KR101066906B1 - Dye-Sensitized Solar Cells Using Novel Amphiphilic Compounds, Methods for Making the Same, and Dye Containing the Same - Google Patents

Abstract

The present invention discloses compounds of formula (1) which are novel amphoteric compounds. The dye containing this amphoteric compound is adsorbed to a metal oxide layer, and the dye-sensitized solar cell excellent in performance can be formed.

<Formula 1>

Description

Novel amphiphilic compounds, methods of preparing the compounds and dye-sensitized solar cells using dyes comprising the compounds}

The present invention relates to a novel amphoteric compound and a dye-sensitized solar cell using the same as a dye.

Dye-sensitized solar cells, unlike silicon solar cells, are photoelectrochemical solar cells composed of photosensitive dye molecules and transition metal oxides. In detail, the photosensitive dye molecule absorbs visible light to generate an electron-hole pair, and the generated electrons are transferred to the substrate by the transition metal oxide to have photoelectrochemical properties.

Representative examples of dye-sensitized solar cells known to date are dye-sensitized solar cells published by Gratzel et al. (S. Patent No. 4,927,721 and No. 5,350,644). In general, dye-sensitized solar cells made by Gratzel et al. Are composed of a semiconductor electrode composed of nanoparticle titanium dioxide (TiO ₂ ) coated with dye molecules, a platinum electrode, and an electrolyte solution filled therebetween. Such dye-sensitized solar cells have been attracting attention because they are useful as solar cells because the manufacturing cost per power is lower than that of silicon solar cells.

On the other hand, the dye used in the conventional dye-sensitized solar cell is known as Ru (dcb) (bpy) _{2 2} ⁺ to which the Ru (II) -polypyridyl compound is linked (see US Patent No. 5,350,644). In addition, there are dyes including various ligands including nitrogen in transition metals such as Ru, Os, Cu, and Zn (US Pat. No. 6,350,946, US Pat. -294306). Among the dyes, compounds having the following formula (trade names: 'N719', 'N3', etc.) showing red orange red and dark blue as Ru-based dyes of nanoparticle dye-sensitized solar cells are most widely used as dyes of highly efficient dye-sensitized solar cells. It is used. However, it is very important to develop dyes of various colors in order to commercialize and expand the applicability of dye-sensitized solar cells.

The technical problem to be solved by the present invention is to provide a novel amphoteric compound.

Another technical problem to be solved by the present invention is to provide a novel method for preparing an affinity compound.

Another technical problem to be solved by the present invention is to provide a dye-sensitized solar cell having excellent performance by using a dye containing the novel compound.

In order to solve the above technical problem, the amphiphilic compound according to the present invention is a compound represented by the following formula (1).

<Formula 1>

R ₁ of Chemical Formula 1 is any one selected from the group consisting of alkyl, phenyl, C1-C20 alkylphenyl, and R ₂ and R ₃ of Chemical Formula 1 Is any one selected from the group consisting of Formulas 4 to 11.

delete

delete

delete

delete

<Formula 4>

<Formula 5>

<Formula 6>

<Formula 7>

<Formula 8>

<Formula 9>

<Formula 10>

<Formula 11>

R ₄ of Formulas 4 to 11 is any one selected from the group consisting of hydrogen, alkyl having 1 to 20 carbon atoms, and alkyloxy having 1 to 20 carbon atoms.

The amphoteric compound according to the present invention may be any one selected from the group consisting of compounds represented by the following Formulas 12, 13 and 16.

<Formula 12>

<Formula 13>

delete

delete

delete

delete

<Formula 16>

delete

delete

delete

delete

delete

delete

In order to solve the above other technical problem, a method for preparing an amphoteric compound according to the present invention is a method for preparing a compound of Formula 1, a compound of Formula 21, a compound of Formula 22 and Reacting the compound of formula 23 sequentially.

<Formula 1>

<Formula 20>

<Formula 21>

<Formula 22>

<Formula 23>

R ₁ of Formula 1 and Formula 20 is any one selected from the group consisting of alkyl having 1 to 20 carbon atoms, phenyl, and alkylphenyl having 1 to 20 carbon atoms. R ₂ and R ₃ are any one selected from the group consisting of the following Chemical Formulas 4 to 11.

delete

delete

delete

delete

<Formula 4>

<Formula 5>

<Formula 6>

<Formula 7>

<Formula 8>

<Formula 9>

<Formula 10>

<Formula 11>

R ₄ of Formulas 4 to 11 is any one selected from the group consisting of hydrogen, alkyl having 1 to 20 carbon atoms, and alkyloxy having 1 to 20 carbon atoms.

In order to solve the above another technical problem, the dye-sensitized solar cell according to the present invention comprises a conductive substrate; A semiconductor electrode formed on the conductive substrate and including a metal oxide layer adsorbed with a dye including the compound of Formula 1; Counter electrode; And an electrolyte solution filling the semiconductor electrode and the counter electrode.

<Formula 1>

R ₁ of Chemical Formula 1 is any one selected from the group consisting of alkyl, phenyl, C1-C20 alkylphenyl, and R ₂ and R ₃ of Chemical Formula 1 Is any one selected from the group consisting of Formulas 4 to 11.

delete

delete

delete

delete

<Formula 4>

<Formula 5>

<Formula 6>

<Formula 7>

<Formula 8>

<Formula 9>

<Formula 10>

<Formula 11>

R ₄ of Formulas 4 to 11 is any one selected from the group consisting of hydrogen, alkyl having 1 to 20 carbon atoms, and alkyloxy having 1 to 20 carbon atoms.

In the dye-sensitized solar cell according to the present invention, any one selected from the group consisting of compounds represented by Formulas 12, 13, and 16 may be used as a dye.

<Formula 12>

<Formula 13>

delete

delete

delete

delete

<Formula 16>

delete

delete

delete

delete

delete

delete

The present invention provides a novel amphoteric compound used as a raw material for dyes and a method for preparing the same. The present invention also provides a dye-sensitized solar cell in which the novel amphiphilic compound is used. The novel zwitterionic compounds can absorb wavelengths different from those absorbed by various conventional dyes, and thus have various uses. The dye-sensitized solar cells using these zwitterionic compounds have a significantly improved J _sc value and thus efficiency. This will be excellent.

The present invention is an amphiphilic compound comprising a compound of formula (1).

<Formula 1>

Here, R ₁ is any one selected from the group consisting of alkyl having 1 to 20 carbon atoms, phenyl, alkylphenyl having 1 to 20 carbon atoms, R ₂ and R ₃ is hydrogen, 1 to It is either alkyl of 20 or alkyloxy of 1 to 20 carbon atoms, or any one selected from the group consisting of Formula 2 to Formula 11.

<Formula 2>

<Formula 3>

<Formula 4>

<Formula 5>

<Formula 6>

<Formula 7>

<Formula 8>

<Formula 9>

<Formula 10>

<Formula 11>

R ₄ in Formulas 2 to 11 is any one selected from the group consisting of hydrogen, alkyl having 1 to 20 carbon atoms, and alkyloxy having 1 to 20 carbon atoms.

Specifically, the compound of Formula 1 may be represented by the compounds of Formula 33 to Formula 43.

<Formula 33>

<Formula 34>

<Formula 35>

<Formula 36>

<Formula 37>

<Formula 38>

<Formula 39>

<Formula 40>

<Formula 41>

<Formula 42>

<Formula 43>

R ₁ of Formula 33 to Formula 43 is any one selected from the group consisting of alkyl having 1 to 20 carbon atoms, phenyl, alkylphenyl having 1 to 20 carbon atoms, R ₅ and R ₆ of Formula 33 to 43 are hydrogen, 1 carbon It is any one selected from the group consisting of alkyl of 20 to 20, alkyloxy of 1 to 20 carbon atoms.

In addition, R ₂ and R ₃ of Formula 1, and R ₅ and R ₆ of Formula 33 to Formula 43 may each have the same formula. Preferred amphoteric compounds according to the invention are those of the formulas (12)-(19).

<Formula 12>

<Formula 13>

<Formula 14>

&Lt; Formula 15 >

<Formula 16>

<Formula 17>

&Lt; Formula 18 >

(19)

Here, the compound of Formula 12 is JK-85, the compound of Formula 13 is JK-86, the compound of Formula 14 is JK-104, the compound of Formula 15 is JK-95, the compound of Formula 16 is JK-99, The compound is named JK-135, the compound of Formula 18 is named JK-94, and the compound of Formula 19 is designated JK-96.

In addition, the present invention includes a method for preparing a compound of formula (1). The compound of Formula 1 may be prepared by sequentially reacting the compound of Formula 21, the compound of Formula 22, and the compound of Formula 23 with the compound of Formula 20.

<Formula 20>

<Formula 21>

<Formula 22>

<Formula 23>

R ₁ in Formula 20 is any one selected from the group consisting of alkyl having 1 to 20 carbon atoms, phenyl, alkylphenyl having 1 to 20 carbon atoms, and R ₂ and R ₃ in Formula 20 are hydrogen, alkyl having 1 to 20 carbon atoms or carbon atoms Alkyloxy of 1 to 20 or any one selected from the group consisting of Formulas 2 to 11. The compound of Formula 21 is dichloro (p-cymene) ruthenium (II) dimer, and the compound of Formula 22 is 2,2'-bipyridine-4-4'dicarboxylic acid. A reaction for preparing the compound of Formula 1 is shown in Scheme 1, which may be carried out in dimethyl-formamide (DMF).

<Scheme 1>

R ₂ and R ₃ in Formula 1 and Formula 20 may have the same formula. In this case, the compound of Formula 20 may be prepared by reacting the compound of Formula 24 with the compound of Formula 25, as shown in Scheme 2.

<Scheme 2>

The reaction of Scheme 2 can be carried out by adding together bis (diphenylphosphanyl) propane (DPPP), Pd ₂ (dba) ₃ (dipalladiumtris (benzylideneacetone) and sodium t-butoxide, and the reaction of Scheme 2 is carried out in toluene. Can be performed.

The compound of Formula 24 may be prepared by reacting the compound of Formula 26 with the compound of Formula 27 as in Scheme 3.

<Scheme 3>

The reaction of Scheme 3 may be performed by adding Pd (PPh ₃ ) ₄ (tetrakis (triphenylphosphine) palladium) and Na ₂ CO ₃ together. And the reaction of Scheme 2 may be carried out in a mixed solution of THF (tetrahydrofuran) and H ₂ O.

When the compound of Formula 24 is a compound of Formula 28, the compound of Formula 28 may be prepared by reacting the compound of Formula 29 with the compound of Formula 30, as shown in Scheme 4.

<Formula 28>

R ₄ in Formula 28 is hydrogen, alkyl having 1 to 20 carbon atoms or alkyloxy having 1 to 20 carbon atoms.

<Scheme 4>

The reaction of Scheme 4 can be carried out by adding potassium t-butoxide together. And the reaction of Scheme 4 can be carried out in THF.

When the compound of Formula 24 is a compound of Formula 31, the compound of Formula 31 may be prepared by reacting the compound of Formula 32 with the compound of Formula 30, as shown in Scheme 5.

<Formula 31>

R ₄ in Formula 31 is hydrogen, alkyl having 1 to 20 carbon atoms or alkyloxy having 1 to 20 carbon atoms.

Scheme 5

The reaction of Scheme 5 may be performed by adding potassium t-butoxide together. And the reaction of Scheme 5 can be carried out in THF.

Hereinafter, the amphoteric compound according to the present invention and a preparation method thereof will be described. The present invention is not limited to the following examples and can be embodied in other forms.

Example  One: JK Preparation of -85 (Compound of Formula 12)

The preparation step of JK-85 is shown in FIG. 1.

1) 2- bromo -4- (5- hexylthiophen -2- yl ) pyridine , Intermediate Compound 1-1 Synthesis

2-bromo-4-iodopyridine (651 mg, 2.3 mmol), 2- (5-hexylthiophen-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (677 mg, 2.3 mmol ), Pd (PPh ₃ ) ₄ (133 mg, 5 mol%) and Na ₂ CO ₃ (244 mg, 2.3 mmol) were dissolved in THF (30 ml) and H ₂ O (20 ml) solution and refluxed for 15 hours. . After evaporating the solvent under reduced pressure, H ₂ O (50 ml) and methylene chloride (50 ml) were added thereto. The organic layer was separated, dried over MgSO ₄ , purified and separated to yield 2-bromo-4- (5-hexylthiophen-2-yl) pyridine. Yield 70%.

¹ H NMR (CDCl ₃ ): 8.25 (d, 1H, J = 5.1 Hz), 7.58 (s, 1H), 7.34-7.30 (m, 2H), 6.79 (d, 1H, J = 3.9 Hz), 2.82 (t, 2H, J = 7.4 Hz), 1.66 (qu, 2H, J = 7.4 Hz), 1.32 (m, 6H), 0.89 (t, 3H, J = 6.6 Hz).

¹³ C NMR (CDCl ₃ ): 150.5, 148.3, 147.8, 140.7, 139.1, 125.8, 124.3, 123.3, 117.8, 31.8, 31.6, 30.4, 28.5, 22.8, 14.5.

2) N-h exyl -4,4'- di (5- hexylthiophen -2- yl ) -2,2'- dipyridylamine , Intermediate Compound 1-2 Synthesis

2-bromo-4- (5-hexylthiophen-2-yl) pyridine 1-1 (550 mg, 1.7 mmol), hexylamine (0.1 mL, 0.8 mmol), DPPP (1,3-bis (diphenylphosphanyl) propane) (27 mg, 0.07 mmol), Pd ₂ (dba) ₃ (dipalladiumtris (benzylideneacetone)) (30 mg, 0.033 mmol) and sodium t-butoxide (220 mg, 2.3 mmol) were mixed in a nitrogen atmosphere, followed by dry toluene ) (50 mL) was added and stirred at 80 ° C for 24 h. After evaporating the solvent under reduced pressure, H ₂ O (50 ml) and methylene chloride (50 ml) were added thereto. The organic layer is separated, dried over MgSO ₄ , purified and separated to yield N-hexyl-4,4'-di (5-hexylthiophen-2-yl) -2,2'-dipyridylamine. there was. Yield 52%.

¹ H NMR (CDCl ₃ ): 8.31 (d, 2H, J = 5.7 Hz), 7.30 (s, 2H), 7.23 (d, 2H, J = 3.9 Hz), 7.02 (d, 2H, J = 5.7 Hz), 6.74 (d, 2H, J = 3.0 Hz), 4.24 (t, 2H, J = 7.5 Hz), 2.80 (t, 4H, J = 7.7 Hz), 1.69 (m, 6H), 1.32 (m, 18H), 0.89 (m, 9H).

¹³ C NMR (CDCl ₃ ): 158.3, 148.9, 148.0, 143.0, 139.0, 125.4, 124.9, 113.5, 110.4, 48.6, 31.8, 31.6, 31.5, 30.4, 28.8, 28.5, 26.8, 22.8, 22.6, 14.1.

3) JK -85 ( cis - bis ( thiocyanato )-(2,2'- bipyridyl -4,4'- dicarboxylato ) [{N-hexyl-4,4'-di (5-hexylthiophen-2-yl)}-2,2'-dipyridylamine] ruthenium (II) di ( tetrabutylammonium ) Synthesis

N-hexyl-4,4'-di (5-hexylthiophen-2-yl) -2,2'-dipyridylamine 1-2 (90 mg, 0.153 mmol) with dichloro (p-cymene) ruthenium (II) dimmer (46 mg, 0.077 mmol) was added to DMF (15 mL) and stirred at 70 ° C. for 4 hours. Subsequently, 2,2'-bipyridine-4,4'-dicarboxylic acid (37 mg, 0.153 mmol) was added and stirred at 160 ° C. for 4 hours. NH ₄ NCS (116 mg, 1.53 mmol) was added thereto, and the reaction was allowed to proceed at 140 ° C. for 4 hours. Then, the mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure. And water was added, filtered and washed, and dried in vacuo. Purification of the dried material and filtration gave JK-85. The yield was 30%.

¹ H NMR (CD ₃ OD): 9.56 (d, 1H), 8.96 (d, 1H), 8.85 (s, 1H), 8.78 (s, 1H), 8.29 (d, 1H), 8.16 (d, 1H) , 7.74 (m, 3H), 7.53 (m, 2H), 7.42 (d, 1H), 7.15 (s, 1H), 6.94 (m, 2H), 6.80 (d, 1H), 4.21 (t, 1H), 3.78 (t, 1H), 2.90 (t, 2H), 2.79 (t, 2H), 1.64 (m, 22H), 1.36 (m, 50H), 0.98 (m, 24H), 0.86 (m, 9H).

Example  2: JK Preparation of -86 (Compound of Formula 13)

The preparation step of JK-86 is shown in FIG. 2.

1) 2- bromo -4- (2- hexylthieno [3,2-b] thiophen-5- yl ) pyridine , Intermediate Compound 2-1 Synthesis

2-bromo-4-iodopyridine (405 mg, 1.43 mmol), 2- (2-hexylthieno [3,2-b] thiophen-5-yl) -4,4,5,5-tetramethyl-1,3,2 -dioxaborolane (500 mg, 1.43 mmol), Pd (PPh ₃ ) ₄ (83 mg, 5 mol%) and Na ₂ CO ₃ (152 mg, 2.3 mmol) in THF (30 ml) and H ₂ O (20 ml) solution Dissolved in and refluxed for 10 hours. After evaporating the solvent under reduced pressure, H ₂ O (50 ml) and methylene chloride (50 ml) were added thereto. The organic layer was separated, dried over MgSO ₄ , purified and separated to yield 2-bromo-4- (2-hexylthieno [3,2-b] thiophen-5-yl) pyridine. Yield 62%.

¹ H NMR (CDCl ₃ ): 8.19 (d, 2H, J = 5.1 Hz), 6.84 (s, 2H), 6.67 (d, 2H, J = 5.1 Hz), 4.10 (t, 2H, J = 7.5, 7.8 Hz), 2.54 (s, 6H), 1.66 (m, 2H), 1.29 (m, 6H), 0.85 (t, 3H, J = 5.1 Hz).

¹³ C NMR (CDCl ₃ ): 158.5, 148.8, 147.6, 146.0, 139.6, 128.1, 126.0, 124.9, 124.8, 113.6, 112.5, 48.8, 31.8, 31.7, 31.6, 30.6, 28.9, 28.8, 28.6, 26.9, 22.8, 22.7, 14.2.

2) N-h exyl -4,4'- di (5- hexylthieno (3,2-b) thiophen) -2,2'- dipyridylamine , Intermediate Compound 2-2 Synthesis

2-bromo-4- (2-hexylthieno [3,2-b] thiophen-5-yl) pyridine 2-1 (550 mg, 1.7 mmol), hexylamine (0.1 mL, 0.8 mmol), DPPP (27 mg, 0.07 mmol), Pd ₂ (dba) ₃ (30 mg, 0.033 mmol) and sodium t-butoxide (220 mg, 2.3 mmol) were mixed in a nitrogen atmosphere, followed by addition of dry toluene (50 mL), Stir at 80 ° C for 24 h. After evaporating the solvent under reduced pressure, H ₂ O (50 ml) and methylene chloride (50 ml) were added thereto. The organic layer was separated, dried over MgSO ₄ , purified and separated to give N-hexyl-4,4'-di (5-hexylthieno [3,2-b] thiophen) -2,2'- Dipyridylamine could be obtained. The yield was 56%.

¹ H NMR (CDCl ₃ ): 8.34 (d, 2H, J = 4.8 Hz), 7.51 (s, 2H), 7.36 (s, 2H), 7.07 (d, 2H, J = 3.9 Hz), 6.90 (s, 2H), 4.25 (t, 2H, J = 6.6 Hz), 2.86 (t, 4H, J = 6.8 Hz), 1.72 (m, 6H), 1.33 (m, 18H), 0.90 (m, 6H).

¹³ C NMR (CDCl ₃ ): 158.3, 150.2, 149.0, 143.3, 141.5, 139.4, 138.1, 117.5, 116.5, 113.5, 110.4, 48.07, 31.8, 31.6, 31.5, 31.3, 28.8, 28.5, 26.9, 22.8, 22.7, 14.2.

3) JK -86 ( cis - bis ( thiocyanato )-(2,2'- bipyridyl -4,4'-dicarboxylato) [{4,4'-di (5-hexylthieno (3,2-b) thiophen)}-2,2'-dipyridylamine] ruthenium (II) di Synthesis of (tetrabutylammonium)

N-hexyl-4,4'-di (5-hexylthieno [3,2-b] thiophen) -2,2'-dipyridylamine 2-2 (90 mg, 0.153 mmol) and dichloro (p-cymene) ruthenium (II ) Dimmer (46 mg, 0.077 mmol) was added to DMF (15 mL) and stirred at 70 ° C. for 4 hours. Subsequently, 2,2'-bipyridine-4,4'-dicarboxylic acid (37 mg, 0.153 mmol) was added and stirred at 160 ° C. for 4 hours. NH ₄ NCS (116 mg, 1.53 mmol) was added thereto, and the reaction was allowed to proceed at 140 ° C. for 4 hours. Then, the mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure. And water was added, filtered and washed, and dried in vacuo. Purification of the dried material and filtration gave JK-86. Yield 27%.

¹ H NMR (CD ₃ OD): 9.56 (d, 1H), 8.97 (d, 1H), 8.85 (s, 1H), 8.78 (s, 1H), 8.28 (d, 1H), 8.16 (d, 1H) , 8.05 (s, 1H), 7.76 (m, 3H), 7.60 (s, 1H), 7.38 (d, 1H), 7.21 (d, 1H), 7.06 (s, 1H), 6.96 (s, 1H), 6.88 (d, 1H), 4.26 (t, 1H), 3.80 (t, 1H), 2.81 (m, 4H), 1.60 (m, 22H), 1.34-1.21 (m, 50H), 0.94 (m, 24H) , 0.81 (m, 9 H).

Example  3: JK Preparation of -104 (Compound of Formula 14)

A manufacturing step of JK-104 is shown in FIG. 3.

1) N- hexyl -4,4'- dimethyl -2,2'- dipyridylamine , Intermediate Compound 3-1 Synthesis

2-bromo-4-methylpyridine (2.0 g, 11.62 mmol), hexylamine (580 mg, 5.8 mmol), DPPP (191 mg, 0.47 mmol), Pd ₂ (dba) ₃ (212 mg, 0.23 mmol) and sodium t- Butoxide (1.56 g, 16.27 mmol) was mixed in a nitrogen atmosphere, and then dry toluene (50 mL) was added and stirred at 80 ° C. for 21 hours. After evaporating the solvent under reduced pressure, H ₂ O (50 ml) and methylene chloride (100 ml) were added. The organic layer was separated, dried over MgSO ₄ , purified and separated to yield N-hexyl-4,4'-dimethyl-2,2'-dipyridylamine. Yield 75%.

¹ H NMR (CDCl ₃ ): 8.19 (d, 2H, J = 5.1 Hz), 6.84 (s, 2H), 6.67 (d, 2H, J = 5.1 Hz), 4.10 (t, 2H, J = 7.5, 7.8 Hz), 2.54 (s, 6H), 1.66 (m, 2H), 1.29 (m, 6H), 0.85 (t, 3H, J = 5.1 Hz).

¹³ C NMR (CDCl ₃ ): 158.5, 148.8, 147.6, 146.0, 139.6, 128.1, 126.0, 124.9, 124.8, 113.6, 112.5, 48.8, 31.8, 31.7, 31.6, 30.6, 28.9, 28.8, 28.6, 26.9, 22.8, 22.7, 14.2.

2) N- hexyl -4,4'- dihexyl -2,2'- dipyridylamine , Intermediate Compound 3-2 Synthesis

N-hexyl-4,4'-dimethyl-2,2'-dipyridylamine 3- 1 (0.5 g, 1.76 mmol) dissolved in THF (15 mL) was added to lithium diisopropylamide (LDA) for 1 hour at room temperature. Stir it. To this mixture was added pentyl bromide (319 mg, 2.11 mmol) dissolved in THF (10 mL) and stirred for 1 hour. After evaporating the solvent under reduced pressure, H ₂ O (50 ml) and methylene chloride (100 ml) were added. The organic layer was separated, dried over MgSO ₄ , purified and separated to yield N-hexyl-4,4'-dihexyl-2,2'-dipyridylamine. Yield 75%.

¹ H NMR (CDCl ₃ ): 8.21 (d, 2H, J = 5.4 Hz), 6.85 (s, 2H), 6.67 (d, 2H, J = 3.6 Hz), 4.11 (t, 2H, J = 6.9, 7.2 Hz), 2.49 (t, 4H, J = 7.5, 7.2 Hz), 1.65 (m, 2H), 1.56 (m, 4H), 1.27 (m, 18H), 0.85 (m, 9H).

¹³ C NMR (CDCl ₃ ): 158.1, 152.9, 148.2, 117.6, 114.8, 77.4, 48.6, 35.6, 31.8, 31.7, 30.4, 29.0, 28.6, 26.9, 22.8, 22.7, 14.2.

3) JK Synthesis of -104

N-hexyl-4,4'-dihexyl-2,2'-dipyridylamine 3-2 (120 mg, 0.283 mmol) and dichloro (p-cymene) ruthenium (II) dimmer (88 mg, 0.142 mmol) were mixed with DMF ( 15 mL) and stirred at 70 ° C. for 4 hours. Subsequently, 2,2'-bipyridine-4,4'-dicarboxylic acid (70 mg, 0.283 mmol) was added and stirred at 160 ° C. for 4 hours. NH ₄ NCS (215 mg, 2.83 mmol) was added, and the reaction was allowed to occur at 140 ° C. for 4 hours. Thereafter, the mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure. And water was added, filtered and washed, and dried in vacuo. Purification of the dried material and filtration gave JK-104. The yield was 60%.

¹ H NMR (CD ₃ OD): 9.54 (d, 1 H, J = 5.4 Hz), 8.90 (d, 1H, J = 6.0 Hz), 8.84 (s, 1 H), 8.77 (s, 1 H), 8.24 (d, 1 H, J = 5.4 Hz), 8.15 (d, 1H, J = 5.7 Hz), 7.75 (m, 2H), 7.45 (m, 3H), 7.13 (d, 1H, J = 3.3 Hz), 7.07 (s, 1H), 7.04-6.90 (m, 4H), 6.78 (d, 1H, J = 3.6 Hz), 6.71 (d, 1H, J = 5.1 Hz), 6.64 (d, 1H, J = 16.5 Hz), 4.18 (t, 1H), 3.72 (t, 1H), 3.22 (t, 16H), 2.84 (t, 2H), 2.79 (t, 2H), 1.63 (m, 22H), 1.35 (m , 34H), 0.98 (m, 24H), 0.87 (m, 9H).

Example  4: JK Preparation of -95 (Compound of Formula 15)

A manufacturing step of JK-95 is shown in FIG. 4.

1) 2- (4- bromophenyl ) -5,5'- dimethyl -1,3- dioxane , Intermediate Compound 4-1 Synthesis

4-bromobenzaldehyde (2.0 g, 10.8 mmol), neopentylglycol (1.7 g, 16.2 mmol) and p-toluenesulfonic acid (410 mg, 0.2 equiv) were dissolved in benzene and refluxed for 7 hours. After evaporating the solvent under reduced pressure, H ₂ O (50 ml) and methylene chloride (50 ml) were added thereto. The organic layer was separated, dried over MgSO ₄ , purified and separated to yield 2- (4-bromophenyl) -5,5'-dimethyl-1,3-dioxane. The yield was 90%.

¹ H NMR (CDCl ₃ ): 7.50 (d, 2H, J = 8.1 Hz), 7.38 (d, 2H, J = 8.7 Hz), 5.35 (s, 1H), 3.76 (d, 2H, J = 11.1 Hz), 3.63 (d, 2H, J = 11.1 Hz), 1.28 (s, 3H), 0.80 (s, 3H).

¹³ C NMR (CDCl ₃ ): 137.7, 131.5, 128.1, 123.0, 101.1, 77.8, 48.3, 30.3, 23.1, 22.0.

2) 5,5'- dimethyl -2- (4- hexylphenyl ) -1,3- dioxane , Intermediate Compound 4-2 Synthesis

To a solution containing 2- (4-bromophenyl) -5,5'-dimethyl-1,3-dioxane 4-1 (1.0 g, 3.7 mmol) in THF (50 mL) at -78 ° C in a nitrogen atmosphere -BuLi (1.6 M (solvent hexane), 2.8 mL, 4.4 mmol) was added and mixed for 30 minutes. And 1-bromohexane (0.56 mL, 4.0 mmol) was added and mixed for 4 hours. After evaporating the solvent under reduced pressure, H ₂ O (50 ml) and methylene chloride (50 ml) were added thereto. The organic layer was separated, dried over MgSO ₄ , purified and separated to give 5,5'-dimethyl-2- (4-hexylphenyl) -1,3-dioxane. Yield 85%.

¹ H NMR (CDCl ₃ ): 7.41 (d, 2H, J = 8.1 Hz), 7.18 (d, 2H, J = 8.4 Hz), 5.37 (s, 1H), 3.77 (d, 2H, J = 11.1 Hz), 3.64 (d, 2H, J = 11.1 Hz), 2.60 (t, 2H, J = 7.7 Hz), 1.58 (m, 2H), 1.30-1.27 (m, 9H), 0.88 (t, 3H, J = 6.6 Hz), 0.80 (s, 3H).

¹³ C NMR (CDCl ₃ ): 143.8, 136.0, 128.5, 126.1, 102.0, 77.8, 48.2, 35.9, 31.9, 31.5, 30.4, 29.0, 23.2, 22.7, 22.0, 14.2.

3) 4- hexylbenzaldehyde , Intermediate Compound 4-3 Synthesis

Trifluoroacetic in 5,5'-dimethyl-2- (4-hexylphenyl) -1,3-dioxane 4-2 (640 mg, 2.3 mmol) dissolved in THF (25 mL) and H ₂ O (10 mL) acid) (0.65 mL) was added and mixed for 4 hours at room temperature. After evaporating the solvent under reduced pressure, H ₂ O (50 ml) and methylene chloride (50 ml) were added thereto. The organic layer was separated, dried over MgSO ₄ , purified and separated, and 4-hexylbenzaldehyde was obtained. The yield was 87%.

¹ H NMR (CDCl ₃ ): 9.97 (s, 1 H), 7.81 (d, 2H, J = 8.1 Hz), 7.34 (d, 2H, J = 8.1 Hz), 2.68 (t, 2H, J = 7.7 Hz), 1.63 (qu, 2H, J = 7.6 Hz), 1.43-1.29 (m, 6H), 0.90 (m, 3H).

¹³ C NMR (CDCl ₃ ): 192.2, 150.6, 134.5, 130.0, 129.2, 36.4, 31.8, 31.2, 29.1, 22.5, 14.1.

4) 2- bromo -4- [4- ( hexyl ) styryl ] pyridine Synthesis of Intermediate Compound 4-4

4-hexylbenzaldehyde 4-4 (310 mg, 1.62 mmol), diethyl (2-bromopyridin-4-yl) methylphosphonate (500 mg, 1.62 mmol) and potassium t-butoxide (289 mg, 2.6 mmol) were dissolved in THF, Mix for 1 hour. After evaporating the solvent under reduced pressure, H ₂ O (50 ml) and methylene chloride (50 ml) were added thereto. The organic layer was separated, dried over MgSO ₄ , purified and separated to yield 2-bromo-4- [4- (hexyl) styryl] pyridine. The yield was 90%.

¹ H NMR (CDCl ₃ ): 8.29 (d, 1H, J = 4.8 Hz), 7.54 (s, 1H), 7.44 (d, 2H, J = 8.1 Hz), 7.30-7.19 (m, 4H), 6.89 (d, 1H, J = 16.2 Hz), 2.63 (t, 2H, J = 8.1 Hz), 1.67-1.59 (m, 2H), 1.42-1.25 (m, 6H), 0.91 (t, 3H, J = 7.5 Hz).

¹³ C NMR (CDCl ₃ ): 150.4, 148.0, 144.6, 143.0, 134.8, 133.2, 129.1, 127.3, 124.9, 123.5, 119.9, 35.8, 33.6, 31.8, 29.1, 22.5, 14.1.

5) N- hexyl -4,4'- di (4- hexylstyryl ) -2,2'- dipyridylamine Synthesis of Intermediate Compound 4-5

2-bromo-4- [4- (hexyl) styryl] pyridine 4-4 (340 mg, 1.0 mmol), hexylamine (50 mg, 0.5 mmol), DPPP (15 mg, 0.035 mmol), Pd ₂ (dba) ₃ (20 mg, 0.022 mmol) and sodium t-butoxide (120 g, 1.3 mmol) were mixed in a nitrogen atmosphere, and then dry toluene (35 mL) was added and mixed at 80 ° C. for 13 hours. After evaporating the solvent under reduced pressure, H ₂ O (50 ml) and methylene chloride (100 ml) were added. The organic layer was separated, dried over MgSO ₄ , purified and separated to yield N-hexyl-4,4'-di (4-hexylstyryl) -2,2'-dipyridylamine. The yield was 55%.

¹ H NMR (CDCl ₃ ): 8.32 (d, 2H, J = 5.1 Hz), 7.41 (d, 4H, J = 8.1 Hz), 7.19 (d, 2H, J = 16.2 Hz), 7.16 (d, 4H, J = 7.8 Hz), 7.11 (s, 2H), 7.01 (d, 2H, J = 5.4 Hz), 6.90 (d, 2H, J = 16.2 Hz), 4.20 (t, 2H, J = 7.2 Hz), 2.60 (t, 4H, J = 7.8 Hz), 1.73 (m, 2H), 1.60 (m, 4H), 1.30-1.23 (m, 18H), 0.88 (m, 9H).

¹³ C NMR (CDCl ₃ ): 158.5, 148.7, 146.3, 143.9, 133.9, 132.7, 129.0, 127.1, 125.8, 113.9, 112.8, 53.6, 48.8, 35.9, 33.6, 31.8, 31.5, 28.6, 26.9, 22.8, 22.7, 14.2, 14.1.

3) JK Synthesis of -95

N-hexyl-4,4'-di (4-hexylstyryl) -2,2'-dipyridylamine 4-5 (105 mg, 0.167 mmol) and dichloro (p-cymene) ruthenium (II) dimmer (51 mg, 0.084 mmol ) Was added to DMF (15 mL) and stirred at 70 ° C. for 4 hours. Subsequently, 2,2'bipyridine-4,4'-dicarboxylic acid (41 mg, 0.167 mmol) was added and stirred at 160 ° C. for 4 hours. NH ₄ NCS (127 mg, 1.67 mmol) was added thereto, and the reaction was performed at 140 ° C. for 4 hours. Then, the mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure. And filtered by adding water, washed, and dried in vacuo. Purification of the dried material and filtration gave JK-95. The yield was 60%.

¹ H NMR (CD ₃ OD): 9.55 (d, 1H, J = 5.1 Hz), 8.94 (d, 1H, J = 6.0 Hz), 8.85 (s, 1H), 8.78 (s, 1H), 8.27 (d, 1H, J) = 6.0 Hz), 8.16 (d, 1H, J = 5.4 Hz), 7.75 (d, 1H, J = 4.8 Hz), 7.67-7.14 (m, 15H), 7.01 (d, 2H, J = 16.2 Hz), 4.21 (m, 2H), 3.21 (t, 16H), 2.61 (m, 4H), 1.64 (m, 22H), 1.36 (m, 34H), 0.98 (m, 24H), 0.86 (m , 9H).

Example  5: JK Preparation of -99 (Compound of Formula 16)

The preparation step of JK-99 is shown in FIG. 5.

1) 2- bromo -4- [2- (5- hexylthiophen -2- yl ) vinyl ] pyridine , Intermediate Compound 5-1 Synthesis

5-hexylthiophene-2-carbaldehyde (190 mg, 1.0 mmol), diethyl (2-bromopyridin-4-yl) methylphosphonate (310 mg, 1.0 mmol) and potassium t-butoxide (200 mg, 1.8 mmol) were dissolved in THF , Mix for 30 minutes. After evaporating the solvent under reduced pressure, H ₂ O (50 ml) and methylene chloride (50 ml) were added thereto. The organic layer was separated, dried over MgSO ₄ , purified and separated to yield 2-bromo-4- [2- (5-hexylthiophen-2-yl) vinyl] pyridine. The yield was 90%.

¹ H NMR (CDCl ₃ ): 8.26 (d, 1 H, J = 5.1 Hz), 7.47 (d, 1H, J = 1.8 Hz), 7.35 (d, 1H, J = 15.6 Hz), 7.23 (dd, 1H, J = 5.1 Hz), 6.98 (d, 1H, J = 3.6 Hz), 6.71 (d, 1H, J = 3.3 Hz), 6.60 (d, 1H, J = 15.6 Hz), 2.81 (t, 2H, J = 7.5, 7.8 Hz), 1.68 (qu, 2H, J = 6.6, 7.8 Hz), 1.33 (m, 6H), 0.89 (t, 3H, J = 6.6, 6.9 Hz).

¹³ C NMR (CDCl ₃ ): 150.3, 148.5, 147.8, 143.0, 138.9, 129.2, 128.1, 125.2, 124.5, 122.4, 119.6, 31.7, 31.6, 30.6 28.9, 22.7, 14.2.

2) N- hexyl -4,4'- di (5- hexylthiophen -2- yl ) vinyl) -2,2'- dipyridylamine , Intermediate Compound 5-2 Synthesis

2-bromo-4- [2- (5-hexylthiophen-2-yl) vinyl] pyridine 5-1 (900 mg, 2.6 mmol), hexylamine (130 mg, 1.3 mmol), DPPP (43 mg, 0.10 mmol), Pd ₂ (dba) ₃ (48 mg, 0.05 mmol) and sodium t-butoxide (350 mg, 3.64 mmol) were mixed in a nitrogen atmosphere, then dry toluene (50 mL) was added and at 80 ° C. Mix for 24 hours. After evaporating the solvent under reduced pressure, H ₂ O (50 ml) and methylene chloride (50 ml) were added thereto. The organic layer is separated, dried over MgSO ₄ , purified and separated to form N-hexyl-4,4'-di (5-hexylthiophen-2-yl) vinyl) -2,2'-dipyridylamine. Could get The yield was 60%.

¹ H NMR (CDCl ₃ ): 8.28 (d, 2H, J = 5.1 Hz), 7.25 (d, 2H, J = 15.9 Hz), 7.02 (s, 2H), 6.92 (m, 4H), 6.67 (d, 2H, J = 3.3 Hz), 6.62 (d, 2H, J = 15.9 Hz), 4.16 (t, 2H, J = 7.5 Hz), 2.78 (t, 4H, J = 7.8 Hz), 1.66 (m, 6H), 1.31 (m, 18H), 0.88 (m, 9H).

¹³ C NMR (CDCl ₃ ): 158.5, 148.8, 147.6, 146.0, 139.6, 128.1, 126.0, 124.9, 124.8, 113.6, 112.5, 48.8, 31.8, 31.7, 31.6, 30.6, 28.9, 28.8, 28.6, 26.9, 22.8, 22.7, 14.2.

3) JK Synthesis of -99

N-hexyl-4,4'-di (5-hexylthiophen-2-yl) vinyl) -2,2'-dipyridylamine 5-2 (112 mg, 0.174 mmol) with dichloro (p-cymene) ruthenium (II) dimmer (54 mg, 0.087 mmol) was added to DMF (15 mL) and stirred at 70 ° C for 4 h. Subsequently, 2,2'bipyridine-4,4'-dicarboxylic acid (43 mg, 0.174 mmol) was added and stirred at 160 ° C. for 4 hours. NH ₄ NCS (132 mg, 1.74 mmol) was added thereto, and the reaction was performed at 140 ° C. for 4 hours. Then, the mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure. And water was added, filtered and washed, and dried in vacuo. Purification of the dried material and filtration gave JK-99. The yield was 60%.

¹ H NMR (CD ₃ OD): 9.54 (d, 1 H, J = 5.4 Hz), 8.90 (d, 1H, J = 6.0 Hz), 8.84 (s, 1 H), 8.77 (s, 1 H), 8.24 (d, 1 H, J = 5.4 Hz), 8.15 (d, 1H, J = 5.7 Hz), 7.75 (m, 2H), 7.45 (m, 3H), 7.13 (d, 1H, J = 3.3 Hz), 7.07 (s, 1H), 7.04-6.90 (m, 4H), 6.78 (d, 1H, J = 3.6 Hz), 6.71 (d, 1H, J = 5.1 Hz), 6.64 (d, 1H, J = 16.5 Hz), 4.18 (t, 1H), 3.72 (t, 1H), 3.22 (t, 16H), 2.84 (t, 2H), 2.79 (t, 2H), 1.63 (m, 22H), 1.35 (m , 34H), 0.98 (m, 24H), 0.87 (m, 9H).

Hereinafter, with reference to the accompanying drawings will be described in detail a preferred embodiment of a dye-sensitized solar cell using a dye comprising a novel amphoteric compound according to the present invention. However, the present invention is not limited to the embodiments disclosed below, but will be implemented in various forms, and only the present embodiments are intended to complete the disclosure of the present invention and to those skilled in the art to fully understand the scope of the invention. It is provided to inform you.

6 is a view schematically showing a dye-sensitized solar cell according to the present invention.

Referring to FIG. 6, the dye-sensitized solar cell 100 according to the present invention includes a first substrate 110, a semiconductor electrode 120, an opposite electrode 130, a second substrate 140, an electrolyte solution 150, and the like. The polymer layer 160 is provided.

The first substrate 110 may be made of conductive glass. Preferably, indium tin oxide (ITO) and fluorine-doped tin oxide (FTO) are coated on a glass substrate. A TiCl ₄ layer (not shown) may be formed between the first substrate 110 and the semiconductor electrode 120.

The semiconductor electrode 120 is formed on the first substrate 110 and is made of nanoparticle metal oxide to which dye is adsorbed. The semiconductor electrode 120 may be formed to a thickness of about 5 to 15 μm. The nanoparticle metal oxide is made of titanium dioxide (TiO ₂ ), tin dioxide (SnO ₂ ) or zinc oxide (ZnO), and may have a size of about 5 to 30 nm. As the dye adsorbed on the nanoparticle metal oxide, an affinity compound composed of the compound of Formula 1 is used. The compound of formula 1 is as described above, preferably R ₂ and R ₃ in formula 1 have the same formula. More preferably, the compound of formula 12 to formula 19 is used as the dye.

The second substrate 140 may be a glass substrate coated with conductive glass, that is, ITO or FTO, like the first substrate 110.

The opposite electrode 130 is formed on the second substrate 140 and may be made of platinum Pt. The counter electrode 130 is disposed to face the semiconductor electrode 120.

Electrolyte solution 150 is a solution for filling a space between the semiconductor electrode 120 and the counter electrode (130), 1-vinyl- 3-methyl-imidazolium iodide and I ₂ the 3-methoxypropionitrile dissolved I ₃ a ^- / I ^It may be an electrolyte solution of-.

Referring to the operation of the dye-sensitized solar cell according to a preferred embodiment of the present invention illustrated in Figure 6 as follows.

First, when the sunlight passing through the first substrate 110 is absorbed by the dye molecules of the compound of formula 1 adsorbed on the nanoparticle metal oxide of the semiconductor electrode 120, the dye molecules excited in the excited state is nano It is injected into the conduction band of the particle metal oxide. Electrons injected into the nanoparticle metal oxide are transferred to the first substrate 110 through the interparticle interface and are moved to the counter electrode 120 through the external wire.

Oxidized as a result of electron transfer dye molecules electrolyte solution iodide redox action of the inside ^{(150) (3I - → I} 3 - + 2e -) and reduced again accept electrons provided by, the oxidized iodine ions (I ₃ ^-) it is reduced again by the electrons reaching the counter electrode 130, thereby completing the operation of the dye-sensitized solar cell.

In order to examine the properties when the amphoteric compound according to the present invention is used in dye-sensitized solar cells, preferred examples of the amphoteric compound according to the present invention are JK-85, JK-86, JK-104, and JK-. 95 and JK-99 were used as dyes, and then dye-sensitized solar cells were fabricated. This is illustrated in FIGS. 7 to 12.

7 is a view showing absorption spectra according to wavelengths when JK-85, JK-86, JK-104, JK-95, and JK-99 are used as dyes in dye-sensitized solar cells.

As shown in FIG. 7, it can be seen that when the amphoteric compound according to the present invention is used as a dye of a dye-sensitized solar cell, light of various wavelengths can be absorbed as the functional group is changed. In particular, it can absorb light in a long wavelength range.

FIG. 8 shows the incident photon-to-current conversion efficiency (IPCE) according to the wavelength when JK-85, JK-86, JK-104, JK-95 and JK-99 are used as dyes for dye-sensitized solar cells. Drawing.

As shown in FIG. 8, when the affinity compound according to the present invention is used as a dye of a dye-sensitized solar cell, it can be seen that the efficiency of converting incident light into electric current has a high IPCE value. have.

FIG. 9 is a diagram showing current density according to voltage when JK-85, JK-86, JK-104, JK-95 and JK-99 are used as dyes of a dye-sensitized solar cell.

As shown in FIG. 9, it can be seen that the short circuit current (J _sc ) and open circuit voltage (V _oc ) values are relatively large and the graph shape is close to a rectangle, thereby showing excellent solar cell characteristics.

10 is a view showing the change in J _sc , V _oc , Fill Factor and efficiency with time, when JK-85 and JK-86 is used as a dye of the dye-sensitized solar cell.

As shown in FIG. 10, it can be seen that J _sc , V _oc , Fill Factor, and efficiency values are almost constant over time, and thus, thermal stability is very excellent.

11 is a view showing the impedance change when the external light is irradiated when JK-85 and JK-86 is used as a dye of the dye-sensitized solar cell, Figure 12 is a dye-sensitized embodiment of JK-85 and JK-86 When used as a dye of a battery, it is a figure which shows the impedance change when no external light is irradiated.

As shown in FIGS. 11 and 12, when external light is irradiated, the current flows smoothly by having a relatively small impedance value, and external light is not irradiated by having a large impedance value when external light is not irradiated. It can be seen that even if not, the discharge is not easy.

In the case of using the amphoteric compound according to the present invention as a dye of the dye-sensitized solar cell, the overall characteristics are shown in Table 1.

As shown in Table 1, when the amphoteric compound according to the present invention is used as a dye of the dye-sensitized solar cell, it can be seen that the overall characteristics are excellent. In particular, in the case of JK-86, the J _sc value is 18.32 mA / cm ^{2, which} is very large, indicating that the efficiency (η) is 9% or more.

Although the preferred embodiments of the present invention have been shown and described above, the present invention is not limited to the specific preferred embodiments described above, and the present invention belongs to the present invention without departing from the gist of the present invention as claimed in the claims. Various modifications can be made by those skilled in the art, and such changes are within the scope of the claims.

1 is a first embodiment of a method for preparing an amphoteric compound according to the present invention, which is a view briefly showing a method for preparing JK-85.

Figure 2 is a second embodiment of the method for producing an amphoteric compound according to the present invention, a view briefly showing the production method of JK-86.

3 is a third embodiment of a method for preparing an amphoteric compound according to the present invention, which is a view briefly showing a method for preparing JK-104.

4 is a fourth embodiment of the method for preparing an amphoteric compound according to the present invention, which is a view briefly showing a method for preparing JK-95.

5 is a fifth embodiment of the method for preparing an amphoteric compound according to the present invention, which is a view briefly showing a method for preparing JK-96.

6 is a view showing a schematic configuration of a dye-sensitized solar cell according to the present invention.

7 is a view showing absorption spectra according to wavelengths when JK-85, JK-86, JK-104, JK-95, and JK-99 are used as dyes in dye-sensitized solar cells.

8 shows the incident photon-to-current conversion efficiency (IPCE) according to wavelength when JK-85, JK-86, JK-104, JK-95, and JK-99 are used as dyes of a dye-sensitized solar cell. Drawing.

FIG. 9 is a diagram showing current density according to voltage when JK-85, JK-86, JK-104, JK-95 and JK-99 are used as dyes of a dye-sensitized solar cell.

10 is a view showing the change in J _sc , V _oc , Fill Factor and efficiency with time, when JK-85 and JK-86 is used as a dye of the dye-sensitized solar cell.

FIG. 11 is a view showing impedance change when external light is irradiated when JK-85 and JK-86 are used as dyes of a dye-sensitized solar cell.

12 is a diagram showing the impedance change when the external light is not irradiated when JK-85 and JK-86 are used as the dye of the dye-sensitized solar cell.

Claims (12)

Amphiphilic compound of formula (1). <Formula 1>

[R ₁ of Formula 1 is any one selected from the group consisting of alkyl having 1 to 20 carbon atoms, phenyl, alkylphenyl having 1 to 20 carbon atoms, R ₂ and R ₃ of Formula 1 is any one selected from the group consisting of Formula 4 to Formula 11, <Formula 4>

<Formula 5>

<Formula 6>

<Formula 7>

<Formula 8>

<Formula 9>

<Formula 10>

<Formula 11>

R ₄ in Formulas 4 to 11 is any one selected from the group consisting of hydrogen, alkyl having 1 to 20 carbon atoms, and alkyloxy having 1 to 20 carbon atoms.] The method of claim 1, Amphiphilic compound, characterized in that R ₂ and R ₃ of Formula 1 have the same formula. The method of claim 1, Amphiphilic compound, characterized in that the compound of Formula 1 is any one selected from the group consisting of compounds of the formula 12, 13, 16. <Formula 12>

<Formula 13>

<Formula 16>

Amphiphilic compound, characterized in that to prepare a compound of formula 1 comprising the step of sequentially reacting a compound of formula 21, a compound of formula 22 and a compound of formula 23 to the compound of formula 20 Manufacturing method. <Formula 1>

<Formula 20>

<Formula 21>

<Formula 22>

<Formula 23>

[R ₁ of Formula 1 and Formula 20 is any one selected from the group consisting of alkyl having 1 to 20 carbon atoms, phenyl, alkylphenyl having 1 to 20 carbon atoms, R ₂ and R ₃ of Formula 1 and Formula 20 are any one selected from the group consisting of Formulas 4 to 11, <Formula 4>

<Formula 5>

<Formula 6>

<Formula 7>

<Formula 8>

<Formula 9>

<Formula 10>

<Formula 11>

R ₄ in Formulas 4 to 11 is any one selected from the group consisting of hydrogen, alkyl having 1 to 20 carbon atoms, and alkyloxy having 1 to 20 carbon atoms.] 5. The method of claim 4, R ₂ and R ₃ in Formula 1 and Formula 20 have the same chemical formula. The method of claim 5, The compound of Formula 20 is prepared by reacting the compound of Formula 24 and the compound of Formula 25 to the preparation of an affinity compound. <Formula 24>

<Formula 25>

The method of claim 6, The compound of formula 24 is prepared by reacting a compound of formula 26 and a compound of formula 27 to the preparation of an affinity compound. <Formula 26>

<Formula 27>

delete The method of claim 6, The compound of formula 24 is a compound of formula 31, wherein the compound of formula 31 is prepared by reacting the compound of formula 32 and the compound of formula 30: <Formula 31>

<Formula 32>

<Formula 30>

Conductive substrates; A semiconductor electrode formed on the conductive substrate and including a metal oxide layer adsorbed with a dye including the compound of Formula 1; Counter electrode; And And an electrolyte solution filling the semiconductor electrode and the counter electrode. <Formula 1>

[R ₁ of Formula 1 is any one selected from the group consisting of alkyl having 1 to 20 carbon atoms, phenyl, alkylphenyl having 1 to 20 carbon atoms, R ₂ and R ₃ of Formula 1 is any one selected from the group consisting of Formula 4 to Formula 11, <Formula 4>

<Formula 5>

<Formula 6>

<Formula 7>

<Formula 8>

<Formula 9>

<Formula 10>

<Formula 11>

R ₄ in Formulas 4 to 11 is any one selected from the group consisting of hydrogen, alkyl having 1 to 20 carbon atoms, and alkyloxy having 1 to 20 carbon atoms.] The method of claim 10, The dye-sensitized solar cell of claim 1, wherein R ₂ and R ₃ have the same formula. The method of claim 10, The compound of Formula 1 is a dye-sensitized solar cell, characterized in that any one selected from the group consisting of compounds of the formula 12, 13, 16. <Formula 12>

<Formula 13>

<Formula 16>

Images