CN114790257A - Novel polymer white light material based on coumarin and rare earth complex and preparation method thereof - Google Patents
Novel polymer white light material based on coumarin and rare earth complex and preparation method thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of organic chemistry and high polymer material chemistry, and discloses a novel polymer white light material based on coumarin and rare earth complexes and a preparation method thereof. Per rare earth complex Eu (TTA) 3 ·(H 2 O) 2 The polymer 4 white light material containing double chromogens is successfully constructed by coordination with the compound 3. The polymer 4 white light material can simultaneously realize the emission of the red light, the blue light of the coumarin derivative and the white light of the rare earth complex in one polymer by accurately regulating and controlling the excitation wavelength (320-450nm) and the CPB concentration (0.034g/L, 0.051g/L, 0.068g/L, 0.085g/L, 0.102g/L and 0.34 g/L).
Description
Technical Field
The invention belongs to the technical field of organic chemistry and high polymer material chemistry, and relates to a novel polymer white light material based on coumarin and rare earth complexes and a preparation method thereof.
Background
White light emitting diodes (WOLEDs) have unique advantages of light weight, ultra-thin profile, and excellent workability through a low-cost solution processing technology, and thus have a wide application prospect in solid-state lighting and liquid light sources, and they have higher electro-optic conversion efficiency compared to conventional light sources, and have become a new growing point in the organic electroluminescence field. An effective strategy to obtain high quality solution processed films is to physically mix the luminescent substance (guest material) into the matrix (host material), which can achieve good device performance and excellent color quality. White electroluminescence is generated by emitting RGB or BO combinations (fluorescence or phosphorescence) at the same time, and white light is obtained by carefully adjusting the mixing ratio of light emitting components in a light emitting layer, controlling their relative luminous intensities and appropriate energy transfer. However, such white light obtained by blending the luminescent components is easily disturbed by factors such as manufacturing conditions. To solve this problem, many organic single-molecule white light materials have been reported, but these white light materials have certain difficulties in both molecular design and synthesis. If a white light material is realized, fluorophores of three primary colors of red, green and blue or two complementary colors are usually adopted to be combined together, but the absorption spectrum and the fluorescence spectrum of the organic fluorophore are relatively wide, and spectral overlapping is easy to occur, so that fluorescence resonance energy transfer between the two fluorophores occurs, fluorescence of the fluorophore serving as a fluorescence donor cannot be released, and finally only single fluorescence emission is presented, and white light is difficult to realize. The rare earth europium has the unique luminescent properties of transition luminescence based on 4f → 4f or 5d → 4f transition, the emission peak is sharp, the quantum yield is high, the surrounding ligand is required to absorb energy to excite the red light emission, and therefore, the rare earth europium-doped.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a novel polymer white light material based on coumarin and rare earth complexes and a preparation method thereof, overcomes the defect that the conventional organic fluorophore is not easy to emit multiple fluorescence, and utilizes rare earth Eu 3 The polymer 4 white light material is different from the traditional organic fluorophore molecules, can realize red light and blue light emission, and can realize white light emission even by reasonably adjusting the excitation wavelength and the solution concentration.
The above purpose of the invention is realized by the following technical scheme:
a novel polymer white light material based on coumarin and rare earth complexes is a polymer 4, and the specific structural formula is as follows:
wherein n is 7-15 and m is 45-70.
By the rare earth complex Eu (TTA) 3 ·(H 2 O) 2 And the compound is coordinated with the compound 3, and a polymer 4 white light material containing double chromogens is successfully constructed. The polymer 4 white light material can simultaneously realize the emission of the red light, the blue light of the coumarin derivative and the white light of the rare earth complex in one polymer by accurately regulating and controlling the excitation wavelength (320-450nm) and the CPB concentration (0.034g/L, 0.051g/L, 0.068g/L, 0.085g/L, 0.102g/L and 0.34 g/L).
The preparation method of the novel polymer white light material based on the coumarin and the rare earth complex comprises the following steps: the method comprises the following specific steps:
s1.6.17mmol of p-hydroxybenzaldehyde, 2-3 times of molar weight of allyl bromide and 2-3 times of molar weight of potassium carbonate are heated and refluxed for two hours in 12-20 mL of acetonitrile solution to obtain a compound 1;
s2.1.82mmol compound 1 and 1.82mmol coumarin hydrazine derivative are heated and refluxed for four hours in 25mL ethanol solution to generate Schiff base reaction to obtain compound 2.
S3.5mmol of methyl methacrylate and 0.125mmol of compound 2 were polymerized by heating in 6mL of Tetrahydrofuran (THF) under the initiation of 0.022mmol of azobisisobutyronitrile for 24 hours to obtain polymer 3, and the polymer 3 was further polymerized with 0.5-fold molar amount of Eu (TTA) in the Tetrahydrofuran (THF) solution 3 ·(H 2 O) 2 Heating and reacting for 24 hours to obtain the polymer 4 white light material.
Compared with the prior art, the invention has the beneficial effects that:
the invention successfully develops a novel color-adjustable polymer white light material by introducing the rare earth europium complex with excellent photophysical performance into a blue light polymer platform MS 1. Because the rare earth complex in the material is different from the luminescence mechanism of the traditional organic fluorophore, the absorption spectrum of the rare earth complex part in the polymer white light material is almost not overlapped with the emission spectrum of the compound 2, so that the fluorescence resonance energy transfer of the compound 2 and the rare earth complex can not be realized. By changing the excitation wavelength and the concentration of the polymer CPB, the emission of blue light and red light can be realized, and even white light emission can be further realized by the complementation of the red light and the blue light. Through research studies, the emission CIE coordinates (0.33,0.31) of near standard white light at 4(0.085g/L) concentration, excited at 388nm, can be achieved in the end. The polymer white light material also provides more possibilities for preparing white light materials by subsequent processing.
The polymer 4 white light material prepared by using the coumarin fluorophore has the advantages of easily obtained raw materials, simple and easy synthesis and low cost. When different excitation wavelengths and different material concentrations are used, red light, blue light and white light emission of the polymer white light material can be respectively realized. The development of the polymer white light material also makes the later application of the polymer white light material to flexible nano materials possible.
Drawings
FIG. 1 shows CDCl of compound 1 of example 1 of the present invention 3 Hydrogen spectrum of nuclear magnetism;
FIG. 2 shows CDCl of compound 1 of example 1 of the present invention 3 Nuclear magnetic carbon spectrum of (1);
FIG. 3 shows CDCl for compound 2 of example 2 of the present invention 3 Hydrogen spectrum of nuclear magnetism in (1);
FIG. 4 shows CDCl of compound 2 of example 2 of the present invention 3 Nuclear magnetic carbon spectrum of (1);
FIG. 5 shows CDCl in polymer 3 of example 3 of the present invention 3 Hydrogen spectrum of nuclear magnetism in (1);
FIG. 6 is a graph of the red, blue and white fluorescence spectra of the white light material of Polymer 4 in example 4 of the present invention;
FIG. 7 shows fluorescence spectra of different excitation wavelengths of the white light material of Polymer 4 in example 4 of the present invention;
FIG. 8 is a graph showing the change of fluorescence color at different excitation wavelengths of the polymer 4 white light material in example 4 of the present invention;
FIG. 9 is a CIE diagram of a polymer 4 white light material in example 4 of the present invention.
Detailed Description
The invention is described in more detail below with reference to specific examples, without limiting the scope of the invention. Unless otherwise specified, the experimental methods adopted by the invention are all conventional methods, and experimental equipment, materials, reagents and the like used in the experimental method can be obtained from commercial sources.
EXAMPLE 1 Synthesis of Compound 1
Synthesis of Compound 1: 6.17mmol of p-hydroxybenzaldehyde, 12.34mmol of bromopropene and 12.34mmol of potassium carbonate were placed in a flask, and 12 ml of acetonitrile were added. The reaction solution was heated under reflux at 70 ℃ for two hours, TLC determined that the reaction was complete (the developing solvent was dichloromethane: petroleum ether (v/v): 6: 1, Rf: 0.6), then cooled and filtered, the filtrate was evaporated under reduced pressure to give a pale yellow oily substance (p-allyloxybenzaldehyde), and the resulting liquid was separated by column chromatography (the distillate was dichloromethane) to give 0.81g of a pale yellow oily product with a yield of 62%.
1 H-NMR(500MHz,CDCl 3 ):δ(ppm)9.88(s,1H,-CHO-),7.84-7.82(d,2H,J＝10Hz,-ArH-),7.02-7.01(d,2H,J＝5Hz,-ArH-),6.03(m,1H,＝CH-),5.46-5.33(m,2H,-C＝CH 2 ),4.63-4.62(d,2H,J＝5Hz,-O-CH 2 -). 13 C-NMR(125MHz,CDCl 3 ):δ(ppm)190.77,163.6,132.2,131.95,130.04,118.34,115.01,69.01.
EXAMPLE 2 Synthesis of Compound 2
Coumarin hydrazine hydrate: coumarin ester (1g, 3.46mmol) was dissolved in 15ml of methanol solution, 2ml of 80% hydrazine hydrate was slowly dropped, the reaction solution was stirred at room temperature for 30 minutes, after TLC confirmed that the reaction was completed, the precipitated solid was filtered to obtain yellow solid powder 0.54g, and the yield was 56%. The product was used in the next reaction without purification.
Synthesis of Compound 2: 1.82mmol coumarin hydrazine hydrate and 1.82mmol compound 1 are placed in a 50 ml flask, 25ml of absolute ethyl alcohol is added, two drops of glacial acetic acid are added to promote the reaction, the heating reflux stirring is carried out, after the reaction is carried out for four hours, TLC determines that the reaction is finished, cooling and filtering are carried out, and a filter cake is washed and filtered for three times by a small amount of ethyl alcohol to obtain 450 mg, and the yield is 60%. The developing solvent is CH 2 Cl 2 ：CH 4 O(v/v)＝50：1，R f ＝0.46。 1 H-NMR(500MHz,CDCl 3 ):δ(ppm)11.79(s,1H,-NH-),8.86(s,1H,-CH＝N-),8.15(s,1H,-ArH-),7.76(q,2H,J＝8.3Hz,-ArH-),7.49(d,1H,J＝8.9Hz,-ArH-),6.94(q,2H,J＝8.3Hz,-ArH-),6.72(d,1H,J＝7.3Hz,-ArH-),6.56(s,1H,-ArH-),6.03(m,1H,-CH＝),5.40(m,2H,J＝10Hz,＝CH 2 ),4.58(d,2H,-CH 2 -),3.48(q,4H,J＝6.75Hz,-N-CH 2 -),1.25(t,6H,J＝6.75Hz,-CH 2 CH 3 ). 13 C-NMR(125MHz,CDCl 3 ):δ(ppm)162.72,160.50,159.56,157.67,152.57,148.98,148.39,132.85,131.38,129.47,126.65,117.95,114.83,110.49,109.51,108.92,97.01,68.83,45.42,12.38.
Example 3 Synthesis of Polymer 3
Synthesis of Polymer 3: mixing purified 500.6mg (5mmol) of methyl methacrylate and 52mg (0.125mmol) of compound 2, placing the mixture in a double-mouth Schlenk bottle, adding 23.7mg (0.065mmol) of 2- (dodecyl trithiocarbonate) -2-methylpropanoic acid and 3.612mg of initiator azobisisobutyronitrile (0.022mmol), dissolving in 6mL of THF, connecting with a double-discharge pipe system, magnetically stirring until complete dissolution, vacuumizing through the double-discharge pipe system, introducing nitrogen gasAnd circulating for 3 times, completely removing oxygen and water, and strictly sealing. The reaction was then placed in a constant temperature oil bath at 70 ℃ for 24 hours. After the reaction was completed, the polymerization reaction was quenched with an ice-water mixture, and after standing for a while in the ice-water mixture, the mixture was poured into methyl t-butyl ether, and the polymer was precipitated, and after repeated dissolution-precipitation with THF and methyl t-butyl ether for 3 times, it was suction-filtered and dried in a vacuum oven at 30 ℃ for 24 hours to a constant weight, to obtain 83mg of a yellow powder product. 1 H-NMR(500MHz,CDCl 3 ):δ(ppm)11.79(11,1H,-NH-),8.85(10,1H,-CH＝N-),8.15(1,1H,-ArH-),7.76-7.75(6,2H,-ArH-),7.48-7.47(2,1H,-ArH-),6.95-6.93(5,2H,-ArH-),6.69-6.67(3,1H,-ArH-),6.52(4,1H,-ArH-),6.1-6.02(8,1H,-CH-),5.32-5.3(9,2H,-CH 2 ),4.58-4.57(7,2H,-O-CH 2 -),3.6(m,3H,-O-CH 3 ),3.48-3.45(12,4H,-N-CH 2 -),1.5-2.0(p,2H,-CH 2 -),1.25(13,6H,-CH 2 -CH 3 ),1.02-0.85(n,3H,-C-CH 3 ) (see the attached figure 5)
Example 4 Synthesis of Polymer 4 white Material
Synthesis of Polymer 4 white light Material: compound 3(40mg,0.0348mmol) was dissolved in 6mL THF, followed by 1/2 fold addition of Eu (TTA) 3 ·(H 2 O) 2 (14.8mg,0.0174 mmol). The reaction mixture was heated at 70 ℃ under reflux for 6 hours. The reaction solution was cooled to room temperature, a small amount of n-hexane diffused to produce a precipitate, which was filtered and the crude product was recrystallized from THF to yield 39mg of a yellow solid in 84.3% yield.
As shown in FIG. 6, when polymer 4(0.085g/L) in acetonitrile is excited at an excitation wavelength of 332nm, which is the absorption region of the rare earth ligand 2-thenoyltrifluoroacetone (TTA), energy is further transferred between TTA and rare earth, only red light of the rare earth part can be emitted, while coumarin hardly absorbs at 332nm, and blue light is hardly seen. When excited at 429nm, the absorption maximum is that of coumarin, and only blue light belonging to coumarin is released. When excited at 388nm, the red light of the rare earth europium complex and the blue light of coumarin can coexist well at the same time, and the polymer 4 white light material emits obvious white light with the quantum yield of 0.12 (acetonitrile solution).
It was observed that by adjusting the excitation wavelength, the color of the white light material solution emitted by polymer 4 can be controlled (see fig. 7). The red light is emitted when the light is excited at 320-380 nm, the blue-green light is emitted when the light is excited at 390-450 nm, and the light is white light between 380-390 nm. The polymer 4 white light material can simultaneously emit three kinds of fluorescence which can not be realized by most of traditional fluorophores, and because the Stokes shift of the traditional fluorophores is small, the spectrums of two organic fluorophores with different wave bands are easy to overlap, thereby generating fluorescence resonance energy transfer, leading the short wavelength fluorophor to be difficult to release fluorescence after energy transfer, and finally only emitting one kind of long wavelength fluorescence. The rare earth europium complex further coordinates with a coumarin polymer (compound 3) to enable energy of coumarin to be reserved so as to emit blue-green light, because ultraviolet absorption of a ligand 2-thenoyltrifluoroacetone (TTA) which depends on red light emission of the rare earth europium is about 332nm, and cross-cover with fluorescence emission (450nm-550nm) of a coumarin derivative is almost avoided, fluorescence resonance energy transfer between the coumarin and the rare earth complex is almost avoided, fluorescence of the two parts can be simultaneously realized, and spectral change accords with a photo (see figure 9).
In order to better understand the influence of the concentration and the excitation wavelength on the fluorescence spectrum of the polymer 4 white light material, the CIE coordinate values corresponding to the fluorescence spectrum of the polymer 4 white light material at different concentrations and excitation wavelengths are further examined. As shown in FIG. 9, the CIE color coordinates of the Polymer 4 white material show that the fluorescent color transitions from red to white to blue at excitation wavelengths from 320 to 450nm when the concentration is fixed; however, as the concentration of polymer 4 white light material increased, the blue light transitioned to green due to the association of coumarin, with the CIE coordinates approaching the green region gradually. When the polymer 4 white material was excited with 388nm (0.085g/L), an almost pure white emission was formed with CIE values (0.33,0.31) close to pure white (0.33 ).
The foregoing examples are provided for illustration and description of the invention and are not intended to limit the invention to the described examples. Furthermore, it will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, and that many variations and modifications may be made in accordance with the teachings of the present invention, all of which fall within the scope of the present invention as claimed.
Claims (3)
1. A polymer white light material based on coumarin and rare earth complexes is characterized by being a polymer 4, and the specific structural formula of the polymer white light material is as follows:
wherein n is 7-15 and m is 45-70.
2. The polymer white-light material based on coumarin and rare earth complex as claimed in claim 1, wherein the polymer 4 white-light material can simultaneously realize the emission of red light, blue light of coumarin derivative and white light of rare earth complex in one polymer by precisely regulating and controlling the excitation wavelength (320-450nm) and the CPB concentration (0.034g/L, 0.051g/L, 0.068g/L, 0.085g/L, 0.102g/L and 0.34 g/L).
3. The method for preparing polymer white-light material based on coumarin and rare earth complex as claimed in claim 1,
s1.6.17mmol of p-hydroxybenzaldehyde, 2-3 times of molar weight of allyl bromide and 2-3 times of molar weight of potassium carbonate are heated and refluxed for two hours in 12-20 mL of acetonitrile solution to obtain a compound 1;
s2.1.82mmol of compound 1 is further heated and refluxed with 1.82mmol of coumarin hydrazine derivative in 25mL of ethanol solution for four hours to generate Schiff base reaction, and then compound 2 is obtained.
S3.5mmol of methyl methacrylate and 0.125mmol of compound 2 are heated and polymerized in 6mL of Tetrahydrofuran (THF) under the initiation of 0.022mmol of azobisisobutyronitrile to obtain a polymer 3, and the polymer 3 is further heated and reacted with 0.5-time molar amount of Eu (TTA) 3- (H2O)2 in the Tetrahydrofuran (THF) solution for 24 hours to obtain a polymer 4 white light material;
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