CN111909687B - Multicolor adjustable luminous organic eutectic heterojunction composite material and preparation and application thereof - Google Patents

Multicolor adjustable luminous organic eutectic heterojunction composite material and preparation and application thereof Download PDF

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CN111909687B
CN111909687B CN202010657714.5A CN202010657714A CN111909687B CN 111909687 B CN111909687 B CN 111909687B CN 202010657714 A CN202010657714 A CN 202010657714A CN 111909687 B CN111909687 B CN 111909687B
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张伟
蒋倩婷
马铭
胡慧平
刘永
曹亚莉
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Hunan Normal University
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Abstract

The invention discloses a multicolor adjustable luminous organic eutectic heterojunction composite material and preparation and application thereof. The preparation method provided by the invention has the advantages of simple process, convenient operation and mild preparation conditions, and avoids the blindness of the heterojunction preparation process to a great extent. Laser excitation of the middle and end portions of the heterojunction, respectively, shows good waveguide performance with concomitant resonance energy transfer. The organic eutectic heterojunction can be applied to optical logic operation by utilizing the light-emitting property of the organic eutectic heterojunction, and has good application prospect in an integrated photonic circuit.

Description

Multicolor adjustable luminous organic eutectic heterojunction composite material and preparation and application thereof
Technical Field
The invention belongs to the technical field of organic heterojunction, and particularly relates to a multicolor adjustable luminous organic eutectic heterojunction composite material as well as a preparation method and application thereof.
Background
The photonic device has the advantages of high speed, high bandwidth, low energy consumption and the like which cannot be compared with an electronic device, and plays a very important role in optical information processing and photonic calculation. The heterojunction is a composite structure material formed by two different materials in contact, and has been widely applied to optical diodes, solar cells, optical logic operations and the like due to good photoelectric properties.
At present, inorganic semiconductor nano materials are used for preparing the heterojunction mostly, the inorganic semiconductor nano materials have better stability and good photoelectric property, but the acting force between the inorganic semiconductor materials is strong ionic bond, so the preparation of the inorganic heterojunction is complex, and harsh preparation conditions such as high temperature and high pressure are generally needed. The acting force among the molecules of the organic semiconductor material is weak intermolecular interaction, has the characteristics of mild preparation conditions, simple assembly method, flexible molecular design and the like, and can well make up the limitation of complex assembly of inorganic semiconductor materials. However, it has been found that the preparation of organic heterojunctions requires satisfying conditions of similar structure in terms of molecular selection, and the preparation requires continuous exploration and trial, with great blindness. Therefore, a simpler and practical method for preparing the organic heterojunction material is needed to be found.
Disclosure of Invention
The technical problem to be solved by the invention is to overcome the defects and shortcomings mentioned in the background technology, and provide a simple and practical multicolor adjustable luminous organic eutectic heterojunction composite material, and a preparation method and application thereof.
In order to solve the technical problems, the technical scheme provided by the invention is as follows:
a multi-color adjustable luminous organic eutectic heterojunction composite material is characterized in that donor molecules of a heterojunction are 9, 10-dimethylanthracene DMA, acceptor molecules are tetrafluoroterephthalonitrile TFP and 1,2,4, 5-pyromellitic nitrile TCNB, the heterojunction is of a one-dimensional three-section structure, two end parts of the heterojunction are DMA-TFP eutectic, and part of TFP in the DMA-TFP in the middle part is replaced and doped by the TCNB.
Further, the ratio of the amounts of DMA-TFP and DMA-TCNB species in the heterojunction is from 1:0.0005 to 1: 0.0087.
Furthermore, the two end parts of the heterojunction emit green light, and the middle part of the heterojunction shows the change from yellow, orange to red along with the increase of the doping proportion of the TCNB.
The invention discloses a preparation method of a multicolor adjustable luminous organic eutectic heterojunction composite material, which comprises the following steps:
s1, mixing a DMA-TFP mixed solution with a DMA-TCNB mixed solution; the DMA-TFP mixed solution is obtained by mixing a TFP solution and a DMA solution, and the DMA-TCNB mixed solution is obtained by mixing a TCNB solution and a DMA solution;
s2, dripping the solution obtained in the step S1 on a substrate, placing the substrate in an anti-solvent atmosphere, and slowly volatilizing the solvent to obtain the multicolor adjustable luminous organic eutectic heterojunction composite material.
Further, the concentration of the DMA solution of S1 is 6-10mM, the concentration of the TFP solution is 6-10mM, and the concentration of the TCNB solution is 6-10 mM.
Further, S1 shows that the volume ratio of the TFP solution to the DMA solution is 1:1, the volume ratio of the TCNB solution to the DMA solution is also 1:1, and the DMA-TCNB mixed solution is diluted to 0.1-0.2mM and then mixed with the DMA-TFP mixed solution.
Further, the mass ratio of the DMA-TFP mixed solution and the DMA-TCNB mixed solution in S1 is 1:0.0005-1: 0.0087.
Further, the solvent used for the solution of S1 is acetonitrile.
Further, the antisolvent of S2 is isopropanol.
The invention also provides application of the multicolor adjustable luminous organic eutectic heterojunction composite material in an optical logic operation device.
The invention adopts a liquid-phase self-assembly method and a co-crystallization strategy to combine organic eutectic materials together, and prepares the multicolor adjustable luminous organic eutectic heterojunction by adjusting the proportion of organic eutectic. Compared with the prior art, the invention has the beneficial effects that:
(1) the invention adopts a cocrystallization strategy, and one donor molecule can be respectively assembled into a eutectic with a plurality of acceptor molecules, so that the donor plays a bridge role between two or more different acceptors to organically combine different parts, thereby effectively avoiding blindness and phase separation in the heterojunction preparation process.
(2) The method for preparing the organic micro-nano heterojunction by adopting the liquid-phase self-assembly method is simple and rapid to operate, mild in preparation conditions, free of mechanical damage, green and environment-friendly, and capable of being prepared in a large scale.
(3) The multicolor adjustable luminous organic micro-nano heterojunction prepared by the invention has better photoelectric property. The two end parts emit green light, and the middle part emits light changed from yellow, orange and red with the increase of doping proportion. Laser excitation of the middle and end portions of the heterojunction, respectively, shows good waveguide performance with concomitant resonance energy transfer. The organic eutectic heterojunction can be applied to optical logic operation by utilizing the light-emitting property of the organic eutectic heterojunction, and has good application prospect in an integrated photonic circuit.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly introduced below, and it is obvious that the drawings in the following description are some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to these drawings without creative efforts.
FIG. 1 is a fluorescence micrograph of an organic eutectic material formed in examples 1 and 2 of the present invention;
FIG. 2 is a diagram of the energy levels of the organic single-component crystal materials DMA, TFP, TCNB of the present invention;
fig. 3 is a diagram of the growth mechanism of the organic eutectic heterojunction of the present invention (DMA-TFP: DMA-TCNB ═ 1: 0.0087);
FIG. 4 is a simplified schematic flow chart of a process for preparing a multi-color tunable light-emitting organic eutectic heterojunction according to an embodiment of the invention;
FIG. 5 is a fluorescence plot of organic eutectic heterojunction materials formed with increasing DMA-TFP and DMA-TCNB ratios for examples 3, 4,5 and 6 of the present invention;
FIG. 6 is a fluorescence micrograph of an organic eutectic heterojunction according to example 6 of the present invention;
FIG. 7 is a fluorescence spectrum of an end point of an organic eutectic heterojunction in example 6 of the present invention;
fig. 8 is a schematic diagram of an optical logic gate implemented by using the organic eutectic heterojunction according to embodiment 6 of the present invention.
Detailed Description
In order to facilitate understanding of the invention, the invention will be described more fully and in detail with reference to the accompanying drawings and preferred embodiments, but the scope of the invention is not limited to the specific embodiments below.
Unless otherwise defined, all terms of art used hereinafter have the same meaning as commonly understood by one of ordinary skill in the art. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to limit the scope of the present invention.
Unless otherwise specifically stated, various raw materials, reagents, instruments, equipment and the like used in the present invention are commercially available or can be prepared by existing methods.
The multicolor adjustable luminous organic eutectic heterojunction is a one-dimensional three-section type material, and molecules of the heterojunction are selected from donor molecules 9, 10-Dimethylanthracene (DMA), acceptor molecules Tetrafluoroterephthalonitrile (TFP) and acceptor molecules 1,2,4, 5-benzenetetracarboxylic nitrile (TCNB).
The molecular formulas are respectively as follows:
Figure BDA0002577351570000031
charge transfer can occur between the donor and acceptor molecules. Fig. 2 is a diagram of the energy levels of DMA, TFP, TCNB, and by combining the HOMO/LUMO energy values of TFP and TCNB, it was deduced that the DMA-based co-crystals have different association abilities, i.e., the charge transfer ability of DMA-TCNB is greater than that of DMA-TFP.
In a specific embodiment, the preparation method of the multicolor adjustable luminescent organic eutectic heterojunction micro-nano composite material comprises the following steps:
1) dissolving DMA in a solvent to obtain a DMA solution;
2) dissolving TFP in a solvent to obtain a TFP solution;
3) dissolving TCNB in a solvent to obtain a TCNB solution;
4) adding a certain amount of the TFP solution obtained in the step 2) into a certain amount of the DMA solution obtained in the step 1) to obtain a DMA-TFP mixed solution;
5) adding a certain amount of the TCNB solution obtained in the step 3) into a certain amount of the DMA solution obtained in the step 1) to obtain a DMA-TCNB mixed solution;
6) mixing the DMA-TFP mixed solution obtained in the step 4) with the DMA-TCNB mixed solution obtained in the step 5) according to a certain proportion;
7) dripping the solution obtained in the step 6) on a glass substrate, placing the glass substrate in an anti-solvent atmosphere, and slowly volatilizing the solvent on the surface of the glass substrate to obtain the multicolor adjustable luminous organic eutectic heterojunction composite material.
In a particular embodiment, in step 1), step 2), step 3), the concentration of the donor molecule DMA solution is between 6 and 10 mM; the concentration of the receptor molecule TFP solution is 6-10 mM; the concentration of the receptor molecule TCNB solution was 6-10 mM.
In one embodiment, in the step 4) and the step 5), the volume ratio of the donor molecule DMA solution to the acceptor molecule TFP solution is 1:1 during the solution mixing process; the volume ratio of the donor molecule DMA solution to the acceptor molecule TCNB solution was also 1:1, and the DMA-TCNB mixed solution was diluted to 0.1-0.2 mM.
In one embodiment, the ratio of the amounts of the materials of the DMA-TFP solution and the DMA-TCNB solution during the solution mixing in step 6) is 1:0.0005 to 1: 0.0087.
In a particular embodiment, in step 1), step 2), step 3), the solvents in the donor molecule DMA solution, the acceptor molecule TFP solution and the acceptor molecule TCNB solution are all acetonitrile. The anti-solvent of step 7) is isopropanol.
FIG. 3 is a schematic diagram of the growth mechanism of the organic eutectic heterojunction DMA-TFP-TCNB, and as can be seen, the DMA-TFP eutectic is firstly self-assembled into green short nanorods, because the DMA and TFP molecules have higher concentration in the original solution and have more chances of mutual collision; within the next few seconds, the emission of the middle part of the nanorods changed from green to red and at the same time the two green light emitting ends continued to grow epitaxially in axial direction, since the charge transfer interaction of DMA-TCNB is stronger than that of DMA-TFP, the TFP molecules were randomly replaced by TCNB molecules during the assembly process; finally, because the TCNB content is very small, the TCNB can be completely consumed quickly, and the DMA-TFP eutectic which is not completely consumed can be further epitaxially grown at two ends of the nanorod to form a three-section heterojunction.
Example 1
The preparation method of the organic eutectic comprises the following specific steps:
taking 9, 10-dimethylanthracene powder (DMA, chemical formula C)16H14) Dissolving in acetonitrile to obtain solution with concentration of 8mMDMA solution; taking tetrafluoroterephthalonitrile powder (TFP, chemical formula C)8F4N2) Dissolving in acetonitrile to prepare TFP solution with the concentration of 8 mM; then mixing the DMA solution and the TFP solution in a ratio of 1: 1; and (3) sucking 100uL of the mixed solution by using a syringe, quickly dripping the mixed solution on a glass substrate, placing the glass substrate in a solvent atmosphere containing an anti-solvent isopropanol, and slowly volatilizing the solvent on the surface of the glass substrate to obtain the DMA-TFP eutectic crystal on the glass substrate.
Example 2
The preparation method of the organic eutectic comprises the following specific steps:
taking 9, 10-dimethylanthracene powder (DMA, chemical formula C)16H14) Dissolving in acetonitrile to obtain DMA solution with concentration of 8 mM; taking 1,2,4, 5-tetracyanobenzene powder (TCNB, chemical formula C)10H2N4) Dissolving in acetonitrile to obtain TCNB solution with concentration of 8 mM; then mixing the DMA solution and the TCNB solution in a ratio of 1: 1; and (3) sucking 100uL of the mixed solution by using a syringe, quickly dripping the mixed solution on a glass substrate, placing the glass substrate in a solvent atmosphere containing an anti-solvent isopropanol, and slowly volatilizing the solvent on the surface of the glass substrate to obtain the DMA-TCNB eutectic crystal on the glass substrate.
The fluorescence patterns of the materials prepared in examples 1 and 2 are shown in FIG. 1, and it can be seen from FIG. 1 that the DMA-TFP eutectic is a rod-shaped crystal (A) emitting green light, and the DMA-TCNB eutectic is a linear crystal (B) emitting red light.
Example 3
The preparation method based on the multicolor adjustable luminescent organic eutectic heterojunction in the embodiment has the flow shown in fig. 4, and comprises the following specific steps:
taking 9, 10-dimethylanthracene powder (DMA, chemical formula C)16H14) Dissolving in acetonitrile to obtain DMA solution with concentration of 8 mM; taking tetrafluoroterephthalonitrile powder (TFP, chemical formula C)8F4N2) Dissolving in acetonitrile to prepare TFP solution with the concentration of 8 mM; taking 1,2,4, 5-tetracyanobenzene powder (TCNB, chemical formula C)10H2N4) Dissolving in acetonitrile to prepare a TCNB solution with the concentration of 8mM, and then mixing a DMA solution and a TFP solution in a volume ratio of 1: 1; mixing DMA solution with TCNBMixing the solution in a volume ratio of 1:1, and then diluting the DMA-TCNB mixed solution to 0.125 mM; and then mixing the DMA-TFP solution and the diluted DMA-TCNB solution according to the molar ratio of 1:0.0005 to obtain a mixed solution, then sucking 100uL of the mixed solution by using an injector, quickly dripping the mixed solution on a glass substrate, placing the glass substrate in a solvent atmosphere containing an anti-solvent isopropanol, slowly volatilizing the mixed solvent on the surface of the glass substrate, and obtaining the DMA-TFP-TCNB organic three-section heterojunction on the glass substrate.
Example 4
The preparation method based on the multicolor adjustable luminescent organic eutectic heterojunction in the embodiment has the flow shown in fig. 4, and comprises the following specific steps:
taking 9, 10-dimethylanthracene powder (DMA, chemical formula C)16H14) Dissolving in acetonitrile to obtain DMA solution with concentration of 8 mM; taking tetrafluoroterephthalonitrile powder (TFP, chemical formula C)8F4N2) Dissolving in acetonitrile to prepare TFP solution with the concentration of 8 mM; taking 1,2,4, 5-tetracyanobenzene powder (TCNB, chemical formula C)10H2N4) Dissolving in acetonitrile to prepare a TCNB solution with the concentration of 8mM, and then mixing a DMA solution and a TFP solution in a volume ratio of 1: 1; mixing the DMA solution and the TCNB solution in a volume ratio of 1:1, and then diluting the DMA-TCNB mixed solution to 0.125 mM; and then mixing the DMA-TFP solution and the diluted DMA-TCNB solution according to the molar ratio of 1:0.0010 to obtain a mixed solution, then sucking 100uL of the mixed solution by using an injector, quickly dripping the mixed solution on a glass substrate, placing the glass substrate in a solvent atmosphere containing an anti-solvent isopropanol, slowly volatilizing the mixed solvent on the surface of the glass substrate, and obtaining the DMA-TFP-TCNB organic three-section heterojunction on the glass substrate.
Example 5
The preparation method based on the multicolor adjustable luminescent organic eutectic heterojunction in the embodiment has the flow shown in fig. 4, and comprises the following specific steps:
taking 9, 10-dimethylanthracene powder (DMA, chemical formula C)16H14) Dissolving in acetonitrile to obtain DMA solution with concentration of 8 mM; taking tetrafluoroterephthalonitrile powder (TFP, chemical formula C)8F4N2) Dissolving in acetonitrile to prepare TFP solution with the concentration of 8 mM; taking 1,2,4, 5-tetracyanobenzene powder (TCNB, chemical formula C)10H2N4) Dissolving in acetonitrile to prepare a TCNB solution with the concentration of 8mM, and then mixing a DMA solution and a TFP solution in a volume ratio of 1: 1; mixing the DMA solution and the TCNB solution in a volume ratio of 1:1, and then diluting the DMA-TCNB mixed solution to 0.125 mM; and then mixing the DMA-TFP solution and the diluted DMA-TCNB solution according to the molar ratio of 1:0.0037 to obtain a mixed solution, then sucking 100uL of the mixed solution by using an injector, quickly dripping the mixed solution on a glass substrate, placing the glass substrate in a solvent atmosphere containing an anti-solvent isopropanol, slowly volatilizing the mixed solvent on the surface of the glass substrate, and obtaining the DMA-TFP-TCNB organic three-section heterojunction on the glass substrate.
Example 6
The preparation method based on the multicolor adjustable luminescent organic eutectic heterojunction in the embodiment has the flow shown in fig. 4, and comprises the following specific steps:
taking 9, 10-dimethylanthracene powder (DMA, chemical formula C)16H14) Dissolving in acetonitrile to obtain DMA solution with concentration of 8 mM; taking tetrafluoroterephthalonitrile powder (TFP, chemical formula C)8F4N2) Dissolving in acetonitrile to prepare TFP solution with the concentration of 8 mM; taking 1,2,4, 5-tetracyanobenzene powder (TCNB, chemical formula C)10H2N4) Dissolving in acetonitrile to prepare a TCNB solution with the concentration of 8mM, and then mixing a DMA solution and a TFP solution in a volume ratio of 1: 1; mixing the DMA solution and the TCNB solution in a volume ratio of 1:1, and then diluting the DMA-TCNB mixed solution to 0.125 mM; and then mixing the DMA-TFP solution and the diluted DMA-TCNB solution according to the molar ratio of 1:0.0087 to obtain a mixed solution, then sucking 100uL of the mixed solution by using an injector, quickly dripping the mixed solution on a glass substrate, placing the glass substrate in a solvent atmosphere containing an anti-solvent isopropanol, slowly volatilizing the mixed solvent on the surface of the glass substrate, and obtaining the DMA-TFP-TCNB organic three-section heterojunction on the glass substrate.
Fig. 5 is a fluorescence spectrum of the organic eutectic heterojunction prepared in example 3, example 4, example 5 and example 6. It can be seen from the figure that the prepared heterojunction is a one-dimensional three-segment structure, two end parts emit green light, and the middle part emits light changed from yellow, orange and red along with the increase of the doping ratio.
As shown in fig. 6, when the left end, the middle and the left end and the middle of the organic eutectic heterojunction are excited, a certain degree of resonance energy transfer occurs, and an optical signal is coupled out from the right end of the organic eutectic heterojunction (three reference numerals 1,2 and 3 in the figure represent the left end, the middle and the left end and the middle of the excitation, respectively). Fig. 7 is a fluorescence spectrum collected at the right end of the organic eutectic heterojunction in three excitation modes, further illustrating the resonance energy transfer of an optical signal in the structure, and realizing the application of a nanophotonics logic gate (fig. 8).
The foregoing is considered as illustrative of the preferred embodiments of the invention and is not to be construed as limiting the invention in any way. Therefore, any simple modification, equivalent change and modification made to the above embodiments according to the technical spirit of the present invention should fall within the protection scope of the technical scheme of the present invention, unless the technical spirit of the present invention departs from the content of the technical scheme of the present invention.

Claims (9)

1. The multicolor adjustable luminous organic eutectic heterojunction composite material is characterized in that donor molecules of a heterojunction are 9, 10-dimethylanthracene DMA, acceptor molecules are tetrafluoroterephthalonitrile TFP and 1,2,4, 5-pyromellitic nitrile TCNB, the heterojunction is of a one-dimensional three-section structure, two end parts of the heterojunction are DMA-TFP eutectic, and part of TFP in the middle part of DMA-TFP is replaced and doped by TCNB.
2. The multi-color tunable luminescent organic eutectic heterojunction composite material of claim 1, wherein the amount of DMA-TFP and DMA-TCNB substances in the heterojunction is in a ratio of 1:0.0005 to 1: 0.0087.
3. The multi-color tunable luminescent organic eutectic heterojunction composite material of claim 2, wherein the two end portions of the heterojunction emit green light, and the middle portion emits light from yellow, orange to red with the increase of the doping ratio of the TCNB.
4. A preparation method of the multicolor tunable light-emitting organic eutectic heterojunction composite material as claimed in any one of claims 1 to 3, characterized by comprising the following steps:
s1, mixing the DMA-TFP mixed solution with the DMA-TCNB mixed solution according to the mass ratio of 1:0.0005-1: 0.0087; the DMA-TFP mixed solution is obtained by mixing a TFP solution and a DMA solution, and the DMA-TCNB mixed solution is obtained by mixing a TCNB solution and a DMA solution;
and S2, dripping the solution obtained in the step S1 on a substrate, placing the substrate in an anti-solvent atmosphere, and slowly volatilizing the solvent to obtain the multicolor adjustable luminous organic eutectic heterojunction composite material.
5. The method according to claim 4, wherein the DMA solution is used at S1 at a concentration of 6-10mM, the TFP solution at a concentration of 6-10mM, and the TCNB solution at a concentration of 6-10 mM.
6. The preparation method according to claim 5, wherein S1 the volume ratio of the TFP solution to the DMA solution is 1:1, the volume ratio of the TCNB solution to the DMA solution is also 1:1, and the DMA-TCNB mixed solution is diluted to 0.1-0.2mM and then mixed with the DMA-TFP mixed solution.
7. The method according to any one of claims 4 to 6, wherein the solvent used for the solution of S1 is acetonitrile.
8. The method according to any one of claims 4 to 6, wherein the antisolvent S2 is isopropanol.
9. The multicolor adjustable luminous organic eutectic heterojunction composite material as claimed in any one of claims 1 to 3, or the application of the multicolor adjustable luminous organic eutectic heterojunction composite material prepared by the preparation method as claimed in any one of claims 4 to 6 in an optical logic operation device.
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