CN114702496A - Organic eutectic material and preparation method and application thereof - Google Patents
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Abstract
The invention discloses an organic eutectic material and a preparation method and application thereof, wherein the organic eutectic material is formed by donor molecules and acceptor molecules through self-assembly non-covalent bonds, wherein the donor molecules are 5, 7-dihydro-indolo [2,3-B ] carbazole, the acceptor molecules are 2,2'- (benzo [1,2-B:4,5-B' ] dithiophene-4, 8-diimine) dipropionitrile, and the ratio of the donor molecules to the acceptor molecules is 1:1 according to the parts of substances. The photoelectric response of the organic micromolecular semiconductor material in near infrared is realized in a eutectic engineering mode; wherein, the organic eutectic material has the advantages of simple and efficient preparation, low cost, good crystallinity and the like; the materials and the structural design can be customized through eutectic engineering, the organic micromolecular semiconductor material with proper band gap and high-efficiency charge transmission is prepared, and the organic micromolecular semiconductor material has good photoelectric property when being applied to a near-infrared transistor.
Description
Technical Field
The invention belongs to the technical field of organic photoelectric semiconductors, and particularly relates to an organic eutectic material and a preparation method and application thereof.
Background
With the rapid development of organic semiconductor materials, the organic semiconductor materials are commonly used in the fields of Organic Light Emitting Diodes (OLEDs), Organic Field Effect Transistors (OFETs), Organic Light Emitting Transistors (OLETs), near infrared Organic Phototransistors (OPT), and the like as active layers. Among them, the near-infrared phototransistor attracts attention of researchers in many aspects such as night visibility, health monitoring and thermal efficiency analysis. At present, most of polymer semiconductors are used as active layers to realize near-infrared photoelectric response, the design structure and synthesis of the polymer semiconductors are complex, the application of semiconductor materials in near-infrared phototransistors is influenced, and the rapid development of the near-infrared phototransistors is hindered.
Disclosure of Invention
In view of the shortcomings of the prior art, the present invention aims to provide an organic eutectic material.
The invention also aims to provide a preparation method of the organic eutectic material.
The invention also aims to provide application of the organic eutectic material in an organic field effect transistor.
The purpose of the invention is realized by the following technical scheme.
An organic eutectic material (5, 7-ICZ-DTTCNQ) is formed by a self-assembly non-covalent bond of a donor molecule and an acceptor molecule, wherein the donor molecule is 5, 7-dihydro-indolo [2,3-B ] carbazole, the acceptor molecule is 2,2'- (benzo [1,2-B:4,5-B' ] dithiophene-4, 8-diimine) dipropionitrile, and the ratio of the donor molecule to the acceptor molecule is 1:1 according to the parts of substances.
In the technical scheme, the organic eutectic material is 5, 7-dihydro-indolo [2,3-B ] carbazole-2, 2'- (benzo [1,2-B:4,5-B' ] dithiophene-4, 8-diylidene) dipropionitrile.
In the above technical scheme, the organic eutectic material is monoclinic system, and the space group is C1 2/c1。
In the above technical solution, the unit cell parameters of the organic eutectic material are as follows: 39.0513(7), 7.11710(10), 19.8653(3), 90 α, 90.130(2), 90 γ.
In the technical scheme, the length of the organic eutectic material is 0.5-10 mm.
The preparation method of the organic eutectic material comprises the following steps:
and dissolving donor molecules and acceptor molecules in a solvent to obtain a mixed solution, keeping the temperature of the mixed solution constant at 80-130 ℃ until the donor molecules and the acceptor molecules are completely dissolved in the solvent, and volatilizing the solvent to obtain the organic eutectic material.
In the technical scheme, the volatilization temperature is 20-25 ℃ at room temperature.
In the technical scheme, the ratio of the donor molecules to the acceptor molecules is 1:1 according to the parts by weight of the substances.
In the technical scheme, the solvent is acetonitrile, toluene and/or chlorobenzene.
In the technical scheme, the concentration of the mixed solution is 0.2-3.0 mg/mL.
In the technical scheme, the constant temperature time is 1-10 hours.
The organic eutectic material is applied to the field effect transistor and is used as an organic semiconductor layer in the field effect transistor.
In the technical scheme, the organic semiconductor layer is positioned on the insulating layer, and the organic eutectic material with the thickness of 30-35nm is prepared on the insulating layer to serve as the organic semiconductor layer.
In the above technical solution, the current switching ratio of the field effect transistor is at most 107The field effect transistor is excited by light with wavelength of 808nm, and the highest light responsivity is 2923A/W.
In the technical scheme, the thickness of the source electrode and the drain electrode of the field effect transistor is 120-150 nm.
The photoelectric response of the organic micromolecular semiconductor material in near infrared is realized in a eutectic engineering mode; wherein, the organic eutectic material has the advantages of simple and efficient preparation, low cost, good crystallinity and the like; the materials and the structural design can be customized through eutectic engineering, the organic micromolecular semiconductor material with proper band gap and high-efficiency charge transmission is prepared, and the organic micromolecular semiconductor material has good photoelectric property when being applied to a near-infrared transistor.
Drawings
FIG. 1 is a schematic structural diagram of an organic eutectic material;
FIG. 2 is a UV-VIS absorption spectrum of a donor molecule, an acceptor molecule, and the organic eutectic material of example 1 in a solid state;
FIG. 3 is a schematic diagram of a field effect transistor;
FIG. 4 is a transfer characteristic curve of a field effect transistor;
FIG. 5 is an output characteristic curve of a field effect transistor;
FIG. 6 is a schematic diagram of a structure of a near-infrared organic phototransistor;
FIG. 7 is a graph of transfer characteristics of a near-infrared organic phototransistor in light and dark;
FIG. 8 is a performance graph of the photoresponse of a near-infrared organic phototransistor as a function of gate voltage;
fig. 9 is an optical microscope image of an organic eutectic material.
Detailed Description
The technical scheme of the invention is further explained by combining specific examples.
The following examples relate to pharmaceutical products as purchasers and purities as follows:
silicon wafer (Si/SiO)2) Wherein, SiO2Chinese electro-technical group forty-six institute of research (research institute) with thickness of 300nm
The following examples relate to some instruments and models for test characterization as follows:
ultraviolet: UV2600 ultraviolet visible spectrophotometer
And (3) testing a device: keithley 4200-scs
Crystal analysis: XtaLAB SuperNova, Kyowa Co Ltd
The method for obtaining the OTS modified silicon wafer comprises the following steps: a substrate silicon wafer (Si/SiO)2) Sequentially putting the mixture into deionized water, acetone and isopropanol, and performing ultrasonic treatment for 10 minutes respectively; heating the silicon wafer in isopropanol to 80 ℃, keeping the temperature for 3 hours, and drying the silicon wafer by using nitrogen; and (3) carrying out oxygen plasma treatment on the silicon wafer for 15 minutes under the following oxygen plasma treatment conditions: the power is 80W, and the gas flow rate of oxygen is 20 sccm; putting the silicon wafer into an oven to modify Octadecyl Trichlorosilane (OTS) under the following conditions: under the vacuum condition, heating the silicon wafer from room temperature to 90 ℃ and keeping the temperature for 60min, dropwise adding 1 drop of OTS, heating to 120 ℃ and keeping the temperature for 120min, and cooling to room temperature; and taking out the silicon wafer, and sequentially putting the silicon wafer into n-hexane, trichloromethane and isopropanol for 10min respectively by ultrasonic treatment to obtain the OTS modified silicon wafer.
Example 1
A preparation method of an organic eutectic material comprises the following steps:
and (2) dissolving donor molecules and acceptor molecules in a solvent to obtain a mixed solution, wherein the ratio of the donor molecules to the acceptor molecules is 1:1 according to the parts by weight of the substances, heating the mixed solution to 80 ℃ by using a heating table, keeping the temperature constant for 3 hours until the donor molecules and the acceptor molecules are completely dissolved in the solvent, and stopping heating. And (3) sucking 30 microliters of the mixed solution by using a liquid transfer gun, dropwise adding the mixed solution to one side of the silicon dioxide of the OTS modified silicon wafer, volatilizing the solvent at room temperature of 20-25 ℃, and obtaining a rod-shaped organic eutectic material with the thickness of 30-35nm on the silicon dioxide side of the OTS modified silicon wafer, wherein the solvent is acetonitrile, and the concentration of the mixed solution is 1 mg/mL.
The donor molecule was 5, 7-dihydro-indolo [2,3-B ] carbazole, and donor molecule (5,7-ICZ) was purchased from tokyo chemical industries, ltd, and has the following structure:
the acceptor molecule is 2,2'- (benzo [1,2-B:4,5-B' ] dithiophene-4, 8-diylidene) dipropionitrile, and the acceptor molecule (DTTCNQ) is purchased from Shanghai Nature chemical Co., Ltd and has the following structure:
an optical microscopic image of the organic eutectic material in example 1 is shown in fig. 9, which shows that the organic eutectic material has a one-dimensional rod shape and a length of 0.5 to 10 mm.
Example 2
Example 1 the resulting organic eutectic material, which is 5, 7-dihydro-indolo [2,3-B ] carbazole-2, 2'- (benzo [1,2-B:4,5-B' ] dithiophene-4, 8-diyl) dipropionitrile (5, 7-ICZ-DTTCNQ), is prepared as shown in fig. 1, and is formed by self-assembling non-covalent bonds of donor molecules and acceptor molecules, wherein the ratio of donor molecules to acceptor molecules in the organic eutectic material is 1:1 in parts by weight of material.
The single crystal X-ray diffraction analysis shows that the organic eutectic material is monoclinic system and the space group is C1 2/c1The unit cell parameters of the organic eutectic material are as follows: 39.0513(7), 7.11710(10), 19.8653(3), 90 α, 90.130(2), 90 γ.
FIG. 2 shows UV-visible absorption spectra of 5,7-ICZ, DTTCNQ and 5, 7-ICZ-DTTCNQ (IDC in FIG. 2) in the solid state. As can be seen from fig. 2, the peak of the maximum absorption side band of the organic eutectic material 5, 7-ICZ-DTTCNQ in the solid state is 1180nm, and the corresponding optical band gap is 0.95eV (the optical band gap is calculated according to the formula Eg 1240/λ, where Eg is the optical band gap and λ is the boundary value of the ultraviolet absorption curve).
Example 3
In example 1, an organic eutectic material is used for an organic semiconductor layer (active layer) in a field effect transistor. The field effect transistor structure is shown in fig. 3, a silicon layer in the OTS modified silicon wafer is a gate electrode, a silicon dioxide layer of the OTS modified silicon wafer is an insulating layer, an organic semiconductor layer (eutectic in fig. 3) is on the insulating layer, and a source electrode and a drain electrode are on the organic semiconductor layer.
Method for preparing source and drain electrodes: pasting copper on OTS modified silicon waferThe screen is used as a mask plate, and the vacuum degree in a vapor deposition chamber is 10-6And (3) evaporating gold on the OTS modified silicon wafer as a source electrode and a drain electrode (the length-width ratio is 8: 1) under the conditions of torr and speed of 0.1nm/s, wherein the thicknesses of the source electrode and the drain electrode are respectively 120 nm. And after the evaporation is finished, uncovering the mask plate.
The source electrode and the drain electrode are transferred to the layered organic eutectic material in example 1 by a probe, and an organic field effect transistor (Si/SiO) with bottom-gate top contact can be constructed2/OTS/5,7-ICZ—DTTCNQ/Au)。
Fig. 4 and 5 are graphs of the transfer and output of a field effect transistor. Equation (i) is calculated using the following saturation region, and the mobility μ is calculated:
the mobility calculation method of formula (i) is detailed in organic field effect transistor in section 2 of the basic introduction of organic field effect transistor in chapter 2 of organic field effect transistor, author: huwenping, press: scientific press, ISBN 9787030320629.
The field effect transistor obtained by combining FIG. 4 and the above formula (I) has a mobility of 0.04cm2V · s, on-off ratio 107The threshold voltage is 3V, and the parameters show that the field effect transistor obtained by the organic eutectic material has good field effect performance, in addition, in the graph of FIG. 5, the current and the voltage are in a linear relation when the output curve is in a lower source-drain voltage range, and the current tends to be saturated along with the increase of the source-drain voltage; indicating that the source and drain electrodes have good contact quality with the organic semiconductor layer.
The near-infrared organic phototransistor can be constructed by irradiating the organic eutectic material 5, 7-ICZ-DTTCNQ with near-infrared light of 808nm, and FIG. 6 is a schematic structural diagram of the near-infrared organic phototransistor.
Fig. 7 is a transfer characteristic curve of a near-infrared organic phototransistor in the presence or absence of light, in which a curve in the direction indicated by an arrow indicates a state in which light is applied. In the near vicinity, compared with the dark conditionUnder the condition of infrared illumination (808nm), the source-drain current corresponding to the same grid voltage is increased, which shows that the device has good response to near-infrared light. Using the formula | Iphoto-Idark|/(SPi) The light responsivity (R) was calculated (reference: adv. mater.2020,32,1907791), it was found that the photoresponse (R) at different illumination intensities varies with the gate voltage (fig. 8). The curve in FIG. 8 shows that the optical responsivity of the device can reach 2923A/W, which indicates that the device has good response characteristics to near infrared light, and is beneficial to preparing high-performance phototransistors and application devices thereof, and further meets the application requirements of flexible wearable electronics.
The above results show that: the near-infrared organic photoelectric transistor with high performance can be prepared based on the organic eutectic material 5, 7-ICZ-DTTCNQ.
The invention has been described in an illustrative manner, and it is to be understood that any simple variations, modifications or other equivalent changes which can be made by one skilled in the art without departing from the spirit of the invention fall within the scope of the invention.
Claims (10)
1. An organic eutectic material is characterized in that the organic eutectic material is formed by self-assembly non-covalent bonds of donor molecules and acceptor molecules, wherein the donor molecules are 5, 7-dihydro-indolo [2,3-B ] carbazole, the acceptor molecules are 2,2'- (benzo [1,2-B:4,5-B' ] dithiophene-4, 8-diylidene) dipropionitrile, and the ratio of the donor molecules to the acceptor molecules is 1:1 according to the weight parts of substances.
2. The organic eutectic material of claim 1, wherein the organic eutectic material is 5, 7-dihydro-indolo [2,3-B ] carbazole-2, 2'- (benzo [1,2-B:4,5-B' ] dithiophene-4, 8-diylidene) dipropionitrile.
3. The organic eutectic material of claim 1, wherein the organic eutectic material is monoclinic and space group is C1 2/c1。
4. The organic eutectic material of claim 1, wherein the organic eutectic material has unit cell parameters of: 39.0513(7), 7.11710(10), 19.8653(3), 90 α, 90.130(2), 90 γ.
5. The organic eutectic material of claim 1, wherein the length of the organic eutectic material is 0.5-10 mm.
6. The method of preparing an organic eutectic material of claim 1, comprising the steps of:
and dissolving donor molecules and acceptor molecules in a solvent to obtain a mixed solution, keeping the temperature of the mixed solution constant at 80-130 ℃ until the donor molecules and the acceptor molecules are completely dissolved in the solvent, and volatilizing the solvent to obtain the organic eutectic material.
7. The preparation method according to claim 6, wherein the volatilization temperature is 20-25 ℃ at room temperature;
according to the weight parts of the substances, the ratio of the donor molecules to the acceptor molecules is 1: 1;
the solvent is acetonitrile, toluene and/or chlorobenzene;
the concentration of the mixed solution is 0.2-3.0 mg/mL;
the constant temperature time is 1-10 hours.
8. Use of an organic eutectic material in a field effect transistor according to any one of claims 1 to 5, wherein the organic eutectic material is used as an organic semiconductor layer in a field effect transistor.
9. Use according to claim 8, wherein the organic semiconductor layer is located on an insulating layer, and wherein an organic eutectic material is prepared as the organic semiconductor layer on the insulating layer with a thickness of 30-35 nm.
10. Use according to claim 9, characterised in that the current switching ratio of the field effect transistor is at most 107Exciting the field effect transistor by using light with wavelength of 808nm, wherein the highest light responsivity is 2923A/W;
the thickness of the source electrode and the drain electrode of the field effect transistor is 120-150 nm.
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| CN115215791A (en) * | 2022-09-02 | 2022-10-21 | 北京仿生界面科学未来技术研究院 | Solvent-free preparation method of organic eutectic material |
| CN116102460A (en) * | 2023-02-13 | 2023-05-12 | 天津大学 | Quaternary spectrum organic eutectic material based on tetracyano-terephthalquinone and application thereof in water evaporation |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115215791A (en) * | 2022-09-02 | 2022-10-21 | 北京仿生界面科学未来技术研究院 | Solvent-free preparation method of organic eutectic material |
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| CN116102460A (en) * | 2023-02-13 | 2023-05-12 | 天津大学 | Quaternary spectrum organic eutectic material based on tetracyano-terephthalquinone and application thereof in water evaporation |
| CN116102460B (en) * | 2023-02-13 | 2023-09-15 | 天津大学 | Quaternary spectrum organic eutectic material based on tetracyano-terephthalquinone and application thereof in water evaporation |
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