CN105968329B - 含1,2,5-苯并硒二唑-n-r1-5,6-二元羧酸酰亚胺的聚合物及其制法与应用 - Google Patents
含1,2,5-苯并硒二唑-n-r1-5,6-二元羧酸酰亚胺的聚合物及其制法与应用 Download PDFInfo
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- CN105968329B CN105968329B CN201610505761.1A CN201610505761A CN105968329B CN 105968329 B CN105968329 B CN 105968329B CN 201610505761 A CN201610505761 A CN 201610505761A CN 105968329 B CN105968329 B CN 105968329B
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- thiophene
- base
- bis
- dicarboxylic acids
- selenole
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- 229920000642 polymer Polymers 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 86
- 229930192474 thiophene Natural products 0.000 claims description 42
- -1 amino, carbonyl Chemical group 0.000 claims description 19
- 239000011669 selenium Substances 0.000 claims description 17
- 150000002518 isoindoles Chemical class 0.000 claims description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- 229910052711 selenium Inorganic materials 0.000 claims description 12
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 150000003949 imides Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000005605 benzo group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 claims description 6
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical class C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 claims description 5
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical class C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 4
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims description 3
- PPWNCLVNXGCGAF-UHFFFAOYSA-N 3,3-dimethylbut-1-yne Chemical compound CC(C)(C)C#C PPWNCLVNXGCGAF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 230000031709 bromination Effects 0.000 claims description 2
- 238000005893 bromination reaction Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000003863 metallic catalyst Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000004867 thiadiazoles Chemical class 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 claims 1
- 229920000547 conjugated polymer Polymers 0.000 abstract description 15
- 238000010521 absorption reaction Methods 0.000 abstract description 8
- 230000005669 field effect Effects 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- PPHPRJQYDNAYPQ-UHFFFAOYSA-N N1N=CC=C1.[Se] Chemical compound N1N=CC=C1.[Se] PPHPRJQYDNAYPQ-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 9
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- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
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- 238000003786 synthesis reaction Methods 0.000 description 7
- 238000010189 synthetic method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000012805 post-processing Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 239000002861 polymer material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000003851 azoles Chemical class 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 229950004394 ditiocarb Drugs 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000004684 trihydrates Chemical class 0.000 description 2
- VWZKHKRVSXWHAC-UHFFFAOYSA-N 3-($l^{1}-oxidanylmethyl)heptane Chemical compound CCCCC(CC)C[O] VWZKHKRVSXWHAC-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- BJYWDJXZPLEHMF-UHFFFAOYSA-N O.O.O.[Na].C(N)(O)=O Chemical compound O.O.O.[Na].C(N)(O)=O BJYWDJXZPLEHMF-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
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- 230000007812 deficiency Effects 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- WWGXHTXOZKVJDN-UHFFFAOYSA-M sodium;n,n-diethylcarbamodithioate;trihydrate Chemical compound O.O.O.[Na+].CCN(CC)C([S-])=S WWGXHTXOZKVJDN-UHFFFAOYSA-M 0.000 description 1
- PAYGMRRPBHYIMA-UHFFFAOYSA-N sodium;trihydrate Chemical compound O.O.O.[Na] PAYGMRRPBHYIMA-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
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- H01L31/0248—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by their semiconductor bodies
- H01L31/0256—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by their semiconductor bodies characterised by the material
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- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
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- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/141—Side-chains having aliphatic units
- C08G2261/1412—Saturated aliphatic units
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Abstract
本发明公开了一种含1,2,5‑苯并硒二唑‑N‑R1‑5,6‑二元羧酸酰亚胺的聚合物及其制法与应用,其结构式如下;本发明所制备的共轭聚合物具有荧光性,对太阳光有较宽的吸收,因此可用于制作聚合物发光二极管器件,聚合物场效应晶体管和聚合物太阳能电池的活性层。
Description
技术领域
本发明涉及聚合物应用于光电子材料与器件领域,特别涉及一种含1,2,5-苯并硒二唑 -N-R1-5,6-二元羧酸酰亚胺的共轭聚合物及其制法与应用。
背景技术
太阳能是一种绿色可再生资源,有机太阳能电池活性层材料的种类繁多且有机分子的化学结构容易修饰,化合物的制备提纯加工简便,可以制成大面积的柔性薄膜器件,拥有未来成本上的优势以及资源的广泛分布性。有机太阳能电池可制备成膜,并且可以制备形成可卷曲折叠的衬底上形成柔性的太阳能电池。有机太阳能电池具有制造面积大、廉价、简易、柔性等优点。因而具有巨大的商业开发和应用前景。但是,目前有机太阳能共轭分子材料种类开发不足,为了实现高效的光电转换,从活性层材料的角度上考虑,需要每个活性层材料对太阳光有高效率的吸收以及高载流子迁移率,从而得到高的转换效率。要实现这些目标,研制更多的新型给体聚合物就显得十分重要。
发明内容
本发明的目的在于针对目前新型共轭分子材料开发的不足,提供能量转换效率较高的一种含1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺单元的聚合物材料。
本发明的另一目的在于提供所述的含1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺的共轭聚合物的制备方法与应用。
本发明通过以下技术方案实现:
一种含1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺的共轭聚合物,其结构式为:
其中,R1为氢原子或烷基链;所述烷基链为具有1~24个碳原子的直链、支链或者环状烷基链,或其中一个或多个碳原子被氧原子、烯基、炔基、芳基、羟基、氨基、羰基、羧基、酯基、氰基或硝基取代,氢原子被卤素原子或上述官能团取代;Ar1、Ar2为芳香基团;D为电子给体单元;所述n为1~10000的自然数,0<x<1,0<y<1,x+y=1。x、y分别为所述共轭聚合物中1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺单元与电子给体单元D的相对含量;电子给体单元D与1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺以共轭方式相连, n为所述共轭聚合物的聚合度。
进一步地,所述芳香基团Ar1、Ar2为如下所述的一种或两种以上:
其中,R2为氢原子或烷基链,或其中一个或多个碳原子被氧原子、烯基、炔基、芳基、羟基、氨基、羰基、羧基、硝基、苯基或噻吩取代基,或其中一个或多个氢原子被卤素原子取代。
进一步地,所述电子给体单元D为如下所示结构的一种或两种以上:
其中,R3、R4为氢原子或烷基链,或其中一个或多个碳原子被氧原子、烯基、炔基、芳基、羟基、氨基、羰基、羧基、硝基、苯基或噻吩取代基,或其中一个或多个氢原子被卤素原子取代。
更进一步地,所述R2、R3、R4为具有1~30个碳原子的直链、支链或者环状烷基链。
以上所述共轭聚合物在制备聚合物发光二极管器件的发光层、制备聚合物场效应晶体管中半导体活性层或制备聚合物太阳能光伏电池的活性层中应用。
本发明通过选择多种共轭电子给体单元分别与含1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺单体进行still偶联共聚,获得含1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺的共轭聚合物。
本发明1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺的共轭聚合物可采用如下方法制备:
(1)以2,5-二噻吩-3,4-并噻唑为母体,与丁炔二酸二甲酯反应,得到4,7-二(噻吩-2- 基)苯并[c][1,2,5]噻二唑-5,6-二甲酸二甲酯;再通过水解,得到4,7-二(噻吩-2-基)苯并[c][1,2,5]噻二唑-5,6-二羧酸;然后与乙酸酐反应,得到4,8-二(噻吩-2-基)异苯并呋喃[5,6-C][1,2,5]噻二唑-5,7-二酮;然后与辛胺反应,得到6-辛基-4,8-二(噻吩-2-基) -5H-[1,2,5]噻二唑并[3,4-f]的异吲哚-5,7(6H)-二酮;再通过铁粉还原,得到5,6-二氨基-4,7-二(噻吩-2-基)-N-R1-异哚吲-1,3-二酮,再将5,6-二氨基-4,7-二(噻吩-2-基)-N-R1-异哚吲-1,3-二酮和二氧化硒进行反应,得到4,7-二(噻吩-2-基)-1,2,5-苯并硒二唑 -N-R1-5,6-二元羧酸酰亚胺,最后通过NBS溴化得到最终单体4,7-二(5-溴-噻吩-2-基)-1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺。
(2)金属催化偶联反应:将含电子给体单元D的具有金属催化偶联反应活性官能团的单体与步骤(1)所得的4,7-二(5-溴-噻吩-2-基)-1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺在金属催化剂下反应,得到初步功能化的含电子给体单元结构和4,7-二(噻吩-2-基) -1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺的共轭聚合物。
(3)在步骤(2)中可以通过D结构的调节变换使4,7-二(噻吩-2-基)-1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺衍生物具有良好的溶液加工性及光电性能,最终成功将4,7- 二(噻吩-2-基)-1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺结构引入到聚合物中,制备系列含4,7-二(噻吩-2-基)-1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺的共轭聚合物。
通过核磁共振(NMR)、质谱(MS)和凝胶色谱(GPC)表征了小分子和聚合物材料的结构,通过紫外可见光谱仪测试聚合物材料的光谱性质,同时将所制得的聚合物制备成光电器件表征他们的光电性能。
本发明1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺中硒原子体积大,电子多,使得含硒原子的聚合物在吸收光谱中易于红移。有望展现出更好的窄带隙太阳电池材料。可以预测,含有1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺的共轭聚合物具有良好的光学性能,是一类具有商业化应用前景的材料。
2,5-二噻吩-3,4-并噻唑和1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺的结构式如下:
基于1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺的共轭聚合物材料作为一类有前途的光电材料。目前为止,在该领域未曾有人报道。本发明首次合成出了含1,2,5-苯并硒二唑 -N-R1-5,6-二元羧酸酰亚胺的共轭聚合物并成功应用于光电领域。
与现有技术相比,本发明具有以下优点:
含1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺的共轭聚合物结构新颖,具有独创性。含1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺的共轭聚合物具有多种功能,苯并硒二唑类化合物有很低的光学带隙和好的稳定性。硒原子半径较大,电子更多,使得含硒原子的聚合物在吸收光谱中易于红移。由于其良好的溶液加工性能、优异的光电性能如带隙较窄,在制作聚合物发光二极管的发光层、聚合物场效应晶体管以及聚合物太阳能电池的活性层领域具有良好的应用。
附图说明
图1为所制备聚合物的薄膜吸收谱图;
图2为所制备聚合物在氯苯溶液中的吸收谱图。
图3、图4为所制备聚合物的电化学曲线图。
具体实施方式
为更好地理解本发明的内容,下面通过具体的实施例来进一步说明本发明的技术方案,具体包括合成、表征与器件制备,但不限于此。
实施例1
4,7-二(5-溴-噻吩-2-基)-1,2,5-苯并噻二唑-N-R1-5,6-二元羧酸酰亚胺的制备路线及合成方法。
(1)4,7-二(噻吩-2-基)苯并[c][1,2,5]噻二唑-5,6-二甲酸二甲酯的制备,合成路线如下:
在250mL的三颈瓶中,氮气保护下,加入2,5-二噻吩-3,4-并噻唑(7.34g,23.99mmol),丁炔二酸二甲酯(6.81g,47.97mmol),再加入150mL二甲苯作溶剂,加热至110℃反应12 小时。后处理:旋蒸,除去二甲苯,再加入DCM,拌硅胶粉,干法上柱。最终得到淡黄色固体产物5.6g。产率:59.01%。
(2)4,7-二(噻吩-2-基)苯并[c][1,2,5]噻二唑-5,6-二羧酸的制备,合成路线与合成方法如下:
在250mL的三颈瓶中,氮气保护下,加入4,7-二(噻吩-2-基)苯并[c][1,2,5]噻二唑 -5,6-二甲酸二甲酯(5.6g,13.46mmol),加入150mL无水甲醇,再逐滴加入NaOH溶液(4.6mol/L,30mL),加热至100℃反应12小时。后处理:在反应混合物中加入盐酸水溶液,搅拌数小时,过滤,得到黄色固体4.46g,产率:85%。
(3)4,8-二(噻吩-2-基)异苯并呋喃[5,6-C][1,2,5]噻二唑-5,7-二酮的制备,合成路线和合成方法如下:
在250mL的三颈瓶中,氮气保护下,加入4,7-二(噻吩-2-基)苯并[c][1,2,5]噻二唑 -5,6-二羧酸(4.46g,11.49mmol)和33.92g乙酸酐,再加入160mL二甲苯作溶剂,加热至110℃反应12小时。后处理:旋蒸,加入无水乙醇然后过滤。得到黄色固体产物3.78g。产率:88%。
(4)6-辛基-4,8-二(噻吩-2-基)-5H-[1,2,5]噻二唑并[3,4-f]的异吲哚-5,7(6H)- 二酮的制备,合成路线和合成方法如下:
在500mL的三颈瓶中,氮气保护下,加入4,8-二(噻吩-2-基)异苯并呋喃[5,6-C][1,2,5] 噻二唑-5,7-二酮(3.78g,10.22mmol)和辛胺(2.64g,20.42mmol),再加入乙酸(180mL),加热至100℃反应8小时,然后用注射器加入乙酸酐(70mL),100℃下反应6小时。后处理: 旋蒸,加入DCM溶解,干法上柱,最后重结晶,得到黄色固体产物3.97g。产率:78%。
(5)5,6-二氨基-4,7-二(噻吩-2-基)-N-辛基-异吲哚-1,3-二酮的制备,合成路线和合成方法如下:
在250mL的三颈瓶中,氮气保护下,加入6-辛基-4,8-二(噻吩-2-基)-5H-[1,2,5]噻二唑并[3,4-f]的异吲哚-5,7(6H)-二酮(3.97g,8.25mmol)和铁粉(5.54g,98.92mmol),加入160mL乙酸作溶剂。加热至130℃反应4小时。后处理:将反应混合物加入至装有水的大烧杯中,吸出铁屑,然后过滤,待吹干后干法上柱。最终得到3.17g黄色固体,产率:85%。
(6)4,7-二(噻吩-2-基)-1,2,5-苯并硒二唑-N-辛基-5,6-二元羧酸酰亚胺的制备,合成路线和合成方法如下:
在250mL的三口瓶中,氮气保护下,加入5,6-二氨基-2-辛基-4,7-二(噻吩-2-基)异吲哚-1,3-二酮(3.17g,7.00mmol),加入80mL乙醇作溶剂,再加入二氧化硒(0.93g,8.40mmol),加热至85℃反应12小时。后处理:旋蒸,重结晶。最终得到红色固体产物2.79g,产率:83%。
(7)4,7-二(5-溴-噻吩-2-基)-1,2,5-苯并硒二唑-N-辛基-5,6-二元羧酸酰亚胺的制备,合成路线和合成方法如下:
在150mL的三口瓶中,氮气保护下,加入6-辛基-4,8-二(噻吩-2-基)-5H-[1,2,5]硒二唑并[3,4-f]的异吲哚-5,7(6H)-二酮(2.79g,5.28mmol)和NBS(2.16g,12.14mmol),再加入100mL氯仿作溶剂,常温反应24小时。后处理:DCM萃取然后干法上柱。最终得到2.68g红色固体产物。产率:76%。核磁共振氢谱:(CDCl3)δ(ppm):1H NMR(500MHz,CDCl3) δ7.68(d,J=4.0Hz,2H),7.21(d,J=4.0Hz,2H),3.78–3.65(m,2H),1.77 –1.60(m,2H),1.29(d,J=17.7,8.6,4.6Hz,12H),0.86(t,J=7.0Hz,4H). 质谱:计算值:868.34;实测值:868.01。
实施例2
聚6辛基-4-(5-(4,4,9,9-四(4-甲氧苯基)-4,9-二氢-s-苯并二茚并[1,2-b:5,6-b'] 吡啶-2-基)噻吩-2-基)-8-(噻吩-2-基)-5H-[1,2,5]硒二唑并[3,4-f]的异吲哚-5,7(6H) -二酮的制备,合成路线和合成步骤如下:
氩气保护下,在10mL微波管内,加入4,7-二(5-溴-噻吩-2-基)-1,2,5-苯并硒二唑-N- 辛基-5,6-二元羧酸酰亚胺(103mg,0.15mmol),(4,4,9,9-四(4-甲氧基苯基)-4,9-二氢-s-苯并二茚并[1,2-B:5,6-b']二-2,7-二基)双(三甲基锡烷)(185mg,0.15mmol),四(三苯基膦)钯(8mg)和二甲苯(4mL),微波200℃反应45min,待反应降至室温后将反应液沉析在甲醇中,先后用甲醇、丙酮、正己烷进行索氏抽提,然后加入二乙基二硫代氨基甲酸钠三水合物的水溶液(225mg,1mmol,100mL水)于60℃搅拌8小时,除去反应中的钯催化剂,用甲醇、丙酮、正己烷进行索氏抽提,干燥,得到深绿色固体(192mg),产率:87.77%。核磁共振氢谱:(CDCl3)δ(ppm):1H NMR(500MHz,CDCl3)δ7.89(d,J=3.5Hz,2H), 7.57(d,J=9.8Hz,2H),7.24(s,2H),7.25(d,J=8.1Hz,8H),7.16(d,J=8.5 Hz,8H),4.83(t,2H),2.55(p,J=17.0Hz,8H),1.76–1.54(m,10H),1.43–1.06 (m,34H),0.88(dd,J=7.8,5.6Hz,15H).元素分析:计算值:C,73.71%;H,6.68%;N, 2.93%;O,2.23%;S,8.94%;Se,5.51%;测试值:C,73.78%;H,6.60%;N,2.93%;O,2.24%; S,8.94%;Se,5.51%。质谱:计算值:1461.99;实测值:1461.07。
实施例3
聚6辛基-4-(5-(4,4,9,9-四(4-甲氧苯基)-4,9-二氢-s-苯并二茚并二[1,2-b:5,6-b']吡啶-2-基)噻吩-2-基)-8-(噻吩-2-基)-5H-[1,2,5]硒二唑并[3,4-f] 的异吲哚-5,7(6H)-二酮的制备,合成路线和合成步骤如下:
氩气保护下,在10mL微波管内,加入4,8-双(5-溴噻吩-2-基)-6-辛基-5H-[1,2,5]硒二唑并[3,4-f]的异吲哚-5,7(6H)-二酮(103mg,0.15mmol),IDTT(207mg,0.15mmol),四(三苯基膦)钯(8mg)和二甲苯(4mL),微波200℃反应45min,待反应降至室温后将反应液沉析在甲醇中,先后用甲醇、丙酮、正己烷进行索氏抽提,然后加入二乙基二硫代氨基甲酸钠三水合物的水溶液(225mg,1mmol,100mL水)于60℃搅拌8小时,除去反应中的钯催化剂,用甲醇、丙酮、正己烷进行索氏抽提,干燥,得到深绿色固体(202mg),产率:87.45%。核磁共振氢谱:(CDCl3)δ(ppm):1H NMR(500MHz,CDCl3)δ7.91(d,J=3.5Hz,2H), 7.77(t,2H),7.53(d,J=9.8Hz,2H),7.29(s,2H),7.21(d,J=8.1Hz,8H),7.12 (d,J=8.5Hz,8H),4.80(t,2H),2.58(p,J=17.0Hz,8H),1.79–1.58(m,10H), 1.47–1.13(m,34H),0.87(dd,J=7.8,5.6Hz,15H).元素分析:计算值:C,71.47%; H,6.19%;N,2.72%;O,2.07%;S,12.44%;Se,5.11%;测试值:C,71.41%;H,6.19%; N,2.74%;O,2.07%;S,12.50%;Se,5.09%。质谱:计算值:1546.11;实测值:1540.78。
实施例4
聚4-(5-(5,10-十二烷基萘并[1,2-B:5,6-B']二噻吩-2-基)噻吩-2-基)-6-辛基-8- (噻吩-2-基)-5H-[1,2,5]硒二唑并[3,4-f]的异吲哚-5,7(6H)-二酮的制备,合成路线和合成步骤如下:
氩气保护下,在10mL微波管内,加入4,8-双(5-溴噻吩-2-基)-6-辛基-5H-[1,2,5]硒二唑并[3,4-f]的异吲哚-5,7(6H)-二酮(103mg,0.15mmol),5,10-二癸萘并[1,2-B: 5,6-b']二-2,7-二基-双-三甲基锡烷(127mg,0.15mmol),四(三苯基膦)钯(8mg)和二甲苯(3mL),微波200℃反应45min,待反应降至室温后将反应液沉析在甲醇中,先后用甲醇、丙酮、正己烷进行索氏抽提,然后加入二乙基二硫代氨基甲酸钠三水合物的水溶液(225mg,1mmol,100mL水)于60℃搅拌8小时,除去反应中的钯催化剂,用甲醇、丙酮、正己烷进行索氏抽提,干燥,得到深绿色固体(137mg),产率:85.09%。核磁共振氢谱:(CDCl3)δ (ppm):1HNMR(500MHz,CDCl3)δ7.91(d,J=3.5Hz,2H),7.53(d,J=9.8Hz, 2H),7.21(d,J=8.1Hz,2H),7.12(d,J=8.5Hz,2H),4.80(t,2H),2.58(p,J= 17.0Hz,2H),1.79–1.58(m,6H),1.47–1.13(m,38H),0.87(dd,J=7.8,5.6Hz, 9H).元素分析:计算值:C,66.51%;H,6.64%;N,4.01%;O,3.06%;S,12.25%;Se,7.54%;测试值:C,66.57%;H,6.66%;N,4.00%;O,3.03%;S,12.22%;Se,7.52%。质谱:计算值:1047.41;实测值:1046.87。
实施例6
聚4-(5-(4,8-双(4-((2-乙基己基)氧基)-3-氟苯基)苯并[1,2-B:4,5-B']噻吩-2-基)噻吩-2-基)-6-辛基-8-(噻吩-2-基)-5H-[1,2,5]硒二唑并[3,4-f]的异吲哚-5,7(6H)-二酮的制备,合成路线和合成步骤如下:
氩气保护下,在10mL微波管内,加入4,8-双(5-溴噻吩-2-基)-6-辛基-5H-[1,2,5]硒二唑并[3,4-f]的异吲哚-5,7(6H)-二酮(103mg,0.15mmol),4,8-双(4-((2-乙基己基)氧基)-3-氟苯基)苯并[1,2-B:4,5-B']噻吩-2,6-二基-双-(三甲基锡烷)(144mg,0.15mmol),四(三苯基膦)钯(8mg)和二甲苯(4mL),微波200℃反应45min,待反应降至室温后将反应液沉析在甲醇中,先后用甲醇、丙酮、正己烷进行索氏抽提,然后加入二乙基二硫代氨基甲酸钠三水合物的水溶液(225mg,1mmol,100mL水)于60℃搅拌8小时,除去反应中的钯催化剂,用甲醇、丙酮、正己烷进行索氏抽提,干燥,得到深绿色固体(127mg),产率:71.35%。核磁共振氢谱:(CDCl3)δ(ppm):7.95(d,J=3.5Hz,2H),7.50(d, J=9.8Hz,2H),7.24(d,J=8.1Hz,4H),7.12(d,J=8.5Hz,4H),4.89(t,6H), 2.52(p,J=17.0Hz,4H),1.71–1.51(m,6H),1.42–1.11(m,26H),0.88(dd,J =7.8,5.6Hz,15H).元素分析:计算值:C,64.12%;H,5.64%;F,3.27%;N,3.62%;O, 5.51%;S,11.04%;Se,6.80%;测试值:C,64.15%;H,5.60%;F,3.24%;N,3.62%;O, 5.55%;S,11.08%;Se,6.76%。质谱:计算值:1161.41;实测值:1160.36。
实施例7
聚4-(5-(4,8-双(3-氟-4-((2-己基癸基)氧基)苯基)苯并[1,2-B:4,5-B']噻吩-2-基)噻吩-2-基)-6-辛基-8-(噻吩-2-基)-5H-[1,2,5]硒二唑并[3,4-f]的异吲哚-5,7(6H)-二酮的制备,合成路线和合成步骤如下:
氩气保护下,在10mL微波管内,加入4,8-双(5-溴噻吩-2-基)-6-辛基-5H-[1,2,5]硒二唑并[3,4-f]的异吲哚-5,7(6H)-二酮(103mg,0.15mmol),(4,8-双(3-氟-4-((2- 己基癸)氧基)苯基)苯并[1,2-B:4,5-B']噻吩-2,6-二基)双(三甲基锡烷)(178mg,0.15mmol),四(三苯基膦)钯(8mg)和二甲苯(4mL),微波200℃反应45min,待反应降至室温后将反应液沉析在甲醇中,先后用甲醇、丙酮、正己烷进行索氏抽提,然后加入二乙基二硫代氨基甲酸钠三水合物的水溶液(225mg,1mmol,100mL水)于60℃搅拌8小时,除去反应中的钯催化剂,用甲醇、丙酮、正己烷进行索氏抽提,干燥,得到深绿色固体(169mg),产率:81.64%。核磁共振氢谱:(CDCl3)δ(ppm):7.97(d,J=3.5Hz,2H),7.56(d,J=9.8Hz,2H), 7.23(d,J=8.1Hz,4H),7.18(d,J=8.5Hz,4H),4.81(t,6H),1.75–1.53(m, 6H),1.46–1.13(m,58H),0.87(dd,J=7.8,5.6Hz,15H).元素分析:计算值:C,67.60%; H,7.05%;F,2.74%;N,3.03%;O,4.62%;S,9.26%;Se,5.70%;测试值:C,67.62%; H,7.01%;F,2.74%;N,3.07%;O,4.63%;S,9.26%;Se,5.67%。质谱:计算值:1385.84;实测值:1385.67。
上述制备的聚合物的紫外-可见光吸收光谱图如图1、图2所示,紫外-可见光吸收光谱在Shimadzu UV-3600紫外分析仪上测量。由图1和图2可以看出,聚合物P1、P2、P3在400-500nm、600-800nm有较强的吸收。其中聚合物P1、P2、P3的薄膜吸收最大峰在465nm,447nm,414nm,在氯化苯中的最大吸收峰在457nm,438nm,406nm,说明上述聚合物对太阳光有较强的吸收。同时,也表明上述聚合物由于硒原子的存在,在薄膜中容易发生红移。表 1为上述聚合物的分子轨道能级和光学带隙。
表1
上述制备的聚合物的电化学曲线如图3、图4所示,可以看出上述聚合物具有较深的HOMO 能级(HOMO能级为最高占据分子轨道、LUMO能级为最低未占分子轨道)。其中聚合物P1、 P2、P3、P4、P5具有较深的HOMO能级。由于硒原子的存在,它们的光学带隙相对都比较窄,与上表数据相符,因此,本发明的共轭聚合物可用于制作聚合物发光二极管器件,聚合物场效应晶体管和聚合物太阳能电池的活性层。
上述实施例为本发明较佳的实施方式,但本发明的实施方式并任何不受上述实施例的限制,其他的未背离本发明的精神实质与原理下所做的改变、修饰、替代、组合、简化,均应为等效的置换方式,都包含在本发明的保护范围之内。
Claims (1)
1.一种含1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺的聚合物的制备方法,其特征在于,步骤如下:
(1)以2,5-二噻吩-3,4-并噻唑为母体,与丁炔二酸二甲酯反应,得到4,7-二(噻吩-2-基)苯并[c][1,2,5]噻二唑-5,6-二甲酸二甲酯;再通过水解,得到4,7-二(噻吩-2-基)苯并[c][1,2,5]噻二唑-5,6-二羧酸;然后与乙酸酐反应,得到4,8-二(噻吩-2-基)异苯并呋喃[5,6-C][1,2,5]噻二唑-5,7-二酮;然后与烷基胺反应,得到6-R1-4,8-二(噻吩-2-基)-5H-[1,2,5]噻二唑并[3,4-f]的异吲哚-5,7(6H)-二酮;再通过铁粉还原,得到5,6-二氨基-4,7-二(噻吩-2-基)-N-R1-异哚吲-1,3-二酮,再将5,6-二氨基-4,7-二(噻吩-2-基)-N-R1-异哚吲-1,3-二酮和二氧化硒进行反应,得到4,7-二(噻吩-2-基)-1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺,最后通过NBS溴化得到最终单体4,7-二(5-溴-噻吩-2-基)-1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺;
(2)金属催化偶联反应:将含电子给体单元D的具有金属催化偶联反应活性官能团的单体与步骤(1)所得的4,7-二(5-溴-噻吩-2-基)-1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺在金属催化剂下反应,得到含1,2,5-苯并硒二唑-N-R1-5,6-二元羧酸酰亚胺的聚合物;
其中,R1为烷基链;所述烷基链为1~24个碳原子的直链、支链或者环状烷基链,或其中一个或多个碳原子被氧原子、烯基、炔基、芳基、羟基、氨基、羰基、羧基、酯基、氰基或硝基取代,氢原子被卤素原子或氧原子、烯基、炔基、芳基、羟基、氨基、羰基、羧基、酯基、氰基或硝基取代;
所述含电子给体单元D为如下结构的一种以上:
其中,R3、R4为氢原子,或者为其中一个或多个碳原子被氧原子、烯基、炔基、羟基、氨基、羰基、羧基、硝基、苯基或噻吩基取代的烷基链,或者其中一个或多个氢原子被卤素原子取代的烷基链。
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