KR101510591B1 - Dye-sensitized solar cell comprising amine-based compound - Google Patents
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Abstract
The present invention provides a dye-sensitized solar cell comprising an amine-based compound.
Description
The present invention relates to a dye-sensitized solar cell comprising an amine-based compound.
This specification claims the benefit of Korean Patent Application No. 10-2013-0115986, filed on September 30, 2013, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.
Recently, a variety of researches have been conducted to replace conventional fossil fuels in order to solve the energy problem faced by reducing the emission of carbon dioxide, which is regarded as a main cause of global warming. Among them, development of dye-sensitized solar cells as solar cells using solar energy is underway.
A dye-sensitized solar cell is a mechanism for absorbing light energy to generate an electron-hole pair. The dye-sensitized solar cell is a photo-electrochemical solar cell having a photosensitive dye molecule and a transition metal oxide to be.
A number of studies have been conducted in this area since the development of dye-sensitized nanoparticle titanium dioxide (anatase structure) solar cells by Michael Gratzel of the Swiss National Lozan Institute for Advanced Technology (EPFL) in 1991.
The present invention aims to provide a dye-sensitized solar cell comprising an amine-based compound.
In one embodiment of the present disclosure, the first electrode;
A second electrode facing the first electrode; And
And an electrolyte layer provided on the first electrode,
Wherein the electrolyte layer comprises a dye comprising an amine compound represented by the following formula (1).
[Chemical Formula 1]
In formula (1)
m and n are each an integer of 0 to 3,
X and Y are the same or different from each other, and are each independently a direct bond; NR; S; Or O,
R is hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1 to C25 alkoxy group; And a substituted or unsubstituted alkenyl group,
A and A 'are the same or different from each other, and each independently O; Or CR'R "
A substituted or unsubstituted C6 to C25 ester group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, A substituted or unsubstituted C1 to C25 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C25 alkoxy group, a substituted or unsubstituted C2 to C25 alkenyl group, A substituted or unsubstituted aryl group of 6 to 40 carbon atoms, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted carbonyl group of 1 to 40 carbon atoms, Or a condensed ring of aliphatic, aromatic, aliphatic hetero or aromatic hetero to each other,
L1 is a direct bond; A substituted or unsubstituted alkylene group having 1 to 10 carbon atoms; A substituted or unsubstituted, substituted or unsubstituted arylene group having 1 to 40 carbon atoms; Or a substituted or unsubstituted C1 to C40 heterocyclic group containing at least one of N, O and S atoms,
R1 to R4 are the same or different and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1 to C25 alkoxy group; A substituted or unsubstituted C2 to C25 alkenyl group; A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms,
R5 and R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms.
The dye-sensitized solar cell comprising an amine compound according to one embodiment of the present invention can increase the photoelectric conversion efficiency.
The amine-based compound according to one embodiment of the present invention has a high decomposition temperature, and thus the dye-sensitized solar cell including the amine-based compound has excellent thermal stability.
1 is a diagram showing UV absorption spectra of Examples and Comparative Examples.
2 is a view showing Incident Photon To Current Efficiency (IPCE) of the embodiment and the comparative example.
3 is a graph showing the JV curves of Examples and Comparative Examples.
Hereinafter, the present invention will be described in detail.
According to one embodiment of the present invention, there is provided a dye-sensitized solar cell comprising the amine compound represented by
The amine compound according to one embodiment of the present disclosure has a dimer structure. In this case, the molecular weight is higher than that of the compound having a monomer structure. Therefore, the dye-sensitized solar cell including the high decomposition temperature has an excellent thermal stability.
In one embodiment of the present invention,
The above * means that the benzene ring of formula (1) is bonded to the benzene ring.
As described above, when the structure is bonded to the benzene ring at the para position, the electrons of the electron-donating functional group including N can be efficiently transferred to the electron acceptor at the para position. As a result, the efficiency of the dye- .
In one embodiment of the present invention, the amine-based compound represented by Formula 1 may include an amine-based compound represented by Formula 2 below.
(2)
In formula (2)
m, n, A, A ', X, Y, L1, R1 to R4, R5 and R6 are as defined in formula (1).
Illustrative examples of such substituents are set forth below, but are not limited thereto.
The term "substituted or unsubstituted" A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; Silyl group; An arylalkenyl group; An aryl group; Carbazole group; Ether group; A fluorenyl group; A nitrile group; A nitro group; A hydroxy group; A cyano group, and a heterocyclic group containing at least one of N, O, S, or P atoms, or has no substituent group.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 25. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl and heptyl.
In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 20 carbon atoms, and particularly preferably a cyclopentyl group and a cyclohexyl group.
In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 25. Specific examples thereof include, but are not limited to, an alkenyl group substituted with an aryl group such as a stilbenyl group or a styrenyl group.
In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specific examples include, but are not limited to, a methoxy group, an ethoxy group, a n-propyloxy group, an iso-propyloxy group, a n-butyloxy group, and a cyclopentyloxy group.
When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 40 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and a stilbenyl group.
When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 40 carbon atoms. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.
In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
When the fluorenyl group is substituted,
In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing O, N or S, and the number of carbon atoms is not particularly limited, but preferably 2 to 40 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a triazine group, , A quinolinyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, And the like, but the present invention is not limited thereto.
In the present specification, the alkylene group means that there are two bonding sites in the alkane. The alkylene group may be linear, branched or cyclic. The number of carbon atoms of the alkylene group is not particularly limited, but is preferably 1 to 10 carbon atoms.
In the present specification, an arylene group means that two aryl positions are present in an aryl group. The number of carbon atoms of the arylene group is not particularly limited, but is preferably 1 to 40 carbon atoms.
In the present specification, the condensed ring of R 'and R "and the aliphatic, aromatic, aliphatic hetero or aromatic hetero is preferably a 5- to 7-membered aliphatic condensed ring, a 5- to 7-membered aromatic condensed ring, , A condensed ring of a 5- to 7-membered aliphatic hetero ring containing at least one of N and S, a condensed ring of a 5- to 7-membered aromatic heterocycle containing at least one of O, N and S as a heteroatom .
In one embodiment of the present specification, L1 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.
In one embodiment of the present invention, L1 is a butylene group having 4 carbon atoms.
In one embodiment of the present disclosure, X is O.
In one embodiment of the present disclosure, Y is O.
In one embodiment of the present invention,
In one embodiment of the present invention,
When
In one embodiment of the present disclosure, A is O.
In one embodiment of the present disclosure, A 'is O.
In one embodiment of the present disclosure, A is CR'R ".
In one embodiment of the present disclosure, A 'is CR'R ".
In one embodiment of the present disclosure, A is CR'R ", and R 'and R "are different from each other and are each a nitrile group or a carboxyl group.
In one embodiment of the present disclosure, A 'is CR'R ", and R' and R" are different from each other and are each a nitrile group or a carboxyl group.
In one embodiment of the present disclosure, A is CR'R ", and R 'and R "together form a condensed ring of aromatic hetero.
In one embodiment of the present specification, A is CR'R ", and R 'and R "form a rhodanine group with respect to each other.
In one embodiment of the present disclosure, A is CR'R ", and R 'and R "form a rhodanine group, and acetic acid may be further substituted.
In one embodiment of the present disclosure, A 'is CR'R "and R' and R" form a condensed ring of aromatic heteroatoms with each other.
In one embodiment of the present specification, A 'is CR'R ", and R' and R "form a rhodanine group with respect to each other.
In one embodiment of the present disclosure, A 'is CR'R ", and R' and R "form a rhodanine group with each other, and acetic acid may be further substituted.
In one embodiment of the present invention, the amine compound represented by
[Formula 1-1]
[Formula 1-2]
[Formula 1-3]
[Formula 1-4]
[Formula 1-5]
The amine compound of
In one embodiment of the present invention, the maximum absorption wavelength (? Max ) of the amine compound is 350 nm to 550 nm. Specifically, the maximum absorption wavelength of the amine compound is 380 nm to 500 nm.
In one embodiment of the present disclosure, there is provided a dye comprising the amine compound.
The dye containing an amine compound having a dimer structure according to one embodiment of the present invention has an effect of increasing the molecular weight and improving the heat resistance. Therefore, the dye-sensitized solar cell containing the dye has an excellent stability.
In one embodiment of the present invention, the dye is composed of the amine compound alone, or further comprises a separate pigment and / or dye to constitute a colorant.
The pigment means a powdery coloring agent which is insoluble in water and an organic solvent, and examples thereof include, but are not limited to, Red 254, Red 177, and the like.
Dye refers to a coloring agent which is dissolved in water and an organic solvent, dispersed as a single molecule, and colored with a molecule such as a fiber.
In one embodiment of the present invention, the dye may be composed of the amine compound represented by
That is, in one embodiment, the content of the amine compound represented by
In another embodiment, the content of the amine compound represented by
In another embodiment, the content of the amine compound represented by
In one embodiment of the present specification, there is provided a dye-sensitized solar cell comprising the dye.
In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And an electrolyte layer disposed between the first electrode and the second electrode, wherein the electrolyte layer comprises a dye comprising an amine compound represented by
In one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode. In another embodiment, the first electrode is a cathode and the second electrode is an anode.
In one embodiment of the present invention, the first electrode is a working electrode, and the second electrode is a counter electrode.
The dye-sensitized solar cell according to one embodiment is a sandwich structure in which a working electrode and a counter electrode are bonded to each other.
In this specification, the first and second electrodes are made of platinum, ruthenium, palladium, iridium, rhodium, osmium, carbon, tungsten oxide (WO 3 ) and titanium dioxide (TiO 2 ) But are not limited thereto.
In one embodiment of the present disclosure, the electrolyte layer comprises a porous membrane and an electrolyte.
In the present specification, the porous film includes a metal oxide particle coated with a dye containing an amine compound represented by the above formula (1). Specifically, the surface of the metal oxide particles is coated with a dye including an amine compound represented by
In the present specification, the metal oxide particles have a fine and uniform average particle diameter, and may be titanium oxide, zinc oxide, tin oxide, strontium oxide, indium oxide, iridium oxide, lanthanum oxide, vanadium oxide, molybdenum oxide, tungsten oxide, , Magnesium oxide, aluminum oxide, yttrium oxide, scandium oxide, samarium oxide, gallium oxide, and strontium titanium oxide.
In this specification, the porous membrane can be easily formed according to a conventional method used in the art. The porous film may specifically include, but not limited to, silicon, titanium dioxide, tin dioxide, zinc dioxide, tungsten dioxide, and niobium pentoxide.
In the present specification, the electrolyte layer receives electrons from the electrode by oxidation and reduction and transfers the dye. The voltage is determined by the difference between the energy level of the dye and the oxidation and reduction levels of the electrolyte.
The electrolyte may be, for example, a solution in which iodine is dissolved in acetonitrile, but is not limited thereto.
Accordingly, when sunlight is incident into the dye-sensitized solar cell, the photons are first absorbed by the dye molecules in the electrolyte layer, and thus the dye molecules are electron-transferred from the ground state to the excited state to form electron-hole pairs, The injected electrons are transferred to the first electrode (working electrode) through the interface, and to the second electrode (counter electrode), which is the opposite electrode, through the external circuit. On the other hand, as a result of the electron transfer, the oxidized dye is reduced by the ions of the oxidation-reduction couple in the electrolyte, and the oxidized ions have electrons reaching the interface of the second electrode (counter electrode) to achieve charge neutrality The fuel-responsive solar cell is operated by a reduction reaction.
In one embodiment of the present disclosure, the dye-sensitized solar cell further comprises a substrate.
The substrate can be selected in consideration of optical properties and physical properties as required. For example, the substrate is preferably transparent. The substrate may be of a rigid material, but may also be of a flexible material such as plastic.
In addition to glass and quartz, the material of the substrate may be selected from the group consisting of polyethyleneterephthalate (PET), polyethylene naphthalate (PEN), polypropylene (PP), polyimide (PI), polycarbonate (PC), polystyrene (PS), polyoxymethylene (acrylonitrile butadiene styrene copolymer), TAC (triacetyl cellulose) and PAR (polyarylate), but are not limited thereto.
Hereinafter, the present invention will be described in detail with reference to examples. The following examples are intended to illustrate the present disclosure and the scope of the present disclosure includes the scope of the following claims and their substitutions and modifications, which are not intended to limit the scope of the embodiments.
Manufacturing example 1) Preparation of 1-1
[1a] [Formula 1-1]
5.39 g (38.812 mmol) of the above 1a, 5.36 g (95.534 mmol) of potassium hydroxide (KOH) and 0.513 g (1.591 mmol) of tetrabutylammonium bromide (TBAB) were placed in 60 ml of tetrahydrofuran . At 100 deg. C, 4.190 g (19.406 mmol) of 1,4-dibromobutane was slowly added. The reaction was carried out at 100 ° C for 24 hours, cooled to room temperature, and then precipitated with 700 ml of distilled water (DI-Water). The precipitated solid was filtered and dried, and then recrystallized in ethyl acetate (EA) to obtain 6.803 g (15.44 mmol) of Compound 1-1. (Yield: 79.57%)
The measurement results using the 1 H-NMR of the above formula 1-1 are as follows.
1 H-NMR (500MHz, CDCl 3, ppm): 10.15 (2H, s, CHO), 7.69-7.67 (2H, d, ArH), 6.27-6.25 (2H, dd, ArH), 6.01 (2H, s, ArH), 4.12-4.10 (4H, m , CH 2), 3.42-3.38 (8H, q, CH 2), 2.07-2.05 (4H, m, CH 2), 1.21-1.18 (12H, t, CH 6)
Manufacturing example 2) Preparation of Formulas 1-2
[Formula 1-1]
2 g (4.54 mmol) of the compound 1-1 obtained in Preparation Example 1, 0.927 g (10.898 mmol) of cyanoacetic acid and 0.155 g (1.816 mmol) of piperidine were dissolved in 60 g of ethyl alcohol And the mixture was stirred at 85 占 폚 for 10 hours. After cooling to room temperature, the precipitate was filtered and dried to obtain 2 g (3.48 mmol) of the formula 1-2. (Yield: 76%)
The measurement results using the 1 H-NMR of the above formula (1-2) are as follows.
1 H-NMR (500MHz, DMSO , ppm): 8.47 (2H, s, CH), 8.18-8.16 (2H, d, ArH), 6.47-6.45 (2H, dd, ArH), 6.16-6.15 (2H, d , ArH), 4.20 (4H, broad, CH 2), 3.50-3.46 (8H, q, CH 2), 1.97 (8H, broad, CH 2), 1.15-1.10 (12H, t, CH 6)
Manufacturing example 3) Preparation of Formulas 1-3
[Formula 1-1]
[Formula 1-3]
1.549 g (3.405 mmol) of the compound 1-1 obtained in Preparation Example 1, 1.367 g (7.149 mmol) of Rhodanine-3-acetic acid and 0.232 g (2.724 mmol) of piperidine, Was added to 40 g of ethyl alcohol (EtOH), and the mixture was stirred at 120 DEG C for 8 hours. After cooling to room temperature, the precipitate was filtered and dried to give 2.1 g (2.668 mmol) of the compound of Formula 1-3. (Yield: 78%)
The measurement results using the 1 H-NMR of the above Formula 1-3 are as follows.
1 H-NMR (500MHz, DMSO , ppm): 7.97 (2H, s, CH), 7.20-7.18 (2H, d, ArH), 6.48-6.48 (2H, dd, ArH), 6.24-6.23 (2H, d , ArH), 4.50 (4H, s, CH 2), 4.20 (4H, s, CH 2), 3.45-3.44 (8H, q, CH 2), 2.00 (4H, s, CH 2), 1.15-1.12 ( 12H, t, CH 6)
Manufacturing example 4) Preparation of Formulas 1-4
[Formula 1-1]
[Formula 1-4]
(2.269 mmol) of the compound 1-1 obtained in Preparation Example 1, 0.193 g (2.269 mmol) of cyanoacetic acid and 0.0386 g (0.454 mmol) of piperidine were dissolved in 23 g of ethyl alcohol (EtOH) And the mixture was stirred at 85 캜 for 6 hours. After cooling to room temperature, the precipitate was filtered and dried. The residue was purified by column (MC: MEOH 10: 1) to obtain 0.577 g (1.136 mmol) of the compound of the formula 1-4. (Yield 50%)
The measurement results using the 1 H-NMR of the above Formula 1-4 are as follows.
1 H-NMR (500MHz, CDCl 3, ppm): 10.00 (1H, s, CHO), 8.59 (1H, s, CH), 8.21 (1H, broad, ArH), 7.55 (1H, broad, ArH), 6.05 -5.83 (4H, broad, ArH) , 4.00 (4H, s, CH 2), 3.30 (8H, broad, CH 2), 1.93 (4H, broad, CH 2), 1.12 (12H, broad, CH 6)
Manufacturing example 5) Preparation of Formulas 1-5
[Formula 1-4]
[Formula 1-5]
0.577 g (1.137 mmol) of the compound 1-4 obtained in Preparation Example 4, 0.260 g (1.137 mmol) of rhodanine-3-acetic acid and 0.0194 g (0.227 mmol) of piperidine, Was added to 23 g of ethyl alcohol (EtOH), and the mixture was stirred at 85 캜 for 6 hours. The precipitate was purified by using a vacuum filter and a column after drying (MC: MEOH 10: 1 to 1: 1) to obtain 0.15 g (0.22 mmol) of the formula 1-5. (Yield: 19.3%)
The measurement results using the 1 H-NMR of the above formula (1-5) are as follows.
1 H-NMR (500MHz, DMSO , ppm): 8.32 (1H, s, CH), 8.11-8.09 (1H, d, ArH), 7.90 (1H, s, CH), 7.21-7.20 (1H, d, ArH ), 6.48-6.46 (1H, d, ArH), 6.39-6.37 (1H, d, ArH), 6.24-6.19 (2H, d, ArH), 4.26 (2H, s, CH 2), 4.24-4.41 (4H , m, CH 2), 3.46-3.40 (8H, q, CH 2), 1.93 (4H, s, CH 2), 1.15-1.11 (12H, t, CH 6)
[Comparative Compound 1] [Comparative Compound 2]
Example 1. Manufacture of dye-sensitized solar cell
(1) Working Electrode Fabrication
FTO substrate (Fluorine-doped tin oxide coated conduction glass, Pilkington, TEC-8) was cut into 1.5 cm to 1.5 cm size and washed with acetone to remove impurities on the substrate. The process of immersing in boiling acetone for 5 minutes and then drying was repeated twice. The substrate was completely immersed in ethanol and sonication was repeated twice for 10 minutes. After this, TiO 2 And a 0.2M titanium (IV) butoxide solution was coated by a spin coating method to increase the contact force, and was completely dried in an oven. Thereafter, TiO 2 (230 (M2331) -2T) was coated on the FTO substrate by a doctor blade technique, dried in an oven at 100 ° C. for 10 minutes, heated to 550 ° C. and sintered for 30 minutes, Micrometer-thick TiO 2 A transparent layer is obtained. TiO 2 (CCIC-1T) was coated and sintered in the same manner to obtain a TiO 2 scattering layer having a thickness of 4 to 5 μm. The thus obtained TiO 2 film was soaked in a 0.5 mM DMF solution prepared using the dye synthesized in Production Example 2 for 40 hours to adsorb the dye on the TiO 2 surface. After the adsorption was completed, the unadsorbed dye was completely washed with the used solvent and dried.
(2) Production of counter electrode
Two holes for injecting electrolyte were drilled in a 1.5 cm × 1.5 cm FTO board using a diamond drill. After that, it was washed and dried in the same manner as the above-mentioned cleaning method. Thereafter, it was immersed in a solution of 0.7 mM hydrogenhexachloroplatinate (H 2 PtCl 6 ) 2-propanol (2-propanol) for 20 minutes, taken out and heat-treated in an oven at 400 ° C. for 30 minutes.
(3) Manufacture of sandwich cell
Suren (Surlyn, Dupont 1702) cut in a rectangular band between the working electrode and the counter electrode was placed, and the two electrodes were stuck to each other using a hot press device. Then, the electrolyte was injected into the counter electrode through two small holes A sandwich cell is fabricated by sealing with a Surlyn strip and a cover glass. Electrolyte solutions were prepared by adding 0.2 M LiI, 0.005 M I2, 0.5 M 1-methyl-3-propylimidazoliumiodide and 0.5 M 4-tert-butylpyridine ( 4-tertbutylpyridine) was prepared by dissolving acetonitrile in a solvent.
(4) Photocurrent-voltage and Incident Photon to Current Efficiency (IPCE) measurements
When the solar cell manufactured above was irradiated with a Xe lamp (300W Xe arc lamp) equipped with a solar simulating filter of AM 1.5, a current-voltage curve was obtained using a Keithly model 2400 source measuring unit . Also, IPCE was measured at a frequency of 10 Hz in a wavelength range of 300 to 800 nm using a monochromic beam of a 75 W Xe lamp, and a silicon photodiode (NIST-calibrated photodiode G425) was used for calibration.
Example 2. Manufacture of dye-sensitized solar cell
A dye-sensitized solar cell was prepared in the same manner as in Example 1 except that the compound of Preparation Example 3 was used instead of the compound of Preparation Example 2 used in Example 1.
Example 3. Manufacture of dye-sensitized solar cell
A dye-sensitized solar cell was prepared in the same manner as in Example 1 except that the compound of Preparation Example 5 was used instead of the compound of Preparation Example 2 applied in Example 1.
Comparative Example 1. Manufacture of dye-sensitized solar cell
A dye-sensitized solar cell was prepared in the same manner as in Example 1, except that
Comparative Example 2. Manufacture of dye-sensitized solar cell
A dye-sensitized solar cell was prepared in the same manner as in Example 1, except that
The characteristics of the dye-sensitized solar cell prepared in Examples 1 to 3 and Comparative Examples 1 and 2 were measured and the results are shown in Table 1.
Absorption λ; nm
(ε; M -1 cm -1 )
485 (45,700)
In the present specification, ε denotes the molar absorbance, Voc denotes the open-circuit voltage, Jsc denotes the short-circuit current, FF denotes the fill factor, and ŋ denotes the energy conversion efficiency. The open-circuit voltage and the short-circuit current are the X-axis and Y-axis intercepts in the fourth quadrant of the voltage-current density curve, respectively. The higher the two values, the higher the efficiency of the solar cell. The fill factor is the width of the rectangle that can be drawn inside the curve divided by the product of the short-circuit current and the open-circuit voltage. The energy conversion efficiency can be obtained by dividing these three values by the intensity of the irradiated light, and a higher value is preferable.
1 is a diagram showing UV absorption spectra of Examples and Comparative Examples.
As can be seen from Fig. 1, the case of including the dimer structure has a wide absorption wavelength range, so that it is possible to absorb light in a wide area, and the photoelectric conversion efficiency is excellent.
2 is a view showing Incident Photon To Current Efficiency (IPCE) of the embodiment and the comparative example.
3 is a view showing the J-V curve of the embodiment and the comparative example.
The above efficiency can be obtained from the following equation (1).
[Formula 1]
η = Jsc × Voc × ff
Claims (8)
A second electrode facing the first electrode; And
And an electrolyte layer provided on the first electrode,
Wherein the electrolyte layer comprises a dye comprising an amine compound represented by the following Formula 1:
[Chemical Formula 1]
In formula (1)
m and n are each an integer of 0 to 3,
X and Y are the same or different from each other, and are each independently a direct bond; NR; S; Or O,
R is hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1 to C25 alkoxy group; And a substituted or unsubstituted alkenyl group,
A and A 'are the same or different from each other, and each independently O; Or CR'R "
A substituted or unsubstituted C6 to C25 ester group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, A substituted or unsubstituted C1 to C25 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C25 alkoxy group, a substituted or unsubstituted C2 to C25 alkenyl group, A substituted or unsubstituted aryl group of 6 to 40 carbon atoms, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted acrylate group, a substituted or unsubstituted amide group, a substituted or unsubstituted carbon number 1 to 40 carbon atoms, or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, or an aliphatic, aromatic, aliphatic or aromatic hetero Sum to form a ring,
L1 is a direct bond; A substituted or unsubstituted alkylene group having 1 to 10 carbon atoms; A substituted or unsubstituted, substituted or unsubstituted arylene group having 1 to 40 carbon atoms; Or a substituted or unsubstituted C1 to C40 heterocyclic group containing at least one of N, O and S atoms,
R1 to R4 are the same or different and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1 to C25 alkoxy group; A substituted or unsubstituted C2 to C25 alkenyl group; A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms,
R5 and R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms.
The dye-sensitized solar cell according to claim 1, wherein the amine compound represented by Formula 1 is represented by Formula 2:
(2)
In formula (2)
m, n, A, A ', X, Y, L1, R1 to R4, R5 and R6 are as defined in formula (1).
And L < 1 > is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.
A and A 'are the same or different from each other, and each independently O; Or CR'R "
R ' and R "are the same or different from each other and each independently form a condensed ring of a nitrile group, a carboxyl group, or an aliphatic, aromatic, aliphatic hetero or aromatic hetero.
And R < 4 > are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms.
The dye-sensitized solar cell according to claim 1, wherein the amine compound represented by Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-5.
[Formula 1-1]
[Formula 1-2]
[Formula 1-3]
[Formula 1-4]
[Formula 1-5]
Wherein the amine compound has a maximum absorption wavelength (? Max ) of 350 nm to 550 nm.
Wherein the content of the amine compound represented by the formula (1) is 0.5 wt% to 30 wt% based on the total weight of the dye.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20100069959A (en) * | 2008-12-17 | 2010-06-25 | 웅진케미칼 주식회사 | Photochromic dye for dye-sensitized solar cell and dye-sensitized solar cell using them |
| KR20110086272A (en) * | 2010-01-22 | 2011-07-28 | 영남대학교 산학협력단 | New triphenylamine derivatives and dye-sensitized solar cell comprising the same |
| KR20120057946A (en) * | 2010-11-29 | 2012-06-07 | 에버라이트 유에스에이, 인코오포레이티드 | Dye-sensitized solar cell and photoanode thereof |
| KR20130066546A (en) * | 2011-12-12 | 2013-06-20 | 고려대학교 산학협력단 | Dual-channel anchorable amine derivatives, organic dye sensitizers containing the same for highly efficient dye-sensitized solar cells and dye-sensitized solar cells containing the same |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20100069959A (en) * | 2008-12-17 | 2010-06-25 | 웅진케미칼 주식회사 | Photochromic dye for dye-sensitized solar cell and dye-sensitized solar cell using them |
| KR20110086272A (en) * | 2010-01-22 | 2011-07-28 | 영남대학교 산학협력단 | New triphenylamine derivatives and dye-sensitized solar cell comprising the same |
| KR20120057946A (en) * | 2010-11-29 | 2012-06-07 | 에버라이트 유에스에이, 인코오포레이티드 | Dye-sensitized solar cell and photoanode thereof |
| KR20130066546A (en) * | 2011-12-12 | 2013-06-20 | 고려대학교 산학협력단 | Dual-channel anchorable amine derivatives, organic dye sensitizers containing the same for highly efficient dye-sensitized solar cells and dye-sensitized solar cells containing the same |
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