CN112599676A - Organic ammonium salt p-type dopant - Google Patents
Organic ammonium salt p-type dopant Download PDFInfo
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Abstract
The invention discloses an organic ammonium salt as a p-type dopant and application thereof in an organic semiconductor photoelectric device. Such a p-type dopant may p-dope the acceptor material by blending with the acceptor material or exposing the acceptor material to a vapor of the p-type dopant. The doping agent added into the p-type semiconductor can improve the properties of the organic semiconductor such as conductivity, hole mobility and the like, so that the doping agent can be applied to the fields of organic light-emitting diodes, organic field effect transistors, organic solar cells, perovskite solar cells and the like.
Description
Technical Field
The invention belongs to the field of organic semiconductor devices, and particularly relates to an organic ammonium salt p-type dopant and application thereof in the field of organic semiconductor photoelectric devices.
Background
Organic semiconductors have been widely studied and applied in the field of organic photoelectric devices such as organic light emitting diodes, organic field effect transistors, organic solar cells, and perovskite solar cells in recent years due to their advantages of solution processability, flexibility, and light weight. However, the carrier mobility and conductivity of organic semiconductors are relatively low compared to inorganic semiconductors, which greatly limits the performance of organic semiconductor optoelectronic devices.
The carrier mobility and the conductivity of the organic semiconductor can be greatly improved by doping the organic semiconductor, so that the performance of the organic photoelectric device is remarkably improved. Currently, the number of p-type semiconductors in organic semiconductors is large, and the number of dopants capable of realizing p-type doping is small compared to the number of p-type organic semiconductors. These dopants have good solubility properties to meet solution processable conditions while achieving high doping efficiencies with a low cost of a few p-type dopants. Therefore, the development of a novel p-dopant is of great significance for realizing high-performance organic semiconductor photoelectric devices and reducing the preparation cost thereof.
Disclosure of Invention
In order to realize efficient doping of a p-type organic semiconductor and greatly improve the performance of an organic photoelectric device, the invention provides an organic ammonium salt p-type dopant and application thereof in the field of organic semiconductor photoelectric devices, so as to solve the technical problems of high development cost, difficulty in solution processing and poor doping effect.
To achieve the above object, according to one aspect of the present invention, there is provided an organic ammonium salt p-type dopant, the p-type dopant being an organic ammonium salt having a structure represented by formula (a) or (b):
wherein R is1，R2，R3，R4，R5，R6，R7Each independently is H, hydroxy, carboxy, substituted or unsubstituted alkyl, cycloalkyl, heterocycloalkyl, heterocycloalkylene, ketoalkyl, alkoxy, alkenyl, ketoalkenyl, alkynyl, aryl, arylene, heteroaryl, heteroarylene, ketoaryl, ketoheteroaryl, haloalkyl, haloketoalkyl, haloalkenyl, haloketoalkenyl, haloalkynyl, haloaryl, haloheteroaryl, wherein one or more non-adjacent CH's are2May be independently substituted by-O-, OH-, -S-, -NH-, -CO-, -COO-, -COOH-, -OCO-O-, -SO 2-, -S-CO-, -CO-S-, -CH-, -C.ident.C-, aryl or heteroaryl; y is independently F, Cl, Br or I.
Further, the P-type dopant is a mixture of one or more organic ammonium salts, or a mixture of one or more organic ammonium salts as an effective component.
According to another aspect of the present invention, there is provided a use of an organic ammonium salt p-type dopant in an organic semiconductor optoelectronic device, wherein the p-type dopant is directly mixed with an acceptor material or the acceptor material is exposed to vapor of the p-type dopant to achieve p-doping of the acceptor material, and the use thereof in the fields of organic light emitting diodes, organic field effect transistors, organic solar cells, perovskite solar cells, and the like.
Further, the acceptor material is all p-type or bipolar organic semiconductors.
Further, the perovskite solar cell has a device structure that: ITO conductive glass as battery cathode, SnO2As a battery electron transport layer, MAPbI3The perovskite light absorption layer is formed by p-doping an acceptor material with a p-type dopant to form a battery hole transmission layer, and the metal Ag is used as a battery anode.
Further, device junction of organic field effect transistorThe structure is as follows: (1) bottom gate top contact: si as a gate, SiO2The p-type dopant is used as an insulating layer, the p-type dopant is used as a p-type semiconductor layer after p-doping is carried out on the receptor material, and Au is used as a source drain electrode; (2) bottom gate bottom contact: si as a gate, SiO2Au is used as an insulating layer, and is used as a source electrode and a drain electrode (Cr, Ni, Ti and the like are used as adhesion layers of Au electrodes), and a p-type dopant is used as a p-type semiconductor layer after p-doping is carried out on an acceptor material; (3) top gate top contact: glass, polyethylene terephthalate (PET) or Polyimide (PI) is used as a substrate, a p-type dopant is used for p-doping an acceptor material to be used as a p-type semiconductor layer, Au is used as a source and drain electrode, perfluoro resin (cytop), polymethyl methacrylate (PMMA) or Polystyrene (PS) is used as a dielectric layer, and Au or Al is used as a grid electrode; (4) top gate bottom contact: glass, polyethylene terephthalate (PET) or Polyimide (PI) as a substrate, Au as a source and drain (Cr, Ni, Ti, etc. as an adhesion layer of an Au electrode), a p-type dopant p-doped with an acceptor material as a p-type semiconductor layer, perfluoro resin (cytop), polymethyl methacrylate (PMMA) or Polystyrene (PS) as a dielectric layer, and Au or Al as a gate.
Furthermore, when the acceptor material is p-doped by the organic ammonium salt p-type dopant and then used as a p-type semiconductor layer or a hole transport layer, the doping concentration is 0.05 mol% to 30 mol%. Under low doping concentration, the hole mobility of the doped p-type or bipolar organic semiconductor is greatly improved; under high doping concentration, the conductivity of the doped p-type or bipolar organic semiconductor is greatly improved.
In summary, compared with the prior art, the above technical solution provided by the present invention can obtain the following beneficial effects:
(1) the p-type dopant provided by the invention can be used for solution processing, and can be directly added into a p-type organic semiconductor or the p-type organic semiconductor is exposed in steam of the p-type dopant to realize p doping on the organic semiconductor, so that the hole mobility and the conductivity of the p-type organic semiconductor are improved; the doped p-type organic semiconductor is further applied to perovskite cells and organic field effect transistors, so that the device performance can be remarkably improved, and the doped p-type organic semiconductor has wide application prospects in the field of other organic semiconductor photoelectric devices.
(2) The invention provides an organic ammonium salt as an effective p-type dopant, which can dope a p-type organic semiconductor by means of blending or steam. The doping method is simple and feasible and is suitable for large-area preparation. The present invention dopes p-type or bipolar organic semiconductors with organic ammonium salt p-type dopants. And the doped P-type or bipolar organic semiconductor is proved to have higher hole mobility and conductivity.
(3) The conductivity of the doped P-type or bipolar organic semiconductor is obviously improved, so that the P-type or bipolar organic semiconductor can be used as a hole transport layer in a perovskite cell device to improve the photoelectric conversion efficiency of the device. And the doping method is simple and is suitable for large-area preparation.
(4) In the organic field effect transistor, the mobility of the doped P-type or bipolar organic semiconductor is obviously improved, and the threshold voltage is obviously reduced.
(5) The preferred organic ammonium salt is cheap and easy to prepare, the doping method is simple, and the operation is easy, so that the organic ammonium salt is beneficial to application and popularization in the field of other semiconductor devices.
Drawings
FIG. 1(a) the electron spin resonance spectrum before and after doping of P3HT with organic ammonium salt in the example of the present invention;
FIG. 1(b) the electron spin resonance spectrum before and after doping PDVT-10 with organic ammonium salt in the embodiment of the present invention;
FIG. 1(c) an electron spin resonance spectrum before and after doping of PCDTPT with an organic ammonium salt in an example of the present invention;
FIG. 1(d) the electron spin resonance spectrum before and after doping of PCDTBT with organic ammonium salt in the example of the present invention;
FIG. 2 is a graph of conductivity versus doping concentration for P3HT doped with an organoammonium salt in an example of the invention;
FIG. 3(a) a schematic structural diagram of a perovskite solar cell as a hole transport layer before and after doping of P3HT with an organic ammonium salt in an embodiment of the present invention;
FIG. 3(b) current density-voltage diagram of perovskite solar cell as hole transport layer before and after doping of P3HT with organic ammonium salt in example of the present invention;
Detailed Description
In order to more clearly illustrate the objects and advantages of the present invention, the following embodiments are further described in detail with reference to the accompanying drawings. The following specific examples are given by way of illustration only and are not intended to be limiting.
The invention provides an organic ammonium salt p-type dopant, wherein the p-type dopant is an organic ammonium salt which has a structure shown as a formula (a) or (b):
wherein R is1，R2，R3，R4，R5，R6，R7Each independently is H, hydroxy, carboxy, substituted or unsubstituted alkyl, cycloalkyl, heterocycloalkyl, heterocycloalkylene, ketoalkyl, alkoxy, alkenyl, ketoalkenyl, alkynyl, aryl, arylene, heteroaryl, heteroarylene, ketoaryl, ketoheteroaryl, haloalkyl, haloketoalkyl, haloalkenyl, haloketoalkenyl, haloalkynyl, haloaryl, haloheteroaryl, wherein one or more of the appropriate groups is not adjacent CH2May be independently substituted by-O-, OH-, -S-, -NH-, -CO-, -COO-, -COOH-, -OCO-O-, -SO2-, -S-CO-, -CO-S-, -CH ═ CH-, -C ≡ C-and may likewise be substituted by aryl or heteroaryl. Y is independently F, Cl, Br, I.
The P-type dopant can P-dope the acceptor material to enhance the hole mobility and conductivity properties of the acceptor material. The acceptor material is all p-type or bipolar organic semiconductors.
The embodiment of the invention realizes P doping on the P-type organic semiconductor by directly blending the organic ammonium salt P-type dopant and the P-type organic semiconductor such as P3HT, PDVT-10, PCDTPT, PCDTBT and the like in an organic solvent. Preferably, when organic ammonium salts are blendedWhen the mole percentage of the hetero P3HT is 10%, the conductivity of the doped P3HT thin film is from 1.3X 10-2S m-1Lifting to 4.0 x 103S m-1. And the doped P3HT is used as a hole transport layer in the perovskite solar cell, so that the device efficiency of the cell is improved from 10.19% to 11.17% of a pure P3HT hole transport layer device.
Example 1
P-doping of P3HT, PDVT-10, PCDTPT and PCDTBT with organic ammonium salts
First, in a glove box filled with argon, the organic ammonium salt, P3HT, PDVT-10, PCDTPT and PCDTBT were dissolved in spectrally pure chlorobenzene to prepare a solution having a concentration of 10 mg/mL. All solutions were then filtered through a filter with a pore size of 0.45 μm. And calculating the volume of the required dopant and acceptor material according to the corresponding doping proportion, mixing the dopant and acceptor material solutions with the corresponding volume, and uniformly stirring at 70 ℃ to realize the doping of the acceptor material. And respectively adding 80 microliters of the solutions with different doping concentrations into a quartz tube, standing the quartz tube at 70 ℃ until the solvent is completely volatilized, and sealing the quartz tube. The quartz tube was taken out of the glove box and subjected to an electron spin resonance test at room temperature, and the electron spin resonance spectrum was as shown in FIG. 1.
This example illustrates that the organic ammonium salt introduces unpaired electrons in the organic semiconductor, i.e. doping of the organic semiconductor is achieved.
Example 2
Variation of conductivity of P3HT for different doping concentrations
The device structure for testing the conductivity of P3HT with different doping concentrations is a glass substrate/electrode (Cr/Au)/poly-3 hexylthiophene or a doped poly-3 hexylthiophene film (glass/(Cr/Au)/P3HT or doped P3 HT). The specific preparation method of example 2 is as follows:
(1) patterned electrodes were prepared on a glass substrate by photolithography and thermal evaporation, the electrodes being Cr/Au (2nm/30 nm).
(2) The glass substrate with the electrode is sequentially subjected to ultrasonic cleaning by deionized water, acetone and isopropanol, then is subjected to ozone treatment and then is transferred into a glove box.
(3) The P3HT solutions with different doping concentrations prepared in example 1 were spin-coated on the cleaned glass substrate with electrodes at 1500 rpm in a glove box filled with argon, and annealed at 130 ℃ for 5 minutes, thereby producing P3HT films with different doping concentrations.
(4) The device current-voltage relationship was measured by a four-probe method using a Keithley 4200 semiconductor analyzer to calculate the film conductivity. The calculation formula is σ ═ IL/(UWD), where I is the current, U is the voltage, L is the device effective channel length (40 μm), W is the device effective channel width (1000 μm), and D is the film thickness. The conductivity-doping concentration relationship for P3HT of different doping concentrations is shown in fig. 2.
This example illustrates that doping of P3HT with an organic ammonium salt significantly increases its conductivity.
Example 3
Preparation of perovskite solar cell
The perovskite solar cell is of a planar face-up structure: indium tin oxide conductive glass/tin dioxide/methylamine lead perovskite/poly-3 hexylthiophene or doped poly-3 hexylthiophene/silver (ITO/SnO)2/MAPbI3P3HT or sequenced P3HT/Ag) as shown in fig. 3 (a). The preparation and assembly steps of each functional layer are as follows:
(1) pretreating an ITO conductive glass substrate by ultraviolet ozone, and then taking a proper amount of SnO2The aqueous sol was spin-coated (3000 rpm, 30 seconds) on top and annealed at 150 ℃ for 30 minutes after the spin-coating was completed, thereby completing the preparation of the double-layer electron transport layer.
(2) The annealed SnO2And (3) carrying out ultraviolet ozone treatment on the sample for 10 minutes to remove organic groups on the surface and enhance the surface wettability, and transferring the sample into a glove box to prepare a perovskite layer and a hole transport layer after the ultraviolet ozone treatment is finished.
(3) The perovskite layer is obtained by continuous deposition in two steps, firstly, a proper amount of PbI is measured by a liquid-transferring gun2Spreading (553mg/mL, DMF) solution on the substrate, two-stage spin coating (front stage low speed spreading solution (800 rpm, 5 s), and rear stage high speed film forming (3000 rpm, 30 s) to obtain PbI2Film, after the spin coating is finished, immediately collectingAnd dynamically spin-coating and blending an MAI (60mg/mL, IPA) solution by using the same spin-coating process, and after the two-step continuous deposition spin-coating is finished, placing a sample on a hot bench and annealing at 100 ℃ for 60 minutes to obtain the perovskite thin film.
(4) And after the sample is cooled, preparing a hole transport layer P3HT or doped P3HT (10mg/mL, CB), preparing by adopting a two-stage spin coating process (800 r/min, 5 s; 3000 r/min, 30 s), annealing at 80 ℃ for 10 min after the spin coating is finished, and evaporating the solvent to obtain a P3HT or doped P3HT film. Preferably, the doping concentration is 0.5 mol%, and the device performance of the battery is optimal.
(5) And after all the functional layers are prepared, transferring the sample into a cavity of a metal vacuum evaporation plating instrument to evaporate Ag with the thickness of about 100nm as a top electrode, namely, the preparation of the perovskite solar cell is completed. The test was carried out by Keithley 2400, the cell effective area being 0.075cm2The intensity of the simulated sunlight is 100mW cm-2AM 1.5G. Fig. 3(b) is a current density-voltage curve for a cell device using pure P3HT and doped P3HT as the hole transport layer.
This example illustrates that organic ammonium salts doped with P3HT can significantly improve the performance of perovskite solar cell devices when used as hole transport layers.
Claims (6)
1. An organic ammonium salt p-type dopant, wherein the p-type dopant is an organic ammonium salt having a structure according to formula (a) or (b):
wherein R is1，R2，R3，R4，R5，R6，R7Each independently is H, hydroxy, carboxy, substituted or unsubstituted alkyl, cycloalkyl, heterocycloalkyl, heterocycloalkylene, ketoalkyl, alkoxy, alkenyl, ketoalkenyl, alkynyl, aryl, arylene, heteroaryl, heteroarylene, ketoaryl, ketoheteroaryl, haloalkyl, haloketoalkyl, haloalkenyl, haloketoalkenylA group, a haloalkynyl group, a haloaryl group, a haloheteroaryl group, wherein one or more are not adjacent CH2May be independently substituted by-O-, OH-, -S-, -NH-, -CO-, -COO-, -COOH-, -OCO-O-, -SO2-, -S-CO-, -CO-S-, -CH ═ CH-, -C ≡ C-, or substituted with aryl or heteroaryl; y is independently F, Cl, Br or I.
2. An organic ammonium salt P-type dopant according to claim 1, which is a mixture of one or more organic ammonium salts or a mixture of one or more organic ammonium salts as an active ingredient.
3. Use of an organic ammonium salt P-type dopant according to any one of claims 1 to 2 in an organic semiconductor optoelectronic device, wherein the organic ammonium salt P-type dopant is mixed directly with an acceptor material or the acceptor material is exposed to a vapour of the organic ammonium salt P-type dopant to effect P-doping of the acceptor material and the P-doped acceptor material is applied to an organic light emitting diode, an organic field effect transistor, an organic solar cell or a perovskite solar cell.
4. Use of the organic ammonium salt p-type dopant according to claim 3 in an organic semiconductor optoelectronic device, wherein the acceptor material is a p-type or a bipolar organic semiconductor.
5. The use of an organic ammonium salt p-type dopant according to claim 4 in an organic semiconductor solar cell, wherein the perovskite solar cell has a device structure of: ITO conductive glass as battery cathode, SnO2As a battery electron transport layer, MAPbI3The organic ammonium salt p-type dopant is used as a battery hole transport layer after p-doping the acceptor material, and the metal Ag is used as a battery anode.
6. As claimed in claim4, the application of the organic ammonium salt p-type dopant in an organic semiconductor field effect transistor is characterized in that the device structure of the organic field effect transistor is as follows: (1) bottom gate top contact: si as a gate, SiO2The organic ammonium salt p-type dopant is used as an insulating layer to perform p-doping on the receptor material to form a p-type semiconductor layer, and Au is used as a source drain electrode; (2) bottom gate bottom contact: si as a gate, SiO2The organic ammonium salt p-type dopant is used as a p-type semiconductor layer after p-doping is carried out on a receptor material; (3) top gate top contact: glass, polyethylene terephthalate or polyimide as a substrate; the organic ammonium salt p-type dopant is used as a p-type semiconductor layer after p-doping is carried out on the receptor material; au is used as a source drain electrode; perfluoro resin, polymethyl methacrylate or polystyrene as dielectric layer; au or Al is used as a grid; (4) top gate bottom contact: glass, polyethylene terephthalate or polyimide as a substrate; au is used as a source drain electrode; the organic ammonium salt p-type dopant is used as a p-type semiconductor layer after p-doping is carried out on the receptor material, and perfluoro resin, polymethyl methacrylate or polystyrene are used as dielectric layers; au or Al is used as the grid.
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