CN109134515A - Six dimmer compound of imidodicarbonic diamide and preparation method, composition and organic solar batteries - Google Patents
Six dimmer compound of imidodicarbonic diamide and preparation method, composition and organic solar batteries Download PDFInfo
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Abstract
The present invention provides a kind of six dimmer compound (HPB-PDI of imidodicarbonic diamide of propeller type6), using hexaphenyl benzene (HPB) as core, the PDI unit of six β substitutions of surrounding connection.Space between the unique molecular configuration of HPB and PDI unit, which is repelled, makes HPB-PDI6Three-dimensional twisted configuration is formd, propeller type is similar to.The structure of this high distortion helps to weaken the aggtegation of PDI.By polymer P TB7-Th and HPB-PDI6It is mixed for preparing organic solar batteries, shows good photovoltaic performance.
Description
Technical field
The present invention relates to technical field of solar batteries, more particularly to a kind of six aggressiveness of imidodicarbonic diamide of propeller type
Compound and preparation method thereof and the application of six dimmer compound of imidodicarbonic diamide in organic solar batteries.
Background technique
Growing with population, demand of the mankind to the energy is also constantly being promoted, the fossils such as coal, oil and natural gas
The exploitation of the energy can not permanently meet the energy demand of the mankind eventually, and these fossil energies can bring environmental pollution and greenhouse to imitate
It answers.Therefore, scientists actively study the reproducible energy of the green such as wind energy, geothermal energy, tide energy and solar energy.Wherein, too
The positive energy that can be inexhaustible, nexhaustible as one kind, it is more safer than nuclear energy, can be with for wind energy and tide energy
It is limited by geographical conditions smaller, is a kind of green energy resource highly paid close attention to.Even if solar energy reaches the part of the earth only
Account for 2 part per billion, reach only the 70% of ground after atmosphere loss, last remaining energy still far more than
The present consumption of the mankind.
Solar battery be broadly divided into inorganic solar cell, dye-sensitized solar cells, organic solar batteries and
Perovskite solar battery.Inorganic solar cell can be divided into inorganic silicon solar cell and based on copper indium gallium selenide, cadmium telluride
With the compound batteries such as GaAs.Silicon solar cell has been realized in extensive commercial applications at present, however monocrystalline silicon and
The processing of polysilicon is complicated, at high cost；Based on toxic heavy metal is applied in the compound batteries such as copper indium gallium selenide, indium and selenium are very
It is rare, it is at high cost, it is difficult to large area preparation；It is leaded in perovskite solar battery, it is not most preferably to select in the long run/term
It selects.The advantages of organic solar batteries, light weight, flexibility can large area preparation processing it is obvious that it is at low cost.Although in early stage
Efficiency is lower, but the research with people to polymeric donor and non-fullerene acceptor, peak efficiency already exceed 14%, from reality
The again close step of existing commercial applications.
First notional organic solar batteries is nineteen fifty-nine Kallmann et al. report by pure monocrystalline anthracene material
Press from both sides the device formed between two electrodes.However be since then up to 25 years, photoelectric conversion efficiency only maintains 0.1% even
In lower level.Until 1986, Tang et al. reported effective organic solar batteries of first efficiency 1%,
It uses double-layer structure, using CuPc and perylene derivative as active layer, by the development of organic solar batteries
A new stage is pushed to.It has been successfully introduced into p-type donor and N-type receptor, and form exciton can be made to efficiently separate to
Acceptor interface.The scientists such as Sariciftci and Yoshino in 1992 have found, use polymer MEH-PPV as electronics to
Body (D), in mixing film system of the C60 as electron acceptor (A), by photoinduction, electronics can between donor and receptor into
Row fast transfer.Based on the phenomenon, Heeger in 1993 et al. is prepared for the organic of the double layer heterojunction structure of MEH-PPV:C60
Solar cell.Since then, the fullerene derivate electron acceptor of C60 one kind starts the development that is widely used.Heeger etc. is
It solves the problems, such as that exciton is efficiently separated and spread, by donor and receptor homogeneous blend, is prepared for the sun of bulk heterojunction structure
Can battery, this structure can effectively overcome double layer heterojunction limited configurations to acceptor interface and exciton diffusion length not
Sufficient device, efficiency are obviously improved.Bulk heterojunction organic solar batteries are the devices that researchers mainly use at present
Structure.Bulk heterojunction solar cell has many good qualities, for example it can carry out solution processing, light weight, at low cost and flexible
Deng.The bulk heterojunction solar cell for being based especially on fullerene derivative receptor has obtained researchers and has widely paid close attention to.
Fullerene derivative has the characteristics that high electron mobility and electron affinity and the transmission of anisotropic charge, often in body
Acceptor material is used as in heterojunction solar battery.Currently, the PCE of the organic solar batteries of unijunction has been over
11%.But fullerene derivate chemical modification is difficult and at high cost, to the absorption difference of visible light, Energies control is limited.Cause
This, it is necessary to develop a kind of active material of new organic solar batteries.
Summary of the invention
Based on the problems of the prior art, the present invention provides a kind of six aggressiveness of imidodicarbonic diamide of novel propeller type
(HPB-PDI6) compound, it is using hexaphenyl benzene (HPB) as core, the PDI unit of six β substitutions of surrounding connection.The present invention
Six dimmer compound of imidodicarbonic diamide has chemical structure shown in formula (I):
Wherein, R1And R2It is each independently selected from the alkyl of C11-C25；
Preferably, R1And R2It is each independently selected from 7- tridecyl.
It is poly- that the carbon chain lengths of substituent group in PDI unit on the N atom of diimide group will affect imidodicarbonic diamide six
The dissolubility of body compound, substituent R1And R2Carbochain it is longer, six dimmer compound of imidodicarbonic diamide is in o-dichlorohenzene, chloroform
Dissolubility in equal solvent is better.In solar cells, need six dimmer compound of imidodicarbonic diamide that there is suitable dissolution
Degree, cannot too greatly can not be too small, therefore select the alkyl of C11-C25, especially 7- tridecyl is a kind of ideal selection.
In the compound shown in formula (I), the connection of PDI and HPB can be ortho position connection, meta position connection and contraposition connection,
Preferably contraposition connection.Due to the influence of steric hindrance, six dimmer compound of imidodicarbonic diamide for aligning connection is easier to synthesize.
In a kind of preferred embodiment of the compound shown in formula (I), six dimmer compound of imidodicarbonic diamide has formula (I-
1) chemical structure shown in:
The energy level difference of the HOMO and LUMO of six dimmer compound of imidodicarbonic diamide of the present invention are 0.47eV.
The present invention also provides the synthetic method of six dimmer compound of imidodicarbonic diamide (I-1), this method includes following step
It is rapid:
(1) 1 compound of formula and 2 compound of formula are dissolved in the mixed solvent or tetrahydrofuran/toluene of tetrahydrofuran and water
With the in the mixed solvent of water, Pd (PPh is added under nitrogen atmosphere3)4, then reacted 48-72 hours at 70-90 DEG C, after
Reason obtains 3 compound of formula；
(2) 3 compound of formula is dissolved in toluene, catalyst Co is added under nitrogen atmosphere2(CO)8, anti-at 90-120 DEG C
It answers 12-24 hours, it is post-treated to obtain six dimmer compound of imidodicarbonic diamide (I-1).
Preferably, the method for the invention the step of in (1), the molar ratio of compound 2 and compound 1 is 1:2.1-
2.6, and in terms of compound 2, Pd (PPh3)4Additional amount be 5-10mol%.
Preferably, the method for the invention the step of in (2), in terms of compound 3, catalyst Co2(CO)8Feed ratio
For 0.01-20mol%；More preferably 0.01-0.05mol%.
HPB-PDI6Co can be passed through2(CO)8The ring closure reaction of catalysis is prepared, yield 50%.Unique point of HPB
Space between sub- configuration and PDI unit, which is repelled, makes HPB-PDI6Three-dimensional twisted configuration is formd, propeller type is similar to.It is this
The structure of high distortion helps to weaken the aggtegation of PDI.
The present invention also provides application of six aggressiveness of imidodicarbonic diamide in organic solar batteries.
The present invention also provides a kind of composition for organic solar batteries, the composition include electron donor with
And six aggressiveness of imidodicarbonic diamide of the present invention, wherein electron donor has complementary absorption with six aggressiveness of imidodicarbonic diamide
With matching energy level.The composition can be fabricated to active layer by being blended, and use in organic solar batteries.
Preferably, in composition of the present invention, the electron donor is PTB7-Th.It is highly preferred that PTB7-Th
Mass ratio with six aggressiveness of imidodicarbonic diamide is 1.5:1-1:1.5, more preferably 1:1.
It is highly preferred that in the composition of the present invention for organic solar batteries, the composition further includes
Additive 1,8- diiodo-octane.
The present invention also provides a kind of organic solar batteries, which includes: anode, cathode, Yi Jiwei
Active layer between anode and cathode, wherein active layer includes composition of the present invention.Preferably, organic sun
Energy battery further includes electron transfer layer and hole transmission layer.Solar energy can be improved in the addition of electron transfer layer and hole transmission layer
The efficiency of organic battery is more advantageous to the commercialization of organic solar batteries.
By HPB-PDI6Active layer is prepared with polymeric donor PTB7-Th blending and is applied in organic solar batteries.
Shown in PTB7-Th structure such as formula (II).Cyclic voltammetric is the result shows that HPB-PDI6Lumo energy be -3.93eV, with PTB7-Th
Match.Based on PTB7-Th:HPB-PDI6Organic solar batteries optimal energy transfer efficiency be 6.63%, open circuit electricity
Press VocFor 0.92V, short-circuit current density JscFor 15.11mAcm-2, fill factor FF is 48.0%.
Detailed description of the invention
Fig. 1 (a) shows HPB-PDI6DSC curve under nitrogen atmosphere；
Fig. 1 (b) shows HPB-PDI6TGA curve under nitrogen atmosphere；
Fig. 2 (a) is HPB-PDI6With ultraviolet-ray visible absorbing map of the PTB7-Th in o-dichlorobenzene solution and film；
Fig. 2 (b) is the ultraviolet-ray visible absorbing map (quality of PTB7-Th:PDI-V and PTB7-Th:PDI-E blend film
Than 1:3)；
Fig. 2 (c) is HPB-PDI6Electrochemistry map；
Fig. 2 (d) is device energy level schematic diagram；
Fig. 3 (a) is shown based on PTB7-Th:HPB-PDI6Organic solar batteries J-V curve；
Fig. 3 (b) is shown based on PTB7-Th:HPB-PDI6Organic solar batteries EQE curve；
Fig. 4 is HPB-PDI6MALDI-TOF map.
Specific embodiment
Embodiment 1
HPB-PDI6The synthesis of acceptor molecule
HPB-PDI6Synthetic route it is as follows.Compound 1 and 2 is prepared by existing document.The preparation of compound 1
It can refer to Y.Zhao, X.Li, Z.Wang, W.Yang, K.Chen, J.Zhao and G.G.Gurzadyan,
J.Phys.Chem.C.,2018,7,3756-3772；The preparation of compound 2 can refer to M.Takase, A.Nakajima and
T.Takeuchi,Tetrahedron Lett.,2005,46,1739-1742。
The synthesis of compound 3
In the round-bottomed flask of 100mL be added compound 1 (485mg, 0.58mmol), compound 2 (100mg,
0.23mmol), catalyst Pd (PPh is added after sufficiently de- ventilation in solvents tetrahydrofurane (40mL) and water (4mL)3)4
(0.012mmol, 13.4mg), then under nitrogen system 80 DEG C at a temperature of react 72 hours.It, will be molten after stopping reaction
Agent boils off, and is extracted with dichloromethane twice, merges organic layer, and anhydrous magnesium sulfate drying is added, and removes solvent and obtains crude product, adopts
Purified with silica gel chromatograph column chromatography, eluant, eluent is petroleum ether/methylene chloride (v/v=1:2), finally obtains red consolidate
Body compound 3, yield are 76% (124mg, 0.073mmol).1H NMR(500MHz,CDCl3,δ):8.70-8.59(m,10H),
8.22-8.19 (m, 2H), 7.93-7.91 (d, J=8.0Hz, 2H), 7.77-7.75 (d, J=8.0Hz, 4H), 7.57-7.55
(d, J=8.1Hz, 4H), 5.22-5.15 (m, 4H), 2.28-2.23 (m, 8H), 1.87-1.84 (m, 8H), 1.33-1.22 (m,
66H),0.85-0.81(m,22H)；13C NMR(100MHz,CDCl3,δ):164.79,163.73,142.68,140.83,
136.17,135.47,134.86,134.37,133.61,132.65,131.62,130.86,130.18,129.85,129.20,
128.85,128.65,128.12,127.55,123.98,123.62,123.48,123.01,122.38,90.52,32.39,
31.78,29.71,29.23,26.92,22.60,14.06；anal.calcd for C114H130N4O8(%): C, 81.29；H,
7.78；N, 3.33.Found (%): C, 81.03；H,7.80；N,3.32.
HPB-PDI6Synthesis
Be added compound 3 (200mg, 119mmol) and toluene (5mL) in 25mL reaction tube, sufficiently degassing inflated with nitrogen it
Catalyst Co is added afterwards2(CO)8(5mg, 0.015mmol), sufficiently deaerate inflated with nitrogen after, 110 DEG C heating stirring 24 hours.
Solvent is removed after reaction and obtains crude product, carries out silica gel chromatographic column chromatographic purifying as eluant, eluent using methylene chloride, most
After obtain red solid HPB-PDI6(100mg, 50%).HPB-PDI6There is good dissolubility in common organic reagent,
Such as chloroform, o-dichlorohenzene and chlorobenzene etc..Anal.calcd for C342H390N12O24(%): C, 81.29；H,7.78；N,
3.33.Found (%): C, 81.15；H,7.82；N,3.30.MALDI-TOF(m/z):Calcd.for C342H390N12O24:
5071.955[M+Na]+,Found5071.952[M+Na]+。
HPB-PDI6Pass through the Co of 1,2- dibenzenyl analog derivative2(CO)8Catalytic cyclization reaction can be easy to prepare
Obtain HPB-PDI6.During the experiment, it was found by the inventors of the present invention that Co in terms of compound 32(CO)8The concentration of catalyst
Even if can also obtain good result down to 0.01-0.05mol%.Compared with prior art, synthetic method of the invention can be with
Substantially reduce Co2(CO)8The usage amount of catalyst.Due to the sky between the unique a propeller configuration of HPB core and PDI unit
Between steric hindrance so that HPB-PDI6Form the three-dimensional structure of a distortion.HPB-PDI6Have in common organic solvent
Good dissolubility, and can be purified simply by silica gel column chromatography.
Embodiment 2
HPB-PDI6Thermodynamic Analysis
HPB-PDI is measured using thermogravimetic analysis (TGA) (TGA) and differential scanning calorimetric analysis (DSC)6Macroscopic property, survey
Fixed condition is all in a nitrogen environment, to be heated with the rate of 10 DEG C/min.As shown in Fig. 1 (a), TGA shows HPB-PDI6Occur
Temperature when 5% mass loss is 400 DEG C, illustrates that it has good thermal stability.As shown in Fig. 1 (b), at 50 DEG C -250
In the range of DEG C, HPB-PDI6DSC result in without apparent peak crystallization or glass transition, show HPB-PDI6It is one
A unbodied small molecule, unbodied film easy to form.
Embodiment 3
Chemical property
HPB-PDI6Electrochemical properties measured with cyclic voltammetry, cyclic voltammetry curve such as Fig. 2 (c) and Fig. 2 (d) institute
Show.Utilize ferrocene/ferrocene salt (Fc/Fc+) for oxidation-reduction pair as internal standard, ferrocene/ferrocene salt redox is electric
Gesture is 0.09eV.The calculation formula of HOMO and lumo energy is EHOMO=-e [Eox+4.80-E(Fc/Fc + )], ELUMO=-e [Ere+
4.80-E(Fc/Fc + )], the HPB-PDI measured by cyclic voltammetry6HOMO and lumo energy be respectively -5.69 and -3.93eV.
HPB-PDI6Energy level difference with the HOMO and LUMO of PTB7-Th is respectively 0.47eV and 0.29eV.
Embodiment 4
The measurement of HPB-PDI6 optical property
Normalized ultra-violet absorption spectrum of the HPB-PDI6 and PTB7-Th under o-dichlorobenzene solution neutralized film state is such as
Shown in Fig. 2 (a) and Fig. 2 (b).In o-dichlorobenzene solution, HPB-PDI6There is strong suction in 400-600nm spectral region
It receives, maximum absorption band is located at 542nm, and the molar extinction coefficient of maximum absorption band is 3.27 × 105M-1·cm-1.From solution shape
State is to filminess, HPB-PDI6Absorption map have almost no change, this indicate filminess under intermolecular phase interaction
With very weak.HPB-PDI can be calculated to obtain by the corresponding wavelength of the initial absorption of ultraviolet spectrogram under filminess6Optical band gap it is wide
Degree is 2.10eV.HPB-PDI6Complementary with the absorption spectrum of PTB7-Th, this is conducive to absorb more sunlights.Related data
It is shown in Table in 1.
Table 1HPB-PDI6With the electrochemical properties and optical property of PTB7-Th
a Eg,opt=1240/ λonset,bIt is measured by cyclic voltammetry.
Embodiment 5
HPB-PDI6The measurement of photovoltaic performance
In order to study HPB-PDI6As the photovoltaic performance of receptor, selects PTB7-Th as donor, prepare with ITO/ZnO/
Active layer/MoO3/ Al is the device of inverted structure.Shown in J-V curve such as Fig. 3 (a).It is added in o-dichlorohenzene with o-dichlorohenzene
Additive 1,8- diiodo-octane (DIO) that the volume ratio of stereometer is 0.1-3% be then added the donor that mass ratio be 1:1 and
Receptor, wiring solution-forming, and after 140 DEG C of thermal annealing 10min, device efficiency is optimal, and energy conversion efficiency is 6.63% at this time, opens
Road voltage VocFor 0.92V, short-circuit current density JscFor 15.11mAcm-2, fill factor FF is 48.0%.It is accurate in order to obtain
Short-circuit current density data, external quantum efficiency EQE is tested in experiment, as shown in Fig. 3 (b).EQE is the result shows that from EQE song
The J that line integral correctsscValue is consistent with the result that J-V is tested.
Inverted structure electronics is transmitted to ZnO (lower layer), and hole is to MoO3(upper layer) transmission, in this way setting be due to receptor with
Donor is distributed difference in active layer, it may be possible to which, since the distribution of active layer lower layer small molecule is more, inverted structure is conducive to electronics
Transmission.
Polymer P TB7-Th and HPB-PDI6With complementary absorption and matched energy level, prepared so the two is blended
Bulk heterojunction organic solar batteries.(polymer of solution used in mass ratio, spin coating including two kinds of compounds is dense for optimization
Degree, the temperature and time of film thermal annealing, additive concentration optimization) after device energy conversion efficiency be 6.63%, open
Road voltage VocFor 0.92V, short-circuit current density JscFor 15.11mAcm-2, fill factor FF is 48.0%.Experimental result table
It is bright, it is provided by the invention to show good photovoltaic by the six non-fullerene acceptors of arm star of end group of six imidodicarbonic diamide
Energy.
It is not for limiting claim, any this field skill although the application is disclosed as above with preferred embodiment
Art personnel without departing from the concept of this application, can make several possible variations and modification, therefore the application
Protection scope should be subject to the range that the claim of this application is defined.
Claims (10)
1. a kind of six dimmer compound of imidodicarbonic diamide, wherein six dimmer compound of the imidodicarbonic diamide has shown in formula (I)
Structure:
Wherein, R1And R2It is each independently selected from the alkyl of C11-C25.
2. six dimmer compound of imidodicarbonic diamide according to claim 1, which is characterized in that R1And R2It selects each independently
From 7- tridecyl.
3. six dimmer compound of imidodicarbonic diamide according to claim 1, which is characterized in that the benzene that PDI is connected at it
Replace on ring for contraposition.
4. six dimmer compound of imidodicarbonic diamide according to claim 1, which is characterized in that the imidodicarbonic diamide six is poly-
Body compound has structure shown in formula (I-1):
5. six dimmer compound of imidodicarbonic diamide according to claim 4, which is characterized in that the imidodicarbonic diamide six is poly-
The energy level difference of the HOMO and LUMO of body compound are 0.47eV.
6. a kind of method for preparing six dimmer compound of imidodicarbonic diamide as claimed in claim 4, which is characterized in that the method
The following steps are included:
(1) formula (1) compound and formula (2) compound are dissolved in the mixed solvent or tetrahydrofuran/toluene of tetrahydrofuran and water
With the in the mixed solvent of water, Pd (PPh is added under nitrogen atmosphere3)4, then reacted 48-72 hours at 70-90 DEG C, after
Reason obtains formula (3) compound；
(2) formula (3) compound is dissolved in toluene, catalyst Co is added under nitrogen atmosphere2(CO)8, reacted at 90-120 DEG C
It is 12-24 hours, post-treated to obtain six dimmer compound of imidodicarbonic diamide (I-1)；
Preferably, in step (1), the molar ratio of compound (2) and compound (1) is 1:2.1-2.6, and with compound
(2) it counts, Pd (PPh3)4Additional amount be 5-10mol%；
Preferably, in step (2), in terms of compound (3), catalyst Co2(CO)8Feed ratio be 0.01-20mol%, it is more excellent
Select 0.01-0.05mol%.
7. a kind of composition for organic solar batteries, the composition includes electron donor and claim 1 to 5 times
Six dimmer compound of imidodicarbonic diamide described in one, wherein electron donor has complementary with six aggressiveness of imidodicarbonic diamide
Absorption and matching energy level；
Preferably, the electron donor is PTB7-Th.
8. composition according to claim 7, which is characterized in that in the composition, PTB7-Th and imidodicarbonic diamide
The mass ratio of six aggressiveness is 1.5:1-1:1.5, preferably 1:1.
9. a kind of organic solar batteries, wherein the organic solar batteries include anode, cathode and are located at anode and yin
Active layer between pole, which is characterized in that the active layer includes composition described in claim 7 or 8.
10. organic solar batteries according to claim 9, which is characterized in that the organic solar batteries further include
Electron transfer layer and hole transmission layer.
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| CN112552318A (en) * | 2020-12-10 | 2021-03-26 | 北京师范大学 | Perylene diimide derivatives, preparation method thereof, use thereof in solar cells and solar cells |
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| 谢苏菲等: "基于苝二酰亚胺超支化聚合物受体在聚合物太阳能电池中的应用", 《中国化学会2017全国高分子学术论文报告会摘要集——主题H：光电功能高分子》 * |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109824703A (en) * | 2019-02-28 | 2019-05-31 | 山东师范大学 | A kind of organic compound and its preparation method and application with non-planar nuclear structure |
| CN109824703B (en) * | 2019-02-28 | 2020-05-05 | 山东师范大学 | Organic compound with non-planar core structure and preparation method and application thereof |
| CN112552318A (en) * | 2020-12-10 | 2021-03-26 | 北京师范大学 | Perylene diimide derivatives, preparation method thereof, use thereof in solar cells and solar cells |
| CN112552318B (en) * | 2020-12-10 | 2022-01-28 | 北京师范大学 | Preparation method of perylene diimide derivative |
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| CN109134515B (en) | 2020-08-14 |
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