KR101483621B1 - Dye for dye sensitized sola cell comprising bicarbazole derivatives and sola cell comprising it - Google Patents
Dye for dye sensitized sola cell comprising bicarbazole derivatives and sola cell comprising it Download PDFInfo
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- 0 CC*1*(ccc(C=O)c2)c2-c2c1ccc(-c1cc(C3=CC(C=O)=CC[C@@]3C=C(C)CC)c(C)cc1)c2 Chemical compound CC*1*(ccc(C=O)c2)c2-c2c1ccc(-c1cc(C3=CC(C=O)=CC[C@@]3C=C(C)CC)c(C)cc1)c2 0.000 description 3
- BKTYLKIJLGCPHO-UHFFFAOYSA-N CCC(C1)=Cc(cccc2)c2-c2c1ccc(-c(cc1)cc3c1[n](CC)c1ccc(C=O)cc31)c2 Chemical compound CCC(C1)=Cc(cccc2)c2-c2c1ccc(-c(cc1)cc3c1[n](CC)c1ccc(C=O)cc31)c2 BKTYLKIJLGCPHO-UHFFFAOYSA-N 0.000 description 1
- PBQMPYPLPTUXDI-WDZFZDKYSA-N CCC(C1)c(cccc2)c2-c2c1ccc(-c1ccc(C)c(-c3ccccc3/C=C\CC)c1)c2 Chemical compound CCC(C1)c(cccc2)c2-c2c1ccc(-c1ccc(C)c(-c3ccccc3/C=C\CC)c1)c2 PBQMPYPLPTUXDI-WDZFZDKYSA-N 0.000 description 1
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- Y02E10/542—Dye sensitized solar cells
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Abstract
The present invention relates to a dye compound for a solar cell comprising a bi-carbazole derivative and a dye-sensitized solar cell comprising the same.
Description
The present invention relates to a dye for a dye-sensitized solar cell comprising a bicalbaazole derivative and a solar cell comprising the same, and more particularly to a dye for a dye-sensitized solar cell comprising a bivalent carbazole derivative having improved photoelectric conversion efficiency, It is about solar cells.
A solar cell is a device that converts light energy into electric energy using photovoltaic effect. Depending on its constituent materials, it is divided into a silicon solar cell, a thin film solar cell, a dye-sensitized solar cell, and an organic polymer solar cell .
Among these, the photosensitive dyes used in the dye-sensitized solar cell are mainly divided into organic metal dyes and organic dyes. The absorption rate of sunlight in the visible light region reaching the index of the dye and the efficiency of the injection into the conduction band of the nano-oxide affect the performance of the dye-sensitized solar cell.
Currently, organic metal dyes are known to have higher efficiency than organic dyes. However, since organic dyes do not contain metals, they have low resource constraints and exhibit a high absorption efficiency (π → π * transition in the molecule), so that the absorption of sunlight is good and the dye design of various structures is easy, And can be synthesized at a lower cost than metal dyes, thereby reducing the manufacturing cost.
However, although organic dyes have advantages over organometallic dyes, they are difficult to use as dyes for dye-sensitized solar cells due to their low photoelectric conversion efficiency.
Accordingly, an object of the present invention is to provide a dye for a dye-sensitized solar cell comprising a bivalent carbazole derivative in which two carbazole compounds having a strong electron donor function are connected, and a solar cell comprising the same.
Disclosed is a dye-sensitized solar cell having improved photoelectric conversion efficiency and a dye used therefor in order to solve the problems of the prior art.
Specifically, the present invention provides a dye compound for a solar cell represented by the following formula (1).
In the above formulas,
(1) R and R 'are independently selected from the group consisting of hydrogen, a C 1-12 alkyl group, a C 2-12 alkenyl group, a C 2-12 alkynyl group, a substituted or unsubstituted aryl group, And a heterocyclic group which may have a substituent.
(2) A 1 and A 2 are independently absent or absent; Hydrogen; Aliphatic hydrocarbons, substituted or unsubstituted C 1 -20; Aromatic hydrocarbons substituted or unsubstituted C 1 -20; A substituted or unsubstituted C 1 -20 heterocycle, and at least one of them contains at least one acidic hydrogen capable of hydrogen bonding with an electron withdrawing group.
(3) Y 1 and Y 2 are a single bond; When A 1 and A 2 are present, a C 1 -12 alkylene group, a C 2-12 alkenylene group, a C 2 -12 alkynylene group, a substituted or unsubstituted arylene group, and a substituted or unsubstituted heteroarylene group Selected from the group consisting of; A case to 1, A 2 is the non-existence of hydrogen, C 1 -12 alkyl, C 2 -12 alkenyl, C 2 -12 alkynyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group consisting of unsubstituted It is selected from the group.
The heterocyclic group refers to a cyclic compound containing at least one heteroatom such as O, N, S, etc., and includes both aromatic and alicyclic rings.
The number of carbon atoms in the aryl group may be 6 to 60, and the number of carbon atoms in the hetero ring may be 2 to 60, unless otherwise specified in the present invention.
Illustratively, Y 1 and Y 2 are substituted or unsubstituted phenyl, naphthyl, anthryl, thiophene or furyl groups, or substituted or unsubstituted phenylene, naphthylene, anthracenylene, 2 Lt; / RTI > or a divalent furyl dile group.
At least one of A 1 and A 2 may include a carboxylic acid group, a phosphorous acid group, a sulfonic acid group, a phosphinic acid group, a hydroxyacid group or an oxycarboxylic acid group.
More specifically, the formula (1) may be represented by the following formula (2).
Wherein X is CH = CH, S, or O, and n is an integer of 0 to 5.
delete
The formula (1) may be one of the compounds represented by the following formulas (3) to (8).
In Formula 3 and Formula 4, n is an integer of 0 to 5, m is an integer of 0 to 11,
And n and m in the general formulas (5) to (8) are integers of 0 to 5.
In addition, the compound represented by the formula (1) of the present invention may be one of the following compounds.
In another aspect, the present invention provides a dye-sensitized solar cell comprising a first electrode, a second electrode, and a dye layer formed between the first electrode and the second electrode, wherein the dye layer comprises the dye of the formula 1 < / RTI >
According to the present invention, photoelectric conversion efficiency of a dye-sensitized solar cell can be improved by including a dye for a dye-sensitized solar cell to which two carbazole compounds having a strong electron donor function are connected.
1 is a graph showing a light absorption spectrum of a dye containing a compound according to an embodiment of the present invention.
2 is a graph showing current-voltage characteristics of a dye-sensitized solar cell including a compound according to an embodiment of the present invention.
Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings in order to facilitate a person skilled in the art to which the present invention pertains. The present invention may be embodied in many different forms and is not limited to the embodiments described herein. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.
The dye compound for a solar cell according to an embodiment of the present invention is represented by the following formula.
In the above formulas,
(1) R and R 'are independently selected from the group consisting of hydrogen, a C 1-12 alkyl group, a C 2-12 alkenyl group, a C 2-12 alkynyl group, a substituted or unsubstituted aryl group, Gt; is selected from the group consisting of < RTI ID = 0.0 >
(2) A 1 and A 2 are independently absent or absent; Hydrogen; Aliphatic hydrocarbons, substituted or unsubstituted C 1 -20; Aromatic hydrocarbons substituted or unsubstituted C 1 -20; A substituted or unsubstituted C 1 -20 heterocycle, at least one of which contains at least one acidic hydrogen capable of hydrogen bonding with an electron withdrawing group,
(3) Y 1 and Y 2 are a single bond; A 1, A 2 is present, when the C 1 -12 alkylene, C 2-12 alkenylene, C 2 -12 alkynyl group, a substituted or unsubstituted aryl group of C 6 ~ C 20 ring group, and a substituted or unsubstituted A substituted or unsubstituted C 2 -C 20 heteroarylene group; A 1, if A 2 is the non-existence of hydrogen, C 1 -12 alkyl, C 2 -12 alkenyl, C 2 -12 alkynyl group, an aryl group, a substituted or unsubstituted C 6 ~ C 20, and a substituted or unsubstituted And a substituted C 2 -C 20 heteroaryl group.
According to another embodiment of the present invention, there is provided a dye-sensitized solar cell comprising the bicarbazole derivative compound of Chemical Formula 1.
BACKGROUND ART A dye-sensitized solar cell is one of organic solar cells, and generally includes a transparent electrode coated on a transparent glass, a nano-semiconductor oxide adhered on the transparent electrode, a dye coated on the nano-semiconductor oxide particle, And an oxidation-reduction electrolyte located in the anode.
The dye absorbs the sunlight and the dye is in an excited state due to the absorption of the sunlight to send electrons to the conduction band of the nano semiconductor oxide and is supplied again from the electrolyte as much as the electrons sent to the conduction band, . Therefore, when the dye absorbs sunlight and becomes an excited state, it is advantageous to emit a large amount of electrons. The dyestuff containing at least one of the bicarbazole derivative compound of formula (1) and the bicarbazole derivative compound of formula (2) according to this embodiment contains two carbazole compounds having a strong electron donor function , It is possible to emit as much electrons as that, and the photoelectric conversion efficiency of the solar cell can be increased.
The transparent electrode may include a transparent electrode. In order to improve the energy efficiency, the opposite electrode on which sunlight is incident may include platinum having good reflectivity. The transparent electrode may include commonly used F-doped SnO 2 (FTO), Sn-doped In 2 O 3 (ITO), ZnO, or the like. The substrate to which the transparent electrode is attached may include glass or a flexible substrate.
The nano-semiconductor oxide may include commonly used TiO 2 , and the oxidation-reduction electrolyte may be composed of oxidation-reduction species such as I - / I 3 - . The source of the I - ion may include LiI, NaI, alkaline ammonium iodide or imidazolium iodine, and the I 3 - ion may be generated by dissolving I 2 in a solvent. As the medium of the electrolyte, a liquid such as acetonitrile, valeronitrile, or a polymer such as PVdF may be used.
Hereinafter, the present invention will be described in more detail with reference to Preparation Examples and Experimental Examples of a dye compound for a solar cell according to an embodiment of the present invention. However, since the number of the compounds belonging to the formula 1 is high, some of the compounds belonging to the formula 1 will be exemplarily explained. Those skilled in the art, that is, those skilled in the art, can prepare the compounds belonging to the present invention which are not illustrated through the following production examples. The following Preparation Examples and Experimental Examples are for the purpose of illustrating the present invention, and the scope of the present invention is not limited thereto.
Synthesis method
[Reaction Scheme 1]
The reaction conditions of Scheme 1, (i) steps, FeCl 3, CHCl 3, and rt (room temperature), 3h, (ii) step is POCl 3, and 1,2-dichoroethane, reflux 12h, ( iii) step Is cyanoacetic acid, piperidine, CHCl 3 , reflux 12 h.
Intermediate 1 (9,9'- Diethyl -3,3'- Bicarbazole ) Synthesis method:
Zinc chloride (III) (15 g) was slowly added to 9-ethylcarbazole (5 g, 0.030 mol) dissolved in 50 ml of chloroform. After stirring at room temperature for 2 hours, the reaction was terminated by TLC. The reaction product was added to 300 ml of methanol. The resulting yellow solid was filtered, washed with dilute aqueous ammonia, water and methanol in order, and 4.3 g (0.011 mol, 74%) of a yellow solid was obtained as an intermediate 1. The chemical characteristics of the intermediate 1 are as follows:
- 1 H-NMR (CDCl 3 ): 1.48 (t, 6H), 4.43 (t, 4H), 7.25, 7.27 (dd, 2H), 7.72 ~ 7.53 (m, 6H), 7.83, 7.85 (dd, 2H) , [Delta] 8.18, 8.20 (d, 2H), 8.41 (d, 2H)
- MS calcd. for C 28 H 24 N 2: 388.5, found: m / z 388.3 (M +)
Intermediate 2 (9,9'- Diethyl -3,3'- Bicabazole -6- Carboaldehyde ) Synthesis method:
After dissolving 1 g of 9,9'-diethyl-3,3'-bicarbazole (intermediate product 1) in 20 ml of 1,2-dichloromethane, the mixture was dissolved in N, N- dimethylformamide (DMF , 5 mL) and phosphorus oxychloride were added in this order, followed by reflux stirring at 80 ° C for 24 hours. After removal of DMF under vacuum, the reaction mixture was neutralized with sodium acetate and extracted with chloroform. Purification by column chromatography using chloroform and acetonitrile as eluent afforded 1 g (2.40 mmol, 44%) of light yellow solid compound as intermediate 2. The chemical characteristics of the
- 1 H-NMR (CDCl 3 ): 1.50 (t, 6H), 4.44 (t, 4H), 7.25 (d, 1H), 7.51 ~ 7.56 (m, 5H), 7.84, 7.91 (dd, 2H), 8.03 , 8.20 (dd, 2H), 8.41,8.48 (dd, 2H), 8.71
- MS calcd. for C 29 H 24 N 2 O : 416.19, found: m / z 416.3 (M + ),
Compound 1 of the present invention:
After dissolving 0.80 g (0.0015 mol) of 9,9'-diethyl-3,3'-bicarbazole-6-carboaldehyde (intermediate product 2) in 20 ml chloroform, 0.37 g (0.0043 mol) of cyanoacetic acid cyanoacetic acid and 0.37 g (0.0043 mol) of piperidine were added in this order, and the mixture was refluxed and stirred for 24 hours. After the completion of the reaction was confirmed by TLC, the solvent was removed by distillation under reduced pressure, and the residue was purified by column chromatography using methanol and chloroform to obtain 0.40 g (0.59 mmol, 40%) of yellow solid compound as Compound 1 of the present invention . The chemical characteristics of the compound 1 of the present invention are as follows.
- 1 H-NMR (CDCl 3 ): 1.59 (t, 6H), 4.42 (t, 4H), 7.02 (d, 1H), 7.16 ~ 7.60 (m, 5H), 8.09 (dd, 2H), 8.19 (dd 2H), 8.36, 8.39 (dd, 2H), 8.44 (d,
- FAB-MS calcd. for C 32 H 25 N 3 O 2 : 483.19, found: m / z 48.43 (M + ),
Intermediate 3 (9,9'- Diethyl -3,3'- Bicabazole -6,6'- Dicarboaldehyde ) synthesis Way:
Intermediate 3 was synthesized in the same manner as
- 1 H-NMR (CDCl3) : 1.56 (t, 6H), 4.48 (t, 4H), 7.53, 7.62 (d, 4H), 7.89, 7.91 (d, 2H), 8.04, 8.06 (d, 2H), 8.47 (s, 2H), 8.71 (s, 2H), 10.14 (br, 2H)
Synthesis is carried out in the same manner as compound 1 of the present invention using Intermediate 3 instead of
- 1 H-NMR (DMSO- d 6): 1.66 (t, 6H), 4.56 (t, 4H), 7.78 ~ 7.82 (dd, 4H), 7.95, 7.97 (d, 2H), 8.25, 8.26 (d, 4H), 8.56 (d, 2H), 8.78 (d, 2H)
- FAB-MS calcd. for C 36 H 26 N 4 O 4: 578.62, found: m / z 578.2 (M +)
[Reaction Scheme 2]
I The reaction conditions in the reaction schemes, (i) steps, FeCl 3, CHCl 3, rt, 3h , and, (ii) step is Br 2, CHCl 3, rt, and 24h, (iii) steps are Tributyl (thiophen-2 and -yl) stannane, Pd (PPh 3 ) 4, THF, reflux 12h, (iv) step is POCl 3, 1,2-dichoroethane, a reflux 12h, (v) steps, Cyanoacetic acid, piperidine, CHCl 3, reflux 12h.
Intermediate 4 (6,6'- Dive Lomo -9,9'- Diethyl -3,3'- Bicabazole ) Synthesis method:
After dissolving 2 g (0.0051 mol) of 9,9'-diethyl-3,3'-bicarbazole (Intermediate 1) in 30 ml of methylene chloride, 1.97 g (0.012 mol) And the mixture was stirred at room temperature for 24 hours. After completion of the reaction was confirmed by TLC, chloroform and water were used to remove salts formed during the reaction. The solvent was removed by reduced pressure distillation and recrystallization with ethanol gave 2.06 g (0.0037 mol, 74%) of the light yellow solid compound as intermediate 4. The chemical characteristics of the intermediate 4 are as follows.
- 1 H-NMR (CDCl 3 ): 1.56 (t, 6H), 4.38 (t, 4H), 7.29, 7.31 (s, 2H), 4.78, 7.50 (s, 2H), 7.55, 7.57 (dd, 2H) , 7.82, 7.84 (dd, 2H), 8.29 (d, 2H), 8.33 (d, 2H)
Intermediate 5 Synthesis method:
2.0 g (0.0036 mol) of 6,6'-dibromo-9,9'-diethyl-3,3'-bicarbazole (intermediate 4) was dissolved in 30 ml of tetrahydrofuran (THF) g (0.0086 mol) of tributylstannylthiophene and 0.17 g (0.18 mmol) of tetrakis (triphenylphosphine) palladium were added in this order, followed by stirring under reflux for 12 hours. After completion of the reaction was confirmed by TLC, chloroform and water were used to remove salts formed during the reaction. Purification by column chromatography using hexane and chloroform gave 1.23 g (0.0022 mol, 61%) of yellow solid compound as
1 H-NMR (CDCl 3 ): 1.48 (t, 6H), 4.43 (t, 4H), 7.11 (dd, 1H), 7.43, 7.52 (dd, 1H), 7.75,7.77 (dd,
Intermediate 6 Synthesis Method:
0.6 g (1.08 mmol) of
- 1 H-NMR (CDCl 3 ): 1.45 (t, 6H), 4.45 (t, 4H), 7.12 (dd, 1H), 7.31,7.33 (d, 1H), 7.37 ~ 7.58 (m, 6H), 7.69 ~ 7.88 (m, 5H), 8.31 ~ 8.52 (d, 4H), 9.89 (s, 1H)
GC-MS calcd. for C 37 H 28 N 4 OS 2 : 580.7, found: m / z 580.1 (M + ).
Synthesis method of Compound 3 of the present invention:
Compound 3 of the present invention is synthesized in the same manner as Compound 1 of the present invention using Intermediate 6 instead of
1 H-NMR (CDCl 3 ): 1.52 (t, 6H), 4.21 (t, 4H), 7.11 (dd, 1H), 7.31,7.37 (M, 2H), 8.24 (d, 1H), 8.33,8.38 (dd, 1H), 8.44-8.47
- MALDI-MS calcd. for C 40 H 29 N 3 O 2 S 2 : 647.81, found: m / z 647.8 (M + ),
Intermediate 7 Synthetic method:
(1.29 mmol, 71%) was obtained as an intermediate 7 by the same method as in the above-obtained intermediate 6. The chemical properties of the intermediate 7 are as follows.
- 1 H-NMR (CDCl3) : 1.50 (t, 6H), 4.46 (t, 4H), 7.47 ~ 7.56 (m, 3H), 7.71 (m, 1H), 7.78, 7.79 (d, 1H), 7.81, (Dd, 1H), 7.89 (dd, 1H), 8.48,8.52
GC-MS calcd. for C 38 H 28 N 2 O 2 S 2 : 608.7, found: m / z 608.1 (M + ).
Compound 4 of the present invention:
Compound 4 of the present invention was synthesized using Intermediate 7 instead of
- 1 H-NMR (CDCl3) : 1.50 (t, 6H), 4.44 (t, 4H), 7.47 ~ 7.56 (m, 3H), 7.71 (m, 1H), 7.78, 7.79 (d, 1H), 7.81 ~ 8.52 (m, 4 H)
- MALDI-MS calcd. for C 44 H 30 N 4 O 4 S 2 : 742.8, found: m / z 742.0 (M + ).
The synthesis step schematically shows synthesis examples of the compounds 1 to 4 according to one embodiment of the present invention. The intermediate products 1 to 7 and the compounds 1 to 4 produced in the above synthesis step were analyzed by NMR (bruker, 400 MHz). The GC-Mass was analyzed by Kyungpook National University joint experimental laboratory, FAB MS, Were measured at the Daegu branch of the research institute.
Preparation of solar cell using dye compound of the present invention:
A conductive glass substrate (FTO; TEC8, Pilkington, 8 Ω / ㎠, Thickness of 2.3 mm) was cleaned in ethanol using ultrasonic waves. Commercially available TiO 2 paste was prepared the (20nm, solarnonix) coating the TiO 2 paste is prepared on a glass substrate, the cleaning using a doctor blade and baked at 500 ℃ for 30 minutes.
The thickness of the baked TiO 2 paste layer was measured using a thin film thickness meter (Alpha-step IQ surface profiler, KLA Tencor). In order to use another TiO 2 paste as a scattering layer, the calcined layer was re-coated with TiO 2 particles having a size of 250 nm and then calcined at 500 ° C for 30 minutes. The prepared TiO 2 film was immersed in 0.04 M TiCl 4 aqueous solution at 70 ° C for 30 minutes.
For dye adsorption, the annealed TiO 2 electrode was immersed in a 0.3 mM dye solution (compounds 1 to 4 of the present invention) at 50 ° C for 3 hours. A Pt counter electrode was prepared by thermally reducing the thin film formed from a 0.7 mM H 2 PtCl 6 solution dissolved in 2-propanol at 400 ° C for 20 minutes.
The dye-adsorbed TiO 2 electrode and the Pt counter electrode were assembled using a 60 μm-thick thinner (Surlyn, Dupont 1702) as a binder. A liquid electrolyte was introduced through the perforation holes on the opposite electrode. The electrolyte was 3-propyl-1-methyl-imidazolyl iodide (PMII, 0.7M), lithium iodide (LiI, 0.2M) dissolved in acetonitrile / valeronitrile (85:15) Iodine (I 2 , 0.05M), t-butylpyridine (TBP, 0.5M).
[ Experimental Example 1] of dye-sensitized solar cell Light absorption spectrum Measure
The light absorption spectrum in the ethanol (EtOH) solution of the dye-sensitized solar cell prepared in Example 12 was measured. The results of the measurement of the light absorption spectrum are shown in Table 1 and FIG.
In the above table,? Represents a molar extinction coefficient.
On the other hand, Fig. 1 shows absorption spectra in an ethanol solution of dyes each containing the compounds 1 to 4 of the present invention.
[ Experimental Example 2] Current-voltage curve analysis of dye-sensitized solar cell
The current-voltage curve of the dye-sensitized solar cell prepared in Example 12 was analyzed. The results are shown in Table 2 and FIG. FIG. 2 shows a current-voltage curve analysis of the dye-sensitized solar cell of Example 2. FIG.
In Table 2, Jsc is short-circuit photocurrent density, Voc is opencircuit photovoltage, ff is a fill factor, and? Is the total photoconversion efficiency. At this time, the performance of the dye-sensitized solar cell of the present invention was measured at a work area of 0.23 cm 2 .
[ Comparative Example ]
As a comparative example, Tzi-Yi Wu et al., Synthesis and Characterization of Organic Dyes Containing Various Donors and Acceptors, Int . J. Mol . Sci . 2010, 11, 329-353, which is a carbazole organic dye having the formula:
As shown in Table 2, the photoelectric conversion efficiency of the solar cell using the dyes containing the compounds 1 to 4 of the present invention was the highest at 5.85% of the efficiency of the compound 3, It was confirmed that the photovoltaic conversion efficiency of the solar cell included as the dye was 2.43%.
These results show that, in the case of the compound of the present invention, two carbazole compounds acting as an electron donor are linked to each other to emit as much electrons, thereby improving photoelectric conversion efficiency.
Although several embodiments of the present invention have been shown and described, those skilled in the art will appreciate that various modifications may be made without departing from the principles and spirit of the invention . The scope of the invention will be determined by the appended claims and their equivalents.
Claims (7)
In Formula 4, n and m are each an integer of 1 to 5.
In the general formulas (7) and (8), R is independently a C 1-12 alkyl group, a C 2-12 alkenyl group, a C 2-12 alkynyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group N is an integer of 1 to 5, and m is an integer of 1.
The dye-sensitized solar cell according to any one of claims 4 to 6, wherein the dye layer comprises the compound of any one of claims 4 to 6.
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| KR20100131068A (en) * | 2009-06-05 | 2010-12-15 | (주)아이티켐 | Carbazole thiophenyl based compounds and organic light emitting device including the same |
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| KR20100131068A (en) * | 2009-06-05 | 2010-12-15 | (주)아이티켐 | Carbazole thiophenyl based compounds and organic light emitting device including the same |
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