KR101757103B1 - Polymers having both electron donor and electron acceptor having new quinoxaline acceptor unit and organic optoelectronics devices using the same - Google Patents

Polymers having both electron donor and electron acceptor having new quinoxaline acceptor unit and organic optoelectronics devices using the same Download PDF

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KR101757103B1
KR101757103B1 KR1020160000449A KR20160000449A KR101757103B1 KR 101757103 B1 KR101757103 B1 KR 101757103B1 KR 1020160000449 A KR1020160000449 A KR 1020160000449A KR 20160000449 A KR20160000449 A KR 20160000449A KR 101757103 B1 KR101757103 B1 KR 101757103B1
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강인남
조은솔
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가톨릭대학교 산학협력단
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Abstract

The present invention relates to an electron donor-electron acceptor polymer comprising a novel quinoxaline acceptor unit and an organic optoelectronic device using the same. According to an electron donor-electron acceptor polymer comprising a novel quinoxaline acceptor unit, It is possible to increase the solubility of the electron-donor-electron acceptor polymer by introducing a plurality of branch side-chain substituents into the substituted phenyl ring, thereby improving the efficiency of the solar cell by maintaining the crystallinity.

Description

[0001] The present invention relates to an electron donor-electron acceptor polymer having a novel quinoxaline acceptor unit and an organic optoelectronic device using the quinoxaline acceptor unit.

The present invention relates to an electron donor-electron acceptor polymer comprising a novel quinoxaline acceptor unit and an organic optoelectronic device using the same.

Organic photovoltaic devices include organic solar cells, organic light emitting diodes, organic transistors, or organic electroluminescent displays. Interest in organic solar cells is increasing as alternative energy sources due to environmental pollution and exhaustion of fossil fuels.

An organic solar cell converts an electromagnetic energy due to a photoelectric effect into electricity, and includes an electrode, a buffer layer, and a photoactive layer. The efficiency of the organic solar cell is determined by the energy conversion efficiency. The efficiency represents the amount of converted electrical energy per incident total energy. The efficiency of solar light absorption, easy separation of electrons and holes, And the charge transport ability.

Various materials have been applied to the photoactive layer and the buffer layer in order to improve the efficiency of the organic solar cell. Particularly, studies on electron donor materials included in the photoactive layer have been actively carried out in order to realize efficiency improvement and large- have.

In general, the photoactive layer is formed by using a mixture of a substance having a low electron affinity (donor) and a substance having a high electron affinity (acceptor), absorbing light to form an exciton, and the exciton is a substance having a low electron affinity Electrons in a material having a low electron affinity move to a material having a high electron affinity at the interface between the material having a high electron affinity and the material, which are separated into holes and electrons, respectively, and are transferred to the electrodes.

Therefore, in order to improve the efficiency of the organic solar cell, the donor material must satisfy both the excellent light absorption ability and the charge transport ability simultaneously. However, as the acceptor material, fullerene and derivatives thereof have been proved as efficient and generally used, but technical difficulties remain in manufacturing a donor material excellent in light absorption ability and charge transporting ability.

Korean Patent Publication No. 2008-0094237

It is an object of the present invention to provide a structure in which the solubility of an electron-donor-electron acceptor polymer is increased and a crystallinity is maintained by introducing a plurality of branch side-chain substituents into a phenyl ring connected to quinoxaline, Thereby improving the efficiency of the solar cell.

In order to achieve the above object, the present invention provides an electron donor-electron acceptor polymer comprising a novel quinoxaline acceptor unit represented by the following general formula (1).

[Chemical Formula 1]

Figure 112016000353103-pat00001

Wherein R 1 is a C 6 to C 30 substituted or unsubstituted linear or branched alkyl group, R 2 to R 5 are the same or different and each is H or a substituted or unsubstituted C 1 to C 30 A is an aromatic monomer having an electron donor function, m is an integer of 0 to 2, and n is an integer of 3 to 10000.

The present invention also provides an organic optical device, comprising the electron-donor-electron acceptor polymer.

According to the electron donor-electron acceptor polymer containing a novel quinoxaline acceptor unit of the present invention, the substitution of quinoxaline for introducing a plurality of branch side-chain substituents into the phenyl ring connected to each other enables solubility of the electron- Can be increased and the crystallinity can be maintained, thereby improving the solar cell efficiency.

1 is a view showing a synthesis path of an electron acceptor according to the first embodiment.
2 is a view showing a synthesis path of an electron acceptor according to Comparative Example 1. Fig.
FIG. 3 is a view showing an electron donor-electron acceptor polymer synthesis path according to Example 1 and Comparative Example 1. FIG.
FIG. 4 is a diagram showing an ultraviolet-visible light spectrum in a solution state of an electron-donor-electron acceptor polymer synthesized according to Example 1 and Comparative Example 1. FIG.
FIG. 5 is a diagram showing an ultraviolet-visible light spectrum in the film state of the electron donor-electron acceptor polymer synthesized according to Example 1 and Comparative Example 1. FIG.
FIG. 6 is a graph showing current-voltage characteristics of a solar cell fabricated using the electron-donor-electron acceptor polymer synthesized according to Example 1 and Comparative Example 1. FIG.

Hereinafter, the present invention will be described in more detail.

The inventors of the present invention have found that when a novel quinoxaline acceptor unit is used, the solubility of the electron-donor-electron acceptor polymer can be increased and the short circuit current (J sc ) of the solar cell is increased, And the present invention has been completed.

The present invention provides an electron donor-electron acceptor polymer comprising a novel quinoxaline acceptor unit represented by the following formula (1).

[Chemical Formula 1]

Figure 112016000353103-pat00002

Wherein R 1 is a C 6 to C 30 substituted or unsubstituted linear or branched alkyl group, R 2 to R 5 are the same or different and each is H or a substituted or unsubstituted C 1 to C 30 A is an aromatic monomer having an electron donor function, m is an integer of 0 to 2, and n is an integer of 3 to 10000.

The aromatic monomer having the electron-donating function may be at least one of the following formulas (2) to (9), but is not limited thereto.

(2)

Figure 112016000353103-pat00003

(3)

Figure 112016000353103-pat00004

[Chemical Formula 4]

Figure 112016000353103-pat00005

[Chemical Formula 5]

Figure 112016000353103-pat00006

[Chemical Formula 6]

Figure 112016000353103-pat00007

(7)

Figure 112016000353103-pat00008

[Chemical Formula 8]

Figure 112016000353103-pat00009

[Chemical Formula 9]

Figure 112016000353103-pat00010

R in formulas (2) to (9) is H or a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms.

The present invention also provides an organic optical device, comprising the electron-donor-electron acceptor polymer.

The organic photonic device may include, but is not limited to, an organic layer including an electron-donor-electron acceptor polymer.

The organic layer is composed of 1: 1 to 1: 5 weight ratio of electron donor-electron acceptor polymer to electron acceptor polymer, and the electron acceptor polymer is fullerene 60, fullerene derivative, PBI (polybenzimidazole), PTCBI (3 , 4,9,10-perylenetetracarboxylic-bis-benzimidazole) and PCBM ([6,6] phenyl-C61-butyricacidmethylester).

The organic photonic device may be an organic solar cell, an organic memory, an organic light emitting diode, an organic sensor, an organic transistor, or an organic electroluminescent display, but is not limited thereto.

Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the present invention is not limited by these examples.

(Example 1)

(1) Synthesis of Compound 2

30 ml of catechol (3.0 g, 27.25 mmol), potassium hydroxide (3.79 g, 68.13 mmol), and dimethyl sulfoxide (DMSO) were added to a 100 ml reaction flask and stirred. To this was added 1-bromo-3,7-dimethyloctane (12.83 mL, 59.95 mmol). The mixture was stirred at room temperature for 12 hours, extracted with water and chloroform, and then dried over anhydrous magnesium sulfate (MgSO 4 ). The solvent was removed using a rotary evaporator, and 8.9 g (84%) of a pure colorless liquid was obtained by silica gel chromatography using a developing solvent of hexane: ethyl acetate = 10: 1. 1 H NMR (CDCl 3 , 300 MHz, ppm):? 6.89 (s, 4H), 4.02 (m, 4H) . 13 C NMR (CDCl 3 , 75 MHz, ppm):? 149.27, 121.00, 114.00, 67.60, 39.32, 37.42, 36.33, 29.97, 28.03, 24.76, 22.75, 22.65, 19.74. Mass (FAB); (m / z): 398 (M < + & gt ; ). Anal. Calcd. for C 14 H 6 Br 2 O 2 S: C, 42.24; H, 1.52; Br, 40.15; O, 8.04; S, 8.06. Found: C, 42.36; H, 1.51; O, 7.75; S, 8.05.

(2) Synthesis of Compound 3

Compound 2 (8.0 g, 20.48 mmol) and acetic acid (100 mL) were placed in a 250 mL reaction flask and N-bromosuccinimide (3.7 g, 20.48 mmol) was added. The mixture was stirred at room temperature for 18 hours, extracted with water and chloroform, and water was removed using anhydrous magnesium sulfate (MgSO 4 ). The solvent was removed using a rotary evaporator, and 7.79 g (81%) of a pure colorless liquid was obtained by silica gel chromatography using a developing solvent of hexane: chloroform = 3: 1. 1 H NMR (CDCl 3 , 300 MHz, ppm):? 7.00-6.96 (m, 2H), 6.73 (d, m, 6H), 0.85 (d, 12H). 13 C NMR (CDCl 3 , 75 MHz, ppm):? 150.05, 148.37, 123.41, 116.81, 115.01, 112.78, 67.86, 67.72, 39.28, 37.35, 36.17, 36.09, 29.92, 28.02, 24.74, 22.64, 19.70.

(3) Synthesis of Compound 4

Compound (3) (5.0 g, 10.65 mmol) was added to a 250 ml reaction flask which had been dehydrated and filled with nitrogen, charged with nitrogen and 50 ml of water-free tetrahydrofuran (THF) Lt; / RTI > After the low-temperature state was sufficiently maintained, n-butyllithium (1.6M hexane) (7.32 mL, 11.71 mmol) was slowly added. Compound 3 (0.73 g, 5.11 mmol) was added thereto, followed by stirring for 5 hours, followed by pouring into 10% aqueous HCl solution and stirring for 30 minutes. Water was extracted with chloroform and water was removed using anhydrous magnesium sulfate (MgSO 4 ). The solvent was removed using a rotary evaporator, and 6.41 g (72%) of a pure yellow liquid was obtained through silica gel chromatography using a developing solvent of hexane: chloroform = 1: 3. 1 H NMR (CDCl 3, 300 MHz, ppm): δ 7.58 (d, 2H), 7.43 (q, 2H), 6.85 (d, 2H), 4.10 (m, 8H), 1.90-0.15 (m, 34H) , 0.95 (q, 14H), 0.87 (q, 28H). 13 C NMR (CDCl 3 , 75 MHz, ppm):? 194.03, 155.14, 149.52, 126.38, 121.15, 112.20, 111.64, 67.77, 67.72, 39.44, 39.42, 37.53, 37.51, 37.49, 37.47, 36.21, 36.01, 30.15, 30.12, 28.20, 28.18, 24.93, 24.90, 22.92, 22.91, 22.82, 19.92, 19.87.

(4) Synthesis of Compound 5

Compound 4 (6.0 g, 7.18 mmol) was added to a 250 ml reaction flask which had been dehydrated and filled with nitrogen and vanadium (V) oxytrifluoride, VOF 3 (2.70 g, 21.55 mmol). Then, 150 ml of anhydrous methylene chloride and boran trifluoride diethyl etherate (BF 3 O (C 2 H 5 ) 2 ) (3.54 ml, 28.72 mmol) were added thereto. The mixture was stirred at room temperature for 12 hours, poured into 10% aqueous citric acid solution, stirred for 30 minutes, extracted with water and chloroform, and water was removed using anhydrous magnesium sulfate (MgSO 4 ). The solvent was removed using a rotary evaporator, and 4.66 g (78%) of a dark red solid was obtained through silica gel chromatography using a chloroform-developing solvent. 1 H NMR (CDCl3, 300 MHz , ppm): δ 7.56 (s, 2H), 7.12 (s, 2H), 4.24 (d, 4H), 4.12 (d, 4H), 1.93-1.17 (m 34H.), 0.98 (q, 14H), 0.87 (d, 28H). 13 C NMR (CDCl 3, 75 MHz, ppm): δ 179.28, 155.55, 149.54, 131.19, 124.52, 112.95, 107.12, 67.92, 67.61, 39.25, 37.38, 37.32, 36.02, 29.97, 28.01, 24.76, 22.72, 22.63, , 19.74. Mass (FAB); (m / z): 833 (M < + & gt ; ). Anal. Calcd. for C 54 H 88 O 6 : C, 77.83; H, 10.64; O, 11.52. Found: C, 77.03; H, 10.79; It's 12.18.

(5) Synthesis of Compound 6

Compound 5 (4.5 g, 5.40 mmol) and compound 2 (1.72 g, 6.48 mmol), ethanol (50 ml) and acetic acid (5 ml) were placed in a 250 ml reaction flask. A condenser was installed, and the mixture was stirred for 12 hours while heated to 80 캜. Water was extracted with chloroform and water was removed using anhydrous magnesium sulfate (MgSO 4 ). The solvent was removed using a rotary evaporator, and the residue was purified by silica gel chromatography using a developing solvent of hexane: chloroform = 3: 2 to obtain 4.82 g (84%) of a red solid. 1 H NMR (CDCl 3, 300 MHz, ppm): δ 8.78 (s, 2H), 7.92 (s, 2H), 7.65 (s, 2H), 4.38-4.31 (. M 8H), 2.04-1.94 (m, 38H), 1.53 (q, 12H), 0.89 (d, 26H). 13 C NMR (CDCl 3 , 75 MHz, ppm): δ 152.38, 149.36, 142.54, 139.18, 131.84, 127.08, 123.79, 122.82, 109.06, 105.94, 67.86, 67.40, 39.32, 37.51, 36.22, 36.14, 30.25, 30.10, 29.73, 28.03, 24.84, 22.76, 22.66, 19.87. Mass (FAB); (m / z): 1063 (M < + & gt ; ). Anal. Calcd. for C 60 H 90 Br 2 N 2 O 4 : C, 67.78; H, 8.53; Br, 15.03; N, 2.63; O, 6.02. Found: C, 68.22; H, 8.57; Br, 14.57; N, 2.61; , 6.03

(6) Synthesis of Compound 7

(4.0 g, 3.76 mmol), tributyl (thiophene-2-yl) stannane (3.09 g, 8.27 mmol), tetra It was added to (0.21 g, 0.19 mmol); tetrakis (triphenylphosphine) palladium (0) (Pd (PPh 3 ) 4 Tetrakis (triphenylphosphine) palladium (0)). Then, a condenser was installed, 50 ml of nitrogen-treated toluene was added, and the mixture was stirred at 110 ° C for 12 hours. Recrystallization in methanol gave 4.0 g (97%) of orange precipitate. 1 H NMR (CDCl 3, 300 MHz, ppm): δ 8.99 (s, 2H), 8.18 (s, 2H), 7.89 (d, 2H), 7.68 (s, 2H), 7.53 (d, 2H), 7.24 (t, 2H), 4.39-4.30 (m, 8H), 2.09-1.29 (m, 36H), 1.22 (t, 14H), 1.08 (d, 26H). 13 C NMR (CDCl 3 , 75 MHz, ppm):? 140.91, 139.04, 137.60, 130.98, 128.30, 126.63, 126.39, 125.85, 123.73, 109.67, 105.88, 67.84, 67.41, 39.38, 39.34, 37.63, 37.57, 36.26, 30.97, 30.42, 30.18, 28.09, 28.06, 24.88, 22.78, 22.68, 19.98, 19.92. Mass (MALDI-TOF); (m / z): 1069 (M < + & gt ; ). Anal. Calcd. for C 68 H 96 N 2 O 4 S 2 : C, 76.36; H, 9.05; N, 2.62; O, 5.98; S, 6.00. Found: C, 76.36; H, 9.08; N, 2.62; O, 5.96; S, 5.98.

(7) Synthesis of Compound 8

Compound 7 (3.0 g, 2.80 mmol) was added to a 250 ml reaction flask and dissolved in 80 ml of chloroform. N-bromosuccinimide (1.0 g, 5.61 mmol) was added at room temperature. After stirring for 12 hours, the mixture was extracted with water and chloroform, and water was removed using anhydrous magnesium sulfate (MgSO 4 ). After concentration using a rotary evaporator, 2.6 g (75%) of red precipitate was obtained in acetone. 1 H NMR (CDCl 3, 300 MHz, ppm): δ 8.89 (s, 2H), 8.05 (s, 2H), 7.68 (s, 2H), 7.53 (d, 2H), 7.15 (d, 2H), 4.46 (s, 4H), 4.32 (s, 4H), 2.17-1.94 (m, 26H), 1.05 (t, 16H), 0.88 (t, 34H). Mass (MALDI-TOF); (m / z): 1227 (M < + & gt ; ). Anal. Calcd. for C 68 H 94 Br 2 N 2 O 4 S 2 : C, 66.54; H, 7.72; Br, 13.02; N, 2.28; O, 5.21; S, 5.22. Found: C, 66.66; H, 7.75; Br, 12.94; N, 2.36; O, 5.14; S, 5.15.

(8) Electron Forgery - Electron Receiver Polymer P1 Synthesis

Compound (8) (0.2 g, 0.16 mmol) and Compound 12 (0.148 g, 0.12 mmol) were placed in a 100 ml reaction flask filled with nitrogen and tetrakis (triphenylphosphine) palladium ); Pd (PPh 3) 4 ) (9 ㎎, 8.15 ㅧ 10 -3 mmol) were placed. Next, 5 ml of anhydrous toluene and 1 ml of dimethylformamide (DMF) were added, and the mixture was heated at 100 ° C and stirred for 24 hours. When the reaction was completed, it was poured into 150 ml of a 10% HCl aqueous solution and stirred for 30 minutes. After filtration under reduced pressure, the filtrate was subjected to soxhlet purification in the order of methanol, acetone, hexane and chloroform. The solvent was removed using a rotary evaporator, and then reprecipitated with methanol to obtain a deep blue-green solid polymer P1 (0.2 g, 74%).

(Comparative Example 1)

(1) Synthesis of Compound 9

Dibromo-1,2-phenylenediamine (0.51 g, 1.92 mmol) and ethanol (20 mL) were added to a 250 mL reaction flask, 2 ml of acetic acid was added. A condenser was installed, and the mixture was stirred for 12 hours while heated to 80 캜. Water was extracted with chloroform and water was removed using anhydrous magnesium sulfate (MgSO 4 ). The solvent was removed using a rotary evaporator, and the residue was purified by silica gel chromatography using a developing solvent of hexane: chloroform = 1: 2 to obtain 1.38 g (80%) of yellow liquid. 1 H NMR (CDCl 3, 300 MHz, ppm): δ 7.85 (s, 2H), 7.28 (d, 2H), 7.27 (s, 2H), 4.04-3.88 (m, 8H), 1.90-1.80 (m, 4H), 1.66 - 1.52 (m, 6H). 1.33-1.15 (m, 28H), 0.94 (t, 6H), 0.87 (q, 26H). 13 C NMR (CDCl 3 , 75 MHz, ppm):? 153.61, 150.58, 148.63, 138.93, 132.51, 130.46,115.27,121.66,67.46,39.24,37.37,36.07,35.98, 19.68, 19.57. Mass (FAB); (m / z): 1065 (M < + & gt ; ). Anal. Calcd. for C 60 H 92 Br 2 N 2 O 4 : C, 67.65; H, 8.71; Br, 15.00; N, 2.63; O, 6.01. Found: C, 68.09; H, 8.88; Br, 14.37; N, 2.96; O, 5.70

(2) Synthesis of Compound 10

(1.27 g, 1.20 mmol), tributyl (thiophene-2-yl) stannane (0.98 g, 2.63 mmol), tetra It was added to (69 ㎎, 0.059 mmol); tetrakis (triphenylphosphine) palladium (0) (Pd (PPh 3 ) 4 Tetrakis (triphenylphosphine) palladium (0)). Then, a condenser was installed, and 15 ml of nitrogen-treated toluene was added thereto, followed by stirring at 110 ° C for 12 hours. The solution was filtered through silica gel, and the solvent was removed using a rotary evaporator. The solvent was removed, and then 1.13 g (88%) of an orange liquid was obtained through silica gel chromatography using a developing solvent of hexane: chloroform = 1: 1. 1 H NMR (CDCl 3, 300 MHz, ppm): δ 8.10 (s, 2H), 7.86 (q, 2H), 7.50 (d, 2H), 7.48 (q, 2H), 7.28 (q, 2H), 7.27 (m, 2H), 6.84 (d, 2H), 4.05-3.98 (m, 8H), 1.89-1.85 (m, 4H), 1.68-1.51 (t, 12H), 0.87 (q, 26H). 13 C NMR (CDCl 3 , 75 MHz, ppm): δ 151.28, 150.05, 148.73, 138.89, 136.84, 131.33, 131.00, 128.59, 126.56, 126.56, 126.20, 123.47, 115.52, 112.54, 67.47, 39.30, 37.44, 30.08, 30.04, 28.04, 28.03, 24.82, 24.76, 22.75, 22.65, 19.77, 19.68. Mass (FAB); (m / z): 1071 (M < + & gt ; ). Anal. Calcd. for C 68 H 98 N 2 O 4 S 2 : C, 76.21; H, 9.22; N, 2.61; O, 5.97; S, 5.98. Found: C, 76.18; H, 9.20; N, 2.62; O, 6.06; S, 5.94.

(3) Synthesis of Compound 11

To a 100 ml reaction flask, 15 ml of chloroform was added to compound 10 (1.04 g, 0.97 mmol), and the mixture was stirred at -20 캜 for 30 minutes. After maintaining at -20 [deg.] C, N-bromosuccinimide (0.35 g, 1.94 mmol) was added. After stirring at -20 占 폚 for 1 hour, the mixture was stirred at room temperature for 3 hours. Water was extracted with chloroform and water was removed using anhydrous magnesium sulfate (MgSO 4 ). The solvent was removed using a rotary evaporator, and the residue was purified by silica gel chromatography using a 1: 1 developing solvent of hexane: chloroform = 1.17 g (98%) as an orange solid. 1 H NMR (CDCl 3, 300 MHz, ppm): δ 7.78 (s, 2H), 7.60 (d, 2H), 7.35 (d, 2H), 7.10 (q, 2H), 7.02 (d, 2H), 6.79 (d, 2H), 4.13-4.06 (m, 8H), 1.94-1.89 (m, 4H), 1.69-1.50 (m, 34H), 0.97 (q, 12H), 0.87 (q, 26H). 13 C NMR (CDCl 3 , 75 MHz, ppm): δ 151.52, 15.23, 149.08, 139.49, 135.95, 130.89, 130.00, 128.85, 125.03, 124.89, 123.65, 116.99, 115.21, 112.24, 67.57, 67.44, 39.34, 37.49, 37.48, 36.38, 36.28, 30.08, 30.06, 28.07, 28.05, 24.89, 24.80, 22.79, 22.69, 19.80. Mass (FAB); (m / z): 1229 (M < + & gt ; ). Anal. Calcd. for C 68 H 96 Br 2 N 2 O 4 S 2 : C, 66.43; H, 7.87; Br, 13.00; N, 2.28; O, 5.21; S, 5.22 Found: C, 66.77; H, 7.89; Br, 12.98; N, 2.28; 4.93; S, 5.15.

(4) Electron emitter-electron acceptor polymer P2 synthesis

Compound 11 (0.35 g, 0.29 mmol) and compound 12 (0.26 g, 0.29 mmol) were placed in a 100 ml reaction flask filled with nitrogen and tetrakis (triphenylphosphine) palladium (0) ); Pd (PPh 3 ) 4 ) (33 mg, 2.85 ㅧ 10 -2 mmol). Then, 4 ml of anhydrous toluene and 1 ml of dimethylformamide (DMF) were added, and the mixture was heated at 120 ° C for 6 hours and then poured into methanol to form a precipitate. After filtration under reduced pressure, soxhlet was purified in acetone and chloroform. The solvent was removed by using a rotary evaporator, and then reprecipitated with methanol to obtain a dark purple solid polymer (0.39 g, 82%).

(Experimental Example 1)

Referring to Table 1, FIG. 4 and FIG. 5, the polymer P1 synthesized by Example 1 exhibits the maximum absorption of a longer wavelength than the polymer P2 synthesized by Comparative Example 1, and the band gap energy (E g ) is considered , The intermolecular attractive force due to the increase in planarity of the polymer P1 is increased, so that a relatively low band gap energy can be seen. This may cause short circuit current (J sc ) and efficiency increase in the solar cell.

Polymer Solution (λ max , nm) Film (λ max , nm) E g (eV) Example 1 (P1) 346, 435, 570 349, 443, 594 1.76 Comparative Example 1 (P2) 359, 426, 559 367, 436, 587 1.82

(Experimental Example 2)

The results of solar cell characteristics with reference to Table 2 and FIG. 6 are as follows. The polymer P1 synthesized by Example 1 has a larger short circuit current (J sc ) than the polymer P2 synthesized by Comparative Example 1, In the case of the power conversion efficiency, it was found that the polymer P1 synthesized by Example 1 was larger, and thus the effect of the present invention was confirmed.

Polymer Mix ratio (weight ratio) V oc (V) J sc (mA / cm 2 ) FF (%) PCE (%) Example 1 (P1) 1: 1 0.82 11.38 0.49 4.62 1: 2 0.80 10.85 0.58 5.03 Comparative Example 1 (P2) 1: 1 0.84 8.59 0.47 3.40 1: 2 0.85 8.96 0.52 3.97

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments. It is to be understood that various modifications and changes may be made without departing from the scope of the appended claims.

Claims (6)

An electron donor-electron acceptor polymer comprising a novel quinoxaline acceptor unit represented by the following formula (1)
[Chemical Formula 1]
Figure 112017037916637-pat00026

Wherein R 1 is a C 6 to C 30 substituted or unsubstituted linear or branched alkyl group,
R 2 to R 3 are H,
A is an aromatic monomer represented by the following formula (5) having an electron donor function,
[Chemical Formula 5]
Figure 112017037916637-pat00027

R in Formula 5 is H or a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms,
and n is an integer from 3 to 10000. delete An organic photonic device comprising the electron donor-electron acceptor polymer of claim 1. [4] The organic photodetector of claim 3, wherein the organic photonic device comprises an organic layer including an electron-donor-electron acceptor polymer. The organic electroluminescent device according to claim 4, wherein the organic layer comprises 1: 1 to 1: 5 weight ratio of electron donor-electron acceptor polymer to electron acceptor polymer, and the electron acceptor polymer is fullerene 60, fullerene derivative, polybenzimidazole (PBI) , PTCBI (3,4,9,10-perylenetetracarboxylic-bis-benzimidazole) and PCBM ([6,6] phenyl-C61-butyricacidmethylester). [4] The organic photodetector of claim 3, wherein the organic photonic device is any one of an organic solar cell, an organic memory, an organic light emitting diode, an organic sensor, an organic transistor, or an organic electroluminescent display.
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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009126118A1 (en) 2008-04-10 2009-10-15 Levent Kamil Toppare Unique processable green polymer with a transmissive oxidized state for realization of commerical rgb based electrochromic device applications

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009126118A1 (en) 2008-04-10 2009-10-15 Levent Kamil Toppare Unique processable green polymer with a transmissive oxidized state for realization of commerical rgb based electrochromic device applications

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Appl. Phys. Lett.. American Institute fo Physics. 2009, 95, 053701
J. Am. Chem. Soc.. American Chemical Society. 2008, Vol. 130, pp 732-742
Journal of Materials Chemistry. The Royal Society of Chemistry. 2011, Vol. 21, pp 4971-4982*

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