Organic metal iridium luminescent material as well as preparation method and application thereof

Abstract

The invention provides an organic metal iridium luminescent material as well as a preparation method and application thereof. The organic metal iridium luminescent material has a structural general formula of Ir (La) 2 (Lb) 1, wherein La represents a first ligand coordinated with a metal, and Lb represents a second ligand coordinated with the metal. The organic light-emitting material is obtained by adjusting the ligand molecular structure and the metal iridium complex, and the organic light-emitting material is used as a light-emitting doping material of an organic electroluminescent device, so that the light-emitting efficiency can be improved, the driving voltage can be reduced, and the service life of the device can be prolonged.

Description

Technical Field

[0001] This invention belongs to the field of organic light-emitting materials, and relates to an organometallic iridium light-emitting material, its preparation method, and its application. Background Technology

[0002] Since its inception, Organic Light Emitting Diodes (OLED) technology has attracted widespread attention and research worldwide, becoming one of the most promising technologies in the modern display and lighting fields. The core of OLED technology lies in organic light-emitting materials, which possess unique photoelectric properties, enabling them to efficiently convert electrical energy into light energy under the influence of an electric field, thereby emitting visible light.

[0003] Organic phosphorescent materials, as an important class of organic optoelectronic functional materials, have shown great application potential in many fields due to their unique photophysical properties, and have become one of the research hotspots in materials science and chemistry in recent years. Phosphorescence originates from the radiative transition from the triplet excited state to the ground state, and compared with fluorescent materials, it has characteristics such as a longer excited-state lifetime and a larger Stokes shift. The triplet excited state of organic molecules is easily deactivated rapidly through non-radiative transitions, making phosphorescence difficult to observe. This limitation greatly restricts the practical application of organic phosphorescent materials.

[0004] Currently, the research focus of organic phosphorescent materials is mainly concentrated on the following aspects: developing novel room temperature organic phosphorescent materials with high quantum yield, long lifetime, and high color purity; exploring the relationship between the structure and properties of materials to reveal the intrinsic mechanism of room temperature phosphorescence generation; and expanding the practical applications of organic phosphorescent materials in various fields.

[0005] Organic iridium complexes, as outstanding representatives of next-generation phosphorescent materials, have driven significant progress in the fields of optoelectronics and biomedicine over the past two decades. Their core advantages include extremely high phosphorescence efficiency and the ability to precisely and conveniently control their emission wavelength by altering the structure of cyclic metal ligands or auxiliary ligands through molecular design, covering a broad spectral range from deep blue to near-infrared and thus controlling the emission color. They also exhibit long phosphorescence lifetimes and good photochemical stability. However, they are costly, and in high concentrations or in solid states, intermolecular interactions can easily lead to a decrease in phosphorescence efficiency.

[0006] Therefore, developing materials to improve the performance and stability of devices remains a key research focus in this field. Summary of the Invention

[0007] To address the shortcomings of existing technologies, the present invention aims to provide an organometallic iridium luminescent material, its preparation method, and its applications. This invention obtains an organic luminescent material by adjusting the ligand molecular structure and its iridium complex. Using this material as a luminescent dopant in organic electroluminescent devices can improve luminous efficiency, reduce driving voltage, and extend device lifetime.

[0008] To achieve this objective, the present invention adopts the following technical solution:

[0009] On one hand, the present invention provides an organometallic iridium luminescent material, wherein the organometallic luminescent material has Ir(L a )2(L b The general structural formula of 1; where L a L represents the first ligand that coordinates with the metal. b This indicates the second ligand coordinated with the metal; "2" represents L. a The number of ligands is two, "1" represents L b The number of ligands is one, wherein the ligand L a general formula:

[0010] ;

[0011] In formula I-La, X can be selected from Si or Ge;

[0012] R1~R 12 Each time it appears, it is selected from the following atoms or groups, either identically or differently: hydrogen, deuterium, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C20 heterocyclic, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C20 arylsilyl, substituted or unsubstituted C3-C20 alkylgermanium, substituted or unsubstituted C6-C20 arylgermanium, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphin, and combinations thereof.

[0013] And R1~R 12 They exist independently or at least two of them can be connected to form a ring structure, and the fused ring structure formed includes an aromatic group of C3 to C20, an aromatic heterocycle of C3 to C20, a cycloalkyl group of C3 to C20, or a heterocyclic group of C3 to C20;

[0014] The heteroatoms in the heteroaryl and heterocyclic groups include one or a combination of at least two of O, N, S, Ge, Si, P, and B;

[0015] In the above formulas I-La, the hydrogen atoms are either independently substituted with deuterium or not substituted with deuterium;

[0016] The ligand L b The general formula is:

[0017] ;

[0018] Where R a ~R c Each is independently a hydrogen atom, deuterium atom, halogen, cyano group, substituted or unsubstituted C1-C. 20 Alkyl, substituted or unsubstituted C3-C 20 cycloalkyl; R a ~R b The substituents at the positions can be the same or different;

[0019] The above group R a ~R c The hydrogen atoms of the substituents are either unsubstituted, partially substituted, or completely substituted with deuterium.

[0020] Furthermore, wherein R1 to R 12 Each of the following is independently selected from hydrogen, deuterium, F, cyano, trifluoromethyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C20 arylsilyl, C3-C10 silyl or germanyl.

[0021] Furthermore, the R1 to R 12 Preferred substituted or unsubstituted C1-C10 alkyl groups include: methyl, ethyl, 2,2-dimethylpropyl, 2-methylbutyl, trimethylpentyl, isopropyl, 2-dimethylpropyl, and tert-butyl.

[0022] Furthermore, the R1 to R 12 Preferred substituted or unsubstituted C6-C12 aryl groups include: benzene ring, naphthyl ring, 1,3-diisopropylphenyl, 1,3-dimethylphenyl, 1,3-ditrifluoromethylphenyl, and 1,3,5-triethylphenyl.

[0023] Furthermore, the R1 to R 12 Preferred substituted or unsubstituted C3-C12 cycloalkyl groups include: cyclopentyl, cyclohexyl, 1,3-dimethylcyclopentyl, 1,3-dimethylcyclohexyl, 1,1-dimethylcyclohexyl, 1-tert-butylcyclopentyl, 1,3,5-triethylcyclohexyl, and neopentylcyclohexyl.

[0024] Furthermore, the R1 to R 12Preferred substituted or unsubstituted C6-C20 arylsilyl, C3-C10 silyl or germanyl groups, including: trimethylsilyl, dimethylphenylsilyl, dimethylcyclohexylsilyl, and trimethylgermanyl.

[0025] Further, the ligand L b It can be any of the following structures:

[0026] .

[0027] Preferably, the organometallic iridium luminescent material has the structure shown in Formula I:

[0028] .

[0029] Preferably, the organometallic iridium luminescent material is any one of the following compounds:

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065] .

[0066] Another object of the present invention is to provide a method for preparing the above-mentioned organometallic iridium luminescent material, comprising the following steps:

[0067] 1) Add (1 eq) reactant 1, (2 eq) reactant 2, (3 eq) anhydrous potassium carbonate, (20 eq) toluene, (10 eq) ethanol, and (10 eq) water to a three-necked flask. After purging with nitrogen, add (2% eq) tetra-triphenylphosphine palladium and purify with nitrogen again. Reflux at 100°C for 24 h. After the reaction is complete, obtain intermediate 1 by separation, rotary evaporation, and column chromatography.

[0068] 2) (1 eq) intermediate 1, (1.02 eq) 4-nitrobenzaldehyde, (3 eq) lithium tert-butoxide, and (20 eq) toluene were added to a three-necked flask. Nitrogen gas was replaced by adding (4% eq) tritert-butylphosphine and (2% eq) bis(μ-chloro-η3-allylpalladium(II)). The reaction was carried out at 120 °C for 10 h. After the reaction was completed, the mixture was cooled by an ice bath and quenched by adding saturated ammonium chloride solution. The organic phases were then extracted with diethyl ether and combined and dried with anhydrous magnesium sulfate. The organic phases were filtered and evaporated to dryness (40 °C). The resulting product was obtained by column chromatography. Formula I-La-1 was then obtained.

[0069] 3) Add (2eq) of formula I-La-1, (20eq) of ethylene glycol ethyl ether, and (10eq) of water to a three-necked flask to replace nitrogen gas. Then add (1eq) of iridium trichloride and replace nitrogen gas again. Reflux at 120°C for 48 hours. After the reaction is completed, filter the system and wash with ethanol and petroleum ether and dry to obtain intermediate 2.

[0070] 4) Add (1eq) intermediate 2, (3eq) ligand Lb, and (20eq) ethylene glycol ethyl ether to a three-necked flask to purge nitrogen. Then add ligand Lb and purge nitrogen again. Reflux at 120°C for 48 h. After the reaction is complete, filter the system and wash with ethanol and dry to obtain formula I.

[0071] .

[0072] The present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising an anode layer, a cathode layer and an organic layer disposed between the anode layer and the cathode layer, the organic layer comprising a light-emitting layer, the light-emitting layer comprising a host material and a dopant material, the dopant material comprising the organometallic iridium light-emitting material as described above.

[0073] Preferably, the organic layer further includes at least one of a hole functional layer and an electronic functional layer, wherein the hole functional layer includes a hole injection layer and a hole transport layer.

[0074] Preferably, the organic electroluminescent device includes a substrate layer and an encapsulation protective layer.

[0075] Preferably, the organic electroluminescent device includes a substrate layer, an anode layer, a hole functional layer (injection layer and transport layer), a light-emitting layer, an electronic functional layer, a cathode layer, and an encapsulation and protection layer.

[0076] The substrate layer is used to support the entire device structure and needs to be flat, heat resistant and flexible. The main materials are glass or plastics such as polyimide (PI).

[0077] Furthermore, the anode layer is used to inject holes (positive charges), which requires high light transmittance. Transparent conductive oxides such as indium tin oxide (ITO) are commonly used to match the hole injection requirements.

[0078] Furthermore, the organic electroluminescent device further includes a hole injection layer. This hole injection layer can be a single-material functional layer or a functional layer containing multiple materials. The main requirement is to reduce the energy barrier between the anode and the hole layer and improve transmission efficiency. The most commonly used multiple materials are hole transport materials doped with a certain proportion of p-type conductive doped materials. Common p-type doped materials include the following or others:

[0079] .

[0080] In this process, the luminescent layer excites the luminescent molecules to generate photons through the recombination of holes and electrons. Its structure includes a host material and a guest material (i.e., a doped material). The host material transfers energy and carries the luminescent guest (e.g., a dual-host design: an electron-donating host and an electron-withdrawing delayed fluorescence host, with an energy range ≤0.2 eV). The guest material, including phosphorescent iridium complexes and thermally activated delayed fluorescence (TADF) materials, determines the luminescence color and efficiency.

[0081] The electronic functional layer transports electrons from the cathode to the light-emitting layer. The material must have high electron mobility (such as imidazole derivatives and metal chelates). Low work function materials are commonly used, such as Mg and Ca (work function -0.2 to -3.5 eV), or transition metal coordination doping, such as o-phenanthroline materials + Ag / Cu, which enhance electron injection through coordination reactions.

[0082] Furthermore, the cathode layer commonly uses metals (Al, Ag) and transparent oxides. Secondly, multilayer cathodes (such as Mg / Ag alloys) are often used to balance conductivity and stability.

[0083] Future devices will continue to optimize the interface and material energy level matching of each layer, developing towards ultrathin, high brightness, and long lifespan. The organic electroluminescent material of this invention is prepared by introducing new compounds formed by the combination of silane and naphthalene rings. The compounds and ligands synthesize new organic electroluminescent materials. Since the naphthalene-silicon (germanium) heterocyclic structure may have both hole and electron transport characteristics (bipolarity), it improves the internal charge balance of the device, reduces the voltage rise caused by carrier accumulation, and can effectively reduce energy consumption. The fusion of naphthalene ring and silicon heterocyclic enhances molecular rigidity, reduces energy loss caused by vibration / rotation, and improves phosphorescence efficiency. The rigid structure of silicon heterocyclic (especially Si-C with high bond energy) and fused ring naphthalene can enhance the thermal stability of the material, slow down decomposition at high temperature, and thus improve the thermal stability of the device and further extend its service life.

[0084] Compared with the prior art, the present invention has the following beneficial effects:

[0085] This invention obtains organic light-emitting materials by adjusting the ligand molecular structure and iridium complex. Using these materials as light-emitting dopant materials for organic electroluminescent devices can improve luminous efficiency, reduce driving voltage, and extend device lifespan. Attached Figure Description

[0086] Figure 1 The 1H NMR spectrum of compound I-40. Detailed Implementation

[0087] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0088] Unless otherwise stated, the raw materials and reagents used in the following examples of the present invention are all commercially available products, and the preparation methods are not limited. Typical but not limited examples are the following compounds, and their synthetic routes and preparation methods are as follows:

[0089] 1. Synthesis of reactant 1-1

[0090]

[0091] In a three-necked flask, isopropanol in 45 times its mass of 4-(dimethylsilyl)benzonitrile was added. After purging with nitrogen twice, 2-bromo-3-iodopyridin-4-amine (1.15 eq) (CAS: 1300750-77-9), 4-(dimethylsilyl)benzonitrile (1 eq) (CAS: 129409-68-3), cuprous iodide (0.8% eq), and ethylene glycol (3 eq) were added. After purging with nitrogen twice, the mixture was reacted at 20°C for 0.5 h. Then, anhydrous potassium carbonate was added, and after purging with nitrogen twice, the mixture was refluxed at 100°C for 20 h. After the reaction was complete, the solvent was removed, the mixture was diluted with 500 mL of acetic acid, and then tert-butylnitrite (2.2 eq) was added. The mixture was stirred overnight at room temperature. After the reaction was complete, the reaction solution was poured into water, and the resulting solid was purified by column chromatography to obtain reactant 1-1 (yield: 40%).

[0092] 2. Synthesis of reactant 2-1

[0093]

[0094] The three-necked flask was purged with nitrogen twice. Under nitrogen protection, (6-tert-butylnaphthyl-1-yl)boric acid (CAS: 2762921-29-7) (1.0 eq) and anhydrous dichloromethane were added and stirred to dissolve. The three-necked flask was placed under liquid nitrogen protection at -78°C. N-bromosuccinimide (NBS) (1.05 eq) was weighed and dissolved in a small amount of anhydrous dichloromethane (or the solid was added directly to the three-necked flask in batches), and the temperature was maintained. If NBS was dissolved in anhydrous dichloromethane, it should be added slowly dropwise while maintaining the temperature. After reacting for 2 hours, the reaction was monitored by TCL. After the starting material disappeared, saturated sodium sulfite aqueous solution was added to quench excess NBS and any HBr that might be generated. The mixture was stirred for a few minutes until the solution decolorized. The organic layer was carefully washed with saturated sodium bicarbonate aqueous solution (to neutralize the acid), and then extracted with water and saturated brine. The organic phase was dried with anhydrous sodium sulfate or anhydrous magnesium sulfate and filtered to remove the solvent. The organic system was then subjected to column chromatography to obtain reactant 2-1 (yield 51%).

[0095] 3. Synthesis of La-40

[0096]

[0097] Add reactant 1-1 (1 eq) and reactant 2-1 (2 eq) to a three-necked flask, then add (20 eq) of toluene by mass of reactant 1-1 and (10 eq) of anhydrous ethanol and water. Purge with nitrogen twice. Then add Pd(pph3)4 (2% eq) and anhydrous potassium carbonate (K2CO3) (3 eq), and purge with nitrogen twice. React at 100 °C for 24 h. After the reaction is complete, extract, rotary evaporate, and column chromatography to obtain intermediate 1-1 (yield: 40%).

[0098] Intermediate 1-1 (1 eq) was added to a three-necked flask along with 4-nitrobenzaldehyde (1.02 eq), lithium tert-butoxide (3 eq), and toluene. Nitrogen gas was purged and tri-tert-butylphosphine (4% eq) and bis(μ-chloro-η3-allylpalladium(II)) (2% eq) were added. The reaction was carried out at 120 °C for 10 h. The reaction was quenched by adding saturated ammonium chloride solution after cooling in an ice bath. The organic phases were then extracted with diethyl ether and dried over anhydrous magnesium sulfate. The organic phases were filtered and evaporated to dryness (40 °C), followed by column chromatography to obtain formula I-La-1 (yield: 65%).

[0099] 4. Synthesis of Equations 1-40

[0100]

[0101] ligand L a -40 (2.5 eq) and IrCl3·3H2O (1 eq) were added to a three-necked flask, followed by the addition of ligand L. a -40 ethylene glycol ethyl ether (15 times by mass) and purified water (3 times by mass) were purged with nitrogen twice and then refluxed at 120°C for 48 h. The mixture was then cooled to room temperature, the precipitate was filtered, washed with anhydrous ethanol and petroleum ether in sequence, and dried to obtain bridged ligand intermediate 2 (yield: 90%).

[0102] Intermediate 2 (1eq), L b Ligand-15 (3 eq) (CAS No.: 1522-20-9) and anhydrous potassium carbonate (10 eq) were added to a three-necked flask, followed by the addition of 20 times the mass of intermediate 2 in ethylene glycol ethyl ether. After purging with nitrogen twice, the mixture was refluxed at 120 °C for 48 h, then cooled to room temperature. The precipitate was filtered, washed with anhydrous ethanol, and dried to obtain the compound with the structure shown in I-40 (yield: 57%), with an HPLC purity greater than 99%.

[0103] MS (ESI, m / Z): [M+H]+: 1181.15.

[0104] NMR hydrogen spectrum as shown Figure 1 As shown.

[0105] The synthesis methods for other compounds are roughly the same, and will not be listed here.

[0106] Device Example 1

[0107] The ITO anode layer on the transparent glass substrate was cleaned by ultrasonic cleaning with deionized water, acetone, and ethanol for 20 minutes each. After cleaning and drying, the substrate was transferred to a plasma cleaner and washed for 5 minutes. Then, ITO anode layer was deposited sequentially by vacuum evaporation.

[0108] 1) Hole injection layer (HIL) material m-MTDATA, thickness 250 Å, evaporation rate 0.2-0.5 Å / s This layer serves as the hole injection layer;

[0109] 2) Hole transport layer (HTL): A 200 Å thick NPB material was deposited at a rate of 0.5 Å / s.

[0110] 3) The main material of the light-emitting layer (EML) is CBP: doped compound I-40 (95:5), with a deposition thickness of 300 Å and a deposition rate of 0.2 Å / s;

[0111] 4) Hole blocking layer / electron transport layer (HBL / ETL): HBL is made of BCP material, with a deposition thickness of 100 Å and a deposition rate of 1 Å / s; ETL is made of Alq3 material, with a deposition thickness of 100 Å and a deposition rate of 1 Å / s.

[0112] 5) Finally, on the electron injection layer, cathode Al is deposited by vacuum evaporation with a thickness of 1000 Å. This layer is used as the cathode conductive electrode and is called the cathode layer.

[0113] The organic electroluminescent device was prepared using the same method as in Device Example 1, with the red light-doped compound in the emitting layer being I-40. The structural formulas of the compounds m-MTDATA, NPB, CBP, Alq3, and BCP used in this invention are as follows:

[0114] .

[0115] Referring to the above method, replace Equation I-40 with Equation I-3; Equation I-8; Equation I-19; Equation I-26; Equation I-27; Equation I-28; Equation I-30; Equation I-34; Equation I-50; Equation I-62; Equation I-80; Equation I-136; Equation I-149; Equation I-205; Equation I-206; Equation I-208; Equation I-219; Equation I-340; Equation I-361; Equation I-410; Equation I-427; Equation I-435; Equation I-442; Equation I-448; Organic electroluminescent devices of the corresponding compounds were prepared using Formula I-464; Formula I-493; Formula I-529; Formula I-545; Formula I-553; Formula I-576; Formula I-579; Formula I-599; Formula I-611; Formula I-621; Formula I-630; Formula I-634; Formula I-648; Formula I-653; Formula I-660; Formula I-667; Formula I-677; Formula I-682; Formula I-687; Formula I-691; Formula I-709; and Formula I-727.

[0116] Comparative Example 1

[0117] An organic electroluminescent device was fabricated using the same method as in Device Example 1, except that the dopant material I-40 in the light-emitting layer was replaced with compound 1-6, and its structure is shown below:

[0118] .

[0119] The prepared organic electroluminescent devices were subjected to the same tests as in Example 1, and the results are shown in Table 1.

[0120] Table 1

[0121]

[0122] As can be seen from Table 1, when the luminance is 3000 cd / cm², 2 In comparison with Comparative Examples 1-6, Examples 1-20 showed increased luminous efficiency and longer lifespan, along with a lower driving voltage. This is attributed to the introduction of silane (germanium) alkyl groups and their combination with the naphthalene ring. While silicon atoms are not as readily associated with heavy metals like Ir / Pt, their spin-orbit coupling (SOC) capability is superior to carbon. The combination with the π-system of the naphthalene ring enhances intersystem crossing (ISC), increasing the phosphorescence radiation rate and reducing energy loss due to vibration / rotation, thus improving phosphorescence efficiency by 10%-27%. The naphthalene-silicon heterocyclic structure may possess both hole and electron transport characteristics (bipolarity), improving the internal charge balance of the device and reducing voltage increases caused by carrier accumulation, thereby lowering the driving voltage by 7%-15%. Simultaneously, silicon atoms may reduce the oxidation sensitivity of the naphthalene ring (compared to pure carbon rings), reducing oxidative degradation products and extending device lifespan by 9%-27%.

[0123] First, because the naphthalene ring has a high HOMO energy level and a narrow bandgap, when the naphthalene ring is fused with silicon (germanium) heterocycles, it will affect the energy level modulation, making the HOMO energy level closer to the ITO anode or hole transport layer, reducing the hole injection barrier, and thus reducing the driving voltage.

[0124] Secondly, the introduction of silane groups enhances their spin-orbit coupling (SOC) capability compared to carbon, and their combination with the π-system of the naphthalene ring can strengthen intersystem crossing (ISC), thereby increasing the phosphorescence radiative rate. Furthermore, fusion with the naphthalene ring increases molecular rigidity, reduces energy loss due to vibration / rotation, and improves phosphorescence efficiency.

[0125] Finally, the rigid structure of silicon (germanium) heterocycles and fused-ring naphthalene can enhance the thermal stability of the material, inhibit crystallization or phase separation, maintain a uniform film morphology, reduce Joule heating-induced degradation, and slow down decomposition at high temperatures. The introduction of silane groups may reduce the oxidation sensitivity of the naphthalene ring (compared to pure carbon rings) and reduce oxidative degradation products.

[0126] The applicant declares that the present invention is illustrated by the above embodiments, but the present invention is not limited to the above process steps, that is, it does not mean that the present invention must rely on the above process steps to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials used in the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organometallic iridium luminescent material, characterized in that, The organometallic luminescent material has Ir(L) a )2(L b The general structural formula of 1; where L a L represents the first ligand that coordinates with the metal. b This indicates the second ligand coordinated with the metal; "2" represents L a The number of ligands is two, "1" represents L b The number of ligands is one, wherein the ligand L a general formula: ； In formula I-La, X can be selected from Si or Ge; R1~R 12 Each time it appears, it is selected from the following atoms or groups, either identically or differently: hydrogen, deuterium, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C20 heterocyclic, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C20 arylsilyl, substituted or unsubstituted C3-C20 alkylgermanium, substituted or unsubstituted C6-C20 arylgermanium, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphin, and combinations thereof. And R1~R 12 They exist independently or at least two of them can be connected to form a ring structure, and the fused ring structure formed includes an aromatic group of C3 to C20, an aromatic heterocycle of C3 to C20, a cycloalkyl group of C3 to C20, or a heterocyclic group of C3 to C20; The heteroatoms in the heteroaryl and heterocyclic groups include one or a combination of at least two of O, N, S, Ge, Si, P, and B; In the above formulas I-La, the hydrogen atoms are either independently substituted with deuterium or not substituted with deuterium; The ligand L b The general formula is: ； Where R a ~R c Each is independently a hydrogen atom, deuterium atom, halogen, cyano group, substituted or unsubstituted C1-C. 20 Alkyl, substituted or unsubstituted C3-C 20 cycloalkyl; R a ~R b The substituents at the positions can be the same or different; The above group R a ~R c The hydrogen atoms of the substituents are either unsubstituted, partially substituted, or completely substituted with deuterium.

2. The organometallic iridium luminescent material according to claim 1, characterized in that, R1~R 12 Each of the following is independently selected from hydrogen, deuterium, F, cyano, trifluoromethyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C20 arylsilyl, C3-C10 silyl or germanyl.

3. The organometallic iridium luminescent material according to claim 2, characterized in that, The substituted or unsubstituted C1-C10 alkyl groups include: methyl, ethyl, 2,2-dimethylpropyl, 2-methylbutyl, trimethylpentyl, isopropyl, 2-dimethylpropyl, and tert-butyl. The substituted or unsubstituted C6-C12 aryl groups include: benzene ring, naphthyl ring, 1,3-diisopropylphenyl, 1,3-dimethylphenyl, 1,3-ditrifluoromethylphenyl, and 1,3,5-triethylphenyl. The substituted or unsubstituted C3-C12 cycloalkyl groups include: cyclopentyl, cyclohexyl, 1,3-dimethylcyclopentyl, 1,3-dimethylcyclohexyl, 1,1-dimethylcyclohexyl, 1-tert-butylcyclopentyl, 1,3,5-triethylcyclohexyl, and neopentylcyclohexyl. The substituted or unsubstituted C6-C20 arylsilyl, C3-C10 silicon or germanyl groups include: trimethylsilyl, dimethylphenylsilyl, dimethylcyclohexylsilyl, and trimethylgermanyl.

4. The organometallic iridium luminescent material according to claim 1, characterized in that, The ligand L b It can be any of the following structures: 。 5. The organometallic iridium luminescent material according to claim 1, characterized in that, The organometallic iridium luminescent material has the structure shown in Formula I: 。 6. The organometallic iridium luminescent material according to claim 1, characterized in that, The organometallic iridium luminescent material is any one of the following compounds: 。 7. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode layer, a cathode layer, and an organic layer disposed between the anode layer and the cathode layer. The organic layer includes a light-emitting layer, which includes a host material and a dopant material. The dopant material includes the organometallic iridium light-emitting material according to any one of claims 1-6.

8. The organic electroluminescent device according to claim 7, characterized in that, The organic layer further includes at least one of a hole functional layer and an electronic functional layer.

9. The organic electroluminescent device according to claim 7, characterized in that, The organic electroluminescent device includes a substrate layer, an anode layer, a hole functional layer, a light-emitting layer, an electronic functional layer, a cathode layer, and an encapsulation and protective layer.

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