171408-76-7

Basic information

• Product Name: 2-Bromo-9,9'-spirobi[9H-fluorene]
• Synonyms: 9,9′-Spirobi[9H-fluorene],2′-bromo;2-BROMO-9,9''-SPIROBIFLUOROENE;2-Bromo-9,9'-spirobi[9H-fluorene];2-Bromo-9,9'-spirobi;2-BroMo-9,9'-spirobiflu;2-BroMo-9,9'-spirobifluoren;2-broMo-9,9'-Spirobi[9H]-fluorene (BSBF);2- broMospirofluorene
• CAS NO: 171408-76-7
• Molecular Formula: C₂₅H₁₅Br
• Molecular Weight: 395.29
• EINECS: 1312995-182-4
• Product Categories: Fluorene Derivatives;Fluorene Series;OLED materials,pharm chemical,electronic;Pyridines
• Mol File: 171408-76-7.mol

Chemical Properties

• Melting Point: 182.0 to 186.0 °C
• Boiling Point: 517.213 °C at 760 mmHg
• Flash Point: 259.774 °C
• Appearance: off-white crystal
• Density: 1.522 g/cm³
• Vapor Pressure: 0-0.001Pa at 20-50℃
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-Bromo-9,9'-spirobi[9H-fluorene](CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-9,9'-spirobi[9H-fluorene](171408-76-7)
• EPA Substance Registry System: 2-Bromo-9,9'-spirobi[9H-fluorene](171408-76-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 171408-76-7(Hazardous Substances Data)

Usage

Chemical Properties

Off-white to light yellow crystal or powder

Synthesis

Synthesis of 2-bromo-spirofluorene2-bromo-9-hydroxy-9-(2-biphenyl)fluorene (2g) dissolved in 25 mL acetic acid (15 mol/L) containing hydrochloric acid (12 mol/L) was refluxed for about 2 h to separate out a white solid, which was recrystallized with ethanol to produce white crystals of 2-bromo-spirofluorene (1.2 g, yield 63%). GC-MS (m/z +): 394. 1HNMR (400 MHz, CDCl3, ppm):δ7.80～7.86 (m, 3H), δ7. 70 (d, 1H),δ7.48 (m, 1H), δ7.36 ～ 7.40 (m, 3H), δ7.13 (m, 3H), δ6.84 (d, 1H), δ6.72 (m, 3H)

References

http://www.sigmaaldrich.com/catalog/product/aldrich/767735?lang=en®ion=USTang, S., et al. "A Molecular Glass for Deep-Blue Organic Light-Emitting Diodes Comprising a 9,9′-Spirobifluorene Core and Peripheral Carbazole Groups." Advanced Functional Materials 17.15(2010):2869-2877.Nakanotani, H., et al. "Extremely Low-Threshold Amplified Spontaneous Emission of 9,9′-Spirobifluorene Derivatives and Electroluminescence from Field-Effect Transistor Structure." Advanced Functional Materials17.14(2010):2328-2335.

Upstream product

• 3096-56-8 2-bromofluoren-9-one 
• 2113-51-1 2-iodobiphenyl 
• 82214-69-5 2-biphenylmagnesium bromide 
• 2052-07-5 2-Bromobiphenyl 
• 159-66-0 9,9'-spirobifluorene 
• 486-25-9 9-fluorenone 
• 583-55-1 1-Bromo-2-iodobenzene 
• 100-58-3 phenylmagnesium bromide 
• 694-80-4 2-bromo-1-chlorobenzene 
• 321-60-8 2-fluorobiphenyl 
• 236389-20-1 9-(biphenyl-2-yl)-2-bromo-9-fluorenol 

Downstream Products

• 782504-06-7 2′-cyano-9,9-spirobifluorene 
• 236389-21-2 9,9'-spirobi[9H-fluoren]-2'-yl-boronic acid 
• 934409-42-4 2-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-spiro-9,9'-bifluorene 
• 1004758-60-4 C₆₈H₄₁N 
• 1160294-61-0 N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-spiro-9,9'-bifluoren-2-amine 
• 1221237-99-5 C₃₁H₁₉Cl 
• 1334287-60-3 4-(9,9'-spirobifluoren-2-yl)benzaldehyde 
• 1241891-64-4 (2'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene]) 
• 1601479-58-6 1,2-bis[4-(9,9'-spirobifluorene-7-yl)phenyl]-1,2-diphenylethene 
• 118951-68-1 9,9'-spirobi(9H-fluorene)-2-amine 
• 1613668-54-4 C₅₄H₃₇NSi 
• 1613668-55-5 C₆₁H₄₁NSi 
• 1613668-58-8 C₄₉H₃₃BrSi 
• 1613668-59-9 C₆₁H₄₀BrNSi 

Relevant articles and documents

Side chain modification on PDI-spirobifluorene-based molecular acceptors and its impact on organic solar cell performances

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.

Spirobifluorene/sulfone hybrid: Highly efficient solution-processable material for UV-violet electrofluorescence, blue and green phosphorescent OLEDs

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.

Poly(vinylspirobifluorene): Synthesis and properties of a novel styrenic polymer

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

Carbohydrate recognition: Enantioselective spirobifluorene diphosphonate receptors

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.

Organic electroluminescent compound and organic electroluminescent device containing same

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.

COMPOUND FOR ORGANIC ELECTRIC ELEMENT, ORGANIC ELECTRIC ELEMENT COMPRISING THE SAME AND ELECTRONIC DEVICE THEREOF

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

Method for synthesizing 9,9'-spirobifluorene derivative

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.

The compound for the electronic element

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.

A kind of 9, 9 the- [...] method for synthesis of derivatives of fluorene

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.

MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES

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.