CN105820190B - Application of the feux rouges to near-infrared phosphorescent iridium complex luminescent material and its in electroluminescent device - Google Patents

Application of the feux rouges to near-infrared phosphorescent iridium complex luminescent material and its in electroluminescent device Download PDF

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CN105820190B
CN105820190B CN201610178409.1A CN201610178409A CN105820190B CN 105820190 B CN105820190 B CN 105820190B CN 201610178409 A CN201610178409 A CN 201610178409A CN 105820190 B CN105820190 B CN 105820190B
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CN105820190A (en
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王悦
刘宇
叶开其
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Jilin University
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    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0033—Iridium compounds
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd

Abstract

A kind of application of feux rouges to near-infrared phosphorescent iridium complex luminescent material and its in organic electroluminescence device, belong to technical field of organic electroluminescence, more particularly to the dark red light that the first ligand is 1- phenyl isoquinolins oxazoline derivates, assistant ligand is guanyl guanidine base class derivative to near-infrared iridium complex phosphorescence luminescent material, compound formula is as follows.More than one feux rouges are doped in the luminescent layer that organic electroluminescence device is constituted in material of main part to near-infrared phosphorescent iridium complex luminescent material as phosphorescent guest.The compounds of this invention has many advantages, such as that preparation process is simple, and manufactured electroluminescent device is efficient, long lifespan.Above-mentioned device can be used for the application fields such as FPD, illumination and light source.

Description

Feux rouges is to near-infrared phosphorescent iridium complex luminescent material and its in electroluminescent device Application
Technical field
The invention belongs to technical field of organic electroluminescence, and in particular to the first ligand derives for 1- phenyl isoquinolin quinoline classes Object, the feux rouges that assistant ligand is guanyl guanidine base class derivative are to near-infrared phosphorescent iridium complex luminescent material and its in organic electroluminescence Application in luminescent device.
Background technology
Pope et al. reports organic electroluminescent phenomenon earliest in earlier 1960s, they are in anthracene single crystal two Side observed the blue light that anthracene is sent out when applying the high pressure of four hectovolts.But since monocrystalline is difficult to grow, device drive voltage is very High (400~2000V), technique is almost without practical use used by them.Until 1987, U.S.'s Kodak Company C.W.Tang et al. uses ultra-thin membrane technology using the preferable aromatic amine of hole transport effect as hole transmission layer, with 8- hydroxyl quinolines The aluminum complex of quinoline is prepared for as luminescent layer using tin indium oxide (ITO) film and metal alloy as anode and cathode Luminescent device.The device has obtained brightness under 10V driving voltages and has been up to 1000cd/m2Green emission, the efficiency of device is 1.5lm/W (see C.W.TangandS.A.VanSlyke, Appl.Phys.Lett., 1987,51,913).This breakthrough So that organic electroluminescent research is able to worldwide in depth have developed rapidly.
Forrest of Princeton university in 1998 et al. is the study found that using general organic material or using glimmering Photoinitiator dye doping techniques prepare organic luminescent device, when electrons and holes meet in luminescent layer and it is compound when will produce Raw singlet excitons (singlet exciton) or triplet exciton (triplet exciton), count according to electron spin The probability that theoretical viewpoint, singlet excitons and three kinds of triplet excitons generate is identical, therefore singlet excitons formation is several Rate only has 25%, and fluorescence luminescent material is sent out exactly using the energy of this part singlet excited come luminous using fluorescence Theoretically its maximum internal quantum efficiency only has 25% to device prepared by luminescent material.The electron transition of triplet excited state under normal circumstances It returns ground state (singlet state) to prohibit and last a long time, often be decayed with non-radiative processes, but containing heavy metal original In the complex of son, since the presence of heavy atom can promote strong Quantum geometrical phase (spin-orbital Coupling) (4 powers for being proportional to the atomic number of heavy atom), this strong free coupling can make the spoke of triplet excited state Decay is penetrated to allow.Based on the above theory, phosphor material is developed and used in organic electroluminescent.They are by phosphorus Photoinitiator dye octaethylporphyrin platinum (PtOEP) is doped in main body luminescent material, and it is 4% to prepare external quantum efficiency, interior quantum effect Luminescent device of the rate up to 23%, to open the frontier of electrophosphorescence (see M.A.Baldo, D.F.O' Brienetal., Nature, 1998,395,151).
In the latest 20 years, application of the phosphorescent light-emitting materials in organic electroluminescent receives academia and widely pays close attention to, Relevant phosphorescent compound is contained with planar structure, d8Pt (II), Pd (II), Au (III) complex of electron configuration, with And with octahedral structure, d6The complexs such as the Ru (II) of electron configuration, Rh (III), Re (I), Ir (III), Os (II).Wherein Study it is more be osmium, iridium, platinum and ruthenium complex, they have preferable luminous efficiency, and partly decline with shorter phosphorescence Phase, to greatly reduce the probability that non-radiative mode fails.In order to find the gold that can improve OLED luminous efficiencies being more suitable for Metal complex, people go deep into the stable state and transient state photophy-sical behavior of systematic research Different Complex, for example, for improving device The mixing of singlet state and triplet MLCT (metal to ligand charge transfer) that efficiency plays an important role is asked The research of topic, and triplet phosphor material is used to be sensitized shining for singlet state dyestuff etc. as sensitizer.Metal iridium complex has There are shorter phosphorescent lifetime, efficient phosphorescent emissions, and its regular octahedron structure will not be as the planar structure one of platinum complex Sample forms intermolecular stacking and influences photophysical property, therefore receives favor.
Application of the new material in organic electroluminescence device is that electroluminescent technology is pushed to be constantly progressive and enter practicality The required means in change stage.In recent years, people have put into huge financial resources and energy, a large amount of function admirables to the exploitation of new material Material make organic electroluminescent achieve some breakthroughs (see U.S.Pat.No.5,150,006；5,141,671；5, 073,446；5,061,569；5,059,862；5,059,861；5,047,687；4,950,950；5,104,740；5,227, 252；5,256,945；5,069,975；5,122,711；5,554,450；5,683,823；5,593,788；5,645,948；5, 451,343；5,623,080；5,395,862).
Red fluorescence material excitation energy is relatively low and generally has big conjugated chain, and energy is easy during deexcitation The loss in a manner of non-radiative, thus high fluorescence efficiency and with good coloration red fluorescence material it is more rare.Preferably Red light material is still based on phosphor material.The best near-infrared phosphorescent devices of efficiency are mainly platinum complex at present, are shone At 700nm, maximum external quantum efficiency up to 14.5% (M.Cocchi, J.Kalinowski, Appl.Phys.Lett., 2008, 92,113302).But platinum complex has longer phosphorescent lifetime, efficiency is roll-offed seriously with the increase of voltage, expensive etc. Disadvantage causes difficulty for large-scale industrial production, at present for, disclosure satisfy that the feux rouges of industrial requirement to near-infrared phosphorescence Luminous luminescent material is still less, and the red phosphorescence material being applied in organic electroluminescence device reported at present is highly concentrated It is all quenched there is more serious triplet-triplet under degree and its carrier transmission characteristics is all poor, this allows for phosphorus Luminescent material is usually doped in material of main part using very low doping concentration and within the scope of very narrow doping as luminescent layer ability It realizes high performance electroluminescent, in addition also has some devices by designing complicated device architecture come limiting carrier and exciton To realize high-performance, this requires more harsh device technology of preparing, is difficult to realize industrialization production large-scale from now on.
First ligand is that the feux rouges of 1- phenyl isoquinolin oxazoline derivates is flat with larger rigidity to near-infrared complex of iridium The good thermal stability of facial bone Jia ﹑ and higher fluorescence quantum efficiency, while having the mono- ﹑ productions Shuai Gao ﹑ purifications of synthesis Jian easy Feature, new assistant ligand such as amidino groups or guanidine radicals are introduced into complex of iridium by we, have synthesized the phosphorus of a series of new Luminescent material.This kind of novel complex of iridium uses the assistant ligand of N^N coordinations, pair with traditional C^N coordinations, O^O coordinations Tooth ligand is different, and the dinitrogen coordination structure of the electron rich in this kind of amidine group and guanidine group is more conducive to stable center trivalent gold Belong to cation, meanwhile, the Cloud Distribution on metal iridium can be also seriously affected, and then for the photo electric of entire complex molecule Matter has a huge impact, and the ligand containing amidino groups or guanidine group has stronger rigidity with the four-membered ring that metal is constituted, and has Conducive to unnecessary vibrational energy loss is reduced, efficient luminescent properties are realized.And this kind of deep complexes of red light iridium of synthesis Material has shorter phosphorescent lifetime, extraordinary thermal stability, excellent double carriers transmission characteristic, and has very excellent Feux rouges CIE chromaticity coordinates, prepared dark red optical device has extraordinary electroluminescent properties, to realize in full-color display Dark red light emitting provides more choices.
Invention content
The purpose of the present invention is to provide being related to, the first ligand is 1- phenyl isoquinolins oxazoline derivates, assistant ligand is amidino groups Application of the feux rouges of guanidine radicals analog derivative to near-infrared phosphorescent iridium complex luminescent material and its in organic electroluminescence device.
Compound formula according to the present invention is as follows：
Wherein R1、R2、R3、R4It is identical or different；
R1、R2For H, F, the linear or branched alkyl group of 1~10 C, the straight or branched alkoxyl of 1~10 C, aromatic radical Deng；
R3It is H, F, the linear or branched alkyl group of 1~10 C, the straight or branched alkoxyl of 1~10 C, 1~10 C Linear chain or branched chain alkyl or the phenyl derivatives of alkoxy substitution, 1~10 C linear chain or branched chain alkyl or alkoxy Substituted carbazole derivates etc.；
R4It is H, F, the linear or branched alkyl group of 1~10 C, the straight or branched alkoxyl of 1~10 C, 1~10 C Linear chain or branched chain alkyl or the phenyl derivatives of alkoxy substitution, 1~10 C linear chain or branched chain alkyl or alkoxy Substituted carbazole derivates etc..
Compound synthesis route general formula according to the present invention is as follows：
According to above-mentioned synthetic reaction general formula, compound according to the present invention can synthesize under similar reaction condition Come.
It is involved in the present invention to representative first ligand be 1- phenyl isoquinolins oxazoline derivates, assistant ligand is amidino groups The feux rouges of guanidine radicals analog derivative is as follows to near-infrared phosphorescent iridium complex (1-121)：
Description of the drawings
Fig. 1：Using the EL device structure schematic diagram of material preparation of the present invention.
Fig. 2：The EL spectra figure prepared using compound 1 of the present invention.
Fig. 3：The EL spectra figure prepared using compound 5 of the present invention.
Fig. 4：The EL spectra figure prepared using compound 12 of the present invention.
Fig. 5：The EL spectra figure prepared using compound 16 of the present invention.
Fig. 6：The EL spectra figure prepared using compound 34 of the present invention.
Fig. 7：The EL spectra figure prepared using compound 38 of the present invention.
Fig. 8：The EL spectra figure prepared using compound 89 of the present invention.
Feux rouges of the present invention to near-infrared phosphorescent iridium complex luminescent material can prepare organic electroluminescence It is applied in terms of part.Organic electroluminescence device is made of one or more layers organic layer between cathode, anode and two electrodes, At least one layer of in organic layer is luminescent layer, more than one feux rouges of the present invention to near-infrared phosphorescent iridium complex luminescent material It is doped in material of main part as phosphorescent guest and constitutes luminescent layer.
Further, the structure for the electroluminescent device that prepared by the present invention is as shown in Figure 1, the names of the parts are：Transparent glass Or other transparent substrates 1, ITO (indium tin oxide) anode 2, NPB (N, the N&apos of attachment on a transparent substrate;- two (1- naphthalenes)-N, N'Diphenyl -1,1'Biphenyl -4,4'Diamines) hole transmission layer 3, comprising material of the present invention luminescent layer 4 (present invention The material is used as phosphorescent guest dopant material, and doping concentration weight percentage is 5~20%, and material of main part uses double (10- Qiang Jibenbings [h]Quinoline) beryllium), bis- (phenolic group pyridine) beryllium (Bepp2) be used as electron transfer layer 5, LiF as electron injection Layer 6, metal Al are as cathode 7.
Electroluminescent device of the present invention can be used for preparing display of organic electroluminescence or organic electroluminescent shines Mingguang City source.
It is bis- (10- hydroxy benzos to prepare used material of main part when device luminescent layer;h]Quinoline) beryllium, molecular structure It is shown below：
NPB and Bepp2Structural formula is as follows：
Specific implementation mode
Embodiment 1：The synthesis of compound 1- phenyl isoquinolins quinoline (PIQ)：
By phenyl boric acid (16mmol), 1- chlorine isoquinolin (12mmol), four (triphenyl phosphorus) palladiums (0.06mmol), 2mol/L's Sodium carbonate liquor (60ml), tetrahydrofuran (60mL) are added in bottle with two necks, N2Under protection, it is small to be heated to reflux 12 in 123 DEG C of oil bath When stop reaction, reaction mixture is poured into distilled water, with dichloromethane extract liquid separation, collect organic phase, then use column layer Analysis method detaches (silica gel, dichloromethane) and obtains white powder target product.
The synthetic method of other 1- octaverines containing various substituent groups according to the present invention is identical, Acquisition can be synthesized according to above-mentioned reaction condition, the phenyl boric acid replaced by corresponding substituent group.
Embodiment 2：Chlorine bridging Zhong Jianti [Ir(piq)2(μ-Cl)]2Synthesis：
By 1- phenyl isoquinolins quinoline (12mmol), three hydrated iridium trichlorides (5mmol), ethylene glycol ethyl ether (15ml), pure water (5ml) is added in bottle with two necks, N2Under protection, 12h is heated to reflux for 150 DEG C in oil bath.Stop reaction, distilled water 150mL analysis is added Go out precipitation, reaction mixture is filtered, absolute ethyl alcohol washs filter cake, and red powder target product is obtained after drying.
The synthetic method phase of other iridium chlorine bridging midbody derivants containing various substituent groups according to the present invention Together, acquisition can be synthesized by corresponding 1- octaverines according to above-mentioned reaction condition.
Embodiment 3：The synthesis of compound 1：
It is added 41mg (0.4mmol) diisopropylamines and 10mL n-hexanes in 50mL there-necked flasks, at nitrogen protection and -78 DEG C, The n-BuLi of the 2.6M/L of 0.15mL is added dropwise, stirs lower reaction one hour, N, N '-diisopropylcarbodiimide 50mg is added dropwise (0.4mmol) is gradually increased to room temperature after dripping, stirring is lower, and the reaction was continued one hour, and 15mL is slowly dropped under nitrogen protection 0.2mmol s &#91 has been added;Ir(piq)2(μ-Cl)]2Hexane solution in.It is added dropwise, is to slowly warm up to 80 DEG C, reaction 8 is small When.Stop reaction, mixed liquor is cooled to room temperature, and decompression is spin-dried for solvent, and obtained solid product is washed three times with ether, every time 20mL.Vacuum sublimation obtains red powder compound 1 (281.2mg, yield 85%), the molecular ion matter that mass spectral analysis determines Amount is：827.18 (calculated value is：827.35)；Theoretical elemental content (%) C43H48IrN5：C, 62.44；H, 5.85；N, 8.47； Survey constituent content (%)：C, 62.24；H, 5.94；N, 8.58.Above-mentioned analysis result shows the production that the product of acquisition is estimated Product.
Other target compounds according to the present invention can utilize the chlorine bridging intermediate containing various substituent groups to spread out Biology forms assistant ligand with diisopropylamine and synthesizes acquisition.
Embodiment 4：The synthesis of compound 2：
It is added 67mg (0.4mmol) carbazoles and 10mL n-hexanes in 50mL there-necked flasks, at nitrogen protection and -78 DEG C, is added dropwise The n-BuLi of 0.15mL 2.6M stirs lower reaction one hour, N, N '-diisopropylcarbodiimide 50mg is added dropwise (0.4mmol) is gradually increased to room temperature after dripping, stirring is lower, and the reaction was continued one hour, and 15mL is slowly dropped under nitrogen protection 0.2mmol s &#91 has been added;Ir(piq)2(μ-Cl)]2Hexane solution in.It is added dropwise, is to slowly warm up to 80 DEG C, reaction 8 is small When.Stop reaction, mixed liquor is cooled to room temperature, and decompression is spin-dried for solvent, and obtained solid product is washed three times with ether, every time 20mL.Vacuum sublimation obtains red powder compound 2 (307.3mg, yield 86%), the molecular ion matter that mass spectral analysis determines Amount is：893.11 (calculated value is：893.31)；Theoretical elemental content (%) C49H42IrN5：C,65.90；H,4.74；N,7.84； Survey constituent content (%)：C, 65.80；H, 4.79；N, 7.89.Above-mentioned analysis result shows the production that the product of acquisition is estimated Product.
Other target compounds according to the present invention can utilize the chlorine bridging intermediate containing various substituent groups to spread out Biology forms assistant ligand with carbazole derivates and synthesizes acquisition.
Embodiment 5：The synthesis of compound 3：
According to the synthesis of compound 2, step is identical, obtains red powder compound 3 (232.2mg, yield 63%), matter Spectrum analysis determine molecular ion quality be：921.47 (calculated value is：921.34)；Theoretical elemental content (%) C51H46IrN5： C,66.50；H,5.03；N,7.60；Survey constituent content (%)：C, 66.57；H, 5.10；N, 7.46.Above-mentioned analysis result table Bright, the product of acquisition is the product being expected.
Embodiment 6：The synthesis of compound 4：
According to the synthesis of compound 2, step is identical, obtains red powder compound 4 (241.3mg, yield 60%), matter Spectrum analysis determine molecular ion quality be：1005.40 (calculated value is：1005.43)；Theoretical elemental content (%) C57H58IrN5：C,68.10；H,5.82；N,6.97；Survey constituent content (%)：C, 68.14；H, 5.78；N, 6.97.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 7：The synthesis of compound 5：
It is added 65mg (0.4mmol) bromobenzenes and 10mL n-hexanes in 50mL there-necked flasks, at nitrogen protection and -78 DEG C, is added dropwise The n-BuLi of 0.15mL 2.6M stirs lower reaction one hour, N, N '-diisopropylcarbodiimide 50mg is added dropwise (0.4mmol) is gradually increased to room temperature after dripping, stirring is lower, and the reaction was continued one hour, and 15mL is slowly dropped under nitrogen protection 0.2mmol s &#91 has been added;Ir(piq)2(μ-Cl)]2Hexane solution in.It is added dropwise, is to slowly warm up to 80 DEG C, reaction 8 is small When.Stop reaction, mixed liquor is cooled to room temperature, and decompression is spin-dried for solvent, and obtained solid product is washed three times with ether, every time 20mL.Vacuum sublimation obtains red powder 205mg, yield 64%.Mass spectral analysis determine molecular ion quality be：804.51 (calculated value is：804.28)；Theoretical elemental content (%) C43H39IrN4：C, 64.24；H, 4.89；N, 6.97, survey constituent content (%)：C, 64.35；H, 4.84；N, 6.91.Above-mentioned analysis result shows the product that the product of acquisition is estimated.
Other target compounds according to the present invention can utilize the chlorine bridging intermediate containing various substituent groups to spread out Biology forms assistant ligand with bromobenzene derivative and synthesizes acquisition.
Embodiment 8：The synthesis of compound 6：
According to the synthesis of compound 5, step is identical, obtains red powder compound 6 (189.8mg, yield 58%), matter Spectrum analysis determine molecular ion quality be：818.27 (calculated value is：818.30)；Theoretical elemental content (%) C44H41IrN4： C,64.60；H,5.05；N,6.85；Survey constituent content (%)：C, 64.70；H, 5.01；N, 6.79.Above-mentioned analysis result table Bright, the product of acquisition is the product being expected.
Embodiment 9：The synthesis of compound 7：
According to the synthesis of compound 5, step is identical, obtains red powder compound 7 (203.1mg, yield 61%), matter Spectrum analysis determine molecular ion quality be：832.27 (calculated value is：832.31)；Theoretical elemental content (%) C45H43IrN4： C,64.96；H,5.21；N,6.73；Survey constituent content (%)：C, 64.97；H, 5.21；N, 6.72.Above-mentioned analysis result table Bright, the product of acquisition is the product being expected.
Embodiment 10：The synthesis of compound 8：
According to the synthesis of compound 5, step is identical, obtains red powder compound 8 (257.3mg, yield 76%), matter Spectrum analysis determine molecular ion quality be：846.30 (calculated value is：846.33)；Theoretical elemental content (%) C46H45IrN4： C,65.90；H,4.74；N,7.84；Survey constituent content (%)：C,65.82H,4.76；N,7.90.Above-mentioned analysis result shows The product of acquisition is the product being expected.
Embodiment 11：The synthesis of compound 9：
According to the synthesis of compound 5, step is identical, obtains red powder compound 9 (231.2mg, yield 65%), matter Spectrum analysis determine molecular ion quality be：888.20 (calculated value is：888.37)；Theoretical elemental content (%) C49H51IrN4： C,66.26；H,5.79；N,6.31；Survey constituent content (%)：C,66.26；H,5.81N,6.29.Above-mentioned analysis result shows The product of acquisition is the product being expected.
Embodiment 12：The synthesis of compound 10：
According to the synthesis of compound 5, step is identical, obtains red powder compound 10 (241.2mg, yield 70%), Mass spectral analysis determine molecular ion quality be：860.33 (calculated value is：860.35)；Theoretical elemental content (%) C47H47IrN4：C,65.63；H,5.51；N,6.51；Survey constituent content (%)：C,65.60；H,5.54；N,6.51.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 13：The synthesis of chemical combination 11：
According to the synthesis of compound 5, step is identical, obtains red powder compound 11 (245.9mg, yield 67%), Mass spectral analysis determine molecular ion quality be：916.38 (calculated value is：916.41)；Theoretical elemental content (%) C51H55IrN4：C,66.86；H,6.05；N,6.11；Survey constituent content (%)：C,66.88；H,6.03；N,6.11.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 14：The synthesis of compound 12：
According to the synthesis of compound 1, step is identical, obtains red powder compound 12 (262.5mg, yield 76%), Mass spectral analysis determine molecular ion quality be：863.54 (calculated value is：863.34)；Theoretical elemental content (%) C43H46F2IrN5：C,59.84；H,5.37；N,8.11；Survey constituent content (%)：C, 59.66；H, 5.46；N, 8.20.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 15：The synthesis of compound 13：
According to the synthesis of compound 2, step is identical, obtains red powder compound 13 (278.8mg, yield 75%), Mass spectral analysis determine molecular ion quality be：929.50 (calculated value is：929.29)；Theoretical elemental content (%) C49H40F2IrN5：C,63.34；H,4.34；N,7.54；Survey constituent content (%)：C, 63.44；H, 4.29；N, 7.49.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 16：The synthesis of compound 14：
According to the synthesis of compound 2, step is identical, obtains red powder compound 14 (233.6mg, yield 61%), Mass spectral analysis determine molecular ion quality be：957.30 (calculated value is：957.32)；Theoretical elemental content (%) C51H44F2IrN5：C,64.00；H,4.63；N,7.32；Survey constituent content (%)：C, 64.03；H, 4.64；N, 7.28.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 17：The synthesis of compound 15：
According to the synthesis of compound 2, step is identical, obtains red powder compound 15 (262.4mg, yield 63%), Mass spectral analysis determine molecular ion quality be：1041.38 (calculated value is：1041.41)；Theoretical elemental content (%) C57H56F2IrN5：C,65.75；H,5.42；N,6.73；Survey constituent content (%)：C, 65.72；H, 5.45；N, 6.73.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 18：The synthesis of compound 16：
According to the synthesis of compound 5, step is identical, obtains red powder compound 16 (262.2mg, yield 78%), Mass spectral analysis determine molecular ion quality be：840.30 (calculated value is：840.26)；Theoretical elemental content (%) C43H37F2IrN4：C,61.48；H,4.44；N,6.67；Survey constituent content (%)：C, 61.58；H, 4.34；N, 6.67.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 19：The synthesis of compound 17：
According to the synthesis of compound 5, step is identical, obtains red powder compound 17 (222.1mg, yield 65%), Mass spectral analysis determine molecular ion quality be：854.32 (calculated value is：854.28)；Theoretical elemental content (%) C44H39F2IrN4：C,61.88；H,4.60；N,6.56；Survey constituent content (%)：C, 61.84；H, 4.63；N, 6.57.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 20：The synthesis of compound 18：
According to the synthesis of compound 5, step is identical, obtains red powder compound 18 (215.3mg, yield 62%), Mass spectral analysis determine molecular ion quality be：868.25 (calculated value is：868.29)；Theoretical elemental content (%) C45H41F2IrN4：C,62.26；H,4.76；N,6.45；Survey constituent content (%)：C, 62.28；H, 4.77；N, 6.42.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 21：The synthesis of compound 19：
According to the synthesis of compound 5, step is identical, obtains red powder compound 19 (232.9mg, yield 66%), Mass spectral analysis determine molecular ion quality be：882.30 (calculated value is：882.31)；Theoretical elemental content (%) C46H43F2IrN4：C,62.64；H,4.91；N,6.35；Survey constituent content (%)：C,62.59H,4.95；N,6.36.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 22：The synthesis of compound 20：
According to the synthesis of compound 5, step is identical, obtains red powder compound 20 (255.1mg, yield 69%), Mass spectral analysis determine molecular ion quality be：924.52 (calculated value is：924.36)；Theoretical elemental content (%) C49H49F2IrN4：C,63.68；H,5.34；N,6.06；Survey constituent content (%)：C,63.75H,5.30；N,6.03.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 23：The synthesis of compound 21：
According to the synthesis of compound 5, step is identical, obtains red powder compound 21 (222.2mg, yield 62%), Mass spectral analysis determine molecular ion quality be：896.28 (calculated value is：896.32)；Theoretical elemental content (%) C47H45F2IrN4：C,63.00；H,5.06；N,6.25；Survey constituent content (%)：C,63.10H,5.01；N,6.20.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 24：The synthesis of compound 22：
According to the synthesis of compound 5, step is identical, obtains red powder compound 22 (228.6mg, yield 60%), Mass spectral analysis determine molecular ion quality be：952.30 (calculated value is：952.39)；Theoretical elemental content (%) C51H53F2IrN4：C,64.33；H,5.61；N,5.88；Survey constituent content (%)：C,64.35H,5.63；N,5.84.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 25：The synthesis of compound 23：
According to the synthesis of compound 1, step is identical, obtains red powder compound 23 (259.0mg, yield 75%), Mass spectral analysis determine molecular ion quality be：863.10 (calculated value is：863.34)；Theoretical elemental content (%) C43H46F2IrN5：C,59.84；H,5.37；N,8.11；Survey constituent content (%)：C, 59.95；H, 5.30；N, 8.07.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 26：The synthesis of compound 24：
According to the synthesis of compound 2, step is identical, obtains red powder compound 24 (252.8mg, yield 68%), Mass spectral analysis determine molecular ion quality be：929.30 (calculated value is：929.29)；Theoretical elemental content (%) C49H40F2IrN5：C,63.34；H,4.34；N,7.54；Survey constituent content (%)：C, 63.24；H, 4.39；N, 7.59.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 27：The synthesis of compound 25：
According to the synthesis of compound 2, step is identical, obtains red powder compound 25 (229.8mg, yield 60%), Mass spectral analysis determine molecular ion quality be：957.30 (calculated value is：957.32)；Theoretical elemental content (%) C51H44F2IrN5：C,64.00；H,4.63；N,7.32；Survey constituent content (%)：C, 64.04；H, 4.63；N, 7.28.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 28：The synthesis of compound 26：
According to the synthesis of compound 2, step is identical, obtains red powder compound 26 (266.6mg, yield 64%), Mass spectral analysis determine molecular ion quality be：1041.38 (calculated value is：1041.41)；Theoretical elemental content (%) C57H56F2IrN5：C,65.75；H,5.42；N,6.73；Survey constituent content (%)：C, 65.71；H, 5.46；N, 6.73.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 29：The synthesis of compound 27：
According to the synthesis of compound 5, step is identical, obtains red powder compound 27 (252.1mg, yield 75%), Mass spectral analysis determine molecular ion quality be：840.30 (calculated value is：840.26)；Theoretical elemental content (%) C43H37F2IrN4：C,61.48；H,4.44；N, 6.67 actual measurement constituent contents (%)：C, 61.48；H, 4.34；N, 6.77.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 30：The synthesis of compound 28：
According to the synthesis of compound 5, step is identical, obtains red powder compound 28 (205.0mg, yield 60%), Mass spectral analysis determine molecular ion quality be：854.32 (calculated value is：854.28)；Theoretical elemental content (%) C44H39F2IrN4：C,61.88；H,4.60；N,6.56；Survey constituent content (%)：C, 61.86；H, 4.61；N, 6.57.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 31：The synthesis of compound 29：
According to the synthesis of compound 5, step is identical, obtains red powder compound 29 (215.3mg, yield 62%), Mass spectral analysis determine molecular ion quality be：868.25 (calculated value is：868.29)；Theoretical elemental content (%) C45H41F2IrN4：C,62.26；H,4.76；N,6.45；Survey constituent content (%)：C, 62.30；H, 4.75；N, 6.42.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 32：The synthesis of compound 30：
According to the synthesis of compound 5, step is identical, obtains red powder compound 30 (225.9mg, yield 64%), Mass spectral analysis determine molecular ion quality be：882.30 (calculated value is：882.31)；Theoretical elemental content (%) C46H43F2IrN4：C,62.64；H,4.91；N,6.35；Survey constituent content (%)：C,62.68H,4.95；N,6.27.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 33：The synthesis of compound 31：
According to the synthesis of compound 5, step is identical, obtains red powder compound 31 (247.7mg, yield 67%), Mass spectral analysis determine molecular ion quality be：924.52 (calculated value is：924.36)；Theoretical elemental content (%) C49H49F2IrN4：C,63.68；H,5.34；N,6.06；Survey constituent content (%)：C,63.62H,5.36；N,6.10.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 34：The synthesis of compound 32：
According to the synthesis of compound 5, step is identical, obtains red powder compound 32 (229.5mg, yield 64%), Mass spectral analysis determine molecular ion quality be：896.20 (calculated value is：896.32)；Theoretical elemental content (%) C47H45F2IrN4：C,63.00；H,5.06；N,6.25；Survey constituent content (%)：C,63.15H,5.01；N,6.15.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 35：The synthesis of compound 33：
According to the synthesis of compound 5, step is identical, obtains red powder compound 33 (232.4mg, yield 61%), Mass spectral analysis determine molecular ion quality be：952.30 (calculated value is：952.39)；Theoretical elemental content (%) C51H53F2IrN4：C,64.33；H,5.61；N,5.88；Survey constituent content (%)：C,64.37H,5.60；N,5.85.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 36：The synthesis of compound 34：
According to the synthesis of compound 1, step is identical, obtains red powder compound 34 (259.0mg, yield 72%), Mass spectral analysis determine molecular ion quality be：899.40 (calculated value is：899.32)；Theoretical elemental content (%) C43H44F4IrN5：C,57.44；H,4.93；N,7.79；Survey constituent content (%)：C, 57.30；H, 5.01；N, 7.86.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 37：The synthesis of compound 35：
According to the synthesis of compound 2, step is identical, obtains red powder compound 35 (270.3mg, yield 70%), Mass spectral analysis determine molecular ion quality be：965.25 (calculated value is：965.27)；Theoretical elemental content (%) C49H38F4IrN5：C,60.98；H,3.97；N,7.26；Survey constituent content (%)：C, 60.95；H, 4.01；N, 7.26.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 38：The synthesis of compound 36：
According to the synthesis of compound 2, step is identical, obtains red powder compound 36 (238.4mg, yield 60%), Mass spectral analysis determine molecular ion quality be：993.35 (calculated value is：993.30)；Theoretical elemental content (%) C51H42F4IrN5：C,61.68；H,4.26；N,7.05；Survey constituent content (%)：C, 61.65；H, 4.29；N, 7.05.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 39：The synthesis of compound 37：
According to the synthesis of compound 2, step is identical, obtains red powder compound 37 (267.2mg, yield 62%), Mass spectral analysis determine molecular ion quality be：1077.33 (calculated value is：1077.39)；Theoretical elemental content (%) C57H54F4IrN5：C,63.55；H,5.05；N,6.50；Survey constituent content (%)：C, 63.52；H, 5.08；N, 6.50.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 40：The synthesis of compound 38：
According to the synthesis of compound 5, step is identical, obtains red powder compound 38 (220.8mg, yield 63%), Mass spectral analysis determine molecular ion quality be：876.5 (calculated value is：876.24)；Theoretical elemental content (%) C43H35F4IrN4：C,58.96；H,4.03；N,6.40；Survey constituent content (%)：C, 58.86；H, 4.08；N, 6.45.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 41：The synthesis of compound 39：
According to the synthesis of compound 5, step is identical, obtains red powder compound 39 (210.1mg, yield 59%), Mass spectral analysis determine molecular ion quality be：890.22 (calculated value is：890.26)；Theoretical elemental content (%) C44H37F4IrN4：C,59.38；H,4.19；N,6.30；Survey constituent content (%)：C, 59.33；H, 4.24；N, 6.30.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 42：The synthesis of compound 40：
According to the synthesis of compound 5, step is identical, obtains red powder compound 40 (227.9mg, yield 63%), Mass spectral analysis determine molecular ion quality be：904.21 (calculated value is：904.27)；Theoretical elemental content (%) C45H39F4IrN4：C,59.79；H,4.35；N,6.20；Survey constituent content (%)：C, 59.77；H, 4.33；N, 6.24.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 43：The synthesis of compound 41：
According to the synthesis of compound 5, step is identical, obtains red powder compound 41 (235.1mg, yield 64%), Mass spectral analysis determine molecular ion quality be：918.36 (calculated value is：918.29)；Theoretical elemental content (%) C46H41F4IrN4：C,60.18；H,4.50；N,6.10；Survey constituent content (%)：C,60.15；H,4.53；N,6.10.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 44：The synthesis of compound 42：
According to the synthesis of compound 5, step is identical, obtains red powder compound 42 (234.3mg, yield 61%), Mass spectral analysis determine molecular ion quality be：960.30 (calculated value is：960.34)；Theoretical elemental content (%) C49H47F4IrN4：C,61.30；H,4.93；N,5.84；Survey constituent content (%)：C,61.34H,4.90；N,5.83.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 45：The synthesis of compound 43：
According to the synthesis of compound 5, step is identical, obtains red powder compound 43 (234.9mg, yield 63%), Mass spectral analysis determine molecular ion quality be：932.30 (calculated value is：932.31)；Theoretical elemental content (%) C47H43F4IrN4：C,60.56；H,4.65；N,6.01；Survey constituent content (%)：C,60.52H,4.69；N,6.01.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 46：The synthesis of compound 44：
According to the synthesis of compound 5, step is identical, obtains red powder compound 44 (241.2mg, yield 61%), Mass spectral analysis determine molecular ion quality be：988.32 (calculated value is：988.37)；Theoretical elemental content (%) C51H51F4IrN4：C,61.99；H,5.20；N,5.67；Survey constituent content (%)：C,61.92；H,5.24；N,5.70.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 47：The synthesis of compound 45：
According to the synthesis of compound 1, step is identical, obtains red powder compound 45 (265.2mg, yield 74%), Mass spectral analysis determine molecular ion quality be：899.51 (calculated value is：899.32)；Theoretical elemental content (%) C43H44F4IrN5：C,57.44；H,4.93；N,7.79；Survey constituent content (%)：C, 57.33；H, 5.04；N, 7.82.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 48：The synthesis of compound 46：
According to the synthesis of compound 2, step is identical, obtains red powder compound 46 (276.3mg, yield 71%), Mass spectral analysis determine molecular ion quality be：965.31 (calculated value is：965.27)；Theoretical elemental content (%) C49H38F4IrN5：C,60.98；H,3.97；N,7.26；Survey constituent content (%)：C, 60.92；H, 4.02；N, 7.29.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 49：The synthesis of compound 47：
According to the synthesis of compound 2, step is identical, obtains red powder compound 47 (242.4mg, yield 61%), Mass spectral analysis determine molecular ion quality be：993.32 (calculated value is：993.30)；Theoretical elemental content (%) C51H42F4IrN5：C,61.68；H,4.26；N,7.05；Survey constituent content (%)：C, 61.72；H, 4.22；N, 7.05.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 50：The synthesis of compound 48：
According to the synthesis of compound 2, step is identical, obtains red powder compound 48 (258.6mg, yield 60%), Mass spectral analysis determine molecular ion quality be：1077.41 (calculated value is：1077.39)；Theoretical elemental content (%) C57H54F4IrN5：C,63.55；H,5.05；N,6.50；Survey constituent content (%)：C, 63.57；H, 5.03；N, 6.50.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 51：The synthesis of compound 49：
According to the synthesis of compound 5, step is identical, obtains red powder compound 49 (226.8mg, yield 64%), Mass spectral analysis determine molecular ion quality be：876.2 (calculated value is：876.24)；Theoretical elemental content (%) C43H35F4IrN4：C,58.96；H,4.03；N,6.40；Survey constituent content (%)：C, 58.76；H, 4.12；N, 6.61.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 52：The synthesis of compound 50：
According to the synthesis of chemical combination 5, step is identical, obtains red powder compound 50 (210.1mg, yield 59%), matter Spectrum analysis determine molecular ion quality be：890.22 (calculated value is：890.26)；Theoretical elemental content (%) C44H37F4IrN4：C,59.38；H,4.19；N,6.30；Survey constituent content (%)：C, 59.31；H, 4.26；N, 6.30.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 53：The synthesis of compound 51：
According to the synthesis of compound 5, step is identical, obtains red powder compound 51 (227.9mg, yield 63%), Mass spectral analysis determine molecular ion quality be：904.21 (calculated value is：904.27)；Theoretical elemental content (%) C45H39F4IrN4：C,59.79；H,4.35；N,6.20；Survey constituent content (%)：C, 59.75；H, 4.35；N, 6.24.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 54：The synthesis of compound 52：
According to the synthesis of compound 5, step is identical, obtains red powder compound 52 (247.1mg, yield 66%), Mass spectral analysis determine molecular ion quality be：918.33 (calculated value is：918.29)；Theoretical elemental content (%) C46H41F4IrN4：C,60.18；H,4.50；N,6.10；Survey constituent content (%)：C,60.19；H,4.55；N,6.27.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 55：The synthesis of compound 53：
According to the synthesis of compound 5, step is identical, obtains red powder compound 53 (246.3mg, yield 63%), Mass spectral analysis determine molecular ion quality be：960.71 (calculated value is：960.34)；Theoretical elemental content (%) C49H47F4IrN4：C,61.30；H,4.93；N,5.84；Survey constituent content (%)：C,61.44H,4.99；N,5.33.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 56：The synthesis of compound 54：
According to the synthesis of compound 5, step is identical, obtains red powder compound 54 (222.9mg, yield 61%), Mass spectral analysis determine molecular ion quality be：932.75 (calculated value is：932.31)；Theoretical elemental content (%) C47H43F4IrN4：C,60.56；H,4.65；N,6.01；Survey constituent content (%)：C,60.82H,4.79；N,5.94.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 57：The synthesis of compound 55：
According to the synthesis of compound 5, step is identical, obtains red powder compound 55 (253.2mg, yield 63%), Mass spectral analysis determine molecular ion quality be：988.12 (calculated value is：988.37)；Theoretical elemental content (%) C51H51F4IrN4：C,61.99；H,5.20；N,5.67；Survey constituent content (%)：C,61.82；H,5.04；N,5.77.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 58：The synthesis of compound 56：
According to the synthesis of compound 1, step is identical, obtains dark red powder shape compound 56 (246.4mg, yield 72%), the molecular ion quality of mass spectral analysis determination is：855.40 (calculated value is：855.39)；Theoretical elemental content (%) C45H52IrN5：C,63.20；H,6.13；N,8.19；Survey constituent content (%)：C, 63.23；H, 6.10；N, 8.19.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 59：The synthesis of compound 57：
According to the synthesis of compound 2, step is identical, obtains dark red powder shape compound 57 (243.2mg, yield 66%), the molecular ion quality of mass spectral analysis determination is：921.40 (calculated value is：921.34)；Theoretical elemental content (%) C51H46IrN5：C,66.50；H,5.03；N,7.60；Survey constituent content (%)：C, 66.55；H, 5.00；N, 7.58.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 60：The synthesis of compound 58：
According to the synthesis of compound 2, step is identical, obtains red powder compound 58 (231.6mg, yield 61%), Mass spectral analysis determine molecular ion quality be：949.33 (calculated value is：949.37)；Theoretical elemental content (%) C53H50IrN5：C,67.06；H,5.31；N,7.38；Survey constituent content (%)：C, 67.03；H, 5.30；N, 7.42.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 61：The synthesis of compound 59：
According to the synthesis of compound 2, step is identical, obtains red powder compound 59 (243.9mg, yield 59%), Mass spectral analysis determine molecular ion quality be：1033.52 (calculated value is：1033.46)；Theoretical elemental content (%) C59H62IrN5：C,68.57；H,6.05；N,6.78；Survey constituent content (%)：C, 68.55；H, 6.07；N, 6.78.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 62：The synthesis of compound 60：
According to the synthesis of compound 5, step is identical, obtains dark red powder shape compound 60 (226.4mg, yield 68%), the molecular ion quality of mass spectral analysis determination is：832.45 (calculated value is：832.31)；Theoretical elemental content (%) C45H43IrN4：C,64.96；H,5.21；N,6.73；Survey constituent content (%)：C, 64.92；H, 5.22；N, 6.76.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 63：The synthesis of compound 61：
According to the synthesis of compound 5, step is identical, obtains red powder compound 61 (216.7mg, yield 64%), Mass spectral analysis determine molecular ion quality be：846.30 (calculated value is：846.33)；Theoretical elemental content (%) C46H45IrN4：C,65.30；H,5.36；N,6.62；Survey constituent content (%)：C, 65.33；H, 5.33；N, 6.62.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 64：The synthesis of compound 62：
According to the synthesis of compound 5, step is identical, obtains red powder compound 62 (206.5mg, yield 60%), Mass spectral analysis determine molecular ion quality be：860.28 (calculated value is：860.34)；Theoretical elemental content (%) C47H47IrN4：C,65.63；H,5.51；N,6.51；Survey constituent content (%)：C, 65.63；H, 5.55；N, 6.47.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 65：The synthesis of compound 63：
According to the synthesis of compound 5, step is identical, obtains red powder compound 63 (210.0mg, yield 60%), Mass spectral analysis determine molecular ion quality be：875.32 (calculated value is：875.37)；Theoretical elemental content (%) C48H49IrN4：C,65.95；H,5.65；N,6.41；Survey constituent content (%)：C,65.90；H,5.62；N,6.49.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 66：The synthesis of compound 64：
According to the synthesis of compound 5, step is identical, obtains red powder compound 64 (245.9mg, yield 67%), Mass spectral analysis determine molecular ion quality be：917.35 (calculated value is：917.41)；Theoretical elemental content (%) C51H55IrN4：C,66.86；H,6.05；N,6.11；Survey constituent content (%)：C,66.80；H,6.05；N,6.17.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 67：The synthesis of compound 65：
According to the synthesis of compound 5, step is identical, obtains red powder compound 65 (217.0mg, yield 61%), Mass spectral analysis determine molecular ion quality be：889.39 (calculated value is：889.38)；Theoretical elemental content (%) C49H51IrN4：C,66.26；H,5.79；N,6.31；Survey constituent content (%)：C,66.19；H,5.87；N,6.30.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 68：The synthesis of compound 66：
According to the synthesis of compound 5, step is identical, obtains red powder compound 66 (234.5mg, yield 62%), Mass spectral analysis determine molecular ion quality be：945.40 (calculated value is：945.44)；Theoretical elemental content (%) C53H59IrN4：C,67.41；H,6.30；N,5.93；Survey constituent content (%)：C,67.35；H,6.35；N,5.94.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 69：The synthesis of compound 67：
According to the synthesis of compound 1, step is identical, obtains dark red powder shape compound 67 (240.4mg, yield 71%), the molecular ion quality of mass spectral analysis determination is：855.71 (calculated value is：855.39)；Theoretical elemental content (%) C45H52IrN5：C,63.20；H,6.13；N,8.19；Survey constituent content (%)：C, 63.33；H, 6.12；N, 8.17.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 70：The synthesis of compound 68：
According to the synthesis of compound 2, step is identical, obtains dark red powder shape compound 68 (230.2mg, yield 64%), the molecular ion quality of mass spectral analysis determination is：921.45 (calculated value is：921.34)；Theoretical elemental content (%) C51H46IrN5：C,66.50；H,5.03；N,7.60；Survey constituent content (%)：C, 66.51；H, 5.09；N, 7.68.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 71：The synthesis of compound 69：
According to the synthesis of compound 2, step is identical, obtains red powder compound 69 (224.1mg, yield 59%), Mass spectral analysis determine molecular ion quality be：949.39 (calculated value is：949.37)；Theoretical elemental content (%) C53H50IrN5：C,67.06；H,5.31；N,7.38；Survey constituent content (%)：C, 67.01；H, 5.32；N, 7.42.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 72：The synthesis of compound 70：
According to the synthesis of compound 2, step is identical, obtains red powder compound 70 (235.6mg, yield 57%), Mass spectral analysis determine molecular ion quality be：1033.55 (calculated value is：1033.46)；Theoretical elemental content (%) C59H62IrN5：C,68.57；H,6.05；N,6.78；Survey constituent content (%)：C, 68.54；H, 6.06；N, 6.80.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 73：The synthesis of compound 71：
According to the synthesis of compound 5, step is identical, obtains dark red powder shape compound 71 (220.4mg, yield 67%), the molecular ion quality of mass spectral analysis determination is：832.66 (calculated value is：832.31)；Theoretical elemental content (%) C45H43IrN4：C,64.96；H,5.21；N,6.73；Survey constituent content (%)：C, 64.98；H, 5.32；N, 6.79.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 74：The synthesis of compound 72：
According to the synthesis of compound 5, step is identical, obtains red powder compound 72 (209.9mg, yield 62%), Mass spectral analysis determine molecular ion quality be：846.30 (calculated value is：846.33)；Theoretical elemental content (%) C46H45IrN4：C,65.30；H,5.36；N,6.62；Survey constituent content (%)：C, 65.32；H, 5.33；N, 6.63.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 75：The synthesis of compound 73：
According to the synthesis of compound 5, step is identical, obtains red powder compound 73 (206.5mg, yield 60%), Mass spectral analysis determine molecular ion quality be：860.22 (calculated value is：860.34)；Theoretical elemental content (%) C47H47IrN4：C,65.63；H,5.51；N,6.51；Survey constituent content (%)：C, 65.65；H, 5.55；N, 6.45.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 76：The synthesis of compound 74：
According to the synthesis of compound 5, step is identical, obtains red powder compound 74 (203.0mg, yield 59%), Mass spectral analysis determine molecular ion quality be：875.63 (calculated value is：875.37)；Theoretical elemental content (%) C48H49IrN4：C,65.95；H,5.65；N,6.41；Survey constituent content (%)：C,65.93；H,5.72；N,6.59.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 77：The synthesis of compound 75：
According to the synthesis of compound 5, step is identical, obtains red powder compound 75 (232.9mg, yield 65%), Mass spectral analysis determine molecular ion quality be：917.75 (calculated value is：917.41)；Theoretical elemental content (%) C51H55IrN4：C,66.86；H,6.05；N,6.11；Survey constituent content (%)：C,66.80；H,6.15；N,6.13.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 78：The synthesis of compound 76：
According to the synthesis of compound 5, step is identical, obtains red powder compound 76 (210.1mg, yield 60%), Mass spectral analysis determine molecular ion quality be：889.66 (calculated value is：889.38)；Theoretical elemental content (%) C49H51IrN4：C,66.26；H,5.79；N,6.31；Survey constituent content (%)：C,66.18；H,5.97；N,6.39.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 79：The synthesis of compound 77：
According to the synthesis of compound 5, step is identical, obtains red powder compound 77 (204.5mg, yield 58%), Mass spectral analysis determine molecular ion quality be：945.61 (calculated value is：945.44)；Theoretical elemental content (%) C53H59IrN4：C,67.41；H,6.30；N,5.93；Survey constituent content (%)：C,67.65；H,6.38；N,5.84.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 80：The synthesis of compound 78
According to the synthesis of compound 1, step is identical, obtains dark red powder shape compound 78 (212.0mg, yield 60%), the molecular ion quality of mass spectral analysis determination is：883.45 (calculated value is：883.42)；Theoretical elemental content (%) C47H56IrN5：C,63.92；H,6.39；N,7.93；Survey constituent content (%)：C, 63.92；H, 6.40；N, 7.92.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 81：The synthesis of compound 79：
According to the synthesis of compound 2, step is identical, obtains dark red powder shape compound 79 (235.4mg, yield 62%), the molecular ion quality of mass spectral analysis determination is：949.40 (calculated value is：949.37)；Theoretical elemental content (%) C53H50IrN5：C,67.06；H,5.31；N,7.38；Survey constituent content (%)：C, 67.02；H, 5.35；N, 7.38.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 82：The synthesis of compound 80：
According to the synthesis of compound 2, step is identical, obtains red powder compound 80 (222.8mg, yield 57%), Mass spectral analysis determine molecular ion quality be：977.44 (calculated value is：977.40)；Theoretical elemental content (%) C55H54IrN5：C,67.60；H,5.57；N,7.17；Survey constituent content (%)：C, 67.58；H, 5.55；N, 7.21.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 83：The synthesis of compound 81：
According to the synthesis of compound 2, step is identical, obtains red powder compound 81 (233.5mg, yield 55%), Mass spectral analysis determine molecular ion quality be：1061.44 (calculated value is：1061.49)；Theoretical elemental content (%) C61H66IrN5：C,69.03；H,6.27；N,6.60；Survey constituent content (%)：C, 69.08；H, 6.21；N, 6.61.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 84：The synthesis of compound 82：
According to the synthesis of compound 5, step is identical, obtains dark red powder shape compound 82 (223.7mg, yield 65%), the molecular ion quality of mass spectral analysis determination is：860.30 (calculated value is：860.34)；Theoretical elemental content (%) C47H47IrN4：C,65.63；H,5.51；N,6.51；Survey constituent content (%)：C, 65.60；H, 5.51；N, 6.54.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 85：The synthesis of compound 83：
According to the synthesis of compound 5, step is identical, obtains red powder compound 83 (206.3mg, yield 59%), Mass spectral analysis determine molecular ion quality be：874.41 (calculated value is：874.36)；Theoretical elemental content (%) C48H49IrN4：C,65.95；H,5.65；N,6.41；Survey constituent content (%)：C, 65.92；H, 5.68；N, 6.41.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 86：The synthesis of compound 84：
According to the synthesis of compound 5, step is identical, obtains red powder compound 84 (202.5mg, yield 57%), Mass spectral analysis determine molecular ion quality be：888.30 (calculated value is：888.37)；Theoretical elemental content (%) C49H51IrN4：C,66.26；H,5.79；N,6.31；Survey constituent content (%)：C, 66.31；H, 5.77；N, 6.29.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 87：The synthesis of compound 85：
According to the synthesis of compound 5, step is identical, obtains red powder compound 85 (234.5mg, yield 65%), Mass spectral analysis determine molecular ion quality be：902.6 (calculated value is：902.39)；Theoretical elemental content (%) C50H53IrN4： C,66.56；H,5.92；N,6.21；Survey constituent content (%)：C,66.72；H,5.74；N,6.41.Above-mentioned analysis result table Bright, the product of acquisition is the product being expected.
Embodiment 88：The synthesis of compound 86：
According to the synthesis of compound 5, step is identical, obtains red powder compound 86 (260.5mg, yield 69%), Mass spectral analysis determine molecular ion quality be：944.32 (calculated value is：944.44)；Theoretical elemental content (%) C53H59IrN4：C,67.41；H,6.30；N,5.93；Survey constituent content (%)：C,67.92；H,6.24；N,5.70.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 89：The synthesis of compound 87：
According to the synthesis of compound 5, step is identical, obtains red powder compound 87 (256.5mg, yield 70%), Mass spectral analysis determine molecular ion quality be：916.32 (calculated value is：916.41)；Theoretical elemental content (%) C51H55IrN4：C,66.86；H,6.05；N,6.11；Survey constituent content (%)：C,66.92；H,6.15；N,5.95.Above-mentioned point Analysis the result shows that, the product of acquisition be it is expected that product.
Embodiment 90：The synthesis of compound 88：
According to the synthesis of compound 5, step is identical, obtains red powder compound 88 (256.6mg, yield 66%), Mass spectral analysis determine molecular ion quality be：972.6 (calculated value is：972.47)；Theoretical elemental content (%) C55H63IrN4： C,67.94；H,6.53；N,5.76；Survey constituent content (%)：C,67.99；H,6.43；N,5.54.Above-mentioned analysis result table Bright, the product of acquisition is the product being expected.
Embodiment 91：The synthesis of compound 89：
According to the synthesis of compound 1, step is identical, obtains red powder compound 89 (277.4mg, yield 72%), Mass spectral analysis determine molecular ion quality be：963.35 (calculated value is：963.33)；Theoretical elemental content (%) C45H46F6IrN5：C,56.12；H,4.81；N,7.27；Survey constituent content (%)：C, 56.11；H, 4.80；N, 7.29.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 92：The synthesis of compound 90：
According to the synthesis of compound 2, step is identical, obtains red powder compound 90 (271.7mg, yield 66%), Mass spectral analysis determine molecular ion quality be：1029.25 (calculated value is：1029.28)；Theoretical elemental content (%) C51H40F6IrN5：C,59.52；H,3.92；N,6.81；Survey constituent content (%)：C, 59.55；H, 3.95；N, 6.75.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 93：The synthesis of compound 91：
According to the synthesis of compound 2, step is identical, obtains red powder compound 91 (258.0mg, yield 61%), Mass spectral analysis determine molecular ion quality be：1057.22 (calculated value is：1057.31)；Theoretical elemental content (%) C53H44F6IrN5：C,60.21；H,4.20；N,6.62；Survey constituent content (%)：C, 60.25；H, 4.16；N, 6.62.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 94：The synthesis of compound 92：
According to the synthesis of compound 2, step is identical, obtains red powder compound 92 (274.0mg, yield 60%), Mass spectral analysis determine molecular ion quality be：1057.22 (calculated value is：1141.41)；Theoretical elemental content (%) C59H56F6IrN5：C,62.09；H,4.95；N,6.14；Survey constituent content (%)：C, 62.05；H, 4.99；N, 6.14.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 95：The synthesis of compound 93：
According to the synthesis of compound 5, step is identical, obtains red powder compound 93 (236.9mg, yield 63%), Mass spectral analysis determine molecular ion quality be：940.22 (calculated value is：940.26)；Theoretical elemental content (%) C45H37F6IrN4：C,57.50；H,3.97；N,5.96；Survey constituent content (%)：C, 57.55；H, 3.91；N, 5.97.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 96：The synthesis of compound 94：
According to the synthesis of compound 5, step is identical, obtains red powder compound 94 (236.7mg, yield 62%), Mass spectral analysis determine molecular ion quality be：954.22 (calculated value is：954.27)；Theoretical elemental content (%) C46H39F6IrN4：C,57.91；H,4.12；N,5.87；Survey constituent content (%)：C, 57.88；H, 4.15；N, 5.87.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 97：The synthesis of compound 95：
According to the synthesis of compound 5, step is identical, obtains red powder compound 95 (232.4mg, yield 60%), Mass spectral analysis determine molecular ion quality be：968.32 (calculated value is：968.29)；Theoretical elemental content (%) C47H41F6IrN4：C,58.31；H,4.27；N,5.79；Survey constituent content (%)：C, 58.27；H, 4.31；N, 5.79.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 98：The synthesis of compound 96：
According to the synthesis of compound 5, step is identical, obtains dark red powder shape compound 96 (232mg, yield 59%), Mass spectral analysis determine molecular ion quality be：982.5 (calculated value is：982.30)；Theoretical elemental content (%) C48H43F6IrN4：C,58.70；H,4.41；N,5.70；Survey constituent content (%)：C,58.92；H,4.22；N,5.62.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 99：The synthesis of compound 97：
According to the synthesis of compound 5, step is identical, obtains dark red powder shape compound 97 (208.8mg, yield 51%), the molecular ion quality of mass spectral analysis determination is：1024.45 (calculated value is：1024.35)；Theoretical elemental content (%) C51H49F6IrN4：C,59.81；H,4.82；N,5.47；Survey constituent content (%)：C,59.92；H,4.94；N,5.52.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 100：The synthesis of compound 98：
According to the synthesis of compound 5, step is identical, obtains dark red powder shape compound 98 (207.2mg, yield 52%), the molecular ion quality of mass spectral analysis determination is：996.66 (calculated value is：996.32)；Theoretical elemental content (%) C49H45F6IrN4：C,59.08；H,4.55；N,5.62；Survey constituent content (%)：C,59.12；H,4.65；N,5.66.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 101：The synthesis of compound 99：
According to the synthesis of compound 5, step is identical, obtains dark red powder shape compound 99 (259.4mg, yield 61%), the molecular ion quality of mass spectral analysis determination is：1052.61 (calculated value is：1052.38)；Theoretical elemental content (%) C53H53F6IrN4：C,60.50；H,5.08；N,5.32；Survey constituent content (%)：C,60.65；H,5.12；N,5.44.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 102：The synthesis of compound 100：
According to the synthesis of compound 1, step is identical, obtains red powder compound 100 (270.4mg, yield 71%), Mass spectral analysis determine molecular ion quality be：963.49 (calculated value is：963.33)；Theoretical elemental content (%) C45H46F6IrN5：C,56.12；H,4.81；N,7.27；Survey constituent content (%)：C, 56.17；H, 4.85；N, 7.39.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 103：The synthesis of compound 101：
According to the synthesis of compound 2, step is identical, obtains red powder compound 101 (262.7mg, yield 65%), Mass spectral analysis determine molecular ion quality be：1029.45 (calculated value is：1029.28)；Theoretical elemental content (%) C51H40F6IrN5：C,59.52；H,3.92；N,6.81；Survey constituent content (%)：C, 59.57；H, 3.85；N, 6.79.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 104：The synthesis of compound 102：
According to the synthesis of compound 2, step is identical, obtains red powder compound 102 (248.0mg, yield 59%), Mass spectral analysis determine molecular ion quality be：1057.36 (calculated value is：1057.31)；Theoretical elemental content (%) C53H44F6IrN5：C,60.21；H,4.20；N,6.62；Survey constituent content (%)：C, 60.31；H, 4.21；N, 6.68.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 105：The synthesis of compound 103：
According to the synthesis of compound 2, step is identical, obtains red powder compound 103 (270.0mg, yield 59%), Mass spectral analysis determine molecular ion quality be：1057.22 (calculated value is：1141.41)；Theoretical elemental content (%) C59H56F6IrN5：C,62.09；H,4.95；N,6.14；Survey constituent content (%)：C, 62.11；H, 4.99；N, 6.36.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 106：The synthesis of compound 104：
According to the synthesis of compound 5, step is identical, obtains red powder compound 104 (236.9mg, yield 63%), Mass spectral analysis determine molecular ion quality be：940.62 (calculated value is：940.26)；Theoretical elemental content (%) C45H37F6IrN4：C,57.50；H,3.97；N,5.96；Survey constituent content (%)：C, 57.58；H, 3.94；N, 5.99.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 106：The synthesis of compound 105：
According to the synthesis of compound 5, step is identical, obtains red powder compound 105 (228.7mg, yield 60%), Mass spectral analysis determine molecular ion quality be：954.22 (calculated value is：954.27)；Theoretical elemental content (%) C46H39F6IrN4：C,57.91；H,4.12；N,5.87；Survey constituent content (%)：C, 57.86；H, 4.36；N, 5.82.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 107：The synthesis of compound 106：
According to the synthesis of compound 5, step is identical, obtains red powder compound 106 (227.4mg, yield 59%), Mass spectral analysis determine molecular ion quality be：968.32 (calculated value is：968.29)；Theoretical elemental content (%) C47H41F6IrN4：C,58.31；H,4.27；N,5.79；Survey constituent content (%)：C, 58.19；H, 4.36；N, 5.88.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 109：The synthesis of compound 107：
According to the synthesis of compound 5, step is identical, obtains dark red powder shape compound 107 (224mg, yield 58%), Mass spectral analysis determine molecular ion quality be：982.5 (calculated value is：982.30)；Theoretical elemental content (%) C48H43F6IrN4：C,58.70；H,4.41；N,5.70；Survey constituent content (%)：C,58.93；H,4.29；N,5.72.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 110：The synthesis of compound 108：
According to the synthesis of compound 5, step is identical, obtains dark red powder shape compound 108 (208.8mg, yield 51%), the molecular ion quality of mass spectral analysis determination is：1024.65 (calculated value is：1024.35)；Theoretical elemental content (%) C51H49F6IrN4：C,59.81；H,4.82；N,5.47；Survey constituent content (%)：C,59.82；H,4.96；N,5.55.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 111：The synthesis of compound 109：
According to the synthesis of compound 5, step is identical, obtains dark red powder shape compound 109 (207.2mg, yield 52%), the molecular ion quality of mass spectral analysis determination is：996.61 (calculated value is：996.32)；Theoretical elemental content (%) C49H45F6IrN4：C,59.08；H,4.55；N,5.62；Survey constituent content (%)：C,59.13；H,4.61；N,5.68.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 112：The synthesis of compound 110：
According to the synthesis of compound 5, step is identical, obtains dark red powder shape compound 110 (252.4mg, yield 61%), the molecular ion quality of mass spectral analysis determination is：1052.41 (calculated value is：1052.38)；Theoretical elemental content (%) C53H53F6IrN4：C,60.50；H,5.08；N,5.32；Survey constituent content (%)：C,60.61；H,5.11；N,5.47.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 113：The synthesis of compound 111：
According to the synthesis of compound 1, step is identical, obtains red powder compound 111 (228.6mg, yield 52%), Mass spectral analysis determine molecular ion quality be：1099.41 (calculated value is：1099.30)；Theoretical elemental content (%) C47H44F12IrN5：C,51.36；H,4.04；N,6.37；Survey constituent content (%)：C, 51.42；H, 4.01；N, 6.46.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 114：The synthesis of compound 112：
According to the synthesis of compound 2, step is identical, obtains red powder compound 112 (209.3mg, yield 42%), Mass spectral analysis determine molecular ion quality be：1165.45 (calculated value is：1165.26)；Theoretical elemental content (%) C53H38F12IrN5：C,54.64；H,3.29；N,6.01；Survey constituent content (%)：C,54.74；H,3.21；N,6.06.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 115：The synthesis of compound 113：
According to the synthesis of compound 2, step is identical, obtains red powder compound 113 (214.4mg, yield 45%), Mass spectral analysis determine molecular ion quality be：1193.42 (calculated value is：1193.29)；Theoretical elemental content (%) C55H42F12IrN5：C,55.36；H,3.55；N,5.87；Survey constituent content (%)：C, C, 55.45；H,3.81；N,5.97.On It states analysis result and shows the product that the product of acquisition is estimated.
Embodiment 116：The synthesis of compound 114：
According to the synthesis of compound 2, step is identical, obtains red powder compound 114 (227.2mg, yield 45%), Mass spectral analysis determine molecular ion quality be：1277.52 (calculated value is：1277.38)；Theoretical elemental content (%) C61H54F12IrN5：C,57.36；H,4.26；N,5.48；Survey constituent content (%)：C,57.46；H,4.36；N,5.68.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 117：The synthesis of compound 115：
According to the synthesis of compound 5, step is identical, obtains red powder compound 115 (220.8mg, yield 51%), Mass spectral analysis determine molecular ion quality be：1076.43 (calculated value is：1076.23)；Theoretical elemental content (%) C47H35F12IrN4：C,52.46；H,3.28；N,5.21；Survey constituent content (%)：C,52.66；H,3.35；N,5.32.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 118：The synthesis of compound 116：
According to the synthesis of compound 5, step is identical, obtains red powder compound 116 (178.1mg, yield 42%), Mass spectral analysis determine molecular ion quality be：1090.44 (calculated value is：1090.25)；Theoretical elemental content (%) C48H37F12IrN4：C,52.89；H,3.42；N,5.14；Survey constituent content (%)：C,52.91；H,3.49；N,5.21.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 119：The synthesis of compound 117：
According to the synthesis of compound 5, step is identical, obtains red powder compound 117 (169.9mg, yield 40%), Mass spectral analysis determine molecular ion quality be：1104.32 (calculated value is：1104.26)；Theoretical elemental content (%) C49H39F12IrN4：C,53.31；H,3.56；N,5.07；Survey constituent content (%)：C,53.31；H,3.56；N,5.07.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 120：The synthesis of compound 118：
According to the synthesis of compound 5, step is identical, obtains red powder compound 118 (205.1mg, yield 46%), Mass spectral analysis determine molecular ion quality be：1118.49 (calculated value is：1118.28)；Theoretical elemental content (%) C50H41F12IrN4：C,53.71；H,3.70；N,5.01；Survey constituent content (%)：C,53.99；H,3.92；N,5.11.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 121：The synthesis of compound 119：
According to the synthesis of compound 5, step is identical, obtains red powder compound 119 (190.2mg, yield 41%), Mass spectral analysis determine molecular ion quality be：1160.62 (calculated value is：1160.32)；Theoretical elemental content (%) C53H47F12IrN4：C,54.87；H,4.08；N,4.83；Survey constituent content (%)：C,54.92；H,4.18；N,4.89.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 122：The synthesis of compound 120：
According to the synthesis of compound 5, step is identical, obtains red powder compound 120 (208.1mg, yield 46%), Mass spectral analysis determine molecular ion quality be：1132.44 (calculated value is：1132.29)；Theoretical elemental content (%) C51H43F12IrN4：C,54.11；H,3.83；N,4.95；Survey constituent content (%)：C,54.22；H,3.92；N,4.91.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 123：The synthesis of compound 121：
According to the synthesis of compound 5, step is identical, obtains red powder compound 121 (185.3mg, yield 39%), Mass spectral analysis determine molecular ion quality be：1188.52 (calculated value is：1188.36)；Theoretical elemental content (%) C55H51F12IrN4：C,55.59；H,4.33；N,4.72；Survey constituent content (%)：C,55.62；H,4.39；N,4.79.It is above-mentioned Analysis result shows the product that the product of acquisition is estimated.
Embodiment 124：Fa Guangqijian [ITO/NPB/Bebq2:Compound 1 (5%)/Bepp2/LiF/Al]
Hole transmission layer NPB (40nm) is deposited successively on the glass substrate for be coated with ito anode, the layer main body that shines is using double (10- Qiang Jibenbings [h]Quinoline) beryllium (Bebq2), guest materials is using the compound 1 prepared for embodiment 3, doping concentration 5% (30nm), electron transfer layer Bepp2(30nm), electron injection material LiFAl cathodesLuminescent layer adulterates A concentration of weight percentage.It is 5 × 10 that pressure is kept during vapor deposition-6Pa.The device cut-in voltage is 2.9V, maximum electricity Flow efficiency 1.17cd/A, power efficiency 1.22lm/W.The device sends out light dark red, peak position 688nm, maximum brightness 3845cd/m2。
Embodiment 125：Fa Guangqijian [ITO/NPB/Bebq2:Compound 5 (5%)/Bepp2/LiF/Al]
Hole transmission layer NPB (40nm) is deposited successively on the glass substrate for be coated with ito anode, the layer main body that shines is using double (10- Qiang Jibenbings [h]Quinoline) beryllium (Bebq2), guest materials uses the compound 5 prepared for embodiment 7, doping concentration (weight Measure percentage composition) it is 5% (30nm), electron transfer layer Bepp2(30nm), electron injection material LiFAl cathodesLuminescent layer doping concentration is weight percentage.It is 5 × 10 that pressure is kept during vapor deposition-6Pa.The device is opened Open voltage 2.7V, maximum current efficiency 1.6cd/A, power efficiency 1.87lm/W.The device sends out light dark red, peak position 676nm, maximum Brightness 5965cd/m2。
Embodiment 126：Fa Guangqijian [ITO/NPB/Bebq2:Compound 12 (5%)/Bepp2/LiF/Al]
Hole transmission layer NPB (40nm) is deposited successively on the glass substrate for be coated with ito anode, the layer main body that shines is using double (10- Qiang Jibenbings [h]Quinoline) beryllium (Bebq2), guest materials uses the compound 12 prepared for embodiment 14, doping concentration (weight percentage) is 5% (30nm), electron transfer layer Bepp2(30nm), electron injection material LiFAl cathodesLuminescent layer doping concentration is weight percentage.It is 5 × 10 that pressure is kept during vapor deposition-6Pa.The device is opened It is 2.4V, maximum current efficiency 5.1cd/A, power efficiency 6.7lm/W to open voltage.The device sends out light dark red, peak position 664nm, most Big brightness 12845cd/m2。
Embodiment 127：Fa Guangqijian [ITO/NPB/Bebq2:Compound 16 (5%)/Bepp2/LiF/Al]
Hole transmission layer NPB (40nm) is deposited successively on the glass substrate for be coated with ito anode, the layer main body that shines is using double (10- Qiang Jibenbings [h]Quinoline) beryllium (Bebq2), guest materials uses the compound 16 prepared for embodiment 18, doping concentration (weight percentage) is 5% (30nm), electron transfer layer Bepp2(30nm), electron injection material LiFAl cathodesLuminescent layer doping concentration is weight percentage.It is 5 × 10 that pressure is kept during vapor deposition-6Pa.The device is opened It is 2.4V, maximum current efficiency 6.7cd/A, power efficiency 8.9lm/W to open voltage.The device sends out light dark red, peak position 652nm, most Big brightness 16345cd/m2。
Embodiment 128：Fa Guangqijian [ITO/NPB/Bebq2:Compound 34 (5%)/Bepp2/LiF/Al]
Hole transmission layer NPB (40nm) is deposited successively on the glass substrate for be coated with ito anode, the layer main body that shines is using double (10- Qiang Jibenbings [h]Quinoline) beryllium (Bebq2), guest materials uses the compound 34 prepared for embodiment 36, doping concentration (weight percentage) is 5% (30nm), electron transfer layer Bepp2(30nm), electron injection material LiFAl cathodesLuminescent layer doping concentration is weight percentage.It is 5 × 10 that pressure is kept during vapor deposition-6Pa.The device is opened It is 2.4V, maximum current efficiency 6.9cd/A, power efficiency 9.1lm/W to open voltage.The device sends out light dark red, peak position 650nm, most Big brightness 14545cd/m2。
Embodiment 129：Fa Guangqijian [ITO/NPB/Bebq2:Compound 38 (5%)/Bepp2/LiF/Al]
Hole transmission layer NPB (40nm) is deposited successively on the glass substrate for be coated with ito anode, the layer main body that shines is using double (10- Qiang Jibenbings [h]Quinoline) beryllium (Bebq2), guest materials uses the compound 38 prepared for embodiment 40, doping concentration (weight percentage) is 5% (30nm), electron transfer layer Bepp2(30nm), electron injection material LiFAl cathodesLuminescent layer doping concentration is weight percentage.It is 5 × 10 that pressure is kept during vapor deposition-6Pa.The device is opened It is 2.6V, maximum current efficiency 8.6cd/A, power efficiency 10.3lm/W to open voltage.The device sends out light dark red, peak position 644nm, most Big brightness 16845cd/m2。
Embodiment 130：Fa Guangqijian [ITO/NPB/Bebq2:Compound 89 (5%)/Bepp2/LiF/Al]
Hole transmission layer NPB (40nm) is deposited successively on the glass substrate for be coated with ito anode, the layer main body that shines is using double (10- Qiang Jibenbings [h]Quinoline) beryllium (Bebq2), guest materials uses the compound 89 prepared for embodiment 91, doping concentration (weight percentage) is 5% (30nm), electron transfer layer Bepp2(30nm), electron injection material LiFAl cathodesLuminescent layer doping concentration is weight percentage.It is 5 × 10 that pressure is kept during vapor deposition-6Pa.The device is opened It is 3V, maximum current efficiency 0.43cd/A, power efficiency 0.45lm/W to open voltage.The device sends out light dark red, peak position 700nm, most Big brightness 2818cd/m2。

Claims (6)

1. a kind of feux rouges is to near-infrared phosphorescent iridium complex luminescent material, shown in one of structural formula is following：
2. a kind of feux rouges is to near-infrared phosphorescent iridium complex luminescent material, shown in one of structural formula is following：
3. a kind of feux rouges as claimed in claim 1 or 2 to near-infrared phosphorescent iridium complex luminescent material is preparing organic electroluminescence hair Application in terms of optical device.
4. a kind of feux rouges as claimed in claim 3 to near-infrared phosphorescent iridium complex luminescent material is preparing organic electroluminescent Application in terms of device, it is characterised in that：Organic electroluminescence device is by one or more layers between cathode, anode and two electrodes Organic layer is constituted, and at least one layer of in organic layer is luminescent layer, more than one feux rouges as claimed in claim 1 or 2 to near-infrared phosphorus Light complex of iridium luminescent material, which is doped in as phosphorescent guest in material of main part, constitutes luminescent layer.
5. a kind of feux rouges as claimed in claim 3 to near-infrared phosphorescent iridium complex luminescent material is preparing organic electroluminescent Application in terms of device, it is characterised in that：The electroluminescent device is used to prepare lighting source or flat-panel monitor.
6. a kind of feux rouges as claimed in claim 4 to near-infrared phosphorescent iridium complex luminescent material is preparing organic electroluminescent Application in terms of device, it is characterised in that：The electroluminescent device is used to prepare lighting source or flat-panel monitor.
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CN108484680B (en) * 2018-01-31 2020-12-11 马鞍山南京大学高新技术研究院 Iridium complex with bis-thio aromatic ring/aromatic heterocyclic phosphoric acid compound as auxiliary ligand
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