CN108341935A - A kind of organic solar batteries anode modification layer material and preparation method - Google Patents
A kind of organic solar batteries anode modification layer material and preparation method Download PDFInfo
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- CN108341935A CN108341935A CN201810319819.2A CN201810319819A CN108341935A CN 108341935 A CN108341935 A CN 108341935A CN 201810319819 A CN201810319819 A CN 201810319819A CN 108341935 A CN108341935 A CN 108341935A
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Abstract
The present invention relates to a kind of organic solar batteries anode modification layer material and preparation method, the preparation method is：2,6 dibromo 4 [1 (potassium sulfonate) butyl] dithieno cyclopentadiene and 2,5 hypoboric acid 3,4 difluoro thiophene carry out Suzuki coupling reactions, it is poly- { 4 [1 (potassium sulfonate) butyl] dithieno cyclopentadiene replace 3,4 difluoro thiophene } with anode modification layer material that organic solar batteries are made.The material is used for organic solar batteries anode modification, has the characteristics that thickness is insensitive.
Description
Technical field
The present invention relates to a kind of electrode modification layer material and preparation method thereof, more particularly to a kind of organic solar batteries sun
Layer material and preparation method thereof is modified in pole, belongs to organic photovoltaic material and its preparing technical field.
Background technology
Organic solar batteries have the advantages that nontoxic, flexible, low weight, low cost, have potential development prospect.Have
Machine solar cell is made of anode, anode modification layer material, active layer, cathodic modification layer material, cathode.Wherein, anode is repaiied
Decorations layer material can regulate and control the work function of anode, reduce the interface abilities between anode and active layer, improve organic solar electricity
The photoelectric conversion efficiency in pond improves the stability of organic solar batteries.
Currently used anode modification layer material is PEDOT:PSS.But PEDOT:PSS is highly acid, can corrode electricity
Pole, to drastically reduce the stability of organic solar batteries.PEDOT:PSS conductivity is relatively low, and the spy processed is needed when use
It is not thin, usually 30 ~ 40 nanometers, processing difficulties.
There are document and patent report recently, using conjugated polyelectrolytes material as organic solar batteries anode modification layer
Material, such as CPE-K, PCP-Na, PCPDT-T, CPEPh-Na, PhNa-1T etc..Conjugated polyelectrolytes anode modification layer material is
Neutral, efficiently solve PEDOT:PSS corroding electrode problems.But yoke polyelectrolyte material conductivity is very low, for sun
When the decorative layer of pole, it is necessary to process extremely thin, thickness is generally less than 10 nanometers.When conjugated polyelectrolytes are used for anode modification layer,
Thickness is more than 10 nanometers, and the photoelectric conversion efficiency of organic solar batteries can rapidly decline with the increase of conjugated polyelectrolytes thickness
Subtract, there are apparent thickness-sensitives, this brings extreme difficulties to battery making.
Invention content
The present invention is intended to provide a kind of high conductivity organic solar batteries anode modification layer material preparation method, described
The structural formula of organic solar batteries anode modification layer material is as follows：
The preparation method is：
Into reaction kettle be added 1.0 moles of bis- bromo- 4- of 2,6- [1- (potassium sulfonate) butyl] dithieno cyclopentadiene, 1.5 moles
2,5- hypoboric acid -3,4- difluoro thiophene and 50.0 milliliters of dimethyl sulfoxide (DMSO)s, by the way of bubbling, with 0.6 liter/min of flow velocity
It is passed through nitrogen 1.0 hours, and under nitrogen protection, adds 0.04 ~ 0.05 mole of tetra-triphenylphosphine palladium and 10.0 milliliter 1.0 is rubbed
You/liter wet chemical be warming up to 90 ~ 100 DEG C, and constant temperature is in 90 ~ 100 DEG C of magnetic force with 10 DEG C/h of heating rate
It is stirred to react 24.0 ~ 36.0 hours；Stop reaction, is down to room temperature, reaction product is poured into 200.0 milliliters of acetone, machinery stirs
It mixes 1.0 hours, filters, remove filtrate, obtain poly- { 4- [1- (potassium sulfonate) butyl] the dithieno ring penta 2 of anode modification layer material
Alkene-alternating -3,4- difluoros thiophene }.
Beneficial effects of the present invention：
Organic solar batteries anode modification layer material electric conductivity of the present invention is higher, reaches 5.6 × 10-3S/cm, for it is organic too
When positive energy galvanic anode modification layer material, processing thickness can reach 120 nanometers, effectively reduce difficulty of processing.
Organic solar batteries anode modification material of the present invention is soluble in water/first of water or methanol or arbitrary proportion
Alcohol in the mixed solvent, and the pH value range of water or methanol or water/mixed alkoxide solution is 7.0 ~ 8.0, it can be molten by water or methanol
Liquid chamber warm working, it is environmentally protective.
Organic solar batteries anode modification material of the present invention can reduce anode and activity with Effective Regulation anode work function number
Interface abilities between layer, to improve the photoelectric conversion efficiency of organic solar batteries.
Specific implementation mode
The present invention is illustrated by the following examples, but the present invention is not limited to the following embodiments, front and back described not departing from
Under the range of objective, change is included in the technical scope of the present invention.
Embodiment 1
Into reaction kettle be added 1.0 moles of bis- bromo- 4- of 2,6- [1- (potassium sulfonate) butyl] dithieno cyclopentadiene, 1.5 moles
2,5- hypoboric acid -3,4- difluoro thiophene and 50.0 milliliters of dimethyl sulfoxide (DMSO)s, by the way of bubbling, with 0.6 liter/min of flow velocity
It is passed through nitrogen 1.0 hours, and under nitrogen protection, adds 0.04 mole of tetra-triphenylphosphine palladium and 10.0 milliliter of 1.0 mol/L
Wet chemical be warming up to 90 DEG C, and constant temperature is in 90 DEG C of magnetic agitations reactions 24.0 with 10 DEG C/h of heating rate
Hour；Stop reaction, be down to room temperature, reaction product is poured into 200.0 milliliters of acetone, mechanical agitation 1.0 hours is filtered, removed
Go filtrate, obtain anode modification layer material of the present invention it is poly- 4- [1- (potassium sulfonate) butyl] dithieno cyclopentadiene-alternating -3,
4- difluoros thiophene }.
Embodiment 2
Into reaction kettle be added 1.0 moles of bis- bromo- 4- of 2,6- [1- (potassium sulfonate) butyl] dithieno cyclopentadiene, 1.5 moles
2,5- hypoboric acid -3,4- difluoro thiophene and 50.0 milliliters of dimethyl sulfoxide (DMSO)s, by the way of bubbling, with 0.6 liter/min of flow velocity
It is passed through nitrogen 1.0 hours, and under nitrogen protection, adds 0.05 mole of tetra-triphenylphosphine palladium and 10.0 milliliter of 1.0 mol/L
Wet chemical be warming up to 100 DEG C, and constant temperature is reacted in 100 DEG C of magnetic agitations with 10 DEG C/h of heating rate
36.0 hours；Stop reaction, be down to room temperature, reaction product is poured into 200.0 milliliters of acetone, mechanical agitation 1.0 hours is taken out
Filter removes filtrate, obtains poly- { 4- [1- (potassium sulfonate) butyl] the dithieno cyclopentadiene-friendship of anode modification layer material of the present invention
For -3,4- difluoros thiophene }.
By following experimental test anode modification layer material of the present invention for after modifying organic solar battery anode
Battery performance.
The anode modification layer material for taking 0.5 mass parts embodiment 1 or embodiment 2 to obtain, is dissolved in 1.0 milliliters of water and methanol etc.
The in the mixed solvent of volume mixture is used in combination 2 um filters to filter, and removes the insoluble impurity of bulky grain, obtains solution.
The pH value of solution is tested with SevenGo pH-SG2 pH meters.
By spin coating instrument, on spin coating anode modification layer material solution to ito anode, then 100 nanometers of spin coating thickness is used
The work function of electrode after the test modification of AXIS Ultra DLD (KRATOS Inc.) ultraviolet photo-electron spectrometer.
By spin coating instrument, on spin coating anode modification layer material solution to ito anode, then 100 nanometers of spin coating thickness is used
Tetra- probe sheet resistance instrument of QLDE tests the conductivity of 100 nanometer thickness anode modification layers.
Use currently used PTB7-Th:PC71BM activity coating systems, by spin coating instrument, prepare " ITO/ embodiments 1 or
Modification layer material/PTB7-Th prepared by embodiment 2:PC71Organic sun of BM active layers/PFN electron transport materials/Al " structures
Energy battery, the thickness of wherein anode modification layer is 100 nanometers, further by 2400 systems of Keithley, tests the light of battery
Photoelectric transformation efficiency.Photoelectric conversion efficiency is averaged by 20 batteries of parallel determination, reduces error.Cell photoelectric conversion effect
Rate is shown in Table 1.
The organic solar batteries of acquisition are placed in nitrogen glove box, by 2400 systems of Keithley, are fixed time
The photoelectric efficiency conversion of battery is tested, record photoelectric conversion efficiency declines the time needed for 5%, obtains stability test.Stability
20 batteries of parallel determination, are averaged, and reduce error.Stability test is shown in Table 1.
Claims (1)
1. a kind of organic solar batteries anode modification layer material and preparation method, it is characterised in that：The organic solar
The structural formula that galvanic anode modifies layer material is as follows：
The preparation method is：
Into reaction kettle be added 1.0 moles of bis- bromo- 4- of 2,6- [1- (potassium sulfonate) butyl] dithieno cyclopentadiene, 1.5 moles
2,5- hypoboric acid -3,4- difluoro thiophene and 50.0 milliliters of dimethyl sulfoxide (DMSO)s, by the way of bubbling, with 0.6 liter/min of flow velocity
It is passed through nitrogen 1.0 hours, and under nitrogen protection, adds 0.04 ~ 0.05 mole of tetra-triphenylphosphine palladium and 10.0 milliliter 1.0 is rubbed
You/liter wet chemical be warming up to 90 ~ 100 DEG C, and constant temperature is in 90 ~ 100 DEG C of magnetic force with 10 DEG C/h of heating rate
It is stirred to react 24.0 ~ 36.0 hours；Stop reaction, is down to room temperature, reaction product is poured into 200.0 milliliters of acetone, machinery stirs
It mixes 1.0 hours, filters, remove filtrate, obtain poly- { 4- [1- (potassium sulfonate) butyl] the dithieno ring penta 2 of anode modification layer material
Alkene-alternating -3,4- difluoros thiophene }.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110563745A (en) * | 2019-09-04 | 2019-12-13 | 南昌航空大学 | micromolecule hole transport material for organic solar cell and preparation method thereof |
| CN110911567A (en) * | 2018-09-18 | 2020-03-24 | 中国科学院宁波材料技术与工程研究所 | Application of sulfonate micromolecule material as cathode interface modification layer material of organic solar cell |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR101815773B1 (en) * | 2016-07-18 | 2018-01-05 | 건국대학교 산학협력단 | Electronic device comprising organic-inorganic hybrid electrolyte and preparation method thereof |
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2018
- 2018-04-11 CN CN201810319819.2A patent/CN108341935A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR101815773B1 (en) * | 2016-07-18 | 2018-01-05 | 건국대학교 산학협력단 | Electronic device comprising organic-inorganic hybrid electrolyte and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| HAITAO XU，ET AL.: "Highly and homogeneously conductive conjugated polyelectrolyte hole transport layers for efficient organic solar cells", 《J. MATER. CHEM. A》 * |
| HAITAO XU，ET AL.: "Highly and homogeneously conductive conjugated polyelectrolyte hole transport layers for efficient organic solar cells（Supplementary Information）", 《J. MATER. CHEM. A》 * |
| KATARZYNA BRYMORA，ET AL.: "Computational design of quadrupolar donor-acceptor-donor molecules with near-infrared light-harvesting capabilities", 《DYES AND PIGMENTS》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110911567A (en) * | 2018-09-18 | 2020-03-24 | 中国科学院宁波材料技术与工程研究所 | Application of sulfonate micromolecule material as cathode interface modification layer material of organic solar cell |
| CN110911567B (en) * | 2018-09-18 | 2023-04-07 | 中国科学院宁波材料技术与工程研究所 | Sulfonate micromolecule material used for organic solar cell cathode interface modification layer |
| CN110563745A (en) * | 2019-09-04 | 2019-12-13 | 南昌航空大学 | micromolecule hole transport material for organic solar cell and preparation method thereof |
| CN110563745B (en) * | 2019-09-04 | 2021-09-03 | 南昌航空大学 | Micromolecule hole transport material for organic solar cell and preparation method thereof |
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