CN110775957A - Preparation method of bio-based electron transport material - Google Patents
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- CN110775957A CN110775957A CN201911171214.4A CN201911171214A CN110775957A CN 110775957 A CN110775957 A CN 110775957A CN 201911171214 A CN201911171214 A CN 201911171214A CN 110775957 A CN110775957 A CN 110775957A
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
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- YFZOUMNUDGGHIW-UHFFFAOYSA-M p-chloromercuribenzoic acid Chemical compound OC(=O)C1=CC=C([Hg]Cl)C=C1 YFZOUMNUDGGHIW-UHFFFAOYSA-M 0.000 description 1
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- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
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Abstract
The invention provides a preparation method of a bio-based electron transport material, which comprises the following steps: putting a biomass raw material, a nitrogen-doped reagent and an organic solvent into a reaction kettle, and firstly carrying out ultrasonic treatment for 2-5 minutes; then the cover is tightly covered, the reaction kettle is placed into a muffle furnace, the temperature is slowly raised to 150 ℃ and 200 ℃ for reaction for 6-8 h; after the reaction is finished, cooling to 20 ℃; filtering to separate large-particle carbide; separating and purifying by silica gel column chromatography, and distilling under reduced pressure to remove the reaction solvent to obtain the biological agent electron transport material. The bio-based electron transport material prepared by the method has high electron transport performance; and the preparation raw materials have wide sources and low price.
Description
Technical Field
The invention relates to the technical field of materials, in particular to a preparation method of a bio-based electron transport material for an organic thin-film solar cell.
Background
Efficient conversion of solar energy to electrical energy remains one of the biggest challenges facing humans. Despite the rapid progress in organic thin film solar cell research in recent years, high purity single crystal silicon is still the leading material in the solar cell industry due to the cost of material production. In fig. 1 a) shows the basic structure of an organic thin film solar cell. Like an organic light emitting diode, it is also a "sandwich" structure in which an organic active layer is sandwiched by electrodes at both ends. The organic active layer is generally composed of a P-type material (e.g., a conductive polymer polythiophene, P3HT) that transports positive holes and an n-type material (a derivative of fullerene, PCBM) that transports electrons. The positive and negative charges generated under the excitation of sunlight respectively pass through the corresponding electrodes conveyed by the P-type material and the n-type material, so that the complete charge separation is realized, and voltage and current are formed in an external circuit. Despite the rapid progress in organic thin film solar cell research in recent years, high purity single crystal silicon remains the dominant material in the solar cell industry due to the expensive synthesis cost of PCBM materials. The bio-based carbon nanodots, which also have electron transport ability and are inexpensive, can be used as an electron transport material for solar cells (b in fig. 1) instead of PCMB, which is expensive in synthesis cost.
Carbon nanodots (Carbon nanodots) are quasi-spherical nanoparticles with discrete particle size ranging from 3 to 10nm and thickness below 1nm, which were first reported by foreign research institutes in 2004, and have been widely studied and reported due to their unique fluorescent properties, excellent biocompatibility (no toxicity), and rapid and inexpensive preparation method. The bio-based carbon nanodots are prepared by using biomass raw materials such as cellulose, starch, chitosan, glucose and the like as carbon sources and carbonizing the biomass raw materials by a solvent method.
At present, the biggest technical problem of the bio-based carbon nanodot fluorescent whitening agent is that the electron transport efficiency is lower compared with that of the conventional electron transport material PCBM. The general method is to introduce electron-rich groups such as N element (such as urea, ethylenediamine and other nitrogen doping agents) into the surface of the carbon nanodots, so as to increase the electron cloud density of the surface of the carbon nanodots, thereby improving the electron mobility of the material and improving the electron transport performance by 10-100 times.
Disclosure of Invention
The invention aims to solve the defects of the prior art and provide a preparation method of a bio-based electron transport material which is cheaper and has higher electron transport efficiency.
A method for preparing a bio-based electron transport material, comprising:
putting a biomass raw material, a nitrogen-doped reagent and an organic solvent into a reaction kettle, and firstly carrying out ultrasonic treatment for 2-5 minutes;
then the cover is tightly covered, the reaction kettle is placed into a muffle furnace, the temperature is slowly raised to 150 ℃ and 200 ℃ for reaction for 6-8 h;
after the reaction is finished, cooling to 20 ℃; filtering to separate large-particle carbide;
separating and purifying by silica gel column chromatography, and distilling under reduced pressure to remove the reaction solvent to obtain the biological agent electron transport material.
Further, in the preparation method of the bio-based electron transport material, the biomass raw material is any one of cellulose, starch, chitosan, lignin, hemicellulose or glucose.
Further, in the preparation method of the bio-based electron transport material, the organic solvent is one or a combination of acetone, hexanone or cyclohexanone.
Further, in the preparation method of the bio-based electron transport material, the nitrogen doping agent is any one of urea or ethylenediamine.
Further, in the preparation method of the bio-based electron transport material, the reaction kettle is a stainless steel reaction kettle.
The bio-based electron transport material prepared according to any one of the above methods.
Compared with the prior art, the invention has the following advantages:
the traditional electron transport material used for the organic thin-film solar cell is fullerene derivative (PCBM) and has high synthesis cost, while the bio-based electron transport material component of the invention is carbon nanodots, and the raw materials for preparing the carbon nanodots are also natural products instead of traditional petrochemicals, so the material is wide and the price is low; more importantly, the electron-rich property of nitrogen element is utilized to increase the electron cloud density on the surface of the carbon nanodots and increase the electron mobility of molecules, so that the conductivity of the material is higher.
Drawings
Fig. 1 is a diagram showing the structure of an organic solar cell and the structure of a cell material used therein.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention are described clearly and completely below, and it is obvious that the described embodiments are some, not all embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
The invention relates to a preparation method of a bio-based electron transport material, which comprises the following steps: putting 10g of cellulose, 100mL of acetone and urea into a reaction kettle, performing ultrasonic treatment for 2 minutes, uniformly mixing the system, putting the reaction kettle into a muffle furnace, reacting at 200 ℃ for 6 hours, cooling to 20 ℃ after the reaction is finished, performing suction filtration, separating large-particle carbide, and performing reduced pressure distillation to remove a reaction solvent; the product solution was separated and purified by silica gel column chromatography in a dichloromethane solvent (dichloromethane and ethanol mixture as mobile phase). Finally, the vacuum degree is between 0.04 and 0.08MPa, and the mixture is steamed under reduced pressureAnd distilling to remove the solvent to prepare the bio-based carbon nano-dot electron transport material. The synthetic yield is 25%; and (3) measuring: conductivity (electron transport property) of 2.2X 10
-4cm
2V
-1s
-1The photoelectric conversion efficiency of the solar cell prepared by mixing P3HT was 3.10%.
Example 2
The invention relates to a preparation method of a bio-based electron transport material, which comprises the following steps: putting 10g of cellulose, 100mL of acetone and ethylenediamine into a reaction kettle, performing ultrasonic treatment for 2 minutes, uniformly mixing the system, putting the reaction kettle into a muffle furnace, reacting at 200 ℃ for 8 hours, cooling to 20 ℃ after the reaction is finished, performing suction filtration, separating large-particle carbide, and performing reduced pressure distillation to remove a reaction solvent; the product solution was separated and purified by silica gel column chromatography in a dichloromethane solvent (dichloromethane and ethanol mixture as mobile phase). And finally, carrying out reduced pressure distillation to remove the solvent under the condition that the vacuum degree is 0.04-0.08MPa, and preparing the bio-based carbon nanodot electron transport material. The synthesis yield is 22%; and (3) measuring: the conductivity (electron transport property) was 2.8X 10
-4cm
2V
-1s
-1The photoelectric conversion efficiency of the solar cell prepared by mixing P3HT was 2.50%.
Example 3
The invention relates to a preparation method of a bio-based electron transport material, which comprises the following steps: putting 10g of starch, 100mL of acetone and urea into a reaction kettle, performing ultrasonic treatment for 2 minutes, uniformly mixing the system, putting the reaction kettle into a muffle furnace, reacting at 200 ℃ for 6 hours, cooling to 20 ℃ after the reaction is finished, performing suction filtration, separating large-particle carbide, and performing reduced pressure distillation to remove a reaction solvent; the product solution was separated and purified by silica gel column chromatography in a dichloromethane solvent (dichloromethane and ethanol mixture as mobile phase). And finally, carrying out reduced pressure distillation to remove the solvent under the condition that the vacuum degree is 0.04-0.08MPa, and preparing the bio-based carbon nanodot electron transport material. The synthesis yield is 20%; and (3) measuring: conductivity (electron transport property) of 1.5X 10
- 4cm
2V
-1s
-1Photoelectric conversion efficiency of solar cell prepared by mixing P3HTThe content was 2.80%.
Example 4
The invention relates to a preparation method of a bio-based electron transport material, which comprises the following steps: putting 10g of chitosan, 100mL of acetone and urea into a reaction kettle, performing ultrasonic treatment for 2 minutes, uniformly mixing the system, putting the reaction kettle into a muffle furnace, reacting at 150 ℃ for 6 hours, cooling to 20 ℃ after the reaction is finished, performing suction filtration, separating large-particle carbide, and performing reduced pressure distillation to remove a reaction solvent; the product solution was separated and purified by silica gel column chromatography in a dichloromethane solvent (dichloromethane and ethanol mixture as mobile phase). And finally, carrying out reduced pressure distillation to remove the solvent under the condition that the vacuum degree is 0.04-0.08MPa, and preparing the bio-based carbon nanodot electron transport material. The synthesis yield is 28%; and (3) measuring: conductivity (electron transport property) of 2.5X 10
-4cm
2V
-1s
-1The photoelectric conversion efficiency of the solar cell prepared by mixing P3HT was 3.20%.
Example 5
The invention relates to a preparation method of a bio-based electron transport material, which comprises the following steps: putting 10g of lignin, 100mL of acetone and urea into a reaction kettle, carrying out ultrasonic treatment for 2 minutes, uniformly mixing the system, putting the reaction kettle into a muffle furnace, reacting at 180 ℃ for 6 hours, cooling to 20 ℃ after the reaction is finished, carrying out suction filtration, separating large-particle carbide, and carrying out reduced pressure distillation to remove a reaction solvent; the product solution was separated and purified by silica gel column chromatography in a dichloromethane solvent (dichloromethane and ethanol mixture as mobile phase). And finally, carrying out reduced pressure distillation to remove the solvent under the condition that the vacuum degree is 0.04-0.08MPa, and preparing the bio-based carbon nanodot electron transport material. The synthesis yield is 20%; and (3) measuring: conductivity (electron transport property) of 1.0X 10
-4cm
2V
-1s
-1The photoelectric conversion efficiency of the solar cell prepared by mixing P3HT was 1.60%.
Example 6
The invention relates to a preparation method of a bio-based electron transport material, which comprises the following steps: putting 10g of chitosan, 100mL of hexanone and urea into a reaction kettle, and performing ultrasonic treatment2 minutes, after the system is uniformly mixed, putting the reaction kettle into a muffle furnace, reacting at 150 ℃ for 6 hours, cooling to 20 ℃ after the reaction is finished, performing suction filtration, separating large-particle carbide, and performing reduced pressure distillation to remove a reaction solvent; the product solution was separated and purified by silica gel column chromatography in a dichloromethane solvent (dichloromethane and ethanol mixture as mobile phase). And finally, carrying out reduced pressure distillation to remove the solvent under the condition that the vacuum degree is 0.04-0.08MPa, and preparing the bio-based carbon nanodot electron transport material. The synthesis yield is 30%; and (3) measuring: the conductivity (electron transport property) was 2.8X 10
-4cm
2V
-1s
-1The photoelectric conversion efficiency of the solar cell prepared by mixing P3HT was 3.5%.
Example 7
The invention relates to a preparation method of a bio-based electron transport material, which comprises the following steps: putting 10g of chitosan, 100mL of hexanone and ethylenediamine into a reaction kettle, performing ultrasonic treatment for 2 minutes, uniformly mixing the system, putting the reaction kettle into a muffle furnace, reacting at 150 ℃ for 6 hours, cooling to 20 ℃ after the reaction is finished, performing suction filtration, separating large-particle carbide, and performing reduced pressure distillation to remove a reaction solvent; the product solution was separated and purified by silica gel column chromatography in a dichloromethane solvent (dichloromethane and ethanol mixture as mobile phase). And finally, carrying out reduced pressure distillation to remove the solvent under the condition that the vacuum degree is 0.04-0.08MPa, and preparing the bio-based carbon nanodot electron transport material. The synthesis yield is 20%; and (3) measuring: conductivity (electron transport property) of 1.7X 10
-4cm
2V
-1s
-1The photoelectric conversion efficiency of the solar cell prepared by mixing P3HT was 2.60%.
Example 8
The invention relates to a preparation method of a bio-based electron transport material, which comprises the following steps: putting 10g of starch, 100mL of acetone and ethylenediamine into a reaction kettle, performing ultrasonic treatment for 2 minutes, uniformly mixing the system, putting the reaction kettle into a muffle furnace, reacting at 180 ℃ for 6 hours, cooling to 20 ℃ after the reaction is finished, performing suction filtration, separating large-particle carbide, and performing reduced pressure distillation to remove a reaction solvent; adding the product solution into dichloromethane solvent, and using siliconSeparation and purification are carried out by gel column chromatography (dichloromethane and ethanol mixture as mobile phase). And finally, carrying out reduced pressure distillation to remove the solvent under the condition that the vacuum degree is 0.04-0.08MPa, and preparing the bio-based carbon nanodot electron transport material. The synthesis yield is 20%; and (3) measuring: conductivity (electron transport property) of 1.0X 10
- 4cm
2V
-1s
-1The photoelectric conversion efficiency of the solar cell prepared by mixing P3HT was 2.00%.
Example 9
The invention relates to a preparation method of a bio-based electron transport material, which comprises the following steps: putting a biomass raw material, a solvent and a nitrogen-doped reagent into a reaction kettle, carrying out ultrasonic treatment for 2 minutes, uniformly mixing the system, putting the reaction kettle into a muffle furnace, reacting at 150 ℃ for 6 hours, cooling to 20 ℃ after the reaction is finished, carrying out suction filtration, separating large-particle carbide, and carrying out reduced pressure distillation to remove the reaction solvent; the product solution was separated and purified by silica gel column chromatography in a dichloromethane solvent (dichloromethane and ethanol mixture as mobile phase). And finally, carrying out reduced pressure distillation to remove the solvent under the condition that the vacuum degree is 0.04-0.08MPa, and preparing the bio-based carbon nanodot electron transport material. The synthesis yield is 20%; and (3) measuring: conductivity (electron transport property) of 1.5X 10
- 4cm
2V
-1s
-1The photoelectric conversion efficiency of the solar cell prepared by mixing P3HT was 2.80%.
The biomass raw material is chitosan. The solvent is the combination of two of acetone and hexanone. The nitrogen doping reagent is urea. The reaction kettle is a stainless steel reaction kettle.
Example 10
The invention relates to a preparation method of a bio-based electron transport material, which comprises the following steps: putting a biomass raw material, a solvent and a nitrogen-doped reagent into a reaction kettle, carrying out ultrasonic treatment for 2 minutes, uniformly mixing the system, putting the reaction kettle into a muffle furnace, reacting at 150 ℃ for 6 hours, cooling to 20 ℃ after the reaction is finished, carrying out suction filtration, separating large-particle carbide, and carrying out reduced pressure distillation to remove the reaction solvent; subjecting the product solution to silica gel column chromatography in dichloromethane solventSeparation and purification (dichloromethane and ethanol mixture as mobile phase). And finally, carrying out reduced pressure distillation to remove the solvent under the condition that the vacuum degree is 0.04-0.08MPa, and preparing the bio-based carbon nanodot electron transport material. The synthesis yield is 18%; and (3) measuring: conductivity (electron transport property) of 1.3X 10
- 4cm
2V
-1s
-1The photoelectric conversion efficiency of the solar cell prepared by mixing P3HT was 2.60%.
The biomass raw material is chitosan. The solvent is the combination of two of acetone and cyclohexanone. The nitrogen doping reagent is urea. The reaction kettle is a stainless steel reaction kettle.
Comparative example:
the preparation method of the bio-based electron transport material without using the nitrogen doping agent comprises the following steps: putting 10g of chitosan and 100mL of hexanone into a reaction kettle, performing ultrasonic treatment for 2 minutes, uniformly mixing the system, putting the reaction kettle into a muffle furnace, reacting at 150 ℃ for 6 hours, cooling to 20 ℃ after the reaction is finished, performing suction filtration, separating large-particle carbide, and performing reduced pressure distillation to remove a reaction solvent; the product solution was separated and purified by silica gel column chromatography in a dichloromethane solvent (dichloromethane and ethanol mixture as mobile phase). And finally, carrying out reduced pressure distillation to remove the solvent under the condition that the vacuum degree is 0.04-0.08MPa, and preparing the bio-based carbon nanodot electron transport material. The synthesis yield is 18%; and (3) measuring: conductivity (electron transport property) of 1.0X 10
- 6cm
2V
-1s
-1The photoelectric conversion efficiency of the solar cell prepared by mixing P3HT was 0.40%.
Comparative example 1 and example 6 using a nitrogen-doping agent (conductivity 2.8X 10)
-4cm
2V
-1s
-1And the photoelectric conversion efficiency of the solar cell prepared by mixing P3HT is 3.5%), the electric conductivity and the photoelectric conversion efficiency of the electron transport material are obviously improved.
Finally, it should be noted that: the above examples are only intended to illustrate the technical solution of the present invention, but not to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions of the embodiments of the present invention.
Claims (6)
1. A method for preparing a bio-based electron transport material, comprising:
putting a biomass raw material, a nitrogen-doped reagent and an organic solvent into a reaction kettle, and firstly carrying out ultrasonic treatment for 2-5 minutes;
then the cover is tightly covered, the reaction kettle is placed into a muffle furnace, the temperature is slowly raised to 150 ℃ and 200 ℃ for reaction for 6-8 h;
after the reaction is finished, cooling to 20 ℃; filtering to separate large-particle carbide;
separating and purifying by silica gel column chromatography, and distilling under reduced pressure to remove the reaction solvent to obtain the biological agent electron transport material.
2. The method for preparing a bio-based electron transport material according to claim 1, wherein: the biomass raw material is any one of cellulose, starch, chitosan, lignin, hemicellulose or glucose.
3. The method for preparing a bio-based electron transport material according to claim 1, wherein: the organic solvent is one or a combination of more of acetone, hexanone or cyclohexanone.
4. The method for preparing a bio-based electron transport material according to claim 1, wherein: the nitrogen doping reagent is any one of urea or ethylenediamine.
5. The method for preparing a bio-based electron transport material according to claim 1, wherein: the reaction kettle is a stainless steel reaction kettle.
6. A bio-based electron transport material prepared according to the method of any one of claims 1 to 5.
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106520116A (en) * | 2016-10-11 | 2017-03-22 | 杭州电子科技大学 | Red luminescent carbon quantum dot, preparation method and application thereof |
| CN106784326A (en) * | 2016-12-28 | 2017-05-31 | 南京大学昆山创新研究院 | The preparation method of the perovskite solar cell with nitrogen-doped carbon point as electron transfer layer and the electron transfer layer based on nitrogen-doped carbon point |
| JP6271745B2 (en) * | 2014-01-17 | 2018-01-31 | カーボン ナノ エンジニアリング システムズ コーポレイション | Large-scale manufacturing method of graphene quantum dots |
| CN107814374A (en) * | 2017-11-07 | 2018-03-20 | 北京化工大学 | A kind of method of regulation and control carbon material pattern |
| CN108767117A (en) * | 2018-06-07 | 2018-11-06 | 吉林大学 | A kind of perovskite solar cell and preparation method thereof being passivated grain boundary defects based on carbon quantum dot doping anti-solvent |
| CN109207148A (en) * | 2017-07-08 | 2019-01-15 | 张宏伟 | A kind of magnanimity preparation method of high yield carbon quantum dot |
| KR101997968B1 (en) * | 2017-07-24 | 2019-07-09 | 재단법인대구경북과학기술원 | Spider network structure composition of N-doped carbon nanofibers containing MnCoOx nanoparticles, the preparation method, and application to anode material for secondary battery |
-
2019
- 2019-11-26 CN CN201911171214.4A patent/CN110775957A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6271745B2 (en) * | 2014-01-17 | 2018-01-31 | カーボン ナノ エンジニアリング システムズ コーポレイション | Large-scale manufacturing method of graphene quantum dots |
| CN106520116A (en) * | 2016-10-11 | 2017-03-22 | 杭州电子科技大学 | Red luminescent carbon quantum dot, preparation method and application thereof |
| CN106784326A (en) * | 2016-12-28 | 2017-05-31 | 南京大学昆山创新研究院 | The preparation method of the perovskite solar cell with nitrogen-doped carbon point as electron transfer layer and the electron transfer layer based on nitrogen-doped carbon point |
| CN109207148A (en) * | 2017-07-08 | 2019-01-15 | 张宏伟 | A kind of magnanimity preparation method of high yield carbon quantum dot |
| KR101997968B1 (en) * | 2017-07-24 | 2019-07-09 | 재단법인대구경북과학기술원 | Spider network structure composition of N-doped carbon nanofibers containing MnCoOx nanoparticles, the preparation method, and application to anode material for secondary battery |
| CN107814374A (en) * | 2017-11-07 | 2018-03-20 | 北京化工大学 | A kind of method of regulation and control carbon material pattern |
| CN108767117A (en) * | 2018-06-07 | 2018-11-06 | 吉林大学 | A kind of perovskite solar cell and preparation method thereof being passivated grain boundary defects based on carbon quantum dot doping anti-solvent |
Non-Patent Citations (4)
| Title |
|---|
| MAREK PIATKOWSKI ET AL.: "Chitosan-Based Carbon Quantum Dots for Biomedical Applications:Synthesis and Characterization", 《NANOMATERIALS》 * |
| PARK, MINKYU ET AL.: "Fabrication of a Combustion-Reacted High-Performance ZnO Electron Transport Layer with Silver Nanowire Electrodes for Organic Solar Cells", 《ACS APPLIED MATERIALS & INTERFACES》 * |
| 张海军: "有机太阳能电池器件的界面修饰和活性层优化的研究", 《中国优秀硕士学位论文全文数据库·工程科技Ⅱ辑》 * |
| 李燕鹏: "氮掺杂型生物质碳点及其复合物的制备与应用研究", 《中国优秀硕士学位论文全文数据库·工程科技Ⅰ辑》 * |
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