CN111471072A - 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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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 66
- -1 iridium metal complex Chemical class 0.000 title claims abstract description 60
- 238000002360 preparation method Methods 0.000 title abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 239000003446 ligand Substances 0.000 claims abstract description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 4
- 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 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims description 2
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 2
- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 claims description 2
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 2
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 2
- 125000006752 (C6-C60) arylthio group Chemical group 0.000 claims description 2
- 229940126062 Compound A Drugs 0.000 claims description 2
- 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 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- LNJXVUXPFZKMNF-UHFFFAOYSA-K iridium(3+);trichloride;trihydrate Chemical compound O.O.O.Cl[Ir](Cl)Cl LNJXVUXPFZKMNF-UHFFFAOYSA-K 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000463 material Substances 0.000 abstract description 25
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000010410 layer Substances 0.000 description 20
- 229910052799 carbon Inorganic materials 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 229910052760 oxygen Inorganic materials 0.000 description 14
- 239000000047 product Substances 0.000 description 10
- MFELLNQJMHCAKI-UHFFFAOYSA-N 3,7-diethylnonane-4,6-dione Chemical compound CCC(CC)C(=O)CC(=O)C(CC)CC MFELLNQJMHCAKI-UHFFFAOYSA-N 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- 239000011259 mixed solution Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- 239000008213 purified water Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 238000005303 weighing Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 6
- 238000000967 suction filtration Methods 0.000 description 6
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000126 substance Substances 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
- 230000008021 deposition Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical group [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000985284 Leuciscus idus Species 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine 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
- 230000007547 defect Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
-
- 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
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- 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]
- H10K50/17—Carrier injection layers
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- 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]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
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- 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]
- H10K50/18—Carrier blocking 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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- 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
- 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)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
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- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to the technical field of red light luminescent materials, and particularly discloses an organic iridium metal complex and a preparation method and application thereof, wherein the organic iridium metal complex has the following structure:
Description
Technical Field
The invention relates to the technical field of red light luminescent materials, in particular to an organic iridium metal complex with a diketone compound as an auxiliary ligand, a preparation method thereof and application of the complex in an organic electroluminescent device.
Background
With the development of science and technology, organic electrophosphorescent materials have become hot spots in the field of electroluminescent research in recent years, because organic electrophosphorescent materials can simultaneously utilize singlet excitons and triplet excitons, and the luminous quantum efficiency of the organic electrophosphorescent materials can theoretically reach 100%. Meanwhile, the iridium complex is also the most interesting electrophosphorescent material due to the advantages of high photoluminescence efficiency, short excited state life, capability of obtaining red, green and blue three-primary-color luminescence and the like.
Therefore, the prior art is still to be improved and developed, and a compound with good thermal stability and high luminous efficiency is designed and searched to be used as a red light emitting material, so as to overcome the defects of the existing red light emitting material in the practical application process, and the red light emitting material is the key point of research work and the future development trend of O L ED (organic light emitting diode) materials.
Disclosure of Invention
The invention aims to provide an organic iridium metal complex, a preparation method thereof and an organic electroluminescent device using the complex, so as to solve the problems in the background technology.
In order to achieve the purpose, the invention provides the following technical scheme:
an organic iridium metal complex has a structure shown as a formula I:
R1、R2、R3、R4And R5Independently selected from one of hydrogen, deuterium, halogen, cyano, mercapto, carbonyl, carboxyl, nitro, hydroxyl, C1-C60 alkyl, C6-C60 aryl, C3-C60 aromatic heterocyclic group, adamantyl, C2-C60 alkynyl, C1-C60 alkoxy, C1-C60 alkylamino, C6-C60 arylamino, C6-C60 aryloxy and C6-C60 arylthio;
and R is1-R5And other substituents on the ring or other adjacent rings mutually form a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C60 aromatic ring, a substituted or unsubstituted C2-C60 aromatic heterocyclic ring, a substituted or unsubstituted C6-C60 fused ring or a substituted or unsubstituted C5-C60 spiro ring.
As a further scheme of the invention: r1、R2、R3、R4And R5May be further substituted with hydrogen, halogen, deuterium, cyano, hydroxy, mercapto, deuterated benzene, C1-C20 alkyl, or C1-C30 alkoxy;
understandably, R1-R5Independently preferred is one of halogen, cyano, carbonyl, C1-C30 alkyl, C6-C30 aryl, C3-C30 aromatic heterocyclyl, C1-C30 alkoxy, C1-C30 alkylamino, C6-C30 arylamino and C6-C30 aryloxy.
As a still further scheme of the invention: the R is1、R2、R3、R4And R5Independently selected from one of fluoro, deuterium, cyano, trifluoromethyl, methyl, hexyl, propyl, isopropyl, butyl, tert-butyl, pentyl, methoxy, phenyl and deuterated phenyl.
As a still further scheme of the invention: the R is1In an amount of 0 to 4, R2The number of (2) is 0-2.
As a still further scheme of the invention: the alkyl is straight-chain alkyl, branched-chain alkyl or cycloalkyl; the alkyl can be further substituted by one or more of halogen, deuterium, cyano, hydroxyl and sulfydryl, the number of the substitution is at least 1, and the halogen comprises fluorine, chlorine, bromine and iodine.
As a still further scheme of the invention: the organic iridium metal complex (namely, the organic luminescent material iridium metal complex) is selected from any one of the following structures:
the preparation method of the organic iridium metal complex comprises the following steps:
1) providing compound a and compound C, respectively, represented by the following structural formulae:
2) under the protection of nitrogen, compound A is mixed with iridium trichloride trihydrate (IrCl)3·3H2O) is mixed according to the molar ratio of 3:1 and then is added into the mixed solvent of ethylene glycol ethyl ether and water for heating reaction to generate a bridging ligand B, wherein the structure of the bridging ligand B is as follows:
3) mixing the bridged ligand B obtained in the step 2) with a compound C, adding ethylene glycol ethyl ether and potassium carbonate, and stirring for 24 hours under the protection of nitrogen at 120 ℃ to fully react to obtain the organic iridium metal complex shown in the formula I.
Specifically, the synthetic route of the steps 1) to 3) is as follows:
further, the organic iridium metal complex is applied to the preparation of organic electroluminescent device products, that is, the invention also provides an organic electroluminescent device containing the organic iridium metal complex shown in the formula I, wherein the organic electroluminescent device comprises:
the iridium complex comprises a first electrode, a second electrode and an organic layer arranged between the first electrode and the second electrode, wherein the organic layer contains the iridium metal complex shown in the chemical formula I; the iridium metal complex shown in the formula I can exist in an organic layer in a single form or in a mixture with other substances.
Further, the organic layer at least comprises one or more of a hole injection layer, a hole transport layer, a layer having both hole injection and hole transport technologies, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a layer having both electron transport and electron injection technologies.
Further, the organic electroluminescent device comprises at least one functional layer containing the iridium metal complex shown in the formula I.
Further, the organic electroluminescent device comprises a light-emitting layer, wherein the light-emitting layer contains an iridium metal complex shown in a formula I; preferably, the light-emitting layer of the organic electroluminescent device comprises a host material and a doping material, wherein the doping material is an iridium metal complex shown in formula I, and further preferably, the mixing ratio of the host material to the doping material of the light-emitting layer is 90:10-99.5: 0.5.
Further, the device of the present invention may be used for an organic light emitting device, an organic solar cell, electronic paper, an organic photoreceptor, or an organic thin film transistor.
Compared with the prior art, the invention has the beneficial effects that:
1. the organic iridium metal complex with the novel structure provided by the invention can adjust the wavelength of the compound by selecting the combination of the specific heterocyclic ligand, and the obtained organic metal compound can improve the luminous efficiency and the brightness of the device after being used in an organic electroluminescent device, and the organic iridium metal complex uses a compound Ir (bty)2Compared with an organic electroluminescent device prepared by using acac as a luminescent layer doping material, the organic electroluminescent device has the advantages that the driving voltage is obviously reduced, and the current efficiency, the power efficiency and the brightness are obviously improved.
2. The preparation method of the organic iridium metal complex provided by the invention has the characteristics of simple synthesis steps, simple post-treatment and high product purity, and solves the problems of low luminous efficiency and pending improvement of thermal stability of the existing red light luminescent material.
Detailed Description
The technical solution of the present invention will be described in further detail with reference to specific embodiments.
Example 1
An organic iridium metal complex C001, which comprises the following specific steps:
1) under nitrogenAs a protective gas system, A1(90.4mmo1, 20g) and IrCl were accurately weighed3·3H2O (30.13mmo1, 10.6g) is put into a reaction system, then a mixed solution of purified water (133m L) and ethylene glycol ethyl ether (400m L) is added, nitrogen is continuously introduced until reflux reaction is carried out for 24 hours, the system is cooled to room temperature after the reaction is stopped, a large amount of precipitate is separated out, the precipitate is filtered by suction, and water, absolute ethyl alcohol and petroleum ether are sequentially washed and dried to obtain a bridge-linked ligand B1(14g, the yield is 69.5%) in an orange-red powder shape;
2) the bridging ligand B1(10.5mmol, 14g) was weighed, 6.7g of the ligand C (3, 7-diethyl-4, 6-nonanedione) was added, ethylene glycol ethyl ether 400m L and potassium carbonate (14.5g) were added to the system, stirring was carried out at 120 ℃ for 24 hours under nitrogen protection, suction filtration, alcohol washing, drying, column chromatography (dichloromethane) was carried out, and the filtrate was concentrated to precipitate a solid, thereby finally obtaining a red compound C001(8.5g, 48% yield).
The compound C001 was analyzed, and the specific results were as follows:
the purity of HP L C is more than 99%.
Mass spectrum: calculated value 844; the test value was 844.3.
Elemental analysis:
the calculated values are: 58.34 percent of C; 5.14 percent of H; 9.96 percent of N; 3.79 percent of O; 22.77 percent of Ir;
the test values are: 58.36 percent of C; 5.15 percent of H; 9.98 percent of N; 3.80 percent of O; 22.78 percent of Ir.
Specifically, the reaction formulae of steps 1) to 2) are as follows:
in the embodiment, the organic iridium metal complex is applied to preparation of an organic electroluminescent device product.
Example 2
An organic iridium metal complex C005 comprises the following specific synthetic steps:
1) accurately weighing A5(84.3mmo1, 20g) and IrCl in a system with nitrogen as protective gas3·3H2O (28mmo1, 9.9g) was put into the reaction systemAdding a mixed solution of purified water (133m L) and ethylene glycol ethyl ether (400m L), continuously introducing nitrogen to reflux reaction for 24 hours, cooling the system to room temperature after the reaction is stopped, separating out a large amount of precipitates, carrying out suction filtration on the precipitates, washing and drying the precipitates with water, absolute ethyl alcohol and petroleum ether in sequence to obtain orange red powdery bridging ligand B5(14g, the yield is 71%);
2) weighing bridging ligand B5(10mmol, 14g), adding ligand C (3, 7-diethyl-4, 6-nonanedione) 6.4g, adding ethylene glycol ethyl ether 400m L and potassium carbonate (13.8g) into the system, stirring at 120 ℃ for 24 hours under the protection of nitrogen, performing suction filtration, washing with alcohol, drying, performing column chromatography (dichloromethane), and concentrating the filtrate until solid is separated out to finally obtain red compound C005(9g, 51% yield).
The compound C005 was analyzed, and the specific results were as follows:
the purity of HP L C is more than 99%.
Mass spectrum: calculated value 876; the test value was 876.2.
Elemental analysis:
the calculated values are: 56.21 percent of C; 4.95 percent of H; 9.59 percent of N; 7.31 percent of O; 21.94 percent of Ir;
the test values are: 56.23 percent of C; 4.96 percent of H; 9.61 percent of N; 7.30 percent of O; 21.95 percent of Ir.
Specifically, the reaction formulae of steps 1) to 2) are as follows:
in the embodiment, the organic iridium metal complex is applied to preparation of an organic electroluminescent device product.
Example 3
The organic iridium metal complex C020 comprises the following specific synthetic steps:
1) accurately weighing A20(84.3mmo1, 20g) and IrCl in a system with nitrogen as protective gas3·3H2O (28mmo1, 9.9g) is put into the reaction system, then the mixed solution of purified water (133m L) and ethylene glycol ethyl ether (400m L) is added, nitrogen is continuously introduced until the reflux reaction is carried out for 24 hours, and after the reaction is stoppedCooling the system to room temperature, precipitating a large amount of precipitate, carrying out suction filtration on the precipitate, and washing and drying the precipitate with water, absolute ethyl alcohol and petroleum ether in sequence to obtain an orange red powdery bridging ligand B20(14g, with the yield of 71%);
2) the bridged ligand B20(11mmol, 15g) is weighed, 6.4g of the ligand C (3, 7-diethyl-4, 6-nonanedione) is added, then ethylene glycol ethyl ether 400m L and potassium carbonate (13.8g) are added into the system, the mixture is stirred for 24 hours at 120 ℃ under the protection of nitrogen, the mixture is filtered, washed with alcohol, dried, subjected to column chromatography (dichloromethane), and concentrated and solid is separated out from the filtrate to obtain the final red compound C020(11g, yield 63%).
The compound C020 is detected and analyzed, and the specific results are as follows:
the purity of HP L C is more than 99%.
Mass spectrum: calculated value 876.03; the test value was 876.29.
Elemental analysis:
the calculated values are: 56.21 percent of C; 4.95 percent of H; 9.59 percent of N; 7.31 percent of O; 21.94 percent of Ir;
the test values are: 56.23 percent of C; 4.96 percent of H; 9.61 percent of N; 7.31 percent of O; 21.95 percent of Ir.
Specifically, the reaction formulae of steps 1) to 2) are as follows:
in the embodiment, the organic iridium metal complex is applied to preparation of an organic electroluminescent device product.
Example 4
The organic iridium metal complex C027 comprises the following specific synthesis steps:
1) accurately weighing A27(72.7mmo1, 20g) and IrCl in a system with nitrogen as a protective gas3·3H2O (24.2mmo1, 8.5g) is put into a reaction system, then a mixed solution of purified water (133m L) and ethylene glycol ethyl ether (400m L) is added, nitrogen is continuously introduced until reflux reaction is carried out for 24 hours, the system is cooled to room temperature after the reaction is stopped, a large amount of precipitate is separated out, the precipitate is filtered by suction, and water, absolute ethyl alcohol and petroleum ether are sequentially washed and dried to obtain the orange red tonerThe powdered bridging ligand B27(12g, 64% yield);
2) intermediate compound B27(7.73mmol, 12g) was weighed, ligand C, i.e., 3, 7-diethyl-4, 6-nonanedione (4.9g) was added, ethylene glycol ethyl ether 400m L and potassium carbonate (10.7g) were added to the system, and the mixture was stirred at 120 ℃ for 24 hours under nitrogen protection, filtered, washed with alcohol, dried, and subjected to column chromatography (dichloromethane), and the filtrate was concentrated to precipitate a solid, to obtain final red compound C027(9g, yield 61%).
Compound C027 was assayed with the following results:
the purity of HP L C is more than 99%.
Mass spectrum: calculated value 951.97; the test value was 952.25.
Elemental analysis:
the calculated values are: 51.73 percent of C; h, 3.92 percent; 8.83 percent of N; 3.36 percent of O; 20.19 percent of Ir; 11.97 percent of F;
the test values are: 51.74 percent of C; h, 3.94 percent; 8.82 percent of N; 3.36 percent of O; 20.18 percent of Ir; f, 11.99 percent.
Specifically, the reaction formulae of steps 1) to 2) are as follows:
in the embodiment, the organic iridium metal complex is applied to preparation of an organic electroluminescent device product.
Example 5
An organic iridium metal complex C028 is synthesized by the following steps:
1) accurately weighing A28(86.1mmo1, 20g) and IrCl in a system with nitrogen as a protective gas3·3H2O (28.7mmo1, 10.12g) is put into a reaction system, then a mixed solution of purified water (133m L) and ethylene glycol ethyl ether (400m L) is added, nitrogen is continuously introduced until reflux reaction is carried out for 24 hours, the system is cooled to room temperature after the reaction is stopped, a large amount of precipitate is separated out, the precipitate is filtered by suction, and water, absolute ethyl alcohol and petroleum ether are sequentially washed and dried to obtain a bridge-linked ligand B28(15.5g, the yield is 78%) in an orange-red powder shape;
2) intermediate compound B28(11.2mmol, 15.5g) was weighed, ligand C, i.e., 3, 7-diethyl-4, 6-nonanedione (7.1g) was added, ethylene glycol ethyl ether 400m L and potassium carbonate (15.5g) were added to the system, and the mixture was stirred at 120 ℃ for 24 hours under nitrogen protection, filtered, washed with alcohol, dried, subjected to column chromatography (dichloromethane), and the filtrate was concentrated to precipitate a solid, to obtain final red compound C028(12g, yield 61%).
The compound C028 is detected and analyzed, and the specific results are as follows:
the purity of HP L C is more than 99%.
Mass spectrum: the calculated value is 866; the test value was 866.26.
Elemental analysis:
the calculated values are: 58.86 percent of C; 4.31 percent of H; 12.94 percent of N; 3.70 percent of O; 22.20 percent of Ir;
the test values are: 58.57 percent of C; 4.32 percent of H; 12.95 percent of N; 3.71 percent of O; 22.22 percent of Ir.
Specifically, the reaction formulae of steps 1) to 2) are as follows:
in the embodiment, the organic iridium metal complex is applied to preparation of an organic electroluminescent device product.
Example 6
An organic iridium metal complex C046 comprises the following specific synthetic steps:
1) accurately weighing A46(70.6mmo1, 20g) and IrCl in a system with nitrogen as a protective gas3·3H2Adding O (23.5mmo1, 8.3g) into a reaction system, adding a mixed solution of purified water (133m L) and ethylene glycol ethyl ether (400m L), continuously introducing nitrogen to reflux reaction for 24 hours, cooling the system to room temperature after the reaction is stopped, precipitating a large amount of precipitate, carrying out suction filtration on the precipitate, and washing and drying the precipitate by using water, absolute ethyl alcohol and petroleum ether in sequence to obtain a bridge-linked ligand B46(13g, the yield is 69.7%) in an orange-red powder shape;
2) intermediate compound B46(8.2mmol, 13g) was weighed, ligand C, i.e., 3, 7-diethyl-4, 6-nonanedione (5.2g) was added, ethylene glycol ethyl ether 400m L and potassium carbonate (11.3g) were added to the system, and the mixture was stirred at 120 ℃ for 24 hours under nitrogen protection, filtered, washed with alcohol, dried, and subjected to column chromatography (dichloromethane), and the filtrate was concentrated to precipitate a solid, to obtain final red compound C046(10g, yield 63%).
The compound C046 is detected and analyzed, and the specific results are as follows:
the purity of HP L C is more than 99%.
Mass spectrum: calculated value 968.17; the test value was 968.33.
Elemental analysis:
the calculated values are: 63.27 percent of C; 4.89 percent of H; 8.68 percent of N; 3.31 percent of O; 19.85 percent of Ir;
the test values are: 63.28 percent of C; 4.90 percent of H; 8.67 percent of N; 3.32 percent of O; 19.86 percent of Ir.
Specifically, the reaction formulae of steps 1) to 2) are as follows:
in the embodiment, the organic iridium metal complex is applied to preparation of an organic electroluminescent device product.
Example 7
An organic iridium metal complex C165 comprises the following specific synthetic steps:
1) accurately weighing A165(70.6mmo1, 20g) and IrCl in a system with nitrogen as a protective gas3·3H2O (23.5mmo1, 8.3g) is put into a reaction system, then a mixed solution of purified water (133m L) and ethylene glycol ethyl ether (400m L) is added, nitrogen is continuously introduced until reflux reaction is carried out for 24 hours, the system is cooled to room temperature after the reaction is stopped, a large amount of precipitate is separated out, the precipitate is filtered by suction, and water, absolute ethyl alcohol and petroleum ether are sequentially washed and dried to obtain a bridge-linked ligand B165(12g, the yield is 64%) in an orange-red powder shape;
2) intermediate compound B165(7.6mmol, 12g) was weighed, ligand C, i.e., 3, 7-diethyl-4, 6-nonanedione (2.9g) was added, ethylene glycol ethyl ether 400m L and potassium carbonate (10.5g) were added to the system, stirring was carried out at 120 ℃ for 24 hours under nitrogen protection, suction filtration, alcohol washing, drying, column chromatography (dichloromethane) was carried out, and the filtrate was concentrated to precipitate a solid, to obtain final red compound C165(10g, yield 74%).
The compound C165 was analyzed, and the specific results were as follows:
the purity of HP L C is more than 99%.
Mass spectrum: calculated value was 884; the test value was 884.24.
Elemental analysis:
the calculated values are: 61.14 percent of C; 3.99 percent of H; 9.51 percent of N; 3.62 percent of O; 21.74 percent of Ir;
the test values are: 61.16 percent of C; 4.01 percent of H; 9.52 percent of N; 3.63 percent of O; 21.75 percent of Ir.
Specifically, the reaction formulae of steps 1) to 2) are as follows:
in the embodiment, the organic iridium metal complex is applied to preparation of an organic electroluminescent device product.
The invention also provides an organic electroluminescent device which is prepared from the organic iridium metal complex.
Example 8
An organic electroluminescent device was prepared using compound C001 prepared in example 1, which is more specifically:
coating with a thickness of
The 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, the substrate was ultrasonically washed in sequence with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a plasma cleaning machine, washed for 5 minutes, and sent to a deposition machine for deposition. Firstly, the upper surface of ITO (anode) is evaporated with CuPc
Followed by deposition of NPB
The host substance 4,4 '-N, N' -biphenyl dicarbazole (CBP) and the doping substance compound C001 are mixed and evaporated according to the weight ratio of 95:5
Evaporated electron transport layer Alq3
Vapor deposition of an electron-injecting layer L iF
Deposition cathode Al
And testing the performance of the obtained device by adopting a KEITH L EY 2400 type source measuring unit and a CS-2000 spectral radiance luminance meter to evaluate the driving voltage, the luminance and the luminous efficiency.
Referring to the above method, the organic electroluminescent device of the corresponding compound was prepared by replacing compound C001 with C005, C020, C027, C028, C046, and C165, respectively.
Comparative example 1
An organic electroluminescent device was prepared in the same manner as in example 8, and the structure of the light-emitting layer-doped compound was as follows:
the same examination as in example 8 was performed on the prepared organic electroluminescent device, and the results are shown in table 1.
Table 1 test results of organic electroluminescent devices in example 8 and comparative example 1
As can be seen from Table 1, the compounds are compared with the useThe material Ir (bty)2Compared with an organic electroluminescent device prepared by using acac as a luminescent layer doping material, the organic electroluminescent device prepared by using the iridium metal complex provided by the invention as the luminescent layer doping material has the advantages that the driving voltage is lower, the stability is favorably improved, the current efficiency is obviously improved, the power efficiency is obviously improved, and the brightness is obviously improved.
The organic iridium metal complex with the novel structure has the beneficial effects that the specific heterocyclic ligand combination is selected, the wavelength of the compound can be adjusted, the obtained organic metal compound is used for an organic electroluminescent device, the luminous efficiency and the brightness of the device are improved, and the organic iridium metal complex with the novel structure is combined with a compound Ir (bty)2Compared with an organic electroluminescent device prepared by using acac as a luminescent layer doping material, the organic electroluminescent device prepared by using acac as a luminescent layer doping material has the advantages that the driving voltage is obviously reduced, the stability is favorably improved, the current efficiency, the power efficiency and the brightness are obviously improved, in addition, the preparation method of the organic iridium metal complex provided by the invention has the characteristics of simple synthesis step, simple post-treatment and high product purity, the prepared organic electroluminescent device has higher luminous efficiency and service life, the problems of low luminous efficiency and to-be-improved thermal stability of the existing red light luminescent material are solved, and the organic electroluminescent device has wide market prospect.
While the preferred embodiments of the present invention have been described in detail, the present invention is not limited to the above embodiments, and various changes can be made without departing from the spirit of the present invention within the knowledge of those skilled in the art. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications of the invention may be made without departing from the scope of the invention.
Claims (7)
1. An organic iridium metal complex has a structure shown as a formula I:
R1、R2、R3、R4And R5Independently selected from one of hydrogen, deuterium, halogen, cyano, mercapto, carbonyl, carboxyl, nitro, hydroxyl, C1-C60 alkyl, C6-C60 aryl, C3-C60 aromatic heterocyclic group, adamantyl, C2-C60 alkynyl, C1-C60 alkoxy, C1-C60 alkylamino, C6-C60 arylamino, C6-C60 aryloxy and C6-C60 arylthio;
and R is1-R5And other substituents on the ring or other substituents on other adjacent rings mutually form one of a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C60 aromatic ring, a substituted or unsubstituted C2-C60 aromatic heterocyclic ring, a substituted or unsubstituted C6-C60 condensed ring and a substituted or unsubstituted C5-C60 spiral ring.
2. The organic iridium metal complex of claim 1 wherein R is1、R2、R3、R4And R5Independently selected from one of fluoro, deuterium, cyano, trifluoromethyl, methyl, hexyl, propyl, isopropyl, butyl, tert-butyl, pentyl, methoxy, phenyl and deuterated phenyl.
3. The organic iridium metal complex according to claim 1 or 2, wherein R is1In an amount of 0 to 4, R2The number of (2) is 0-2.
4. The organic iridium metal complex of claim 3, wherein the organic iridium metal complex is selected from any one of the following structures:
5. a method for producing the organic iridium metal complex as claimed in any one of claims 1 to 4, comprising the steps of:
1) providing compound a and compound C, respectively, represented by the following structural formulae:
2) under the protection of nitrogen, mixing a compound A and iridium trichloride trihydrate according to a molar ratio of 3:1, adding the mixture into a mixed solvent of ethylene glycol ethyl ether and water, and carrying out heating reaction to generate a bridged ligand B, wherein the bridged ligand B has a structure as follows:
3) mixing the bridged ligand B obtained in the step 2) with a compound C, adding ethylene glycol ethyl ether and potassium carbonate, and stirring at 120 ℃ for 24 hours under the protection of nitrogen to obtain the organic iridium metal complex.
6. An organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode, the organic layer comprising the organic iridium metal complex as claimed in any one of claims 1 to 4.
7. Use of the organic electroluminescent device as claimed in claim 6 for the production of organic solar cells, electronic paper, organophotoreceptors and organic thin film transistors.
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| CN113402563A (en) * | 2021-06-16 | 2021-09-17 | 吉林奥来德光电材料股份有限公司 | Iridium complex, preparation method thereof, organic electroluminescent device and display device |
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