CN102268250A - Novel electrically-neutral tridentate iridium [III] complex red luminescent material and preparation method - Google Patents
Novel electrically-neutral tridentate iridium [III] complex red luminescent material and preparation method Download PDFInfo
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Abstract
The invention relates to synthetic technology of a new luminescent material, and is a novel electrically-neutral tridentate iridium [III] complex red luminescent material and a preparation method. The material is a 6-[5-trifluoromethyl pyrazole]-2,2'-dipyridine*2,6-diphenyl pyridine iridium [III] complex. The preparation method comprises the following steps: heating a trihydrate iridium trichloride [III] metal salt reagent and a 6-[5-trifluoromethyl pyrazole]-2,2'-dipyridine tridentate chelating ligand in ethanol with the protection of nitrogen, performing suction drying, recrystallization, filtration, washing and vacuum drying of the reaction solution to obtain an orange solid intermediate; in a nitrogen glove box, well mixing the orange intermediate, silver trifluomethanesulfonate, and 2,6-dibenzyl pyridine ligands, pulverizing the mixture into powder, heating, cooling the reaction solution to normal temperature, collecting the filtrate, performing suction drying to obtain a crude product, separating the crude product, collecting a second-segment orange-red eluate, performing suction drying to obtain a final product with a yield of 30-68%.
Description
Technical field
The present invention relates to luminous novel material synthetic technology, particularly a kind of novel electric neutrality three tooth iridium [III] title complex red light material and preparation methods.
Background technology
The trivalent iridium metal complex of octahedra configuration is because heavy atoms effect and strong spin coupling show good phosphorescence luminescent properties, as have the luminescent lifetime of higher luminous quantum efficiency and microsecond level.In addition, by the modification transformation of ligand structure, can realize the luminous whole visible region of containing from the blue light to ruddiness of iridium [III] title complex.As a kind of good phosphorescent light-emitting materials, can be applicable to various fields such as electroluminescent device, chemical sensor, nonlinear optical material, dye sensitization solar battery, biomarker and probe.
Use trivalent complex of iridium, especially [Ir (C^N) that three bidentate chelating ligands make up
3-n(L^X)
n] (n=0-3; The Cyclometalated part of C^N=single anion type bidentate; L^X=single anion type bidentate chelating ligand) complex of iridium of type owing to have good solution and solid luminescent performance and electric neutrality characteristics, is one of optimal candidate of luminescent material in the electroluminescent device, has become a class of current broad research.Yet; complex of iridium with above-mentioned general formula is because the introducing of asymmetric chelating ligand; can cause the generation of many geometrical isomers; these geometrical isomers exist and separate purification difficult; and isomerization or decomposing phenomenon take place in regular meeting under external stimuluss such as photoelectric heat, bring many disadvantageous effects for its practical application.
The complex of iridium that adopts two three tooth chelating ligands to constitute, have the complex of iridium that constitutes by three bidentate chelating ligands incomparable geometry advantage, can significantly reduce even thoroughly eliminate the generation of geometrical isomer.Research shows that also the introducing of fluoro-containing group can significantly improve the photic and electroluminescent properties of luminescent material and the volatility of material.Yet it is considerably less to use the research that two three tooth chelating ligands make up the complex of iridium luminescent material, and based on complex of iridium luminescent material of the dipyridyl pyrazoles three tooth chelating ligands that contain trifluoromethyl and preparation method thereof, report is not arranged as yet at present.
Summary of the invention
The purpose of this invention is to provide a kind of novel electric neutrality three tooth iridium [III] title complex red light material and preparation methods.
Technical solution of the present invention: a kind of novel electric neutrality three tooth iridium [III] title complex red light materials are 6-[5-trifluoromethyl pyrazols]-2,2 '-dipyridyl 2,6-phenylbenzene pyridine closes iridium [III] title complex, and its molecular structural formula is:
The method for preparing described novel electric neutrality three tooth iridium [III] title complex red light materials, comprise the steps: under nitrogen protection, by mol ratio is 1: 1.05 three water iridous chloride [III] metal-salt reagent and 6-[5-5-flumethiazine]-2,2 '-dipyridyl [be called for short bpyfpzH] three tooth chelating ligands were heated to 78 ℃ of back flow reaction 2 days in ethanolic soln, after stop the heating, after question response liquid returns to normal temperature, reaction solution is drained on Rotary Evaporators, with volume ratio is that acetone-ether mixed solvent of 1: 6 carries out recrystallization, the throw out that filtration and recrystallization obtains, with ether washing precipitate 3-4 time, can obtain an orange-yellow solid-state intermediate after the vacuum-drying;
In nitrogen glove box, be 1: 3 with mol ratio: the above-mentioned orange-yellow solid-state intermediate of 10-50, silver triflate and 2,6-phenylbenzene pyridine [is called for short dppyH
2] part uniform mixing in mortar; and be milled into 400-500 purpose powder; place the single port round-bottom reaction flask then; under nitrogen protection; with three's mixture heating up to 110 ℃; and remain under this temperature and to continue stirring reaction 24 hours; stop heating; the question response liquid cooling is to normal temperature; with the dichloromethane solvent dissolving, remove by filter insoluble solid, the filtrate of collection is drained on Rotary Evaporators and is obtained crude product; the crude product wash-out on silica gel column chromatography that obtains is separated; as eluent, collect second section orange-red eluate with methylene dichloride, the orange red elutriant of collecting is drained on Rotary Evaporators; can obtain orange-red solid-state pure products after the vacuum-drying---novel electric neutrality three tooth iridium [III] title complex red light materials, its productive rate reaches 30-68%.
Preferably, described orange-yellow solid-state intermediate, silver triflate and 2,6-phenylbenzene pyridine three's mol ratio is 1: 3: 30, its resultant orange-red solid-state pure products---novel electric neutrality three tooth iridium [III] title complex red light materials, productive rate is 60%.
Reaction mechanism of the present invention is:
The physical parameter of gained title complex is as follows:
Molecular formula: C
31H
19F
3N
6Ir
Molecular weight: 724.75
Chinese: 6-[5-trifluoromethyl pyrazol]-2,2 '-dipyridyl 2,6-phenylbenzene pyridine iridium [III] title complex
English name: Ir[III] [6-[5-trifluoromethylpyrazol-3-yl]-2,2 '-bipyridine] [2,6-diphenylpyridine], be abbreviated as: Ir[III] [bpyfpz] [dppy]
Introduced fluoro-containing group in the title complex of the present invention, mainly contained following advantage: fluoro-containing group can effectively reduce the generation of by product in the reaction to the sterically hindered effect of contiguous nitrogen-atoms; Fluoro-containing group hale electronic effect, can strengthen the proton acidity of NH, make the easier deprotonation of NH; The introducing of fluoro-containing group helps to improve luminous efficiency and increases solvability.
The photoluminescence performance test result shows that this title complex has good photoluminescence performance when solid-state, shows a strong red emission, and its maximum value is positioned at 630nm, and luminescent lifetime is 2160ns, and the quantum luminous efficiency is 0.17.
Obtain orange-red solid-state pure products according to preparation method of the present invention---novel electric neutrality three tooth iridium [III] title complex red light materials, its productive rate reaches 30-68%, and production efficiency is very high, and economic benefit is very remarkable.
Do not use any organic solvent as reaction media in the second step building-up reactions of the inventive method, promptly adopt and exempt from the solvent synthesis method.What add in this reaction is excessive greatly 2 in step, and 6-phenylbenzene pyridine except as the three tooth chelating ligands, is in the excess ligand of molten state also as reaction media under 110 ℃.If in this step, introduced any organic solvent, will cause the failure of whole compound experiment, therefore, above-mentioned synthetic method has good novelty and uniqueness.
Embodiment
Following examples are used to illustrate the present invention, but are not used for limiting the scope of the invention.
Wherein, three hydration iridous chlorides (III): available from the chemical company limited of A Faaisha (Tianjin)
2,6-phenylbenzene pyridine: available from the chemical company limited of A Faaisha (Tianjin)
Silver triflate: available from Shanghai reagent company of traditional Chinese medicines group
6-(5-trifluoromethyl pyrazol)-2,2 '-dipyridyl: according to the preparation of document record method (K.-S.Chen, W.-H.Liu, Y.-H.Wang, C.-H.Lai, P.-T.Chou, G.-H.Lee, K.Chen, H.-Y.Chen, Y.Chi, F.-C.Tung, Advanced Functional Materials 2007,17,2964).
Embodiment 1
Under nitrogen protection; three water iridous chloride [III] metal-salt reagent (353mg; 1.00mmol) and the 6-[5-5-flumethiazine]-2,2 '-(303.7mg, 1.05mmol) (both mol ratios are 1: 1.05) was heated to 78 ℃ of back flow reaction 2 days to dipyridyl three tooth chelating ligands in 30mL ethanol.Stop heating, after question response liquid is cooled to normal temperature, on Rotary Evaporators, reaction solution is drained, with the solid dissolving that obtains, in stirring, add the 60mL ether then its precipitation is separated out with 10mL acetone.The throw out that obtains is separated out in filtration, and with ether washing precipitation 3-4 time, (535mg, 0.91mmol), productive rate is about 91% to obtain an orange-yellow solid-state intermediate after the vacuum-drying.
In nitrogen glove box, with above-mentioned complex of iridium intermediate (535mg, 0.91mmol), silver triflate (702mg, 2.73mmol) and 2,6-phenylbenzene pyridine ligand (2.11g, 9.10mmol) (three's mol ratio is 1: 3: 10) uniform mixing in mortar, and be milled into 400-500 purpose powder, place 50mL single port round-bottom reaction flask then.Under nitrogen protection, reaction mixture is heated to 110 ℃, and remains under this temperature and to continue stirring reaction 24 hours.Stop heating, the question response liquid cooling is dissolved it with the 200mL dichloromethane solvent to normal temperature, removes by filter insoluble solid, and the filtrate of collection is drained on Rotary Evaporators and obtained crude product.The crude product that obtains carries out wash-out on silica gel (100-200 order) chromatography column separates, with methylene dichloride as eluent, collect second section orange-red eluate, the orange red elutriant of collecting is drained on Rotary Evaporators, can obtain orange-red solid-state pure products (198mg after the vacuum-drying, 0.273mmol), productive rate is 30%.
MS(FAB，
193Ir)：m/z?711(M
+).
1H?NMR(Acetone-d
6，500MHz)δ：8.58(d，1H，J＝8.0Hz)，8.53(d，1H，J＝7.5Hz)，8.25(d，1H，J＝8.0Hz)，8.13(t，1H，J＝8.0Hz)，7.95-7.88(m，4H)，7.79(d，1H，J＝6.0Hz)，7.75(td，2H，J＝7.5Hz)，7.24(td，1H，6.6，1.3Hz)，7.08(s，1H)，6.82(t，2H，J＝7.5Hz)，6.63(t，2H，J＝6.9Hz)，6.22(d，2H，J＝7.0Hz)
19F?NMR(Acetone-d6，470MHz)δ：-60.17(3F，s，CF
3)
Anal.Calcd?for?C
31H
19F
3N
6Ir：C?52.39，H?2.69，N?9.85；found：C?52.16，H?3.09，N9.67.
Embodiment 2
Under nitrogen protection; three water iridous chloride [III] metal-salt reagent (353mg; 1.00mmol) and the 6-[5-5-flumethiazine]-2,2 '-(303.7mg, 1.05mmol) (both mol ratios are 1: 1.05) was heated to 78 ℃ of back flow reaction 2 days to dipyridyl three tooth chelating ligands in 30mL ethanol.Stop heating, after question response liquid is cooled to normal temperature, on Rotary Evaporators, reaction solution is drained, with the solid dissolving that obtains, in stirring, add the 60mL ether then its precipitation is separated out with 10mL acetone.The throw out that obtains is separated out in filtration, and with ether washing precipitation 3-4 time, (532mg, 0.90mmol), productive rate is about 90% to obtain an orange-yellow solid-state intermediate after the vacuum-drying.
In nitrogen glove box, with above-mentioned complex of iridium intermediate (532mg, 0.90mmol), silver triflate (702mg, 2.73mmol) and 2,6-phenylbenzene pyridine ligand (4.21g, 18.20mmol) (three's mol ratio is 1: 3: 20) uniform mixing in mortar, and be milled into 400-500 order powder, place 50mL single port round-bottom reaction flask then.Under nitrogen protection, reaction mixture is heated to 110 ℃, and remains under this temperature and to continue stirring reaction 24 hours.Stop heating, the question response liquid cooling is dissolved it with the 200mL dichloromethane solvent to normal temperature, removes by filter insoluble solid, and the filtrate of collection is drained on Rotary Evaporators and obtained crude product.The crude product that obtains carries out wash-out on silica gel (100-200 order) chromatography column separates, with methylene dichloride as eluent, collect second section orange-red eluate, the orange red elutriant of collecting is drained on Rotary Evaporators, can obtain orange-red solid-state pure products (297mg after the vacuum-drying, 0.410mmol), productive rate is 45%; The experimental data of proton nmr spectra, fluorine spectrum, mass spectrum and ultimate analysis is with embodiment 1.
Embodiment 3
Under nitrogen protection; three water iridous chloride [III] metal-salt reagent (353mg; 1.00mmol) and the 6-[5-5-flumethiazine]-2,2 '-(303.7mg, 1.05mmol) (both mol ratios are 1: 1.05) was heated to 78 ℃ of back flow reaction 2 days to dipyridyl three tooth chelating ligands in 30mL ethanol.Stop heating, after question response liquid is cooled to normal temperature, on Rotary Evaporators, reaction solution is drained, with the solid dissolving that obtains, in stirring, add the 60mL ether then its precipitation is separated out with 10mL acetone.The throw out that obtains is separated out in filtration, and with ether washing precipitation 3-4 time, (540mg, 0.92mmol), productive rate is about 92% to obtain an orange-yellow solid-state intermediate after the vacuum-drying.
In nitrogen glove box, with above-mentioned complex of iridium intermediate (540mg, 0.92mmol), silver triflate (702mg, 2.73mmol) and 2,6-phenylbenzene pyridine ligand (6.32g, 27.30mmol) (three's mol ratio is 1: 3: 30) uniform mixing in mortar, and be milled into 400-500 purpose powder, place 50mL single port round-bottom reaction flask then.Under nitrogen protection, reaction mixture is heated to 110 ℃, and remains under this temperature and to continue stirring reaction 24 hours.Stop heating, the question response liquid cooling is dissolved it with the 200mL dichloromethane solvent to normal temperature, removes by filter insoluble solid, and the filtrate of collection is drained on Rotary Evaporators and obtained crude product.The crude product that obtains carries out wash-out on silica gel (100-200 order) chromatography column separates, with methylene dichloride as eluent, collect second section orange-red eluate, the orange red elutriant of collecting is drained on Rotary Evaporators, can obtain orange-red solid-state pure products (396mg after the vacuum-drying, 0.546mmol), productive rate is 60%; The experimental data of proton nmr spectra, fluorine spectrum, mass spectrum and ultimate analysis is with embodiment 1.
Embodiment 4
Under nitrogen protection; three water iridous chloride [III] metal-salt reagent (353mg; 1.00mmol) and the 6-[5-5-flumethiazine]-2,2 '-(303.7mg, 1.05mmol) (both mol ratios are 1: 1.05) was heated to 78 ℃ of back flow reaction 2 days to dipyridyl three tooth chelating ligands in 30mL ethanol.Stop heating, after question response liquid is cooled to normal temperature, on Rotary Evaporators, reaction solution is drained, with the solid dissolving that obtains, in stirring, add the 60mL ether then its precipitation is separated out with 10mL acetone.The throw out that obtains is separated out in filtration, and with ether washing precipitation 3-4 time, (546mg, 0.93mmol), productive rate is about 93% to obtain an orange-yellow solid-state intermediate after the vacuum-drying.
In nitrogen glove box, with above-mentioned complex of iridium intermediate (546mg, 0.93mmol), silver triflate (702mg, 2.73mmol) and 2,6-phenylbenzene pyridine ligand (8.42g, 36.40mmol) (three's mol ratio is 1: 3: 40) uniform mixing in mortar, and be milled into 400-500 purpose powder, place 50mL single port round-bottom reaction flask then.Under nitrogen protection, reaction mixture is heated to 110 ℃, and remains under this temperature and to continue stirring reaction 24 hours.Stop heating, the question response liquid cooling is dissolved it with the 200mL dichloromethane solvent to normal temperature, removes by filter insoluble solid, and the filtrate of collection is drained on Rotary Evaporators and obtained crude product.The crude product that obtains carries out wash-out on silica gel (100-200 order) chromatography column separates, with methylene dichloride as eluent, collect second section orange-red eluate, the orange red elutriant of collecting is drained on Rotary Evaporators, can obtain orange-red solid-state pure products (429mg after the vacuum-drying, 0.592mmol), productive rate is 65%; The experimental data of proton nmr spectra, fluorine spectrum, mass spectrum and ultimate analysis is with embodiment 1.
Embodiment 5
Under nitrogen protection; three water iridous chloride [III] metal-salt reagent (353mg; 1.00mmol) and the 6-[5-5-flumethiazine]-2,2 '-(303.7mg, 1.05mmol) (both mol ratios are 1: 1.05) was heated to 78 ℃ of back flow reaction 2 days to dipyridyl three tooth chelating ligands in 30mL ethanol.Stop heating, after question response liquid is cooled to normal temperature, on Rotary Evaporators, reaction solution is drained, with the solid dissolving that obtains, in stirring, add the 60mL ether then its precipitation is separated out with 10mL acetone.The throw out that obtains is separated out in filtration, and with ether washing precipitation 3-4 time, (538mg, 0.91mmol), productive rate is about 91% to obtain an orange-yellow solid-state intermediate after the vacuum-drying.
In nitrogen glove box, with above-mentioned complex of iridium intermediate (538mg, 0.91mmol), silver triflate (702mg, 2.73mmol) and 2,6-phenylbenzene pyridine ligand (10.53g, 45.50mmol) (three's mol ratio is 1: 3: 50) uniform mixing in mortar, and be milled into 400-500 purpose powder, place 50mL single port round-bottom reaction flask then.Under nitrogen protection, reaction mixture is heated to 110 ℃, and remains under this temperature and to continue stirring reaction 24 hours.Stop heating, the question response liquid cooling is dissolved it with the 200mL dichloromethane solvent to normal temperature, removes by filter insoluble solid, and the filtrate of collection is drained on Rotary Evaporators and obtained crude product.The crude product that obtains carries out wash-out on silica gel (100-200 order) chromatography column separates, with methylene dichloride as eluent, collect second section orange-red eluate, the orange red elutriant of collecting is drained on Rotary Evaporators, can obtain orange-red solid-state pure products (449mg after the vacuum-drying, 0.619mmol), productive rate is 68%; The experimental data of proton nmr spectra, fluorine spectrum, mass spectrum and ultimate analysis is with embodiment 1.
Claims (3)
1. novel electric neutrality three tooth iridium [III] title complex red light materials are 6-[5-trifluoromethyl pyrazols]-2,2 '-dipyridyl 2,6-phenylbenzene pyridine closes iridium [III] title complex, and it is characterized in that: molecular structural formula is:
2. the method for preparing described novel electric neutrality three tooth iridium [III] title complex red light materials, comprise the steps: under nitrogen protection, by mol ratio is 1: 1.05 three water iridous chloride [III] metal-salt reagent and 6-[5-5-flumethiazine]-2,2 '-dipyridyl [be called for short bpyfpzH] three tooth chelating ligands were heated to 78 ℃ of back flow reaction 2 days in ethanolic soln, after stop the heating, after question response liquid returns to normal temperature, reaction solution is drained on Rotary Evaporators, with volume ratio is that acetone-ether mixed solvent of 1: 6 carries out recrystallization, the throw out that filtration and recrystallization obtains, with ether washing precipitate 3-4 time, can obtain an orange-yellow solid-state intermediate after the vacuum-drying;
In nitrogen glove box, be 1: 3 with mol ratio: the above-mentioned orange-yellow solid-state intermediate of 10-50, silver triflate and 2,6-phenylbenzene pyridine [is called for short dppyH
2] part uniform mixing in mortar; and be milled into 400-500 purpose powder; place the single port round-bottom reaction flask then; under nitrogen protection; with three's mixture heating up to 110 ℃; and remain under this temperature and to continue stirring reaction 24 hours; stop heating; the question response liquid cooling is to normal temperature; with the dichloromethane solvent dissolving, remove by filter insoluble solid, the filtrate of collection is drained on Rotary Evaporators and is obtained crude product; the crude product wash-out on silica gel column chromatography that obtains is separated; as eluent, collect second section orange-red eluate with methylene dichloride, the orange red elutriant of collecting is drained on Rotary Evaporators; can obtain orange-red solid-state pure products after the vacuum-drying---novel electric neutrality three tooth iridium [III] title complex red light materials, its productive rate reaches 30-68%.
3. according to the method for described novel electric neutrality three tooth iridium [III] the title complex red light materials of the described preparation of claim 2, it is characterized in that: preferably, described orange-yellow solid-state intermediate, silver triflate and 2,6-phenylbenzene pyridine three's mol ratio is 1: 3: 30, its resultant orange-red solid-state pure products---novel electric neutrality three tooth iridium [III] title complex red light materials, productive rate is 60%.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105801627A (en) * | 2014-12-23 | 2016-07-27 | 季昀 | Iridium metal complex containing double tridentate ligand |
| US10153442B2 (en) | 2015-12-31 | 2018-12-11 | National Tsing Hua University | Iridium complex, OLED using the same, and nitrogen-containing tridentate ligand having carbene unit |
| US10825997B2 (en) | 2015-06-25 | 2020-11-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11168103B2 (en) | 2017-11-17 | 2021-11-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11233205B2 (en) | 2017-12-14 | 2022-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN114057931A (en) * | 2021-12-06 | 2022-02-18 | 南京工业职业技术大学 | Temperature response polymer material with iridium complex and europium chelate as monomers, and preparation method and application thereof |
-
2011
- 2011-05-31 CN CN2011101426741A patent/CN102268250A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| JING-LIN CHEN等: "Iridium(III) Bis-tridentate Complexes with 6-(5-Trifluoromethylpyrazol-3-yl)-2,20-bipyridine Chelating Ligands Synthesis, Characterization, and Photophysical Properties", 《ORGANOMETALLICS》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105801627A (en) * | 2014-12-23 | 2016-07-27 | 季昀 | Iridium metal complex containing double tridentate ligand |
| CN105801627B (en) * | 2014-12-23 | 2018-06-08 | 季昀 | Iridium metal complex containing double tridentate ligand |
| US10825997B2 (en) | 2015-06-25 | 2020-11-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10153442B2 (en) | 2015-12-31 | 2018-12-11 | National Tsing Hua University | Iridium complex, OLED using the same, and nitrogen-containing tridentate ligand having carbene unit |
| US11168103B2 (en) | 2017-11-17 | 2021-11-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11233205B2 (en) | 2017-12-14 | 2022-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN114057931A (en) * | 2021-12-06 | 2022-02-18 | 南京工业职业技术大学 | Temperature response polymer material with iridium complex and europium chelate as monomers, and preparation method and application thereof |
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