CN110156780A - One kind is the non-fullerene acceptor material of imidodicarbonic diamide of core based on 8-hydroxyquinoline aluminium - Google Patents

One kind is the non-fullerene acceptor material of imidodicarbonic diamide of core based on 8-hydroxyquinoline aluminium Download PDF

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CN110156780A
CN110156780A CN201910166038.9A CN201910166038A CN110156780A CN 110156780 A CN110156780 A CN 110156780A CN 201910166038 A CN201910166038 A CN 201910166038A CN 110156780 A CN110156780 A CN 110156780A
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small molecule
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fullerene
hydroxyquinoline
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CN110156780B (en
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彭强
张光军
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Sichuan University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/06—Aluminium compounds
    • C07F5/069—Aluminium compounds without C-aluminium linkages
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • 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
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

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Abstract

The invention discloses a kind of non-fullerene small molecule receptor material of the star-like imidodicarbonic diamide of broad-band gap and its applications in organic solar batteries.The present invention, which passes through, will have the 8-hydroxyquinoline aluminium of electron-withdrawing energy and high electron mobility as core cell, upper imidodicarbonic diamide (PDI) or its dimer (PDI2) are connected in the position 5- of 8-hydroxyquinoline by suzuki reaction, two 8-hydroxyquinoline derivatives are synthesized, and by itself and Al3+Coordination forms the non-fullerene acceptor material of two broad-band gaps.Small molecule receptor material provided by the invention and narrow band gap donor material PPTEA are capable of forming that good absorption is complementary and level-density parameter.It is used in organic solar batteries that 0.85 volt of open-circuit voltage can be obtained, 71.27% fill factor, the high-energy conversion efficiency for thus obtaining 9.54%, sufficiently shows application prospect of the star-like non-fullerene small molecule of such broad-band gap in organic photovoltaic field.

Description

One kind is the non-fullerene acceptor of imidodicarbonic diamide of core based on 8-hydroxyquinoline aluminium Material
Technical field
The invention belongs to organic semiconductor material field, it is related to wide using 8-hydroxyquinoline aluminium as the imidodicarbonic diamide class of core Band gap small molecule receptor material and preparation method thereof and the application in organic solar batteries.
Background technique
Solar energy has received the extensive of people as a kind of inexhaustible, nexhaustible renewable and clean energy resource Concern.Wherein, organic solar batteries have light weight, flexibility, it is at low cost, can the advantages such as roll-to-roll progress large area production, Wide application prospect is made it have, the Typical Representative of next-generation solar battery is widely regarded as.In the past twenty years In, by the synthesis of material and the optimization of device preparation technology, the energy conversion efficiency of organic solar batteries has been obtained Great raising, great industrialization prospect.
For fullerene acceptor system, existing some defects, such as: visible region absorption is weaker, synthesis is pure Change more difficult, easy aggregation inversion device stability difference of higher cost, Energies control etc., limits the further of such photovoltaic device Development.The shortcomings that for fullerene and its derivative, develops alternative, high performance non-fullerene acceptor material gesture must Row.
Significant progress has been obtained in polymer donor material, and it is efficient to have emerged in large numbers a batch PTB7-Th, PPTEA etc. Rate low bandgap material.Preferable absorption spectrum is complementary in order to be formed with this kind of material, and the high-performance for developing alternative fullerene is wide Band gap acceptor material seems very urgent.Imidodicarbonic diamide is a kind of typical n-type organic semiconducting materials, is had good Photo and thermal stability, stronger visible region absorb compared with and the features such as higher quantum yield, be widely used in organic light It lies prostrate in device.However, the rigid structure of diimide compounds would generally make such molecule self aggregation serious, it is serious to make About the further increasing of its photovoltaic efficiency.In order to prepare efficient non-fullerene acceptor material using the advantage of imidodicarbonic diamide Material, novel imidodicarbonic diamide acceptor material urgently further develop, and are promoted with solving such molecule self aggregation and photovoltaic efficiency Contradiction.Currently, reported imidodicarbonic diamide acceptor material usually selects electron donor structure as intercooler core unit.For The electronic transmission performance for enhancing such acceptor material, using with high mobility, inhale the group of electrical property as core cell, With good advantage.
In active layer of the preparation based on imidodicarbonic diamide receptoroid material, 1,8- diiodo-octane (DIO) is usually added As additive to improve its active layer pattern, but this would generally make device open-circuit voltage reduce, and device stability It can reduce.For practical needs, how to select suitable additive aobvious for the organic photovoltaic devices for preparing efficient stable It obtains particularly critical.
Summary of the invention
The object of the present invention is to provide a kind of novel diimide compounds and its preparation side with three-dimensional structure Method, and the application as acceptor material in organic photovoltaic devices.The serious self aggregation of such material is solved, to effectively change Kind device photoelectric transfer efficiency.Meanwhile selecting the 8-hydroxyquinoline aluminium for having electrons high mobility, suction electrical as core cell It can effectively improve the electron mobility of acceptor material.Work can be effectively adjusted when 4,4 '-bipyridyl of Halogen additive is added Property layer pattern, increase photoelectric conversion efficiency while promoted device stability.
The technical scheme is that
A kind of non-fullerene acceptor material of the novel imidodicarbonic diamide with high fill factor has following general formula knot Structure:
Wherein, X selects Al, Ga or In atom；Ar selects formula II, formula III, diamide groups shown in formula IV:
Wherein, R1For C1-C12Linear or branched alkyl group.
Preferred scheme, X are Al atom；R is C1-C12Straight chained alkyl；Ar selects diamides shown in formula I and formula II Group:
Wherein, the preferred C of R1-C6Straight chained alkyl.
Most preferably had based on the non-fullerene small molecule receptor material of broad-band gap that 8-hydroxyquinoline aluminium is core following Molecular structural formula:
Main advantages of the present invention are:
1, being had based on the non-fullerene small molecule receptor material of broad-band gap that 8-hydroxyquinoline aluminium is core for being invented is good Good dissolubility, can be dissolved in most of common organic solvents, such as: toluene, chloroform, chlorobenzene etc..
2, invented based on 8-hydroxyquinoline aluminium be core the non-fullerene small molecule receptor material of broad-band gap in shortwave There is preferable absorption in long range, it is complementary preferable optical absorption to be formed with individual materials such as low bandgap material PPTEA.
3, that is invented is had based on the star-like non-fullerene small molecule receptor material of broad-band gap that 8-hydroxyquinoline aluminium is core There is higher electron mobility.When Halogen additive 4,4'-Bipyridine is added in active layer, active layer pattern can be improved, Device efficiency and device stability are improved simultaneously.
Detailed description of the invention
Fig. 1 is Alq of the invention3The uv-visible absorption spectra of-PDI small molecule receptor material；
Fig. 2 is Alq of the invention3The uv-visible absorption spectra of-PDI2 small molecule receptor material；
Fig. 3 is made based on the non-fullerene small molecule receptor of broad-band gap that 8-hydroxyquinoline aluminium is core using of the invention Current density-voltage (J-V) curve graph of standby organic solar batteries.
Specific embodiment
Below by way of specific embodiment, further the present invention will be described.
Embodiment 1
A kind of chemical structure is Alq3- PDI small molecule receptor, synthetic route are as follows:
The synthesis of compound 3: by compound 1 (0.10 gram, 0.28 mM), compound 2 (0.24 gram, 0.33 mmoles You), the solution of potassium carbonate (2 milliliters) of 2 mol/Ls is dissolved in 10 milliliters of toluene, removes oxygen, Pd is added under nitrogen protection (PPh3)4(1.3 milligrams, 2% mM), back flow reaction 12 hours.It is cooled to room temperature after reaction, solvent, column is removed under reduced pressure Chromatography purity obtains black solid product, yield 52%.
The nuclear magnetic data and Elemental analysis data of compound 3: nucleus magnetic hydrogen spectrum (400MHz, CDCl3,δ/ppm):9.03(m, 1H,ArH),8.66-8.73(m,4H,ArH),8.53(s,1H,ArH),7.90-7.93(m,2H,ArH),7.59-7.64(m, 3H,ArH),7.43-7.49(m,3H,ArH),7.35-7.39(m,1H,ArH),7.28-7.30(m,1H,ArH),7.21(d, 1H,7.3Hz,ArH),5.58(d,2H,7.2Hz,CH2),5.15(d,2H,7.2Hz,CH2),2.11-2.33(m,4H,CH2), 1.76-1.96(m,4H,CH2),1.19-1.39(m,16H,CH2),0.78-0.91(m,12H,CH3).Nuclear-magnetism carbon spectrum (100MHz, CDCl3,δ/ppm):153.08,148.66,139.03,134.48,134.36,133.39,130.70,129.17,128.94, 128.81,128.70,128.59,127.92,127.25,125.22,123.62,111.09,54.78,54.61,32.09, 32.01,29.71,29.37,29.12,29.08,22.64,22.59,14.06,14.01.Elemental analysis (C58H57N3O5): it calculates Value: C, 79.51；H,6.56；N,4.80；Measured value: C, 79.59；H,6.89；N,4.95.
The synthesis of compound 4: compound 3 (0.20 gram, 0.23 mM) is dissolved in 50 milliliters of glacial acetic acids, is added 15 milliliters of hydrobromic acids.Reactant reacts 2 hours at 120 DEG C.After reaction, it is cooled to room temperature.Filtering, obtained solid column Chromatography purity obtains black solid product, yield 56.52%.
The nuclear magnetic data and Elemental analysis data of compound 4: nucleus magnetic hydrogen spectrum (400MHz, CDCl3,δ/ppm):8.81- 8.83(m,1H,ArH),8.65-8.75(m,3H,ArH),8.58(s,1H,ArH),7.86-7.93(m,2H,ArH),7.67- 7.73(d,1H,7.2Hz,ArH),7.61-7.65(d,1H,7.2Hz,ArH),7.35-7.40(d,1H,6.8Hz,ArH), 7.27-7.29(m,2H,ArH),5.04-5.25(m,2H,CH2),2.09-2.33(m,4H,CH2),1.75-1.93(m,4H, CH2),1.17-1.37(m,16H,CH2),0.77-0.91(m,12H,CH3).Nuclear-magnetism carbon composes (100MHz, CDCl3,δ/ppm): (100MHz,CDCl3,δ/ppm):154.97,150.15,141.36,138.06,136.44,134.97,134.31,133.94, 133.02,132.34,129.16,128.95,128.81,128.66,128.13,127.90,127.31,127.27,127.23, 126.39,123.60,122.84,122.60,110.82,77.35,77.23,77.03,76.71,71.04,54.76,54.59, 32.08,31.99,29.11,29.09,22.64,22.60,14.07,14.05,14.02.Elemental analysis (C51H51N3O5): it calculates Value: C, 77.94；H,6.54；N,5.35；Measured value: C, 78.11；H,6.87；N,5.62.
The synthesis of compound Alq3-PDI: anhydrous AlCl3 (0.017 gram, 0.127 mM) is dissolved in 10 milliliters of toluene In, it is slowly added dropwise in compound 4 (0.3 gram, 0.382 mM), back flow reaction is stayed overnight at 110 DEG C, and reaction terminates 5 milliliters of decompression concentrated solution afterwards, filtering, gained crude product are washed with n-hexane, and chloroform and methanol (10:15, V/V) are tied again Crystalline substance, dry gained crude product carry out column chromatography purification with neutral alumina, obtain black solid product, yield 42.52%.
The nuclear magnetic data and Elemental analysis data of compound Alq3-PDI: nucleus magnetic hydrogen spectrum (400MHz, CDCl3,δ/ppm): 8.57-8.81(m,15H,ArH),8.23(m,3H,ArH),7.49-7.52(m,18H,ArH),5.23(m,6H,CH2),2.09- 2.35(m,12H,CH2),1.75-1.94(m,12H,CH2),1.15-1.39(m,48H,CH2),0.75-0.92(m,36H, CH3).Nuclear-magnetism carbon composes (100MHz, CDCl3,δ/ppm):152.57,149.85,139.65,138.83,137.25,129.48, 123.75,118.35,118.12,114.93,114.68,76.53,75.42,73.26,53.54,31.86,29.56,26.54, 22.96,22.70,14.14,14.10,10.93.Mass spectrum (MALDI-TOF, m/z): calculated value (C153H150AlN9O15): 2380.107；Measured value: 2380.106.
Embodiment 2
A kind of chemical structure is Alq3- PDI small molecule receptor, synthetic route are as follows:
The synthesis of compound 6: by compound 1 (0.10 gram, 0.28 mM), compound 2 (0.46 gram, 0.33 mmoles You), the solution of potassium carbonate (2 milliliters) of 2 mol/Ls is dissolved in 10 milliliters of toluene, removes oxygen, Pd is added under nitrogen protection (PPh3)4(1.3 milligrams, 2% mM), back flow reaction 12 hours.It is cooled to room temperature after reaction, solvent, column is removed under reduced pressure Chromatography purity obtains dark red solid product, yield 48.85%.
The nuclear magnetic data and Elemental analysis data of compound 6: nucleus magnetic hydrogen spectrum (400MHz, CDCl3,δ/ppm):10.32(m, 3H,ArH),9.47(d,2H,7.2Hz,ArH),8.97-9.28(m,4H,ArH),8.31-8.51(m,2H,ArH),7.9-8.0 (m,1H,ArH),7.6-7.79(m,3H,ArH),7.29-7.54(m,6H,ArH),5.67(d,2H,7.6Hz,CH2),5.19- 5.42(m,4H,7.6Hz,CH2),2.16-2.47(m,8H,CH2),1.80-2.08(m,8H,CH2),1.05-1.52(m,32H, CH2),0.64-0.96(m,24H,CH3).Nuclear-magnetism carbon composes (100MHz, CDCl3,δ/ppm):164.89,163.79,154.88, 150.03,138.63,136.35,134.00,133.80,133.33,132.74,128.89,128.27,127.92,127.31, 126.84,126.49,126.26,125.81,125.19,124.32,123.94,122.72,111.13,55.11,32.39, 31.94,31.78,29.72,26.74,22.59,14.10,14.07,13.98. elemental analysis (C102H99N5O9): calculated value: C, 79.61；H,6.48；N,4.55；Measured value: C, 79.88；H,6.56；N,4.75.
The synthesis of compound 7: compound 3 (0.35 gram, 0.23 mM) is dissolved in 50 milliliters of glacial acetic acids, is added 15 milliliters of hydrobromic acids.Reactant reacts 2 hours at 120 DEG C.After reaction, it is cooled to room temperature.Filtering, obtained solid column Chromatography purity obtains dark red solid product, yield 50.03%.
The nuclear magnetic data and Elemental analysis data of compound 7: nucleus magnetic hydrogen spectrum (400MHz, CDCl3,δ/ppm):10.33(m, 3H,ArH),9.45(d,2H,7.2Hz,ArH),8.94-9.31(m,4H,ArH),8.34-8.57(m,2H,ArH),7.31- 7.54(m,6H,ArH),5.66(d,2H,7.6Hz,CH2),5.19-5.44(m,4H,7.2Hz,CH2),2.16-2.49(m,8H, CH2),1.81-2.11(m,8H,CH2),1.03-1.55(m,32H,CH2),0.64-0.98(m,24H,CH3).Nuclear-magnetism carbon spectrum (100MHz,CDCl3,δ/ppm):165.19,164.29,156.78,152.13,148.85,139.13,137.25,135.08, 133.92,133.53,132.82,128.94,128.65,127.35,127.21,126.84,126.59,126.38,125.89, 125.34,124.56,124.04,123.52,111.56,55.41,32.46,32.04,31.64,29.80,26.78,22.49, 14.16,14.09,13.86.Elemental analysis (C95H93N5O9): calculated value: C, 78.76；H,6.47；N,4.83；Measured value: C, 79.08；H,6.58；N,4.95.
The synthesis of compound Alq3-PDI2: the synthesis of compound Alq3-PDI: by anhydrous AlCl3 (0.017 gram, 0.127 MM) be dissolved in 10 milliliters of toluene, it is slowly added dropwise in compound 4 (0.55 gram, 0.382 mM), at 110 DEG C Back flow reaction is stayed overnight, the 5 of decompression concentrated solution milliliter after reaction, and filtering, gained crude product is washed with n-hexane, chloroform with And methanol (10:15, V/V) recrystallization, dry gained crude product carry out column chromatography purification with neutral alumina, it is solid to obtain peony Body product, yield 40.85%.
The nuclear magnetic data and Elemental analysis data of compound Alq3-PDI2: nucleus magnetic hydrogen spectrum (400MHz, CDCl3, δ/ppm): 10.35(m,9H,ArH),8.57-9.46(m,21H,ArH),7.36-7.55(m,18H,ArH),5.21-5.46(m,12H, CH2),2.15-2.51(m,24H,CH2),1.81-2.15(m,24H,CH2),1.01-1.58(m,96H,CH2),0.61-0.98 (m,72H,CH3).Nuclear-magnetism carbon composes (100MHz, CDCl3, δ/ppm): 165.11,163.71,139.87,136.75,135.65, 134.98,131.26,132.67,131.66,130.56,128.98,128.12,127.98,125.26,123.45,122.76, 76.35,76.24,76.02,75.69,55.45,55.06,32.68,32.36,31.98,31.78,30.76,28.68, 25.48,14.98,14.28.Mass spectrum (MALDI-TOF, m/z): calculated value (C285H276AlN15O27): 4367.050；Measured value: 4367.050。
Embodiment 3
Alq3- PDI and Alq3The uv-visible absorption spectra of-PDI2 small molecule receptor material is tested
Fig. 1 and Fig. 2 is respectively Alq3- PDI and Alq3Purple of-PDI2 small molecule receptor the material in chloroformic solution and film Outside-visible absorption spectra.
As shown in Figure 1, Alq3For the maximum value of its film absorption of-PDI at 498 nanometers, initial absorption peak is 636 nanometers of left sides The right side, optical band gap are 1.95 electron-volts.
As shown in Figure 2, Alq3For the maximum value of its film absorption of-PD2I at 545 nanometers, initial absorption peak is 660 nanometers of left sides The right side, optical band gap are 1.95 electron-volts.
Embodiment 4
Small organic molecule acceptor material Alq3- PDI and Alq3The photovoltaic performance of-PDI2 is tested
The present invention selects narrow band gap polymer donor material PPTEA (optical band gap is near 1.60 electron-volts), point Minor structure is as follows:
The preparation process and its performance test of solar photovoltaic device: in clean ito glass on piece spin coating ZnO precursor Solution handles 30 minutes at 150 DEG C, obtains about 30 nanometers of ZnO thin layer.Acceptor material of the invention is blended with PPTEA (weight ratio 1:1.5), and in blend solution be added 0.5% 4,4'-Bipyridine.Then work is prepared by way of spin coating Property layer.Finally, depositing the MoO of 10 nanometer thickness respectively by the way of vacuum evaporation3With the Al electrode of 100 nanometer thickness.It is simulating Sunlight (AM 1.5；100 milliwatts/square centimeter) under measure the photovoltaic performance of related device.
Based on Alq3The photovoltaic performance of-PDI, as shown in Figure 3: short circuit current is 13.56mA cm-2, open-circuit voltage is 0.87V, fill factor 66.33%, thus its energy conversion efficiency are 7.82%.
Based on Alq3The photovoltaic performance of-PDI2, as shown in Figure 3: short circuit current is 15.74mA cm-2, open-circuit voltage is 0.85V, fill factor 71.27%, thus its energy conversion efficiency are 9.54%.
Table 1 is based on Alq3- PDI and Alq3- PDI2 is the photovoltaic performance data of acceptor material

Claims (5)

1. it is a kind of based on 8-hydroxyquinoline aluminium be core the non-fullerene small molecule receptor material of broad-band gap, which is characterized in that institute The molecular structure of acceptor material is stated as shown in formula I:
Wherein, X selects Al, Ga or In atom；Ar selects formula II, formula III, diimide group shown in formula IV:
Wherein, R C1-C12Linear or branched alkyl group.
2. it is as described in claim 1 the non-fullerene small molecule receptor material of broad-band gap of core based on 8-hydroxyquinoline aluminium, It is characterized in that X preferentially selects Al atom.
3. it is as described in claim 1 the non-fullerene small molecule receptor material of broad-band gap of core based on 8-hydroxyquinoline aluminium, It is characterized in that R preferentially selects C1-C12Straight chained alkyl.
4. it is as described in claim 1 the non-fullerene small molecule receptor material of broad-band gap of core based on 8-hydroxyquinoline aluminium, It is characterized in that Ar preferentially selects following imidodicarbonic diamide structure:
5. it is according to claim 4 based on 8-hydroxyquinoline aluminium be core the non-fullerene small molecule receptor material of broad-band gap Material, it is characterised in that R preferentially selects C1-C6Straight chained alkyl.
CN201910166038.9A 2019-03-06 2019-03-06 Perylene diimide non-fullerene acceptor material based on 8-hydroxyquinoline aluminum as core Expired - Fee Related CN110156780B (en)

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