CN111039995A - Phosphorescent complex, preparation method thereof and organic electroluminescent device - Google Patents
Phosphorescent complex, preparation method thereof and organic electroluminescent device Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 239000003446 ligand Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 238000001035 drying Methods 0.000 claims description 19
- 238000001816 cooling Methods 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 16
- 238000010992 reflux Methods 0.000 claims description 16
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 239000012044 organic layer Substances 0.000 claims description 9
- 238000003786 synthesis reaction Methods 0.000 claims description 9
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 8
- 239000000126 substance 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
- 238000000967 suction filtration Methods 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- -1 amino, silyl Chemical group 0.000 claims description 4
- 125000005594 diketone group Chemical group 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 230000001376 precipitating effect Effects 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N isonitrile group Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 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
- 125000004149 thio group Chemical group *S* 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 2
- 239000011259 mixed solution Substances 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000010410 layer Substances 0.000 description 28
- 239000000463 material Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000002386 leaching Methods 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 12
- 238000005303 weighing Methods 0.000 description 11
- 239000012065 filter cake Substances 0.000 description 10
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 238000003828 vacuum filtration Methods 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 238000000643 oven drying Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 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 4
- 238000004140 cleaning Methods 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 239000000758 substrate 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
- 239000012153 distilled water Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 150000003057 platinum Chemical class 0.000 description 3
- 238000004506 ultrasonic cleaning Methods 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000012805 post-processing Methods 0.000 description 2
- HNFHVPDEAVTSAR-UHFFFAOYSA-N 1,5-diphenylpentane-2,4-dione Chemical compound C=1C=CC=CC=1CC(=O)CC(=O)CC1=CC=CC=C1 HNFHVPDEAVTSAR-UHFFFAOYSA-N 0.000 description 1
- WPTZNYNYUKBMIW-UHFFFAOYSA-N 2,4,6-trimethylheptane-3,5-dione Chemical compound CC(C)C(=O)C(C)C(=O)C(C)C WPTZNYNYUKBMIW-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001308 synthesis method Methods 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
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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
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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
- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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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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- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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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)
- Crystallography & Structural Chemistry (AREA)
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- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a phosphorescent complex, a preparation method thereof and an organic electroluminescent device, wherein the phosphorescent complex has a structural general formula
Description
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to a phosphorescent complex, a preparation method thereof and an organic electroluminescent device.
Background
In recent years, organic electroluminescent diodes (OLEDs) have been favored because of their excellent characteristics, such as being ultra-thin, flexible, self-emissive, and wide viewing angle. At present, the efficiency and the service life of the green and yellow organic phosphorescent materials basically meet the requirements of industrial production, but high-performance red phosphorescent materials still need to be developed.
In 1963, the Pope research group applied 400V direct current to vapor-deposited micron-sized single-crystal anthracene, and under the vacuum condition, the organic electroluminescence phenomenon was observed for the first time. In 2011, Kwon research combined a red-light iridium complex, i.e. a phosphorescent complex shown in formula 1, and Bebq is adopted2The maximum emission wavelength of the electroluminescent device as a light-emitting body is 620nm, the driving voltage is only 2.4V at a low level, the CIE color coordinates are (0.64, 0.35), and the maximum current efficiency is 30.1 cd/A. In 2017, Kido researches combine a deep red phosphorescent complex, namely the phosphorescent complex shown in formula 2, and the phosphorescent complex is used as a main material to prepare an evaporation type photoelectric device, wherein the maximum emission peak position is 670nm, the driving voltage is 2.4V, and the CIE color coordinate is (0.70, 0.29);
the lack of the current high-efficiency red-light phosphorescent luminescent material always restricts the rapid development of the organic electroluminescent material. In recent years, the most used red phosphorescent materials are mainly platinum complexes, but the platinum complexes are planar structures, so that aggregation is easy to occur, and the photoelectric properties of the platinum complexes are affected. In contrast, the octahedral cyclometalated iridium complex has the characteristics of short phosphorescence life, high efficiency, simple synthesis, easy adjustment of light color and the like, and becomes a very important research direction for designing novel efficient red light phosphorescence luminescent materials at present.
Disclosure of Invention
In view of the above, the present invention provides a phosphorescent compound, a method for preparing the same, and an organic electroluminescent device, wherein the phosphorescent compound is applied to the electroluminescent device, and the organic electroluminescent device prepared by using the phosphorescent compound has high current efficiency, low driving voltage, and long phosphorescent lifetime.
In order to achieve the purpose, the invention adopts the following technical scheme:
a phosphorescent complex has a structure shown as formula G:
wherein:
R1～R5each independently represents hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid group, ester group, nitrile group, isonitrile group, thio group, sulfinyl group, sulfonyl group, phosphino group; or said R1～R6Wherein any adjacent substituents are optionally joined or fused to form a ring;
R1～R3the substituent position of (A) is any position of the ring, R1～R3The number of the substituents is 0 to 4, R4～R6The number of the substituents is 0 to 1.
Preferably, said R is1～R3Form a ring with each other between any adjacent substituents, or said R1～R3Form a ring with other substituents on the ring, and the R4～R6Any adjacent substituents form a ring with each other.
Preferably, the alkyl is a straight chain alkyl, a branched chain alkyl, a cyclic alkyl, a straight chain alkyl substituted with at least 1 substituent, a branched chain alkyl substituted with at least 1 substituent, or a cyclic alkyl substituted with at least 1 substituent, wherein the substituents are independently selected from deuterium, methyl, ethyl, isopropyl, nitro, halogen, and a combination of one or more of carboxyl.
Preferably, the aryl group is an unsubstituted aryl group or an aryl group substituted with at least 1 substituent; wherein the substituent groups are independently selected from one or more of deuterium, nitro, halogen, nitrile group, methyl, isopropyl and tert-butyl.
Preferably, the heteroaryl is unsubstituted heteroaryl or heteroaryl substituted with at least 1 substituent; wherein the heteroatom in the heteroaryl group is selected from one or more of nitrogen, sulfur or oxygen in combination.
Preferably, the halogen is selected from one or more of fluorine, chlorine and bromine.
Preferably, said R is1～R6The hydrogen atom in the group or substituent group of (a) is deuterated.
Preferably, the specific structural formula of the phosphorescent complex shown in chemical formula 1 is:
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 invention also provides a preparation method of the phosphorescent complex, which comprises the following steps:
s1, dissolving iridium trichloride of a compound shown as a formula A in ethylene glycol ethyl ether and water, carrying out reflux reaction for 20-36h under the protection of inert gas, and after the reaction is finished, cooling, precipitating, filtering, washing and drying to obtain a bridged ligand compound shown as a formula B;
s2, sequentially adding the bridged ligand compound shown in the formula B, the diketone derivative shown in the formula C, anhydrous potassium carbonate and ethylene glycol ethyl ether into a three-necked bottle, carrying out reflux reaction under the protection of inert gas for 20-36h, and after the reaction is finished, cooling, precipitating, carrying out suction filtration, washing, drying, carrying out column chromatography and concentrating to obtain the phosphorescent complex shown in the formula G;
the synthesis route of the phosphorescent complex is as follows:
preferably, in step S1, the reaction molar ratio of the compound represented by formula a to iridium trichloride is 2.5: 1.
Preferably, in the step S2, the reaction molar ratio of the bridged ligand compound represented by the formula B to the diketone derivative represented by the formula C is 1: 3.
Preferably, in the step S1, the reaction temperature is 110-125 ℃.
Preferably, in the step S2, the reaction temperature is 110-125 ℃.
Preferably, in step S1, the post-processing procedure is: and cooling to room temperature, separating out a precipitate, performing vacuum filtration, sequentially leaching with absolute ethyl alcohol and petroleum ether, and drying to obtain the bridged ligand compound shown in the formula B.
Preferably, in step S2, the post-processing procedure is: cooling to room temperature, carrying out vacuum filtration, leaching a filter cake with ethanol, drying under-0.1 Mpa at 50 ℃, passing through a silica gel column, and spin-drying the obtained filtrate to obtain the phosphorescent complex shown in the formula G.
Preferably, the diketone derivative represented by the formula C is selected from the following compounds:
the invention further provides the application of the phosphorescent complex in an organic electroluminescent device.
The invention also provides an organic electroluminescent device containing the phosphorescent complex.
The organic electroluminescent device includes: a first electrode, a second electrode and at least one organic layer, said organic layer being located between said first electrode and said second electrode and at least one of said organic layers comprising a phosphorescent complex according to any one of claims 1 to 7; the phosphorescent complex exists in the organic layer in a single form or in a mixture with other substances.
Preferably, the organic layer includes at least 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.
Preferably, the organic electroluminescent device includes a light-emitting layer containing the above-described phosphorescent complex.
Preferably, the light-emitting layer includes a host material and a dopant material, the host material includes a fluorescent host and a phosphorescent host, and the dopant material is the phosphorescent complex.
Preferably, the mixing ratio of the host material to the dopant material is (90:10) - (99.5: 0.5).
The invention further provides application of the organic electroluminescent device in an organic light-emitting device, an organic solar cell, electronic paper, an organic photoreceptor or an organic thin film transistor.
According to the technical scheme, compared with the prior art, the invention provides the phosphorescent complex, the preparation method thereof and the organic electroluminescent device, and the phosphorescent complex has the following beneficial effects:
(1) the invention provides a phosphorescence complex with a novel structure, and an organic electroluminescent device prepared by using the phosphorescence complex has higher current efficiency, low driving voltage and longer phosphorescence service life.
(2) The preparation method of the phosphorescent complex provided by the invention has the advantages of simple and efficient process and high purity of the prepared product.
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
The synthesis of the compound G002 comprises the following specific steps:
s1, weighing A-002(55.68mmol, 15.00g) and IrCl3·3H2O (22.28mmol, 7.80g), ethylene glycol ethyl ether (300mL), and water (100mL) were added to the reaction system, respectively, under N2Heating and refluxing for 24h under protection, then cooling to room temperature, separating out precipitate, performing vacuum filtration, sequentially leaching with anhydrous ethanol and petroleum ether, and oven drying to obtain B-002(8.5mmol, 13.00g) with a yield of 76.5%.
S2, weighing B-002(8.50mmol, 13.00g), K2CO3(85.02mmol, 11.75g), ethylene glycolEther (100mL) was added to the reaction system separately under N2Adding C-002(3, 7-diethyl-4, 6-nonanedione) (25.5mmol, 5.41G) under protection, heating and refluxing for 24h, cooling to room temperature, carrying out suction filtration under reduced pressure, leaching a filter cake with ethanol, drying the filter cake under the conditions of-0.1 Mpa and 50 ℃, passing through a silica gel column, and carrying out spin drying on the obtained filtrate to obtain G-002(10.52mmol, 9.90G) with the yield of 61.9%.
HPLC purity: 99 percent.
Mass spectrum: theoretical value 940.22; test value 940.36.
Elemental analysis:
theoretical value C, 67.71%; h, 5.47%; ir, 20.44%; n, 2.98%; o, 3.40%;
test value C, 67.73%; h, 5.49%; ir, 20.44%; n, 2.96%; o,3.41 percent.
Example 2
The synthesis of the compound G-007 comprises the following specific steps:
s1, weighing A-007(50.43mmol, 15.00g) and IrCl3·3H2O (20.17mmol, 7.11g), ethylene glycol ethyl ether (300mL), and water (100mL) were added to the reaction system, respectively, under N2Heating and refluxing for 24h under protection, then cooling to room temperature, separating out precipitate, performing vacuum filtration, sequentially leaching with anhydrous ethanol and petroleum ether, and oven drying to obtain B-007(7.31mmol, 12.00g) with a yield of 72.4%.
S2, weighing B-007(7.31mmol, 12.00g), K2CO3(73.08mmol, 10.10g) and ethylene glycol ethyl ether (100mL) were added to the reaction system separately in N2Adding C-007(3, 7-diethyl-4, 6-nonanedione) (21.93mmol, 4.64G) under protection, heating and refluxing for 24h, cooling to room temperature, carrying out suction filtration under reduced pressure, leaching a filter cake with ethanol, drying the filter cake under the conditions of-0.1 Mpa and 50 ℃, passing through a silica gel column, and carrying out spin drying on the obtained filtrate to obtain G-007(8.02mmol, 8.01G) with the yield of 54.9%.
HPLC purity: 99 percent.
Mass spectrum: theoretical value 996.33; test value 996.42.
Elemental analysis:
theoretical value C, 68.72%; h, 5.97%; ir, 19.29%; n, 2.81%; o, 3.21%;
test value C, 68.73%; h,5.99 percent; ir, 19.28%; n, 2.80%; and 3.23 percent of O.
Example 3
The synthesis of the compound G-050 comprises the following specific steps:
s1, weighing A-050(47.56mmol, 15.00g) and IrCl3·3H2O (19.02mmol, 6.71g), ethylene glycol ethyl ether (300mL), and water (100mL) were added to the reaction system, respectively, under N2Heating and refluxing for 24h under protection, then cooling to room temperature, separating out precipitate, performing vacuum filtration, sequentially leaching with anhydrous ethanol and petroleum ether, and oven drying to obtain B-050(6.97mmol, 12.00g) with a yield of 75.1%.
S2, weighing B-050(6.97mmol, 12.00g), K2CO3(69.68mmol, 9.63g) and ethylene glycol ethyl ether (100mL) were added to the reaction system separately in N2Adding C-050(3, 7-diethyl-4, 6-nonanedione) (20.91mmol, 4.43G) under protection, heating and refluxing for 24h, cooling to room temperature, carrying out suction filtration under reduced pressure, leaching a filter cake with ethanol, drying the filter cake under the conditions of-0.1 Mpa and 50 ℃, passing through a silica gel column, and carrying out spin drying on the obtained filtrate to obtain G-050(7.26mmol, 7.50G) with the yield of 52.1%.
HPLC purity: 99 percent.
Mass spectrum: theoretical value 1032.31; test value 1032.40.
Elemental analysis:
theoretical value C, 66.32%; h, 5.57%; f, 3.68%; ir, 18.62%; n, 2.71%; o, 3.10%;
test value C, 66.30%; h, 5.54%; f, 3.67%; ir, 18.61%; n, 2.73%; and 3.11 percent of O.
Example 4
The synthesis of the compound G-070 comprises the following specific steps:
s1, weighing A-070(43.80mmol, 15.00g) and IrCl3·3H2O (17.52mmol, 6.18g), ethylene glycol ethyl ether (300mL), and water (100mL) were added to the reaction system, respectively, under N2Heating and refluxing for 24h under protection, then cooling to room temperature, separating out precipitate, performing vacuum filtration, sequentially leaching with anhydrous ethanol and petroleum ether, and oven drying to obtain B-070(5.49mmol, 10.00g) with a yield of 64.57%.
S2, weighing B-070(5.49mmol, 10.00g), K2CO3(54.84mmol, 7.58g) and ethylene glycol ethyl ether (100mL) were added to the reaction system separately in N2Adding C-070(2,4, 6-trimethyl-3, 5-heptanedione) (16.47mmol, 2.77G) under protection, heating and refluxing for 24h, cooling to room temperature, vacuum filtering, leaching a filter cake with ethanol, drying under the conditions of-0.1 Mpa and 50 ℃, passing through a silica gel column, and spin-drying the obtained filtrate to obtain G-070(5.45mmol, 5.70G) with the yield of 49.7%.
HPLC purity: 99 percent.
Mass spectrum: theoretical value 1044.24; test value 1044.34.
Elemental analysis:
theoretical value C, 62.11%; h, 4.92%; ir, 18.41%; n, 5.37%; o, 9.19%;
test value C, 62.14%; h, 4.95%; ir, 18.41%; n, 5.36%; and O,9.21 percent.
Example 5
The synthesis of the compound G-093 comprises the following specific steps:
s1, weighing A-093(39.86mmol, 15.00g) and IrCl3·3H2O (15.94mmol, 5.62g), ethylene glycol ethyl ether (300mL), and water (100mL) were added to the reaction system, respectively, under N2Heating and refluxing for 24 hr under protection, cooling to room temperature to precipitate, vacuum filtering, and purifying with anhydrousEthanol and petroleum ether were sequentially eluted and dried to give B-093(5.93mmol, 11.00g) in 74% yield.
S2, weighing B-093(5.93mmol, 11.00g), K2CO3(59.33mmol, 8.2g) and ethylene glycol ethyl ether (100mL) were added to the reaction system separately in N2Adding C-093(1, 5-diphenyl-2, 4-pentanedione) (17.79mmol, 3.95G) under protection, heating and refluxing to 120 ℃, cooling to room temperature, vacuum filtering, leaching a filter cake with ethanol, drying under-0.1 Mpa at 50 ℃, passing through a silica gel column, and spin-drying the obtained filtrate to obtain G-093(6.17mmol, 7.20G) with a yield of 52.1%.
HPLC purity: 99 percent.
Mass spectrum: theoretical value 1166.05; test value 1166.13.
Elemental analysis:
theoretical value C, 60.77%; h, 3.89%; br, 13.71%; ir, 16.48%; n, 2.40%; o, 2.74%;
test value C, 60.74%; h, 3.83%; br, 13.70%; ir, 16.46%; n, 2.41%; o,2.73 percent.
Example 6
The synthesis of the compound G-097 comprises the following specific steps:
s1, weighing A-097(45.26mmol, 15.00g) and IrCl3·3H2O (18.10mmol, 6.38g), ethylene glycol ethyl ether (300mL), and water (100mL) were added to the reaction system, respectively, under N2Heating and refluxing for 24h under protection, then cooling to room temperature, separating out precipitate, performing vacuum filtration, sequentially leaching with anhydrous ethanol and petroleum ether, and oven drying to obtain B-097(6.78mmol, 12.05g) with a yield of 74.6%.
S2, weigh B-004(6.75mmol, 12.00g), K2CO3(67.51mmol, 9.33g) and ethylene glycol ethyl ether (100mL) were added to the reaction system, respectively, under N2Adding C-097(3, 7-diethyl-4, 6-nonanedione) (20.25mmol, 4.29g) under protection, heating to 120 deg.C, refluxing for 24h, and cooling to room temperatureVacuum filtering, leaching the filter cake with ethanol, oven drying at-0.1 Mpa and 50 deg.C, passing through silica gel column, and spin drying the obtained filtrate to obtain G-097(6.12mmol, 6.51G) with yield of 45.2%.
HPLC purity: 99 percent.
Mass spectrum: theoretical value 1064.30; test value 1064.37.
Elemental analysis:
theoretical value C, 62.07%; h, 5.59%; ir, 18.06%; n, 5.26%; o, 9.02%;
test value C, 62.08%; h,5.60 percent; ir, 18.07%; n, 5.27%; and O,9.03 percent.
Examples 7 to 21
The target compounds of examples 7 to 21 can be synthesized by the synthesis method of example 1 by replacing the corresponding reactants, and the specific structural chemical formulas and the results of MS (i.e., mass spectrum) are shown in table 1.
TABLE 1 chemical formulas of target compounds of examples 7 to 16 and MS results
Example 22
The embodiment provides an organic electroluminescent device, which comprises a substrate, an anode layer arranged on the substrate, a hole injection layer arranged on the anode layer, a hole transport layer arranged on the hole injection layer, an organic light emitting layer arranged on the hole transport layer, an electron transport layer arranged on the organic light emitting layer, an electron injection layer arranged on the electron transport layer and a cathode layer arranged on the electron injection layer.
The preparation method of the organic electroluminescent device comprises the following steps:
coating with a thickness of
The ITO glass substrate is put in distilled water to be cleaned for 2 times,ultrasonic cleaning for 30 minutes, repeatedly cleaning with distilled water for 2 times, ultrasonic cleaning for 15 minutes, after the cleaning with distilled water is finished, sequentially ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, methanol, etc., drying, transferring to a plasma cleaning machine, cleaning the substrate for 5 minutes, and transferring to a deposition machine. Firstly, the upper surface of ITO (anode) is evaporated with CuPc
Followed by deposition of NPB
Host substance 4,4'-N, N' -biphenyl dicarbazole ('CBP') and doping substance compound G-002 are mixed for evaporation
Wherein the weight ratio of CBP to dopant compound G-002 is 95: 5; vapor deposition of electron transport layer Alq3"
Evaporation of electron injection layer LiF
Deposition cathode Al
The organic electroluminescent device is prepared in the form of.
By referring to the method, G002 is respectively replaced by G-001, G-007, G-010, G-013, G-026, G-035, G-041, G-045, G-050, G-052, G-055, G-063, G-070, G-075, G-080, G-086, G-090, G-093, G-097 and G-100, and the organic electroluminescent devices of the corresponding compounds are prepared.
Comparative example 1
An organic electroluminescent device was fabricated in the same manner as in example 22, except that the dopant compound G002 of the organic light-emitting layer was replaced with the compound Ir (bty)2(acac), organic electroluminescent device obtained, Compound Ir (bty)2The structural formula of (acac) is shown below:
to further illustrate the luminescence properties of the novel iridium complex as a phosphorescent material, the devices obtained in example 22 and comparative example 1 were tested for their luminescence properties, and the results of driving voltage, luminescence brightness, and luminescence efficiency were evaluated using a KEITHLEY model 2400 source measuring unit, a CS-2000 spectroradiometer, and are shown in table 2.
Table 2 test results of organic electroluminescent devices in example 22 and comparative example 1
As can be seen from Table 2, the light-emitting luminance was 4000cd/cm2Compared with a comparative example 1, the driving voltage of the device provided by the invention is 3.92-4.56V, which is obviously lower than that of the comparative example 1, the efficiency (34.6-42.1) is far higher than that of the comparative example 1, and the service life (641-745) is 4-5 times that of the comparative example 1, so that the organic electroluminescent device prepared by using the phosphorescent complex provided by the invention as a luminescent layer material is superior to the organic electroluminescent device of the comparative phosphorescent complex, the driving voltage is obviously reduced, the current efficiency is obviously improved, and the phosphorescent service life is obviously improved.
It will be apparent to those skilled in the art that many modifications and variations can be made in the present invention without departing from the spirit and scope of the invention. It is therefore contemplated that the present invention cover the modifications and variations of this invention provided they come within the scope of the appended claims and their equivalents.
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. A phosphorescent complex is characterized in that the structure of the phosphorescent complex is shown as formula G:
wherein:
R1～R6each independently represents hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid group, ester group, nitrile group, isonitrile group, thio group, sulfinyl group, sulfonyl group, phosphino group;
R1～R3the substituent position of (A) is any position of the ring, R1～R3The number of the substituents is 0 to 4, R4～R6The number of the substituents is 0 to 1.
2. The phosphorescent complex of claim 1, wherein R is1～R3Form a ring with each other between any adjacent substituents, or said R1～R3Form a ring with other substituents on the ring, and the R4～R6Any adjacent substituents form a ring with each other.
3. The phosphorescent complex of claim 1, wherein the alkyl group is a linear alkyl group, a branched alkyl group, a cyclic alkyl group, a linear alkyl group substituted with at least 1 substituent, a branched alkyl group substituted with at least 1 substituent, or a cyclic alkyl group substituted with at least 1 substituent, wherein the substituents are independently selected from deuterium, methyl, ethyl, isopropyl, nitro, halogen, and a combination of one or more of carboxyl groups.
4. A phosphorescent 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 substituent groups are independently selected from one or more of deuterium, nitro, halogen, nitrile group, methyl, isopropyl and tert-butyl.
5. The phosphorescent complex of claim 1, wherein the heteroaryl group is an unsubstituted heteroaryl group or a heteroaryl group substituted with at least 1 substituent; wherein the heteroatom in the heteroaryl group is selected from one or more of nitrogen, sulfur or oxygen in combination.
6. A phosphorescent complex according to claim 1 wherein the halogen is selected from the group consisting of fluorine, chlorine and bromine.
7. A phosphorescent complex according to any one of claims 1 to 6 wherein R is1～R6The hydrogen atom in the group or substituent group of (a) is deuterated.
8. A method for preparing a phosphorescent complex according to any one of claims 1 to 7, comprising the steps of:
s1, dissolving the compound shown in the formula A and iridium trichloride into a mixed solution of ethylene glycol ethyl ether and water, carrying out reflux reaction for 20-36h under the protection of inert gas, and after the reaction is finished, cooling, precipitating, carrying out suction filtration, washing and drying to obtain a bridged ligand compound shown in the formula B;
s2, sequentially adding the bridged ligand compound shown in the formula B, the diketone derivative shown in the formula C, anhydrous potassium carbonate and ethylene glycol ethyl ether into a three-necked bottle, carrying out reflux reaction under the protection of inert gas for 20-36h, and after the reaction is finished, cooling, precipitating, carrying out suction filtration, washing, drying, carrying out column chromatography and concentrating to obtain the phosphorescent complex shown in the formula G;
the synthesis route of the phosphorescent complex is as follows:
9. use of a phosphorescent complex according to any one of claims 1 to 7 in an organic electroluminescent device.
10. An organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer, wherein the organic layer is located between the first electrode and the second electrode, and wherein at least one of the organic layers comprises the phosphorescent complex of any one of claims 1 to 7; the phosphorescent complex exists in the organic layer in a single form or in a mixture with other substances.
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| CN113214325A (en) * | 2020-07-15 | 2021-08-06 | 奥来德(上海)光电材料科技有限公司 | Organic iridium metal complex and preparation method and application thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110818741A (en) * | 2019-11-15 | 2020-02-21 | 吉林奥来德光电材料股份有限公司 | Organic doped luminescent compound, preparation method thereof and organic electroluminescent device |
| CN113387983A (en) * | 2020-03-11 | 2021-09-14 | 北京夏禾科技有限公司 | Metal complex of ligand with polysubstituted biaryl structure |
| CN113387983B (en) * | 2020-03-11 | 2023-04-18 | 北京夏禾科技有限公司 | Metal complex of ligand with polysubstituted biaryl structure |
| CN113214325A (en) * | 2020-07-15 | 2021-08-06 | 奥来德(上海)光电材料科技有限公司 | Organic iridium metal complex and preparation method and application thereof |
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