CN112552353A - Iridium metal complex and organic photoelectric element using same - Google Patents
Iridium metal complex and organic photoelectric element using same Download PDFInfo
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- CN112552353A CN112552353A CN202011571808.7A CN202011571808A CN112552353A CN 112552353 A CN112552353 A CN 112552353A CN 202011571808 A CN202011571808 A CN 202011571808A CN 112552353 A CN112552353 A CN 112552353A
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- -1 Iridium metal complex Chemical class 0.000 title claims abstract description 51
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- 230000005525 hole transport Effects 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000012044 organic layer Substances 0.000 claims description 7
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
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- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- IZUQUDLUTSCHMX-UHFFFAOYSA-N iridium;1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 IZUQUDLUTSCHMX-UHFFFAOYSA-N 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- 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
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Abstract
The invention belongs to the field of organic photoelectricity, and particularly relates to an iridium metal complex and an organic photoelectric element comprising the same, in particular to an organic electroluminescent diode, wherein the iridium metal complex has a structure shown in a formula (I):
Description
Technical Field
The invention belongs to the field of organic photoelectricity, and particularly relates to an iridium metal complex and a photoelectric element comprising the iridium metal complex, in particular to an organic electroluminescent diode.
Background
As a novel display technology, the organic light-emitting diode (OLED) has the unique advantages of self luminescence, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, high response speed, wide applicable temperature range, low driving voltage, capability of manufacturing flexible, bendable and transparent display panels, environmental friendliness and the like, can be applied to flat panel displays and new generation illumination, and can also be used as a backlight source of an LCD.
Since the invention of the 20 th century and the 80 th century, organic electroluminescent devices have been used in industry, such as display screens of mobile phones, but the current OLED devices have limited their wider application, especially large screen displays, due to low efficiency and short service life. And the most important factor restricting the wide application thereof is the performance of the organic electroluminescent material. Meanwhile, when an OLED device is operated by applying a voltage, joule heat is generated, so that organic materials are easily crystallized, and the lifetime and efficiency of the device are affected.
The OLED emission is divided into two modes of fluorescence emission and phosphorescence emission, and it is theorized that the ratio of a singlet excited state to a triplet excited state due to charge binding is 1: 3. Professor Baldo and Forrest in 1998 discovered that triplet phosphorescence can be utilized at room temperature, and the upper limit of the original internal quantum efficiency is increased to 100%, and triplet phosphors are often complexes composed of heavy metal atoms, and by utilizing the heavy atom effect, the strong spin-orbit coupling effect causes the energy levels of a singlet excited state and a triplet excited state to be mixed with each other, so that the originally forbidden triplet energy is relieved to emit light in the form of phosphorescence, and the quantum efficiency is also greatly improved.
At present, almost all light emitting layers in an OLED module use a host-guest light emitting system mechanism, that is, a guest light emitting material is doped in a host material, and generally, the energy gap of an organic host material is larger than that of the guest material, that is, energy is transferred from the host to the guest, so that the guest material is excited to emit light. A commonly used phosphorescent organic host material such as CBP (4, 4' -bis (9-carbazolyl) -biphenyl) has a high efficiency and a high triplet energy level, and when it is used as an organic material, the triplet energy can be efficiently transferred from a light emitting organic material to a guest phosphorescent light emitting material. The common organic guest material is an iridium metal compound, and the iridium metal compound is mainly applied to commercial OLED materials at present, but still has some technical difficulties, such as high OLED efficiency, longer service life and lower operating voltage.
The invention discovers that the conjugation of the ligand of the iridium metal compound is expanded, the specific cyclic structure, the substituent group and the like are introduced to improve the luminous efficiency of the iridium metal compound, and the iridium metal compound is applied to an organic photoelectric element on the premise of ensuring the thermal stability of the iridium metal compound, and particularly in an organic electroluminescent device, the iridium metal compound can improve the current efficiency, reduce the operating voltage of the element and prolong the service life.
Disclosure of Invention
The invention aims to provide an iridium metal complex and a photoelectric device comprising the same, in particular to an organic electroluminescent diode.
The iridium metal complex provided by the invention has a structure shown as a formula (I):
wherein, X is selected from NR1, O, S, CR1R2, SiR1R2, O-P-R1 or B-R1; y is selected from N or C-R1; R1-R8 are independently selected from any one of hydrogen, deuterium, halogen, C1-C18 alkyl, C1-C18 alkoxy, C1-C18 alkylsilyl, C1-C18 alkoxysilyl, C6-C40 aryl, C1-C40 heteroaryl, substituted or unsubstituted arylether group, substituted or unsubstituted heteroarylether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamine group, substituted or unsubstituted arylsilicon group, substituted or unsubstituted heteroarylsilicon group, substituted or unsubstituted aryloxysilyl group, substituted or unsubstituted arylacyl group, substituted or unsubstituted heteroarylacyl group, and substituted or unsubstituted phosphinyl group; (L ^ Z) is an auxiliary ligand, a bidentate ligand, the same as or different from the main ligand on the left side of the structural formula; all groups may be partially or fully deuterated; m is taken from 1, 2 or 3, and m + n is 3; heteroaryl means containing B, N, O, S, P (═ O), Si, and at least one heteroatom of P.
Preferably, in the iridium metal complex formula (I), L ^ Z is selected from one of the following representative structural formulas, but does not represent the limitation:
wherein Y1 is independently selected from O or N, R1-R3 are independently selected from C1-C18 alkyl, C1-C18 alkoxy, C1-C18 alkylsilyl, C1-C18 alkoxysilyl, C6-C40 aryl and C1-C40 heteroaryl; a and B are selected from C1-C60 alkyl, C1-C60 alkoxy, C1-C60 alkylsilyl, C1-C60 alkoxysilyl, C6-C40 aryl and C1-C40 heteroaryl in a ring-forming or non-ring-forming manner, and A and B can be mono-substituted or multi-substituted according to the valence bond principle.
Preferably, the iridium metal complex of the present invention is selected from one of the following structures, but does not represent a limitation thereto:
wherein X, Y, R1 to R8, A and B are the same as described above.
Preferably, the iridium metal complex of the present invention, wherein (L ^ Z) in formula (I) is selected from one of the following representative structural formulas, but not limited thereto:
wherein X is selected from NR1, O, S, CR1R2, SiR1R2, O ═ P-R1 or B-R1; R1-R3 are independently selected from C1-C18 alkyl, C1-C18 alkoxy, C1-C18 alkylsilyl, C1-C18 alkoxysilyl, C6-C40 aryl and C1-C40 heteroaryl, and can be partially deuterated or fully deuterated.
Preferably, the iridium metal complex of the present invention is selected from one of the following representative structural formulae, but does not represent a limitation thereto:
the solvent used in the preparation of the iridium metal complex comprises unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetrahydronaphthalene, decahydronaphthalene, bicyclohexane, n-butylbenzene, sec-butylbenzene and tert-butylbenzene, halogenated saturated hydrocarbon solvents such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane and bromocyclohexane, halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and trichlorobenzene, ether solvents such as tetrahydrofuran and tetrahydropyran, ester solvents such as alkyl benzoate and the like, which are well known to those skilled in the art.
The present invention also relates to an organic opto-electronic device comprising: a first electrode;
a second electrode facing the first electrode;
the organic functional layer is clamped between the first electrode and the second electrode;
wherein the organic functional layer comprises the iridium metal complex.
The invention also relates to an organic electroluminescent device which comprises a cathode layer, an anode layer and an organic layer, wherein the organic layer comprises at least one of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron injection layer and an electron transport layer, and the light emitting layer of the device contains the iridium metal complex.
The luminescent layer of the organic electroluminescent device contains the iridium metal complex and a corresponding main material, wherein the mass percentage of the iridium metal complex is 0.1-50%.
The Organic electroluminescent device of the present invention is any one of an Organic photovoltaic device, an Organic Light Emitting Device (OLED), an Organic Solar Cell (OSC), electronic paper (e-paper), an Organic Photoreceptor (OPC), an Organic Thin Film Transistor (OTFT), an Organic Memory device (Organic Memory Element), a lighting device, and a display device.
In the present invention, the organic photoelectric device is an anode which can be formed by depositing a metal or an oxide having conductivity and an alloy thereof on a substrate by a sputtering method, electron beam evaporation, vacuum evaporation, or the like; and sequentially evaporating a hole injection layer, a hole transport layer, a luminescent layer, a hole blocking layer and an electron transport layer on the surface of the prepared anode, and then evaporating a cathode. The organic electroluminescent device is prepared by vapor deposition of the cathode, the organic layer and the anode on the substrate except the above method. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, and an electron transport layer. In the invention, the organic layer is prepared by adopting a high polymer material according to a solvent engineering (spin-coating), tape-casting (tape-casting), doctor-blading (sector-Printing), Screen-Printing (Screen-Printing), ink-jet Printing or Thermal-Imaging (Thermal-Imaging) method instead of an evaporation method, so that the number of the device layers can be reduced.
The materials used for the organic electroluminescent device according to the present invention may be classified into top emission, bottom emission, or double-sided emission. The compounds of the organic electroluminescent device according to the embodiment of the present invention can be applied to the aspects of organic solar cells, illuminating OLEDs, flexible OLEDs, organic photoreceptors, organic thin film transistors and other electroluminescent devices by a similar principle of the organic light emitting device.
The invention has the beneficial effects that:
the iridium metal compound has good thermal stability, has good electron receiving capacity, and can improve energy transmission between a host and an object, and is particularly characterized in that the iridium metal compound is used as a functional layer, especially used as a light-emitting layer to manufacture an organic electroluminescent device, the current efficiency of the organic electroluminescent device is improved, the starting voltage is reduced, the service life of the device is greatly improved, and the energy is effectively transferred to the iridium metal compound for light emission after most electrons and holes are compounded.
Drawings
FIG. 1 is a structural diagram of an organic electroluminescent diode device according to the present invention.
Where 110 denotes a substrate, 120 denotes an anode, 130 denotes a hole injection layer, 140 denotes a hole transport layer, 150 denotes a light emitting layer, 160 denotes a hole blocking layer, 170 denotes an electron transport layer, 180 denotes an electron injection layer, and 190 denotes a cathode.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
In a preferred embodiment of the present invention, the OLED device according to the invention comprises a hole transport layer, which may preferably be selected from known or unknown materials, particularly preferably from the following structures, without representing the present invention being limited to the following structures:
in a preferred embodiment of the present invention, the hole transport layer contained in the OLED device of the present invention comprises one or more p-type dopants. Preferred p-type dopants of the present invention are, but do not represent a limitation of the present invention to:
in a preferred embodiment of the present invention, the electron transport layer may be selected from at least one of the compounds ET-1 to ET-13, but does not represent that the present invention is limited to the following structures:
the present invention also provides a formulation comprising the composition and a solvent, and the solvent used is not particularly limited, and there may be used unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetrahydronaphthalene, decahydronaphthalene, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, etc., halogenated saturated hydrocarbon solvents such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, etc., halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene, etc., ether solvents such as tetrahydrofuran, tetrahydropyran, etc., ester solvents such as alkyl benzoate, etc., which are well known to those skilled in the art. The preparation is directly used for preparing photoelectric devices.
Hereinafter, the general synthetic procedure for the guest compounds of formula (I) is as follows, based on the available literature and the relevant technical reserves of the inventors:
the general procedure is as follows,
(1) under the protection of argon, ligand 1 or L ^ Z (0.10 mol) and IrCl3.3H2Heating and refluxing a mixed solution of O (0.045 mol), 2-ethoxyethanol (300 ml) and water (100 ml) for 16-20 hours until a supernatant is obtained, detecting the content of the ligand 1 by using high performance liquid chromatography to be less than 5%, stopping heating, cooling to room temperature, performing suction filtration by using a Buchner funnel, leaching a filter cake by using a mixed solution of water and 2-ethoxyethanol, and drying to obtain a bridging dimer 2 or 3 of yellow powder, wherein the yield is 81-89%.
(2) Adding dichloro crosslinked dimer complex (2.2mmol), ligand L ^ Z or ligand 1(2.4mmol), anhydrous sodium carbonate (1.2g,10.8mmol) and 80ml of 2-ethoxyethanol into a double-neck round-bottom flask, heating and refluxing for 6 hours, stopping heating, cooling to room temperature, adding a proper amount of distilled water, and filtering to obtain a solid. The solid was dissolved in dichloromethane and passed through a short column of silica gel. Removing the solvent under reduced pressure, and washing the solid obtained by concentration with methanol and petroleum ether in sequence to obtain the final target product.
The preparation method of the iridium metal compound, i.e., the guest compound, and the light emitting property of the device are explained in detail with reference to the following examples, and the ligand 1 is obtained by custom synthesis. These are merely examples illustrating embodiments of the present invention and the scope of the present invention is not limited thereto.
Example 1: synthesis of Compound 1
Referring to the general synthetic route, L ^ Z represents n-pentane-2, 4-dione, and the yield of the final product is 70%. Mass spectrum m/z, theoretical 892.31; found M + H: 893.3.
example 2: synthesis of Compound 2
Referring to the general synthetic route, L ^ Z represents n-pentane-2, 4-dione, and the yield of the final product is 75%. Mass spectrum m/z, theoretical 1004.43; found M + H: 1005.4.
example 3: synthesis of Compound 3
Referring to the general synthetic route, L ^ Z represents n-pentane-2, 4-dione, and the yield of the final product is 76%. Mass spectrum m/z, theoretical 948.37; found M + H: 949.3.
example 4: synthesis of Compound 4
Referring to the general synthetic route, L ^ Z represents n-pentane-2, 4-dione, and the yield of the final product is 72%. Mass spectrum m/z, theoretical 976.39; found M + H: 977.4.
example 5: synthesis of Compound 5
Referring to the general synthetic route, L ^ Z represents 2, 6-dimethylheptane-3, 5-dione, with a yield of 80% of the final product. Mass spectrum m/z, theoretical 984.35; found M + H: 985.3.
example 6: synthesis of Compound 6
Referring to the general synthetic route, L ^ Z represents 2, 6-dimethylheptane-3, 5-dione, with a yield of 80% of the final product. Mass spectrum m/z, theoretical 1096.47; found M + H: 1097.4.
example 7: synthesis of Compound 7
Referring to the general synthetic route, L ^ Z represents 3, 7-diethylnonane-4, 6-dione, with a yield of 73% of the final product. Mass spectrum m/z, theoretical 1068.43; found M + H: 1069.4.
example 8: synthesis of Compound 8
Referring to the general synthetic route, L ^ Z represents 3, 7-diethylnonane-4, 6-dione, with a yield of 68% of the final product. Mass spectrum m/z, theoretical 1180.57; found M + H: 1181.5.
example 9: synthesis of Compound 9
Referring to the general synthetic route, L ^ Z represents 3, 7-diethylnonane-4, 6-dione, with a yield of 83% of the final product. Mass spectrum m/z, theoretical 1180.57; found M + H: 1181.5.
example 10: synthesis of Compound 10
Referring to the general synthetic route, L ^ Z represents n-pentane-2, 4-dione, and the yield of the final product is 69%. Mass spectrum m/z, theoretical 958.31; found M + H: 959.3.
example 11: synthesis of Compound 11
Referring to the general synthetic route, L ^ Z represents n-pentane-2, 4-dione, and the yield of the final product is 78%. Mass spectrum m/z, theoretical 1070.43; found M + H: 1071.43.
example 12: synthesis of Compound 12
Referring to the general synthetic route, L ^ Z represents n-pentane-2, 4-dione, and the yield of the final product is 83%. Mass spectrum m/z, theoretical 1070.43; found M + H: 1071.43.
example 13: synthesis of Compound 13
Referring to the general synthetic route, L ^ Z represents n-pentane-2, 4-dione, and the yield of the final product is 86%. Mass spectrum m/z, theoretical 898.29; found M + H: 899.3.
example 14: synthesis of Compound 14
Referring to the general synthetic route, L ^ Z represents n-pentane-2, 4-dione, and the yield of the final product is 80%. Mass spectrum m/z, theoretical 1010.41; found M + H: 1011.4.
example 15: synthesis of Compound 15
Referring to the general synthetic route, L ^ Z represents n-pentane-2, 4-dione, and the yield of the final product is 81%. Mass spectrum m/z, theoretical 984.31; found M + H: 985.3.
example 16: synthesis of Compound 16
Referring to the general synthetic route, L ^ Z represents n-pentane-2, 4-dione, and the yield of the final product is 76%. Mass spectrum m/z, theoretical 960.23; found M + H: 961.2.
example 17: synthesis of Compound 17
Referring to the general synthetic route, L ^ Z represents 3-methylpentane-2, 4-dione, with a yield of 76% of the final product. Mass spectrum m/z, theoretical 1054.42; found M + H: 1055.4.
example 18: synthesis of Compound 18
Referring to the general synthetic route, L ^ Z represents n-pentane-2, 4-dione, and the yield of the final product is 76%. Mass spectrum m/z, theoretical 902.27; found M + H: 903.3.
example 19: synthesis of Compound 19
Referring to the general synthetic route, L ^ Z represents 3, 7-diethylnonane-4, 6-dione, with a yield of 76% of the final product. Mass spectrum m/z, theoretical 1124.49; found M + H: 1125.5.
example 20: synthesis of Compound 20
Referring to the general synthetic route, L ^ Z represents 4-methyl-2- (4-methylphenyl) pyridine, and the yield of the final product is 68%. Mass spectrum m/z, theoretical 889.30; found M + H: 890.3.
example 21: synthesis of Compound 21
Referring to the general synthetic route, L ^ Z represents 4-methyl-2- (4-methylphenyl) pyridine, and the yield of the final product is 68%. Mass spectrum m/z, theoretical 1039.35; found M + H: 1040.3.
manufacturing of OLED device:
a P-doped material P-1 to P-5 is evaporated on the surface or anode of ITO/AG/ITO glass with the size of 2mm multiplied by 2mm in light emitting area or the P-doped material is co-evaporated with the compound in the table with the concentration of 1% to 50% to form a Hole Injection Layer (HIL) with the thickness of 5 nm to 100nm and a Hole Transport Layer (HTL) with the thickness of 5 nm to 200nm, then a light emitting layer (EML) (which can contain the compound) with the thickness of 10 nm to 100nm is formed on the hole transport layer, finally an Electron Transport Layer (ETL) with the thickness of 20 nm to 200nm and a cathode with the thickness of 50 nm to 200nm are formed by the compound in sequence, if necessary, an Electron Blocking Layer (EBL) is added between the HTL and the EML layer, and an Electron Injection Layer (EIL) is added between the ETL and the cathode. The OLEDs were tested by standard methods, as listed in table 1.
To better illustrate the practical gain effects of the present invention, OLED devices were prepared by comparing the following commonly used iridium metal complexes RD-1 to RD-5.
In the specific embodiment, the OLED device is structurally characterized in that the OLED device is arranged on ITO/AG/ITO-containing glass, HIL is HT-1: P-3(95:5 v/v%), and the thickness is 10 nanometers; HTL is HT-1, and the thickness is 90 nanometers; EBL is HT-8, thickness is 10 nm, EML is H-1: iridium metal compound (97:3 v/v%), thickness is 35 nm, ETL is ET-13: LiQ (50:50 v/v%) with a thickness of 35 nm was evaporated to a cathode Yb of 1 nm and Ag of 14 nm, and characteristics of current efficiency, voltage and life according to the above examples and comparative examples are shown in Table 1 below.
The characteristics of efficiency, driving voltage, life, etc. according to the above examples and comparative examples are shown in table 1 below.
TABLE 1
As can be seen from Table 1, from the incorporation of a 5-membered ring in the ligand structure, the use of the iridium metal compound provided by the present invention as a guest material can significantly improve the current efficiency and reduce the driving voltage of the OLED device, and the lifetime is greatly improved, compared with the comparative devices 1 to 4 in devices 1 to 16. Compared with phenyl isoquinoline iridium metal complexes (RD-1-RD-4) (comparison devices 1-4), the organic electroluminescent device (device example 1-device example 16) prepared by using the iridium metal compound provided by the invention as a luminescent layer doping material has the advantages that the efficiency is improved by 40-65%, the driving voltage is reduced from 4.2 volts to 3.7 volts, and the service life is doubled. Compound 19 is most similar to RD-5, but compound 19 of the present invention has significant advantages, and the OLED device (device example 14) prepared using it as a doping material has an efficiency improved by 62%, a voltage reduced by 0.5 v, and a lifetime improved by 53% compared to comparative device 5. The iridium metal complex provided by the invention has obvious superiority and commercial application value.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (12)
1. An iridium metal complex, which is characterized in that the structural formula of the iridium metal complex is shown as a formula (I)
Wherein, X is selected from NR1, O, S, CR1R2, SiR1R2, O-P-R1 or B-R1; y is selected from N or C-R1; R1-R8 are independently selected from any one of hydrogen, deuterium, halogen, C1-C18 alkyl, C1-C18 alkoxy, C1-C18 alkylsilyl, C1-C18 alkoxysilyl, C6-C40 aryl, C1-C40 heteroaryl, substituted or unsubstituted arylether group, substituted or unsubstituted heteroarylether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamine group, substituted or unsubstituted arylsilicon group, substituted or unsubstituted heteroarylsilicon group, substituted or unsubstituted aryloxysilyl group, substituted or unsubstituted arylacyl group, substituted or unsubstituted heteroarylacyl group, and substituted or unsubstituted phosphinyl group; (L ^ Z) is an auxiliary ligand, a bidentate ligand, the same as or different from the main ligand on the left side of the structural formula; all groups may be partially or fully deuterated; m is taken from 1, 2 or 3, and m + n is 3; heteroaryl means containing B, N, O, S, P (═ O), Si, and at least one heteroatom of P.
2. The iridium metal complex of claim 1 wherein (L ^ Z) in the formula (I) is one selected from the group consisting of the following representative structural formulae:
wherein Y1 is independently selected from O or N, R1-R3 are independently selected from C1-C18 alkyl, C1-C18 alkoxy, C1-C18 alkylsilyl, C1-C18 alkoxysilyl, C6-C40 aryl and C1-C40 heteroaryl; a and B are selected from C1-C60 alkyl, C1-C60 alkoxy, C1-C60 alkylsilyl, C1-C60 alkoxysilyl, C6-C40 aryl and C1-C40 heteroaryl in a ring-forming or non-ring-forming manner, and A and B can be mono-substituted or multi-substituted according to the valence bond principle.
3. The iridium metal complex according to any one of claims 1 to 2, wherein the iridium metal complex structural formula (I) is selected from the following representative structures:
wherein X, Y, R1 to R8, A and B are the same as described in claim 1 and claim 2.
4. The iridium metal complex according to any one of claims 1 to 3, wherein (L ^ Z) in the formula (I) is one selected from the following representative formulae:
wherein X is selected from NR1, O, S, CR1R2, SiR1R2, O ═ P-R1 or B-R1; R1-R3 are independently selected from C1-C18 alkyl, C1-C18 alkoxy, C1-C18 alkylsilyl, C1-C18 alkoxysilyl, C6-C40 aryl and C1-C40 heteroaryl, and can be partially deuterated or fully deuterated.
5. The iridium metal complex according to any one of claims 1 to 4, wherein the iridium metal complex structural formula (I) is selected from the following representative structures:
6. a formulation characterized by comprising the iridium metal complex of any one of claims 1 to 5 and at least one solvent.
7. An organic optoelectronic device, comprising:
a first electrode;
a second electrode facing the first electrode;
the organic functional layer is clamped between the first electrode and the second electrode;
wherein the organic functional layer comprises the iridium metal complex of any one of claims 1 to 5.
8. An organic photoelectric element comprising a cathode layer, an anode layer and an organic layer, the organic layer comprising at least one of a hole injection layer, a hole transport layer, a light emitting layer or an active layer, an electron injection layer, and an electron transport layer, wherein: the iridium metal complex as recited in claims 1 to 5 is contained in any one layer of the device.
9. The organic photoelectric element according to claim 7 is an organic electroluminescent device, wherein the iridium metal complex and a corresponding host material are contained in a light-emitting layer, wherein the iridium metal complex is present in an amount of 1 to 50% by mass, and the host material is not limited at all.
10. A preparation according to claim 6, wherein said iridium metal complex and said solvent form a preparation, and the solvent used is not particularly limited, and a halogenated saturated hydrocarbon solvent such as toluene, xylene, mesitylene, tetralin, decahydronaphthalene, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane and the like, a halogenated unsaturated hydrocarbon solvent such as chlorobenzene, dichlorobenzene, trichlorobenzene and the like, an ether solvent such as tetrahydrofuran, tetrahydropyran and the like, an ester solvent such as alkyl benzoate and the like, which are well known to those skilled in the art can be used.
11. The Organic optoelectronic device according to claim 7, wherein the Organic optoelectronic device is an Organic photovoltaic device, an Organic Light Emitting Device (OLED), an Organic Solar Cell (OSC), an electronic paper (e-paper), an Organic Photoreceptor (OPC), an Organic Thin Film Transistor (OTFT) and an Organic Memory device (Organic Memory Element), a lighting and display device.
12. A display or lighting device comprising the organic electroluminescent element according to claim 9.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190052504A (en) * | 2017-11-08 | 2019-05-16 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent compound and organic electroluminescent device comprising the same |
| CN111655706A (en) * | 2018-05-14 | 2020-09-11 | 株式会社Lg化学 | Compound and organic light emitting device including the same |
| CN111848687A (en) * | 2020-07-15 | 2020-10-30 | 奥来德(长春)光电材料科技有限公司 | Red light organic electroluminescent material, preparation method thereof and photoelectric device |
| CN112010908A (en) * | 2020-08-31 | 2020-12-01 | 奥来德(上海)光电材料科技有限公司 | Iridium complex for red light electroluminescent material, preparation method thereof and photoelectric device |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190052504A (en) * | 2017-11-08 | 2019-05-16 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent compound and organic electroluminescent device comprising the same |
| CN111655706A (en) * | 2018-05-14 | 2020-09-11 | 株式会社Lg化学 | Compound and organic light emitting device including the same |
| CN111848687A (en) * | 2020-07-15 | 2020-10-30 | 奥来德(长春)光电材料科技有限公司 | Red light organic electroluminescent material, preparation method thereof and photoelectric device |
| CN112010908A (en) * | 2020-08-31 | 2020-12-01 | 奥来德(上海)光电材料科技有限公司 | Iridium complex for red light electroluminescent material, preparation method thereof and photoelectric device |
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