Organic iridium metal complex luminescent material, preparation method thereof and organic electroluminescent device

Abstract

The invention discloses an organic iridium metal complex luminescent material and a preparation method thereof, and an organic electroluminescent device, the organic iridium metal complex luminescent material can be used as a doping material of a luminescent part of the organic electroluminescent device, and because the organic iridium metal complex luminescent material has more benzene ring structures and is relatively symmetrical, the luminescent part of the organic electroluminescent device can be used as a doping material of the luminescent part of the organic electroluminescent device. Therefore, the wavelength of the fluorescence can be adjusted by changing the types and the number of the substituent groups on the benzene ring, so that the purposes of high luminous efficiency and prolonging of the service life of a device are achieved.

Description

Technical Field

[0001] The invention belongs to the technical field of optoelectronic materials, and in particular relates to an organic iridium metal complex luminescent material and a preparation method thereof and an organic electroluminescent device. Background Art

[0002] With the increasing pursuit of color and quality for mobile phones, TVs, computers and other related screens, research on OLEDs has made significant progress in the past few decades. This is because compared with other lighting sources, OLEDs can emit light directly from the surface, not only can the shape be customized, but also the same luminous flux can be achieved under reduced light intensity conditions, making OLEDs highly efficient.

[0003] The materials of the light-emitting part of OLED 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 only rely 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 devoted themselves to the research of heavy metal coordinated organic fluorescent materials, especially the research of metal iridium complex organic fluorescent materials.

[0004] However, from the perspective of the luminescent materials currently discovered, their synthesis cost is relatively high, the synthesis process requirements are relatively complex, and there are disadvantages such as difficulty in purification during the synthesis process, short lifespan, and low efficiency. Therefore, developing a material with high luminescence efficiency and long lifespan is an urgent problem to be solved. Summary of the invention

[0005] In order to solve the above problems, the present invention provides an organic iridium metal complex luminescent material, a preparation method thereof and an organic electroluminescent device. The organic iridium metal complex luminescent material has a large number of benzene ring structures and is relatively symmetrical. Therefore, the wavelength of fluorescence can be adjusted by changing the type and number of substituents on the benzene ring. When used as a doping material for the light-emitting part of an organic electroluminescent device, a higher luminescent efficiency can be achieved and the service life of the device can be extended.

[0006] In order to achieve the above object, the present invention provides the following technical solutions:

[0007] An organic iridium metal complex luminescent material, the general structural formula of the organic iridium metal complex is as shown in Formula I:

[0008]

[0009] In Formula I, R1 to R6 are each independently selected from hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amino, sulfonic acid, substituted or unsubstituted C1-C 40 Alkyl, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C6-C 40 Heteroaryl, substituted or unsubstituted C3-C 40 Cycloalkyl, substituted or unsubstituted C1-C 40 Alkoxy, substituted or unsubstituted C1-C 40 Alkylamino, substituted or unsubstituted C2-C 40 Alkenyl or alkyne, substituted or unsubstituted C2-C 40 Heterocyclyl, substituted or unsubstituted C8-C 40 Condensed ring group, substituted or unsubstituted C5-C 40 Spirocyclyl, substituted or unsubstituted C1-C 40 Silane, substituted or unsubstituted C1-C 40 The germanium alkyl group, the substituents at the positions of R1 to R6 are the same or different; the positions of R1 to R5 are any positions of the benzene ring, the number of R1, R2, R4 and R5 substituents is 0 to 4, the number of R3 substituents is 0 to 5, and the number of R6 substituents is 0 to 1.

[0010] In one embodiment of the present invention, each of R1 to R6 independently represents hydrogen, deuterium, cyano, fluorine, trimethylsilyl, trimethylgermanyl, substituted or unsubstituted C1-C 15 Alkyl, substituted or unsubstituted C3-C 15 Cycloalkyl, substituted or unsubstituted C1-C 15 Alkoxy, substituted or unsubstituted C2-C 15 Heterocyclic, substituted or unsubstituted C6-C 15 Aryl, substituted or unsubstituted C8-C 20 The fused ring group, R1 to R6 are the same or different.

[0011] In one embodiment of the present invention, 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.

[0012] In one embodiment of the present invention, the substituted or unsubstituted C6-C 15 The aryl group includes any one of a phenyl group, a tolyl group, a chlorophenyl group, a bromophenyl group, a fluorophenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, and a phenanthryl group.

[0013] In one embodiment of the present invention, the substituted or unsubstituted C3-C 15 The cycloalkyl group includes any one of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.

[0014] In one embodiment of the present invention, 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.

[0015] In one embodiment of the present invention, the substituted or unsubstituted C2-C 15 The heterocyclic group is 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 Ge.

[0016] For example, oxirane, thiirane, tetrahydrofuran, thiophene, pyrrole, pyridine, tetrahydrothiophene, pyrazine, imidazole and the like.

[0017] In one embodiment of the present invention, the substituted or unsubstituted C8-C 20 The fused ring group includes indole, quinoline, benzofuran, benzothiophene, isoquinoline, benzimidazole, 2-phenylpyridine and its derivatives, dibenzofuran, dibenzothiophene and the like.

[0018] In one embodiment of the present invention, in the organic iridium metal complex luminescent material, the R1 to R6 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 40 Alkyl, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Cycloalkyl, substituted or unsubstituted C4-C 50 Heterocyclic, substituted or unsubstituted C 10 -C 40 A fused ring group, a substituted or unsubstituted C5-C 40 The spirocyclic group may or may not contain any one or more of O, S, N, P, B, Si and Ge in the formed condensed ring.

[0019] In one embodiment of the present invention, the hydrogen atoms in the groups or substituent groups of R1 to R6 may be deuterated.

[0020] In one embodiment of the present invention, the specific structure of the iridium metal heterocyclic complex luminescent material can be:

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[0102] The present invention also provides a method for preparing an organic metal complex luminescent material, and the specific synthesis route is as follows:

[0103]

[0104] In the above formula, R1 to R6 are as defined in the above general formula I.

[0105] In one embodiment of the present invention, the specific preparation method comprises the following steps:

[0106] S1. Add 1,4-dioxane as a solvent to a three-necked flask, then add a compound of formula II and formula III and potassium acetate, replace nitrogen twice, add tris(dibenzylideneacetone)palladium (DBA palladium) and 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (X-phos), replace nitrogen twice again, react at a certain temperature for a period of time to obtain a compound of formula IV;

[0107] S2. Toluene, ethanol and water were added as solvents to a three-necked flask, and a compound of formula IV, a compound of formula V and anhydrous potassium carbonate were added to the three-necked flask, and then nitrogen was replaced twice, and tetrakis(triphenylphosphine)palladium (Pd(pph3)4) was added to react at a certain temperature for a period of time to prepare a compound of formula VI;

[0108] S3. Add 1,4-dioxane as a solvent to a three-necked flask, then add the compound of formula VI and formula III and potassium acetate, replace nitrogen twice, add DBA palladium and X-phos, replace nitrogen twice again, and react at a certain temperature for a period of time to obtain a compound of formula VII;

[0109] S4. Toluene, ethanol and water were added as solvents to a three-necked flask, and the compound of formula VII, the compound of formula VIII and anhydrous potassium carbonate were added to the three-necked flask, and then nitrogen was replaced twice and Pd(pph3)4 was added, and the reaction was carried out at a certain temperature for a period of time to prepare a compound of formula IX;

[0110] S5. Under a nitrogen atmosphere, a compound of formula Ⅹ and iridium trichloride, ethylene glycol ethyl ether and water as a solvent were added to a flask three after the reaction at a certain temperature for a period of time to obtain a compound of formula Ⅺ;

[0111] S6. Add dichloromethane and methanol as solvents to a three-necked flask, add a compound of formula Ⅺ and silver trifluoromethane sulfonate, and then replace nitrogen twice, react at a certain temperature for a period of time to obtain a compound of formula Ⅻ;

[0112] S7. Add anhydrous ethanol as a reaction solvent into a three-necked flask, add the compound of formula XII and the compound of formula IX, replace nitrogen twice, and react at a certain temperature for a period of time to obtain the compound of formula I.

[0113] In one embodiment of the present invention, in step S1, the molar ratio of the compound of formula II to the compound of formula III is 1:(1-2.2), preferably 1:2.

[0114] In one embodiment of the present invention, the amount of DBA palladium added in step S1 is 0.8% to 2.5% of the amount of the compound of formula II, and the preferred amount is 2%.

[0115] In one embodiment of the present invention, the amount of X-phos added in step S1 is 6% to 12% of the amount of the compound of formula II, and the preferred amount is 8%.

[0116] In one embodiment of the present invention, the molar ratio of potassium acetate to the compound of formula II in step S1 is (2-3):1, preferably 2.5:1.

[0117] In one embodiment of the present invention, the volume of 1,4-dioxane in step S1 is (15 to 25) times the mass of the compound of formula II.

[0118] In one embodiment of the present invention, the reaction temperature in step S1 is 70° C. to 100° C., and the reaction time is 12 h to 48 h.

[0119] In one embodiment of the present invention, in the compound of formula V in step S2, X is chlorine or bromine.

[0120] In one embodiment of the present invention, the molar ratio of the compound of formula IV to the compound of formula V in step S2 is (1-1.5):1, preferably 1.1:1.

[0121] In one embodiment of the present invention, the amount of Pd(pph3)4 added in step S2 is 2% to 4% of the amount of the compound of formula V.

[0122] In one embodiment of the present invention, the ratio of the amount of anhydrous potassium carbonate to the compound of formula V in step S2 is (2-4):1, preferably 3:1.

[0123] In one embodiment of the present invention, the volume of toluene in step S2 is (15 to 25) times the mass of the compound of formula V, and the added amounts of anhydrous ethanol and water are the same, which is 0.5 times the volume of toluene.

[0124] In one embodiment of the present invention, the reaction temperature in step S2 is 70° C. to 100° C., and the reaction time is 12 h to 36 h.

[0125] In one embodiment of the present invention, the ratio of reactants, the amount of catalyst and solvent added, and the reaction temperature and time in step S3 are consistent with those in step S1.

[0126] In one embodiment of the present invention, the reactant ratio, catalyst and solvent addition amount, and reaction temperature and time in step S4 are consistent with those in step S2.

[0127] In one embodiment of the present invention, the molar ratio of the compound of formula X to iridium trichloride in step S5 is (2-3):1, preferably 2.5:1;

[0128] In one embodiment of the present invention, the volume of ethylene glycol ethyl ether in step S5 is 20 times the mass of the compound of formula X, wherein the volume ratio of ethylene glycol ethyl ether to water is 4:1;

[0129] In one embodiment of the present invention, the reaction temperature in step S5 is 120° C., and the reaction time is 24 h to 48 h.

[0130] In one embodiment of the present invention, the molar ratio of the compound of formula XI to silver trifluoromethanesulfonate in step S6 is 1:(2-3), preferably 1:2.5.

[0131] In one embodiment of the present invention, the volume of methanol in step S6 is (6 to 9) times the mass of the compound of formula XI, and the volume ratio of methanol to dichloromethane is 1:(3 to 5).

[0132] In one embodiment of the present invention, the reaction temperature in step S6 is 25° C., and the reaction time is 24 h to 48 h.

[0133] In one embodiment of the present invention, the molar ratio of the compound of formula XII to the compound of formula IX in step S7 is (1.5-2.5):1, wherein the optimal ratio is 2:1.

[0134] In one embodiment of the present invention, the volume of anhydrous ethanol in step S7 is 20 times the mass of the compound of formula IX.

[0135] In one embodiment of the present invention, the reaction temperature in step S7 is 70° C. to 100° C., and the reaction time is 24 h to 48 h.

[0136] The present invention also provides an organic electroluminescent device, which comprises an organic layer; the organic layer contains the above-mentioned organic metal complex luminescent material.

[0137] In one embodiment of the present invention, the organic electroluminescent device further comprises a first electrode and a second electrode; wherein the organic layer is disposed between the first electrode and the second electrode; the organic layer comprises 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; wherein the luminescent layer comprises the organic metal complex luminescent material, and the organic metal complex luminescent material is used as a doping material therein.

[0138] In one embodiment of the present invention, the light-emitting layer comprises a host material and a doping material, and the mass ratio of the host material to the doping material is (90-99.5):(0.5-10).

[0139] The present invention has the following beneficial effects:

[0140] The organometallic complex luminescent material provided by the present invention adjusts the fluorescence wavelength of the organometallic complex by selecting a complex with a specific multi-benzene ring structure, such as combining a benzofuran derivative ligand with a multi-benzene ring and a specific 2-phenylpyridine derivative ligand through iridium metal, thereby obtaining a photoelectric material with a specific fluorescence wavelength. After the organometallic complex photoelectric material is used in an organic electroluminescent device, the driving voltage of the organic electroluminescent device is reduced, and at the same time the luminous efficiency is improved and the service life is extended. BRIEF DESCRIPTION OF THE DRAWINGS

[0141] Figure 1 This is the hydrogen nuclear magnetic resonance spectrum of the compound of structural formula Ⅰ-853 prepared by the present invention. DETAILED DESCRIPTION

[0142] The following will be clearly and completely described in conjunction with the technical solutions of the synthesis examples and embodiments of the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all of the embodiments. Based on the embodiments of the present invention, all embodiments obtained by ordinary technicians in this field without making creative work are within the scope of protection of the present invention.

[0143] Example 1

[0144] The synthetic route of steps S1 to S4 in formula Ⅰ-1 is as follows Figure 1 As shown:

[0145]

[0146] S1. Add Ⅱ-1 (1eq) (CAS: 2722774-62-9), pinacol borate (2eq) and potassium acetate (2.5eq) into a three-necked flask, then add 1,4-dioxane (20 times the mass of formula Ⅱ-1) as a solvent, replace nitrogen twice, add DBA (0.02eq) and X-phos (0.08eq), replace nitrogen twice again, and react at 80°C for 36h to obtain formula Ⅳ-1 (yield: 80.2%).

[0147] S2. Add IV-1 (1.1 eq), formula V (1 eq) and anhydrous potassium carbonate (3 eq) into a three-necked flask, then add 20 times the mass of formula V toluene, 0.5 times the mass of toluene in ethanol and water as solvents, replace nitrogen twice, add Pd(pph3)4 (0.03 eq), replace nitrogen twice again, react at 80°C for 24 hours, and obtain formula VI-1 (yield: 64.6%).

[0148] S3. Add VI-1 (1 eq), pinacol borate (2 eq) and potassium acetate (2.5 eq) into a three-necked flask, then add 1,4-dioxane (20 times the mass of formula VI-1) as a solvent, replace nitrogen twice, add DBA (0.02 eq) and X-phos (0.08 eq), replace nitrogen twice again, and react at 80°C for 48 hours to obtain formula VII-1 (yield: 72.4%).

[0149] S4. Add Ⅶ-1 (1.1 eq), formula VIII (1 eq) and anhydrous potassium carbonate (3 eq) into a three-necked flask, then add 20 times the mass of formula VIII toluene, 0.5 times the mass of toluene in ethanol and water as solvents, replace nitrogen twice and then add Pd(pph3)4 (0.03 eq), replace nitrogen twice again, react at 80°C for 24 hours, and obtain formula Ⅸ-1 (yield: 61.1%).

[0150] The synthetic route of steps S5 to S7 in formula Ⅰ-1 is as follows:

[0151]

[0152] S5. Add formula Ⅹ-1 (2.5eq) and iridium trichloride (1eq) into a three-necked flask, 20 times the mass of ethylene glycol ethyl ether of formula Ⅹ-1 and 0.25 times the mass of ethylene glycol ethyl ether in water as solvent, then replace nitrogen twice, react at 120°C for 48h, filter and dry to obtain formula Ⅺ-1 (yield: 68.7%).

[0153] S6. Add formula Ⅺ-1 (1 eq) into a three-necked flask, then add 8 times the mass of methanol of formula Ⅺ-1 and 4 times the mass of methanol in dichloromethane as solvent, replace the nitrogen twice, add silver trifluoromethanesulfonate (2.5 eq), then replace the nitrogen twice, and react at 25°C for 48 hours to obtain formula Ⅻ-1 (yield: 63.7%).

[0154] S7. Add formula XII-1 (1 eq) and formula IX-1 (2 eq) into a three-necked flask, then add 20 times the mass of anhydrous ethanol of formula IX-1, replace the nitrogen twice, react at 80°C for 36 hours, and obtain formula I-1 (yield: 39.2%, purity: 99.3%) by column chromatography (eluent: dichloromethane and hexane).

[0155] Mass spectrum: Test value is 821.46

[0156] Elemental analysis: C:65.84, H:3.68, O:1.95, N:5.12, Ir:23.41; test value: C:64.52, H:3.14, O:2.04, N:5.83.

[0157] NMR data: 1 H NMR(400MHz,Chloroform-d)δ9.24(s,1H),8.93(dd,2H),8.16(dd,1H),8.07(ddd,4H),7.91(dt,1H),7 .60-7.49(m,4H),7.49-7.33(m,6H),7.34(p,3H),7.35-7.29(m,2H),7.20-7.06(m,4H),7.02(dd,2H).

[0158] Example 2

[0159] The synthetic route of steps S1 to S4 in formula Ⅰ-444 is shown below.

[0160]

[0161] S1. Add Ⅱ-2 (1eq) (CAS: 2725785-66-8), pinacol borate (2eq) and potassium acetate (3eq) into a three-necked flask, then add 1,4-dioxane (20 times the mass of formula Ⅱ-2) as a solvent, replace nitrogen twice, add DBA (0.02eq) and X-phos (0.08eq), replace nitrogen twice again, and react at 80°C for 36h to obtain formula Ⅳ-2 (yield: 75.3%).

[0162] S2. Add IV-2 (1.1 eq), formula V (1 eq) and anhydrous potassium carbonate (3 eq) into a three-necked flask, then add 20 times the mass of formula V toluene, 0.5 times the mass of toluene in ethanol and water as solvents, replace nitrogen twice, add Pd(pph3)4 (0.03 eq), replace nitrogen twice again, react at 80°C for 36 hours, and obtain formula VI-2 (yield: 61.8%).

[0163] S3. Add VI-2 (1 eq), pinacol borate (2 eq) and potassium acetate (3 eq) into a three-necked flask, then add 1,4-dioxane (20 times the mass of formula VI-2) as a solvent, replace nitrogen twice, add DBA (0.02 eq) and X-phos (0.08 eq), replace nitrogen twice again, and react at 80°C for 40 hours to obtain formula VII-2 (yield: 73.3%).

[0164] S4. Add Ⅶ-2 (1.1 eq), formula VIII-1 (1 eq) (CAS: 2621-46-7) and anhydrous potassium carbonate (3 eq) into a three-necked flask, then add 20 times the mass of formula VIII-1 toluene, 0.5 times the mass of toluene in ethanol and water as solvents, replace nitrogen twice and then add Pd(pph3)4 (0.03 eq), replace nitrogen twice again, react at 80°C for 30 hours, and obtain formula IX-2 (yield: 58.6%).

[0165] The synthetic route of steps S5 to S7 in formula I-444 is as follows:

[0166]

[0167] S5. Add formula Ⅹ-2 (2.5eq) (CAS: 92646-00-9) and iridium trichloride (1eq) into a three-necked flask, 20 times the mass of ethylene glycol ether of formula Ⅹ-2 and 0.25 times the mass of ethylene glycol ether in water as solvent, then replace nitrogen twice, react at 120°C for 48h, filter and dry to obtain formula Ⅺ-2 (yield: 70.2%).

[0168] S6. Add formula Ⅺ-2 (1 eq) into a three-necked flask, then add 8 times the mass of methanol of formula Ⅺ-2 and 4 times the mass of methanol in dichloromethane as solvent, replace nitrogen twice, add silver trifluoromethanesulfonate (2.5 eq), then replace nitrogen twice, and react at 25°C for 48 hours to obtain formula Ⅻ-2 (yield: 67.3%).

[0169] S7. Add formula XII-2 (1eq) and formula IX-2 (2eq) into a three-necked flask, then add 20 times the mass of anhydrous ethanol of formula IX-2, replace nitrogen twice, react at 70°C for 36 hours, and obtain formula I-444 (yield: 35.3%, purity: 99.2%) by column chromatography (eluent: dichloromethane and hexane).

[0170] Mass spectrum: Test value is 1025.63

[0171] Elemental analysis: C:70.29, H:5.31, O:1.56, N:4.10, Ir:18.75; test value: C:71.03, H:5.49, O:1.84N:4.01.

[0172] NMR data: 1 H NMR(400MHz,Chloroform-d)δ9.30(d,1H),9.22(d,2H),8.41(d,2H),8.17(td,3H),8.06(d,1H),7. 95-7.85(m,3H),7.53-7.39(m,6H),7.39-7.30(m,5H),7.20-7.06(m,6H),2.9(d,1H)1.29(d,24H).

[0173] Example 3

[0174] The synthetic route of steps S1 to S4 in formula I-535 is as follows:

[0175]

[0176] Steps S1 to S3 are consistent with the operation steps S1 to S3 in Example 1.

[0177] S4. Add Ⅶ-1 (1.1 eq), formula Ⅷ-3 (1 eq) (CAS: 56866-67-2) and anhydrous potassium carbonate (3 eq) into a three-necked flask, then add 20 times the mass of formula Ⅷ-1 toluene, 0.5 times the mass of toluene ethanol and water as solvents, replace nitrogen twice and then add Pd(pph3)4 (0.03 eq), replace nitrogen twice again, react at 80°C for 30 hours, and purify by column chromatography (eluent: hexane and ethyl acetate) to obtain formula Ⅸ-3 (yield: 59.7%).

[0178] The synthetic route of steps S5 to S7 in formula I-535 is as follows:

[0179]

[0180] S5. Add formula Ⅹ-3 (2.5eq) (CAS: 1883378-94-6) and iridium trichloride (1eq) into a three-necked flask, 20 times the mass of ethylene glycol ether of formula Ⅹ-3 and 0.25 times the mass of ethylene glycol ether in water as solvent, then replace nitrogen twice, react at 120°C for 48h, filter and dry to obtain formula Ⅺ-3 (yield: 68.5%).

[0181] S6. Add formula Ⅺ-3 (1 eq) to a three-necked flask, then add 8 times the mass of formula Ⅺ-3 in methanol and 4 times the mass of methanol in dichloromethane as solvent, replace nitrogen twice, add silver trifluoromethanesulfonate (2.5 eq), then replace nitrogen twice, and react at 25 ° C for 48 h to obtain formula Ⅻ-3 (yield: 65.7%);

[0182] S7. Add formula Ⅻ-3 (1eq) and formula Ⅸ-3 (2eq) into a three-necked flask, then add 20 times the mass of anhydrous ethanol of formula Ⅸ-3, replace the nitrogen twice, react at 80°C for 40 hours, and obtain formula Ⅰ-535 (yield: 31.2%, purity: 99.4%) by column chromatography (eluent: dichloromethane and hexane).

[0183] Mass spectrum: Test value is 1107.71

[0184] Elemental analysis: C:65.16, H:5.65, O:1.45, N:3.80, Ir:18.75, Ge:6.57; tested value: C:65.23, H:5.41, O:1.87N:3.26, Ge:6.17.

[0185] NMR data: 1 H NMR(400MHz,Chloroform-d)δ9.24(s,1H),9.12(t,2H),8.19-8.13(m,1H),7.9(m,1H),7.86-7.79(m,2H),7.76-7. 67(m,6H),7.48-7.30(m,6H),7.20-7.13(m,2H),6.84(d,2H),2.28(s,6H),2.21(s,6H),1.33(s,18H),0.71(s,9H).

[0186] Example 4

[0187] The synthetic route of steps S1 to S4 in formula Ⅰ-627 is shown below.

[0188]

[0189] Step S1 is the same as step S1 of Example 1.

[0190] S2. Add IV-1 (1.1 eq), formula V-4 (1 eq) (CAS: 51624-36-3) and anhydrous potassium carbonate (3 eq) into a three-necked flask, then add 20 times the mass of formula V-4 in toluene, 0.5 times the mass of toluene in ethanol and water as solvents, replace nitrogen twice, add Pd(pph3)4 (0.03 eq), replace nitrogen twice again, react at 80°C for 36 hours, and obtain formula VI-4 (yield: 62.6%).

[0191] S3. Add VI-4 (1eq), bipyralidin (2eq) and potassium acetate (3eq) into a three-necked flask, then add 1,4-dioxane (20 times the mass of VI-4) as a solvent, replace nitrogen twice, add DBA (0.02eq) and X-phos (0.08eq), replace nitrogen twice again, and react at 80°C for 36h to obtain VII-4 (yield: 69.8%).

[0192] S4. Add Ⅶ-4 (1.1 eq), formula Ⅷ-4 (1 eq) (CAS: 24788-10-1) and anhydrous potassium carbonate (3 eq) into a three-necked flask, then add 20 times the mass of formula Ⅷ-4 toluene, 0.5 times the mass of toluene ethanol and water as solvents, replace nitrogen twice and then add Pd(pph3)4 (0.03 eq), replace nitrogen twice again, react at 80°C for 36 hours, and obtain formula Ⅸ-4 (yield: 55.7%).

[0193] The synthetic route of steps S5 to S7 in formula I-627 is as follows:

[0194]

[0195] S5. Add formula Ⅹ-4 (2.5eq) (CAS: 2925321-33-9) and iridium trichloride (1eq) into a three-necked flask, 20 times the mass of ethylene glycol ether of formula Ⅹ-4 and 0.25 times the mass of ethylene glycol ether in water as solvent, then replace nitrogen twice, react at 120°C for 48h, filter and dry to obtain formula Ⅺ-4 (yield: 69.4%).

[0196] S6. Add formula Ⅺ-4 (1 eq) into a three-necked flask, then add 8 times the mass of methanol of formula Ⅺ-4 and 4 times the mass of methanol in dichloromethane as solvent, replace nitrogen twice, add silver trifluoromethanesulfonate (2.5 eq), then replace nitrogen twice, and react at 25°C for 48 hours to obtain formula Ⅻ-4 (yield: 65.7%).

[0197] S7. Add formula Ⅻ-4 (1eq) and formula Ⅸ-4 (2eq) into a three-necked flask, then add 20 times the mass of anhydrous ethanol of formula Ⅸ-4, replace the nitrogen twice, react at 80°C for 36 hours, and obtain formula Ⅰ-627 (yield: 33.8%, purity: 99.2%) by column chromatography (eluent: dichloromethane and hexane).

[0198] Mass spectrum: Test value is 1140.74.

[0199] Elemental analysis: C:71.61, H:6.45, O:1.40, N:3.68, Ir:16.85; test value: C:71.23, H:6.71, O:1.83N:3.29.

[0200] NMR data: 1 H NMR(400MHz,Chloroform-d)δ9.26(s,1H),8.92(d,2H),8.38(d,2H),8.12(d,1H),7.94-7.88(m,1H),7.79-7.74(m, 2H),7.48-7.31(m,7H),7.26(d,1H),7.24-7.08(m,5H),6.84(d,2H),2.53(t,2H),2.45-2.40(m,10H),1.05(s,27H).

[0201] Example 5

[0202] The synthetic route of steps S1 to S4 in formula I-853 is as follows:

[0203]

[0204] Steps S1 to S3 are the same as steps S1 to S3 of Example 1.

[0205] S4. Add Ⅶ-1 (1.1 eq), formula Ⅷ-5 (1 eq) (CAS: 95347-95-8) and anhydrous potassium carbonate (3 eq) into a three-necked flask, then add 20 times the mass of formula Ⅶ-1 toluene, 0.5 times the mass of toluene ethanol and water as solvents, replace nitrogen twice and then add Pd(pph3)4 (0.03 eq), replace nitrogen twice again, react at 80°C for 40 hours, and obtain formula Ⅸ-5 (yield: 53.9%).

[0206] Wherein, the synthetic route of formula X-5 is as follows:

[0207]

[0208] ① Add X-5-1 (1 eq) (CAS: 325958-97-2), pinacol borate (2 eq) and potassium acetate (3 eq) into a three-necked flask, then add 1,4-dioxane (20 times the mass of formula X-5-1) as a solvent, replace nitrogen twice, add DBA palladium (0.02 eq) and X-phos (0.08 eq), replace nitrogen twice again, and react at 80 ° C for 36 hours to obtain formula X-5-2 (yield: 79.7%).

[0209] ② Add Ⅹ-5-2 (1.1 eq), formula Ⅹ-5-3 (1 eq) (CAS: 3972-55-2) and anhydrous potassium carbonate (3 eq) into a three-necked flask, then add 20 times the mass of formula Ⅹ-5-3 toluene, 0.5 times the mass of toluene in ethanol and water as solvents, replace nitrogen twice, add Pd(pph3)4 (0.03 eq), replace nitrogen twice again, react at 80°C for 24 hours, and obtain formula Ⅹ-5 (yield: 62.1%).

[0210] The synthetic route of steps S5 to S7 in formula I-853 is as follows:

[0211] S5. Add formula Ⅹ-5 (2.5eq) and iridium trichloride (1eq) into three flasks, 20 times the mass of ethylene glycol ether of formula Ⅹ-5 and 0.25 times the mass of ethylene glycol ether in water as solvent, then replace nitrogen twice, react at 120°C for 48h, filter and dry to obtain formula Ⅺ-5 (yield: 71.3%).

[0212] S6. Add formula Ⅺ-5 (1 eq) into a three-necked flask, then add 8 times the mass of methanol of formula Ⅺ-5 and 4 times the mass of methanol in dichloromethane as solvent, replace nitrogen twice, add silver trifluoromethanesulfonate (2.5 eq), then replace nitrogen twice, and react at 25°C for 48 hours to obtain formula Ⅻ-5 (yield: 67.6%).

[0213] S7. Add formula Ⅻ-5 (1eq) and formula Ⅸ-5 (2eq) into a three-necked flask, then add 20 times the mass of anhydrous ethanol of formula Ⅸ-5, replace nitrogen twice, react at 80°C for 30 hours, and obtain formula Ⅰ-853 (yield: 32.7%, purity: 99.3%) by column chromatography (eluent: dichloromethane and hexane).

[0214] Mass spectrum: Test value is 1147.92.

[0215] Elemental analysis: C:66.98, H:6.32, O:1.39, N:3.66, Ir:16.75, Si:4.89; test value: C:67.12, H:6.17, O:1.75N:3.64, Si:5.13.

[0216]

[0217] Wherein, the nuclear magnetic resonance hydrogen spectrum of formula I-853 is as follows Figure 1 shown.

[0218] The synthesis methods of other target structural compounds are the same as above and are not described here one by one. Their relevant structures, yields and mass spectrometry data are shown in Table 1 below.

[0219] Table 1 shows the structures, yields and mass spectrometry data of target compounds of Examples 6 to 15.

[0220] Example structure Molecular formula Yield (%) Mass spectrometry 6 Formula I-2 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 46 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 32 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 31.2 835.46 7 Formula I-30 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 50 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 35 <h2 style=";text-align:left;direction:ltr"> D5IrN3O]]><h2 style=";text-align:left;direction:ltr"> 33.7 896.52 8 Formula I-149 <![CDATA[C 54 H 38 D7IrN4O]]> 29.4 965.86 9 Formula I-212 <![CDATA[C 53 H 33 D 12 GeIrN4O]]> 31.4 1032.63 10 Formula I-316 <![CDATA[C 59 H 28 D 27 IrN4O]]> 28.5 1055.92 11 Formula I-369 <![CDATA[C 58 H 29 D 24 IrN4O]]> 35.3 1038.91 12 Formula I-391 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 70 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 36 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 34.8 1183.73 13 Formula I-502 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 61 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 61 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 31.4 1044.54 14 Formula I-660 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 72 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 68 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 30.5 1141.81 15 Formula I-854 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 65 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 69 <h2 style=";text-align:left;direction:ltr"> D5IrN3OSi2]]><h2 style=";text-align:left;direction:ltr"> 36.6 1166.74

[0221] Light emitting device embodiment 1

[0222] In the light emitting device embodiment 1, an organic electroluminescent device is provided, including 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.

[0223] The preparation method of the organic electroluminescent device is as follows:

[0224] (1) Preparation of ITO anode

[0225] The ITO glass substrate with a coating thickness of 1500 angstroms 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, ultrasonically cleaned with isopropyl alcohol, acetone, methanol and other solvents in turn, dried, and then transferred to a plasma cleaning machine, washed the above substrate for 5 minutes, and sent to a vapor deposition machine to evaporate other functional layers.

[0226] (2) Hole injection layer and hole transport layer

[0227] Formula A and Formula B were vacuum evaporated in the hole injection layer at an evaporation rate of 1 angstrom / second, with an evaporation rate ratio of 96:4. The structures of Formula A and Formula B are shown below. Formula A with a thickness of 118 nm was evaporated on the hole injection layer at an evaporation rate of 1.5 angstroms / second as a hole transport layer.

[0228]

[0229] (3) Organic light-emitting layer

[0230] At a deposition rate of 1 angstrom / second, a 27 nm light-emitting layer was deposited using 4,4'-N,N'-biphenyldicarbazole ("CBP") as a main material and Formula I-1 as a doping material, wherein the mass ratio of CBP to Compound Formula I-1 was 94:6.

[0231] (4) Hole blocking layer

[0232] Formula C was vacuum evaporated at a rate of 0.5 Å / s to form a hole blocking layer with a thickness of 5.0 nm.

[0233]

[0234] (5) Electron transport layer, electron injection layer

[0235] The electron transport layer of "Alq3" with a thickness of 35nm was vacuum-deposited at a deposition rate of 1 angstrom / second. The electron injection layer of LiF film with a thickness of 0.5nm was vacuum-deposited at a deposition rate of 0.5 angstrom / second.

[0236] (6) Cathode layer

[0237] Silver was evaporated to a thickness of 15 nm at an evaporation rate of 1 angstrom / second to obtain an organic electroluminescent device.

[0238] Referring to the light-emitting device embodiment 1, the doping material formula Ⅰ-1 in the organic electroluminescent device is replaced by formula Ⅰ-2, Ⅰ-30, Ⅰ-149, Ⅰ-212, Ⅰ-316, Ⅰ-369, Ⅰ-391, Ⅰ-444, Ⅰ-502, Ⅰ-535, Ⅰ-627, Ⅰ-660, Ⅰ-853, and Ⅰ-854, and they are prepared into organic electroluminescent devices respectively.

[0239] Comparative Example 1

[0240] An organic electroluminescent device is prepared by the same method as in Example 1 of the light-emitting device, and the doping material of Formula I-1 in the light-emitting layer is replaced by a compound of Formula D, the structure of which is shown below:

[0241]

[0242] Comparative Example 2

[0243] An organic electroluminescent device is prepared by the same method as in Example 1 of the light-emitting device, and the doping material of Formula I-1 in the light-emitting layer is replaced by a compound of Formula E. The structure of Formula E is shown below.

[0244]

[0245] Comparative Example 3

[0246] An organic electroluminescent device is prepared by the same method as in Example 1 of the light-emitting device, and the doping material of Formula I-1 in its light-emitting layer is replaced by a compound of Formula F, the structure of which is shown below.

[0247]

[0248] Comparative Example 4

[0249] An organic electroluminescent device is prepared by the same method as in Example 1 of the light-emitting device, and the doping material of Formula I-1 in its light-emitting layer is replaced by the compound of Formula G. The structure of Formula G is shown below.

[0250]

[0251] In order to further illustrate the luminescent properties of the organic metal complex luminescent material prepared in the present invention, the luminescent properties of the organic light-emitting devices prepared in the examples and the devices obtained in comparative examples 1, 2, 3 and 4 were tested. The measurements were made 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.

[0252] Table 2 Luminescence detection data of organic electroluminescent devices of Examples 1-15 and Comparative Examples 1-4

[0253]

[0254]

[0255] It can be seen from Table 2 that when the brightness is the same, compared with Comparative Examples 1-4, the driving voltage of the organic electroluminescent devices prepared in Examples 1-15 of the present invention is reduced, and the efficiency and life are improved. This is because the benzene derivatives connected to benzofuran can adjust the fluorescence wavelength of the substance, so that the corresponding substance has better luminous efficiency and life.

[0256] 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.

[0257] It will be apparent to those skilled in the art that many modifications and variations of the present invention are possible without departing from the spirit and scope of the present invention. It is therefore contemplated that the present invention covers modifications and variations of the present invention provided within the scope of the appended claims and their equivalents.

[0258] The above description of the disclosed embodiments enables those skilled in the art to implement or use the present invention. Various modifications to these embodiments will be apparent to those 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 organic iridium metal complex luminescent material, characterized in that: It has the general structural formula shown in Formula I: In Formula I, R1 to R6 are each independently selected from hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amino, sulfonic acid, substituted or unsubstituted C1-C 40 Alkyl, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C6-C 40 Heteroaryl, substituted or unsubstituted C3-C 40 Cycloalkyl, substituted or unsubstituted C1-C 40 Alkoxy, substituted or unsubstituted C1-C 40 Alkylamino, substituted or unsubstituted C2-C 40 Alkenyl or alkyne, substituted or unsubstituted C2-C 40 Heterocyclyl, substituted or unsubstituted C8-C 40 Condensed ring group, substituted or unsubstituted C5-C 40 Spirocyclyl, substituted or unsubstituted C1-C 40 Silane, substituted or unsubstituted C1-C 40 Germanyl; The substituents at positions R1 to R6 are the same or different; The positions of R1 to R5 are any positions of the benzene ring, the number of R1, R2, R4 and R5 substituents is 0 to 4, the number of R3 substituents is 0 to 5, and the number of R6 substituents is 0 to 1.

2. The organic iridium metal complex luminescent material according to claim 1, characterized in that: The R1 to R6 each independently represent hydrogen, deuterium, cyano, fluorine, trimethylsilyl, trimethylgermanyl, substituted or unsubstituted C1-C 15 Alkyl, substituted or unsubstituted C3-C 15 Cycloalkyl, substituted or unsubstituted C1-C 15 Alkoxy, substituted or unsubstituted C2-C 15 Heterocyclic, substituted or unsubstituted C6-C 15 Aryl, substituted or unsubstituted C8-C 20 In the fused ring group, substituents of R1 to R6 are the same or different.

3. The organic iridium metal complex luminescent material according to claim 1, characterized in that: The substituted or unsubstituted C1-C 15 The alkyl group is independently selected from one or more of methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, isopentyl, neopentyl, hexyl, 2-methylpentyl, 3-methylpentyl, 2,3-dimethylbutyl and 2,2-dimethylbutyl; Preferably, the substituted or unsubstituted C6-C 15 The aryl group is independently selected from one or more of phenyl, tolyl, chlorophenyl, bromophenyl, fluorophenyl, biphenyl, terphenyl, naphthyl, anthracenyl and phenanthryl; Preferably, the substituted or unsubstituted C3-C 15 The cycloalkyl group is independently selected from one or more of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl; Preferably, the substituted or unsubstituted C1-C 15 The alkoxy group is independently selected from one or more of methoxy, ethoxy, propoxy and phenoxy; Preferably, the substituted or unsubstituted C2-C 15 The heterocyclic group is independently selected from an aromatic or non-aromatic cyclic group having at least one heteroatom, wherein the heteroatom is selected from one or more combinations of O, S, N, P, B, Si and Ge.

4. The organic iridium metal complex luminescent material according to claim 1, characterized in that: The C2-C 15 The heterocyclic groups are independently selected from oxirane, thiirane, tetrahydrofuran, thiophene, pyrrole, pyridine, tetrahydrothiophene, pyrazine, imidazole; The C8-C 20 The fused ring group is independently selected from one or more of indole, quinoline, benzofuran, benzothiophene, isoquinoline, benzimidazole, 2-phenylpyridine and its derivatives, dibenzofuran and dibenzothiophene.

5. The organic iridium metal complex luminescent material according to claim 1, characterized in that: The R1 to R6 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 40 Alkyl, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Cycloalkyl, substituted or unsubstituted C4-C 50 Heterocyclic, substituted or unsubstituted C 10 -C 40 A fused ring group, a substituted or unsubstituted C5-C 40 The spirocyclic group may or may not contain any one or more of O, S, N, P, B, Si and Ge in the formed condensed ring.

6. The organic iridium metal complex luminescent material according to claim 1, characterized in that: The hydrogen atoms in the groups or substituent groups of R1 to R6 may be deuterated.

7. The organic iridium metal complex luminescent material according to claim 1, characterized in that: The specific structure of the iridium metal heterocyclic complex luminescent material includes:

8. The method for preparing the organometallic complex luminescent material according to any one of claims 1 to 7, characterized in that: The specific preparation method comprises the following steps: S1. Add 1,4-dioxane as a solvent to a three-necked flask, then add the compound of formula II and formula III and potassium acetate, replace nitrogen, add tris(dibenzylideneacetone)palladium (DBA palladium) and 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (X-phos), replace nitrogen again, react at a certain temperature for a period of time to obtain a compound of formula IV; S2. Toluene, ethanol and water are added as solvents to a three-necked flask, and a compound of formula IV, a compound of formula V and anhydrous potassium carbonate are added to the three-necked flask, and then after replacing nitrogen, tetrakis(triphenylphosphine)palladium (Pd(pph3)4) is added to react at a certain temperature for a period of time to prepare a compound of formula VI; S3. Add 1,4-dioxane as a solvent to a three-necked flask, then add the compound of formula VI and formula III and potassium acetate, replace nitrogen, add DBA palladium and X-phos, replace nitrogen again, react at a certain temperature for a period of time to obtain a compound of formula VII; S4. Toluene, ethanol and water are added as solvents into a three-necked flask, and the compound of formula VII, the compound of formula VIII and anhydrous potassium carbonate are added into the three-necked flask, and then Pd(pph3)4 is added after replacing the nitrogen, and the reaction is carried out at a certain temperature for a period of time to prepare the compound of formula IX. S5. Under a nitrogen atmosphere, a compound of formula Ⅹ and iridium trichloride, ethylene glycol ethyl ether and water as a solvent were added to the three flasks, and the reaction was carried out at a certain temperature for a period of time to obtain a compound of formula Ⅺ; S6. Add dichloromethane and methanol as solvents to a three-necked flask, add a compound of formula Ⅺ and silver trifluoromethane sulfonate, and then replace nitrogen twice, react at a certain temperature for a period of time to obtain a compound of formula Ⅻ; S7. Anhydrous ethanol was added to a three-necked flask as a reaction solvent, and the compound of formula Ⅻ and the compound of formula Ⅸ were added thereto. After nitrogen was replaced, the reaction was carried out at a certain temperature for a period of time to obtain a compound of formula Ⅰ; The specific synthetic route of the general structural formula shown in Formula I is as follows: In the above synthesis route, R1-R6 are defined as in the general formula I as described in any one of claims 1 to 7.

9. The preparation method according to claim 8, characterized in that: In the step S1, the molar ratio of the compound of formula II to the compound of formula III is 1:(1-2.2), preferably 1:2; Preferably, the amount of DBA palladium added in step S1 is 0.8% to 2.5% of the amount of the compound of formula II, preferably 2%; Preferably, the amount of X-phos added in step S1 is 6% to 12% of the amount of the compound of formula II, preferably 8%; Further preferably, in step S1, the ratio of the amount of potassium acetate to the compound of formula II is (2-3):1, preferably 2.5:1; Preferably, the volume of 1,4-dioxane in step S1 is 15 to 25 times the mass of the compound of formula II; Preferably, the reaction temperature in step S1 is 70°C to 100°C, and the reaction time is 12h to 48h; Preferably, in the step S2, X in the structure of the compound of formula V is independently selected from chlorine or bromine; Preferably, in step S2, the molar ratio of the compound of formula IV to the compound of formula V is (1-1.5):1, for example, 1.1:1; Preferably, the amount of Pd(pph3)4 added in step S2 is 2% to 4% of the amount of the compound of formula V; Preferably, the ratio of the amount of anhydrous potassium carbonate to the amount of the compound of formula V in step S2 is (2-4):1, preferably 3:1; Preferably, the volume of toluene in step S2 is 15 to 25 times the mass of the compound of formula V, and the volume of anhydrous ethanol and water is the same, which is 0.5 times the volume of toluene; Preferably, the reaction temperature in step S2 is 70°C to 100°C, and the reaction time is 12h to 36h; Preferably, the reactant ratio, catalyst and solvent addition amount, reaction temperature and time in step S3 are the same as those in step S1; Preferably, the reactant ratio, catalyst and solvent addition amount, reaction temperature and time in step S4 are the same as those in step S2; Preferably, in step S5, the molar ratio of the compound of formula X to iridium trichloride is (2-3):1, for example, 2.5:1; Preferably, the volume of ethylene glycol ethyl ether in step S5 is 20 times the mass of the compound of formula X, wherein the volume ratio of ethylene glycol ethyl ether to water is 4:1; Preferably, the reaction temperature in step S5 is 120° C. and the reaction time is 24 h to 48 h; Preferably, in step S6, the molar ratio of the compound of formula XI to silver trifluoromethanesulfonate is 1:(2-3), for example, 1:2.5; Furthermore, in step S6, the volume of methanol is (6 to 9) times the mass of the compound of formula XI, and the volume ratio of methanol to dichloromethane is 1:(3 to 5); Preferably, the reaction temperature in step S6 is 25° C. and the reaction time is 24 h to 48 h; Preferably, in step S7, the ratio of the amount of the compound of formula XII to the amount of the compound of formula IX is (1.5-2.5):1, wherein the optimal ratio is 2:1; Preferably, the volume of anhydrous ethanol in step S7 is 20 times the mass of the compound of formula IX; Preferably, the reaction temperature in step S7 is 70° C. to 100° C., and the reaction time is 24 h to 48 h.

10. An organic electroluminescent device, characterized in that: An organic layer comprising an organic layer containing the organic metal complex luminescent material according to any one of claims 1 to 7; Preferably, 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; the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer; wherein the light-emitting layer comprises an organic metal complex light-emitting material as a doping material; Preferably, the light-emitting layer comprises a host material and a doping material, and the mass ratio of the host material to the doping material is 90-99.5:0.5-10.

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