CN101240064B - Application of quinoline aluminum coordination macromolecule - Google Patents
Application of quinoline aluminum coordination macromolecule Download PDFInfo
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- CN101240064B CN101240064B CN2008100340544A CN200810034054A CN101240064B CN 101240064 B CN101240064 B CN 101240064B CN 2008100340544 A CN2008100340544 A CN 2008100340544A CN 200810034054 A CN200810034054 A CN 200810034054A CN 101240064 B CN101240064 B CN 101240064B
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- oxine
- quinoline
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Abstract
The invention relates to a kind of quinoline aluminum coordinated macromolecular, particularly relates to application of 3,5-2(8-hydroxyl quinoline)-benzoic acid-aluminium coordinated macromolecular, and pertains to luminescent materials. The invention includes adding 5-acryl-8-hydroxyl quinoline and 3,5-2aminobenzoic acid at a mole ratio of 2:1 into toluol, heating reflux for over 48 hours, scrubbing with ethanol and trichloromethane respectively after filtering; adding product of previous step and adequate aluminium salt needed according to coordination ratio into ethanol or methanol, stirring, waiting the solution to be clarified. The inventive quinoline aluminum coordinated macromolecular can irradiate blue light OLED needed, and can be used in organic light emitting diode as blue light material.
Description
Technical field
The present invention relates to the high molecular application of quinoline aluminum coordination, belong to field of light emitting materials.
Background technology
1987, organic small molecule material---three (oxine) aluminium (AlQ) is as luminescent layer for the employing of Kodak company, manufactured a kind of organic electroluminescence device (OLED) of green light, this ultra-thin flat device has low driving voltage, high brightness, advantage such as energy-conservation.From then on the ORGANIC ELECTROLUMINESCENCE DISPLAYS technology enters a brand-new era as third generation technique of display, and has obtained vigorous growth.
The oxine metal complexes is still the of paramount importance a kind of material in OLED field at present.It not only can be used for luminescent layer, also is widely used as the electric transmission layer material of OLED simultaneously.But because of its as small molecules, in the device configuration process, mainly based on vacuum evaporation deposition, complex process, cost height, and be not easy to make large-sized indicating meter.People such as Tan Songting handle for the liquid phase that realizes the oxine metal complex, two oxine-Schiff's base-zinc the polymer complex that has synthesized a kind of green light is for the high molecular of oxine metal complexes provides a good idea.But this coordination high polymer can only be dissolved in N, in the high boiling point intensive polar solvents such as dinethylformamide, limited its structure device feasibility.
Summary of the invention
The purpose of this invention is to provide the high molecular application of quinoline aluminum coordination, be specifically related to 3,5-two (oxine)-phenylformic acid-aluminium coordination high polymer is to solve above-mentioned problems of the prior art.
Provided by the invention 3,5-two (oxine)-phenylformic acid-aluminium coordination high polymer is by building-up process preparation shown in Figure 1, now comments as follows:
(1) with 5-aldehyde radical-oxine and 3, the 5-diaminobenzoic acid joins in the toluene with 2: 1 ratio of molar weight, and reflux 24～72 hours is filtered the back also respectively with ethanol and trichloromethane washing;
(2) with the product of step (1) with add in ethanol or the methyl alcohol by the required capacity metallic aluminium salt of coordination ratio, stir, treat the solution clarification.
Described 5-aldehyde radical-oxine all has synthetic at the traditional literature report, preferable methods is the back flow reaction recrystallization method.
The preferred soluble metal aluminium of described metallic aluminium salt salt is as aluminum chloride, aluminum nitrate, aluminium hydroxide etc.
Provided by the invention 3,5-two (oxine)-phenylformic acid-aluminium coordination high polymer structural formula such as Fig. 2.
Provided by the present invention 3,5-two (oxine)-phenylformic acid-aluminium coordination high polymer has the following advantages:
(1) can launch OLED blue-light-emitting in short supply, be used for light-emitting display device as blue light material.
(2) be dissolved in usual vehicle, and by method systems such as ink-jet, spin coating film.
(3) can be doped in the inorganic matrix by the method for collosol and gel, and keep its characteristics of luminescence, it is simple to can be used for organic-inorganic photoluminescence coating doping way
(4) technology is simple, and cost is low.
Quinoline aluminum coordination polymer of the present invention can be used for light-emitting display device.
Description of drawings
The synthesis flow of Fig. 1 oxine aluminium provided by the invention coordination high polymer.
Fig. 2 is of the present invention 3,5-two (oxine)-phenylformic acid-aluminium coordination high polymer.
The mass spectrum of Figure 35-aldehyde radical-oxine.Synthetic this compound of proof.
Figure 43,5-two (the oxine)-benzoic proton nmr spectra that in the deuterated dimethyl sulfoxide solvent, records.Synthetic this compound of proof.
Fig. 5 is with concentration 3, the luminescent spectrum that the aluminium coordination product of 5-two (oxine)-phenylformic acid and oxine separately excitation peak position about 365nm excites.Solid line is 3, the fluorescence emission peak of 5-two (oxine)-phenylformic acid-aluminium coordination high polymer.Dotted line is the fluorescence emission peak of oxine aluminium.By the amount conversion that contains quinoline, though both concentration ratios are 2: 1, the luminous strength ratio of the former with the latter was greater than 3: 1.The former spectrum also blue shift to the 471nm place.
Fig. 6 presses the oxine aluminium polymer complex of embodiment 4 preparations and the luminescent spectrum of zirconic organic/inorganic composite film.Emission peak is at the 474nm place.
Embodiment
Mode illustrates the present invention by the following examples, but is not limited only to following examples.
Embodiment
25g analytical pure oxine is dissolved in the 100mL dehydrated alcohol, adds NaOH solution (50gNaOH is dissolved in the 70mL deionized water), mix and cool off the back and drip trichloromethane (25mL dripped off in 1 hour).After trichloromethane drips, intensification stirring and refluxing reaction 18 hours.Steam excessive trichloromethane and ethanol on Rotary Evaporators, residual residue is dissolved in the 600mL deionized water, regulates pH value to 5～6 with dilute hydrochloric acid, and the precipitation generation is arranged, suction filtration and behind the deionized water wash throw out placed 80 ℃ oven drying.Dried solid grinding powder with the Petroleum ether extraction of 90～120 ℃ of boiling ranges 48 hours, with the extracting solution cooling, filters and collects precipitate, with the dehydrated alcohol recrystallization in the fat extraction device.Obtain 5-aldehyde radical-oxine.Mass spectral characteristi the results are shown in Figure 2.
With 0.27g 5-aldehyde radical-oxine and 0.618g 3, the 5-diaminobenzoic acid joins in the toluene, reflux 48 hours.Filter products therefrom, and respectively with ethanol and trichloromethane washing.Treat 80 ℃ of following dryings.Get 3,5-two (oxine)-phenylformic acid.Proton nmr spectra characterization result (see figure 3): 1H NMR (500MHz, DMSO-d6): δ 13.12 (br, 1H), 10.68 (br, 2H), 9.92 (d, 2H), 9.13 (s, 2H), 8.96 (d, 2H), 8.16 (d, J=7.8Hz, 2H), 7.76-7.73 (m, 4H), 7.59 (s, 1H), 7.24 (d, J=7.8Hz, 2H) .Anal.Calcd for C27H18N4O4:C 70.12%; H 3.92%; N 12.11%.Found:C 69.30%; H 4.04%; N 12.07%.
With 0.115g 3,5-two (oxine)-phenylformic acid and 0.06g Aluminium chloride hexahydrate add in the 20mL ethanol, vigorous stirring, and solution is slowly clarified.Because 3,5-two (oxine)-phenylformic acid utmost point is insoluble in ethanol, the clarification explanation 3 of solution, 5-two (oxine)-phenylformic acid has entered in the polymer complex network with the form of part.
In tetrabutyl zirconate: Glacial acetic acid: methyl ethyl diketone: propyl alcohol: ethanol: water=20: 12: 5: 20: 5: 5 ratio preparation zirconia sol, to join solution and zirconia sol among the embodiment 3 with 1: 20 mixed, with spin-coating legal system film, drying is 2 hours in 80 ℃ of baking ovens.Its fluorescence emission spectrum is seen Fig. 5.
Claims (1)
1. quinoline aluminum coordination polymer, its structural formula is
Be used for light-emitting display device.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008100340544A CN101240064B (en) | 2008-02-28 | 2008-02-28 | Application of quinoline aluminum coordination macromolecule |
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| CN2008100340544A CN101240064B (en) | 2008-02-28 | 2008-02-28 | Application of quinoline aluminum coordination macromolecule |
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| CN101240064A CN101240064A (en) | 2008-08-13 |
| CN101240064B true CN101240064B (en) | 2011-06-01 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006112225A1 (en) * | 2005-03-31 | 2006-10-26 | Nippon Steel Chemical Co., Ltd. | Organic el material, organic el element employing the same, and process for producing organic el element |
| CN1944440A (en) * | 2006-10-31 | 2007-04-11 | 延边大学 | Process for preparing 8-hydroxy quinoline aluminum |
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2008
- 2008-02-28 CN CN2008100340544A patent/CN101240064B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006112225A1 (en) * | 2005-03-31 | 2006-10-26 | Nippon Steel Chemical Co., Ltd. | Organic el material, organic el element employing the same, and process for producing organic el element |
| CN1944440A (en) * | 2006-10-31 | 2007-04-11 | 延边大学 | Process for preparing 8-hydroxy quinoline aluminum |
Non-Patent Citations (1)
| Title |
|---|
| Yanting Yang，etc..First-principle Band Structure Calculations of Tris(8-hydroxyquinolinato)aluminum.《J. Phys. Chem. B》.2006,第110卷第3180-3184页. * |
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