CN101538286B - Monomer for organic electro-phosphorescent polymer - Google Patents
Monomer for organic electro-phosphorescent polymer Download PDFInfo
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- CN101538286B CN101538286B CN2009100220316A CN200910022031A CN101538286B CN 101538286 B CN101538286 B CN 101538286B CN 2009100220316 A CN2009100220316 A CN 2009100220316A CN 200910022031 A CN200910022031 A CN 200910022031A CN 101538286 B CN101538286 B CN 101538286B
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- phosphorescent polymer
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Abstract
The invention discloses a monomer for an organic electro-phosphorescent polymer. The monomer for the organic electro-phosphorescent polymer is formed by using end alkene beta-diketone as a ligand and complexing metal iridium ions. The structure of the monomer is given as below, wherein R is a hydrogen atom or a fluorine atom. It proves that the monomer for the organic electro-phosphorescent polymer is an electroluminescent material containing a polymerization activity center and can be used as an organic electroluminescent material or is used for preparing the organic electro-phosphorescent polymer.
Description
Technical field
The present invention relates to a kind of monomer for organic electro-phosphorescent polymer, this monomer for organic electro-phosphorescent polymer is a kind of complex of iridium that contains with end alkene beta-diketon.
Background technology
Development along with the information age; Have efficient, energy-conservation, light-weight organic electroluminescent flat-panel screens (OLEDs) and more and more receive people's attention, this type of active illuminating, light, thin, good contrast, the organic electroluminescence device that energy consumption is low have proposed higher requirement to luminescent material.The organic electroluminescence device can be divided into small molecules organic electroluminescence device and polymer organic electroluminescence device according to the difference of its material.
The small molecules organic electroluminescence device thin layer crystallization occurs easily when practical application, thereby influences device lifetime.
In order to solve the problem that the small molecules organic electroluminescence device exists; Best bet is the synthetic luminescence polymer of design; Simultaneously because the polymer organic electroluminescence device manufacture method is simple, cost of manufacture is low, and favorable mechanical character is arranged, and makes it become the research focus.Yet this type of organic electro-phosphorescent polymer monomeric species seldom at present.
Summary of the invention
Defective or deficiency to above-mentioned prior art existence; The objective of the invention is to; A kind of monomer for organic electro-phosphorescent polymer is provided, and this monomer for organic electro-phosphorescent polymer not only has end alkene polymerization activity center, but also has higher luminous efficiency; Can be as electroluminescent organic material, or be used to prepare organic electro-phosphorescent polymer.
In order to realize above-mentioned task, the present invention takes following technical solution:
A kind of monomer for organic electro-phosphorescent polymer is characterized in that, this monomer for organic electro-phosphorescent polymer that makes is the complex of iridium that contains with end alkene beta-diketon, and its general structure is following:
Wherein R is Wasserstoffatoms or fluorine atom.
When R is a Wasserstoffatoms, obtain compound two (2-phenylpyridine) [1-methyl isophthalic acid 3-tetradecene-2,4-diketone] and close iridium, its structural formula is following:
When R is fluorine atom, obtain compound two (2-(4 ', 6 '-difluoro) phenylpyridine) (13-tetradecene-2,4-diketone) and close iridium, its structural formula is following:
The present invention is synthetic with reference to following route:
Through experiment showed, monomer for organic electro-phosphorescent polymer of the present invention, contain the end alkene at polymerization activity center, can further prepare the iridium-containing phosphorescent polymer luminescent material, and can directly use as electroluminescent organic material.
Description of drawings
Fig. 1 is the spectrogram that compound two (2-phenylpyridine) [1-methyl isophthalic acid 3-tetradecene-2,4-diketone] closes iridium;
Fig. 2 is that two compounds (2-(4 ', 6 '-difluoro) phenylpyridine) (13-tetradecene-2,4-diketone) close the spectrogram of iridium.
The embodiment that provides below in conjunction with accompanying drawing and contriver does further detailed description to the present invention.
Embodiment
According to monomer for organic electro-phosphorescent polymer general structure of the present invention, the contriver provides following examples, need to prove, these embodiment are mainly used in those skilled in the art to further understanding of the present invention, the invention is not restricted to these embodiment.
Embodiment 1: preparation compound two (2-phenylpyridine) [1-methyl isophthalic acid 3-tetradecene-2,4-diketone] closes iridium (ppy)
2Ir (bsh)
1.1 synthetic route
1.2 synthesis step:
1.2.12-phenylpyridine chlorine closes iridium (ppy)
4Ir
2Cl
2Synthetic
In the there-necked flask of 250mL, add phenylpyridine Hppy 2.3g successively, IrCl
3.3H
2O 2.63g, 500mL water, 150mL ethylene glycol ethyl ether, N
2Under the protection, back flow reaction 24h.Reacting liquid filtering, washing is to neutrality, oven for drying.Separate for the eluent silica gel column chromatography with the normal hexane.Get 3.3g thionaphthene yl pyridines chlorine and close iridium.
1.2.2 1-methyl isophthalic acid 3-tetradecene-2,4-diketone (bsh) synthetic
Add the 9.3g potassium tert.-butoxide in the 250mL there-necked flask successively, 5.0g acetone, the own ester of 12.9g undecylenic acid stirs 72h under the room temperature.Reaction solution is poured in the 150mL frozen water, fully stirred.Hydrogen chloride with 10% is regulated PH to 5-6, leaves standstill.Tell organic phase and washing to neutral, use anhydrous magnesium sulfate drying, the filtering and concentrating mother liquor.Silica gel column chromatography separates (eluent is a normal hexane) and gets 1-(9,9-dihexyl-2-fluorenyl)-12-tridecylene-1,3-diketone 1.8g.
1.2.3 two (2-phenylpyridines) [1-methyl isophthalic acid 3-tetradecene-2,4-diketone] close iridium ((ppy)
2Synthesizing Ir (bsh))
In the 250ml there-necked flask, add successively (ppy)
2Ir
2Cl
40.67g, bsh 0.5g, K
2CO
30.8g, 1,2-ethylene dichloride 100mL, nitrogen protection refluxed reaction 24h, reacting liquid filtering, the organic phase washing is to neutral, and anhydrous MgSO4 is dry, filtering and concentrating.For the eluent silica gel column chromatography separates, get 0.4g orange solid (ppy) with the normal hexane
2Ir (bsh).
1.3 structure is identified
Magnetic resonance spectroscopy: (
1H-NMR, CDCl
3, 500MHz, δ (ppm)): 8.503 (d, 2H), 7.855～7.805 (m, 2H), 7.727～7.682 (m, 2H); 7.558～7.516 (m, 2H), 7.120～7.085 (m, 2H), 6.790 (t, 2H), 6.695～6.660 (m, 2H); 6.327 (d, 1H), 6.250 (d, 1H), 5.858～5.777 (m, 1H), 5.185 (s, 1H); 5.008 (d, 2H), 2.075～1.912 (m, 5H), 1.787 (s, 3H), 1.676～1.594 (m, 1H); 1.376～1.300 (m, 3H), 1.232～1.167 (m, 2H), 1.152～1.036 (m, 4H), 1.022～0.897 (m, 2H).
Ir spectra (KBr, cm
-1): 3037,1266 (C=C-H); 2925,2851,1477 (CH
2-); 1606 (C=O) 1578,1434,754 (pyridine).
Ultimate analysis: calculated value (%): C:52.7, H:5.48, N:5.62;
Measured value (%): C:52.89, H:5.38, N:5.68.
Mass spectrum: (724M
+).
The compound that the above-mentioned reaction of above data acknowledgement obtains is that two (2-phenylpyridines) [1-methyl isophthalic acid 3-tetradecene-2,4-diketone] close iridium, and its structural formula is following:
1.4 optical performance test
Fluorescence spectrum: with 970CRT type fluorescent spectrophotometer assay, recording the fluorescence spectrum peak wavelength is 520nm, belongs to the green glow category, and fluorescence spectrum is as shown in Figure 1.
Embodiment 2: preparation compound two (2-(4 ', 6 '-difluoro) phenylpyridine) (13-tetradecene-2,4-diketone) closes iridium (46f
2Ppy)
2Ir (bsh)
2.1 synthetic route
2.2 synthesis step
2.2.1 (46f
2Ppy)
4Ir
2Cl
2Synthetic
Under the nitrogen protection, add 5.0g 46f in the 500mL there-necked flask
2PpyH, 4.62g IrCl
33H
2O, 150mLl, cellosolvo and 40mL water, heat temperature raising to back flow reaction 24 hours.Be cooled to room temperature, cross and filter yellow solid 7.41g.
2.2.2 1-methyl isophthalic acid 3-tetradecene-2, the synthetic of 4-diketone (bsh) is synthetic
The present embodiment operation steps is identical with embodiment 1 part bsh.
(3) two (2-(4 ', 6 '-difluoro) phenylpyridine) (1-methyl isophthalic acid 3-tetradecene-2,4-diketone) closes iridium [(46f
2Ppy)
2Ir (bsh)] synthetic
In the 250ml there-necked flask, add (46f successively
2PPy)
4Ir
2Cl
20.8g, bsh 0.5g, K
2CO
30.8g, 1,2-two chloroethene 100mL, nitrogen protection refluxed reaction 24h, reacting liquid filtering, the organic phase washing is to neutral, and anhydrous MgSO4 is dry, filtering and concentrating.For the eluent silica gel column chromatography separates, get the 0.2g yellow solid with the normal hexane.
2.3 structure is identified
Magnetic resonance spectroscopy: (
1H-NMR, CDCl
3, 500MHz, δ (ppm)): 8.426 (t, 3H), 8.264～8.217 (m, 2H), 7.807～7.757 (m, 2H), 7.180～7.146 (m; 2H), 6.354～6.306 (m, 2H), 5.734 (d, 1H), 5.651 (d, 1H), 5.446～5.374 (m, 2H); 5.017～4.932 (m, 1H), 2.076～1.970 (m, 4H), 1.965～1.896 (m, 1H), 1.818 (s, 1H), 1.653 (s; 1H), 1.613 (d, 1H), 1.406～1.28 (m, 3H), 1.919～1.023 (m, 4H), 1.020～0.910 (m, 2H).
Ir spectra (KBr, cm
-1): 3066,1265 (C=C-H); 2926,2853,1474 (CH
2-); 1604 (C=O); 1574,1477,757 (pyridines); 988 (C-F).
Ultimate analysis: calculated value (%): C:49.57, H:4.83, N:5.28;
Measured value (%): C:50.02, H:4.92, N:5.36.
Mass spectrum: (796M
+).
The compound that the above-mentioned reaction of above data acknowledgement obtains is that two (2-(4 ', 6 '-difluoro) phenylpyridine) (1-methyl isophthalic acid 3-tetradecene-2,4-diketone) closes iridium.Its structural formula is following:
2.4 optical performance test
Fluorescence spectrum: with 970CRT type fluorescent spectrophotometer assay, recording the fluorescence spectrum peak wavelength is 487nm, belongs to the blue light category, and fluorescence spectrum is as shown in Figure 2.
Claims (1)
1. one kind contains complex of iridium, it is characterized in that structural formula is following:
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| CN1554128A (en) * | 2001-06-20 | 2004-12-08 | �Ѻ͵繤��ʽ���� | Light emitting material and organic light-emitting device |
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| CN1554128A (en) * | 2001-06-20 | 2004-12-08 | �Ѻ͵繤��ʽ���� | Light emitting material and organic light-emitting device |
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