CN103013494A - Bonding type polymer-rare earth ternary complex luminescent material and preparation method thereof - Google Patents
Bonding type polymer-rare earth ternary complex luminescent material and preparation method thereof Download PDFInfo
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- CN103013494A CN103013494A CN2012104737272A CN201210473727A CN103013494A CN 103013494 A CN103013494 A CN 103013494A CN 2012104737272 A CN2012104737272 A CN 2012104737272A CN 201210473727 A CN201210473727 A CN 201210473727A CN 103013494 A CN103013494 A CN 103013494A
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- 239000000463 material Substances 0.000 title claims abstract 16
- 229910052761 rare earth metal Inorganic materials 0.000 title claims abstract 16
- 238000002360 preparation method Methods 0.000 title claims abstract 5
- 239000003446 ligand Substances 0.000 claims abstract 11
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims abstract 10
- 229920000642 polymer Polymers 0.000 claims abstract 9
- 238000000034 method Methods 0.000 claims abstract 7
- 150000003384 small molecules Chemical class 0.000 claims abstract 4
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims abstract 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 239000013078 crystal Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000004793 Polystyrene Substances 0.000 claims 2
- 229920002492 poly(sulfone) Polymers 0.000 claims 2
- 229920002223 polystyrene Polymers 0.000 claims 2
- 150000002910 rare earth metals Chemical class 0.000 claims 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- NNMXSTWQJRPBJZ-UHFFFAOYSA-K europium(iii) chloride Chemical compound Cl[Eu](Cl)Cl NNMXSTWQJRPBJZ-UHFFFAOYSA-K 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- -1 rare earth ions Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000002131 composite material Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 229920002521 macromolecule Polymers 0.000 abstract 1
- 239000011159 matrix material Substances 0.000 abstract 1
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Abstract
本发明属于稀土-高分子复合发光材料领域，具体涉及一种键合型聚合物-稀土三元配合物发光材料及其制备方法。本发明以键合萘甲酸配基的聚合物为大分子配基，以萘甲酸、邻菲罗啉和2,2′-联吡啶中的任意一种为小分子配体，与稀土离子配位所得。制备了键合型聚合物-稀土三元配合物发光材料。该方法不但容易实现，而且所得的材料其发光性能大幅度提高，解决了现有技术中稀土配合物存在分散不均、聚合物基质性能差等问题，对制备新型的稀土—高分子发光材料开辟了一条新的途径。
The invention belongs to the field of rare earth-polymer composite luminescent materials, and in particular relates to a bonded polymer-rare earth ternary complex luminescent material and a preparation method thereof. In the present invention, a polymer bonded with a naphthoic acid ligand is used as a macromolecule ligand, and any one of naphthoic acid, o-phenanthroline, and 2,2'-bipyridine is used as a small molecule ligand to coordinate with a rare earth ion income. A bonded polymer-rare earth ternary complex luminescent material was prepared. This method is not only easy to implement, but also the luminescent performance of the obtained material is greatly improved, which solves the problems of uneven dispersion and poor performance of the polymer matrix in the prior art, and opens up new opportunities for the preparation of new rare earth-polymer luminescent materials. a new way.
Description
Technical field
The invention belongs to rare earth-macromolecule composite luminescent material field, be specifically related to a kind of bonding type polymkeric substance-rare earth ternary complexes luminescent material and preparation method thereof.
Background technology
It is good that the rare earth organic complex luminescent material has fluorescence monochromaticity, luminous intensity is high, the characteristics such as internal quantum efficiency is high, fluorescence lifetime is long, be the luminescent material of a class unique properties, all have important application prospect in fields such as luminescence display, probe and sensor, fluoroimmunoassay, electroluminescent devices.But small molecules rare earth organic complex existence and stability is poor, poor and be difficult to the shortcoming such as machine-shaping with the matrix consistency, greatly limited its application.With the rare earth organic complex chamical binding on macromolecular chain, form bonding type polymkeric substance-rare-earth complexes luminous material, this luminescent material is with the electroluminescence performance of rare earth ion excellence and macromolecular compound good mechanical property and the characteristics that are easy to machine-shaping, also can make luminescent material inside be equal phase behaviour, it is the high performance rare-earth complexes luminous material of a class, especially aspect the preparation of electroluminescent device, bonding type polymkeric substance-rare earth luminescent material demonstrates obvious advantage, although polymkeric substance-rare-earth complexes luminous material of having reported at present is also less, has good development prospect.
The chemical structure of bonding type polymkeric substance-rare earth compounding, its characteristics generally are that bonding has the small molecules aglucon on polymer lateral chain, by bonding aglucon and the small molecules aglucon of working in coordination with and the coordination between the rare earth ion, form polymkeric substance-rare earth compounding.The energy absorption of aglucon and shift (Antenna effect) to the energy of rare earth ion causes polymkeric substance-rare earth compounding to launch high-intensity rare earth ion characteristic fluorescence.In the polymer of having reported-rare earth compounding luminescence system, aglucon on the polymer lateral chain mostly is fat carboxyl and mainly comes from the acid of monomer acrylic or methacrylic, carboxyl only plays the mating reaction to rare earth ion, need to add the sensitization aglucon, namely need to add the collaborative coordination of other small molecules part, could form polymkeric substance-rare earth luminescent material.For strengthening the luminescent properties of polymer-rare earth compounding, can introduce the directly aglucon of sensitization rare earth luminescence at polymer lateral chain, such as 1, the parts such as 10-phenanthroline (Phen) part and Schiff alkali, when making aglucon and rare earth generation coordination, directly to rare earth ion generation sensibilized, carry out energy and shift, greatly strengthened the electroluminescence performance of bonding type polymkeric substance-rare earth compounding.
Summary of the invention
The problems referred to above that exist in order to solve existing bonding type polymkeric substance-rare-earth complexes luminous material the invention provides a kind of bonding type polymkeric substance-rare earth ternary complexes luminescent material and preparation method thereof.
Used functional polymer PSFNA and PSNA among the present invention can be according to document [Mingjuan WANG, Gao Baojiao, Du Junmei, the preparation of naphthoic acid functionalization polysulfones and with the fluorescence emitting characteristics of Eu (III) rare earth ion title complex, applied chemistry, 2012] described in method obtain.
The present invention adopts following technical scheme to realize: the preparation method of a kind of bonding type polymkeric substance-rare earth ternary complexes luminescent material, and step is as follows:
(1) preparation of solution I: the small molecules part of 0.2-0.22mmol is dissolved in the 15-25mL solvent, regulates pH with NaOH solution, add 0.213mmol rare earth crystal, be warming up to 45-55 ℃, isothermal reaction 3-4h is solution I;
(2) preparation of solution II: the polymkeric substance that takes by weighing the bonding naphthoic acid aglucon of 0.62-0.65mmol is dissolved in the 25-35mL solvent, and regulates pH with NaOH solution, is the solution II;
(3) solution I and solution II are mixed, and are warming up to 45-55 ℃, isothermal reaction 7-8h, and reaction is settled out polymkeric substance with precipitation agent after finishing, and washing, drying get bonding type polymkeric substance-rare earth ternary complexes luminescent material.
Described small molecules part be naphthoic acid, phenanthroline or 2,2 '-in the dipyridyl any one; Described rare earth crystal is the europium chloride crystallization; Described functional polymer is any one in naphthoic acid functionalization polysulfones or the naphthoic acid functional polystyrene; Described solvent is any one in dimethyl sulfoxide (DMSO), N,N-DIMETHYLACETAMIDE or the dimethyl formamide; The pH that transfers is 6-7; Described precipitation agent is ethanol.
The bonding type polymkeric substance that aforesaid method makes-rare earth ternary complexes luminescent material, described luminescent material is take the polymkeric substance of bonding naphthoic acid aglucon as the macromole aglucon, with naphthoic acid, phenanthroline and 2,2 '-in the dipyridyl any one is the small molecules part, with the rare-earth ion coordination gained, its structural formula is as follows:
。
For the characteristics of luminescence of the present invention is described, study the luminescent properties of this material with fluorescence emission spectrum.With the chloroformic solution casting film-forming of bonding type polymkeric substance-rare earth ternary complexes of preparation, after the oven dry, survey its fluorescence emission spectrum.
Fig. 1 is PSFNA and ternary complex PSF-(NA)
3-Eu (III)-(Phen)
1Infrared spectra.In the spectrogram of modification polysulfones PSFNA, except the whole characteristic absorbance that show polysulfones, at 1710cm
-1The stretching vibration charateristic avsorption band of ligand N A carboxylic carbonyl C=O has appearred in the place, at 3420cm
-1The stretching vibration charateristic avsorption band of carboxylic hydroxyl has appearred in the place.At ternary complex PSF-(NA)
3-Eu (III)-(Phen)
1Spectrogram in, same, the stretching vibration absorption peak of NA carboxylic carbonyl C=O disappears, 1565 and 1407cm
-1Antisymmetric stretching vibration absorption peak and the symmetrical stretching vibration absorption peak of carboxyl appearred in the place, coordination has all occured with Eu (III) ion in two Sauerstoffatoms that ligand N A carboxyl is described, namely the carboxyl of NA with the form of bidentate aglucon and Eu (III) ion huge legendary turtle has occured and closes coordination.In addition, at 413cm
-1The stretching vibration absorption peak of Eu-O key has also appearred in the place; In addition, also at 1552cm
-1The charateristic avsorption band that C=N key in the Phen molecule after the red shift occurred.Above-mentioned variation fully confirms, the collaborative Phen of the carboxyl of NA with Eu (III) ion the coordination huge legendary turtle has occured and closes formation ternary complex PSF-(NA) on the NAPSF macromolecular chain
3-Eu (III)-(Phen)
1
Fig. 2 is PSNA and ternary complex PS-(NA)
3-Eu (III)-(Phen)
1Infrared spectra.In the spectrogram of modified polystyrene PSNA, except the whole characteristic absorbance that show polystyrene, at 1708cm
-1The peak at place is the stretching vibration charateristic avsorption band of ligand N A carboxylic carbonyl C=O, 3421cm
-1The peak at place is the stretching vibration characteristic absorbance of carboxylic hydroxyl.At ternary complex PS-(NA)
3-Eu (III)-(Phen)
1Spectrogram in, NA carboxylic carbonyl C=O is in 1708cm
-1The place the stretching vibration absorption peak disappear, at 1542cm and 1415cm
-1Antisymmetric stretching vibration absorption peak and the symmetrical stretching vibration absorption peak of carboxyl appearred in the place, coordination has all occured with Eu (III) ion in two Sauerstoffatoms that ligand N A carboxyl is described, be that the carboxyl of NA with the form of bidentate aglucon and Eu (III) ion huge legendary turtle has occured and closes coordination, at 416cm
-1The stretching vibration absorption peak of Eu-O key has also appearred in the place; In addition, also at 1564cm
-1The charateristic avsorption band that C=N key in the Phen molecule after the red shift occurred.Above-mentioned variation fully confirms, the collaborative Phen of the carboxyl of NA with Eu (III) ion the coordination huge legendary turtle has occured and closes formation ternary complex PS-(NA) on the PSNA macromolecular chain
3-Eu (III)-(Phen)
1
The present invention compared with prior art, adopting bonding that the polymkeric substance of naphthoic acid (NA) aglucon is arranged is the macromole aglucon, introducing has the small molecules aglucon of strong sensibilized to rare earth ion, can not only the reinforcing copolymer aglucon and the small molecules aglucon to the Transfer of energy of rare earth ion, strengthen luminescent properties, and make prepared polymkeric substance-rare earth ternary complexes luminescent material have good chemical stability and processing characteristics; Adopting polysulfones (PSF) is polymeric matrix, makes resulting polymers-rare earth ternary complexes luminescent material have good mechanical property and thermostability (thermostability: the bisphenol-a polysulfone second-order transition temperature is 150 ℃).
Description of drawings
Fig. 1 is the prepared polymkeric substance of PSFNA and embodiment 1-ternary complex PSF-(NA)
3-Eu (III)-(Phen)
1Infrared spectra;
Fig. 2 is the prepared polymkeric substance of PSNA and embodiment 3-ternary complex PS-(NA)
3-Eu (III)-(Phen)
1Infrared spectra;
Fig. 3 is the prepared polymkeric substance of embodiment 1-ternary complex PSF-(NA)
3-Eu (III)-(Phen)
1Solid film and Eu (III) Cl
3Fluorescence emission spectrum;
Fig. 4 is the prepared polymkeric substance of embodiment 2-ternary complex PSF-(NA)
3-Eu (III)-(Bipy)
1Solid film and Eu (III) Cl
3Fluorescence emission spectrum;
Fig. 5 is the prepared polymkeric substance of embodiment 3-ternary complex PS-(NA)
3-Eu (III)-(Phen)
1Solid film and Eu (III) Cl
3Fluorescence emission spectrum;
Fig. 6 is the prepared polymkeric substance of embodiment 4-ternary complex PS-(NA)
3-Eu (III)-(NA)
1Solid film and Eu (III) Cl
3Fluorescence emission spectrum;
Fig. 7 is the prepared polymkeric substance of embodiment 5-ternary complex PSF-(NA)
3-Eu (III)-(NA)
1Solid film and Eu (III) Cl
3Fluorescence emission spectrum;
Fig. 8 is the prepared polymkeric substance of embodiment 6-ternary complex PS-(NA)
3-Eu (III)-(Bipy)
1Solid film and Eu (III) Cl
3Fluorescence emission spectrum.
Embodiment
The present invention will be further described below in conjunction with specific embodiment, but protection scope of the present invention is not limited to this.
Embodiment 1: in the Erlenmeyer flask of 100mL, the phenanthroline of 0.213mmol is dissolved in the 25mL solvent dimethyl formamide, regulates pH=6-7 with NaOH solution, add again 0.213mmol europium chloride crystal, be warming up to 50 ℃, isothermal reaction 3.5h becomes the solution I; The naphthoic acid functionalization polysulfones (PSFNA) that takes by weighing 0.639mmol is dissolved in the 25mL dimethyl formamide, and regulates pH=6-7 with NaOH solution, becomes the solution II; Solution I and solution II are mixed, and are warming up to 50 ℃, isothermal reaction 8h, and reaction is settled out polymkeric substance with ethanol after finishing, and washing, drying namely get bonding type polymkeric substance-rare earth ternary complexes luminescent material PSF-(NA)
3-Eu (III)-(Phen)
1The ternary complex of preparation is dissolved in the chloroform, and casting film-forming after the oven dry, take 343nm as excitation wavelength, is surveyed its fluorescence emission spectrum, sees Fig. 3.As seen from the figure, the luminous intensity of the luminous strength ratio europium chloride of this prepared ternary complex luminescent material has improved 41 times.
Embodiment 2: in the Erlenmeyer flask of 100mL, 2,2 of 0.2mmol '-dipyridyl is dissolved in the 15mL solvent N,N-DIMETHYLACETAMIDE, regulate pH=6-7 with NaOH solution, add again 0.213mmol europium chloride crystal, be warming up to 55 ℃, isothermal reaction 3h becomes the solution I; The naphthoic acid functionalization polysulfones (PSFNA) that takes by weighing again 0.62mmol is dissolved in the 35mL N,N-DIMETHYLACETAMIDE, and regulates pH=6-7 with NaOH solution, becomes the solution II; Solution I and solution II are mixed, and are warming up to 55 ℃, isothermal reaction 7h, and reaction is settled out polymkeric substance with ethanol after finishing, and washing, drying namely get bonding type polymkeric substance-rare earth ternary complexes luminescent material PSF-(NA)
3-Eu (III)-(Bipy)
1The ternary complex of preparation is dissolved in the chloroform, and casting film-forming after the oven dry, take 343nm as excitation wavelength, is surveyed its fluorescence emission spectrum, sees Fig. 4.As seen from the figure, the luminous intensity of the luminous strength ratio europium chloride of this prepared ternary complex luminescent material has improved 33 times.
Embodiment 3: in the Erlenmeyer flask of 100mL, the phenanthroline of 0.21mmol is dissolved in the 20mL solvent dimethyl sulfoxide (DMSO), regulates pH=6-7 with NaOH solution, add 0.213mmol europium chloride crystal again, be warming up to 55 ℃, isothermal reaction 3h becomes the solution I; The naphthoic acid functional polystyrene (PSNA) that takes by weighing again 0.65mmol is dissolved in the 30mL dimethyl sulfoxide (DMSO), and regulates pH=6-7 with NaOH solution, becomes the solution II; Solution I and solution II are mixed, and are warming up to 45 ℃, isothermal reaction 8h, and reaction is settled out polymkeric substance with ethanol after finishing, and washing, drying namely get bonding type polymkeric substance-rare earth ternary complexes luminescent material PS-(NA)
3-Eu (III)-(Phen)
1The ternary complex of preparation is dissolved in the chloroform, and casting film-forming after the oven dry, take 343nm as excitation wavelength, is surveyed its fluorescence emission spectrum, sees Fig. 5.As seen from the figure, the luminous intensity of the luminous strength ratio europium chloride of this prepared ternary complex luminescent material has improved 39 times.
Embodiment 4: in the Erlenmeyer flask of 100mL, the naphthoic acid of 0.22mmol is dissolved in the 25mL solvent dimethyl sulfoxide (DMSO), regulates pH=6-7 with NaOH solution, add 0.213mmol europium chloride crystal again, be warming up to 45 ℃, isothermal reaction 4h becomes the solution I; The naphthoic acid functional polystyrene (PSNA) that takes by weighing again 0.64mmol is dissolved in the 25mL dimethyl sulfoxide (DMSO), and regulates pH=6-7 with NaOH solution, becomes the solution II; Solution I and solution II are mixed, and are warming up to 55 ℃, isothermal reaction 7.5h, and reaction is settled out polymkeric substance with ethanol after finishing, and washing, drying namely get bonding type polymkeric substance-rare earth ternary complexes luminescent material PS-(NA)
3-Eu (III)-(NA)
1The ternary complex of preparation is dissolved in the chloroform, and casting film-forming after the oven dry, take 343nm as excitation wavelength, is surveyed its fluorescence emission spectrum, sees Fig. 6.As seen from the figure, the luminous intensity of the luminous strength ratio europium chloride of this prepared ternary complex luminescent material has improved 45 times.
Embodiment 5: in the Erlenmeyer flask of 100mL, the naphthoic acid of 0.22mmol is dissolved in the 25mL solvent dimethyl formamide, regulates pH=6-7 with NaOH solution, add 0.213mmol europium chloride crystal again, be warming up to 51 ℃, isothermal reaction 3.5h becomes the solution I; The naphthoic acid functionalization polysulfones (PSFNA) that takes by weighing 0.65mmol is dissolved in the 25mL dimethyl formamide, and regulates pH=6-7 with NaOH solution, becomes the solution II; Solution I and solution II are mixed, and are warming up to 49 ℃, isothermal reaction 7.5h, and reaction is settled out polymkeric substance with ethanol after finishing, and washing, drying namely get bonding type polymkeric substance-rare earth ternary complexes luminescent material PSF-(NA)
3-Eu (III)-(NA)
1The ternary complex of preparation is dissolved in the chloroform, and casting film-forming after the oven dry, take 343nm as excitation wavelength, is surveyed its fluorescence emission spectrum, sees Fig. 7.As seen from the figure, the luminous intensity of the luminous strength ratio europium chloride of this prepared ternary complex luminescent material has improved 46 times.
Embodiment 6: in the Erlenmeyer flask of 100mL, 2,2 of 0.21mmol '-dipyridyl is dissolved in the 25mL solvent N,N-DIMETHYLACETAMIDE, regulate pH=6-7 with NaOH solution, add again 0.213mmol europium chloride crystal, be warming up to 55 ℃, isothermal reaction 3h becomes the solution I; The naphthoic acid functional polystyrene (PSNA) that takes by weighing 0.62mmol is dissolved in the 25mL N,N-DIMETHYLACETAMIDE, and regulates pH=6-7 with NaOH solution, becomes the solution II; Solution I and solution II are mixed, and are warming up to 50 ℃, isothermal reaction 7.5h, and reaction is settled out polymkeric substance with ethanol after finishing, and washing, drying namely get bonding type polymkeric substance-rare earth ternary complexes luminescent material PS-(NA)
3-Eu (III)-(Bipy)
1The ternary complex of preparation is dissolved in the chloroform, and casting film-forming after the oven dry, take 343nm as excitation wavelength, is surveyed its fluorescence emission spectrum, sees Fig. 8.As seen from the figure, the luminous intensity of the luminous strength ratio europium chloride of this prepared ternary complex luminescent material has improved 34 times.
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Cited By (9)
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| CN104004121A (en) * | 2014-05-29 | 2014-08-27 | 常州大学 | Method for preparing aromatic carboxylic acid macromolecular fluorescent rare-earth complex |
| CN104674368A (en) * | 2015-01-28 | 2015-06-03 | 南通华纶化纤有限公司 | Organic rare earth europium luminescent nylon and preparation method thereof |
| CN105218818A (en) * | 2015-09-11 | 2016-01-06 | 中北大学 | Functionalization polysulfones-Tb (III) ionic complex luminescent material preparation method |
| CN105544203A (en) * | 2016-01-28 | 2016-05-04 | 江苏侨新纤维有限公司 | Preparation method for fluorescent spandex utilizing spandex waste fiber as raw material |
| CN106243355A (en) * | 2016-07-08 | 2016-12-21 | 中北大学 | Amino phenolic bidentate Schiff's base ligand functionalized polymer rare earth complex luminescent material and preparation method thereof |
| CN106349483A (en) * | 2016-08-14 | 2017-01-25 | 衡阳师范学院 | Multicore calcium polymer containing naphthylcarboxymethyl and phenanthroline and preparation method and application thereof |
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| CN104004121A (en) * | 2014-05-29 | 2014-08-27 | 常州大学 | Method for preparing aromatic carboxylic acid macromolecular fluorescent rare-earth complex |
| CN104674368A (en) * | 2015-01-28 | 2015-06-03 | 南通华纶化纤有限公司 | Organic rare earth europium luminescent nylon and preparation method thereof |
| CN105218818A (en) * | 2015-09-11 | 2016-01-06 | 中北大学 | Functionalization polysulfones-Tb (III) ionic complex luminescent material preparation method |
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