CN115304622A - Fluorene molecular lock micromolecule cathode interface layer and preparation method thereof - Google Patents
Fluorene molecular lock micromolecule cathode interface layer and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a fluorene molecular lock micromolecule cathode interface layer and a preparation method thereof, pyridine is grafted on 2, 7-dibromofluorene by a Williamson synthesis method to synthesize bromofluorene derivatives, and the bromofluorene derivatives are coupled with fluorobenzene to obtain a product. Firstly, pyridine can endow the material with alcohol solubility, and form a dipole at an interface to reduce the work function, thereby further reducing the interface potential barrier between an electrode and an active layer and improving the carrier mobility and the open-circuit voltage; nitrogen atoms on the pyridine can realize n-type doping of an active layer receptor, and contact between the active layer and a metal cathode is optimized; the hydrogen atoms on the fluorene and fluorine atoms on the benzene ring form F \8230, and H weak bonds form a 'molecular lock', so that the planarity of molecules is effectively improved, the molecules have good molecular accumulation, and the stability and efficiency of the device are improved. Secondly, the strong electronegativity exhibited by the fluorine atoms causes the molecules to exhibit highly electron deficient regions and lowers the lowest unoccupied orbital level, facilitating electron transfer from the acceptor to the cathode interface layer.
Description
Technical Field
The invention relates to the technical field of cathode interface layers of organic solar cells, in particular to a preparation method of a fluorene molecular locked small molecule cathode interface layer.
Background
In the twenty-first century, with the continuous development of the world economy, the global population is rapidly increased, so that people consume a large amount of fossil energy, the emission of greenhouse gases is greatly increased, and a series of environmental problems such as global warming are caused. Further, fossil energy is becoming increasingly scarce due to excessive exploitation of fossil energy represented by petroleum. Therefore, the development and utilization of new clean renewable energy sources has become a key issue of attention in various countries.
At present, the main clean and renewable energy sources are solar energy, tidal energy, wind energy and the like, and since the solar energy has the unique advantages of abundant reserves, no limitation of geographical conditions, relatively safe use and the like, more and more students are conducting research on the development and utilization of the solar energy. At present, the most common and efficient way for people to utilize solar energy is to directly convert the solar energy into electric energy through solar cells. The solar cell is mainly divided into an inorganic solar cell and an organic solar cell, and the inorganic silicon solar cell is the most widely used cell in the market at present, and the energy conversion efficiency of the inorganic silicon solar cell exceeds 26%. However, since the inorganic solar cell has disadvantages of high production cost, complex preparation process, non-flexibility, etc., it has limited large-scale development and application. The organic solar cell has the advantages of low cost, light weight, simple process, bending resistance, large-area preparation and the like, and thus, the organic solar cell becomes one of the fastest-developing and most active research fields in recent years.
Organic Solar Cells (OSCs) have made significant progress over the past few decades, mainly due to the tremendous efforts of researchers in device optimization and organic semiconductor synthesis, especially with recent advances in non-fullerene electron acceptors, and today the energy conversion efficiencies of the most advanced OSCs with high performance non-fullerene acceptors have been over 19%. One limitation that still exists in OSCs is the limitation of charge extraction and transport between the metal electrodes and the organic semiconductor. The mismatch in energy levels typically results in additional energy loss, preventing efficient transport of charge. In order to achieve energy level matching, it is important to prepare a high-performance interface layer.
Fluorene micromolecules are used as a representative micromolecule in a cathode interface layer, a fluorene ring is a special rigid plane biphenyl structure, two benzene rings are connected with a bridged methylene through a C-C single bond, the two benzene rings and the methylene are almost on the same plane, so that the fluorene derivative has stronger rigidity and thermal stability, the carbons at the 2 position, the 7 position and the 9 position of the fluorene ring are easy to carry out structural modification, and various functional groups are introduced for synthesizing the fluorene derivative.
Disclosure of Invention
The invention provides a preparation method of a fluorene molecular lock micromolecule cathode interface layer and application of the fluorene molecular lock micromolecule cathode interface layer in a non-fullerene solar cell. Based on the advantages of an interface dipole and a molecular lock, the fluorenyl is structurally optimized, and the polar pyridyl modifying group is introduced into the side chain, so that the material is environment-friendly in water/alcohol solubility processing, the interface dipole can be formed at the interface, the work function of a cathode is reduced, and good ohmic contact is formed, so that the interface barrier between an electrode and an active layer is further reduced, and the carrier mobility and the open-circuit voltage are improved. Second, sp of the nitrogen atom on the pyridyl group 2 The hybrid orbit has lone pair electrons, shows electron donating effect, reduces charge transport loss through n-type doped active layer receptors, and improves the contact between the active layer and the metal cathode. Thirdly, by attaching fluorobenzene to fluorenyl groupThe group is F\8230formedby hydrogen atoms on a fluorene ring and fluorine atoms on a benzene ring, and a weak H bond forms a molecular lock, so that the fluorene group and the pyridine group keep a good coplanar, the rigid planar structure of small molecules is enhanced, the molecular stacking is facilitated, and the electron mobility is improved. And thirdly, fluorine atoms show strong electron-withdrawing capability, so that molecules show a high electron-deficient region, and the transfer of electrons from an acceptor to a cathode interface layer is promoted. In addition, the fluorine atom enables the fluorenyl to have a lower lowest unoccupied orbital level, improves the level matching degree at the FPy-FP/cathode interface, obtains more favorable electron extraction efficiency, and shows higher electron mobility and better interface compatibility.
The invention aims to provide a preparation method and application of a fluorene molecular lock micromolecule cathode interface layer. The non-fullerene solar cell device prepared by the fluorene molecule locked small molecule cathode interface layer is applied.
The technical scheme adopted by the invention is as follows: a fluorene molecule-locked small molecule cathode interface layer is characterized in that: has a structure shown in formula 1, as follows:
the other technical scheme of the invention is as follows: a fluorene molecule lock micromolecule cathode interface layer containing a structure shown in a formula I is characterized by comprising the following steps:
the method comprises the following steps: synthesis of pyridyl side chain of 2, 7-dibromofluorene FPy-2 Br:
(1) Weighing 1.2mmol of reactants 2, 7-dibromo-9, 9-di (6-bromohexyl) fluorene and 2.64mmol of 4-hydroxypyridine, adding into a flask, adding 500mg of potassium carbonate into the flask, building a reflux device, vacuumizing for 3 minutes, introducing N 2 5 minutes (3 replicates). In general N 2 In the case of (1), 40mL of ultra-dry DMF as a solvent for the reaction was injected through a rubber tube connected to the flask via a branch tube by a syringe, the needle hole was sealed with a sealing tape after the injection was completed, the magnetic stirrer was turned on to sufficiently dissolve the reactant, the flask was evacuated again for 5 minutes, and N was introduced 2 5 points ofA clock. Then, the mixture is wrapped by a black plastic bag and protected from light, is fixed by a bandage, and is heated, stirred and refluxed for reaction for 24 hours at 125 ℃.
(2) After the reaction is finished, the device is disassembled, and the reaction solution is cooled to room temperature in a dark place. And (3) building a reduced pressure distillation device, carrying out reduced pressure distillation on the reaction liquid at the temperature of 115-120 ℃ for 5 hours, and distilling out the DMF solvent to obtain a small amount of light yellow emulsion.
(3) After dissolving the mixture in 30mL of methylene chloride, the mixture was extracted with 3 volumes of water, the lower organic phase was collected as a yellow liquid, the extraction was repeated 3 times, and a suitable amount of anhydrous magnesium sulfate was added to the collected lower liquid to remove the water remaining therein, followed by stirring and standing. The magnesium sulfate was removed by suction filtration.
(4) Putting the obtained yellow liquid into a heart-shaped bottle, performing rotary evaporation at 40 ℃ to remove dichloromethane in the heart-shaped bottle to obtain a foamy solid substance, and drying the foamy solid substance in a vacuum drying oven at 60 ℃ for 24 hours to obtain a light yellow solid crude product of FPy-2 Br.
(5) The crude product was dissolved with dichloromethane and purified with methanol: and (3) taking ethyl acetate =1 as a developing solvent spot plate, irradiating and observing by using an ultraviolet analyzer, purifying the product by performing column chromatography, and loading the product by adopting a wet method and a dry method. And (3) spin-drying the obtained light yellow liquid, putting the light yellow liquid into a vacuum drying oven for drying for 24h, and scraping the product to obtain light yellow solid FPy-2Br with the yield of 45%.
Step two: and (3) synthesizing a fluorene molecular lock small molecule cathode interface layer FPy-FP:
(1) 0.5mmol of FPy-2Br and 1.2mmol of 2-fluorobenzeneboronic acid pinacol ester are taken as reactants and added into a flask, and 500mg of potassium carbonate and 50mg of catalyst Pd (PPh) are added 3 ) 4 . Building a reflux device, vacuumizing for 3 minutes, and introducing N 2 5 minutes (3 replicates). In general N 2 In the case of (1), 20mL of ultra-dry DMF was injected with a syringe, the respective raw materials were mixed, evacuated again for 5 minutes, and N was introduced 2 Heated and refluxed for 24h at 105 ℃ for 5 minutes, and the black plastic bag is protected from light.
(2) Cooling the reaction to room temperature, building a vacuum distillation device, carrying out vacuum distillation on the reaction liquid at the temperature of 115-120 ℃ for 5 hours, and distilling out the DMF solvent to obtain a small amount of light yellow emulsion.
(3) It was extracted with water and dichloromethane to remove the water solubles and the catalyst. After the extraction was completed, an appropriate amount of anhydrous magnesium sulfate was added to remove residual water in the liquid, and the solvent was spin-dried to obtain a crude product.
(4) Crude product was purified using methanol in volume ratio: ethyl acetate =1.5, and the resulting liquid was spin-dried, placed in a vacuum oven for drying for 24h, and the product was scraped off to give off-white solid FPy-FP with a yield of 88%.
The other technical scheme of the invention is as follows: a non-fullerene solar cell device with a fluorene molecule locked small molecule cathode interface layer is characterized in that:
the electrode comprises an ITO glass layer, a PEDOT (polymer stabilized organic light emitting diode) PSS (positive electrode active material) interface layer arranged on the ITO glass layer, an active layer arranged on the PEDOT PSS layer, a fluorene molecular locking micromolecule cathode interface layer arranged on the active layer, and an Al electrode layer arranged on the fluorene molecular locking micromolecule cathode interface layer.
The other technical scheme of the invention is as follows: a method for synthesizing a fluorene molecular locked small molecule cathode interface layer (FPy-FP) is characterized by comprising the following steps: the reaction equation of the specific synthetic route is as follows:
compared with the prior art, the invention has the beneficial effects that:
(1) The novel non-fullerene small-molecule cathode interface layer material FPy-FP provided by the invention has a simple synthesis process, can obtain a product by only two steps, and can realize high conductivity, high electron mobility and environment-friendly water/alcohol-soluble processing.
(2) Due to the fact that the side chain of the small molecule contains the pyridyl modification group, the nitrogen atom and the electrode substrate or even the active layer interact with each other, an interface dipole can be formed, the interface potential barrier is reduced, ohmic contact is formed, selective transport and a built-in electric field of electrons are improved, the electrons are collected by a cathode, and the electron mobility is improved accordingly.
(3) The hydrogen atom on the conjugated fluorene skeleton and the fluorine atom on the connected fluorobenzene form F \8230andH bond, so that the planarity of FPy-FP molecules is enhanced, the stacking among molecules is facilitated, the crystallinity is properly improved, the transportation of electrons is promoted to a certain extent, and the electron mobility is improved.
(4) Fluorine on the connected benzene ring enables the fluorenyl group to have a lower lowest unoccupied orbital level (-3.56 eV), improves the level matching degree at the FPy-FP/cathode interface, obtains favorable electron extraction efficiency, and shows higher electron mobility and better interface compatibility.
(5) Because oxygen and fluorine atoms have electron-withdrawing capabilities (i.e., strong electronegativity), negative potentials are predominantly distributed on the oxygen and fluorine atoms, while positive potentials are distributed on the hydrogen atoms on the conjugated structure. The uneven distribution of the electrostatic potential causes a highly electron-deficient region to appear in the molecule, thereby promoting the transfer of electrons from the acceptor to the cathode interface layer and showing better electron selectivity.
Drawings
FIG. 1 is a structural diagram of a fluorene molecule-locked small molecule cathode interface layer FPy-FP according to the present invention.
FIG. 2 is a structural diagram of a device of a fluorene molecule-locked small molecule cathode interface layer FPy-FP according to the present invention.
FIG. 3 is a specific synthesis route diagram of a fluorene molecule-locked small molecule cathode interface layer FPy-FP according to the present invention.
Detailed description of the invention
The invention is further described below with reference to the accompanying drawings.
The reaction of the invention is shown in the attached figure, and the specific reaction steps are as follows: a synthesis step of a fluorene molecular lock small molecule cathode interface layer FPy-FP comprises the following steps:
the method comprises the following steps: synthesis of pyridyl side chain of 2, 7-dibromofluorene FPy-2 Br:
(1) Weighing 1.2mmol of reactants 2, 7-dibromo-9, 9-di (6-bromohexyl) fluorene and 2.64mmol of 4-hydroxypyridine, adding into a flask, adding 500mg of potassium carbonate into the flask, building a reflux device, vacuumizing for 3 minutes, introducing N 2 5 minutes (3 replicates). In general on N 2 In the case of (2), 40mL of ultra-dry DMF was injected as a reaction solution through a rubber tube connected to a flask via a syringe along a branch lineSealing the pinhole with sealing tape after injection, starting magnetic stirrer to dissolve the reactant, vacuumizing for 5 min, and introducing N 2 For 5 minutes. Then, the mixture is wrapped by a black plastic bag and protected from light, is fixed by a bandage, and is heated, stirred and refluxed for reaction for 24 hours at 125 ℃.
(2) After the reaction is finished, the device is disassembled, and the reaction solution is cooled to room temperature in a dark place. And (3) building a reduced pressure distillation device, carrying out reduced pressure distillation on the reaction liquid at the temperature of 115-120 ℃ for 5 hours, and distilling out the DMF solvent to obtain a small amount of light yellow emulsion.
(3) After adding 30mL of dichloromethane to dissolve, extracting with 3 times volume of water, collecting the lower layer organic phase yellow liquid, repeating for 3 times, adding appropriate amount of anhydrous magnesium sulfate into the collected lower layer liquid, removing the residual water, stirring, and standing. The magnesium sulfate was removed by suction filtration.
(4) Putting the obtained yellow liquid into a heart-shaped bottle, performing rotary evaporation at 40 ℃ to remove dichloromethane in the heart-shaped bottle to obtain a foamy solid substance, and drying the foamy solid substance in a vacuum drying oven at 60 ℃ for 24 hours to obtain a light yellow solid crude product of FPy-2 Br.
(5) The crude product was dissolved with dichloromethane and purified with methanol: and (3) dropping a plate as a developing solvent by using ethyl acetate =1. And (3) spin-drying the obtained light yellow liquid, putting the light yellow liquid into a vacuum drying oven for drying for 24h, and scraping the product to obtain light yellow solid FPy-2Br with the yield of 45%.
Step two: and (3) synthesizing a fluorene type molecular lock small molecular cathode interface layer FPy-FP:
(1) 0.5mmol of FPy-2Br and 1.2mmol of 2-fluorophenylboronic acid pinacol ester are taken as reactants and added into a flask, and 500mg of potassium carbonate and 50mg of catalyst Pd (PPh) 3 ) 4 . Building a reflux device, vacuumizing for 3 minutes, and introducing N 2 5 minutes (3 replicates). In general on N 2 In the case of (1), 20mL of ultra-dry DMF was injected with a syringe, the respective raw materials were mixed, evacuated again for 5 minutes, and N was introduced 2 For 5 minutes. Heating and refluxing for 24h at 105 ℃, and shading the black plastic bag.
(2) And cooling the reaction to room temperature, building a reduced pressure distillation device, carrying out reduced pressure distillation on the reaction liquid at the temperature of 115-120 ℃ for 5 hours, and distilling out the DMF solvent to obtain a small amount of light yellow emulsion.
(3) It was extracted with water and dichloromethane to remove the water solubles and the catalyst. After the extraction was completed, an appropriate amount of anhydrous magnesium sulfate was added to remove residual water in the liquid, and the solvent was spin-dried to obtain a crude product.
(4) Crude product was purified using methanol in volume ratio: ethyl acetate =1.5, the resulting liquid was spun dry, placed in a vacuum oven to dry for 24h, and the product was scraped off to give FPy-FP as an off-white solid in 88% yield.
The beneficial effects of the invention are: the invention discloses a preparation method of a fluorene molecular lock micromolecule cathode interface layer, which is characterized in that a pyridyl group is connected on a 2, 7-dibromofluorene side chain through a Williamson synthesis method to synthesize a bromofluorene derivative, and a Suzuki reaction is carried out to connect fluorobenzene on the 2, 7-site carbon of a fluorene ring to obtain a product. Firstly, the side chain of the metal cathode/cathode electrode active layer contains a pyridyl modification group, so that the metal cathode/cathode electrode active layer has good alcohol solubility, an interface dipole can be formed at the interface of the metal cathode/cathode interface layer and the active layer, the cathode work function is reduced, and the receptor and the cathode are promoted to form good ohmic contact, so that the interface barrier between the electrode and the active layer is further reduced, and the carrier mobility and the open-circuit voltage are improved; sp of nitrogen atom on pyridyl 2 Lone-pair electrons exist in the hybrid track, an electron donating effect is shown, charge transport loss is reduced through an n-type doped active layer receptor, and the contact between the active layer and a metal cathode is improved; the hydrogen atom on the fluorene ring and the fluorine atom on the fluorobenzene form F \8230, and the H weak bond forms a molecular lock, so that the planarity of molecules is greatly enhanced, the molecules have good molecular accumulation, and the stability and the efficiency of the device are finally improved due to proper crystallinity. Secondly, the strong electron-withdrawing ability of fluorine atoms enables molecules to present a highly electron-deficient region, and promotes the transfer of electrons from an acceptor to a cathode interface layer. In addition, due to the existence of the fluorine atom, the fluorenyl group has a lower lowest unoccupied orbital level, the energy level matching degree at the FPy-FP/cathode interface is improved, the electron extraction efficiency is improved, and the fluorenyl group has higher electron mobility and better interface compatibility.
Claims (6)
1. A fluorene molecule locks micromolecule negative pole interface layer which characterized in that: has a structure shown in formula I, and comprises the following components:
2. a preparation method of a cathode interface layer containing the fluorene molecule lock micromolecules as claimed in claim 1 is characterized by comprising the following steps:
the method comprises the following steps: synthesizing a pyridyl side chain FPy-2Br of 2, 7-dibromofluorene;
step two: and (3) synthesizing a fluorene molecular locked small molecular cathode interface layer FPy-FP.
3. The method according to claim 2, wherein the interface layer comprises a fluorene molecule-locked small molecule cathode, and the interface layer comprises: the synthesis of pyridyl side chain FPy-2Br of 2, 7-dibromo fluorene comprises the following specific steps:
(1) Weighing 1.2mmol of reactant 2, 7-dibromo-9, 9-di (6-bromohexyl) fluorene and 2.64mmol of 4-hydroxypyridine, adding into a flask, adding 500mg of potassium carbonate into the flask, building a reflux device, vacuumizing for 3 minutes, introducing N 2 5 minutes after N introduction 2 In the case of (1), 40mL of ultra-dry N, N-dimethylformamide was injected as a solvent for the reaction using a rubber tube connected along a branch tube of the flask with a syringe, the needle hole was sealed with a sealing tape after the injection was completed, the magnetic stirrer was turned on to dissolve the reactant sufficiently, vacuum was applied again for 5 minutes, and N was introduced 2 The time is 5 minutes; then wrapping the film with a black plastic bag in a dark place, fixing the film with a binding tape, and heating and refluxing the film for 24 hours at 125 ℃;
(2) After the reaction is finished, disassembling the device, cooling the reaction liquid to room temperature in a dark place, building a reduced pressure distillation device, carrying out reduced pressure distillation on the reaction liquid at the temperature of 115-120 ℃ for 5 hours, and distilling out the solvent N, N-dimethylformamide to obtain a small amount of light yellow emulsion;
(3) Adding 30mL of dichloromethane for dissolution, extracting with 3 times of water, collecting lower organic phase yellow liquid, repeating for 3 times, adding appropriate amount of anhydrous magnesium sulfate into the collected lower liquid, removing residual water, stirring, standing, vacuum filtering, and removing magnesium sulfate;
(4) Putting the obtained yellow liquid into a heart-shaped bottle, performing rotary evaporation at 40 ℃ to remove dichloromethane in the yellow liquid to obtain a foamed solid substance, and drying the foamed solid substance in a vacuum drying oven at 60 ℃ for 24 hours to obtain a light yellow solid crude product of FPy-2 Br;
(5) The crude product was dissolved with dichloromethane and purified with methanol: and (2) taking ethyl acetate =1 as a developing agent, spotting the plate by using an ultraviolet analyzer for irradiation observation, then purifying the product by using column chromatography, loading the column by using a wet method, loading the sample by using a dry method, spin-drying the obtained light yellow liquid, putting the light yellow liquid into a vacuum drying oven for drying for 24 hours, and scraping the product to obtain light yellow solid FPy-2Br with the yield of 45%.
4. The method for preparing a fluorene molecule-locked small molecule cathode interface layer according to claim 2, wherein the method comprises the following steps: the synthesis of the fluorene molecular lock micromolecule cathode interface layer FPy-FP comprises the following specific steps:
(1) 0.5mmol FPy-2Br and 1.2mmol 2-fluorophenylboronic acid pinacol ester are weighed into a flask, and 500mg potassium carbonate and 50mg catalyst Pd (PPh) are added 3 ) 4 (ii) a Building a reflux device, vacuumizing for 3 minutes, and introducing N 2 5 minutes; in general N 2 In the case of (1), 20mL of ultra-dry DMF was injected with a syringe, the respective raw materials were mixed, evacuated again for 5 minutes, and N was introduced 2 The time is 5 minutes, the mixture is heated and refluxed for 24 hours at 105 ℃, and a black plastic bag is protected from light;
(3) After the reaction is cooled to room temperature, a reduced pressure distillation device is set up, the reaction liquid is subjected to reduced pressure distillation at the temperature of 115-120 ℃ for 5 hours, and the solvent N, N-dimethylformamide is evaporated to obtain a small amount of light yellow emulsion;
(4) Extracting with water and dichloromethane to remove water soluble substances and catalyst, adding appropriate amount of anhydrous magnesium sulfate to remove residual water in the liquid after extraction is completed, and spin-drying the solvent to obtain a crude product;
(5) Crude product was purified using methanol in volume ratio: ethyl acetate =1.5, and the resulting liquid was spin-dried, placed in a vacuum oven for drying for 24h, and the product was scraped off to give off-white solid FPy-FP with a yield of 88%.
5. A non-fullerene solar cell device with a fluorene-based molecule locked small molecule cathode interface layer according to claim 1, wherein:
the electrode comprises an ITO glass layer, a PEDOT PSS anode interface layer arranged on the ITO glass layer, an active layer arranged on the PEDOT PSS layer, a fluorene molecular locking micromolecule cathode interface layer arranged on the active layer and an Al electrode layer arranged on the fluorene molecular locking micromolecule cathode interface layer.
6. The method for synthesizing FPy-FP on the interface layer of the fluorene molecular locked small molecule cathode according to claim 1, wherein the method comprises the following steps: the reaction equation of the specific synthetic route is as follows:
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030091859A1 (en) * | 2001-05-22 | 2003-05-15 | Hyun-Nam Cho | Fluorene compounds containing various functional groups, polymers thereof and el element using the same |
| CN102712652A (en) * | 2010-03-23 | 2012-10-03 | 海洋王照明科技股份有限公司 | Copolymer containing fluorenylporphyrin-benzene, preparation method and use thereof |
| CN103666453A (en) * | 2013-11-22 | 2014-03-26 | 宁波大学 | Blue fluorescent material containing trifluoromethylfluorene and preparation method thereof |
| US20140374724A1 (en) * | 2011-12-07 | 2014-12-25 | Doosan Corporation | Organic light-emitting compound and organic electroluminescent device using same |
| US20150236271A1 (en) * | 2012-08-10 | 2015-08-20 | Doosan Corporation | Novel compound and organic electroluminescence device comprising same |
| CN105330825A (en) * | 2015-11-01 | 2016-02-17 | 华南理工大学 | Water/alcohol-soluble conjugated polymer with side chain containing pyridine and preparation method and application of water/alcohol-soluble conjugated polymer |
| US20200231602A1 (en) * | 2019-01-18 | 2020-07-23 | Beijing Summer Sprout Technology Co., Ltd. | Organic compound and electroluminescent device containing the same |
-
2022
- 2022-08-08 CN CN202210946671.1A patent/CN115304622A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030091859A1 (en) * | 2001-05-22 | 2003-05-15 | Hyun-Nam Cho | Fluorene compounds containing various functional groups, polymers thereof and el element using the same |
| CN102712652A (en) * | 2010-03-23 | 2012-10-03 | 海洋王照明科技股份有限公司 | Copolymer containing fluorenylporphyrin-benzene, preparation method and use thereof |
| US20140374724A1 (en) * | 2011-12-07 | 2014-12-25 | Doosan Corporation | Organic light-emitting compound and organic electroluminescent device using same |
| US20150236271A1 (en) * | 2012-08-10 | 2015-08-20 | Doosan Corporation | Novel compound and organic electroluminescence device comprising same |
| CN103666453A (en) * | 2013-11-22 | 2014-03-26 | 宁波大学 | Blue fluorescent material containing trifluoromethylfluorene and preparation method thereof |
| CN105330825A (en) * | 2015-11-01 | 2016-02-17 | 华南理工大学 | Water/alcohol-soluble conjugated polymer with side chain containing pyridine and preparation method and application of water/alcohol-soluble conjugated polymer |
| US20200231602A1 (en) * | 2019-01-18 | 2020-07-23 | Beijing Summer Sprout Technology Co., Ltd. | Organic compound and electroluminescent device containing the same |
Non-Patent Citations (2)
| Title |
|---|
| LIN LIN等: "Alcohol-soluble fluorene derivate functionalized with pyridyl groups as a high-performance cathode interfacial material in organic solar cells", 《NEW JOURNAL OF CHEMICAL》, vol. 45, no. 10, pages 4584 - 4591 * |
| 赵亚云等: "两种新型芴衍生物的合成、晶体结构及光谱性能", 《发光学报》, vol. 35, no. 2, pages 156 - 164 * |
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