CN107365318A - A kind of organic molecule donor photovoltaic material containing fluorine with BTA and preparation method thereof and its application - Google Patents
A kind of organic molecule donor photovoltaic material containing fluorine with BTA and preparation method thereof and its application Download PDFInfo
- Publication number
- CN107365318A CN107365318A CN201710017444.XA CN201710017444A CN107365318A CN 107365318 A CN107365318 A CN 107365318A CN 201710017444 A CN201710017444 A CN 201710017444A CN 107365318 A CN107365318 A CN 107365318A
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- formula
- organic
- organic photoelectric
- group
- alkyl
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- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 239000011737 fluorine Substances 0.000 title claims abstract description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 title claims abstract 4
- 239000000463 material Substances 0.000 title abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 10
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 230000005669 field effect Effects 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- -1 Halo C1-C30 alkyl Chemical group 0.000 claims description 22
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 8
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000010703 silicon Substances 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical class 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 238000006555 catalytic reaction Methods 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 150000003053 piperidines Chemical class 0.000 claims description 4
- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001299 aldehydes Chemical group 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 19
- 230000005611 electricity Effects 0.000 abstract description 5
- 238000013086 organic photovoltaic Methods 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910003472 fullerene Inorganic materials 0.000 description 9
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000002484 cyclic voltammetry Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 0 C*(*=*)*=C1C(c2ccc(CC(*)C(OCC(N)N)=O)[n]2)=C(C(C)=C)C(N)=C(C2=CC=C(C3=Cc4c(-c5ccc([C@](C)*)[n]5)c([n]c(-c5ccc(-c(c(**(*6)C7I=*7)c6c(-c6ccc(C=C(*)C(*CC(CC7(C)N*7C)NC7=NC[C@]7C)=O)[o]6)c6N)c6N)[o]5)c5)c5c(-c([n]5)ccc5P)c4[U]3)I2)C1=* Chemical compound C*(*=*)*=C1C(c2ccc(CC(*)C(OCC(N)N)=O)[n]2)=C(C(C)=C)C(N)=C(C2=CC=C(C3=Cc4c(-c5ccc([C@](C)*)[n]5)c([n]c(-c5ccc(-c(c(**(*6)C7I=*7)c6c(-c6ccc(C=C(*)C(*CC(CC7(C)N*7C)NC7=NC[C@]7C)=O)[o]6)c6N)c6N)[o]5)c5)c5c(-c([n]5)ccc5P)c4[U]3)I2)C1=* 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002932 luster Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 238000004847 absorption spectroscopy Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 150000004816 dichlorobenzenes Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005518 electrochemistry Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 1
- QUTGXAIWZAMYEM-UHFFFAOYSA-N 2-cyclopentyloxyethanamine Chemical compound NCCOC1CCCC1 QUTGXAIWZAMYEM-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- MCEWYIDBDVPMES-UHFFFAOYSA-N [60]pcbm Chemical compound C123C(C4=C5C6=C7C8=C9C%10=C%11C%12=C%13C%14=C%15C%16=C%17C%18=C(C=%19C=%20C%18=C%18C%16=C%13C%13=C%11C9=C9C7=C(C=%20C9=C%13%18)C(C7=%19)=C96)C6=C%11C%17=C%15C%13=C%15C%14=C%12C%12=C%10C%10=C85)=C9C7=C6C2=C%11C%13=C2C%15=C%12C%10=C4C23C1(CCCC(=O)OC)C1=CC=CC=C1 MCEWYIDBDVPMES-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 1
- WINTXHPCODMMRI-UHFFFAOYSA-N benzene naphthalene Chemical compound C1=CC=CC=C1.C1=CC=CC=C1.C1=CC=CC2=CC=CC=C21 WINTXHPCODMMRI-UHFFFAOYSA-N 0.000 description 1
- UGYRYNXDEOFIQB-UHFFFAOYSA-N benzene thiophene Chemical compound S1C=CC=C1.C1=CC=CC=C1.C1=CC=CC=C1 UGYRYNXDEOFIQB-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical class O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002467 indacenes Chemical class 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 238000013087 polymer photovoltaic Methods 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/083—Syntheses without formation of a Si-C bond
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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Abstract
The invention discloses a kind of organic molecule donor photovoltaic material containing fluorine with BTA and preparation method thereof and its application.Shown in formula I, in formula, X is H or F to the structural formula of the organic molecule donor photovoltaic material；Z is O, S or Se；R1、R2And R3Independently selected from H, C1 C30 alkyl, C3 C30 cycloalkyl, C1 C30 alkoxies, C1 C30 alkylthio groups, halo C1 C30 alkyl, halo C3 C30 cycloalkyl and halo C1 C30 alkoxies；A1And A2It is organic conjugate unit；N is the natural number between 1~10.Application of the organic photoelectric compound in following function performance metering device falls within protection scope of the present invention：Solar cell, field-effect transistor, Organic Light Emitting Diode and photovoltaic device.The synthesis step of organic photoelectric compound provided by the invention is simple, easily purifies, structure determination, has superior photovoltaic performance with organic photovoltaic devices prepared by the organic photoelectrical material in the present invention, its electricity conversion can reach 9.5%.
Description
Technical field
The present invention relates to a kind of organic molecule donor photovoltaic material containing fluorine with BTA and preparation method thereof
And its application.
Background technology
With the increasingly depleted of fossil energy, energy shortage turns into the problem of whole world is extremely urgent；Solar energy have cleaning,
Green non-pollution, it is widely distributed, renewable the advantages that and it is most with prospects, develop and utilize solar energy will be that one kind has effect
Solution method to energy crisis.Organic solar batteries possess low cost, in light weight, flexible, solution processable and can
The advantages that being prepared with large area, therefore widely paid close attention in academia.Up to the present, by molecular structure, device
The optimization of structure and processing technology, the solar-electricity prepared based on polymeric donor or small molecule donor with fullerene acceptor blending
The electricity conversion in pond has broken through 10%, and this shows the huge applications prospect of organic solar batteries (see Li Yong boats etc.《It is poly-
Compound solar cell material and device》).But be the fullerene derivate acceptor of representative there is shortcomings using PCBM, such as
Visible region absorb it is weaker, energy level is difficult to, purification it is more difficult cause it is expensive etc..Therefore, Recent study personnel
In order to replace the fullerene acceptor in organic solar batteries, synthesize a series of containing imidodicarbonic diamide, benzene-naphthalene diimide, two
The new small molecules such as thieno indacene and the non-fullerene acceptor material of polymer.Recently, based on polymer donor material with it is non-
The electricity conversion that fullerene acceptor material blending prepares solar cell has reached 8%-12%, shows excellent
Photovoltaic performance.Organic molecule has molecular structural formula determination, and no batch difference, synthesis and purification are simple, and cost is low to dive
In advantage, but the electricity conversion of the non-fullerene solar cell based on organic molecule donor material compares polymer
For solar cell or relatively low, thus develop it is a kind of efficiently with the organic molecule that non-fullerene acceptor matches to
Body material becomes study hotspot.
The content of the invention
It is an object of the invention to provide a kind of organic molecule donor photovoltaic material with BTA containing fluorine and its
Preparation method and applications, the organic molecule donor photovoltaic material have higher photoelectric transformation efficiency, can be applied to light
Electrical domain.
Present invention firstly provides organic photoelectric compound shown in Formulas I,
In formula, X is H or F；
Z is O, S or Se；
R1、R2And R3Independently selected from H, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkoxies, C1-C30 alkane sulphur
Base, C1-C30 alkane silicon substrate, halo C1-C30 alkyl, halo C3-C30 cycloalkyl and halo C1-C30 alkoxies；
A is organic conjugate unit；
Ar is any in following units：
N is the natural number between 1~10.
In described organic photoelectric compound, the C1-C30 alkyl, the C3-C30 cycloalkyl, the C1-C30 alcoxyls
Base, the C1-C30 alkylthio groups, the C1-C30 alkane silicon substrate are substituted or unsubstituted group；
When for substituted group when, the substituent that is connected is at least one of following radicals：
Cycloalkyl, aryl, heteroaryl, heteroalicyclyl, hydroxyl, alkoxy, aryloxy group, sulfydryl, alkylthio group, arylthio, cyanogen
Base, halo, carbonyl, thiocarbonyl, carbamoyl, thiocarbamoyl, acylamino-, sulfonamido, carboxyl, isocyanic acid
Root, thiocyano, isosulfocyanate radical, nitro, silicyl, three halide sulfonyls, single-substituted amino group, di-substituted
Amino group and the protected derivative of the amino group.
In described organic photoelectric compound, R5Can be H, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkoxies,
The derivative of C1-C30 alkylthio groups, C1-C30 alkane silicon substrate or their halogen substitution, the halogen is bromine, chlorine, fluorine or iodine；
Y is O, S or Se.
The organic conjugate unit is specially any in following units：
In each unit, R4For H, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkoxies, C1-C30 alkylthio groups, C1-
C30 alkane silicon substrate or the derivative of their halogen substitution, the halogen is bromine, chlorine, fluorine or iodine.
The organic photoelectric compound is specifically as shown in formula II, formula III, formula IV or formula V：
In formula, R6And R7Independently selected from hydrogen atom, alkyl, ester group, carbonyl, aralkyl, miscellaneous alkyl, the alkyl is 1-
The straight or branched alkyl of 30 carbon atoms.
Wherein, the organic photoelectric compound of formula II is specifically as shown in formula II -1, formula II -2 or formula II -3：
Organic photoelectric compound shown in formula IV is specifically as shown in formula IV -1：
Organic photoelectric compound shown in formula V is specifically as shown in formula V -1：
The present invention further provides the preparation method of the organic photoelectric compound, by by dialdehyde end group compound with
End group precursor compound carries out Ke Neifeinageer (Knoevenagel) condensation reactions and is made, and comprises the following steps：
(1) under argon gas protection, in Pd (PPh3)4Under catalysis, single aldehyde end group bromo-derivative shown in formula 1 and double tin shown in formula 2
Monomer is reacted to obtain dialdehyde end group compound shown in formula 3；
(2) under the catalysis of piperidines, dialdehyde end group compound shown in formula 3 contracts with the group A through Ke Neifeinageer
Conjunction, which is reacted, produces the organic photoelectric compound；
The group A is organic conjugate unit.
It is above-mentioned it is various in, X, Z, R1、R2、R3, A and n be defined as above.
In above-mentioned preparation method, in step (1), the reaction is being heated to reflux lower progress；
The solvent of the reaction is toluene；
The time of the reaction is 1~3 day；
After the reaction terminates, purified in the following way：Using dichloromethane-petroleum ether as eluant, eluent, post point is crossed
From.
In above-mentioned preparation method, in step (1), the mass ratio of single aldehyde end group bromo-derivative and double tin monomers
Can be 2：1；
The dosage of the solvent of the reaction can be：Double tin monomers described in 10~100L/mol；
Pd (the PPh3)4Mol ratio with above-mentioned double tin monomers can be 0.1~20：100.
In above-mentioned preparation method, in step (2), the reaction is being heated to reflux lower progress；
The solvent of the reaction is chloroform；
The time of the reaction is 12~48 hours；
The dialdehyde end group compound and the mol ratio of the end group precursor compound are 1：10~100；
After the reaction terminates, purified in the following way：With chloroform extraction, merge organic phase, anhydrous sulphur
Sour sodium is dried, removal of solvent under reduced pressure, through post separation.
Present invention also offers a kind of photoactive layer, is made up of the organic photoelectric compound and n-type electron acceptor, institute
The mol ratio for stating n-type electron acceptor and the organic photoelectric compound is 1：0.1~10, such as 1：1；
The n-type electron acceptor is non-fowler vinyl polymer, concretely IC-C6IDT-IC (its structural formula such as Fig. 1
It is shown).
The application of the organic photoelectric compound or the photoactive layer in following function performance metering device falls within this
The protection domain of invention：Solar cell, field-effect transistor, Organic Light Emitting Diode and photovoltaic device.
The synthesis step of organic photoelectric compound provided by the invention is simple, easily purifies, structure determination, with the present invention
Organic photoelectrical material prepare organic photovoltaic devices there is superior photovoltaic performance, its electricity conversion can reach
9.5%.
Brief description of the drawings
Fig. 1 is non-fullerene small molecule receptor IC-C6IDT-IC molecular structural formula.
Fig. 2 is the ultraviolet-visible absorption spectroscopy figure of compound shown in formula II -1.
Fig. 3 is the ultraviolet-visible absorption spectroscopy figure of compound shown in formula V -1.
Fig. 4 is the electrochemistry cyclic voltammetry curve figure of compound shown in formula II -1.
Fig. 5 is the electrochemistry cyclic voltammetry curve figure of compound shown in formula V -1.
Fig. 6 is current density voltage curve of the compound under optimal device conditions shown in formula II -1.
Fig. 7 is current density voltage curve of the compound under optimal device conditions shown in formula V -1.
Embodiment
Experimental method used in following embodiments is conventional method unless otherwise specified.
Material used, reagent etc., unless otherwise specified, are commercially obtained in following embodiments.
Embodiment 1,
The organic photoelectric compound of the present embodiment is made up of big organic conjugate unit system and alkane or class alkane structure,
For the black solid powder with metallic luster, the chemical structure of general formula of its compound is as shown in formula II：
Wherein：R6For 2- ethylhexyls, R7For 2- hexyl octyl groups, i.e., the chemical structural formula of the compound is as shown in formula II -1：
This be used for solar cell organic photoelectric compound preparation method, by by dialdehyde end group compound with end
Based precursor compound carries out Ke Neifeinageer (Knoevenagel) condensation reactions and is made, and comprises the following steps：
1) under argon gas protection, by 5- (7- (5- bromothiophene -2- bases) -5,6- bis- fluoro- 2- (the 2- hexyl last of the ten Heavenly stems) -2H- benzos
[d] [1,2,3] triazole-4-yl) substitution of thiophene -2-formaldehyde 3.25g (5.0mmol) and 2- ethylhexyls thienyl the thiophene of benzo two
The double tin monomer 2.26g (2.5mmol) of fen, 30mL dry toluenes and triphenylphosphine palladium 0.05g (0.043mmol) mixing, heating
Back flow reaction 1 day, then pours into reaction solution in 100mL water, is extracted 3 times with 40mL dichloromethane, organic phase is washed with 50mL
Wash 3 times, after anhydrous sodium sulfate drying, toluene is removed under reduced pressure, using dichloromethane-petroleum ether as eluant, eluent, post separation is crossed, in being made
Mesosome dialdehyde end group compound, its structural formula are as follows：
2) by above-mentioned dialdehyde end group compound 0.859g (0.5mmol), 2- ethylhexyls -2- in 100mL bottle with two necks
Cyan-acetic ester 0.985g (5.0mmol), the chloroform 50mL dried and piperidines 0.01g (0.05mmol) mixing, are heated back
Stream 24 hours, with chloroform extraction, merge organic phase, anhydrous sodium sulfate drying, removal of solvent under reduced pressure, through post separation, be made
Metallic luster black solid is organic photoelectric compound 0.934g, yield 90%.
1H NMR(400MHz,CDCl3):δ(ppm)8.26-8.25(d,2H),8.15-8.14(d,2H),8.12(s,
2H),7.81-7.80(d,2H),7.50(s,2H)7.36-7.35(d,2H),7.14(s,2H),7.00-6.99(d,2H),
4.74-4.73(d,4H),4.20-4.18(m,4H),2.99-2.98(d,4H)2.31-2.27(m,2H),1.87-1.80(m,
2H),1.57-1.51(m,2H),1.48-1.37(m,80H),1.28-1.22(m,6H),1.0-0.92(m,18H),0.87-
0.82(m,12H).
13C NMR(100MHz,CDCl3),δ(ppm):163.0,156.9,148.2,145.6,145.5,142.9,
142.7,141.7,139.1,138.7,138.2,137.1,136.2,132.4,131.1,130.5,129.7,128.7,
128.5,125.1,124.8,124.2,122.0,121.9,121.7,115.7,99.6,68.9,60.4,39.1,38.9,
31.9,31.8,31.5,30.4,29.8,29.5,29.3,28.9,26.3,26.2,23.8,22.9,22.6,14.0,11.0.
MALDI-TOF MS:calcd.for C118H150F4N8O4S8M/z=2077.02；found 2076.0.
Through characterizing, prepared compound structure is correct.
Embodiment 2,
The organic photoelectric compound of the present embodiment is made up of big organic conjugate unit system and alkane or class alkane structure,
For the black solid powder with metallic luster, the chemical structure of general formula of its compound is as shown in following formula V：
Wherein, R7For 2- hexyl octyl groups, R8For 2- ethylhexyls, i.e. the chemical structural formula of the compound is formula V -1：
The preparation method that this is used for the organic photoelectric compound of solar cell is substantially the same manner as Example 1, difference
It is that the double tin monomers of thiophene substitute the double tin monomers of benzene thiophene of 2- ethylhexyls thienyl substitution, equally with chloroform
For solvent, using piperidines as catalyst, organic photoelectric compound, yield 85% is made.
1H NMR(400MHz,CDCl3):δ(ppm)8.21-8.20(m,4H),8.18(s,2H),7.77-7.76(d,
2H),7.11-7.10(m,4H),4.75-4.74(d,4H),4.17-4.09(m,8H),2.32-2.30(m,2H),1.83-1.72
(m,4H),1.55-1.25(m,80H),1.18-1.14(t,6H),1.10-1.07(t,6H),0.97-0.91(m,12H),
0.89-0.83(m,12H).
13C NMR(100MHz,CDCl3),δ(ppm):162.9,149.6,147.5,145.7,144.0,141.7,
140.7,137.2,137.0,136.6,136.2,132.6,132.0,131.0,129.1,126.0,125.2,124.6,
116.6,115.8,112.0,108.2,99.1,69.0,60.6,41.0,39.3,39.0,32.0,31.9,31.6,30.7,
30.5,30.1,29.9,29.7,29.5,29.1,26.5,26.4,24.1,23.9,23.5,23.1,22.8,14.5,14.2,
11.6,11.2.MALDI-TOF MS:Calcd.for C110H146F4N8O6S6M/z=1943.97；Found 1944.0.
Elemental analysis:Calcd for C110H146F4N8O6S6(%):C,67.93；H,7.57；N,
5.76.Found (%):C,68.02；H,7.62；N,5.81.
Through characterizing, prepared compound structure is correct.
Embodiment 3, the film forming of the small molecule of the present invention and dissolubility test.
Compound shown in the formula II -1 and formula V -1 that embodiment 1 is prepared with embodiment 2 is put respectively several to be had common
In solvent, such as chlorobenzene, dichloro-benzenes, chloroform, toluene, trichloro-benzenes, methanol.It was found that compound has well in chlorinated solvent
Dissolubility, it is but insoluble in methyl alcohol.Three solutions of chlorine of compound are spin-coated on sheet glass, the thin of high-quality can be made
Film.
Embodiment 4, using absorption spectrum its optical band gap is measured.
The absorption spectrum that compound prepared by Examples 1 and 2 determines under chloroformic solution and film is shown in Fig. 2.
The optical band gap of compound can be by empirical equation (Eg=1240/ λABSORPTION EDGE) calculate and be shown in Table 1.
Optical absorption data shown in the formula II -1 of table 1 and formula V -1
| Compound | λmax | λedge | Eg opt(eV) |
| Formula II -1 | 558 | 663 | 1.87 |
| Formula V -1 | 618 | 673 | 1.84 |
The absorption maximum of compound shown in formula II -1 and formula V -1 prepared by Examples 1 and 2 respectively in 558nm and 618nm,
ABSORPTION EDGE is respectively 1.87eV and 1.84eV in 663nm and 673nm, corresponding optical band gap.As a result show formula II -1 and formula V -
Compound shown in 1 is typical intermediate band gap compound-material.
Embodiment 5, the highest occupied molecular orbital HOMO energy levels using electrochemical cyclic voltammetry measure compound of the invention
It is not occupied by an electron, the molecular orbit of minimum energy is lowest unoccupied molecular orbital lumo energy.
Compound (0.5mg) shown in formula II -1 and formula V -1 prepared by Examples 1 and 2 is dissolved in 1mL chloroforms, then
To will be added dropwise in the solution on working electrode such as platinized platinum；Using 0.1mol/L tetrabutyl ammonium hexafluorophosphates acetonitrile solution as
Electrolyte；Using platinum filament as to electrode；Reference electrode is used as using filamentary silver.Using electrochemical cyclic voltammetry measurement in the system
Carry out.Identical program is repeated to determine HOMO, the lumo energy of other compounds of the present invention.
Embodiments of the invention 1 and it is 2-in-1 into formula II -1 and formula V -1 shown in the cyclic voltammetric data of compound be shown in figure
3.The HOMO energy levels of compound are -5.29eV shown in the formula II -1 of embodiments of the invention 1, and lumo energy is -2.92eV.This hair
The HOMO energy levels of compound are -5.35eV shown in the formula V -1 of bright embodiment 2, and lumo energy is -3.08eV.
Embodiment 6, the organic photovoltaic devices for preparing conventional structure
By any compound produced by the present invention and non-fullerene acceptor (IC-C6IDT-IC, structural formula are as shown in Figure 1)
Using weight ratio as 1：1 blending is dissolved in the blending active layer solution that dichloro-benzenes prepares 16g/L.Served as a contrast in transparent indium tin oxide (ITO)
Organic photovoltaic devices are prepared on bottom.By conventional anode modification strata 3,4- ethyldioxythiophenes:Poly styrene sulfonate
(PEDOT:PSS ITO surfaces) are spin-coated on to be modified, PEDOT is tested using Dektak XT film thickness gauges:The thickness of PSS layer is
30nm.Then the active layer solution spin coating thin layer of above-mentioned blending.Then about 10-4Successive evaporation calcium and aluminium under Pa pressure
Thin layer, obtain the polymer photovoltaics of conventional structure.In filling N2Glove box in use AAA level solar simulators
AM1.5G(100mW/cm2) intensity under prepared organic photovoltaic devices open-circuit voltage, short circuit current, fill factor, curve factor and energy
Conversion efficiency is tested.
Embodiment 7,
Compound shown in the formula II -1 prepared based on embodiment 1, the conventional knot for preparing and testing according to the step of embodiment 6
The organic solar batteries device of structure.Current density voltage curve after test is shown in Fig. 4.Wherein open-circuit voltage is 0.97V,
Short circuit current is 15.21mA/cm2, fill factor, curve factor 65.46%, energy conversion efficiency 9.7%.
The device parameters of compound shown in the formula V -1 prepared under the same terms are that open-circuit voltage is 0.98V, short circuit current
For 10.87mA/cm2, fill factor, curve factor 52.46%, energy conversion efficiency 5.8%.
Claims (10)
1. organic photoelectric compound shown in Formulas I,
In formula, X is H or F；
Z is O, S or Se；
R1、R2And R3Independently selected from H, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkoxies, C1-C30 alkylthio groups,
Halo C1-C30 alkyl, halo C3-C30 cycloalkyl and halo C1-C30 alkoxies；
A1And A2It is organic conjugate unit；
Ar is any in following units：
N is the natural number between 1~10.
2. organic photoelectric compound according to claim 1, it is characterised in that：The C1-C30 alkyl, the C3-C30
Cycloalkyl, the C1-C30 alkoxies and the C1-C30 alkylthio groups are substituted or unsubstituted group；
When for substituted group when, the substituent that is connected is at least one of following radicals：
Cycloalkyl, aryl, heteroaryl, heteroalicyclyl, hydroxyl, alkoxy, aryloxy group, sulfydryl, alkylthio group, arylthio, cyano group, halogen
Generation, carbonyl, thiocarbonyl, carbamoyl, thiocarbamoyl, acylamino-, sulfonamido, carboxyl, isocyano, cyanogen
Sulfenyl, isosulfocyanate radical, nitro, silicyl, three halide sulfonyls, single-substituted amino group, the ammonia of di-substituted
Base group and the protected derivative of the amino group.
3. organic photoelectric compound according to claim 1 or 2, it is characterised in that：R5For H, C1-C30 alkyl, C3-C30
Cycloalkyl, C1-C30 alkoxies, C1-C30 alkylthio groups, C1-C30 alkane silicon substrate or the derivative of their halogen substitution, the halogen
Element is bromine, chlorine, fluorine or iodine；
Y is O, S or Se.
4. the organic photoelectric compound according to any one of claim 1-3, it is characterised in that：The organic conjugate unit
To be any in following units：
5. organic photoelectric compound according to claim 4, it is characterised in that：R4For H, C1-C30 alkyl, C3-C30 cycloalkanes
Base, C1-C30 alkoxies, C1-C30 alkylthio groups, C1-C30 alkane silicon substrate or the derivative of their halogen substitution, the halogen are
Bromine, chlorine, fluorine or iodine.
6. the organic photoelectric compound according to any one of claim 1-5, it is characterised in that：The organic photoelectric chemical combination
Thing is specifically as shown in formula II, formula III, formula IV or formula V：
In formula, R6And R7Independently selected from hydrogen atom, alkyl, ester group, carbonyl, aralkyl, miscellaneous alkyl,
The alkyl is the straight or branched alkyl of 1-30 carbon atom.
7. organic photoelectric compound according to claim 6, it is characterised in that：The organic photoelectric compound is specifically such as formula
II -1, shown in formula II -2, formula II -3, formula IV -1 or formula V -1：
8. the preparation method of organic photoelectric compound, comprises the following steps any one of claim 1-7：
(1) under argon gas protection, in Pd (PPh3)4Under catalysis, single aldehyde end group bromo-derivative shown in formula 1 and double tin monomers shown in formula 2
Reacted to obtain dialdehyde end group compound shown in formula 3；
(2) under the catalysis of piperidines, dialdehyde end group compound shown in formula 3 is condensed anti-with the group A through Ke Neifeinageer
The organic photoelectric compound should be produced；
The group A is organic conjugate unit.
In formula 1 and formula 3, X, Z, R1、R2、R3Definition with n is the same as in claim 1；
In formula 2 and formula 3, Ar definition is the same as in claim 1.
9. a kind of photoactive layer, organic photoelectric compound and n-type electron acceptor form any one of claim 1-7,
The mol ratio of the n-type electron acceptor and the organic photoelectric compound is 1：0.1~10；
The n-type electron acceptor is non-fowler vinyl polymer.
10. photoactive layer described in any one of the claim 1-7 organic photoelectric compounds or claim 9 is preparing following work(
Application in energy performance metering device：Solar cell, field-effect transistor, Organic Light Emitting Diode and photovoltaic device.
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| CN111704623A (en) * | 2020-06-10 | 2020-09-25 | 山西大学 | Organic electroluminescent red light material and preparation method and application thereof |
| CN112759770A (en) * | 2020-12-31 | 2021-05-07 | 江汉大学 | Functional NH2-MIL125(Ti) and preparation method and application thereof |
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