CN113214325A - Organic iridium metal complex and preparation method and application thereof - Google Patents
Organic iridium metal complex and preparation method and application thereof Download PDFInfo
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- CN113214325A CN113214325A CN202110292642.3A CN202110292642A CN113214325A CN 113214325 A CN113214325 A CN 113214325A CN 202110292642 A CN202110292642 A CN 202110292642A CN 113214325 A CN113214325 A CN 113214325A
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 68
- -1 iridium metal complex Chemical class 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000000463 material Substances 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 239000003446 ligand Substances 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims abstract description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 7
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 59
- 229910052757 nitrogen Inorganic materials 0.000 claims description 49
- 238000000967 suction filtration Methods 0.000 claims description 37
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 33
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 238000001035 drying Methods 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 15
- 238000005406 washing Methods 0.000 claims description 14
- 235000019441 ethanol Nutrition 0.000 claims description 13
- 239000000706 filtrate Substances 0.000 claims description 13
- 239000003208 petroleum Substances 0.000 claims description 13
- 238000010898 silica gel chromatography Methods 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 9
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 229940126062 Compound A Drugs 0.000 claims description 5
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- 230000000903 blocking effect Effects 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- LNJXVUXPFZKMNF-UHFFFAOYSA-K iridium(3+);trichloride;trihydrate Chemical compound O.O.O.Cl[Ir](Cl)Cl LNJXVUXPFZKMNF-UHFFFAOYSA-K 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 230000005525 hole transport Effects 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 238000002386 leaching Methods 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 13
- 238000003786 synthesis reaction Methods 0.000 abstract description 13
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 10
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 abstract description 8
- 150000004696 coordination complex Chemical class 0.000 abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 abstract description 4
- 229910052751 metal Inorganic materials 0.000 abstract description 4
- 239000002184 metal Substances 0.000 abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 150000002736 metal compounds Chemical class 0.000 abstract description 2
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 36
- 238000012360 testing method Methods 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000007787 solid Substances 0.000 description 22
- 229910052760 oxygen Inorganic materials 0.000 description 20
- 229910052799 carbon Inorganic materials 0.000 description 16
- 238000001819 mass spectrum Methods 0.000 description 13
- 238000000921 elemental analysis Methods 0.000 description 11
- 239000003480 eluent Substances 0.000 description 11
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- 239000008213 purified water Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 230000001376 precipitating effect Effects 0.000 description 7
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 4
- 101100490479 Lactococcus lactis subsp. lactis (strain IL1403) addA gene Proteins 0.000 description 4
- 101100027846 Lactococcus lactis subsp. lactis (strain IL1403) obg gene Proteins 0.000 description 4
- 101100000975 Lactococcus lactis subsp. lactis (strain IL1403) rexB gene Proteins 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000002503 iridium Chemical class 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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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
- C09K2211/1029—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
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
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- Spectroscopy & Molecular Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
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Abstract
The invention discloses an organic iridium metal complex, which has a structural general formula shown in chemical formula 1:
Description
Technical Field
The invention belongs to the technical field of organic light-emitting devices, and particularly relates to an organic iridium metal complex, a preparation method thereof and application thereof in preparation of organic electroluminescent devices.
Background
In 1987, doctor dung Qing cloud reported an electroluminescent diode technology based on organic luminescent material, which mainly adopts a vacuum evaporation way to prepare a double-layer device with a transmission layer and a luminescent layer, improves the quantum efficiency to 1 percent and can reach 1000cd/m under the working voltage lower than 10V2The brightness of the organic electroluminescence device promotes the organic electroluminescence technology to move to the practical stage. Electroluminescent devices have an all-solid-state structure, and organic electroluminescent materials are the core and foundation of the device. The development of new materials is a source for promoting the continuous progress of the electroluminescent technology. The preparation of the original material and the optimization of the device are also the research hotspots of the organic electroluminescent industry at present.
The phenomenon of phosphorescence has been pursued since the discovery, and since the luminous efficiency of phosphorescence materials is obviously higher than that of fluorescence, theoretically 100%, many research and development institutions are increasing the research and development efforts of phosphor materials, and trying to accelerate the industrialization development through phosphorescence materials. However, the development of the market is greatly hindered due to the high synthesis price of the phosphorescent material, the complex synthesis process, the environmental pollution during the synthesis process, the low synthesis purity, the low efficiency and the like.
Therefore, it is an urgent need to solve the technical problems of the art to provide a phosphorescent material for an organic light emitting device, which has low synthesis cost, simple synthesis process, no pollution, and high synthesis purity and efficiency.
Disclosure of Invention
The invention provides an organic iridium metal complex, a preparation method thereof and application thereof in preparing organic electroluminescent devices.
In order to achieve the purpose, the invention adopts the following technical scheme:
an organic iridium metal complex, the structural general formula of which is shown in chemical formula 1:
Wherein: r1, R2, R3, R4, R5, R6, R7 each independently represent hydrogen, deuterium, amino, hydroxyl, halogen, cyano, alkyl, alkoxy, aryl or an aromatic heterocyclic group.
Further, the halogen is specifically one or more of F, Cl, Br and I, and is preferably F.
Further, the alkyl is one of C1-C8 alkyl;
the above-mentioned C1-C8 alkyl group is selected from a substituted or unsubstituted straight-chain alkyl group, a substituted or unsubstituted branched-chain alkyl group, a substituted or unsubstituted cycloalkyl group; and the substituents are independently selected from deuterium, amino, hydroxy, halogen, cyano;
further, the alkoxy is one of C1-C8 alkoxy;
the alkylene is one of C2-C6 alkylene;
the alkynyl is one of C2-C6 alkynyl;
the aryl is one of C6-C18 aryl;
the above aryl group is selected from an unsubstituted aryl group or an aryl group having at least one substituent;
further, the aromatic heterocyclic group is one of C4-C12 aromatic heterocyclic groups;
the above aromatic heterocyclic groups are independently selected from unsubstituted aromatic heterocyclic groups or aromatic heterocyclic groups having at least one substituent; and the substituent is independently selected from one or more of deuterium, amino, hydroxyl, halogen and cyano.
Preferably, the primary ligand C is selected from any one of the following structural formulas:
more preferably, the structural formula of the organic iridium metal complex is any one of the following structural formulas:
the invention also provides a preparation method of the organic iridium metal complex, which comprises the following steps:
(1) under the protection of nitrogen, mixing the compound A and iridium trichloride trihydrate, adding the mixture into a solvent I for heating reaction, performing suction filtration after the reaction is finished, leaching with water, absolute ethyl alcohol and petroleum ether in sequence, and drying to obtain a bridging ligand B;
(2) under the protection of nitrogen, mixing the bridged ligand B obtained in the step (1) with a compound C, adding the mixture into a solvent II for heating reaction, after the reaction is finished, sequentially performing suction filtration, alcohol washing, drying and silica gel column chromatography, and concentrating the filtrate to obtain the organic iridium metal complex shown in the chemical formula 1;
the synthetic route of the organic iridium metal complex shown in chemical formula 1 is as follows:
further, in the step (1), the molar ratio of the compound A to the iridium trichloride trihydrate is (2.5-4) to 1;
the solvent I is ethylene glycol ethyl ether aqueous solution, and the volume ratio of the ethylene glycol ethyl ether to the water is (2.5-4) to 1; the molar ratio of the ethylene glycol ethyl ether to the compound A is 73: 1;
further, in step (2), the molar ratio of compound C to bridging ligand B is (2.5-4): 1;
the solvent II is a mixed solution of ethylene glycol ethyl ether and anhydrous potassium carbonate; the molar ratio of the ethylene glycol ethyl ether to the anhydrous potassium carbonate is 35: 1;
the molar ratio of ethylene glycol ethyl ether to compound C is 350: 1;
further, in the step (1), the reaction temperature is 100-130 ℃, and the reaction time is 20-24 h.
Furthermore, in the step (2), the reaction temperature is 100-130 ℃, and the reaction time is 20-24 h.
The invention also provides application of the organic iridium metal complex in preparing organic electroluminescent devices.
Preferably, the organic electroluminescent device comprises: the organic electroluminescent device comprises a first electrode, an organic electroluminescent material layer and a second electrode; wherein the organic electroluminescent material layer includes the organic iridium metal complex of claim 1.
More preferably, the organic electroluminescent material layer comprises, in order by evaporation: one or more layers of a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer, and at least one of them comprises the organic iridium metal complex according to claim 1.
The invention has the beneficial effects that: the invention provides an organic iridium metal complex phosphor luminescent material and a preparation method thereof, the phosphor luminescent material is used as a complex with a novel structure, an organic metal compound is obtained by combining metal iridium with a specific heterocyclic ligand, and the phosphor luminescent material can obviously improve the luminous efficiency of an organic electroluminescent device after being applied to the organic electroluminescent device. The preparation method of the phosphor luminescent material provided by the invention has the characteristics of simple synthesis steps, mild condition requirements and high yield of target products, and solves the problems of high synthesis price and higher synthesis process requirements of the existing phosphor luminescent material.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Compound L001 was prepared by the following specific steps:
(1) a-001(85.2mmol, 21.73g) and IrCl were charged into a nitrogen-substituted reactor under a nitrogen atmosphere3·3H2O (28.4mmo1, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water are refluxed at 120 ℃ for 24 hours under the nitrogen atmosphere, then the mixture is cooled to room temperature, precipitates are separated out, solid is obtained by suction filtration, and is sequentially leached by 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether and dried to obtain red powdery bridging ligand B-001(13.26g, the yield is 61%);
(2) adopting a nitrogen replacement reactor, adding B-001(8mmol, 11.78g) and C-001(24mmol, 2.37g) into the reactor under the nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and 11.04g of potassium carbonate into the system, stirring for 24 hours at 120 ℃ under the nitrogen atmosphere, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, concentrating the filtrate, precipitating a solid, and carrying out suction filtration to finally obtain a red compound L001(6.33g, the yield is 49.5%).
Specifically, the reaction formulae of steps (1) to (2) are as follows:
the compound L001 was analyzed, and the specific results were as follows:
HPLC purity: greater than 99%.
Mass spectrum: calculated value 799.95; the test value was 800.23.
Elemental analysis:
the calculated values are: 64.56 percent of C; 3.91 percent of H; 3.50 percent of N; 4.00 percent of O; 24.03 percent of Ir;
the test values are: 64.55 percent of C; 3.90 percent of H; 3.51 percent of N; 4.01 percent of O; 24.04 percent of Ir.
The comparison of the calculated value and the test value proves that the measured value is basically consistent with the theoretical value, so that the organic iridium metal complex can be successfully synthesized by the technical scheme disclosed by the invention.
Example 2
The method for preparing the organic iridium metal complex phosphor luminescent material L015 comprises the following specific steps:
(1) a-015(85.2mmol, 24.81g) is added into a nitrogen displacement reactor in the nitrogen atmosphere,IrCl3·3H2O (28.4mmo1, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water are refluxed at 120 ℃ for 24 hours under the atmosphere of nitrogen, then the mixture is cooled to room temperature, precipitates are separated out, solid is obtained by suction filtration, and is sequentially leached by 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether and dried to obtain red powdery bridging ligand B-015(14.46g, the yield is 63%);
(2) adopting a nitrogen replacement reactor, adding B-015(8mmol, 12.93g) and C-015(24mmol, 2.37g) into the reactor in a nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and 11.04g of potassium carbonate into the system, stirring for 24 hours at 120 ℃ in the nitrogen atmosphere, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, concentrating the filtrate, precipitating a solid, and carrying out suction filtration to finally obtain a red compound L015(6.76g, the yield is 48.5%).
Specifically, the reaction formulae of steps (1) to (2) are as follows:
the compound L015 is subjected to detection analysis, and specific results are as follows:
HPLC purity: greater than 99%.
Mass spectrum: calculated value 871.91; the test value was 872.72.
Elemental analysis:
the calculated values are: 59.23 percent of C; 3.12 percent of H; 3.21 percent of N; 3.67 percent of O; 22.05 percent of Ir; 8.72 percent of F;
the test values are: 59.22 percent of C; 3.13 percent of H; 3.22 percent of N; 3.68 percent of O; 22.04 percent of Ir; f, 8.73 percent.
The comparison of the calculated value and the test value proves that the measured value is basically consistent with the theoretical value, so that the organic iridium metal complex can be successfully synthesized by the technical scheme disclosed by the invention.
Example 3
The compound with the number of L016 is prepared by the following specific synthetic steps:
(1) replacing the reactor with nitrogen, and adding into the reactor under nitrogen atmosphereA-016(85.2mmol, 21.73g), IrCl3·3H2O (28.4mmo1, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water are refluxed at 120 ℃ for 24 hours under the nitrogen atmosphere, then the mixture is cooled to room temperature, precipitates are separated out, solid is obtained by suction filtration, and is sequentially leached by 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether and dried to obtain red powdery bridging ligand B-016(12.7g, the yield is 61%);
2) adopting a nitrogen replacement reactor, adding B-016(8mmol, 11.78g) and C-016(24mmol, 3.72g) into the reactor under the nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and 11.04g of potassium carbonate into the system, stirring at 120 ℃ for 24 hours under the nitrogen atmosphere, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, concentrating the filtrate, precipitating a solid, and carrying out suction filtration to finally obtain a red compound L016(6.5g, the yield is 47.5%).
Specifically, the reaction formulae of steps (1) to (2) are as follows:
the compound L016 was analyzed and the specific results are as follows:
HPLC purity: greater than 99%.
Mass spectrum: calculated value 856.06; the test value was 857.17.
Elemental analysis:
the calculated values are: 65.94 percent of C; 4.59 percent of H; 3.27 percent of N; 3.74 percent of O; 22.45 percent of Ir;
the test values are: c, 65.95 percent; 4.58 percent of H; 3.26 percent of N; 3.75 percent of O; 22.44 percent of Ir.
The comparison of the calculated value and the test value proves that the measured value is basically consistent with the theoretical value, so that the organic iridium metal complex can be successfully synthesized by the technical scheme disclosed by the invention.
Example 4
The compound with the number L025 is prepared by the following specific synthetic steps:
(1) replacing the reactor with nitrogen gas, and introducing into the reactor under nitrogen gas atmosphereAdding A-025(85.2mmol, 26.53g) and IrCl3·3H2O (28.4mmo1, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water are refluxed at 120 ℃ for 24 hours under the nitrogen atmosphere, then the mixture is cooled to room temperature, precipitates are separated out, solid is obtained by suction filtration, and is sequentially leached by 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether and dried to obtain red powdery bridging ligand B-025(14.21g, the yield is 59%);
(2) adopting a nitrogen replacement reactor, adding B-025(8mmol, 13.57g) and C-025(24mmol, 3.72g) into the reactor under the nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and potassium carbonate (11.04g) into the system, stirring for 24 hours at 120 ℃ under the nitrogen atmosphere, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, concentrating the filtrate, precipitating a solid, and carrying out suction filtration to finally obtain a red compound L025(7.6g, yield 50%).
Specifically, the reaction formulae of steps (1) to (2) are as follows:
the compound L025 was subjected to detection analysis, and the specific results were as follows:
HPLC purity: greater than 99%.
Mass spectrum: calculated value 968.27; the test value was 969.34.
Elemental analysis:
the calculated values are: 68.23 percent of C; 5.73 percent of H; 2.89 percent of N; 3.30 percent of O; 19.85 percent of Ir;
the test values are: 68.24 percent of C; 5.72 percent of H; 2.88 percent of N; 3.31 percent of O; 19.84 percent of Ir.
The comparison of the calculated value and the test value proves that the measured value is basically consistent with the theoretical value, so that the organic iridium metal complex can be successfully synthesized by the technical scheme disclosed by the invention.
Example 5
The compound with the number of L035 was prepared by the following specific synthetic steps:
(1) replacing the reactor with nitrogen gas, and introducing into the reactor under nitrogen gas atmosphereAdding A-035(85.2mmol, 25.67g) and IrCl3·3H2O (28.4mmo1, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water are refluxed at 120 ℃ for 24 hours under the nitrogen atmosphere, then the mixture is cooled to room temperature, precipitates are separated out, solid is obtained by suction filtration, and is sequentially leached by 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether and dried to obtain red powdery bridging ligand B-035(14.58g, the yield is 62%);
(2) by adopting a nitrogen replacement reactor, adding B-035(8mmol, 13.25g) and C-035(24mmol, 4.06g) into the reactor under the nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and potassium carbonate (11.04g) into the system, stirring for 24 hours at 120 ℃ under the nitrogen atmosphere, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, carrying out solid precipitation after concentration on the filtrate, and carrying out suction filtration to finally obtain a red compound L035(7.31g, the yield is 47.5%).
Specifically, the reaction formulae of steps (1) to (2) are as follows:
the compound L035 was analyzed and the results were as follows:
HPLC purity: greater than 99%.
Mass spectrum: calculated value 962.17; the test value was 963.52.
Elemental analysis:
the calculated values are: 64.91 percent of C; 4.92 percent of H; 2.91 percent of N; 3.33 percent of O; 19.98 percent of Ir;
the test values are: c, 64.90 percent; 4.93 percent of H; 2.92 percent of N; 3.32 percent of O; 19.99 percent of Ir.
The comparison of the calculated value and the test value proves that the measured value is basically consistent with the theoretical value, so that the organic iridium metal complex can be successfully synthesized by the technical scheme disclosed by the invention.
Example 6
The compound with the number of L041 is prepared by the following specific synthetic steps:
(1) using a nitrogen replacement reactor, and reacting in a nitrogen atmosphereA-041(85.2mmol, 22.94g) and IrCl were added into the reactor3·3H2O (28.4mmo1, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water are refluxed at 120 ℃ for 24 hours under the nitrogen atmosphere, then the mixture is cooled to room temperature, precipitates are separated out, solid is obtained by suction filtration, and is sequentially leached by 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether and dried to obtain red powdery bridging ligand B-041(13.67g, the yield is 63%);
(2) adopting a nitrogen replacement reactor, adding B-041(8mmol, 12.22) and C-041(24mmol, 4.06g) into the reactor under the nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and potassium carbonate (11.04g) into the system, stirring for 24 hours at 120 ℃ under the nitrogen atmosphere, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, concentrating the filtrate, precipitating a solid, and carrying out suction filtration to finally obtain a red compound L041(7.02g, the yield is 48.9%).
Specifically, the reaction formulae of steps (1) to (2) are as follows:
the compound L041 is detected and analyzed, and the specific results are as follows:
HPLC purity: greater than 99%.
Mass spectrum: calculated value 898.14; the test value was 899.21.
Elemental analysis:
the calculated values are: 66.87 percent of C; 5.05 percent of H; 3.12 percent of N; 3.56 percent of O; 21.40 percent of Ir;
the test values are: c, 66.88 percent; 5.04 percent of H; 3.13 percent of N; 3.55 percent of O; 21.41 percent of Ir.
The comparison of the calculated value and the test value proves that the measured value is basically consistent with the theoretical value, so that the organic iridium metal complex can be successfully synthesized by the technical scheme disclosed by the invention.
Example 7
The compound numbered L046 was prepared by the following specific synthetic procedure:
(1) adopting a nitrogen replacement reactor, under the nitrogen atmosphere,a-046(85.2mmol, 21.73g), IrCl were added to the reactor3·3H2O (28.4mmo1, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water are refluxed at 120 ℃ for 24 hours under the atmosphere of nitrogen, then the mixture is cooled to room temperature, precipitates are separated out, solid is obtained by suction filtration, and is sequentially leached by 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether and dried to obtain red powdery bridging ligand B-046(13.26g, the yield is 61%);
(2) adopting a nitrogen replacement reactor, adding B-046(8mmol, 11.78g) and C-046(24mmol, 4.39g) into the reactor under the nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and potassium carbonate (11.04g) into the system, stirring for 24 hours at 120 ℃ under the nitrogen atmosphere, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, carrying out solid precipitation after concentration on the filtrate, and carrying out suction filtration to finally obtain a red compound L046(6.95g, the yield is 49.2%).
Specifically, the reaction formulae of steps (1) to (2) are as follows:
the compound L046 is detected and analyzed, and the specific results are as follows:
HPLC purity: greater than 99%.
Mass spectrum: calculated value 884.11; the test value was 885.28.
Elemental analysis:
the calculated values are: 66.57 percent of C; 4.90 percent of H; 3.17 percent of N; 3.62 percent of O; 21.74 percent of Ir;
the test values are: c, 66.56 percent; 4.91 percent of H; 3.18 percent of N; 3.61 percent of O; 21.73 percent of Ir.
The comparison of the calculated value and the test value proves that the measured value is basically consistent with the theoretical value, so that the organic iridium metal complex can be successfully synthesized by the technical scheme disclosed by the invention.
Example 8
The compound with the serial number of L061 is prepared by the following specific synthetic steps:
(1) using a nitrogen displacement reactor in a nitrogen atmosphereNext, A-061(85.2mmol, 21.73g), IrCl was charged to the reactor3·3H2O (28.4mmo1, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water are refluxed at 120 ℃ for 24 hours under the nitrogen atmosphere, then the mixture is cooled to room temperature, precipitates are separated out, solid is obtained by suction filtration, and is sequentially leached by 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether and dried to obtain red powdery bridging ligand B-061(13.26g, the yield is 61%);
(2) adopting a nitrogen replacement reactor, adding B-061(8mmol, 11.77g) and C-061(24mmol, 5.68g) into the reactor in a nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and 11.04g of potassium carbonate into the system, stirring for 24 hours at 120 ℃ in the nitrogen atmosphere, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, concentrating the filtrate, precipitating a solid, and carrying out suction filtration to finally obtain a red compound L061(7.3g, the yield is 48.7%).
Specifically, the reaction formulae of steps (1) to (2) are as follows:
the compound L061 was analyzed, and the specific results were as follows:
HPLC purity: greater than 99%.
Mass spectrum: calculated value 938.12; the test value was 939.24.
Elemental analysis:
the calculated values are: 69.14 percent of C; 3.98 percent of H; 2.99 percent of N; 3.41 percent of O; 20.49 percent of Ir;
the test values are: 69.15 percent of C; 3.99 percent of H; 2.98 percent of N; 3.40 percent of O; 20.48 percent of Ir.
The comparison of the calculated value and the test value proves that the measured value is basically consistent with the theoretical value, so that the organic iridium metal complex can be successfully synthesized by the technical scheme disclosed by the invention.
Example 9
The compound with the number of L093 is prepared by the following specific synthetic steps:
(1) replacing the reactor with nitrogen gas in the presence of nitrogenA-093(85.2mmol, 25.67g), IrCl were added to the reactor under an atmosphere3·3H2O (28.4mmo1, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water are refluxed at 120 ℃ for 24 hours under the nitrogen atmosphere, then the mixture is cooled to room temperature, precipitates are separated out, solid is obtained by suction filtration, and is sequentially leached by 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether and dried to obtain red powdery bridging ligand B-093(15.29g, the yield is 65%);
(2) adopting a nitrogen replacement reactor, adding B-093(8mmol, 13.25g) and C-095(24mmol, 5.74g) into the reactor under a nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and potassium carbonate (11.04g) into the system, stirring at 120 ℃ for 24 hours under the nitrogen atmosphere, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, concentrating the filtrate, precipitating a solid, and carrying out suction filtration to finally obtain a red compound L093(7.84g, 47.5% of yield).
Specifically, the reaction formulae of steps (1) to (2) are as follows:
the compound L093 was analyzed, and the specific results were as follows:
HPLC purity: greater than 99%.
Mass spectrum: calculated value 1032.31; the test value was 1033.24.
Elemental analysis:
the calculated values are: 66.32 percent of C; 5.57 percent of H; 2.71 percent of N; 3.10 percent of O; 18.62 percent of Ir; 3.68 percent of F;
the test values are: 66.33 percent of C; 5.56 percent of H; 2.72 percent of N; 3.11 percent of O; 18.61 percent of Ir; f, 3.69 percent.
The comparison of the calculated value and the test value proves that the measured value is basically consistent with the theoretical value, so that the organic iridium metal complex can be successfully synthesized by the technical scheme disclosed by the invention.
Example 10
The compound with the number of L101 is prepared by the following specific synthetic steps:
(1) by usingThe reactor was purged with nitrogen, and A-101(85.2mmol, 22.94g) and IrCl were added to the reactor under a nitrogen atmosphere3·3H2O (28.4mmo1, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water are refluxed at 120 ℃ for 24 hours under the nitrogen atmosphere, then the mixture is cooled to room temperature, precipitates are separated out, solid is obtained by suction filtration, and is sequentially leached by 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether and dried to obtain red powdery bridging ligand B-101(13.66g, the yield is 63%);
(2) adopting a nitrogen replacement reactor, adding B-101(8mmol, 12.22g) and C-101(24mmol, 5.74g) into the reactor under the nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and potassium carbonate (11.04g) into the system, stirring for 24 hours at 120 ℃ under the nitrogen atmosphere, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, carrying out solid precipitation after filtrate concentration, and carrying out suction filtration to finally obtain a red compound L101(7.66g, yield 49.5%).
Specifically, the reaction formulae of steps (1) to (2) are as follows:
the compound L101 was analyzed, and the specific results are as follows:
HPLC purity: greater than 99%.
Mass spectrum: calculated value 968.27; the test value was 969.31.
Elemental analysis:
the calculated values are: 68.23 percent of C; 5.73 percent of H; 2.89 percent of N; 3.30 percent of O; 19.85 percent of Ir; 3.68 percent of F;
the test values are: 68.24 percent of C; 5.72 percent of H; 2.88 percent of N; 3.31 percent of O; 19.86 percent of Ir; f, 3.67 percent.
The comparison of the calculated value and the test value proves that the measured value is basically consistent with the theoretical value, so that the organic iridium metal complex can be successfully synthesized by the technical scheme disclosed by the invention.
Example 11
The compound with the number of L108 is prepared by the following specific synthetic steps:
(1) the reactor was purged with nitrogen and A-108(85.2mmol, 25.67g), IrCl were added to the reactor under a nitrogen atmosphere3·3H2O (28.4mmo1, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water are refluxed at 120 ℃ for 24 hours under the nitrogen atmosphere, then the mixture is cooled to room temperature, precipitates are separated out, solid is obtained by suction filtration, and is sequentially leached by 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether and dried to obtain red powdery bridging ligand B-108(15.29g, the yield is 65%);
(2) adopting a nitrogen replacement reactor, adding B-108(8mmol, 13.25g) and C-108(24mmol, 5.09g) into the reactor under the nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and potassium carbonate (11.04g) into the system, stirring for 24 hours at 120 ℃ under the nitrogen atmosphere, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, carrying out solid precipitation after concentration on the filtrate, and carrying out suction filtration to finally obtain a red compound L108(7.23g, yield 45%).
Specifically, the reaction formulae of steps (1) to (2) are as follows:
the compound L108 was analyzed, and the specific results were as follows:
HPLC purity: greater than 99%.
Mass spectrum: calculated value 1004.25; the test value was 1004.60.
Elemental analysis:
the calculated values are: c, 65.78; h is 5.32; f is 3.78; 19.14 parts of Ir; n is 2.79; o is 3.19.
The test values are: c, 65.79; h is 5.33; f is 3.79; 19.15 parts of Ir; 2.78 of N; o is 3.16.
The comparison of the calculated value and the test value proves that the measured value is basically consistent with the theoretical value, so that the organic iridium metal complex can be successfully synthesized by the technical scheme disclosed by the invention.
The preparation methods of other organic iridium complexes are the same as those described above, and are not repeated here, and the mass spectrum and the molecular formula of other organic iridium complexes are shown in table 1 below:
TABLE 1 molecular formula and Mass Spectrometry of other organic Iridium Metal complexes
Complexes | Molecular formula | Calculated mass spectrum | Mass spectrometric test values |
L008 | C47H39IrN2O2 | 856.06 | 857.13 |
L027 | C53H45D6IrN2O2 | 946.26 | 947.62 |
L050 | C53H49F2IrN2O2 | 976.20 | 977.18 |
L063 | C57H51IrN2O2 | 988.26 | 989.51 |
L087 | C49H31D12IrN2O2 | 896.19 | 897.23 |
L098 | C55H51F4IrN2O2 | 1040.24 | 1040.58 |
L120 | C53H47F4IrN2O2 | 1012.18 | 1012.49 |
EXAMPLE 12 electroluminescent device implementation
Coating with a thickness ofThe ITO glass substrate of (1) was washed in distilled water for 2 times, ultrasonically for 30 minutes, repeatedly washed in distilled water for 2 times, ultrasonically for 10 minutes, and after the washing with distilled water was completed, solvents such as isopropyl alcohol, acetone, and methanol were ultrasonically washed in this order, dried, transferred to a plasma cleaning machine, washed for 5 minutes, and sent to an evaporation coater.
First, vapor deposition is carried out on the ITO (anode)Followed by evaporationHost substance 4,4'-N, N' -biphenyl dicarbazole ('CBP') and doping substance complex L00195:5 weight ratio are mixed for evaporationVapor deposition electron transport layerVapor deposition of electron injection layerEvaporation cathodeAnd (4) preparing the organic electroluminescent device.
The luminous characteristics of the organic electroluminescent device obtained above were tested using a KEITHLEY model 2400 source measurement unit and a CS-2000 spectroradiometer to evaluate the driving voltage, lifetime, and current efficiency of the device.
Referring to the preparation method of the organic electroluminescent device, the organic iridium metal complex L001 is replaced by L008, L015, L016, L025, L027, L035, L041, L046, L050, L061, L063, L087, L093, L098, L101, L108 and L120 respectively, and the organic electroluminescent device of the corresponding organic iridium metal complex is prepared.
Comparative example 1:
an organic electroluminescent device in which an organic metal complex doped in a light-emitting layer has the following structure was prepared in the same manner as in example 11:
and the same examination as in example 12 was performed on the prepared organic electroluminescent device, and the results are shown in table 2 below.
Table 2 results of measuring performance of electroluminescent devices of example 12, comparative example 1 and doped with other organic iridium metal complexes
As can be seen from Table 2, the organic electroluminescent device prepared by using the organic iridium metal complex provided by the invention as a luminescent layer doping material is superior to the organic electroluminescent device of the comparative complex, the driving voltage is obviously reduced, and the current efficiency and the service life are obviously improved.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (10)
1. An organic iridium metal complex is characterized in that the structural general formula of the organic iridium metal complex is shown as chemical formula 1:
wherein: r1, R2, R3, R4, R5, R6 and R7 each independently represent hydrogen, deuterium, amino, halogen, C1-C8 alkyl, C6-C18 aryl or C4-C12 aromatic heterocyclic group.
2. The organic iridium metal complex according to claim 1,
the halogen is one or more of F, Cl, Br and I, and is preferably F.
The C1-C8 alkyl is selected from substituted or non-substituted straight-chain alkyl, substituted or non-substituted branched-chain alkyl, substituted or non-substituted cycloalkyl; and substituents are selected from deuterium, amino, hydroxy, halogen, cyano;
the C6-C18 aryl is selected from substituted or unsubstituted aryl;
the C4-C12 aromatic heterocyclic group is selected from substituted or unsubstituted aromatic heterocyclic groups; and the substituents are selected from deuterium, amino, hydroxy, halogen, cyano.
3. A method for producing the organic iridium metal complex as claimed in claim 1 or 2, comprising the steps of:
(1) under the protection of nitrogen, mixing the compound A and iridium trichloride trihydrate, adding the mixture into a solvent I for heating reaction, performing suction filtration after the reaction is finished, leaching with water, absolute ethyl alcohol and petroleum ether in sequence, and drying to obtain a bridging ligand B;
(2) under the protection of nitrogen, mixing the bridged ligand B obtained in the step (1) with a compound C, adding the mixture into a solvent II for heating reaction, after the reaction is finished, sequentially performing suction filtration, alcohol washing, drying and silica gel column chromatography, and concentrating the filtrate to obtain the organic iridium metal complex shown in the chemical formula 1;
the synthetic route of the organic iridium metal complex shown in chemical formula 1 is as follows:
4. the method for producing an organic iridium metal complex according to claim 3, wherein in the step (1), the molar ratio of the compound A to iridium trichloride trihydrate is (2.5-4): 1;
the solvent I is ethylene glycol ethyl ether aqueous solution, and the volume ratio of the ethylene glycol ethyl ether to the water is (2.5-4) to 1;
the molar ratio of ethylene glycol ethyl ether to compound a was 73: 1.
5. The process for producing an organic iridium metal complex according to claim 3, wherein in the step (2), the molar ratio of the compound C to the bridging ligand B is (2.5 to 4): 1;
the solvent II is a mixed solution of ethylene glycol ethyl ether and anhydrous potassium carbonate;
the molar ratio of the ethylene glycol ethyl ether to the anhydrous potassium carbonate is 35: 1;
the molar ratio of ethylene glycol ethyl ether to compound C was 350: 1.
6. The method of preparing an organic iridium metal complex according to claim 3, wherein the reaction temperature in step (1) is 100 ℃ to 130 ℃ and the reaction time is 20 to 24 hours.
7. The method of preparing an organic iridium metal complex according to claim 3, wherein the reaction temperature in step (2) is 100 ℃ to 130 ℃ and the reaction time is 20 to 24 hours.
8. Use of the organic iridium metal complex as claimed in claim 1 or 2 in the preparation of an organic electroluminescent device.
9. An organic electroluminescent device is characterized by comprising a first electrode, an organic electroluminescent material layer and a second electrode which are sequentially evaporated; wherein the organic electroluminescent material layer includes the organic iridium metal complex of claim 1 or 2.
10. The organic electroluminescent device according to claim 9, wherein the organic electroluminescent material layer comprises one or more layers selected from a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer, which are sequentially evaporated, and at least one of the layers comprises the organic iridium metal complex according to claim 1 or 2.
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