Organic metal luminescent material, preparation method and organic electroluminescent device

Abstract

The invention provides an organic metal luminescent material, a preparation method and an organic electroluminescent device.The organic metal luminescent material has the structure shown in the formula I. When the organic metal luminescent material serves as a doping material of a luminescent layer in the organic electroluminescent device, the device can have high luminescent efficiency, and the luminescent efficiency of the device is improved. And the service life of the device can be prolonged.

Description

Technical Field

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

[0002] The application areas of OLED technology are constantly expanding. Beyond its traditional applications in smartphones and televisions, OLEDs are also finding applications in wearable devices, automotive displays, and medical equipment. With the advent of the 5G era, the increasing use of mobile video and gaming applications is driving higher demands for screen displays, which in turn is driving the development of OLED technology. Compared to other lighting sources, OLEDs can emit light directly from their surfaces, allowing for customizable shapes and achieving the same luminous flux at reduced light intensity. This results in high luminous efficiency.

[0003] The materials used for the light-emitting portion of OLEDs are primarily organic fluorescent materials, which can be broadly categorized into three types: red, blue, and green. Recent research has shown that in the electroluminescence of organic fluorescent materials, the generation of singlet excitons and triplet excitons typically follows a 1:3 ratio determined by spin statistics. Unlike traditional fluorescent materials that rely solely on singlet excitons, organic phosphors can increase their internal quantum efficiency to 100% by incorporating heavy metals. These metals promote stable spin-orbit coupling and facilitate the mixing of singlet and triplet states. Consequently, in recent years, research has focused on heavy metal-coordinated organic fluorescent materials, particularly iridium complexes.

[0004] With the continuous advancement of technology, research on organic optoelectronic materials is moving towards higher performance, lower cost, and greater multifunctionality. However, current research also has shortcomings. For one thing, the luminous efficiency and lifespan of OLED materials are generally low. Furthermore, the production cost of conventional OLED materials is high, resulting in low production capacity and yield rates. Therefore, developing materials with high luminous efficiency and a long lifespan is a technical challenge that needs to be addressed. Summary of the Invention

[0005] To address the problems of low luminous efficiency and short service life, the present invention provides an organometallic luminescent material, preparation method, and organic electroluminescent device. The organometallic luminescent material has a relatively large number of benzene ring structures, thereby increasing the rigidity of the overall structure, reducing non-radiative transitions, and improving the phosphorescence quantum yield. Furthermore, the fluorinated alkyl and cyano groups in the structure can effectively adjust the color and efficiency of the electroluminescent device through electronic effects, steric hindrance, and intermolecular forces. Furthermore, the wavelength of fluorescence can be adjusted by varying the type and number of substituents on the benzene ring. When used as a dopant material for the light-emitting layer of an organic electroluminescent device, the device can have a higher luminous efficiency and a longer service life.

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

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

[0008]

[0009] In formula I, R1 to R5 are each independently hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amino, sulfonic acid, substituted or unsubstituted C1-C 40 Alkyl, substituted or unsubstituted C1-C 40 Alkoxy, substituted or unsubstituted C1-C 40 Alkylamino, substituted or unsubstituted C2-C 40 Heterocyclic group, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Heteroaryl, substituted or unsubstituted C2-C 40 Alkenyl, substituted or unsubstituted C2-C 40 Alkyne, substituted or unsubstituted C5-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 Any two adjacent substituents may be connected to each other.

[0010] The substituents at positions R1 to R5 are the same or different; the positions of the substituents R1 to R5 are any positions on the benzene ring, the number of substituents R1 to R3 is 0 to 4, the number of substituents R4 is 0 to 2, and the number of substituents R5 is 0 to 3.

[0011] In some embodiments of the present invention, each of R1 to R5 independently represents hydrogen, deuterium, fluorine, cyano, trimethylsilyl, trimethylgermanyl, substituted or unsubstituted C1-C15 Alkyl, substituted or unsubstituted C1-C 15 Alkoxy, substituted or unsubstituted C1-C 20 Alkylamino, substituted or unsubstituted C2-C 15 Heterocyclic group, substituted or unsubstituted C6-C 20 Aryl, substituted or unsubstituted C3-C 20 Heteroaryl, substituted or unsubstituted C2-C6 alkene, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C8-C 20 Condensed ring group, substituted or unsubstituted C5-C 30 Spirocyclic group, R1 to R5 are the same or different.

[0012] In some embodiments of the present invention, 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.

[0013] In some embodiments of the present invention, the substituted or unsubstituted C1-C 15 Alkoxy includes any one of methoxy, ethoxy, propoxy, phenoxy, butoxy to alkoxy, phenoxy, isopropoxy, tert-butoxy, neopentyloxy. In some embodiments of the present invention, substituted or unsubstituted C1-C 20 The alkylamino group includes a methylamino group, an ethylamino group, a propylamino group, a butylamino group, a pentylamino group, and a 2-chloroethylamino group.

[0014] In some embodiments 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.

[0015] For example, oxirane, thiirane, substituted or unsubstituted pyrazole, substituted or unsubstituted imidazole, substituted or unsubstituted oxazole, substituted or unsubstituted thiazole, substituted or unsubstituted tetrahydrothiophene, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted benzimidazole, substituted or unsubstituted benzothiazole.

[0016] In some embodiments of the present invention, substituted or unsubstituted C6-C 20 The aryl group includes any one of phenyl, tolyl, chlorophenyl, bromophenyl, fluorophenyl, biphenyl, terphenyl, naphthyl, anthracenyl, and phenanthrenyl.

[0017] In some embodiments of the present invention, substituted or unsubstituted C3-C20 Heteroaryl groups include substituted or unsubstituted pyridyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl and isoquinolinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothienyl.

[0018] In some embodiments of the present invention, the substituted or unsubstituted C2-C6 olefin groups include ethenyl, propenyl, butenyl, pentenyl, hexenyl, vinyl chloride, and methacryl.

[0019] In some embodiments of the present invention, the substituted or unsubstituted C2-C6 alkynyl group includes ethynyl, propynyl, butynyl, pentynyl, hexynyl, chloroethynyl, and methylethynyl.

[0020] In some embodiments of the present invention, substituted or unsubstituted C5-C 30 The spirocyclic group includes any one of a [4.4]nonyl group, a spiro[5.5]undecyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[3.3.1]nonyl group, a spirobifluorenyl group, a spirofluorenoxanthenyl group, a spiro(indenothiophene)fluorenyl group, and a spiro(cyclopentadithiophene)fluorenyl group.

[0021] In some embodiments of the present invention, in the organic metal luminescent material, R1 to R5 can be arbitrarily connected to form a ring, and the ring can be a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed ring group, or a substituted or unsubstituted spirocyclic group, and the formed condensed ring may contain or not contain any one or more of O, S, N, P, B, Si and Ge.

[0022] In some embodiments of the present invention, the hydrogen atoms in the substituent groups of R1 to R5 are substituted with deuterium, partially substituted with deuterium, or not substituted with deuterium.

[0023] In some embodiments of the present invention, the specific structure of the organic metal luminescent material may be the following structures, but is not limited to these:

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[0068]

[0069] In the present invention, the synthetic route of formula I is as follows Figure 1 As shown:

[0070]

[0071] The synthesis steps are as follows:

[0072] 1. Add ethylene glycol ether and water to a three-necked flask, place the compound of formula II into the reaction system, replace the nitrogen, then add iridium trichloride, reflux under nitrogen protection, then cool to room temperature, precipitate is precipitated, filter the precipitate, rinse with water, anhydrous ethanol, and petroleum ether in sequence, and dry to obtain the compound of formula III shown.

[0073] 2. Weigh the intermediate compound of formula III, add silver trifluoromethanesulfonate, then add dichloromethane and methanol to the system, replace the nitrogen, react at room temperature, and finally pass through column chromatography (short column). The filtrate is concentrated to a solid to obtain the iridium complex intermediate compound of formula IV shown.

[0074] 3. Weigh the intermediate compound of Formula IV and add the ligand of Formula V. Then, add anhydrous ethanol to the system. After replacing the nitrogen atmosphere, react at a certain temperature. Then, filter, wash with ethanol, and dry to obtain a crude product. Finally, use dichloromethane and petroleum ether as eluents and perform silica gel column chromatography to obtain the final product of Formula I.

[0075] The present invention also provides an organic electroluminescent device comprising a first electrode, a second electrode, and an organic thin film layer disposed between the first and second electrodes, the organic thin film layer comprising a hole transport region, a light-emitting layer, and an electron transport region. The light-emitting layer comprises a host material and a dopant material, the dopant material comprising the above-described organometallic light-emitting material.

[0076] The first electrode can be deposited on the substrate by sputtering or deposition. The first electrode can be made of oxides such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), and zinc oxide (ZnO). When the first electrode serves as a cathode, metals such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) can be used as the plating material.

[0077] The organic thin film layer can be deposited on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The material used as the organic material layer can be an organic small molecule, an organic macromolecule, or a polymer. The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a hole transport layer (HTL) with a single-layer structure, including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multi-layer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0078] The material of the hole transport layer can be a phthalocyanine derivative, a conductive polymer or a polymer containing a conductive dopant such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphorsulfonic acid, polyaniline / poly(4-styrenesulfonate), aromatic amine derivatives, etc.

[0079] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds, such as aromatic amine derivatives, formula A and formula B, etc.

[0080]

[0081] The light-emitting layer includes a dopant material that can emit light at different wavelengths, and may also include a host material. Depending on the technology, the light-emitting layer material can be a phosphorescent electroluminescent material, a thermally activated delayed fluorescent material, or other materials. Formula I of the present invention is used as the dopant material in the light-emitting layer.

[0082] The electron transport region is generally a single-layer structure, wherein the material used can be a single compound or a combination of multiple compounds. The electron transport region can also be a multi-layer structure such as an electron injection layer, an electron transport layer, and a hole blocking layer.

[0083] The electron injection layer is located between the electron transport layer and the cathode, and the electron injection layer material can be LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, or Ca.

[0084] Compared with the prior art, the present invention has the following advantages: by adjusting the substituent groups on the left side of the ligand of Formula I, the electronegativity and spatial structure of the substituent groups are changed, thereby changing the overall electron cloud distribution and the molecular spatial structure. At the same time, by introducing fluorinated alkyl and cyano groups into the right side of the ligand, the color and efficiency of the electroluminescent device can be effectively adjusted. When the compound of the present invention is used as a doping material for the light-emitting layer, the organic electroluminescent device prepared has a significantly lower driving voltage and a significantly improved luminous efficiency and life compared with the organic electroluminescent device prepared in the comparative example. BRIEF DESCRIPTION OF THE DRAWINGS

[0085] Figure 1 This is the hydrogen nuclear magnetic resonance spectrum of the organometallic compound I-38 (Formula I-38) synthesized in Example 1. DETAILED DESCRIPTION

[0086] The technical solution of the present invention is further described below by way of specific embodiments. It should be understood by those skilled in the art that the embodiments are merely to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0087] Example 1

[0088] This synthesis example provides an organometallic compound I-38, i.e., compound numbered I-38. The specific synthesis steps are as follows:

[0089] Step 1: Synthesis of the compound of formula III

[0090] Formula II (1 eq) (CAS: 1710506-23-2), 1-bromopyrrolidine-2,5-dione (1.05 eq), palladium acetate (0.05 eq), and K2S2O8 (1.05 eq) were dissolved in 1,2-dichloroethane. After nitrogen was replaced twice, trifluoromethanesulfonic acid (1 eq) was added under a nitrogen atmosphere. The mixture was then heated to 80°C and stirred to react overnight. After the reaction, the pH was adjusted to neutral using a NaHCO3 solution, and the liquids were separated. The remaining layers were then dried by spin drying, and the crude product was purified by column chromatography (dichloromethane and petroleum ether) to obtain the product compound of formula III (yield 34.3%).

[0091] Mass spectrometry test value: 305.13.

[0092]

[0093] Step 2: Synthesis of the compound of formula VI

[0094]

[0095] 1. In a three-necked flask, IV (1 eq) (CAS: 2259751-85-2), diboronic acid pinacol ester (2 eq) and potassium acetate (2.5 eq) were added, and then 20 times the mass of Formula IV was added as a solvent. After replacing nitrogen twice, DBA (0.02 eq) and X-phos (0.08 eq) were added. After replacing nitrogen twice again, the reaction was carried out at 80 ° C. for 36 h to obtain Formula V (yield: 73.6%).

[0096] 2. Add III (1 eq), formula V (1.1 eq) and anhydrous potassium carbonate (3 eq) to a three-necked flask, then add 20 times the mass of formula III in toluene, 10 times the mass of ethanol and 10 times the mass of water as solvents, replace nitrogen twice, add Pd(pph3)4 (0.03 eq), replace nitrogen twice again, react at 100 ° C. for 24 h, and purify by column chromatography (eluent: hexane and ethyl acetate) to obtain formula VI (yield: 77.3%).

[0097] Mass spectrometry test value: 338.47.

[0098] Step 3: Synthesis of the compound of formula I-38

[0099]

[0100] 1. A compound of formula VII (CAS: 27012-22-2) (2.5 eq) and IrCl3·3H2O (1 eq) were placed in a three-necked flask. Ethylene glycol ether (15 times the mass of formula VII) and purified water (3 times the mass) were then added. After nitrogen displacement twice, the mixture was refluxed at 120°C for 48 hours. The mixture was then cooled to room temperature. A precipitate formed, which was filtered, rinsed with anhydrous ethanol, and then dried with petroleum ether. The bridged ligand shown in formula VII-1 was obtained (yield: 57.3%).

[0101]

[0102] 2. The weighed intermediate formula Ⅶ-1 (1 eq) and silver trifluoromethanesulfonate (2.2 eq) were added to a three-necked flask, and then 20 times the mass of dichloromethane and 3 times the mass of methanol were added to the system. Under nitrogen protection, refluxed for 30 hours, cooled to room temperature, and then purified and concentrated by silica gel funnel to obtain the iridium complex intermediate formula Ⅶ-2 shown (yield 89.3%).

[0103]

[0104] 3. Weigh the intermediate formula VII-2 (1 eq) and the ligand formula VI (2.5 eq) into a three-necked flask. Then, add 20 times the mass of anhydrous ethanol of formula VII-2 to the system. After replacing the nitrogen atmosphere twice, reflux the reaction at 80°C for 48 hours. After cooling to room temperature, filter, wash with alcohol, dry, and column chromatography (eluents: dichloromethane and hexane) to obtain the final compound shown in formula I-38 (yield 31.4%), with an HPLC purity greater than 99%.

[0105] Mass spectrometry test value: 866.53.

[0106] H NMR spectrum Figure 1 shown.

[0107] Light-emitting device embodiment 1

[0108] The organic metal luminescent material of formula I-38 is prepared into an organic electroluminescent device. The more specific preparation method is as follows:

[0109] 1. On the anode, the ITO patterned glass substrate was cut into a size of 50 mm × 50 mm × 0.5 mm, ultrasonically treated with deionized water and isopropyl alcohol for 10 minutes, and then exposed to ultraviolet light and ozone for 30 minutes for cleaning.

[0110]

[0111] 2. Load the glass substrate onto a vacuum deposition device, first evaporate a hole injection layer of formula A with a thickness of 100 angstroms on the anode, and then evaporate a hole transport layer of formula C with a thickness of 900 angstroms on the hole injection layer.

[0112] 3. A light-emitting layer of a host material 4,4'-N,N'-biphenyldicarbazole ("CBP") and a dopant material compound of formula I-38 (95:5) is evaporated to a thickness of 400 angstroms, followed by an electron transport layer with a thickness of 400 angstroms on the light-emitting layer, and a LiQ electron injection layer with a thickness of 150 angstroms on the electron transport layer. Finally, a cathode material Al is evaporated to a thickness of 1000 angstroms on the electron injection layer to obtain an organic electroluminescent device.

[0113] Referring to the light-emitting device embodiment 1, the dopant formula Ⅰ-38 in the organic electroluminescent device is replaced by formulas Ⅰ-1, Ⅰ-21, Ⅰ-103, Ⅰ-132, Ⅰ-212, Ⅰ-300, Ⅰ-389, Ⅰ-452, Ⅰ-519, and Ⅰ-619 to prepare them into organic electroluminescent devices respectively.

[0114] Comparative Example 1

[0115] An organic electroluminescent device was prepared by the same method as in Example 1 of the light-emitting device, except that the doping material of Formula I-38 in the light-emitting layer was replaced with a compound of Formula D. The structure of Formula D is shown below:

[0116]

[0117] Comparative Example 2

[0118] An organic electroluminescent device was prepared by the same method as in Example 1 of the light-emitting device, except that the doping material of Formula I-38 in the light-emitting layer was replaced with a compound of Formula E. The structure of Formula E is shown below:

[0119]

[0120] Comparative Example 3

[0121] An organic electroluminescent device was prepared by the same method as in Example 1 of the light-emitting device, and the doping material of Formula I-38 in the light-emitting layer was replaced by a compound of Formula F. The structure of Formula F is shown below:

[0122]

[0123] In order to further illustrate the luminescent properties of the organometallic luminescent materials 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 and 3 were tested. The measurements were made using a KEITHLEY 2400 source measurement unit and a CS-2000 spectroradiometer to evaluate the driving voltage, luminous efficiency and lifetime. The results are shown in Table 1 (the test results are normalized based on Comparative Example 3).

[0124] Table 1 Luminescence detection data of organic electroluminescent devices of Examples 1-11 and Comparative Examples 1-3

[0125]

[0126]

[0127] It can be seen from Table 2 that when the brightness is 15000cd / cm 2 , the driving voltage of Comparative Example 3 is slightly lower than that of Comparative Examples 1 and 2, while the lifespan and efficiency are increased; the driving voltage of Examples 1 to 11 is lowered, while the lifespan and efficiency are increased compared with Comparative Example 3. The reason for this phenomenon may be the introduction of fluorinated alkyl and cyano groups into the ligand. Both groups have large electronegativity, which can reduce the LUMO energy level of the molecule and promote charge transfer and anti-intersystem crossing. On the other hand, structurally, the introduction of fluorinated alkyl and cyano groups can enhance molecular conjugation, optimize intramolecular charge transfer and molecular planarity, reduce vibration coupling, and improve the stability of the material. In summary, in the present invention, by simultaneously introducing fluorinated alkyl and cyano groups into the molecule, an organic optoelectronic material with better efficiency and service life can be obtained.

[0128] It can be seen from this 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.

[0129] It will be apparent to those skilled in the art that many modifications and variations are possible without departing from the spirit and scope of the present invention. It is therefore contemplated that the present invention encompasses modifications and variations of the present invention provided within the scope of the appended claims and their equivalents.

[0130] The above description of the disclosed embodiments is intended to enable one skilled in the art to implement or use the present invention. Various modifications to these embodiments will be readily 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 is not limited to the embodiments shown herein, but is intended to be construed in the widest manner consistent with the principles and novel features disclosed herein.

Claims

1. An organic metal luminescent material, characterized in that: It has the general structural formula shown in Formula I: In formula I, R1 to R5 are each independently hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amino, sulfonic acid, substituted or unsubstituted C1-C 40 Alkyl, substituted or unsubstituted C1-C 40 Alkoxy, substituted or unsubstituted C1-C 40 Alkylamino, substituted or unsubstituted C2-C 40 Heterocyclic group, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C3-C 40 Heteroaryl, substituted or unsubstituted C2-C 40 Alkenyl, substituted or unsubstituted C2-C 40 Alkyne, substituted or unsubstituted C5-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 Any two adjacent substituents may be connected to each other. The substituents at positions R1 to R5 are the same or different; the positions of the substituents R1 to R5 are any positions on the benzene ring, the number of substituents R1 to R3 is 0 to 4, the number of substituents R4 is 0 to 2, and the number of substituents R5 is 0 to 3.

2. The organic iridium metal complex luminescent material according to claim 1, wherein: The R1 to R5 each independently represent hydrogen, deuterium, fluorine, cyano, trimethylsilyl, trimethylgermanyl, substituted or unsubstituted C1-C 15 Alkyl, substituted or unsubstituted C1-C 15 Alkoxy, substituted or unsubstituted C1-C 20 Alkylamino, substituted or unsubstituted C2-C 15 Heterocyclic group, substituted or unsubstituted C6-C 20 Aryl, substituted or unsubstituted C3-C 20 Heteroaryl, substituted or unsubstituted C2-C6 alkene, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C8-C 20 Condensed ring group, substituted or unsubstituted C5-C 30 Spirocyclic group, R1 to R5 are the same or different.

3. The organic iridium metal complex luminescent material according to claim 2, wherein: 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. The substituted or unsubstituted C1-C 15 The alkoxy group includes any one of methoxy, ethoxy, propoxy, phenoxy, butoxy, alkoxy, phenoxy, isopropoxy, tert-butoxy, and neopentyloxy. The substituted or unsubstituted C1-C 20 The alkylamino group includes a methylamino group, an ethylamino group, a propylamino group, a butylamino group, a pentylamino group, and a 2-chloroethylamino group. 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. For example, oxirane, thiirane, substituted or unsubstituted pyrazole, substituted or unsubstituted imidazole, substituted or unsubstituted oxazole, substituted or unsubstituted thiazole, substituted or unsubstituted tetrahydrothiophene, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted benzimidazole, substituted or unsubstituted benzothiazole. The substituted or unsubstituted C6-C 20 The aryl group includes any one of phenyl, tolyl, chlorophenyl, bromophenyl, fluorophenyl, biphenyl, terphenyl, naphthyl, anthracenyl, and phenanthrenyl. The substituted or unsubstituted C3-C 20 Heteroaryl groups include substituted or unsubstituted pyridyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl and isoquinolinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothienyl. The substituted or unsubstituted C2-C6 olefin groups include ethenyl, propenyl, butenyl, pentenyl, hexenyl, vinyl chloride, and methacryl. The substituted or unsubstituted C2-C6 alkynyl group includes ethynyl, propynyl, butynyl, pentynyl, hexynyl, chloroethynyl, and methylethynyl. The substituted or unsubstituted C5-C 30 The spirocyclic group includes any one of spiro[4.4]nonyl, spiro[5.5]undecyl, bicyclo[2.2.1]heptyl, bicyclo[3.3.1]nonyl, spirobifluorenyl, spirofluorenoxanthenyl, spiro(indenothiophene)fluorenyl, and spiro(cyclopentadithiophene)fluorenyl.

4. The organic iridium metal complex luminescent material according to claim 1, wherein: The R1 to R5 can be arbitrarily connected to form a ring, and the ring is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed ring group, or a substituted or unsubstituted spirocyclic group, and the formed condensed ring may or may not contain any one or more of O, S, N, P, B, Si and Ge.

5. The organic iridium metal complex luminescent material according to claim 1, wherein: The hydrogen atoms in the substituent groups of R1 to R5 are all substituted with deuterium, partially substituted with deuterium, or not substituted with deuterium.

6. The organic iridium metal complex luminescent material according to claim 1, wherein: The specific structure of the organic metal luminescent material can be the following structures, but is not limited to these:

7. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises the organometallic complex luminescent material according to claim 1 .

8. The organic electroluminescent device according to claim 7, wherein: The organic electroluminescent device includes a first electrode, a second electrode, and an organic thin film layer disposed between the first electrode and the second electrode. The organic thin film layer includes a hole transport region, a light emitting layer, and an electron transport region.

9. The organic electroluminescent device according to claim 8, wherein: The light-emitting layer includes a host material and a doping material, and the doping material includes the organic metal light-emitting material according to claim 1 .

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