WO2012163108A1 - 一种稀土铕配合物及其作为发光材料的应用 - Google Patents
一种稀土铕配合物及其作为发光材料的应用 Download PDFInfo
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- WO2012163108A1 WO2012163108A1 PCT/CN2012/071298 CN2012071298W WO2012163108A1 WO 2012163108 A1 WO2012163108 A1 WO 2012163108A1 CN 2012071298 W CN2012071298 W CN 2012071298W WO 2012163108 A1 WO2012163108 A1 WO 2012163108A1
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- KPOWFCVWFASZNK-UHFFFAOYSA-N Cc(ccnc12)c1ncc(C#N)c2O Chemical compound Cc(ccnc12)c1ncc(C#N)c2O KPOWFCVWFASZNK-UHFFFAOYSA-N 0.000 description 2
- IBKMZYWDWWIWEL-UHFFFAOYSA-N Cc(ccnc1)c1N Chemical compound Cc(ccnc1)c1N IBKMZYWDWWIWEL-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N c1cc(-c2ccccn2)ncc1 Chemical compound c1cc(-c2ccccn2)ncc1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N c1cc(ccc2c3nccc2)c3nc1 Chemical compound c1cc(ccc2c3nccc2)c3nc1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic System
- C07F1/08—Copper compounds
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic System without C-Metal linkages
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H—ELECTRICITY
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- 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
- H10K85/351—Metal complexes comprising lanthanides or actinides, e.g. comprising europium
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- 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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/182—Metal complexes of the rare earth metals, i.e. Sc, Y or lanthanide
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
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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
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
Definitions
- the invention relates to the field of rare earth complex luminescent materials, in particular to a novel rare earth lanthanum complex with high efficiency photoluminescence and electroluminescence properties. Background technique
- LED Light-emitting Diode
- OLED Organic Light-emitting Diode
- OLED In addition, in terms of full color display, OLED also has attractive application prospects. At present, most of the color displays used by people are cathode ray tubes or liquid crystal displays. Cathode ray tubes are being phased out due to their large size, slow response, and low efficiency. At present, the most widely used liquid crystal display on the market is small in size and improved in performance, but there are also passive light sources, small viewing angles, and slow response. Organic electroluminescence has great appeal because it has the following characteristics: 1. Full-color active illumination, bright colors (LCD screen requires background light source); 2. Ultra-thin display, flexible bending; 3. Fast response speed (liquid crystal 100 times), the viewing angle range is as wide as 180° (the LCD screen is only 45°); 4. The driving voltage is low, only 3-10 volts DC voltage is required, and the luminous efficiency is high; 5. Simple production and low cost.
- organic molecular luminescent materials have important application prospects in terms of illumination and display.
- rare earth luminescent materials have advantages in both of these aspects due to their unique properties. The superiority of rare earth complex luminescent materials is mainly reflected in:
- Rare earth elements have a unique electronic arrangement and energy level structure, especially its 4f electron layer is rich in energy levels, and rare earth elements are often between 4f layers. It has a high level of energy, and at the same time it is an inner layer of electrons. The outer layer of electrons shields it, so its luminescence is very little interfered by external factors, and it has a sharp narrow-band emission.
- red, green and blue RGB three primary colors need to be obtained by filters or other methods, so that there is a certain amount of light energy was wasted.
- Rare earth compounds have narrow bands with color coordinates less than 10 nm Emission, so it is also important to apply it to organic electroluminescent materials.
- the luminescence process of the rare earth complex is caused by the excitation of the singlet between the organic ligands and the triplet state, and then the energy is transferred to the rare earth ions to excite the 4f electrons, and then return to the ground state to emit light. Since both singlet and triplet states can pass energy, in theory, the internal quantum efficiency can reach 100%.
- the ligand modification does not affect the wavelength of light emission.
- various modifications are usually made to the ligand. Since the luminescent group of the rare earth complex is a central rare earth ion, the ligand modification does not cause a change in the spectral peak shift. Therefore, rare earth complex luminescent materials have unique advantages in material design modification.
- the rare earth complex has superior luminescent properties and has broad application prospects in the fields of photoluminescence and electroluminescence.
- a red-emitting krypton and a green-light down-converting photoluminescent material can be used as the phosphor.
- the most commonly used trichromatic phosphors in fluorescent lamps are rare earth green powder (Ce, Tb) MgAI "O 19 , blue powder (Ba, Mg, Eu) 3 AI 16 0 27 and red powder Y 2 O 3 : Eu 3+ These are all rare earth-containing inorganic solid luminescent materials.
- the complex fluorescent material can reduce the amount of rare earth and reduce the cost.
- the trivalent ruthenium complex can absorb ultraviolet light efficiently and emit bright red light, which can be used as an organic red light conversion material. Gong Mengyu and others from Zhongshan University synthesized one.
- a series of rare earth Eu complexes containing a carbazole-based ⁇ -diketone ligand, and this complex is coated as a down-converting luminescent phosphor on a near-ultraviolet InGaN substrate to produce a red-emitting LED device (M ⁇ Gong et al, Appl. Phys. B, 2010, 99, 757).
- LED devices utilizing Eu complex photoluminescence there is thermal quenching and instability of color mixing that may occur with voltage changes. problem.
- the rare earth ruthenium complexes under study are basically using ⁇ -diketones as antenna ligands, and compounds with high photoluminescence quantum yield are not lacking, but in down-converting LED materials or electro-optical
- the application in OLEDs is not smooth. The main reason is that these ligands have some important defects: 1.
- the ⁇ -diketone structure complex is prone to thermal quenching.
- the ⁇ -diketone structural complexes have poor carrier transport properties when electroluminescent. These disadvantages seriously affect the efficiency of electroluminescence of ⁇ -diketone ruthenium complexes and their temperature rise during device operation. Stability. Summary of the invention
- R 2 , R 3 , R 4 and R 5 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, an alkyl group, a halogen-substituted alkyl group, an alkenyl group, a block group, an amino group, an N-substituted amine.
- halogen atom means ", CI, and the like.
- the above alkyl group is preferably a C1 to C24 linear or branched alkyl group, more preferably a C1 to C6 linear or branched alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group or a different group. Butyl, tert-butyl, sec-butyl, pentyl, neopentyl, hexyl and the like. A linear or branched alkyl group of C1 to C4 is particularly preferred.
- the above halogen-substituted alkyl group is preferably a C1 to C24 linear or branched halogen-substituted alkyl group, preferably a C1-C6 linear or branched halogen-substituted alkyl group, for example: a halogenated methyl group, a halogenated ethyl group, a halogen A propyl group, a halogenated isopropyl group, a halogenated butyl group, a halogenated isobutyl group, a halogenated t-butyl group, a halogenated sec-butyl group or the like, and particularly preferably a C1-C3 linear or branched haloalkyl group, for example Trifluoromethyl, pentafluoroethyl.
- the above alkenyl group or block group is preferably a C2-C24 linear or branched alkenyl group or a blocked group, preferably a C2-C6 linear or branched alkenyl group or a blocked group, particularly preferably a C2-C4 linear or branched alkene.
- Base or block group for example: vinyl, ethyl group, 1-propenyl group,
- the above N-substituted amine group is preferably an amine group substituted with a C1-C6 alkyl group, such as a dimethylamino group.
- the above alkoxy group is preferably a C1 to C24 linear or branched alkoxy group, more preferably a C1 to C6 linear or branched alkoxy group, particularly preferably a C1 to C4 linear or branched alkoxy group, for example: Methoxy, ethoxy, propoxy, isopropoxy, butoxy Base, isobutoxy and the like.
- the above ester group refers to a carboxylate group having a structure of -COOR, wherein R is preferably a C1 to C24 linear or branched alkyl group or a halogen-substituted alkyl group, more preferably R is a C1 to C6 linear or branched alkyl group.
- a halogen-substituted alkyl group particularly preferably a linear or branched alkyl group or a halogen-substituted alkyl group wherein R is C1 - C4, such as a methyl carboxylate group, an ethyl carboxylate group, a propyl carboxylate group.
- the above acyl group means a group of the structure -COR, wherein R is preferably a C1 - C24 linear or branched alkyl group, more preferably a C1 - C6 linear or branched alkyl group, particularly preferably a C1 - C4 linear chain. Or a branched alkyl group, for example, an acetyl group, a propionyl group, an isopropionyl group, a butyryl group or the like.
- the above N-substituted amide group preferably has a substituent on N which is a C1 to C24 linear or branched alkyl group, more preferably an N group substituent is a C1 to C6 linear or branched alkyl group. Particularly preferred is a amide group of a C1 to C4 linear or branched alkyl group, for example, N,N-dimethylformamido, N,N-diethylformamido or the like.
- the above aryl or heterocyclic aryl group is preferably a C5-C10 unsubstituted aryl group, a heterocyclic aryl group or a substituted aryl group or a heterocyclic aryl group such as a phenyl group, a furyl group, a pyrazolyl group, a pyridyl group, Oxadiazolyl and the like.
- R 2 , R 3 , R 4 and R 5 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, an alkyl group, a halogen-substituted alkyl group, an alkenyl group, a blocked group, an amino group, an N-substituted amino group.
- A is an anion other than ND Body
- L is a neutral ligand
- x 1, 2 or 3
- y 0, 1 or 2
- x+y 3
- m 0, 1, 2 or 3
- m depends on the specific value Dependent on neutral ligands. The preferred ranges for the various groups are as previously described.
- R a and R b are each independently an aromatic group such as a phenyl group or a naphthyl group, or a heterocyclic aryl group such as a thienyl group, a furyl group or a pyridyl group, or a fluorine-containing alkyl group such as a trifluoromethyl group or a pentafluoroethyl group; .
- Preferred ⁇ -diketone anionic ligands are dibenzoylmethyl (DBM), trifluoroacetylthiophenemethyl (anthracene), dinaphthoylmethyl (DNM), trifluoroacetylnaphthoyl ( ⁇ ) and so on.
- DBM dibenzoylmethyl
- DMD trifluoroacetylthiophenemethyl
- DCM dinaphthoylmethyl
- ⁇ trifluoroacetylnaphthoyl
- the 4-hydroxy-1,5-naphthyridine ligand (ND) becomes a tridentate anion ligand, and the formed
- This type of tridentate anion ligand is a novel ligand, and has stable coordination, good sublimation film formation, and coordination of three tridentate anion ligands with a trivalent europium ion. Advantages of sexual ligands. Therefore, this novel tridentate anionic ligand and the synthesized ruthenium complex are within the scope of this patent.
- the nitrogen-containing ligand-bearing group is usually an aza 5-membered ring aryl group and an aza 6-membered ring aryl group such as pyrrolyl group, imidazolyl group, pyridyl group, oxazolyl group and the like.
- R 5 is a pyridyl group
- the complex formed by the tridentate ligand and Eu has the following structural formula (Formula III):
- the tridentate ligand includes both its enol and ketone resonance structures.
- Ri, R 2 , R 3 , and R 4 are as defined above; and R 6 , R 7 , R 8 , and R 9 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a nitro group, a cyano group, an alkyl group, and a halogen-substituted alkyl group. , amino, N-substituted amine, alkoxy.
- the preferred ranges for the various groups are as previously described.
- A is an anionic ligand other than ND
- L is a neutral ligand
- x 1, 2 or 3
- y 0, 1 or 2
- x + y 3
- m 0, 1 or 2
- m The specific value depends on the different neutral ligands.
- the oxygen-containing ligand-containing group mainly refers to a carbonyl group-containing group.
- R 5 is a carbonyl group-containing group
- the complex structure of the tridentate ligand and Eu has the following structural formula (Formula IV):
- the tridentate ligand includes both its enol and ketone resonance structures.
- R 2 R 3 and R 4 are as defined above; and R 1 C ) is selected from the group consisting of a hydroxyl group, an alkyl group, a substituted alkyl group, an amino group, an N-substituted amino group, and an alkoxy group.
- the preferred ranges for the various groups are as previously described.
- A is an anionic ligand other than ND
- L is a neutral ligand
- x 1, 2 or 3
- y 0, 1 or 2
- x + y 3
- m 0, 1 or 2
- m The specific value depends on the different neutral ligands.
- the 4-hydroxy-1,5-naphthyridine ligand of the present invention is similar to the 8-hydroxyquinoline structure of the star molecule Alq 3 in the conventional electroluminescent material, and Alq 3 has excellent electron transporting ability.
- the 4-hydroxy-1,5-naphthyridine ligand has a lower HOMO level, while the LUMO level remains almost unchanged, so that electrons are well injected at the LUMO level. At the same time of conduction, it can greatly enhance the conduction ability of its holes at the HOMO level.
- a red-emitting electroluminescent device can be produced by using a complex formed by a trivalent europium ion and the ligand.
- Photoluminescence quantum yield is another important parameter for photoluminescent and electroluminescent materials.
- a ruthenium complex Eu (8mCND) 3 L can be obtained by sublimation to obtain Eu (8mCND) 3 .
- the measured photoluminescence quantum yield was about 40% (in acetonitrile solution, without oxygen scavenging), which was at a higher level in the ruthenium complex.
- the 4-hydroxy-1,5-naphthyridine ruthenium complex in the present invention has the advantages of compact structure rigidity, strong carrier transport ability, and the like, and is very suitable as a conventional ⁇ -diketone ruthenium complex. Electroluminescent and photoluminescent materials.
- Fig. 1 is a photoluminescence spectrum of Eu (8mCND) 3 measured in Example 5 of the present invention.
- Figure 2 is a schematic view showing the structure of an electroluminescent device prepared in Example 5 of the present invention.
- Fig. 3 is a graph showing the electroluminescence spectrum of the electroluminescent device according to Embodiment 5 of the present invention as a function of voltage.
- the photoluminescence quantum yield measured by using a bipyridyl hydrazine aqueous solution as a reference is about 40% (in acetonitrile solution, no oxygen removal), and is in the ruthenium complex. Higher level. From the excitation spectrum (EuL 3 -ex) and emission spectrum (EuL 3 -em) of the complex (Fig. 1), this type of ruthenium complex can absorb ultraviolet light and down-convert to emit red light, which can be used as an LED. Red phosphor in the middle.
- the fluorescence quantum yield is higher.
- the molecular structure of the complex is relatively compact, and it is not easy to generate thermal quenching, and the thermal stability of the luminescence is very good.
- the use of this type of ruthenium complex for LED phosphors can effectively reduce the amount of rare earth Eu, thereby greatly reducing the cost.
- the material used for the rare earth lanthanum complex electroluminescent device of the present embodiment comprises a conductive glass (ITO) substrate layer, and the hole transport layer is selected from the group consisting of ruthenium, ⁇ 'diphenyl-fluorene, ⁇ '-bis(1-naphthyl)-1. , 1'-diphenyl-4,4'-diamine ( ⁇ ), Eu (8mCND) 3 for the luminescent layer, 2,9-dimethyl-4,7-diphenyl-1 for the hole blocking layer , 10-phenanthroline (BCP), the electron transport layer is 8-hydroxyquinoline aluminum (AIQ), and the cathode layer is a magnesium-silver alloy.
- ITO conductive glass
- Electroluminescent devices can be made by methods known in the art, such as by reference (Appl. Phys. Lett 1987, 51,
- the specific method is: sequentially depositing a hole transporting material, a luminescent material, an electron transporting material and a cathode material on a cleaned conductive glass (ITO) substrate under a high vacuum (less than 8 ⁇ 10 ⁇ 5 Pa).
- ITO glass (effective area: 3x3 mm 2 ), ultrasonically cleaned with organic solvent, dried, ozone cleaned and placed in a vacuum coater, under high vacuum conditions less than 8 x 10 - 5 Pa a quartz oscillator monitor the thickness of each layer, the hole transport material, an organic small molecule, an electron transporting material and a metal cathode magnesium-silver alloy (Mg 0. 9 Ago.i) are sequentially deposited on the conductive glass.
- the thickness of each organic layer can vary.
- the ITO electrode When measuring device performance and electroluminescence spectroscopy, the ITO electrode is always connected to the positive electrode.
- the electroluminescence spectrum was measured by applying a constant voltage (usually between 3 and 30 volts) to the device on a PR650 spectrometer or Hitachi F4500 fluorescence spectrometer (see Figure 3).
- the voltage-current (I-V) curve and the voltage-luminance (L-V) curve are measured on a computer-controlled Keithley 2400 Sourcemeter Unit, and the brightness is corrected by a silicon photodiode (see Figure 4).
- the iridium complex electroluminescent device illuminates at 9 V, and the luminance reaches 100 cd m- 2 at 15.5 V.
- the power efficiency is 0.34 lm W" 1 and the current efficiency is 1.67 cd A" 1 .
- the brightness is 868 cd m- 2 . This is a result of the device being unoptimized and is a medium level in the electroluminescence of the ruthenium complex. It is believed that the optimized processing can further improve the luminescent performance.
Abstract
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CN109852377A (zh) * | 2019-01-18 | 2019-06-07 | 江西师范大学 | 七核Ln-Ba团簇晶态材料及其制备方法和应用 |
CN114133406A (zh) * | 2021-11-24 | 2022-03-04 | 南京邮电大学 | 一种铕(ⅲ)的共轭有机配合物及其制备方法和应用 |
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CN103588800B (zh) * | 2013-11-22 | 2016-03-30 | 中国计量学院 | 一种稀土配合物发光材料及其制备方法和应用 |
CN104844594B (zh) * | 2015-03-24 | 2017-06-06 | 北京大学 | 离子型稀土配合物发光材料及其制备方法与应用 |
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CN113416337A (zh) * | 2021-06-21 | 2021-09-21 | 河北工业大学 | 一种具有抗反射、高透过率的太阳能聚光器及其制备方法 |
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2011
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CN109852377A (zh) * | 2019-01-18 | 2019-06-07 | 江西师范大学 | 七核Ln-Ba团簇晶态材料及其制备方法和应用 |
CN109852377B (zh) * | 2019-01-18 | 2023-03-21 | 江西师范大学 | 七核Ln-Ba团簇晶态材料及其制备方法和应用 |
CN114133406A (zh) * | 2021-11-24 | 2022-03-04 | 南京邮电大学 | 一种铕(ⅲ)的共轭有机配合物及其制备方法和应用 |
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JP5957518B2 (ja) | 2016-07-27 |
KR20140049991A (ko) | 2014-04-28 |
CN102796133A (zh) | 2012-11-28 |
JP2014516040A (ja) | 2014-07-07 |
CN102796133B (zh) | 2015-05-20 |
KR101591484B1 (ko) | 2016-02-18 |
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