formula, R1 is any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, or a group represented by General Formula 2. Each of R2 and R3 is either hydrogen or an alkyl group having 1 to 4 carbon atoms and may be identical or different. R4 is an aryl group having 6 to 15 carbon atoms. Each of R5 and R6 is any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 15 carbon atoms and may be identical or different.)
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Page/Page column 81-82
(2008/06/13)
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- Pi-conjugated compound having cardo structure, process for preparing same and use of same
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A π-conjugated compound having a cardo structure of formula (1): where R1 and R2 are hydrogen, alkyl, alkoxy, phenyl, naphthyl, phenoxy or halogen; Ar1 is a group of formula (2) or (3): where R3 thru R6 are hydrogen, alkyl, alkoxy, aryl, hetero-aryl, aryloxy or a halogen, and l and m are 0-3, and n is 0-2; and Ar2 is aryl or hetero aryl. The π-conjugated compound has good stability and is used as light emitting material.
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(2008/06/13)
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- ANTHRACENE DERIVATIVES AND ORGANIC ELECTROLUMINESCENT DEVICES MADE BY USING THE SAME
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An anthracene derivative represented by the following general formula (1) which enables an organic electroluminescence device to exhibit a great efficiency of light emission and uniform light emission even at high temperatures since crystallization is suppressed and no thermal decomposition takes place during vapor deposition and an organic electroluminescence device utilizing the derivative, are provided. [Ar represents a group represented by the following general formula (2): (L1 and L2 each represent a substituted or unsubstituted methylene group, ethylene group or the like, and at least one of them is present), Ar' represents a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, X represent an alkyl group or the like, a and b each represent an integer of 0 to 4, and n represents an integer of 1 to 3.]
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(2010/02/11)
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- BENZIDINE DERIVATIVE, AND LIGHT-EMITTING DEVICE AND ELECTRIC APPLIANCE USING THE BENZIDINE DERIVATIVE AS THE HOLE TRANSPORTING MATERIAL
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According to the present invention, a material that can be used as a hole transporting material is provided. Further, a material that is easily kept in a non-crystalline state and can be used as a hole transporting material is also provided. One embodiment of the present invention is a compound represented by a general formula (1). In the general formula (1), R1 is hydrogen or an alkyl group having 1-4 carbon atoms. Further, one embodiment according to the present invention is a hole transporting material containing the compound represented by the general formula (1).
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Page/Page column 32-34
(2008/06/13)
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- ETHYNYL CONTAINING ELECTRON TRANSPORT AGENTS AND THEIR USE IN ORGANIC LUMINESCENT DEVICES
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Compounds of formula (I), compositions, organic electronic devices, and methods for preparing organic electronic devices are described. The compounds of the invention contain at least two carbon-carbon triple bonds and a heteroaromatic ring E having at least one -C=N unit. The compounds can be used as electron transport agents in organic electronic devices such as organic electroluminescent devices.
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- Spiro compounds, and their use
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The present invention relates to novel spiro compounds of the formula (I)
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- Ter(9,9-diarylfluorene)s: Highly efficient blue emitter with promising electrochemical and thermal stability
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Novel ter(9,9-diarylfluorene)s were synthesized by a Suzuki-coupling reaction of 2-bromofluorene (1) and 2,7-fluorenediboronic ester derivatives (3) with high isolated yields (63-86%). The X-ray structure analysis of ter(9,9′-spirobifluorene) (4aa) revealed that the conjugated chromophore adopts a helical conformation. This conformation effectively releases the steric interaction between the fluorene moieties and prevents inter-chromophore interactions. The introduction of aryl groups at the C9 position of fluorene was highly beneficial to the thermal and morphological stability of these oligomers. These terfluorenes exhibit intense blue fluorescence with excellent quantum yields both in solution (～100%) and in solid state (66-90%), and possess interesting reversible redox properties. Highly efficient blue light-emitting OLED devices were fabricated using 4aa and 4cc as emitters as well as hole transporters. The devices exhibit low turn-on voltage (～3 V) and high EL external quantum efficiency (2.5-3%). Copyright
- Wong, Ken-Tsung,Chien, Yuh-Yih,Chen, Ruei-Tang,Wang, Chung-Feng,Lin, Yu-Ting,Chiang, Huo-Hsien,Hsieh, Ping-Yuan,Wu, Chung-Chih,Chou, Chung Hsien,Su, Yuhlong Oliver,Lee, Gene-Hsiang,Peng, Shie-Ming
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p. 11576 - 11577
(2007/10/03)
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- Head-to-tail regioregular oligothiophene-functionalized 9,9′-spirobifluorene derivatives. 1. Synthesis
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Two series of novel fully conjugated oligomers, oligothiophene-functionalized 9,9′-spirobifluorene derivatives, have been developed in this contribution. First, four 9,9′-spirobifluorene bromide derivatives (compounds 1a-d) are prepared through various synthetic routes. Oligothiophene derivatives with or without substituents are synthesized through the Grignard and Suzuki coupling reactions. The Negishi coupling reactions between oligothienylzinc chloride and various 9,9′spirobifluorene bromides with Pd(PPh3)4 as catalyst successfully produce the desired compounds, unsubstituted oligothiophene-functionalized 9,9′-spirobifluorene derivatives, compounds 2 to 4ad. Since the Negishi coupling reactions afford regioregularly head-to-tail (H-T) oligo(4-nhexylthiophene)-functionalized 9,9′-spirobifluorene derivatives in poor yields, the Suzuki coupling reactions between sodium 4-n-hexylthienyl-2-boronate 8, and various 9,9′-spirobifluorene-based bromides 1a-d and 9-16 are employed to produce highly regioregular head-to-tail oligothiophenefunctionalized 9,9′-spirobifluorene derivatives (compounds 5 to 7a-d) in very high yields. We also investigate the effect of solvents on the Suzuki coupling reactions. The structure and purity of all compounds are verified by FT-IR, 1H and 13C NMR, MS, and elemental analysis.
- Pei, Jian,Ni, Jing,Zhou, Xing-Hua,Cao, Xiao-Yu,Lai, Yee-Hing
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p. 4924 - 4936
(2007/10/03)
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- 113. Analogs of Cinchona alkaloids incorporating a 9,9′-spirobifluorene moiety
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The Cinchona alkaloid analogs (+)- and (-)-5 with a quinuclidine-2-methanol residue attached to C(2) of a 9,9′-spirobifluorene moiety were prepared as a racemic mixture by reacting lithiated 2-bromo-9,9′-spirobifluorene 7 with (2-ethoxycarbonyl)quinuclidine (±)-6 to give ketone (±)-8, followed by diastereoselective reduction with diisobutylaluminum hydride (DIBAL-H). The absolute configuration at C(9) and C(8), i.e., at the methanol bridge and the adjacent quinuclidine C-atom, in the two enantiomers of 5 is identical to the configuration at the corresponding centers in (-)-quinine (1) and (+)-quinidine (2), respectively. For the optical resolution of (±)-5, a chiral stationary phase for HPLC was prepared by covalently bonding quinine via a thiol spacer to a silica-gel surface. The enantiomer separation was accomplished at an a value of 1.61 with (±)-5 being eluted last, in agreement with 1H-NMR studies in CDCl3 which showed that (+)-5 underwent a more stable host-guest association with quinine than (-)-5. 1H{1H} Nuclear Overhauser effect (NOE) difference spectroscopical analysis of the host-guest associations with quinine in CDCl3, combined with computer-model examinations, allowed the assignment of the absolute configurations as (+)-(8R,9S)-5 and (-)-(8S,9R)-5. A detailed conformational analysis displayed excellent agreement between the results of computational methods (Monte Carlo multiple minimum simulations, analyses of the total energy as a function of the flexible dihedral angles in the molecule) and 1H{1H}-NOE difference spectroscopical data. It was found that (-)-5 and (+)-5 differ significantly in their conformational preference from their natural counterparts quinine (1) and quinidine (2) Whereas the natural alkaloids prefer the 'open' conformation, with the quinuclidine N-atom pointing away from the quinoline ring, analog (±)-5 adopts preferentially (by ca 4 kcal mol-1) a 'closed' conformation, in which the quinuclidine N-atom points into the cleft of the 9,9′-spirobifluorene moiety. Since the basic quinuclidine N-atom in the 'closed' conformation is sterically shielded from forming strong H-bonds, the new Cinchona alkaloid analogs form less stable host-guest associations via H-bonding than quinine or quinidine.
- Winter-Werner, Barbara,Diederich, Francois,Gramlich, Volker
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p. 1338 - 1360
(2007/10/03)
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