CN104130771A - Triple-core rare earth europium complex luminescent material, preparation method and application thereof - Google Patents
Triple-core rare earth europium complex luminescent material, preparation method and application thereof Download PDFInfo
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- CN104130771A CN104130771A CN201410316865.9A CN201410316865A CN104130771A CN 104130771 A CN104130771 A CN 104130771A CN 201410316865 A CN201410316865 A CN 201410316865A CN 104130771 A CN104130771 A CN 104130771A
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- rare earth
- europium complex
- earth europium
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Abstract
The invention provides a triple-core rare earth europium complex luminescent material, a preparation method and an application, the triple-core rare earth europium complex is the luminescent material with good heat stability and high luminescence efficiency, the preparation method comprises the following steps: reacting an early stage complex Eu(beta-dione)3.2H2O and a dipyridine derivative (tristpy), washing and drying distilled water and ethanol under vacuum to obtain the complex luminescent material. The complex luminescent material is solid powder with cream yellow color, and the synthetic method has the advantages of simple operation and low production cost. The complex luminescent material has important significance for the development of the next generation flat panel display devices having superior performance. The triple-core rare earth europium complex has the advantages of good dissolving performance, high luminescence efficiency and good heat stability, and can be used for a latent material in photoluminescence or electroluminescent field.
Description
Technical field
The present invention relates to rare earth luminescent material field, particularly a kind of three arm terpyridyls (tristpy) are as three core Rare Earth Europium Complex luminescent materials and preparation and the application of neutral ligand.
Background technology
The series of advantages such as rare earth luminescent material has that emission band is sharp-pointed, half-peak width (being generally less than 10nm), internal quantum efficiency is high, fluorescence lifetime is long and resistance toheat is superior are the study hotspots in luminous organic material field always.China has abundant rare earth resources, and A wide selection of colours and designs, and this application that is rare earth luminescent material provides good guarantee.At present, the research and development of rare earth luminescent material has covered whole luminous field, and has formed certain commercial production scale and market, and rare earth luminescent material has become the leading of current luminescent material.Therefore, the rare-earth products of active development high-tech content, is converted into science and technology competition advantage by the rare earth resources advantage of China, and for the industrial transformation and the upgrading that promote China, and it is all significant to promote international competitiveness.
Material is one of three large pillars of society development in science and technology, and luminescent material is a kind of important functional materials wherein.The transition of the energy level that rare earth ion is abundant and 4f layer electronics, makes rare earth ion become huge luminous treasure-house.Design and synthesize the rare earth compounding with excellent luminescent properties is the target that various countries investigators pursue always, because the distinctive 4f layer of rare earth ion electronics is subject to outer 5S
25P
6the shielding effect of layer electronics, makes rare earth ion be subject to the impact of Ligand Field very little, so luminescence rare earth ion generally has the advantages such as narrow band fluorescent emission, purity of color is high, luminous by force, luminescent lifetime is long.Yet the specific absorbance of rare earth ion is very little, need to carry out by means of " antenna effect " of part the transmission of energy, the feature that could effectively strengthen rare earth ion is luminous.
According to energy level matching principle, the part that rare earth ion is conventional is divided into two kinds of anion ligand and neutral ligands.Wherein anion ligand mainly comprises beta-diketon class part and carboxylic-acid part; Neutral ligand mainly contains the heterocyclic ligands such as phenanthroline, second bipyridine, triphenylphosphine oxide derivative.Numerous neutral ligands of finding report are mainly to play the requirement that meets rare-earth ion coordination number at present, and what the transmission ofenergy effect between part and rare earth ion was risen has little effect.Luminous efficiency and the thermal stability of Rare Earth Europium Complex luminescent material are not high enough, and this remains restriction, and it obtains the key issue of application at key areas such as organic electroluminescents.
Summary of the invention
For above shortcomings in prior art, the object of the invention is to solve luminous efficiency and the not high enough problem of thermal stability of prior art europium complex luminescent material, a kind of three core Rare Earth Europium Complex luminescent material and application thereof with high luminescent properties and high thermal stability are provided.
Another object of the present invention is to provide that a kind of production cost is low, the method for the preparation of easy handling three core Rare Earth Europium Complex luminescent materials.
Realize goal of the invention, the present invention adopts following technical scheme: a kind of three core Rare Earth Europium Complex luminescent materials, and the general structure of this three core Rare Earth Europium Complex luminescent material is as shown in (I):
Wherein, R be H or-CH
3; R
1for-CH
3,-CF
3, phenyl or naphthyl; R
2for-CH
3, thienyl, phenyl or naphthyl.
The preparation method of above-mentioned three core Rare Earth Europium Complex luminescent materials, comprises the following steps:
1) be that the ratio of 1～10:1 is got the europium complex Eu (beta-diketon) shown in formula II in molar ratio
3.2H
2o mixes with three arm terpyridyls (tristpy) shown in formula III, adds good solvent, stirs, and makes dissolution of solid, reactant is warming up to 40～90 ℃, sustained reaction 3～12 hours.
2) by step 1) products therefrom is cooled to room temperature, remove precipitation, solvent evaporated obtains solute, uses successively distilled water and washing with alcohol solute, by the vacuum-drying 12～24 hours under 60 ℃ of conditions of the solute after washing, obtain three above-mentioned core Rare Earth Europium Complex luminescent materials.
Compared to existing technology, the present invention has following beneficial effect:
1, this three core Rare Earth Europium Complex luminescent material mostly is milk yellow powder, and this luminescent material molecule has three arm configurations, by three identical europium complex unit Eu (beta-diketon)
3(TPY) form each Eu (beta-diketon)
3(TPY) unit is by an Eu
3+form nine coordination structures, Eu with six Sauerstoffatoms and three nitrogen-atoms from terpyridyl from three beta-diketonate ligands
3+be positioned at coordination polyhedron center, on part, contain rigidity phenyl ring and aromatic heterocycle, strengthened rigidity and the stability of agent structure, be also conducive to compound and by " antenna effect ", realize high efficiency luminous simultaneously.Described luminescent material, under the ultraviolet excitation of certain wavelength, all be take the 613nm ruddiness strong as maximum emission peak sends, and can be used as red photoluminescent material, or is used as the luminescent layer material in multilayer electroluminescent device.
2,, in the present invention, neutral ligand tristpy can while and three Eu
3+coordination, so just make in conventional monokaryon europium complex 1 of luminescence center in same light emitting molecule be increased to 3, thereby improved the energy transfer efficiency of part to rare-earth europium central ion, therefore the present invention's three core Rare Earth Europium Complexes are compared with conventional monokaryon Rare Earth Europium Complex, and luminescent properties is more superior.Therefore the present invention's three core Rare Earth Europium Complex luminescent materials have, good stability, solvability are good, good film-forming property, long service life and luminous efficiency high, are conducive to processing and are prepared into large-area display device, and application prospect is very wide; Particularly can be used as the potential material in photoluminescence or electroluminescent field.
3, the present invention prepares three core Rare Earth Europium Complex luminescent material methods, step 1) in three arm terpyridyls (tristpy) contain three terpyridyl unit, can simultaneously carry out coordination with three rare-earth europium ions.Neutral ligand tristpy has very strong coordination ability, under room temperature, can carry out effective coordination with rare-earth europium ion.The energy level of tristpy and europium ion
5d
0energy level matches, thus tristpy part can be effectively by the transmission ofenergy absorbing to europium ion, thereby improved the luminous efficiency of this three core Rare Earth Europium Complex material.In addition, rare earth ion and stable aromaticity part tristpy organically combine, and the thermostability of this three core Rare Earth Europium Complex is improved greatly.
The present invention is under solution reaction condition, by title complex Eu in early stage (beta-diketon)
3.2H
2o and three arm terpyridyl derivatives (tristpy) reaction preparation.Therefore, the present invention has simple, and the feature that manufacturing cost is low is significant for the flat panel display device of development superior performance of future generation.
Accompanying drawing explanation
Fig. 1 is the infrared spectrogram (pressing potassium bromide troche) of three core Rare Earth Europium Complexes of the embodiment of the present invention 1 gained.
Fig. 2 is the uv absorption spectra of three core Rare Earth Europium Complexes of the embodiment of the present invention 1 gained.
Fig. 3 is the fluorescent exciting spectrogram (emission wavelength: 613nm, slit 5nm, solid state powder) of three core Rare Earth Europium Complexes of the embodiment of the present invention 1 gained.
Fig. 4 is the fluorescence emission spectrogram (excitation wavelength: 368nm, slit 5nm, solid state powder) of three core Rare Earth Europium Complexes of the embodiment of the present invention 1 gained.
Fig. 5 is the thermogravimetric curve (N of three core Rare Earth Europium Complexes of the embodiment of the present invention 1 gained
2protection, 15 ℃/min of temperature rise rate).
Embodiment
Below in conjunction with embodiment and accompanying drawing, the present invention is described in further detail, but embodiments of the present invention are not limited to this.
Embodiment 1:
1) getting material tristpy shown in the europium complex shown in the formula IV of 0.3mmol and 0.1mmol formula (V) is placed in one and stirs and the 100ml there-necked flask of reflux with magneton, then add 60ml tetrahydrofuran (THF) (THF), the concentration 1 * 10 of THF solution
-5mol/L, stirs and to allow dissolution of solid, and now solution is light yellow, is warming up to 70 ℃, refluxes 6 hours.
2) by step 1) products therefrom is cooled to room temperature, remove precipitation, evaporate to dryness THF obtains solute, then uses successively distilled water and washing with alcohol solute, by the vacuum-drying 24 hours under 60 ℃ of conditions of the solute after washing, obtain three core Rare Earth Europium Complex Eu shown in formula VI
3(TTA)
9(tristpy), milk yellow pressed powder, productive rate 97%.
Three prepared core Rare Earth Europium Complexes are soluble in common organic solvent, and as acetone, tetrahydrofuran (THF), trichloromethane or DMF etc., hence one can see that, and this title complex has good film forming properties.
This three core Rare Earth Europium Complex infrared spectrogram as shown in Figure 1, near being arranged in 581nm, there is a new vibration peak that part tristpy does not have, the stretching vibration peak that this belongs to N → Eu in three core europium complexes, shows part tritpy and europium ion success coordination.As shown in Figure 2, this three core europium complex, 250～400nm region in ultra-violet absorption spectrum has very strong extinction ability to uv absorption spectra as shown in Figure 2.Fluorescent exciting spectrogram as shown in Figure 3, in 200～450nm region, three core europium complex excitation peak intensity are higher, in addition, do not see obvious europium ion characteristic emission peak in excitation spectrum, this shows that part tristpy is very effective to the ability transmission between luminescence center europium ion.
Fluorescence emission spectrogram as shown in Figure 4.As can be seen from Figure 4, this three core Rare Earth Europium Complex shows as pure red emission, its peak width at half height is about 10nm, and the emission peak without part occurs in fluorescence radiation spectrum (PL), and this shows that be completely by organic ligand to the transmission ofenergy luminescence center europium ion.As shown in Figure 5, as can be seen from Figure 5, the corresponding temperature of the mass loss of this title complex 5% is 206 ℃ to thermogravimetric curve, has good resistance toheat.
As can be seen from the above results, this trinuclear complex has good solubility property, film forming properties, and photoluminescence performance and thermal stability, be to prepare the required potential luminescent material of large-area displays device.
Embodiment 2:
1) getting material tristpy shown in the europium complex shown in the formula (VII) of 0.3mmol and 0.1mmol formula (V) is placed in one and stirs and the 100ml there-necked flask of reflux with magneton, then add 60ml tetrahydrofuran (THF) (THF), stirring allows dissolution of solid, now solution is light yellow, be warming up to 70 ℃, reflux 4 hours;
2) by step 1) products therefrom is cooled to room temperature, remove precipitation, rotary evaporation is removed THF and is obtained solute, then uses successively distilled water and washing with alcohol solute, by the vacuum-drying 12 hours under 60 ℃ of conditions of the solute after washing, obtain three core Rare Earth Europium Complex Eu shown in formula (VIII)
3(DBM)
9(tristpy), light yellow solid powder, productive rate 91%.
Three prepared core Rare Earth Europium Complexes are soluble in common organic solvent, and as trichloromethane, methylene dichloride, acetone, tetrahydrofuran (THF) or DMF etc., hence one can see that, and this three core Rare Earth Europium Complex has good film forming properties.
Finally explanation is, above embodiment is only unrestricted in order to technical scheme of the present invention to be described, although the present invention is had been described in detail with reference to preferred embodiment, those of ordinary skill in the art is to be understood that, can modify or be equal to replacement technical scheme of the present invention, and not departing from aim and the scope of technical solution of the present invention, it all should be encompassed in the middle of claim scope of the present invention.
Claims (6)
1. three core Rare Earth Europium Complex luminescent materials, is characterized in that, this three core Rare Earth Europium Complex luminescent material has following general structure:
Wherein, R be H or-CH
3; R
1for-CH
3,-CF
3, phenyl or naphthyl; R
2for-CH
3, thienyl, phenyl or naphthyl.
2. a preparation method for three core Rare Earth Europium Complex luminescent materials, is characterized in that, comprises the following steps:
1) be that the ratio of 1～10:1 is got europium complex Eu (beta-diketon) in molar ratio
3.2H
2o mixes with three arm terpyridyls, adds good solvent, stirs, and makes dissolution of solid, reactant is warming up to 40～90 ℃, sustained reaction 3～12 hours;
2) by step 1) products therefrom is cooled to room temperature, removes precipitation, and solvent evaporated obtains solute; Use successively distilled water and washing with alcohol solute, by the solute after washing, under 40～90 ℃ of conditions, vacuum-drying 12～24 hours, obtains three core Rare Earth Europium Complex luminescent materials claimed in claim 1;
Described europium complex Eu (beta-diketon)
3.2H
2o has following general structure:
Described three arm terpyridyls have following general structure:
3. the preparation method of three core Rare Earth Europium Complex luminescent materials as claimed in claim 2, is characterized in that, the temperature of described step 1 is preferably 70 ℃.
4. the preparation method of three core Rare Earth Europium Complex luminescent materials as claimed in claim 2, is characterized in that, the good solvent of described step 1 is tetrahydrofuran (THF), acetone, DMF, methylene dichloride or trichloromethane.
5. the preparation method of three core Rare Earth Europium Complex luminescent materials as claimed in claim 2, is characterized in that, in described step 1, and europium complex Eu (beta-diketon)
3.2H
2the mol ratio of O and three arm terpyridyls is preferably 3:1.
6. an application for three core Rare Earth Europium Complex luminescent materials, is characterized in that, three core Rare Earth Europium Complex luminescent materials claimed in claim 1 are applied to red photoluminescent material, or as the luminescent layer luminescent material in multilayer electroluminescent device.
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Cited By (10)
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| CN104829639A (en) * | 2015-04-24 | 2015-08-12 | 嘉兴学院 | Hyperbranched polyester rare earth complex containing nitrogen heterocyclic terminal group, and preparation method and use thereof |
| CN105086996A (en) * | 2015-08-26 | 2015-11-25 | 重庆理工大学 | Luminescent material with cyclotriphosphazene cross-linked rare-earth complexes and method for preparing luminescent material |
| CN106432341A (en) * | 2016-09-12 | 2017-02-22 | 重庆理工大学 | Hyperbranched CTP-TPY (Cyclotriphosphazene Terpyridyl), preparation method and recognition method of metal ions |
| CN109438941A (en) * | 2018-10-31 | 2019-03-08 | 重庆理工大学 | A kind of preparation method and application of biodegradable rare-earth fluorescent film |
| CN110003278A (en) * | 2019-04-23 | 2019-07-12 | 重庆理工大学 | A kind of six core tripolyphosphazene europium complex luminescent materials of excited by visible light and its preparation method and application |
| CN110551292A (en) * | 2019-09-18 | 2019-12-10 | 贵州师范大学 | preparation method of rare earth luminescent material with adjustable light color |
| CN111518141A (en) * | 2020-05-19 | 2020-08-11 | 中国科学院化学研究所 | Star trinuclear metal ruthenium complex and application thereof in near-infrared electrochromic film |
| CN111606934A (en) * | 2020-06-06 | 2020-09-01 | 桂林理工大学 | Preparation, structure and fluorescence application of bteb bridged binuclear europium complex |
| CN113896904A (en) * | 2021-11-16 | 2022-01-07 | 曲阜师范大学 | Quaternary supermolecule anti-counterfeiting system of cucurbituril [8] -diarylethene derivative-terpyridyl imidazole-europium and preparation method thereof |
| CN115466404A (en) * | 2022-09-16 | 2022-12-13 | 贵州师范大学 | Preparation and application of homonuclear rare earth coordination polymer white light material |
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| CN104829639A (en) * | 2015-04-24 | 2015-08-12 | 嘉兴学院 | Hyperbranched polyester rare earth complex containing nitrogen heterocyclic terminal group, and preparation method and use thereof |
| CN105086996A (en) * | 2015-08-26 | 2015-11-25 | 重庆理工大学 | Luminescent material with cyclotriphosphazene cross-linked rare-earth complexes and method for preparing luminescent material |
| CN105086996B (en) * | 2015-08-26 | 2018-05-15 | 重庆理工大学 | A kind of tripolyphosphazene crosslinking rare-earth complexes luminous material and preparation method thereof |
| CN106432341A (en) * | 2016-09-12 | 2017-02-22 | 重庆理工大学 | Hyperbranched CTP-TPY (Cyclotriphosphazene Terpyridyl), preparation method and recognition method of metal ions |
| CN106432341B (en) * | 2016-09-12 | 2018-05-15 | 重庆理工大学 | Hyperbranched tripolyphosphazene terpyridyl and preparation and the recognition methods to metal ion |
| CN109438941A (en) * | 2018-10-31 | 2019-03-08 | 重庆理工大学 | A kind of preparation method and application of biodegradable rare-earth fluorescent film |
| CN110003278A (en) * | 2019-04-23 | 2019-07-12 | 重庆理工大学 | A kind of six core tripolyphosphazene europium complex luminescent materials of excited by visible light and its preparation method and application |
| CN110003278B (en) * | 2019-04-23 | 2021-07-27 | 重庆理工大学 | Visible light excited six-core triphosphazene europium complex luminescent material and preparation method and application thereof |
| CN110551292A (en) * | 2019-09-18 | 2019-12-10 | 贵州师范大学 | preparation method of rare earth luminescent material with adjustable light color |
| CN111518141A (en) * | 2020-05-19 | 2020-08-11 | 中国科学院化学研究所 | Star trinuclear metal ruthenium complex and application thereof in near-infrared electrochromic film |
| CN111518141B (en) * | 2020-05-19 | 2023-08-08 | 中国科学院化学研究所 | Star-shaped trinuclear metal ruthenium complex and application thereof in near-infrared electrochromic film |
| CN111606934A (en) * | 2020-06-06 | 2020-09-01 | 桂林理工大学 | Preparation, structure and fluorescence application of bteb bridged binuclear europium complex |
| CN113896904A (en) * | 2021-11-16 | 2022-01-07 | 曲阜师范大学 | Quaternary supermolecule anti-counterfeiting system of cucurbituril [8] -diarylethene derivative-terpyridyl imidazole-europium and preparation method thereof |
| CN115466404A (en) * | 2022-09-16 | 2022-12-13 | 贵州师范大学 | Preparation and application of homonuclear rare earth coordination polymer white light material |
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