Iridium metal heterocyclic complex luminescent material, preparation method and organic electroluminescent device

Abstract

The invention belongs to the field of organic electroluminescence, and provides an iridium metal heterocyclic complex luminescent material, a preparation method and an organic electroluminescent device. The structural general formula of the iridium metal heterocyclic complex light-emitting material is as follows: # imgabs0. According to the iridium metal heterocyclic complex light-emitting material provided by the invention, a di (2-phenylpyridine) ligand with a substituent group and a specific heterocyclic ligand are combined with iridium metal, so that the wavelength of a compound is adjusted, and an organic light-emitting material with certain symmetry is obtained. After the compound is applied to the organic electroluminescent device, the driving voltage of the organic electroluminescent device is reduced, the luminous efficiency is improved, and the service life is prolonged.

Description

Technical Field

[0001] The invention belongs to the field of organic photoelectric materials, relates to organic synthesis and organic photoelectric materials, and specifically relates to an iridium metal heterocyclic complex luminescent material, a preparation method and an organic electroluminescent device. Background Art

[0002] As a promising solid-state lighting technology, OLEDs are under active development. They have attracted considerable attention in research over the past few decades and have made remarkable progress. Recent achievements in efficiency and life span have not only facilitated commercial mass production, but also shifted the focus to the exploration of production costs, yields, and aesthetic features that distinguish them from their inorganic counterparts. Compared with other point-like lighting sources, OLEDs are unique in that they emit light directly from the surface, have a wider illumination range, can achieve the same luminous flux at lower light intensities, and have higher efficiency. In terms of light characteristics, OLEDs emit a soft, diffuse light, similar to traditional incandescent lamps, which helps create a visually comfortable atmosphere with the added benefit of energy efficiency.

[0003] The materials of the OLED light-emitting part are mainly organic fluorescent materials, which can be roughly divided into three types: red light, blue light, and green light. In recent studies, it was found that in the electroluminescence of organic fluorescent materials, the generation of singlet excitons and triplet excitons usually follows a 1:3 ratio determined by spin statistics. Unlike traditional fluorescent materials that rely only on singlet excitons, organic phosphors can increase the internal quantum efficiency to 100% by adding heavy metals. These metals promote stable spin-orbit coupling and promote the mixing of singlets and triplets. Therefore, in recent years, people have been committed to the research of heavy metal coordinated organic fluorescent materials, especially the research of metal iridium complex organic fluorescent materials. However, the currently disclosed luminescent materials have high synthesis prices and synthesis process requirements, and have the disadvantages of high purification requirements, short life, and low efficiency during the synthesis process. Therefore, the development of a material with high luminescence efficiency and long life is a technical problem that needs to be solved at present. Summary of the invention

[0004] In view of this, the present invention provides an iridium metal heterocyclic complex luminescent material, a preparation method and an organic electroluminescent device. The organic fluorescent material prepared by the present invention can be used as the light-emitting part of the organic electroluminescent device, which can improve the luminous efficiency and extend the service life of the device.

[0005] In order to achieve the above object, the present invention adopts the following technical solution:

[0006] The first technical purpose of the present invention is to provide an iridium metal heterocyclic complex luminescent material, the general structural formula of the iridium metal heterocyclic complex luminescent material is as shown in Formula I:

[0007]

[0008] wherein R1 to R7 each independently represent hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amino, sulfonic acid, substituted or unsubstituted C1-C 50 Alkyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C5-C 50 Heteroaryl, substituted or unsubstituted C3-C 50 Cycloalkyl, substituted or unsubstituted C1-C 50 Alkoxy, substituted or unsubstituted C1-C 50 Alkylamino, substituted or unsubstituted C2-C 50 Alkenyl or alkyne, substituted or unsubstituted C2-C 50 Heterocyclyl, substituted or unsubstituted C 10 -C 50 Condensed ring group, substituted or unsubstituted C5-C 50 Spirocyclyl, substituted or unsubstituted C1-C 50 Silane, substituted or unsubstituted C1-C 50 The substituents at the positions of R1 to R7 are the same or different; the positions of R1 to R7 are any positions of the benzene ring, the number of R1 to R4 substituents is 0 to 4, and the number of R5 to R7 substituents is 0 to 2.

[0009] Preferably, the R1 to R7 each independently represent hydrogen, deuterium, cyano, substituted or unsubstituted C1-C 15 Alkyl, substituted or unsubstituted C6-C 15 Aryl, substituted or unsubstituted C3-C 15 Cycloalkyl, substituted or unsubstituted C1-C 15 Alkoxy, substituted or unsubstituted C2-C 15 Heterocyclic, substituted or unsubstituted C 10 -C 20 Condensed ring group, substituted or unsubstituted C1-C 15 Silane, substituted or unsubstituted C1-C 15 Germanyl.

[0010] Preferably, the substituted or unsubstituted C1-C 15 The alkyl group includes any one of methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, isopentyl, neopentyl, hexyl, 2-methylpentyl, 3-methylpentyl, 2,3-dimethylbutyl and 2,2-dimethylbutyl.

[0011] Preferably, the substituted or unsubstituted C6-C 15The aryl group includes any one of phenyl, tolyl, chlorophenyl, bromophenyl, fluorophenyl, biphenyl, terphenyl, naphthyl, anthracenyl and phenanthryl.

[0012] Preferably, the substituted or unsubstituted C3-C 15 The cycloalkyl group includes any one of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.

[0013] Preferably, the substituted or unsubstituted C1-C 15 The alkoxy group includes any one of a methoxy group, an ethoxy group, a propoxy group, and a phenoxy group.

[0014] Preferably, the substituted or unsubstituted C2-C 15 The heterocyclic group includes an aromatic or non-aromatic cyclic group containing at least one heteroatom, wherein the heteroatom is selected from one or more combinations of O, S, N, P, B, Si, and Se.

[0015] Preferably, the R1 to R7 can be arbitrarily combined to form a substituted or unsubstituted condensed ring, and the substituents that do not form a condensed ring include hydrogen, deuterium, cyano, substituted or unsubstituted C1-C 50 Alkyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C3-C 15 Cycloalkyl, substituted or unsubstituted C2-C 50 Heterocyclic, substituted or unsubstituted C 10 -C 20 A fused ring group, a substituted or unsubstituted C5-C 50 The spirocyclic group may or may not include any one or more combinations of O, S, N, P, B, Si, and Se in the formed condensed ring.

[0016] Preferably, the hydrogen atoms in the groups or substituent groups of R1 to R7 may be deuterated.

[0017] Specifically, the iridium metal heterocyclic complex luminescent material is selected from any one of the compounds represented by the following structural formulas:

[0018]

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[0091] The second technical purpose of the present invention is to provide a method for preparing the iridium metal heterocyclic complex luminescent material. The iridium metal heterocyclic complex luminescent material of the present invention can be prepared by a synthetic method known to those skilled in the art. Alternatively, the following reaction process is preferably used for preparation, and the specific synthetic route is as follows:

[0092]

[0093] In the above formula, R1 to R7 are as defined in the above general formula I.

[0094] Specific preparation method:

[0095] S1. Under a nitrogen atmosphere, hexane and TMEDA are added to the compound of formula II, and then alkyl lithium is added to react at a low temperature to prepare formula III, and then a halogen boron reagent is added dropwise to prepare formula IV;

[0096] S2. Under a nitrogen atmosphere, a compound of formula IV, a compound of formula IX, tetrakis(triphenylphosphine)palladium, toluene, EtOH, sodium carbonate, and water are reacted to prepare a compound of formula V;

[0097] S3. At a certain temperature and under a nitrogen atmosphere, the compound of formula VI is reacted with iridium trichloride in a mixed solution of ethylene glycol ether and water to obtain a compound of formula VII;

[0098] S4. At a certain temperature and under a nitrogen atmosphere, the compound of formula Ⅶ is reacted with silver trifluoromethanesulfonate in a mixed solution of methanol and dichloromethane to obtain a compound of formula Ⅷ;

[0099] S5. Under a nitrogen atmosphere, react the compound of formula V with the compound of formula VIII in a single solvent of EtOH or ethylene glycol ethyl ether, and obtain a compound of formula I after post-treatment, namely the iridium metal heterocyclic complex luminescent material.

[0100] Preferably, the alkyl lithium used in step S1 is n-butyl lithium, tert-butyl lithium, or hexyl lithium, n-butyl lithium is in 1.5M or 2.5M hexane solvent, tert-butyl lithium is in 1.2M or 1.5M hexane solvent, and hexyl lithium is in 2.4M or 2.5M hexane solvent; the molar ratio of the compound of formula II to the alkyl lithium is (1.05-1.25):1, and the amount of hexane added is 5-6 times the equivalent of the compound of formula II.

[0101] Further, the molar ratio of TMEDA to alkyl lithium is 1:(1-1.2); the temperature range of the low temperature reaction is -30°C to -5°C. Further, the halogen boron reagent includes (NMe2)ClB-BCl(NMe2), (NEt2)ClB-BCl(NEt2),

[0102] (NMe2)BrB-BBr(NMe2), (NEt2)ClB-BCl(NEt2); the molar ratio of the halogen boron reagent to the compound of formula II is (1.05-1.3):1.

[0103] Preferably, in step S2, the carbonate is potassium carbonate or sodium carbonate, and the molar ratio of the compound of formula IV to the carbonate is 1:(1.5-2.0)

[0104] Furthermore, the molar ratio of the compound of formula IV to the compound of formula IX (halogenated pyridine) is (1-1.5):1; the molar ratio of the compound of formula IV to tetrakis(triphenylphosphine)palladium is 1:(0.8%-1.5%); and the volumes of toluene, EtOH and water are the same, which is 4-5 times the equivalent of the compound of formula IV alone.

[0105] Preferably, in step S3, the molar ratio of the compound of formula VI to iridium trichloride is (2-3):1; the volume ratio of ethylene glycol ethyl ether to water is (3-5):1, and the amount of ethylene glycol ethyl ether added is 20-30 times the equivalent of the compound of formula VI.

[0106] Furthermore, the reaction temperature in step S3 is 115-125° C., and the reaction time is 20-30 hours.

[0107] Preferably, in step S4, the molar ratio of the compound of formula VII to silver trifluoromethanesulfonate is 1:(2.2-3.5); the volume ratio of methanol to dichloromethane is 1:(2-5), and the amount of methanol used is 6-9 times the equivalent of the compound of formula VII.

[0108] Furthermore, the reaction temperature in step S4 is 20-25° C., and the reaction time is 24-48 hours.

[0109] Preferably, in step S5, the molar ratio of the compound of formula V to the compound of formula VIII is (1.5-3.5):1; the volume of anhydrous ethanol or ethylene glycol ethyl ether is 15-20 times the equivalent of the compound of formula V.

[0110] Furthermore, the reaction temperature in step S5 is 80° C. and the reaction time is 30-40 h.

[0111] The third technical purpose of the present invention is to provide an organic electroluminescent device, which comprises an organic layer; the organic layer contains the iridium metal heterocyclic complex luminescent material as described above.

[0112] Furthermore, the organic electroluminescent device further comprises a first electrode and a second electrode; the organic layer is disposed between the first electrode and the second electrode; wherein,

[0113] The organic layer comprises at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a luminescence auxiliary layer, a luminescent layer, a hole blocking layer, an electron transport layer and an electron injection layer; the luminescent layer comprises the iridium metal heterocyclic complex luminescent material.

[0114] Specifically, the light-emitting layer comprises a main material and a doping material, and the mass ratio of the main material to the doping material is 90-99.5:0.5-10; and the iridium metal heterocyclic complex light-emitting material is used as the doping material.

[0115] It can be seen from the above technical solution that compared with the prior art, the present invention has the following beneficial effects:

[0116] The iridium metal heterocyclic complex luminescent material provided by the invention selects a specific heterocyclic complex and adjusts the wavelength of the compound. After the obtained iridium metal heterocyclic complex is used in an organic electroluminescent device, the luminous efficiency of the device is improved and the service life is extended.

[0117] Specifically, the iridium metal heterocyclic complex luminescent material provided by the present invention combines a substituted di(2-phenylpyridine) ligand and a specific heterocyclic ligand with iridium metal, thereby adjusting the wavelength of the compound to obtain an organic luminescent material with a certain symmetry. After using it in an organic electroluminescent device, the driving voltage of the organic electroluminescent device is reduced, the luminous efficiency is improved, and the service life is extended. BRIEF DESCRIPTION OF THE DRAWINGS

[0118] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings required for use in the embodiments or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are only embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on the provided drawings without paying creative work.

[0119] Figure 1 This is the hydrogen nuclear magnetic resonance spectrum of compound formula Ⅰ-28 in Example 2 of the present invention. DETAILED DESCRIPTION

[0120] The technical solutions in the embodiments of the present invention are described clearly and completely below. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0121] The embodiment of the present invention discloses a method for preparing an iridium metal heterocyclic complex luminescent material and an organic electroluminescent device containing the same.

[0122] In addition, it should be noted that the numerical values ​​given in the following examples are as accurate as possible, but those skilled in the art understand that due to unavoidable measurement errors and experimental operation problems, each number should be understood as an approximate number rather than an absolutely accurate value.

[0123] Example 1

[0124] The synthetic routes of steps S1 and S2 of formula Ⅰ-1 are as follows:

[0125]

[0126] S1. Under nitrogen atmosphere, add formula II-1 (8 g, 25.97 mmol, CAS No.: 2639628-83-2), TMEDA (3.62 g, 31.16 mmol) and 40 ml of hexane in a three-necked flask, stir until the solution becomes clear, then add 1.5 M (21 ml, 31.16 mmol) of n-butyl lithium hexane solution, heat to reflux reaction for 2.5 h, then cool to -10 ° C, add (NMe2)ClB-BCl(NMe2) (5.63 g, 31.16 mmol) dropwise, and react at -10 ° C for 5 h. After the reaction is completed by TLC detection, 10% dilute hydrochloric acid is added dropwise to the three-necked flask at 0 ° C to quench n-butyl lithium, and the liquid is extracted with ethyl acetate. The obtained organic layer was spin-dried, and 20 ml of methanol was added to dissolve the crude product. Then 60 ml of pure water was added to precipitate the product, which was filtered and dried to obtain a compound with structure IV-1 (3.2 g, yield 35%, HPLC: 98.5%).

[0127] S2. Add IV-1 (8 g, 22.72 mmol), 2-bromopyridine (Formula IX-1, 4.27 g, 27.27 mmol, CAS No.: 163928-56-1) and sodium carbonate (4.81 g, 45.55 mmol) into a three-necked flask, then add 40 ml of equal volumes of toluene, anhydrous ethanol and purified water respectively, and start stirring. After replacing the nitrogen, add tetrakis(triphenylphosphine)palladium (0.26 g, 0.22 mmol) and reflux for 12 hours; after the reaction is completed by TLC detection, separate the liquids, extract the aqueous phase twice with ethyl acetate, and then combine the organic phases and spin-dry; finally, perform column chromatography (dichloromethane and hexane as eluents) to obtain a compound with the structure of formula V-1 (7 g, yield 80%, HPLC: 99.3%).

[0128] The synthetic routes of steps S3, S4 and S5 of formula Ⅰ-1 are as follows:

[0129]

[0130] S3. Under a nitrogen atmosphere, add formula VI-1 (8 g, 51.59 mmol, CAS No.: 121697-60-7) and IrC13·3H2O (7.26 g, 20.64 mmol) into a three-necked flask, then add 160 mL of ethylene glycol ethyl ether and 40 ml of purified water, reflux for 24 hours under nitrogen protection, cool to room temperature, and a precipitate will be precipitated; filter the precipitate, rinse and dry it with EtOH and petroleum ether in turn, and then column chromatography (dichloromethane and hexane as eluents) to obtain VII-1 (6.39 g, yield is 60%, HPLC: 99.4%).

[0131] S4. Weigh Ⅶ-1 (8 g, 7.74 mmol) and silver trifluoromethanesulfonate (5.96 g, 23.23 mmol) in a three-necked flask, then add 192 ml of dichloromethane and 64 ml of methanol to the system, reflux for 24 hours under nitrogen protection, and cool to room temperature; obtain iridium complex formula Ⅷ-1 (9.78 g, yield 92%, HPLC: 99.5%) by column chromatography.

[0132] S5, weigh formula V-1 (8 g, 20.77 mmol) and formula VIII-1 (4.93 g, 6.92 mmol) in a three-necked flask, then add 120 ml of anhydrous ethanol, reflux for 24 hours under nitrogen protection, filter, wash with alcohol, and dry; finally, obtain formula by column chromatography

[0133] Ⅰ-1 (HPLC: 99.3%).

[0134] The results of mass spectrometry and elemental analysis of compound formula I-1 are as follows:

[0135] Test value: 885.47.

[0136] Elemental analysis: calculated values ​​are C: 66.50; H: 3.42; Ir: 21.72; N: 4.75; O: 3.62; tested values ​​are C: 66.48; H: 3.44; N: 4.73; O: 3.65.

[0137] NMR data: 1 H NMR(400MHz,Chloroform-d)δ8.32(ddd,3H),8.19(ddd,2H),8.10(d,1H),8.07-7.98(m,3H),7.93-7.88(m,1H),7.81-7.77(m,1H ),7.75(dd,1H),7.68(tt,5H),7.63-7.58(m,2H),7.56(d,1H),7.49(ddd,1H),7.33(td,1H),7.33-7.20(m,6H),7.08(dddd,2H).

[0138] Example 2

[0139] The synthetic routes of steps S1 and S2 of formula I-28 are as follows:

[0140]

[0141] S1. In a three-necked flask under nitrogen atmosphere, add formula II-1 (8 g, 25.97 mmol, CAS No.: 2639628-83-2), TMEDA (3.62 g, 31.16 mmol) and 40 ml of hexane were stirred until the solution became clear and then 1.2 M (26 ml, 31.16mmol) tert-butyl lithium hexane solution, heated to reflux reaction for 2.5h and then cooled to -10°C, (NMe2)ClB-BCl(NMe2) (5.63g, 31.16mmol) was added dropwise, and the reaction was carried out at -10°C for 5h. After the reaction was completed by TLC detection, 10% dilute hydrochloric acid was added dropwise to a three-necked flask at 0°C to quench n-butyl lithium, and ethyl acetate was used to extract the liquid. After the obtained organic layer was spin-dried, 20ml of methanol was added to dissolve the crude product, and then 60ml of pure water was added to precipitate the product, filtered, and dried to obtain a compound of IV-1 structure (3.1g, yield 35%, HPLC: 98.7%).

[0142] S2. Add IV-1 (8 g, 22.72 mmol), formula IX-2 (4.66 g, 27.27 mmol, CAS No.: 3430-13-5) and sodium carbonate (4.81 g, 45.55 mmol) into a three-necked flask, then add 40 ml of equal volumes of toluene, anhydrous ethanol and purified water respectively, and start stirring. After replacing the nitrogen, add tetrakis(triphenylphosphine)palladium (0.26 g, 0.22 mmol) and reflux for 12 hours; after the reaction is completed by TLC detection, separate the liquids, extract the aqueous phase twice with ethyl acetate, and then combine the organic phases and spin-dry; finally, perform column chromatography (dichloromethane and hexane as eluents) to obtain a compound with the structure of formula V-2 (6.5 g, yield 72%, HPLC: 99.5%).

[0143] S3. Under a nitrogen atmosphere, add formula VI-2 (8 g, 47.31 mmol, CAS No.: 27012-22-2) and IrC13·3H2O (5.56 g, 15.77 mmol) into a three-necked flask, then add 160 mL of ethylene glycol ethyl ether and 40 ml of purified water, reflux for 24 h under nitrogen protection, cool to room temperature, and a precipitate will be precipitated; filter the precipitate, rinse and dry it with EtOH and petroleum ether in turn, and then perform column chromatography (dichloromethane and hexane as eluents) to obtain VII-2 (5.36 g, yield is 64%, HPLC: 99.3%).

[0144] The synthetic routes of steps S3, S4 and S5 of formula I-28 are as follows:

[0145]

[0146] S4. Weigh Ⅶ-2 (8 g, 7.09 mmol) and silver trifluoromethanesulfonate (5.47 g, 21.27 mmol) into a three-necked flask, then add 192 ml of dichloromethane and 64 ml of methanol to the system, reflux for 24 hours under nitrogen protection, and cool to room temperature; obtain iridium complex formula Ⅷ-2 (9.53 g, yield 91%) by column chromatography.

[0147] S5, weigh formula V-2 (8 g, 20.04 mmol) and formula VIII-2 (4.94 g, 6.68 mmol) in a three-necked flask, then add 120 ml of anhydrous ethanol, reflux for 24 hours under nitrogen protection, filter, wash with alcohol, and dry; finally, obtain formula by column chromatography

[0148] Ⅰ-28 (HPLC: 99.6%).

[0149] The results of mass spectrometry and elemental analysis of compound I-28 are as follows:

[0150] Test value: 927.26.

[0151] Elemental analysis: calculated values ​​are C: 66.37; H: 3.91; Ir: 20.73; N: 4.53; O: 3.45. Test values ​​are C: 66.65; H: 3.69; N: 4.69; O: 3.52.

[0152] The nuclear magnetic resonance hydrogen spectrum (Formula I-28) is as follows Figure 1 shown.

[0153] Example 3

[0154] The synthetic routes of steps S1 and S2 of formula I-1155 are as follows:

[0155]

[0156] S1. Under nitrogen atmosphere, add formula II-1 (8 g, 25.97 mmol), TMEDA (3.62 g, 31.16 mmol) and 40 ml of hexane in a three-necked flask, stir until the solution becomes clear, then add 1.2 M (26 ml, 31.16 mmol) of tert-butyl lithium hexane solution, heat to reflux reaction for 2.5 h, then cool to -10 ° C, add (NEt2)ClB-BCl(NEt2) (7.13 g, 31.16 mmol), and react at -10 ° C for 5 h. After the reaction is completed by TLC detection, 10% dilute hydrochloric acid is added to the three-necked flask at 0 ° C to quench n-butyl lithium, and the liquid is extracted with ethyl acetate. The obtained organic layer was spin-dried, and 20 ml of methanol was added to dissolve the crude product. Then 60 ml of pure water was added to precipitate the product, which was filtered and dried to obtain a compound with structure IV-1 (2.93 g, yield 32%, HPLC: 98.3%).

[0157] S2. Add IV-1 (8 g, 22.72 mmol), formula IX-3 (4.74 g, 27.27 mmol, CAS No.: 1185312-36-0) and sodium carbonate (4.81 g, 45.55 mmol) into a three-necked flask, then add 40 ml of equal volumes of toluene, anhydrous ethanol and purified water respectively, and start stirring. After replacing the nitrogen, add tetrakis(triphenylphosphine)palladium (0.26 g, 0.22 mmol) and reflux for 12 hours; after the reaction is completed by TLC detection, separate the liquids, extract the aqueous phase twice with ethyl acetate, and then combine the organic phases and spin-dry; finally, perform column chromatography (dichloromethane and hexane as eluents) to obtain a compound with the structure of formula V-3 (6.85 g, yield 75%, HPLC: 99.1%).

[0158] The synthetic routes of steps S3, S4 and S5 of formula Ⅰ-1155 are as follows:

[0159]

[0160] S3. Under a nitrogen atmosphere, add formula VI-3 (8 g, 46.48 mmol, CAS No.: 1622235-49-7) and IrC13·3H2O (5.45 g, 15.49 mmol) into a three-necked flask, then add 160 mL of ethylene glycol ethyl ether and 40 ml of purified water, reflux for 24 hours under nitrogen protection, cool to room temperature, and a precipitate will be precipitated; filter the precipitate, rinse and dry it with EtOH and petroleum ether in turn, and then column chromatography (dichloromethane and hexane as eluents) to obtain VII-3 (5.75 g, yield is 65.1%, HPLC: 99.4%).

[0161] S4. Weigh Ⅶ-3 (8 g, 7.02 mmol) and silver trifluoromethanesulfonate (5.39 g, 21.05 mmol) into a three-necked flask, then add 192 ml of dichloromethane and 64 ml of methanol to the system, reflux for 24 hours under nitrogen protection, and cool to room temperature; obtain iridium complex formula Ⅷ-3 (9.66 g, yield 92.4%) by column chromatography.

[0162] S5. Weigh formula V-3 (8 g, 20.04 mmol) and formula VIII-3 (4.96 g, 6.63 mmol) into a three-necked flask, then add 120 ml of anhydrous ethanol, reflux for 24 hours under nitrogen protection, filter, wash with alcohol, and dry; finally, obtain formula I-1155 (HPLC: 99.6%) through column chromatography.

[0163] Test value: 936.42.

[0164] Elemental analysis: calculated values ​​are C: 66.72; H: 4.84; Ir: 20.53; N: 4.49; O: 3.42. Test values ​​are C: 66.24; H: 4.31; N: 4.66; O: 3.49.

[0165] NMR data: 1 HNMR(400MHz,Chloroform-d)δ9.21(d,1H),8.42(dd,2H),8.18(dd,2H),8.09(dd,2H),8.01(dd,1H),7.93–7.88(m,1H),7.84(d,1H),7.81–7.76 (m,1H),7.69(d,1H),7.64(dd,3H),7.61(d,1H),7.56(d,1H),7.49(ddd, 1H),7.37–7.30(m,2H),7.29(dd,1H),7.27–7.20(m,4H),7.11(ddd,2H).

[0166] Example 4

[0167] The synthetic routes of steps S1 and S2 of formula I-1450 are as follows:

[0168]

[0169] The preparation process of S1 and IV-1 structure compounds is consistent with step S1 of Example 2.

[0170] S2. Add IV-1 (8 g, 22.72 mmol), formula IX-4 (6.24 g, 27.27 mmol, CAS No.: 291312-74-81) and sodium carbonate (4.81 g, 45.55 mmol) into a three-necked flask, then add 40 ml of equal volumes of toluene, anhydrous ethanol and purified water respectively, and start stirring. After replacing the nitrogen, add tetrakis(triphenylphosphine)palladium (0.26 g, 0.22 mmol) and reflux for 12 hours; after the reaction is completed by TLC detection, separate the liquids, extract the aqueous phase twice with ethyl acetate, and then combine the organic phases and spin-dry; finally, perform column chromatography (dichloromethane and hexane as eluents) to obtain a compound with the structure of formula V-4 (7.93 g, yield 76.3%, HPLC: 99.1%).

[0171] S3. Under a nitrogen atmosphere, add formula VI-1 (8 g, 51.59 mmol, CAS No.: 121697-60-7) and IrC13·3H2O (9.08 g, 25.79 mmol) into a three-necked flask, then add 160 mL of ethylene glycol ethyl ether and 40 ml of purified water, reflux for 24 hours under nitrogen protection, cool to room temperature, and a precipitate will be precipitated; filter the precipitate, rinse and dry it with EtOH and petroleum ether in turn, and then column chromatography (dichloromethane and hexane as eluents) to obtain VII-1 (7.22 g, yield is 54.2%, HPLC: 99.6%).

[0172] S4. Weigh Ⅶ-1 (8 g, 7.74 mmol) and silver trifluoromethanesulfonate (5.96 g, 23.23 mmol) in a three-necked flask, then add 192 ml of dichloromethane and 64 ml of methanol to the system, reflux for 24 hours under nitrogen protection, and cool to room temperature; obtain iridium complex formula Ⅷ-1 (10.22 g, yield 92.7%, HPLC: 99.2%) by column chromatography.

[0173] The synthetic routes of steps S3, S4 and S5 of formula Ⅰ-1450 are as follows:

[0174]

[0175] S5. Weigh formula V-4 (8 g, 17.5 mmol) and formula VIII-1 (4.15 g, 5.83 mmol) into a three-necked flask, then add 120 ml of anhydrous ethanol, reflux for 24 hours under nitrogen protection, filter, wash with alcohol, and dry; finally, obtain formula Ⅰ-1450 (HPLC: 99.8%) through column chromatography.

[0176] Test value: 957.25.

[0177] Elemental analysis: C: 65.25; H: 4.00; Ir: 20.08; N: 4.39; O: 3.34; Si: 2.93 The tested values ​​are C: 65.23; H: 3.98; N: 4.40; O: 3.31, Si: 2.92.

[0178] NMR data: 1HNMR(400MHz,Chloroform-d)δ8.60(d,1H),8.31(dd,2H),8.21(dd,2H),8.09(dd,2H),8.01(dd,1H),7.93-7.88(m,1H),7.84(d,1H),7 .81-7.76(m,1H),7.75-7.59(m,7H),7.56(d,1H),7.54-7.46(m,2H),7.37-7.30(m,2H),7.30-7.19(m,4H),7.02(ddd,2H),0.31(s,9H).

[0179] Example 5

[0180] The synthetic routes of steps S1 and S2 of formula I-1455 are as follows:

[0181]

[0182] The preparation process of S1 and IV-1 structure compounds is consistent with step S1 in Example 3.

[0183] S2. Add IV-1 (8 g, 22.72 mmol), formula IX-4 (6.24 g, 27.27 mmol, CAS No.: 291312-74-8) and potassium carbonate (6.28 g, 45.55 mmol) into a three-necked flask, then add 40 ml of equal volumes of toluene, anhydrous ethanol and purified water respectively, and start stirring. After replacing the nitrogen, add tetrakis(triphenylphosphine)palladium (0.26 g, 0.22 mmol) and reflux for 12 hours; after the reaction is completed by TLC detection, separate the liquids, extract the aqueous phase twice with ethyl acetate, and then combine the organic phases and spin-dry; finally, perform column chromatography (dichloromethane and hexane as eluents) to obtain a compound with the structure of formula V-4 (7.87 g, yield 75.8%, HPLC: 99.3%).

[0184] The synthetic routes of steps S3, S4 and S5 of formula I-1455 are as follows:

[0185]

[0186] S3. Under a nitrogen atmosphere, add formula VI-5 (8 g, 35.23 mmol, CAS No.: 128945-73-3) and IrC13·3H2O (4.13 g, 11.74 mmol) into a three-necked flask, then add 160 mL of ethylene glycol ethyl ether and 40 ml of purified water, reflux for 24 hours under nitrogen protection, cool to room temperature, and a precipitate will be precipitated; filter the precipitate, rinse and dry it with EtOH and petroleum ether in turn, and then column chromatography (dichloromethane and hexane as eluents) to obtain VII-5 (4.3 g, yield is 53.9%, HPLC: 99.2%).

[0187] S4. Weigh Ⅶ-5 (8 g, 5.88 mmol) and silver trifluoromethanesulfonate (4.51 g, 17.64 mmol) in a three-necked flask, then add 192 ml of dichloromethane and 64 ml of methanol to the system, reflux for 24 hours under nitrogen protection, and cool to room temperature; obtain iridium complex formula Ⅷ-5 (9.67 g, yield 93.3%, HPLC: 99.3%) by column chromatography.

[0188] S5, weigh formula V-4 (8 g, 17.5 mmol) and formula VIII-5 (5.14 g, 5.83 mmol) in a three-necked flask, then add 120 ml of anhydrous ethanol, reflux for 24 hours under nitrogen protection, filter, wash with alcohol, and dry; finally, obtain formula by column chromatography

[0189] Ⅰ-1455 (HPLC: 99.7%).

[0190] Test value: 1101.36.

[0191] Elemental analysis: C:63.24; H:4.94; Ir:17.45; N:3.81; O:2.90; Si:7.65; tested values ​​are C:63.21; H:4.89; N:3.77; O:2.92, Si:7.62.

[0192] NMR data: 1 HNMR(400MHz,Chloroform-d)δ9.49-9.45(m,1H),9.21(d,1H),8.60(d,2H), 8.33(dd,2H),8.09(dd,2H),7.93-7.88(m,1H),7.84(d,1H),7.81-7.76(m,1H ),7.69(d,1H),7.64(dd,3H),7.61(d,1H),7.56(d,1H),7.49(ddd,1H),7.37 -7.30(m,2H),7.29(dd,1H),7.27-7.20(m,4H),7.11(ddd,2H),2.26(d,27H).

[0193] Example 6

[0194] The synthetic routes of steps S1 and S2 of formula I-1349 are as follows:

[0195]

[0196] S1. Under nitrogen atmosphere, add formula II-1 (8 g, 25.97 mmol), TMEDA (3.62 g, 31.16 mmol) and 40 ml of hexane in a three-necked flask, stir until the solution becomes clear, then add 2.4 M (13 ml, 31.16 mmol) of hexyl lithium hexane solution, heat to reflux reaction for 2.5 h, then cool to -10 ° C, add (NMe2)ClB-BCl(NMe2) (5.63 g, 31.16 mmol) dropwise, and react at -10 ° C for 5 h. After the reaction is completed by TLC detection, 10% dilute hydrochloric acid is added dropwise to the three-necked flask at 0 ° C to quench n-butyl lithium, and the liquid is extracted with ethyl acetate. The obtained organic layer was spin-dried, and 20 ml of methanol was added to dissolve the crude product. Then 60 ml of pure water was added to precipitate the product, which was filtered and dried to obtain a compound with structure IV-1 (2.98 g, yield 32.6%, HPLC: 99.1%).

[0197] S2. Add IV-1 (8 g, 22.72 mmol), formula IX-6 (6.24 g, 27.27 mmol, CAS No.: 27012-25-5) and sodium carbonate (4.81 g, 45.55 mmol) into a three-necked flask, then add 40 ml of equal volumes of toluene, anhydrous ethanol and purified water respectively, and start stirring. After replacing the nitrogen, add tetrakis(triphenylphosphine)palladium (0.26 g, 0.22 mmol) and reflux for 12 hours; after the reaction is completed by TLC detection, separate the liquids, extract the aqueous phase twice with ethyl acetate, and then combine the organic phases and spin-dry; finally, perform column chromatography (dichloromethane and hexane as eluents) to obtain a compound with the structure of formula V-6 (7.72 g, yield 73.7%, HPLC: 99.5%).

[0198] S3. Under a nitrogen atmosphere, add formula VI-6 (8 g, 34.62 mmol) and IrC13·3H2O (4.87 g, 13.85 mmol) into a three-necked flask, then add 160 mL of ethylene glycol ethyl ether and 40 ml of pure water, reflux for 24 h under nitrogen protection, cool to room temperature, and a precipitate will be precipitated; filter the precipitate, rinse and dry it with EtOH and petroleum ether in turn, and then column chromatography (dichloromethane and hexane as eluents) to obtain Ⅶ-6 (5.16 g, yield is 54.2%, HPLC: 99.3%).

[0199] S4. Weigh Ⅶ-6 (8 g, 5.81 mmol) and silver trifluoromethanesulfonate (4.46 g, 17.43 mmol) in a three-necked flask, then add 192 ml of dichloromethane and 64 ml of methanol to the system, reflux for 24 hours under nitrogen protection, and cool to room temperature; obtain iridium complex formula Ⅷ-6 (9.20 g, yield 91.7%, HPLC: 99.1%) by column chromatography.

[0200] The synthetic routes of steps S3, S4 and S5 of formula I-1349 are as follows:

[0201]

[0202] S5. Weigh formula V-6 (8 g, 17.34 mmol, CAS No.: 15827-72-2) and formula VIII-6 (4.99 g, 5.78 mmol) into a three-necked flask, then add 120 ml of anhydrous ethanol, reflux for 24 hours under nitrogen protection, filter, wash with alcohol, and dry; finally, obtain formula I-1349 (HPLC: 99.6%) through column chromatography.

[0203] Test value: 1113.37.

[0204] Elemental analysis: C:72.28; H:3.80; Ir:17.27; N:3.77; O:2.87; tested value is C:72.33; H:3.60; N:4.08; O:2.95.

[0205] NMR data: 1 HNMR(400MHz,Chloroform-d)δ9.63(d,1H),9.59(d,2H),8.25(dd,2H),8.09(dd,2H),8.04-7.88(m,5H),7.88-7.76( m,5H),7.69(d,1H),7.63(dd,1H),7.57(ddd,7H),7.52-7.43(m,7H),7.42-7.30(m,6H),7.23(td,1H),7.11(ddd,2H).

[0206] Example 7

[0207] The synthetic routes of steps S1 and S2 of formula I-1432 are as follows:

[0208]

[0209] The preparation process of S1 and IV-1 structure compounds is consistent with step S1 of Example 2.

[0210] S2. Add IV-1 (8 g, 22.72 mmol), formula IX-7 (6.24 g, 27.27 mmol, CAS No.: 97483-77-7) and sodium carbonate (4.81 g, 45.55 mmol) into a three-necked flask, then add 40 ml of equal volumes of toluene, anhydrous ethanol and purified water respectively, and start stirring. After replacing the nitrogen, add tetrakis(triphenylphosphine)palladium (0.26 g, 0.22 mmol) and reflux for 12 hours; after the reaction is completed by TLC detection, separate the liquids, extract the aqueous phase twice with ethyl acetate, and then combine the organic phases and spin-dry; finally, perform column chromatography (dichloromethane and hexane as eluents) to obtain a compound with the structure of formula V-7 (7.09 g, yield 76.1%, HPLC: 99.2%).

[0211] The synthetic routes of steps S3, S4 and S5 of formula I-1432 are as follows:

[0212]

[0213] S3. Under a nitrogen atmosphere, add formula VI-7 (8 g, 39.01 mmol, CAS No.: 1699174-68-9) and IrC13·3H2O (5.49 g, 15.61 mmol) into a three-necked flask, then add 160 mL of ethylene glycol ethyl ether and 40 ml of purified water, reflux for 24 hours under nitrogen protection, cool to room temperature, and a precipitate will be precipitated; filter the precipitate, rinse and dry it with EtOH and petroleum ether in turn, and then column chromatography (dichloromethane and hexane as eluents) to obtain VII-7 (5.23 g, yield is 52.7%, HPLC: 99.4%).

[0214] S4. Weigh Ⅶ-7 (8 g, 6.29 mmol) and silver trifluoromethanesulfonate (4.83, 18.87 mmol) in a three-necked flask, then add 192 ml of dichloromethane and 64 ml of methanol to the system, reflux for 24 hours under nitrogen protection, and cool to room temperature; obtain iridium complex formula Ⅷ-7 (9.32 g, yield 91.4%, HPLC: 99.3%) by column chromatography.

[0215] S5. Weigh formula V-7 (8 g, 19.51 mmol) and formula VIII-7 (5.27 g, 6.50 mmol) into a three-necked flask, then add 120 ml of anhydrous ethanol, reflux for 24 hours under nitrogen protection, filter, wash with alcohol, and dry; finally, obtain formula I-1432 (HPLC: 99.6%) by column chromatography.

[0216] Test value: 1010.35.

[0217] Elemental analysis: C: 64.21; H: 2.49; Ir: 19.03; N: 11.09; O: 3.17; tested value is C: 64.77; H: 2.64; N: 10.97; O: 3.32.

[0218] NMR data: 1 HNMR(400MHz,Chloroform-d)δ9.78(dd,3H),8.73(dd,3H),8.09(d,2H),8.01(dd,1H),7.93-7.88(m,1H),7.87- 7.80(m,3H),7.82-7.76(m,4H),7.69(d,1H),7.66-7.61(m,3H),7.56(d,1H),7.49(ddd,1H),7.38-7.30(m,2H).

[0219] Example 8

[0220] The synthetic routes of steps S1 and S2 of formula Ⅰ-1474 are as follows:

[0221]

[0222] The preparation process of S1 and IV-1 structure compounds is consistent with step S1 of Example 1.

[0223] S2. Add IV-1 (8 g, 22.72 mmol), 2-bromopyridine (Formula IX-1, 4.27 g, 27.27 mmol, CAS No.: 163928-56-1) and sodium carbonate (4.81 g, 45.55 mmol) into a three-necked flask, then add 40 ml of equal volumes of toluene, anhydrous ethanol and purified water respectively, and start stirring. After replacing the nitrogen, add tetrakis(triphenylphosphine)palladium (0.26 g, 0.22 mmol) and reflux for 12 hours; after the reaction is completed by TLC detection, separate the liquids, extract the aqueous phase twice with ethyl acetate, and then combine the organic phases and spin-dry; finally, perform column chromatography (dichloromethane and hexane as eluents) to obtain a compound with the structure of formula V-1 (7 g, yield 80%, HPLC: 99.4%).

[0224] S3. Under a nitrogen atmosphere, add formula VI-8 (8 g, 29.30 mmol, CAS No.: 1402249-71-1) and IrC13·3H2O (4.13 g, 11.72 mmol) into a three-necked flask, then add 160 mL of ethylene glycol ethyl ether and 40 ml of purified water, reflux for 24 h under nitrogen protection, cool to room temperature, and a precipitate will be precipitated; filter the precipitate, rinse and dry it with EtOH and petroleum ether in turn, and then column chromatography (dichloromethane and hexane as eluents) to obtain VII-8 (4.68 g, yield is 51.8%, HPLC: 99.5%).

[0225] S4. Weigh Ⅶ-8 (8 g, 5.18 mmol) and silver trifluoromethanesulfonate (3.98 g, 15.54 mmol) in a three-necked flask, then add 192 ml of dichloromethane and 64 ml of methanol to the system, reflux for 24 hours under nitrogen protection, and cool to room temperature; obtain iridium complex formula Ⅷ-8 (9.03 g, yield 92.1%, HPLC: 99.2%) by column chromatography.

[0226] The synthetic routes of steps S3, S4 and S5 of formula Ⅰ-1474 are as follows:

[0227]

[0228] S5. Weigh formula V-1 (8 g, 20.77 mmol) and formula VIII-8 (6.55 g, 6.92 mmol) into a three-necked flask, then add 120 ml of anhydrous ethanol, reflux for 24 hours under nitrogen protection, filter, wash with alcohol, and dry; finally, obtain formula I-1474 (HPLC: 99.6%) by column chromatography.

[0229] Test value: 1121.39.

[0230] Elemental analysis: C:59.06; H:4.15; Ge:12.99; Ir:17.19; N:3.76; O:2.86; tested value is C:58.98; H:4.10; Ge:12.31; N:3.88; O:2.83.

[0231] NMR data: 1H NMR(400MHz,Chloroform-d)δ9.59(dd,2H),8.36-8.29(m,3H),8.09(dd,2H),8.01(dd,1H),7.93-7.88(m,1H),7.84(d,1H),7.81-7.73(m,2 H),7.73-7.66(m,2H),7.63(dd,1H),7.61-7.54(m,5H),7.49(ddd,1H),7.37-7.26(m,3H),7.26-7.20(m,2H),7.11(ddd,2H),0.57(s,18H).

[0232] The synthesis methods of other target structural compounds are the same as above, and are not described here one by one. The relevant structures, yields and mass spectrometry data are shown in Table 1:

[0233] Table 1 shows the structures, yields and mass spectrometry data of target compounds in Examples 9 to 20.

[0234]

[0235]

[0236] Device Example 1

[0237] In device embodiment 1, an organic electroluminescent device is provided, comprising a substrate, an anode layer, a hole injection layer, a hole transport layer, an organic light emitting layer, an air barrier layer, an electron transport layer, an electron injection layer and a cathode layer. The preparation method of the organic electroluminescent device is as follows:

[0238] (1) Preparation of ITO anode

[0239] The coating thickness is The ITO glass substrate was cleaned twice in distilled water, ultrasonically cleaned for 30 minutes using an ultrasonic device, and then repeatedly cleaned twice with distilled water and ultrasonically cleaned for 10 minutes; after the cleaning, it was ultrasonically cleaned in turn with isopropanol, acetone, methanol and other solvents, dried, and then transferred to a plasma cleaning machine, the above substrate was washed for 5 minutes, and sent to a vapor deposition machine to evaporate other functional layers.

[0240] (2) Hole injection layer and hole transport layer

[0241] by Formula-A and Formula-B are vacuum-deposited in the hole injection layer at a deposition rate of 95:5. The chemical formula of Formula-A / B is shown below. At a deposition rate of , 120 nm of Formula-A was evaporated on the hole injection layer as a hole transport layer.

[0242]

[0243] (3) Organic light-emitting layer

[0244] by The evaporation rate is 28 nm, and a luminescent layer is evaporated with 4,4'-N,N'-biphenyldicarbazole ("CBP") as the main material and formula Ⅰ-1 as the doping material, wherein the mass ratio of CBP to compound formula Ⅰ-1 is 95:5.

[0245] (4) Hole blocking layer

[0246] by The formula-C was vacuum evaporated at a deposition rate to form a hole blocking layer with a thickness of 5.0 nm.

[0247]

[0248]

[0249] (5) Electron transport layer, electron injection layer

[0250] by The deposition rate is 35 nm, and the electron transport layer of "Alq3" is vacuum-deposited. The evaporation rate is 0.5nm, and the electron injection layer of LiF film is vacuum evaporated.

[0251] (6) Cathode layer

[0252] by The evaporation rate ratio is 15nm, and 15nm of silver is evaporated to obtain an organic electroluminescent device.

[0253] Referring to device example 1, the doping material formula Ⅰ-1 in the organic electroluminescent device is replaced by formula Ⅰ-28, Ⅰ-1155, Ⅰ-1450, Ⅰ-1455, Ⅰ-1349, Ⅰ-1432, Ⅰ-1474, Ⅰ-2, Ⅰ-10, Ⅰ-22, Ⅰ-202, Ⅰ-771, Ⅰ-779, Ⅰ-796, Ⅰ-872, Ⅰ-938, Ⅰ-1144, Ⅰ-1267 and Ⅰ-1456, and they are prepared into relevant organic electroluminescent devices respectively.

[0254] Comparative Example 1

[0255] An organic electroluminescent device is prepared using the preparation method of device example 1, and the doping material of formula I-1 in its light-emitting layer is replaced by a compound of formula D, the structure of which is shown below.

[0256]

[0257] In order to further illustrate the luminescent properties of the novel iridium metal heterocyclic complex luminescent material provided by the present invention, the luminescent properties of the organic light-emitting device prepared in the device example and the device obtained in Comparative Example 1 were tested. The measurement was carried out using a KEITHLEY 2400 source measurement unit and a CS-2000 spectroradiometer to evaluate the driving voltage, luminescent brightness, and luminescent efficiency. The results are shown in Table 2.

[0258] Table 2 Luminescence detection data of organic electroluminescent devices of device examples 1-20 and comparative example 1

[0259]

[0260]

[0261] It can be seen from Table 2 that when the brightness is the same, the driving voltage of the device provided by the present invention is lower, and the efficiency and life are also improved compared with Comparative Example 1. It can be seen that the organic electroluminescent device prepared by using the compound provided by the present invention as the doping material of the light-emitting layer has better luminous efficiency and longer service life.

[0262] The above description of the disclosed embodiments enables one skilled in the art to implement or use the present invention. Various modifications to these embodiments will be apparent to one skilled in the art, and the general principles defined herein may be implemented in other embodiments without departing from the spirit or scope of the present invention. Therefore, the present invention will not be limited to the embodiments shown herein, but rather to the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. An iridium metal heterocyclic complex luminescent material, characterized in that: The structure of the iridium metal heterocyclic complex luminescent material is shown in Formula I: wherein R1 to R7 each independently represent hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amino, sulfonic acid, substituted or unsubstituted C1-C 50 Alkyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C5-C 50 Heteroaryl, substituted or unsubstituted C3-C 50 Cycloalkyl, substituted or unsubstituted C1-C 50 Alkoxy, substituted or unsubstituted C1-C 50 Alkylamino, substituted or unsubstituted C2-C 50 Alkenyl or alkyne, substituted or unsubstituted C2-C 50 Heterocyclyl, substituted or unsubstituted C 10 -C 50 Condensed ring group, substituted or unsubstituted C5-C 50 Spirocyclyl, substituted or unsubstituted C1-C 50 Silane, substituted or unsubstituted C1-C 50 A germanyl group; and the substituents at positions R1 to R7 are the same or different; The positions of R1 to R7 are any positions of the benzene ring, the number of R1 to R4 substituents is 0 to 4, and the number of R5 to R7 substituents is 0 to 2.

2. The iridium metal heterocyclic complex luminescent material according to claim 1, characterized in that: The R1-R7 each independently represents hydrogen, deuterium, cyano, substituted or unsubstituted C1-C 15 Alkyl, substituted or unsubstituted C6-C 15 Aryl, substituted or unsubstituted C3-C 15 Cycloalkyl, substituted or unsubstituted C1-C 15 Alkoxy, substituted or unsubstituted C2-C 15 Heterocyclic, substituted or unsubstituted C 10 -C 20 Condensed ring group, substituted or unsubstituted C1-C 15 Silane, substituted or unsubstituted C1-C 15 Germanyl.

3. The iridium metal heterocyclic complex luminescent material according to claim 2, characterized in that: The substituted or unsubstituted C1-C 15 The alkyl group includes any one of methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, isopentyl, neopentyl, hexyl, 2-methylpentyl, 3-methylpentyl, 2,3-dimethylbutyl and 2,2-dimethylbutyl.

4. The iridium metal heterocyclic complex luminescent material according to claim 2, characterized in that: The substituted or unsubstituted C6-C 15 The aryl group includes any one of phenyl, tolyl, chlorophenyl, bromophenyl, fluorophenyl, biphenyl, terphenyl, naphthyl, anthracenyl and phenanthryl.

5. The iridium metal heterocyclic complex luminescent material according to claim 2, characterized in that: The substituted or unsubstituted C3-C 15 The cycloalkyl group includes any one of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.

6. The iridium metal heterocyclic complex luminescent material according to claim 2, characterized in that: The substituted or unsubstituted C1-C 15 The alkoxy group includes any one of a methoxy group, an ethoxy group, a propoxy group, and a phenoxy group.

7. The iridium metal heterocyclic complex luminescent material according to claim 2, characterized in that: The substituted or unsubstituted C2-C 15 The heterocyclic group includes an aromatic or non-aromatic cyclic group containing at least one heteroatom, wherein the heteroatom is selected from one or more combinations of O, S, N, P, B, Si, and Se.

8. The iridium metal heterocyclic complex luminescent material according to claim 1, characterized in that: The R1 to R7 can be combined arbitrarily to form a substituted or unsubstituted condensed ring, and the substituents that do not form a condensed ring include hydrogen, deuterium, cyano, substituted or unsubstituted C1-C 50 Alkyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C3-C 15 Cycloalkyl, substituted or unsubstituted C2-C 50 Heterocyclic, substituted or unsubstituted C 10 -C 20 A fused ring group, a substituted or unsubstituted C5-C 50 The spirocyclic group may or may not include any one or more combinations of O, S, N, P, B, Si, and Se in the formed condensed ring.

9. The iridium metal heterocyclic complex luminescent material according to claim 1, characterized in that: The iridium metal heterocyclic complex luminescent material has the following structure:

10. A method for preparing the iridium metal heterocyclic complex luminescent material as claimed in claim 1, characterized in that: The following steps are involved: S1. Under a nitrogen atmosphere, hexane and TMEDA are added to the compound of formula II, and then alkyl lithium is added to react at a low temperature to prepare formula III, and then a halogen boron reagent is added dropwise to prepare formula IV; S2. Under a nitrogen atmosphere, a compound of formula IV, a compound of formula IX, tetrakis(triphenylphosphine)palladium, toluene, EtOH, sodium carbonate, and water are reacted to prepare a compound of formula V; S3. Under a nitrogen atmosphere, reacting the compound of formula VI with iridium trichloride to obtain a compound of formula VII; S4. Under a nitrogen atmosphere, the compound of formula Ⅶ is reacted with silver trifluoromethanesulfonate to obtain a compound of formula Ⅷ; S5. Under a nitrogen atmosphere, the compound of formula Ⅴ and the compound of formula Ⅷ are reacted in a single solvent of anhydrous ethanol or ethylene glycol ethyl ether to obtain a compound having a structure of formula I, that is, the iridium metal heterocyclic complex luminescent material; The specific synthetic route is as follows:

11. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a first electrode, an organic electroluminescent material layer, and a second electrode; the organic electroluminescent material layer comprises a light-emitting layer, and the light-emitting layer comprises a host material and the iridium metal heterocyclic complex light-emitting material as claimed in claim 1.

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