CN116606323A - Cyclic imitation homoleptic iridium complex and preparation method and application thereof - Google Patents
Cyclic imitation homoleptic iridium complex and preparation method and application thereof Download PDFInfo
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- CN116606323A CN116606323A CN202310616524.2A CN202310616524A CN116606323A CN 116606323 A CN116606323 A CN 116606323A CN 202310616524 A CN202310616524 A CN 202310616524A CN 116606323 A CN116606323 A CN 116606323A
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 36
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 125000004122 cyclic group Chemical group 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 9
- 238000010668 complexation reaction Methods 0.000 title description 2
- 239000003446 ligand Substances 0.000 claims abstract description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 230000005525 hole transport Effects 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 229940093475 2-ethoxyethanol Drugs 0.000 claims description 2
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical group C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 claims description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical group C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical group [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 230000010287 polarization Effects 0.000 abstract description 8
- 238000004020 luminiscence type Methods 0.000 abstract description 7
- 150000002503 iridium Chemical class 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 5
- PUYOAVGNCWPANW-UHFFFAOYSA-N 2-methylpropyl 4-aminobenzoate Chemical group CC(C)COC(=O)C1=CC=C(N)C=C1 PUYOAVGNCWPANW-UHFFFAOYSA-N 0.000 abstract description 3
- 238000009825 accumulation Methods 0.000 abstract description 3
- 238000013461 design Methods 0.000 abstract description 3
- 238000005286 illumination Methods 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 3
- 238000000859 sublimation Methods 0.000 abstract description 3
- 230000008022 sublimation Effects 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 238000007385 chemical modification Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- -1 2-pyridine boric acid derivative Chemical class 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YWKKLBATUCJUHI-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C)=CC=1)C1=CC=CC=C1 YWKKLBATUCJUHI-UHFFFAOYSA-N 0.000 description 1
- UFWDOFZYKRDHPB-UHFFFAOYSA-N 9-[3-[6-(3-carbazol-9-ylphenyl)pyridin-2-yl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=CC=C(N=2)C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 UFWDOFZYKRDHPB-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- UMLDUMMLRZFROX-UHFFFAOYSA-N pyridin-2-ylboronic acid Chemical compound OB(O)C1=CC=CC=N1 UMLDUMMLRZFROX-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- 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 Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to a novel ternary homoleptic iridium complex containing a cycloimitated structure, wherein ligands in molecules of the iridium complex are cycloimitated nitrogen heterocyclic units. Compared with iridium complexes which have been widely researched and reported, the novel iridium complexes have the advantages of high luminous efficiency, stable chemical property, easy sublimation and purification and the like, and due to the introduction of a cycloform structure, on one hand, the periphery of the complexes has larger steric hindrance, the molecular accumulation is effectively inhibited, and the luminous efficiency is improved; on the other hand, the complex has circular polarization luminescence property due to the planar chiral characteristic brought by the cyclostyle. In addition, through modifying the nitrogen heterocyclic structure, the luminous position of the complex can be adjusted in the visible wavelength range, which provides convenience for the design and production of the organic electroluminescent display and the illumination light source. Meanwhile, the synthesis method of a series of novel iridium complexes is simple, the yield is high, and the chemical modification for the ligand is flexible.
Description
[ field of technology ]
The invention relates to the technical field of organic electroluminescent devices, in particular to an iridium complex, a preparation method and application thereof.
[ background Art ]
Under the great background of the growing global energy demands and the environmental concerns, the governments of various countries are continuously developing sustainable energy-saving technology and industry based on high technology. Organic electroluminescent devices (OLEDs) are attracting attention because of their wide viewing angle, high brightness, low power consumption, and capability of producing flexible devices, which are a key technology that will dominate the future display world. In recent years, a great deal of research has shown that iridium complexes are considered to be the most desirable choice of OLEDs phosphorescent materials among a wide variety of heavy metal element complexes. With 5d 7 6s 2 The iridium atom of the outer electron structure has 5d after forming +3-valent cations 6 The electronic configuration has a stable hexacoordinated octahedral structure, so that the material has higher chemical stability and thermal stability. Meanwhile, ir (III) has a large spin-orbit coupling constant (ζ=3909 cm) -1 ) The internal quantum yield of the complex is improved, the light-emitting service life is reduced, and the overall performance of the light-emitting device is improved.
Recently, the chiral luminescent material is used as a luminescent center to prepare the OLED device, so that circular polarization electroluminescence (Circularly Polarized Electroluminescence, CPEL), namely a circular polarization organic light emitting diode (CP-OLED), can be directly emitted, the complex light filtering structure and the loss of brightness efficiency are avoided, the OLED device has great application prospect in the fields of 3D display, photoelectric communication and the like, and a new research direction is provided for the development of the next-generation OLED material and device.
Accordingly, there is a need to provide an iridium complex OLED device having circularly polarized light emission and high device efficiency.
[ invention ]
The invention aims to provide an iridium complex which takes a cyclonitrogen-simulated heterocyclic ligand and has circular polarization luminescence and a preparation method thereof, and the complex can be used as a luminescence center and applied to an organic electroluminescent device.
The invention provides an iridium complex which is characterized by comprising three identical ring imitation linksThe nitrogen heterocyclic ring ligand is a compound,wherein R is 1 ,R 2 Is a hydrogen atom, alkyl group, alkoxy group, aryl group, halogen, etc.
Preferably, the cyclic imitation is selected from any one of the following:
preferably, the nitrogen heterocycleSelected from any one of the following:
preferred iridium complexes have one of the following structures:
the invention also provides a preparation method of the iridium complex, which comprises the following steps: ring imitation of a company nitrogen heterocyclic ligand and IrCl trichloride 3 Mixing; adding 2-ethoxyethanol solution, heating at 80-130 ℃ for reaction for 24-48 h, cooling to room temperature, adding water, and suction filtering to obtain yellow solid; adding yellow solid into glycerol, heating at 200-250deg.C for reaction for 24-48 hr, cooling to room temperature, distilling under reduced pressure to remove solvent, extracting with dichloromethane, concentratingSeparating by column chromatography to obtain iridium complex crude product with cycloazacyclo-simulated as ligand, and sublimating and purifying to obtain iridium complex, which can be applied to organic electroluminescent device.
The invention also provides application of the iridium complex in preparation of an organic electroluminescent device.
The invention has the beneficial effects that: the iridium complex provided by the invention has the characteristics of high luminous efficiency, stable chemical property, easiness in sublimation and purification and circular polarization luminescence. The iridium complex has the advantages of simple preparation method and high yield. Due to the introduction of the cycloform structure, the periphery of the complex has larger steric hindrance, so that the molecular accumulation is effectively inhibited, and the luminous efficiency is improved; on the other hand, the complex has circular polarization luminescence property due to the planar chiral characteristic brought by the cyclostyle. In addition, through modifying the nitrogen heterocyclic structure, the electron transmission performance can be improved, the luminous position of the complex can be adjusted in the visible light wavelength range, and convenience is provided for the design and production of the organic electroluminescent display and the illumination light source.
[ description of the drawings ]
FIG. 1 shows an electroluminescent spectrum of an iridium complex Ir01 used for an organic electroluminescent device;
FIG. 2 shows the photoelectric properties of Ir01 iridium complex provided by the invention for organic electroluminescent devices;
FIG. 3 shows the photoelectric properties of Ir01 iridium complex provided by the invention for organic electroluminescent devices;
fig. 4 shows the photoelectric properties of the iridium complex Ir01 provided by the invention for an organic electroluminescent device.
FIG. 5 shows an isomer (S) of Ir01 as an iridium complex according to the present invention P ) Ir01 is used for the circularly polarized electroluminescent spectrum of organic electroluminescent devices.
[ detailed description ] of the invention
The invention is described in further detail below with reference to the drawings and examples. The terms used in the present invention generally have the meanings commonly understood by those of ordinary skill in the art unless otherwise indicated.
The iridium complex of the invention adopts iridium trichloride, 4-bromocycloform, 2-pyridine boric acid derivative and the like in the synthesis process, and the synthesis method is similar. The invention will be further understood by the following examples, without limiting the scope of the invention.
Synthesis method of complex Ir01
4-Bromocyclic (2.86 g,10.0 mmol), 2-pyridineboronic acid (1.48 g,12.0 mmol), tetrakis (triphenylphosphine) palladium (0.23 g,0.2 mmol) and potassium carbonate (2.76 g,20.0 mmol) were dissolved in 90mL tetrahydrofuran and 30mL water, reacted under reflux for 24 hours, cooled, water and dichloromethane were added and the organic layer was concentrated to give the cycloazacyclic main ligand (2.11 g, 70.1% yield). The main ligand (2.11 g,7.0 mmol) and iridium trichloride (0.90 g,3.0 mmol) are dissolved in 50mL of ethoxyethanol and 25mL of water, the mixture is reacted for 24h at 120 ℃, cooled to room temperature, 100mL of water is added, suction filtration is carried out to obtain a pale yellow solid, the pale yellow solid is added into 50mL of glycerol, then the cycloazacyclo main ligand (1.50 g,5.0 mmol) and potassium carbonate (7.0 mmol,0.96 g) are added, the mixture is reacted for 36h at 220 ℃, cooled to room temperature, the solvent is distilled off under reduced pressure, the dichloromethane is used for extraction, concentration and column chromatography separation are carried out, thus obtaining iridium complex Ir01 (0.64 g, 20.1%) which takes cycloazacyclo as ligand is obtained through sublimation purification.
Ir01： 1 H NMR(400MHz,CDCl 3 )δ8.37(d,2H),8.21(d,2H),7.45(d,2H),7.38(d,1H),7.14(d,J＝4.0Hz,2H),7.08(d,1H),3.05(t,2H),3.01(t,2H),2.79(t,2H),2.61(t,2H).EI[M]calcd for C 64 H 58 IrN 3 ,1061.42；found1061.49.
The invention designs and synthesizes a series of homoleptic iridium complexes with different luminescent colors by taking the cyclosilatrane as a ligand. The purpose of regulating and controlling the luminous color of the complex is achieved by designing the ligand or the complex structure and modifying the ligand by a simple chemical substituent.
The iridium complex has the advantages of simple preparation method and high yield. Due to the introduction of the cycloform structure, the periphery of the complex has larger steric hindrance, so that the molecular accumulation is effectively inhibited, and the luminous efficiency is improved; on the other hand, the complex has circular polarization luminescence property due to the planar chiral characteristic brought by the cyclostyle. In addition, by modifying the nitrogen heterocyclic structure, the electron transmission performance can be improved, and the luminous position of the complex can be regulated in the visible wavelength range.
Preparation of organic electroluminescent device
Ir01 is used as a luminescent material to prepare the organic electroluminescent device.
The classical structure of OLEDs devices is: substrate/anode/hole transport layer/organic light emitting layer/electron transport layer/cathode.
In the manufacture of the device, the substrate is glass, and the anode material is Indium Tin Oxide (ITO); the hole transport layer uses 4,4' -cyclohexyl di [ N, N-di (4-methylphenyl) aniline (TAPC), the electron transport layer uses 3,3' - (5 ' - (3- (pyridin-3-yl) phenyl) - [1,1':3', 1' -triphenyl ] -3, 3' -diyl) bipyridine (TmPyPB), the thickness is 60nm, and the evaporation rate is 0.05nm/s; the cathode adopts LiF/Al, the LiF thickness is 1nm, the evaporation rate is 0.01nm/s, the Al thickness is 100nm, and the evaporation rate is 0.2nm/s. The organic light-emitting layer adopts a doped structure, the main material is 26DCzPPy, the selected light-emitting material is Ir01, the thickness is 30nm, the evaporation rate is 0.05nm/s, and the mass fraction of Ir01 is 10%.
The structures of several materials used in the invention are as follows:
the invention selects a green light complex to prepare the organic electroluminescent device. Referring to fig. 1, fig. 2, fig. 3 and fig. 4 together, fig. 1 is an electroluminescence spectrum of an iridium complex provided by the present invention for an organic electroluminescent device, fig. 2 is a photoelectric property of the iridium complex provided by the present invention for an organic electroluminescent device, fig. 3 is a photoelectric property of the iridium complex provided by the present invention for an organic electroluminescent device, and fig. 4 is a photoelectric property of the iridium complex provided by the present invention for an organic electroluminescent device. As shown in figures 1-4 of the drawings,the starting voltage of the organic electroluminescent device is 3.9V, and the maximum current efficiency and the power efficiency are 45.4cdA respectively -1 And 28.2lm W -1 . When the applied voltage of the organic electroluminescent device is 11.0V, the device reaches the maximum brightness 24222cd m -2 . An isomer (S) of Ir01 after resolution P ) The device prepared with Ir01 as the luminescence center showed a circularly polarized electroluminescent signal (FIG. 5), with an asymmetry factor of-0.005.
The research on photoelectric properties shows that the phosphorescence iridium complex of the cyclonitrogen-simulated heterocyclic ligand has higher luminous efficiency.
Therefore, the cyclic imitation nitrogen heterocycle ligand can be used for effectively synthesizing complexes with high luminescence performance and different colors, and shows good device performance, and the split complex device shows good circular polarization electroluminescent signals, so that the material has practical application value in the fields of display, illumination and the like.
The phosphorescence material provided by the invention can be used as a luminescence center to be applied to an emission layer of phosphorescence OLEDs, and the purpose of regulating and controlling the luminescence color of the complex is achieved by designing a ligand or complex structure and modifying chemical substituents of the ligand.
While the invention has been described with respect to the above embodiments, it should be noted that modifications can be made by those skilled in the art without departing from the inventive concept, and these are all within the scope of the invention.
Claims (6)
1. An iridium complex, characterized in that it comprises three identical cyclonitrogen-imitating heterocyclic ligands,wherein R is 1 ,R 2 Is a hydrogen atom, alkyl group, alkoxy group, aryl group, halogen, etc.
2. Iridium complex according to claim 1, characterized in that the cyclic imitation is selected from any one of the following:
the nitrogen heterocycleSelected from any one of the following:
3. iridium complex according to claim 2, characterized in that it has one of the following structures:
4. a process for preparing iridium complex features that cyclic-simulated biazacyclic ligand and iridium trichloride IrCl 3 Mixing; adding 2-ethoxyethanol solution, heating at 80-130 ℃ for reaction for 24-48 h, cooling to room temperature, adding water, and suction filtering to obtain yellow solid; adding yellow solid into glycerol, heating at 200-250deg.C for reaction for 24-48 h, cooling to room temperature, distilling under reduced pressure to remove solvent, extracting with dichloromethane, concentrating, separating by column chromatography to obtain iridium complex crude product with cycloazacyclo-as ligand, and sublimatingAnd purifying to obtain iridium complex.
5. The method for producing an iridium complex according to claim 4, wherein a molar ratio of iridium trichloride to the cyclosilatrane ligand is 1:4.
6. an electroluminescent device using the iridium complex as claimed in any one of claims 1 to 5, comprising a substrate, an anode, a hole transport layer, an organic light-emitting layer, an electron transport layer and a cathode, characterized in that: the substrate is glass, the anode is indium tin oxide, the hole transport layer is TAPC material, and the electron transport layer is TmPyPB material.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202310616524.2A CN116606323A (en) | 2023-05-26 | 2023-05-26 | Cyclic imitation homoleptic iridium complex and preparation method and application thereof |
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| CN202310616524.2A CN116606323A (en) | 2023-05-26 | 2023-05-26 | Cyclic imitation homoleptic iridium complex and preparation method and application thereof |
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| CN116606323A true CN116606323A (en) | 2023-08-18 |
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- 2023-05-26 CN CN202310616524.2A patent/CN116606323A/en not_active Withdrawn
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