CN110606816A - Water-soluble hole transport material for polymer solar cell and preparation method thereof - Google Patents
Water-soluble hole transport material for polymer solar cell and preparation method thereof Download PDFInfo
- Publication number
- CN110606816A CN110606816A CN201910831434.9A CN201910831434A CN110606816A CN 110606816 A CN110606816 A CN 110606816A CN 201910831434 A CN201910831434 A CN 201910831434A CN 110606816 A CN110606816 A CN 110606816A
- Authority
- CN
- China
- Prior art keywords
- room temperature
- reaction kettle
- hole transport
- water
- temperature
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/24—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of a carbon skeleton containing six-membered aromatic rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Photovoltaic Devices (AREA)
Abstract
The invention relates to a water-soluble hole transport material for a polymer solar cell and a preparation method thereof, wherein the preparation method specifically comprises the steps of obtaining an intermediate product A through an addition reaction of fluorene and 1, 4-butanesultone, brominating the intermediate product A, and then carrying out a coupling reaction with 3- (trifluoromethoxy) phenylboronic acid to obtain a final product 2, 7-bis (3- (trifluoromethoxy)) - [9, 9- (4, 4-di-butylpotassium sulfonate) -fluorene. The water-soluble hole transport material prepared by the invention is used for polymer solar cells, can be processed by aqueous solution, is green and environment-friendly, and has high photoelectric conversion efficiency.
Description
Technical Field
The invention relates to a water-soluble hole transport material for a polymer solar cell and a preparation method thereof, and particularly belongs to the technical field of photoelectric materials.
Background content
The energy problem is the biggest problem facing human beings, solar energy is the most common and most green energy, and the utilization of solar energy is one of approaches for solving the human energy problem. Solar cells currently being developed are: silicon solar cells, organic solar cells, and the like. Although the silicon solar cell has high energy conversion efficiency, the raw material cost is high and the production process causes large pollution.
The polymer solar cell is a novel solar cell and has the advantages of low cost, softness, lightness, thinness, portability, high photoelectric conversion efficiency and the like. The hole transport layer is an indispensable component of the polymer solar cell and has an important influence on the photoelectric conversion efficiency and stability of the cell.
At present, the most commonly used polymer hole transport material of polymer solar cells is poly (3, 4-ethylenedioxythiophene): polystyrene sulfonate (PEDEOT: PSS). PEDOT: PSS can be processed by aqueous solution, and is suitable for large-scale large-area production, and the preparation process comprises the steps of dissolving sodium poly-styrene sulfonate in a certain amount of deionized water, dropwise adding 3, 4-ethylenedioxythiophene monomer, slowly stirring for 5 minutes, dropwise adding hydrochloric acid to control the pH value of the system to be 2 ~ 3, slowly dropwise adding ammonium persulfate and ferric sulfate mixed solution, quickly stirring for reaction for 24 hours, and respectively exchanging inorganic salt ions for 4 hours by using anion exchange resin and cation exchange resin to obtain a PEDOT: PSS dark blue solution, wherein the molar ratio of PSS to EDOT is 2:1, the molar ratio of ammonium persulfate to EDOT is 1.5:1, and the molar ratio of ferric sulfate to EDOT is 0.002: 1.
Conjugated polymer hole transport materials such as poly (4, 4-potassium dibutylsulfonate-alt-benzothiadiazole) (CPE-K), poly [2,6- (4, 4-di-butylsodium sulfonate-4 hydro-cyclopenta [2,1-b;3, 4-b']Dithiophene) -alt-1, 4-benzenes](CPEPh-Na). CPE-K and CPEPh-Na are neutral and do not corrode the electrode; but its conductivity is low (1.5X 10)-3S/cm), the very thin to be processed can achieve good results, so that the large-scale use thereof is limited.
The hole transport material has excellent water solubility, good film forming property and simple manufacturing process; the material is neutral and does not corrode an electrode, so that the stability of the solar cell is improved; the material has high conductivity (5.3 × 10)-3S/cm), can keep higher efficiency even when the thickness is larger, and is suitable for large-scale production.
Disclosure of Invention
In view of the problems of PEDOT and PSS, the invention aims to provide a water-soluble hole transport material. Compared with acid PEDOT and PSS, the water-soluble hole transport material provided by the invention is neutral, and is beneficial to improving the stability of the battery.
The chemical structural formula of the water-soluble hole transport material for the polymer solar cell is as follows:
the preparation method comprises the following steps:
step 1: adding 1.0 mol part of fluorene and 150.0 ml of tetrahydrofuran into a glass reaction kettle at the temperature of-78 ℃, adding 2.0 mol part of n-butyllithium, magnetically stirring for 45 minutes, adding 2.0 mol part of 1, 4-butanesultone into the reaction kettle, raising the temperature of the reaction kettle to room temperature, magnetically stirring for reaction for 8.0 hours at the room temperature, pouring all reactants in the reaction kettle into 200.0 ml of distilled water, mechanically stirring for 30 minutes at the room temperature, extracting an aqueous solution with 150.0 ml of diethyl ether, separating liquid, taking a diethyl ether phase, drying the diethyl ether phase with 25.0 g of anhydrous sodium sulfate, carrying out suction filtration to remove the anhydrous sodium sulfate, taking a filtrate, carrying out reduced pressure distillation on the filtrate at the temperature of 40 ℃, and removing the diethyl ether to obtain an intermediate product A;
step 2: completely wrapping a glass reaction kettle by using 2.0 mm thick tinfoil, adding 1.0 mol part of intermediate product A and 100.0 ml of trichloromethane into the glass reaction kettle at 0 ℃, adding 2.0 mol part of liquid bromine and 24.0 g of ferric trichloride, raising the temperature of the reaction kettle to room temperature, carrying out magnetic stirring reaction at the room temperature for 24.0 hours, pouring all solutions in the reaction kettle into 100.0 ml of distilled water, mechanically stirring at the room temperature for 30 minutes, extracting an aqueous solution by using 200.0 ml of dichloromethane, separating liquid, taking a dichloromethane phase, drying the dichloromethane phase by using 40.0 g of anhydrous sodium sulfate, carrying out suction filtration, removing the anhydrous sodium sulfate, and distilling a filtrate at 50 ℃ under reduced pressure to remove dichloromethane and trichloromethane to obtain an intermediate product B;
and 3, adding 1.0 mol part of the intermediate product B and 3- (trifluoromethoxy) phenylboronic acid into a glass reaction kettle, adding 50.0 ml of N, N-dimethylformamide, magnetically stirring for 30 minutes at room temperature, introducing nitrogen at the flow rate of 1.0 liter/minute in a bubbling manner for 1.0 hour, then adding 0.04 ~ 0.05.05 mol of tetratriphenylphosphine palladium and 30.0 ml of 1.0 mol/minute aqueous solution of potassium carbonate, heating the reaction kettle to 90 ~ 100 ℃ at the speed of 10 ℃/minute, magnetically stirring for 24.0 ~ 36.0.0 hours at the constant temperature of 90 ~ 100 and 100 ℃, stopping the reaction, cooling to room temperature, pouring all reactants in the reaction kettle into 100.0 ml of acetone, magnetically stirring for 30 minutes at room temperature, and filtering to obtain a light yellow solid final product, namely 2, 7-bis (3- (trifluoromethoxy)) [9, 9- (4, 4-di-butylsulfonic acid potassium) -fluorene.
The invention has the beneficial effects that:
the water-soluble hole transport material can be processed by aqueous solution, can be produced in large scale and is environment-friendly.
The water-soluble hole transport material disclosed by the invention has neutral aqueous solution, cannot corrode an electrode, and is beneficial to improving the stability of a battery.
The water-soluble hole transport material is a micromolecule and has a simple preparation process.
Drawings
FIG. 1 is a chemical structural formula of the water-soluble small molecule hole transport material of the present invention.
Detailed Description
The present invention is described by the following examples, but is not limited to the following examples, and all changes and modifications are included in the technical scope of the present invention without changing the gist of the present invention described before and after.
Example 1
Step 1: adding 1.0 mol part of fluorene and 150.0 ml of tetrahydrofuran into a glass reaction kettle at the temperature of-78 ℃, adding 2.0 mol part of n-butyllithium, magnetically stirring for 45 minutes, adding 2.0 mol part of 1, 4-butanesultone into the reaction kettle, raising the temperature of the reaction kettle to room temperature, magnetically stirring for reaction for 8.0 hours at the room temperature, pouring all reactants in the reaction kettle into 200.0 ml of distilled water, mechanically stirring for 30 minutes at the room temperature, extracting an aqueous solution with 150.0 ml of diethyl ether, separating liquid, taking a diethyl ether phase, drying the diethyl ether phase with 25.0 g of anhydrous sodium sulfate, carrying out suction filtration to remove the anhydrous sodium sulfate, taking a filtrate, carrying out reduced pressure distillation on the filtrate at the temperature of 40 ℃, and removing the diethyl ether to obtain an intermediate product A;
step 2: completely wrapping a glass reaction kettle by using 2.0 mm thick tinfoil, adding 1.0 mol part of intermediate product A and 100.0 ml of trichloromethane into the glass reaction kettle at 0 ℃, adding 2.0 mol part of liquid bromine and 24.0 g of ferric trichloride, raising the temperature of the reaction kettle to room temperature, carrying out magnetic stirring reaction at the room temperature for 24.0 hours, pouring all solutions in the reaction kettle into 100.0 ml of distilled water, mechanically stirring at the room temperature for 30 minutes, extracting an aqueous solution by using 200.0 ml of dichloromethane, separating liquid, taking a dichloromethane phase, drying the dichloromethane phase by using 40.0 g of anhydrous sodium sulfate, carrying out suction filtration, removing the anhydrous sodium sulfate, and distilling a filtrate at 50 ℃ under reduced pressure to remove dichloromethane and trichloromethane to obtain an intermediate product B;
and step 3: adding 1.0 mol portion of intermediate product B and 3- (trifluoromethoxy) phenylboronic acid into a glass reaction kettle, adding 50.0 ml of N, N-dimethylformamide, magnetically stirring for 30 minutes at room temperature, then, nitrogen was introduced at a flow rate of 1.0 liter/min by bubbling for 1.0 hour, then 0.04 mol of tetrakistriphenylphosphine palladium and 30.0 ml of a 1.0 mol/l aqueous solution of potassium carbonate were added, heating the reaction kettle to 90 ℃ at the speed of 10 ℃/min, reacting for 24.0 hours at the constant temperature of 90 ℃ by magnetic stirring, stopping the reaction, cooling to room temperature, pouring all reactants in the reaction kettle into 100.0 ml of acetone, magnetically stirring for 30 minutes at room temperature, and filtering by suction to obtain a light yellow solid final product, namely 2, 7-bis (3- (trifluoromethoxy)) - [9, 9- (4, 4-di-butyl potassium sulfonate) -fluorene.
Example 2
Step 1: adding 1.0 mol part of fluorene and 150.0 ml of tetrahydrofuran into a glass reaction kettle at the temperature of-78 ℃, adding 2.0 mol part of n-butyllithium, magnetically stirring for 45 minutes, adding 2.0 mol part of 1, 4-butanesultone into the reaction kettle, raising the temperature of the reaction kettle to room temperature, magnetically stirring for reaction for 8.0 hours at the room temperature, pouring all reactants in the reaction kettle into 200.0 ml of distilled water, mechanically stirring for 30 minutes at the room temperature, extracting an aqueous solution with 150.0 ml of diethyl ether, separating liquid, taking a diethyl ether phase, drying the diethyl ether phase with 25.0 g of anhydrous sodium sulfate, carrying out suction filtration to remove the anhydrous sodium sulfate, taking a filtrate, carrying out reduced pressure distillation on the filtrate at the temperature of 40 ℃, and removing the diethyl ether to obtain an intermediate product A;
step 2: completely wrapping a glass reaction kettle by using 2.0 mm thick tinfoil, adding 1.0 mol part of intermediate product A and 100.0 ml of trichloromethane into the glass reaction kettle at 0 ℃, adding 2.0 mol part of liquid bromine and 24.0 g of ferric trichloride, raising the temperature of the reaction kettle to room temperature, carrying out magnetic stirring reaction at the room temperature for 24.0 hours, pouring all solutions in the reaction kettle into 100.0 ml of distilled water, mechanically stirring at the room temperature for 30 minutes, extracting an aqueous solution by using 200.0 ml of dichloromethane, separating liquid, taking a dichloromethane phase, drying the dichloromethane phase by using 40.0 g of anhydrous sodium sulfate, carrying out suction filtration, removing the anhydrous sodium sulfate, and distilling a filtrate at 50 ℃ under reduced pressure to remove dichloromethane and trichloromethane to obtain an intermediate product B;
and step 3: adding 1.0 mol portion of intermediate product B and 3- (trifluoromethoxy) phenylboronic acid into a glass reaction kettle, adding 50.0 ml of N, N-dimethylformamide, magnetically stirring for 30 minutes at room temperature, then, nitrogen was introduced at a flow rate of 1.0 liter/min by bubbling for 1.0 hour, then 0.05 mol of tetrakistriphenylphosphine palladium and 30.0 ml of a 1.0 mol/l aqueous solution of potassium carbonate were added, heating the reaction kettle to 100 ℃ at the speed of 10 ℃/min, carrying out magnetic stirring reaction at the constant temperature of 100 ℃ for 36.0 hours, stopping the reaction, cooling to room temperature, pouring all reactants in the reaction kettle into 100.0 ml of acetone, magnetically stirring for 30 minutes at room temperature, and filtering by suction to obtain a light yellow solid final product, namely 2, 7-bis (3- (trifluoromethoxy)) - [9, 9- (4, 4-di-butyl potassium sulfonate) -fluorene.
0.2 g of 2, 7-bis (3- (trifluoromethoxy)) - [9, 9- (4, 4-di-butylsulfonic acid potassium) -fluorene from example 1 or example 2, respectively, was dissolved in 10.0 ml of water and mechanically stirred at room temperature for 30 minutes, and then the solution was filtered through a 2.2 μm filter head to obtain a solution of 2, 7-bis (3- (trifluoromethoxy)) - [9, 9- (4, 4-di-butylsulfonic acid potassium) -fluorene.
The pH of the solution was measured using a SevenGo-cell pH-SG2 pH meter.
Hole testing for both examples using space charge limited current methodMobility (mu)h) The device structure was indium tin oxide glass (ITO)/2, 7-bis (3- (trifluoromethoxy)) - [9, 9- (4, 4-di-butylsulfonic acid potassium) -fluorene/gold (Au) prepared in example 1 or example 2. spin coating conditions of a solution of 2, 7-bis (3- (trifluoromethoxy)) - [9, 9- (4, 4-di-butylsulfonic acid potassium) -fluorene were 3000 rpm 30 sec. Au was processed by vacuum evaporation to a thickness of 70 ~ 80 nm.
The photoelectric conversion efficiency of 2, 7-bis (3- (trifluoromethoxy)) - [9, 9- (4, 4-di-butylsulfonic acid potassium) -fluorene was tested by a forward organic solar cell device. The device structure is as follows: ITO/2, 7-bis (3- (trifluoromethoxy)) - [9, 9- (4, 4-di-butylsulfonic acid potassium) -fluorene/poly [ 2-ethylhexyl-6- (4, 8-bis (5- (2-ethylhexyl) thiophen-2-yl) benzo [1,2-b:4,5-b 'prepared in example 1 or example 2']Dithien-2-yl) -3-fluorothieno [3,4-b]Thiophene-2-carboxyl](PBDTTT-EFT), with [6,6 ]]-phenyl C71 butyric acid methyl ester (PC)71BM) blended active layer/PFN/aluminum (Al). Spin coating conditions for 2, 7-bis (3- (trifluoromethoxy)) - [9, 9- (4, 4-di-butylsulfonic acid potassium) -fluorene were 3000 revolutions for 35 seconds. PBDTTT-EFT and PC71The mass ratio of BM was 1:1, the thickness of PFN was 5 ~ 10 nm, the evaporation thickness of Al was 80 ~ 100 nm, for comparison, organic solar cells of the same structure were also fabricated using PEDOT: PSS (4083) hole transport layer, the photoelectric conversion efficiency of the fabricated organic solar cells was further tested by Keithley2400 system, the photoelectric conversion efficiency was an average of 10 cells.
The data such as the photoelectric conversion efficiency of the battery are as follows:
μhfor hole mobility, VocIs an open circuit voltage. J. the design is a squarescFor short circuit current, FF is the fill factor, PCE is the energy conversion efficiency, and S is the battery stability.
Claims (2)
1. A water-soluble hole transport material for a polymer solar cell, characterized in that: the chemical structural formula of the water-soluble hole transport material is as follows:
。
2. a water-soluble hole transport material for a polymer solar cell and a preparation method thereof are characterized in that: the preparation method comprises the following steps:
step 1: adding 1.0 mol part of fluorene and 150.0 ml of tetrahydrofuran into a glass reaction kettle at the temperature of-78 ℃, adding 2.0 mol part of n-butyllithium, magnetically stirring for 45 minutes, adding 2.0 mol part of 1, 4-butanesultone, raising the temperature of the glass reaction kettle to room temperature, magnetically stirring for reaction for 8.0 hours at the room temperature, pouring a reaction product into 200.0 ml of distilled water, mechanically stirring for 30 minutes at the room temperature, extracting an aqueous solution with 150.0 ml of diethyl ether, taking an diethyl ether phase after liquid separation, drying the diethyl ether phase with 25.0 g of anhydrous sodium sulfate, carrying out suction filtration, removing the anhydrous sodium sulfate, distilling the filtrate at the temperature of 40 ℃ under reduced pressure, and removing the diethyl ether to obtain an intermediate product A;
step 2: completely wrapping a glass reaction kettle by using 2.0 mm thick tinfoil, adding 1.0 mol part of intermediate product A and 100.0 ml of trichloromethane into the glass reaction kettle at 0 ℃, adding 2.0 mol part of liquid bromine and 24.0 g of ferric trichloride, raising the temperature of the glass reaction kettle to room temperature, carrying out magnetic stirring reaction at the room temperature for 24.0 hours, pouring 100.0 ml of distilled water into the reaction product, mechanically stirring for 30 minutes at the room temperature, extracting with 200.0 ml of dichloromethane, separating liquid, taking a dichloromethane phase, drying the dichloromethane phase by using 40.0 g of anhydrous sodium sulfate, carrying out suction filtration to remove the anhydrous sodium sulfate, and distilling the obtained filtrate at 50 ℃ under reduced pressure to remove dichloromethane and trichloromethane to obtain an intermediate product B;
and 3, adding 1.0 mol part of the intermediate product B and 3- (trifluoromethoxy) phenylboronic acid into a glass reaction kettle, adding 50.0 ml of N, N-dimethylformamide, magnetically stirring for 30 minutes at room temperature, introducing nitrogen for 1.0 hour in a bubbling manner at the flow rate of 1.0 liter/minute, adding 0.04 ~ 0.05.05 mol part of tetratriphenylphosphine palladium and 30.0 ml of 1.0 mol/minute aqueous solution of potassium carbonate, heating the glass reaction kettle to 90 ~ 100 ℃ at the speed of 10 ℃/minute, magnetically stirring for 24.0 ~ 36.0.0 hours at the temperature of 90 ~ 100 ℃ at 100 ℃, stopping the reaction, cooling to room temperature, pouring the reaction product in the glass reaction kettle into 100.0 ml of acetone, magnetically stirring for 30 minutes at room temperature, and performing suction filtration to obtain a light yellow solid product 2, 7-bis (3- (trifluoromethoxy)) [9, 9- (4, 4-di-butylsulfonic acid potassium) -fluorene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910831434.9A CN110606816A (en) | 2019-09-04 | 2019-09-04 | Water-soluble hole transport material for polymer solar cell and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910831434.9A CN110606816A (en) | 2019-09-04 | 2019-09-04 | Water-soluble hole transport material for polymer solar cell and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110606816A true CN110606816A (en) | 2019-12-24 |
Family
ID=68892183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910831434.9A Pending CN110606816A (en) | 2019-09-04 | 2019-09-04 | Water-soluble hole transport material for polymer solar cell and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110606816A (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130068305A1 (en) * | 2010-05-26 | 2013-03-21 | Gwangju Institute Of Science And Technology | P-doped conjugated polymer electrolyte and an organic electronic device using the same |
| CN103408728A (en) * | 2013-07-16 | 2013-11-27 | 常州大学 | Fluorene based sulfonic acid type water/alcohol-soluble conjugated polymer and preparation method thereof |
| CN105720210A (en) * | 2014-12-23 | 2016-06-29 | 光州科学技术院 | P-doped conjugated small molecular electrolyte and organic electronic devices using the same |
| CN105968126A (en) * | 2016-03-31 | 2016-09-28 | 华南理工大学 | Dipyridine/phenanthroline onium salt-containing water/alcohol-soluble conjugated micromolecule and preparation method and application thereof |
| CN108470837A (en) * | 2018-04-11 | 2018-08-31 | 南昌航空大学 | A kind of anode of polymer solar cell modification layer material and preparation method |
| CN108467402A (en) * | 2018-04-16 | 2018-08-31 | 太原理工大学 | Fluorine replaces organic molecule hole mobile material and its application |
-
2019
- 2019-09-04 CN CN201910831434.9A patent/CN110606816A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130068305A1 (en) * | 2010-05-26 | 2013-03-21 | Gwangju Institute Of Science And Technology | P-doped conjugated polymer electrolyte and an organic electronic device using the same |
| CN103408728A (en) * | 2013-07-16 | 2013-11-27 | 常州大学 | Fluorene based sulfonic acid type water/alcohol-soluble conjugated polymer and preparation method thereof |
| CN105720210A (en) * | 2014-12-23 | 2016-06-29 | 光州科学技术院 | P-doped conjugated small molecular electrolyte and organic electronic devices using the same |
| CN105968126A (en) * | 2016-03-31 | 2016-09-28 | 华南理工大学 | Dipyridine/phenanthroline onium salt-containing water/alcohol-soluble conjugated micromolecule and preparation method and application thereof |
| CN108470837A (en) * | 2018-04-11 | 2018-08-31 | 南昌航空大学 | A kind of anode of polymer solar cell modification layer material and preparation method |
| CN108467402A (en) * | 2018-04-16 | 2018-08-31 | 太原理工大学 | Fluorine replaces organic molecule hole mobile material and its application |
Non-Patent Citations (5)
| Title |
|---|
| ERDOGAN A.等: ""Surface modifi cation of CdSeS nanocrystals for polymer hybrid solar cells"", 《RSC ADV.》 * |
| SEUNG HYUN KIM等: ""Synthesis and surface modification of hybrid multiblock gold-nickel-polypyrrole nanorods by poly(fluorene) and their optical properties"", 《JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY》 * |
| 于跃等: "氟代有机光电功能小分子材料的研究", 《中国材料进展》 * |
| 张婧等: "钙钛矿太阳能电池中小分子空穴传输材料的研究进展", 《物理化学学报》 * |
| 袁峰等: "有机太阳能电池空穴传输材料的研究进展", 《功能高分子学报》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5665992B2 (en) | Benzodithiophene organic semiconductor material and preparation method thereof | |
| CN104910372B (en) | Aryl polyphenol and the injection of 1,3,5 s-triazine cross-linked polymer holes and transmission material and preparation method and application | |
| CN111909169B (en) | Hole transport material with benzodithiophene dione as core, synthesis method and application of hole transport material in perovskite solar cell | |
| CN110416412A (en) | It is a kind of for improving the electron transfer layer and preparation method of reversed perovskite solar cell stability | |
| CN102686636B (en) | Conjugated fluorene polymer, preparing method thereof and solar battery component | |
| CN102391533B (en) | Method for preparing nanometer ordered porous organic film based on polythiophene- fullerene- polylactic acid triblock copolymer | |
| CN105914298A (en) | Polymer photovoltaic cell taking isoindigo derivative as cathode interface modification layer | |
| CN104119501A (en) | Conjugated polymer material containing thienothiophene-dithienodiazosulfide-diazosulfide and preparation method and application thereof | |
| CN102816297A (en) | Polymer based on biphenyl thiadiazole, and preparation method and application thereof | |
| CN110563615A (en) | Water/alcohol soluble micromolecule hole transport material and preparation method thereof | |
| CN110606816A (en) | Water-soluble hole transport material for polymer solar cell and preparation method thereof | |
| CN107286177A (en) | A kind of indacene 1,4-Dithiapentalene class photovoltaic material and its preparation method and application | |
| CN108659019A (en) | Perovskite hole mobile material and preparation method thereof based on triptycene parent nucleus | |
| CN102643284B (en) | Preparation method and application of 4,9-bisalkylene indene thieno[3,2-b]thiophene derivative and conjugated polymer thereof | |
| CN103435785B (en) | Polymkeric substance and its preparation method, organic polymer solar cell | |
| CN104045813B (en) | A kind of containing indenes ketone-carbazole-benzo two thiophene copolymers and its preparation method and application | |
| CN109232527A (en) | The organic photovoltaic cell of self-doping type fullerene pyridiniujm electron transport material and its composition | |
| CN103923106A (en) | Low-energy-gap and broad-absorption conjugated polymer and preparation method thereof | |
| CN111171289B (en) | TEMPO oxidized cellulose/PEDOT polymer and preparation method and application thereof | |
| CN110498793B (en) | Small-molecule photovoltaic bulk phase material based on rhodanine and application thereof | |
| CN102827185A (en) | D-A-D conjugated molecule based on triphenylamine-thiophene imide, and preparation method and application thereof | |
| CN110563745B (en) | Micromolecule hole transport material for organic solar cell and preparation method thereof | |
| CN111205307A (en) | Thienobenzothiadiazoledione organic compound, and preparation method and application thereof | |
| CN110635045B (en) | Water/alcohol soluble organic solar cell anode modification layer material and preparation method thereof | |
| CN106129250B (en) | A kind of preparation method of the polymer solar battery based on Lorentz force |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20191224 |
|
| WD01 | Invention patent application deemed withdrawn after publication |