CN112201754B - Ultrathin crystalline continuous organic semiconductor film and preparation method and application thereof - Google Patents
Ultrathin crystalline continuous organic semiconductor film and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses an ultrathin crystalline continuous organic semiconductor film, a preparation method and application thereof, wherein the preparation method comprises the following steps: and dripping 10-20 mu l of semiconductor solution into the first base solution, standing to obtain a second base solution, vertically inserting the PTS modified carrier into the second base solution, and vertically pulling the PTS modified carrier upwards at the speed of 5-10um/s to obtain the ultrathin crystalline continuous organic semiconductor film on the surface of the PTS modified carrier, wherein the semiconductor solution is a mixture of a semiconductor and an organic solvent, the concentration of the semiconductor in the semiconductor solution is 0.5-1mg/mL, the first base solution is a mixture of tetrabutylammonium bromide and water, the concentration of the tetrabutylammonium bromide in the first base solution is 8-10mg/mL, and the organic solvent is toluene or chlorobenzene. The invention uses less organic semiconductor to generate large-area continuous semiconductor film, which can be applied to the preparation of large-area integrated circuit.
Description
Technical Field
The invention belongs to the technical field of organic semiconductors, and particularly relates to an ultrathin crystalline continuous organic semiconductor film, and a preparation method and application thereof.
Background
The two-dimensional organic single crystal semiconductor film combines the advantages of easy solution method preparation, flexibility, designable organic material structure, easy dissolution of organic material, less charge defect, higher photoelectric performance and the like, and the prepared organic single crystal semiconductor film plays an important role in the fields of organic field effect transistors, organic light emitting diodes, organic photodiodes, organic field effect waveguides, organic memristors and the like.
The dipping and pulling method is a method for growing a two-dimensional crystal film, and has the advantages of wide application, low price, simple operation, controllable crystal growth speed, capability of growing organic single crystals on a three-dimensional substrate and the like. Based on these advantages, the dip-coating method is widely used for growing crystal films. However, the continuous two-dimensional semiconductor thin film grown by the dip-coating method has some problems, which are as follows: first, a large amount of organic solution containing organic small molecule solute is needed in the dipping and pulling process, and the organic small molecule may have problems of small preparation amount or high price, and the like, thereby causing waste of the organic small molecule. Secondly, strips or dendrites are easy to grow in the pulling process. The stripe-shaped thin film has a certain directivity, and it is difficult to construct a large-area integrated circuit on a stripe or a dendritic thin film because the anisotropy of the thin film needs to be taken into consideration when constructing an integrated circuit on the thin film.
Disclosure of Invention
The invention aims to provide a preparation method of an ultrathin crystalline continuous organic semiconductor film, which takes water as a base solution and dropwise adds a small amount of semiconductor solution, namely, a double-phase pulling method is used for preparing the ultrathin crystalline continuous organic semiconductor film, namely, the semiconductor solution containing a small amount of semiconductors is dropwise added on the surface of water containing a surfactant, and after the solution is kept still for a period of time, the pulling speed of a pulling machine is controlled to pull out a carrier, so that small organic molecules are induced to grow into a large-area continuous organic semiconductor film on the surface of the carrier.
The purpose of the invention is realized by the following technical scheme.
A preparation method of an ultrathin crystalline continuous organic semiconductor film comprises the following steps: dropwise adding 10-20 mu l of semiconductor solution into the first base solution, standing for 8-9min to obtain a second base solution, vertically inserting a PTS modified carrier into the second base solution, and vertically lifting the PTS modified carrier upwards at a speed of 5-10um/s until the PTS modified carrier is removed from the second base solution, so as to obtain the ultrathin crystalline continuous organic semiconductor film on the surface of the PTS modified carrier, wherein the semiconductor solution is a mixture of a semiconductor and an organic solvent, the concentration of the semiconductor in the semiconductor solution is 0.5-1mg/mL, the first base solution is a mixture of tetrabutylammonium bromide (TBAB) and water, the concentration of the tetrabutylammonium bromide in the first base solution is 8-10mg/mL, and the organic solvent is toluene or chlorobenzene.
In the technical scheme, the ratio of the semiconductor solution to the first base solution is 1 (500-1000) by volume.
In the technical scheme, the semiconductor is dihexyl substituted-2, 6-diphenylanthracene (C6-DPA) or perylene.
In the above technical solution, the method for obtaining the PTS modified vector includes steps 1) to 2):
1) treating the carrier plasma for 10-15min under the vacuum degree of 0.3-0.4 mbar;
in the step 1), the carrier is a silicon wafer.
In the step 1), a plasma machine is used for carrying out plasma treatment on the carrier, and the power of the plasma machine is 75-85W when the carrier is subjected to the plasma treatment.
In the step 1), the method for realizing the vacuum degree comprises the following steps: and vacuumizing a sample bin for placing the carrier by using a plasma machine, and introducing oxygen into the sample bin until the vacuum degree in the sample bin is 0.3-0.4 mbar.
In the step 1), the carrier is cleaned before plasma treatment of the carrier: and (3) placing the carrier in deionized water for ultrasonic treatment for 8-10min, taking the carrier out of the deionized water, placing the carrier in acetone for ultrasonic treatment for 8-10min, taking the carrier out of the acetone, placing the carrier in isopropanol for ultrasonic treatment for 8-10min, and then blowing the carrier dry by nitrogen or inert gas.
2) Removing water in a carrier, placing the carrier in a container, dropping PTS (phenyl trimethoxy silane) on the container around the carrier, sealing the container, heating the container at 110-120 ℃ for 110-120min in a vacuum state, naturally cooling to room temperature of 20-25 ℃, taking out the carrier from the container, and cleaning the carrier to obtain the PTS modified carrier, wherein the ratio of the area part of the carrier, the volume part of the container and the volume part of the PTS is [ 1000-pi (100/2) ] 2 ]：π(100/2) 2 X 10 (0.5-1), wherein the unit of the area parts is mm 2 The unit of volume fraction and volume fraction is mm 3 ；
In the step 2), the operation of removing the moisture in the carrier is as follows: heating the carrier at 90-100 ℃ for 50-60min under vacuum.
In the step 2), the step of washing the carrier is: putting the carrier in n-hexane for ultrasonic treatment for 8-10 min; taking out the carrier from the normal hexane, and placing the carrier in chloroform for ultrasonic treatment for 8-10 min; and taking out the carrier from the trichloromethane, putting the carrier into isopropanol, carrying out ultrasonic treatment for 8-10min, and drying the carrier by using nitrogen or inert gas.
In the step 2), the container is a watch glass.
In the step 2), when the number of the carriers is multiple, the cross section of the container is circular, the multiple carriers are placed in the container along the circumferential direction, and the PTS is dripped on the container positioned at the circle center position among the multiple carriers.
The ultrathin crystalline continuous organic semiconductor film obtained by the preparation method.
In the above technical solution, the average number of Rq of the ultra-thin crystalline continuous organic semiconductor thin film is 0.38nm and the average number of Ra is 0.24 nm.
The application of the ultrathin crystalline continuous organic semiconductor film in an organic field effect transistor.
In the technical scheme, the average value of the mobility of the organic field effect transistor made of the ultrathin crystalline continuous organic semiconductor film is 1.14cm 2 (iv)/Vs, maximum value 1.45cm 2 /Vs。
The invention has the following beneficial effects:
the invention uses less organic semiconductor to generate large-area continuous semiconductor film, which can be applied to the preparation of large-area integrated circuit. The ultrathin crystalline continuous organic semiconductor film prepared by the invention is a large-area continuous organic semiconductor film, so that anisotropy does not exist, and an integrated circuit can be randomly arranged on the ultrathin crystalline continuous organic semiconductor film.
Drawings
FIG. 1 is a schematic view of a production process of the present invention;
FIG. 2 is a molecular formula of a material used in the present invention, wherein FIG. a is C6-DPA, FIG. b is perylene, and FIG. C is TBAB;
FIG. 3 is a schematic view of a microscope of the ultra-thin crystalline continuous organic semiconductor thin film obtained in example 1;
FIG. 4 is a schematic view of a microscope of the ultra-thin crystalline continuous organic semiconductor thin film obtained in example 2;
FIG. 5 is a schematic view of a microscope of the ultra-thin crystalline continuous organic semiconductor thin film obtained in example 3;
FIG. 6 is a schematic microscopic view of the product obtained in comparative example 3;
FIG. 7 is a schematic microscopic view of the product obtained in comparative example 4;
FIG. 8 is a schematic microscopic view of the product obtained in comparative example 5;
FIG. 9 is a schematic microscopic view of the product obtained in comparative example 6;
FIG. 10 is a schematic view of a microscope of a product obtained in comparative example 7;
FIG. 11 is a schematic microscopic view of the product obtained in comparative example 8;
FIG. 12 is a schematic view under a microscope of a product obtained in comparative example 9;
FIG. 13 is an XRD representation of the ultra-thin crystalline continuous organic semiconductor film obtained in example 3;
FIG. 14 is an AFM characterization picture of an ultra-thin crystalline continuous organic semiconductor thin film;
FIG. 15 is a graph showing electrical characteristics of an organic field effect transistor formed from an ultra-thin crystalline continuous organic semiconductor thin film;
FIG. 16 is a schematic microscopic view, FIG. 16a is a schematic microscopic view of a product obtained in comparative example 10, and FIG. 16b is a schematic microscopic view of an ultra-thin crystalline continuous organic semiconductor thin film obtained in example 4;
fig. 17 is a schematic view of a microscope.
Detailed Description
The technical scheme of the invention is further explained by combining specific examples.
The main experimental materials in the following examples
Example Main test Equipment
| Device name | Model number | Origin of |
|
| 1 | Polarizing microscope | Nikon OptiPlex 3046 | Japanese |
| 2 | Atomic force microscope | Dimension Icon | Chinese Beijing |
| 3 | X-ray diffractometer | PANalytical/Empyrean | The Netherlands |
| 4 | Probe station | Keithley 4200 | Chinese Beijing |
| 5 | Constant-temperature type dipping pulling film coating machine | SYDC-100H | Shanghai, China |
| 6 | Plasma cleaning machine | Diener ZEPTO | Shanghai, China |
| 7 | Numerical control ultrasonic cleaner | KQ5200DE | Chinese Kunshan |
| 8 | Electrothermal blowing dry box | DH-101 | Tianjin of China |
| 9 | Contact angle measuring instrument | OCA100 | Germany |
| 10 | Transmission electron microscope | JEOL JEM-2010 | Japanese language |
The following carrier is a silicon wafer (SiO) of 8mm × 10mm size 2 (300nm)/Si), during cleaning, the silicon wafer is put on a washing basket, and then the silicon wafer and the washing basket are put into a 250mL beaker together, and the beaker is put into an ultrasonic machine.
In step 2), when the number of the carriers is multiple, the cross section of the container is circular, the multiple carriers are placed in the container along the circumferential direction, and the PTS is dripped on the container positioned at the circle center position among the multiple carriers.
Deionized water is used as water.
The preparation method of the silicon chip with the hydrophilic surface and the distributed hydroxyl groups comprises the following steps: preparing a silicon wafer as a carrier, placing the carrier in deionized water for ultrasonic treatment for 10min, taking out the carrier from the deionized water, placing the carrier in acetone for ultrasonic treatment for 10min, taking out the carrier from the acetone, placing the carrier in isopropanol for ultrasonic treatment for 10min, taking out the carrier, and then drying the carrier by using nitrogen. Placing the carrier in a sample chamber of a plasma machine, opening a vacuum switch of the plasma machine, vacuumizing the sample chamber for 10min, introducing oxygen into the sample chamber until the vacuum degree in the sample chamber is 0.4mbar, and keeping the vacuum degree for 10 min. Adjusting the power of a plasma machine to 80W, starting a generator, treating carrier plasma for 10min by using the plasma machine with white light appearing in a sample bin as a time starting point, and taking out to obtain the silicon wafer with the hydrophilic surface fully distributed with hydroxyl groups.
Examples 1 to 3
A preparation method of an ultrathin crystalline continuous organic semiconductor film comprises the following steps: and (3) dripping 20 mul of semiconductor solution into the first base solution, standing for 8min to obtain a second base solution, wherein the ratio of the semiconductor solution to the first base solution is 1:1000 according to parts by volume. Vertically inserting the PTS modified carrier into a second base solution until the PTS modified carrier is completely immersed, and vertically pulling the PTS modified carrier upwards at a speed of V um/s until the PTS modified carrier is removed from the second base solution, so as to obtain the ultrathin crystalline continuous organic semiconductor film on the surface of the PTS modified carrier, wherein the semiconductor solution is a mixture of dihexyl substituted-2, 6-diphenylanthracene (C6-DPA) and an organic solvent, the concentration of the dihexyl substituted-2, 6-diphenylanthracene in the semiconductor solution is 1mg/mL, the first base solution is a mixture of tetrabutylammonium bromide (TBAB) and water, the concentration of the tetrabutylammonium bromide in the first base solution is 10mg/mL, and the tetrabutylammonium bromide is a surfactant, so that the interfacial tension can be reduced, and the spreading of the semiconductor solution on the water surface is promoted.
The method for obtaining the PTS modified vector comprises the steps 1) to 2):
1) and (3) cleaning the carrier: preparing a silicon wafer as a carrier, placing the carrier in deionized water for ultrasonic treatment for 10min, taking out the carrier from the deionized water, placing the carrier in acetone for ultrasonic treatment for 10min, taking out the carrier from the acetone, placing the carrier in isopropanol for ultrasonic treatment for 10min, taking out the carrier, and then drying the carrier by using nitrogen.
Placing the carrier in a sample chamber of a plasma machine, opening a vacuum switch of the plasma machine, vacuumizing the sample chamber for 10min, introducing oxygen into the sample chamber until the vacuum degree in the sample chamber is 0.4mbar, and keeping for 10 min. Adjusting the power of the plasma machine to 80W, turning on a generator, treating the carrier plasma for 10min by using the plasma machine with the white light appearing in the sample bin as a time starting point, and taking out the carrier. The plasma treatment can oxidize the adsorbed organic substances remaining on the surface of the carrier to expose a clean surface and generate Si — OH.
2) Heating the carrier at 90 deg.C for 60min under vacuum for removing water, and placing the carrier in a container, which is a watch glass. Dropping PTS on a container around the carrier, sealing the container, placing the container in a drying oven, heating the drying oven at 120 ℃ for 120min in a vacuum state, naturally cooling to room temperature of 20-25 ℃, taking out the carrier from the container, and cleaning the carrier to obtain the PTS modified carrier, wherein the ratio of the area parts of the carrier, the volume parts of the container and the volume parts of the PTS is 1000: pi (100/2) 2 X 10:0.5, unit of area fraction is mm 2 Volume fraction and volume fraction are in mm 3 (ii) a The step of cleaning the carrier in the step 2) is as follows: putting the carrier in n-hexane for ultrasonic treatment for 10 min; taking out the carrier from the normal hexane, and putting the carrier in chloroform for ultrasonic treatment for 10 min; and taking out the carrier from the trichloromethane, putting the carrier into isopropanol, performing ultrasonic treatment for 10min, taking out the carrier, and drying by using nitrogen or inert gas.
In the above examples, V and the organic solvent are shown in Table 1.
TABLE 1
Comparative examples 1 to 7
A method of making, comprising: and (3) dropwise adding 20 mu l of semiconductor solution into the first base solution, standing for T min to obtain a second base solution, wherein the ratio of the semiconductor solution to the first base solution is 1:1000 in parts by volume. And vertically inserting the PTS modified carrier into the second base solution until the PTS modified carrier is completely immersed, vertically pulling the PTS modified carrier upwards at a speed of V um/s until the PTS modified carrier is removed from the second base solution, and testing the surface of the PTS modified carrier, wherein the testing results are shown in table 2, the semiconductor solution is a mixture of dihexyl substituted-2, 6-diphenylanthracene (C6-DPA) and an organic solvent, the concentration of the dihexyl substituted-2, 6-diphenylanthracene in the semiconductor solution is 1mg/mL, the first base solution is a mixture of tetrabutylammonium bromide (TBAB) and water, the concentration of the tetrabutylammonium bromide in the first base solution is 10mg/mL, and the tetrabutylammonium bromide is a surfactant, so that the interface tension can be reduced, and the spreading of the semiconductor solution on the water surface can be promoted.
The method for obtaining the PTS modified vector comprises the steps 1) to 2):
1) and (3) cleaning the carrier: preparing a silicon wafer as a carrier, placing the carrier in deionized water for ultrasonic treatment for 10min, taking out the carrier from the deionized water, placing the carrier in acetone for ultrasonic treatment for 10min, taking out the carrier from the acetone, placing the carrier in isopropanol for ultrasonic treatment for 10min, taking out the carrier, and then drying the carrier by using nitrogen.
Placing the carrier in a sample chamber of a plasma machine, opening a vacuum switch of the plasma machine, vacuumizing the sample chamber for 10min, introducing oxygen into the sample chamber until the vacuum degree in the sample chamber is 0.4mbar, and keeping for 10 min. Adjusting the power of the plasma machine to 80W, turning on a generator, treating the carrier plasma for 10min by using the plasma machine with the white light appearing in the sample bin as a time starting point, and taking out the carrier. The plasma treatment can oxidize the adsorbed organic matter remaining on the surface of the carrier to expose a clean surface and generate Si — OH.
2) Heating the carrier at 90 deg.C for 60min under vacuum for removing water, and placing the carrier in a container, which is a watch glass. Dropping PTS on a container around the carrier, sealing the container, placing the container in a drying oven, heating the drying oven at 120 ℃ for 120min in a vacuum state, naturally cooling to room temperature of 20-25 ℃, taking out the carrier from the container, and cleaning the carrier to obtain the PTS modified carrier, wherein the ratio of the area parts of the carrier, the volume parts of the container and the volume parts of the PTS is 1000: pi (100/2) 2 X 10:0.5, unit of area fraction is mm 2 Volume fraction and volume fraction are in mm 3 (ii) a The step of cleaning the carrier in the step 2) is as follows: putting the carrier in n-hexane for ultrasonic treatment for 10 min; taking out the carrier from the normal hexane, and putting the carrier in chloroform for ultrasonic treatment for 10 min; and taking out the carrier from the trichloromethane, putting the carrier into isopropanol, performing ultrasonic treatment for 10min, taking out the carrier, and drying by using nitrogen or inert gas.
In the above examples, V, T, organic solvents, and test results are shown in Table 2.
TABLE 2
Comparative example 8
A method, comprising: preparing a silicon wafer as a carrier, placing the carrier in deionized water for 10min by ultrasound, taking out the carrier from the deionized water, placing the carrier in acetone for 10min by ultrasound, taking out the carrier from the acetone, placing the carrier in isopropanol for 10min by ultrasound, taking out the carrier, and then blowing the carrier by nitrogen for drying.
And (3) dripping 20 mul of semiconductor solution into the first base solution, standing for 8min to obtain a second base solution, wherein the ratio of the semiconductor solution to the first base solution is 1:1000 according to parts by volume. And vertically inserting a carrier into the second base liquid until the carrier is completely immersed, and vertically pulling the carrier upwards at a speed of 10um/s until the carrier is removed from the second base liquid, wherein no substances are deposited on the surface of the carrier, the semiconductor solution is a mixture of dihexyl substituted-2, 6-diphenylanthracene (C6-DPA) and an organic solvent, the organic solvent is chlorobenzene, the concentration of the dihexyl substituted-2, 6-diphenylanthracene in the semiconductor solution is 1mg/mL, the first base liquid is a mixture of tetrabutylammonium bromide (TBAB) and water, the concentration of the tetrabutylammonium bromide in the first base liquid is 10mg/mL, and the tetrabutylammonium bromide is a surfactant, so that the interfacial tension can be reduced, and the spreading of the semiconductor solution on the water surface can be promoted.
Comparative example 9
A method, comprising: and (3) dropwise adding 20 mu l of semiconductor solution into the first base solution, and standing for 8min to obtain a second base solution, wherein the ratio of the semiconductor solution to the first base solution is 1:1000 in parts by volume. Preparing a silicon wafer with hydrophilic surface and full of hydroxyl groups as a carrier, vertically inserting the carrier into a second base solution until the carrier is completely immersed, vertically pulling the carrier upwards at the speed of 10 mu m/s until the carrier is removed from the second base solution, obtaining a square organic semiconductor crystal film on the surface of the carrier, the semiconductor solution is a mixture of dihexyl substituted-2, 6-diphenyl anthracene (C6-DPA) and an organic solvent, the organic solvent is chlorobenzene, the concentration of the dihexyl substituted-2, 6-diphenyl anthracene in the semiconductor solution is 1mg/mL, the first base solution is a mixture of tetrabutylammonium bromide (TBAB) and water, the concentration of the tetrabutylammonium bromide in the first base solution is 10mg/mL, and the tetrabutylammonium bromide is a surfactant, so that the interfacial tension can be reduced, and the semiconductor solution can be promoted to spread on a water surface.
FIG. 1 is a schematic view of the preparation method of the present invention, wherein the upper diagram is an enlarged schematic view of the pulling process, and the rest is a schematic view of the whole experimental process.
FIG. 2 shows the molecular formula of the chemical molecules used in the present invention, FIG. 2a shows dihexyl substituted-2, 6-diphenylanthracene (C6-DPA), FIG. 2b shows the organic semiconductor perylene, and FIG. 2C shows the molecular formula of tetrabutylammonium bromide (TBAB) as a surfactant.
The ultra-thin crystalline continuous organic semiconductor films obtained in the above examples 1 to 3 and the products obtained in the above comparative examples were tested, and the specific test results were as follows:
FIG. 3 is a schematic view of a microscope (photographed by a Nikon OptiPlex 3046 polarizing microscope) of the ultrathin crystalline continuous organic semiconductor film obtained in example 1. Wherein, fig. 3a and fig. 3b are the topography of the ultra-thin crystalline continuous organic semiconductor thin film obtained in example 1, and it can be known that the ultra-thin crystalline continuous organic semiconductor thin film obtained in example 1 is a large-area continuous organic thin film. Fig. 3c and 3d are polarization microscope pictures of the ultra-thin crystalline continuous organic semiconductor film obtained in example 1, fig. 3c is a photograph taken when the ultra-thin crystalline continuous organic semiconductor film is horizontally placed at an angle of 0 degree, and fig. 3d is a photograph taken when the ultra-thin crystalline continuous organic semiconductor film is horizontally rotated at an angle of 45 degrees, and it can be seen that there is an obvious change in brightness, which indicates that the ultra-thin crystalline continuous organic semiconductor film is a whole piece of film with uniform orientation.
FIG. 4 is a schematic view of a microscope (photographed by using a Nikon OptiPlex 3046 polarizing microscope) of the ultra-thin crystalline continuous organic semiconductor film obtained in example 2. Wherein, fig. 4a and 4b are the morphology diagrams of the ultra-thin crystalline continuous organic semiconductor thin film obtained in example 2, and it can be seen from the diagrams that the ultra-thin crystalline continuous organic semiconductor thin film obtained in example 2 forms a continuous organic thin film with a large area. Fig. 4c and 4d are polarization microscope pictures of the ultra-thin crystalline continuous organic semiconductor film obtained in example 2, fig. 4c is a photograph taken when the ultra-thin crystalline continuous organic semiconductor film is horizontally placed at an angle of 0 degree, and fig. 4d is a photograph taken when the ultra-thin crystalline continuous organic semiconductor film is horizontally rotated at an angle of 45 degrees, and it can be seen that there is an obvious change in brightness, which indicates that the ultra-thin crystalline continuous organic semiconductor film is a whole piece of film with uniform orientation. Fig. 4e and fig. 4f are the morphology diagrams obtained by observing the ultrathin crystalline continuous organic semiconductor film in a large area, respectively, and it can be seen from the diagrams that the film coverage is high.
FIG. 5 is a schematic view of a microscope (photographed by a Nikon OptiPlex 3046 polarizing microscope) of the ultrathin crystalline continuous organic semiconductor film obtained in example 3. Wherein, fig. 5a and 5b are the topography of the ultra-thin crystalline continuous organic semiconductor thin film obtained in example 3, and it can be seen from the topography that the ultra-thin crystalline continuous organic semiconductor thin film obtained in example 3 forms a large-area continuous organic thin film. Fig. 5c and 5d are polarization microscope pictures of the ultra-thin crystalline continuous organic semiconductor film obtained in example 3, fig. 5c is a photograph taken when the ultra-thin crystalline continuous organic semiconductor film is horizontally placed at an angle of 0 degree, and fig. 5d is a photograph taken when the ultra-thin crystalline continuous organic semiconductor film is horizontally rotated at an angle of 45 degrees, and it can be seen that there is an obvious change in brightness, which indicates that the ultra-thin crystalline continuous organic semiconductor film is a whole piece of film with uniform orientation.
The PTS modified carriers obtained in comparative examples 1 and 2 were tested for no deposition on the surface.
FIG. 6 is a schematic microscope image of the product obtained in comparative example 3 (photographed using a Nikon OptiPlex 3046 polarizing microscope). Wherein, fig. 6a is a topography view of a certain portion of the product obtained in comparative example 3, and fig. 6c is a close-up enlarged view of fig. 6a, it can be seen that the product obtained in example 3 does not form a continuous organic semiconductor thin film but scatters spots on the surface of the carrier sporadically. Fig. 6b is another topographical view of the product obtained in comparative example 3, and fig. 6d is a close-up view of fig. 6b, in which it can be seen that the product obtained in comparative example 3 does not form a continuous organic semiconductor thin film here, but the organic semiconductor is not sufficiently spread and deposited stacked on the support surface.
FIG. 7 is a schematic microscopic view of the product obtained in comparative example 4 (photographed using a Nikon OptiPlex 3046 polarizing microscope). Wherein, fig. 7a is a topography view of a certain part of the product obtained in the comparative example 4, and fig. 7c is a close-up enlarged view of fig. 7a, and it can be seen that the product obtained in the comparative example 4 does not form a continuous organic semiconductor thin film, but a thick platelet film which is not completely covered. Fig. 7b is another topographical view of the product obtained in comparative example 4, and fig. 7d is a close-up view of fig. 7b, from which it can be seen that the product obtained in comparative example 4 does not form a continuous organic semiconductor thin film here, but the organic semiconductor is not sufficiently spread out, deposited on the support and deposited thickly.
FIG. 8 is a schematic view of the morphology of the product obtained in comparative example 5 (photographed using a Nikon OptiPlex 3046 polarizing microscope and a JEOL JEM-2010 transmission electron microscope SEM). Wherein, fig. 8a is a topography map of a certain part of the product obtained in the comparative example 5, fig. 8b is a close-up enlarged view of fig. 8a, and fig. 8c is a topography map of the part photographed by SEM, and it can be known that the product obtained in the comparative example 5 does not form a continuous organic semiconductor film here, but forms a stripe-like organic semiconductor film covering the substrate in a dendritic form. Fig. 8d is a schematic diagram of a certain portion of the product obtained in comparative example 5, fig. 8e is a close-up enlarged view of fig. 8d, and fig. 8f is a schematic diagram of the topography of the portion photographed by SEM, and it can be seen that the product obtained in comparative example 5 does not form a continuous organic semiconductor thin film here, but covers the disc-like scattered organic semiconductor on the carrier.
FIGS. 9a and 9b are the topographical maps of the product obtained in comparative example 6, in which ribbon-like crystals, rather than a continuous organic semiconductor thin film, are obtained on a support.
FIGS. 10a and 10b are topographical maps of the product obtained in comparative example 7, in which the organic semiconductor thin film was obtained on the support with low coverage.
FIGS. 11a and 11b are the topographical maps generated for the product obtained in comparative example 8, which shows that no material is generated on the support.
FIG. 12 is a microscope photograph of the product obtained in comparative example 9 (photographed using a Nikon OptiPlex 3046 polarizing microscope). In which fig. 12a and 12b are topographical views of the product obtained in comparative example 9, and it can be seen that the product obtained in comparative example 9 does not form a continuous organic semiconductor thin film, but is dispersed plate-like crystals. Fig. 12c and 12d are polarization microscope pictures of the product obtained in comparative example 9, fig. 12c is a photograph of the product obtained in comparative example 9 taken at a horizontal angle of 0 degrees, and fig. 12d is a photograph of the product obtained in comparative example 9 taken at a horizontal rotation angle of 45 degrees, and a clear change in brightness is observed, indicating that flaky crystals are formed, respectively.
Fig. 13 is an XRD characterization of the ultra-thin crystalline continuous organic semiconductor film obtained in example 3, which shows that the peak position is about 3 ° and the peak shape is good.
FIGS. 14a and 14b are AFM test charts (tested using a Dimension Icon atomic force microscope) of the ultra-thin crystalline continuous organic semiconductor thin film obtained in example 3. As can be seen from fig. 14a, the height difference between the layers is about 3.0nm, which is the height of a single layer of molecules, and the surface roughness R of the frame-out portion is 0.36nm, so that the surface of the ultra-thin crystalline continuous organic semiconductor thin film obtained in example 3 is atomically flat. FIG. 14b is an AFM graph of the thickness difference between single, double and single double layers of the ultra-thin crystalline continuous organic semiconductor thin film obtained in example 3. Firstly, the thickness difference of a monomolecular layer is 3.085nm, secondly, the thickness difference of a bilayer is 6.462nm, and thirdly, the thickness difference between the bilayer and the monolayer is 3.029nm, and the thickness difference is about one molecular layer.
The carrier loaded with the ultrathin crystalline continuous organic semiconductor film is made into an organic field effect transistor, and the preparation method of the organic field effect transistor comprises the following steps: first, a support loaded with an ultra-thin crystalline continuous organic semiconductor thin film was placed on a Keithley4200 probe station, and two gold films (length 210 μm × width 38 μm, thickness 150nm) prepared in the previous stage were transferred onto the ultra-thin crystalline continuous organic semiconductor thin film using a probe, and the two gold films were placed in parallel in the "═ form. The gold films function as voltage electrodes and as a source electrode and a drain electrode (any one of the gold films is the source electrode, and the other gold film is the drain electrode).
Fig. 15 shows performance tests of the organic field effect transistor made of the ultra-thin crystalline continuous organic semiconductor thin film (relevant tests performed by Keithley4200 probe station). Fig. 15a is a transfer characteristic curve of an organic field effect transistor prepared from the ultra-thin crystalline continuous organic semiconductor thin film obtained in example 1, and fig. 15b is an output characteristic curve of the organic field effect transistor. The mobility maximum value can be calculated to be 0.03.cm 2 Vs, average at 0.01cm 2 and/Vs.
Fig. 15c is a transfer characteristic curve of an organic field effect transistor prepared from the ultra-thin crystalline continuous organic semiconductor thin film obtained in example 3, and fig. 15d is an output characteristic curve of the organic field effect transistor. The mobility maximum value can be calculated to reach 1.45.cm through calculation 2 Vs, average at 1.14cm 2 It can be seen that the mobility of the films produced in the toluene solution is somewhat higher than in the chlorobenzene solution.
Example 4
A preparation method of an ultrathin crystalline continuous organic semiconductor film comprises the following steps: and (3) dripping 20 mul of semiconductor solution into the first base solution, standing for 8min to obtain a second base solution, wherein the ratio of the semiconductor solution to the first base solution is 1:1000 according to parts by volume. Vertically inserting the PTS modified carrier into a second base solution until the PTS modified carrier is completely immersed, then vertically pulling the PTS modified carrier upwards at a speed of 10um/s until the PTS modified carrier is removed from the second base solution, and obtaining the ultrathin crystalline continuous organic semiconductor film on the surface of the PTS modified carrier, wherein the semiconductor solution is a mixture of perylene and an organic solvent, the concentration of perylene in the semiconductor solution is 1mg/mL, the organic solvent is toluene, the first base solution is a mixture of tetrabutylammonium bromide (TBAB) and water, the concentration of tetrabutylammonium bromide in the first base solution is 10mg/mL, and the tetrabutylammonium bromide is a surfactant, so that the interfacial tension can be reduced, and the semiconductor solution is promoted to spread on the water surface.
The method for obtaining the PTS modified vector comprises the steps 1) to 2):
1) and (3) cleaning the carrier: preparing a silicon wafer as a carrier, placing the carrier in deionized water for 10min by ultrasound, taking out the carrier from the deionized water, placing the carrier in acetone for 10min by ultrasound, taking out the carrier from the acetone, placing the carrier in isopropanol for 10min by ultrasound, taking out the carrier, and then blowing the carrier by nitrogen for drying.
Placing the carrier in a sample chamber of a plasma machine, opening a vacuum switch of the plasma machine, vacuumizing the sample chamber for 10min, introducing oxygen into the sample chamber until the vacuum degree in the sample chamber is 0.4mbar, and keeping for 10 min. Adjusting the power of the plasma machine to 80W, turning on a generator, treating the carrier plasma for 10min by using the plasma machine with the white light appearing in the sample bin as a time starting point, and taking out the carrier. The plasma treatment can oxidize the adsorbed organic matter remaining on the surface of the carrier to expose a clean surface and generate Si — OH.
2) Heating the carrier at 90 deg.C for 60min under vacuum for removing water, and placing the carrier in a container, which is a watch glass. Dropping PTS on a container around the carrier, sealing the container, placing the container in a drying oven, heating the drying oven at 120 ℃ for 120min in a vacuum state, naturally cooling to room temperature of 20-25 ℃, taking out the carrier from the container, and cleaning the carrier to obtain the PTS modified carrier, wherein the area fraction of the carrier and the volume of the containerThe ratio of parts to PTS parts by volume is 1000: pi (100/2) 2 X 10:0.5, unit of area fraction is mm 2 Volume fraction and volume fraction are in mm 3 (ii) a The step of cleaning the carrier in the step 2) is as follows: putting the carrier in n-hexane for ultrasonic treatment for 10 min; taking out the carrier from the normal hexane, and putting the carrier in chloroform for ultrasonic treatment for 10 min; and taking out the carrier from the trichloromethane, putting the carrier into isopropanol, performing ultrasonic treatment for 10min, taking out the carrier, and drying by using nitrogen or inert gas.
COMPARATIVE EXAMPLE 10 (traditional Single phase Czochralski method)
A method, comprising: the PTS modified carrier in example 3 is vertically inserted into 8mL of semiconductor solution until the PTS modified carrier is completely immersed, and then the PTS modified carrier is vertically pulled up to the PTS modified carrier at a speed of 10um/s and removed from the semiconductor solution, wherein the semiconductor solution is a mixture of perylene and an organic solvent, the organic solvent is toluene, and the concentration of perylene in the semiconductor solution is 1 mg/mL.
COMPARATIVE EXAMPLE 11 (traditional Single-phase Czochralski method)
A method, comprising: the PTS modified carrier in example 3 was vertically inserted into 8mL of semiconductor solution until the PTS modified carrier was completely immersed, and then the PTS modified carrier was vertically pulled up to the PTS modified carrier at a speed of 10um/s and removed from the semiconductor solution, wherein the semiconductor solution was a mixture of dihexyl-substituted-2, 6-diphenylanthracene (C6-DPA) and an organic solvent, the organic solvent was toluene, and the concentration of dihexyl-substituted-2, 6-diphenylanthracene in the semiconductor solution was 1 mg/mL.
FIG. 16 is a schematic drawing of a microscope (taken using a Nikon OptiPlex 3046 polarizing microscope). Wherein, FIG. 16a is the topography of the product obtained in comparative example 10, which results in dendritic crystal stripes, and FIG. 16b is the topography of the ultra-thin crystalline continuous organic semiconductor film obtained in example 4, which results in a relatively spread organic field effect film.
FIG. 17 is a schematic microscope image of the product obtained in comparative example 11 (photographed using a Nikon OptiPlex 3046 polarizing microscope). In which fig. 17a and 17b obtain a crystalline continuous organic semiconductor film having irregular or dendritic or round shape instead of ultra-thin.
As can be seen from fig. 16 and 17, in the conventional single-phase pulling method, an ultra-thin crystalline continuous organic semiconductor film cannot be obtained, and most of the ultra-thin crystalline continuous organic semiconductor film has a dendritic, strip-shaped or disc-shaped morphology, which cannot be applied and popularized better; the invention adopts double-phase lifting, and the preparation method can obtain the ultrathin crystalline continuous organic semiconductor film, the thickness is in the nanometer level, the appearance is uniform and smooth, and the preparation method is beneficial to industrial production and preparation.
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 (7)
1. A method for preparing an ultrathin crystalline continuous organic semiconductor film is characterized by comprising the following steps: dripping 10-20 μ l of semiconductor solution into the first base solution, standing for 8-9min to obtain a second base solution, and vertically inserting phenyltrimethoxysilane modified carrier
Putting the phenyltrimethoxysilane modified carrier into the second base solution, and vertically pulling the phenyltrimethoxysilane modified carrier upwards at a speed of 5-10um/s until the phenyltrimethoxysilane modified carrier is removed from the second base solution, so as to obtain the ultrathin crystalline continuous organic semiconductor film on the surface of the phenyltrimethoxysilane modified carrier, wherein the semiconductor solution is a mixture of a semiconductor and an organic solvent, the concentration of the semiconductor in the semiconductor solution is 0.5-1mg/mL, the first base solution is a mixture of tetrabutylammonium bromide and water, the concentration of the tetrabutylammonium bromide in the first base solution is 8-10mg/mL, and the organic solvent is toluene or chlorobenzene;
wherein the ratio of the semiconductor solution to the first base solution is 1 (500-1000) in parts by volume;
the semiconductor is dihexyl substituted-2, 6-diphenyl anthracene or perylene;
the method for obtaining the phenyltrimethoxysilane modified carrier comprises the following steps 1) to 2):
1) treating the carrier plasma at vacuum degree of 0.3-0.4mbar for 10-15 min;
2) removing water in the carrier, placing the carrier in a container, dripping phenyltrimethoxysilane on a container around the carrier, sealing the container, heating the container at 110-120 ℃ for 120min under a vacuum state, naturally cooling to room temperature of 20-25 ℃, taking out the carrier from the container, and cleaning the carrier to obtain the phenyltrimethoxysilane modified carrier, wherein the ratio of the area part of the carrier, the volume part of the container and the volume part of the phenyltrimethoxysilane is [ 1000-pi (100/2) 2 ]：π(100/2) 2 X 10 (0.5-1), wherein the unit of the area parts is mm 2 The volume parts and the volume parts are in mm 3 。
2. The production method according to claim 1, wherein, in the step 1), the support is a silicon wafer;
in the step 1), carrying out plasma treatment on the carrier by using a plasma machine, wherein the power of the plasma machine is 75-85W when the carrier is subjected to the plasma treatment;
in the step 1), the method for realizing the vacuum degree comprises the following steps: vacuumizing a sample bin for placing the carrier by using a plasma machine, and introducing oxygen into the sample bin until the vacuum degree in the sample bin is 0.3-0.4 mbar;
in the step 1), the carrier is cleaned before plasma treatment of the carrier: putting the carrier into deionized water, performing ultrasonic treatment for 8-10min, taking out the carrier from the deionized water, putting the carrier into acetone, performing ultrasonic treatment for 8-10min, taking out the carrier from the acetone, putting the carrier into isopropanol, performing ultrasonic treatment for 8-10min, and drying the carrier by nitrogen or inert gas.
3. The method according to claim 2, wherein in the step 2), the operation of removing moisture from the carrier is: heating the carrier at 90-100 deg.C for 50-60min under vacuum;
in the step 2), the step of washing the carrier is: putting the carrier in n-hexane for ultrasonic treatment for 8-10 min;
taking out the carrier from the normal hexane, and placing the carrier in chloroform for ultrasonic treatment for 8-10 min; taking out the carrier from the trichloromethane, placing the carrier in isopropanol, performing ultrasonic treatment for 8-10min, and drying the carrier by using nitrogen or inert gas, wherein in the step 2), the container is a watch glass;
in the step 2), when the number of the carriers is multiple, the cross section of the container is circular, the multiple carriers are placed in the container along the circumferential direction, and the phenyltrimethoxysilane is dripped on the container at the position of the center of a circle between the multiple carriers.
4. The ultra-thin crystalline continuous organic semiconductor thin film obtained by the production method according to any one of claims 1 to 3.
5. The ultra-thin crystalline continuous organic semiconductor film of claim 4, wherein the ultra-thin crystalline continuous organic semiconductor film has an average number of Rq's of 0.38nm and an average number of Ra's of 0.24 nm.
6. Use of the ultra-thin crystalline continuous organic semiconductor thin film obtained by the preparation method according to any one of claims 1 to 3 in an organic field effect transistor.
7. Use according to claim 6, wherein the mobility of the organic field effect transistor made of the ultra-thin crystalline continuous organic semiconductor thin film has an average value of 1.14cm 2 Vs, maximum 1.45cm 2 /Vs。
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