CN103740361A - Dye/metal-organic framework composite material for white light emission and preparation method thereof - Google Patents
Dye/metal-organic framework composite material for white light emission and preparation method thereof Download PDFInfo
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- CN103740361A CN103740361A CN201310724074.5A CN201310724074A CN103740361A CN 103740361 A CN103740361 A CN 103740361A CN 201310724074 A CN201310724074 A CN 201310724074A CN 103740361 A CN103740361 A CN 103740361A
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Abstract
The invention discloses a dye/metal-organic framework composite material for white light emission. The dye/metal-organic framework composite material for white light emission is composed of 70-90% of indium-containing metal-organic framework, 5-15% of pyridine hemicyanine dye and 5-15% of acridine dye by molar percent. The preparation method comprises the steps of: firstly, synthesizing the indium-containing metal-organic framework from a benzene polycarboxylic acid organic ligand and an indium salt through a solvothermal reaction, and secondly, introducing the pyridine hemicyanine dye and the acridine dye into the indium-containing metal-organic framework by the ion exchange method to obtain the dye/metal-organic framework composite material. The synthetic method is simple in process and mild in conditions; the raw materials are easy to get and the yield of the dye/metal-organic framework composite material is high; the prepared dye/metal-organic framework composite material is high in chemical stability; the chromaticity coordinates of the emitted color are quite close to the chromaticity coordinates of the ideal white light; the color rendering index of the composite material is higher than 80 and the luminous quantum efficiency of the composite material is greater than 20%; therefore, the dye/metal-organic framework composite material for white light emission is expected to be applied to the fields of display and light emitting devices and the like as a novel white light emitting material.
Description
Technical field
The present invention relates to a kind of dyestuff/metal organic frame matrix material for white light emission and preparation method thereof.
Background technology
Luminescent material becomes the study hotspot in international forward position in recent ten years in the application in many fields such as luminescent lamp, plasma flat-plate demonstration, photoswitch, photodiode.It is the target that numerous physics and chemistry men pursue that design and development has long lifetime, less energy-consumption, high efficiency luminescent material.The advantages such as volume is little, thermal value is low, current consumption is little, the life-span is long make white light LEDs become energy-conserving light source of new generation.Traditional LED white emitting fluorescent powder is that multiple color phosphor combination forms, and does not have single fluorescent material.And conventional fluorescent powder has that colour rendering index is low, colour temperature is low, low etc. the shortcoming of luminous efficiency, need to further improve.Utilize dyestuff/metal organic frame matrix material to prepare and realize single fluorescent material, the white light that irradiate under ultraviolet excitation that colour rendering index is high, color temperature value meets the requirements, luminous efficiency promotes, thereby the design of its material and preparation are significant.
Metal organic frame is a kind ofly by metal ion or metal cluster and organic bridge ligand, to assemble the novel porous crystalline material forming by coordination.Similar to the porous material that zeolite molecular sieve etc. is traditional, metal organic frame material has the duct of systematicness and specific dimensions and the shape of special topological framework, internal arrangement equally, but frame material shows larger structurally variable, tunable characteristic and the physicochemical property of horn of plenty more.Metal organic frame material not only has the luminescent properties that traditional material has, and the characteristic of material itself has also derived new optics behavior.Luminescent material with other is compared, metal organic frame material has designing and can cutting out characteristic of synthesizing, in addition, the luminescent properties of frame material and chemical environment, coordination configuration, crystalline structure and with duct in the interaction of guest molecule also all closely related, this just makes luminescent metal-organic framework materials not only can contain the luminescent properties that traditional title complex has, also have and produce new luminescent properties and the potentiality of luminous behavior, thereby there is great using value in field of light emitting materials.
In dyestuff/metal organic frame matrix material, not only inorganic metal ion and organic ligand can provide unique luminescent properties, and the dyestuff guest molecule of assembling in frame material duct also can produce luminous.The luminous mechanism in solution is identical with them with the luminous of dyestuff guest molecule for organic ligand, all originate from the transition to ground state by the first excited singlet state of organic ligand and guest molecule, but because making the rigidity of part, the coordination of metal ion in frame material and part increases, and framework duct significantly reduces the probability of nonradiative transition to the separation assembling of dyestuff guest molecule, thereby luminous intensity and the luminous quantum efficiency of organic ligand and dyestuff guest molecule have greatly been strengthened, in addition, the thermo-chemical stability of dye molecule can also be further improved in the duct of metal organic frame to the assembling of dye molecule, for practical in luminescent material of organic dye molecule provides new approach.Therefore this novel matrix material can further promote white light emission performance, promotes the progress of luminescent material in many fields such as luminescent lamp, plasma flat-plate demonstration, photoswitch, photodiodes.
Summary of the invention
The object of the invention is to provide a kind of dyestuff/metal organic frame matrix material for white light emission and preparation method thereof, with solve current organic fluorescent dye molecule under solid-state because concentration quenching causes the difficult problem that luminous efficiency is low, thermo-chemical stability is not high.
Composition and the mole percent level of the dyestuff/metal organic frame matrix material for white light emission of the present invention are: containing the metal organic frame 70-90% of indium, pyridine hemicyanine dye 5-15%, acridine dye 5-15%.
The preparation method who is used for dyestuff/metal organic frame matrix material of white light emission, comprises the following steps:
(1) containing the preparation of the metal organic frame of indium:
Benzene polycarboxylic acid's part of 0.1-1mmol and 1-2mmol indium salt are dissolved in the mixed solvent of 10-100mL organic solvent and 1-50mL water, after stirring, the hydrochloric acid that the mass concentration that dropwise adds 0.1-0.5 μ L is 36.5% puts into airtight reactor, at 60-150 ℃ of isothermal reaction 1-7 days, obtain the metal organic frame containing indium;
(2) ion exchange reaction of pyridine hemicyanine dye and acridine dye and metal organic frame:
The pyridine hemicyanine dye of getting 1-10mg is dissolved in the N of 100-200mL, in N solvent dimethylformamide, inwardly add again the metal organic frame containing indium prepared by 0.1-1g step (1) to carry out ion exchange reaction 1-24h, filter and take out completely reacted metal organic frame, join again the N that contains 0.1-10mg acridine dye, in N dimethyl formamide solution, carry out ion exchange reaction 1-24h, after filtration, with alcohol solvent, clean, obtain dyestuff/metal organic frame matrix material.
In above-mentioned preparation method's step (1), said benzene polycarboxylic acid's part is [1,1 ': 4 ", 1 " terphenyl]-3,3 ", 5,5 " tetracarboxylic acid, terephthalic acid, 4,4 '-biphenyl dicarboxylic acid or 1,3,5-tri-(4-carboxyl benzene) benzene.Said indium salt is indium chloride, indium nitrate or indium acetate.Said organic solvent is DMF, N,N-dimethylacetamide, tetrahydrofuran (THF), methyl alcohol, ethanol or acetone.
In step (2), said pyridine hemicyanine dye is 4-(4-dimethylamino vinylbenzene)-1-picoline salt compounded of iodine, 4-(4-dimethylamino vinylbenzene)-1-picoline sulfonate, 4-(4-(hexichol amido vinylbenzene)-1-picoline salt compounded of iodine or 4-(4-(N-alkyl) amino-benzene ethene) pyridinium iodide.Said acridine dye is the amino salt compounded of iodine, 3 of acridine-9-, 6-diaminostilbene 0-methyl isophthalic acid 0-Acrizane hydrochlorate or N-methylacridine salt compounded of iodine.
Beneficial effect of the present invention is:
1, metal organic frame of the present invention is anionic skeleton construction, can with cationic dyestuff generation ion exchange reaction, it is high that the exchange of dyestuff substitutes concentration, the interaction of dye molecule and metal organic frame is strong.The crystallization degree of metal organic frame is high, and crystalline size is large, good stability, and it is simple to have synthesis technique, productive rate is compared with advantages of higher;
2, the duct of metal organic frame of the present invention can be played and separate and provide protection dye molecule; reduced the nonradiative transition probability of dye molecule; thereby greatly strengthened luminous intensity and the luminous quantum efficiency of dye molecule, and improved the thermo-chemical stability of dye molecule.
3, metal organic frame of the present invention has stronger designability, can just can realize by converting different organic ligands the regulation and control of luminescent properties, in addition, can also, by changing the content of pyridine hemicyanine dye and acridine dye, realize adjusting and optimization to performance perameters such as colour rendering index, luminous efficiencies.
Embodiment
Embodiment 1:
(1) containing the preparation of the metal organic frame of indium:
Take [1 of 0.1mmol, 1 ': 4 "; 1 "-terphenyl]-3,3 ", 5,5 " tetracarboxylic acid part and 1mmol indium chloride are dissolved in 60mLN, the mixed solvent of dinethylformamide and 10mL water, after the hydrochloric acid that the mass concentration that dropwise adds 0.1 μ L is 36.5% stirs, put into airtight reactor, 70 ℃ of isothermal reactions 1 day, obtain the metal organic frame containing indium.
(2) ion exchange reaction of pyridine hemicyanine dye and acridine dye and metal organic frame:
Pyridine hemicyanine dye 4-(4-dimethylamino vinylbenzene)-1-picoline salt compounded of iodine of getting 1mg is dissolved in the N of 100mL, in N solvent dimethylformamide, inwardly add again the metal organic frame containing indium prepared by 0.8g step (1) to carry out after ion exchange reaction 3h, filter and take out completely reacted metal organic frame, join again the N that contains 0.3mg acridine dye N-methylacridine salt compounded of iodine, in N dimethyl formamide solution, carry out ion exchange reaction 5h, after filtering, use ethanol to clean 3 times, obtain dyestuff/metal organic frame matrix material.
The luminous quantum efficiency of pyridine hemicyanine dye 4-(4-dimethylamino the vinylbenzene)-1-picoline salt compounded of iodine in this matrix material is higher than 40%, and the luminous quantum efficiency of comparing this dyestuff 1% left and right in dilute solution state is significantly increased.The luminous efficiency of acridine dye N-methylacridine salt compounded of iodine also promotes greatly.Dyestuff/metal organic frame the matrix material making excites the good white light emission of lower generation at the ultraviolet lamp of 365nm, the chromaticity coordinates value of glow color is (0.309,0.323), with the chromaticity coordinates of ideal white light very near, in addition, colour temperature is 6738K, colour rendering index is 85, total luminous quantum efficiency is 23%, the good thermal stability of dyestuff/metal organic frame matrix material, heat decomposition temperature, higher than 260 ℃, is expected in fields such as display and lightings, to obtain application as the excellent white light emitting material of one.
Embodiment 2:
(1) containing the preparation of the metal organic frame of indium:
Take 1 of 0.3mmol, 3,5-tri-(4-carboxyl benzene) phenylformic acid and 2mmol indium chloride are dissolved in the mixed solvent of 100mL ethanol and 20mL water, after stirring, the hydrochloric acid that the mass concentration that dropwise adds 0.3 μ L is 36.5% puts into airtight reactor, 80 ℃ of isothermal reactions 2 days, obtain the metal organic frame containing indium.
(2) ion exchange reaction of pyridine hemicyanine dye and acridine dye and metal organic frame:
(4-(hexichol amido vinylbenzene)-1-picoline salt compounded of iodine is dissolved in the N of 150mL to get the pyridine hemicyanine dye 4-of 3mg, in N solvent dimethylformamide, inwardly add again the metal organic frame containing indium prepared by 0.1g step (1) to carry out after ion exchange reaction 10h, filter and take out completely reacted metal organic frame, join again the N that contains 0.4mg acridine dye N-methylacridine salt compounded of iodine, in N dimethyl formamide solution, carry out ion exchange reaction 1h, after filtering, use ethanol to clean 3 times, obtain dyestuff/metal organic frame matrix material.
(luminous quantum efficiency of 4-(hexichol amido vinylbenzene)-1-picoline salt compounded of iodine is higher than 50%, compares this dyestuff luminous quantum efficiency of 1% in dilute solution state and is significantly increased for pyridine hemicyanine dye 4-in this matrix material.The luminous efficiency of acridine dye N-methylacridine salt compounded of iodine is also corresponding.Dyestuff/metal organic frame the matrix material making excites the good white light emission of lower generation at the ultraviolet lamp of 365nm, the chromaticity coordinates value of glow color is (0.335,0.313), with the chromaticity coordinates of ideal white light very near, in addition, colour temperature is 5358K, and colour rendering index is 86, total luminous quantum efficiency is 27%, is expected in fields such as display and lightings, to obtain application as the excellent white light emitting material of one.
Embodiment 3:
(1) containing the preparation of the metal organic frame of indium:
Take the mixed solvent that the terephthalic acid of 0.7mmol and 2mmol indium acetate are dissolved in 100mL tetrahydrofuran (THF) and 50mL water, after stirring, the hydrochloric acid that the mass concentration that dropwise adds 0.5 μ L is 36.5% puts into airtight reactor, 60 ℃ of isothermal reactions 7 days, obtain the metal organic frame containing indium.
(2) ion exchange reaction of pyridine hemicyanine dye and acridine dye and metal organic frame:
Pyridine hemicyanine dye 4-(4-dimethylamino vinylbenzene)-1-picoline sulfonate of getting 5mg is dissolved in the DMF solvent of 200mL, inwardly add again the metal organic frame containing indium prepared by 1g step (1) to carry out after ion exchange reaction 1h, filter and take out completely reacted metal organic frame, join again the N that contains the amino salt compounded of iodine of 10mg acridine dye acridine-9-, in N dimethyl formamide solution, carry out ion exchange reaction 10h, after filtering, use ethanol to clean 3 times, obtain dyestuff/metal organic frame matrix material.
(the luminous quantum efficiency scope of 4-(hexichol amido vinylbenzene)-1-picoline salt compounded of iodine is 30%-50%, compares this dyestuff luminous quantum efficiency of 2% in dilute solution state and is significantly increased for pyridine hemicyanine dye 4-in this matrix material.The luminous efficiency of the amino salt compounded of iodine of acridine dye acridine-9-also promotes greatly.In addition, the dyestuff/metal organic frame matrix material making also can produce good white light emission under the ultraviolet lamp of 365nm excites, and chromaticity coordinates is between (0.31,0.33) to (0.33,0.33).
Embodiment 4:
(1) containing the preparation of the metal organic frame of indium:
Take 4 of 1mmol, 4 '-biphenyl dicarboxylic acid and 2mmol indium nitrate are dissolved in 10mL N, the mixed solvent of N-N,N-DIMETHYLACETAMIDE and 1mL water, after stirring, the hydrochloric acid that the mass concentration that dropwise adds 0.5 μ L is 36.5% puts into airtight reactor, 150 ℃ of isothermal reactions 5 days, obtain the metal organic frame containing indium.
(2) ion exchange reaction of pyridine hemicyanine dye and acridine dye and metal organic frame:
Pyridine hemicyanine dye 4-(4-(N-alkyl) amino-benzene ethene) pyridinium iodide of getting 10mg is dissolved in the N of 200mL, in N dimethyl formamide, inwardly add again the metal organic frame containing indium prepared by 1g step (1) to carry out after ion exchange reaction 24h, filter and take out completely reacted metal organic frame, join again and contain 0.1mg acridine dye 3, the N of 6-diaminostilbene 0-methyl isophthalic acid 0-Acrizane hydrochlorate, in N dimethyl formamide solution, carry out ion exchange reaction 24h, after filtering, use ethanol to clean 2 times, obtain dyestuff/metal organic frame matrix material.
The luminous quantum efficiency scope of pyridine hemicyanine dye 4-(4-(N-alkyl) amino-benzene ethene) pyridinium iodide in this matrix material is 30%-50%, compares this dyestuff luminous quantum efficiency of 2% in dilute solution state and is significantly increased.Acridine dye 3, the luminous efficiency of 6-diaminostilbene 0-methyl isophthalic acid 0-Acrizane hydrochlorate also promotes greatly.In addition, the dyestuff/metal organic frame matrix material making also can produce good white light emission under the ultraviolet lamp of 365nm excites, and chromaticity coordinates is between (0.31,0.33) to (0.33,0.33).
Claims (7)
1. for dyestuff/metal organic frame matrix material of white light emission, it is characterized in that its composition and mole percent level are: containing the metal organic frame 70-90% of indium, pyridine hemicyanine dye 5-15%, acridine dye 5-15%.
2. the method for the preparation dyestuff/metal organic frame matrix material for white light emission claimed in claim 1, is characterized in that comprising the following steps:
(1) containing the preparation of the metal organic frame of indium:
Benzene polycarboxylic acid's part of 0.1-1 mmol and 1-2 mmol indium salt are dissolved in the mixed solvent of 10-100 mL organic solvent and 1-50 mL water, after stirring, the hydrochloric acid that the mass concentration that dropwise adds 0.1-0.5 μ L is 36.5% puts into airtight reactor, at 60-150
oc isothermal reaction 1-7 days, obtains the metal organic frame containing indium;
(2) ion exchange reaction of pyridine hemicyanine dye and acridine dye and metal organic frame:
The pyridine hemicyanine dye of getting 1-10 mg is dissolved in the N of 100-200 mL, in N solvent dimethylformamide, inwardly add again the metal organic frame containing indium prepared by 0.1-1 g step (1) to carry out ion exchange reaction 1-24 h, filter and take out completely reacted metal organic frame, join again the N that contains 0.1-10 mg acridine dye, in N dimethyl formamide solution, carry out ion exchange reaction 1-24 h, after filtration, with alcohol solvent, clean, obtain dyestuff/metal organic frame matrix material.
3. the method for the dyestuff/metal organic frame matrix material for white light emission according to claim 2, it is characterized in that in step (1), said benzene polycarboxylic acid's part is [1,1 ': 4 ' ', 1 ' '-terphenyl]-3,3 ' ', 5,5 ' '-tetracarboxylic acid, terephthalic acid, 4,4'-biphenyl dicarboxylic acid or 1,3,5-tri-(4-carboxyl benzene) benzene.
4. the method for the dyestuff/metal organic frame matrix material for white light emission according to claim 2, is characterized in that in step (1), said indium salt is indium chloride, indium nitrate or indium acetate.
5. the method for the dyestuff/metal organic frame matrix material for white light emission according to claim 2, it is characterized in that in step (1), said organic solvent is N, N dimethyl formamide, N,N-dimethylacetamide, tetrahydrofuran (THF), methyl alcohol, ethanol or acetone.
6. the method for the dyestuff/metal organic frame matrix material for white light emission according to claim 2, is characterized in that in step (2), said pyridine hemicyanine dye is 4-(4-dimethylamino vinylbenzene)-1-picoline salt compounded of iodine, 4-(4-dimethylamino vinylbenzene)-1-picoline sulfonate, 4-(4-(hexichol amido vinylbenzene)-1-picoline salt compounded of iodine or 4-(4-(N-alkyl) amino-benzene ethene) pyridinium iodide.
7. the method for the dyestuff/metal organic frame matrix material for white light emission according to claim 2, it is characterized in that in step (2), said acridine dye is the amino salt compounded of iodine, 3 of acridine-9-, 6-diaminostilbene 0-methyl isophthalic acid 0-Acrizane hydrochlorate or N-methylacridine salt compounded of iodine.
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| CN113201326A (en) * | 2021-04-22 | 2021-08-03 | 浙江大学 | Dye/perovskite quantum dot loaded metal-organic framework material and preparation method thereof |
| CN116120230A (en) * | 2023-04-19 | 2023-05-16 | 季华实验室 | Fluorescent material with one-dimensional chain structure, synthesis method thereof and fluorescent device |
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