CN105646596A - Iridium complex and preparation method and application thereof - Google Patents
Iridium complex and preparation method and application thereof Download PDFInfo
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- CN105646596A CN105646596A CN201610126337.6A CN201610126337A CN105646596A CN 105646596 A CN105646596 A CN 105646596A CN 201610126337 A CN201610126337 A CN 201610126337A CN 105646596 A CN105646596 A CN 105646596A
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- iridium
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- phosphoric acid
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- 0 *P(c1ccccn1)(C1=CC=C*(C(F)(F)F)C=C1)=O Chemical compound *P(c1ccccn1)(C1=CC=C*(C(F)(F)F)C=C1)=O 0.000 description 3
- MYFLOVPLGXPZAV-MAGPIRRDSA-N C/C=C\C(\P(c1ncccc1)(O)=O)=C/C=C\F Chemical compound C/C=C\C(\P(c1ncccc1)(O)=O)=C/C=C\F MYFLOVPLGXPZAV-MAGPIRRDSA-N 0.000 description 1
- URLKIFVGDJRJFH-KRCYNEMASA-N C/[F]=C\C=C/C=C(\[NH-])/P([n]1nccc1)(O)=O Chemical compound C/[F]=C\C=C/C=C(\[NH-])/P([n]1nccc1)(O)=O URLKIFVGDJRJFH-KRCYNEMASA-N 0.000 description 1
- CJWZMZPGOUBPEX-UHFFFAOYSA-N FC(c(c(F)c(cc1)-c2ncccc2)c1F)(F)F Chemical compound FC(c(c(F)c(cc1)-c2ncccc2)c1F)(F)F CJWZMZPGOUBPEX-UHFFFAOYSA-N 0.000 description 1
- UCTUOFPJTWPPDY-UHFFFAOYSA-N FC(c(cc1)cc(C(F)(F)F)c1-c1ncccc1)(F)F Chemical compound FC(c(cc1)cc(C(F)(F)F)c1-c1ncccc1)(F)F UCTUOFPJTWPPDY-UHFFFAOYSA-N 0.000 description 1
- PNKSSGFRIVHGLE-UHFFFAOYSA-N Fc(cc1)nc(F)c1-c1ncccc1 Chemical compound Fc(cc1)nc(F)c1-c1ncccc1 PNKSSGFRIVHGLE-UHFFFAOYSA-N 0.000 description 1
- RKGNWPYWRICEMN-UHFFFAOYSA-N Fc(ccc(-c1ncccc1)c1F)c1F Chemical compound Fc(ccc(-c1ncccc1)c1F)c1F RKGNWPYWRICEMN-UHFFFAOYSA-N 0.000 description 1
- FBTBZEMNUJXILX-UHFFFAOYSA-N Fc1cc(F)c(C2N=CC=CC2)cc1 Chemical compound Fc1cc(F)c(C2N=CC=CC2)cc1 FBTBZEMNUJXILX-UHFFFAOYSA-N 0.000 description 1
- VPLQYLXMULIYLP-UHFFFAOYSA-N O=PC1=CC=CCN1 Chemical compound O=PC1=CC=CCN1 VPLQYLXMULIYLP-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 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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- 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
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- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Abstract
The invention provides an iridium complex and a preparation method thereof. The iridium complex uses aromatic ring and nitrogen heterocycle as a first main ligand and azo-heterocyclic phosphate as a second main ligand; in the aromatic ring and nitrogen heterocycle of the first main ligand, Ar is substituted phenyl ring, substituent is F, CF3 or CN, and N is pyridyl; in the azo-heterocyclic phosphate of the second main ligand, R is aryl or pyridyl, substituent is F or CF3, and N is pyridyl. The iridium complex is prepared by mixing iridium dimer bridged complex, azo-heterocyclic phosphate and an alkali carbonate as materials, adding 2-ethoxyethanol solution to a mixture and thermally reacting. The iridium complex of the invention is simple to prepare, high in yield and applicable to the preparation of organic electroluminescent devices.
Description
[technical field]
The present invention relates to organic electroluminescence device technical field, particularly relate to class complex of iridium and its preparation method and application.
[background technology]
Under the overall background that and ecological environment growing at global energy requirements causes anxiety, national governments greatly develop in succession based on high-tech energy sustainability technology and industry. Organic electroluminescence device (OLEDs) because its visual angle is wide, brightness is high, energy consumption is low and can prepare the plurality of advantages such as flexible device, and receive much attention, it is referred to as the key technology by dominating display in the future world. In recent years, big quantity research shows, in numerous heavy metal element coordination compounds, complex of iridium is considered as OLEDsThe most ideal chose of phosphor material. There is the iridium atom of 5d76s2 outer electronic structure after forming+3 valency cationes, there is 5d6 electron configuration, there is stable hexa-coordinate octahedral structure, make material have higher chemical stability and heat stability. Meanwhile, Ir (III) has bigger spin orbit coupling constant (��=3909cm-1), is conducive to improving the interior quantum yield of coordination compound and reducing luminescent lifetime, thus improving the overall performance of luminescent device.
Compared to HONGGUANG and green glow complex of iridium, the energy of blue emission is of a relatively high, and this just requires that blue phosphorescent complex of iridium has higher T1 energy level and wider HOMO/LUMO energy level difference. Research shows, rising along with triplet, the speed of radiation transistion and nonradiative transition all can increase, and the increase amplitude of the latter often becomes apparent from, cause that luminous efficiency declines, therefore, launch the blue shift of wavelength and high internal quantum efficiency be contradictory relation, this just exploitation to blue light compound add difficulty. It addition, have the blue light compound of relatively bob ejected wave length, its luminous efficiency is all relatively low.
Therefore, it is necessary to provide the complex of iridium that a kind of luminous efficiency is high.
[summary of the invention]
It is an object of the invention to provide blue light and the luminous complex of iridium of other different colours and preparation method thereof that a class is the second main part with azacyclo-phosphoric acid, azacyclo-phosphoric acid can prepare efficient phosphorescent iridium complex as assistant ligand, such coordination compound as the centre of luminescence, can be applied in organic electroluminescence device.
The present invention provides a class complex of iridium, and it is using aromatic ring azino heterocycle as the first main part, using azacyclo-phosphoric acid as the second main part.
Described aromatic ring azino heterocycle is selected from:
Ar is aromatic ring, and N is pyridine radicals;
Described azacyclo-phosphoric acid is selected from:
R is aryl or pyridine radicals, and B is pyridine radicals.
Preferably, the Ar of described aromatic ring azino heterocycle is phenyl, its optional one or more independent replacing selected from following substituent group: F, CF3Or CN, N are pyridine radicals, described aromatic ring azino heterocycle is selected from:
Preferably, the R of described azacyclo-phosphoric acid is aryl or pyridine radicals, and substituent group is F or CF3, B is pyridine radicals or pyrazolyl, and described azacyclo-phosphoric acid is selected from:
Preferably, described complex of iridium one of is structured with:
The preparation method that the present invention provides described complex of iridium: connect coordination compound, azacyclo-phosphoric acid and alkali carbonate for raw material with iridium dimerization bridge, cellosolvo solution is added after being mixed by raw material, reaction it is heated at 115-130 DEG C, response time 10-12h, after after reaction, gained solution is cooled to room temperature, again with dichloromethane extraction, concentration, obtain complex of iridium crude product through chromatography.
Preferably, described alkali carbonate is any one or both mixture in sodium carbonate and potassium carbonate.
Preferably, described iridium dimerization bridge connects coordination compound and contains pyridine derivate, and the mol ratio that described iridium dimerization bridge connects coordination compound, azacyclo-phosphoric acid and potassium carbonate is 1:2:3.
The present invention also provides for the application in preparing organic electroluminescence device of the described complex of iridium.
Beneficial effects of the present invention: complex of iridium provided by the invention has the feature of luminous efficiency height, stable chemical nature, easy sublimation purification. The preparation method of described complex of iridium is simple, and productivity is higher. Due to the introducing of phosphorus oxygen key of polarization, the glow color of coordination compound and improve electronic transmission performance can Effective Regulation; By modifying the molecular structure of the first main part and the second main part, it is possible to regulate the luminous position of coordination compound in all visible wavelength ranges, the design production for display of organic electroluminescence and lighting source is provided convenience.
[accompanying drawing explanation]
Fig. 1 is complex of iridium provided by the invention ultraviolet-visible absorption spectroscopy at ambient temperature and photoluminescence spectra;
Fig. 2 is the complex of iridium provided by the invention electroluminescent spectrum for organic electroluminescence device;
Fig. 3 is the complex of iridium provided by the invention photoelectric properties for organic electroluminescence device;
Fig. 4 is the complex of iridium provided by the invention photoelectric properties for organic electroluminescence device;
Fig. 5 is the complex of iridium provided by the invention photoelectric properties for organic electroluminescence device.
[detailed description of the invention]
Below in conjunction with drawings and Examples, the present invention is described in further detail.
The term used in the present invention, except as otherwise noted, is generally the implication that those of ordinary skill in the art are generally understood that. In the examples below, the various processes not being described in detail and method are conventional methods as known in the art.
[complex of iridium with azacyclo-phosphoric acid for the second main part]
The complex of iridium of the present invention, it is with aromatic ring azino heterocycle for the first main part, with azacyclo-phosphoric acid for the second main part;
Described aromatic ring azino heterocycle is selected from:
Ar is substituted or non-substituted aromatic ring, and N is pyridine radicals. Wherein, Ar may be selected to be phenyl ring or pyridine ring, and substituent group is F, CF3 or CN.
Described aromatic ring azino heterocycle preferably one of is structured with:
Described azacyclo-phosphoric acid is selected from:
R is aryl or pyridine radicals, and B is pyridine radicals.Wherein, the R of azacyclo-phosphoric acid may select phenyl ring or substituted benzene ring, and substituent group is F or CF3; B can be pyridine radicals or pyrazolyl. Described azacyclo-phosphoric acid preferably one of is structured with:
Described complex of iridium, it is preferable that one of be structured with:
[preparation method of complex of iridium]
The complex of iridium of the present invention employs the compounds such as iridous chloride, 2-bromopyridine, 2,4 difluorobenzene boric acid in building-up process, and its preparation method is similar. The complex of iridium with above-mentioned first preferred structure can be prepared by following reaction equation.
By 2-bromopyridine (4.17g, 26.39mmol), 2,4-difluorobenzene boric acid (5.00g, 31.66mmol), four triphenyl phosphorus palladium (0.91g, 0.79mmol) and sodium carbonate (6.36g, 60.00mmol) be dissolved in 100mL oxolane, back flow reaction 24 hours, cooling, add water and dichloromethane, organic layer evaporating column chromatography obtains the first main part 3.84g, and productivity is 76.18%. The iridium dimerization bridge that described first main part is containing pyridine derivate connects coordination compound. By described first main part (2.50g, 13.08mmol) and iridous chloride (2.30g, 6.23mmol) it is dissolved in the cellosolvo of 15mL, mixture back flow reaction 12h, it is subsequently adding pyridine phosphoric acid (1.36g, 6.23mmol) with potassium carbonate (1.30g, 9.35mmol), continue back flow reaction 12h. System is cooled to room temperature, and decompression distillation, except solvent, adds water and dichloromethane, and organic layer evaporating column chromatography obtains yellow solid 1.06g, and described yellow solid is complex of iridium (IrA), and productivity is 21.5%.
Further, it is 1:2:3 that iridium dimerization bridge connects the mol ratio of coordination compound and azacyclo-phosphoric acid and potassium carbonate, heats, react 12 hours at 105 DEG C-130 DEG C, and productivity is 30%-40%.
Iridium dimerization bridge of the present invention connects coordination compound and is referred to open source literature [(a) S.Lamansky, P.Djurovich, D.Murphy, F.Abdel-Razzaq, H.E.Lee, C.Adachi, P.E.Burrow, S.R.Forrest, M.E.Thompson, J.Am.Chem.Soc., 2001,123,4304-4312; (b) S.Lamansky, P.Djurovich, D.Murphy, F.Abdel-Razzaq, R.Kwong, I.Tsyba, M.Bortz, B.Mui, R.Bau, M.E.Thompson, Inorg.Chem., 2001,40,1704-1711.] preparation method obtain.
1HNMR(400MHz,CDCl3, ��): 9.66 (d, J=5.5Hz, 1H), 8.38 (d, J=8.8Hz, 1H), 8.23 (d, J=8.4Hz, 1H), 7.91 (t, J=5.8Hz, 1H), 7.81 7.73 (m, 4H), 7.42 7.31 (m, 5H), 7.23 (dd, J=7.2,5.7Hz, 1H), 7.15 (td, J=7.5,3.0Hz, 2H), 6.79 (t, J=6.2Hz, 1H), 6.53 6.39 (m, 2H), 5.76 (dd, J=8.8,2.2Hz, 1H), 5.61 (dd, J=8.7,2.2Hz, 1H).31PNMR(400MHz,CDCl3,��):34.31ppm(s).EI,[M]calcdforC33H21F4IrN3O2P, 790.72; Found790.00.
Measuring ultraviolet-visible absorption spectroscopy and the photoluminescence spectra of complex of iridium of the present invention at ambient temperature, result is as shown in Figure 1.
The present invention is with azacyclo-phosphoric acid for the second main part, and design has synthesized a series of blue light and the complex of iridium of other different colours luminescence. By designing part or complex structure, and by the modification of simple chemical substituents on part, reach the purpose of regulation and control coordination compound glow color.
The phosphorus oxygen key of described azacyclo-phosphoric acid and azacyclo-are all the groups having stronger electron-transporting, effectively in the injection of equilbrium carrier and transmission, improve luminous efficiency.
Described complex of iridium has higher interior quantum yield, and after optimized checking, its preparation method is simple, and productivity is higher.
[preparation of organic electroluminescence device]
Described complex of iridium (IrA) can prepare organic electroluminescence device as luminescent material. The classical architecture of organic electroluminescence device is: substrate/anode/hole transmission layer/organic luminous layer/electron transfer layer/negative electrode.
The present invention makes the material of organic electroluminescence device:
Substrate is glass; Anode material is indium stannum oxygen (ITO); Hole transmission layer uses 4,4'-cyclohexyl two [N, N-bis-(4-aminomethyl phenyl) aniline (TAPC); Electron transport layer materials uses 3,3'-(5'-(3-(pyridin-3-yl) phenyl)-[1,1':3'; 1 "-triphenyl]-3; 3 "-two bases) two pyridines (TmPyPB), thickness is 60nm, and evaporation rate is 0.05nm/s; Negative electrode adopts LiF/Al, LiF thickness to be 1nm, and evaporation rate is 0.01nm/s, Al thickness is 100nm, and evaporation rate is 0.2nm/s; Organic luminous layer adopts doped structure, and material of main part is with 1,3-bis-(9H-carbazole-9-base) benzene (mCP), selected luminescent material is complex of iridium (IrA), thickness is 40nm, and evaporation rate is 0.05nm/s, IrA mass fraction 8%.
The material structure that the luminescent material of organic luminous layer and material of main part, hole transmission layer and electron transfer layer adopt is as follows:
The present invention selects a kind of blue light complex preparation organic electroluminescence device. See also Fig. 2, Fig. 3, Fig. 4 and Fig. 5, Fig. 2 is the complex of iridium provided by the invention electroluminescent spectrum for organic electroluminescence device, Fig. 3 is the complex of iridium provided by the invention photoelectric properties for organic electroluminescence device, Fig. 4 is the complex of iridium provided by the invention photoelectric properties for organic electroluminescence device, and Fig. 5 is the complex of iridium provided by the invention photoelectric properties for organic electroluminescence device. As Figure 2-Figure 5, when the startup voltage of described organic electroluminescence device is 2.9V, its maximum power efficiency, current efficiency and external quantum efficiency respectively 50.89lm/W, 50.99cd/A and 25.1%. During the applied voltage 10.0V of organic electroluminescence device, it reaches high-high brightness 34153cd/m2. By studying photophysical property, it was shown that the phosphorescent iridium complex of this kind of assistant ligand containing azacyclo-phosphorus oxygen structure has higher luminous efficiency.
Therefore, utilize azacyclo-phosphoric acid as the second cyclic metal complexes can the coordination compound of effectively synthesizing high lumineseent performance, different colours, and show good device performance, it was shown that this kind of material has actual application value in fields such as display and illuminations.
Such phosphor material provided by the invention can be applied to the emission layer of phosphorescent OLED s as the centre of luminescence, by designing part or complex structure, and by the chemical substituents of described part is modified, invention achieves the purpose of regulation and control coordination compound glow color.
Above-described is only embodiments of the present invention, it should be noted here that for the person of ordinary skill of the art, without departing from the concept of the premise of the invention, it is also possible to make improvement, but these belong to protection scope of the present invention.
Claims (8)
1. a complex of iridium, it is characterised in that described complex of iridium includes: using aromatic ring azino heterocycle as the first main part and using azacyclo-phosphoric acid as the second main part;
Described aromatic ring azino heterocycle is selected from:
Wherein, Ar is aromatic ring, and N is pyridine radicals;
Described azacyclo-phosphoric acid is selected from:
Wherein, R is aryl or pyridine radicals, and B is pyridine radicals.
2. complex of iridium according to claim 1, it is characterised in that the Ar of described aromatic ring azino heterocycle is phenyl, its optional one or more independent replacing selected from following substituent group: F, CF3And CN, N are pyridine radicals, described aromatic ring azino heterocycle is selected from:
3. complex of iridium according to claim 2, it is characterised in that the R of described azacyclo-phosphoric acid is aryl or pyridine radicals, substituent group is F or CF3, B is pyridine radicals or pyrazolyl, and described azacyclo-phosphoric acid is selected from:
4. complex of iridium according to claim 3, it is characterised in that described complex of iridium one of is structured with:
5. one kind arbitrary in claim 1-4 as described in the preparation method of complex of iridium: connect coordination compound, azacyclo-phosphoric acid and alkali carbonate for raw material with iridium dimerization bridge, cellosolvo solution is added after being mixed by raw material, reaction it is heated at 115-130 DEG C, response time 10-12h, after after reaction, gained solution is cooled to room temperature, again with dichloromethane extraction, concentration, obtain complex of iridium crude product through chromatography.
6. the preparation method of complex of iridium according to claim 5, it is characterised in that described alkali carbonate is the mixture of any one or two kinds in sodium carbonate and potassium carbonate.
7. the preparation method of complex of iridium according to claim 5, it is characterised in that described iridium dimerization bridge connects coordination compound and contains pyridine derivate, and the mol ratio that described iridium dimerization bridge connects coordination compound, azacyclo-phosphoric acid and potassium carbonate is 1:2:3.
8. one kind arbitrary in claim 1-4 as described in the application of complex of iridium, it is characterised in that use it in organic electroluminescence device.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114456462A (en) * | 2021-10-13 | 2022-05-10 | 中国科学院江西稀土研究院 | High-weather-resistance light conversion film and preparation method and application thereof |
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Cited By (2)
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| CN114456462A (en) * | 2021-10-13 | 2022-05-10 | 中国科学院江西稀土研究院 | High-weather-resistance light conversion film and preparation method and application thereof |
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