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CN113234008A - Fluorescent organic matter, fluorescent dye and sequential color light emission regulation method - Google Patents

Fluorescent organic matter, fluorescent dye and sequential color light emission regulation method Download PDF

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CN113234008A
CN113234008A CN202110460532.3A CN202110460532A CN113234008A CN 113234008 A CN113234008 A CN 113234008A CN 202110460532 A CN202110460532 A CN 202110460532A CN 113234008 A CN113234008 A CN 113234008A
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fluorescent
fluorescent organic
pmma
organic matter
sequential color
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郭鹍鹏
李洁
梁效中
李达
张征
王思静
李芷君
邢艺凡
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Taiyuan University of Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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Abstract

The invention relates to the technical field of sequential color luminescence, in particular to a fluorescent organic matter, a fluorescent dye and a sequential color luminescence regulation and control method, wherein a nitrogenous aromatic ring derivative is used as a central group, an aromatic ring is used as a peripheral group, and the central group is connected with the peripheral group through a flexible chain. The invention also provides a fluorescent dye which is prepared by adopting a fluorescent organic matter as a raw material and physically doping PMMA in the fluorescent organic matter.

Description

Fluorescent organic matter, fluorescent dye and sequential color light emission regulation method
Technical Field
The invention relates to the technical field of sequential color luminescence, in particular to a fluorescent organic matter, a fluorescent dye and a sequential color luminescence regulation and control method.
Background
The luminous intensity and the luminous color are two important characteristics of light, and much research has been conducted on a gorgeous luminescent material. Currently, strategies to obtain fluorescent color modulation include: regulating the size of the carbon quantum dot, controlling the halogen type and proportion in the organic-inorganic hybrid perovskite structure, changing the substituent in the organic molecule, and the like. Wherein, the organic molecule has the characteristics of rich raw material sources, easy structure modification and the like, and becomes an important branch for the research and commercialization of the fluorescent dye. The current common strategy for obtaining different fluorescence colors is to change the energy level structure by changing the molecular structure (e.g. introducing different substituents) to realize different luminescence colors. However, this strategy not only requires tedious organic synthesis, but also the prepared dye emission color is difficult to realize fine sequential control. Therefore, the development of the fluorescent dye with adjustable sequential color luminescence has important research significance and application prospect.
Disclosure of Invention
In order to solve the problems in the background art, the invention provides an organic matter, and a fluorescent dye is formed by physically doping PMMA, and on the basis, a method for regulating and controlling sequential color luminescence is provided, so that the problems in the background art are effectively solved, and the technical scheme adopted by the invention is as follows:
a fluorescent organic matter takes a nitrogenous aromatic ring derivative as a central group, takes an aromatic ring as a peripheral group, and the central group and the peripheral group are connected through a flexible chain, and has the following structural general formula:
Figure BDA0003042076860000021
wherein R1 is independently represented by H, CH3, C2H5, C3H7, C4H9, C5H11, C6H13, C7H15, or C8H17, and R2 is independently represented by benzene, naphthalene, anthracene, or pyrene.
In an absolute ethyl alcohol solution, 9-alkyl-carbazole-3, 6-dicarboxaldehyde and acetylpyrene are subjected to chalcone condensation reaction under the catalysis of a sodium hydroxide solution with the concentration of 40%, and then are recrystallized in absolute ethyl alcohol, cooled and filtered to obtain a powdery sample.
The alkyl in the 9-alkyl-carbazole-3, 6-dicarbaldehyde is specifically hexyl.
The acetylpyrene can also be replaced by one of acetophenone, acetonaphthone or acetyl anthracene.
The feeding molar ratio of the 9-alkyl-carbazole-3, 6-dicarboxaldehyde to the acetylpyrene is 1: 2.4.
A fluorescent dye is prepared by physically doping PMMA in a fluorescent organic matter serving as a raw material.
The mass fraction of PMMA doped in the fluorescent organic substance may be 0%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, or 90%.
A method for regulating and controlling sequential color luminescence of fluorescent dye is characterized by comprising the following steps:
s1, preparing a fluorescent organic matter;
s2, weighing the powdery fluorescent organic material and PMMA powder, and dissolving the powdery fluorescent organic material and the PMMA powder in a tetrahydrofuran solution. Dripping the prepared mixed solution on a quartz plate, and forming a fluorescent film after the solvent is volatilized;
s3, dividing the fluorescent organic matters prepared in S1 into a plurality of groups, and doping PMMA with the mass fraction of 0%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80% and 90% in S2 in sequence to form fluorescent films with different colors;
s4, arranging the fluorescent films in the S3 according to the mass fraction of the doped PMMA from small to large, and under the excitation of 365nm blue light, the films can emit sequence fluorescence from red to blue, wherein the span of the sequence fluorescence is 613nm-498 nm.
The method also comprises a step S5, wherein the specific step S5 is as follows: and preparing the fluorescent film on the inner wall of the LED lamp bead as described in S3.
In the S3, the mass fraction of the doped PMMA can be 0-90%.
Compared with the prior art, the invention has the beneficial effects that:
1. after physical doping is carried out on PMMA with different mass fractions, the samples can emit sequence fluorescence from red to blue with the span of 613nm-498nm under the excitation of 365nm blue light.
2. According to the invention, the organic dye is simply and physically doped, the doping quality fraction of the physical substrate is controlled, the continuous adjustment of the luminescent color is realized, the sequential color fluorescence regulation and control method is obtained, and the sequential color LED lamp bead is prepared by utilizing the characteristic. Among them, the emission color sequence formed by the dye is preferably covered between 613nm-498 nm.
3. The fluorescent organic matter is prepared by chalcone condensation reaction, the preparation method is simple, the yield is more than 60%, and the obtained organic fluorescent material has an accurate molecular structure.
In conclusion, the invention has the advantages of ingenious design and novel concept, provides a simple and easily obtained sequential color light-emitting regulation and control method, and has very obvious popularization significance.
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FIG. 1 is a scheme showing the synthesis route of the fluorescent organic substance of the present invention;
FIG. 2 is a nuclear magnetic hydrogen spectrum (a) of the fluorescent organic substance of the present invention;
FIG. 3 is a nuclear magnetic hydrogen spectrum (b) of the fluorescent organic substance of the present invention;
FIG. 4 shows photoluminescence spectra of films prepared by mixing the fluorescent organic substance of the present invention with PMMA powder of different mass fractions.
FIG. 5 shows an electroluminescence spectrum of an LED lamp bead prepared by mixing a fluorescent organic substance and PMMA powder with different mass fractions.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Referring to fig. 1 to 5, the present invention provides a fluorescent organic substance, which uses a nitrogen-containing aromatic ring derivative as a central group, uses an aromatic ring as a peripheral group, and the central group and the peripheral group are connected by a flexible chain, and has the following structural general formula:
Figure BDA0003042076860000041
wherein R1 is independently represented by H, CH3, C2H5, C3H7, C4H9, C5H11, C6H13, C7H15, or C8H17, and R2 is independently represented by benzene, naphthalene, anthracene, or pyrene.
The preparation method of the fluorescent organic matter comprises the following steps: in an absolute ethyl alcohol solution, 9-alkyl-carbazole-3, 6-dicarboxaldehyde and acetylpyrene are subjected to chalcone condensation reaction under the catalysis of a sodium hydroxide solution with the concentration of 40%, and then are recrystallized in absolute ethyl alcohol, cooled and filtered to obtain a powdery sample.
The alkyl in the 9-alkyl-carbazole-3, 6-dicarbaldehyde is specifically hexyl.
The acetylpyrene can also be replaced by one of acetophenone, acetonaphthone or acetyl anthracene.
The feeding molar ratio of the 9-alkyl-carbazole-3, 6-dicarboxaldehyde to the acetylpyrene is 1: 2.4.
The invention also provides a fluorescent dye which is prepared by physically doping PMMA in a fluorescent organic matter serving as a raw material.
The mass fraction of PMMA doped in the fluorescent organic substance may be 0%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, or 90%.
The invention also provides a method for regulating and controlling sequential color luminescence by using the fluorescent dye, which is characterized by comprising the following steps of:
s1, preparing a fluorescent organic matter;
s2, weighing the powdery fluorescent organic material and PMMA powder, and dissolving the powdery fluorescent organic material and the PMMA powder in a tetrahydrofuran solution. Dripping the prepared mixed solution on a quartz plate, and forming a fluorescent film after the solvent is volatilized;
s3, dividing the fluorescent organic matters prepared in S1 into a plurality of groups, and doping PMMA with the mass fraction of 0%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80% and 90% in S2 in sequence to form fluorescent films with different colors;
s4, arranging the fluorescent films in the S3 according to the mass fraction of the doped PMMA from small to large, and under the excitation of 365nm blue light, the films can emit sequence fluorescence from red to blue, wherein the span of the sequence fluorescence is 613nm-498 nm.
As a preferred embodiment, the present embodiment further includes step S5, where the specific step S5 is: and preparing the fluorescent film on the inner wall of the LED lamp bead as described in S3.
As a preferable example, in S3 described in this embodiment, the mass fraction of doped PMMA may be 0-90%.
The specific preparation process of the fluorescent organic matter comprises the following steps: (examples of 9-hexyl-carbazole-3, 6-dicarbaldehyde and acetylpyrene)
Weighing 307.0mg (1.0mmol) of 9-hexyl-carbazole-3, 6-dimethyl aldehyde, adding 20mL of absolute ethyl alcohol into a 100mL round-bottom flask, stirring in an ice bath until the absolute ethyl alcohol is completely dissolved, weighing 652.0mg (2.4mmol) of acetylpyrene, dissolving in 20mL of ethanol solution, slowly dripping into a reaction system, stirring at 0 ℃ for 30 minutes, then stirring at room temperature for 6 hours, standing and filtering after the reaction is completely finished to obtain orange red powder, recrystallizing absolute ethyl alcohol to obtain bright red powder, filtering to obtain 460mg of a product, and obtaining the yield of 61.1%. The nuclear magnetic resonance hydrogen spectrum of the fluorescent organic matter is as follows:
1H NMR(600MHz,CDCl3)δ8.61(d,J＝9.2Hz,2H)，8.29–8.21(m,9H)，8.17(t,J＝8.3Hz,4H)，8.12(d,J＝8.9Hz,2H)，8.06(t,J＝7.6Hz,2H)，7.79(dd,J＝22.2,12.2Hz,4H)，7.49(dd,J＝15.8,9.0Hz,2H)，7.42(d,J＝8.6Hz,2H)，4.32(dd,J＝17.5,10.3Hz,2H)，1.91–1.83(m,2H)，1.39–1.26(m,6H)，0.89–0.81(m,3H)。
13C NMR(151MHz,CDCl3)δ196.11(s)，147.31(s)，142.45(s)，134.48(s)，133.03(s)，131.19(s)，130.74(s)，129.26(s)，128.95(d,J＝13.7Hz)，127.24(s)，126.86(s)，126.58(s)，126.34(s)，126.04(d,J＝14.5Hz)，125.85(s)，125.25(s)，124.90(d,J＝6.4Hz)，124.51(s)，124.13(s)，123.27(s)，121.79(s)，109.68(s)，31.34(s)，28.95(s)，26.88(s)，22.51(s)，13.98(s)。
preparation of a doped thin film:
firstly, 0.05g of fluorescent organic matter and 0.05g of PMMA powder are weighed and dissolved in 1mL of tetrahydrofuran solution. Dropping the prepared mixed solution on a quartz plate, after the solvent is volatilized, finishing the film and the manufacture, sequentially dissolving the powder with the mass fraction of 0, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80% and 90% of the fluorescence organic matter physically doped with PMMA in 1mL of tetrahydrofuran solution, and respectively dropping the powder on the quartz plate. The photoluminescence spectrum of the prepared film is shown in fig. 4. Table 1 shows the emission wavelength of the films at different PMMA doping ratios.
Figure BDA0003042076860000061
TABLE 1
Preparing an LED lamp bead:
respectively mixing the fluorescent organic matter and powder with the mass fractions of 0, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80% and 90% of PMMA, then sequentially dissolving the mixture in 1ml of tetrahydrofuran solution, carrying out ultrasonic treatment for 1 hour, and uniformly dispersing the mixture in the tetrahydrofuran solution. Slowly dripping the mixed solution into the inner wall of the LED lamp bead, and naturally air-drying the LED lamp bead for 3 hours to form a film at a ventilated position. Finally, combining the LED lamp beads with a 365nm ultraviolet LED light source to obtain LEDs, and testing to obtain an electroluminescence spectrum of the LEDs, as shown in fig. 5, the electroluminescence spectrum of the prepared LED lamp beads is shown, and table 2 shows the light emitting wavelengths of the LED lamp beads at different PMMA doping ratios.
Figure BDA0003042076860000071
TABLE 2
Although only the preferred embodiments of the present invention have been described in detail, the present invention is not limited to the above embodiments, and various changes can be made without departing from the spirit of the present invention within the knowledge of those skilled in the art, and all changes are encompassed in the scope of the present invention.

Claims (10)

1.一种荧光有机物，其特征在于，以含氮芳香环衍生物为中心基团，以芳香环作为外围基团，中心基团和外围基团通过柔性链相连，具有以下结构通式：1. a fluorescent organic substance is characterized in that, with nitrogen-containing aromatic ring derivative as central group, with aromatic ring as peripheral group, central group and peripheral group are connected by flexible chain, have following general structural formula:
Figure FDA0003042076850000011
Figure FDA0003042076850000011
 其中R1独立地表示为H、CH3、C2H5、C3H7、C4H9、C5H11、C6H13、C7H15或C8H17，R2独立地表示为苯、萘、蒽或芘。wherein R 1 is independently represented as H, CH 3 , C 2 H 5 , C 3 H 7 , C 4 H 9 , C 5 H 11 , C 6 H 13 , C 7 H 15 or C 8 H 17 , and R 2 is independently Denoted as benzene, naphthalene, anthracene or pyrene. 2.根据权利要求1所述的一种荧光有机物的制备方法，其特征在于：在无水乙醇溶液中，9-烷基-咔唑-3,6-二甲醛与乙酰芘在40％浓度下的氢氧化钠溶液催化下进行查尔酮缩合反应，然后在无水乙醇中重结晶，冷却过滤后得到粉末状样品。2. the preparation method of a kind of fluorescent organic matter according to claim 1 is characterized in that: in absolute ethanol solution, 9-alkyl-carbazole-3,6-dicarboxaldehyde and acetylpyrene are under 40% concentration The chalcone condensation reaction was carried out under the catalysis of sodium hydroxide solution, and then recrystallized in absolute ethanol, and the powder sample was obtained after cooling and filtration. 3.根据权利要求2所述的一种荧光有机物的制备方法，其特征在于：所述9-烷基-咔唑-3,6-二甲醛中的烷基具体为己基。3 . The method for preparing a fluorescent organic substance according to claim 2 , wherein the alkyl group in the 9-alkyl-carbazole-3,6-dicarbaldehyde is specifically hexyl. 4 . 4.根据权利要求2所述的一种荧光有机物的制备方法，其特征在于：所述乙酰芘还可替换为乙酰苯、乙酰萘或乙酰蒽中的其中一种。4 . The method for preparing a fluorescent organic substance according to claim 2 , wherein the acetylpyrene can also be replaced with one of acetophenone, acetylnaphthalene or acetylanthracene. 5 . 5.根据权利要求2所述的一种荧光有机物的制备方法，其特征在于：所述9-烷基-咔唑-3,6-二甲醛与乙酰芘的投料摩尔比为1:2.4。5. The preparation method of a fluorescent organic matter according to claim 2, wherein the molar ratio of the 9-alkyl-carbazole-3,6-dicarbaldehyde to acetylpyrene is 1:2.4. 6.一种荧光染料，其特征在于：采用权利要求1所述的一种荧光有机物为原料，在所述荧光有机物中物理掺杂PMMA制备得到。6. A fluorescent dye, characterized in that it is prepared by using the fluorescent organic substance according to claim 1 as a raw material and physically doping PMMA in the fluorescent organic substance. 7.根据权利要求6所述的一种荧光染料，其特征在于：所述荧光有机物中掺杂的PMMA的质量分数可为0％，10％，20％，30％，40％，50％，60％，70％，80％，或90％。7. The fluorescent dye according to claim 6, wherein the mass fraction of PMMA doped in the fluorescent organic material can be 0%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, or 90%. 8.根据权利要求6或7所述的一种荧光染料进行序列色发光调控的方法，其特征在于，包括以下步骤：8. the method that a kind of fluorescent dye according to claim 6 or 7 carries out sequential color luminescence regulation, is characterized in that, comprises the following steps: S1、制备荧光有机物；S1, prepare fluorescent organic matter; S2、称取粉末状的荧光有机物材料和PMMA粉末，溶解于四氢呋喃溶液中。将制备好的混合溶液滴在石英片上，待溶剂挥发干后形成荧光薄膜；S2. Weigh the powdery fluorescent organic material and PMMA powder, and dissolve them in a tetrahydrofuran solution. Drop the prepared mixed solution on the quartz plate, and form a fluorescent film after the solvent is evaporated and dried; S3、将S1中制备的荧光有机物分为若干组，并在S2中依次掺杂质量分数为0％，10％，20％，30％，40％，50％，60％，70％，80％，90％的PMMA形成不同颜色的荧光薄膜；S3. Divide the fluorescent organic compounds prepared in S1 into several groups, and sequentially dope them in S2 with mass fractions of 0%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80% , 90% of PMMA forms fluorescent films of different colors; S4、将S3中的荧光薄膜按照掺杂的PMMA质量分数由小到大的顺序排列，在365nm蓝光激发下，薄膜可发出跨度在613nm-498nm的由红到蓝的序列荧光。S4. Arrange the fluorescent films in S3 in order of doped PMMA mass fraction from small to large. Under the excitation of 365nm blue light, the film can emit a sequence of fluorescence from red to blue with a span of 613nm-498nm. 9.根据权利要求8所述的一种荧光染料进行序列色发光调控的方法，其特征在于，还包括步骤S5，所述S5的具体步骤为：在LED灯珠内壁上制备如S3中所述的荧光薄膜。9 . The method for controlling sequential color luminescence with a fluorescent dye according to claim 8 , further comprising step S5 , and the specific step of S5 is: preparing on the inner wall of the LED lamp bead as described in S3 . fluorescent film. 10.根据权利要求8所述的一种荧光染料进行序列色发光调控的方法，其特征在于，所述S3中，掺杂的PMMA质量分数可为0-90％。10 . The method for controlling sequential color luminescence with a fluorescent dye according to claim 8 , wherein, in the S3 , the mass fraction of doped PMMA can be 0-90%. 11 .
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