CN108467476A - A kind of hole mobile material used for solar batteries and preparation method - Google Patents

A kind of hole mobile material used for solar batteries and preparation method Download PDF

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CN108467476A
CN108467476A CN201810319686.9A CN201810319686A CN108467476A CN 108467476 A CN108467476 A CN 108467476A CN 201810319686 A CN201810319686 A CN 201810319686A CN 108467476 A CN108467476 A CN 108467476A
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solar batteries
hole mobile
mobile material
preparation
butyl
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徐海涛
符祥
张意晨
曾光
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Nanchang Hangkong University
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    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
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    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
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    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/141—Side-chains having aliphatic units
    • C08G2261/1412—Saturated aliphatic units
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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
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Abstract

The present invention relates to a kind of hole mobile materials used for solar batteries and preparation method, preparation method to be：9 [1 (sodium sulfonate) butyl] 2,7 dibromo carbazoles and 2,7 bis- (4,4,5,51,3,2 dioxaborinate of tetramethyl, 2 base) 9,9 dioctyl fluorenes carry out Suzuki coupling reaction, it is poly- { 9 [1 (sodium sulfonate) butyl] 2,7 carbazoles replace 9,9 dioctyl fluorenes } to obtain hole mobile material used for solar batteries.Hole mobile material prepared by the present invention is used for solar cell, has many advantages, such as that handling ease, the processing of room temperature water-alcohol solution, neutral, photoelectric conversion efficiency is high.

Description

A kind of hole mobile material used for solar batteries and preparation method
Technical field
The present invention relates to a kind of hole mobile material used for solar batteries and preparation methods, particularly belong to organic solar electricity Pond interlayer materials technical field.
Background technology
Organic solar batteries have many advantages, such as at low cost, light weight, can large area processing, flexible, application field is wide, With bright application prospect.
Organic solar batteries have a major impact its photoelectric conversion efficiency and stability with hole mobile material.Hole passes Defeated material can prevent active layer from reacting with electrode, to improve the stability of organic solar batteries.Hole transport material Material can improve collection and the efficiency of transmission in hole, adjustment active layer and interelectrode interface potential barrier, to improve it is organic too The photoelectric conversion efficiency of positive energy battery.
The common hole mobile material of organic solar batteries is PEDOT: PSS at present.But PEDOT: PSS has by force Acidity, meeting corroding electrode, is unfavorable for the steady in a long-term of organic solar batteries.In addition, PEDOT: PSS has strong hygroscopicity, hold The moisture in air is easily absorbed, the stability of organic solar batteries is unfavorable for.In addition, PEDOT: the hole transport of PSS respectively to The opposite sex is also unfavorable for transmission and the mobile phone in hole, is unfavorable for the photoelectric conversion efficiency of organic solar batteries.
There is the hole transport that document and patent report use conjugated polyelectrolytes material as organic solar batteries at present Layer material, such as PCP-Na, PFS, CPE-K, CPEPh-Na, PhNa-1T etc..But above-mentioned conjugated polyelectrolytes material has The shortcomings that low hole mobility, be used for organic solar batteries hole transmission layer when, it is necessary to processing it is extremely thin, thickness is generally low In 10 nanometers, it just can guarantee that battery has high photoelectric conversion efficiency, requirement of the so thin thickness to processing technology very severe It carves.
Invention content
The present invention is intended to provide a kind of novel organic solar hole mobile material.Hole transport material provided by the invention Material have many advantages, such as high hole mobility, can room temperature water-alcohol solution processing, neutrality, photoelectric conversion efficiency it is high.
A kind of hole mobile material used for solar batteries of the present invention and preparation method, the hole used for solar batteries pass The structural formula of defeated material is as follows：
The preparation method is as follows：
Into reaction kettle be added 1.0 moles of 9- [1- (sodium sulfonate) butyl] -2,7- dibromos carbazoles, 1.0 moles of 2,7- it is bis- (4,4, 5,5- tetramethyl -1,3,2- dioxaborinate -2- bases) -9,9- dioctyl fluorenes, 0.05 mole of tetra-triphenylphosphine palladium and 50.0 Milliliter dimethyl sulfoxide (DMSO) is passed through nitrogen 1.0 hours with 0.6 liter/min of flow velocity, is then added by way of bubbling The wet chemical of 10.0 milliliter of 2.0 mol/L is stirred at room temperature 0.5 hour, make raw material be uniformly mixed, then with 5 DEG C/it is small When heating rate, be warming up to 90 ~ 100 DEG C, constant temperature is stirred to react 24.0-36.0 hours at 90 ~ 100 DEG C；Stop reaction, is down to Room temperature pours into reaction product in 200.0 milliliters of acetone, mechanical agitation 0.5 hour, filters, and removes organic solvent, obtains the sun Energy battery hole mobile material is poly- { 9- [1- (sodium sulfonate) butyl] -2,7- carbazoles-alternating -9,9- dioctyl fluorenes }.
Beneficial effects of the present invention：
Present invention hole mobile material hole mobility used for solar batteries is high, is used for organic solar batteries hole transmission layer, It may be implemented 100 nanoprocessings, the effective solution problem of processing technology harshness.In addition, the hole transmission layer material of the present invention The pH value range of aqueous solution or methanol solution or water/methanol mixed solution of material can pass through water at room temperature 7.0 ~ 7.5 Solution or methanol solution or water/methanol mixed solution dissolving processing, material are in neutrality, will not corroding electrode, can effectively improve The stability of polymer solar battery has high hole mobility, the processing of room temperature water-alcohol solution, neutral, photoelectric conversion efficiency The advantages that high.
Specific implementation mode
The principles and features of the present invention are described below, and illustrated embodiment is served only for explaining the present invention, is not intended to Limit the scope of the present invention.
Embodiment 1
Into reaction kettle be added 1.0 moles of 9- [1- (sodium sulfonate) butyl] -2,7- dibromos carbazoles and 1.0 moles of 2,7- it is bis- (4,4, 5,5- tetramethyl -1,3,2- dioxaborinate -2- bases) -9,9- dioctyl fluorenes and 0.05 mole of tetra-triphenylphosphine palladium and 50.0 milliliters of dimethyl sulfoxide (DMSO)s are passed through nitrogen 1.0 hours by way of bubbling with 0.6 liter/min of flow velocity, then add again The wet chemical for entering 10.0 milliliter of 2.0 mol/L is stirred at room temperature 0.5 hour, make raw material be uniformly mixed, then with 5 DEG C/ The heating rate of hour, is warming up to 90 DEG C, constant temperature is stirred to react 24.0 hours at 90 DEG C；Stop reaction, is down to room temperature, will react Product pours into 200.0 milliliters of acetone, mechanical agitation 0.5 hour, filters, and removes organic solvent, obtains sky used for solar batteries Hole transport materials are poly- { 9- [1- (sodium sulfonate) butyl] -2,7- carbazoles-alternating -9,9- dioctyl fluorenes }.
Embodiment 2
Into reaction kettle be added 1.0 moles of 9- [1- (sodium sulfonate) butyl] -2,7- dibromos carbazoles and 1.0 moles of 2,7- it is bis- (4,4, 5,5- tetramethyl -1,3,2- dioxaborinate -2- bases) -9,9- dioctyl fluorenes and 0.05 mole of tetra-triphenylphosphine palladium and 50.0 milliliters of dimethyl sulfoxide (DMSO)s are passed through nitrogen 1.0 hours by way of bubbling with 0.6 liter/min of flow velocity, then add again The wet chemical for entering 10.0 milliliter of 2.0 mol/L is stirred at room temperature 0.5 hour, make raw material be uniformly mixed, then with 5 DEG C/ The heating rate of hour, is warming up to 100 DEG C, constant temperature is stirred to react 36.0 hours at 100 DEG C；Stop reaction, is down to room temperature, it will be anti- Product is answered to pour into 200.0 milliliters of acetone, mechanical agitation 0.5 hour filters, and removes organic solvent, obtains used for solar batteries Hole mobile material is poly- { 9- [1- (sodium sulfonate) butyl] -2,7- carbazoles-alternating -9,9- dioctyl fluorenes }.
Pass through the performance of the hole mobile material for organic solar batteries of the following experimental test present invention.
The hole mobile material for taking 0.5 mass parts embodiment 1 or embodiment 2 to obtain, is dissolved in the bodies such as 1.0 milliliters of water and methanol The mixed in the mixed solvent of product, is used in combination 2 um filters to filter, and removes the insoluble impurity of bulky grain, obtains hole mobile material solution.
The pH value of hole mobile material solution is tested with SevenGo pH-SG2 pH meters.
Using space charge limited current method, by " hole mobile material prepared by ITO/ embodiments 1 or embodiment 2/ The hole mobility of hole mobile material prepared by Au " structures, testing example 1 or embodiment 2.
Use currently used PTB7-Th:PC71BM activity coating systems, by spin coating instrument, prepare " ITO/ embodiments 1 or Hole mobile material/PTB7-Th prepared by embodiment 2:PC71BM active layers/PFN electron transport materials/Al " structures it is organic too Positive energy battery tests the photoelectric conversion efficiency of battery further by 2400 systems of Keithley.Photoelectric conversion efficiency passes through 20 batteries of parallel determination, are averaged, and reduce error.Cell photoelectric transfer efficiency 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.
The foregoing is merely the section Examples of the present invention, are not intended to limit the invention.

Claims (1)

1. a kind of hole mobile material used for solar batteries and preparation method, it is characterised in that：The sky used for solar batteries The structural formula of hole transport materials is as follows：
The preparation method is as follows：
Into reaction kettle be added 1.0 moles of 9- [1- (sodium sulfonate) butyl] -2,7- dibromos carbazoles, 1.0 moles of 2,7- it is bis- (4,4, 5,5- tetramethyl -1,3,2- dioxaborinate -2- bases) -9,9- dioctyl fluorenes, 0.05 mole of tetra-triphenylphosphine palladium and 50.0 Milliliter dimethyl sulfoxide (DMSO) is passed through nitrogen 1.0 hours with 0.6 liter/min of flow velocity, is then added by way of bubbling The wet chemical of 10.0 milliliter of 2.0 mol/L is stirred at room temperature 0.5 hour, make raw material be uniformly mixed, then with 5 DEG C/it is small When heating rate, be warming up to 90 ~ 100 DEG C, constant temperature is stirred to react 24.0-36.0 hours at 90 ~ 100 DEG C；Stop reaction, is down to Room temperature pours into reaction product in 200.0 milliliters of acetone, mechanical agitation 0.5 hour, filters, and removes organic solvent, obtains the sun Energy battery hole mobile material is poly- { 9- [1- (sodium sulfonate) butyl] -2,7- carbazoles-alternating -9,9- dioctyl fluorenes }.
CN201810319686.9A 2018-04-11 2018-04-11 A kind of hole mobile material used for solar batteries and preparation method Pending CN108467476A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110183624A (en) * 2019-06-12 2019-08-30 南昌航空大学 A kind of preparation method of hyperbranched carbazole triphen amine conjugated polymer electrolyte cathode interface layer

Citations (2)

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Publication number Priority date Publication date Assignee Title
CN105384917A (en) * 2015-11-10 2016-03-09 华南理工大学 Conjugated polymer with side chain containing sulfonic acid or sulfonate and plane-inverted organic/inorganic hybrid perovskite solar cell prepared from conjugated polymer
KR101815773B1 (en) * 2016-07-18 2018-01-05 건국대학교 산학협력단 Electronic device comprising organic-inorganic hybrid electrolyte and preparation method thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105384917A (en) * 2015-11-10 2016-03-09 华南理工大学 Conjugated polymer with side chain containing sulfonic acid or sulfonate and plane-inverted organic/inorganic hybrid perovskite solar cell prepared from conjugated polymer
KR101815773B1 (en) * 2016-07-18 2018-01-05 건국대학교 산학협력단 Electronic device comprising organic-inorganic hybrid electrolyte and preparation method thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HAITAO XU，ET AL.: "Highly and homogeneously conductive conjugated polyelectrolyte hole transport layers for efficient organic solar cells（Supplementary Information部分）", 《J. MATER. CHEM. A》 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110183624A (en) * 2019-06-12 2019-08-30 南昌航空大学 A kind of preparation method of hyperbranched carbazole triphen amine conjugated polymer electrolyte cathode interface layer

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