CN102140119A - Phosphorescent iridium complex and electroluminescence device thereof - Google Patents

Phosphorescent iridium complex and electroluminescence device thereof Download PDF

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CN102140119A
CN102140119A CN2010105902954A CN201010590295A CN102140119A CN 102140119 A CN102140119 A CN 102140119A CN 2010105902954 A CN2010105902954 A CN 2010105902954A CN 201010590295 A CN201010590295 A CN 201010590295A CN 102140119 A CN102140119 A CN 102140119A
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iridium complex
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密保秀
高志强
黄维
廖章金
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Nanjing Post and Telecommunication University
Nanjing University of Posts and Telecommunications
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Abstract

The invention discloses a phosphorescent iridium complex with high luminescent quantum efficiency and thermal stability and an electroluminescence device of the complex. In the phosphorescent iridium complex, the ligands are characterized by 3-or 6-phenyl pyridazine, a central metal ion is Ir (III), and the metal ion and three ligands form a neutral complex with the same cyclic metal ligands. In the ligand in the invention, the atom adjacent to coordination N atom is also N atom, thereby avoiding the interference of H atom on the adjacent C atom on complexing of N and metal when pyridine is taken as ligand so that the binding between the ligands and the metal ion is firmer and metal ligand charge transfer (MLCT) process is facilitated. Thus, the iridium complex has high luminescent quantum efficiency and thermal stability. Simultaneously, the energy gap of the iridium complex can be regulated through changing other functional groups on the ligand, so as to regulate the emission wavelength of a material. The iridium complex has an application potential in the aspects of organic electroluminescent display based on red-blue-green three primary colors, backlight in liquid crystal display, organic solid illumination and the like.

Description

A kind of phosphorescent iridium complex and electroluminescent device thereof
Technical field
The invention belongs to organic phosphorescent material and organic electroluminescent Application Areas, comprise complex of iridium material and electroluminescent thereof that efficient triplet state is luminous, they are expected to be applied at the backlight of ORGANIC ELECTROLUMINESCENCE DISPLAYS, liquid crystal and the luminous field of organic solid.
Background technology
Organic electroluminescent LED (OLED) is to utilize organic materials luminous device under electricity injects, it have all solid state, from main light emission, brightness height, visual angle wide (reaching more than 170 degree), response speed fast (about tens nanoseconds), thin thickness, can use flexible base, board, low voltage direct drive (3～10V), low in energy consumption, advantage such as operating temperature range is wide.And, simple based on the device making technics of organic materials, be easy to large-area preparation, environmental friendliness can adopt the lower method for manufacturing thin film of temperature, and as spin coating, spray ink Printing, impregnating technology, cost of manufacture is lower.OLED has huge application potential at aspects such as the backlight of flat panel display of new generation, liquid-crystal display and solid-state illuminations.Therefore, electroluminescent organic material and device have caused the extensive concern of scientific circles and international renowned company and have played an active part in.
According to the difference of principle of luminosity, organic electroluminescence material can be divided into based on the luminous organic electroluminescent fluorescent materials of singlet exciton with based on the luminous organic electromechanical phosphorescent material of triplet excitons.Different with photoluminescence, in the organic electroluminescent process, singlet exciton and triplet excitons generate simultaneously.According to spin quantum statistical theory, the generating probability ratio of singlet exciton and triplet excitons is 1: 3, and according to the effect of prohibiting of quantum statistics, non-radiative decay mainly takes place triplet excitons, and is minimum to luminous contribution, have only singlet exciton auxilliary penetrate luminous.Therefore the maximum internal quantum efficiency based on the device of common organic electroluminescent fluorescent materials is 25%.In the phosphorescence heavy metal complex, because the introducing of heavy metal atom will produce between metal and the part from the stronger orbit coupling of revolving, make the triplet state feature of track thicken, thereby cause the radiative transition of triplet excitons, produce phosphorescence.That is to say that the phosphorescence heavy metal complex can utilize singlet exciton, can utilize triplet excitons again, in theory, can reach 100% based on the OLED internal quantum efficiency of phosphorescence heavy metal complex material.Therefore, phosphor material has important status in organic electroluminescent.The heavy metal atom that is used for phosphor material has platinum (Pt), osmium (Os), iridium (Ir), gold (Au), palladium (Pd) and ruthenium (Ru) etc.Studies show that, be the phosphorescent emissive material of tool potentiality in the electromechanical phosphorescent material based on the title complex of metal iridium.
Be applied to electroluminescent device, phosphor materials such as complex of iridium often have thermostability good inadequately, and luminous intensity awaits improving, and easily produce more serious triplet state-triplet state quencher, the such or such problem of the not ideal enough grade of level structure.This class phosphorescent iridium complex that the present invention provides has advantages such as luminous intensity height, Heat stability is good, is expected to be applied in each Application Areas of organic electroluminescence device.
Summary of the invention
Technical problem: purpose of the present invention provides a kind of phosphorescent iridium complex and electroluminescent device thereof, can improve the electric property of this class complex of iridium, and luminous efficiency can be improved, thermostability improves.
Technical scheme: phosphorescent iridium complex of the present invention is that part complexing trivalent iridium belongs to ion and forms with 3-phenyl or 6-phenyl pyridazine and derivative thereof, and its structure is as follows:
Figure BSA00000387069700021
In the said structure formula, 3-phenyl or 6-phenyl pyridazine are precursor structure, R 1, R 2Be not have two kinds of related groups, get one of following material respectively: hydrogen atom, halogen atom, nitro, cyano group, acyl group, sulfuryl, alkyl, substituted alkyl, cycloalkyl, cycloalkenyl group, alkoxyl group, aryloxy, alkylthio, replacement be silica-based, replace the fused ring aryl that siloxy, trifluoromethyl, aromatic amino, fatty amido, aromatic base or heterocyclic radical, fused ring aryl and heteroatoms replace; Simultaneously, do not get rid of R 1Or R 2Part or all of group and precursor structure forms ring texture.
Described ring texture comprises furans, thiophene, pyrroles, pyrazoles, oxazole, thiazole, imidazoles, pyridine, pyrans, pyrazine, pyrimidine, carbazole, quinoline, isoquinoline 99.9, indoles, pteridine, acridine, azophenlyene, thiodiphenylamine or purine.
Organic electroluminescence device comprises the substrate layer that sets gradually from the bottom to top, anode, hole injection layer or hole transmission layer, buffer layer or blocking layer, luminescent layer, buffer layer or blocking layer, electron injecting layer or electron transfer layer and negative electrode, the hole transmission layer that contains multilayer film structure in the organic electroluminescence device, buffer layer or blocking layer, luminescent layer, buffer layer or blocking layer, all or part of in electron injecting layer or the electron transfer layer, and the wherein one deck in this multilayer film structure or multilayer contain the described phosphorescent iridium complex of claim 1.
Above-mentioned iridium complex phosphorescence material, its preparation technology has two steps: first step is the synthetic of 3-phenyl or 6-phenyl pyridazine class part; Second step is that part and trivalent iridium belong to the synthetic of the formed complex of iridium of ion.Preparation process is all carried out under nitrogen protection, and what particularly point out is that second step was to carry out under high temperature (～200 ℃) condition.
Complex of iridium class phosphor material of the present invention is mainly used in the preparation organic electroluminescence device.Its structure comprises all or part of of following thin film layer: substrate layer, anode, hole injection layer or hole transmission layer, blocking layer or buffer layer, luminescent layer, blocking layer or buffer layer, electron injecting layer or electron transfer layer, and negative electrode.Have at least one deck to comprise above-mentioned phosphorescent iridium complex in the above-mentioned thin film layer.
Substrate is the supporting layer of device, can be quartz plate, sheet glass, tinsel or film, plastic film.Anode places on the substrate, usually, is made by the higher metal of work function (gold and silver, aluminium, nickel etc.), metal oxide (Indium sesquioxide, stannic oxide etc.), carbon black, conductive polymers etc.Negative electrode is to be made of the metal or metal alloy than low work function, for example: magnesium, aluminium, silver, indium metal or their alloy.The thickness that negative electrode and anode are general is 5-1000nm, and its making can be vacuum evaporation or sputter; If material is very thin particle, as metal, carbon black, metal oxide, conductive polymers etc., electrode can obtain by the spin coating of solution; In addition, electrochemical deposition also can make corresponding electrode.Further, negative electrode and anode can have multilayered structure, and for example, negative electrode can be made of the lithium fluoride of 0.1-1nm and the aluminium of 10-100nm.Based on self luminous requirement, it is transparent that an electrode will be arranged at least, and the transmitance more than 60% is arranged.Luminescent layer can be that material of main part is luminous, also can be that luminescent material is doped in the material of main part; Can be the single-shot photosphere, also can be multi-luminescent layer; Require as white light parts in order to reach different spectrum, hole transmission layer and electron transfer layer also can produce light emission; One of luminescent material wherein is a phosphorescent iridium complex of the present invention.Similarly, electronics injects and transport layer can be an individual layer, also can be multilayer, and its composition of every layer promptly can be that single-material also can be a mixing material.Especially, electronics injects and transport material will have good transmission electronic ability, and bigger electron affinity is arranged, for example, 4,7-phenylbenzene 1,10-phenanthroline (BPhen) and oxine aluminium (Alq 3).
Beneficial effect: organic electrofluorescent iridium complex material provided by the present invention has the following advantages:
1, owing to group around the coordination N atom in the part is less, make it become key time space steric hindrance less with Ir (III) coordination, thereby combine more firm between part and the central metallic ions, help the MLCT process, and the luminous efficiency of the complex of iridium class phosphor material that forms can be improved, thermostability improves.
2, be convenient in 3-phenyl or 6-phenyl pyridazine group, introduce various different functional groups, regulate the emission wavelength of this class complex of iridium.
3, be convenient in 3-phenyl or 6-phenyl pyridazine group, introduce all kinds of functional groups, improve the electric property of this class complex of iridium with electrons/injection or transmission performance.
4, be convenient in 3-phenyl or 6-phenyl pyridazine group, introduce big steric group, form the cladodification structure and produce certain steric effect, thereby reduce the direct effect between the title complex luminescence center, reduce the self quenching phenomenon of triplet excitons, improve the luminescent properties of phosphor material.
5. complex of iridium provided by the invention is introduced organic electroluminescence device, can obtain the organic electroluminescence device of the different glow colors of excellent property.
Description of drawings
Fig. 1 title complex (Ir (MDFPPya) 3) synthesis path.
Fig. 2 is the structural representation of phosphorescent iridium complex electroluminescent device.
Fig. 3 phosphorescent iridium complex (Ir (MDFPPya) 3) UV, visible light in dichloromethane solution absorbs (UV/vis) spectrum, photoluminescence (PL) spectrum.
Fig. 4 phosphorescent iridium complex (Ir (BFPPya) 3) UV, visible light in dichloromethane solution absorbs (UV/vis) spectrum, photoluminescence (PL) spectrum.
Current density-the voltage of electroluminescent device among Fig. 5 embodiment 6-luminosity graphic representation.
Current density-the voltage of electroluminescent device among Fig. 6 embodiment 7-luminosity graphic representation.
Embodiment
In order to understand the content of patent of the present invention better, further specify technical scheme of the present invention below by concrete example and legend, but these embodiments do not limit the present invention, and other application in the invention essential scope and variation and modification comprise in the present invention too.
This complex structure formula (I) is as follows:
Figure BSA00000387069700041
In the said structure formula, 3-phenyl or 6-phenyl pyridazine are precursor structure, R 1, R 2Be not have two kinds of related groups, get one of following material respectively: hydrogen atom, halogen atom, nitro, cyano group, acyl group, sulfuryl, alkyl, substituted alkyl, cycloalkyl, cycloalkenyl group, alkoxyl group, aryloxy, alkylthio, replacement be silica-based, replace the fused ring aryl that siloxy, trifluoromethyl, aromatic amino, fatty amido, aromatic base or heterocyclic radical, fused ring aryl and heteroatoms replace; Simultaneously, do not get rid of R 1Or R 2Part or all of group and precursor structure forms ring texture.
Described ring texture comprises furans, thiophene, pyrroles, pyrazoles, oxazole, thiazole, imidazoles, pyridine, pyrans, pyrazine, pyrimidine, carbazole, quinoline, isoquinoline 99.9, indoles, pteridine, acridine, azophenlyene, thiodiphenylamine or purine.
Organic electroluminescence device 100 comprises the substrate layer 101 that sets gradually from the bottom to top, anode 102, hole injection layer or hole transmission layer 103, buffer layer or blocking layer 104, luminescent layer 105, buffer layer or blocking layer 106, electron injecting layer or electron transfer layer 107 and negative electrode 108, the hole transmission layer 103 that contains multilayer film structure in the organic electroluminescence device 100, buffer layer or blocking layer 104, luminescent layer 105, buffer layer or blocking layer 106, all or part of in electron injecting layer or the electron transfer layer 107, and the wherein one deck in this multilayer film structure or multilayer contain the described phosphorescent iridium complex of claim 1.
Embodiment 1,3-methyl-6-22 ', 4 '-(fluorophenyl) pyridazine [3-methyl-6-(2,4-difluoro-phenyl) pyridazine abbreviates MDFPPya as] synthetic.Get the 2,4 difluorobenzene boric acid of 250mg 3-methyl-6-chlorine pyridazine, 463mg and 67mg tetraphenylphosphonium palladium in two mouthfuls of flasks, add the K of 12ml toluene, 2ml ethanol and 2.1ml 2M 2CO 3Solution.Under 100 ℃ of temperature, backflow 24h.Leave standstill cooling, quench with methylene dichloride and get, dewater with anhydrous magnesium sulfate again.Decompression is steamed to slip to remove and is desolvated, and silica gel column chromatography obtains part MDFPPya (79%).
Embodiment 2, three (3-methyl-6-two (2 ', 4 '-fluorophenyl) pyridazine) close iridium [tris[3-(and 2,4-difluoro-phenyl)-6-methylpyridazinato-N 1, C 2] iridium, abbreviate Ir (MDFPPya) as 3] synthetic.Get part 3-methyl-6-two (2 ', 4 '-fluorophenyl) pyridazine (MDFPPya) 163mg and 100mg IrCl 3H 2O adds 6ml cellosolvo and 2ml and goes dried up in two mouthfuls of flasks.Under 110 ℃ of temperature, backflow 12h.Leave standstill cooling, add the 5ml deionized water, filter.60 ℃ of vacuum-drying 4h get 151mg (75%) chlorine bridge dimer.Then with dimer, 62mg MDFPPya and 104mg K 2CO 3Join in two mouthfuls of bottles, add 5ml glycerine.Under 185 ℃ of temperature, reaction 12h.Leave standstill cooling, quench with methylene dichloride and get decompression steaming slide except that desolvating, silica gel column chromatography obtains end product Ir (MDFPPya) 3135mg (71%).Ir (MDFPPya) 3Nuclear magnetic spectrogram be: 1(TMS is interior mark to HNMR, solvent C DCl 3) δ (ppm): 8.26-8.24 (m, J=2.0Hz, 3H), 7.22 (d, J=8.8Hz, 6H, 6.45-6.38 (m, J=3.6Hz, 6H), 2.30 (s, 9H).Ir (MDFPPya) 3Synthetic route see Fig. 1.
Embodiment 3, three-(3,6-two (4 '-fluorophenyl) pyridazine) closes iridium [tris[3,6-bis (4-fluorophenyl) pyri-dazinato-N 1, C 2] iridium, abbreviate Ir (BFPPya) as 3] synthetic.At N 2Under the protection, with 378.0mg 3,6-two (4 '-fluorophenyl) pyridazine (BFPPya) and 172.4mg three (methyl ethyl diketone root) close iridium (III) [Ir (acac) 3] join in the 5ml glycerine.Be warming up to 50 ℃, with the vacuum pump 4h that bleeds.Be warming up to 190 ℃ subsequently, backflow 12h.After having treated that a large amount of yellow solids are separated out, stopped reaction is cooled to room temperature, uses dichloromethane extraction, and underpressure distillation removes and desolvates, and filters, and washs with small amount of methanol, and vacuum-drying obtains orange/yellow solid powder 232mg (thick productive rate is 67.6%).And then separate for the eluent silica gel column chromatography with the methylene dichloride, obtain the orange/yellow solid powder.Ir (BFPPya) 3Nuclear magnetic spectrogram be: 1(TMS is interior mark to HNMR, solvent C DCl 3) δ (ppm): 7.92 (d, J=8.8Hz, 3H), 7.73 (d, J=8.8Hz, 3H), 7.59 (t, J=7.2Hz, 3H), 7.51 (t, J=6.4Hz, 6H), 6.87 (d, J=10.0Hz, 3H), 6.73-6.67 (m, J=9.2Hz, 9H)
Embodiment 4, title complex Ir (MDFPPya) 3The optical physics characteristic research.Shown in Figure 3 is title complex Ir (MDFPPya) 3The absorption of the dilute solution that in methylene dichloride, forms and emmission spectrum.The absorption peak position λ max=352nm of this title complex, emission peak position λ Max=506nm.With the Ir under the same terms (ppy) 3(the luminescent quantum productive rate is: luminous quantum efficiency Φ=0.37 of this title complex that 0.4) records for standard.
Embodiment 5, title complex Ir (BFPPya) 3The optical physics characteristic research.Shown in Figure 4 is title complex Ir (BFPPya) 3The absorption of the dilute solution that in methylene dichloride, forms and emmission spectrum.The absorption peak position λ of this title complex Max=375nm, emission peak position λ Max=524nm.With the Ir under the same terms (ppy) 3(the luminescent quantum productive rate is: luminous quantum efficiency Φ=0.44 of this title complex that 0.4) records for standard.
Embodiment 6, contain title complex Ir (MDFPPya) 3Organic electroluminescence device.With ito glass one after the other in clean-out system and deionized water with ultrasonic cleaning 30 minutes.5 minutes oxygen plasma treatment is done ito glass in vacuum-drying 2 hours (105 ℃) then again, is sent to preparation organic membrane and metal electrode in the vacuum chamber.The device architecture of this experiment is: ITO/NPB (50nm)/TCTA (10nm)/TPBI:14%Ir (MDFPPya) 3(50nm)/LiF (1nm)/Al (100nm).Wherein ITO is the transparency electrode of square resistance 30 Ω, and NPB is N, N '-phenylbenzene-N, N '-(1-naphthyl) 4,4 '-benzidine; TCTA is 4,4 ', 4 "-three (carbazole-9-yl) triphenylamine; Three (4-carbazole-9 bases-phenyl) amine; TPBI is 1,3, the 5-three (benzene of 1-phenyl-1H-benzimidazolyl-2 radicals-yl).Current-voltage-the brightness curve of this device is seen Fig. 5.The voltage that opens of device is 3.0V; Current density is 1 and 20mA/cm 2The time, current efficiency is respectively 17.7cd/A and 13.3cd/A, and maximum efficiency is 35.1cd/A (19.85%).
Embodiment 7, contain title complex Ir (BFPPya) 3Organic electroluminescence device.With ito glass one after the other in clean-out system and deionized water with ultrasonic cleaning 30 minutes.Vacuum-drying 2 hours (105 ℃) then, the UV/ozone of again ito glass being done 25 minutes is handled, and is sent to preparation organic membrane and metal electrode in the vacuum chamber.The device architecture of this experiment is: ITO/NPB (60nm)/CBP:7%Ir (BFPPya) 3(40nm)/BPhen (20nm)/LiF (1nm)/Al (100nm).Wherein ITO is the transparency electrode of square resistance 50 Ω, and NPB is N, N '-phenylbenzene-N, N '-(1-naphthyl) 4,4 '-benzidine; CBP is 4,4 '-two (N-carbazyl) biphenyl; BPhen is 4,7-phenylbenzene-1,10-phenanthroline.Current-voltage-the brightness curve of this device is seen Fig. 6.It opens voltage is 5.2V; Current density is 1 and 20mA/cm 2The time, current efficiency is respectively 22.4cd/A and 18.4cd/A, and maximum efficiency is 22.4cd/A (6.25%).

Claims (3)

1. phosphorescent iridium complex is characterized in that this complex structure formula (I) is as follows:
Figure FSA00000387069600011
In the said structure formula, 3-phenyl or 6-phenyl pyridazine are precursor structure, R 1, R 2Be not have two kinds of related groups, get one of following material respectively: hydrogen atom, halogen atom, nitro, cyano group, acyl group, sulfuryl, alkyl, substituted alkyl, cycloalkyl, cycloalkenyl group, alkoxyl group, aryloxy, alkylthio, replacement be silica-based, replace the fused ring aryl that siloxy, trifluoromethyl, aromatic amino, fatty amido, aromatic base or heterocyclic radical, fused ring aryl and heteroatoms replace; Simultaneously, do not get rid of R 1Or R 2Part or all of group and precursor structure forms ring texture.
2. phosphorescent iridium complex as claimed in claim 1 is characterized in that described ring texture comprises furans, thiophene, pyrroles, pyrazoles, oxazole, thiazole, imidazoles, pyridine, pyrans, pyrazine, pyrimidine, carbazole, quinoline, isoquinoline 99.9, indoles, pteridine, acridine, azophenlyene, thiodiphenylamine or purine.
3. phosphorescent iridium complex organic electroluminescence device as claimed in claim 1, it is characterized in that organic electroluminescence device (100) comprises the substrate layer (101) that sets gradually from the bottom to top, anode (102), hole injection layer or hole transmission layer (103), buffer layer or blocking layer (104), luminescent layer (105), buffer layer or blocking layer (106), electron injecting layer or electron transfer layer (107) and negative electrode (108), the hole transmission layer (103) that contains multilayer film structure in the organic electroluminescence device (100), buffer layer or blocking layer (104), luminescent layer (105), buffer layer or blocking layer (106), all or part of in electron injecting layer or the electron transfer layer (107), and the wherein one deck in this multilayer film structure or multilayer contain the described phosphorescent iridium complex of claim 1.
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CN103965886A (en) * 2013-01-30 2014-08-06 海洋王照明科技股份有限公司 Blue light-emitting organic electroluminescent material and its preparation method and use
CN103965881A (en) * 2013-01-30 2014-08-06 海洋王照明科技股份有限公司 Blue light-emitting organic electroluminescent material, its preparation method and organic electroluminescent device
CN103965883A (en) * 2013-01-30 2014-08-06 海洋王照明科技股份有限公司 Blue light-emitting organic electroluminescent material, its preparation method and organic electroluminescent device
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CN109678908A (en) * 2019-01-08 2019-04-26 安徽工业大学 It is a kind of using pyridyl derivatives as bicyclic metal platinum (II) complex of ligand and its preparation method and application
CN110790792A (en) * 2019-04-03 2020-02-14 云南师范大学 Iridium complex with 3-methyl-6-phenylimidazole [2,1-b ] thiazole derivative as main ligand
CN110390827A (en) * 2019-08-16 2019-10-29 扬州市腾飞钢杆照明器材有限公司 One kind being based on the electroluminescent intelligent signal lamp of phosphorescent iridium complex
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