CN104230773A - Organic hole-transport material applied to all-solid-state perovskite sensitized solar cell - Google Patents
Organic hole-transport material applied to all-solid-state perovskite sensitized solar cell Download PDFInfo
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- CN104230773A CN104230773A CN201410459003.1A CN201410459003A CN104230773A CN 104230773 A CN104230773 A CN 104230773A CN 201410459003 A CN201410459003 A CN 201410459003A CN 104230773 A CN104230773 A CN 104230773A
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- Y02E10/549—Organic PV cells
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Abstract
The invention provides an organic hole-transport material which is applied to an all-solid-state perovskite sensitized solar cell and takes spirobifluorene as a core. The organic hole-transport material is characterized by taking the spirobifluorene as the core, the spirobifluorene is bridged with diarylamine, a sulphur-containing group is introduced at a tail end for modifying, a structural general formula of the organic hole-transport material is described in the specification, and in a structural formula of a compound IV, R1 and R2 are one of C1-C12 alkyls respectively. The organic hole-transport material has the advantages that the spirobifluorene is taken as the core, so that the organic hole-transport material is of an orthogonal three-dimensional structure, glassy state forming capability is enhanced, and crystallization of the hole-transport material is avoided; and the organic hole-transport material can serve as a hole transport layer in an all-solid-state perovskite sensitized solar cell device structure, so that photoelectric conversion efficiency of the existing perovskite solar cell is improved.
Description
Technical field
The invention belongs to technical field of solar batteries, particularly relate to a kind of novel application of organic hole transport material in all solid state uhligite sensitization solar battery being core with spiral shell two fluorenes.
Background technology
Along with global warming and fossil energy use totally, clean reproducible novel energy is the target that the mankind pursue always.Sun power is the focus that people study as inexhaustible clean energy always.Solar cell is direct is the device of electric energy by solar energy converting.Be obtained for from traditional silicon solar cell novel battery that is representative with dye sensitization solar battery and organic solar batteries up till now again and develop rapidly.All solid state uhligite sensitization solar battery development in nearly 2 years rapidly, becomes an international study hotspot.In uhligite solar cell device structure, hole mobile material is very crucial part, and it plays the effect of conduction hole.Adopt organic hole transport material to replace liquid electrolyte can be assembled into all solid state uhligite sensitization solar battery, the volatilization leakage problem of liquid electrolyte can be solved.In the high-level efficiency uhligite solar cell device of current bibliographical information in the world, major part uses
sprio-MeOTAD as hole transmission layer, such as document (1) Dianyi L, Timothy L. K. nature photonics 2014,8,133-138; Document (2) Michael M. L, Joel T, Tsutomu M, Takurou N. M, Henry J. S, science 2012,338,643-647; (3) Ball J M, Lee M M, Hey A, Snaith H J, Energy Environ. Sci., reported in 2013,6,1739 – 1743 grades.In order to improve the photoelectric transformation efficiency of uhligite solar cell further, scientists is also exploring novel organic hole transport material row as document (1) Anurag K, Dharani S always, Hairong L, Jun Y, Pablo P. B, Cesare S, Subodh G. M, Andrew C. G, Chem. Sci., 2014,5,2702 – 2709; (2) Nam J J, Hag G L, Young C K, Jangwon S, Jun H N, Jaemin L, Sang S, J. Am. Chem. Soc. 2014,136,7,837 7840; (3) reported in Hairong L, Kunwu F, Anders H, Michael G, Subodh G. M, Andrew C. G, Angew. Chem. Int. Ed. 2014,53,4085 – 4088 grade.
Summary of the invention
The invention provides a kind of for all solid state uhligite sensitization solar battery with spiral shell two fluorenes for core organic hole transport material, it is characterized in that described organic hole transport material with spiral shell two fluorenes for core overseas Chinese federation diaryl-amine, at tail end thiylation, group modifies, and its general structure is:
In compound IV structural formula, R1 and R2 refers to the one in C1-C12 alkyl.
A kind of preparation method being applied to all solid state uhligite solar cell organic hole transport material of the present invention, comprises the following steps:
A. grignard reagent reaction: under protection of inert gas, 2-bromo biphenyl is dissolved in appropriate non-polar solvent, drops in magnesium chips, prepare Grignard reagent; Fluorenone is dissolved in non-polar solvent, drops in above-mentioned grignard reagent, after reaction for some time, obtain product 1;
In above-mentioned steps a, 2-bromo biphenyl and the ratio of the volume number of ether dissolution are 1 mmol:5 mL ~ 10 mL; The consumption mol ratio of three kinds of reactants, i.e. 2-bromo biphenyl: magnesium chips: the mol ratio of Fluorenone is 1:1.01:1.1 ~ 1:1.2:1.5;
B. be oxidized substitution reaction: joined by step a products therefrom 1 in the mixing solutions of the vitriol oil, acetic acid and water, after being heated to certain temperature, add iodine and acid iodide, then react for some time under this system temperature;
In above-mentioned steps b, product 1 is 16:1 ~ 17:1 with the ratio of the volume number of the vitriol oil, and product is 4:1 ~ 6:1 with the ratio of the volume number of water, and product 1 is 1:5:3:2 ~ 1:5:4:3 with the mol ratio of acetic acid, iodine, acid iodide;
C. bromo-amine condensation: under protection of inert gas, by 4-(alkylthio) aniline is dissolved in dimethyl sulfoxide (DMSO), adds appropriate 4-bromine sulfo-phenylate, L-PROLINE, cuprous iodide and salt of wormwood, is warming up to 90 DEG C ~ 100 DEG C, after reaction one end time, obtains product 3;
In above-mentioned steps c, 4-(alkylthio) the mmole number of aniline is 1 mmol:5 mL ~ 10 mL with the ratio of the volume number of dimethyl sulfoxide (DMSO); 4-(alkylthio) mol ratio of aniline and 4-bromine sulfo-phenylate, L-PROLINE, cuprous iodide and salt of wormwood is 1:2:0.2:0.1:2 ~ 1:3:0.3:0.2;
D., under protection of inert gas, step b and step c products therefrom 2 and product 3 are dissolved in weak polar solvent, add organophosphorus, organic palladium and highly basic, reacting by heating, obtain compound IV;
In above-mentioned steps d, the mmole number of product 2 and the ratio of the volume number of toluene are 1 mmol:5 mL ~ 10 mL; Product 2 is 1:4:4:0.1:0.05 ~ 1:5:5:0.2:0.1 with the mol ratio of products therefrom 3, highly basic, organophosphor ligand and palladium catalyst.
Further, in described step a, non-polar solvent is ether or tetrahydrofuran (THF), and the reaction times is 12 hours ~ 24 hours; In described step b, Heating temperature is 90 DEG C ~ 100 DEG C, and the reaction times is 4 hours ~ 5 hours; In described step c, the reaction times is 24 hours ~ 48 hours; In steps d, Heating temperature is 110 DEG C ~ 120 DEG C, and the reaction times is 12 hours ~ 48 hours.
Further, the organophosphor ligand in described steps d is trimethyl-phosphine, triphenylphosphine, tri-butyl phosphine, and palladium catalyst is Pd (PPh
3)
4, PdCl
2(dppf), Pd (OAc)
2.
A kind of all solid state uhligite sensitization solar battery, comprise the transparent substrate, transparency conducting layer, tight zone, porous dielectric layer, the organo-metallic semi-conductor light absorbing material with perovskite structure, organic cavity transmission layer and the metal electrode that stack gradually, it is characterized in that, the material of organic cavity transmission layer is compound IV.
Further, described transparent substrate is transparent glass, and transparency conducting layer is FTO film.Described tight zone is by TiO
2film is formed; Dense layer thickness is between 20-200 nm; Be preferably 50 nm.
Further, described porous dielectric layer is by Al
2o
3or ZrO
2or SiO
2formed, the thickness of described porous dielectric layer between 200-1500 nm, Al
2o
3or ZrO
2or SiO
2pattern is nano particle or nanometer rod or nano wire.
Further, described tight zone, porous dielectric layer are formed by silk screen print method.
Further, it is (RNH that the organo-metallic semi-conductor light absorbing material described in perovskite structure is selected from chemical general formula
3) BX
my
nin one or more materials, wherein R=CH
3, C
4h
9, C
8h
9; B=Pb, Sn; X, Y=Cl, Br, I; M=1,2,3; N=3-m.
Further, described metal electrode is gold or silver-colored.
A preparation method for all solid state uhligite sensitization solar battery, comprising:
The transparent substrate providing surface to have transparency conducting layer, the tight zone that described transparency conducting layer is formed semiconductor material, described tight zone is formed porous dielectric layer, porous dielectric layer is formed perovskite structure organo-metallic semi-conductor light-absorption layer, perovskite structure organo-metallic semi-conductor light-absorption layer forms organic cavity transmission layer and in organic cavity transmission layer, forms metal counter electrode layer, encapsulation, it is characterized in that, compound IV is spun on calcium titanium ore bed as organic hole transport material, prepares hole transmission layer; Will to electrode evaporation to hole transmission layer surface by vacuum vapour deposition to electrode.
Further, described tight zone, porous dielectric layer are formed by silk screen print method.
The novel organic hole transport material that the present invention relates to synthesis is with spiral shell two fluorenes for core, and overseas Chinese federation's diaryl-amine take sulfur-containing group as tail end.Computer theory analog calculation result carried out to the material of different tail end as follows:
From calculating simulation data, we can see, the introducing of sulphur atom changes HOMO and the lumo energy of hole mobile material.This may be because the existence of sulphur atom eliminates intermolecular C-H π effect, and introduces hydrogen bond, π π effect and SS effect, and the appearance of these effects can strengthen Intermolecular Forces, and stronger Intermolecular Forces is favourable for transferring charge.
In addition, make material morphologically can form good amorphous state with spiral shell two fluorenes for core and there is good solvability certainly, being soluble in most of organic solvent.Amorphous state and high solvability make material can be good at penetrating into mesoporous TiO
2in film; On molecular structure, make material have three orthogonal structure with spiral shell two fluorenes for core, enhance vitreous state Forming ability, avoid the crystallization of hole mobile material; As the hole transmission layer in all solid state uhligite sensitization solar battery device architecture, to improve the photoelectric transformation efficiency of current uhligite solar cell.
Accompanying drawing explanation
Fig. 1 is the synthetic route chart of embodiment 1 and embodiment 2.
Fig. 2 is the structural representation of the uhligite solar cell device that embodiment 3 is prepared.
Embodiment
Below in conjunction with accompanying drawing embodiment, the present invention is described in further detail, it is pointed out that the following stated embodiment is intended to be convenient to the understanding of the present invention, and any restriction effect is not play to it.
embodiment 1:
In this enforcement, novel hole transport material is with spiral shell two fluorenes for core, and introduce thiomethyl (compound 4) at tail end, its structural formula is:
As shown in Figure 1, R
1and R
2be methyl, the preparation method of above-mentioned novel hole transport material comprises the steps.
(1) synthesis of compound 1
Under nitrogen protection, 2-bromo biphenyl (11.65g, 50 mmol) is dissolved in 20ml anhydrous diethyl ether, is added drop-wise in the round-bottomed flask filling magnesium chips (1.26g, 52.5 mmol), after question response is initiated, continues slowly to drip 2-bromo biphenyl solution, then refluxes 3 hours.In reaction system, drip 9-Fluorenone (9.9g, 55 mmol) diethyl ether solution, dropwise rear backflow and spend the night.Cold filtration yellow solid, washed with ether, joined by washing gained solid in ammonium chloride solution and stir 2 hours, filtration drying obtains white solid.Put into by gained white solid in the acetic acid solution (100 mL) of boiling, cooling, is poured into water, and separates out white solid, and filter, ethyl alcohol recrystallization obtains colorless plate crystal 14.2g, productive rate 90%.
(2) synthesis of compound 2
Add compound 1(1.9g in 100 mL single necked round bottom flask, 6 mmol), the vitriol oil (0.36 mL), acetic acid (30 ml) and water (1.2 mL) is heated to 90 DEG C.Then iodine (4.87g, 19.2 mmol) and acid iodide (2.11g, 12 mmol) is added.React four hours at 90 DEG C, poured into by mixing solutions in frozen water, filter and obtain pink solid, re crystallization from toluene obtains white powder 2.02 g, productive rate 41.1%.
(3) synthesis of compound 3
Under nitrogen protection; 4-bromine thioanisole (6.093 g are added in 250 mL two-mouth bottles; 30 mmol), 4-(methyl thio) aniline (2.78 g; 20 mmol), salt of wormwood (5.53 g; 40 mmol), L-PROLINE (0.46 g; 4 mmol), cuprous iodide (0.38 g, 2 mmol) and 30 mL dimethyl sulfoxide (DMSO) are heated to 90 DEG C, reaction 27h.Solution is cooled to room temperature, and washing, extraction into ethyl acetate, anhydrous sodium sulfate drying, revolve and steam desolventizing, and solid silicagel column is separated, and sherwood oil and ethyl acetate (1:9) do eluent, obtain yellow solid 4.7 g, productive rate 60%.
(4) synthesis of compound 4
Under nitrogen protection; people's compound 2(0.41 g is added in 25 ml two-mouth bottles; 0.5 mmol), compound 3(0.661 g; 2.5 mmol), potassium tert.-butoxide (0.35 g; 3.16 mmol), tributylphosphine (0.01 g, 0.05 mmol), palladium (5.6 mg, 0.025 mmol) and 5 mL toluene; be heated to 120 DEG C, react 24 hours.System is cooled to room temperature, adds water, chloroform extraction, washing, anhydrous sodium sulfate drying; Revolve and steam removing trichloromethane, solid silicagel column is separated, and sherwood oil and ethyl acetate (1:9) do eluent, obtain yellow solid 450 mg, productive rate 67%.
embodiment 2:
In this enforcement, novel hole transport material is with spiral shell two fluorenes for core, and introduce sulphur ethyl (compound 6) at tail end, its structural formula is:
As shown in Figure 1, R
1and R
2be ethyl, the preparation method of above-mentioned novel hole transport material comprises the steps:
Step (1) is identical with (2) with the step (1) in example 1 with (2).
(3) synthesis of compound 5
Under nitrogen protection; 4-bromine thio phenyl ether (6.514 g are added in 250 ml two-mouth bottles; 30 mmol), 4-(ethylenebis dithiocarbamate) aniline (3.065 g; 20 mmol), salt of wormwood (5.53g; 40 mmol), L-PROLINE (0.46 g; 4 mmol), cuprous iodide (0.38 g, 2 mmol) and 30ml dimethyl sulfoxide (DMSO) be heated to 90 DEG C, reacts 27 h.Solution is cooled to room temperature, and washing, extraction into ethyl acetate, anhydrous sodium sulfate drying, revolve and steam desolventizing, and solid silicagel column is separated, and sherwood oil and ethyl acetate (1:9) do eluent, obtain yellow solid 3.5 g, productive rate 60%.
(4) synthesis of novel hole transport material 6
Under nitrogen protection; people's compound 2(0.41 g is added in 25 ml two-mouth bottles; 0.5 mmol), compound 5(0.723 g; 2.5 mmol), potassium tert.-butoxide (0.35g; 3.1 6mmol), tributylphosphine (0.01g, 0.05 mmol), palladium (5.6 mg, 0.025 mmol) and 5 mL toluene; be heated to 120 DEG C, react 24 hours.System is cooled to room temperature, adds water, chloroform extraction, washing, anhydrous sodium sulfate drying; Revolve and steam removing trichloromethane, solid silicagel column is separated, and sherwood oil and ethyl acetate (1:9) do eluent, obtain yellow solid 370 mg, productive rate 50.5%.
The molecular center of above-mentioned obtained compound 4 and 6 has spiral shell two fluorenes kernel, makes whole molecular juction form 3-D solid structure.These two kinds of compounds have good solubility, can be dissolved in and common are machine solvent.Tail end thiylation group simultaneously, the introducing of sulphur-sulfide linkage makes intermolecular reactive force strengthen, and the mobility of material is improved.This bi-material can as the hole transmission layer of uhligite sensitization solar battery.
Above-described embodiment has been described in detail technical scheme of the present invention; be understood that and the foregoing is only specific embodiments of the invention; be not limited to the present invention; all make in spirit of the present invention any amendment, supplement or similar fashion substitute etc., all should be included within protection scope of the present invention.
embodiment 3:novel hole transport material 5 prepares uhligite sensitization solar battery
The solar cell that preparation 5 is in parallel on one piece of conductive glass, step is as follows:
Conductive glass pre-treatment: sheet glass conductive glass being cut into 20 mm × 12 mm sizes, successively with washing composition, deionized water, EtOH Sonicate cleaning.
Silk screen printing molding step: use screen process press, the conductive glass cleaned prints one deck TiO
2(20 mm × 10 mm) tight zone slurry, obtains fine and close TiO through 80 DEG C of oven dry, 450 DEG C of sintering after 30 minutes
2film, film thickness can be optional between 20-150 nm; The Al of 20 mm × 10 mm is of a size of again at its surface printing one deck
2o
3nano particle slurry, through 80
oc is dried, 450 DEG C of sintering obtained Al after 30 minutes
2o
3porous membrane, film thickness can be directly optional at 200-150 nm.
Uhligite filling step: the uhligite solution device of above-mentioned preparation being dripped 10 mg/mL, spin coating, vacuum drying oven 80 DEG C keeps 1 hour.
Hole transmission layer preparation process: the hole mobile material chlorobenzene solution device of above-mentioned preparation being dripped 5 mg/mL, spin coating, vacuum drying oven 80
oc keeps 1 hour.
To electrode evaporation step: will to electrode gold evaporation to hole transmission layer surface by vacuum vapour deposition, thickness be about 60 nm.
Encapsulation step: hot melt adhesive film, cover glass are put into thermocompressor successively, hot pressing 15 seconds.A structure monoblock uhligite sensitization solar battery as shown in Figure 2 can be obtained.
Claims (10)
1. for an organic hole transport material for all solid state uhligite sensitization solar battery, it is characterized in that, described organic hole transport material is with spiral shell two fluorenes for core overseas Chinese federation diaryl-amine, and at tail end thiylation, group modifies, and its general structure is:
In compound IV structural formula, R1 and R2 refers to the one in C1-C12 alkyl.
2. a kind of preparation method being applied to all solid state uhligite sensitization solar battery organic hole transport material according to claim 1, comprises the following steps:
A. grignard reagent reaction: under protection of inert gas, 2-bromo biphenyl is dissolved in appropriate non-polar solvent, drops in magnesium chips, prepare Grignard reagent; Fluorenone is dissolved in non-polar solvent, drops in above-mentioned grignard reagent, after reaction for some time, obtain product 1;
B. be oxidized substitution reaction: joined by step a products therefrom 1 in the mixing solutions of the vitriol oil, acetic acid and water, after being heated to certain temperature, add iodine and acid iodide, then react for some time under this system temperature;
C. bromo-amine condensation: under protection of inert gas, by 4-(alkylthio) aniline is dissolved in dimethyl sulfoxide (DMSO), adds appropriate 4-bromine sulfo-phenylate, L-PROLINE, cuprous iodide and salt of wormwood, is warming up to 90 DEG C ~ 100 DEG C, after reaction one end time, obtains product 3;
D., under protection of inert gas, step b and step c products therefrom 2 and product 3 are dissolved in weak polar solvent, add organophosphor ligand, palladium catalyst and highly basic, reacting by heating, obtain product IV.
3. a kind of preparation method being applied to all solid state uhligite sensitization solar battery organic hole transport material according to claim 2, it is characterized in that, in described step a, non-polar solvent is ether or tetrahydrofuran (THF), and the reaction times is 12 hours ~ 24 hours; In described step b, Heating temperature is 90 DEG C ~ 100 DEG C, and the reaction times is 4 hours ~ 5 hours; In described step c, the reaction times is 24 hours ~ 48 hours; In steps d, Heating temperature is 110 DEG C ~ 120 DEG C, and the reaction times is 12 hours ~ 48 hours.
4. a kind of preparation method being applied to all solid state uhligite sensitization solar battery organic hole transport material according to claim 2, it is characterized in that, organophosphor ligand in described steps d is trimethyl-phosphine, triphenylphosphine, tri-butyl phosphine, and palladium catalyst is Pd (PPh
3)
4, PdCl
2(dppf), Pd (OAc)
2.
5. an all solid state uhligite sensitization solar battery, comprise the transparent substrate, transparency conducting layer, tight zone, porous dielectric layer, the organo-metallic semi-conductor light absorbing material with perovskite structure, organic cavity transmission layer and the metal electrode that stack gradually, it is characterized in that, the material of organic cavity transmission layer is compound IV.
6. all solid state uhligite sensitization solar battery according to claim 5, it is characterized in that, described tight zone is by TiO
2film is formed; Dense layer thickness is between 20-200 nm; Be preferably 50 nm.
7. all solid state uhligite sensitization solar battery according to claim 5, it is characterized in that, described porous dielectric layer is by Al
2o
3or ZrO
2or SiO
2formed, the thickness of described porous dielectric layer between 200-1500 nm, Al
2o
3or ZrO
2or SiO
2pattern is nano particle or nanometer rod or nano wire.
8. all solid state uhligite sensitization solar battery according to claim 5 or 6 or 7, it is characterized in that, described tight zone, porous dielectric layer are formed by silk screen print method.
9. all solid state uhligite sensitization solar battery as claimed in claim 5, is characterized in that, it is (RNH that the organo-metallic semi-conductor light absorbing material with perovskite structure is selected from chemical general formula
3) BX
my
nin one or more materials, wherein R=CH
3, C
4h
9, C
8h
9; B=Pb, Sn; X, Y=Cl, Br, I; M=1,2,3; N=3-m.
10. a preparation method for all solid state uhligite sensitization solar battery, comprising:
The transparent substrate providing surface to have transparency conducting layer, the tight zone that described transparency conducting layer is formed semiconductor material, described tight zone is formed porous dielectric layer, porous dielectric layer is formed perovskite structure organo-metallic semi-conductor light-absorption layer, perovskite structure organo-metallic semi-conductor light-absorption layer forms organic cavity transmission layer and in organic cavity transmission layer, forms metal counter electrode layer, encapsulation, it is characterized in that, Compound Compound IV is spun on calcium titanium ore bed as organic hole transport material, prepares hole transmission layer; Will to electrode evaporation to hole transmission layer surface by vacuum vapour deposition to electrode.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104891563A (en) * | 2015-04-24 | 2015-09-09 | 南京正春电子科技有限公司 | Method for preparation of mesoporous titanium dioxide by template method and application thereof in preparation of organic perovskite solar cell |
| CN106654022A (en) * | 2015-11-03 | 2017-05-10 | 北京大学深圳研究生院 | Organic cavity transmission material, solar cell and manufacturing method thereof |
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| CN110148672A (en) * | 2019-05-30 | 2019-08-20 | 南方科技大学 | Hole transport material, preparation method and application thereof, and perovskite solar cell comprising hole transport material |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104891563A (en) * | 2015-04-24 | 2015-09-09 | 南京正春电子科技有限公司 | Method for preparation of mesoporous titanium dioxide by template method and application thereof in preparation of organic perovskite solar cell |
| CN106654022A (en) * | 2015-11-03 | 2017-05-10 | 北京大学深圳研究生院 | Organic cavity transmission material, solar cell and manufacturing method thereof |
| CN108970913A (en) * | 2017-06-02 | 2018-12-11 | 杭州纤纳光电科技有限公司 | A kind of perovskite thin film coating apparatus and application method and application |
| CN108970913B (en) * | 2017-06-02 | 2023-09-01 | 杭州纤纳光电科技有限公司 | Perovskite film coating equipment, use method and application |
| CN108155293A (en) * | 2017-12-30 | 2018-06-12 | 凯盛光伏材料有限公司 | A kind of copper indium gallium selenide perovskite lamination solar cell and preparation method thereof |
| CN110148672A (en) * | 2019-05-30 | 2019-08-20 | 南方科技大学 | Hole transport material, preparation method and application thereof, and perovskite solar cell comprising hole transport material |
| CN113087726A (en) * | 2021-02-24 | 2021-07-09 | 浙江大学 | Arylamine organic semiconductor material and application thereof in photoelectric device |
| CN113698398A (en) * | 2021-08-26 | 2021-11-26 | 北京化工大学 | Cross-linkable organic ligand for perovskite solar cell and preparation method and application thereof |
| CN115215754A (en) * | 2022-07-28 | 2022-10-21 | 华北电力大学 | Spirobifluorene compound with terminal extension and preparation method and application thereof |
| CN115215754B (en) * | 2022-07-28 | 2024-04-12 | 华北电力大学 | Spirobifluorene compound with terminal extension and preparation method and application thereof |
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Application publication date: 20141224 |