CN110408007B - Preparation method of POSS hybrid conjugated polymer - Google Patents
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Abstract
The invention relates to a preparation method of a POSS hybrid conjugated polymer. The preparation method comprises the steps of preparing an iridium complex from 2- (4-bromophenyl) -benzimidazole and 2-phenylbenzothiazole, preparing 3, 6-dibromocarbazole phenyl POSS from trisilanol phenyl POSS, and carrying out Suzuki polycondensation on the iridium complex, the 3, 6-dibromocarbazole phenyl POSS, 2, 7-dibromo-9, 9-dioctyl fluorene and 9, 9-dioctyl-2, 7-dipicolinic acid boronate fluorene under the action of a palladium tetratriphenylphosphine catalyst to obtain the POSS hybrid conjugated polymer. The polyfluorene host unit, the iridium complex object unit and the nano POSS are bonded and combined to obtain the high-efficiency and stable luminescent conjugated polymer hybrid material which can be used in the fields of photoluminescence, electroluminescence, information storage, sensors and the like.
Description
Technical Field
The invention relates to the technical field of luminescence, in particular to a POSS hybrid conjugated polymer and a preparation method thereof.
Background
Phosphorescent metal complexes have relatively long phosphorescence lifetime and are easy to cause concentration quenching and triplet-triplet annihilation, so that the phosphorescent metal complexes are usually bonded to a polymer host material as a guest to achieve the purposes of inhibiting exciton quenching and improving device efficiency. The polyfluorene material has a wide energy band structure, high fluorescence quantum yield and carrier mobility and deep blue spectral characteristics, is an ideal blue light main body material of a conjugated polymer, and can introduce a phosphorescent metal complex into a side chain or a main chain of the conjugated polymer to obtain the conjugated main chain polymer phosphorescent material.
The conjugated polymer luminescent materials such as polyfluorene and the like have poor luminescent stability and environmental stability, and meanwhile, the molecules are parallel to each other due to pi-pi interaction between the molecules and a rigid plane structure, so that the face-to-face tightly stacked aggregate is easy to form, the solubility is poor, the processing and film-forming properties are influenced, and meanwhile, the blue shift of an electron absorption spectrum is caused by the aggregation, the peak shape is widened, the aggregation even causes fluorescence quenching, so that the development of the luminescent materials in the field of electronic devices is influenced to a certain extent. The defects can be better overcome by introducing polyhedral oligomeric silsesquioxane (POSS) with a nano-size cage shape into conjugated polymers such as polyfluorene and the like, so that the performance of the polymer is improved. POSS can generally be incorporated into polymers as the core of dendrimeric/hyperbranched polymers (chem. mater.,2006,18:3780), as well as the side groups (Macromolecules,2005,38:7453,24) or the ends (adv. funct. mater.,2003,13:25) or blocks (polym.,2014,55:6696) of the polymer chains.
The invention discovers that POSS is vertically grafted to a conjugated main chain containing an iridium complex/polyfluorene to obtain a POSS hybrid conjugated polymer material taking the iridium complex as an object and the polyfluorene as a main body, and the POSS hybrid conjugated polymer material has excellent luminous performance and stability, has good solubility and film forming property, and can be used in the fields of electroluminescence, photoluminescence, electrical storage information, chemistry, biosensors and the like.
Disclosure of Invention
The invention aims to provide a POSS hybrid conjugated polymer material which can be used in the fields of electroluminescence, photoluminescence, electric storage information, chemistry, biosensors and the like.
The invention also aims to provide a preparation method of the POSS hybrid conjugated polymer. The preparation method comprises the steps of preparing an iridium complex from 2- (4-bromophenyl) -benzimidazole and 2-phenylbenzothiazole, preparing 3, 6-dibromocarbazole phenyl POSS from trisilanol phenyl POSS, and carrying out Suzuki polycondensation on the iridium complex, the 3, 6-dibromocarbazole phenyl POSS, the 2, 7-dibromo-9, 9-dioctyl fluorene and the 9, 9-dioctyl-2, 7-dipicolinyl boronate fluorene under the action of a tetratriphenylphosphine palladium catalyst to obtain the POSS hybrid conjugated polymer.
The technical scheme adopted for realizing the purpose of the invention is as follows:
(1) preparation of iridium complexes
The preparation method comprises the steps of heating and refluxing iridium trichloride and 2- (4-bromophenyl) -benzimidazole in a mixed solvent of ethylene glycol monoethyl ether and water to prepare a chlorine-bridged iridium dimer, and then heating and refluxing the chlorine-bridged iridium dimer and 2-phenyl benzothiazole in a solvent of ethylene glycol monoethyl ether under the action of anhydrous sodium carbonate to react to prepare the iridium complex.
The structural formula of the iridium complex is as follows:
the structural formula of the 3, 6-dibromo carbazole phenyl POSS is as follows:
(2) preparation of 3, 6-dibromo carbazole phenyl POSS
Under the action of triethylamine, trisilanol phenyl POSS reacts with bromopropyl trichlorosilane to obtain bromopropyl phenyl POSS, and then reacts with 3, 6-dibromocarbazole under the alkaline condition to prepare the 3, 6-dibromocarbazole phenyl POSS.
(3) Preparation of POSS hybrid conjugated polymer
Under the protection of nitrogen, dissolving an iridium complex, 3, 6-dibromocarbazole phenyl POSS, 2, 7-dibromo-9, 9-dioctyl fluorene and 9, 9-dioctyl-2, 7-dipicolinic acid ester fluorene according to molar ratio in a toluene solvent and a 2M potassium carbonate aqueous solution, adding a proper amount of tetratriphenylphosphine palladium catalyst and tetra-n-butyl ammonium iodide phase transfer agent, magnetic stirring reflux polymerization reaction is carried out for 48 hours at 110 ℃ under nitrogen, then phenyl boric acid and bromobenzene are sequentially used as end capping agents for end capping reaction for 8 hours respectively, and cooling to room temperature, precipitating with methanol, filtering to collect a solid, sequentially carrying out soxhlet extraction with methanol and acetone to remove small molecules and oligomers, collecting a polymer solution subjected to soxhlet extraction with chloroform, concentrating to a proper concentration, precipitating with methanol, collecting a finally obtained flocculent solid, and carrying out vacuum drying for 12 hours to obtain the POSS hybrid conjugated polymer.
The ratio of the total mole number of the iridium complex, 3, 6-dibromo carbazole phenyl POSS and 2, 7-dibromo-9, 9-dioctyl fluorene to the mole number of 9, 9-dioctyl-2, 7-dipicolinic acid ester fluorene is 1: 1.
The molar ratio of the iridium complex to 9, 9-dioctyl-2, 7-dipinacolol borate fluorene is 0.1-10: 100.
The molar ratio of the 3, 6-dibromocarbazole phenyl POSS to the 9, 9-dioctyl-2, 7-dipinacolol borate fluorene is 0.1-6: 100.
The toluene solvent and the aqueous potassium carbonate solution need to be sufficiently deoxygenated beforehand.
The invention has the following advantages:
1. according to the invention, polyfluorene is taken as a host and an iridium complex is taken as an object, POSS is introduced into the host and the object, and the isolation and dilution effects of a cage-shaped polyhedral structure of POSS are utilized to inhibit the aggregation of luminescent groups, so that the fluorescence of the polyfluorene of the host is effectively transferred to the phosphorescence of the iridium complex of the object, and the luminescent property of the material is improved.
2. The nanometer POSS group is hung and connected to the rigid main chain, so that the reduction of the solubility of the polymer caused by the stacking of the rigid main chain can be effectively avoided, the obtained polymer material has excellent solubility and film-forming property, and the performance of an OLED device can be effectively improved.
3. The POSS nano-material and the organic/inorganic hybrid characteristics can be fully exerted, so that the thermal stability and the luminescent color stability of the luminescent material are improved.
Drawings
FIG. 1 is the fluorescence emission spectra of the iridium complex (curve a) and POSS hybrid conjugated polymer (curve b) solid powders of example 1 under 365nm wavelength excitation.
FIG. 2 is an infrared spectrum of a POSS hybrid conjugated polymer of example 1.
FIG. 3 is the fluorescence emission spectra of the POSS hybrid conjugated polymer of example 2 with a solid powder of POSS free polymer (curve a) at 365nm wavelength excitation.
Figure 4 is an atomic force microscope image of a POSS hybrid conjugated polymer thin film of example 2.
FIG. 5 is an atomic force microscope image of a control film without POSS polymer.
Detailed Description
The invention is further illustrated by the following specific examples, which are not intended to limit the scope of the invention in any way.
In FIG. 3, curve a shows the fluorescence emission spectrum of the POSS-free polymer of example 2; curve b represents the fluorescence emission spectrum of the POSS hybrid conjugated polymer of example 2.
Example 1
1. Preparation of iridium complexes
Under argon protection, 0.35g of IrCl was added to a round bottom flask3·3H2O, 0.63g of 2- (4-bromophenyl) -benzimidazole, 30mL of ethylene glycol monoethyl ether and 10mL of distilled water, refluxing at 120 ℃ for 24 hours, cooling to room temperature, extracting with saturated brine and ethyl acetate, removing the organic phase, and drying in vacuum to obtain the 2- (4-bromophenyl) -benzimidazole chlorine bridged dimer.
Under the protection of argon, 0.3g of 2- (4-bromophenyl) -benzimidazole chlorine bridged dimer, 0.1g of 2-phenylbenzothiazole and 30mg of anhydrous sodium carbonate are added into a round-bottom flask, the round-bottom flask is vacuumized, nitrogen is introduced, 50mL of ethylene glycol monoethyl ether is injected by a syringe, reflux reaction is carried out for 12 hours at 120 ℃ under argon, the round-bottom flask is cooled to room temperature, reaction liquid is extracted by saturated saline and ethyl acetate, a yellow solid is obtained by spin-drying a solvent, column chromatography purification is carried out by taking dichloromethane as an eluent, and the iridium complex is obtained by spin-drying the solvent. The yield was 50%.
1H NMR(400MHz,HDMSO)δ8.21–8.07(m,2H),7.67(d,J＝8.0Hz,3H),7.58(d,J＝8.3Hz, 3H),7.15(t,J＝7.5Hz,3H),7.07(d,J＝8.1Hz,3H),6.72(s,2H),6.67(s,3H),5.98–5.88(m,3H), 3.43(d,J＝6.9Hz,2H)。
The fluorescence emission spectrum of the prepared iridium complex solid powder under 365nm wavelength excitation is shown as a curve a in figure 1, the emission peaks are positioned at 546nm and 585nm, and yellow light is emitted.
2. Preparation of 3, 6-dibromo carbazole phenyl POSS
0.38g of bromopropyltrichlorosilane was weighed into a round-bottomed flask, evacuated and purged with nitrogen. 30mL of tetrahydrofuran and 20mL of triethylamine are added, 0.93g of trisilanol phenyl POSS is diluted by 10mL of tetrahydrofuran and then slowly added into a flask dropwise, the mixture is stirred at room temperature for reaction, white turbidity is generated, and after the reaction is carried out for 4 hours, the mixture is extracted by saturated saline to obtain white solid bromopropylphenyl POSS, wherein the yield is 86%.
Adding 0.325g of 3, 6-dibromocarbazole and 5mL of dimethyl sulfoxide into a round-bottom flask, dropwise adding 5mL of 10% NaOH solution after dissolving, stirring for 20min at normal temperature, slowly dropwise adding 10mL of dimethyl sulfoxide solution dissolved with 0.863g of bromopropylphenyl POSS, and heating to 40 ℃ for reaction for 5 hours. After the reaction is finished, adjusting the pH value to be neutral by using dilute hydrochloric acid, filtering, and recrystallizing by using ethanol to obtain white flocculent solid. The yield was 78%.
1H NMR(400MHz,CDCl3)δ8.03(s,7H),7.81–7.71(m,14H),7.52–7.32(m,14H), 3.60–3.48(m,2H),2.97(s,2H),2.90(d,J＝0.5Hz,2H),2.06–1.91(m,2H),1.64(s,2H),1.06–0.94 (m,2H)。
3. Preparation of POSS hybrid conjugated polymer
Under the protection of nitrogen, 0.01mmol of iridium complex, 0.01mmol of 3, 6-dibromocarbazole phenyl POSS, 0.98mmol of 2, 7-dibromo-9, 9-dioctyl fluorene and 1mmol of 9, 9-dioctyl-2, 7-dipicolinic acid borate fluorene are dissolved in 10mL of toluene and 4mL of 2M potassium carbonate aqueous solution which are fully deoxidized in advance, 20mg of tetratriphenylphosphine palladium catalyst and 30mg of tetra-n-butyl ammonium iodide phase transfer agent are added, after the magnetic stirring reflux polymerization reaction is carried out for 48 hours under nitrogen at 110 ℃, 0.2g of phenylboronic acid and 0.2mL of bromobenzene are sequentially used as end capping reagents for carrying out end capping reaction for 8 hours respectively, the mixture is cooled to room temperature, methanol is used for precipitation, the solid is collected by filtration, small molecules and oligomers are removed by sequential methanol and acetone, the polymer solution of chloroform extraction is collected, methanol is used for precipitation after being concentrated to proper concentration, the finally obtained flocculent solid is collected, vacuum drying for 12 hours to obtain POSS hybrid conjugated polymer solid powder with the yield of 60 percent and the number average molecular weight of 1.2 multiplied by 104The molecular weight distribution PDI was 1.7.
The infrared spectrum of the POSS hybrid conjugated polymer solid powder prepared in the example is shown in the attached figure 2.
The fluorescence emission spectrum of the POSS hybrid conjugated polymer solid powder under 365nm wavelength excitation is shown as curve b in figure 1, and blue light and yellow light bipolar emission are shown.
The polymeric material has the following structural formula:
example 2
Preparation of iridium complex and preparation of 3, 6-dibromocarbazole phenyl POSS are the same as in example 1.
The experimental procedure for the preparation of POSS hybrid conjugated polymers was as in example 1, wherein the iridium complexes, 3, 6-dibromocarbazolylphenyl POSS, 2, 7-dibromo-9, 9-dioctylfluorene and 9, 9-dioctyl2, 7-dipinacoloborate fluorene molar charge are shown in table 1.
TABLE 1
FIG. 3 shows the fluorescence emission spectra of the POSS hybrid conjugated polymer prepared in this example (curve b) and the control sample without POSS polymer (curve a) under 365nm wavelength excitation, and it can be seen that the polymer containing POSS has stronger fluorescence in the yellow part, indicating that the introduction of POSS makes the host blue fluorescence more shifted to the guest yellow. By measuring the fluorescence quantum yield of the polymer powder, the fluorescence quantum yield of the polymer of the example is 13.86%, while the fluorescence quantum yield of the polymer without POSS is 10.43%, which shows that the introduction of POSS can improve the luminescence property of the polymer.
The thermal stability analysis of the POSS hybrid conjugated polymer material prepared in the embodiment shows that the temperature corresponding to the polymer is 302 ℃ when the weight loss is 5%, which shows that the prepared POSS hybrid conjugated polymer material has excellent thermal stability.
FIGS. 4 and 5 show that the POSS-containing conjugated polymer film (FIG. 4) has a smoother surface and reduced surface roughness with an RMS deviation of 3.03nm, while the POSS-free polymer film (FIG. 5) has an RMS deviation of 5.30nm, indicating that the introduction of POSS is effective in improving the solubility and film-forming properties of the polymer.
Claims (3)
1. A preparation method of POSS hybrid conjugated polymer is characterized in that under the protection of nitrogen, iridium complex, 3, 6-dibromocarbazole phenyl POSS, 2, 7-dibromo-9, 9-dioctyl fluorene and 9, 9-dioctyl-2, 7-dipivalol borate fluorene are dissolved in a toluene solvent and a 2M potassium carbonate aqueous solution according to molar ratio, a proper amount of tetrakis (triphenylphosphine) palladium and tert-butyl ammonium iodide are added, stirring reflux reaction is carried out at 110 ℃ under nitrogen atmosphere for 48 hours, then end-capping reaction is carried out by phenylboronic acid and bromobenzene for 8 hours respectively, cooling to room temperature, precipitating with methanol, filtering, sequentially carrying out soxhlet extraction on a filter cake with methanol and acetone to remove small molecules and oligomers, then carrying out soxhlet extraction with chloroform, concentrating the soxhlet extraction solution to a proper concentration, precipitating with methanol, filtering, and carrying out vacuum drying to obtain the POSS hybrid conjugated polymer;
the structural formula of the iridium complex is as follows:
the structural formula of the 3, 6-dibromo carbazole phenyl POSS is as follows:
the ratio of the total mole number of the iridium complex, 3, 6-dibromo carbazole phenyl POSS and 2, 7-dibromo-9, 9-dioctyl fluorene to the mole number of 9, 9-dioctyl-2, 7-dipicolinic acid ester fluorene is 1: 1;
the molar ratio of the 3, 6-dibromocarbazole phenyl POSS to the 9, 9-dioctyl-2, 7-dipinacolol borate fluorene is 0.1-6: 100.
2. The preparation method of the POSS hybrid conjugated polymer as claimed in claim 1, wherein the molar ratio of the iridium complex to 9, 9-dioctyl-2, 7-dipinacolone boronate fluorene is 0.1-10: 100.
3. The method of claim 1, wherein the toluene solvent and the aqueous potassium carbonate solution are pre-deoxygenated.
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| CN104059631A (en) * | 2013-03-19 | 2014-09-24 | 宁波大学 | Iridium-containing polymer red-light material and synthetic method thereof |
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| CN104059631A (en) * | 2013-03-19 | 2014-09-24 | 宁波大学 | Iridium-containing polymer red-light material and synthetic method thereof |
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| Luminescent Molecular Octopuses with a Polyhedral Oligomeric Silsesquioxane (POSS) Core and Iridium(III) Polypyridine Arms: Synthesis, Aggregation Induced Emission, Cellular Uptake, and Bioimaging Studies;Jing-Hui Zhu, et al.;《Chem. Eur. J.》;20190709;10633-10641 * |
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