CN109851571A - A kind of organic photovoltaic cell being conjugated small organic molecule modifying interface material, preparation method and its composition - Google Patents
A kind of organic photovoltaic cell being conjugated small organic molecule modifying interface material, preparation method and its composition Download PDFInfo
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Abstract
The invention discloses a kind of conjugation small organic molecule modifying interface materials, the organic photovoltaic cell of preparation method and its composition.Small organic molecule modifying interface material SAM1, SAM2 and SAM3 of the invention is obtained with 1,3- indandione rodenticide, Rao Danning, rich one step of the tannin condensation synthesis of dicyanogen methyl isophorone respectively by terephthalaldehydic acid.The small organic molecule modifying interface material can be surface modified zinc oxide by physical absorption and chemical reaction, the hydroxyl hanging key defect density of states of zinc oxide surface can not only be reduced, energy level arrangement, which can also be optimized, reduces interface electron-transport potential barrier, so that the interface charge for promoting solar cell device is extracted and reduction interface carrier is compound.It is modified in transoid organic photovoltaic cell using material preparation, device efficiency is obviously improved.After wherein having modified SAM1, the device efficiency that the device efficiency of PBDB-T/ITIC system is improved by 10.13% to 10.82%, PBDB-T-SF/IT-4F system is promoted to 13.25% by 12.18%.
Description
Technical field
The invention belongs to field of energy source materials more particularly to a kind of conjugation small organic molecule modifying interface materials, preparation side
The organic photovoltaic cell of method and its composition.
Background technique
It is electric energy come efficiently conversion solar light by solar cell is that academia and industrial circle are paid close attention to and ground all the time
The hot spot studied carefully.Silica-based solar cell is that leading inorganic solar cell is to develop product the most mature in current all solar cells
Kind, there is relatively high incident photon-to-electron conversion efficiency, but energy consumption and pollution high during the manufacturing brings high production
Cost, while surrounding enviroment are polluted.
The solar cell of solution processable can be cleaned by the realization of roll-to-roll technology, is efficient, extensive batch
Production, is one of the direction of solar cell future development.Representative solution processable solar cell (such as dye-sensitized cell,
Organic (polymer) battery, hybrid inorganic-organic battery, quantum dot sensitized battery etc.) photoelectric conversion efficiency research fast
Speed development.Wherein efficiency is developed rapidly organic photovoltaic cell in recent years, and by 2018, organic sun electricity was reported in research
The peak efficiency in pond be more than 14% (Z.Zheng, Q.Hu, S.Zhang, D.Zhang, J.Wang, S.Xie, R.Wang, Y.Qin,
W.Li,L.Hong,N.Liang,F.Liu,Y.Zhang,Z.Wei,Z.Tang,T.P.Russell,J.Hou and H.Zhou,
Adv.Mater.,2018,DOI:10.1002/adma.201801801；X.Che,Y.Li,Y.Qu and S.R.Forrest,
Nat.Energy, 2018,3,422-427.), illustrate that organic photovoltaic cell has good industrialization prospect.
In organic photovoltaic cell, used electron transport material is confined to metal oxide, interfacial polymerization object at present
PFN-Br etc..Wherein, this quasi-metal oxides of zinc oxide light transmittance with higher and electric conductivity, are widely used in organic sun
It can be in the transoid device of battery, however, surface forms the energy of more defect state and zinc oxide to zinc oxide in process
Grade causes carrier in the serious compound of interface with non-fullerene acceptor level mismatch.Meanwhile the photocatalysis of zinc oxide is living
Property makes organic active layer degrade, and seriously affects the stability of organic solar batteries.Therefore, exploitation suitably has altogether
The organic supramolecular Iy self-assembled layer of yoke structure improves the extractability of interface carrier, improves device stability for device
The promotion of energy is played the role of vital.
Summary of the invention
It is an object of the invention to overcome the shortage of prior art, and provide a kind of conjugation small organic molecule modifying interface material
Material.The conjugation small organic molecule modifying interface material is for passing through self assembly mode modifying metallic oxide surface.
Specific technical solution of the present invention is as follows:
A kind of conjugation small organic molecule modifying interface material is SAM1, SAM2 or SAM3；Described SAM1, SAM2 and SAM3's
Particular chemical formula is respectively as follows:
The present invention also provides a kind of preparation methods of small organic molecule modifying interface material；Its include the following steps: by
Raw material, terephthalaldehydic acid and Beta-alanine are added in dry reaction flask, and mixed solvent is then added；It is anti-being heated to reflux
The solid that reaction is precipitated is obtained by filtration in Ying Hou；It is finally obtained later with the solid that methanol, mixed solvent wash precipitation repeatedly organic
Small molecule modifying interface material；The raw material is one of rich tannin of 1,3- indandione rodenticide, Rao Danning and dicyanogen methyl isophorone, is used respectively
In preparation SAM1, SAM2 and SAM3；The mixed solvent is made of ethyl alcohol and 1,2- dichloroethanes.
Preferably, the molar equivalent ratio of the raw material, terephthalaldehydic acid and Beta-alanine is 1:(1.2~2):
(0.1~1)；Inventory of the mixed solvent in back flow reaction is that 10ml is added in raw material described in every 2mmol；The mixing is molten
The volume ratio of ethyl alcohol and 1,2- dichloroethanes is 1:2 in agent；Back flow reaction temperature is 80 DEG C, reaction time 8h.
The present invention also provides a kind of organic photovoltaic cells based on conjugation small organic molecule modifying interface material.This is organic
Solar cell includes the substrate that successively stratiform is arranged from the bottom to top, transparent electrode layer, metal oxide electron transport layer, small molecule
Interface-modifying layer, active layer, hole transmission layer, metal electrode layer；The small molecule interface-modifying layer is small organic molecule interface
Any one in decorative material SAM1, SAM2 and SAM3, the particular chemical formula of SAM1, SAM2 and SAM3 are as follows:
Preferably, the small molecule interface-modifying layer is the cathodic modification for modifying metallic oxide electron transfer layer
Layer.
Preferably, the active layer is the blend film of organic electronic donor material and organic electronic acceptor material；It is described
Organic electronic donor material is PBDB-T or PBDB-T-SF；The organic electronic acceptor material is ITIC or IT-4F.
Preferably, the material of the substrate is glass or quartz or flexibility PET or flexibility PEN.
Preferably, the material of the transparent electrode layer is that tin indium oxide or fluorine mix tin oxide or sheet metal；It is described
Prescribed electrode layer with a thickness of 1-500nm.
Preferably, the sheet metal is silver or copper or gold.
Preferably, the metal electrode layer with a thickness of 1-300nm；The material of metal electrode layer be silver, aluminium, magnesium, copper,
Gold, tin indium oxide and fluorine mix one of tin oxide.
The preparation process of solar cell of the present invention is as follows:
By the transparent conducting glass that surface etch has strip tin indium oxide ITO (cathode) successively use cleaning agent, deionized water,
It is dry with nitrogen stream after acetone and isopropanol sonic oscillation clean 30 minutes, then 10 points are handled with ultraviolet, ozone plasma
Clock；Zinc oxide precursor liquid solution is spun on the surface ITO with the revolving speed of 3500r/min, and anneals 20 minutes under the conditions of 170 DEG C,
It is transferred to glove box.Configuration concentration is the small organic molecule modifying interface material solution of 1mg/mL, and with the rotation of the speed of 4000rmp
It is applied to zinc oxide surface, is then annealed 10 minutes at 100 DEG C；Active layer solution is configured later；When active layer solution is PBDB-T/
When ITIC (20mg/mL, weight ratio 1:1,0.5%DIO), active layer solution is spun on small molecule circle with the revolving speed of 2500rmp
On the decorative layer of face, and anneal 10 minutes at 100 DEG C；When active layer solution is PBDB-T-SF/IT-4F (16mg/mL, weight
Than 1:1,0.5%DIO) when, active layer solution is spun on small molecule interface-modifying layer with the revolving speed of 3000rmp, and
It anneals 30 minutes at 160 DEG C.Finally 2 × 10-4Under the conditions of Pa, vacuum chamber deposits the molybdenum oxide sky of 8 nanometer thickness on active layer
The Ag electrode (anode) of cave transport layer and 100 nanometer thickness.The zinc oxide is used in metal oxide electron transport layer
Material can replace with other metal oxides according to demand.
The present invention in terms of existing technologies, has the advantages that
The present invention is prepared for the conjugation small organic molecule of three kinds of metal oxides using the simple method for synthesizing that a step is condensed
Modifying interface material SAM1, SAM2 and SAM3.By adjusting the electronegativity of end structure, three kinds of molecules can be in zinc oxide surface
Different interface dipoles is formed, the energy level arrangement of zinc oxide is changed.Using the zinc oxide of modified as the electricity of organic photovoltaic cell
When sub- transport layer, the performance of organic photovoltaic cell can be effectively improved.Wherein modification SAM1 can obtain highest photoelectric conversion effect
Rate, the zinc oxide of SAM1 modified can reduce the work content of zinc oxide, make the conduction band of zinc oxide and the LUMO of non-fullerene acceptor
Energy level more matches, and reduces electron-transport potential barrier, improves the recovery rate of interface carrier, reduce the compound of carrier.It will
When SAM1 is applied to PBDB-T/ITIC photoactive layer system, device efficiency is improved by 10.13% to 10.82%；It is applied to
When PBDB-T-SF/IT-4F system, device efficiency is promoted to 13.25% by 12.18%.
Detailed description of the invention
Fig. 1 is the structural schematic diagram of organic photovoltaic cell in embodiment.
Fig. 2 is the current -voltage curve of organic photovoltaic cell.
Fig. 3 is the current -voltage curve of organic photovoltaic cell.
Fig. 4 is the nucleus magnetic hydrogen spectrum of SAM1.
Fig. 5 is the nucleus magnetic hydrogen spectrum of SAM2.
Fig. 6 is the nucleus magnetic hydrogen spectrum of SAM3.
Specific embodiment
The present invention is further elaborated and is illustrated with reference to the accompanying drawings and detailed description.Each implementation in the present invention
The technical characteristic of mode can carry out the corresponding combination under the premise of not conflicting with each other.
The present invention uses terephthalaldehydic acid, and tannin of having mercy on respectively with 1,3- indandione rodenticide, Rao Danning, dicyanogen methyl isophorone carries out a step contracting
Close small organic molecule the decorative material SAM1, SAM2, SAM3 for being prepared for three kinds of conjugated structures.Small organic molecule modifying interface material
The synthetic reaction equation of SAM1, SAM2, SAM3 are as shown above.Wherein, 1,3- indandione rodenticide, Rao Danning, dicyanogen methyl isophorone rich tannin, β-
Alanine and terephthalaldehydic acid pass through commercialization approach and buy.
Embodiment 1
Be added in dry reaction flask the 1,3- indandione rodenticide of 1 molar equivalent, 1.2 molar equivalents terephthalaldehydic acid with
And 0.1 molar equivalent Beta-alanine.Then according to inventory, 1, the 3- indandione rodenticide of every 2mmol be added the ethyl alcohol of 10ml with
1,2- dichloroethanes mixed solvent, wherein ethyl alcohol and 1, the volume ratio of 2- dichloroethanes are 1:1.Then under 80 DEG C of reflux states
React 8h.There is yellow solid precipitation in reaction process, to filter the solid being precipitated after reaction.By solid ethyl alcohol with
1,2- dichloroethanes mixed solvent washs 3 times, obtains SAM1.The nuclear magnetic spectrogram of SAM1 is as shown in Figure 4.1H NMR(DMSO-d6,
500MHz): δ 13.28 (s, 1H), 8.48 (d, J=10Hz, 2H), 8.02 (d, J=10Hz, 2H), 7.94-8.00 (m, 4H),
7.86(s,1H)。
Embodiment 2
The rich tannin of 1 molar equivalent, the terephthalaldehydic acid of 2 molar equivalents are added in dry reaction flask and 1 rubs
The Beta-alanine of your equivalent.Then according to inventory, the ethyl alcohol and 1 of 10ml, 2- dichloroethanes is added in the rich tannin of every 2mmol
Mixed solvent, wherein ethyl alcohol and 1, the volume ratio of 2- dichloroethanes are 1:1.Then 8h is reacted under 80 DEG C of reflux states.Reaction
There is yellow solid precipitation in the process, to filter the solid being precipitated after reaction.By solid ethyl alcohol and bis- chloroethene of 1,2-
Alkane mixed solvent washs 3 times, obtains SAM2.The nuclear magnetic spectrogram of SAM2 is as shown in Figure 5.1H NMR(DMSO-d6,500MHz):δ
8.05 (d, J=10Hz, 2H), 7.85 (s, 1H), 7.73 (d, 2H), 4.06-4.10 (m, 4H), 1.19 (t, J=7.5Hz, 3H).
Embodiment 3
The rich tannin of dicyanogen methyl isophorone of 1 molar equivalent, the terephthalaldehydic acid of 1.6 molar equivalents are added in dry reaction flask
And 0.6 molar equivalent Beta-alanine, wherein ethyl alcohol and 1, the volume ratio of 2- dichloroethanes is 1:1, wherein ethyl alcohol and 1,
The volume ratio of 2- dichloroethanes is 1:1.Then according to inventory, the dicyanogen methyl isophorone of every 2mmol have mercy on tannin be added the ethyl alcohol of 10ml with
1,2- dichloroethanes mixed solvent.Then 8h is reacted under 80 DEG C of reflux states.There is yellow solid precipitation in reaction process, to anti-
The solid being precipitated is filtered after answering.By solid ethyl alcohol and 1,2- dichloroethanes mixed solvent is washed 3 times, is obtained
SAM3.The nuclear magnetic spectrogram of SAM3 is as shown in Figure 6.1H NMR(DMSO-d6,500MHz):δ8.09-8.11(m,3H),7.78(d,J
=10Hz, 2H), 4.13-4.17 (m, 2H), 1.28-1.31 (t, J=7.5Hz, 3H).
Embodiment 4
The transparent conducting glass that surface etch has strip ITO (cathode) is successively used into cleaning agent, deionized water, acetone and different
It is dry with nitrogen stream after propyl alcohol sonic oscillation cleans 30 minutes, then handled 10 minutes with ultraviolet, ozone plasma；Zinc oxide
Precursor solution is spun on the surface ITO with the revolving speed of 3500r/min, and anneals 20 minutes under the conditions of 170 DEG C, is transferred to gloves
Case.Configuration concentration is the SAM1 solution of 1mg/mL, then it is spun on zinc oxide surface with the speed of 4000rmp, then 100
DEG C annealing 10 minutes；Configure PBDB-T/ITIC solution later (specific proportion is 20mg/mL, weight ratio 1:1,0.5%DIO).Again
PBDB-T/ITIC solution is spun on SAM1 with the revolving speed of 2500rmp, and is annealed 10 minutes at 100 DEG C.Finally 2
×10-4Under the conditions of Pa, vacuum chamber deposits the molybdenum oxide hole transmission layer of 8 nanometer thickness and the Ag electricity of 100 nanometer thickness on active layer
Pole (anode).Made organic photovoltaic cell structure is as shown in Figure 1, successively substrate 1, the transparent electrode of stratiform arrangement from the bottom to top
Layer 2, metal oxide electron transmitting layer 3, small molecule interface-modifying layer 4, active layer 5, hole transmission layer 6, metal electrode layer 7.
Its i-v curve test result such as Fig. 2.
Embodiment 5
The transparent conducting glass that surface etch has strip ITO (cathode) is successively used into cleaning agent, deionized water, acetone and different
It is dry with nitrogen stream after propyl alcohol sonic oscillation cleans 30 minutes, then handled 10 minutes with ultraviolet, ozone plasma；Zinc oxide
Precursor solution is spun on the surface ITO with the revolving speed of 3500r/min, and anneals 20 minutes under the conditions of 170 DEG C, is transferred to gloves
Case.Configuration concentration is the SAM2 solution of 1mg/mL, then it is spun on zinc oxide surface with the speed of 4000rmp, then 100
DEG C annealing 10 minutes；Configure PBDB-T/ITIC solution later (specific proportion is 20mg/mL, weight ratio 1:1,0.5%DIO).Again
PBDB-T/ITIC solution is spun on SAM2 with the revolving speed of 2500rmp, and is annealed 10 minutes at 100 DEG C.Finally 2 ×
10-4Under the conditions of Pa, vacuum chamber deposits the molybdenum oxide hole transmission layer of 8 nanometer thickness and the Ag electrode of 100 nanometer thickness on active layer
(anode).I-v curve test result such as Fig. 2.
Embodiment 6
The transparent conducting glass that surface etch has strip ITO (cathode) is successively used into cleaning agent, deionized water, acetone and different
It is dry with nitrogen stream after propyl alcohol sonic oscillation cleans 30 minutes, then handled 10 minutes with ultraviolet, ozone plasma；Zinc oxide
Precursor solution is spun on the surface ITO with the revolving speed of 3500r/min, and anneals 20 minutes under the conditions of 170 DEG C, is transferred to gloves
Case.Configuration concentration is the SAM3 solution of 1mg/mL, then it is spun on zinc oxide surface with the speed of 4000rmp, then 100
DEG C annealing 10 minutes；Configure PBDB-T/ITIC solution later (specific proportion is 20mg/mL, weight ratio 1:1,0.5%DIO)；Again
PBDB-T/ITIC solution is spun on SAM3 with the revolving speed of 2500rmp, and is annealed 10 minutes at 100 DEG C；Finally 2
×10-4Under the conditions of Pa, vacuum chamber deposits the molybdenum oxide hole transmission layer of 8 nanometer thickness and the Ag electricity of 100 nanometer thickness on active layer
Pole (anode).I-v curve test result such as Fig. 2.
Comparative example 1
The transparent conducting glass that surface etch has strip ITO (cathode) is successively used into cleaning agent, deionized water, acetone and different
It is dry with nitrogen stream after propyl alcohol sonic oscillation cleans 30 minutes, then handled 10 minutes with ultraviolet, ozone plasma；Zinc oxide
Precursor solution is spun on the surface ITO with the revolving speed of 3500r/min, and anneals 20 minutes under the conditions of 170 DEG C, is transferred to gloves
Case.Configure PBDB-T/ITIC solution later (specific proportion is 20mg/mL, weight ratio 1:1,0.5%DIO)；Again by PBDB-T/
ITIC solution is spun on zinc oxide with the revolving speed of 2500rmp, and is annealed 10 minutes at 100 DEG C；Finally 2 × 10-4Pa
Under the conditions of, vacuum chamber deposits the molybdenum oxide hole transmission layer of 8 nanometer thickness and the Ag electrode (sun of 100 nanometer thickness on active layer
Pole).I-v curve test result such as Fig. 2.
Embodiment 7
The transparent conducting glass that surface etch has strip ITO (cathode) is successively used into cleaning agent, deionized water, acetone and different
It is dry with nitrogen stream after propyl alcohol sonic oscillation cleans 30 minutes, then handled 10 minutes with ultraviolet, ozone plasma；Zinc oxide
Precursor solution is spun on the surface ITO with the revolving speed of 3500r/min, and anneals 20 minutes under the conditions of 170 DEG C, is transferred to gloves
Case.Configuration concentration is the SAM1 solution of 1mg/mL, then it is spun on zinc oxide surface with the speed of 4000rmp, then 100
DEG C annealing 10 minutes；Configure later PBDB-T-SF/IT-4F solution (specific proportion is 16mg/mL, weight ratio 1:1,0.5%
DIO)；PBDB-T-SF/IT-4F solution is spun on SAM1 with the revolving speed of 3000rmp again, and is annealed 30 points at 160 DEG C
Clock；Finally 2 × 10-4Under the conditions of Pa, the molybdenum oxide hole transmission layer and 100 that vacuum chamber deposits 8 nanometer thickness on active layer is received
The thick Ag electrode (anode) of rice.I-v curve test result such as Fig. 3.
Comparative example 2
The transparent conducting glass that surface etch has strip ITO (cathode) is successively used into cleaning agent, deionized water, acetone and different
It is dry with nitrogen stream after propyl alcohol sonic oscillation cleans 30 minutes, then handled 10 minutes with ultraviolet, ozone plasma；Zinc oxide
Precursor solution is spun on the surface ITO with the revolving speed of 3500r/min, and anneals 20 minutes under the conditions of 170 DEG C, is transferred to gloves
Case.Configure PBDB-T-SF/IT-4F solution later (specific proportion is 16mg/mL, weight ratio 1:1,0.5%DIO)；Again will
PBDB-T-SF/IT-4F solution is spun on zinc oxide with the revolving speed of 3000rmp, and is annealed 30 minutes at 160 DEG C；Finally
2 × 10-4Under the conditions of Pa, vacuum chamber deposits the molybdenum oxide hole transmission layer of 8 nanometer thickness and the Ag of 100 nanometer thickness on active layer
Electrode (anode).I-v curve test result such as Fig. 3.
Test result analysis
It is 100mW/cm in intensity of illumination2AM 1.5G simulated solar irradiation irradiation under, test embodiment 4-7 and comparison
The current -voltage curve of example 1,2.
Test results are shown in figure 2 for PBDB-T/ITIC system.Wherein, comparative example 1 (i.e. without carry out SAM modification)
The open-circuit voltage of device is 0.89V, short-circuit current density 16.12mA/cm2, fill factor 0.73, photovoltaic energy conversion effect
Rate is 10.13%.The open-circuit voltage of 4 device of embodiment based on SAM1 decorative layer is 0.89V, and short-circuit current density is
17.52mA/cm2, fill factor 0.73, photovoltaic energy conversion efficiency is 10.82%.Embodiment 5 based on SAM2 decorative layer
The open-circuit voltage of device is 0.89V, short-circuit current density 16.50mA/cm2, fill factor 0.73, photovoltaic energy conversion effect
Rate is 10.44%；6 device parameters open-circuit voltage of embodiment based on SAM3 decorative layer is 0.65V, and short-circuit current density is
17.21mA/cm2, fill factor 0.56, photovoltaic energy conversion efficiency is 6.54%.
Test results are shown in figure 3 for PBDB-T-SF/IT-4F system.Wherein, comparative example 2 (is repaired without carrying out SAM
Decorations) device open-circuit voltage be 0.87V, short-circuit current density 19.31mA/cm2, fill factor 0.72, photoelectric energy turn
Changing efficiency is 12.18%.The open-circuit voltage of 7 device of embodiment based on SAM1 decorative layer is 0.87V, and short-circuit current density is
20.80mA/cm2, fill factor 0.73, photovoltaic energy conversion efficiency is 13.25%.
It can be seen that not only reducing zinc oxide surface when being surface modified using these three materials to zinc oxide
Defect state density, can also be by adjusting the electronegativity of end structure, and then adjusts the dipole of molecule.Using SAM to zinc oxide
Carrying out modification can cause the energy level arrangement of zinc oxide to change, and reduce interface electron-transport potential barrier, reduce interface
Carrier recombination rate enhances its charge-extraction and transmittability.Prepared transoid organic solar batteries are with higher short
Road electric current Jsc, and obtain higher device efficiency.When SAM1 being wherein applied to PBDB-T/ITIC photoactive layer system, device
Efficiency is improved by 10.13% to 10.82%；When applied to PBDB-T-SF/IT-4F system, device efficiency is promoted by 12.18%
To 13.25%.
Above-mentioned embodiment is only a preferred solution of the present invention, so it is not intended to limiting the invention.Have
The those of ordinary skill for closing technical field can also make various changes without departing from the spirit and scope of the present invention
Change and modification.Therefore all mode technical solutions obtained for taking equivalent substitution or equivalent transformation, all fall within guarantor of the invention
It protects in range.
Claims (10)
1. a kind of conjugation small organic molecule modifying interface material, which is characterized in that the small organic molecule modifying interface material is
SAM1, SAM2 or SAM3；The particular chemical formula of described SAM1, SAM2 and SAM3 are respectively as follows:
2. a kind of preparation method of small organic molecule modifying interface material as described in claim 1, which is characterized in that including such as
Lower step: raw material, terephthalaldehydic acid and Beta-alanine are added in dry reaction flask, mixed solvent is then added；?
After heating reflux reaction, the solid that reaction is precipitated is obtained by filtration；The solid of precipitation is washed repeatedly most with methanol, mixed solvent later
Small organic molecule modifying interface material is obtained eventually；The raw material is in the rich tannin of 1,3- indandione rodenticide, Rao Danning and dicyanogen methyl isophorone
One kind being respectively used to preparation SAM1, SAM2 and SAM3；The mixed solvent is made of ethyl alcohol and 1,2- dichloroethanes.
3. the preparation method of small organic molecule modifying interface material as claimed in claim 2, which is characterized in that the raw material,
The molar equivalent of terephthalaldehydic acid and Beta-alanine ratio is 1:(1.2~2): (0.1~1)；The mixed solvent is flowing back
Inventory in reaction is that 10ml is added in raw material described in every 2mmol；The body of the in the mixed solvent ethyl alcohol and 1,2- dichloroethanes
Product is than being 1:2；Back flow reaction temperature is 80 DEG C, reaction time 8h.
4. it is a kind of based on conjugation small organic molecule modifying interface material organic photovoltaic cell, which is characterized in that including by down toward
On successively stratiform arrangement substrate (1), transparent electrode layer (2), metal oxide electron transport layer (3), small molecule modifying interface
Layer (4), active layer (5), hole transmission layer (6), metal electrode layer (7)；The small molecule interface-modifying layer (4) is organic small point
Any one in sub-interface decorative material SAM1, SAM2 and SAM3, the particular chemical formula of SAM1, SAM2 and SAM3 are as follows:
5. organic photovoltaic cell as claimed in claim 4, which is characterized in that the small molecule interface-modifying layer (4) is as yin
Pole decorative layer is used for modifying metallic oxide electron transfer layer (3).
6. organic photovoltaic cell as claimed in claim 4, which is characterized in that the active layer (5) is organic electronic donor material
The blend film of material and organic electronic acceptor material；The organic electronic donor material is PBDB-T or PBDB-T-SF；It is described organic
Electron acceptor material is ITIC or IT-4F.
7. organic photovoltaic cell as claimed in claim 4, which is characterized in that the material of the substrate (1) is glass or quartz
Or flexibility PET or flexibility PEN.
8. organic photovoltaic cell as claimed in claim 4, which is characterized in that the material of the transparent electrode layer (2) is oxidation
Indium tin or fluorine mix tin oxide or sheet metal；The transparent electrode layer (2) with a thickness of 1-500nm.
9. organic photovoltaic cell as claimed in claim 8, which is characterized in that the sheet metal is silver or copper or gold.
10. organic photovoltaic cell as claimed in claim 4, which is characterized in that the metal electrode layer (7) with a thickness of 1-
300nm；The material of metal electrode layer (7) is that silver, aluminium, magnesium, copper, gold, tin indium oxide and fluorine mix one of tin oxide.
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| CN111883661A (en) * | 2020-08-28 | 2020-11-03 | 电子科技大学 | Thick-film large-area organic photovoltaic device and preparation method thereof |
| CN113809271A (en) * | 2020-06-15 | 2021-12-17 | Tcl科技集团股份有限公司 | Composite material, preparation method thereof and quantum dot light-emitting diode |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04134043A (en) * | 1990-09-25 | 1992-05-07 | Kao Corp | New alpha-benzylidene ketone derivative, ultraviolet absorber and cosmetic containing said absorber |
| JP2005222929A (en) * | 2004-12-07 | 2005-08-18 | Matsushita Electric Ind Co Ltd | Electroluminescent element |
| WO2018114965A1 (en) * | 2016-12-23 | 2018-06-28 | Technische Universität München | Clpx inhibitory compounds for the treatment of multi resistant staphylococcus aureus virulence and for the treatment of leukemia |
-
2019
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04134043A (en) * | 1990-09-25 | 1992-05-07 | Kao Corp | New alpha-benzylidene ketone derivative, ultraviolet absorber and cosmetic containing said absorber |
| JP2005222929A (en) * | 2004-12-07 | 2005-08-18 | Matsushita Electric Ind Co Ltd | Electroluminescent element |
| WO2018114965A1 (en) * | 2016-12-23 | 2018-06-28 | Technische Universität München | Clpx inhibitory compounds for the treatment of multi resistant staphylococcus aureus virulence and for the treatment of leukemia |
Non-Patent Citations (3)
| Title |
|---|
| ACS: "RN:107625-05-8", 《STN-REGISTRY数据库》 * |
| CHRISTIAN FETZER等: "A Chemical Disruptor of the ClpX Chaperone Complex Attenuates the Virulence of Multidrug-Resistant Staphylococcus aureus", 《ANGEW.CHEM.INT.ED.》 * |
| 斐娟等: "异质结界面修饰对TiO2/P3HT杂化太阳电池光电性能的增强作用", 《化学学报》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113809271A (en) * | 2020-06-15 | 2021-12-17 | Tcl科技集团股份有限公司 | Composite material, preparation method thereof and quantum dot light-emitting diode |
| CN113809271B (en) * | 2020-06-15 | 2022-12-06 | Tcl科技集团股份有限公司 | Composite material, preparation method thereof and quantum dot light-emitting diode |
| CN111883661A (en) * | 2020-08-28 | 2020-11-03 | 电子科技大学 | Thick-film large-area organic photovoltaic device and preparation method thereof |
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