CN102584870A - Rare-earth 2,4,6-tri(2-pyridyl) triazine complex containing aromatic carboxylic acid and preparation method for complex - Google Patents
Rare-earth 2,4,6-tri(2-pyridyl) triazine complex containing aromatic carboxylic acid and preparation method for complex Download PDFInfo
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Abstract
The invention discloses a rare-earth organic luminous complex containing europium, terbium, samarium, 2,4,6-tri(2-pyridyl) triazine (TPTZ) and aromatic carboxylate radical ions and derivatives thereof and a preparation method for the rare-earth organic luminous complex. The invention is characterized in that a chemical formula of the rare-earth organic luminous complex is Rex(TPTZ)xAyBz(C2H5OH).nH2O, wherein RE may be one of Sm<3+>, Eu<3+> and Tb<3+>, A is aromatic carboxylic acid and derivatives thereof, B is negative monovalent inorganic anions, x is equal to 1 or 2, y is more than 0, z is more than or equal to 0, and n is a positive integer of between 1 and 8; when A is a monocarboxylic acid radical, 3x is equal to a sum of y and z; and when A is a dicarboxylic acid radical, 3x is equal to a sum of 2y and z; TPTZ is 2,4,6-tri(2-pyridyl) triazine. The rare-earth organic luminous complex contains two organic ligands, namely TPTZ and the aromatic carboxylate radical ions and the derivatives, is high in stability and dissolubility, long in service life and high in luminous efficiency. The preparation method is easy and convenient to operate, mild in condition, high in controllability, short in treatment time and low in energy consumption.
Description
Technical field
The present invention relates to a kind of organic light-emitting rare earth complexe and preparation method thereof, relate in particular to a kind of europium, terbium, samarium and 2,4 of containing, title complex of 6-TPTZ and aromatic carboxylic acid radical ion and verivate thereof and preparation method thereof.
Background technology
Rare earth organic complex is the luminescent material of one type of better performances owing to have good arrowband luminescent properties and long fluorescence lifetime, has obtained using widely at optical field.In addition because its luminous intensity is high, monochromaticity is good, so also be widely used in fields such as bioanalysis chemistry, laserable material, anti-false trademark, color shifting inks.
The aromatic carboxylic acid radical ion is a kind of organic anion part commonly used, and they can form stable title complex with rare earth ion, and can play " antenna ", and the luminous energy that absorbs is shifted to rare earth ion.Because the Coulomb repulsion effect between the inorganic anion, only to be difficult to make rare earth ion reach coordination saturated for inorganic anion, causes more solvent molecule to participate in the coordination of rare earth ion, and the luminous efficiency of rare earth ion is reduced.
Neutral organic ligand such as nitrogenous aromatic heterocycle be owing to absorb ultraviolet or visible luminous energy well, and can energy efficient shifted and pass to and its coordinate rare earth ion, thereby strengthen the luminous intensity of rare earth compounding.And they can replace solvent molecule and rare-earth ion coordination, thereby reduce the power loss that solvent molecule causes.But the title complex that only neutral organic ligand and rare earth ion form often contains more inorganic anions such as hydroxide radical, with the luminescence quenching of rare earth ion.Therefore, studying the title complex of being made up of organic anion part and neutral organic ligand and rare earth ion has great importance to the rare earth compound that obtains higher luminous efficiency.
2,4, and 6-three pyridyl-1,3,5-triazines (2,4,6-tri (2-pyridyl)-1,3,5-triazine is called for short TPTZ) and have a plurality of aromatic nucleus, fine to the absorption of light, also can well pass ability.Simultaneously, this part has a plurality of nitrogen-atoms haptos, and ability and rare earth ion form five-ring, make title complex have special stability.1969, people such as Durham synthesized 2,4 of lanthanon first in ethanolic soln, 6-TPTZ title complex [Ln (TPTZ) (NO
3)
3(H
2O)] 2H
2O (Ln=La-Nd, Sm-Lu, Y; Journal of Inorganic Nuclear Chemistry, 1969,31,571).About the report of rare earth ion and TPTZ and organic anion part seldom, people such as Zhiping Zheng had synthesized Eu (DBM) in 2004
3(TPTZ) ternary complex, and report that this title complex has stronger luminous intensity (Inorganica Chimica Acta, 2004,357,630), wherein DBM is the part of beta-diketon class.
Summary of the invention
The shortcoming that the objective of the invention is to overcome prior art provides a kind of organic light-emitting rare earth complexe that contains europium, terbium, samarium and TPTZ and aromatic carboxylic acid radical ion and verivate thereof and preparation method thereof with not enough.It is characterized in that containing simultaneously two kinds of organic ligands of TPTZ and aromatic carboxylic acid radical ion and verivate thereof, compare with the title complex that only contains this a kind of neutral organic ligand of TPTZ, this type of title complex has stronger luminous intensity.Organic light-emitting rare earth complexe good stability provided by the invention, solvability are good, long service life, luminous efficiency are high.Preparing method of the present invention is easy and simple to handle, mild condition, and controllability is strong, and the treatment time is short, and energy expenditure is low.
The object of the invention is realized through following technical scheme:
A kind of organic light-emitting rare earth complexe that contains europium, terbium, samarium and TPTZ and aromatic carboxylic acid radical ion and verivate thereof, the chemical formula that it is characterized in that it is RE
x(TPTZ)
xA
yB
z(C
2H
5OH) nH
2O, wherein RE is Sm
3+, Eu
3+, Tb
3+In a kind of, A is aromatic carboxylic acid root and verivate thereof, B is negative univalent inorganic anion, x=1 or 2, y＞0, z>=0, n is the positive integer of 1-8; When A is the monocarboxylic acid root, 3x=y+z; When A is the di-carboxylic acid root, 3x=2y+z; TPTZ is 2,4, the 6-TPTZ, and its structural formula is:
Described aromatic carboxylic acid root and verivate (A) thereof are selected from a kind of in benzoate anion, phenoxy acetic acid root, salicylic acid root, m-Salicylic acid root, PHB root, p-Nitrobenzenecarboxylic acid root, para hydroxybenzene fluoroacetic acid root, phthalate, m-phthalic acid root, terephthaldehyde's acid group, the 1-naphthoic acid root.
Described negative univalent inorganic anion (B) is selected from Cl
-, Br
-, I
-, ClO
4 -, NO
3 -In one or more.
A kind of preparation contains the organic light-emitting rare earth complexe RE of europium, terbium, samarium and TPTZ and aromatic carboxylic acid root and verivate thereof
x(TPTZ)
xA
yB
z(C
2H
5OH) nH
2The method of O may further comprise the steps:
(1) TPTZ is used anhydrous alcohol solution, 30 ℃ to reflux temperature, stir and to add a certain amount of inorganic salt of rare earth REB down
3Ethanolic soln, 30 ℃ to the temperature of reaction of reflux temperature heated and stirred 0.5-24 hour, add the ethanol and the water mixed solution of a certain amount of aromatic carboxylic acid and verivate thereof then, regulate the pH value to 5-8, continued heated and stirred 1-24 hour, hold over night.
Wherein, the concentration of the ethanolic soln of described TPTZ is 0.001-1.0mol/L;
Wherein, described inorganic salt of rare earth REB
3With the mol ratio of TPTZ be 1: 1;
Wherein, the mol ratio of described aromatic carboxylic acid and verivate thereof and TPTZ is 0.5-3: 1;
Wherein, the volume ratio of second alcohol and water is 20: 1 to 1: 20 in described ethanol and the water mixed solution;
Wherein, described temperature of reaction further is optimized for 50 ℃ to reflux temperature, and said pH value scope further is optimized for 6-7, and the time of said heated and stirred further is optimized for 1-5 hour, and the time of said continuation heated and stirred further is optimized for 1-5 hour;
(2) mixture with step (1) gained filters, and filter cake is used absolute ethanol washing, and oven dry gets rare earth organic complex.
Description of drawings
Fig. 1 is Eu (the TPTZ) (NO of comparative example 1 preparation
3)
3(C
2H
5OH) H
2The fluorescent emission spectrogram of O.
Fig. 2 is Eu (the TPTZ) (C of inventive embodiments 1 preparation
6H
5COO)
34H
2The fluorescent emission spectrogram of O.
Fig. 3 is the Eu of inventive embodiments 2 preparations
2(TPTZ)
2(C
8H
4O
4) (NO
3)
4(C
2H
5OH) H
2The fluorescent emission spectrogram of O.
Fig. 4 is Tb (the TPTZ) (NO of comparative example 2 preparations
3)
3(C
2H
5OH) H
2The fluorescent emission spectrogram of O.
Fig. 5 is Tb (the TPTZ) (C of inventive embodiments 3 preparations
7H
5O
3)
3(C
2H
5OH) 2H
2The fluorescent emission spectrogram of O.
Fig. 6 is the Tb of inventive embodiments 4 preparations
2(TPTZ)
2(C
8H
4O
4) (NO
3)
4(C
2H
5OH) H
2The fluorescent emission spectrogram of O.
Fig. 7 is Sm (the TPTZ) (NO of comparative example 3 preparations
3)
3(C
2H
5OH) H
2The fluorescent emission spectrogram of O.
Fig. 8 is Sm (the TPTZ) (C of inventive embodiments 5 preparations
7H
5O
3)
3(C
2H
5OH) 2H
2The fluorescent emission spectrogram of O.
Embodiment
Below in conjunction with accompanying drawing and specific embodiment the present invention is further described, but do not limit the present invention in any way.
The measuring method of complex fluorescent spectrum and fluorescence quantum yield: at room temperature; The pressed powder of title complex is measured its fluorescence spectrum with the FLS-920 XRF; Exciting and launching slit of europium, terbium, samarium complex is respectively 3nm, 1nm, 5nm, and excitation wavelength is respectively 362nm, 355nm, 370nm.Fluorescence quantum yield calculates according to fluorescence intensity, the fluorescence lifetime of title complex and gets (Journal of Fluorescence, 2009,19,641).
Comparative example 1
Take by weighing TPTZ 0.936g (3.0mmol), add the 30mL anhydrous alcohol solution, after 50 ℃ stirring was dissolved fully down, adding 30mL concentration was the Eu (NO of 0.1mol/L
3)
3Ethanol solution, the use mass concentration is 7% ammoniacal liquor adjust pH to 6.2, white precipitate occurs, continues stirring reaction 3 hours, hold over night.White solid after filtering, the white powder that obtains with the absolute ethanol washing after drying is Eu (TPTZ) (NO
3)
3(C
2H
5OH) H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 33.28 (33.63); H%, 2.91 (2.82); N%, 17.52 (17.65); Eu%, 21.28 (21.27).Fluorescence emission spectrum (Fig. 1) shows that this title complex shows as pure red emission, and the strongest emission wavelength is 615nm, and intensity is 9.3 * 10
3A.u..The fluorescence quantum yield of this title complex is 12.29%.
Embodiment 1
Take by weighing TPTZ 0.936g (3.0mmol), add the 30mL anhydrous alcohol solution, after 50 ℃ stirring was dissolved fully down, adding 30mL concentration was the EuCl of 0.1mol/L
3Ethanol solution, stirring and refluxing 1 hour, adding 30mL concentration then is the benzoic ethanol/water solution (volume ratio of ethanol and water is 1: 1) of 0.3mol/L; The use mass concentration is 7% ammoniacal liquor adjust pH to 6.5; White precipitate occurs, continue stirring and refluxing reaction 2 hours, hold over night.White solid after filtering, the white powder that obtains with absolute ethyl alcohol and water washing after drying is Eu (TPTZ) (C
6H
5COO)
34H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 52.28 (52.06); H%, 3.76 (3.92); N%, 9.45 (9.34); Eu%, 16.47 (16.89).Fluorescence emission spectrum (Fig. 2) shows that this title complex shows as pure red emission, and the strongest emission wavelength is 616nm, and intensity is 2.8 * 10
5A.u..The fluorescence quantum yield of this title complex is 15.23%.
Embodiment 2
Take by weighing TPTZ 0.936g (3.0mmol), add the 30mL anhydrous alcohol solution, after 50 ℃ stirring was dissolved fully down, adding 30mL concentration was the Eu (NO of 0.1mol/L
3)
3Ethanol solution; 70 ℃ were stirred 1 hour, added the ethanol/water solution that 30mL concentration is the terephthalic acid of 0.05mol/L (volume ratio of ethanol and water is 10: 1) then, and the use mass concentration is 7% ammoniacal liquor adjust pH to 6.3; Continued stirring reaction 2 hours, hold over night.White solid after filtering, the white powder that obtains with the absolute ethanol washing after drying is Eu
2(TPTZ)
2(C
8H
4O
4) (NO
3)
4(C
2H
5OH) H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 39.12 (39.33); H%, 2.62 (2.58); N%, 15.82 (15.95); Eu%, 21.42 (21.63).Fluorescence emission spectrum (Fig. 3) shows that this title complex shows as pure red emission, and the strongest emission wavelength is 616nm, and intensity is 1.0 * 10
6A.u..The fluorescence quantum yield of this title complex is 43.95%.
Comparative example 2
Take by weighing TPTZ 0.936g (3.0mmol), add the 30mL anhydrous alcohol solution, after 60 ℃ stirring was dissolved fully down, adding 30mL concentration was the Tb (NO of 0.1mol/L
3)
3Ethanol solution, the use mass concentration is 7% ammoniacal liquor adjust pH to 6.2, white precipitate occurs, continues stirring reaction 3 hours, hold over night.White solid after filtering, the white powder that obtains with the absolute ethanol washing after drying is Tb (TPTZ) (NO
3)
3(C
2H
5OH) H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 33.32 (33.30); H%, 2.63 (2.79); N%, 17.42 (17.48); Tb%, 22.12 (22.03).Fluorescence emission spectrum (Fig. 4) shows that this title complex shows as pure green emission, and the strongest emission wavelength is 542nm, and intensity is 2.4 * 10
4A.u..
Embodiment 3
Take by weighing TPTZ 0.936g (3.0mmol), add the 30mL anhydrous alcohol solution, after 60 ℃ stirring was dissolved fully down, adding 30mL concentration was the Tb (NO of 0.1mol/L
3)
3Ethanol solution; 70 ℃ were stirred 1 hour, added the ethanol/water solution that 30mL concentration is the PHB of 0.3mol/L (volume ratio of ethanol and water is 10: 1) then, and the use mass concentration is 7% ammoniacal liquor adjust pH to 6.4; Continued stirring reaction 2 hours, hold over night.White solid after filtering, the white powder that obtains with the absolute ethanol washing after drying is Tb (TPTZ) (C
7H
5O
3)
3(C
2H
5OH) 2H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 50.14 (51.05); H%, 4.17 (3.87); N%, 8.59 (8.71); Tb%, 16.52 (16.47).Fluorescence emission spectrum (Fig. 5) shows that this title complex shows as pure green emission, and the strongest emission wavelength is 542nm, and intensity is 2.6 * 10
4A.u..
Embodiment 4
Take by weighing TPTZ 0.936g (3.0mmol), add the 30mL anhydrous alcohol solution, after 55 ℃ stirring was dissolved fully down, adding 30mL concentration was the Tb (NO of 0.1mol/L
3)
3Ethanol solution; 70 ℃ were stirred 1 hour, added the ethanol/water solution that 30mL concentration is the terephthalic acid of 0.05mol/L (volume ratio of ethanol and water is 10: 1) then, and the use mass concentration is 7% ammoniacal liquor adjust pH to 6.6; Continued stirring reaction 2 hours, hold over night.White solid after filtering, the white powder that obtains with the absolute ethanol washing after drying is Tb
2(TPTZ)
2(C
8H
4O
4) (NO
3)
4(C
2H
5OH) H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 38.52 (38.94); H%, 2.67 (2.56); N%, 15.54 (15.80); Tb%, 22.27 (22.40).Fluorescence emission spectrum (Fig. 6) shows that this title complex shows as pure green emission, and the strongest emission wavelength is 542nm, and intensity is 9.3 * 10
4A.u..
Comparative example 3
Take by weighing TPTZ 0.936g (3.0mmol), add the 30mL anhydrous alcohol solution, after 60 ℃ stirring was dissolved fully down, adding 30mL concentration was the Sm (NO of 0.1mol/L
3)
3Ethanol solution, the use mass concentration is 7% ammoniacal liquor adjust pH to 6.2, white precipitate occurs, continues stirring reaction 3 hours, hold over night.White solid after filtering, the white powder that obtains with the absolute ethanol washing after drying is Sm (TPTZ) (NO
3)
3(C
2H
5OH) H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 33.63 (33.70); H%, 2.55 (2.83); N%, 17.65 (17.69); Sm%, 21.00 (21.09).Fluorescence emission spectrum shows that the strongest emission wavelength of this title complex is 595nm, and intensity is 1.2 * 10
4A.u..
Embodiment 5
Take by weighing TPTZ 0.936g (3.0mmol), add the 30mL anhydrous alcohol solution, after stirring was dissolved fully, adding 60mL concentration was the Sm (NO of 0.1mol/L
3)
3Ethanol solution; 70 ℃ were stirred 1 hour, added the ethanol/water solution that 30mL concentration is the PHB of 0.3mol/L (volume ratio of ethanol and water is 10: 1) then, and the use mass concentration is 7% ammoniacal liquor adjust pH to 6.4; Continued stirring reaction 2 hours, hold over night.White solid after filtering, the white powder that obtains with the absolute ethanol washing after drying is Sm (TPTZ) (C
7H
5O
3)
3(C
2H
5OH) 2H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 51.14 (51.50); H%, 4.10 (3.90); N%, 8.76 (8.79); Sm%, 15.41 (15.73).Fluorescence emission spectrum shows that the emission wavelength of this title complex is 595nm, and intensity is 1.6 * 10
4A.u..
From comparative example and embodiment, can find out; With europium, terbium, samarium and 2; 4, the binary rare-earth organic light emission title complex that the 6-TPTZ forms is compared, and introduces the ternary RE ion that forms behind the aromatic carboxylic acid root part and has stronger luminous intensity and higher fluorescence quantum yield.
Claims (10)
1. one kind contains europium, terbium, samarium and 2,4, the organic light-emitting rare earth complexe of 6-TPTZ and aromatic carboxylic acid radical ion and verivate thereof, and the chemical formula that it is characterized in that it is RE
x(TPTZ)
xA
yB
z(C
2H
5OH) nH
2O, wherein RE is Sm
3+, Eu
3+, Tb
3+In a kind of, A is aromatic carboxylic acid root and verivate thereof, B is negative univalent inorganic anion, x=1 or 2, y＞0, z>=0, n is the positive integer of 1-8; When A is the monocarboxylic acid root, 3x=y+z; When A is the di-carboxylic acid root, 3x=2y+z; TPTZ is 2,4, the 6-TPTZ, and its structural formula is:
2. one kind prepares the organic light-emitting rare earth complexe RE that contains europium, terbium, samarium and TPTZ and aromatic carboxylic acid root and verivate thereof
x(TPTZ)
xA
yB
z(C
2H
5OH) nH
2The method of O may further comprise the steps:
(1) TPTZ is used anhydrous alcohol solution, is made into the solution that concentration is 0.001-1.0mol/L, 30 ℃ to reflux temperature, stir and to add a certain amount of inorganic salt of rare earth REB down
3Ethanolic soln, 30 ℃ to the temperature of reaction of reflux temperature heated and stirred 0.5-24 hour, add the ethanol and the water mixed solution of a certain amount of aromatic carboxylic acid and verivate thereof then, regulate the pH value to 5-8, continued heated and stirred 1-24 hour, hold over night.
(2) mixture with step (1) gained filters, and filter cake is used absolute ethanol washing, and oven dry gets rare earth organic complex.
3. title complex as claimed in claim 1; It is characterized in that described aromatic carboxylic acid root and verivate (A) thereof are selected from a kind of in benzoate anion, phenoxy acetic acid root, salicylic acid root, m-Salicylic acid root, PHB root, p-Nitrobenzenecarboxylic acid root, para hydroxybenzene fluoroacetic acid root, phthalate, m-phthalic acid root, terephthaldehyde's acid group, the 1-naphthoic acid root.
4. title complex as claimed in claim 1 is characterized in that, described aromatic carboxylic acid root and verivate (A) thereof are selected from a kind of in benzoate anion, PHB root, the terephthaldehyde's acid group.
5. title complex as claimed in claim 1 is characterized in that, described negative univalent inorganic anion (B) is selected from Cl
-, Br
-, I
-, ClO
4 -, NO
3 -In one or more.
6. method as claimed in claim 2 is characterized in that, described inorganic salt of rare earth REB
3With the mol ratio of TPTZ be 1: 1.
7. method as claimed in claim 2 is characterized in that, the mol ratio of aromatic carboxylic acid and verivate thereof and TPTZ is 0.5-3: 1.
8. method as claimed in claim 2 is characterized in that, the volume ratio of second alcohol and water is 20: 1 to 1: 20 in described ethanol and the water mixed solution.
9. method as claimed in claim 2 is characterized in that, said temperature of reaction can further be optimized for 50 ℃ to reflux temperature.
10. method as claimed in claim 2 is characterized in that, said pH value scope can further be optimized for 6-7.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103834380A (en) * | 2014-03-06 | 2014-06-04 | 内蒙古大学 | Organic aromatic carboxylic acid rare earth complex-coated Ag@SiO2 solid compound having shell structure and preparation method thereof |
| CN103992341A (en) * | 2014-05-30 | 2014-08-20 | 天津师范大学 | Mixed organic carboxylic acid containing rare earth complex as well as preparation method and application of mixed organic carboxylic acid containing rare earth complex |
| CN106832316A (en) * | 2017-01-19 | 2017-06-13 | 陕西师范大学 | One class bimetallic porous coordination and preparation method thereof |
| CN108593609A (en) * | 2018-03-27 | 2018-09-28 | 南昌大学 | A kind of method of highly sensitive highly selective fluoroscopic examination magnesium ion |
| CN112121464A (en) * | 2020-10-22 | 2020-12-25 | 广西大学 | Method for separating dysprosium and neodymium from nitrate based on solid nitrogen-containing composite functional adsorbing material |
| CN114853791A (en) * | 2022-06-14 | 2022-08-05 | 重庆师范大学 | Rare earth complex red fluorescent material and preparation method thereof |
-
2012
- 2012-01-09 CN CN2012100038103A patent/CN102584870A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| 李海燕，等: "2，4，6-三吡啶基三嗪-芳香羧酸镝配合物的合成及其荧光性能", 《发光学报》 * |
| 赵艳芳，等: "稀土配合物RE( TPTZ) Cl3 的合成、表征及荧光性能研究", 《光谱学与光谱分析》 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103834380A (en) * | 2014-03-06 | 2014-06-04 | 内蒙古大学 | Organic aromatic carboxylic acid rare earth complex-coated Ag@SiO2 solid compound having shell structure and preparation method thereof |
| CN103992341A (en) * | 2014-05-30 | 2014-08-20 | 天津师范大学 | Mixed organic carboxylic acid containing rare earth complex as well as preparation method and application of mixed organic carboxylic acid containing rare earth complex |
| CN103992341B (en) * | 2014-05-30 | 2017-02-15 | 天津师范大学 | Mixed organic carboxylic acid containing rare earth complex as well as preparation method and application of mixed organic carboxylic acid containing rare earth complex |
| CN106832316A (en) * | 2017-01-19 | 2017-06-13 | 陕西师范大学 | One class bimetallic porous coordination and preparation method thereof |
| CN106832316B (en) * | 2017-01-19 | 2020-04-24 | 陕西师范大学 | Bimetal porous complex and preparation method thereof |
| CN108593609A (en) * | 2018-03-27 | 2018-09-28 | 南昌大学 | A kind of method of highly sensitive highly selective fluoroscopic examination magnesium ion |
| CN112121464A (en) * | 2020-10-22 | 2020-12-25 | 广西大学 | Method for separating dysprosium and neodymium from nitrate based on solid nitrogen-containing composite functional adsorbing material |
| CN114853791A (en) * | 2022-06-14 | 2022-08-05 | 重庆师范大学 | Rare earth complex red fluorescent material and preparation method thereof |
| CN114853791B (en) * | 2022-06-14 | 2023-10-13 | 重庆师范大学 | Rare earth complex red fluorescent material and preparation method thereof |
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Application publication date: 20120718 |