CN101787020A - Organic conjugated molecule capable of being processed by solution and application thereof in solar cells - Google Patents
Organic conjugated molecule capable of being processed by solution and application thereof in solar cells Download PDFInfo
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Abstract
The invention, which belongs to the technical field of solar cells, relates to a donor-acceptor type organic conjugated molecule based on 2-pyran-4-ylidene malononitrile as acceptor and the application of the organic conjugated molecule in bulk heterojunction solar cells. The invention provides a series of low-HOMO energy level (high open circuit voltage and high stability), narrow-bandgap, high-absorbability and high-mobility donor-acceptor type organic conjugated molecule solar cell materials by selecting different donor units to couple with 2-pyran-4-ylidene malononitrile (acceptor unit); when the organic conjugated molecule is used in the production of solar cells, an element with a high open circuit voltage and high photoelectric conversion efficiency can be obtained; and moreover, the element production technique is simple, can be easily repeated, and is favorable for the industrialized batch production of elements.
Description
Technical field
The invention belongs to technical field of solar batteries, being specifically related to a kind of is the organic conjugated molecule and the application of this organic conjugated molecule in the bulk heterojunction solar cell of basic structural unit based on 2-pyrans-4-subunit third dicyan.
Background technology
Along with petering out of primary energy source such as coal, oil, the eco-friendly renewable energy source of human active demand.Solar cell can directly be converted to electric energy with sun power, is the effective means of utilizing sun power.
U.S.'s Bell Laboratory was successfully developed first monocrystaline silicon solar cell in 1954, had opened a fan gate of human use's solar electrical energy generation.Solar cell at first was applied on spacecraft in 1958.Early 1970s, solar cell begins in Ground Application.But preparation technology is numerous and diverse, cost is high, environmental pollution is serious etc., has limited the broader applications based on the solar cell of silicon materials to a certain extent.
Based on the solar cell of organic polymer and organic small molecule material because of its preparation technology simple (but as spin coating, spray ink Printing etc.), cheap, be easy to realize advantages such as big area and flexibility, and people's attention extremely.Comparatively speaking, the solubility organic molecule is owing to have clear and definite molecular structure, the fixed molecular weight, and advantages such as higher purity and better repeatability more and more are subjected to people's favor.2005, people such as this academician of primary track were applied to BDHT in the organic molecule solar cell as active coating by the method for spin coating, have obtained 0.03% photoelectric transformation efficiency; 2007, people such as professor Li Yongfang will be based on the small molecules of triphenylamine and DCM cell formation as donor material, and the bulk heterojunction solar cell that the method that is acceptor with PCBM by spin coating makes has been obtained 0.79% photoelectric transformation efficiency; 2009, people such as professor Tian Wenjing were applied to the organic molecule solar cell with DADP, had obtained 1.50% high light photoelectric transformation efficiency.2009, people such as Nguyen were applied to organic molecule SMDPPEH in the organism heterojunction solar battery, had obtained 3.0% photoelectric transformation efficiency.
At present, the photoelectric transformation efficiency based on the organic molecule solar cell of solution processable has surpassed 4%.But for organic polymer solar cell, a lot of weak points of still existence of organic molecule solar cell.Wherein, not match be primary factor for absorption spectrum and solar spectrum.And have to the organic conjugated molecule of receptor structure because can be by introducing the different acceptor groups of giving, coplanarity, the intramolecular charge of regulating molecule shift (ICT) intensity, thereby regulate absorbent properties, level structure and the carrier mobility etc. of molecule, thereby become the organic molecule solar cell material that a class has development potentiality.
Summary of the invention
The purpose of this invention is to provide a series of can the combination with 2-pyrans-4-subunit third dicyan (acceptor) by selecting the different body units of giving with strong electron-withdrawing power, thereby that realizes low HOMO energy level (high open circuit voltage and high stability), narrow band gap, wide absorption, high mobility gives the acceptor organic conjugated molecule, and this type of organic conjugated molecule is used to prepare solar cell.
Use material of the present invention, can simplify device preparation technology, to adapt to the industrialized mass production needs of device.
Finding after deliberation, is that the acceptor organic conjugated molecule of giving of acceptor has good solar cell properties with 2-pyrans-4-subunit third dicyan.
Of the present inventionly give the acceptor organic conjugated molecule shown in general formula (I) based on 2-pyrans-4-subunit third dicyan:
General formula (I) representative is the basic structure skeleton of giving the acceptor organic conjugated molecule of acceptor with 2-pyrans-4-subunit third dicyan, and D represents 3,4-two positive alkyl (C
6-C
13) thiophene, to two positive alkoxyl group (C
6-C
13) benzene, the positive alkyl (C of 10-
6-C
13) thiodiphenylamine, the positive alkyl (C of 9-
6-C
13) carbazole, triphenylamine.D
*Represent thiophene, company's two thiophene, three to connect thiophene, 9,10-dialkyl group (C
4-C
9) fluorenes, the positive alkyl (C of 10-
6-C
13) thiodiphenylamine, triphenylamine, the positive alkyl (C of 9-
6-C
13) carbazole.
Its example molecular formula is as follows,
10 〉=n 〉=4 wherein, promptly the number of carbon atom is 4 to 10, the number of hydrogen atom is 9 to 21.
Preparation 2-pyrans-4-subunit third dicyan conjugation oligopolymer is undertaken by following reaction pattern:
In the reaction pattern, contain the two bromine monomers and the Compound D of 2-pyrans-4-subunit third dicyan
*Single boronation or single tin monomer at toluene/salt of wormwood (K
2CO
3) or toluene/N, in dinethylformamide (DMF) solution, with tetra-triphenylphosphine palladium (Pd (PPh
3)
4) be catalyzer, Suzuki or Stille reaction take place under heating condition, can obtain target compound (I).
Further, when D is a substituted thiophene, D
*During for triphenylamine, its structural formula is as follows:
R is for being positioned at the C of 3,4 in thiophene
6-C
13Alkyl.
Among the present invention, give the receptor type organic conjugated molecule, can give body group D and D by what select different electron donations and coplanarity suc as formula the 2-pyrans shown in (I)-4-subunit third dicyan
*, regulate effectively to the intramolecular charge in the acceptor organic conjugated molecule and shift the intensity of (ICT) and the HOMO energy level of molecule, thus the organic conjugate small molecules photovoltaic material of realization narrow band gap, high mobility and high open circuit voltage.
Organic conjugated molecule of the present invention has low HOMO energy level (being lower than 5.2eV), narrow band gap (less than 2.0eV), wide absorption (350-750nm), be applicable to the preparation high performance solar cells, and device preparation technology is simple, repeats easily, is beneficial to the device industrialized mass production.
Organic conjugated molecule of the present invention (I) can be used as the donor material of active coating in the interpenetrating(polymer)networks body phase heterojunction solar battery device, preparation organic molecule solar cell device.So-called active coating is meant and can absorbs photon and produce exciton, charge transfer and charge separation can take place, and have the organic thin film layer of charge transport properties.
By ultraviolet-visible absorption spectroscopy, fluorescence spectrum, electrochemistry cyclic voltammetric method, atomic force microscope, current/voltage characteristic analytical procedure test material and device performance, utilize the solar cell device characteristic of formula of the present invention (I) organic conjugated molecule preparation as follows: UV, visible light absorbs and can reach more than the 700nm, the solar device open circuit voltage is 0.90V, and short-circuit current is 4.27mA/cm
2, maximum photoelectric transformation efficiency is 1.15%.This shows that the organic conjugated molecule synthetic method of formula of the present invention (I) is simple, purification is convenient, be applied to solar cell device has characteristics such as high open circuit voltage, good stability, high-photoelectric transformation efficiency.
Description of drawings
Fig. 1: use organic molecule solar cell device structural representation of the present invention.
Use organic conjugated molecule of the present invention and can prepare solar cell device efficiently.These solar cell devices can be applicable to independent system, photovoltaic water pump (drinking-water or irrigate), the communication power supply of solar energy garden lamp, solar power system, stockaded village power supply etc.
Now the application of formula of the present invention (I) organic conjugated molecule in solar cell device is described in conjunction with Fig. 1.Object of the present invention can be used for preparing single solar cell device with one or more active coatings or tandem, parallel connection type solar battery device, and in these active coatings at least one deck contain one or more compounds of the present invention.Active coating is by the method preparation of spin coating or vacuum evaporation.The basic structure of the solar cell device of this type of organic conjugated molecule as shown in Figure 1, this figure is typical bulk heterojunction device, it is by attached to ITO (tin indium oxide) conductive layer (anode) 2 on transparent glass or the flexible substrates 1, PEDOT:PSS (anode modification layer) 3, LiF (cathodic modification layer) 6 and metal (Al, Mg:Ag alloy, Ca, Na, K) layer (negative electrode) 7 and the photoactive layer 4 that is clipped between the two poles of the earth constitute.Between photoactive layer and negative electrode, also can add one deck exciton barrier-layer 5 (2,9-dimethyl-4,7-phenylbenzene-1,10-phenanthroline (BCP) is to improve device performance.Wherein photoactive layer 4 is films of giving the preparation of receptor type organic conjugated molecule with of the present invention, or adopts and of the present inventionly give receptor type conjugated small molecule material as giving body and acceptor molecule (as: [6,6]-phenyl-C
61-methyl-butyrate (PC
61BM) or [6,6]-phenyl-C
71-methyl-butyrate (PC
71BM)) mix the film that the back prepares.
Fig. 2: the organic conjugated molecule of example 1,2,3 material preparations and the atomic power surface topography map of PCBM mixture film (weight ratio respectively was 1: 1,3: 7,1: 1).Experiment records its surfaceness and is followed successively by: 0.369nm, 0.419nm, 1.510nm.As can be seen from Figure 2, the film that forms after prepared molecule mixes with PCBM is more smooth, has preferably to be separated.
Table 1: the organic solar batteries performance of Application Example 1,2,3 material preparations relatively
(light intensity is 100mW/cm
2The AM1.5 illuminate condition is measured down)
Embodiment
Further illustrate the preparation and the application of organic conjugated molecule of the present invention below by example, rather than will limit the present invention with these examples.
Embodiment 1:4TPM's is synthetic
(5.76 grams 0.24mol) mix with 20ml exsiccant ether, and are cooled to 0 ℃ to put into magnesium chips in there-necked flask.(44 milliliters, 0.312mol) joining in the mixing solutions dropwise dropwises the back and refluxed 2 hours down at 50 ℃, reacts completely up to Mg with N-Hexyl Bromide.Then temperature of reaction is cooled to room temperature, and with 1, two (diphenylphosphine propane) dichloride nickel (dppp) Cl of 3-
2(240 milligrams, 0.367mmol) add in the reaction soln, and dropwise with 3, the 4-dibromo thiophene (11.36 milliliters, 0.1mol) in the adding solution dropwise.Dropwise the back at 50 ℃ of reaction 24h.Reactant poured into use extracted with diethyl ether in the water, merge organic solvent, and use the saturated common salt water washing, use anhydrous magnesium sulfate drying then, except that desolvating.As developping agent, silica gel obtains 18.9 gram weak yellow liquids 3,4-two hexane thiophene as stationary phase by column chromatography separation method with sherwood oil.
With 5.5 grams 3,4-two hexane thiophene incorporate in 50 milliliters of tetrahydrofuran (THF)s (THF), mix.Slowly add inferior acid amides (NBS) 7.2g of N-bromo amber then, react and after 4 hours solvent is removed, again 200 milliliters normal hexane is joined in the reactant, generated a large amount of precipitations, and sedimentation and filtration is fallen.Collect filtrate, remove and desolvate, the method by underpressure distillation obtains 6.73 gram colourless liquids 2,5-two bromo-3,4-two hexane thiophene.
With 1 gram 2,5-two bromo-3,4-two hexane thiophene dissolve among 30 milliliters of exsiccant THF, are cooled to-78 ℃, under nitrogen atmosphere, add the n-Butyl Lithium (hexane solution of 2.5M/L) that dropwise adds 0.98 milliliter, dropwise the back and under-78 ℃ of temperature, reacted 2 hours.The dimethyl formamide (DMF) that adds 0.03ml then fast, and with temperature recovery to room temperature, and kept room temperature reaction 24 hours.Reactant is poured in the water, merged organic solvent, and use the saturated common salt water washing, use anhydrous magnesium sulfate drying then.Remove and desolvate.Use sherwood oil: 2: 1 ratio of methylene dichloride (volume ratio) is as developping agent, and silica gel obtains 5-bromo-3 as stationary phase by column chromatography separation method, 4-two hexane thiophene-2-formaldehydes 0.46 gram.
In round-bottomed flask, put into 3.65 gram 5-bromo-3,4-two hexane thiophene-2-formaldehydes, 0.8 gram 2,6-dimethyl-4H-4-pyranylidene propane dinitrile and 1 milliliter of piperidines, and add 80 milliliters of second cyanogen, stirring and dissolving.Under nitrogen protection, be heated to 90 ℃, after reacting 12 hours, pour into and use dichloromethane extraction in the water, merge organic solvent, and use the saturated common salt water washing, use anhydrous magnesium sulfate drying then.Remove and desolvate, sherwood oil: 5: 1 ratio of methylene dichloride is as developping agent, and silica gel is as stationary phase, by obtaining 2-(2 after the column chromatography separation method purification, 6-two ((E)-2-(5-bromo-3,4-two hexane thiophene-2 vinyl)-2-pyrans-4-subunit) third dicyan (TMT) 2.1 grams.
In round-bottomed flask, add 295 milligram 4,4,5 successively, 5-tetramethyl--2-thiophene-1,3,2-two dislikes boron, the Pd (PPh of 500 milligrams of TMT and catalytic amount (2%mol)
3)
4, vacuumize logical nitrogen, under nitrogen protection, add 6 milliliters of toluene and 4 milliliters of Na with syringe successively
2CO
3(2M).95 ℃ are reacted after 48 hours down, are cooled to room temperature, reactant is poured into used dichloromethane extraction in the water, merge organic solvent, and use the saturated common salt water washing, use anhydrous magnesium sulfate drying then.Remove and desolvate sherwood oil: 3: 2 ratio of methylene dichloride is as developping agent, and silica gel is as stationary phase, by obtaining 2-(2 after the column chromatography separation method purification, 367 milligrams of 6-two ((E)-2-(3,4-two hexanes-2,2 '-two thiophene-5-vinyl)-4H-pyrans-4-subunit) third dicyan.Productive rate: 75.0%.
1H NMR (300MHz, CDCl3, TMS): δ (ppm) 7.614 (d, 2H, J=15.6Hz ,-vinylic), 7.388 (d, 2H ,-Th), 7.225 (d, 2H ,-Th), 7.109 (t, 2H ,-Th), 6.614 (s, 2H ,-PM), 6.474 (d, 2H, J=15.3Hz ,-vinylic), 2.716 (t, 8H ,-CH2), 1.545 (m, 8H ,-CH2), 1.316 (m, 16H ,-CH2), 1.257 (m, 8H ,-CH2), 0.879 (m, 12H ,-CH3).
13C NMR (75MHz, CDCl3, TMS): δ (ppm) 158.090,155.319,146.964,140.278,135.606,134.272,133.099,128.402,127.627,125.708,125.528,125.403,116.344,115.450,105.519,58.902,31.707,31.611,31.484,30.446,29.502,29.448,27.870,27.445,22.593,14.020,13.969. mass spectrograph point counting minor C
52H
64N
2OS
4Obtain 861.34; Its structural formula of experimental value: 861.40. is as follows:
Embodiment 2:6TPM's is synthetic
6TPM's is synthetic the same with embodiment 1.Just replace 4,4,5 with 2,2 '-two thiophene-5-tributyl tin, 5-tetramethyl--2-thiophene-1,3,2-two dislikes boron.Productive rate: 80.3%.
1H NMR (500MHz, CDCl3, TMS): δ (ppm) 7.608 (d, 2H, J=15.6Hz,-vinylic), 7.269 (s, 2H ,-Th), 7.224 (d, 2H ,-Th), 7.167 (d, 2H ,-Th), 7.136 (d, 2H ,-Th), 7.054 (m, 2H,-Th), 6.618 (s, 2H ,-PM), 6.473 (d, 2H, J=15.3Hz ,-vinylic), 2.730 (m, 8H,-CH2), 1.573 (m, 8H ,-CH2), 1.445 (m, 8H ,-CH2), 1.332 (m, 16H ,-CH2), 0.921 (m, 6H,-CH3), 0.859 (m, 6H ,-CH3).
13C NMR (75MHz, CDCl3, TMS): δ (ppm) 140.273,138.264,136.727,134.399,134.067,133.136,128.196,127.946,124.904,124.590,124.101,123.966,116.411,115.416,106.503,58.901,31.675,31.610,31.460,30.334,29.500,29.499,27.965,27.721,22.619,22.585,14.015,13.969. mass spectrograph point counting minor C
60H
68N
2OS
6Obtain 1025.58; Its structural formula of experimental value: 1025.70. is as follows:
Embodiment 3:8TPM's is synthetic
8TPM's is synthetic the same with embodiment 1.Be with 2,2:5,2-three thiophene-5-tin trimethyl-tin trimethyl replaces 4,4,5,5-tetramethyl--2-thiophene-1,3,2-two dislikes boron.Productive rate: 72.6%.
1H NMR (500MHz, CDCl3, TMS): δ (ppm) 7.601 (d, 2H, J=15.6Hz ,-vinylic), 7.252 (m, 2H,-Th), 7.202 (m, 2H ,-Th), 7.134 (m, 8H ,-Th), 7.042 (m, 2H ,-Th), 6.605 (s, 2H ,-PM), 6.460 (d, 2H, J=15.3Hz ,-vinylic), 2.733 (m, 8H ,-CH2), 1.587 (m, 8H ,-CH2), 1.460 (m, 8H ,-CH2), 1.323 (m, 16H,-CH2), 0.927 (m, 6H ,-CH3), 0.864 (m, 6H ,-CH3).
13C NMR (75MHz, CDCl3, TMS): δ (ppm) 158.021,155.199,147.211,147.119,140.325,137.928,136.925,136.888,135.445,134.542,134.048,133.028,128.167,127.923,127.294,124.717,124.571,124.419,124.035,123.883,116.482,106.558,58.964,31.696,31.638,31.493,30.334,29.688,29.537,29.482,28.033,27.746,22646,14.050,13.992. mass spectrograph point counting minor C
68H
72N
2OS
8Obtain 1189.83; Its structural formula of experimental value: 1189.20. is as follows:
Embodiment 4:ATPM's is synthetic
ATPM's is synthetic the same with embodiment 1.Just use N, and N '-hexichol-4-(4,4,5,5-tetramethyl--1,3,2-two dislikes boron-2-aniline) and replace 4,4,5,5-tetramethyl--2-thiophene-1,3,2-two dislikes boron.Productive rate: 72.0%.
1H?NMR(300MHz，CDCl3，TMS)：δ(ppm)7.033(d，2H，J＝15.6Hz，-vinylic)，7.297(d，8H，-TPA)，7.248(s，4H，-TPA)，7.146(d，8H，-TPA)，7.068(t，8H，-TPA)，6.581(s，2H，-PM)，6.447(d，2H，J＝15.6Hz，-vinylic)，2.719(t，4H，-CH2)，2.586(t，4H，-CH2)，1.421(m，32H，-CH2)，0.853(t，12H，-CH3).
13C?NMR(75MHz，CDCl3，TMS)：δ(ppm)158.328，155.438，147.887，147.319，146.953，141.858，139.406，132.873，129.780，129.374，128.816，127.538，124.929，123.474，122.529，115.672，115.618，106.249，58.353，31.840，31.615，31.388，30.721，29.489，29.348，27.830，27.314，22.614，22.522，14.002，13.945.
Mass spectrograph point counting minor C
80H
86N
4OS
2Obtain 1183.70; Its structural formula of experimental value: 1183.10. is as follows:
Embodiment 5:AAPM's is synthetic
AAPM's is synthetic the same with embodiment 4.Just with 2-(2,6-two (4-((4-dibromobenzene) (benzene) amine) vinylbenzene)-4H-pyrans-4-subunit) third dicyan replace 2-(2,6-two ((E)-2-(5-bromo-3,4-two hexane thiophene-2 vinyl)-2-pyrans-4-subunit) third dicyan.Productive rate: 80.0%.
1H?NMR(500MHz，CDCl3，TMS)：δ(ppm)7.522(d，4H，-Ph)，7.455(m，10H，-Ph)，7.345(t，4H，-Ph)，7.283(t，4H，-Ph)，7.200(m，8H，-Ph)，7.153(t，13H，-Ph)，7.102(d，4H，-Ph)，7.049(t，4H，-Ph)，6.651(s，2H，-PM)，6.623(d，2H，-vinylic).
13CNMR(75MHz，CDCl3，TMS)：δ(ppm)158.731，155.830，149.894，147.636，147.096，146.627，145.486，137.431，136.425，134.205，129.607，129.274，129.037，127.582，127.382，125.610，125.529，124.422，124.388，124.378，123.882，122.988，121.745，115.780，115.854，106.340，58.270.
Mass spectrograph point counting minor C
84H
60N
6O obtains 1169.41; Its structural formula of experimental value: 1169.50. is as follows:
Embodiment 6:TAPM's is synthetic
TAPM's is synthetic the same with embodiment 5.Just with 4,4,5,5-tetramethyl--2-thiophene-1,3,2-two are disliked boron and are replaced N, and N '-hexichol-4-(4,4,5,5-tetramethyl--1,3,2-two dislikes boron-2-aniline).Productive rate: 76.0%
1H?NMR(300MHz，CDCl3，TMS)：δ(ppm)7.538，(d，4H，-Ph)，7.441(t，7H，-Ph)，7.330(t，4H，-Ph，-vinylic)，7.267(s，2H，-Ph)，7.120(m，17H，-Ph)，6.640(s，3H，-PM，-vinylic)，6.586(s，1H，-vinylic).
13C?NMR(75MHz，CDCl3，TMS)：δ(ppm)158.634，155.712，148.037，146.432，145.946，143.788，137.347，130.164，129.607，129.035，128.027，127.806，126.906，125.624，125.272，124.815，124.406，122.001，121.921，115.891，115.545，106.323，58.397.
Mass spectrograph point counting minor C
56H
38N
4OS
2Obtain 847.06; Its structural formula of experimental value: 846.90. is as follows:
Embodiment 7:BTAPM's is synthetic
BTAPM's is synthetic the same with embodiment 6.Just replace 4,4,5 with 2,2 '-two thiophene-5-tributyl tin, 5-tetramethyl--2-thiophene-1,3,2-two dislikes boron.Productive rate: 40.0%.
1H?NMR(500MHz，CDCl3，TMS)：δ(ppm)7.517(d，4H，-Ph)，7.434(m，6H，-Ph)，7.334(t，4H，-Ph?and-vinylic)，7.215(d，2H，-Ph)，7.169(t，8H，-Ph)，7.131(t，6H，-Ph)，7.089(d，4H，-Ph)，7.024(t，2H，-Ph)，6.637(s，2H，-PM)，6.612(d，2H，J＝16Hz，-vinylic).
13C?NMR(75MHz，CDCl3，TMS)：δ(ppm)158.742，155.771，149.743，146.574，146.260，142.677，137.502，137.417，136.561，129.909，129.703，129.079，128.169，127.839，126.728，125.781，125.260，124.697，124.656，124.379，123.645，123.370，122.231，116.205，115.463，106.409，58.893.
Mass spectrograph point counting minor C
64H
42N
4OS
4Obtain 1011.30; Its structural formula of experimental value: 1010.90. is as follows:
Embodiment 8:APPM's is synthetic
APPM's is synthetic the same with embodiment 4, just with 2-(2,6-two ((E)-2-(7-bromo-10-hexane-10H-thiodiphenylamine vinyl)-2-pyrans-4-subunit) third dicyan replacement 2-(2,6-two ((E)-2-(5-bromo-3,4-two hexane thiophene-2 vinyl)-2-pyrans-4-subunit) third dicyan.Promptly get the product productive rate: 76.0%
1H?NMR(500MHz，CDCl3，TMS)：δ(ppm)7.354(m，14H，-Ph)，7.273(d，2H，-Ph)，7.250(s，2H，-Ph)，7.116(t，12H，-Ph)，7.031(t，4H，-Ph)，6.875(d，4H，-Ph)，6.591(d，4H，-PM，-vinylic).
13C?NMR(75MHz，CDCl3，TMS)：δ(ppm)158.293，155.554，147.611，147.083，146.830，142.467，136.455，135.004，133.497，129.250，128.883，128.739，127.852，127.086，126.238，125.547，125.225，124.743，124.382，123.887，122.945，116.088，115.784，115.484，115.140，106.480，58.731，47.881，31.387，26.743，26.541，22.580，13.951.
Mass spectrograph point counting minor C
64H
42N
4OS
4Obtain 1245.64; Its structural formula of experimental value: 1245.60. is as follows:
Embodiment 9:TPPM's is synthetic
TPPM's is synthetic the same with embodiment 1, just with 2-(2,6-two ((E)-2-(7-bromo-10-hexane-10H-thiodiphenylamine vinyl)-2-pyrans-4-subunit) third dicyan replacement 2-(2,6-two ((E)-2-(5-bromo-3,4-two hexane thiophene-2 vinyl)-2-pyrans-4-subunit) third dicyan.Promptly get the product productive rate: 76.0%.Chemical formula C is pressed in ultimate analysis
56H
50N
4OS
4Calculate: C, 72.85; H, 5.46; N, 6.07; O, 1.73; S, 13.89.Experimental value: C, 72.83; H, 5.48; N, 6.06; O, 1.75; S, 13.88.Its structural formula is as follows,
Embodiment 10:BTPPM's is synthetic
BTPPM's is synthetic the same with embodiment 9, just replaces 4,4,5 with 2,2 '-two thiophene-5-tributyl tin, 5-tetramethyl--2-thiophene-1,3, and 2-two dislikes boron.Promptly get the product productive rate: 50%.Chemical formula C is pressed in ultimate analysis
64H
54N
4OS
6Calculate: C, 70.68; H, 5.00; N, 5.15; O, 1.47; S, 17.69.Experimental value: C, 70.65; H, 5.02; N, 5.16; O, 1.48; S, 17.68.Its structural formula is as follows,
Embodiment 11:TTPPM's is synthetic
TTPPM's is synthetic the same with embodiment 3, just with 2-(2,6-two ((E)-2-(7-bromo-10-decane-lysivane vinyl)-2-pyrans-4-subunit) third dicyan replacement 2-(2,6-two ((E)-2-(5-bromo-3,4-two hexane thiophene-2 vinyl)-2-pyrans-4-subunit) third dicyan.Promptly get the product productive rate: 60.0%.Chemical formula C is pressed in ultimate analysis
80H
74N
4OS
8Calculate: C, 70.44; H, 5.47; N, 4.11; O, 1.17; S, 18.81.Experimental value: C, 70.42; H, 5.49; N, 4.10; O, 1.16; S, 18.83.Its structural formula is as follows,
Embodiment 12:PPPM's is synthetic
PPPM's is synthetic the same with embodiment 9, just replaces 4,4,5 with 10-hexane-3-(4,4,5,5-tetramethyl--1,3,2-two evil boron)-lysivane, 5-tetramethyl--2-thiophene-1,3, and 2-two dislikes boron.Promptly get the product productive rate: 76.0%.Chemical formula C is pressed in ultimate analysis
84H
84N
6OS
4Calculate: C, 76.32; H, 6.41; N, 6.36; O, 1.21; S, 9.70.Experimental value: C, 76.30; H, 6.42; N, 6.37; O, 1.20; S, 9.71.Its structural formula is as follows,
Embodiment 13:CPPM's is synthetic
CPPM's is synthetic the same with embodiment 9, just replaces 4,4,5 with 10-hexane-3-(4,4,5,5-tetramethyl--1,3,2-two evil boron)-10-carbazole, 5-tetramethyl--2-thiophene-1,3, and 2-two dislikes boron.Promptly get the product productive rate: 74.0%.Chemical formula C is pressed in ultimate analysis
84H
84N
6OS
2Calculate: C, 80.22; H, 6.73; N, 6.68; O, 1.27; S, 5.10.Experimental value: C, 80.20; H, 6.74; N, 6.67; O, 1.28; S, 5.11.Its structural formula is as follows,
Embodiment 14:FPPM's is synthetic
Synthesizing of FPPM is the same with embodiment 9, and just (9,9-dibutyl-9-fluorenes-2-)-4,4,5,5-tetramethyl--1,3,2-two are disliked boron and replaced 4,4,5,5-tetramethyl--2-thiophene-1,3,2-two evil boron with 2-.Promptly get the product productive rate: 78.0%.Chemical formula C is pressed in ultimate analysis
90H
94N
4OS
2Calculate: C, 82.40; H, 7.22; N, 4.27; O, 1.22; S, 4.89.Experimental value: C, 82.37; H, 7.24; N, 4.26; O, 1.23; S, 4.90.Its structural formula is as follows,
Embodiment 15:FCPM's is synthetic
FCPM's is synthetic the same with embodiment 13, just with 2-(2,6-two ((E)-2-(6-bromo-9-hexane-9-carbazole vinyl)-2-pyrans-4-subunit) third dicyan replacement 2-(2,6-two ((E)-2-(7-bromo-10-hexane-10H-thiodiphenylamine vinyl)-2-pyrans-4-subunit) third dicyan.Promptly get the product productive rate: 70.0%.Chemical formula C is pressed in ultimate analysis
90H
94N
4O calculates: C, 86.63; H, 7.59; N, 4.49; O, 1.28.Experimental value: C, 86.61; H, 7.60; N, 4.48; O, 1.30.Its structural formula is as follows,
Embodiment 16:FAPM's is synthetic
FAPM's is synthetic the same with embodiment 13, just with 2-(2,6-two (4-((4-dibromobenzene) (benzene) amine) vinylbenzene)-4H-pyrans-4-subunit) third dicyan replace 2-(2,6-two ((E)-2-(7-bromo-10-hexane-10H-thiodiphenylamine vinyl)-2-pyrans-4-subunit) third dicyan.Promptly get the product productive rate: 70.0%.Chemical formula C is pressed in ultimate analysis
90H
82N
4O calculates: C, 87.48; H, 6.69; N, 4.53; O, 1.29.Experimental value: C, 87.46; H, 6.71; N, 4.52; O, 1.30.Its structural formula is as follows,
Embodiment 17:FTPM's is synthetic
FTPM's is synthetic the same with 13, just with 2-(2,6-two ((E)-2-(5-bromo-3,4-two hexane thiophene-2 vinyl)-2-pyrans-4-subunit) third dicyan replacement 2-(2,6-two ((E)-2-(7-bromo-10-hexane-10H-thiodiphenylamine vinyl)-2-pyrans-4-subunit) third dicyan.Promptly get the product productive rate: 71.0%.Chemical formula C is pressed in ultimate analysis
86H
108N
2OS
2Calculate: 82.64; H, 8.71; N, 2.24; O, 1.28; S, 5.13.Experimental value: 82.62; H, 8.73; N, 2.23; O, 1.27; S, 5.15.Its structural formula is as follows,
Embodiment 18:PTPM's is synthetic
PTPM's is synthetic the same with embodiment 11, just with 2-(2,6-two ((E)-2-(5-bromo-3,4-two hexane thiophene-2 vinyl)-2-pyrans-4-subunit) third dicyan replacement 2-(2,6-two ((E)-2-(7-bromo-10-hexane-10H-thiodiphenylamine vinyl)-2-pyrans-4-subunit) third dicyan.Promptly get product productive rate: 73.5.0%.Chemical formula C is pressed in ultimate analysis
80H
98N
4OS
4Calculate: C, 76.26; H, 7.84; N, 4.45; O, 1.27; S, 10.18.Experimental value: C, 76.24; H, 7.86; N, 4.43; O, 1.26; S, 10.19.Its structural formula is as follows,
Embodiment 19:PBPM's is synthetic
PBPM's is synthetic the same with embodiment 17, just replace 2-(2 with 2-(2,6-two (4-two bromo-2,5-two hexyloxy benzene-2-vinyl)-2-pyrans-4-subunit) third dicyan, 6-two ((E)-2-(5-bromo-3,4-two hexanes thiophene-2-vinyl)-2-pyrans-4-subunit) third dicyan.Promptly get product productive rate: 73.5.0%.Chemical formula C is pressed in ultimate analysis
84H
102N
4O
5S
2Calculate: C, 76.91; H, 7.84; N, 4.27; O, 6.10; S, 4.89.Experimental value: C, 76.88; H, 7.86; N, 4.26; O, 6.11; S, 4.90.Its structural formula is as follows,
Embodiment 20:CBPM's is synthetic
Synthesizing of CBPM is the same with embodiment 18, just replaces 10-hexane-3-(4,4,5,5-tetramethyl--1,3,2-two evil boron)-lysivane with 10-hexane-3-(4,4,5,5-tetramethyl--1,3,2-two evil boron)-10-carbazole.Promptly get product productive rate: 73.5.0%.Chemical formula C is pressed in ultimate analysis
84H
102N
4O
5Calculate: C, 76.91; H, 7.84; N, 4.27; O, 6.10; S, 4.89.Experimental value: C, 76.89; H, 7.86; N, 4.25; O, 6.11; S, 4.90.Its structural formula is as follows,
Embodiment 20:ABPM's is synthetic
ABPM's is synthetic the same with embodiment 18, just uses N, N '-hexichol-4-(4,4,5,5-tetramethyl--1,3,2-two dislikes boron-2-aniline) replacement 10-hexane-3-(4,4,5,5-tetramethyl--1,3,2-two dislikes boron)-lysivane.Promptly get product productive rate: 73.5.0%.Chemical formula C is pressed in ultimate analysis
84H
90N
4O
5Calculate: C, 81.65; H, 7.34; N, 4.53; O, 6.47.Experimental value:: C, 81.63; H, 7.36; N, 4.51; O, 6.49.Its structural formula is as follows,
Embodiment 21:FBPM's is synthetic
Synthesizing of FBPM is the same with embodiment 18, and just (9,9-dibutyl-9-fluorenes-2-)-4,4,5,5-tetramethyl--1,3,2-two are disliked boron and replaced 10-hexane-3-(4,4,5,5-tetramethyl--1,3,2-two evil boron)-lysivane with 2-.Promptly get product productive rate: 73.5.0%.Chemical formula C is pressed in ultimate analysis
90H
112N
2O
5Calculate: C, 83.03; H, 8.67; N, 2.15; O, 6.14.Experimental value: C, 83.01; H, 8.69; N, 2.14; O, 6.15.Its structural formula is as follows,
Embodiment 22:4TBPM's is synthetic
4TBPM's is synthetic the same with embodiment 2, just replace 2-(2 with 2-(2,6-two (4-two bromo-2,5-two hexyloxy benzene-2-vinyl)-2-pyrans-4-subunit) third dicyan, 6-two ((E)-2-(5-bromo-3,4-two hexanes thiophene-2-vinyl)-2-pyrans-4-subunit) third dicyan.Promptly get the product productive rate: 73.0%.Chemical formula C is pressed in ultimate analysis
64H
72N
2O
5S
4Calculate: C, 71.34; H, 6.74; N, 2.60; O, 7.42; S, 11.90.Experimental value: C, 71.33; H, 6.75; N, 2.58; O, 7.43; S, 11.91.Its structural formula is as follows,
Embodiment 23:6TBPM's is synthetic
6TBPM's is synthetic the same with embodiment 2, just replace 2-(2 with 2-(2,6-two (4-two bromo-2,5-two hexyloxy benzene-2-vinyl)-2-pyrans-4-subunit) third dicyan, 6-two ((E)-2-(5-bromo-3,4-two hexanes thiophene-2-vinyl)-2-pyrans-4-subunit) third dicyan.Promptly get the product productive rate: 73.0%.Chemical formula C is pressed in ultimate analysis
72H
76N
2O
5S
6Calculate: C, 69.64; H, 6.17; N, 2.26; O, 6.44; S, 15.49.Experimental value: C, 69.66; H, 6.19; N, 2.24; O, 6.43; S, 15.52.Its structural formula is as follows,
Embodiment 24: be the solar cell device to body with 4TPM
Device architecture is ITO/PEDOT:PSS/4TPM:PCBM/LiF/Al, concrete preparation process is: at first with ITO (tin indium oxide, anode) glass carries out pre-treatment, concrete steps are as follows: at first clean ito glass with clean-out system, deionized water rinsing is clean, then ito glass is used successively acetone, isopropanol solvent ultrasonic cleaning each 20 minutes, taking out the back rinses well with deionized water, put it into and boil 3-5 minute in the hydrogen peroxide, the taking-up back is rinsed well with deionized water and is put into oven dry under the infrared lamp again.Spin coating one deck PEDOT:PSS (3 on pretreated ito glass then, 4-enedioxy thiophene/polystyrolsulfon acid, 3 of one deal, the aqueous dispersion Baytron P VP Al 4083 that the polystyrolsulfon acid of 4-enedioxy thiophene and 6 deals is mixed with into poly-(3,4-vinyl dioxy thiophene) poly-(styrene sulfonate)) as the anode modification layer
Treat PEDOT:PSS behind 20 minutes complete dryinies of 120 ℃ of heating, with 4TPM: the chloroformic solution of PCBM mixture (4TPM: the PCBM mass ratio is 1: 1, and total concn is 20mg/ml) is spin-coated on the PEDOT:PSS surface as active coating with 2000 rev/mins of speed
And then evaporation LiF
And metal electrode Al
Keeping vacuum tightness in evaporate process is 4 * 10
-6Torr.Under standard sunlight (AM1.5) radiation parameter, the Keithley 2400 digital source tables of the control that uses a computer are tested device performance.Light intensity is 100mW/cm
2, the AM1.5 illuminate condition measures down, recording the device open circuit voltage is 0.70V, short-circuit current is 0.25mA/cm
2, packing factor is 0.26, effciency of energy transfer is 0.05%.Concrete device parameters sees attached list 1,4TPM: the chloroformic solution of PCBM mixture is spin-coated on the substrate of glass surface topography of formed film and sees Fig. 2 a.The hybrid films of 4TPM: PCBM relatively evenly (r.m.s. roughness is 0.33nm) significantly is not separated.
Embodiment 25: be the solar cell device to body with 6TPM
Device architecture is ITO/PEDOT:PSS/6TPM:PCBM/LiF/Al, concrete preparation process is: at first with ITO (tin indium oxide, anode) glass carries out pre-treatment, concrete steps are as follows: at first clean ito glass with clean-out system, deionized water rinsing is clean, then ito glass is used acetone successively, isopropanol solvent ultrasonic cleaning each 20 minutes, taking out the back rinses well with deionized water, put it into and boil 3-5 minute in the hydrogen peroxide, the taking-up back is rinsed well with deionized water and is put into oven dry under the infrared lamp again.Then on pretreated ito glass spin coating one deck PEDOT:PSS (3,4-enedioxy thiophene/polystyrolsulfon acid, Baytron P VP Al4083) as the anode modification layer
After treating the PEDOT:PSS complete drying, with 6TPM: the chloroformic solution of PCBM mixture (6TPM: the PCBM mass ratio is 3: 7, and total concn is 20mg/ml) is spin-coated on the PEDOT:PSS surface as active coating with 2000 rev/mins of speed
And then evaporation LiF
And metal electrode Al
Keeping vacuum tightness in evaporate process is 4 * 10
-6Torr.Light intensity is 100mW/cm
2, the AM1.5 illuminate condition measures down, the open circuit voltage of device is 0.90V, short-circuit current is 7.27mA/cm
2, packing factor is 0.30, effciency of energy transfer is 1.15%.Concrete device parameters sees attached list 1,6TPM: the chloroformic solution of PCBM mixture is spin-coated on the surface topography surface topography of formed film on the substrate of glass and sees Fig. 2 b.The hybrid films of 6TPM: PCBM more smooth (r.m.s. roughness is 0.32nm).6TPM and PCBM have good Combination, and hybrid films significantly is not separated for the homogeneous film.
Embodiment 26: be the solar cell device to body with 8TPM
Device architecture is ITO/PEDOT:PSS/6TPM:PCBM/LiF/Al, concrete preparation process is: at first with ITO (tin indium oxide, anode) glass carries out pre-treatment, concrete steps are as follows: at first clean ito glass with clean-out system, deionized water rinsing is clean, then ito glass is used acetone successively, isopropanol solvent ultrasonic cleaning each 20 minutes, taking out the back rinses well with deionized water, put it into and boil 3-5 minute in the hydrogen peroxide, the taking-up back is rinsed well with deionized water and is put into oven dry under the infrared lamp again.Then on pretreated ito glass spin coating one deck PEDOT:PSS (3,4-enedioxy thiophene/polystyrolsulfon acid, Baytron P VPAl4083) as the anode modification layer
After treating the PEDOT:PSS complete drying, with 8TPM: the chloroformic solution of PCBM mixture (8TPM: the PCBM mass ratio is 1: 1, and total concn is 20mg/ml) is spin-coated on the PEDOT:PSS surface as active coating with 2000 rev/mins of speed
And then evaporation LiF
And metal electrode Al
Keeping vacuum tightness in evaporate process is 4 * 10
-6Torr.Light intensity is 100mW/cm
2, the AM1.5 illuminate condition measures down, the open circuit voltage of device is 0.80V, short-circuit current is 4.08mA/cm
2, packing factor is 0.30, effciency of energy transfer is 0.97%.Concrete device parameters sees attached list 1,8TPM: the chloroformic solution of PCBM mixture is spin-coated on surface topography such as Fig. 2 c of formed film on the substrate of glass.The hybrid films of 8TPM: PCBM more smooth (r.m.s. roughness is 0.80nm) also has certain being separated, and PCBM aggregate (lead zone) randomly is distributed in blended 8TPM: in the PCBM matrix.
Claims (4)
- A solution processable with 2-pyrans-4-subunit third dicyan be acceptor give the receptor type organic conjugated molecule, its structural formula is as follows:
Wherein, D is
D *For
10≥n≥4。 - 2. as claimed in claim 1 a kind of with 2-pyrans-4-subunit third dicyan be acceptor give the receptor type organic conjugated molecule, it is characterized in that: D is a substituted thiophene, D *Be triphenylamine, its structural formula is as follows:
Wherein, R is for being positioned at the C of 3,4 in thiophene 6～C 12Alkyl. - Claim 1 or 2 described with 2-pyrans-4-subunit third dicyan be acceptor give the receptor type organic conjugated molecule in the application that is used to prepare aspect the solar cell.
- 4. as claimed in claim 3 with 2-pyrans-4-subunit third dicyan be acceptor give the receptor type organic conjugated molecule in the application that is used to prepare aspect the solar cell, it is characterized in that: the photoactive layer that is used to prepare solar cell.
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Open date: 20100728 |