CN102924694A - Perylene tetracarboxylic carboxylic ester group polymer acceptor materials and application thereof to solar battery - Google Patents

Perylene tetracarboxylic carboxylic ester group polymer acceptor materials and application thereof to solar battery Download PDF

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CN102924694A
CN102924694A CN201210434230XA CN201210434230A CN102924694A CN 102924694 A CN102924694 A CN 102924694A CN 201210434230X A CN201210434230X A CN 201210434230XA CN 201210434230 A CN201210434230 A CN 201210434230A CN 102924694 A CN102924694 A CN 102924694A
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thiophene
perylene tetracarboxylic
tetracarboxylic acid
ester group
benzo
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CN102924694B (en
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肖生强
蒋友宇
詹春
蒋尊龙
夏飞
程金波
吴迪
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Wuhan University of Technology WUT
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Abstract

The invention discloses perylene tetracarboxylic carboxylic ester group polymer acceptor materials and application thereof to a solar battery. The materials include a structure as refined in formula 1, in the formula 1, M is diazosulfide, dithienyl diazosulfide, selenole, dithienyl selenole, diselenium thiophene selenole, thiophene, dithiophene, terthienyl, benzene, selenophen, diselenide thiophene, terselenide thiophene, thiophene thiophthene, benzo dithiophene, benzo ditellurium thiophene, benzo ditellurium thiophene, or one of derivatives made on the basis of the compounds. R is a linear chain with more than four carbon atoms, a branched chain or an alkyl chain containing different heteroatoms. N is a natural number of 1-1000. By introducing comonomer M on the perylene ring skeletons 1, 7 positions, the level structure of polymer materials can be adjusted, and at the same time, optical property is improved, and use ratio of the materials to light is enhanced. By introducing R, dissolubility of the polymer materials can be adjusted, and utilization of a solution processing technology with low cost is facilitated. The materials can be applied to the field of organic optoelectronics.

Description

Perylene tetracarboxylic acid ester group polymeric acceptor material and the application in solar cell thereof
Technical field
The invention belongs to the organic photoelectric technical field, what be specifically related to Ji Yu perylene tetracarboxylic acid ester derivative has an adjustable photoelectric functional polymer semiconductor acceptor material of energy band structure, relates to simultaneously its application in organic solar batteries.
Background technology
Organic semiconductor material has caused widely interest of researchist because of the photoelectric properties with a series of excellences.Recent two decades comes, and the organic electronics take organic semiconductor material and device as research object is rapidly developed.Than the semiconductor material of other type, organic semiconductor material can modify realize that its solubility property in different solvents also can obtain corresponding adjusting to its level structure and to the adjusting of sunlight absorption region and intensity by chemical structure.Organic semiconductor material has the solution processable performance, can reduce greatly tooling cost on the one hand, it is used in and carries out large-area manufacturing on the different base on the other hand, and its superior flex capability can be used for making difform semi-conductor flexible device, has enlarged greatly its range of application.Wherein, organic photovoltaic battery has demonstrated widely application prospect in the organic photoelectric field.
At present, reach about 9% based on the effciency of energy transfer of the organic solar batteries of polymkeric substance and soccerballene system, but this type of organic photovoltaic battery still faces many difficult problems.Such as fullerene derivate, the change of its chemical structure and modification are limited for impact and the regulating power of its electronic structure, as the N-shaped material, its low lumo energy that distributes may cause with p-type material energy level when making up heterojunction, the too much loss of the solar energy that absorbs may cause low battery open circuit voltage in the quantity of photogenerated charge transfer process.On the other hand, fullerene derivate is unfavorable for that heterojunction is to the absorption of solar energy a little less than visible region absorbs.Therefore, seek at visible region have wide and strong absorption, energy band structure is easy to, photoelectric properties are good, stable novel organic semi-conductor acceptor material has very important scientific and technical meaning.
Summary of the invention
The object of the present invention is to provide 1 of the novel multipolymer semiconductor electronic acceptor material Li Yong perylene ring of a class, 7 advantages that are easy to modify, selection has different from being subjected to the monomer of electronic capability Yu the copolymerization of perylene tetracarboxylic acid ester, can obtain the regulatable polymer materials of a series of energy levels, Effective Raise itself and electron donor material energy level matching degree; Introduce simultaneously the length that different comonomers can change conjugated chain, improve the spectral response of material, the conjugated polymers acceptor material that this type of is novel is used for organic solar batteries, to obtain preferably photoelectric properties.
For achieving the above object, concrete technical scheme is as follows:
Yi Lei perylene tetracarboxylic acid ester group polymeric acceptor material is characterized in that such material has formula 1 structure,
Figure BDA00002349105600011
In the formula 1, M has different comonomer diazosulfide, dithienyl diazosulfide, selenole, dithienyl selenole, two selenophen base selenoles, thiophene, di-thiophene, connection three thiophene, benzene, selenophen, di-selenophen, connection three selenophens, thienothiophene, benzo two thiophene, benzo two selenophens, benzo two tellurium fens or a kind of based in the derivative of above-claimed cpd to being subjected to electronic capability; R has 4 carbon atoms above straight chain, side chain or contains different heteroatomic alkyl chains; N is the polymerization degree of polymer materials, is 1～10000 natural number.
Described comonomer M is a kind of in the structural compounds as follows:
Figure BDA00002349105600021
Described R is a kind of in the structural compounds as follows:
Figure BDA00002349105600022
Formula 1 Biao Shi De perylene tetracarboxylic acid ester group polymeric acceptor material of the present invention is applied to the organic photoelectrical material field.
The application of formula 1 Biao Shi De perylene tetracarboxylic acid ester group polymeric acceptor material of the present invention is characterized in that the active layer material for organic solar batteries.
Ti Gong De perylene tetracarboxylic acid ester group polymeric acceptor material of the present invention can obtain as follows:
(1) obtains different alkyl chain De perylene tetracarboxylic acid esters take the perylene acid anhydride as raw material by esterification;
(2) by 1,7 bromination of Dui Shang Shu perylene tetracarboxylic acid ester cpds, obtain 1,7 dibromo and replace De perylene tetracarboxylic acid ester monomer;
(3) 1,7 dibromo is replaced De perylene tetracarboxylic acid ester monomer and react the conjugated polymers acceptor material that obtains a series of Ji Yu perylene tetracarboxylic acid ester derivatives by transition metal-catalyzed cross-coupling condensation polymerization with the monomer material with metal catalytic coupling activity that contains the M structure.
The structure of related monomer material characterizes by methods such as nucleus magnetic resonance (NMR), mass spectrums (MS) among the present invention, by the structure of the characterize polymers materials such as nucleus magnetic resonance (NMR), ultimate analysis, gel permeation chromatography (GPC) and the molecular weight of polymkeric substance, tested the optical absorption property of polymkeric substance by uv-visible absorption spectra (UV-Vis), adopt electrochemical method to characterize the level structure of polymer materials, the polymkeric substance that obtains can be used as electron acceptor(EA) and is used for active layer material and is prepared into solar cell device.
Description of drawings
Fig. 1 is the absorption spectrum of different polymkeric substance in dichloromethane solution among the embodiment 1-5;
Fig. 2 is the absorption spectrum of different polymeric films among the embodiment 1-5 (spin coating of ODCB solution);
Fig. 3 is the CV figure of different polymkeric substance among the embodiment 1-5;
Fig. 4 is the I-V curve of different polymkeric substance and P3HT among the embodiment 1-5.
Embodiment
In order better to set forth content of the present invention, contain preparation and the application thereof of perylene tetracarboxylic acid ester conjugated polymers below by concrete example explanation, but content of the present invention is not limited only to the following examples.
Embodiment 1
Poly-3,4,9,10-perylene tetracarboxylic acid-four (2-hexyl decyl) ester-alt-4,7-two (base [c] 2,1 of thiophene-2-), the preparation of 3-diazosulfide (being abbreviated as PPTTE-DTBT-a)
Synthetic route is as follows:
Figure BDA00002349105600031
(1) 3, the preparation of 4,9,10-perylene tetracarboxylic acid-four (2-hexyl decyl) ester
3.92g PTCDA (10mmol) is joined in the two neck bottles of 250mL, add again 100mL acetonitrile solution, 14.52g2-hexyl decyl alcohol (60mmol), 18.32g 1-bromo-2-hexyl decane (60mmol) and 2.43g DBU (80mmol), reflux, then the TLC monitoring is cooled to room temperature.Washing, petroleum ether extraction, organic phase is concentrated.2-hexyl decyl alcohol is removed in underpressure distillation, and crude product obtains 9.93g pure compound (1) through silica gel column chromatography, and productive rate is 75%.
1H NMR (400MHz, CDCl 3) δ [ppm]: 8.33 (d, J=8.1Hz, 4H), 8.04 (d, J=7.9Hz, 4H), 4.23 (d, J=6.0Hz, 8H), 1.82 (m, 4H), 1.3 (m, 96H), 0.86 (m, 24H); MALDI-TOF MS:C 88H 140O 8Calculated value 1325.05; Measured value: 1347.9 (M+Na +).
(2) 1,7-two bromo-3,4,9, the preparation of 10-perylene tetracarboxylic acid-four (2-hexyl decyl) ester
With 2.69g 3,4,9,10-perylene tetracarboxylic acid-four (2-hexyl decyl) ester (2mmol) joins single neck bottle of 200mL, adds the K of 8 times of amounts 2CO 3(2.21g, 16mmol) and 30mLCH 2Cl 2, stirring under the room temperature, the bromine (5.12g, 32mmol) of measuring 16 times of amounts with transfer pipet adds wherein, stirs under the room temperature.The TLC monitoring reaction, approximately behind the 5h, stopped reaction is removed excessive bromine, and organic phase is dry, and is concentrated.The crude product that obtains take methylene dichloride/sherwood oil (v/v=2/1) as eluent, obtains pure compound (2) 21.6g through silica gel column chromatography, and productive rate is 54%.
1H NMR (400MHz, CDCl 3) δ [ppm]: 8.96 (d, J=7.9Hz, 2H), 8.26 (s, 2H), 8.06 (d, J=7.92Hz, 2H), 4.24 (d, J=6.0Hz, 8H), 1.82 (m, 4H), 1.32 (m, 96H), 0.86 (t, J=5.6Hz, 24H); MALDI-TOF MS:C 88H 138Br 2O 8Calculated value 1480.88; Measured value: 1503.7 (M+Na +).
(3) 4,7-two (base of 2-trimethyl-tin-radical-thiophene-5-) [c] 2,1, the preparation of 3-diazosulfide
Under 0 ℃ and N2 protection; THF solution (7.0mL with 2M diisopropylamine lithium (LDA); 14.0mmol) dropwise join and contain 0.6g 4, the 7-two (base of thiophene-2-) [c] 2,1; in the 200mL anhydrous ether solution of 3-diazosulfide (2.0mmol); dropwise afterreaction 3 hours, and added again the hexane solution (1M, 10mL) of Me3SnCl with syringe; continue stirring reaction, the TLC monitoring reaction carries out.After 30 minutes, add 50mL distilled water cancellation reaction, separatory, water extracted with diethyl ether, organic phase merges, concentrating under reduced pressure, the solid crude product that obtains adds cold normal hexane, and is ultrasonic, decompress filter, a small amount of cold normal hexane washing solid obtains the pure solid product of 0.64g (3), and productive rate is 50%.
1H NMR (400MHz, CDCl 3, δ ppm): 8.19 (d, J=3.44Hz, 2H), 7.88 (s, 2H), 7.30 (d, J=3.44Hz, 2H), 0.44 (s, 18H, CH 3) .MALDI-TOF MS (m/z): C 20H 24N 2S 3Sn 2, calculated value 627.91; Measured value: 628.04 (M +).
(4) preparation of polymkeric substance
Under the nitrogen protection, take by weighing successively 1,7-, two bromo-3; 4,9,10-perylene tetracarboxylic acid-four (2-hexyl decyl) ester (0.5mmol), 0.313g4; 7-two (base of 2-trimethyl-tin-radical-thiophene-5-) [c] 2,1,3-diazosulfide (0.5mmol), 14.0mg Pd 2(dba) 3And 27.4mgP (o-Tol) 3Join in the single neck bottle of 50mL, then change the 20mL dry toluene over to, reflux, reaction 48h, stopped heating is cooled to room temperature, dropwise splash in the 200mL methyl alcohol, filter, the solid that obtains with 20mL anhydrous methanol washing suction filtration again, drying, solid crude product are used acetone and normal hexane extracting successively, and the hexane solution that obtains is concentrated, join coagulation in the methyl alcohol, filter vacuum-drying, obtain the 0.683g polymkeric substance, productive rate is 83.8%.
Polymer architecture characterizes as follows: GPC:Mn=17.444K, Mw=43.480K, PDI=2.609, n=10.C 102H 144N 2O 8S 3Ultimate analysis, calculated value: C, 75.55; H, 8.89; N, 1.73; S, 5.92; Measured value: C, 74.88; H, 8.69; N, 1.96; S, 6.15.
Embodiment 2
Poly-3,4,9,10-perylene tetracarboxylic acid-four (2-ethylhexyl) ester-alt-4,7-two (base [c] 2,1 of thiophene-2-), the preparation of 3-diazosulfide (being abbreviated as PPTTE-DTBT-b)
Synthetic route is as follows:
Figure BDA00002349105600051
The synthetic method of compound in the synthetic route (4) is synthetic with compound (1) among the embodiment 1, replaces 2-hexyl decyl alcohol and 1-bromo-2-hexyl decane with 2-Ethylhexyl Alcohol and 1-bromo-2-ethyl hexane.Wherein compound (5) synthesizes synthesizing with compound (2) among the embodiment 1.
(1) poly-3,4,9,10-perylene tetracarboxylic acid-four (2-ethylhexyl) ester-alt-4,7-two (base [c] 2,1 of thiophene-2-), the preparation of 3-diazosulfide
Under the nitrogen protection, take by weighing successively 0.517g 1,7-two bromo-3; 4,9,10-perylene tetracarboxylic acid-four (2-ethylhexyl) ester (0.5mmol), 0.313g 4; 7-two (base of 2-trimethyl-tin-radical-thiophene-5-) [c] 2,1,3-diazosulfide (0.5mmol), 14.0mgPd 2(dba) 3With 27.4mg P (o-Tol) 3Join in the single neck bottle of 50mL, then add the 20mL dry toluene, reflux, reaction 48h, stopped heating, reaction solution is cooled to room temperature, it is dropwise splashed into coagulation in the 100mL anhydrous methanol, suction filtration then, the methanol wash that the solid that obtains is used, vacuum-drying, the solid crude product that obtains is used acetone, normal hexane, chloroform soln extracting successively, and the chloroform extraction liquid that obtains is concentrated, adds normal hexane in the above-mentioned concentrated solution, suction filtration, vacuum-drying obtain 500mg polymkeric substance (productive rate 85%).
Polymer architecture characterizes as follows: GPC:Mn=33.76K, Mw=303.39K, PDI=8.98, n=28.8. ultimate analysis C 70H 80N 2O 8S 3: calculated value: C, 71.67; H, 6.82; N, 2.38; S, 8.19; Measured value: C, 71.00; H, 6.92; N, 2.41; S, 8.04.
Embodiment 3
Poly-3,4,9,10-perylene tetracarboxylic acid-four (2-octyl group) ester-alt-4,7-two (base [c] 2,1 of thiophene-2-), the preparation of 3-diazosulfide (being abbreviated as PPTTE-DTBT-c)
Synthetic route is as follows:
Figure BDA00002349105600061
The synthetic method of compound in the synthetic route (6) is synthetic with compound (1) among the embodiment 1, replaces 2-hexyl decyl alcohol and 1-bromo-2-hexyl decane with 1-octanol and 1-bromooctane.The synthetic method of compound (7) is synthetic with compound (2) among the embodiment 1.The synthetic polymer method is with embodiment 2, and with 1,7-, two bromo-3,4,9,10-perylene tetracarboxylic acid-four (2-octyl group) ester replaces 1,7-, two bromo-3,4,9,10-perylene tetracarboxylic acid-four (2-ethylhexyl) ester.
Polymer architecture characterizes as follows: GPC:Mn=105.59K, Mw=311.187K, PDI=2.94, n=90. ultimate analysis C 70H 80N 2O 8S 3Calculated value: C, 71.67; H, 6.82; N, 2.38; S, 8.19; Measured value: C, 70.16; H, 6.76; N, 2.35; S, 8.10.
Embodiment 4
Poly-3,4,9,10-perylene tetracarboxylic acid-four (2-decyl) ester-alt-4,7-two (base [c] 2,1 of thiophene-2-), the preparation of 3-diazosulfide (being abbreviated as PPTTE-DTBT-d)
Synthetic route is as follows:
Figure BDA00002349105600062
The synthetic method of compound in the synthetic route (8) is synthetic with compound (1) among the embodiment 1, replaces 2-hexyl decyl alcohol and 1-bromo-2-hexyl decane with 1-decanol and 1-bromo-decane.The synthetic method of compound (9) is synthetic with compound (2) among the embodiment 1.The synthetic polymer method is with embodiment 2, and with 1,7-, two bromo-3,4,9,10-perylene tetracarboxylic acid-four (2-decyl) ester replaces 1,7-, two bromo-3,4,9,10-perylene tetracarboxylic acid-four (2-ethylhexyl) ester.
Polymer architecture characterizes as follows: n=15. 1H NMR (CDCl3), δ [ppm]: 8.35-8.02 (br, 6H), 7.92 (br, 2H), 7.73 (br, 2H), 7.32 (brs, 2H), 4.31 (brz, 8H), 1.76 (br, 8H), 1.23 (br, 56H), 0.85 (br, 12H).
Embodiment 5
Poly-3,4,9,10-perylene tetracarboxylic acid-four (2-dodecyl) ester-alt-4,7-two (base [c] 2,1 of thiophene-2-), the preparation of 3-diazosulfide (being abbreviated as PPTTE-DTBT-e)
Synthetic route is as follows:
Figure BDA00002349105600071
The synthetic method of compound in the synthetic route (10) is synthetic with compound (1) among the embodiment 1, replaces 2-hexyl decyl alcohol and 1-bromo-2-hexyl decane with 1-lauryl alcohol and Dodecyl Bromide alkane.The synthetic method of compound (11) is synthetic with compound (2) among the embodiment 1.The synthetic polymer method is with embodiment 2, and with 1,7-, two bromo-3,4,9,10-perylene tetracarboxylic acid-four (2-dodecyl) ester replaces 1,7-, two bromo-3,4,9,10-perylene tetracarboxylic acid-four (2-ethylhexyl) ester.
Polymer architecture characterizes as follows: n=20. 1H NMR (CDCl3), δ [ppm]: 8.24-8.10 (br, 6H), 7.93 (brs, 2H), 7.73 (brs, 2H), 7.30 (brs, 2H), 4.32 (br, 8H), 1.82 (br, 8H), 1.22 (br, 72H), 0.85 (br, 12H).
Embodiment 6
Poly-3,4,9,10-perylene tetracarboxylic acid-four (2-hexyl decyl) ester-alt-2, the preparation of 6-two (trimethyl-tin-radical)-benzo [1,2-b:4,5-b '] two thiophene
Synthetic route is as follows:
Figure BDA00002349105600072
Method is with embodiment 2.2,6-two (trimethyl-tin-radical)-benzo [1,2-b:4,5-b '], two thiophene replace 4,7-two (base [c] 2,1 of 2-trimethyl-tin-radical-thiophene-5-), 3-diazosulfide.
Synthesizing of (1) 2,6-two (trimethyl-tin-radical)-benzo [1,2-b:4,5-b '] two thiophene
Under 0 ℃ and N2 protection; 0.76g benzo [1,2-b:4,5-b '] two thiophene (4mmol) are joined in the two neck bottles of 100mL; then add the anhydrous THF of 40mL; slowly drip again n-BuLi (2.5M in hexane) (8.2mmol 3.3mL), behind the reaction 2h, add 10mL trimethyltin chloride (1M in hexane) (10mmol); reaction 12h; add 50mL deionized water cancellation reaction, separatory, water extracted with diethyl ether; organic phase merges; anhydrous magnesium sulfate drying, concentrated, add the 10mL anhydrous methanol; ultrasonic; suction filtration, filter cake washs with the 5mL anhydrous methanol, and vacuum-drying obtains compound 1.65g (productive rate 80%).
1H?NMR(CDCl3)，δ[ppm]：8.27(s，2H)，7.41(s，2H)，0.53-0.31(m，18H)。
Polymer architecture characterizes as follows: GPC:Mn=18.61kDa; Mw=38.23kDa, PDI=2.05, n=12. ultimate analysis C 98H 142O 8S 2Calculated value C, 77.88; H, 9.40; S, 4.23; Measured value: C, 77.11; H, 9.63; S, 4.18.
Embodiment 7
Poly-3,4,9,10-perylene tetracarboxylic acid-four (2-hexyl decyl) ester-alt-2, the preparation of 5-two (trimethyl-tin-radical)-thieno-[3,2-b] thiophene
Synthetic route is as follows:
Figure BDA00002349105600081
Method is with embodiment 2.Replace 4,7-two (base [c] 2,1 of 2-trimethyl-tin-radical-thiophene-5-), 3-diazosulfide with 2,5-two (trimethyl-tin-radical)-thieno-[3,2-b] thiophene.
Synthesizing of (1) 2,5-two (trimethyl-tin-radical)-thieno-[3,2-b] thiophene
Under 0 ℃ and N2 protection, dropwise splash into the pentane solution (6.9mL) of 1.6M tert-butyl lithium in the anhydrous THF solution that contains 0.7g thieno-[3,2-b] thiophene, after dripping, continue reaction 2h, add Me with syringe again 3The hexane solution (1M, 12mL) of SnCl continues reaction 2h, rear adding 50mL deionized water cancellation reaction, separatory, water extracted with diethyl ether (2 * 20mL), organic phase merges, and anhydrous magnesium sulfate drying filters, concentrating under reduced pressure, the solid crude product that obtains adds the cold methyl alcohol of 10mL, and is ultrasonic, decompress filter, a small amount of cold methanol wash obtains solid product 1.17g (productive rate 50%).
The structural characterization of polymkeric substance is as follows: n=14. 1H NMR (CDCl3), δ [ppm]: 8.37-8.00 (br, 6H), 7.75 (brs, 1H), 7.47 (brs, 1H), 4.26 (br, 8H), 1.87 (br, 4H), 1.43 (br, 96H), 0.83 (br, 24H).
Embodiment 8
The preparation of polymer solar cell device and performance
Ito glass (indium tin oxide-coated glass) is through ultrasonic cleaning, clean through UV ozone again, spin coating PEDOT:PSS on above-mentioned ito glass again, then the polymkeric substance that obtains in the above-mentioned example and P3HT are mixed with the active coating solution that obtains in the spin coating of PEDOT:PSS upper strata, the solvent that active coating adopts is orthodichlorobenzene, last evaporation Ca/Al electrode, the photovoltaic performance of device is at 100mW/m 2AM1.5 simulated solar rayed under measure, embodiment 1-3 is based on poly-3 of different alkyl chains, 4,9,10-perylene tetracarboxylic acid-four (2-alkyl chain) ester-alt-4, the 7-two (base of thiophene-2-) [c] 2,1,3-diazosulfide polymkeric substance, with itself and P3HT blend as active coating, photovoltaic performance such as the table 1 of the device that obtains.
Table 1:
Figure BDA00002349105600091

Claims (5)

1. Yi Lei perylene tetracarboxylic acid ester group polymeric acceptor material, it is characterized in that: such material has formula 1 structure,
Figure FDA00002349105500011
In the formula 1, M has different comonomer diazosulfide, dithienyl diazosulfide, selenole, dithienyl selenole, two selenophen base selenoles, thiophene, di-thiophene, connection three thiophene, benzene, selenophen, di-selenophen, connection three selenophens, thienothiophene, benzo two thiophene, benzo two selenophens, benzo two tellurium fens or a kind of based in the derivative of above-claimed cpd to being subjected to electronic capability; R has 4 carbon atoms above straight chain, side chain or contains different heteroatomic alkyl chains; N is the polymerization degree of polymer materials, is 1～10000 natural number.
2. such as claim 1 Suo Shu De perylene tetracarboxylic acid ester group polymeric acceptor material, it is characterized in that: described comonomer M is any in the structural compounds as follows,
Figure FDA00002349105500012
3. such as claim 1 Suo Shu De perylene tetracarboxylic acid ester group polymeric acceptor material, it is characterized in that: described R is any in the structural compounds as follows,
4. such as the application of claim 1 Suo Shu De perylene tetracarboxylic acid ester group polymeric acceptor material, it is characterized in that: be used for the organic photoelectrical material field.
5. such as the application of claim 1 Suo Shu De perylene tetracarboxylic acid ester group polymeric acceptor material, it is characterized in that: the active layer material that is used for organic solar batteries.
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