CN115304610A - Pyrrolo-pyrrole diketo red light conversion agent material - Google Patents
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Abstract
The invention discloses a pyrrolo-pyrrole diketo red light conversion agent material. The material can regulate and control the luminous property of the material by regulating and controlling the type of the bridging group and the length of the alkyl chain. The red light conversion agent material can emit red light of 600-750nm under the excitation of light of 300-600nm, the absorption matching degree of the red light and the plant chlorophyll on the red light part is higher, the photosynthesis of plants can be effectively improved, and the red light conversion agent material can be used in the field of light conversion agricultural films.
Description
Technical Field
The invention relates to the field of organic small molecule luminescent materials, in particular to a pyrrolo-pyrrole diketo red light conversion agent material.
Background
The organic small molecule luminescent material has important research significance in the light conversion luminescent material, has the characteristics of easily regulated structure, easily purified material, excellent luminescent performance and the like, and is widely applied to the fields of light conversion agricultural films, illumination, display, detection and the like. The pyrrolopyrrole-dione is an important artificially synthesized dye and has the advantages of bright color, excellent light stability and thermal stability and the like. In recent years, as an electron acceptor unit, a series of DPP-based conjugated molecules and polymers have been constructed in the academic world, and have been widely used in research in the fields of organic field effect transistors, organic photovoltaic devices, organic thermoelectricity, singlet fission, photodynamic therapy, and the like. Most DPP derivatives have alkyl side chains at the N-position, and conjugated units such as thiophene are connected with DPP through single bonds.
The plant can not grow away from the sun, sunlight is the energy source for photosynthesis of the plant, however, different light substances have different effects on the growth and development of the plant, such as: blue light is beneficial to the growth of plant stems and leaves, and red light is beneficial to improving the taste and quality of fruits and vegetables. Photosynthesis of plants occurs in chloroplasts, pigments in chloroplasts absorb light waves of 400 to 480nm of blue light and 600 to 680nm of red orange light at the maximum, and ultraviolet light below 380nm and green light of 500 to 580nm are reflected without being absorbed basically. Therefore, it is necessary to develop an efficient light conversion material, which converts green light and ultraviolet light, which are harmful or harmful to plants, into red light and blue light required for photosynthesis, so as to improve the utilization efficiency of light energy of plants, and thus, the purpose of increasing the yield of crops, promoting the early ripening and improving the nutrient content is achieved.
Disclosure of Invention
In view of the above-mentioned problems and needs in the art, it is an object of the present invention to provide a pyrrolopyrroledione based red light conversion material. The material can regulate and control the luminescent property of the material by regulating and controlling the type of the bridging group and the length of the alkyl chain, and effectively solves the defects of the prior art.
In order to achieve the above objects or other objects, the present invention provides a pyrrolopyrroledione-based red light conversion agent material.
The structural general formula of the pyrrolo-pyrrole diketo red light conversion agent material provided by the invention is shown as (I), wherein X is a bridging group, and n is selected from any one of 1-18.
Further, the bridging group is any one of formula (II), wherein x represents a bonding position.
Further, the pyrrolopyrrole diketo-based red light conversion agent material is selected from any one of the following compounds:
the preparation method of the pyrrolo-pyrrole diketo red light conversion agent material provided by the invention comprises the following steps: the preparation method comprises the steps of firstly reacting pyrrolopyrrole-dione with haloalkane compounds with different chain lengths to generate alkyl pyrrolopyrrole-dione compounds with different alkyl chain lengths, then brominating the alkyl pyrrolopyrrole-dione compounds with N-bromosuccinimide, and finally carrying out Suzuki coupling reaction with 9-anthracene boric acid to obtain the final pyrrolopyrrole-dione-based red light conversion agent material. The preparation method adopted by the invention is the conventional technology in the field.
The invention also provides application of the pyrrolo-pyrrole diketo red light conversion agent material in the field of light conversion agricultural films. Preferably, the pyrrolo-pyrrole diketo-red light conversion agent material is modified by adopting the conventional technology in the field of agricultural films, and is added into the agricultural films to prepare the light conversion agricultural films.
The pyrrolo-pyrrole diketo red light conversion agent material provided by the invention can regulate and control the light emitting property of the material by regulating and controlling the type of a bridging group and the length of an alkyl chain. The red light conversion agent material can emit 600-750nm red light under the excitation of 300-600nm light, the absorption matching degree of the red light and plant chlorophyll on the red light part is higher, the photosynthesis of plants can be effectively improved, and the red light conversion agent material can be used in the field of light conversion agricultural films.
Drawings
FIG. 1 is an excitation spectrum of a pyrrolopyrroledionyl red light conversion agent material prepared in example 1.
FIG. 2 is an emission spectrum of the pyrrolo-pyrrole diketo-based red light conversion agent material prepared in example 1.
Detailed Description
The following description of the embodiments of the present invention is provided by way of specific examples, and other advantages and effects of the present invention will be readily apparent to those skilled in the art from the disclosure herein. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention.
It is to be noted that the features in the following embodiments and examples may be combined with each other without conflict. It is also to be understood that the terminology used in the examples is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present invention. Test methods in which specific conditions are not specified in the following examples are generally carried out under conventional conditions or under conditions recommended by the respective manufacturers.
When numerical ranges are given in the examples, it is understood that both endpoints of each of the numerical ranges and any value therebetween can be selected unless the invention otherwise indicated. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs and the description of the present invention, and any methods, apparatuses, and materials similar or equivalent to those described in the examples of the present invention may be used to practice the present invention.
Example 1:
synthesis of 3,6-bis (thien-2-yl) -2,5-dimethylpyrrole [3,4-c ] pyrrole-1,4-dione
3,6-di (thiophen-2-yl) -2,5-dihydropyrrole [3,4-c]Pyrrole-1,4-dione (2.00g, 6.66mmol), potassium carbonate (2.76g, 19.98mmol) and a magnetic stirrer were charged into a 100 ml three-necked flask, nitrogen was purged three times, and then 30 ml of anhydrous N, N-dimethylformamide was added into the three-necked flask by a needle tube, and the reaction was stirred at 120 ℃ for 1 hour. Methyl iodide (2.36g, 16.65mmol) was sufficiently dissolved in 5 ml of anhydrous N, N-dimethylformamide, followed by dropwise addition to a three-necked flask with a needle tube, followed by reaction at 130 ℃ for 24 hours. After the reaction is finished, the reaction solution is cooled to room temperature, dichloromethane is used for extraction, anhydrous magnesium sulfate is used for drying, filtration and rotary evaporation are carried out to obtain a crude product, and the crude product is separated by column chromatography to obtain a dark purple solid 1.95g (the yield: 89.04%) (namely 3,6-di (thiophene-2-yl) -2,5-dimethylpyrrole [3,4-c ]]Pyrrole-1,4-dione). The dark purple solid is subjected to nuclear magnetic hydrogen spectrum test, and the result is that: 1 HNMR(500MHz,CDCl 3 ,ppm)δ7.95(d,J＝8.5Hz,2H),7.85(d,J＝7.9Hz,2H),7.36(t,J＝9.1Hz,2H),3.67(s,6H)。
synthesis of 3,6-bis (5-bromothien-2-yl) -2,5-dimethylpyrrole [3,4-c ] pyrrole-1,4-dione
The prepared 3,6-di (thiophen-2-yl) -2,5-dimethylpyrrole [3,4-c]Pyrrole-1,4-dione (1.50g, 4.57mmol), N-bromosuccinimide (1.79g, 10.05mmol) and a magnetic stirrer were charged into a 100 ml one-neck flask, 40 ml of chloroform was added, and the mixture was stirred at room temperature for 8 hours. After the reaction is finished, 2.01g of purple solid is obtained by column chromatography (the yield is 90.54 percent), namely 3,6-di (5-bromothiophene-2-yl) -2,5-dimethylpyrrole [3,4-c)]Pyrrole-1,4-diketone, which is subjected to nuclear magnetic hydrogen spectrum test, 1 HNMR(500MHz,CDCl 3 ,ppm)δ7.58(d,J＝9.3Hz,2H),7.26(d,J＝7.5Hz,2H),3.65(s,6H)。
synthesis of pyrrolopyrroledione base red light conversion agent material
The prepared 3,6-bis (5-bromothien-2-yl) -2,5-dimethylpyrrole [3,4-c]Pyrrole-1,4-dione, 9-anthraceneboronic acid and tetrakis (triphenylphosphine) palladium 1.1:0.005 portion is added into three ports of 250 mlIn the flask, nitrogen gas was purged three times, and then 2 mol/l potassium carbonate solution (15 ml), ethanol (15 ml) and toluene (30 ml) were added to the flask, and nitrogen gas was purged three times, and the reaction was stirred at 90 ℃ for 12 hours. After the reaction is finished, cooling the reaction liquid to room temperature, distilling off redundant toluene and ethanol, extracting with dichloromethane and water, drying with anhydrous magnesium sulfate, filtering to obtain a crude product, purifying the crude product by column chromatography to obtain a red solid, namely the required pyrrolo-pyrrole diketo red light conversion agent material, and performing nuclear magnetic test on the red light conversion agent material: 1 H NMR(500MHz,CDCl 3 ,ppm)δ8.55(s,2H),8.20(d,J＝5.6Hz,6H),8.01(d,J＝7.8Hz,4H),7.85(d,J＝6.6Hz,2H),7.48(t,J＝8.6Hz,8H),3.65(s,6H)； 13 C NMR(125MHz,CDCl 3 ) δ 165.4,142.6,136.3,134.2,132.2,130.4,129.8,128.1,127.9,125.6,124.0,113.6,32.9; HRMS (APCI) theoretical value C 44 H 28 N 2 O 2 S 2 680.84; experimental values: 681.7581[ m ] +H] + 。
Example 2
Synthesis of 3,6-bis (thien-2-yl) -2,5-dibutylpyrrole [3,4-c ] pyrrole-1,4-dione
3,6-di (thiophen-2-yl) -2,5-dihydropyrrole [3,4-c]Pyrrole-1,4-dione (2.00g, 6.66mmol), potassium carbonate (2.76g, 19.98mmol) and a magnetic stirrer were added to a 100 ml three-necked flask, nitrogen was purged three times, and then 30 ml of anhydrous N, N-dimethylformamide was added to the three-necked flask by a needle cannula, and the reaction was stirred at 120 ℃ for 1 hour. Bromobutane (2.28g, 16.65mmol) was sufficiently dissolved in 5 ml of anhydrous N, N-dimethylformamide, followed by dropwise addition to a three-necked flask with a needle tube, followed by reaction at 130 ℃ for 24 hours. After the reaction is finished, cooling the reaction liquid to room temperature, extracting by using dichloromethane, drying by using anhydrous magnesium sulfate, filtering, carrying out rotary evaporation to obtain a crude product, and separating the crude product by using column chromatography to obtain a deep purple solid 2.55g (yield: 92.73 percent), namely 3,6-di (thiophene-2-yl) -2,5-dibutyl pyrrole [3,4-c ]]Pyrrole-1,4-dione, which was subjected to nuclear magnetic testing: 1 H NMR(500MHz,CDCl 3 ,ppm)δ7.89(d,J＝8.2Hz,2H),7.78(d,J＝4.5Hz,2H),7.37(t,J＝8.7Hz,2H),3.48(m,4H),1.50(m,4H),1.30(m,4H),0.91(t,J＝8.6,6H)。
synthesis of 3,6-bis (5-bromothien-2-yl) -2,5-dibutylpyrrole [3,4-c ] pyrrole-1,4-dione
3,6-di (thiophen-2-yl) -2,5-dibutylpyrrole [3,4-c]Pyrrole-1,4-dione (2.00g, 4.85mmol), N-bromosuccinimide (1.90g, 10.67mmol) and a magnetic stirrer were charged into a 100 ml single-neck flask, 40 ml of chloroform was added, and stirring was carried out at room temperature for 8 hours. After the reaction is finished, 2.48g of purple solid is obtained by column chromatography (the yield is 89.53 percent), namely 3,6-di (5-bromothiophene-2-yl) -2,5-dibutyl pyrrole [3,4-c)]Pyrrole-1,4-dione, which was subjected to nuclear magnetic testing: 1 H NMR(500MHz,CDCl 3 ,ppm)δ7.57(d,J＝8.8Hz,2H),7.19(d,J＝5.7Hz,2H),3.46(m,4H),1.52(m,4H),1.33(m,4H),0.90(t,J＝7.7,6H)。
synthesis of pyrrolopyrroledione base red light conversion agent material
3,6-bis (5-bromothien-2-yl) -2,5-dibutylpyrrole [3,4-c]Pyrrole-1,4-dione, 9-anthraceneboronic acid and tetrakis (triphenylphosphine) palladium 1.1:0.005 was charged into a 250 ml three-necked flask, nitrogen gas was purged three times, and then a 2 mol/l potassium carbonate solution (15 ml), ethanol (15 ml) and toluene (30 ml) were added to the flask, nitrogen gas was purged three times, and the reaction was stirred at 90 ℃ for 12 hours. After the reaction is finished, cooling the reaction liquid to room temperature, distilling off redundant toluene and ethanol, extracting with dichloromethane and water, drying with anhydrous magnesium sulfate, filtering to obtain a crude product, purifying the crude product by column chromatography to obtain a red solid, namely the required pyrrolo-pyrrole diketo red light conversion agent material, and performing nuclear magnetic test on the red light conversion agent material: 1 H NMR(500MHz,CDCl 3 ,ppm)δ8.54(s,2H),8.22(d,J＝7.8Hz,6H),8.04(d,J＝4.4Hz,4H),7.83(d,J＝5.2Hz,2H),7.51(t,J＝9.6Hz,8H),3.46(m,4H),1.50(m,4H),1.31(m,4H),0.94(t,J＝5.6,3H)；
13 C NMR(125MHz,CDCl 3 )δ165.1,142.3,136.1,134.2,132.1,130.6,129.7,128.2,127.8,125.3,124.1,113.4,45.1,30.4,20.2,13.8；
HRMS (APCI) theoretical value C 50 H 40 N 2 O 2 S 2 765.00; experimental values: 765.9593[ mu ] M +H] + 。
Example 3
Synthesis of 3,6-bis (furan-2-yl) -2,5-dimethylpyrrole [3,4-c ] pyrrole-1,4-dione
3,6-bis (furan-2-yl) -2,5-dihydropyrrole [3,4-c]Pyrrole-1,4-dione, potassium carbonate and a magnetic stirrer were added to a 100 ml three-necked flask, nitrogen was purged three times, and then 30 ml of anhydrous N, N-dimethylformamide was added to the three-necked flask by a needle cannula, and the reaction was stirred at 120 ℃ for 1 hour. Methyl iodide was sufficiently dissolved in 5 ml of anhydrous N, N-dimethylformamide, and then added dropwise to a three-necked flask with a needle cannula, followed by reaction at 130 degrees celsius for 24 hours. After the reaction is finished, cooling the reaction liquid to room temperature, extracting by dichloromethane, drying by anhydrous magnesium sulfate, filtering, carrying out rotary evaporation to obtain a crude product, and separating the crude product by column chromatography to obtain a dark purple solid which is 3,6-di (furan-2-yl) -2,5-dimethylpyrrole [3,4-c ]]Pyrrole-1,4-dione, nuclear magnetic testing: 1 H NMR(500MHz,CDCl 3 ,ppm)δ7.99(d,J＝7.8Hz,2H),7.83(d,J＝6.3Hz,2H),7.33(t,J＝1.5Hz,2H),3.65(s,6H)。
synthesis of 3,6-bis (5-bromofuran-2-yl) -2,5-dimethylpyrrole [3,4-c ] pyrrole-1,4-dione
3,6-bis (furan-2-yl) -2,5-dimethylpyrrole [3,4-c]Pyrrole-1,4-dione, N-bromosuccinimide and a magnetic stirrer were added to a 100 ml single-neck flask, 40 ml of chloroform was added, and the mixture was stirred at room temperature for 8 hours. After the reaction is finished, a purple solid is obtained by column chromatography, and the purple solid is 3,6-di (5-bromofuran-2-yl) -2,5-dimethylpyrrole [3,4-c]Pyrrole-1,4-dione, for nuclear magnetic testing, 1 H NMR(500MHz,CDCl 3 ,ppm)δ7.61(d,J＝7.9Hz,2H),7.30(d,J＝6.3Hz,2H),3.67(s,6H)。
synthesis of pyrrolopyrroledione base red light conversion agent material
3,6-bis (5-bromofuran-2-yl) -2,5-dimethylpyrrole [3,4-c]Pyrrole-1,4-dione, 9-anthraceneboronic acid and tetrakis (triphenylphosphine) palladium 1.1:0.005 was charged into a 250 ml three-necked flask, nitrogen gas was purged three times, and then a 2 mol/l potassium carbonate solution (15 ml), ethanol (15 ml) and toluene (30 ml) were added to the flask, nitrogen gas was purged three times, and the reaction was stirred at 90 ℃ for 12 hours. After the reaction is finished, cooling the reaction liquid to room temperature, distilling off redundant toluene and ethanol, extracting with dichloromethane and water, drying with anhydrous magnesium sulfate, filtering to obtain a crude product, purifying the crude product by column chromatography to obtain a red solid, namely the required pyrrolo-pyrrole diketo red light conversion agent material, and performing nuclear magnetic test on the red light conversion agent material: 1 H NMR(500MHz,CDCl 3 ,ppm)δ8.57(s,2H),8.18(d,J＝7.7Hz,6H),8.05(d,J＝6.3Hz,4H),7.90(d,J＝5.9Hz,2H),7.47(t,J＝9.3Hz,8H),3.67(s,6H)；
13 C NMR(125MHz,CDCl 3 )δ165.6,142.4,136.5,134.3,132.4,130.3,129.8,128.1,127.9,125.6,124.0,113.6,33.1；
HRMS (APCI) theoretical value C 44 H 28 N 2 O 4 648.72; experimental values: 649.8184[ m ] +H] + 。
Example 4
Synthesis of 3,6-bis (furan-2-yl) -2,5-dimethylpyrrole [3,4-c ] pyrrole-1,4-dione
3,6-bis (furan-2-yl) -2,5-dihydropyrrole [3,4-c]Pyrrole-1,4-dione, potassium carbonate and a magnetic stirrer were added to a 100 ml three-necked flask, nitrogen was purged three times, and then 30 ml of anhydrous N, N-dimethylformamide was added to the three-necked flask by a needle cannula, and the reaction was stirred at 120 ℃ for 1 hour. Bromooctane was sufficiently dissolved in 5 ml of anhydrous N, N-dimethylformamide, and then added dropwise to a three-necked flask with a needle, followed by 130 intakesThe reaction was carried out at Deg.C for 24 hours. After the reaction is finished, cooling the reaction liquid to room temperature, extracting with dichloromethane, drying with anhydrous magnesium sulfate, filtering, and rotary evaporating to obtain a crude product, and separating the crude product by column chromatography to obtain a dark purple solid which is 3,6-di (furan-2-yl) -2,5-dimethylpyrrole [3,4-c ]]Pyrrole-1,4-dione with nuclear magnetic test results: 1 H NMR(500MHz,CDCl 3 ,ppm)δ8.62(d,J＝8.2Hz,2H),8.58(d,J＝4.5Hz,2H),7.24(t,J＝8.7Hz,2H),3.48(m,4H),1.63(m,4H),1.28(m,20H),0.88(t,J＝8.6,6H)。
synthesis of 3,6-bis (5-bromofuran-2-yl) -2,5-dioctylpyrrole [3,4-c ] pyrrole-1,4-dione
3,6-di (thiophen-2-yl) -2,5-dioctylpyrrole [3,4-c]Pyrrole-1,4-dione, N-bromosuccinimide and a magnetic stirrer were added to a 100 ml single-neck flask, 40 ml of chloroform was added, and the mixture was stirred at room temperature for 8 hours. After the reaction is finished, a purple solid is obtained through column chromatography, and the nuclear magnetic test result is as follows: 1 H NMR(500MHz,CDCl 3 ,ppm)δ7.27(d,J＝8.8Hz,2H),6.89(d,J＝5.7Hz,2H),3.48(m,4H),1.63(m,4H),1.28(m,20H),0.88(t,J＝8.6,6H)。
synthesis of pyrrolopyrroledione base red light conversion agent material
3,6-bis (5-bromofuran-2-yl) -2,5-dioctylpyrrole [3,4-c]Pyrrole-1,4-dione, 9-anthraceneboronic acid and tetrakis (triphenylphosphine) palladium 1.1:0.005 was charged into a 250 ml three-necked flask, nitrogen gas was purged three times, and then a 2 mol/l potassium carbonate solution (15 ml), ethanol (15 ml) and toluene (30 ml) were added to the flask, nitrogen gas was purged three times, and the reaction was stirred at 90 ℃ for 12 hours. After the reaction is finished, cooling the reaction liquid to room temperature, evaporating redundant toluene and ethanol, then extracting by using dichloromethane and water, drying by using anhydrous magnesium sulfate, filtering to obtain a crude product, purifying the crude product by column chromatography to obtain a red solid, namely the required pyrrolo-pyrrole diketo red light conversion agent material, wherein the nuclear magnetic test result is as follows: 1 H NMR(500MHz,CDCl 3 ,ppm)δ8.54(s,2H),8.22(d,J＝7.8Hz,6H),8.04(d,J＝4.4Hz,4H),7.83(d,J＝5.2Hz,2H),7.51(t,J＝9.6Hz,8H),3.48(m,4H),1.63(m,4H),1.28(m,20H),0.88(t,J＝7.6,6H)；
13 C NMR(125MHz,CDCl 3 )δ165.1,142.3,136.1,134.2,132.1,130.6,129.7,128.2,127.8,125.3,124.1,113.4,43.0,30.5,31.9,29.3,27.1,22.7,14.1；
HRMS (APCI) theoretical value C 58 H 56 N 2 O 4 845.10; experimental values: 846.2138[ M ] +H] + 。
Performance testing
1. The excitation spectrum of example 1 was measured under 650nm detection compensation using the pyrrolopyrroledione based red light conversion agent material prepared in example 1, and the results are shown in fig. 1, and it can be seen from fig. 1 that the pyrrolopyrroledione based red light conversion agent material can be excited by 330-660nm light and emit 650nm red light.
2. The emission spectrum of the pyrrolopyrroledione-based red light conversion agent material prepared in example 1 is measured under the excitation of light of 400nm, and the result is shown in fig. 2, and it can be seen from fig. 2 that under the excitation of light of 400nm, the pyrrolopyrroledione-based red light conversion agent material can emit red light of 650 nm.
3. The fluorescence quantum efficiencies of the pyrrolopyrroledione-based red light conversion agent materials prepared in the examples 1 to 4 were measured by using an integrating sphere, and the results are shown in table 1, and it can be seen from the data in table 1 that the fluorescence quantum efficiencies of the examples 1 to 4 are all at a higher level, and the materials have better light conversion efficiency.
TABLE 1 fluorescence quantum efficiencies of the materials obtained in examples 1 to 4
| Compound (I) | Fluorescent quantum efficiency (PLQY) |
| Example 1 | 52.1％ |
| Example 2 | 54.8％ |
| Example 3 | 49.7％ |
| Example 4 | 53.3％ |
In conclusion, the pyrrolo-pyrrole diketo red light conversion agent material prepared by the invention can emit 600-750nm red light under the excitation of 300-600nm light, has better light conversion efficiency, is used in agricultural films, and has better light conversion effect.
The foregoing embodiments are merely illustrative of the principles of the present invention and its efficacy, and are not to be construed as limiting the invention. Any person skilled in the art can modify or change the above-mentioned embodiments without departing from the spirit and scope of the present invention. Accordingly, it is intended that all equivalent modifications or changes which can be made by those skilled in the art without departing from the spirit and technical spirit of the present invention be covered by the claims of the present invention.
Claims (3)
1. A pyrrolo-pyrrole diketo red light conversion agent material is characterized in that the structural general formula is shown as (I), wherein X is a bridging group, and n is selected from any one of 1 to 18.
2. The pyrrolopyrroledionyl red light conversion agent material of claim 1 wherein the bridging group is of any one of formula (II) wherein x represents a bonding position.
3. The pyrrolopyrroledione based red light converter material of claim 1 selected from any one of the following compounds:
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| CN101889016A (en) * | 2007-10-09 | 2010-11-17 | 巴斯夫欧洲公司 | Pyrrolopyrrole derivatives, its preparation and purposes |
| CN102388046A (en) * | 2009-04-08 | 2012-03-21 | 巴斯夫欧洲公司 | Pyrrolopyrrole derivatives, their manufacture and use as semiconductors |
| JP2014075441A (en) * | 2012-10-03 | 2014-04-24 | Toyo Ink Sc Holdings Co Ltd | Material for organic thin film solar cell element and use of the same |
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Patent Citations (4)
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| CN101889016A (en) * | 2007-10-09 | 2010-11-17 | 巴斯夫欧洲公司 | Pyrrolopyrrole derivatives, its preparation and purposes |
| CN102388046A (en) * | 2009-04-08 | 2012-03-21 | 巴斯夫欧洲公司 | Pyrrolopyrrole derivatives, their manufacture and use as semiconductors |
| JP2014078701A (en) * | 2012-09-21 | 2014-05-01 | Toyo Ink Sc Holdings Co Ltd | Material for organic thin film solar cell element and application thereof |
| JP2014075441A (en) * | 2012-10-03 | 2014-04-24 | Toyo Ink Sc Holdings Co Ltd | Material for organic thin film solar cell element and use of the same |
Non-Patent Citations (2)
| Title |
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| SHIAN YING ET AL.: "9-Anthryl-capped DPP-based dyes: aryl spacing induced differential optical properties" * |
| ZHONGXIN CHEN ET AL.: "Evolution of the electronic structure in open-shell donor-acceptor organic semiconductors" * |
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