KR101340255B1 - new dyes for DSSCs and manufacturing method thereof - Google Patents
new dyes for DSSCs and manufacturing method thereof Download PDFInfo
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- 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
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Abstract
The present invention relates to a novel organic dye KS-5 and a method for preparing the same, wherein the organic dye according to the present invention includes two anchoring groups and crosses two planes to increase the bonding strength of the dye on the TiO 2 surface and By preventing the association, when used as a dye for a dye-sensitized solar cell, it can be strongly adsorbed on the surface of TiO 2 to produce a stable and high photoelectric conversion efficiency.
Description
The present invention includes two anchoring groups and crosses two planes, thereby inhibiting association between dyes. Thus, when used as a dye for a dye-sensitized solar cell, the present invention provides a strong adsorption on the surface of TiO 2 and a stable and high photoelectric conversion efficiency. The present invention relates to a novel dye which can be produced and a method for preparing the same.
Solar cells are known as environmentally friendly energy sources, such as silicon solar cells, dye-sensitized solar cells. Dye-sensitized solar cells (DSSCs) are attracting attention as a replacement for traditional silicon-based solar cells due to their low cost and high availability in various fields. The most important part of dye-sensitized solar cells is the photosensitizer. Ruthenium (Ru) photosensitizers are photoelectric conversion efficiencies up to 11% under AM 1.5 radiation, but due to their high cost and toxicity, they are environmentally friendly and therefore need to develop inexpensive, easy to synthesize and environmentally friendly organic dyes. It is true. Recently, much progress has been made in developing dye-sensitized solar cells based on organic dyes. However, existing organic dyes have low photoelectric conversion efficiency and stability, and there is a need for development of new dyes.
The biggest factor affecting the photoelectric conversion efficiency and stability of dye-sensitized solar cells is the strength of dyes attached to TiO 2 surfaces. TiO 2 The intensity of attaching the dye to the dye increases not only the absorbance but also the efficient charge injection. While the Ru (II) sensitizer effectively conducts electron transfer in the 1-4 anchoring group, one of the biggest disadvantages of the conventional organic dye molecule is that there is only one anchoring group. In order to solve the above problem, there have been recently reported cases of developing an organic sensitizer of a double / multi electron acceptor type. However, the study of the molecular structure of the double electron acceptor type is rather insufficient. By attaching a dye to the TiO 2 surface, it is important to efficiently charge and transfer electrons while maintaining physical isolation between the photo-oxidation donor and the photo-injected electrons.
It is also an important issue to prevent organic dyes from accumulating on TiO 2 surfaces in dye-sensitized solar cells. However, conventionally, bulky groups have been introduced, and two are arranged in a spiral arrangement similar to Ru-dye. Unique approaches to linking chromophores have also been attempted.
In order to solve the problems of the prior art, the present inventors synthesized a novel KS-5 organic dye by combining two L1 dye molecules and then used as a photosensitizer to examine the photoelectric conversion efficiency in dye-sensitized solar cells (DSSCs) In addition, the present invention was completed by confirming that the photoelectric conversion efficiency is superior to that of the conventional organic dyes and that dye accumulation can be reduced.
The main object of the present invention is to provide a novel organic dye compound KS-5 and a method for synthesizing the same, which have two anchoring groups and are suitable for application to dye-sensitized solar cells.
In order to achieve the above object, the present invention provides a novel organic dye KS-5 derivative represented by the following formula (1):
[Formula 1]
In this case, R is OR 'or NR' 2 , R 'is C n H 2n + 1 -or C n H 2n + 2 (n is 1 to 20), m is 1 to 3.
More specifically, the present invention synthesizes N 1 , N 4 -bis (4-bromophenyl) -N 1 , N 4 -diphenylbenzene-1,4-diamine using the
(2E, 2'E) -3,3 '-(5,5'-(4,4 '-(1,4-phenylenebis (phenylazanediyl) bis (4,1) using the 4P compound -phenylene) bis (thiophene -5,2- diyl)) bis (2-cyano-arc Lyric Acid) (represented by the formula (1) through a process comprising a step of synthesizing a KS -5) KS-5 Can be prepared.
(2)
In addition, the present invention provides an organic dye for a dye-sensitized solar cell comprising the KS-5 derivative represented by the formula (1).
The novel organic dye KS-5 according to the present invention has a unique structure in which two planes intersect, thereby minimizing dye accumulation in an adsorbed state.
In addition, the novel organic dye KS-5 according to the present invention contains two anchoring groups, thereby increasing the bonding strength of the dye on the TiO 2 surface, and thus, when used as a dye for a dye-sensitized solar cell, a low-cost stable and high photoelectric conversion efficiency The battery can be manufactured.
1 schematically shows a process of manufacturing KS-5 according to the present invention.
2 shows that KS-5 according to the present invention has a broader light absorption region than L1, and KS-5 hardly associates dyes.
Figure 3 shows a: front, b: side with the geometry of KS-5 according to the present invention.
Figure 4 shows the HOMO and LUMO structure of KS-5 according to the present invention shows that the charge separation is well.
Figure 5 shows a comparison of the photoelectric conversion efficiency spectrum according to the wavelength of the dye-sensitized solar cells of KS-5 and L1 according to the present invention.
Figure 6 shows the comparison of the conversion efficiency curve to the voltage curve for the photocurrent density in the dye-sensitized solar cells of KS-5 and L1 according to the present invention.
Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the present invention is not limited by these examples.
Compounds and solvents used in this example were used as commercially available products without further purification unless otherwise indicated. Parent dye L1 was synthesized according to known methods.
Example 1 Novel Organic Dyes KS -5 Synthesis Method
One. N One , N 4 - Vis (4- Bromophenyl ) - N One , N 4 - Diphenylbenzene -1,4- Diamine Synthesis step ( 2P )
500 mg (1.92 mmol, 1 eq), 1,4 dibromobenzene 1.81 g (7.68 mmol, 4) in N, N'-diphenyl-1,4-phenylenediamine ( 1P ) in 80 ml of dry toluene eq), 554 mg (5.76 mmol, 3 eq) of sodium t-butoxide, 111 mg (0.2 mmol, 1 eq) of dppf and 18 mg (0.0 8 mmol, 1 eq) of Pd (OAc) 2 were added to the flask. . The air was removed and calcined with reflux under an argon atmosphere for 8 hours. After cooling to room temperature, distilled water was poured out, cooled and extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO 4 and evaporated in vacuo. The reaction mixture collected by extraction was purified by silica gel column chromatography, which was first extracted with hexane and then with hexane: toluene (7: 1). 770 mg (1.35 mmol, 70%) of a white solid were obtained in 2P . mp 228-229 ° C. IR: 3082, 3056, 3033, 2922, 2351, 1596, 1582, 1505, 1484, 1308, 1270, 1069, 1004, 833, 815, 745, 693, 529, 520, 508. 1 H NMR (500 MHz, CDCl 3 ) δ7.32 (d, 4H, J = 9 Hz), 7.27 (dd, 4H, J = 8 Hz and 8 Hz), 7.08 (d, 4H, J = 8 Hz), 7.02 (t, 2H, J = 8 Hz), 6.96 (s, 4H), 6.95 (d, 4H, J = 9 Hz). 13 CNMR (125 MHz, CDCl 3 ) δ 147.3, 146.9, 142.7, 132.1, 129.4, 125.5, 124.8, 124.1, 123.1, 114.6. HRMS (FAB) m / z: calcd. for C 30 H 22 Br 2 N 2 , 568.0149; found, 568.0143.
2. 5,5 '-(4,4' (1,4- Phenylene bis (phenylazanediyl) bis (4,1- Phenylene ) Dithiophene Synthesis step of 2-carbaldehyde ( 3P )
Toluene (dry toluene) 500 mg (0.876 mmol, 1 eq) the product of 2P to 50 ml, PdCl 2 (PPh 2 ) 2 60 mg mixture of (0.08 mmol, 0.1 eq) and dppf 48 mg (0.08 mmol, 0.1 eq) To a solution, 15 ml of toluene was mixed with 274 mg (1.75 mmol, 2 eq) of 5-formylthiophen-2-yl-2-boronic acid and 725 mg (5.25 mmol, 6 eq) of K 2 CO 3 . Added. The mixture was calcined in a microwave oven at 70 ° C. for 12 minutes. Distilled water was poured, the reaction was cooled and extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO 4 and purified. The solvent was evaporated to reflux by silica gel column chromatography, which was first extracted with toluene and then with hexane: ethyl acetate (4: 1) to give 310 mg (0.49 mmol, 56%) of a yellow solid at 3P . mp 245-246 ° C. IR: 3025, 2918, 2360, 2341, 1692, 1588, 1506, 1311, 1271. 1 H NMR (500 MHz, CDCl 3 ) δ9.84 (2H, s), 7.70 (d, 2H, J = 4 Hz) , 7.53 (d, 4H, J = 8.5 Hz), 7.32 (dd, 4H, J = 8 Hz and
7.5 Hz), 7.30 (d, 2H, J = 4 Hz), 7.17 (d, 4H, J = 8 Hz), 7.09 (t, 2H, J = 7.5 Hz), 7.08 (d, 4H, J = 8.5 Hz ), 7.05 (s, 4H). 13 CNMR (125 MHz, CDCl 3 ) δ 182.6, 154.5, 148.9, 146.8, 142.7, 141.3, 137.8, 131.5, 129.5, 127.3, 126.1, 125.1, 123.9, 122.8, 122.1. HRMS (FAB) m / z: calcd. for C 40 H 28 N 2 O 2 S 2 , 632.1592; found, 632.1586.
3. (2E, 2'E)-
Tert
-
Toluene 200 mg (0.316 mmol, 1 eq) of 3P product, 180 mg (1.26 mmol, 4 eq) of tert-butyl cyanoacetate, 96 mg (1.26 mmol, 4 eq) of ammonium acetate and 2 ml of acetic acid were added to the flask Mixed. The air was removed and calcined under reflux under an argon atmosphere for 45 minutes. After cooling, distilled water was poured, cooled and extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO 4 and evaporated in vacuo. The product was purified by silica gel column chromatography which extracted with toluene. 248 mg (0.284 mmol, 95%) of an orange solid were obtained in 4P . mp 231-232 ° C. IR: 3031, 2978, 2924, 2981, 2360, 2335, 2216, 1715, 1584, 1499, 1281, 1155. 1 H NMR (500 MHz, CDCl 3 ) δ8.18 (s, 2H), 7.69 (d, 2H , J = 4 Hz), 7.56 (d,
4H, J = 9 Hz), 7.32 (dd, 4H, J = 8.5 Hz and 7.5 Hz), 7.30 (d, 2H, J = 4 Hz), 7.17 (d, 4H, J = 7.5 Hz), 7.09 (t , 2H, J = 8.5 Hz), 7.08 (d, 4H, J = 9 Hz), 7.06 (s, 4H), 1.57 (s, 18H). 13 CNMR (125 MHz, CDCl 3 ) δ 162.03, 154.3, 149.03, 149.01, 146.7, 145.7, 142.7, 138.9, 133.9, 129.5, 127.3, 126.1, 125.1, 123.9, 123.02, 122.09, 116.5, 98.7, 83.2, 28.02 . HRMS (FAB) m / z: calcd. for C 54 H 46 N 4 O 4 S 2 , 878.2960; found, 878.2966.
4. (2E, 2'E) -3,3 '-(5,5'-(4,4 '-(1,4- Phenylene bis (phenylazanediyl) bis (4,1- Pe Nilene) Vis (Thiophene-5,2- Dill )) Vis (2- Cyanoacrerick Acid ) ( KS -5 Step)
200 mg (0.224 mmol) of 4P product and 20 ml of trifluoroacetic acid were mixed with 200 ml of water and stirred for 15 minutes, followed by purification of 3 mg (0.213 mmol, 95%) of a dark red solid. mp 288-289 ° C. IR: 3443, 3032, 2923, 2958, 2963, 2345, 2215, 1685, 1571, 1492, 1436, 1412, 1316. 1 H NMR (500 MHz, DMSO-d 6 ), δ 8.45 (s, 2H), 7.98 (d, 2H, J = 4 Hz), 7.68 (d, 4H, J = 8.5 Hz), 7.63 (d, 2H, J = 4 Hz), 7.38 (dd, 4H, J = 8.5 Hz and 7.5 Hz) , 7.15 (m, 6H), 7.09 (s, 4H), 7.01 (d, 4H, J = 8.5 Hz). 13 CNMR (125 MHz, DMSO-d 6 ) δ 164.2, 153.7, 149.08, 147.1, 146.6, 142.7, 142.3, 133.9, 130.3, 127.9, 126.8, 125.6, 125.4, 124.7, 124.3, 121.9, 117.08, 97.5. HRMS (FAB) m / z: calcd. for C 46 H 30 N 4 O 4 S 2 , 766.17085; found, 766.1713.
1 H and 13 C NMR analyzes were analyzed by
Example 2 Fabrication of Dye-Sensitized Solar Cell
Using a scaffold with 20 nm size TiO 2 particles (CICC, PST-18NR) on a fluorine-doped SnO 2 conductive glass substrate (FTO, Pilkington TEC-8 glass, 6-9 Ohms / sq, 2.3 mm thick) The composed paste was coated and then dried in air for 2 hours. The TiO 2 The film was calcined stepwise at 325 ° C. for 5 minutes, at 375 ° C. for 5 minutes, at 450 ° C. for 15 minutes and at 500 ° C. for 15 minutes. A second scattering layer was made of a paste containing 400 nm anatase TiO 2 particles (CICC, PST-400C) and coated on the first layer to form a light-scattering layer. The second layer was dried in air and then sintered in the same manner as the first layer. TiO 2 The electrode was immersed in an aqueous 40 mM TiCl 4 solution for 30 minutes at 70 ℃, washed with water and ethanol and then fired for 30 minutes at 500 ℃. After cooling to 80 ° C., the TiO 2 electrode was immersed in a dye solution (0.4 mM for L1 and 0.2 mM for KS-5 in DMSO: ethanol (1: 1) solvent) for 2 hours. The dye-coated electrode was quickly washed with ethanol. To prepare the platinum counter electrode, a small hole was made in the FTO glass and a drop of H 2 PtCl 6 solution (2 mg Pt in 1 ml of ethanol) was placed on the FTO plate by sintering at 400 ° C. for 15 minutes. Dye-Adsorbed TiO 2 The electrode and the platinum counter electrode were assembled into a sealed sandwich type cell using a thin Surlyn polymer transparent film (SX 1170-25, 25 mm) as a binder. The sandwich cell was compressed at 110 ° C. to seal both electrodes. Using a vacuum backfilling method, a thin layer of electrodes was introduced from the counter electrode into the internal electrode space through the drilled holes. The electrolyte was 0.6 M 1-butyl-3-methylimidazolium iodide (BMII), 0.04 MI 2 , 0.025 M lithium iodide (LiI), 0.05 dissolved in valeronitrile: acetonitrile (15:85). Guanidinium thiocyanate (GUNCS), 0.25 M 4-t-butylpyridine (TBP). The perforations were sealed with Surlyn and microscope cover slides to prevent leakage of the electrolyte solution.
(1) Evaluation method
The current-voltage characteristics were measured under AM 1.5G radiation using an Xe-lamp (Oriel 300 W solar simulator) attached to a 2400 source meter and measured with a crystalline silicon reference cell (VLSI standards, PVM-495-KG5). Solar cell efficiency
(η) η = (J sc · V oc · FF) / P in, where Jsc (mA cm -2) is a short-circuit photoelectric current density, V oc (V) is an open-circuit voltage, fill factor FF is, P in is the inlet Radiation energy (1 sun illumination (AM 1.5G),
P in = 100 mW cm -2 ). For this measurement, a dark film was applied to the TiO 2 background region having a light emitting active region of 0.159 cm 2 .
(2) Evaluation of optical properties of organic dyes
As shown in FIG. 2, the UV-visible absorption spectrum of KS-5 in DMSO: ethanol (1: 1) solution showed a high point in the visible region. Since KS-5 increased the conjugation length by phenylenediamine, the absorbance spectrum of KS-5 was wider and red shifted (418-425 nm) than that of L1.
For L1 the maximum light absorption region is in solution and in TiO 2 The adsorption state differs, indicating that L1 has a partial J-type association. On the other hand, in the case of KS-5, the maximum absorption region is the same in the solution and in the TiO 2 adsorption state. It can be seen from this that KS-5 hardly associates with dyes. This is the result predicted from the non-planar geometry in the state of adsorption on TiO 2 of KS-5.
As shown in Table 1, the molar extinction coefficient (epsilon) of KS-5 was 2 times higher than the parent dye L1. This means that the light absorption efficiency of KS-5 is higher than that of L1.
(3) organic dyes sunlight Performance
As shown in FIG. 3, KS-5 has two D- [pi] -A branches at 88.6 [deg.] And are not coplanar but have a geometry in which the two planes intersect. This is the reverse current to the electron donor part of the TiO 2 surface flows off because the electron donor part of the KS-5 is a 9.2Å spatial separation at the surface of TiO 2 is more efficient electron transfer. In the case of typical mono anchoring dye molecules, some dye molecules are aligned horizontally on the TiO 2 surface so that the reverse current can reduce the efficiency. On the other hand, since KS-5 is more strongly adsorbed on the TiO 2 surface by using two anchoring groups, vertical alignment is more advantageous on the TiO 2 surface, thereby preventing reverse current.
In case of L1, when ultrasonic wave is applied in KOH methanol solution, L1 adsorbed on TiO 2 surface is desorbed within 5 seconds. However, at least 5 minutes are required to completely remove KS-5 from the TiO 2 surface under the same conditions. It can be seen from this that KS-5 was very strongly adsorbed to TiO 2 .
TiO 2 The amount of dye adsorbed on the film (4.5 μm) was calculated by measuring the absorbance of the desorbed dye solution. The adsorption amount (moles) of KS-5 (3.94 × 10 -5 mmol / cm 2 ) was less than that of L1 (4.86 × 10 -5 mmol / cm 2 ), but KS-5 consists of two molecules of L1 and a molar extinction coefficient. Since is more than twice, the amount of light absorption by KS-5 is more than 1.5 times compared to L1. It was found that the stronger the binding force of the dye increases the amount of dye adsorbed on the TiO 2 surface. A common way to increase the amount of dye adsorbed on the TiO 2 surface is to use a thick TiO 2 film, but this results in a relatively low open voltage (V oc ), which results in lower efficiency. It can be seen that KS-5 can exhibit high efficiency in dye-sensitized solar cells even when the TiO 2 film having an ideal thickness (2-4 μm) is used.
The maximum efficiencies (IPCEs) of converting photons to currents with L1 and KS-5 dyes are shown in FIG. 5. The maximum IPCE value of KS-5 was 87% at 460 nm. It was found that the IPCE value of the general organic dye was broader than the IPCE spectrum showing 70% or more in the analysis range of 400 nm to 540 nm. On the other hand, the IPCE spectrum of L1 was only 74% at 460 nm, which was lower than that of KS-5. Compared with L1, KS-5 has a broader light absorption spectrum and a higher IPCE value, so it can show high efficiency in photoelectric conversion.
Photocurrent-voltage (JV) curves are shown in FIG. 6 and Table 1 shows the data in this regard. Organic dyes for dye-sensitized solar cells under the standard condition of AM1.5. KS-5 is 0.159 cm 2 In the active region, a dye factor of 70.2 corresponds to a short photocurrent density (J sc ) of 13.4 mA cm -2 , an open voltage (V oc ) of 0.646, and a total conversion efficiency (η) of 6.1%, while the base dye L1 It showed low short-circuit photocurrent density (J sc ) and low conversion efficiency (η) of 4.2% in dye-sensitized solar cells. It has been reported that the conversion efficiency (η) of L1 is 2.75% (3 μm) and 5.2% (6 μm) in a situation where the thickness of the electrolyte solution or the TiO 2 film is different.
(4) Electrochemical Properties of Organic Dyes
The redox properties of organic dyes were calculated by cyclic current voltammetry. HOMO level of KS-5 is I -1 / I 3 - (0.4 V vs NHE) is lower than the LUMO level of electrode pairs exhibits a value higher than the conduction band ends of the TiO 2 (-0.5 V vs NHE) , in the photoelectric conversion It can be seen that efficient electron injection is possible. Comparing the redox properties of KS-5 and L1, KS-5 can efficiently donate electrons because the E ox and E o -o values of KS-5 are lower than L1.
As described above in detail specific parts of the present invention, it is apparent to those skilled in the art that these specific descriptions are merely preferred embodiments, and thus the scope of the present invention is not limited thereto. Accordingly, the actual scope of the present invention will be defined by the appended claims and their equivalents.
Claims (4)
[Chemical Formula 1]
In this case, R is OR 'or NR' 2 , R 'is C n H 2n + 1 -or C n H 2n + 2 (n is 1 to 20), m is 1 to 3.
Synthesis of 5,5 '-(4,4' (1,4-phenylenebis (phenylazanediyl) bis (4,1-phenylene) dithiophene-2-carbaldehyde using the 2P compound Step 3P ;
(2E, 2'E) -tert-butyl 3,3 '-(5,5'-(4,4 '-(1,4-phenylenebis (phenylazanediyl)) using the above compound of 3P Synthesis step ( 4P ) of bis (4,1-phenylene) bis (thiophen-5,2-diyl)) bis (2-cyanoacrylate); and
(2E, 2'E) -3,3 '-(5,5'-(4,4 '-(1,4-phenylenebis (phenylazanediyl) bis) (4, 1-phenylene) bis (thiophen-5,2-diyl)) bis (2-cyanoacrylic acid) ( KS-5 )
KS-5 production method represented by the following formula (1) comprising a.
[Chemical Formula 1]
In this case, R is OR 'or NR' 2 , R 'is C n H 2n + 1 -or C n H 2n + 2 (n is 1 to 20), m is 1 to 3.
(2)
[Chemical Formula 1]
In this case, R is OR 'or NR' 2 , R 'is C n H 2n + 1 -or C n H 2n + 2 (n is 1 to 20), m is 1 to 3.
[Chemical Formula 1]
In this case, R is OR 'or NR' 2 , R 'is C n H 2n + 1 -or C n H 2n + 2 (n is 1 to 20), m is 1 to 3.
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