CN105140407A - Reduced graphene oxide-3,4,9,10-perylenetetracarboxylic acid potassium compound, preparation method and use thereof - Google Patents

Reduced graphene oxide-3,4,9,10-perylenetetracarboxylic acid potassium compound, preparation method and use thereof Download PDF

Info

Publication number
CN105140407A
CN105140407A CN201510602655.0A CN201510602655A CN105140407A CN 105140407 A CN105140407 A CN 105140407A CN 201510602655 A CN201510602655 A CN 201510602655A CN 105140407 A CN105140407 A CN 105140407A
Authority
CN
China
Prior art keywords
preparation
acid potassium
graphene oxide
buffer layer
compound
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.)
Granted
Application number
CN201510602655.0A
Other languages
Chinese (zh)
Other versions
CN105140407B (en
Inventor
冯莱
顾正艮
周东营
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Suzhou University
Original Assignee
Suzhou University
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Suzhou University filed Critical Suzhou University
Priority to CN201510602655.0A priority Critical patent/CN105140407B/en
Publication of CN105140407A publication Critical patent/CN105140407A/en
Application granted granted Critical
Publication of CN105140407B publication Critical patent/CN105140407B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • 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
    • H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
    • 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

Abstract

The present invention discloses a reduced graphene oxide-3,4,9,10-perylenetetracarboxylic acid potassium compound, a preparation method and a use thereof. Specifically, the preparation method of the present invention comprises the steps of 1) mixing the graphene oxide and the 3,4,9,10-perylenetetracarboxylic acid potassium to obtain a mixed liquor according to the mass ratio of the graphene oxide and the 3,4,9,10-perylenetetracarboxylic acid potassium=1:1.1-1.5; 2) adding the sodium borohydride in the mixed liquor according to the mass ratio of the graphene oxide and the sodium borohydride=1:1.1-1.3, carrying out a reflux reaction to obtain a reaction liquid; 3) putting the reaction liquid in a dialysis bag to dialyse, cooling and drying to obtain the compound. The compound of the present invention possesses a good light absorption characteristic, has a device efficiency obviously higher than a device not having a cathode buffer layer, is controllable in thickness when a liquor method is used to prepare the cathode buffer layer, is low in cost, and has a good air stability which is obviously higher than the air stability of the device taking the calcium metal as the cathode buffer layer.

Description

A kind of redox graphene-3,4,9,10-perylene tetracarboxylic acid potassium compound and its production and use
Technical field
The invention belongs to organic photovoltaic Material Field, relate to a kind of redox graphene-3,4,9,10-perylene tetracarboxylic acid potassium compound, its preparation method, and preparing organic photovoltaic devices as cathode cushioning layer material, the purposes particularly in organic polymer solar cell.
Background technology
Organic polymer solar cell (OrganicPolymerSolarCell, OPSC) is a class novel thin film solar cell.This kind of battery has flexible, advantages of environment protection, and expection will have good Commercial Prospect.In recent years, the efficiency propagation of this kind of battery is very fast, and the efficiency of the stacking polymer solar cell of latest report reaches 11.3%.But the stability of this kind of battery still has much room for improvement, and in production cost, also there is certain compression stroke.
Specifically, the cathode buffer layer of organic polymer solar cell generally adopts calcium metal or lithium fluoride.Because the electronic transmission performance of this kind of material is better, and its surperficial work content is all comparatively mated with the lumo energy of the metal aluminium electrode commonly used and acceptor material, and the efficiency of the device therefore prepared as cathode buffer layer using calcium or lithium fluoride is higher.But calcium or lithium fluoride resilient coating all need the method preparation by vacuum evaporation or sputtering, and preparation cost is higher.In addition, due to this kind of material to water and air all very responsive, and easily to photoactive layer diffusion, thus efficiency decay is very fast in atmosphere to cause device, less stable.
Given this, study and develop a kind of cathode cushioning layer material with lower preparation cost and higher stability and will there is important significance of scientific research and economic worth.
Summary of the invention
Graphene has the large pi-conjugated structure of two dimension, can be used for the novel semiconductor material that preparation property is adjustable.Wherein, redox graphene (rGO) has relatively high conductivity and stability, is a kind of good electron transport material.But because the work content (4.4 ~ 4.5eV) of redox graphene is mated poor with the lumo energy of aluminium electrode and acceptor material, therefore the efficiency of the simple device prepared as cathode buffer layer (or electron transfer layer) using redox graphene is very low.The work content of Graphene can be reduced by the method for chemical modification or modification, thus more effectively collect electronics, can be applied in organic polymer solar cell as cathode buffer layer (or electron transfer layer).
The present invention adopts the method for non-covalent bond chemical modification to prepare redox graphene and 3,4,9,10-perylene tetracarboxylic acid potassium (K 4pTC) compound, method is simple, is easy to a large amount of preparation.Because the dispersiveness of this compound in water or organic solvent is better, solwution method is therefore adopted to prepare the controlled cathode buffer layer of thickness, and for constructing organic polymer solar cell.Obtained device not only battery efficiency is higher, and aerial stability is better, and preparation cost significantly reduces.
On the one hand, the invention provides a kind of preparation method of redox graphene-3,4,9,10-perylene tetracarboxylic acid potassium compound, it comprises the steps:
1) graphene oxide (GO) is dispersed in water, according to graphene oxide: 3,4,9,10-perylene tetracarboxylic acid potassium (K 4the mass ratio of PTC)=1:1.1 ~ 1.5, adds 3,4,9,10-perylene tetracarboxylic acid potassium and mixes, obtaining mixed liquor;
2) according to graphene oxide: the mass ratio of sodium borohydride=1:1.1 ~ 1.3, sodium borohydride (NaBH in the mixed liquor obtained in step 1), is added 4), be heated to backflow, be cooled to room temperature after reacting 3 ~ 4 hours under agitation, obtain reactant liquor;
3) by step 2) in the reactant liquor that obtains put into bag filter dialysis 2 ~ 3 days, content in freeze drying bag filter, obtains redox graphene-3,4,9,10-perylene tetracarboxylic acid potassium compound.
Preferably, in above-mentioned preparation method, graphene oxide described in step 1) is obtained by Hummers method.
Preferably, in above-mentioned preparation method, water described in step 1) is distilled water.
Preferably, in above-mentioned preparation method, mix described in step 1) and completed by mode that is ultrasonic or that add thermal agitation; Preferred, the described ultrasonic time is 2 ~ 3 hours; The described temperature adding thermal agitation is 40 ~ 60 DEG C, and the time is 8 ~ 12 hours.
Preferably, in above-mentioned preparation method, the molecular cut off of bag filter described in step 3) is 1000.K that is free, that do not adsorb can be removed by dialysis procedure 4pTC and other small molecule salt classes, and by saturated adsorption K 4the rGO of PTC stays in bag filter, reaches the effect of separation and purification.
On the other hand, the invention provides a kind of redox graphene-3,4,9,10-perylene tetracarboxylic acid potassium compound prepared by above-mentioned preparation method.
Last aspect, the invention provides above-mentioned redox graphene-3,4,9,10-perylene tetracarboxylic acid potassium compound and is preparing organic photovoltaic devices as cathode buffer layer, the purposes particularly in organic polymer solar cell.
Organic polymer solar cell in the present invention can be prepared by laxative remedy: first on transparent conductive anode, coated anode resilient coating such as PEDOT:PSS(gathers (3, 4-ethylenedioxythiophene): poly-(styrene sulfonic acid)), then on anode buffer layer, photoactive layer is applied as poly-3-hexyl thiophene (P3HT) and 6, the mixture of 6-phenyl carbons 61 methyl butyrate (PCBM), then on photoactive layer, solution as the above-mentioned compound of cathode buffer layer is applied (such as at water/N, solution in dinethylformamide or water/ethanol), last on cathode buffer layer deposition or evaporation metal negative electrode as aluminium, thus obtain required organic polymer solar cell.
Compared with prior art, rGO-K of the present invention 4pTC compound tool has the following advantages:
1) with traditional cathode cushioning layer material as compared with calcium metal or lithium fluoride, rGO-K of the present invention 4pTC compound disperses better in the mixture of water and water and organic solvent, and solwution method can be adopted to prepare cathode buffer layer, and buffer layer thickness is controlled, and preparation cost is lower;
2) rGO-K prepared in the present invention 4pTC compound has good optical absorption characteristics (as shown in Figure 1) within the scope of visible region;
3) rGO-K of the present invention 4pTC compound can mate preferably with conventional acceptor material and aluminium electrode, therefore can be used as the resilient coating (or electron transfer layer) between active layer and aluminium electrode, using compound as the device efficiency of cathode buffer layer apparently higher than the device without cathode buffer layer, close using calcium metal as the device efficiency of cathode buffer layer;
4) rGO-K of the present invention 4the aerial stability of PTC compound is better, and therefore the stability of corresponding device is apparently higher than using calcium metal as the device of cathode buffer layer.
Accompanying drawing explanation
Fig. 1 is the rGO-K of preparation in embodiment 1 4the uv-visible absorption spectra figure of PTC compound.
Fig. 2 is with rGO-K of the present invention 4pTC compound is as the structural representation of the polymer solar battery of cathode buffer layer, and wherein 1 is negative electrode (Al), and 2 is cathode buffer layer (rGO-K 4pTC compound), 3 is photoactive layer (P3HT:PCBM), and 4 is anode buffer layer (PEDOT:PSS), and 5 is anode (ITO electro-conductive glass).
Fig. 3 is respectively with calcium metal, K 4pTC, rGO-K 4pTC compound is as the I-V performance diagram of cathode buffer layer and the polymer solar battery without cathode buffer layer.
Fig. 4 is respectively with calcium metal, K 4pTC, rGO-K 4pTC compound is as the stability test result of the polymer solar battery of cathode buffer layer.
Embodiment
If no special instructions, the material, reagent etc. that use in following embodiment all can be obtained by commercial sources or prepare according to method described in document.
Embodiment 1:rGO-K 4the preparation of PTC compound.
Take GO(5mg), be dispersed in distilled water (10mL), add the K of 1.1 times amount 4pTC(5.5mg), add thermal agitation 8h in 60 DEG C, then add NaBH 4(5.6mg), be heated to backflow, after reacting 4h under agitation, be cooled to room temperature, reactant mixture is loaded dialysis 2d in bag filter (molecular cut off of bag filter is 1000), to remove a small amount of free K 4pTC and small molecule salt, freeze drying, obtains rGO-K 4pTC compound (10mg).
Gained compound is scattered in distilled water, measures its ultraviolet-visible (UV-Vis) spectrum (as shown in Figure 1), therefrom clearly can observe characteristic absorption peak (220 ~ 260nm) and the K of rGO 4the characteristic absorption peak (400 ~ 500nm) of PTC, shows successfully to prepare rGO-K 4pTC compound.
Embodiment 2:rGO-K 4the preparation of PTC compound.
Take GO(5mg), be dispersed in distilled water (10mL), add the K of 1.5 times amount 4pTC(7.5mg), add thermal agitation 12h in 40 DEG C, then add NaBH 4(6.7mg), be heated to backflow, after reacting 3h under agitation, be cooled to room temperature, reactant mixture is loaded dialysis 2d in bag filter (molecular cut off of bag filter is 1000), to remove free K 4pTC and small molecule salt, freeze drying, obtains rGO-K 4pTC compound (10mg).
Ultraviolet-visible (UV-Vis) spectrum of this compound is similar to Fig. 1, clearly can observe rGO and K 4the characteristic absorption peak of PTC.Although the similitude of spectrum also illustrates in preparation process add excessive K simultaneously 4pTC, but do not increase rGO surface K 4the adsorbance of PTC, rGO and K in the compound obtained 4the compound that the ratio of PTC is obtained with embodiment 1 is consistent, is same compound.
Embodiment 3:rGO-K 4the preparation of PTC compound.
Take GO(5mg), be dispersed in distilled water (10mL), add the K of 1.5 times amount 4pTC(7.5mg), in the ultrasonic 3h of room temperature, then NaBH is added 4(6.7mg), be heated to backflow, after reacting 3h under agitation, be cooled to room temperature, reactant mixture is loaded dialysis 2d in bag filter (molecular cut off of bag filter is 1000), to remove free K 4pTC and small molecule salt, freeze drying, obtains rGO-K 4pTC compound (10mg), its ultraviolet-visible (UV-Vis) spectrum is also similar to Fig. 1, clearly can observe rGO and K 4the characteristic absorption peak of PTC.
Configuration embodiment 1: with rGO-K 4pTC compound makes organic polymer solar cell (structure as shown in Figure 2) as cathode buffer layer (or electron transfer layer).
The rGO-K of preparation in preparation embodiment 1 4pTC compound is at H 2o:DMF(v:v=1:2) solution (concentration is about 0.3mg/mL) in, stand-by.At the PEDOT:PSS anode buffer layer (or hole transmission layer) that the electro-conductive glass cleaned up (ITO) upper coating one deck about 30 ~ 40nm is thick, and in 150 DEG C of annealing 30min, then on ITO/PEDOT:PSS, spin coating one deck is about the thick P3HT:PCBM(mass ratio 1:1 of 100nm) photoactive layer, in 150 DEG C of thermal annealing 10min, then adopt above-mentioned rGO-K 4pTC complex solution on photoactive layer spin coating one deck as cathode buffer layer (or electron transfer layer), (rotating speed is 2000rpm, time is 40s, and thickness is about 3 ~ 5nm), and put on hot plate in 80 DEG C of annealing 2min, last evaporation thickness is about the Al electrode of 100nm, obtains with rGO-K 4pTC compound is as the organic polymer solar cell of cathode buffer layer (or electron transfer layer).
Under the light intensity of AM1.5 is irradiated, the open circuit voltage of this organic polymer solar cell is 0.64V, and short circuit current is 8.13mAcm -2, fill factor, curve factor is 60.13%, and photoelectric conversion efficiency is that 3.13%(is see table 1), I-V characteristic curve is as shown in Figure 3.
Configuration embodiment 2: with K 4pTC makes organic polymer solar cell as cathode buffer layer.
Preparation K 4pTC is at H 2o:DMF(v:v=1:2) solution (concentration is about 0.3mg/mL) in, stand-by.Adopt the method in embodiment 2, prepare under the same conditions with K 4pTC is as the organic polymer solar cell of cathode buffer layer.
Under the light intensity of AM1.5 is irradiated, the open circuit voltage of this organic polymer solar cell is 0.63V, and short circuit current is 8.72mAcm -2, fill factor, curve factor is 56.50%, and photoelectric conversion efficiency is that 3.09%(is see table 1), I-V characteristic curve is as shown in Figure 3.
Comparing embodiment 1: make the organic polymer solar cell without cathode buffer layer.
Adopt the method in embodiment 2, prepare the organic polymer solar cell without cathode transport layer under the same conditions.The open circuit voltage of this organic polymer solar cell is 0.59V, and short circuit current is 6.28mAcm -2, fill factor, curve factor is 57.26%, and photoelectric conversion efficiency is that 2.13%(is see table 1), I-V characteristic curve is as shown in Figure 3.It can thus be appreciated that, insert based on rGO-K between the photoactive layer and negative electrode of photovoltaic device 4the cathode buffer layer of PTC compound, is conducive to the photoelectric conversion efficiency improving device.
Comparing embodiment 2: make organic polymer solar cell as cathode buffer layer using calcium metal.
Adopt the method in embodiment 2, prepare the organic polymer solar cell using calcium metal (about 10nm is thick) as cathode buffer layer under the same conditions.The open circuit voltage of this organic polymer solar cell is 0.63V, and short circuit current is 8.52mAcm -2, fill factor, curve factor is 58.18%, and photoelectric conversion efficiency is that 3.14%(is see table 1), and with rGO-K 4pTC or K 4pTC compound as the device of cathode buffer layer efficiency quite or slightly high, the I-V characteristic curve of this organic polymer solar cell is as shown in Figure 3.
The device of preparation in configuration embodiment 1, configuration embodiment 2 and comparing embodiment 2 is positioned over (relative humidity is about 60%RH) in air, and its efficiency change situation as shown in Figure 4.Result shows, with rGO-K 4pTC compound as the stability of the device of cathode buffer layer significantly better than with K 4pTC or calcium metal are as the device of cathode buffer layer.
From the result of above-described embodiment, rGO-K disclosed by the invention 4its preparation process of PTC compound is simple, and better dispersed in the mixture of water and water and organic solvent, and the standby cathode buffer layer based on this compound of Solution legal system, preparation cost is lower.The efficiency comprising the organic polymer solar cell of the cathode buffer layer based on this compound is close using calcium metal as the battery efficiency of cathode buffer layer, and aerial stability is significantly improved.

Claims (10)

1. the preparation method of redox graphene-3,4,9, a 10-perylene tetracarboxylic acid potassium compound, it comprises the steps:
1) graphene oxide is dispersed in water, according to graphene oxide: the mass ratio of 3,4,9,10-perylene tetracarboxylic acid potassium=1:1.1 ~ 1.5, adds 3,4,9,10-perylene tetracarboxylic acid potassium and mix, obtaining mixed liquor;
2) according to graphene oxide: the mass ratio of sodium borohydride=1:1.1 ~ 1.3, in the mixed liquor obtained in step 1), add sodium borohydride, be heated to backflow, be cooled to room temperature after reacting 3 ~ 4 hours under agitation, obtain reactant liquor;
3) by step 2) in the reactant liquor that obtains put into bag filter dialysis 2 ~ 3 days, content in freeze drying bag filter, obtains redox graphene-3,4,9,10-perylene tetracarboxylic acid potassium compound.
2. preparation method according to claim 1, is characterized in that, graphene oxide described in step 1) is obtained by Hummers method.
3. preparation method according to claim 1, is characterized in that, water described in step 1) is distilled water.
4. preparation method according to claim 1, is characterized in that, mixes and completed by mode that is ultrasonic or that add thermal agitation described in step 1).
5. preparation method according to claim 4, is characterized in that, the described ultrasonic time is 2 ~ 3 hours.
6. preparation method according to claim 4, is characterized in that, described in add thermal agitation temperature be 40 ~ 60 DEG C, the time is 8 ~ 12 hours.
7. preparation method according to claim 1, is characterized in that, the molecular cut off of bag filter described in step 3) is 1000.
8. redox graphene-3,4,9, the 10-perylene tetracarboxylic acid potassium compound prepared of preparation method according to any one of claim 1 to 7.
9. redox graphene-3,4,9,10-perylene tetracarboxylic acid potassium compound according to claim 8 is preparing the purposes in organic photovoltaic devices as cathode buffer layer.
10. purposes according to claim 9, is characterized in that, described organic photovoltaic devices is organic polymer solar cell.
CN201510602655.0A 2015-09-21 2015-09-21 A kind of tetracarboxylic acid potassium compound of redox graphene 3,4,9,10 and its production and use Active CN105140407B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201510602655.0A CN105140407B (en) 2015-09-21 2015-09-21 A kind of tetracarboxylic acid potassium compound of redox graphene 3,4,9,10 and its production and use

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201510602655.0A CN105140407B (en) 2015-09-21 2015-09-21 A kind of tetracarboxylic acid potassium compound of redox graphene 3,4,9,10 and its production and use

Publications (2)

Publication Number Publication Date
CN105140407A true CN105140407A (en) 2015-12-09
CN105140407B CN105140407B (en) 2018-04-03

Family

ID=54725686

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201510602655.0A Active CN105140407B (en) 2015-09-21 2015-09-21 A kind of tetracarboxylic acid potassium compound of redox graphene 3,4,9,10 and its production and use

Country Status (1)

Country Link
CN (1) CN105140407B (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103399061A (en) * 2013-07-31 2013-11-20 盐城工学院 Preparation method of perylene tetracarboxylic acid-graphene heterojunction based photo-anode material
CN104103812A (en) * 2014-07-21 2014-10-15 国家纳米科学中心 Composite flexible electrode material as well as preparation method and application thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103399061A (en) * 2013-07-31 2013-11-20 盐城工学院 Preparation method of perylene tetracarboxylic acid-graphene heterojunction based photo-anode material
CN104103812A (en) * 2014-07-21 2014-10-15 国家纳米科学中心 Composite flexible electrode material as well as preparation method and application thereof

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
ANINDARUPA CHUNDER,ET AL: "Reduced Graphene Oxide/Copper Phthalocyanine Composite and Its Optoelectrical Properties", 《J. PHYS. CHEM. C》 *
LINGYAN FENG, ET AL: "A graphene functionalized electrochemical aptasensor for selective label-free detection of cancer cells", 《BIOMATERIALS》 *
MINGHUA HUANG,ET AL: "Polymer-Induced Self-Assembly of Small Organic Molecules into Ultralong Microbelts with Electronic Conductivity", 《J. AM.CHENM.SOC.》 *
XIANXUE GAN,ET AL: "3,4,9,10-Perylenetetracarboxylic dianhydride functionalized graphene sheet as labels for ultrasensitive electrochemiluminescent detection of thrombin", 《ANALYTICA CHIMICA ACTA》 *

Also Published As

Publication number Publication date
CN105140407B (en) 2018-04-03

Similar Documents

Publication Publication Date Title
Chang et al. Tuning perovskite morphology by polymer additive for high efficiency solar cell
Ye et al. CuSCN-based inverted planar perovskite solar cell with an average PCE of 15.6%
KR101571528B1 (en) Perovskite solar cell improving photoelectric conversion efficiency and the manufacturing method thereof
CN103626975B (en) A kind of semiconductive conjugated polymer and preparation method thereof
CN106397355B (en) A kind of auto-dope conjugated phenols amine hole mobile material and preparation and application
CN105470399A (en) Perovskite solar cell based on undoped organic hole transport layer and preparation method
CN105968126A (en) Dipyridine/phenanthroline onium salt-containing water/alcohol-soluble conjugated micromolecule and preparation method and application thereof
CN106410037A (en) Small organic molecule donor material based double-junction solar cell device and preparation method thereof
CN111081883B (en) Efficient and stable planar heterojunction perovskite solar cell and preparation method
CN105280818A (en) Stable planar heterojunction perovskite solar cell and manufacturing method thereof
CN112646129B (en) N-type water/alcohol-soluble conjugated polyelectrolyte containing benzobisthiadiazole and preparation and application thereof
CN109216554B (en) Perovskite solar cell with P3 HT/graphene as hole transport layer and preparation method thereof
Shang et al. Ethanol‐Processable Polyfuran Derivative for Eco‐Friendly Fabrication of Organic Solar Cells Featuring Self‐Healing Function
CN110265552A (en) Perovskite solar battery and preparation method based on preceding oxidation composite hole transporting layer
CN220023501U (en) Crystalline silicon/perovskite laminated solar cell
CN102593362B (en) Organic solar cell
CN108682740A (en) Perovskite battery and preparation method thereof
CN111303590B (en) Organic ionic salt additive for modifying PEDOT PSS and application thereof
CN109851571B (en) Conjugated organic small molecule interface modification material, preparation method and organic solar cell formed by conjugated organic small molecule interface modification material
CN102790177B (en) Polymer solar battery and preparation method thereof
CN106410033A (en) Polymer film and preparation method and application thereof
CN102386333A (en) Laminated organic thin film solar cell
CN102945925B (en) Improve the method for organic solar batteries photoelectric conversion efficiency
CN112646130B (en) N-type water/alcohol-soluble conjugated polyelectrolyte based on double free radical benzobisthiadiazole, and preparation and application thereof
CN109378388A (en) Efficient ternary organic solar batteries and preparation method thereof

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant