CN111471071A - Iridium metal complex, preparation method thereof and organic electroluminescent device - Google Patents
Iridium metal complex, preparation method thereof and organic electroluminescent device Download PDFInfo
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 48
- -1 Iridium metal complex Chemical class 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 239000003446 ligand Substances 0.000 claims abstract description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 3
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 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 2
- 239000002994 raw material Substances 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 4
- 150000002736 metal compounds Chemical class 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 238000005406 washing Methods 0.000 description 12
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 238000001035 drying Methods 0.000 description 9
- 238000000967 suction filtration Methods 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 7
- 238000005303 weighing Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 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
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 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 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 241000985284 Leuciscus idus Species 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 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
- 230000008021 deposition Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
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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)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses an iridium metal complex, a preparation method thereof and an organic electroluminescent device, wherein the iridium metal complex has the following structural formula:
Description
Technical Field
The invention relates to the field of organic photoelectric materials, in particular to an iridium metal complex, a preparation method thereof and an organic electroluminescent device.
Background
The organic electroluminescence technology is a latest generation flat panel display technology, and can be used for flat panel displays and illumination light sources, and currently, commercial flat panel displays are put into the market, and the illumination light sources are rapidly industrialized due to their own absolute advantages. The electroluminescent device has an all-solid-state structure, organic electroluminescent materials are the core and the foundation of the device, and the development of new materials is the source power 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 phosphorescence luminescent phenomenon is always favored since the discovery, because the luminescent efficiency of the phosphorescence material is obviously higher than the luminescent efficiency of the fluorescence, theoretically reaching 100 percent of the luminescent efficiency, many scientific research institutions are increasing the research and development of the phosphorescence material and trying to accelerate the industrialized development through the phosphorescence material; however, the phosphor material has high synthesis cost, high synthesis process requirements, high purification requirements and low efficiency, and easily pollutes the environment in the synthesis process.
Disclosure of Invention
The iridium metal complex with a novel structure provided by the invention adjusts the wavelength of the compound by selecting the combination of specific heterocyclic ligands, so that the luminous efficiency of the device is improved after the obtained organic metal compound is used in an organic electroluminescent device.
In order to achieve the purpose, the invention provides the following technical scheme:
an iridium metal complex having a structural formula shown in chemical formula 1:
R1、R2、R3、R4、R5、R6and R7Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C4-C12 aromatic heterocyclic group, or substituted or unsubstituted C8-C16 condensed ring group, R4Is an alkane, R5、R6Is methyl.
As a further scheme of the invention: r1、R2、R3The substitution position is any position of the ring; r1The number of the substituents is 0-3, R2The number of substituents is 0-4, R3The number of the substituents is 0 to 4.
As a still further scheme of the invention: the alkyl is straight-chain alkyl, branched-chain alkyl, cycloalkyl, straight-chain alkyl substituted by at least 1 substituent, branched-chain alkyl substituted by at least 1 substituent or cycloalkyl substituted by at least 1 substituent; wherein, the substituent is one or more of halogen, deuterium, cyano, hydroxyl and sulfydryl independently.
As a still further scheme of the invention: the aryl group is preferably an unsubstituted aryl group or an aryl group substituted with at least 1 substituent; wherein the substituents are independently selected from halogen, deuterium, amino, cyano, nitro, hydroxy or mercapto.
As a still further scheme of the invention: the aromatic heterocyclic group is preferably an unsubstituted heteroaryl group or an aromatic heterocyclic group substituted with at least 1 substituent; wherein the heteroatom in the heteroaryl group is nitrogen, sulfur or oxygen; the substituents are independently selected from halogen, deuterium, amino, cyano, nitro, hydroxyl or mercapto;
R1、R2、R3independently form a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C60 aromatic ring with other substituents on the ringA substituted C2-C60 heteroaromatic ring, a substituted or unsubstituted C6-C60 fused ring, or a substituted or unsubstituted C5-C60 spirocyclic ring;
or R1、R2、R3Form a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C60 aromatic ring, a substituted or unsubstituted C2-C60 aromatic heterocycle, a substituted or unsubstituted C6-C60 fused ring, or a substituted or unsubstituted C5-C60 spiro ring;
the substituent on the substituent group is at least one selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C4-C12 aromatic heterocyclic group, substituted or unsubstituted C8-C16 condensed ring group and substituted or unsubstituted C5-C60 spiral ring.
In the above-described aspect, it is most preferable that the iridium metal complex is selected from any one of the following structures.
Some specific structural forms are listed above, but the series of compounds are not limited to the above molecular structures, and other specific molecular structures can be obtained through simple transformation of the groups and the substituted groups and substituted positions thereof, which is not described in detail herein.
The preparation method of the iridium metal complex comprises the following steps:
1) providing compound a and compound C, respectively, represented by the following structural formulae:
wherein R is1、R2、R3、R4、R5、R6And the number of substituents of each thereof is in accordance with the range defined in chemical formula 1;
2) fully reacting the raw material A with iridium trichloride to prepare a bridging ligand intermediate B;
3) and fully reacting the intermediate B with the intermediate C to obtain the iridium metal complex shown in the chemical formula 1.
As a still further scheme of the invention: the structure of bridging ligand intermediate B is:
the synthetic route is as follows:
wherein: r1、R2、R3、R4、R5、R6And the number of substituents of each thereof is in accordance with the range defined in chemical formula 1.
An organic electroluminescent device comprises the iridium metal complex, a first electrode, a second electrode and an organic layer arranged between the two electrodes, wherein the organic layer comprises the iridium metal complex shown in the chemical formula 1; the iridium metal complex of chemical formula 1 of the present invention may be present in the organic material layer in a single form or in a mixture with other materials.
The organic layer at least comprises one or more of a hole injection layer, a hole transport layer, a layer with hole injection and hole transport functions, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a layer with electron transport and electron injection functions.
The organic electroluminescent device comprises at least one functional layer containing an iridium metal complex represented by chemical formula 1 of the present invention.
The organic electroluminescent device includes a light emitting layer containing an iridium metal complex represented by chemical formula 1 of the present invention. Preferably, the light emitting layer of the organic electroluminescent device includes a host material and a dopant material, and the dopant material is an iridium metal complex represented by chemical formula 1 of the present invention. Further preferably, the mixing ratio of the host material and the doping material of the light-emitting layer is 90:10-99.5: 0.5.
The device of the invention can 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: the iridium metal complex with the novel structure provided by the invention has the advantages that the specific heterocyclic ligand combination is selected, the wavelength of the compound is adjusted, and the obtained organic metal compound is used for an organic electroluminescent device, so that the luminous efficiency and the brightness of the device are improved.
Detailed Description
The technical solutions of the present invention will be described in further detail with reference to specific embodiments, and it should be apparent 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
An iridium metal complex L001, namely a compound with the number of 001, comprises the following specific synthetic steps:
1) weighing A-001(63mol, 20g) and IrCl under the protection of nitrogen3·3H2O21mmo1 (namely 7.4 is put into a reaction system, a mixed solution of 600m L ethylene glycol ethyl ether and 200m L pure water is added, the mixture is refluxed for 24 hours under the protection of nitrogen, then cooled to room temperature, precipitates are separated out, the precipitates are filtered, and water, absolute ethyl alcohol and petroleum ether are used for washing and drying in sequence to obtain a red powder bridging ligand B-001(9g, the yield is 50%);
2) weighing intermediate B-0015.23ol (9 g), adding ligand 3, 7-diethyl-4, 6-nonanedione C-001(3.3), adding ethylene glycol ethyl ether 200m L and potassium carbonate (8g) into the system, stirring at 120 ℃ for 24 hours under the protection of nitrogen, performing suction filtration, washing with alcohol, drying, using dichloromethane as a solvent, performing silica gel column chromatography, concentrating the filtrate, and precipitating a solid to obtain a final red compound L001 (3.4g, yield 31);
the purity of HP L C is more than 99.5%;
mass spectrum calculated 1036.54; test value 1036.50; .
Elemental analysis calculated C: 63.73%; 6.52 percent of H; 2.70 percent of N; 3.09 percent of O; 18.54 percent of Ir; 5.42 of Si; the test value is C: 63.70%; 6.50 percent of H; 2.75 percent of N; 3.10 percent of O; 18.50 percent of Ir; 5.40 of Si.
Specifically, the reaction formulae of steps 1) to 2) are as follows:
in the embodiment, the iridium metal complex is applied to preparation of organic electroluminescent device products.
Example 2
An iridium metal complex L008, namely a compound with the number of 008, comprises the following specific synthetic steps:
1) a-008(69mmol, 20g) and IrCl were weighed under a nitrogen protection system3·3H2Placing O23mmo1 (namely 8.1g) into a reaction system, adding a mixed solution of 600m L ethylene glycol ethyl ether and 200m L purified water, refluxing for 24 hours under the protection of nitrogen, cooling to room temperature, separating out a precipitate, performing suction filtration on the precipitate, and sequentially washing and drying with water, absolute ethyl alcohol and petroleum ether to obtain bridging ligand B-008(9.6g, the yield is 52%) of red powder;
2) intermediate B-0085.97mmol (9.6 g) was weighed, ligand 3, 7-diethyl-4, 6-nonanedione C-005(3.8g) was added, ethylene glycol ethyl ether 200m L and potassium carbonate (8.5g) were added to the system, the mixture was stirred at 120 ℃ for 24 hours under nitrogen protection, filtered, washed with alcohol, dried, dichloromethane was used as a solvent, silica gel column chromatography was performed, and the filtrate was concentrated to precipitate a solid, to obtain final red compound L008 (3.7g, yield 32%).
The purity of HP L C is more than 99.5%.
Mass spectrum calculated 980.43; the test value was 980.40.
Elemental analysis, calculated value C is 62.48 percent; 6.07 percent of H; 2.86 percent of N; 3.26 percent of O; 19.61 percent of Ir; 5.73 percent of Si; the test value is 62.5 percent of C; 6.1 percent of H; 2.90 percent of N; 3.28 percent of O; 19.60 percent of Ir; 5.70 percent of Si.
Specifically, the reaction formulae of steps 1) to 2) are as follows:
in the embodiment, the iridium metal complex is applied to preparation of organic electroluminescent device products.
Example 3
An iridium metal complex L017, namely a compound numbered 017, is prepared by the following specific synthesis steps:
1) weighing A-017(57.9mmol, 20g IrCl) under the protection of nitrogen3·3H2Placing O19.3mmo1 (namely 6.8g) into a reaction system, adding a mixed solution of 600m L ethylene glycol ethyl ether and 200m L purified water, refluxing for 24 hours under the protection of nitrogen, cooling to room temperature, separating out a precipitate, performing suction filtration on the precipitate, and washing and drying with water, absolute ethyl alcohol and petroleum ether in sequence to obtain a red powdered bridging ligand B-017(9.9g, the yield is 56%);
2) weighing intermediate B-0175.4mmol (9.9 g), adding ligand acetylacetone C-01716.2mmol (1.6g), adding ethylene glycol ethyl ether 200m L and potassium carbonate (7.8g) into the system, stirring for 24 hours at 120 ℃ under the protection of nitrogen, performing suction filtration, alcohol washing, petroleum ether washing, drying, using dichloromethane as a solvent, performing silica gel column chromatography, and concentrating and separating solid from filtrate to obtain a final red compound L017 (4g, yield 38%);
the purity of HP L C is more than 99.5%;
mass spectrum calculated 866.10; test value 866.20;
elemental analysis, calculated value C is 62.48 percent; 6.07 percent of H; 2.86 percent of N; 3.26 percent of O; 19.61 percent of Ir; 5.73 percent of Si; the test value is C: 62.50%; 6.10 percent of H; 2.85 percent of N; 3.30 percent of O; 19.60 percent of Ir; 5.70 percent of Si.
Specifically, the reaction formulae of steps 1) to 2) are as follows:
in the embodiment, the iridium metal complex is applied to preparation of organic electroluminescent device products.
Example 4
An iridium metal complex L055, namely a compound numbered 055, comprises the following specific synthetic steps:
1) weighing A-055(63.0mmol, 20g), IrCl3·3H2O21mmo1 (7.4 g) is put into a reaction system, a mixed solution of 600m L ethylene glycol ethyl ether and 200m L pure water is added, and nitrogen protection is carried outRefluxing for 24 hours, then cooling to room temperature, separating out a precipitate, carrying out suction filtration on the precipitate, and sequentially washing and drying with water, absolute ethyl alcohol and petroleum ether to obtain a red powdered bridging ligand B-055(9g, the yield is 50%);
2) weighing intermediate B-0555.23mmol (9 g), adding ligand C-05515.7mmol (2.5g), adding ethylene glycol ethyl ether 180m L and potassium carbonate (7.8g), stirring at 120 ℃ for 24 hours under the protection of nitrogen, performing suction filtration, performing alcohol washing, performing petroleum ether washing, drying, using dichloromethane as a solvent, performing silica gel column chromatography, and concentrating the filtrate to separate out solid to obtain final red compound L055 (3.7g, 36% yield).
Specifically, the reaction formulae of steps 1) to 2) are as follows:
in the embodiment, the iridium metal complex is applied to preparation of organic electroluminescent device products.
Example 5
An iridium metal complex L089, namely a compound with the number of 089, comprises the following specific synthetic steps:
1) a-089(57.9mmol, 20g), Cl, was weighed out under nitrogen protection3·3H2Placing O19.3mmo1 (6.8 g) into a reaction system, adding a mixed solution of 600m L ethylene glycol ethyl ether and 200m L purified water, refluxing for 24 hours under the protection of nitrogen, cooling to room temperature, separating out a precipitate, performing suction filtration on the precipitate, and washing and drying with water, absolute ethyl alcohol and petroleum ether in sequence to obtain a red powdered bridging ligand B-089(9.9g, the yield is 56%);
2) weighing intermediate B-0895.4mmol (9.9 g), adding ligand C-08918mmol (2.53g), adding ethylene glycol ethyl ether 200m L and potassium carbonate (7.5g) into the system, stirring for 24 hours at 120 ℃ under the protection of nitrogen, performing suction filtration, washing with alcohol, drying, using dichloromethane as a solvent, performing silica gel column chromatography, and concentrating the filtrate to separate out solid to obtain a final red compound L089 (3.7g, yield 33%);
the purity of HP L C is more than 99.5%;
mass spectrum calculated 1036.54; test value 1036.50;
elemental analysis calculated C: 63.73%; 6.52 percent of H; 2.70 percent of N; 3.09 percent of O; 18.54 percent of Ir; 5.42 percent of Si; the test value is C: 63.70%; 6.50 percent of H; 2.73 percent of N; 3.10 percent of O; 18.50 percent of Ir; 5.40 percent of Si.
Specifically, the reaction formulae of steps 1) to 2) are as follows:
in the embodiment, the iridium metal complex is applied to preparation of organic electroluminescent device products.
The present invention also provides an organic electroluminescent device made of the iridium metal complex, more particularly, the iridium metal complex represented by chemical formula 1.
Example 6
An organic electroluminescent device was prepared using compound L001 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, solvents such as isopropyl alcohol, acetone, and methanol were ultrasonically washed in this order, dried, transferred to a plasma cleaning machine, and the substrate was washed for 5 minutes and sent to an evaporation coater. Firstly, the upper surface of ITO (anode) is evaporated with CuPc
Followed by deposition of NPB
Host material 4, 4'-N, N' -biphenyl dicarbazole ("CBP") and doping material compound L00195: 5 weight ratio were mixed for evaporation
Evaporated electron transport layer "Alq3"
Vapor deposition of an electron-injecting layer L iF
Deposition cathode Al
And testing the performance luminescence characteristics of the obtained device by adopting a KEITH L EY2400 type source measuring unit and a CS-2000 spectral radiance luminance meter to evaluate driving voltage, current efficiency and power efficiency.
Referring to the above method, compounds L001 were replaced with L008, L017, L055, and L089, respectively, to prepare organic electroluminescent devices of the corresponding compounds.
Comparative example 1
An organic electroluminescent device was prepared in the same manner as in example 6, and the structure of the light-emitting layer-doped compound was as follows:
the same examination as in example 6 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 6 and comparative example 1
As can be seen from Table 1, the organic electroluminescent device prepared using the iridium metal complex provided by the present invention as a doping material for the light emitting layer and the comparative compound Ir (pq)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 and the power efficiency are obviously improved.
The invention has the beneficial effects that: the iridium metal complex with the novel structure provided by the invention has the advantages that the specific heterocyclic ligand combination is selected, the wavelength of the compound is adjusted, and the obtained organic metal compound is used for an organic electroluminescent device, so that the luminous efficiency and the brightness of the device are improved.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Furthermore, it should be understood that although the present description refers to embodiments, not every embodiment may contain only a single embodiment, and such description is for clarity only, and those skilled in the art should integrate the description, and the embodiments may be combined as appropriate to form other embodiments understood by those skilled in the art.
Claims (8)
1. An iridium metal complex having a structural formula shown in chemical formula 1:
R1、R2、R3、R4、R5、R6and R7Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C4-C12 aromatic heterocyclic group, or substituted or unsubstitutedCondensed cyclic group of C8-C16, R4Is an alkane, R5、R6Is methyl.
2. The iridium metal complex of claim 1 wherein R is1、R2、R3The substitution position is any position of the ring; r1The number of the substituents is 0-3, R2The number of substituents is 0-4, R3The number of the substituents is 0 to 4.
3. The iridium metal complex of claim 1 wherein the alkyl group is a straight chain alkyl group, a branched alkyl group, a cycloalkyl group, a straight chain alkyl group substituted with at least 1 substituent group, a branched alkyl group substituted with at least 1 substituent group, or a cycloalkyl group substituted with at least 1 substituent group; wherein, the substituent is one or more of halogen, deuterium, cyano, hydroxyl and sulfydryl independently.
4. An iridium metal complex according to claim 1, wherein the aryl group is an unsubstituted aryl group or an aryl group substituted with at least 1 substituent; wherein the substituents are independently selected from halogen, deuterium, amino, cyano, nitro, hydroxy or mercapto.
5. An iridium metal complex according to claim 4, wherein the aromatic heterocyclic group is an unsubstituted heteroaryl group or an aromatic heterocyclic group substituted with at least 1 substituent; wherein the heteroatom in the heteroaryl group is nitrogen, sulfur or oxygen; the substituents are independently selected from halogen, deuterium, amino, cyano, nitro, hydroxyl or mercapto.
6. A process for producing an iridium metal complex according to any one of claims 1 to 5, which comprises the steps of:
1) providing compound a and compound C, respectively, represented by the following structural formulae:
wherein R is1、R2、R3、R4、R5、R6And the number of substituents of each thereof is in accordance with the range defined in chemical formula 1;
2) fully reacting the raw material A with iridium trichloride to prepare a bridging ligand intermediate B;
3) and fully reacting the intermediate B with the intermediate C to obtain the iridium metal complex shown in the chemical formula 1.
7. The method for producing an iridium metal complex according to claim 6, wherein the bridged ligand intermediate B has the structure:
8. an organic electroluminescent device comprising the phosphor light-emitting material according to any one of claims 1 to 5.
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