An organic metal complex and its application

Abstract

The present invention provides an organic metal complex and application thereof. After the organic metal complex is used in an organic electroluminescent device, the starting voltage of the device is reduced, and the luminous efficiency and life of the device are improved, and the organic metal complex has broad application prospects.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic electroluminescent materials, and relates to an organometallic complex and its application, in particular to an organometallic complex and its application in an organic electroluminescent device. Background Art

[0002] As a new generation of display technology, organic electroluminescent materials (OLEDs) have the advantages of being ultra-thin, self-luminous, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, and low energy consumption, and have been widely used in industries such as flat panel displays, flexible displays, solid state lighting, and vehicle-mounted displays.

[0003] Since the first report of highly efficient organic light-emitting diodes, the industry has been committed to researching how to improve the efficiency and stability of devices. Phosphorescent materials have a strong spin-orbit coupling effect and can utilize both singlet and triplet excitons simultaneously, making the internal quantum efficiency of phosphorescent electroluminescent devices reach 100% in theory.

[0004] However, in the prior art, when phosphorescent materials are applied to organic light-emitting devices, there are problems of low efficiency and short lifespan. Therefore, how to provide an organic electroluminescent material with long lifespan, high efficiency, and low driving voltage is an urgent problem to be solved by those skilled in the art. Summary of the Invention

[0005] Aiming at the deficiencies of the prior art, the purpose of the present invention is to provide an organometallic complex and its application, in particular to provide an organometallic complex and its application in an organic electroluminescent device. After the organometallic complex of the present application is used in an organic electroluminescent device, the startup voltage of the device is reduced, and the luminous efficiency and lifespan of the device are improved.

[0006] To achieve this purpose, the present invention adopts the following technical solutions:

[0007] On the one hand, the present invention provides an organometallic complex, and the organometallic complex has the following structure: M(L A ) p (L B ) q ;

[0008] where p is 2, q is 1, M is a metal, L A and L B are both ligands, and L A is LB is

[0009] Among them, ring C is selected from N-containing heteroaryl groups with C5-C30 (for example, the number of carbon atoms is 5, 8, 10, 13, 15, 18, 20, 23, 25, 28 or 30), and ring D is selected from aryl groups with C6-C30 (for example, the number of carbon atoms is 6, 8, 10, 13, 15, 18, 20, 23, 25, 28 or 30);

[0010] Ar 1 and Ar 2 are independently selected from -H, -D (deuterium), -T (tritium), -F, -CN, -CH 3 -, -CD 3 -, -CT 3 -, -CF 3 -, -CH 2 F, -CHF 2 -, substituted or unsubstituted C2-C6 alkyl, substituted or unsubstituted C6-C10 (such as C6, C7, C8, C9 or C10) aryl, and substituted or unsubstituted 4-membered - 8-membered (such as 4-membered, 5-membered, 6-membered, 7-membered or 8-membered) aromatic heterocyclic groups;

[0011] m is an integer between 1 and 10 (such as 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10), and n is an integer between 1 and 6 (such as 1, 2, 3, 4, 5 or 6).

[0012] The substituents on the aforementioned substituents are at least selected from one of -H, -D (deuterium), -T (tritium), -F, -CN, -CH3, -CD3, -CT 3 -, -CF 3 -, -CH 2 F or -CHF 2 ;

[0013] Preferably, ring C is selected from one of the following C-1 to C-23 structures:

[0014]

[0015] Among them, * is a connecting bond; X is selected from C or Si, and Y is selected from O or S; R 1 and R 2 are independently selected from -H, -D (deuterium), -T (tritium), -CH 3 -, -CD 3 - or -CH 2 CH 3 ;

[0016] Preferably, ring D is selected from one of the following D-1 to D-5 structures:

[0017]

[0018] Among them, * represents the connecting bond and position.

[0019] In the present invention, the alkyl group includes a linear alkyl group, a branched alkyl group or a cycloalkyl group.

[0020] In the present invention, the C2-C6 alkyl group may exemplarily include ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, n-hexyl, cyclobutyl, cyclopentyl or cyclohexyl.

[0021] In Ar defined in the present invention 1 and Ar 2 the heteroatoms in the heteroaryl group are each independently selected from at least one of N, S and O.

[0022] Preferably, the organometallic compound is selected from one of the following structures:

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033] where D represents deuterium and T represents tritium.

[0034] In the present invention, the preparation process of the organometallic complex is as follows:

[0035]

[0036] where the definition of the group is the same as above and will not be repeated here.

[0037] On the other hand, the present invention provides an organic electroluminescent material, and the organic electroluminescent material includes the organometallic complex as described above.

[0038] On the other hand, the present invention provides an organic electroluminescent device, which includes a first electrode, a second electrode, and an organic thin film layer disposed between the first electrode and the second electrode, and the organic thin film layer includes the organic metal complex as described above.

[0039] Preferably, the organic thin film layer includes a light-emitting layer, the light-emitting layer contains a host material and a doping material, and the doping material includes the organic metal complex as described above.

[0040] Preferably, the percentage of the doping material in the total mass of the materials of the light-emitting layer is 0.5-10%.

[0041] In the present invention, the light-emitting layer may include light-emitting dyes (i.e., dopants) that can emit spectra of different wavelengths, and may also include a host material at the same time. The light-emitting layer may be a monochromatic light-emitting layer that emits a single color such as red, green, or blue. Multiple monochromatic light-emitting layers of different colors may be arranged in a planar pattern according to a pixel pattern, or may be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they may be separated from each other or connected to each other. The light-emitting layer may also be a single color light-emitting layer that can simultaneously emit different colors such as red and green.

[0042] According to different technologies, the light-emitting layer material may adopt different materials such as phosphorescent electroluminescent materials and thermally activated delayed fluorescence light-emitting materials. In an OLED device, a single light-emitting technology may be adopted, or a combination of multiple different light-emitting technologies may be adopted. These different light-emitting materials classified by technology may emit light of the same color or different colors. Preferably, the light-emitting layer adopts the technology of phosphorescent electroluminescence.

[0043] Preferably, the organic thin film layer further includes any one layer or a combination of at least two layers of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, or an electron injection layer.

[0044] In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, waterproofness, and transparency. In addition, a thin film transistor (TFT) may also be provided on the substrate for a display.

[0045] The first electrode can be formed by sputtering or depositing a material serving as the first electrode on a substrate. When the first electrode serves as an anode, oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), etc., and any combination thereof can be used. In addition, the anode material can also be selected from materials and their combinations that contribute to hole injection other than the listed anode materials, including known materials suitable for making an anode. When the first electrode serves as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc., and any combination thereof can be used. In addition to the listed cathode materials above, the cathode material can also be materials and their combinations that contribute to electron injection, including known materials suitable for making a cathode.

[0046] The organic material layer can be formed on the electrode by methods such as vacuum thermal evaporation, spin coating, printing, etc. Compounds used as the organic material layer can be organic small molecules, organic macromolecules, and polymers, as well as their combinations. The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multi-layer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0047] The material of the hole transport layer can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers, or polymers containing conductive dopants such as poly(phenylene vinylene), polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives such as the compounds shown as HT-1 to HT-34 below; or any combination thereof.

[0048]

[0049]

[0050] But not limited to the above several materials.

[0051] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can adopt one or more of the above-mentioned compounds HT-1 to HT-34, or one or more of the following compounds HI-1 to HI-3; it can also adopt one or more of the compounds HT-1 to HT-34 doped with one or more of the compounds HI-1 to HI-3:

[0052] However, it is not limited to the above several materials.

[0053] The OLED organic material layer can also include an electron transport region between the light-emitting layer and the cathode. The electron transport region can be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region can also be a multi-layer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0054] In one aspect of the present invention, the electron transport layer material can be selected from, but not limited to, one or more combinations of the following listed ET-1 to ET-57.

[0055]

[0056]

[0057]

[0058] However, it is not limited to the above several materials.

[0059] The device can also include an electron injection layer between the electron transport layer and the cathode. The electron injection layer material includes, but is not limited to, one or more combinations of the following listed: LiF, NaCl, CsF, Li 2 O, Cs 2 CO 3 , BaO, Na, Li or Ca.

[0060] On the other hand, the present invention provides a display panel, and the display panel includes the above-mentioned organic electroluminescent device.

[0061] Compared with the prior art, the present invention has the following beneficial effects:

[0062] The organometallic complex of the present invention is used as a light-emitting layer doping material in an organic electroluminescent device, which can effectively reduce the driving voltage of the organic electroluminescent device, improve the current efficiency, solve the problem of low life, and has broad application prospects. Detailed Embodiments

[0063] The technical solutions of the present invention will be further described below through specific embodiments. Those skilled in the art should understand that the embodiments are only for helping to understand the present invention and should not be regarded as specific limitations on the present invention.

[0064] Synthesis Example 1

[0065] This synthesis example provides an organometallic compound I-001, that is, the compound numbered I-001. The specific synthesis steps are as follows:

[0066] Among them: The synthesis of the intermediate 3,7-diethyl-1,1,1-trifluoro-9-methyldodecane-4,6-dione is shown below, and the following is the same and will not be repeated one by one:

[0067]

[0068] 1) Under the condition of a water bath and N 2 protection, dissolve the raw material 1H-benzo[d][1,2,3]triazol-1-ol hydrate (CAS: 80029-43-2) (15.31 g, 100 mmol) in 238 mL of dichloromethane, add triethylamine (12.14 g, 120 mmol) to this reaction system, then dropwise add the raw material 2-ethyl-4,4,4-trifluorobutyryl chloride (18.86 g, 100 mmol). After dropping, keep warm and stir for 6 h. At this temperature, quench the reaction with 5% HCl solution, then naturally warm up, continue to stir for 15 min, extract the aqueous phase with ethyl acetate, combine the organic phases and rotate until no liquid flows out. The intermediate T-01-structured compound is obtained by column chromatography separation, with a mass of 24.41 g and a yield of 85%.

[0069] The intermediate T-01 was subjected to the following analysis and testing:

[0070] HPLC purity: greater than 98%;

[0071] Mass spectrometry: Calculated value is 287.24; Test value is 287.45.

[0072] Elemental analysis: Calculated values are C: 50.18; H: 4.21; F: 19.84; N: 14.63; O: 11.14. Test values are C: 50.19; H: 4.22; F: 19.86; N: 14.61; O: 11.12.

[0073] 2) Under N2 protection, add raw material 2-ethyl-4-methylvaleric acid (50.47 g, 350 mmol) and N,N'-carbonyldiimidazole (68.10 g, 420 mmol) into a 500 mL reaction flask, dissolve them with 200 mL of tetrahydrofuran, stir at 25 °C for 0.5 h. Meanwhile, under N2 protection, add dimethylhydroxylamine hydrochloride (34.14 g, 350 mmol) and triethylamine (42.50 g, 420 mmol) into another 500 mL reaction flask, dissolve them with 170 mL of tetrahydrofuran, stir at 25 °C for 0.5 h. Then, under N2 protection, mix the two reaction systems in a 1000 mL reaction flask, stir at 25 °C for 0.5 h, then heat to reflux for 5 h, and after cooling to room temperature, add 200 mL of deionized water, extract with ethyl acetate to obtain 62.3 g of intermediate T-02 structural compound, with a yield of 95%, which can be directly used for the next step without purification;

[0074] Perform the following analytical tests on intermediate T-02:

[0075] HPLC purity: greater than 98%;

[0076] Mass spectrometry: calculated value is 187.28; measured value is 187.30.

[0077] Elemental analysis: calculated values are C: 64.13; H: 11.30; N: 7.48; O: 17.09. Measured values are C: 64.12; H: 11.31; N: 7.49; O: 17.08.

[0078] 3) Under N 2 protection, dissolve intermediate T-02 (61.80 g, 330 mmol) in 300 mL of tetrahydrofuran solution, place the reaction system in a liquid nitrogen-acetone bath to make the reaction system temperature -78 °C, slowly dropwise add methylmagnesium bromide (247.5 mL, 2 M) solution. After the addition is complete, stir the reaction system at 0 °C for 5 h, then quench the reaction with saturated ammonium chloride solution, extract with ethyl acetate, combine the organic phases and rotate until no liquid flows out, and obtain 23.47 g of intermediate T-03 structural compound by column chromatography separation, with a yield of 50%

[0079] Perform the following analytical tests on intermediate T-03:

[0080] HPLC purity: greater than 99%;

[0081] Mass spectrometry: calculated value is 142.24; measured value is 142.20.

[0082] Elemental analysis: calculated values are C: 76.00; H: 12.76; O: 11.25. Measured values are C: 76.01; H: 12.73; O: 11.27.

[0083] 4) Under N2 protection, dissolve the intermediate T-01 structure compound (23.55 g, 82 mmol) prepared in the previous step in 200 mL of dichloromethane. When maintaining the internal temperature at 0 °C, add lithium diisopropylamide (82 mL, 2 M) dropwise to the system, keep the temperature for reaction for 2 h, then add the intermediate T-03 structure compound (23.33 g, 164 mmol) dropwise to the reaction system. After dropping, raise the temperature to room temperature and stir for 3 h. Then, quench the reaction system with 10% HCl solution, extract with dichloromethane, and separate by column chromatography to obtain 16.41 g of the product 3,7-diethyl-1,1,1-trifluoro-9-methyldodecane-4,6-dione, with a yield of 68%.

[0084] Perform the following analytical tests on the intermediate 3,7-diethyl-1,1,1-trifluoro-9-methyldodecane-4,6-dione:

[0085] HPLC purity: greater than 99%;

[0086] Mass spectrometry: calculated value is 294.36; measured value is 294.57.

[0087] Elemental analysis: calculated values are C: 61.21; H: 8.56; F: 19.36; O: 10.87. Measured values are C: 61.23; H: 8.54; F: 19.34; O: 10.89.

[0088] Under a nitrogen protection system, weigh compound VII-001 (1,6-dichloroisoquinoline, CAS: 630421-73-7) (19.81 g, 100 mmol), formula VI-001 (isopropylboronic acid, CAS: 80041-89-0) (8.79 g, 100 mmol), and anhydrous potassium carbonate (41.4 g, 300 mmol) into the reaction system. Add 200 ml of toluene, 100 mL of absolute ethanol, and 100 mL of pure water. Under nitrogen protection, add Pd(PPh 3 ) 4 (1.16 g, 1 mmol). Under nitrogen protection, reflux at 100 °C for 24 h, then cool to 25 °C, filter by suction. Wash the filter cake with petroleum ether, dry the filter cake under vacuum, add 100 ml of dichloromethane to dissolve it. Subject the solution to column chromatography (200 - 300 mesh, 450 g) with the developing agent DCM:PE = 3:1. Rotate the receiving solution until no liquid flows out, and dry it under vacuum at 50 °C to obtain the indicated compound formula IV-001 (14.60 g, with a yield of 71%). Perform the following analytical tests on the intermediate compound formula IV-001:

[0089] HPLC purity: greater than 99.5%;

[0090] Mass spectrometry: Calculated value is 205.69; measured value is 205.82.

[0091] Elemental analysis: Calculated values are C: 70.07; H: 5.88; Cl: 17.24; N: 6.81. Measured values are C: 70.09; H: 5.86; Cl: 17.25; N: 6.80.

[0092] Under a nitrogen protection system, weigh compound Ⅳ-001 (14.40 g, 70 mmol), formula Ⅴ-001 (3,5-dimethylphenylboronic acid, CAS: 172975-69-8) (11.55 g, 77 mmol), and anhydrous potassium carbonate (28.98 g, 210 mmol) into the reaction system. Add 170 ml of toluene, 85 ml of absolute ethanol, and 85 ml of pure water. Under nitrogen protection, add Pd(PPh 3 ) 4 (0.81 g, 0.7 mmol). Reflux at 100 °C for 24 h under nitrogen protection, then cool to 25 °C, filter by suction. Wash the filter cake with petroleum ether, dry the filter cake under vacuum. Dissolve the product in 150 ml of toluene by heating to 110 °C, cool to 25 °C to precipitate, filter by suction. Wash the filter cake with petroleum ether, dry at 50 °C under vacuum to obtain the indicated compound formula Ⅲ-001 (14.32 g, yield 74%). Analyze and test the intermediate compound formula Ⅲ-001 as follows:

[0093] HPLC purity: greater than 99.5%;

[0094] Mass spectrometry: Calculated value is 275.40; measured value is 275.59.

[0095] Elemental analysis: Calculated values are C: 87.23; H: 7.69; N: 5.09. Measured values are C: 87.26; H: 7.68; N: 5.07.

[0096] Under a nitrogen protection system, weigh ligand Ⅲ-001 (13.77 g, 50 mmol) and IrC1 3 ·3H 2 0 (7.76 g, 22 mmol) into the reaction system. Add a mixed solution of 390 mL of ethylene glycol monoethyl ether and 130 mL of pure water. Reflux for 26 hours under nitrogen protection, then cool to room temperature. Precipitation occurs. Filter the precipitate by suction and wash and dry it successively with water, absolute ethanol, and petroleum ether. The mass of the bridged ligand Ⅱ-001 obtained as a dark red powder is 9.22 g, and the yield is 54%.

[0097] Weigh the bridging ligand II-001 (8.54 g, 5.5 mmol), add anhydrous potassium carbonate (7.59 g, 55 mmol), then add 170 ml of ethylene glycol monoethyl ether to the system, displace nitrogen three times, add 3,7-diethyl-1,1,1-trifluoro-9-methyldodecane-4,6-dione (4.04 g, 13.75 mmol) under nitrogen, reflux for 22 hours under nitrogen protection, cool down, filter by suction, wash with alcohol, and dry. Use dichloromethane as the solvent and carry out column chromatography on neutral alumina. Concentrate the filtrate to precipitate the solid, and finally obtain the organophosphorus luminescent material shown in I-001, with a mass of 4.09 g and a yield of 36%.

[0098] Perform the following analytical tests on the organometallic compound I-001:

[0099] HPLC purity: greater than 99.5%;

[0100] Mass spectrometry: Calculated value is 1034.34; Measured value is 1034.57.

[0101] Elemental analysis: Calculated values are C: 63.87; H: 6.24; F: 5.51; Ir: 18.58; N: 2.71; O: 3.09. Measured values are C: 63.85; H: 6.22; F: 5.50; Ir: 18.59; N: 2.75; O: 3.09.

[0102] Synthesis Example 2

[0103] This synthesis example provides an organometallic compound I-040, that is, the compound numbered I-040. The specific synthesis steps are as follows:

[0104]

[0105] Under a nitrogen protection system, weigh the compound IV-040 (1-chloro-7-fluorobenzo[g]isoquinoline) (16.22 g, 70 mmol), formula V-040 (3,5-dimethylphenylboronic acid, CAS: 172975-69-8) (12.60 g, 84 mmol), and anhydrous potassium carbonate (28.98 g, 210 mmol) into the reaction system, add 160 ml of toluene, 80 mL of absolute ethanol, 80 mL of pure water, and add Pd(PPh 3 ) 4(0.81 g, 0.7 mmol), refluxed at 100 °C for 24 h under nitrogen protection, then cooled to 25 °C, filtered by suction, the filter cake was rinsed with petroleum ether, the filter cake was dried in vacuo, 100 ml of dichloromethane was added to dissolve it, the solution was subjected to column chromatography (200 - 300 mesh, 450 g), the eluent was DCM:PE = 3:1, the receiving solution was rotated until no liquid flowed out, petroleum ether was added and stirred for 20 min, filtered by suction, the filter cake was rinsed with petroleum ether, the filter cake was dried in vacuo, to obtain the shown compound of formula Ⅲ - 040 (17.09 g, yield 81%). The intermediate compound of formula Ⅲ - 040 was subjected to the following analysis and testing:

[0106] HPLC purity: greater than 99.5%;

[0107] Mass spectrometry: calculated value is 301.36; measured value is 301.54.

[0108] Elemental analysis: calculated values are C: 83.70; H: 5.35; F: 6.30; N: 4.65. Measured values are C: 83.72; H: 5.33; F: 6.31; N: 4.64.

[0109] Under a nitrogen protection system, weigh out the ligand Ⅲ - 040 (15.07 g, 50 mmol), IrC1 3 ·3H 2 0 (7.05 g, 20 mmol) was placed into the reaction system, 350 mL of a mixed solution of ethylene glycol monoethyl ether and 150 mL of pure water was added, refluxed for 26 hours under nitrogen protection, then cooled to room temperature, a precipitate was formed, the precipitate was filtered by suction, rinsed and dried successively with water, absolute ethanol, and petroleum ether. The mass of the bridged ligand Ⅱ - 040 obtained as a dark red powder was 9.94 g, and the yield was 60%.

[0110] Weigh out the bridged ligand Ⅱ - 040 (9.11 g, 5.5 mmol), add anhydrous potassium carbonate (7.59 g, 55 mmol), then add 180 ml of ethylene glycol monoethyl ether to the system, displace nitrogen three times, add 3,7 - diethyl - 1,1,1 - trifluoro - 9 - methyldodecane - 4,6 - dione (4.86 g, 16.5 mmol) under nitrogen, reflux for 22 hours under nitrogen protection, cool down, filter by suction, wash with alcohol, and dry. Using dichloromethane as the solvent, column chromatography was carried out with neutral alumina, the filtrate was concentrated and a solid was precipitated. Finally, the organophosphorus luminescent material shown as Ⅰ - 040 was obtained, with a mass of 3.83 g and a yield of 32%.

[0111] The organometallic compound Ⅰ - 040 was subjected to the following analysis and testing:

[0112] HPLC purity: greater than 99.5%;

[0113] Mass spectrometry: Calculated value is 1087.29; measured value is 1087.51.

[0114] Elemental analysis: Calculated values are C: 62.97; H: 5.10; F: 8.74; Ir: 17.68; N: 2.58; O: 2.94. Measured values are C: 62.95; H: 5.12; F: 8.76; Ir: 17.66; N: 2.59; O: 2.93.

[0115] Synthesis Example 3

[0116] This synthesis example provides an organometallic compound I-049, that is, the compound numbered I-049. The specific synthesis steps are as follows:

[0117] Under a nitrogen protection system, weigh compound IV-049 (4-chloro-7-fluorobenzo[f]isoquinoline, CAS: 2414465-05-5) (16.22 g, 70 mmol), formula V-049 (3,5-dimethylphenylboronic acid, CAS: 172975-69-8) (11.55 g, 77 mmol), and anhydrous potassium carbonate (28.98 g, 210 mmol) into the reaction system. Add 200 ml of toluene, 100 mL of absolute ethanol, and 100 mL of pure water. Under nitrogen protection, add Pd(PPh 3 ) 4 (0.81 g, 0.7 mmol). Reflux at 100 °C for 24 h under nitrogen protection, then cool to 25 °C, filter by suction. Wash the filter cake with petroleum ether, dry the filter cake under vacuum. Dissolve the product in 150 ml of toluene, heat to 110 °C to dissolve, cool to 25 °C to precipitate, filter by suction. Wash the filter cake with petroleum ether, dry under vacuum at 50 °C to obtain the shown compound formula III-049 (22.90 g, yield 76%). Analyze and test the intermediate compound formula III-049 as follows:

[0118] HPLC purity: greater than 99.5%;

[0119] Mass spectrometry: Calculated value is 301.36; measured value is 301.41.

[0120] Elemental analysis: Calculated values are C: 83.70; H: 5.35; F: 6.30; N: 4.65. Measured values are C: 83.72; H: 5.32; F: 6.30; N: 4.66.

[0121] Under a nitrogen protection system, weigh ligand III-049 (15.07 g, 50 mmol), IrC1 3 ·3H 20 (7.76 g, 22 mmol) was placed into the reaction system. A mixed solution of 360 mL of ethylene glycol monoethyl ether and 120 mL of pure water was added. Under nitrogen protection, the mixture was refluxed for 26 hours, and then cooled to room temperature. A precipitate was formed. The precipitate was filtered by suction and washed successively with water, absolute ethanol, and petroleum ether, and then dried. The mass of the bridged ligand II-049 obtained as a dark red powder was 10.57 g, and the yield was 58%.

[0122] Weigh the bridged ligand II-049 (9.94 g, 6 mmol), add potassium carbonate anhydrous (8.28 g, 60 mmol), and then add 200 ml of ethylene glycol monoethyl ether to the system. Nitrogen was displaced three times, and 3,7-diethyl-1,1,1-trifluoro-9-methyldodecane-4,6-dione (5.30 g, 18 mmol) was added under nitrogen. Under nitrogen protection, the mixture was refluxed for 22 hours, cooled, filtered by suction, washed with alcohol, and dried. Dichloromethane was used as the solvent, and column chromatography on neutral alumina was carried out. The filtrate was concentrated and a solid was precipitated. Finally, the organophosphorus luminescent material shown as I-049 was obtained, with a mass of 3.78 g and a yield of 29%.

[0123] The organometallic compound I-049 was subjected to the following analytical tests:

[0124] HPLC purity: greater than 99.5%;

[0125] Mass spectrometry: calculated value was 1087.29; measured value was 1087.62.

[0126] Elemental analysis: calculated values were C: 62.97; H: 5.10; F: 8.74; Ir: 17.68; N: 2.58; O: 2.94. Measured values were C: 62.95; H: 5.12; F: 8.73; Ir: 17.69; N: 2.55; O: 2.97.

[0127] Synthesis Example 4

[0128] This synthesis example provides an organometallic compound I-075, namely the compound numbered I-075. The specific synthesis steps are as follows:

[0129]

[0130] Under a nitrogen protection system, weigh compound VIII-075 (1,6-dichloroisoquinoline, CAS: 630421-73-7) (49.51 g, 250 mmol) and put it into the reaction system. Add 500 mL of n-heptane. Cool down to 0 °C under nitrogen protection, and dropwise add N,N-dimethylethanolamine (49.02 g, 550 mmol). Keep the internal temperature at ±5 °C and react for 3 h. Then dropwise add n-BuLi (220 mL, 550 mmol, 2.5 M). Keep the internal temperature at ±5 °C and react for 3 h. Then start to add 100 mL of D2O, stir for 30 min, let it stand for liquid separation, rotary evaporate the organic phase. Dissolve the reaction solution in 200 mL of developing agent EA:PE = 1:15. Column chromatograph the solution (200 - 300 mesh, 700 g) with the developing agent EA:PE = 1:15. Rotary evaporate the receiving solution until no liquid flows out to obtain the shown compound formula VII-075 (17.71 g, yield 65%). Analyze and test the intermediate compound formula VII-075 as follows:

[0131] HPLC purity: greater than 99.5%;

[0132] Mass spectrometry: calculated value is 200.06; measured value is 200.21.

[0133] Elemental analysis: calculated values are C: 54.03; H: 3.53; Cl: 35.44; N: 7.00. Measured values are C: 54.02; H: 3.52; Cl: 35.43; N: 7.03.

[0134] Under a nitrogen protection system, weigh compound VII-075 (22.01 g, 110 mmol), formula VI-075 (cyclopentylmethylboronic acid, CAS: 848029-29-8) (14.08 g, 110 mmol), and anhydrous potassium carbonate (45.54 g, 330 mmol) and put them into the reaction system. Add 220 ml of toluene, 110 mL of absolute ethanol, and 110 mL of pure water. Add Pd(PPh 3 ) 4 (1.27 g, 1.1 mmol) under nitrogen protection. Reflux at 100 °C for 24 h, then cool to 25 °C, filter by suction. Wash the filter cake with petroleum ether, vacuum dry the filter cake. Dissolve the filter cake in 600 ml of dichloromethane. Column chromatograph the solution (200 - 300 mesh, 800 g) with the developing agent DCM:PE = 2:1. Rotary evaporate the receiving solution until no liquid flows out. Add petroleum ether and stir for 20 min, filter by suction. Wash the filter cake with petroleum ether, vacuum dry the filter cake to obtain the shown compound formula IV-075 (17.71 g, yield 65%). Analyze and test the intermediate compound formula IV-075 as follows:

[0135] HPLC purity: greater than 99.5%;

[0136] Mass spectrometry: calculated value is 247.76; measured value is 247.84.

[0137] Elemental analysis: calculated values are C: 72.72; H: 7.32; Cl: 14.31; N: 5.65. Measured values are C: 72.70; H: 7.34; Cl: 14.32; N: 5.64.

[0138] Under a nitrogen protection system, weigh compound Ⅳ-075 (17.34 g, 70 mmol), formula Ⅴ-075 (3,5-dimethylphenylboronic acid, CAS: 172975-69-8) (11.55 g, 77 mmol), and anhydrous potassium carbonate (28.98 g, 210 mmol) into the reaction system. Add 210 ml of toluene, 105 mL of absolute ethanol, and 105 mL of purified water. Under nitrogen protection, add Pd(PPh 3 ) 4 (0.81 g, 0.7 mmol). Reflux at 100 °C for 24 h under nitrogen protection, then cool to 25 °C, filter by suction. Wash the filter cake with petroleum ether, dry the filter cake under vacuum. Add 200 ml of dichloromethane to dissolve it. Subject the solution to column chromatography (200 - 300 mesh, 500 g) with the developing solvent DCM:PE = 3:1. Rotate the receiving solution until no liquid flows out. Add petroleum ether and stir for 20 min, filter by suction. Wash the filter cake with petroleum ether, dry the filter cake under vacuum to obtain the shown compound formula Ⅲ-075 (17.78 g, yield 80%). Analyze and test the intermediate compound formula Ⅲ-075 as follows:

[0139] HPLC purity: greater than 99.5%;

[0140] Mass spectrometry: calculated value is 317.47; measured value is 317.52.

[0141] Elemental analysis: calculated values are C: 87.02; H: 8.57; N: 4.41. Measured values are C: 87.05; H: 8.55; N: 4.40.

[0142] Under a nitrogen protection system, weigh ligand Ⅲ-075 (15.87 g, 50 mmol), IrC1 3 ·3H 2 0 (7.76 g, 22 mmol) into the reaction system. Add a mixed solution of 450 mL of ethylene glycol monoethyl ether and 150 mL of purified water. Reflux for 26 hours under nitrogen protection, then cool to room temperature. Precipitation occurs. Filter the precipitate by suction and wash and dry it successively with water, absolute ethanol, and petroleum ether. The mass of the bridged ligand Ⅱ-075 obtained as a dark red powder is 10.79 g, and the yield is 57%.

[0143] Weigh the bridging ligand II-075 (10.33 g, 6 mmol), add anhydrous potassium carbonate (8.28 g, 60 mmol), then add 180 ml of ethylene glycol monoethyl ether to the system, displace nitrogen three times, and add 3,7-diethyl-1,1,1-trifluoro-9-methyldodecane-4,6-dione (7.06 g, 24 mmol) under nitrogen. Under nitrogen protection, reflux for 22 hours, cool down, filter by suction, wash with alcohol, and dry. Use dichloromethane as the solvent and perform column chromatography on neutral alumina. Concentrate the filtrate to precipitate the solid, and finally obtain the organophosphorus luminescent material shown in I-075, with a mass of 5.24 g and a yield of 39%.

[0144] Perform the following analytical tests on the organometallic compound I-075:

[0145] HPLC purity: greater than 99.5%;

[0146] Mass spectrometry: Calculated value is 1119.50; measured value is 1119.28.

[0147] Elemental analysis: Calculated values are C: 65.45; H: 6.93; F: 5.09; Ir: 17.17; N: 2.50; O: 2.86. Measured values are C: 65.47; H: 6.94; F: 5.06; Ir: 17.15; N: 2.54; O: 2.84.

[0148] Synthesis Example 5

[0149] This synthesis example provides an organometallic compound I-124, namely the compound numbered I-124. The specific synthesis steps are as follows:

[0150]

[0151] Under a nitrogen protection system, weigh the compound IV-124 (3-bromo-7-fluorobenzo[h]isoquinoline) (19.33 g, 70 mmol), formula V-124 (3,5-dimethylphenylboronic acid, CAS: 172975-69-8) (12.60 g, 84 mmol), and anhydrous potassium carbonate (28.98 g, 210 mmol) into the reaction system, add 200 ml of toluene, 100 mL of absolute ethanol, and 100 mL of pure water. Under nitrogen protection, add Pd(PPh 3 ) 4(0.81 g, 0.7 mmol), refluxed at 100 °C for 24 h under nitrogen protection, then cooled to 25 °C, filtered by suction, the filter cake was rinsed with petroleum ether, the filter cake was dried in vacuo, dissolved in 150 ml of dichloromethane, the solution was column chromatographed (200 - 300 mesh, 500 g) with the eluent DCM:PE = 4:1, the receiving solution was rotated until no liquid flowed out, the filter cake was dried in vacuo, and the shown compound Formula III - 124 (15.19 g, yield 72%) was obtained. The intermediate compound Formula III - 124 was subjected to the following analytical tests:

[0152] HPLC purity: greater than 99.5%;

[0153] Mass spectrometry: calculated value is 301.36; measured value is 301.49.

[0154] Elemental analysis: calculated values are C: 83.70; H: 5.35; F: 6.30; N: 4.65. Measured values are C: 83.72; H: 5.36; F: 6.30; N: 4.62.

[0155] Under a nitrogen protection system, weigh out the ligand III - 124 (15.07 g, 50 mmol), IrC1 3 ·3H 2 0 (7.05 g, 20 mmol) was placed into the reaction system, a mixed solution of 420 mL of ethylene glycol monoethyl ether and 140 mL of pure water was added, refluxed for 26 hours under nitrogen protection, then cooled to room temperature, a precipitate was formed, the precipitate was filtered by suction, rinsed and dried successively with water, absolute ethanol, and petroleum ether. The bridged ligand II - 124 as a dark red powder was obtained with a mass of 8.28 g and a yield of 50%.

[0156] Weigh out the bridged ligand II - 124 (8.28 g, 5 mmol), add anhydrous potassium carbonate (6.9 g, 50 mmol), then add 160 ml of ethylene glycol monoethyl ether to the system, displace nitrogen three times, add 3,7 - diethyl - 1,1,1 - trifluoro - 9 - methyldodecane - 4,6 - dione (5.15 g, 17.5 mmol) under nitrogen, reflux for 22 hours under nitrogen protection, cool down, filter by suction, wash with alcohol, and dry. Using dichloromethane as the solvent, column chromatography was carried out with neutral alumina, the filtrate was concentrated and a solid was precipitated, and finally the organophosphorus luminescent material shown as I - 124 was obtained with a mass of 4.46 g and a yield of 41%.

[0157] The organometallic compound I - 124 was subjected to the following analytical tests:

[0158] HPLC purity: greater than 99.5%;

[0159] Mass spectrometry: calculated value is 1087.29; measured value is 1087.51.

[0160] Elemental analysis: Calculated values are C: 62.97; H: 5.10; F: 8.74; Ir: 17.68; N: 2.58; O: 2.94. Measured values are C: 62.94; H: 5.15; F: 8.72; Ir: 17.65; N: 2.58; O: 2.97.

[0161] Synthesis Example 6

[0162] This synthesis example provides an organometallic compound I-148, that is, the compound numbered I-148. The specific synthesis steps are as follows:

[0163]

[0164] Under a nitrogen protection system, weigh compound IV-148 (4-chloro-7-fluorobenzo[f]isoquinoline, CAS: 2414465-05-5) (16.22 g, 70 mmol), formula V-148 (3,5-difluorophenylboronic acid, CAS: 156545-07-2) (13.26 g, 84 mmol), and anhydrous potassium carbonate (28.98 g, 210 mmol) into the reaction system. Add 190 ml of toluene, 95 mL of absolute ethanol, and 95 mL of pure water. Under nitrogen protection, add Pd(PPh 3 ) 4 (0.81 g, 0.7 mmol). Reflux at 100 °C for 24 h under nitrogen protection, then cool to 25 °C, filter by suction. Wash the filter cake with petroleum ether, dry the filter cake under vacuum. Add 100 ml of dichloromethane to dissolve it. Subject the solution to column chromatography (200 - 300 mesh, 450 g) with the eluent DCM:PE = 2:1. Rotate the receiving solution until no liquid flows out. Dry the filter cake under vacuum to obtain the shown compound formula III-148 (17.75 g, yield 82%). Analyze and test the intermediate compound formula III-148 as follows:

[0165] HPLC purity: greater than 99.5%;

[0166] Mass spectrometry: Calculated value is 309.29; Measured value is 309.46.

[0167] Elemental analysis: Calculated values are C: 73.78; H: 3.26; F: 18.43; N: 4.53. Measured values are C: 73.79; H: 3.25; F: 18.45; N: 4.51.

[0168] Under a nitrogen protection system, weigh ligand III-148 (15.46 g, 50 mmol), IrC1 3 ·3H 20 (7.05 g, 20 mmol) was placed into the reaction system, and a mixed solution of 360 mL of ethylene glycol monoethyl ether and 120 mL of pure water was added. Under nitrogen protection, the mixture was refluxed for 26 hours, then cooled to room temperature, and a precipitate formed. The precipitate was filtered by suction and washed successively with water, absolute ethanol, and petroleum ether, and then dried. The obtained dark red powder of the bridging ligand II-148 had a mass of 9.96 g and a yield of 59%.

[0169] Weigh the bridging ligand II-148 (9.29 g, 5.5 mmol), add anhydrous potassium carbonate (7.59 g, 55 mmol), and then add 170 ml of ethylene glycol monoethyl ether to the system. Nitrogen was displaced three times, and 3,7-diethyl-1,1,1-trifluoro-9-methyldodecane-4,6-dione (4.05 g, 13.75 mmol) was added under nitrogen. Under nitrogen protection, the mixture was refluxed for 22 hours, cooled, filtered by suction, washed with alcohol, and dried. Using dichloromethane as the solvent, column chromatography was performed on neutral alumina. The filtrate was concentrated and a solid precipitated. Finally, the organophosphorus luminescent material shown in I-148 was obtained, with a mass of 4.61 g and a yield of 38%.

[0170] The organometallic compound I-148 was subjected to the following analytical tests:

[0171] HPLC purity: greater than 99.5%;

[0172] Mass spectrometry: calculated value was 1103.14; measured value was 1103.69.

[0173] Elemental analysis: calculated values were C: 57.71; H: 3.93; F: 15.50; Ir: 17.42; N: 2.54; O: 2.90. Measured values were C: 57.70; H: 3.94; F: 15.51; Ir: 17.43; N: 2.51; O: 2.91.

[0174] Synthesis Example 7

[0175] This synthesis example provides an organometallic compound I-153, that is, the compound numbered I-153. The specific synthesis steps are as follows:

[0176]

[0177] Under a nitrogen protection system, weigh the compound IV-153 (4-chloro-7-fluorobenzo[f]isoquinoline) (16.22 g, 70 mmol), formula V-153 (4-fluoro-3-methylphenylboronic acid, CAS: 139911-27-6) (11.85 g, 77 mmol), and anhydrous potassium carbonate (28.98 g, 210 mmol) and place them into the reaction system. Add 160 ml of toluene, 80 mL of absolute ethanol, and 80 mL of pure water. Under nitrogen protection, add Pd(PPh 3) 4 (0.81 g, 0.7 mmol), refluxed at 100 °C for 24 h under nitrogen protection, then cooled to 25 °C, filtered by suction, the filter cake was rinsed with petroleum ether, the filter cake was dried in vacuo, the product was dissolved in 150 ml of toluene, heated to 110 °C for dissolution, cooled to 25 °C for precipitation, filtered by suction, the filter cake was rinsed with petroleum ether, and dried in vacuo at 50 °C to obtain the shown compound of formula III-153 (17.10 g, yield 80%). The intermediate compound of formula III-153 was subjected to the following analytical tests:

[0178] HPLC purity: greater than 99.5%;

[0179] Mass spectrometry: calculated value is 305.33; measured value is 305.38.

[0180] Elemental analysis: calculated values are C: 78.68; H: 4.29; F: 12.44; N: 4.59. Measured values are C: 78.69; H: 4.28; F: 12.47; N: 4.56.

[0181] Under a nitrogen protection system, weigh out the ligand III-153 (15.27 g, 50 mmol), IrC1 3 ·3H 2 0 (7.76 g, 22 mmol) and place it into the reaction system. Add a mixed solution of 360 mL of ethylene glycol monoethyl ether and 120 mL of pure water. Reflux for 26 hours under nitrogen protection, then cool to room temperature. Precipitation occurs. Filter the precipitate by suction and rinse and dry it successively with water, absolute ethanol, and petroleum ether. The mass of the bridged ligand II-153 obtained as a dark red powder is 11.41 g, and the yield is 62%.

[0182] Weigh out the bridged ligand II-153 (9.20 g, 5.5 mmol), add anhydrous potassium carbonate (7.59 g, 55 mmol), then add 170 ml of ethylene glycol monoethyl ether to the system, displace nitrogen three times, add 3,7-diethyl-1,1,1-trifluoro-9-methyldodecane-4,6-dione (4.86 g, 16.5 mmol) under nitrogen, reflux for 22 hours under nitrogen protection, cool down, filter by suction, wash with alcohol, and dry. Use dichloromethane as the solvent and perform column chromatography on neutral alumina. The filtrate is concentrated and the solid precipitates. Finally, the organophosphorus luminescent material shown as I-153 is obtained, with a mass of 3.86 g and a yield of 32%.

[0183] The organometallic compound I-153 was subjected to the following analytical tests:

[0184] HPLC purity: greater than 99.5%;

[0185] Mass spectrometry: calculated value is 1095.21; measured value is 1095.45.

[0186] Elemental analysis: Calculated values are C: 60.32; H: 4.51; F: 12.14; Ir: 17.55; N: 2.56; O: 2.92. Measured values are C: 60.33; H: 4.50; F: 12.12; Ir: 17.54; N: 2.59; O: 2.92.

[0187] Synthesis Example 8

[0188] This synthesis example provides an organometallic compound I-160, that is, the compound numbered I-160. The specific synthesis steps are as follows:

[0189]

[0190] Under a nitrogen protection system, weigh compound IV-160 (2-chloro-4,5,7-trimethyl-quinoline, CAS: 329210-71-1) (14.40 g, 70 mmol), formula V-160 ([4-(tert-butyl)naphthalene]-2-boronic acid pinacol ester, CAS: 2217657-10-6) (23.89 g, 77 mmol), and anhydrous potassium carbonate (28.98 g, 210 mmol) into the reaction system. Add 190 ml of toluene, 95 mL of anhydrous ethanol, and 95 mL of pure water. Under nitrogen protection, add Pd(PPh 3 ) 4 (0.81 g, 0.7 mmol). Reflux at 100 °C for 24 h under nitrogen protection, then cool to 25 °C, filter by suction. Wash the filter cake with petroleum ether, dry the filter cake under vacuum, dissolve it in 200 ml of dichloromethane, subject the solution to column chromatography (200 - 300 mesh, 500 g), with the eluent DCM:PE = 1:1. Rotate the receiving solution until no liquid flows out, dry the filter cake under vacuum to obtain the shown compound formula III-160 (21.28 g, yield 86%). Analyze and test the intermediate compound formula III-160 as follows:

[0191] HPLC purity: greater than 99.5%;

[0192] Mass spectrometry: Calculated value is 353.51; Measured value is 353.87.

[0193] Elemental analysis: Calculated values are C: 88.34; H: 7.70; N: 3.96. Measured values are C: 88.32; H: 7.73; N: 3.95.

[0194] Under a nitrogen protection system, weigh ligand III-160 (21.21 g, 60 mmol), IrC1 3 ·3H 20 (8.46 g, 24 mmol) was placed into the reaction system, and a mixed solution of 420 mL of ethylene glycol monoethyl ether and 140 mL of pure water was added. It was refluxed for 26 hours under nitrogen protection, then cooled to room temperature, and a precipitate was formed. The precipitate was filtered by suction and washed successively with water, absolute ethanol, and petroleum ether, and then dried. The mass of the bridged ligand II-160 obtained as a dark red powder was 11.19 g, and the yield was 50%.

[0195] Weigh the bridged ligand II-160 (11.19 g, 6 mmol), add potassium carbonate anhydrous (8.28 g, 60 mmol), and then add 180 ml of ethylene glycol monoethyl ether to the system. Nitrogen was displaced three times, and 3,7-diethyl-1,1,1-trifluoro-9-methyldodecane-4,6-dione (6.18 g, 21 mmol) was added under nitrogen. Under nitrogen protection, it was refluxed for 22 hours, cooled, filtered by suction, washed with alcohol, and dried. Dichloromethane was used as the solvent, and it was chromatographed on a neutral alumina column. The filtrate was concentrated and a solid was precipitated. Finally, the organic phosphorus luminescent material shown as I-160 was obtained, with a mass of 6.29 g and a yield of 44%.

[0196] The organometallic compound I-160 was subjected to the following analytical tests:

[0197] HPLC purity: greater than 99.5%;

[0198] Mass spectrometry: calculated value was 1191.58; measured value was 1191.37.

[0199] Elemental analysis: calculated values were C: 67.54; H: 6.51; F: 4.78; Ir: 16.13; N: 2.35; O: 2.69. Measured values were C: 67.55; H: 6.50; F: 4.76; Ir: 16.15; N: 2.38; O: 2.66.

[0200] The synthesis methods of other compounds were the same as above and will not be elaborated one by one here. The mass spectrometry or molecular formulas of other synthesis examples are shown in Table 1 below:

[0201] Table 1

[0202] Compound Molecular formula Calculated value of mass spectrum Measured value of mass spectrum Formula Ⅰ-004 <![CDATA[C 61 H 72 F 3 IrN 2 O 2 > 1114.47 1114.68 Formula Ⅰ-028 <![CDATA[C 45 H 55 D 6 F 3 Ge 2 IrN 2 O 2 > 1062.50 1062.27 Formula Ⅰ-052 <![CDATA[C 57 H 43 D 12 F 5 IrN 2 O 2 > 1099.36 1099.58 Formula Ⅰ-108 <![CDATA[C 59 H 55 F 9 IrN 2 O 2 > 1187.30 1187.62 Formula Ⅰ-139 <![CDATA[C 57 H 43 D 12 F 5 IrN 2 O 2 > 1099.36 1099.52 Formula Ⅰ-150 <![CDATA[C 73 H 80 F 3 IrN 2 O 2 S 2 > 1330.79 1330.51

[0203] Example 1

[0204] Device Fabrication

[0205] The ITO glass substrate with a coating thickness of 150 nm was placed in distilled water and washed twice, ultrasonically washed for 30 minutes, repeatedly washed with distilled water twice, ultrasonically washed for 10 minutes. After the distilled water washing was completed, solvents such as isopropanol, acetone, and methanol were ultrasonically washed in sequence and then dried. It was transferred to a plasma cleaner, and the above substrate was washed for 5 minutes and then sent to an evaporation coater. First, compound HT-12 was vacuum-evaporated on ITO (anode) to form a hole injection layer with a thickness of 55 nm; on the hole injection layer, compound HT-7 material was vacuum-evaporated to form a hole transport layer with a thickness of 35 nm, and the evaporation rate was 0.1 nm / s; an electroluminescent layer was formed on the above hole transport layer. The specific operation was as follows: The host material of the present invention, Host-01, as the light-emitting layer was placed in a chamber of a vacuum vapor deposition device, and the dopant I-001 was placed in another chamber of the vacuum vapor deposition device. The two materials were evaporated simultaneously at different rates, and the concentration of I-001 was 6%, and the total evaporation film thickness was 40 nm; on the light-emitting layer, ET-5 was vacuum-evaporated to form an electron transport layer with a film thickness of 20 nm, and its evaporation rate was 0.1 nm / s; on the electron transport layer (ETL), LiF with a thickness of 0.5 nm was vacuum-evaporated as an electron injection layer, and on the electron injection layer, an Al layer with a thickness of 150 nm was vacuum-evaporated as the cathode of the device.

[0206] Example 2

[0207] Referring to the method of Example 1 above, the only difference was that the doping material I-001 was replaced with I-004.

[0208] Example 3

[0209] Referring to the method of Example 1 above, the only difference was that the doping material I-001 was replaced with I-028.

[0210] Example 4

[0211] Referring to the method of Example 1 above, the only difference was that the doping material I-001 was replaced with I-040.

[0212] Example 5

[0213] Referring to the method of Example 1 above, the only difference was that the doping material I-001 was replaced with I-049.

[0214] Example 6

[0215] Referring to the method of Example 1 above, the only difference was that the doping material I-001 was replaced with I-052.

[0216] Example 7

[0217] Referring to the method of Example 1 above, the only difference is that the doping material I-001 is replaced with I-075.

[0218] Example 8

[0219] Referring to the method of Example 1 above, the only difference is that the doping material I-001 is replaced with I-108.

[0220] Example 9

[0221] Referring to the method of Example 1 above, the only difference is that the doping material I-001 is replaced with I-124.

[0222] Example 10

[0223] Referring to the method of Example 1 above, the only difference is that the doping material I-001 is replaced with I-139.

[0224] Example 11

[0225] Referring to the method of Example 1 above, the only difference is that the doping material I-001 is replaced with I-148.

[0226] Example 12

[0227] Referring to the method of Example 1 above, the only difference is that the doping material I-001 is replaced with I-150.

[0228] Example 13

[0229] Referring to the method of Example 1 above, the only difference is that the doping material I-001 is replaced with I-153.

[0230] Example 14

[0231] Referring to the method of Example 1 above, the only difference is that the doping material I-001 is replaced with I-160.

[0232] Comparative Example 1

[0233] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the compound (btp)2Ir(acac) was used to replace the doping compound I-001 in Example 1.

[0234] Comparative Example 2

[0235] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the compound PRD-01 was used to replace the doping compound I-001 in Example 1.

[0236] Comparative Example 3

[0237] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the doping compound I-001 in Example 1 was replaced with PRD-02.

[0238] Comparative Example 4

[0239] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the doping compound I-001 in Example 1 was replaced with PRD-03.

[0240] Comparative Example 5

[0241] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the doping compound I-001 in Example 1 was replaced with PRD-04.

[0242] Comparative Example 6

[0243] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the doping compound I-001 in Example 1 was replaced with PRD-05.

[0244] Comparative Example 7

[0245] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the doping compound I-001 in Example 1 was replaced with PRD-06.

[0246] Comparative Example 8

[0247] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the doping compound I-001 in Example 1 was replaced with PRD-07.

[0248] Comparative Example 9

[0249] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the doping compound I-001 in Example 1 was replaced with PRD-08.

[0250] Comparative Example 10

[0251] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the doping compound I-001 in Example 1 was replaced with PRD-09.

[0252] Comparative Example 11

[0253] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the doping compound I-001 in Example 1 was replaced with PRD-10.

[0254] Comparative Example 12

[0255] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the doping compound Ⅰ-001 in Example 1 was replaced with PRD-11.

[0256] Comparative Example 13

[0257] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the doping compound Ⅰ-001 in Example 1 was replaced with PRD-12.

[0258] Comparative Example 14

[0259] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the doping compound Ⅰ-001 in Example 1 was replaced with PRD-13.

[0260] The structures of the compounds used are as follows:

[0261]

[0262]

[0263] The driving voltage, luminous efficiency, and lifetime of the organic electroluminescent devices obtained from the above device examples and device comparative examples were characterized at a brightness of 1000 (nits). The test results are shown in Table 2 below:

[0264] Table 2

[0265]

[0266]

[0267] As can be seen from Table 2, compared with the organic electroluminescent devices prepared in the comparative examples, the organic electroluminescent devices prepared using the compounds provided by the present invention as the doping materials for the light-emitting layer have significantly reduced driving voltages, and significantly improved luminous efficiency and lifetime. The driving voltage of the organic electroluminescent device of the present invention is as low as below 3.81 V, the luminous efficiency is as high as above 55.7 cd / A, and the device lifetime is above 925 h.

[0268] The above examples only list the effect data of the devices made of a part of the structural formulas. This is a representative sampling test. Judging from the experimental data, the overall data do not differ much and can represent the effects of other unlisted structures.

[0269] The applicant declares that the present invention illustrates the organometallic complex and its application of the present invention through the above embodiments, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, the equivalent substitution of each raw material of the products of the present invention, the addition of auxiliary components, the selection of specific methods, etc., all fall within the protection scope and the disclosure scope of the present invention.

Claims

1. An organometallic complex, characterized in that: The organometallic complex is selected from one of the following structures: ； ； ； Where D stands for deuterium.

2. An organic photoelectric material, characterized in that: The organic photoelectric material comprises any one or a combination of at least two of the organic metal complexes as claimed in claim 1.

3. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a first electrode, a second electrode and an organic thin film layer disposed between the first electrode and the second electrode, wherein the organic thin film layer comprises the organic metal complex as claimed in claim 1 .

4. The organic electroluminescent device according to claim 3, characterized in that: The organic thin film layer is a light-emitting layer, and the light-emitting layer comprises a main material and a doping material, and the doping material is the organic metal complex according to claim 1.

5. The organic electroluminescent device according to claim 4, characterized in that: The percentage of the doping material in the total material mass of the light-emitting layer is 0.5-10%.

6. The organic electroluminescent device according to claim 4, characterized in that: The organic thin film layer further comprises any one of a hole injection layer, a hole transport layer, a luminescence auxiliary layer, an electron blocking layer, a hole blocking layer, an electron transport layer or an electron injection layer, or a combination of at least two layers.

7. A display panel, characterized in that: The display panel comprises the organic electroluminescent device according to any one of claims 3 to 6.

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