An organic metal iridium compound and its application

Abstract

The present invention relates to an organic metal iridium compound and its application. The organic metal iridium compound has a structure shown in formula (1). The compound provided by the present invention has the advantages of high light and electrochemical stability, 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 green light-emitting dopant, it has the possibility of being applied to the AMOLED industry. #imgabs0#

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 molecules, 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 organic metal iridium compounds as phosphorescent materials. For example, the invention patent CN1726606 discloses a class of aromatic benzimidazole iridium compounds, but the luminous efficiency of such compounds is far from meeting the market demand; Wen et al. published a non-patent document (Chem. Mater. 2004, 16, 2480-2488) in 2004, disclosing a class of benzimidazole-type metal iridium complexes with aromatic rings, which exhibits a certain luminous efficiency, but due to the large half-peak width of the material, the device life, especially T95, is very short, which is difficult to meet the market application and needs to be further improved; Patent document CN102272261 discloses a class of iridium compounds with sterically hindered aromatic substituted benzimidazoles connected to N, but the color saturation, emission spectrum half-width and device performance of such compounds, especially luminous efficiency and device life, need to be improved; Patent document CN103396455 discloses a class of substituted benzimidazole iridium compounds with alkyl groups connected to N, and similarly, such compounds also have problems such as poor color saturation, excessive emission spectrum half-width, insufficient device efficiency, and short device life, which need to be improved. Patent document CN103254238 discloses a class of iridium compounds with sterically hindered aromatic substituted benzimidazoles connected to dibenzoheterocycles on N, but such compounds also have problems such as excessive emission spectrum half-width, insufficient device efficiency, and short device life, which need to be improved. Patent document CN102898477 discloses The iridium compounds shown, however, also have problems such as large half-peak width of emission spectrum, insufficient device efficiency, and short device life that need to be improved. 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 a structure shown in formula (1). The iridium complex provided by the present invention has the advantages of good optical and electrical stability, narrow emission half-peak width, high luminous efficiency, long life, high color saturation, etc., and can be used in organic light-emitting devices, especially as a green light-emitting phosphorescent material, and has the possibility of being applied to the AMOLED industry.

[0007] An organic metal iridium compound, the structural formula of which is shown in formula (1):

[0008]

[0009] in, For L1, is L2;

[0010] Wherein, m is 1 or 2 or 3. When m is 1, two L2s are the same or different. When m is greater than 1, multiple L1s are the same or different.

[0011] The number of Ra, Rb, and Rc represents one from 1 to the maximum number of substitutions;

[0012] wherein Ra, Rb, Rc, Rd, and Re are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted tri-C1-C10 alkylsilyl, substituted or unsubstituted tri-C6-C12 arylsilyl, substituted or unsubstituted di-C1-C10 alkyl-C6-C30 arylsilyl;

[0013] wherein at least one of the Rd and Re is not hydrogen;

[0014] Wherein, R1-R8 are independently selected from hydrogen, deuterium, halogen, hydroxyl, thiol, 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, or two adjacent groups of R1-R8 can be connected to each other to form an alicyclic ring or an aromatic ring structure;

[0015] wherein the heteroalkyl and heteroaryl groups contain at least one O, N or S heteroatom;

[0016] Wherein, the substitution is substitution by deuterium, F, Cl, Br, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkyl substituted by amine, nitrile, isonitrile, phosphine, wherein the substitution is from single substitution to maximum number substitution.

[0017] Where m is 1 or 2, and the two L1s or the two L2s are the same.

[0018] As a preferred organometallic iridium compound, at least one of Rd and Re is not hydrogen, and at least one of Rd and Re is a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C3-C6 cycloalkyl group.

[0019] As a preferred organometallic iridium compound, Ra is hydrogen.

[0020] As a preferred organometallic iridium compound, at least one of R1 to R4 is not hydrogen.

[0021] As a preferred organometallic iridium compound, at least one of R5 to R8 is not hydrogen.

[0022] As a preferred organometallic iridium compound, at least one of R1 to R4 is not hydrogen and at least one of R5 to R8 is not hydrogen.

[0023] As a preferred organometallic iridium compound, one of R1-R4 is deuterium, deuterium substituted or unsubstituted C1-C5 alkyl, deuterium substituted or unsubstituted C3-C5 cycloalkyl, one of R5-R8 is deuterium, deuterium substituted or unsubstituted C1-C5 alkyl, deuterium substituted or unsubstituted C3-C5 cycloalkyl, and the rest are hydrogen.

[0024] As a preferred organometallic iridium compound, R5 and R6, R6 and R7, and R7 and R8 are interconnected to form a ring structure shown in formula (2):

[0025]

[0026] Where * indicates the location of the connection.

[0027] Y1-Y4 are independently CR0 or N,

[0028] Z1 is selected from O, S,

[0029] R0 is independently hydrogen, deuterium, F, 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;

[0030] The substitution is substituted by deuterium, F, Cl, Br, C1-C4 alkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C1-C4 alkyl substituted by amine, nitrile, isonitrile, phosphine.

[0031] As a preferred organometallic iridium compound, R4 and R5 are connected to each other to form an aliphatic ring structure shown in formula (3):

[0032]

[0033] Where * indicates the location of the connection.

[0034] Z2 and Z3 are independently selected from O, S, N(R0), C(R0)2, and at least one of Z2 and Z3 is C(R0)2;

[0035] R0 is independently hydrogen, deuterium, F, 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;

[0036] The substitution is substituted by deuterium, F, Cl, Br, C1-C4 alkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C1-C4 alkyl substituted by amine, nitrile, isonitrile, phosphine.

[0037] As a preferred organometallic iridium compound, at least one of Rb and Rc is not hydrogen.

[0038] As a preferred organometallic iridium compound, at least one of Rb and Rc is a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C3-C6 cycloalkyl group.

[0039] As a preferred organometallic iridium compound, one of Rb and Rc is a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C3-C6 cycloalkyl group, and the other is hydrogen.

[0040] As a preferred organometallic iridium compound, L1 is preferably one of the following structural formulas, or a corresponding partially or completely deuterated or fluorinated one,

[0041]

[0042]

[0043] As a preferred organometallic iridium compound, L2 is preferably one of the following structural formulas, or a corresponding partially or completely deuterated or fluorinated one,

[0044]

[0045]

[0046] As the preferred organometallic iridium compound, the formula (1) is preferably one of the following structural formulas or their corresponding partially or completely deuterated products or their corresponding partially or completely fluorinated products,

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062] Another object of the present invention is to provide an OLED phosphorescent material containing the above compound.

[0063] Another object of the present invention is to provide an OLED device containing the above compound.

[0064] The material of the present invention has the advantages of high optical and electrochemical stability, 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 green luminescent dopant, it has the possibility of being applied to the AMOLED industry. DETAILED DESCRIPTION

[0065] The compound of the present invention has a structural formula as shown in formula (1):

[0066]

[0067] in, For L1, is L2;

[0068] Wherein, m is 1 or 2 or 3. When m is 1, two L2s may be the same or different. When m is greater than 1, multiple L1s may be the same or different.

[0069] Where Ra, Rb, and Rc independently represent no substitution to the maximum possible substitution;

[0070] wherein Ra, Rb, Rc, Rd, and Re are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted tri-C1-C10 alkylsilyl, substituted or unsubstituted tri-C6-C12 arylsilyl, substituted or unsubstituted di-C1-C10 alkyl-C6-C30 arylsilyl;

[0071] wherein at least one of the Rd and Re is not hydrogen;

[0072] wherein R1-R8 are independently selected from hydrogen, deuterium, halogen, hydroxyl, thiol, 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;

[0073] Wherein, two adjacent groups of R1-R4 and R5-R8 can be connected to each other to form an alicyclic ring or an aromatic ring structure;

[0074] The heteroalkyl group is an alkyl group containing at least one heteroatom such as O, N, S, etc.

[0075] Wherein, the substitution is deuterium, F, Cl, Br, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkyl substituted amine, nitrile, isonitrile, phosphine, wherein the substitution is from mono-substitution to the maximum possible substitution.

[0076] In the formula (1), when there are two or more Ra, Rb or Rc, the plurality of Ra, Rb or Rc may be the same or different.

[0077] In formula (1), when there are two or more substituents, the multiple substituents may be the same or different. In formula (1), at least one of Rb and Rc is deuterium, fluorine, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C6 cycloalkyl, which means that Rb is selected from the above groups and Rc is not; Rc is selected from the above groups and Rb is not; Rb and Rc are selected from the above groups at the same time.

[0078] Hereinafter, examples of each group of the compound represented by formula (1) will be described.

[0079] 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.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] 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.

[0084] 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.

[0085] 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.

[0086] 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.

[0087] The raw materials and solvents involved in the synthesis of the compounds of the present invention were purchased from suppliers such as Alfa and Acros, which are well known to those skilled in the art.

[0088] Synthesis of common intermediate L1:

[0089]

[0090] Synthesis of compound L1-2:

[0091] Compound L1-1 (40.0 g, 0.28 mol, 1.0 eq), La001-2 (35.33 g, 0.33 mol, 1.20 eq), acetic acid (25 g, 0.42 mol, 1.5 eq) and toluene (200 ml) were added to a 500 ml three-necked flask, and the flask was evacuated and replaced with nitrogen three times. Under nitrogen protection, the mixture was stirred and refluxed at 110 ° C for 18 hours. TLC monitoring showed that the reaction of raw material L1-1 was complete. After cooling to room temperature, 120 ml of deionized water was added, the liquid was washed with water, the upper organic phase was collected and concentrated to remove the organic solvent, and the organic phase was separated by column chromatography after being spin-dried (the eluent was ethyl acetate: n-hexane = 1:20). After drying, an off-white solid was obtained to obtain compound L1-2 (40.73 g, yield: 63.2%). Mass spectrum: 233.28 (M+H).

[0092] Synthesis of compound L1-3:

[0093] In a 1L three-necked flask, add compound L1-2 (30g, 129.1mmol, 1.0eq), cuprous chloride (1.28g, 12.92mmol, 0.1eq), tert-butyl hydroperoxide (23.28g, 258.3mmol, 2.0eq), trifluoroethanol (300ml) in sequence, evacuate, replace with nitrogen 3 times, heat the oil bath to about 50°C, stir for 6h, take a sample and monitor the basic reaction of raw material La001-3 by TLC. Cool to room temperature, add deionized water to wash 3 times (150ml / time), separate the liquids, and concentrate the organic phase under reduced pressure to a solid. The crude product is separated by column chromatography (EA: Hex = 1:10), and the obtained product is dried to obtain an off-white solid compound L1-3 (19.3g, 60.8%). Mass spectrum: 247.2 (M+H).

[0094] Synthesis of compound L1:

[0095] In a 1L three-necked flask, compound L1-3 (15g, 60.91mmol, 1.0eq), dimethyl zinc (17.44g, 182.7mmol, 3.0eq), 1,2-dichloromethane (300ml) were added in sequence, vacuumed, replaced with nitrogen 3 times, the reaction system was cooled to -30°C, titanium tetrachloride (34.66g, 182.7mmol, 3.0eq) was slowly added dropwise, and the mixture was returned to room temperature and stirred for 2h after the addition was completed. Samples were taken by TLC to monitor that the raw material L1-3 was basically reacted. Deionized water (200ml) was slowly added to quench, and ethyl acetate (350ml) was added, the extraction was stirred and separated, and the organic phase was concentrated under reduced pressure to a solid. The crude product was separated by column chromatography (EA: Hex = 1:20), and the obtained product was dried to obtain an off-white solid compound L1 (12.18g, 76.8%). Mass spectrum: 261.3 (M+H).

[0096] Synthesis of compound CPD 1

[0097]

[0098] Synthesis of compound CPD 1-1

[0099] Compound L1 (27.0 g, 103.7 mmol, 3.0 eq) and IrCl3.3H2O (12.19 g, 34.57 mol, 1.0 eq) were placed in a 1L single-necked flask, and ethylene glycol ethyl ether (270 ml) and deionized water (90 ml) were added. The mixture was replaced by vacuum for 3 times. The mixture was stirred and refluxed at 110°C for 16 hours under the protection of N2. After cooling to room temperature, the mixture was filtered, and the residue was successively treated with methanol (100 ml*3) and n-hexane (100 ml*3) and dried to obtain compound CPD 1-1 (22.86 g, 88.6%). The obtained compound was used directly in the next step without purification.

[0100] Synthesis of compound CPD 1-2

[0101] Add dimer CPD 1-1 (20.0 g, 26.8 mmol, 1.0 eq) and dichloromethane (1.5 L) to a 3 L three-necked flask and stir to dissolve. Dissolve silver trifluoromethanesulfonate (13.77 g, 53.6 mmol, 2.0 eq) in methanol (1.2 L) and add it to the original reaction flask solution. Vacuum replace 3 times. The mixed solution is stirred at room temperature for 16 hours under N2 protection. Then filter the reaction solution through diatomaceous earth, rinse the filter residue with dichloromethane (150 ml), and spin dry the filtrate to obtain compound CPD 1-2 (13.69 g, 80.5%). The obtained compound is used directly in the next step without purification.

[0102] Synthesis of compound CPD 1

[0103] Compound CPD1-2 (7.5 g, 8.12 mmol, 1.0 eq) and L2 (2.52 g, 16.23 mmol, 2.0 eq) were added to a 250 ml three-necked flask, ethanol (75 ml) was added, vacuum replacement was performed 3 times, and stirring and refluxed for 16 hours under the protection of N2. After cooling to room temperature, the mixture was filtered, the solid was collected and dissolved with dichloromethane (150 ml), filtered on silica gel, and the filter cake was rinsed with dichloromethane (50 ml). After the filtrate was dried, it was separated by column chromatography (developing agent dichloromethane: n-hexane = 1:5) to obtain a crude product, which was then recrystallized from tetrahydrofuran / methanol twice (product: tetrahydrofuran: methanol = 1:5:5), and then slurried once with n-hexane (80 ml), and dried to obtain compound CPD 1 (4.62 g, 65.8%). 4.62 g of crude CPD 1 was purified by sublimation to obtain pure CPD1 (2.88 g, 62.33%). Mass spectrum: 866.06 (M+H). 1H NMR(400MHz, CDCl3)δ8.37(d,1H),8.16(d,1H),7.77(m,3H),7.56–7.34(m,9 H),7.22–7.02(m,5H),6.90(m,3H),6.50(d,2H),5.76(d,2H),1.75(s,12H).

[0104] Synthesis of compound CPD 6

[0105]

[0106] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 6 (5.11 g, 63.8%). 5.11 g of crude CPD 6 was purified by sublimation to obtain sublimation pure CPD 6 (3.24 g, 63.4%). Mass spectrum: 1026.27 (M+H). 1 H NMR(400MHz,DMSO)δ8.50(d,1H),7.98(d,1H),7.87–7.66(m,4H),7.58–7.27(m,9H), 7.22–7.01(m,6H),6.52(m,4H),5.76(m,2H),3.21(s,2H),1.75(s,12H),0.85(s,9H).

[0107] Synthesis of compound CPD 12

[0108]

[0109] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 12 (3.66 g, 48.3%). 3.66 g of crude CPD 12 was purified by sublimation to obtain sublimation pure CPD 12 (2.12 g, 65.43%). Mass spectrum: 1046.31 (M+H). 1 H NMR (400MHz, DMSO) δ8.49(d,J=5.0Hz,2H),7.88–7.66(m,4H),7.46(m,9H),7.21–6.98(m,6H),6.61(d,2H),5.76(s,2H),1.76(s,12H),1.01(s,9H).

[0110] Synthesis of common intermediate L5:

[0111]

[0112] Synthesis of compound L5-2:

[0113] Referring to the synthesis and purification method of compound L1-2, only the corresponding raw materials need to be changed to obtain the target compound L5-2 (16.3 g, 63.5%). Mass spectrum: 247.3 (M+H).

[0114] Synthesis of compound L5-3:

[0115] Referring to the synthesis and purification method of compound L1-3, only the corresponding raw materials need to be changed to obtain the target compound L5-3 (11.8 g, 53.8%). Mass spectrum: 261.2 (M+H).

[0116] Synthesis of compound L5:

[0117] Referring to the synthesis and purification method of compound L1, only the corresponding raw materials need to be changed to obtain the target compound L5 (9.8 g, 67.9%). Mass spectrum: 275.3 (M+H).

[0118] Synthesis of compound CPD 19

[0119]

[0120] Synthesis of compound CPD 19-1:

[0121] Referring to the synthesis and purification method of compound CPD 1-1, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0122] Synthesis of compound CPD 19-2:

[0123] Referring to the synthesis and purification method of compound CPD 1-2, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0124] Synthesis of compound CPD 19:

[0125] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 19 (3.77 g, 56.8%). 3.77 g of crude CPD 19 was purified by sublimation to obtain sublimation pure CPD 19 (2.45 g, 64.98%). Mass spectrum: 1052.3 (M+H). 1H NMR (400MHz, CDCl3) δ8.52(d,1H),7.98(d,1H),7.87–7.66(m,6H),7.58–7.27(m,9H),7.17(d,3H) ),7.06(d,J=10.0Hz,3H),5.54(s,2H),2.97(m,1H),1.99(d,J=23.0Hz,8H),1.85–1.58(m,18H).

[0126] Synthesis of common intermediate L8:

[0127]

[0128] Synthesis of compound L8-2:

[0129] In a 500ml three-necked flask, compound L8-1 (22g, 98.62mmol, 1.0eq), isopropylboric acid (10.4g, 118.35mmol, 1.2eq), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (II) (1.4g, 1.97mmol, 0.02eq), K3PO4 (41.87g, 197.25mmol, 2.0eq), toluene (220ml) were added in sequence, vacuumed, replaced with nitrogen 3 times, heated in an oil bath to about 70°C, stirred for 16h, and sampled by TLC to monitor that the raw material L8-1 was basically reacted. Cooled to room temperature, washed with deionized water 3 times (120ml / time), separated, and the organic phase was concentrated under reduced pressure to a solid. The crude product was separated by column chromatography (EA:Hex=1:20), and the obtained product was dried to obtain an off-white solid compound L8-2 (14.83 g, 78.3%). Mass spectrum: 187.25 (M+H).

[0130] Synthesis of compound L8-3:

[0131] Referring to the synthesis and purification method of compound L1-2, only the corresponding raw materials need to be changed to obtain the target compound L8-3 (17.1 g, 57.7%). Mass spectrum: 275.3 (M+H).

[0132] Synthesis of compound L8-4:

[0133] Referring to the synthesis and purification method of compound L1-3, only the corresponding raw materials need to be changed to obtain the target compound L8-4 (13.4 g, 50.7%). Mass spectrum: 289.3 (M+H).

[0134] Synthesis of compound L8:

[0135] Referring to the synthesis and purification method of compound L1, only the corresponding raw materials need to be changed to obtain the target compound L8 (8.7 g, 63.9%). Mass spectrum: 303.4 (M+H).

[0136] Synthesis of compound CPD 34

[0137]

[0138] Synthesis of compound CPD 34-1:

[0139] Referring to the synthesis and purification method of compound CPD 1-1, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0140] Synthesis of compound CPD 34-2:

[0141] Referring to the synthesis and purification method of compound CPD 1-2, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0142] Synthesis of compound CPD 34:

[0143] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 34 (3.05 g, 47.6%). 3.05 g of crude CPD 34 was purified by sublimation to obtain sublimation pure CPD 34 (1.87 g, 61.31%). Mass spectrum: 1025.44 (M+H). 1 H NMR(400MHz, CDCl3) δ8.47(d,J=26.0Hz,2H),7.87–7.66(m,4H),7.46(d,J=40.0Hz,6H),7.22–6.97 (m,9H),5.54(s,2H),3.21(s,2H),2.94(m,2H),2.68(s,3H),1.74(s,12H),0.94(d,J=95.0Hz,21H).

[0144] Synthesis of common intermediate L10:

[0145]

[0146] Synthesis of compound L10-2:

[0147] Referring to the synthesis and purification method of compound L1-2, only the corresponding raw materials need to be changed to obtain the target compound L10-2 (13.7 g, 69.4%). Mass spectrum: 247.3 (M+H).

[0148] Synthesis of compound L10-3:

[0149] Referring to the synthesis and purification method of compound L1-3, only the corresponding raw materials need to be changed to obtain the target compound L10-3 (10.7 g, 65.2%). Mass spectrum: 261.2 (M+H).

[0150] Synthesis of compound L10:

[0151] Referring to the synthesis and purification method of compound L1, only the corresponding raw materials need to be changed to obtain the target compound L10 (8.64 g, 63.9%). Mass spectrum: 275.3 (M+H).

[0152] Synthesis of compound CPD 50

[0153]

[0154] Synthesis of compound CPD 50-1:

[0155] Referring to the synthesis and purification method of compound CPD 1-1, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0156] Synthesis of compound CPD 50-2:

[0157] Referring to the synthesis and purification method of compound CPD 1-2, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0158] Synthesis of compound CPD 50:

[0159] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 50 (3.52 g, 50.9%). 3.52 g of crude CPD 50 was purified by sublimation to obtain sublimation pure CPD 50 (2.23 g, 63.35%). Mass spectrum: 908.13 (M+H). 1 H NMR(400MHz, CDCl3)δ8.46(m,1H),8.21(m,2H),7.78–7.44(m,9H),7.02(m,6H) ,6.59(d,J=22.3Hz,3H),5.92(s,2H),2.76(s,3H),2.22(s,6H),1.74(s,12H).

[0160] Synthesis of common intermediate L12:

[0161]

[0162] Synthesis of compound L12-2:

[0163] Referring to the synthesis and purification method of compound L8-2, only the corresponding raw materials need to be changed to obtain the target compound L12-2 (15.6 g, 63.7%). Mass spectrum: 213.3 (M+H).

[0164] Synthesis of compound L12-3:

[0165] Referring to the synthesis and purification method of compound L1-2, only the corresponding raw materials need to be changed to obtain the target compound L12-3 (12.4 g, 52.3%). Mass spectrum: 301.4 (M+H).

[0166] Synthesis of compound L12-4:

[0167] Referring to the synthesis and purification method of compound L1-3, only the corresponding raw materials need to be changed to obtain the target compound L12-4 (11.3 g, 61.7%). Mass spectrum: 315.3 (M+H).

[0168] Synthesis of compound L12:

[0169] Referring to the synthesis and purification method of compound L1, only the corresponding raw materials need to be changed to obtain the target compound L12 (7.9 g, 56.4%). Mass spectrum: 329.4 (M+H).

[0170] Synthesis of compound CPD 78

[0171]

[0172] Synthesis of compound CPD 78-1:

[0173] Referring to the synthesis and purification method of compound CPD 1-1, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0174] Synthesis of compound CPD 78-2:

[0175] Referring to the synthesis and purification method of compound CPD 1-2, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0176] Synthesis of compound CPD 78:

[0177] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 78 (3.31 g, 51.3%). 3.31 g of crude CPD 78 was purified by sublimation to obtain sublimation pure CPD 78 (1.87 g, 56.49%). Mass spectrum: 1162.5 (M+H). 1 H NMR(400MHz, CDCl3)δ8.53(d,1H),7.98(d,1H),7.88–7.60(m,6H),7.58–7.24(m,7H),7.05(m,6H), 6.56(d,2H),5.92(d,2H),3.21(s,2H),3.09(m,2H),2.00(m,4H),1.86–1.54(m,24H),0.85(s,9H).

[0178] Synthesis of common intermediate L13:

[0179]

[0180] Synthesis of compound L13-2:

[0181] Referring to the synthesis and purification method of compound L8-2, only the corresponding raw materials need to be changed to obtain the target compound L13-2 (16.9 g, 53.7%). Mass spectrum: 187.2 (M+H).

[0182] Synthesis of compound L13-3:

[0183] Referring to the synthesis and purification method of compound L1-2, only the corresponding raw materials need to be changed to obtain the target compound L13-3 (14.7 g, 57.2%). Mass spectrum: 275.3 (M+H).

[0184] Synthesis of compound L13-4:

[0185] Referring to the synthesis and purification method of compound L1-3, only the corresponding raw materials need to be changed to obtain the target compound L13-4 (12.6 g, 58.1%). Mass spectrum: 289.3 (M+H).

[0186] Synthesis of compound L13:

[0187] Referring to the synthesis and purification method of compound L1, only the corresponding raw materials need to be changed to obtain the target compound L13 (10.2 g, 55.4%). Mass spectrum: 303.4 (M+H).

[0188] Synthesis of compound CPD 107:

[0189]

[0190] Synthesis of compound CPD 107-1:

[0191] Referring to the synthesis and purification method of compound CPD 1-1, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0192] Synthesis of compound CPD 107-2:

[0193] Referring to the synthesis and purification method of compound CPD 1-2, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0194] Synthesis of compound CPD 107:

[0195] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 107 (2.88 g, 46.3%). 2.88 g of crude CPD 107 was purified by sublimation to obtain sublimation-purified CPD 107 (1.46 g, 50.69%). Mass spectrum: 1123.4 (M+H). 1 H NMR(400MHz, CDCl3)δ8.52(d,1H),8.31(d,1H),7.87–7.64(m,4H),7.46(d,J=40.0Hz,6H),7.25–6.96(m, 9H),6.85(m,2H),2.68(s,3H),2.49(m,1H),2.30(m,2H),2.02(m,2H),1.87–1.59(m,18H),1.04(d,12H).

[0196] Synthesis of common intermediate L15:

[0197]

[0198] Synthesis of compound L15-2:

[0199] Referring to the synthesis and purification method of compound L1-2, only the corresponding raw materials need to be changed to obtain the target compound L15-2 (14.8 g, 66.3%). Mass spectrum: 247.3 (M+H).

[0200] Synthesis of compound L15-3:

[0201] Referring to the synthesis and purification method of compound L1-3, only the corresponding raw materials need to be changed to obtain the target compound L15-3 (13.1 g, 70.2%). Mass spectrum: 261.2 (M+H).

[0202] Synthesis of compound L15:

[0203] Referring to the synthesis and purification method of compound L1, only the corresponding raw materials need to be changed to obtain the target compound L15 (9.3 g, 67.3%). Mass spectrum: 275.3 (M+H).

[0204] Synthesis of compound CPD 136:

[0205]

[0206] Synthesis of compound CPD 136-1:

[0207] Referring to the synthesis and purification method of compound CPD 1-1, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0208] Synthesis of compound CPD 136-2:

[0209] Referring to the synthesis and purification method of compound CPD 1-2, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0210] Synthesis of compound CPD 136:

[0211] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 136 (3.31 g, 52.3%). 3.31 g of crude CPD 136 was purified by sublimation to obtain sublimation-purified CPD 136 (1.94 g, 58.61%). Mass spectrum: 984.1 (M+H). 1 H NMR(400MHz, CDCl3)δ8.37(d,1H),7.98(d,1H),7.73(d,J=40.0Hz,3H),7.63–7.26(m, 10H),7.16(m,6H),6.90(d,1H),6.54(d,2H),5.76(s,2H),2.31(s,6H),1.74(s,12H).

[0212] Synthesis of common intermediate L17:

[0213]

[0214] Synthesis of compound L17-2:

[0215] Referring to the synthesis and purification method of compound L8-2, only the corresponding raw materials need to be changed to obtain the target compound L17-2 (16.9 g, 53.7%). Mass spectrum: 187.2 (M+H).

[0216] Synthesis of compound L17-3:

[0217] Referring to the synthesis and purification method of compound L1-2, only the corresponding raw materials need to be changed to obtain the target compound L17-3 (14.7 g, 57.2%). Mass spectrum: 275.3 (M+H).

[0218] Synthesis of compound L17-4:

[0219] Referring to the synthesis and purification method of compound L1-3, only the corresponding raw materials need to be changed to obtain the target compound L17-4 (12.6 g, 58.1%). Mass spectrum: 289.3 (M+H).

[0220] Synthesis of compound L17:

[0221] Referring to the synthesis and purification method of compound L1, only the corresponding raw materials need to be changed to obtain the target compound L17 (10.2 g, 55.4%). Mass spectrum: 303.4 (M+H).

[0222] Synthesis of compound CPD 150:

[0223]

[0224] Synthesis of compound CPD 150-1:

[0225] Referring to the synthesis and purification method of compound CPD 1-1, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0226] Synthesis of compound CPD 150-2:

[0227] Referring to the synthesis and purification method of compound CPD 1-2, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0228] Synthesis of compound CPD 150:

[0229] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 150 (3.02 g, 53.1%). 3.02 g of crude CPD 150 was purified by sublimation to obtain sublimation pure CPD 150 (1.68 g, 55.6%). Mass spectrum: 1110.43 (M+H). 1H NMR(400MHz, CDCl3)δ8.50(d,1H),7.98(d,1H),7.88–7.66(m,7H),7.59–7.25(m,11H),7.05(d,1 H),6.56(d,2H),5.76(d,2H),3.21(s,2H),2.87(m,2H),1.74(s,12H),1.20(d,12H),0.85(s,9H).

[0230] Synthesis of common intermediate L18:

[0231]

[0232] Synthesis of compound L18-1:

[0233] Referring to the synthesis and purification method of compound L8-2, only the corresponding raw materials need to be changed to obtain the target compound L18-1 (15.4 g, 58.9%). Mass spectrum: 213.2 (M+H).

[0234] Synthesis of compound L18-2:

[0235] Referring to the synthesis and purification method of compound L1-2, only the corresponding raw materials need to be changed to obtain the target compound L18-2 (14.6 g, 60.7%). Mass spectrum: 301.4 (M+H).

[0236] Synthesis of compound L18-3:

[0237] Referring to the synthesis and purification method of compound L1-3, only the corresponding raw materials need to be changed to obtain the target compound L18-3 (11.3 g, 53.8%). Mass spectrum: 315.3 (M+H).

[0238] Synthesis of compound L18:

[0239] Referring to the synthesis and purification method of compound L1, only the corresponding raw materials need to be changed to obtain the target compound L18 (8.9 g, 62.1%). Mass spectrum: 329.4 (M+H).

[0240] Synthesis of compound CPD 171:

[0241]

[0242] Synthesis of compound CPD 171-1:

[0243] Referring to the synthesis and purification method of compound CPD 1-1, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0244] Synthesis of compound CPD 171-2:

[0245] Referring to the synthesis and purification method of compound CPD 1-2, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0246] Synthesis of compound CPD 171:

[0247] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 171 (2.65 g, 43.8%). 2.65 g of crude CPD 171 was purified by sublimation to obtain sublimation-purified CPD 171 (1.44 g, 54.3%). Mass spectrum: 1028.3 (M+H) 1 H NMR (400MHz, CDCl3) δ8.35(d,1H),7.77(m,3H),7.46(d,J=40.0Hz,7H),7.36–7.03(m,6H),6. 67(m,3H),5.54(s,2H),2.97(d,J=20.0Hz,4H),2.80(m,2H),1.87–1.44(m,24H),1.30(m,4H).

[0248] Synthesis of compound CPD 195:

[0249]

[0250] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 195 (2.73 g, 47.9%). 2.73 g of crude CPD 195 was purified by sublimation to obtain sublimation-purified CPD 195 (1.48 g, 54.2%). Mass spectrum: 1084.4 (M+H) 1 H NMR(400MHz, CDCl3)δ8.55(d,1H),7.77(d,2H),7.61–7.25(m,9H),7.12(m,7 H),6.67(t,1H),5.54(s,2H),2.42(m,2H),1.92–1.43(m,24H),1.32(m,16H).

[0251] Synthesis of compound CPD 198:

[0252]

[0253] Synthesis of compound CPD 198-1:

[0254] Referring to the synthesis and purification method of compound CPD 1-1, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0255] Synthesis of compound CPD 198-2:

[0256] Referring to the synthesis and purification method of compound CPD 1-2, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0257] Synthesis of compound CPD 198:

[0258] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 198 (2.53 g, 40.7%). 2.53 g of crude CPD 198 was purified by sublimation to obtain sublimation pure CPD 198 (1.21 g, 48.7%). Mass spectrum: 1026.3 (M+H) 1 H NMR(400MHz, CDCl3)δ8.50(d,1H),7.98(d,1H),7.87–7.66(m,6H),7.59–7.27(m,9H), 7.22–7.00(m,6H),6.53(d,2H),5.76(d,2H),3.21(s,2H),1.74(s,12H),0.85(s,9H).

[0259] Synthesis of compound CPD 244:

[0260]

[0261] Synthesis of compound CPD 244-1:

[0262] Referring to the synthesis and purification method of compound CPD 1-1, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0263] Synthesis of compound CPD 244-2:

[0264] Referring to the synthesis and purification method of compound CPD 1-2, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0265] Synthesis of compound CPD 244:

[0266] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 244 (2.61 g, 46.1%). 2.61 g of crude CPD 244 was purified by sublimation to obtain sublimation-pure CPD 244 (1.55 g, 59.3%). Mass spectrum: 1108.4 (M+H) 1 H NMR (400MHz, CDCl3) δ8.54(d,1H),7.98(d,1H),7.87–7.65(m,4H),7.58–7.26(m,11H),7.05( m,4H),6.51(d,2H),5.76(d,2H),2.85(m,3H),2.03(m,2H),1.85–1.59(m,18H),1.20(s,12H).

[0267] Synthesis of common intermediate L21:

[0268]

[0269] Synthesis of compound L21:

[0270] Referring to the synthesis and purification method of compound L1-2, only the corresponding raw materials need to be changed to obtain the target compound L21 (15.3 g, 65.7%). Mass spectrum: 247.3 (M+H).

[0271] Synthesis of compound CPD 324:

[0272]

[0273] Synthesis of compound CPD 324-1:

[0274] Referring to the synthesis and purification method of compound CPD 1-1, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0275] Synthesis of compound CPD 324-2:

[0276] Referring to the synthesis and purification method of compound CPD 1-2, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0277] Synthesis of compound CPD 324:

[0278] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 324 (2.66 g, 45.9%). 2.66 g of crude CPD 324 was purified by sublimation to obtain sublimation-pure CPD 324 (1.27 g, 47.7%). Mass spectrum: 998.2 (M+H) 1 H NMR (400MHz, CDCl3) δ8.52(d,1H),7.98(d,1H),7.89–7.66(m,6H),7.60–7.26(m,9H),7.25– 7.00(m,6H),6.55(d,2H),5.76(q,2H),5.58(dt,2H),3.21(s,2H),1.72(d,6H),0.85(s,9H).

[0279] Synthesis of common intermediate L22:

[0280]

[0281] Synthesis of compound L22-2:

[0282] Referring to the synthesis and purification method of compound L8-2, only the corresponding raw materials need to be changed to obtain the target compound L22-2 (12.2 g, 62.7%). Mass spectrum: 227.3 (M+H).

[0283] Synthesis of compound L22:

[0284] Referring to the synthesis and purification method of compound L1-2, only the corresponding raw materials need to be changed to obtain the target compound L22 (8.5 g, 48.6%). Mass spectrum: 315.4 (M+H).

[0285] Synthesis of compound CPD 337:

[0286]

[0287] Synthesis of compound CPD 337-1:

[0288] Referring to the synthesis and purification method of compound CPD 1-1, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0289] Synthesis of compound CPD 337-2:

[0290] Referring to the synthesis and purification method of compound CPD 1-2, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0291] Synthesis of compound CPD 337:

[0292] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 337 (3.22 g, 46.1%). 3.22 g of crude CPD 337 was purified by sublimation to obtain sublimation-purified CPD 337 (1.37 g, 42.5%). Mass spectrum: 1079.3 (M+H). 1 H NMR(400MHz, CDCl3)δ8.49(d,1H),8.23(d,1H),7.73(dd,J=40.0Hz,3H),7.56–7.30(m,9H),7.2 5–6.85(m,8H),5.91(m,2H),5.54(d,2H),2.68(s,3H),2.55(dt,2H),1.64(m,18H),1.30(m,4H).

[0293] Synthesis of common intermediate L24:

[0294]

[0295] Synthesis of compound L24:

[0296] Referring to the synthesis and purification method of compound L1-2, only the corresponding raw materials need to be changed to obtain the target compound L24 (14.2 g, 52.8%). Mass spectrum: 261.3 (M+H).

[0297] Synthesis of compound CPD 348:

[0298]

[0299] Synthesis of compound CPD 348-1:

[0300] Referring to the synthesis and purification method of compound CPD 1-1, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0301] Synthesis of compound CPD 348-2:

[0302] Referring to the synthesis and purification method of compound CPD 1-2, only the corresponding raw materials need to be changed, and the obtained compound is directly used in the next step without purification.

[0303] Synthesis of compound CPD 348:

[0304] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 348 (2.66 g, 43.7%). 2.66 g of crude CPD 348 was purified by sublimation to obtain sublimation-purified CPD 348 (1.38 g, 51.8%). Mass spectrum: 1026.2 (M+H). 1 H NMR(400MHz, CDCl3)δ8.55(d,1H),7.98(dd,1H),7.88–7.65(m,7H),7.59–7.25(m,9H),7.18(d,2H),7. 05(dd,1H),6.49(d,2H),5.76(m,2H),5.49(m,2H),3.21(s,2H),2.31(s,6H),1.67(d,6H),0.85(s,9H).

[0305] Synthesis of compound CPD 360:

[0306]

[0307] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 360 (2.59 g, 43.7%). 2.59 g of crude CPD 360 was purified by sublimation to obtain sublimation-purified CPD 360 (1.41 g, 54.4%). Mass spectrum: 1000.2 (M+H). 1 H NMR(400MHz, CDCl3)δ8.45(d,1H),7.77(d,2H),7.46(m,7H),7.34–7.02(m,8H),6.67(t,2 H),5.53(m,4H),2.97(m,4H),2.60(m,2H),1.85–1.60(m,14H),1.55(m,4H),1.30(m,4H).

[0308] Synthesis of compound CPD 381:

[0309]

[0310] Referring to the synthesis and purification method of compound CPD 1, only the corresponding raw materials need to be changed to obtain the target compound CPD 381 (2.33 g, 40.2%). 2.33 g of crude CPD 381 was purified by sublimation to obtain sublimation-purified CPD 381 (1.12 g, 48.0%). Mass spectrum: 1071.3 (M+H). 1H NMR(400MHz, CDCl3)δ8.53(dd,1H),8.21(dd,2H),7.76(m,8H),7.42(m,4H),7.20(m,5H),6.3 5(dt,2H),5.54(dd,2H),4.15(m,1H),2.58(m,2H),1.67(m,18H),1.33(m,10H),1.17(d,6H).

[0311] By selecting the corresponding materials, similar methods can be used to synthesize and sublimate other compounds.

[0312] Application example: Fabrication of organic electroluminescent devices

[0313] 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 N2 Plasma 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 1 and the main material 2 and the doping compound (comparative compound X, CPD X) 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 45%:45%:10%. ETL:EIL was then evaporated on the light-emitting layer in sequence, with a film thickness of 35nm, and the ratio of ETL to EIL was 50%:50%. Finally, a layer of metal Al (100 nm) was evaporated as an electrode.

[0314]

[0315] Evaluation: The above device was subjected to device performance test. 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 (LT95) when the test brightness reached 95% of the initial brightness were measured at the same time. The results are as follows:

[0316]

[0317] 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 shows more superior performance in terms of driving voltage, luminous efficiency and device life compared with the comparative compound.

[0318] The above results show that the compounds of the present invention have the advantages of high light and electrochemical stability, 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 green light-emitting dopant, it has the potential to be applied to the OLED industry.

Claims

1. An organic metal iridium compound, the structural formula of which is shown in formula (1): in, For L1, is L2; Wherein, m is 1 or 2 or 3. When m is 1, two L2s are the same or different. When m is greater than 1, multiple L1s are the same or different. The number of Ra, Rb, and Rc represents one from 1 to the maximum number of substitutions; Wherein Ra, Rb, and Rc are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C10 alkyl, and substituted or unsubstituted C3-C20 cycloalkyl; Rd and Re are independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl; wherein at least one of the Rd and Re is not hydrogen; Wherein, R1-R8 are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl; or wherein R5 and R6, R6 and R7, R7 and R8 are connected to each other to form a ring structure shown in formula (2): Where * indicates the location of the connection. Y1-Y4 are independently CR0 or N, Z1 is selected from O, S, Or R4 and R5 are connected to each other to form an aliphatic ring structure shown in formula (3): Where * indicates the location of the connection. Z2 and Z3 are independently selected from N(R0) and C(R0)2, and at least one of Z2 and Z3 is C(R0)2; R0 is independently hydrogen, deuterium, F, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C20 cycloalkyl; wherein the substitution is substitution by deuterium, F, Cl, Br, C1-C6 alkyl, cyano, isocyano, wherein the substitution is single substitution to the maximum number of substitutions.

2. The organometallic iridium compound according to claim 1, wherein m is 1 or 2, and two L1s or two L2s are the same.

3. The organometallic iridium compound according to claim 2, wherein at least one of Rd and Re is not hydrogen, and at least one of Rd and Re is a substituted or unsubstituted C1-C6 alkyl group. The organometallic iridium compound according to claim 3 , wherein Ra is hydrogen.

5. The organometallic iridium compound according to claim 3, wherein at least one of R1 to R4 is not hydrogen.

6. The organometallic iridium compound according to claim 3, wherein at least one of R5-R8 is not hydrogen.

7. The organometallic iridium compound according to claim 3, wherein at least one of R1-R4 is not hydrogen and at least one of R5-R8 is not hydrogen.

8. The organometallic iridium compound according to claim 7, wherein one of R1-R4 is deuterium, deuterium-substituted or unsubstituted C1-C5 alkyl, or deuterium-substituted or unsubstituted C3-C5 cycloalkyl, one of R5-R8 is deuterium, deuterium-substituted or unsubstituted C1-C5 alkyl, or deuterium-substituted or unsubstituted C3-C5 cycloalkyl, and the rest are hydrogen.

9. The organometallic iridium compound according to any one of claims 1 to 8, wherein at least one of Rb and Rc is not hydrogen.

10. The organometallic iridium compound according to claim 9, wherein at least one of Rb and Rc is a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C3-C6 cycloalkyl group.

11. The organometallic iridium compound according to claim 10, wherein one of Rb and Rc is a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C3-C6 cycloalkyl group, and the other is hydrogen.

12. The organometallic iridium compound according to claim 3, wherein L1 is one of the following structural formulas, 13. The organometallic iridium compound according to claim 3, wherein L2 is one of the following structural formulas, 14. The organometallic iridium compound according to claim 1, wherein formula (1) is one of the following structural formulas, 15. Use of the organometallic iridium compound according to any one of claims 1 to 14 in an organic electroluminescent device.

16. The use according to claim 15, wherein the organometallic iridium compound is used as a green light-emitting doping material in a light-emitting layer of an organic electroluminescent device.

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