CN108017676B - Polyhydroxy yellow phosphorescent iridium complex and preparation method thereof - Google Patents
Polyhydroxy yellow phosphorescent iridium complex and preparation method thereof Download PDFInfo
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 69
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 57
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000010668 complexation reaction Methods 0.000 title description 2
- IPQKDIRUZHOIOM-UHFFFAOYSA-N Oroxin A Natural products OC1C(O)C(O)C(CO)OC1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC=CC=1)O2 IPQKDIRUZHOIOM-UHFFFAOYSA-N 0.000 claims abstract description 39
- IKIIZLYTISPENI-ZFORQUDYSA-N baicalin Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC=CC=1)O2 IKIIZLYTISPENI-ZFORQUDYSA-N 0.000 claims abstract description 39
- 229960003321 baicalin Drugs 0.000 claims abstract description 39
- AQHDANHUMGXSJZ-UHFFFAOYSA-N baicalin Natural products OC1C(O)C(C(O)CO)OC1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC=CC=1)O2 AQHDANHUMGXSJZ-UHFFFAOYSA-N 0.000 claims abstract description 39
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical group C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000003446 ligand Substances 0.000 claims abstract description 11
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims abstract description 7
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 48
- 239000007787 solid Substances 0.000 claims description 33
- 239000000706 filtrate Substances 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 238000001914 filtration Methods 0.000 claims description 20
- 239000008367 deionised water Substances 0.000 claims description 15
- 229910021641 deionized water Inorganic materials 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 10
- 239000012535 impurity Substances 0.000 claims description 10
- 238000003760 magnetic stirring Methods 0.000 claims description 10
- 239000012046 mixed solvent Substances 0.000 claims description 10
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 230000001681 protective effect Effects 0.000 claims description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 3
- 230000000694 effects Effects 0.000 abstract description 3
- 230000000171 quenching effect Effects 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract 2
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 description 14
- YOLNUNVVUJULQZ-UHFFFAOYSA-J iridium;tetrachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Ir] YOLNUNVVUJULQZ-UHFFFAOYSA-J 0.000 description 7
- 239000003814 drug Substances 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WKAXDAMWMOBXMP-UHFFFAOYSA-N 2,3-diphenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=C1 WKAXDAMWMOBXMP-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 208000030961 allergic reaction Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012984 biological imaging Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- 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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Abstract
The invention relates to a polyhydroxy yellow phosphorescent iridium complex and a preparation method thereof, belonging to the technical field of electrophosphorescence. The main ligand of the polyhydroxy yellow phosphorescent iridium complex is 2-phenylpyridine, and the auxiliary ligand is baicalin; the preparation method comprises the steps of synthesizing the 2-phenylpyridine iridium dichloride bridge by using 2-phenylpyridine and iridium trichloride as raw materials, and preparing the polyhydroxy yellow phosphorescent iridium complex by using baicalin and the 2-phenylpyridine iridium dichloride bridge as raw materials. The polyhydroxy yellow phosphorescent iridium complex has a larger steric hindrance effect, can effectively prevent a concentration quenching effect, and improves the luminous efficiency.
Description
Technical Field
The invention relates to a polyhydroxy yellow phosphorescent iridium complex and a preparation method thereof, belonging to the technical field of electrophosphorescence.
Background
The OLED organic electrophosphorescent luminescent material is known as a next generation display device due to the excellent luminescent performance of the OLED organic electrophosphorescent luminescent material. Compared with the quantum efficiency of 25% of the traditional fluorescent material, the theoretical quantum efficiency of the phosphorescent material which can be utilized is 100%. The organometallic complex luminescent material has the stability of a fluorescent material and higher luminescent efficiency than the fluorescent material, and can obtain luminescence in the whole visible wavelength range by adjusting the structure of a ligand, so that the organometallic complex luminescent material is called as a most promising luminescent material.
At present, most iridium-based phosphorescent material complexes for OLEDs are C ^ N type ring metal complexes, and auxiliary ligands, besides the C ^ N type complexes, also include ketones and the like. The invention selects the diphenylpyridine as a main ligand and the baicalin as an auxiliary ligand to synthesize the polyhydroxy yellow phosphorescent material. Baicalin (BC, an abbreviation of baicalin) is an important drug, and metal complexes thereof are widely applied in medicine, but iridium and complex synthesized by the same are not reported at present.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a polyhydroxy yellow phosphorescent iridium complex, wherein the main ligand of the polyhydroxy yellow phosphorescent iridium complex is 2-phenylpyridine, the auxiliary ligand is baicalin, and the chemical structural formula is shown in the specification
The polyhydroxy yellow phosphorescent iridium complex can be named Ir (ppy)2(BC) a complex;
the invention also aims to provide a preparation method of the polyhydroxy yellow phosphorescent iridium complex, which comprises the following specific steps:
(1) synthesis of iridium dichloro bridge: dissolving 2-phenylpyridine and iridium trichloride into a mixed solvent A, wherein the mixed solvent A is a mixture of deionized water and ethylene glycol ethyl ether, performing reflux reaction for 12-24 hours under the conditions of protecting gas nitrogen atmosphere, magnetically stirring and at the temperature of 120-130 ℃, filtering to obtain a filtrate A and a solid A, washing the solid for 3-5 times by using the deionized water, ethanol and acetone in sequence, dissolving in dichloromethane to remove impurities, filtering to obtain a filtrate B and a solid B, and performing vacuum concentration and drying on the filtrate B to obtain the iridium dichloro-bridge complex, wherein the specific synthetic route is as follows:
(2) synthesis of polyhydroxy yellow phosphorescent iridium complex: dissolving baicalin in ethylene glycol ethyl ether at the temperature of 70-80 ℃, adding the iridium dichloro-bridge complex and sodium carbonate obtained in the step (1), heating to 110-130 ℃, carrying out reflux reaction for 20-48 under the conditions of constant temperature, magnetic stirring and protective gas nitrogen atmosphere, washing for 3-4 times by using deionized water and ethanol in sequence, filtering to obtain filtrate C and solid C, dissolving the solid C in dichloromethane to remove impurities, filtering to obtain filtrate D and solid D, and carrying out vacuum concentration and crystallization on the filtrate D to obtain the polyhydroxy yellow phosphorescent iridium complex, wherein the specific synthetic route is as follows:
the molar ratio of the 2-phenylpyridine to the iridium trichloride in the step (1) is 2-2.6: 1;
the molar ratio of the baicalin to the iridium dichloro-bridge complex in the step (2) is 2-2.3: 1;
the stirring speed of the magnetic stirring is 300-400 r/min;
the iridium trichloride can be iridium trichloride hydrate or anhydrous iridium trichloride;
polyhydroxy phosphorescent yellow Iridium Complex of the invention (Ir (ppy)2(BC) complex) has an absorption peak at 450 nm and 490nm respectively; polyhydroxy yellow phosphorescent iridium complex (Ir (ppy)2(BC) Complex) phosphorescent Spectroscopy yellow light emission with a maximum emission wavelength of 580 nm.
The invention has the beneficial effects that:
(1) in the prior phosphorescent luminescent material, a small-molecule phosphorescent material is doped into a polymer host as an object to prepare a phosphorescent device, and the service life of the device is shortened due to poor compatibility of the host and the object and phase separation between the host and the object;
(2) the larger steric hindrance effect of the complex can effectively reduce the concentration quenching effect;
(3) baicalin is used as an important traditional Chinese medicine, the metal complex of the baicalin has obvious effects on the aspects of resisting tumors, enhancing anti-allergic reaction, resisting aging and the like, the luminous performance of the iridium complex is commonly used in the fields of biological imaging, biological analysis and the like in medicine, the baicalin is used as an auxiliary ligand to be coordinated with iridium to generate the complex, and the complex can be used as a medical material.
Drawings
FIG. 1 shows a polyhydroxy phosphorescent yellow iridium complex (Ir (ppy) prepared in example 12(BC) complex) uv-vis absorption spectrum in dichloromethane;
FIG. 2 shows the polyhydroxy phosphorescent yellow iridium complex (Ir (ppy) prepared in example 12(BC) complex) PL fluorescence spectrum in dichloromethane (ex =290 nm).
Detailed Description
The present invention will be described in further detail with reference to specific embodiments, but the scope of the present invention is not limited to the description.
Example 1: a preparation method of polyhydroxy yellow phosphorescent iridium complex comprises the following steps:
(1) synthesis of iridium dichloro bridge: dissolving 2.83g of 2-phenylpyridine and 2.36g of iridium trichloride hydrate into a mixed solvent A in a round-bottom three-neck flask, wherein the molar ratio of the 2-phenylpyridine to the iridium trichloride hydrate is 2.6:1, the mixed solvent A is a mixture of 20mL of deionized water and 80mL of ethylene glycol ethyl ether, carrying out reflux reaction for 24 hours under the conditions of protecting gas and nitrogen atmosphere, magnetic stirring (the stirring speed is 300 r/min) and the temperature is 120 ℃, filtering to obtain a filtrate A and a solid A, washing the solid for 3 times by using the deionized water, ethanol and acetone in sequence, dissolving the solid in dichloromethane to remove impurities, filtering to obtain a filtrate B and a solid B, concentrating and drying the filtrate B in vacuum to obtain an iridium dichloro-bridge complex, and carrying out mass spectrum (MS/ESI)+) 1075, the specific synthetic route is:
(2) synthesis of polyhydroxy yellow phosphorescent iridium complex: dissolving 1.83g of Baicalin (BC) in 100mL of ethylene glycol ethyl ether in a round-bottom flask at the temperature of 75 ℃, then adding 1.92g of iridium dichloro bridge complex obtained in the step (1) and 0.6g of anhydrous sodium carbonate, wherein the molar ratio of the baicalin to the iridium dichloro bridge complex is 2.3:1, heating to 120 ℃, carrying out reflux reaction for 24 hours under the conditions of constant temperature, magnetic stirring and protective gas nitrogen atmosphere, washing for 3 times by using deionized water and ethanol in sequence, filtering to obtain a filtrate C and a solid C, dissolving the solid C in dichloromethane to remove impurities, filtering to obtain a filtrate D and a solid D, and carrying out vacuum concentration and crystallization on the filtrate D to obtain the polyhydroxy yellow phosphorescent iridium complex, wherein the specific synthetic route is as follows:
the polyhydroxy yellow phosphorescent iridium complex of the embodiment is a yellow crystal;
the structural characterization data of the polyhydroxy phosphorescent yellow iridium complex of the embodiment are as follows:
MS（m/z）：940（M+）。
1H NMR(CDCl3/TMS)，δ：9.83（dd，J=5.7，57.8Hz，4H），7.89～7.85（m，8H），7.78（t，J=7.45Hz，2H），7.53（dd，J=1.05，6.75Hz，2H），7.31（s，1H），6.89（t，J=7.4Hz，2H），6.84（t，J=7.5Hz，2H），6.79（t，J=7.6Hz，2H），6.74（t，J=7.45Hz，2H），6.45（d，J=7.65Hz，2H），5.77（d，J=7.65Hz，2H），5.27（s，1H），1.97（s，3H）。
elemental analysis: c43H33IrN2O11
Calculated values: c54.60%, H3.49%, N2.96%;
measured value: c53.81%, H3.99%, N3.23%
The data show that the polyhydroxy yellow phosphorescent iridium complex (baicalin metal iridium complex) prepared by the invention is bis (2-phenylpyridine) baicalin iridium [ Ir (ppy)2(BC)]；
The polyhydroxy phosphorescent yellow iridium complex of the example was subjected to measurement of ultraviolet-visible absorption spectrum using methylene chloride as a solvent (Ir (ppy)2(BC) Complex) ultraviolet-visible absorption Spectrum of the polyhydroxy phosphorescent yellow Iridium Complex (Ir (ppy)2(BC) Complex the ultraviolet visible absorption spectrum of the (BC) complex in methylene chloride is shown in FIG. 1. As can be seen from FIG. 1, the polyhydroxy phosphorescent yellow iridium complex (Ir (ppy)2(BC) complex) with a wavelength range of 400-600 nm, wherein 450 nm and 490nm respectively have an absorption peak;
the polyhydroxy phosphorescent yellow iridium complex of the example was subjected to fluorescence spectroscopy (PL) measurement using methylene chloride as a solvent and light having a wavelength of 290nm as an excitation wavelength, and the polyhydroxy phosphorescent yellow iridium complex (Ir (ppy)2PL fluorescence spectra of (BC) Complex in methylene chloride As shown by the Table, polyhydroxy yellow phosphorescent Iridium Complex (Ir (ppy)2(BC) Complex) has a PL emission peak at 580nm, indicating a majorityHydroxyl yellow phosphorescent iridium complex (Ir (ppy)2(BC) complexes) are yellow phosphorescent materials.
Example 2: a preparation method of polyhydroxy yellow phosphorescent iridium complex comprises the following steps:
(1) synthesis of iridium dichloro bridge: dissolving 1.87g of 2-phenylpyridine and 2.12g of iridium trichloride hydrate into a mixed solvent A in a round-bottom three-neck flask, wherein the molar ratio of the 2-phenylpyridine to the iridium trichloride hydrate is 2:1, the mixed solvent A is a mixture of 30mL of deionized water and 70mL of ethylene glycol ethyl ether, carrying out reflux reaction for 12 hours under the conditions of protecting gas and nitrogen atmosphere, magnetic stirring (stirring speed is 350 r/min) and temperature of 130 ℃, filtering to obtain a filtrate A and a solid A, washing the solid for 5 times by using the deionized water, ethanol and acetone in sequence, dissolving the solid in dichloromethane to remove impurities, filtering to obtain a filtrate B and a solid B, concentrating and drying the filtrate B in vacuum to obtain an iridium dichloro bridge complex, and carrying out mass spectrometry (MS/ESI)+) 1075, the specific synthetic route is:
(2) synthesis of polyhydroxy yellow phosphorescent iridium complex: dissolving 1.5g of Baicalin (BC) in 120mL of ethylene glycol ethyl ether in a round-bottom flask at the temperature of 80 ℃, then adding 1.7g of iridium dichloro bridge complex obtained in the step (1) and 0.4g of anhydrous sodium carbonate, wherein the molar ratio of the baicalin to the iridium dichloro bridge complex is 2.15:1, heating to 130 ℃, carrying out reflux reaction for 48 hours under the conditions of constant temperature, magnetic stirring and protective gas nitrogen atmosphere, washing for 4 times by using deionized water and ethanol in sequence, filtering to obtain a filtrate C and a solid C, dissolving the solid C in dichloromethane to remove impurities, filtering to obtain a filtrate D and a solid D, and carrying out vacuum concentration and crystallization on the filtrate D to obtain the polyhydroxy yellow phosphorescent iridium complex, wherein the specific synthetic route is as follows:
example 3: a preparation method of polyhydroxy yellow phosphorescent iridium complex comprises the following steps:
(1) synthesis of iridium dichloro bridge: dissolving 2.5g of 2-phenylpyridine and 2.47g of iridium trichloride hydrate into a mixed solvent A in a round-bottom three-neck flask, wherein the molar ratio of the 2-phenylpyridine to the iridium trichloride hydrate is 2.3:1, the mixed solvent A is a mixture of 30mL of deionized water and 100mL of ethylene glycol ethyl ether, carrying out reflux reaction for 18h under the conditions of protecting gas and nitrogen atmosphere, magnetic stirring (the stirring speed is 400 r/min) and the temperature is 125 ℃, filtering to obtain a filtrate A and a solid A, washing the solid for 4 times by using the deionized water, ethanol and acetone in sequence, dissolving the solid in dichloromethane to remove impurities, filtering to obtain a filtrate B and a solid B, concentrating and drying the filtrate B in vacuum to obtain an iridium dichloro-bridge complex, and carrying out mass spectrum (MS/ESI)+) 1075, the specific synthetic route is:
(2) synthesis of polyhydroxy yellow phosphorescent iridium complex: dissolving 1.65g of Baicalin (BC) in 150mL of ethylene glycol ethyl ether in a round-bottom flask at the temperature of 80 ℃, then adding 1.98g of iridium dichloro bridge complex obtained in the step (1) and 0.8g of anhydrous sodium carbonate, wherein the molar ratio of the baicalin to the iridium dichloro bridge complex is 2:1, heating to 110 ℃, carrying out reflux reaction for 36 hours under the conditions of constant temperature, magnetic stirring and protective gas nitrogen atmosphere, washing for 3 times by using deionized water and ethanol in sequence, filtering to obtain a filtrate C and a solid C, dissolving the solid C in dichloromethane to remove impurities, filtering to obtain a filtrate D and a solid D, and carrying out vacuum concentration and crystallization on the filtrate D to obtain the polyhydroxy yellow phosphorescent iridium complex, wherein the specific synthetic route is as follows:
Claims (5)
1. a polyhydroxy phosphorescent yellow iridium complex is characterized in that: the main ligand is 2-phenylpyridine, the auxiliary ligand is baicalin, and the chemical structural formula is shown in the specification
2. The preparation method of the polyhydroxy phosphorescent yellow iridium complex of claim 1 is characterized by comprising the following specific steps:
(1) synthesis of iridium dichloro bridge: dissolving 2-phenylpyridine and iridium trichloride into a mixed solvent A, wherein the mixed solvent A is a mixture of deionized water and ethylene glycol ethyl ether, performing reflux reaction for 12-24 hours under the conditions of protecting gas nitrogen atmosphere, magnetically stirring and at the temperature of 120-130 ℃, filtering to obtain a filtrate A and a solid A, washing the solid A with deionized water, ethanol and acetone for 3-5 times in sequence, dissolving in dichloromethane to remove impurities, filtering to obtain a filtrate B and a solid B, and performing vacuum concentration and drying on the filtrate B to obtain an iridium dichloro-bridge complex, wherein the specific synthetic route is as follows:
(2) synthesis of polyhydroxy yellow phosphorescent iridium complex: dissolving baicalin in ethylene glycol ethyl ether at the temperature of 70-80 ℃, adding the iridium dichloro-bridge complex and sodium carbonate obtained in the step (1), heating to 110-130 ℃, performing reflux reaction for 20-48 h under the conditions of constant temperature, magnetic stirring and protective gas nitrogen atmosphere, washing for 3-4 times by using deionized water and ethanol in sequence, filtering to obtain filtrate C and solid C, dissolving the solid C in dichloromethane to remove impurities, filtering to obtain filtrate D and solid D, and performing vacuum concentration and crystallization on the filtrate D to obtain the polyhydroxy yellow phosphorescent iridium complex, wherein the specific synthetic route is as follows:
3. the method for preparing polyhydroxy phosphorescent yellow iridium complex according to claim 2, wherein: in the step (1), the molar ratio of 2-phenylpyridine to iridium trichloride is 2-2.6: 1.
4. The method for preparing polyhydroxy phosphorescent yellow iridium complex according to claim 2, wherein: the molar ratio of the baicalin to the iridium dichloro-bridge complex in the step (2) is 2-2.3: 1.
5. The method for preparing polyhydroxy phosphorescent yellow iridium complex according to claim 2, wherein: the stirring speed of the magnetic stirring is 300-400 r/min.
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| CN106279295A (en) * | 2016-08-05 | 2017-01-04 | 昆明贵金属研究所 | Two kinds of yellow iridium phosphorescent complexes and preparation method thereof |
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