CN105218791A - Containing 2-(4-thiophene-2-phenyl) polymkeric substance of thiophene and its preparation method and application - Google Patents

Containing 2-(4-thiophene-2-phenyl) polymkeric substance of thiophene and its preparation method and application Download PDF

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CN105218791A
CN105218791A CN201510715669.3A CN201510715669A CN105218791A CN 105218791 A CN105218791 A CN 105218791A CN 201510715669 A CN201510715669 A CN 201510715669A CN 105218791 A CN105218791 A CN 105218791A
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thiophene
phenyl
formula
polymkeric substance
preparation
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肖生强
黄轩
徐彪
尤为
詹春
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Wuhan University of Technology WUT
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract

The present invention relates to a kind of polymkeric substance containing 2-(4-thiophene-2-phenyl) thiophene and preparation thereof and methods and applications, its general formula of molecular structure is as shown in the formula I: in formula I, arbitrary integer of n=1 ~ 200; R 1, R 2be selected from H or C 1~ C 20alkyl, alkoxyl group, phenyl or phenoxy group; Ar is for containing thiophene or benzene unit group.Advantage of the present invention: synthesis step is simple, productive rate is higher, is applied in organic polymer solar cell, obtains higher electricity conversion.

Description

Containing 2-(4-thiophene-2-phenyl) polymkeric substance of thiophene and its preparation method and application
Technical field
The invention belongs to organic compound synthesis field, be specifically related to a kind of new polymers being applied to photoelectron material and devices field, more specifically relate to a kind of contain 2-(4-thiophene-2-phenyl) thiophene polymkeric substance and preparation and methods and applications.
Background technology
Compare with traditional inorganic semiconductor material, organic photoelectric semiconductor material has the advantage of flexibility, low cost, solution processable, thus causes the concern widely of people in recent years in academic research and industrial production.In addition, can by realizing organic compound to the change of molecular structure to the absorption region of sunlight and intensity and to its level structure and deliquescent adjustment.
CuPc CuPc is used in double-deck organic photovoltaic devices by the people such as Tang in 1986, obtains the efficiency of conversion close to 1%, achieves the feasibility of organic solar batteries as Novel photovoltaic technology.The photoelectric transformation efficiency of the bulk heterojunction device that after this Heeger seminar employing solution blending mode obtains is 10 times of planar heterojunction device, has started the beginning of bulk heterojunction organic solar batteries thus.Up to the present, the photoelectric transformation efficiency of polymer solar battery reaches 10.8%.But relative to inorganic solar cell, organic solar batteries electricity conversion is still relatively low.Researchist is making great efforts the method seeking to improve polymer solar battery performance always, and material is one of most important factor.So develop more new polymers semiconductor material to become one of important channel of improving polymer solar battery electricity conversion.
Summary of the invention
The object of the invention is to develop a class containing the polymkeric substance of 2-(4-thiophene-2-phenyl) thiophene and preparation thereof and method, this multipolymer stability and solvability is good, absorbancy is strong, light absorption range is wide, improve its electricity conversion.
Another object of the present invention there are provided a class containing the application of 2-(4-thiophene-2-phenyl) thiophene copolymers in organic photoelectrical material, polymer solar battery, organic electroluminescence device, Fluorescence Chemical Sensor, organic field effect tube, organic optical memory part, organic non-linear optical properties and organic laser apparatus.
The present invention solves the problems of the technologies described above adopted technical scheme: containing the polymkeric substance of 2-(4-thiophene-2-phenyl) thiophene, its general formula of molecular structure is as shown in the formula I:
In formula I, arbitrary integer of n=1 ~ 200; R 1, R 2be selected from H or C 1~ C 20alkyl, alkoxyl group, phenyl or phenoxy group; Ar is for containing thiophene or benzene unit group.
By such scheme, described Ar is one or more groups following:
In formula, R 3, R 4, R 5be selected from H, C 1~ C 20alkyl or alkoxyl group; Y is selected from any one atom in H, F, Cl, Br, I.
The preparation method of the described polymkeric substance containing 2-(4-thiophene-2-phenyl) thiophene, is characterized in that preparing carrying out copolymerization containing the group described in the monomer of 2-(4-thiophene-2-phenyl) thiophene and formula II;
In formula, R 3, R 4, R 5be selected from H, C 1~ C 20alkyl or alkoxyl group; Y is selected from any one atom in H, F, Cl, Br, I.
By such scheme, the described monomer containing 2-(4-thiophene-2-phenyl) thiophene, the following formula III of its general formula of molecular structure:
In formula III, R 1, R 2be selected from H or C 1~ C 20alkyl, alkoxyl group, phenyl or phenoxy group.
The described polymkeric substance containing 2-(4-thiophene-2-phenyl) thiophene is applied in a semiconductor material.
By such scheme, described semiconductor material is organic photoelectrical material.
By such scheme, containing 2-(4-thiophene-2-phenyl) thiophene polymkeric substance as polymer body heterojunction solar cell give body phase, with electron acceptor material C 70or derivatives thereof is mixed and made into solution, and be coated on ito glass and be prepared into film, then on film, evaporation metal is prepared into device.
Advantage of the present invention: synthesis step is simple, productive rate is higher, is applied in organic polymer solar cell, obtains higher electricity conversion.
Accompanying drawing explanation
Fig. 1 is the structural representation of the solar cell device adopting the multipolymer of embodiment 13 to prepare as active coating.
Embodiment
In order to make the technical problem to be solved in the present invention, technical scheme and beneficial effect clearly understand, below in conjunction with example, the present invention is further elaborated.Should be appreciated that specific embodiment described herein only in order to explain the present invention, be not intended to limit the present invention.
For achieving the above object, technical scheme of the present invention is as follows:
Embodiment 1:
The preparation of compound 1, reaction formula is as follows:
With R 1for 2-ethylhexyl is that example is explained.Get 100mL bis-neck round-bottomed flask, add 2,5-bis-bromo-Isosorbide-5-Nitrae-Benzenediol (2.70g, 10mmol) successively, 20mLDMF, K 2cO 3(8.8g, 65.2mmol) and bromo-iso-octane (2.3g, 12mmol), stirring heating 80 DEG C reaction 12h.Whole reaction is carried out under the protection of nitrogen.After stopped reaction, solid-liquid separation aftertreatment respectively.Liquid adds 50mL water, extracted with diethyl ether, then washes; Solid adds 250mL water dissolution, extracted with diethyl ether, and organic phase merges, dry, and the crude product obtained after concentrated is through silicagel column (200-300 order) chromatography, and sherwood oil makes eluent, obtains colourless transparent liquid. 1HNMR(400MHz,CDCl 3δppm)7.08(s,2H),3.82(d,J＝5.6Hz,4H),1.76(m,2H),1.30–1.56(m,16H),0.89–0.95(m,12H).
R 1also comprise: methyl, ethyl, 2-butyl octyl, 2-hexyl decyl etc., but be not limited only to this.
Embodiment 2:
The preparation of compound 2:
Method is with embodiment 1.Use R 2for 2-butyl octyl replaces R 1for 2-ethylhexyl. 1HNMR(400MHz,CDCl 3δppm)7.08(s,2H),3.83(d,J＝5.6Hz,4H),1.81(m,2H),1.29–1.57(m,32H),0.87–0.93(m,12H).
Embodiment 3:
The preparation of compound 3:
Method is with embodiment 1.Use R 3for 2-hexyl decyl replaces R 1for 2-ethylhexyl. 1HNMR(400MHz,CDCl 3δppm)7.08(s,2H),3.81(d,J＝5.4Hz,4H),1.78(m,2H),1.27–1.55(m,48H),0.86–0.89(m,12H).
Embodiment 4
The preparation of compound 4, reaction formula is as follows:
With R 1for 2-ethylhexyl is that example is explained.Add compound 1 in 50mL two-neck bottle, after add tributyl (2-thienyl) tin (2.2mmol, 0.83g), proceed in glove box and take Pd (PPh 3) 4(0.42g, 0.4mmol), N 2protection, adds DMF10ml, and heating, oil bath temperature is set to 110 DEG C, and the crude product arrived is through silicagel column (200-300 order) chromatography, and sherwood oil makes eluent, obtains faint yellow solid. 1HNMR(400MHz,CDCl 3,δppm)7.52(d,2H,J＝3.2Hz),7.34(d,J＝4.4Hz,2H),7.26(s,2H),7.09(dd,J＝5.2Hz,J＝3.8Hz,2H),3.98(d,J＝4.8Hz,4H),1.83(m,2H),1.26-1.61(m,16H),0.86-0.96(m,12H).
R 1also comprise: methyl, ethyl, 2-butyl octyl, 2-hexyl decyl etc., but be not limited only to this.
Embodiment 5:
The preparation of compound 5:
Method is with embodiment 4.Use R 2for 2-butyl octyl replaces R 1for 2-ethylhexyl. 1HNMR(400MHz,CDCl 3,δppm)7.54(d,2H,J＝3.6Hz),7.35(d,J＝4.2Hz,2H),7.26(s,2H),7.09(dd,J＝5.2Hz,J＝4.4Hz,2H),3.98(d,J＝5.6Hz,4H),1.90(m,2H),1.28-1.56(m,32H),0.86-0.96(m,12H).
Embodiment 6:
The preparation of compound 6:
Method is with embodiment 4.Use R 3for 2-hexyl decyl replaces R 1for 2-ethylhexyl. 1HNMR(400MHz,CDCl 3,δppm)7.51(d,2H,J＝3.2Hz),7.33(d,J＝4.8Hz,2H),7.24(s,2H),7.10(dd,J＝5.2Hz,J＝4.4Hz,2H),3.96(d,J＝4.2Hz,4H),1.88(m,2H),1.26-1.88(m,48H),0.85-0.94(m,12H).
Embodiment 7
The preparation of compound 7, reaction formula is as follows:
With R 1for 2-ethylhexyl is that example is explained.Get 50mL two-neck bottle Weigh Compound 2 (0.35g, 0.7mmol), reinject anhydrous and oxygen-free 20mL tetrahydrofuran (THF), and ice bath, dropwise drips 0.7mLn-BuLi (2.4M, 1.68mmol).After dropwising, return to room temperature after continuing to stir 1h, then inject trimethyltin chloride (1.68ml, 1.68mmol), continue reaction 1h.Reaction Bi Shuixi, separatory, petroleum ether extraction, organic phase merging anhydrous magnesium sulfate drying, filter, the crude product after concentrating under reduced pressure is put in vacuum oil pump and drains, and obtains solid product. 1HNMR(400MHz,CDCl 3,δppm)7.65(d,J＝3.2Hz,2H),7.25(s,2H),7.18(d,J＝3.6Hz,2H),3.97(d,J＝5.6Hz,4H),1.83(m,2H),1.25-1.61(m,16H),0.89-0.95(m,12H),0.32-0.39(m,18H).
R 1also comprise: methyl, ethyl, 2-butyl octyl, 2-hexyl decyl etc., but be not limited only to this.
Embodiment 8:
The preparation of compound 8:
Method is with embodiment 7.Use R 2for 2-butyl octyl replaces R 1for 2-ethylhexyl. 1HNMR(400MHz,CDCl 3,δppm)7.65(d,J＝3.2Hz,2H),7.23(s,2H),7.18(d,J＝3.2Hz,2H),3.95(d,J＝3.6Hz,4H),1.89(m,2H),1.29-1.58(m,32H),0.80-0.90(m,12H),0.32-0.39(m,18H).
Embodiment 9:
The preparation of compound 9:
Method is with embodiment 7.Use R 3for 2-hexyl decyl replaces R 1for 2-ethylhexyl. 1HNMR(400MHz,CDCl 3,δppm)7.64(d,J＝3.2Hz,2H),7.24(m,2H),7.18(d,J＝3.6Hz,2H),3.96(d,J＝5.6Hz,4H),1.89(m,2H),1.27-1.55(m,48H),0.80-0.90(m,12H),0.32-0.39(m,18H).
Embodiment 10
Polymer P 1preparation, reaction formula is as follows:
Get the mono-neck bottle of 50mL and under the protection of nitrogen, add compound 7 (0.248g, 0.3mmol) successively, 4,7 two bromo-2-(2-butyl octyl)-5,6-bis-fluoro-2H-benzo [1,2,3] triazole (0.144g, 0.3mmol), Pd 2(dba) 3(0.0082g, 0.009mmol) and P (o-tol) 3after (0.0164g, 0.054mmol), inject anhydrous and oxygen-free 10mL toluene, 1mLDMF, after nitrogen bubble10min, after heated and stirred back flow reaction 48h, stopped reaction, is added drop-wise to coagulation in 50mL methanol solution, decompress filter by reaction mixture.Gained solid uses acetone successively by apparatus,Soxhlet's, normal hexane, methylene dichloride extracting.Get methylene dichloride extract concentrating under reduced pressure, vacuum drying solid polymer P 1.The number-average molecular weight of resulting polymers is 16890, weight-average molecular weight 23300.
Embodiment 11
Polymer P 2preparation, reaction formula is as follows:
Get the mono-neck bottle of 50mL and under the protection of nitrogen, add compound 8 (0.281g, 0.3mmol) successively, 4,7 two bromo-2-(2-butyl octyl)-5,6-bis-fluoro-2H-benzo [1,2,3] triazole (0.281g, 0.3mmol), Pd 2(dba) 3(0.0082g, 0.009mmol) and P (o-tol) 3after (0.0164g, 0.054mmol), inject anhydrous and oxygen-free 10mL toluene, 1mLDMF, after nitrogen bubble10min, after heated and stirred back flow reaction 48h, stopped reaction, is added drop-wise to coagulation in 50mL methanol solution, decompress filter by reaction mixture.Gained solid uses acetone successively by apparatus,Soxhlet's, normal hexane extracting.Get normal hexane extract concentrating under reduced pressure, vacuum drying solid polymer P 2.The number-average molecular weight of resulting polymers is 11000, weight-average molecular weight 14200.
Embodiment 12
Polymer P 3preparation, reaction formula is as follows:
Get the mono-neck bottle of 50mL and under the protection of nitrogen, add compound 9 (0.315g, 0.3mmol) successively, 4,7 two bromo-2-(2-butyl octyl)-5,6-bis-fluoro-2H-benzo [1,2,3] triazole (0.144g, 0.3mmol), Pd 2(dba) 3(0.0082g, 0.009mmol) and P (o-tol) 3after (0.0164g, 0.054mmol), inject anhydrous and oxygen-free 10mL toluene, 1mLDMF, after nitrogen bubble10min, after heated and stirred back flow reaction 48h, stopped reaction, is added drop-wise to coagulation in 50mL methanol solution, decompress filter by reaction mixture.Gained solid uses acetone successively by apparatus,Soxhlet's, normal hexane extracting.Get normal hexane extract concentrating under reduced pressure, vacuum drying solid polymer P 3.The number-average molecular weight of resulting polymers is 13200, weight-average molecular weight 21400.
Embodiment 13
Polymer P 4preparation, reaction formula is as follows:
Get the mono-neck bottle of 50mL under the protection of nitrogen, add compound 7 (0.248g successively; 0.3mmol); 3; two (2-octyldodecyl) pyrrolo-[3, the 4-C] pyrroles-1 of 6-two (5-bromothiophene-2-base)-2,5-; 4 (2H; 5H) diketone (0.306g, 0.3mmol), Pd 2(dba) 3(0.0082g, 0.009mmol) and P (o-tol) 3after (0.0164g, 0.054mmol), inject anhydrous and oxygen-free 10mL toluene, 1mLDMF, after nitrogen bubble10min, after heated and stirred back flow reaction 48h, stopped reaction, is added drop-wise to coagulation in 50mL methanol solution, decompress filter by reaction mixture.Gained solid uses acetone successively by apparatus,Soxhlet's, normal hexane, methylene dichloride, trichloromethane extracting.Get trichloromethane extract concentrating under reduced pressure, vacuum drying solid polymer P 4.The number-average molecular weight of resulting polymers is 27100, weight-average molecular weight 54800.
Embodiment 14
Polymer P 5preparation, reaction formula is as follows:
Get the mono-neck bottle of 50mL under the protection of nitrogen, add compound 8 (0.281g successively; 0.3mmol); 3; two (2-octyldodecyl) pyrrolo-[3, the 4-C] pyrroles-1 of 6-two (5-bromothiophene-2-base)-2,5-; 4 (2H; 5H) diketone (0.306g, 0.3mmol), Pd 2(dba) 3(0.0082g, 0.009mmol) and P (o-tol) 3after (0.0164g, 0.054mmol), inject anhydrous and oxygen-free 10mL toluene, 1mLDMF, after nitrogen bubble10min, after heated and stirred back flow reaction 48h, stopped reaction, is added drop-wise to coagulation in 50mL methanol solution, decompress filter by reaction mixture.Gained solid uses acetone successively by apparatus,Soxhlet's, normal hexane, methylene dichloride extracting.Get methylene dichloride extract concentrating under reduced pressure, vacuum drying solid polymer P 5.The number-average molecular weight of resulting polymers is 21800, weight-average molecular weight 52000.
Embodiment 15
Polymer P 6preparation, reaction formula is as follows:
Get the mono-neck bottle of 50mL under the protection of nitrogen, add compound 9 (0.315g successively; 0.3mmol); 3; two (2-octyldodecyl) pyrrolo-[3, the 4-C] pyrroles-1 of 6-two (5-bromothiophene-2-base)-2,5-; 4 (2H; 5H) diketone (0.306g, 0.3mmol), Pd 2(dba) 3(0.0082g, 0.009mmol) and P (o-tol) 3after (0.0164g, 0.054mmol), inject anhydrous and oxygen-free 10mL toluene, 1mLDMF, after nitrogen bubble10min, after heated and stirred back flow reaction 48h, stopped reaction, is added drop-wise to coagulation in 50mL methanol solution, decompress filter by reaction mixture.Gained solid uses acetone successively by apparatus,Soxhlet's, normal hexane, methylene dichloride extracting.Get methylene dichloride extract concentrating under reduced pressure, vacuum drying solid polymer P 6.The number-average molecular weight of resulting polymers is 16890, weight-average molecular weight 23300.
Embodiment 16
Using the 2-of embodiment 13 (4-thiophene-2-phenyl) thiophene to electron donating monomer multipolymer as the application of active coating in solar cell device:
Refer to accompanying drawing 1, adopt 2-(4-thiophene-2-phenyl) thiophene of above-described embodiment 13 to electron donating monomer multipolymer as active coating at solar cell device, it comprises the transparent base layer 1, transparent anode 2, middle supplementary layer 3, active coating 4, the negative electrode 5 that stack gradually.Transparent base layer can adopt the plastic-substrates of glass or other flexible and transparents.Transparent anode can adopt tin indium oxide (being called for short ITO), and preferred square resistance is 10 Ω/cm 2tin indium oxide.Middle supplementary layer can adopt Polyethylene di: polystyrene-sulfonic acid matrix material (referred to as PEDOT:PSS) or molybdic oxide (MoO 3).Active coating comprises electron donor material and electron acceptor material, and what electron donor material adopted above-mentioned example 13 to prepare contains fluorene derivatives to electron donating monomer multipolymer, and electron acceptor material adopts the derivative of soccerballene, such as [6,6] phenyl-C 61-methyl-butyrate (referred to as PC61BM) or [6,6] phenyl-C 71-methyl-butyrate is (referred to as PC 71bM).Negative electrode can adopt metal electrode or double-metal layer electrode, such as Ag or Ca/Al etc.
Embodiment 17
The preparation of the polymer solar cells device being negative electrode with metal Ca/Al and performance:
The structure of the polymer solar cells device being negative electrode with metal Ca/Al is: ITO/PEDOT:PSS/ polymer solar cells active coating/Ca/Al.Device fabrication processes is: with the ito glass cleaned in advance for anode, spin coating water soluble mixt PEDOT:PSS on ito glass, continues spin on polymers solar cell active coating, dry final vacuum evaporation Ca/Al metal electrode after dry.Between ITO and metal electrode, apply positive bias, under the irradiation of the AM1.5 simulated solar irradiation of 100 milliwatt every square centimeter, measure its battery performance.
Polymer P 4 prepared by experimental example 13 and P 61solvent made by CBM orthodichlorobenzene, by polymkeric substance and P 61cBM mass ratio is the active coating of 1:2 mixing spin on polymers solar cell, the open circuit voltage of gained battery device 0.78 volt, and short-circuit current is 8.78 milliamperes every square centimeter, packing factor 52.45%, and effciency of energy transfer is 2.47%.

Claims (7)

1., containing the polymkeric substance of 2-(4-thiophene-2-phenyl) thiophene, its general formula of molecular structure is as shown in the formula I:
In formula I, arbitrary integer of n=1 ~ 200; R 1, R 2be selected from H or C 1~ C 20alkyl, alkoxyl group, phenyl or phenoxy group; Ar is for containing thiophene or benzene unit group.
2. the polymkeric substance containing 2-(4-thiophene-2-phenyl) thiophene according to claim 1, is characterized in that described Ar is one or more groups following:
In formula, R 3, R 4, R 5be selected from H, C 1~ C 20alkyl or alkoxyl group; Y is selected from any one atom in H, F, Cl, Br, I.
3. the preparation method of the polymkeric substance containing 2-(4-thiophene-2-phenyl) thiophene according to claim 1, is characterized in that preparing carrying out copolymerization containing the group described in the monomer of 2-(4-thiophene-2-phenyl) thiophene and formula II;
In formula, R 3, R 4, R 5be selected from H, C 1~ C 20alkyl or alkoxyl group; Y is selected from any one atom in H, F, Cl, Br, I.
4. the preparation method of the polymkeric substance containing 2-(4-thiophene-2-phenyl) thiophene according to claim 3, is characterized in that the described monomer containing 2-(4-thiophene-2-phenyl) thiophene, the following formula III of its general formula of molecular structure:
In formula III, R 1, R 2be selected from H or C 1~ C 20alkyl, alkoxyl group, phenyl or phenoxy group.
5. the polymkeric substance containing 2-(4-thiophene-2-phenyl) thiophene according to claim 1 is applied in a semiconductor material.
6. application according to claim 4, is characterized in that described semiconductor material is organic photoelectrical material.
7. application according to claim 4, it is characterized in that containing 2-(4-thiophene-2-phenyl) thiophene polymkeric substance as polymer body heterojunction solar cell give body phase, with electron acceptor material C 70or derivatives thereof is mixed and made into solution, and be coated on ito glass and be prepared into film, then on film, evaporation metal is prepared into device.
CN201510715669.3A 2015-10-28 2015-10-28 Containing 2-(4-thiophene-2-phenyl) polymkeric substance of thiophene and its preparation method and application Pending CN105218791A (en)

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CN106008454A (en) * 2016-05-19 2016-10-12 国家纳米科学中心 P-phenyl diether dithienyl organic photoelectric compound and preparing method and application thereof
WO2019006852A1 (en) * 2017-07-07 2019-01-10 South University Of Science And Technology Of China Hole transporting layer containing organic conjugated polymer semiconductor material and use thereof
CN112225882A (en) * 2020-09-11 2021-01-15 华南理工大学 N-type polymer containing non-condensed ring acceptor unit and preparation method and application thereof

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CN102276803A (en) * 2010-06-13 2011-12-14 海洋王照明科技股份有限公司 Polymeric material containing anthracene and pyrrole-pyrrole-dione unit, preparation method thereof and application thereof
CN104292432A (en) * 2013-07-19 2015-01-21 海洋王照明科技股份有限公司 Polymer containing difluorobenzotriazole unit, and preparation method and application thereof

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Publication number Priority date Publication date Assignee Title
CN101479272A (en) * 2006-06-30 2009-07-08 西巴控股有限公司 Diketopyrrolopyrrole polymers as organic semiconductors
CN102276803A (en) * 2010-06-13 2011-12-14 海洋王照明科技股份有限公司 Polymeric material containing anthracene and pyrrole-pyrrole-dione unit, preparation method thereof and application thereof
CN104292432A (en) * 2013-07-19 2015-01-21 海洋王照明科技股份有限公司 Polymer containing difluorobenzotriazole unit, and preparation method and application thereof

Cited By (4)

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Publication number Priority date Publication date Assignee Title
CN106008454A (en) * 2016-05-19 2016-10-12 国家纳米科学中心 P-phenyl diether dithienyl organic photoelectric compound and preparing method and application thereof
WO2019006852A1 (en) * 2017-07-07 2019-01-10 South University Of Science And Technology Of China Hole transporting layer containing organic conjugated polymer semiconductor material and use thereof
CN112225882A (en) * 2020-09-11 2021-01-15 华南理工大学 N-type polymer containing non-condensed ring acceptor unit and preparation method and application thereof
CN112225882B (en) * 2020-09-11 2021-11-23 华南理工大学 N-type polymer containing non-condensed ring acceptor unit and preparation method and application thereof

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