CN112679552A - Iridium metal complex and organic photoelectric element using same - Google Patents
Iridium metal complex and organic photoelectric element using same Download PDFInfo
- Publication number
- CN112679552A CN112679552A CN202011571820.8A CN202011571820A CN112679552A CN 112679552 A CN112679552 A CN 112679552A CN 202011571820 A CN202011571820 A CN 202011571820A CN 112679552 A CN112679552 A CN 112679552A
- Authority
- CN
- China
- Prior art keywords
- metal complex
- iridium metal
- organic
- substituted
- layer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Images
Landscapes
- Electroluminescent Light Sources (AREA)
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 industrially, OLED light emission is divided into two modes of fluorescence light emission and phosphorescence light emission, and it is theorized that the ratio of singlet excited state to triplet excited state caused by charge binding is 1:3, so that only 25% of the total energy that can be used for light emission is used with a small molecular fluorescent material, and the remaining 75% of the energy is lost due to the non-light emission mechanism of the triplet excited state, so that the internal quantum efficiency limit of the fluorescent material is generally considered to be 25%. 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 raised to 100%, and triplet phosphors are complex compounds composed of heavy metal atoms, and by utilizing the heavy atom effect, the strong spin-orbit coupling effect causes the energy levels of singlet excited states and triplet excited states 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 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 system of an organic host material is larger than that of a guest material, that is, the 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, long service life and lower operating voltage.
The invention discovers that the conjugation of an iridium metal compound ligand is expanded, a specific cyclic structure, a substituent group and the like are introduced to improve the luminous efficiency of the iridium metal compound, the thermal stability of the iridium metal compound is improved, the iridium metal compound is applied to an organic photoelectric device, and particularly in an organic electroluminescent device, the current efficiency can be improved, the operating voltage of the device can be reduced, and the organic photoelectric element with long service life can be obtained.
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 invention provides an iridium metal complex, which is characterized in that: the iridium metal complex has a structure shown as formula (I):
wherein A1 constitutes five-membered or more rings selected from C2-C60 alkyl, C1-C60 alkoxy, C1-C60 alkylsilyl, C1-C60 alkoxysilyl, C6-C40 aryl, and C1-C40 heteroaryl; x is selected from NR1, O, S, CR1R2, SiR1R2, O ═ P-R1 or B-R1; y is selected from N or C-R3; R1-R5 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 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; a2 and B are selected from C1-C60 alkyl, C1-C60 alkoxy, C1-C60 alkylsilyl, C1-C60 alkoxysilyl, C6-C40 aryl and C1-C40 heteroaryl, wherein A2 and B can be mono-substituted or poly-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, Y1, R1-R8 and A1 form five-membered rings selected from C1-C60 alkyl, C1-C60 alkoxy, C1-C60 alkylsilyl, C1-C60 alkoxysilyl, C6-C40 aryl and C1-C40 heteroaryl; a2 and B are the same as described above; all groups may be partially deuterated or fully deuterated.
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, Y1, R1 to R8, a2 and B are the same as described above; all groups may be partially deuterated or fully deuterated.
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 instead of heat 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 with the yield of 78-88%.
(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 74%. Mass spectrum m/z, theoretical 1112.6; found M + H: 1113.6.
example 2: synthesis of Compound 2
Referring to the general synthetic route, L ^ Z represents n-heptane-3, 5-dione, with a yield of 72% of the final product. Mass spectrum m/z, theoretical 1054.6; found M + H: 1055.6.
example 3: synthesis of Compound 3
Referring to the general synthetic route, L ^ Z represents 2, 6-dimethylheptane-3, 5-dione, with a yield of 75% of the final product. Mass spectrum m/z, theoretical 1140.6; found M + H: 1141.6.
example 4: synthesis of Compound 4
Referring to the general synthetic route, L ^ Z represents 2, 2, 6, 6-tetramethylheptane-3, 5-dione, and the yield of the final product is 79%. Mass spectrum m/z, theoretical 1054.58; found M + H: 1055.6.
example 5: synthesis of Compound 5
Referring to the general synthetic scheme, L ^ Z represents 3, 7-diethyl, 3, 7-dimethylnonane 4, 6-dione, with a yield of 73% of the final product. Mass spectrum m/z, theoretical 1220.65; found M + H: 1221.6.
example 6: synthesis of Compound 6
Referring to the general synthetic route, L ^ Z represents n-pentane-2, 4-dione, and the yield of the final product is 71%. Mass spectrum m/z, theoretical 1086.51; found M + H: 1087.5.
example 7: synthesis of Compound 7
Referring to the general synthetic route, L ^ Z represents n-heptane-3, 5-dione, with a yield of 76% of the final product. Mass spectrum m/z, theoretical 1028.54; found M + H: 1029.5.
example 8: synthesis of Compound 8
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 1010.45; found M + H: 1011.4.
example 9: synthesis of Compound 9
Referring to the general synthetic route, L ^ Z represents n-heptane-3, 5-dione, with a yield of 82% of the final product. Mass spectrum m/z, theoretical 1120.44; found M + H: 1121.4.
example 10: synthesis of Compound 10
Referring to the general synthetic route, L ^ Z represents 2, 6-dimethylheptane-3, 5-dione, with a yield of 83% of the final product. Mass spectrum m/z, theoretical 1148.47; found M + H: 1149.4.
example 11: synthesis of Compound 11
Referring to the general synthetic route, L ^ Z represents 3, 7-diethylnonane-4, 6-dione with a yield of 71% of the final product. Mass spectrum m/z, theoretical 1204.53; found M + H: 1205.5.
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 69%. Mass spectrum m/z, theoretical 1080.5; found M + H: 1081.5.
example 13: synthesis of Compound 13
Referring to the general synthetic route, L ^ Z represents 2, 6-dimethylheptane-3, 5-dione, with a yield of 76% of the final product. Mass spectrum m/z, theoretical 1050.6; found M + H: 1051.6.
example 14: synthesis of Compound 14
Referring to the general synthetic route, L ^ Z represents 3, 7-diethylnonane-4, 6-dione, with a yield of 74% of the final product. Mass spectrum m/z, theoretical 1136.6; found M + H: 1137.6.
example 15: synthesis of Compound 15
Referring to the general synthetic scheme, L ^ Z represents 3, 7-diethyl, 3, 7-dimethylnonane 4, 6-dione, with a yield of 72% of the final product. Mass spectrum m/z, theoretical 1192.66; found M + H: 1193.7.
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 71%. Mass spectrum m/z, theoretical 1144.5; found M + H: 1145.5.
example 17: synthesis of Compound 17
Referring to the general synthetic route, L ^ Z represents n-heptane-3, 5-dione, with a yield of 76% of the final product. Mass spectrum m/z, theoretical 1144.52; found M + H: 1145.5.
example 18: synthesis of Compound 18
Referring to the general synthetic route, L ^ Z represents 2, 6-dimethylheptane-3, 5-dione, with a yield of 77% of the final product. Mass spectrum m/z, theoretical 1200.57; found M + H: 1201.6.
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 79% of the final product. Mass spectrum m/z, theoretical 1114.57; found M + H: 1115.5.
example 20: synthesis of Compound 20
Referring to the general synthetic route, L ^ Z represents n-heptane-3, 5-dione, with a yield of 74% of the final product. Mass spectrum m/z, theoretical 1030.48; found M + H: 1031.4.
example 21: synthesis of Compound 21
Referring to the general synthetic route, L ^ Z represents 2, 6-dimethylheptane-3, 5-dione, with a yield of 81% of the final product. Mass spectrum m/z, theoretical 1116.4; found M + H: 1117.4.
example 22: synthesis of Compound 22
Referring to the general synthetic route, L ^ Z represents 3, 7-diethylnonane-4, 6-dione, with a yield of 80% of the final product. Mass spectrum m/z, theoretical 1116.51; found M + H: 1117.5.
example 23: synthesis of Compound 23
Referring to the general synthetic route, L ^ Z represents 3, 7-diethyl, 3, 7-dimethylnonane 4, 6-dione, with a yield of 81% of the final product. Mass spectrum m/z, theoretical 1144.54; found M + H: 1145.5.
example 24: synthesis of Compound 24
Referring to the general synthetic route, L ^ Z represents n-heptane-3, 5-dione, with a yield of 78% of the final product. Mass spectrum m/z, theoretical 946.42; found M + H: 947.4.
example 25: synthesis of Compound 25
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 1060.45; found M + H: 1061.45.
example 26: synthesis of Compound 26
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 1218.72; found M + H: 1219.7.
example 27: synthesis of Compound 27
Referring to the general synthetic route, the yield of the final product was 71%. Mass spectrum m/z, theoretical 882.37; found M + H: 883.4.
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
| Examples | Iridium metal compound | Driving voltage (volt) | Current efficiency (cd/A) | LT95 (hours) |
| Comparison device 1 | RD-1 | 4.3 | 28.3 | 72 |
| Comparison device 2 | RD-2 | 4.3 | 35.7 | 87 |
| Comparison device 3 | RD-3 | 4.2 | 39.6 | 96 |
| Comparison device 4 | RD-4 | 4.2 | 38.7 | 136 |
| Comparison device 5 | RD-5 | 4.2 | 38.3 | 113 |
| Device example 1 | Compound 1 | 3.8 | 57.4 | 166 |
| Device example 2 | Compound 2 | 3.8 | 57.1 | 160 |
| Device example 3 | Compound 4 | 3.7 | 60.3 | 189 |
| Device example 4 | Compound 7 | 3.9 | 57.4 | 148 |
| Device example 5 | Compound 9 | 3.9 | 56.7 | 156 |
| Device example 6 | Compound 16 | 3.8 | 59.1 | 174 |
| Device example 7 | Compound 18 | 3.7 | 60.1 | 200 |
| Device example 8 | Compound 19 | 3.7 | 63.9 | 232 |
| Device example 9 | Compound 20 | 3.8 | 61.1 | 210 |
| Device example 10 | Compound 21 | 3.8 | 59.1 | 200 |
| Device example 11 | Compound 24 | 3.8 | 57.5 | 170 |
As can be seen from table 1, from the incorporation of fused rings on the ligand structure, device 1 to device example 11, compared with comparative devices 1 to 5, the use of the iridium metal compound provided by the present invention as a guest material can significantly improve the current efficiency of the OLED device and reduce the driving voltage, while the lifetime is greatly improved. Compared with phenyl isoquinoline iridium metal complexes (RD-1-RD-5) (comparison devices 1-4), the efficiency of the organic electroluminescent device (device example 1-device example 11) prepared by using the iridium metal compound provided by the invention as a luminescent layer doping material is improved by 43-125%, the driving voltage is reduced from 4.3V to 3.7V, and the service life is prolonged by 220% at most. Particularly, the current efficiency of the device 8 prepared from the compound 19 reaches 63.9cd/A, which is 1.7 times that of the comparison device 5, and the service life of the device is 2.1 times that of the comparison device 5, so that the iridium metal complex provided by the invention has remarkable 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 (13)
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 A1 constitutes five-membered or more rings selected from C2-C60 alkyl, C1-C60 alkoxy, C1-C60 alkylsilyl, C1-C60 alkoxysilyl, C6-C40 aryl, and C1-C40 heteroaryl; x is selected from NR1, O, S, CR1R2, SiR1R2, O ═ P-R1 or B-R1; y is selected from N or C-R3; R1-R5 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 following representative formulae:
wherein Y1 is 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; a2 and B are selected from C1-C60 alkyl, C1-C60 alkoxy, C1-C60 alkylsilyl, C1-C60 alkoxysilyl, C6-C40 aryl and C1-C40 heteroaryl, wherein A2 and B can be mono-substituted or poly-substituted according to the valence bond principle; all groups may be partially deuterated or fully deuterated.
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, Y1, R1 to R8, a1 is the same as described in claim 1; a2 and B are the same as in claim 2.
4. The iridium metal complex according to any one of claims 1 to 3, wherein the iridium metal complex structural formula (I) is selected from the following representative structures:
wherein X, Y1, R1 to R8, a2 and B are the same as described in claim 1 and claim 2.
5. The iridium metal complex of claim 2 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.
6. The iridium metal complex according to any one of claims 1 to 5, wherein the iridium metal complex structural formula (I) is selected from the following representative structures:
7. a formulation characterized by comprising the iridium metal complex of any one of claims 1 to 6 and at least one solvent.
8. 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 6.
9. 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 6 is contained in any one layer of the device.
10. The organic photoelectric element according to claims 8 to 9, wherein the light-emitting layer contains the iridium metal complex and a corresponding host material, wherein the mass percentage of the iridium metal complex is 1% to 50%, and the host material is not limited at all.
11. A preparation according to claim 7, 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.
12. The Organic optoelectronic device according to claim 8, 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), an Organic Memory device (Organic Memory Element), a lighting and display device.
13. A display or lighting device comprising the organic electroluminescent element according to claim 10.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011571820.8A CN112679552A (en) | 2020-12-27 | 2020-12-27 | Iridium metal complex and organic photoelectric element using same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011571820.8A CN112679552A (en) | 2020-12-27 | 2020-12-27 | Iridium metal complex and organic photoelectric element using same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112679552A true CN112679552A (en) | 2021-04-20 |
Family
ID=75452042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011571820.8A Withdrawn CN112679552A (en) | 2020-12-27 | 2020-12-27 | Iridium metal complex and organic photoelectric element using same |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112679552A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113416536A (en) * | 2021-06-09 | 2021-09-21 | 上海大学 | Host-guest composition and organic electroluminescent element comprising same |
| CN113583055A (en) * | 2021-08-02 | 2021-11-02 | 浙江华显光电科技有限公司 | Organic metal complex and organic photoelectric element containing same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019221446A1 (en) * | 2018-05-14 | 2019-11-21 | 주식회사 엘지화학 | Compound and organic light emitting device comprising same |
| CN111116674A (en) * | 2019-12-27 | 2020-05-08 | 吉林奥来德光电材料股份有限公司 | Iridium metal complex luminescent material and preparation method and application thereof |
| CN111995999A (en) * | 2020-05-06 | 2020-11-27 | 浙江华显光电科技有限公司 | Combination of deuterated guest compound and host compound and photoelectric device comprising same |
-
2020
- 2020-12-27 CN CN202011571820.8A patent/CN112679552A/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019221446A1 (en) * | 2018-05-14 | 2019-11-21 | 주식회사 엘지화학 | Compound and organic light emitting device comprising same |
| CN111116674A (en) * | 2019-12-27 | 2020-05-08 | 吉林奥来德光电材料股份有限公司 | Iridium metal complex luminescent material and preparation method and application thereof |
| CN111995999A (en) * | 2020-05-06 | 2020-11-27 | 浙江华显光电科技有限公司 | Combination of deuterated guest compound and host compound and photoelectric device comprising same |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113416536A (en) * | 2021-06-09 | 2021-09-21 | 上海大学 | Host-guest composition and organic electroluminescent element comprising same |
| CN113416536B (en) * | 2021-06-09 | 2022-08-02 | 上海大学 | Host-guest composition and organic electroluminescent element comprising same |
| CN113583055A (en) * | 2021-08-02 | 2021-11-02 | 浙江华显光电科技有限公司 | Organic metal complex and organic photoelectric element containing same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111995999B (en) | Combination of deuterated guest compound and host compound and photoelectric device comprising same | |
| CN112680219B (en) | Composition and organic electroluminescent element comprising same | |
| CN112614964B (en) | Composition and organic electroluminescent element comprising same | |
| CN112645985A (en) | Iridium metal complex and organic photoelectric element using same | |
| CN112724178A (en) | Iridium metal compound with deuterium-fluorine synergistic effect and photoelectric element comprising iridium metal compound | |
| CN114644660A (en) | Organometallic complex, preparation, organic photoelectric device and display or lighting device | |
| CN113717232A (en) | Organometallic complex, preparation, organic photoelectric device and display or lighting device | |
| CN112679552A (en) | Iridium metal complex and organic photoelectric element using same | |
| CN112670426B (en) | Composition and organic electroluminescent element comprising same | |
| CN112851714A (en) | Iridium metal complex and organic photoelectric element using same | |
| CN112645988A (en) | Iridium metal complex and organic photoelectric element using same | |
| CN112645987A (en) | Iridium metal complex and organic photoelectric element using same | |
| CN112694502A (en) | Iridium metal complex and organic photoelectric element using same | |
| CN112679550A (en) | Iridium metal complex and organic photoelectric element using same | |
| CN114315914B (en) | Organometallic complex, preparation, organic photoelectric device and display or lighting device | |
| CN112694501A (en) | Iridium metal complex and organic photoelectric element using same | |
| CN112713250B (en) | Composition and organic electroluminescent element comprising same | |
| CN112687824B (en) | Composition and organic electroluminescent element comprising same | |
| CN112802970B (en) | Composition and organic electroluminescent element comprising same | |
| CN112652731B (en) | Composition and organic electroluminescent element comprising same | |
| CN112687819B (en) | Composition and organic electroluminescent element comprising same | |
| CN112687822B (en) | Composition and organic electroluminescent element comprising same | |
| CN112687823B (en) | Composition and organic electroluminescent element comprising same | |
| CN112652730B (en) | Composition and organic electroluminescent element comprising same | |
| CN112645986A (en) | Iridium metal complex and organic photoelectric element using same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WW01 | Invention patent application withdrawn after publication | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20210420 |