CN116284052B - Preparation of organic conjugated cyclic molecule and application of organic conjugated cyclic molecule in organic photovoltaics - Google Patents
Preparation of organic conjugated cyclic molecule and application of organic conjugated cyclic molecule in organic photovoltaics Download PDFInfo
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- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 59
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 238000013086 organic photovoltaic Methods 0.000 title claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 36
- 238000000034 method Methods 0.000 abstract description 5
- 238000006619 Stille reaction Methods 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 3
- 238000007363 ring formation reaction Methods 0.000 abstract description 3
- 238000010521 absorption reaction Methods 0.000 abstract description 2
- 238000005580 one pot reaction Methods 0.000 abstract description 2
- 239000012535 impurity Substances 0.000 abstract 1
- 230000003595 spectral effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 239000000463 material Substances 0.000 description 38
- 150000001875 compounds Chemical class 0.000 description 29
- 239000002904 solvent Substances 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- 238000010586 diagram Methods 0.000 description 19
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 229930192474 thiophene Natural products 0.000 description 10
- 229940126062 Compound A Drugs 0.000 description 9
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical group ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 8
- 230000009471 action Effects 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 150000003606 tin compounds Chemical class 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- POXIZPBFFUKMEQ-UHFFFAOYSA-N 2-cyanoethenylideneazanide Chemical group [N-]=C=[C+]C#N POXIZPBFFUKMEQ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 3
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 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 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000003577 thiophenes Chemical class 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- -1 3, 4-difluorothienyl Chemical group 0.000 description 1
- OWEQSMBFLCRRMV-UHFFFAOYSA-N 4,7-dibromo-2h-benzotriazole Chemical compound BrC1=CC=C(Br)C2=NNN=C12 OWEQSMBFLCRRMV-UHFFFAOYSA-N 0.000 description 1
- RWEKWRQKAHQYNE-UHFFFAOYSA-N 7-(bromomethyl)pentadecane Chemical compound CCCCCCCCC(CBr)CCCCCC RWEKWRQKAHQYNE-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 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 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 229940071182 stannate Drugs 0.000 description 1
- 229910001134 stannide Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains four or more hetero rings
-
- 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
- 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
- C07D495/22—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 four or more hetero rings
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Photovoltaic Devices (AREA)
Abstract
The invention discloses preparation of an organic conjugated cyclic molecule and application thereof in organic photovoltaics, relates to the technical field of organic photovoltaic cell devices, and mainly prepares an organic cyclic molecule containing an A-DA' D-A small molecular receptor by a Stille coupling method (one-pot method), and has the advantages of high cyclization yield, few generated impurities, easy purification and the like. In addition, the cyclic molecular structure is easy to modify, can adjust the solubility and crystallinity, has wider spectral absorption, and can obtain better photoelectric conversion efficiency when being applied to an organic solar cell as a receptor.
Description
Technical Field
The invention relates to the technical field of organic photovoltaic cell devices, in particular to preparation of an organic conjugated cyclic molecule and application of the organic conjugated cyclic molecule in organic photovoltaic.
Background
The organic solar cell prepared from the organic semiconductor material has the advantages of simple preparation process, low cost, large-area preparation, capability of being manufactured into flexible devices and the like, and has great application prospects in the fields of portable charging equipment, flexible wearable electronic equipment, photovoltaic building integration and the like. In order to rapidly advance the commercial application of organic solar cells, the development of active layer materials to achieve high efficiency and high stability remains worth exploring. The cyclic conjugated organic molecule has a rigid conjugated framework structure, unique photoelectric property, thermal stability, structural stability and the like, has wide potential application in material science, and is widely focused and interested by researchers. In addition, cyclic conjugated organic molecules can form ordered molecular structures through intermolecular aromatic packing. The invention discloses a preparation method of an organic conjugated cyclic molecule containing multiple D-A actions and application of the organic conjugated cyclic molecule in an organic photovoltaic cell.
The following problems exist in the prior art:
The existing organic solar cell has poor film forming property, low stability and the like of an organic receptor material; the existing organic solar cell has the problems of low photoelectric conversion efficiency and poor device stability during preparation; the existing organic solar cell has the problems of few application, difficult modification of the structure, difficult regulation and control of the performance, lower synthesis yield and difficult purification of the organic conjugated cyclic molecule.
Disclosure of Invention
The invention provides a preparation method of an organic conjugated cyclic molecule and application of the organic conjugated cyclic molecule in organic photovoltaics, so as to solve the problems in the background technology.
In order to solve the above technical problems, a first object of the present invention is to provide a cyclic organic conjugated acceptor material with multiple D-a actions, which has good film forming property and high photoelectric conversion efficiency.
A second object of the present invention is to provide a method for preparing a cyclic organic conjugate material having multiple D-A actions simply by purification under mild conditions, with a simple operation (one-pot method), with a high yield (more than 50%).
A third object of the present invention is to provide the use of cyclic organic conjugated materials with multiple D-a actions, which have more complementary absorption with the donor material, have more matching energy levels with the donor material and have high and balanced carrier mobility, which can be used for the preparation of organic solar cells with high short-circuit currents and energy conversion efficiency.
In order to achieve the above technical object, the present invention provides a conjugated cyclic molecule having a structure of formula 1.
In the formula 2, R1 comprises identical or different hydrogen atoms, straight-chain or branched-chain alkyl groups and alkoxy groups with the carbon number of 2-20; r2 comprises identical or different hydrogen atoms, straight-chain or branched alkyl groups with 2-20 carbon atoms, alkoxy groups or cycloalkyl groups with 5-9 carbon atoms; r3 comprises H, F, C identical or different straight-chain alkanes with 1-6 carbon atoms.
Formula 1 is a schematic structural diagram of the organic cyclic conjugated molecule containing multiple D-A actions.
Formula 2 is the structural formula of the organic cyclic conjugated molecule containing multiple D-A actions.
The organic conjugated cyclic material comprises a small molecule acceptor unit (five-membered ring A-DA' D-A type acceptor molecule) and a pi unit (thiophene and derivatives thereof), wherein the small molecule acceptor unit is connected with the pi unit through C4-8 linear alkane, and two ends of the small molecule acceptor unit are connected with the pi unit to form a cyclic molecule.
The invention provides a preparation method of a cyclic organic conjugated material, which comprises the following steps:
step S1: under the protection of inert gas, preparing a compound A with two central cores A' connected by straight-chain alkane with 4-8 carbon atoms;
Step S2: carrying out the Stille (Stille) coupling and column chromatography on the initial product A obtained in the step S1 and the R2 substituted monothiophene stannate to obtain an intermediate product B; wherein R2 is the same or different hydrogen atoms, straight-chain or branched-chain alkyl groups with 2-20 carbon atoms, alkoxy groups or cycloalkyl groups with 5-9 carbon atoms;
Step S3: carrying out karduo (Cadogan) condensation ring-closure reaction on the product B obtained in the step S2 to obtain a ring-closure product C, and carrying out nucleophilic substitution reaction on the ring-closure product C and halogenated alkane to obtain a DA' D fused ring compound D; wherein R1 is one of the same or different hydrogen atoms, straight-chain or branched-chain alkyl groups with 2-20 carbon atoms and alkoxy groups;
Step S4: carrying out Wilsmeier-Haack (Vilsmeier-Haack) reaction on the product D obtained in the step S3 to obtain a compound E;
Step S5: reacting the product E obtained in the step S4 with 5-bromo-3- (dicyanomethylene) indigoketone through Knoevenagel (Knoevenagel) to obtain two five-membered ring A-DA' D-A type small molecule connected compound (DSMA);
Step S6: carrying out a Stille coupling reaction on the A-DA' D-A type small molecules and small molecule receptors (SMA) obtained in the step S5 and a double tin compound (pi) of thiophene or derivatives thereof to obtain a final organic cyclic conjugated molecule (RQM); wherein R3 is one of same or different H, F, C or straight-chain alkane with 1-6 carbon atoms.
The invention also provides a preparation method of the organic cyclic conjugated molecule, which comprises the following steps:
the G1 reaction conditions: under the protection of inert gas, N, N-Dimethylformamide (DMF) is taken as a solvent, potassium carbonate (K 2CO3) is taken as alkali, a dibromoalkyl chain and 4, 7-dibromo-2H-benzotriazole are subjected to substitution reaction, and a binuclear brominated product is obtained, purified by column chromatography and dried; a compound A prepared by preparing mixed acid from trifluoromethanesulfonic acid and fuming nitric acid, and then performing nitration reaction on the obtained bromide;
The G2 reaction conditions: the solvent is toluene, the catalyst is ditolylphosphine palladium dichloride, and the addition amount of the catalyst is 0.01-10% of the molar amount of the compound A; the molar ratio of the compound A to the R1 substituted thiophene stannide is 1:4.2-5.5; reflux reaction is carried out for 12 to 24 hours at the temperature of 80 to 100 ℃;
The G3 reaction conditions: the solvent is o-dichlorobenzene, and the catalyst is triphenylphosphine; the molar weight of the catalyst and the compound B is 20-30:1; reflux reaction is carried out for 16 to 20 hours at the temperature of 160 to 180 ℃; the conditions of the nucleophilic substitution reaction are as follows: n, N-dimethylformamide is taken as a solvent, potassium hydroxide is taken as alkali, and the molar ratio of halogenated alkane to compound C is 6-12:1; reflux reaction is carried out for 16 to 24 hours at the temperature of 80 to 100 ℃;
The G4 reaction conditions: the solvent is N, N-dimethylformamide, phosphorus oxychloride is formylating agent, and the molar ratio of the compound D to the phosphorus oxychloride is 1: 15-25; reflux reaction is carried out at the temperature of 80-105 ℃ for 12-24 hours;
the G5 reaction conditions: toluene is used as solvent, boron trifluoride diethyl etherate is used as catalyst, acetic anhydride and the molar ratio of the compound E to 5-bromo-3- (dicyanomethylene) indigoketone is 1:4 to 4.4; reacting for 15-30 minutes at room temperature;
The G6 reaction conditions: the solvent is toluene, the catalyst is one of tetra-triphenylphosphine palladium (Pd (pph 3)4) or tris (dibenzylideneacetone) dipalladium (Pd 2(dba)3), the mol ratio of the small molecule receptor (SMA) to the double tin compound (pi) of thiophene or a derivative thereof is 1-1.2:1, the adding amount of the catalyst is 10-15% of the small molecule receptor (SMA), and the reaction is carried out for 2-6 hours at the temperature of 110 ℃.
The invention also provides application of the organic cyclic conjugated molecule as an acceptor material in an organic solar cell.
Preferably, the organic cyclic conjugated molecules are used as acceptor materials and electron donor materials to form an active layer for the organic solar cell device. The specific preparation process of the active layer comprises the following steps: mixing an organic annular conjugated molecular acceptor material with an electron donor material, adding a solvent for dissolution (such as chlorobenzene, o-dichlorobenzene, chloroform or tetrahydrofuran, and the like) to obtain a slurry, preparing a layer of film on conductive glass by spin coating or other modes, and then preparing an organic solar cell device.
In a more preferred embodiment, the molar ratio of electron donor material to organic cyclic conjugated molecular acceptor material to electron donor material is 1:1 to 1.5.
More preferably, the electron donor materials are PM6, PTQ10 and D18, and other organic electron donor materials.
By adopting the technical scheme, compared with the prior art, the invention has the following technical progress:
1. The invention provides a preparation method of an organic conjugated cyclic molecule and application thereof in organic photovoltaics, wherein a linear alkane with 4-8 carbon atoms is used for connecting two small molecule receptor units through nucleophilic substitution with an A' unit, so that the spatial position of the molecule can be fixed to a certain extent, and the yield of the cyclic molecule is increased.
2. The invention provides a preparation method of an organic conjugated cyclic molecule and application thereof in organic photovoltaics, which introduces alkyl chains or conjugated side chains with different lengths, bifurcation positions and functionalization on a thiophene unit beta position in a small molecule acceptor, can regulate electron cloud density distribution of the molecule, influence molecular accumulation and the like, and can further improve material solubility and processing performance.
3. The invention provides a preparation method of an organic conjugated cyclic molecule and application thereof in organic photovoltaics, wherein alkyl chains with different lengths and branching positions are introduced on pyrrole ring nitrogen atoms in a small molecule receptor, so that the solubility and crystallinity of the molecule can be effectively regulated.
4. The invention provides a preparation method of an organic conjugated cyclic molecule and application thereof in organic photovoltaics, wherein alkyl chains, halogen atoms, ester chains or other functional groups are introduced into the 3, 4-position of thiophene serving as pi units, so that physical and chemical properties of the cyclic molecule are influenced.
5. The invention provides preparation of an organic conjugated cyclic molecule and application thereof in organic photovoltaics, which have good solubility, are easy to process into films, have stronger visible near infrared absorbance performance, and have excellent film forming property and stability. The preparation method can be used for preparing solar cell materials with high voltage and energy conversion efficiency, and is a class of potential acceptor materials. In addition, compared with the existing organic conjugated cyclic molecules, the organic conjugated cyclic molecule structure is easy to modify, the performance is easy to regulate and control, the synthesis yield is high, and the organic conjugated cyclic molecule is easy to purify, and is an organic photoelectric functional material with great potential.
Drawings
FIG. 1 is a schematic structural view of formula 1 of the present invention;
FIG. 2 is a schematic structural view of formula 2 of the present invention;
FIG. 3 is a schematic structural diagram of Compound A of the present invention;
FIG. 4 is a schematic structural diagram of intermediate B of the present invention;
FIG. 5 is a schematic diagram of the structure of the closed-loop product C of the present invention;
FIG. 6 is a schematic structural diagram of a fused ring compound D of the present invention;
FIG. 7 is a schematic structural diagram of Compound E of the present invention;
FIG. 8 is a schematic structural diagram of a compound (DSMA) of the present invention;
FIG. 9 is a schematic diagram of the structure of an organic cyclic conjugated molecule (RQM) of the present invention;
FIG. 10 is a schematic structural diagram of R1 of the present invention;
FIG. 11 is a schematic structural diagram of R2 of the present invention;
FIG. 12 is a schematic structural diagram showing the synthesis of Compound A of the present invention;
FIG. 13 is a schematic structural diagram showing the synthesis of Compound B of the present invention;
FIG. 14 is a schematic structural diagram showing the synthesis of Compound D of the present invention;
FIG. 15 is a schematic structural diagram showing the synthesis of Compound E of the present invention;
FIG. 16 is a schematic structural diagram of the synthesis of compound F (DSMA) of the present invention;
FIG. 17 is a schematic diagram of the synthesis of a cyclic molecule RQM of the invention;
FIG. 18 is a schematic diagram showing the synthesis of the cyclic molecule RQM-2F of the invention;
FIG. 19 is a schematic structural diagram of the structural formula of the compounds PM6, PTQ10 of the present invention;
FIG. 20 is a synthetic route diagram of the acceptor material RQM1 prepared by the invention;
FIG. 21 shows 1HNMR of the acceptor material RQM1 prepared according to the present invention;
FIG. 22 is a mass spectrum of the acceptor material RQM1 prepared by the invention;
FIG. 23 is a mass spectrum of the acceptor material RQM-2F prepared by the invention;
FIG. 24 is an absorption spectrum of the RQM1 receptor material prepared by the invention in chloroform solution and in a thin film state;
FIG. 25 is a cyclic voltammogram of the acceptor material RQM1 prepared according to the invention;
FIG. 26 is a graph of current-voltage (J-V) curve for the preparation of an organic solar cell according to the present invention;
Fig. 27 is an External Quantum Efficiency (EQE) graph of the present invention for preparing an organic solar cell.
Detailed Description
The invention is further illustrated by the following examples:
Example 1
The invention provides an organic conjugated cyclic molecule containing multiple D-A actions, wherein two A-DA' D-A receptor micromolecular center cores in the cyclic molecule are connected by an alkyl chain, two ends of the cyclic molecule are blocked by pi units (thiophene and derivatives thereof) to form a closed-loop molecule, the structural formula of the organic conjugated cyclic molecule is shown as a formula I, and the formula 1 is shown as a formula II; wherein R1 comprises the same or different hydrogen atoms, straight-chain or branched-chain alkyl, alkoxy, cycloalkyl or side chain containing aromatic units (benzene ring or thiophene) with the carbon number of 2-20; r2 comprises identical or different hydrogen atoms, straight-chain or branched alkyl groups with 2-20 carbon atoms, alkoxy groups or cycloalkyl groups with 5-9 carbon atoms or side chains containing aromatic units (benzene rings or thiophenes); r3 comprises identical or different H, F, C or straight-chain alkanes or branched alkyl groups with 1-6 carbon atoms.
Example 2
The invention provides a technical scheme that: preferably, when R1 is (as shown in fig. 10:), R2 is (as shown in fig. 11:), and R3 is H, the preparation of the organic conjugated cyclic molecule RQM1 is as follows:
Step G1: under the protection of inert gas, 4, 7-dibromo-2H-benzo [ d ] [1,2,3] triazole and dibromoalkyl chain undergo substitution reaction to obtain a compound 1, and two central cores A' are prepared into a compound A connected by straight-chain alkane with 4-8 carbon atoms after nitration;
Synthesis of compound a:
4, 7-dibromo-2H-benzo [ d ] [1,2,3] triazole (16.59 g,40.0 mmol), a dibromoalkyl chain (20.0 mmol) and anhydrous potassium carbonate (27.6 g,200 mmol) were weighed into a 500mL three-necked round bottom flask, N-Dimethylformamide (DMF) was added, the gas was replaced three times, and the reaction was carried out at 150℃under argon atmosphere for 24 hours. After the reaction, cooling to room temperature, extracting with Dichloromethane (DCM), spin-drying the solvent, separating and purifying the crude product by column chromatography, wherein Dichloromethane (DCM) is used as an eluent to obtain a white solid product, namely the compound 1 (6.6 g, yield 59.0%);
hydrogen spectrum (400 MHz, deuterated chloroform) )(1HNMR(400MHz,Chloroform-d))δ7.44(s,4H),4.78(t,J＝7.3Hz,4H),2.16(qt,J＝7.4,3.9Hz,4H),1.49-1.43(m,4H);
Fuming nitric acid (23.7 g,158.0 mmol) was added dropwise to a three-necked round bottom flask containing trifluoromethanesulfonic acid (19.9 g,316 mmol) in an ice-water bath, after the dropwise addition, stirring was continued in the ice-water bath for 30 minutes, after the mixed acid was prepared, compound 1 (5.0 g,7.9 mmol) was added to the mixed acid in portions, and after the addition, the reaction was carried out at room temperature for 1 hour. Pouring the reactant into crushed ice, adding sodium carbonate for neutralization, washing to be neutral, and drying in a vacuum drying oven to obtain a white solid product A (5.45 g, yield 85.0%);
Hydrogen spectrum (400 MHz, deuterated dimethyl sulfoxide) (1 HNMR (400 MHz, dmso-d 6)) δ4.95 (t, j=7.0 hz, 4H), 2.06 (p, j=7.1, 5.9hz, 4H), 1.45-1.31 (m, 4H).
Step G2: the compound B is obtained by a Stille coupling reaction of a compound A and 4-isooctylthiophene-2-tributyltin;
Synthesis of Compound B: compound A (5.0 g,6.1 mmol) and 4-isooctylthiophene-2-tributyltin (28.1 mmol) were weighed into a 250mL two-necked flask, the atmosphere was replaced three times, and bis-triphenylphosphine palladium dichloride and toluene were added under argon atmosphere and reacted at 110℃for 24 hours. After cooling the reaction to room temperature, the solvent was dried, extracted with Dichloromethane (DCM), the organic phases combined and the solvent was dried. The crude product was purified by column chromatography to give compound B as a yellow solid (6.7 g, 86.0% yield);
hydrogen spectrum (400 MHz, deuterated chloroform) )(1HNMR(400MHz,Chloroform-d))δ7.27(d,J＝1.4Hz,4H),7.20(d,J＝1.4Hz,4H),4.81(t,J＝7.1Hz,4H),2.58(d,J＝6.8Hz,8H),2.15(tt,J＝7.1,3.6Hz,4H),1.57–1.51(m,4H),1.51–1.44(m,4H),1.32–1.23(m,32H),0.88(t,J＝7.3Hz,24H).
Step G3: under the protection of inert gas, compound B is catalyzed by triphenylphosphine and subjected to ring closure reaction to obtain compound 2, and then nucleophilic substitution reaction is carried out on the compound 2 and bromoalkane in an alkaline environment to synthesize compound C;
Synthesis of Compound C: compound B (2.5 g,1.9 mmol) and triphenylphosphine (3.0 g,11.4 mmol) were reacted overnight at 180℃in a 250mL single neck round bottom flask with o-dichlorobenzene added, the gas replaced three times under argon. The reaction was stopped, cooled to room temperature, and the solvent was removed under reduced pressure and then directly subjected to the next step. Potassium hydroxide (1.1 g,19 mmol) was weighed separately, potassium iodide (315 mg,1.9 mmol) was placed in a round bottom flask containing 2, and then 7- (bromomethyl) pentadecane (2.9 g,9.5 mmol) and several N, N-dimethylformamide were added. The reaction is carried out for 24 hours at 90 ℃ under the protection of argon. After cooling to room temperature, the reaction mixture was extracted with Dichloromethane (DCM) and the crude product was purified by column chromatography to give compound C as an orange viscous compound, (2.9 g, 75% yield);
Hydrogen spectrum (400 MHz, deuterated chloroform) )(1HNMR(400MHz,Chloroform-d))δ6.94(s,4H),4.80(t,J＝7.4Hz,4H),4.40(d,J＝16.3Hz,8H),2.99–2.64(m,8H),2.21(q,J＝7.0Hz,4H),1.86(q,J＝6.2Hz,4H),1.72(s,4H),1.40–0.33(m,172H),-0.15(d,J＝86.7Hz,8H).
Step G4: under the protection of inert gas, the compound D is formylated under the action of phosphorus oxychloride and DMF to obtain a compound E by Vilsmeier-Haack (Vilsmeier-Haack);
Synthesis of compound E: compound D (1 g,0.49 mmol) was weighed into a 100mL two-necked round bottom flask, dissolved with ultra-dry N, N-dimethylformamide, the gas was replaced three times, protected by argon, phosphorus oxychloride (3.0 g,19.6 mmol) was added under ice bath, stirred for 30 minutes, and then heated to 90 ℃ for reaction overnight. The reaction was stopped, cooled to room temperature, extracted with Dichloromethane (DCM) and the solvent was dried. The crude product was purified by column chromatography to give compound D as an orange viscous compound (898 mg, 85% yield);
Hydrogen spectrum (400 MHz, deuterated chloroform) )(1HNMR(400MHz,Chloroform-d))δ10.11(s,4H),4.81(t,J＝7.3Hz,4H),4.44(d,J＝8.6Hz,8H),3.51-3.39(m,4H),2.96(s,4H),2.21(d,J＝8.0Hz,4H),1.93-1.85(m,4H),1.74(s,4H),1.36-1.10(m,84H),0.98-0.68(m,56H),0.64-0.10(m,36H),-0.07--0.17(m,4H),-0.36(s,4H).
Step G5: reacting the compound D with 5-bromo-3- (dicyanomethylene) indigoketone through Knoevenagel (Knoevenagel) to obtain a compound F (DSMA) with two five-membered rings A-DA' D-A connected with small molecules;
Synthesis of Compound F (DSMA): compound E (431 mg,0.2 mmol) and 5-bromo-3- (dicyanomethylene) indidone (242 mg,0.84 mmol) were weighed into a 100mL three-necked round bottom flask, dissolved in toluene, added boron trifluoride diethyl ether (2.8 g,4.0 mmol) with acetic anhydride 0.4mL under stirring at room temperature, reacted for 15 min, the reaction stopped, the solvent was dried by spinning, extracted with Dichloromethane (DCM), and the solvent was dried by spinning. The crude product was purified by column chromatography as dark blue solid compound F, (571 mg, 90% yield).
Hydrogen spectrum (400 MHz, deuterated chloroform) )(1HNMR(400MHz,Chloroform-d))δ9.22(dd,J＝7.3,3.3Hz,4H),8.56(d,J＝8.4Hz,4H),8.06-7.97(m,4H),7.85(ddd,J＝8.5,4.0,2.0Hz,4H),4.90(t,J＝7.3Hz,4H),4.49(dd,J＝29.2,13.7Hz,8H),3.42(q,J＝15.5,13.5Hz,4H),3.17(d,J＝16.5Hz,4H),2.35(s,4H),1.92(s,4H),1.77(s,2H),1.66(s,2H),1.25(s,84H),1.07-0.69(m,60H),0.59-0.27(m,28H),-0.01(s,4H),-0.26(s,4H).
Step G6: and (3) carrying out a Stille coupling reaction on the compound F and a double tin compound (pi) of thiophene or a derivative thereof to obtain the final organic cyclic conjugated molecule (RQM).
Synthesis of cyclic molecule RQM: compound F (100 mg,0.03 mmol) and 2, 5-bis (trimethyltin) thiophene (27 mg,0.06 mmol) were weighed into a round bottom flask, the gas was replaced three times, under the protection of argon, toluene and tetrakis triphenylphosphine palladium were added, and the reaction was completed at 110 ℃ for 2 hours. The reaction was cooled to room temperature, the solvent was dried, extracted with Dichloromethane (DCM) and the solvent was dried. The crude product was purified by column chromatography on a blue-black solid organic cyclic molecule RQM (54 mg, 60% yield);
hydrogen spectrum (400 MHz, deuterated chloroform) )(1HNMR(400MHz,Chloroform-d))δ9.21(s,4H),8.71(d,J＝8.3Hz,4H),8.24(s,4H),8.04(dd,J＝8.3,2.0Hz,4H),7.61(s,4H),4.83(s,4H),4.51(d,J＝19.5Hz,8H),3.47-3.31(m,4H),3.19(t,J＝9.8Hz,4H),2.20(s,4H),1.97(s,4H),1.86-1.76(m,4H),1.60-1.19(m,84H),1.06–0.29(m,88H),0.11–0.01(m,4H),-0.15(s,4H).
Example 3
Synthesis of cyclic molecule RQM-2F: compound F (100 mg,0.03 mmol) and (3, 4-difluorothienyl) bis-trimethyltin (26.7 mg,0.06 mmol) were weighed into a round-bottomed flask, the gas was replaced three times, argon was purged, toluene and tetrakis triphenylphosphine palladium were added, and the reaction was carried out at 110 ℃ for 2 hours, and the reaction was ended. The reaction was cooled to room temperature, the solvent was dried, extracted with Dichloromethane (DCM) and the solvent was dried. The crude product was purified by column chromatography on the dark green solid organic cyclic molecule RQM-2F, (57 mg, 61% yield);
Mass spectrometry (time of flight mass spectrometry) (MS (MALDITOF))
m/z:[M+H]+,calcdforC190H229F4N18O4S6,3094.65,found:3094.278.
Example 4
The organic cyclic molecule prepared in example 1 was applied to an organic photovoltaic cell as an electron acceptor material.
The photoelectric conversion layer is prepared from organic annular molecules and electron donor materials and used for an organic solar cell device, and the specific preparation process of the photoelectric conversion layer comprises the following steps: mixing an organic annular molecular acceptor material with an electron donor material, adding a solvent for dissolution to obtain slurry, coating the slurry on conductive glass to prepare a film, and then preparing the organic solar cell device. The solvent is generally at least one of chloroform, o-dichlorobenzene and tetrahydrofuran. The molar ratio of the quasi-polymer non-fullerene acceptor material to the electron donor material is 1-1.5:1, and the electron donor material is PM6 or PTQ 10.
Structural formulas of the compounds PM6 and PTQ10 (shown in the figure 19);
The technical effects actually achieved are as described in table 1:
Table 1 is based on PM6/PTQ10: OSCS photovoltaic Performance parameters of RQM
The foregoing invention has been generally described in great detail, but it will be apparent to those skilled in the art that modifications and improvements can be made thereto. Accordingly, it is intended to cover modifications or improvements within the spirit of the inventive concepts.
Claims (3)
1. An organic conjugated cyclic molecule, characterized in that: the conjugated cyclic molecule has the following structure:
Wherein R 1 is a straight-chain or branched-chain alkyl group having 2 to 20 carbon atoms; r 2 is a straight-chain or branched-chain alkyl group having 2 to 20 carbon atoms; r 3 is the same or different H, F or straight-chain alkane with 1-6 carbon atoms.
2. A preparation method of an organic conjugated cyclic molecule RQM1 is characterized by comprising the following steps: the synthetic route of the organic cyclic conjugated molecule RQM1 is as follows:
3. use of an organic conjugated cyclic molecule according to claim 1 in organic photovoltaics, characterized in that: the organic photovoltaic device is an organic solar cell.
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