CN108383853B - A kind of donor material based on fluorine-containing Oxoindole and preparation method thereof and device - Google Patents

A kind of donor material based on fluorine-containing Oxoindole and preparation method thereof and device Download PDF

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CN108383853B
CN108383853B CN201810088117.8A CN201810088117A CN108383853B CN 108383853 B CN108383853 B CN 108383853B CN 201810088117 A CN201810088117 A CN 201810088117A CN 108383853 B CN108383853 B CN 108383853B
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donor material
thiophene
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CN108383853A (en
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李公强
杨宇婷
王楷
郭霄
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Nanjing Shile Photoelectric Technology Co Ltd
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Nanjing Tech University
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • 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
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    • Y02E10/549—Organic PV cells

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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

The invention discloses the donor material based on fluorine-containing Oxoindole, general formula of the chemical structure is as follows:, the organic photoelectrical material synthesis step is simple, it is easy purifying, structure determination, and with the organic photovoltaic devices of the organic donor material preparation in the present invention, without cumbersome post-processing, the thick devices with high light electrotransformation efficiency only can be obtained by simple solution spin coating, and active layer thickness range can tolerate variation within the scope of 120nm-230nm, its incident photon-to-electron conversion efficiency may remain between 5.3%-7.8%, highest optoelectronic transformation efficiency can be up to 7.80%, potentiality and good application value with " roll-to-roll " preparation or printing preparation large area photovoltaic device.

Description

A kind of donor material based on fluorine-containing Oxoindole and preparation method thereof and device
Technical field
This application involves solar cell material field, especially a kind of donor material based on fluorine-containing Oxoindole and its Preparation method and device.
Background technique
Solar energy is one of ideal alternative energy source most safe, most green, most environmentally friendly at present, and solar-photovoltaic technology is also One of the important channel of fossil energy crisis is solved at present.Compared with traditional inorganic silicon-based solar battery, organic solar Battery has many advantages, such as light weight, at low cost, solution-processible, high mechanical flexibility, can be made into large area flexible device, by Favor, the development advanced by leaps and bounds in recent years.Nevertheless, cumbersome device optimization process (such as additive, thermal annealing Or solvent anneal etc.) due to the high difficulty that it accurately controls pattern, it is repeatable to result in the extremely low batch of Efficient devices Property.In addition to this, the active layer production of device is partially thin at present, and change in film thickness tolerance is very low, generally needs accurately Controlling it, higher transfer efficiency just can be achieved with a thickness of 100nm or less, in device preparation " roll-to-roll " Or the application of inkjet printing technology, and the preparation of novel donor material is vital for the improvement of the above phenomenon.
Summary of the invention
The purpose of the present invention is analyzing in view of the above technology, a kind of organic photoelectric compound, the organic photoelectrical material are provided Preparation step is simple, is easy purifying, structure determination, with the organic photovoltaic devices of the organic photoelectrical material preparation in the present invention, nothing Cumbersome optimal conditions (such as additive, thermal annealing or solvent anneal etc.) are needed, only can be obtained by simple solution spin coating The thick devices of incident photon-to-electron conversion efficiency with higher.
Technical solution of the present invention:
A kind of organic photoelectric compound, is made of big organic conjugate unit system and alkane or class alkane structure, for tool There is the dark green solid powder of metallic luster, the general formula of the chemical structure of compound is as follows:
Wherein:
R1Selected from H, C1-C8Alkyl, C1-C8Alkyl substituent, C3-C8Naphthenic base, C3-C8Naphthenic substituent, C1-C8Alcoxyl Base, R2-R5The derivative that respectively H, halogenated or its halogen replace, the halogen mean bromine, chlorine, fluorine or iodine, R2-R5It can phase It is same to can also be different；R6-R8Respectively H, C1-C30Alkyl, C1-C30Alkyl substituent, C3-C30Naphthenic base, C3-C30Naphthenic base takes Dai Ji, C1-C30Alkoxy, C1-C30Alkylthio group, halogenated C1-C30Alkyl, halogenated C3-C30Naphthenic base or halogenated C1-C30Alkoxy, And R6And R7It can be the same or different；Alkyl group can be it is any substituted that is, substituted or unsubstituted, when being taken Dai Shi, substituent group are individually and one or more group independently selected from the following: naphthenic base, aryl, heteroaryl, miscellaneous Alcyl, hydroxyl, alkoxy, aryloxy group, sulfydryl, alkylthio group, arylthio, cyano, halogenated, carbonyl, thiocarbonyl, O- amino first Acyl group, N- carbamoyl, O- thiocarbamoyl, N- thiocarbamoyl, C- acylamino-, N- acylamino-, the Asia S- sulphur Acylamino-, N- sulfonamido, C- carboxyl, O- carboxyl, isocyanato-, thiocyano, isothiocyanato, nitro, monosilane Base, three halide sulfonyls ,-NR ' R " or amino including mono- and di- substituted amino group and its protected Derivative；Group of naphthene base can be any substituted that is, substituted or unsubstituted；When substituted, substituent group is single Solely and one or more group independently selected from the following: naphthenic base, aryl, heteroaryl, heteroalicyclyl, hydroxyl, alcoxyl Base, aryloxy group, sulfydryl, alkylthio group, arylthio, cyano, halogenated, carbonyl, thiocarbonyl, O- carbamoyl, N- carbamyl Base, O- thiocarbamoyl, N- thiocarbamoyl, C- acylamino-, N- acylamino-, S- sulfonamido, N- sulfenyl Amino, C- carboxyl, O- carboxyl, isocyanato-, thiocyano, isothiocyanato, nitro, silicyl, three halide sulphurs Acyl group ,-NR ' R " or amino and its protected derivative including mono- and di- substituted amino group；
N and m takes 1 to 50 positive integer, and n and m can be the same or different；
The organic photoelectric compound, structural formula are as follows:
Wherein, R1Selected from H, C1-C8Alkyl, C1-C8Alkyl substituent, C3-C8Naphthenic base, C3-C8Naphthenic substituent, C1- C8Alkoxy, R2-R4Separately it is selected from H, C1-C30Alkyl, C1-C30Alkyl substituent, C3-C30Naphthenic base, C3-C30Cycloalkanes Base substituent group, C1-C30Alkoxy, C1-C30Alkylthio group, halogenated C1-C30Alkyl, halogenated C3-C30Naphthenic base or halogenated C1-C30Alcoxyl Base, wherein R2And R3It can be the same or different.
The organic photoelectric compound, structural formula are as follows:
The preparation method of the donor material, by the way that dialdehyde cardinal extremity based compound and fluorine-containing Oxoindole end group is precursor Object is closed to carry out Ke Neifeinageer (Knoevenagel) condensation reaction and be made, comprising the following steps:
1) under protection of argon gas, by bromo list aldehyde radical end group compound and the double tin of the alkyl-substituted benzene thiophene of thiophene Monomer, solvent a n,N-Dimethylformamide and the mixing of catalyst a tetra-triphenylphosphine palladium, heating reflux reaction 1-7 days, with dichloro Methane-petroleum ether is eluant, eluent, and column chromatography for separation obtains intermediate double aldehyde radical end group compound；The bromo list aldehyde radical end group Compound is 5 "-bromo- 3,3 ",-dioctyl-[2,2':5', 2 "-four thiophene] -5- aldehyde；
The structure of the double tin monomers of the alkyl-substituted benzene thiophene of thiophene are as follows:
2) above-mentioned dialdehyde cardinal extremity based compound, fluorine-containing Oxoindole end group precursor compound, solvent b and catalyst b are mixed It closes, under argon gas protection, is heated to reflux 24 hours, with chloroform extraction, merge organic phase, anhydrous sodium sulfate is dry, and decompression removes Solvent is removed, organic photoelectric compound is made in column chromatography for separation；
The structural formula of the dialdehyde cardinal extremity based compound is as follows:
Fluorine-containing Oxoindole end group precursor compound is the fluoro- 1,3- dihydro -2H- indol-2-one of 1- ethyl -5,6- two.
The preparation method of the donor material, bromo list aldehyde radical end group compound and the alkyl-substituted benzene thiophene of thiophene The mass ratio of double tin monomers is 2:1, solvent a n,N-Dimethylformamide and the double tin of the alkyl-substituted benzene thiophene of thiophene Change monomer amount ratio be 10-100 liter/mole, catalyst a Pd (PPh3)4With the double tin of the alkyl-substituted benzene thiophene of thiophene The molar ratio for changing monomer is 0.1-20:100.
The preparation method of the donor material, the solvent b are in chloroform, chloroform, methylene chloride and tetrahydrofuran One or more kinds of arbitrary proportions mixture；The amount ratio of solvent b and dialdehyde cardinal extremity based compound is 10-30 liter/rub You.
The preparation method of the donor material, the catalyst b be one or both of triethylamine, pyridine and piperidines with The mixing of one or more of the mixture and ammonium acetate of upper arbitrary proportion, propionic acid ammonium and butyric acid ammonium arbitrary proportion Object；The molar ratio of catalyst b and dialdehyde cardinal extremity based compound is 2:10.
A kind of solar cell photovoltaic device: the activity using the donor material as solar cell photovoltaic device Layer.
The invention has the advantages that the organic photoelectrical material synthesis step is simple, is easy purifying, structure determination, and with this hair The organic photovoltaic devices of organic donor material preparation in bright, without cumbersome post-processing (such as additive, thermal annealing or solvent Annealing etc.), the thick devices with high light electrotransformation efficiency, and active thickness only can be obtained by simple solution spin coating Degree range can tolerate 120nm-230nm within the scope of variation, incident photon-to-electron conversion efficiency may remain in 5.3%-7.8% it Between, highest optoelectronic transformation efficiency can be up to 7.80%, the potentiality with " roll-to-roll " preparation or printing preparation large area photovoltaic device With good application value.
Detailed description of the invention
Fig. 1 is the ultraviolet-visible absorption spectroscopy of compound solution prepared by embodiment 1 and film.
Fig. 2 is current density voltage curve of the compound of the preparation of embodiment 1 under optimal device conditions.
Fig. 3 is thermogravimetric analysis (TGA) curve of compound prepared by embodiment 1.
Fig. 4 is differential scanning calorimetry (DSC) curve of compound prepared by embodiment 1.
Specific embodiment
In the following description, including certain concrete details are to provide comprehensive reason to each disclosed embodiment Solution.However, those skilled in the relevant art are not, it will be recognized that use one or more of these concrete details, and use other Embodiment can be achieved in the case where method, component, material etc..
Embodiment 1:
A kind of organic photoelectric compound, is made of big organic conjugate unit system and alkane or class alkane structure, for tool There is the dark green solid powder of metallic luster, the general formula of the chemical structure of compound is as follows:
Wherein: R1For ethyl, R2And R3For fluorine atom, R4And R5For n-octyl, R6For 2- ethylhexyl, i.e. the compound Chemical structural formula are as follows:
This for solar battery organic photoelectric compound preparation method, by by dialdehyde cardinal extremity based compound with contain Fluorine Oxoindole end group precursor compound carries out Ke Neifeinageer (Knoevenagel) condensation reaction and is made, including following Step:
1) under protection of argon gas, by 5 "-bromo- 3,3 ",-dioctyl-[2,2':5', 2 "-four thiophene] -5- aldehyde 3.85g (6.63mmol) and the alkyl-substituted benzene thiophene of thiophene double tin monomer 3.00g (3.32mmol), 60mL dry N, N- bis- Methylformamide and tetra-triphenylphosphine palladium 0.20g (0.17mmol) mixing, heating reflux reaction 1 day, then pour into reaction solution It in 100mL water, is extracted 3 times with 40mL methylene chloride, organic phase is with 50mL water washing 3 times, and after anhydrous sodium sulfate is dry, decompression is removed N,N-Dimethylformamide is gone, using dichloromethane-petroleum ether as eluant, eluent, intermediate double aldehyde radical end group is made in column chromatography for separation Compound, structural formula are as follows:
2) by above-mentioned dialdehyde cardinal extremity based compound 1.00g (0.63mmol), 1- ethyl -5,6- two in 100mL bottle with two necks Fluoro- 1,3- dihydro -2H- indol-2-one 1.25g (6.34mmol), dry chloroform 150mL and piperidines 0.01g (0.05mmol) mixing is heated to reflux 24 hours under argon gas protection, with chloroform extraction, merges organic phase, anhydrous sodium sulfate It is dry, solvent is removed under reduced pressure, metallic luster dark green solid, that is, organic photoelectric compound 1.00g, yield is made in column chromatography for separation It is 81.5%.1H NMR (500MHz, CDCl3) δ 7.61 (dd, J=13.8,6.0Hz, 3H), 7.46 (dd, J=48.1, 23.7Hz, 2H), 7.34-7.28 (m, 4H), 7.12 (s, 4H), 6.95 (d, J=3.2Hz, 2H), 6.81-6.64 (m, 2H), 3.91-3.78 (m, 6H), 2.93-2.75 (m, 18H), 1.71 (d, J=6.9Hz, 16H), 1.51-1.20 (m, 100H), 0.98 (dd, J=18.9,11.5Hz, 16H), 0.88 (t, J=6.3Hz, 14H) .HRMS (MALDI-TOF): m/z calcd for C112H132F4N2O2S10:1934.90.Found:1930.596[M]+.
The test method of the ultraviolet-visible absorption spectroscopy of compound obtained:
Organic photoelectric compound obtained is made into 10 respectively-5Mol/L and 10-2The chloroformic solution of mol/L, former solution For measuring solution UV absorption, the latter solution in 1200rpm on quartz plate after rejection film, for measuring the UV absorption of film, Scanning range is 300-900 nanometers, measuring instrument SHIMADZUUV-1750.Ultraviolet-visible absorption spectroscopy is as shown in Figure 1. The solution of the compound has good absorption in the range of 300-800 nanometers, and film has more than 59 nanometers relative to solution Red shift, and there is wider absorption region, it help to obtain higher incident photon-to-electron conversion efficiency.
The test method of the thermogravimetric analysis of compound obtained:
By organic photoelectric compound obtained in a vacuum drying oven it is dry for 24 hours, remove remaining a small amount of organic solvent and Water weighs 3mg in ceramic crucible, carries out thermogravimetric analysis, journey on thermogravimetric analyzer METTLER TOLEDO TGA2 after dry Sequence gas is nitrogen, flow 50mL/min.The temperature range of measurement is 30-600 DEG C.
The test method of the differential scanning calorimetric curve of compound obtained:
By organic photoelectric compound obtained in a vacuum drying oven it is dry for 24 hours, remove remaining a small amount of organic solvent and Water weighs 3mg in aluminum cup, using the dress sample loading mode for covering punching, in analyzer NETZSCH after dry Differential scanning calorimetric analysis is carried out on DSC214Polym, purge gass and protection gas are nitrogen, and flow is respectively 40mL/min And 60mL/min.The temperature range of measurement is 30-300 DEG C.
The preparation of solar cell device is used for using organic photoelectric compound obtained as electron donor:
Device architecture is ITO/PEDOT:PSS/ donor molecule: PC71BM/PFN-Br/Al.Specific preparation process are as follows: first ITO (tin indium oxide, anode) glass is pre-processed, the specific steps are as follows: first by ito glass successively with dish washing liquid, go Ionized water, acetone, isopropanol solvent are cleaned by ultrasonic each 20 minutes, are dried up after taking-up with nitrogen gun, and UV-Ozone handles 30min. Then one layer of PEDOT:PSS (CleviosPVPAl4083) of spin coating is used as anode modification layer on pretreated ito glass, to PEDOT:PSS dries 10 minutes at 150 DEG C in an oven, the compound and PC for preparing embodiment 1 after cooling71The mixture of BM Chloroformic solution is spin-coated on the surface PEDOT:PSS as active layer, then carries out thermal annealing and solvent vapo(u)r annealing, spin coating with a thickness of The methanol solution of the PFN-Br of 10nm, last evaporation thickness are the metal electrode Al of 100nm.Vacuum degree is kept during vapor deposition Lower than 2 × 10-6Pa.Under standard sunlight (AM1.5G) radiation parameter, keep the Keithley2400 to computerized control digital Source table tests device performance, and performance parameter is listed in table 1-3.
Table 1: compound is compared to/receptor than the solar cell properties of preparation with difference
(light intensity 100mW/cm2It is measured under AM1.5G irradiation condition)
Table 2: compound is compared with solar cell properties prepared by different activities thickness degree
(light intensity 100mW/cm2It is measured under AM1.5G irradiation condition)
Table 3: compound is compared with solar cell properties prepared by different interfaces
(light intensity 100mW/cm2It is measured under AM1.5G irradiation condition)
Fig. 2 is current density voltage curve of the compound of the preparation of embodiment 1 under optimal device conditions, is shown in figure: Open-circuit voltage (the V of the corresponding battery of organic solar batteries optimised devices based on compoundoc) it is 0.84V, short circuit current is close Spend (Jsc) it is 13.0mA/cm2, fill factor (FF) is 71.8%, and it is high performance that photoelectric conversion efficiency (PCE), which is 7.80%, Organic solar batteries.
In conclusion using the compounds of this invention preparation solution processing bulk heterojunction solar cells device without It post-processes (such as additive, thermal annealing or solvent anneal etc.), can be obtained the thick devices with preferable photovoltaic performance, Maximum photoelectric conversion efficiency can reach 7.80%.And the active layer prepared using the compound of the present invention, thickness range can Changed with tolerating within the scope of 120nm-230nm, incident photon-to-electron conversion efficiency may remain between 5.3%-7.8%, have " volume To volume " prepare or print the potentiality and good application value that prepare large area photovoltaic device.
It should be understood that for those of ordinary skills, it can be modified or changed according to the above description, And all these modifications and variations should all belong to the protection domain of appended claims of the present invention.

Claims (6)

1. a kind of donor material based on fluorine-containing Oxoindole, which is characterized in that structural formula are as follows:
2. a kind of preparation method of donor material as described in claim 1, it is characterised in that: by by dialdehyde cardinal extremity based compound Ke Neifeinageer (Knoevenagel) condensation reaction is carried out with fluorine-containing Oxoindole end group precursor compound and is made, including Following steps:
1) under protection of argon gas, by bromo list aldehyde radical end group compound and the double tin lists of the alkyl-substituted benzene thiophene of thiophene Body, solvent a n,N-Dimethylformamide and the mixing of catalyst a tetra-triphenylphosphine palladium, heating reflux reaction 1-7 days, with dichloromethane Alkane-petroleum ether is eluant, eluent, and column chromatography for separation obtains intermediate double aldehyde radical end group compound；The bromo list aldehyde radical end group Closing object is 5 "-bromo- 3,3 ",-dioctyl-[2,2':5', 2 "-four thiophene] -5- aldehyde；
The structure of the double tin monomers of the alkyl-substituted benzene thiophene of thiophene are as follows:
2) above-mentioned dialdehyde cardinal extremity based compound, fluorine-containing Oxoindole end group precursor compound, solvent b and catalyst b are mixed, argon It under gas shielded, is heated to reflux 24 hours, with chloroform extraction, merges organic phase, anhydrous sodium sulfate is dry, is removed under reduced pressure molten Organic photoelectric compound is made in agent, column chromatography for separation；
The structural formula of the dialdehyde cardinal extremity based compound is as follows:
Fluorine-containing Oxoindole end group precursor compound is the fluoro- 1,3- dihydro -2H- indol-2-one of 1- ethyl -5,6- two.
3. the preparation method of donor material according to claim 2, it is characterised in that: bromo list aldehyde radical end group compound and thiophene The mass ratio of the double tin monomers of the benzene thiophene that alkylated phenothiazine replaces is 2:1, solvent a n,N-Dimethylformamide and thiophane The amount ratio of the double tin monomers of the benzene thiophene that base replaces be 10-100 liter/mole, catalyst a Pd (PPh3)4With thiophane The molar ratio of the double tin monomers of the benzene thiophene that base replaces is 0.1-20:100.
4. the preparation method of donor material according to claim 2, it is characterised in that: the solvent b is chloroform, three chloromethanes The mixture of one or more of alkane, methylene chloride and tetrahydrofuran arbitrary proportion；Solvent b and dialdehyde cardinal extremity base chemical combination The amount ratio of object be 10-30 liter/mole.
5. the preparation method of donor material according to claim 2, it is characterised in that: the catalyst b is triethylamine, pyridine With one of the mixture of one or more of piperidines arbitrary proportion and ammonium acetate, propionic acid ammonium and butyric acid ammonium or The mixture of two or more arbitrary proportions；The molar ratio of catalyst b and dialdehyde cardinal extremity based compound is 2:10.
6. a kind of solar cell photovoltaic device, it is characterised in that: using donor material described in claim 1 as solar-electricity The active layer of pond photovoltaic device.
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