An organometallic iridium compound

Abstract

The present invention relates to an organic metal iridium compound and its application. The organic metal iridium compound has the general formula of Ir(La)(Lb)(Lc), wherein La is the structure shown in formula (1), and Lb is the structure shown in formula (2). The compound provided by the present invention has the advantages of high optical and electrical stability, low sublimation temperature, narrow emission half-peak width, high color saturation, high luminous efficiency, long device life, etc., and can be used in organic electroluminescent devices. In particular, as a red light-emitting dopant, it has the possibility of being applied to the AMOLED industry.

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescence, in particular to an organic luminescent material suitable for an organic electroluminescent device, and more particularly to an organic metal iridium compound and its application in an organic electroluminescent device. Background Art

[0002] At present, organic electroluminescent devices (OLEDs), as a new generation of display technology, have received more and more attention in both display and lighting technology, and have a wide range of application prospects. However, compared with market application requirements, the performance of OLED devices such as luminous efficiency, driving voltage, and service life still needs to be further strengthened and improved.

[0003] Generally speaking, the basic structure of an OLED device is a thin film of organic functional materials with various functions sandwiched between metal electrodes, like a sandwich structure. Driven by electric current, holes and electrons are injected from the positive and negative electrodes respectively. After moving a certain distance, the holes and electrons are recombined in the light-emitting layer and released in the form of light or heat, thus generating the light emission of the OLED. However, organic functional materials are the core components of organic electroluminescent devices. The thermal stability, photochemical stability, electrochemical stability, quantum yield, film formation stability, crystallinity, color saturation, etc. of the materials are the main factors affecting the performance of the device.

[0004] Generally, organic functional materials include fluorescent materials and phosphorescent materials. Fluorescent materials are usually small organic molecule materials, which can generally only utilize 25% of the singlet state to emit light, so the luminous efficiency is relatively low. However, due to the spin-orbit coupling caused by the heavy atom effect, phosphorescent materials can utilize the energy of 75% of the triplet excitons in addition to the 25% singlet state, so the luminous efficiency can be improved. However, compared with fluorescent materials, phosphorescent materials started later, and the thermal stability, lifespan, color saturation, etc. of the materials need to be improved, which is a challenging topic. Some people have developed various organometallic iridium compounds as phosphorescent materials. For example, patent document US20050123798 discloses a class of iridium-based complexes with indole as a ligand. Although this type of material exhibits a good red emission wavelength, the device luminescence efficiency of this type of material is low and the color saturation needs to be further improved to meet the display requirements of DCIP3 and even BT2020; Patent document CN107722062 discloses a type of iridium platinum complex constructed with acenaphthylene as a unit This type of material shows blue or green luminescence; Patent document CN110317231 discloses a type of metal complex constructed with acenaphthylene as a unit This type of material shows deep blue luminescence. In order to meet the market demand for higher stability, longer life, more saturated color purity and higher luminous efficiency, more new materials need to be developed to meet the growing technical needs of the market. Summary of the invention

[0005] In order to solve the above-mentioned defects, the present invention provides a high-performance organic electroluminescent device and an organic metal iridium compound material capable of realizing such an organic electroluminescent device.

[0006] The organometallic iridium compound of the present invention has the general formula of Ir(La)(Lb)(Lc), wherein La is the structure shown in formula (1), and Lb is the structure shown in formula (2). The iridium compound provided by the present invention has the advantages of high optical and electrical stability, low sublimation temperature, narrow emission half-peak width, high color saturation, high luminous efficiency, long device life, etc., and can be used in organic electroluminescent devices. In particular, as a red light-emitting dopant, it has the possibility of being applied to the AMOLED industry, especially for display, lighting and automobile taillights.

[0007] An organic metal iridium compound having the general formula of Ir(La)(Lb)(Lc), wherein La is a structure shown in formula (1),

[0008]

[0009] Wherein, the dotted line indicates the position connected with metal Ir;

[0010] Wherein, X1 is N or CR1, X2 is N or CR2, X3 is N or CR3, X4 is N or CR4, X5 is N or CR5, and X6 is N or CR6;

[0011] wherein at most one of X1-X6 is N, and when X1-X6 is CR1-CR6, at least one of R1-R6 is not H;

[0012] Among them, R1-R 10 independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, thiol, amine, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C17 heteroaryl, substituted or unsubstituted tri-C1-C10 alkylsilyl, substituted or unsubstituted tri-C6-C12 arylsilyl, substituted or unsubstituted di-C1-C10 alkyl-C6-C30 arylsilyl, substituted or unsubstituted mono-C1-C10 alkyldi-C6-C30 arylsilyl, or R1-R6, R7-R 10Two adjacent groups may be connected to form an aliphatic ring or an aromatic ring; and R7-R 10 At least one of them is not hydrogen;

[0013] Wherein Lb is the structure shown in formula (2),

[0014]

[0015] The dotted line position indicates the position connected to the metal Ir;

[0016] Wherein, Ra-Rg are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl; or Ra, Rb, Rc are connected in pairs to form an aliphatic ring, and Re, Rf, Rg are connected in pairs to form an aliphatic ring;

[0017] The substitution is substituted by an amino group, a cyano group, an isonitrile group or a phosphine group substituted by deuterium, F, Cl, Br, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C3-C6 cycloalkyl group or a C1-C6 alkyl group, wherein the number of substitutions ranges from a single substitution to a maximum number of substitutions;

[0018] Wherein, the heteroalkyl, heterocycloalkyl and heteroaryl groups contain at least one O, N or S heteroatom;

[0019] Among them, Lc is a monoanionic bidentate ligand, Lc is different from Lb and is not an OO type ligand;

[0020] Wherein, Lc and La are the same or different, and the difference is that the parent core structures are different, or the parent core structures are the same but the substituents are different, or the parent core structures are the same and the substituents are the same but the positions of the substituents are different;

[0021] Alternatively, two or three of La, Lb, and Lc are connected to each other to form a multidentate ligand.

[0022] Preferably: wherein La is a structure represented by formula (3),

[0023]

[0024] Wherein, the dotted line indicates the position connected with metal Ir;

[0025] Among them, R1-R 10R1-R6, R7-R 10 Two adjacent groups are connected to form an aliphatic ring or an aromatic ring;

[0026] Among them, at least one of R1-R6 is not H, R7-R 10 At least one of them is not hydrogen;

[0027] Wherein, the heteroalkyl and heteroaryl groups contain at least one O, N or S heteroatom;

[0028] Wherein, the substitution is substitution by an amino group, a cyano group, an isonitrile group or a phosphine group substituted by deuterium, F, Cl, Br, a C1-C4 alkyl group, a C3-C6 cycloalkyl group or a C1-C4 alkyl group, wherein the number of substitutions ranges from a single substitution to a maximum number of substitutions.

[0029] In formula (3), R1 and / or R3 and / or R4 and / or R5 are not hydrogen.

[0030] In formula (3), R1, R3, R4, and R5 are independently selected from deuterium, halogen, substituted or unsubstituted C1-C10 alkyl, and substituted or unsubstituted C3-C20 cycloalkyl.

[0031] In the formula (3), at least two of R1-R6 are not H.

[0032] In formula (3), R2 and R6 are hydrogen.

[0033] Preferably: In formula (3), R8 and / or R 10 Not hydrogen.

[0034] In formula (3), R8 and R 10 is not hydrogen, said R8, R 10 R7 and R9 are independently selected from deuterium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, and are hydrogen.

[0035] Where R7 and R8, R8 and R9, or R9 and R 10are connected to each other to form a structure shown in formula (4),

[0036]

[0037] Where * indicates the location of the connection.

[0038] Y1-Y4 are independently CR0 or N,

[0039] Z1 is selected from O, S,

[0040] R0 is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C1-C30 heteroaryl, substituted or unsubstituted tri-C1-C10 alkylsilyl, substituted or unsubstituted tri-C6-C30 arylsilyl, substituted or unsubstituted di-C1-C10 alkyl-C6-C30 arylsilyl; the substitution is substituted by deuterium, F, Cl, Br, C1-C4 alkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C1-C4 alkyl, amine, cyano, isonitrile or phosphine.

[0041] Wherein R7 and R8 are connected to each other to form a structure shown in formula (4),

[0042]

[0043] Where * indicates the location of the connection.

[0044] Y1-Y4 are independently CR0,

[0045] Z1 is selected from O.

[0046] Where Lc is the same as La.

[0047] Wherein Lc is different from La, and Lc is the structure shown in formula (5).

[0048]

[0049] Wherein, the dotted line indicates the position connected with metal Ir;

[0050] Among them, R 11 -R 18R is independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, amino, amine, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C17 heteroaryl, substituted or unsubstituted tri-C1-C10 alkylsilyl, substituted or unsubstituted tri-C6-C12 arylsilyl, substituted or unsubstituted di-C1-C10 alkyl-C6-C30 arylsilyl, substituted or unsubstituted mono-C1-C10 alkyldi-C6-C30 arylsilyl; wherein R 15 -R 18 At least two of them are not hydrogen; or, R 11 -R 14 At least one set of two adjacent groups forms an aromatic ring structure as shown in the following formula (6);

[0051]

[0052] Wherein, the dotted line indicates the position of connection with the pyridine ring;

[0053] Among them, R 19 -R 22 R is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C17 heteroaryl, substituted or unsubstituted tri-C1-C10 alkylsilyl, substituted or unsubstituted tri-C6-C12 arylsilyl, substituted or unsubstituted di-C1-C10 alkyl-C6-C30 arylsilyl, substituted or unsubstituted mono-C1-C10 alkyldi-C6-C30 arylsilyl, or R 19 -R 22 Two adjacent groups are connected to form an aliphatic ring or an aromatic ring;

[0054] The substitution is substituted by an amino group, a cyano group, an isonitrile group or a phosphine group substituted by deuterium, F, Cl, Br, a C1-C4 alkyl group, a C1-C4 alkoxy group, a C3-C6 cycloalkyl group or a C1-C4 alkyl group.

[0055] As a preferred organometallic iridium compound, wherein La is one of the following structural formulas, or a corresponding partially or completely deuterated or fluorinated one,

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065] As a preferred organometallic iridium compound, Lb is one of the following structural formulas, or a corresponding partially or completely deuterated or fluorinated one,

[0066]

[0067]

[0068] As a preferred organometallic iridium compound, Lc is one of the following structural formulas, or a corresponding partially or completely deuterated or fluorinated one,

[0069]

[0070]

[0071] Another object of the present invention is to use the above-mentioned organometallic iridium compound in an organic electroluminescent device.

[0072] Another object of the present invention is to use the above-mentioned organometallic iridium compound as a red light-emitting doping material in a light-emitting layer of an organic electroluminescent device.

[0073] The material of the present invention has the advantages of high optical and electrical stability, low sublimation temperature, narrow emission half-peak width, high color saturation, high luminous efficiency, and long device life. As a phosphorescent material, the material of the present invention can convert the triplet excited state into light, so it can improve the luminous efficiency of the organic electroluminescent device, thereby reducing energy consumption. In particular, as a red light-emitting dopant, it has the possibility of being applied to the AMOLED industry. DETAILED DESCRIPTION

[0074] The compound of the present invention, an organometallic iridium compound, has the general formula of Ir(La)(Lb)(Lc), wherein La is a structure shown in formula (1),

[0075]

[0076] Wherein, the dotted line indicates the position connected with metal Ir;

[0077] Wherein, X1 is N or CR1, X2 is N or CR2, X3 is N or CR3, X4 is N or CR4, X5 is N or CR5, and X6 is N or CR6;

[0078] wherein at most one of X1-X6 is N, and when X1-X6 is CR1-CR6, at least one of R1-R6 is not H;

[0079] Among them, R1-R 10 independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, thiol, amine, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C17 heteroaryl, substituted or unsubstituted tri-C1-C10 alkylsilyl, substituted or unsubstituted tri-C6-C12 arylsilyl, substituted or unsubstituted di-C1-C10 alkyl-C6-C30 arylsilyl, substituted or unsubstituted mono-C1-C10 alkyldi-C6-C30 arylsilyl, or R1-R6, R7-R 10 Two adjacent groups can be connected to each other to form an aliphatic ring or an aromatic ring structure; and R7-R 10 At least one of them is not hydrogen; the substitution is substituted by an amino group, a cyano group, an isonitrile group or a phosphine group substituted by deuterium, F, Cl, Br, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, or C1-C6 alkyl, wherein the number of substitutions is from a single substitution to a maximum number of substitutions;

[0080] Wherein, the heteroalkyl and heteroaryl groups contain at least one O, N or S heteroatom;

[0081] Wherein Lb is the structure shown in formula (2),

[0082]

[0083] The dotted line position indicates the position connected to the metal Ir;

[0084] Wherein, Ra-Rg are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl; Ra, Rb, Rc are connected in pairs to form an aliphatic ring structure, and Re, Rf, Rg are connected in pairs to form an aliphatic ring structure;

[0085] Wherein, the heteroalkyl group and the heterocycloalkyl group contain at least one heteroatom of O, N or S;

[0086] Among them, Lc is a monoanionic bidentate ligand, Lc and Lb are different and not OO type ligands;

[0087] Wherein, Lc and La are the same or different, and the difference is that the parent core structures are different, or the parent core structures are the same but the substituents are different, or the parent core structures are the same and the substituents are the same but the positions of the substituents are different;

[0088] Among them, La, Lb, and Lc are connected to each other in pairs or in triplets to form a multidentate ligand.

[0089] Hereinafter, examples of each group of the compounds represented by formula (1) to formula (5) will be described.

[0090] In the present specification, the "carbon number a to b" in the expression "substituted or unsubstituted X group having a to b carbon atoms" refers to the carbon number when the X group is unsubstituted, and does not include the carbon number of the substituent when the X group is substituted.

[0091] The C1-C10 alkyl group is a straight-chain or branched alkyl group, specifically, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl and its isomers, n-hexyl and its isomers, n-heptyl and its isomers, n-octyl and its isomers, n-nonyl and its isomers, n-decyl and its isomers, etc., preferably, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, and more preferably, propyl, isopropyl, isobutyl, sec-butyl and tert-butyl.

[0092] Examples of the C3-C20 cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl, and cyclopentyl and cyclohexyl are preferred.

[0093] Examples of the C2-C10 alkenyl group include vinyl, propenyl, allyl, 1-butadienyl, 2-butadienyl, 1-hexatrienyl, 2-hexatrienyl, and 3-hexatrienyl, and propenyl and allyl are preferred.

[0094] The C1-C10 heteroalkyl group is a straight-chain or branched alkyl group, cycloalkyl group, etc. containing atoms other than carbon and hydrogen, and examples thereof include mercaptomethylmethyl, methoxymethyl, ethoxymethyl, tert-butoxymethyl, N,N-dimethylmethyl, butylene oxide, cyclopentyl, hexyl oxide, etc., and preferably methoxymethyl and cyclopentyl.

[0095] Specific examples of the aryl group include phenyl, naphthyl, anthracenyl, phenanthrenyl, tetraphenyl, pyrene, chrysene, benzo[c]phenanthrenyl, benzo[g]chrysene, fluorenyl, benzofluorenyl, dibenzofluorenyl, biphenyl, terphenyl, quaterphenyl, and fluoranthenyl, preferably phenyl and naphthyl.

[0096] Specific examples of the heteroaryl group include pyrrolyl, pyrazinyl, pyridyl, pyrimidinyl, triazine, indolyl, isoindolyl, imidazolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, azadibenzofuranyl, azadibenzothiophenyl, diazadibenzofuranyl, diazadibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, Phenazinyl, phenothiazinyl, phenoxazinyl, oxazolinyl, oxadiazolyl, furazanyl, thienyl, benzothienyl, dihydroacridinyl, azacarbazolyl, diazacarbazolyl, quinazolinyl, etc., preferably pyridyl, pyrimidinyl, triazine, dibenzofuranyl, dibenzothienyl, azadibenzofuranyl, azadibenzothienyl, diazadibenzofuranyl, diazadibenzothienyl, carbazolyl, azacarbazolyl, diazacarbazolyl.

[0097] The following embodiments are only for facilitating the understanding of the technical invention and should not be regarded as specific limitations of the present invention.

[0098] The raw materials and solvents involved in the synthesis of the compounds in the present invention were purchased from suppliers known to those skilled in the art such as Alfa and Acros.

[0099] Synthesis of ligand La003

[0100]

[0101] Synthesis of compound La003-3

[0102] Compound La003-1 (30.00 g, 135.08 mmol), dichloromethane (300 ml), triethylamine (15.03 g, 148.59 mmol) were added to a 1000 ml three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Under nitrogen protection, La003-2 (25.06 g, 148.59 mmol) was diluted with dichloromethane (125 ml) and added dropwise to the above reaction system. The addition was completed in 15 minutes, and the mixture was stirred at room temperature for 1 hour. TLC monitoring (developing solvent: ethyl acetate: petroleum ether = 1:1) showed that the reaction of the raw material La003-1 was complete.

[0103] Deionized water (50 ml) was added dropwise to quench the reaction, and the organic phase was washed with deionized water (3*150 ml). The organic phase was separated and concentrated, and then subjected to silica gel column chromatography (200-300 mesh silica gel, eluent ethyl acetate: petroleum ether = 1:15). After concentration, a light yellow solid was obtained, which was compound La003-3 (40.67 g, purity: 99.81%, yield: 85.00%), mass spectrum: 354.25 (M+H).

[0104] Synthesis of Compound La003-4

[0105] Compound La003-3 (35.00 g, 98.80 mmol), toluene (175 ml), phosphorus oxychloride (30.30 g, 197.60 mmol) were added to a 500 ml three-necked round-bottom flask, vacuum nitrogen replacement was performed 3 times, and heating reflux was stirred for 8 hours. TLC monitoring (developing solvent: ethyl acetate: petroleum ether = 1:15) showed that the raw material La003-3 was completely reacted.

[0106] The temperature was cooled to room temperature, and the reaction solution was added dropwise into deionized water (500 ml) to quench the reaction. 500 ml of acetic acid was added for extraction and separation. The organic phase was washed with deionized water (3*200 ml), and the organic phase was concentrated and then subjected to silica gel column chromatography (200-300 mesh silica gel, eluent ethyl acetate: petroleum ether = 1:25). After concentration, a white solid was obtained, which was compound La003-4 (24.01 g, purity: 99.77%, yield: 72.31%), with a mass spectrum of 336.16 (M+H).

[0107] Synthesis of compound La003

[0108] Compound La003-4 (23.50 g, 69.89 mmol), isobutylboric acid (10.69 g, 104.83 mmol), tris(dibenzylideneacetone)dipalladium (1.28 g, 1.40 mmol), 2-dicyclohexylphosphine-2′,6′-dimethoxy-biphenyl (1.15 g, 2.80 mmol), potassium phosphate (29.67 g, 139.78 mmol), toluene (350 ml) were added to a 1000 ml three-necked round-bottom flask, vacuum nitrogen was replaced 3 times, and stirred at 105° C. for 6 hours under nitrogen protection. TLC monitoring (developing solvent: ethyl acetate: petroleum ether = 1:15) showed that the raw material La003-4 was completely reacted.

[0109] The mixture was cooled to room temperature, ethyl acetate (500 ml) was added, and the mixture was washed with deionized water (3*450 ml). The organic phase was concentrated and then chromatographed on a silica gel column (200-300 mesh silica gel, eluent: ethyl acetate: petroleum ether = 1:20). After concentration, a white sugar-like solid was obtained, which was compound La003 (16.07 g, purity: 99.61%, yield: 73.35%), with a mass spectrum of 314.26 (M+H).

[0110] Synthesis of Compound Ir(La003)2(Lb005)

[0111]

[0112] Synthesis of Compound Ir(La003)-1

[0113] Compound La003 (15.56 g, 49.63 mmol) and iridium trichloride trihydrate (5.00 g, 14.18 mmol) were added into a 500 ml three-necked round-bottom flask, and ethylene glycol ether (180 ml) and deionized water (60 ml) were added. The vacuum was replaced with nitrogen three times, and then heated to 105 °C and stirred under reflux for 24 hours.

[0114] After cooling to room temperature, methanol (300 ml) was added, slurried at room temperature for 1 h, filtered, the filter cake was washed with methanol (50 ml), and the solid was vacuum dried at 80°C to obtain compound Ir(La003)-1 (10.05 g, yield: 83.12%). The obtained compound was used directly in the next step without purification.

[0115] Synthesis of Compound Ir(La003)2(Lb005)

[0116] Compound Ir(La003)-1 (9.8 g, 5.75 mmol), Lb005 (6.10 g, 28.74 mmol), sodium carbonate (6.09 g, 57.50 mmol) and ethylene glycol ethyl ether (100 ml) were added into a 500 ml single-necked round-bottom flask, vacuum nitrogen replacement was performed three times, stirring was performed at 50°C for 24 hours, and TLC monitoring (developing solvent: methanol: dichloromethane = 1:100) showed that the reaction of Ir(La003)-1 was complete.

[0117] After cooling to room temperature, methanol (150 ml) was added and the mixture was slurried at room temperature for 2 h, and then filtered. The filter cake was dissolved in dichloromethane (300 ml) to filter 200-300 mesh silica gel (60 g). The filtrate was washed with deionized water (3*100 ml), and concentrated at 50°C to obtain a dark red solid. The red solid was recrystallized twice with toluene and methanol to obtain compound Ir(La003)2(Lb005) (4.52 g, purity: 99.89%, yield: 38.21%). 4.52 g of crude Ir(La003)2(Lb005) was purified by sublimation to obtain sublimation pure Ir(La003)2(Lb005) (2.54 g, purity: 99.78%, yield: 56.19%), mass spectrum: 1029.32 (M+H).

[0118] 1 H NMR (400MHz, CDCl3) δ7.87(m,2H),7.81(m,2H),7.68(s,2H),7.49-7.47(m,2H),7.45(d,J=7.5Hz,2H),6.92(d,J=1.6Hz,2H),6.91(s,2H),4.7 2(s,1H),2.91(m,4H),2.34(s,12H),1.81-1.79(m,2H),1.32-1.23(m, 8H),1.03-1.01(m,2H),0.94(t,J=6.7Hz,12H),0.87(d,J=6.3Hz,12H).

[0119] Synthesis of Compound Ir(La003)2(Lb007)

[0120]

[0121] Synthesis of Compound Ir(La003)2(Lb007)

[0122] Referring to the synthesis and purification method of compound Ir(La003)2(Lb005), only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La003)2(Lb007) (2.35 g, purity: 99.82%, yield: 37.64%). 2.35 g of crude Ir(La003)2(Lb007) was sublimated and purified to obtain sublimation pure Ir(La003)2(Lb007) (1.28 g, purity: 99.76%, yield: 54.46%), mass spectrum: 1057.52 (M+H).

[0123] 1 H NMR (400MHz, CDCl3) δ7.89-7.86(m,2H),7.81(m,2H),7.68(s,2H),7.50-7.46(m,4H),6.9-6.91(m,2H),6.88(s ,2H),4.75(s,1H),2.92-2.90(m,4H),2.34(s,12H),1.85-1.75(m,2H),1.05-0.99(m,14H),0.92-0.85(m,24H).

[0124] Synthesis of Ligand La006

[0125]

[0126] Synthesis of compound La006

[0127] Referring to the synthesis and purification method of compound La003, it is only necessary to change the corresponding raw materials to obtain the target compound La006 (18.54 g, purity: 99.77%, yield: 68.78%), mass spectrum: 326.28 (M+H).

[0128] Synthesis of Compound Ir(La006)2(Lb005)

[0129]

[0130] Synthesis of Compound Ir(La006)-1

[0131] Referring to the synthesis and purification method of compound Ir(La003)-1, only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La006)-1 (9.81 g, yield: 68.21%), which was used directly in the next step without purification.

[0132] Synthesis of Compound Ir(La006)2(Lb005)

[0133] Referring to the synthesis and purification method of compound Ir(La003)2(Lb005), only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La006)2(Lb005) (2.12 g, purity: 99.80%, yield: 38.88%). 2.12 g of crude Ir(La006)2(Lb005) was sublimated and purified to obtain sublimation pure Ir(La006)2(Lb005) (1.03 g, purity: 99.75%, yield: 48.58%), mass spectrum: 1053.16 (M+H).

[0134] 1 H NMR (400MHz, CDCl3) δ7.88-7.86(m,2H),7.81(m,2H),7.68(s,2H),7.49- 7.47(m,2H),7.45(d,J=7.5Hz,2H),6.92-6.89(m,4H),4.75(s,1H),2.34( s,12H),1.91-1.89(m,4H),1.77-1.76(m,4H),1.70-1.64(m,8H),1.32-1 .31(m,4H),1.27-1.21(m,4H),1.03-1.00(m,4H),0.94(t,J=6.6Hz,12H).

[0135] Synthesis of ligand La015

[0136]

[0137] Synthesis of compound La015-3

[0138] Referring to the synthesis and purification method of compound La003-3, it is only necessary to change the corresponding raw materials to obtain a white solid compound La015-3 (35.47 g, purity: 99.81%, yield: 84.74%), mass spectrum: 368.08 (M+H).

[0139] Synthesis of Compound La015-4

[0140] Referring to the synthesis and purification method of compound La003-4, it is only necessary to change the corresponding raw materials to obtain a white solid compound La015-4 (20.63 g, purity: 99.83%, yield: 71.55%), mass spectrum: 350.16 (M+H).

[0141] Synthesis of compound La015

[0142] Referring to the synthesis and purification method of compound La003, only the corresponding raw materials need to be changed to obtain a white sugar-like solid compound La015 (15.22 g, purity: 99.75%, yield: 68.73%), mass spectrum: 328.48 (M+H). Synthesis of compound Ir(La015)2(Lb005)

[0143]

[0144] Synthesis of Compound Ir(La015)-1

[0145] Referring to the synthesis and purification method of compound Ir(La003)-1, only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La015)-1 (8.78 g, yield: 65.13%), which was used directly in the next step without purification.

[0146] Synthesis of Compound Ir(La015)2(Lb005)

[0147] Referring to the synthesis and purification method of compound Ir(La003)2(Lb005), only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La015)2(Lb005) (1.98 g, purity: 99.88%, yield: 40.05%). 1.98 g of crude Ir(La015)2(Lb005) was sublimated and purified to obtain sublimation pure Ir(La015)2(Lb005) (1.10 g, purity: 99.75%, yield: 55.55%), mass spectrum: 1057.32 (M+H).

[0148] 1 H NMR (400MHz, CDCl3) δ7.88-7.86(m,2H),7.81(m,2H),7.68(m,2H),7.63(s,2H ),7.49-7.47(m,2H),6.92(s,2H),4.75(s,1H),2.92(d,J=6.8Hz,4H),2.70(s ,6H),2.34(d,J=15.0Hz,12H),1.83-1.77(m,2H),1.34-1.28(m,4H),1.25-1. 23(m,4H),1.03-1.00(m,2H),0.94(t,J=6.7Hz,12H),0.87(d,J=6.3Hz,12H).

[0149] Synthesis of ligand La029

[0150]

[0151] Synthesis of compound La029-2

[0152] La029-1 (50.00 g, 191.48 mmol) and dry tetrahydrofuran (500 ml) were added to a 1000 ml three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then the system was cooled to -78 ° C, and n-butyl lithium (86.25 ml, 210.63 mmol, 2.5 mol / l n-hexane solution) was added dropwise over 30 minutes; the temperature was maintained at -78 ° C and stirred for 1 hour, and N, N-dimethylformamide (27.99 g, 382.96 mmol) was added dropwise over 10 minutes, and the temperature was maintained at -78 ° C and stirred for 1 hour. TLC monitoring (developing solvent is petroleum ether) showed that the raw material La029-1 was completely reacted.

[0153] Deionized water (100 ml) was added dropwise to quench the reaction, the temperature was raised to room temperature, and tetrahydrofuran was removed by concentration. Ethyl acetate (500 ml) was added, and the organic phase was washed with deionized water (3*150 ml), separated, and the organic phase was concentrated and subjected to silica gel column chromatography (200-300 mesh silica gel, eluent ethyl acetate: petroleum ether = 1:12). After concentration, a light yellow liquid was obtained, which was compound La029-2 (28.63 g, purity: 99.51%, yield: 71.12%), mass spectrum: 211.06 (M+H).

[0154] Synthesis of compound La029-3

[0155] La029-2 (28.11 g, 133.71 mmol) and dichloromethane (300 ml) were added to a 1000 ml three-necked round-bottom flask, and sodium hypochlorite (49.76 g, 668.55 mmol, calculated as sodium hypochlorite) with 13% active chlorine was added dropwise (the pH of sodium hypochlorite was adjusted to 6 with 20% mass concentration of sulfuric acid in advance), and the addition was completed over 40 minutes; the mixture was stirred at room temperature for 1 hour. The reaction of the raw material La029-2 was completed by TLC monitoring (developing solvent: ethyl acetate: petroleum ether = 1:10).

[0156] The organic phase was separated, and deionized water was added to wash (3*100 ml). The organic phase was separated, and concentrated to obtain a light yellow liquid compound La029-3 (25.75 g, purity: 99.32%, yield: 85.12%), mass spectrum: 227.16 (M+H). The crude product was used directly in the next step without purification.

[0157] Synthesis of compound La029-4

[0158] La029-3 (23.54 g, 104.05 mmol) and dichloromethane (250 ml) were added to a 500 ml three-necked round-bottom flask, and the atmosphere was replaced with nitrogen three times under vacuum. Dichlorothionyl (24.76 g, 208.11 mmol) was added dropwise under stirring at room temperature for 10 minutes, and the mixture was stirred at room temperature for 40 minutes. The reaction of the raw material La029-3 was completed by TLC monitoring (developing solvent: ethyl acetate: petroleum ether = 1:10).

[0159] The reaction solution was directly concentrated, and the organic phase was concentrated to obtain a light yellow liquid compound La029-4 (19.31 g, yield: 75.85%). The crude product was used directly in the next step without purification.

[0160] Synthesis of Compound La029-5

[0161] Referring to the synthesis and purification method of compound La003-3, it is only necessary to change the corresponding raw materials to obtain a white solid compound La029-5 (30.11 g, purity: 99.78%, yield: 83.34%), mass spectrum: 430.06 (M+H).

[0162] Synthesis of Compound La029-6

[0163] Referring to the synthesis and purification method of compound La003-4, it is only necessary to change the corresponding raw materials to obtain a white solid compound La029-6 (18.67 g, purity: 99.83%, yield: 68.56%), mass spectrum: 412.04 (M+H).

[0164] Synthesis of compound La029

[0165] Referring to the synthesis and purification method of compound La003, only the corresponding raw materials need to be changed to obtain a white sugar-like solid compound La029 (11.62 g, purity: 99.75%, yield: 65.81%), mass spectrum: 416.2 (M+H). Synthesis of compound Ir(La029)2(Lb005)

[0166]

[0167] Synthesis of Compound Ir(La029)-1

[0168] Referring to the synthesis and purification method of compound Ir(La003)-1, only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La029)-1 (9.31 g, yield: 68.18%), which was used directly in the next step without purification.

[0169] Synthesis of Compound Ir(La029)2(Lb005)

[0170] Referring to the synthesis and purification method of compound Ir(La003)2(Lb005), only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La029)2(Lb005) (2.52 g, purity: 99.85%, yield: 43.33%). 2.52 g of crude Ir(La029)2(Lb005) was sublimated and purified to obtain sublimation pure Ir(La029)2(Lb005) (1.31 g, purity: 99.82%, yield: 51.98%), mass spectrum: 1233.54 (M+H).

[0171] 1 H NMR (400MHz, CDCl3) δ7.99-7.97(m,2H),7.88-7.86(m,2H),7.81-7.80(m,4H),7.55-7.53(m,2H), 7.49-7.47(dd,J=7.4,1.5Hz,2H),7.45(d,J=7.5Hz,2H),7.41-7.37(m,2H),7.33-7.29(m,2H),6.9 1(s,2H),4.74(s,1H),2.92(d,J=7.6Hz,4H),2.34(s,6H),1.91-1.90(m,4H),1.77-1.75(m,4H),1 .68-1.63(m,8H),1.33-1.28(m,4H),1.26-1.21(m,4H),1.03-1.00(m,4H),0.94(t,J=6.6Hz,12H).

[0172] Synthesis of Compound Ir(La029)2(Lb009)

[0173]

[0174] Synthesis of Compound Ir(La029)2(Lb009)

[0175] Referring to the synthesis and purification method of compound Ir(La003)2(Lb005), only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La029)2(Lb009) (1.99 g, purity: 99.90%, yield: 45.25%). 1.99 g of crude Ir(La029)2(Lb009) was sublimated and purified to obtain sublimation pure Ir(La029)2(Lb009) (1.20 g, purity: 99.88%, yield: 60.30%), mass spectrum: 1229.18 (M+H).

[0176] 1H NMR (400MHz, CDCl3) δ7.99(m,2H),7.88-7.86(m,2H),7.81-7.80(m,4H),7.55-7.53(m,2H),7.49- 7.43(m,2H),7.45(d,J=7.5Hz,2H),7.41-7.37(m,2H),7.33-7.29(m,2H),6.91(s,2H),4.75(s,1H) ,2.91(dd,J=5.7,2.2Hz,4H),2.34(s,6H),2.22-2.18(m,2H),1.93-1.87(m,4H),1.79-1.73(m,8H) ),1.70-1.61(m,14H),1.57-1.53(m,2H),1.40-1.37(m,2H),1.32-1.28(m,2H),1.02-0.98(m,2H).

[0177] Synthesis of ligand La039

[0178]

[0179] Synthesis of compound La039-1

[0180] Referring to the synthesis and purification method of compound La003, it is only necessary to change the corresponding raw materials to obtain compound La039-1 (35.42 g, purity: 99.80%, yield: 68.44%), mass spectrum: 200.06 (M+H).

[0181] Synthesis of compound La039-2

[0182] La039-1 (30.00 g, 150.53 mmol) and acetonitrile (300 ml) were added to a 1000 ml three-necked round-bottom flask, and the atmosphere was replaced with nitrogen three times under vacuum. Then the system was cooled to 0°C, and N-bromosuccinimide (8.99 g, 158.06 mmol) was added in three batches over 15 minutes, and stirred at room temperature for 5 hours. The reaction of the raw material La039-1 was completed by TLC monitoring (developing solvent: ethyl acetate: petroleum ether = 2:1).

[0183] Deionized water (100 ml) was added dropwise to quench the reaction, and ethyl acetate (800 ml) was added for extraction. The organic phase was washed with deionized water (3*280 ml). The organic phase was concentrated and then subjected to silica gel column chromatography (200-300 mesh silica gel, eluent ethyl acetate: petroleum ether = 1:2). After concentration, a light yellow liquid was obtained, which was compound La039-2 (37.69 g, purity: 99.73%, yield: 90.00%), mass spectrum: 278.16 (M+H).

[0184] Synthesis of compound La039-3

[0185] La039-2 (30.00 g, 107.84 mmol), palladium acetate (484.94 mg, 2.16 mmol), n-butyl di(1-adamantyl) phosphine (1.55 g, 4.32 mmol), dried potassium phosphate (45.78 g, 215.68 mmol), deuterated tert-butyl alcohol (16.20 g, 215.68 mmol), and dried toluene (300 ml) were added to a 1000 ml three-necked round-bottom flask, vacuum nitrogen was replaced three times, and the mixture was heated to 100° C. and refluxed overnight for 16 h. The reaction of the raw material La039-2 was completed by TLC monitoring (developing solvent: ethyl acetate: petroleum ether = 2:1).

[0186] The mixture was cooled to room temperature, ethyl acetate (300 ml) was added, and the mixture was washed with deionized water (3*200 ml). The organic phase was concentrated and then chromatographed on a silica gel column (200-300 mesh silica gel, eluent: ethyl acetate: petroleum ether = 1:2). After concentration, a light yellow liquid was obtained, which was compound La039-3 (20.52 g, purity: 99.85%, deuteration rate: 99%, yield: 95.00%), mass spectrum: 201.26 (M+H).

[0187] Synthesis of compound La039-4

[0188] Referring to the synthesis and purification method of compound La003-3, it is only necessary to change the corresponding raw materials to obtain compound La039-4 (27.63 g, purity: 99.78%, yield: 83.15%), mass spectrum: 409.20 (M+H).

[0189] Synthesis of compound La039

[0190] Referring to the synthesis and purification method of compound La003-4, it is only necessary to change the corresponding raw materials to obtain compound La039 (18.76 g, purity: 99.73%, yield: 70.26%), mass spectrum: 391.28 (M+H).

[0191] Synthesis of Compound Ir(La039)2(Lb005)

[0192]

[0193] Synthesis of Compound Ir(La039)-1

[0194] Referring to the synthesis and purification method of compound Ir(La003)-1, only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La039)-1 (7.89 g, yield: 68.78%), which was used directly in the next step without purification.

[0195] Synthesis of Compound Ir(La039)2(Lb005)

[0196] Referring to the synthesis and purification method of compound Ir(La003)2(Lb005), only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La039)2(Lb005) (1.56 g, purity: 99.89%, yield: 48.68%). 1.56 grams of crude Ir(La039)2(Lb005) was sublimated and purified to obtain sublimation pure Ir(La039)2(Lb005) (0.98 g, purity: 99.88%, deuteration rate: 99%, yield: 62.82%), mass spectrum: 1183.50 (M+H).

[0197] 1 H NMR(400MHz, CDCl3)δ7.98(m,2H),7.86-7.84(m,3H),7.81-7.79(m,5H),7.54-7.52(m,2H),7.50-7.46(m,2H),7.42-7.36(m,2H),7.34-7.27( m,2H),4.75(s,1H),2.92(d,J=5.7Hz,4H),2.31(s,6H),1.85-1.75(m,2 H),1.25-1.16(m,10H),0.94(t,J=6.7Hz,12H),0.87(d,J=6.3Hz,12H).

[0198] Synthesis of ligand La051

[0199]

[0200] Synthesis of compound La051-3

[0201] Referring to the synthesis and purification method of compound La003-3, it is only necessary to change the corresponding raw materials to obtain a white solid compound La015 (40.33 g, purity: 99.79%, yield: 85.63%), mass spectrum: 410.08 (M+H).

[0202] Synthesis of compound La051-4

[0203] Referring to the synthesis and purification method of compound La003-4, it is only necessary to change the corresponding raw materials to obtain a white solid compound La051-4 (26.09 g, purity: 99.83%, yield: 72.36%), mass spectrum: 392.08 (M+H).

[0204] Synthesis of compound La051

[0205] Referring to the synthesis and purification method of compound La003, only the corresponding raw materials need to be changed to obtain a white sugar-like solid compound La051 (19.05 g, purity: 99.78%, yield: 70.01%), mass spectrum: 370.28 (M+H). Synthesis of compound Ir(La051)2(Lb005)

[0206]

[0207] Synthesis of Compound Ir(La051)-1

[0208] Referring to the synthesis and purification method of compound Ir(La003)-1, only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La051)-1 (10.87 g, yield: 68.45%), which was used directly in the next step without purification.

[0209] Synthesis of Compound Ir(La051)2(Lb005)

[0210] Referring to the synthesis and purification method of compound Ir(La003)2(Lb005), only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La051)2(Lb005) (3.50 g, purity: 99.88%, yield: 43.52%). 3.50 g of crude Ir(La051)2(Lb005) was sublimated and purified to obtain sublimation pure Ir(La051)2(Lb005) (2.13 g, purity: 99.82%, yield: 60.85%), mass spectrum: 1141.64 (M+H).

[0211] 1 H NMR (400MHz, CDCl3) δ7.88-7.84(m,4H),7.81(t,J=7.4Hz,2H),7.49(dd,J=7 .4,1.5Hz,2H),7.45(d,J=7.5Hz,2H),7.24(d,J=1.4Hz,2H),6.91(s,2H),4.7 4(s,1H),2.92-2.84(m,8H),1.81-1.79(m,2H),1.31-1.30(m,4H),1.25-1.1 6(m,28H),1.03-1.00(m,2H),0.94(t,J=6.7Hz,12H),0.87(d,J=6.3Hz,12H).

[0212] Synthesis of ligand La076

[0213]

[0214] Synthesis of compound La076-3

[0215] Referring to the synthesis and purification method of compound La003-3, it is only necessary to change the corresponding raw materials to obtain a white solid compound La076-3 (25.10 g, purity: 99.75%, yield: 84.46%), mass spectrum: 354.04 (M+H).

[0216] Synthesis of compound La076-4

[0217] Referring to the synthesis and purification method of compound La003-4, it is only necessary to change the corresponding raw materials to obtain a white solid compound La076-4 (16.80 g, purity: 99.73%, yield: 70.08%), mass spectrum: 336.23 (M+H).

[0218] Synthesis of compound La076

[0219] Referring to the synthesis and purification method of compound La003, only the corresponding raw materials need to be changed to obtain a white sugar-like solid compound La076 (8.92 g, purity: 99.81%, yield: 68.61%), mass spectrum: 328.24 (M+H). Synthesis of compound Ir(La076)2(Lb005)

[0220]

[0221] Synthesis of Compound Ir(La076)-1

[0222] Referring to the synthesis and purification method of compound Ir(La003)-1, only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La076)-1 (7.56 g, yield: 65.63%), which was used directly in the next step without purification.

[0223] Synthesis of Compound Ir(La076)2(Lb005)

[0224] Referring to the synthesis and purification method of compound Ir(La003)2(Lb005), only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La076)2(Lb005) (1.79 g, purity: 99.81%, yield: 40.11%). 1.79 g of crude Ir(La076)2(Lb005) was sublimated and purified to obtain sublimation pure Ir(La076)2(Lb005) (1.15 g, purity: 99.77%, yield: 64.24%), mass spectrum: 1057.53 (M+H).

[0225] 1H NMR (400MHz, CDCl3) δ7.68(m,2H),7.61-7.59(m,2H),7.44-7.39(m,4H),7.08(t,J=7.5Hz,2H),6.99(d,J=7.3Hz,2H),6.92(s, 2H),4.73(s,1H),3.09(d,4H),2.34-2.31(s,12H),1.34-1.22(m,8H),1.03-1.00(m,2H),0.94(t,J=6.7Hz,12H),0.85(s,18H).

[0226] Synthesis of ligand La083

[0227]

[0228] Synthesis of compound La083

[0229] Referring to the synthesis and purification method of compound La003, only the corresponding raw materials need to be changed to obtain a white sugar-like solid compound La083 (7.66 g, purity: 99.78%, yield: 63.31%), mass spectrum: 326.23 (M+H). Synthesis of compound Ir(La083)2(Lb005)

[0230]

[0231] Synthesis of Compound Ir(La083)-1

[0232] Referring to the synthesis and purification method of compound Ir(La003)-1, only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La083)-1 (6.83 g, yield: 75.63%), which was used directly in the next step without purification.

[0233] Synthesis of Compound Ir(La083)2(Lb005)

[0234] Referring to the synthesis and purification method of compound Ir(La003)2(Lb005), only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La083)2(Lb005) (1.38 g, purity: 99.89%, yield: 45.31%). 1.38 g of crude Ir(La083)2(Lb005) was sublimated and purified to obtain sublimation pure Ir(La083)2(Lb005) (0.66 g, purity: 99.86%, yield: 47.82%), mass spectrum: 1053.28 (M+H).

[0235] 1H NMR (400MHz, CDCl3) δ7.68(m,2H),7.62-7.58(m,2H),7.45-7.39(m,4H),7.08(t,J=14.9Hz,2H),6.98(d,J=15.0H z,2H),6.92(s,2H),4.74(s,1H),2.34-2.31(s,12H),1.92-1.63(m,16H),1.33-1.19(m,12H),1.08-0.89(m,12H).

[0236] Synthesis of ligand La091

[0237]

[0238] Synthesis of compound La091-3

[0239] Referring to the synthesis and purification method of compound La003-3, it is only necessary to change the corresponding raw materials to obtain a white solid compound La091-3 (25.16 g, purity: 99.75%, yield: 86.74%), mass spectrum: 368.08 (M+H).

[0240] Synthesis of compound La091-4

[0241] Referring to the synthesis and purification method of compound La003-4, it is only necessary to change the corresponding raw materials to obtain a white solid compound La091-4 (17.63 g, purity: 99.80%, yield: 70.55%), mass spectrum: 350.16 (M+H).

[0242] Synthesis of compound La091

[0243] Referring to the synthesis and purification method of compound La003, only the corresponding raw materials need to be changed to obtain a white sugar-like solid compound La091 (12.00 g, purity: 99.78%, yield: 68.77%), mass spectrum: 382.26 (M+H). Synthesis of compound Ir(La091)2(Lb005)

[0244]

[0245] Synthesis of Compound Ir(La091)-1

[0246] Referring to the synthesis and purification method of compound Ir(La003)-1, only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La091)-1 (8.08 g, yield: 78.03%), which was used directly in the next step without purification.

[0247] Synthesis of Compound Ir(La091)2(Lb005)

[0248] Referring to the synthesis and purification method of compound Ir(La003)2(Lb005), only the corresponding raw materials need to be changed to obtain the red solid compound Ir(La091)2(Lb005) (2.31 g, purity: 99.87%, yield: 45.55%). 2.31 g of crude Ir(La091)2(Lb005) was sublimated and purified to obtain sublimation pure Ir(La091)2(Lb005) (1.11 g, purity: 99.82%, yield: 48.05%), mass spectrum: 1165.62 (M+H).

[0249] 1 H NMR (400MHz, CDCl3) δ7.68(m,2H),7.40(d,J=7.5Hz,2H),7.26(d,J=7.5Hz,2H),7.06(d,J=7.5Hz,2H),6.99(d,J=7.3Hz,2H),6.92(s,2H),4. 75(s,1H),2.70(s,6H),2.34-2.31(s,12H),1.33-1.23(m,16H),1.12- 1.10(m,5H),1.03-1.00(m,7H),0.94(t,J=6.6Hz,12H),0.87(s,12H).

[0250] Synthesis of ligand La111

[0251]

[0252] Synthesis of compound La111-3

[0253] Referring to the synthesis and purification method of compound La003-3, it is only necessary to change the corresponding raw materials to obtain a white solid compound La111-3 (24.38 g, purity: 99.71%, yield: 81.22%), mass spectrum: 354.26 (M+H).

[0254] Synthesis of Compound La111-4

[0255] Referring to the synthesis and purification method of compound La003-4, it is only necessary to change the corresponding raw materials to obtain a white solid compound La111-4 (15.00 g, purity: 99.73%, yield: 72.63%), mass spectrum: 336.04 (M+H).

[0256] Synthesis of compound La111

[0257] Referring to the synthesis and purification method of compound La003, only the corresponding raw materials need to be changed to obtain a white sugar-like solid compound La111 (10.23 g, purity: 99.78%, yield: 67.43%), mass spectrum: 314.12 (M+H). Synthesis of compound Ir(La111)2(Lb005)

[0258]

[0259] Synthesis of Compound Ir(La111)-1

[0260] Referring to the synthesis and purification method of compound Ir(La003)-1, only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La111)-1 (7.06 g, yield: 75.38%), which was used directly in the next step without purification.

[0261] Synthesis of Compound Ir(La111)2(Lb005)

[0262] Referring to the synthesis and purification method of compound Ir(La003)2(Lb005), only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La111)2(Lb005) (1.87 g, purity: 99.89%, yield: 48.52%). 1.87 g of crude Ir(La111)2(Lb005) was sublimated and purified to obtain sublimation pure Ir(La111)2(Lb005) (1.01 g, purity: 99.86%, yield: 54.01%), mass spectrum: 1029.38 (M+H).

[0263] 1 H NMR(400MHz, CDCl3)δ7.68(s,2H),7.76-7.60(m,4H),7.48-7.43(m,4H),7.08(m,2H),6.92(s,2H),4.75(s,1H),2 .54-2.53(dd,J=10.6,3.9Hz,4H),2.34-2.31(s,12H),1.85-1.77(m,2H),1.34-1.19(m,10H),1.16-0.78(m,24H).

[0264] Synthesis of ligand La135

[0265]

[0266] Synthesis of compound La135-1

[0267] Referring to the synthesis and purification method of compound La003, it is only necessary to change the corresponding raw materials to obtain compound La135-1 (38.96 g, purity: 99.68%, yield: 60.41%), mass spectrum: 200.04 (M+H).

[0268] Synthesis of compound La135-2

[0269] Referring to the synthesis and purification method of compound La039-2, it is only necessary to change the corresponding raw materials to obtain compound La135-2 (32.77 g, purity: 99.71%, yield: 85.55%), mass spectrum: 278.06 (M+H).

[0270] Synthesis of compound La135-3

[0271] Referring to the synthesis and purification method of compound La003, it is only necessary to change the corresponding raw materials to obtain compound La135-3 (16.21 g, purity: 99.75%, yield: 58.43%), mass spectrum: 242.48 (M+H).

[0272] Synthesis of Compound La135-4

[0273] Referring to the synthesis and purification method of compound La003-3, it is only necessary to change the corresponding raw materials to obtain compound La135-4 (22.14 g, purity: 99.68%, yield: 86.15%), mass spectrum: 374.20 (M+H).

[0274] Synthesis of compound La135

[0275] Referring to the synthesis and purification method of compound La003-4, it is only necessary to change the corresponding raw materials to obtain compound La135 (13.51 g, purity: 99.68%, yield: 74.61%), mass spectrum: 356.16 (M+H).

[0276] Synthesis of Compound Ir(La135)2(Lb005)

[0277]

[0278] Synthesis of Compound Ir(La135)-1

[0279] Referring to the synthesis and purification method of compound Ir(La003)-1, only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La135)-1 (9.89 g, yield: 74.01%), which was used directly in the next step without purification.

[0280] Synthesis of Compound Ir(La135)2(Lb005)

[0281] Referring to the synthesis and purification method of compound Ir(La003)2(Lb005), only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La135)2(Lb005) (3.55 g, purity: 99.87%, yield: 49.33%). 3.55 g of crude Ir(La135)2(Lb005) was sublimated and purified to obtain sublimation pure Ir(La135)2(Lb005) (2.13 g, purity: 99.86%, yield: 60.00%), mass spectrum: 1113.28 (M+H).

[0282] 1 H NMR (400MHz, CDCl3) δ7.97(s,2H),7.83(m,2H),7.68(d,J=1.4Hz,2H),7.45(d,J=7.5Hz,2H),6.92-6.89(m,4H),4.73(s,1H),2.90-2.85(m,2H) ,2.55(d,J=7.4Hz,4H),2.34(s,12H),1.85-1.79(m,2H),1.32-1.21(m, 20H),1.03-1.00(m,2H),0.94(t,J=6.7Hz,12H),0.87(d,J=6.3Hz,12H).

[0283] Synthesis of ligand La155

[0284]

[0285] Synthesis of compound La155-1

[0286] Referring to the synthesis and purification method of compound La003-3, it is only necessary to change the corresponding raw materials to obtain compound La155-1 (30.56 g, purity: 99.75%, yield: 85.66%), mass spectrum: 430.02 (M+H).

[0287] Synthesis of Compound La155-2

[0288] Referring to the synthesis and purification method of compound La003-4, it is only necessary to change the corresponding raw materials to obtain compound La155-2 (18.35 g, purity: 99.78%, yield: 73.43%), mass spectrum: 412.02 (M+H).

[0289] Synthesis of Compound La155-4

[0290] La155-2 (25.03 g, 60.71 mmol), La115-3 (15.16 g, 72.85 mmol), bis(4-dimethylaminophenyl di-tert-butylphosphine) palladium dichloride (859.73 mg, 1.21 mmol), potassium carbonate (16.78 g, 121.42 mmol), 1,4-dioxane (300 ml), and deionized water (100 ml) were added to a 1000 ml single-mouth round-bottom flask, vacuum nitrogen replacement 3 times, and stirred at 80°C for 2 hours. TLC monitoring (developing solvent: ethyl acetate: petroleum ether = 1:5) showed that the raw material La115-2 was completely reacted.

[0291] The mixture was cooled to room temperature and concentrated to remove the solvent. Dichloromethane (500 ml) was added and the mixture was washed with deionized water (3*150 ml). The organic phase was concentrated and then chromatographed on a silica gel column (200-300 mesh silica gel, eluent: ethyl acetate: petroleum ether = 1:10). After concentration, a white solid was obtained, which was compound La115-4 (21.34 g, purity: 99.62%, yield: 85.02%). Mass spectrum: 414.16 (M+H).

[0292] Synthesis of Compound La115-5

[0293] La115-4 (15.03 g, 36.35 mmol), ammonium formate (22.92 g, 363.50 mmol), platinum dioxide (825.45 mg, 3.64 mmol), and tetrahydrofuran (150 ml) were added to a 500 ml three-necked round-bottom flask, vacuum nitrogen was replaced three times, and stirred at 65° C. for 6 hours. The reaction of the raw material La115-4 was completed by TLC monitoring.

[0294] The mixture was cooled to room temperature and concentrated to remove the solvent. Dichloromethane (500 ml) was added and the mixture was washed with deionized water (3*150 ml). The organic phase was concentrated and then chromatographed on a silica gel column (200-300 mesh silica gel, eluent: ethyl acetate: petroleum ether = 1:12). After concentration, a white sugar-like solid was obtained, which was compound La115-5 (10.56 g, purity: 99.63%, yield: 72.36%). Mass spectrum: 416.26 (M+H).

[0295] Synthesis of compound La155

[0296] La115-5 (21.65 g, 52.15 mmol) and dichloromethane (200 ml) were added to a 500 ml three-necked round-bottom flask, and the flask was evacuated and replaced with nitrogen three times. Bis(2-methoxyethyl)aminosulfur trifluoride (23.07 g, 104.30 mmol) was added dropwise under stirring at room temperature, and stirred at room temperature overnight. TLC monitoring (developing solvent: ethyl acetate: petroleum ether = 1:10) showed that the raw material La115-5 was completely reacted.

[0297] The reaction solution was added dropwise to a saturated aqueous sodium bicarbonate solution to quench the reaction, the pH value of the system was adjusted to 8, and the tetrahydrofuran was removed by concentration. Dichloromethane (500 ml) was added, the solution was separated, and the solution was washed with deionized water (3*150 ml). The organic phase was concentrated and then subjected to silica gel column chromatography (200-300 mesh silica gel, eluent ethyl acetate: petroleum ether = 1:20). After concentration, a white sugar-like solid was obtained, which was compound La155 (15.60 g, purity: 99.73%, yield: 68.45%), mass spectrum: 438.20 (M+H).

[0298] Synthesis of Compound Ir(La155)2(Lb005)

[0299]

[0300] Synthesis of Compound Ir(La155)-1

[0301] Referring to the synthesis and purification method of compound Ir(La003)-1, only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La155)-1 (8.69 g, yield: 75.46%), which was used directly in the next step without purification.

[0302] Synthesis of Compound Ir(La155)2(Lb005)

[0303] Referring to the synthesis and purification method of compound Ir(La003)2(Lb005), only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La155)2(Lb005) (2.73 g, purity: 99.86%, yield: 41.22%). 2.73 g of crude Ir(La155)2(Lb005) was purified by sublimation to obtain sublimation pure Ir(La155)2(Lb005) (1.19 g, purity: 99.86%, yield: 43.58%), mass spectrum: 1277.46 (M+H).

[0304] 1 H NMR (400MHz, CDCl3) δ7.97(m,2H),7.82(m,2H),7.68(s,2H),7.61-7.59(m,4H),7.44-7.42(m,2H),7.39-7.32(m,2H),7.30-7.2 6(m,4H),7.10(m,2H),4.73(s,1H),2.32(s,6H),1.95-1.60(m,10H),1.34-1.28(m,6H),1.11-0.97(m,8H),0.97-0.89(m,12H).

[0305] Synthesis of ligand La172

[0306]

[0307] Synthesis of compound La172-2

[0308] Referring to the synthesis and purification method of compound La003, it is only necessary to change the corresponding raw materials to obtain compound La172-2 (27.47 g, purity: 99.63%, yield: 55.45%), mass spectrum: 284.24 (M+H).

[0309] Synthesis of compound La172-3

[0310] Referring to the synthesis and purification method of compound La003-3, it is only necessary to change the corresponding raw materials to obtain compound La172-3 (20.05 g, purity: 99.70%, yield: 75.65%), mass spectrum: 464.26 (M+H).

[0311] Synthesis of compound La172

[0312] Referring to the synthesis and purification method of compound La003-4, it is only necessary to change the corresponding raw materials to obtain compound La172-3 (15.36 g, purity: 99.76%, yield: 71.11%), mass spectrum: 474.18 (M+H).

[0313] Synthesis of Compound Ir(La172)2(Lb005)

[0314]

[0315] Synthesis of Compound Ir(La172)-1

[0316] Referring to the synthesis and purification method of compound Ir(La003)-1, only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La172)-1 (7.35 g, yield: 67.91%), which was used directly in the next step without purification.

[0317] Synthesis of Compound Ir(La172)2(Lb005)

[0318] Referring to the synthesis and purification method of compound Ir(La003)2(Lb005), only the corresponding raw materials need to be changed to obtain the red solid compound Ir(La172)2(Lb005) (1.56g, purity: 99.82%, yield: 46.12%). 1.56g of crude Ir(La172)2(Lb005) was sublimated and purified to obtain sublimation pure Ir(La172)2(Lb005) (0.72g, purity: 99.78%, yield: 46.15%), mass spectrum: 1349.68(M+H).

[0319] 1 H NMR (400MHz, CDCl3) δ7.99-7.97(m,2H),7.81(m,2H),7.60-7.58(m,4H),7.54-7.53(m,2H),7.39-7.31(m,2H),7.30-7.28(m,4H),7. 10(t,J=1.4Hz,2H),4.72(s,1H),2.54(t,J=3.8Hz,8H),2.34(s,6H),1.34-1.21(m,10H),0.94(t,J=6.7Hz,12H),0.89-0.83(m,36H).

[0320] Synthesis of Compound Ir(La003)(Lb005)(Lc004)

[0321]

[0322] Synthesis of Compound [Ir(La003)(COD)]-1

[0323] La003 (14.27 g, 45.52 mmol), silver oxide (5.27 g, 22.76 mmol), 4A powdered molecular sieve (30 g), and dichloromethane (320 ml) were added to a 1000 ml single-mouth round-bottom flask, and the vacuum nitrogen was replaced 3 times. The reaction was stirred at room temperature for 5 hours, and the reaction liquid turned into a brown-black turbid liquid. TLC monitoring (developing solvent was ethyl acetate: petroleum ether = 1:15) showed that the raw material La003 was completely consumed. Then 1,5-cyclooctadiene iridium chloride dimer (15.28 g, 22.76 mmol) was added, and stirred at room temperature overnight for 16 hours. TLC monitoring (developing solvent was methanol: dichloromethane = 1:90) showed that a large amount of highly polar red products were generated, and the reaction was stopped.

[0324] Filter, collect the filtrate and concentrate, add n-hexane (150 ml), slurry at room temperature for 2 hours, filter with suction, and dry the filter cake to obtain a red solid [Ir(La003)(COD)]-1 (10.67 g, yield: 70.71%), mass spectrum: 648.19 (M+H)

[0325] Synthesis of Compound [Ir(La003)(Lc004)]-1

[0326] Compound [Ir(La003)(COD)]-1 (10.00 g, 15.45 mmol), Lc004 (13.40 g, 46.35 mmol), ethylene glycol ether (180 ml) were added to a 500 ml three-necked round-bottom flask, vacuum replaced 3 times, heated to 120°C and stirred overnight for 24 hours. TLC monitoring (developing solvent: methanol: dichloromethane = 1:97) showed that the raw material [Ir(La003)(COD)]-1 was completely consumed.

[0327] After cooling to room temperature, methanol (350 ml) was added, filtered, and the filter cake was dried under vacuum at 80°C to obtain compound [Ir(La003)(Lc004)]-1 (5.34 g, yield: 41.96%). The obtained compound was used directly in the next step without purification.

[0328] Synthesis of Compound Ir(La003)(Lb005)(Lc004)

[0329] Referring to the synthesis and purification method of compound Ir(La003)2(Lb005), only the corresponding raw materials need to be changed to obtain the red solid compound Ir(La003)(Lb005)(Lc004) (2.85g, purity: 99.87%, yield: 43.21%). 2.85g of crude Ir(La003)(Lb005)(Lc004) was sublimated and purified to obtain sublimation pure Ir(La003)(Lb005)(Lc004) (1.63g, purity: 99.81%, yield: 57.19%), mass spectrum: 1005.28 (M+H)

[0330] 1 H NMR(400MHz, CDCl3)δ8.59(d,J=7.5Hz,1H),8.20(d,J=1.4Hz,1H),7.96-7.82(m,1H), 7.83-7.76(m,2H),7.68(d,J=1.4Hz,3H),7.52-7.49(m,2H),7.45(d,J=7.5Hz,1H),6. 92-6.89(m,3H),4.76(s,1H),2.91(d,J=7.2Hz,2H),2.43(d,J=7.8Hz,2H),2.32(s,12 H),1.85-1.77(m,2H),1.36-1.21(m,10H),0.94(t,J=6.7Hz,12H),0.88-0.85(m,12H).

[0331] Synthesis of Compound Ir(La029)(Lb005)(Lc011)

[0332]

[0333] Synthesis of Compound [Ir(La029)(COD)]-1

[0334] Referring to the synthesis and purification method of compound [Ir(La003)(COD)]-1, only the corresponding raw materials need to be changed to obtain compound [Ir(La029)(COD)]-1 (12.54 g, yield: 72.36%), mass spectrum: 751.24 (M+H)

[0335] Synthesis of Compound [Ir(La029)(Lc011)]-1

[0336] Referring to the synthesis and purification method of compound [Ir(La003)(Lc004)]-1, only the corresponding raw materials need to be changed to obtain a red solid compound [Ir(La029)(Lc011)]-1 (7.01 g, yield: 52.64%). The obtained compound was used directly in the next step without purification.

[0337] Synthesis of Compound Ir(La029)(Lb005)(Lc011)

[0338] Referring to the synthesis and purification method of compound Ir(La003)2(Lb005), only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La029)(Lb005)(Lc011) (2.33 g, purity: 99.89%, yield: 46.77%). 2.33 g of crude Ir(La029)(Lb005)(Lc011) was sublimated and purified to obtain sublimation pure Ir(La029)(Lb005)(Lc011) (1.40 g, purity: 99.87%, yield: 60.08%), mass spectrum: 1107.20 (M+H).

[0339] 1H NMR (400MHz, CDCl3) δ8.61(d,J=7.5Hz,1H),8.07(d,J=1.4Hz,1H),7.99-7.94(m,2H),7.88-7.86(m,3H ),7.67-7.64(m,1H),7.55-7.53(m,1H),7.48(dd,J=7.4,1.5Hz,1H),7.44(d,J=7.5Hz,1H),7.40-7.29 (m,3H),7.19(m,1H),6.92-6.89(m,2H),4.74(s,1H),2.91(d,J=7.5Hz,2H),2.48(d,J=7.2Hz,2H),2.3 4-2.31(m,10H),1.95-1.63(m,9H),1.36-1.22(m,10H),0.94(t,J=6.7Hz,12H),0.86(d,J=6.3Hz,6H).

[0340] Synthesis of Compound Ir(La076)(Lb005)(Lc023)

[0341]

[0342] Synthesis of Compound [Ir(La076)(COD)]-1

[0343] Referring to the synthesis and purification method of compound [Ir(La003)(COD)]-1, only the corresponding raw materials need to be changed to obtain compound [Ir(La076)(COD)]-1 (14.52 g, yield: 70.11%), mass spectrum: 663.22 (M+H)

[0344] Synthesis of Compound [Ir(La076)(Lc023)]-1

[0345] Referring to the synthesis and purification method of compound [Ir(La003)(Lc004)]-1, only the corresponding raw materials need to be changed to obtain a red solid compound [Ir(La076)(Lc023)]-1 (6.88 g, yield: 53.57%). The obtained compound was used directly in the next step without purification.

[0346] Synthesis of Compound Ir(La029)(Lb005)(Lc023)

[0347] Referring to the synthesis and purification method of compound Ir(La003)2(Lb005), only the corresponding raw materials need to be changed to obtain a red solid compound Ir(La029)(Lb005)(Lc023) (2.12 g, purity: 99.88%, yield: 48.44%). 2.12 g of crude Ir(La029)(Lb005)(Lc023) was sublimated and purified to obtain sublimation pure Ir(La029)(Lb005)(Lc023) (1.08 g, purity: 99.85%, yield: 50.94%), mass spectrum: 1081.28 (M+H).

[0348] 1 H NMR (400MHz, CDCl3) δ8.53 (d, J = 1.4Hz, 1H), δ8.23 (m, 1H), 7.98-7.77 (m, 2H), 7. 68(d,J=2.9Hz,1H),7.62-7.57(m,4H),7.51-7.31(m,5H),7.08(t,J=14.9Hz,1H ),6.99-6.92(m,2H),4.74(s,1H),3.09(s,2H),2.892-2.82(m,1H),2.34-2.31( s,9H),1.37-1.26(m,10H),1.24-1.19(m,6H),1.09-0.94(m,12H),0.85(s,9H).

[0349] Application example: Fabrication of organic electroluminescent devices

[0350] A 50mm*50mm*1.0mm glass substrate with an ITO (100nm) transparent electrode was ultrasonically cleaned in ethanol for 10 minutes, dried at 150 degrees, and then treated with N2Plasma for 30 minutes. The washed glass substrate was mounted on a substrate support of a vacuum evaporation device, and the compound HATCN was firstly evaporated on the surface of the transparent electrode line in a manner of covering the transparent electrode to form a film with a thickness of 5nm, followed by evaporation of a layer of HTM1 to form a film with a thickness of 60nm, and then a layer of HTM2 was evaporated on the HTM1 film to form a film with a thickness of 10nm, and then the main material and the doping compound (comparative compound X, the compound of the present invention) were evaporated on the HTM2 film layer in a co-evaporation mode, with a film thickness of 30nm, and the ratio of the main material to the doping material was 90%:10%. ETL film layer (25nm) and LiQ film layer (1nm) were then evaporated on the light-emitting layer in sequence, and finally a layer of metal Al (100nm) was evaporated as an electrode.

[0351]

[0352] evaluate:

[0353] The above device was subjected to device performance testing. In each embodiment and comparative example, a constant current power supply (Keithley 2400) was used to flow a fixed current density through the light-emitting element, and a spectroradiometer (CS 2000) was used to test the luminous spectrum. The voltage value and the time (LT90) when the test brightness reached 90% of the initial brightness were measured at the same time. The results are as follows:

[0354]

[0355]

[0356] From the data comparison in the above table, it can be seen that the organic electroluminescent device using the compound of the present invention as a dopant has a narrower emission spectrum and a higher color saturation than the comparative compound, and exhibits more superior performance in terms of driving voltage, luminous efficiency, and device life.

[0357] Sublimation temperature comparison: Sublimation temperature is defined as: at 10 -7 Torr vacuum degree, the temperature corresponding to the evaporation rate of 1 angstrom per second. The test results are as follows:

[0358]

[0359]

[0360] From the comparison of the data in the above table, it can be seen that the compound of the present invention has a lower sublimation temperature, which is conducive to industrial application.

[0361] The present invention unexpectedly provides better device luminous efficiency and improved lifespan through special matching of substituents, and unexpectedly provides a lower sublimation temperature compared to the prior art. The above results show that the compound of the present invention has the advantages of low sublimation temperature, high light and electrochemical stability, high color saturation, high luminous efficiency, long device life, etc., and can be used in organic electroluminescent devices. In particular, as a red light-emitting dopant, it has the possibility of being applied to the OLED industry.

[0362] The material of the present invention has the advantages of high optical and electrical stability, low sublimation temperature, narrow emission half-peak width, high color saturation, high luminous efficiency, long device life, etc. As a phosphorescent material, the material of the present invention can convert the triplet excited state into light, so it can improve the luminous efficiency of the organic electroluminescent device, thereby reducing energy consumption. In particular, as a red light-emitting dopant, it has the possibility of being applied to the AMOLED industry.

Claims

1. An organometallic iridium compound having the general formula of Ir(La)(Lb)(Lc), wherein La is a structure shown in formula (3), in, The dotted line indicates the location of connection with metal Ir; Among them, R1-R 10 are independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl; or wherein R7 and R8, R8 and R9, or R9 and R 10 are connected to each other to form a structure shown in formula (4), Where * indicates the location of the connection. Y1-Y4 are independently CR0 or N, Z1 is selected from O, S, R0 is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl; Among them, at least one of R1-R6 is not H, R7-R 10 At least one of them is not hydrogen; Where Lb is one of the following formulas Or it is the structure shown in formula (2), The dotted line position indicates the position connected to the metal Ir; wherein Ra-Rg are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl; Wherein, the heterocycloalkyl group contains at least one O, N or S heteroatom; Among them, Lc is a monoanionic bidentate ligand, Lc is different from Lb and is not an OO type ligand; Wherein, Lc and La are the same or different, and the difference is that the parent core structures are different, or the parent core structures are the same but the substituents are different, or the parent core structures are the same and the substituents are the same but the positions of the substituents are different; When Lc is different from La, Lc is one of the following formulas: Or it is the structure shown in formula (5), Wherein, the dotted line indicates the position connected with metal Ir; Among them, R 11 -R 18 are independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl; wherein R 15 -R 18 At least two of them are not hydrogen; or, R 11 -R 14 At least one set of two adjacent groups forms an aromatic ring structure as shown in the following formula (6); Wherein, the dotted line indicates the position of connection with the pyridine ring; Among them, R 19 -R 22 Independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl; Wherein, the substitution is substitution by deuterium, F, Cl, Br, C1-C4 alkyl, C3-C6 cycloalkyl, wherein the number of substitutions is from single substitution to the maximum number of substitutions.

2. The organometallic iridium compound according to claim 1, wherein in formula (3), R1 and / or R3 and / or R4 and / or R5 are not hydrogen.

3. The organometallic iridium compound according to claim 2, wherein in formula (3), R1, R3, R4, and R5 are independently selected from deuterium, halogen, substituted or unsubstituted C1-C10 alkyl, and substituted or unsubstituted C3-C20 cycloalkyl.

4. The organometallic iridium compound according to claim 3, wherein at least two of R1-R6 in the formula (3) are not H.

5. The organometallic iridium compound according to claim 4, wherein in formula (3), R2 and R6 are hydrogen.

6. The organometallic iridium compound according to claim 1, wherein in formula (3), R8 and / or R 10 Not hydrogen.

7. The organometallic iridium compound according to claim 6, wherein in formula (3), R8 and R 10 is not hydrogen, said R8, R 10 R7 and R9 are independently selected from deuterium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, and are hydrogen.

8. The organometallic iridium compound according to claim 1, wherein R7 and R8 are connected to each other to form a structure shown in formula (4), Where * indicates the location of the connection. Y1-Y4 are independently CR0, Z1 is selected from O.

9. The organometallic iridium compound according to any one of claims 1 to 8, wherein Lc is the same as La.

10. The organometallic iridium compound according to claim 1, wherein La is one of the following structural formulas, 11. The organometallic iridium compound according to claim 1, wherein Lb is one of the following structural formulas, 12. The organometallic iridium compound according to claim 1, wherein Lc is one of the following structural formulas, 13. Use of the organometallic iridium compound according to any one of claims 1 to 12 in an organic electroluminescent device.

14. The use according to claim 13, wherein the organometallic iridium compound is used as a red light-emitting doping material in a light-emitting layer of an organic electroluminescent device.

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