CN105646591A - Blue light iridium complex taking bromine-contained benzimidazoles as cyclometalated ligands and preparation method of blue light iridium complex - Google Patents
Blue light iridium complex taking bromine-contained benzimidazoles as cyclometalated ligands and preparation method of blue light iridium complex Download PDFInfo
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 45
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 150000001556 benzimidazoles Chemical class 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 239000003446 ligand Substances 0.000 title abstract 4
- 229910052751 metal Inorganic materials 0.000 claims description 34
- 239000002184 metal Substances 0.000 claims description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 28
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 24
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 24
- 229910052794 bromium Inorganic materials 0.000 claims description 24
- 125000004122 cyclic group Chemical group 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000012153 distilled water Substances 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 239000000539 dimer Substances 0.000 claims description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 6
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 4
- 229910052786 argon Inorganic materials 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 239000012065 filter cake Substances 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000001291 vacuum drying Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000010898 silica gel chromatography Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 13
- 125000001246 bromo group Chemical group Br* 0.000 abstract description 3
- 239000000178 monomer Substances 0.000 abstract description 3
- 238000005424 photoluminescence Methods 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- YRWMGOSKROWAIT-UHFFFAOYSA-N 2-(4-bromophenyl)-1h-benzimidazole Chemical compound C1=CC(Br)=CC=C1C1=NC2=CC=CC=C2N1 YRWMGOSKROWAIT-UHFFFAOYSA-N 0.000 abstract 1
- 238000005401 electroluminescence Methods 0.000 abstract 1
- 230000005284 excitation Effects 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 238000000103 photoluminescence spectrum Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a co-ordinate blue light iridium complex taking bromine-contained benzimidazoles as cyclometalated ligands and a preparation method of the blue light iridium complex. The structural general formula of the blue light iridium complex is Ir(BrPhBI)3, wherein the BrPhBI is 2-(4-bromophenyl)-benzimidazole cyclometalated ligands. For the Ir(BrPhBI)3 iridium complex, a fluorescence emission peak under the excitation of 365nm wavelength is positioned between 400nm and 550nm, and a maximum emission peak is positioned near 436nm; the Ir(BrPhBI)3 iridium complex emits blue light, can be used as a blue light luminescent material and is applied to the fields of photoluminescence, electroluminescence and the like. Meanwhile, the Ir(BrPhBI)3 iridium complex contains bromine atoms in structure, so the Ir(BrPhBI)3 iridium complex can be used as an active monomer and is used for developing polymer luminescent materials; a bromine-contained benzimidazole derivative ligand is simple in synthesis method and is high in yield. Therefore, the blue light iridium complex as the luminescent material has a good application prospect.
Description
Technical field
The present invention relates to field of luminescent technology, specifically relate to a class taking the benzimidazoles containing bromine as the blue light complex of iridium of cyclic metal complexes and its preparation method.
Background technology
Organic Light Emitting Diode (OrganicLight-EmittingDiodes, OLED) utilizes electronics and hole to combine the exciton diffusion produced luminescence to luminescent layer again, has huge application prospect in flat pannel display and illumination. The core material of OLED is electroluminescent material, is one of research focus always. The electroluminescent phosphorescence phenomenon based on heavy metal complex is in succession reported from the horse what light teach problem group of the Forrest teach problem group of Princeton university in 1998 and Jilin University, triplet state phosphorescence can be utilized in room temperature, and successfully develop the heavy metal complex phosphorescence device that theoretical internal quantum efficiency can reach 100%, make the research focus that organic electromechanical phosphorescent material becomes new. Organic electromechanical phosphorescent material great majority are for having d6And d8Heavy metal atom (such as platinum, iridium, the osmium) title complex of electronic structure, it is possible to utilize singlet and triplet excitons simultaneously, quantum yield is improved. Electrophosphoresceniridium iridium complex because its phosphorescent lifetime is relatively short, quantum yield height, the position changing substituting group and kind can regulate emission wavelength, and then realize the total colouring such as red, green, blue, it is a kind of phosphor material that research also has most at most application prospect.
Usually, the main part of ring metal iridium complex needs to be prepared by Stille or Suzuki linked reaction etc., harsh reaction conditions and the problem such as high cost, low-yield so that it is be difficult to industrialization. Therefore, the selection of part and preparation are significant for the new electromechanical phosphorescent material of exploitation. Wei-ShengHuang in 2004 has delivered at ChemistryofMaterials and has synthesized the excellent complex of iridium of luminescent properties by cyclic metal complexes of benzimidizole derivatives compounds. Based on advantages such as benzimidizole derivatives compounds synthetic method are simple, the present invention, taking the benzimidizole derivatives containing bromine as cyclic metal complexes, synthesizes equal coordination complex of iridium, and the complex of iridium obtained presents blue emission.
Summary of the invention
An object of the present invention is to provide a kind of blue light complex of iridium of benzimidazoles as cyclic metal complexes to contain bromine, directly can be used for the field such as photoluminescence and electroluminescent as luminescent material, simultaneously structurally containing bromine atoms, can be used as reactive monomer, for the exploitation of polymer luminescent material.
The two of the object of the present invention are to provide a kind of method of benzimidazoles as the preparation of the blue light complex of iridium of cyclic metal complexes to contain bromine.
The technical scheme adopted for realizing the object of the present invention is:
1, a kind of blue light complex of iridium of benzimidazoles as cyclic metal complexes to contain bromine, it is characterised in that the general structure that the described benzimidazoles containing bromine is the blue light complex of iridium of cyclic metal complexes is Ir (BrPhBI)3, wherein BrPhBI is the benzimidazoles cyclic metal complexes containing bromine; The structural formula that the described benzimidazoles containing bromine is the blue light complex of iridium of cyclic metal complexes is as follows:
In structural formula I, R is hydrogen atom or alkyl
2, to contain the preparation method of benzimidazoles as the blue light complex of iridium of cyclic metal complexes of bromine
1) preparation of 2-(4-bromophenyl)-benzimidazoles chlorine bridge connection dimer
Under protection of inert gas, in round-bottomed flask, adding hydrated iridium trichloride, 2-(4-bromophenyl)-benzimidazoles cyclic metal complexes and appropriate ethylene glycol monoethyl ether and distilled water mixed solution, heating reflux reaction, after 24 hours, is cooled to room temperature, reaction product is filtered, filter cake respectively washs three times with distilled water, ethanol respectively, vacuum-drying, obtains 2-(4-bromophenyl)-benzimidazoles chlorine bridge connection dimer, without the need to further purification, sealed and saved backup;
Described hydrated iridium trichloride, 2-(4-bromophenyl)-benzimidazoles cyclic metal complexes add according to the mol ratio of 1:2��3.
In described mixed solution, ethylene glycol monoethyl ether and distilled water volume ratio are 3:1.
Described rare gas element is argon gas or nitrogen.
2) to contain the preparation of benzimidazoles as the blue light complex of iridium of the equal coordination of cyclic metal complexes of bromine
Under protection of inert gas, by above-mentioned 2-(4-bromophenyl)-benzimidazoles chlorine bridge connection dimer, 2-(4-bromophenyl)-benzimidazoles cyclic metal complexes and Anhydrous potassium carbonate are dissolved in qs glycerin, after reacting by heating, it is cooled to room temperature, pour in the beaker of appropriate distilled water, with dichloromethane extraction aqueous phase three times, merge organic phase and with saturated common salt water washing three times, anhydrous magnesium sulfate drying, filter, revolve and boil off except solvent, the ethyl acetate/dichloromethane of crude product 1:10 (volume ratio) makes eluent, silica gel column chromatography is separated, obtain the blue light complex of iridium of equal coordination, product rate is 25��35%, its structure is such as formula shown in I.
Described 2-(4-bromophenyl)-benzimidazoles chlorine bridge connection dimer, 2-(4-bromophenyl)-benzimidazoles cyclic metal complexes and Anhydrous potassium carbonate add according to the mol ratio of 1:2��3:2��5.
Described reacting by heating, Heating temperature is 190��210 DEG C, and the reaction times is 24��48 hours.
The present invention provides a kind of blue light complex of iridium of benzimidazoles as cyclic metal complexes to contain bromine, it is possible to be directly used for the field such as photoluminescence and electroluminescent as luminescent material; Simultaneously structurally containing bromine atoms, can be used as reactive monomer, for the exploitation of polymer luminescent material; Cyclic metal complexes is simple containing the benzimidizole derivatives synthetic method of bromine, product rate height.Therefore, the blue light complex of iridium of the present invention has good application prospect as luminescent material.
Embodiment
Below by specific embodiment, the present invention is further illustrated, but the protection domain that these specific embodiments do not limit the present invention in any way.
Embodiment 1
The synthesis of Lan Guangsan (2-(4-bromophenyl)-1-hydrogen-benzoglyoxaline) complex of iridium.
Under argon gas shielded, round-bottomed flask adds 353mg (1.00mmol) IrCl3��3H2O, 628mg (2.30mmol) 2-(4-bromophenyl)-1-hydrogen-benzoglyoxaline, 30mL ethylene glycol monoethyl ether and 10mL distilled water, heating reflux reaction is after 24 hours, it is cooled to room temperature, reaction product is filtered, filter cake respectively washs three times with distilled water, ethanol respectively, vacuum-drying, obtains 2-(4-bromophenyl)-1-hydrogen-benzoglyoxaline chlorine bridge connection dimer, without the need to further purification, sealed and saved backup.
Under argon gas shielded, round-bottomed flask adds 308mg (0.20mmol) 2-(4-bromophenyl)-1-hydrogen-benzoglyoxaline chlorine bridge connection dimer, 164mg (0.60mmol) 2-(4-bromophenyl)-1-hydrogen-benzoglyoxaline, 100mg Anhydrous potassium carbonate and 15mL glycerine, it is heated to 210 DEG C of reactions after 24 hours, it is cooled to room temperature, pour in the beaker filling 50mL distilled water, with dichloromethane extraction aqueous phase three times, merge organic phase and with saturated common salt water washing three times, anhydrous magnesium sulfate drying, filter, revolve and boil off except solvent, crude product ethyl acetate/dichloromethane (1:10) makes eluent column chromatography, obtain 120mg tri-(2-(4-bromophenyl)-1-hydrogen-benzoglyoxaline) complex of iridium white solid, product rate is 30%.
1HNMR(400MHz,CDCl3) �� 7.72 7.61 (m, 9H), 7.49 (t, J=1.9Hz, 6H), 7.30 7.27 (m, 6H), 5.34 (dd, J=13.7,9.3Hz, 3H).
Anal.calcdforC39H24Br3IrN6 (%): C46.44, H2.40, N8.33; Found (%): C46.21, H2.60, N8.47.
Being dissolved in methylene dichloride by three (2-(4-bromophenyl)-1-hydrogen-benzoglyoxaline) complex of iridium, (concentration is about 1 �� 10-5Mol/L), measure its photoluminescence spectra under room temperature condition. Fluorescence emission peak under 365nm wavelength excites is positioned at 400��550nm, and maximum emission peak is positioned at 436nm, is blue emission, and chromaticity coordinates is (0.173,0.144), is positioned at blue region.
Embodiment 2
The synthesis of Lan Guangsan (2-(4-bromophenyl)-1-methyl-benzoglyoxaline) complex of iridium.
Under nitrogen protection, round-bottomed flask adds 353mg (1.00mmol) IrCl3��3H2O, 689mg (2.40mmol) 2-(4-bromophenyl)-1-methyl-benzoglyoxaline, 30mL ethylene glycol monoethyl ether and 10mL distilled water, heating reflux reaction is after 24 hours, it is cooled to room temperature, reaction product is filtered, filter cake respectively washs three times with distilled water, ethanol respectively, vacuum-drying, obtains 2-(4-bromophenyl)-1-methyl-benzoglyoxaline chlorine bridge connection dimer, without the need to further purification, sealed and saved backup.
Under nitrogen protection, round-bottomed flask adds 320mg (0.2mmol) 2-(4-bromophenyl)-1-methyl-benzoglyoxaline chlorine bridge connection dimer, 161mg (0.56mmol) 2-(4-bromophenyl)-1-methyl-benzoglyoxaline, 110mg Anhydrous potassium carbonate and 15mL glycerine, it is heated to 200 DEG C of reactions after 36 hours, it is cooled to room temperature, pour in the beaker filling 50mL distilled water, with dichloromethane extraction aqueous phase three times, merge organic phase and with saturated common salt water washing three times, anhydrous magnesium sulfate drying, filter, revolve and boil off except solvent, crude product ethyl acetate/dichloromethane (1:10) makes eluent column chromatography, obtain 132mg tri-(2-(4-bromophenyl)-1-methyl-benzoglyoxaline) complex of iridium white solid, product rate is 31.4%.
1HNMR(400MHz,CDCl3) �� 7.74 7.63 (m, 9H), 7.55 (t, J=1.9Hz, 6H), 7.28 7.26 (m, 6H), 4.12 (m, 9H).
Anal.calcdforC42H30Br3IrN6 (%): C48.00, H2.86, N8.00; Found (%): C48.11, H2.78, N8.07.
Being dissolved in methylene dichloride by three (2-(4-bromophenyl)-1-methyl-benzoglyoxaline) complex of iridium, (concentration is about 1 �� 10-5Mol/L), measure its photoluminescence spectra under room temperature condition. Fluorescence emission peak under 365nm wavelength excites is positioned at 400��550nm, and maximum emission peak is positioned at 434nm, is blue emission, and chromaticity coordinates is (0.171,0.156), is positioned at blue region.
Claims (7)
1. one kind taking the benzimidazoles containing bromine as the blue light complex of iridium of cyclic metal complexes, it is characterised in that the general structure that the described benzimidazoles containing bromine is the blue light complex of iridium of cyclic metal complexes is Ir (BrPhBI)3, wherein BrPhBI is the benzimidazoles cyclic metal complexes containing bromine; The structural formula that the described benzimidazoles containing bromine is the blue light complex of iridium of cyclic metal complexes is as follows:
In structural formula I, R is hydrogen atom or alkyl.
2., taking the benzimidazoles containing bromine as a preparation method for the blue light complex of iridium of cyclic metal complexes, it is characterized in that:
1) preparation of 2-(4-bromophenyl)-benzimidazoles chlorine bridge connection dimer
Under protection of inert gas, in round-bottomed flask, adding hydrated iridium trichloride, 2-(4-bromophenyl)-benzimidazoles cyclic metal complexes and appropriate ethylene glycol monoethyl ether and distilled water mixed solution, heating reflux reaction, after 24 hours, is cooled to room temperature, reaction product is filtered, filter cake respectively washs three times with distilled water, ethanol respectively, vacuum-drying, obtains 2-(4-bromophenyl)-benzimidazoles chlorine bridge connection dimer, without the need to further purification, sealed and saved backup;
2) to contain the preparation of benzimidazoles as the blue light complex of iridium of the equal coordination of cyclic metal complexes of bromine
Under protection of inert gas, by above-mentioned 2-(4-bromophenyl)-benzimidazoles chlorine bridge connection dimer, 2-(4-bromophenyl)-benzimidazoles cyclic metal complexes and Anhydrous potassium carbonate are dissolved in qs glycerin, after reacting by heating, it is cooled to room temperature, pour in the beaker of appropriate distilled water, with dichloromethane extraction aqueous phase three times, merge organic phase and with saturated common salt water washing three times, anhydrous magnesium sulfate drying, filter, revolve and boil off except solvent, the ethyl acetate/dichloromethane that crude product volume ratio is 1:10 makes eluent, silica gel column chromatography is separated, obtain the blue light complex of iridium of equal coordination.
3. according to claim 2 a kind of taking containing the benzimidazoles of bromine as the preparation method of the blue light complex of iridium of cyclic metal complexes, it is characterized in that step 1) hydrated iridium trichloride, 2-(4-bromophenyl)-benzimidazoles cyclic metal complexes add according to the mol ratio of 1:2��3.
4. according to claim 2 a kind of taking the benzimidazoles containing bromine as the preparation method of the blue light complex of iridium of cyclic metal complexes, it is characterized in that in described mixed solution, ethylene glycol monoethyl ether and distilled water volume ratio are 3:1.
5. according to claim 2 a kind of taking the benzimidazoles containing bromine as the preparation method of the blue light complex of iridium of cyclic metal complexes, it is characterized in that described rare gas element is argon gas or nitrogen.
6. according to claim 2 a kind of taking the benzimidazoles containing bromine as the preparation method of the blue light complex of iridium of cyclic metal complexes, it is characterized in that described 2-(4-bromophenyl)-benzimidazoles chlorine bridge connection dimer, 2-(4-bromophenyl)-benzimidazoles cyclic metal complexes and Anhydrous potassium carbonate add according to the mol ratio of 1:2��3:2��5.
7. a kind of benzimidazoles to contain bromine according to claim 2 is as the preparation method of the blue light complex of iridium of cyclic metal complexes, it is characterized in that described reacting by heating, and Heating temperature is 190��210 DEG C, and the reaction times is 24��48 hours.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1726606A (en) * | 2002-11-08 | 2006-01-25 | 通用显示公司 | Organic light emitting materials and devices |
| US20110050093A1 (en) * | 2009-08-31 | 2011-03-03 | Fujifilm Corporation | Method of forming metal complex compound, and organic electroluminescence device |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1726606A (en) * | 2002-11-08 | 2006-01-25 | 通用显示公司 | Organic light emitting materials and devices |
| US20110050093A1 (en) * | 2009-08-31 | 2011-03-03 | Fujifilm Corporation | Method of forming metal complex compound, and organic electroluminescence device |
Non-Patent Citations (2)
| Title |
|---|
| 吕剑虹等: "基于氟代苯并咪唑配体的绿光铱配合物的合成与表征", 《应用化学》 * |
| 曾惠卷等: "主链型铱配合物电磷光聚合物的合成与性能的研究", 《中国化学会第29届学术年会摘要集——第17分会：光电功能器件》 * |
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