CN109337046B - Polymer donor material containing dibenzothiophene sulfoxide unit and preparation thereof - Google Patents
Polymer donor material containing dibenzothiophene sulfoxide unit and preparation thereof Download PDFInfo
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- CN109337046B CN109337046B CN201811055667.6A CN201811055667A CN109337046B CN 109337046 B CN109337046 B CN 109337046B CN 201811055667 A CN201811055667 A CN 201811055667A CN 109337046 B CN109337046 B CN 109337046B
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- polymer
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- dibenzothiophene sulfoxide
- dibenzothiophene
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- 229920000642 polymer Polymers 0.000 title claims abstract description 40
- 239000000463 material Substances 0.000 title claims abstract description 38
- NGDPCAMPVQYGCW-UHFFFAOYSA-N dibenzothiophene 5-oxide Chemical group C1=CC=C2S(=O)C3=CC=CC=C3C2=C1 NGDPCAMPVQYGCW-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 11
- -1 fullerene small molecule Chemical class 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 8
- 229910003472 fullerene Inorganic materials 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 claims description 3
- TXZZSZDCOCQKCS-UHFFFAOYSA-N C(C)C(CN1C(C2=C(N(C(C2=C1C=1SC(=CC=1)[Sn](C)(C)C)=O)CC(CCCC)CC)C=1SC(=CC=1)[Sn](C)(C)C)=O)CCCC Chemical compound C(C)C(CN1C(C2=C(N(C(C2=C1C=1SC(=CC=1)[Sn](C)(C)C)=O)CC(CCCC)CC)C=1SC(=CC=1)[Sn](C)(C)C)=O)CCCC TXZZSZDCOCQKCS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000000950 dibromo group Chemical group Br* 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 238000010898 silica gel chromatography Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000005893 bromination reaction Methods 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000004062 sedimentation Methods 0.000 claims 1
- 238000000967 suction filtration Methods 0.000 claims 1
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 6
- 238000000862 absorption spectrum Methods 0.000 abstract description 5
- 230000003647 oxidation Effects 0.000 abstract description 3
- 230000008033 biological extinction Effects 0.000 abstract 1
- 238000001514 detection method Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 7
- 238000012986 modification Methods 0.000 description 7
- 230000004048 modification Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class 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 5
- 230000031700 light absorption Effects 0.000 description 5
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 229920000547 conjugated polymer Polymers 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 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 2
- WFUBUHFODBEPNY-UHFFFAOYSA-N 2,8-dioctyldibenzothiophene Chemical compound C1=C(CCCCCCCC)C=C2C3=CC(CCCCCCCC)=CC=C3SC2=C1 WFUBUHFODBEPNY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 238000000944 Soxhlet extraction Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 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 2
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- IBXMKLPFLZYRQZ-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 IBXMKLPFLZYRQZ-UHFFFAOYSA-N 0.000 description 1
- WNEXSUAHKVAPFK-UHFFFAOYSA-N 2,8-dibromodibenzothiophene Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3SC2=C1 WNEXSUAHKVAPFK-UHFFFAOYSA-N 0.000 description 1
- HQOWCDPFDSRYRO-CDKVKFQUSA-N CCCCCCc1ccc(cc1)C1(c2cc3-c4sc5cc(\C=C6/C(=O)c7ccccc7C6=C(C#N)C#N)sc5c4C(c3cc2-c2sc3cc(C=C4C(=O)c5ccccc5C4=C(C#N)C#N)sc3c12)(c1ccc(CCCCCC)cc1)c1ccc(CCCCCC)cc1)c1ccc(CCCCCC)cc1 Chemical compound CCCCCCc1ccc(cc1)C1(c2cc3-c4sc5cc(\C=C6/C(=O)c7ccccc7C6=C(C#N)C#N)sc5c4C(c3cc2-c2sc3cc(C=C4C(=O)c5ccccc5C4=C(C#N)C#N)sc3c12)(c1ccc(CCCCCC)cc1)c1ccc(CCCCCC)cc1)c1ccc(CCCCCC)cc1 HQOWCDPFDSRYRO-CDKVKFQUSA-N 0.000 description 1
- 238000006619 Stille reaction Methods 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 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
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- IOOQQIVFCFWSIU-UHFFFAOYSA-M magnesium;octane;bromide Chemical compound [Mg+2].[Br-].CCCCCCC[CH2-] IOOQQIVFCFWSIU-UHFFFAOYSA-M 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [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 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- 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
- C08G61/126—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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- 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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/12—Copolymers
- C08G2261/124—Copolymers alternating
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/141—Side-chains having aliphatic units
- C08G2261/1412—Saturated aliphatic units
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/18—Definition of the polymer structure conjugated
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3241—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3243—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
- C08G2261/414—Stille reactions
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/91—Photovoltaic applications
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- 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
Abstract
The invention discloses a polymer solar cell donor material containing dibenzothiophene sulfoxide units and a preparation method thereof. The molecular main chain of the polymer donor material contains dibenzothiophene sulfoxide units with medium electron withdrawing capability, and the dibenzothiophene sulfoxide units and the strong electron donating or electron withdrawing units are polymerized by Stille to prepare the novel medium-wide band gap donor material. The polymer has the characteristics of excellent oxidation resistance, lower HOMO energy level, adjustable absorption spectrum, high molar extinction coefficient, good solubility and the like, and has great potential application value in the fields of organic solar cells, fluorescence sensors and biological detection.
Description
Technical Field
The invention relates to a conjugated polymer donor material applied to a photosensitive active layer of an organic solar cell, in particular to a conjugated polymer donor material containing dibenzothiophene sulfoxide units and a preparation method thereof.
Background
Organic solar cells (OPVs) are becoming a research hotspot in the photovoltaic field due to their light weight, low cost, flexibility, and large area printing. Wherein the photoactive active layer material is the host material for converting sunlight into electrical energy, is a key factor in determining OPV performance, and generally consists of a donor material and a acceptor material. In the development history of OPV, fullerene derivatives have long been dominant as acceptor materials. The professor of the Beijing university, occupying the Showcase, reports the condensed ring non-fullerene-like small molecule acceptor ITIC for the first time, and the photoelectric conversion efficiency of the condensed ring non-fullerene-like organic solar cell (NF-OPV) is greatly improved, the photovoltaic efficiency of the condensed ring non-fullerene-like organic solar cell is over 13%, and the overtaking of the fullerene-like OPV is realized.
Fused ring non-fullerene-like receptors (NF) differ from fullerene derivatives in having an anisotropic conjugated backbone, a similar chemical structure to the conjugated polymeric donor material and a narrower band gap, and thus donor materials that were originally blended with fullerene receptors to obtain excellent photoelectric properties show inapplicability in NF systems. Research shows that the medium-wide band gap donor material can form complementary absorption spectrum with condensed ring non-fullerene acceptor, and has relatively high open circuit voltage (V oc ). Thus, wide band gap donor materials in the design have a critical role in advancing NF-OPV development.
Barbarella [1] The et al found that the sulfur atom of thiophene was subjected toOxidation can effectively reduce HOMO and LUMO (lowest unoccupied molecular orbital) of thiophene groups, converting thiophene from electron-rich wide bandgap p-type semiconductors with higher HOMO energy levels to electron-deficient n-type semiconductors. North China tally worker Yang Wei and the like [2-3] Taking S, S-dioxy-dibenzothiophene as an acceptor unit, taking IDT as an electron donor group, and performing Stille coupling polymerization to obtain a polymer donor PIDT-DHTSO with a band gap of 2.2eV, wherein the HOMO and LUMO energy levels are respectively-5.33, -3.13eV, and the hole mobility is 2.3X10 -4 cm 2 Vs and fullerene PC 71 The PCE of the device prepared by BM blending reaches 3.8 percent, is superior to the polymer without sulfone group of the same type, and is an ideal wide band gap donor material. They did not investigate the performance of devices made by blending with NF receptors.
Compared with S, S-dioxo-dibenzothiophene, dibenzothiophene sulfoxide has better solubility due to non-planarity of-SO group [4] . The strong polarity of sulfoxide groups can enhance pi-pi and dipole action among molecules, optimize crystallization performance of the molecules and improve morphology of the photoactive layer. As weak acceptor units, dibenzothiophene sulfoxides can be copolymerized with strong donor groups or strong acceptor groups to form stronger intramolecular push-pull actions on conjugated backbones. Meanwhile, due to the condensation effect of phenyl groups on two sides of thiophene, the stability of dibenzothiophene sulfoxide can be ensured. In addition, dibenzothiophene exists in a large amount in gasoline, and is a petrochemical product with wide sources. Therefore, the development of the intermediate and broadband donor material based on the dibenzothiophene sulfoxide unit has wide application prospect in NF-OSC devices.
The method comprises the following steps: reference to the literature
[1]Barbarella G,Favaretto L,Sotgiu G,et al.Modified oligothiophenes with High photo-and electroluminescence efficiencies[J].Advanced Materials,1999,11(16):1375-1379.
[2]He R,Xu J,Yang Y,et al.Dibenzothiophene-S,S-dioxide based medium-band-gap polymers for efficient bulk heterojunction solar cells[J].Organic Electronics,2014,15(11):2950-2958.
[3] Yang Wei, he Ruifeng, and the like, electron donor polymers containing s, s-dioxy-dibenzothiophene units and their use are described in CN 104004165A [ P ] 2014.
[4]Di Maria F,Zangoli M,PalamáI E,et al.Improving the Property-Function Tuning Range of Thiophene Materials via Facile Synthesis of oligo/polythiophene-S-oxides and mixed oligo/polythiophene-S-oxides/oligo/polythiophene-S,S-dioxides[J].Advanced Functional Materials,2016,26(38):6970-6984.
Disclosure of Invention
The invention provides a polymer donor material containing dibenzothiophene sulfoxide units, which has the following molecular structural formula:
wherein n represents a natural number in the polymerization degree, preferably 1 to 500; r is R 1 、R 2 H, F, independently, having C 1 ～C 30 Straight-chain or branched alkyl, alkoxy or thioalkyl radicals, R 1 、R 2 The same or different.
Pi units are heterocyclic groups of moderate electron donating ability:
wherein R is 3 、R 4 H, F, independently, having C 1 ～C 30 Straight-chain or branched alkyl, alkoxy or thioalkyl radicals, R 3 、R 4 The same or different; x is a heteroatom such as O, S, se, te.
The B unit is one of the following strong electron donating or strong electron withdrawing units:
the strong electron donating unit is as follows:
the strong electron-withdrawing unit is as follows:
wherein R is C 1 ～C 30 Straight or branched alkyl of (a).
The preparation method of the polymer donor material containing the dibenzothiophene sulfoxide unit comprises the following steps:
(1) Synthesis of dibenzothiophene sulfoxide acceptor units
Compound M 1 Dispersing zirconium tetrachloride in methanol, dropwise adding hydrogen peroxide at 0deg.C, stirring at room temperature, performing oxidation reaction, extracting the product with dichloromethane after the reaction, drying, and performing silica gel column chromatography to obtain dibenzothiophene sulfoxide M 2 . Mixing the product with quantitative N-bromosuccinimide, and brominating to obtain dibromo product M of acceptor unit dibenzothiophene sulfoxide 3 。
(2) Synthesis of polymers containing dibenzothiophene sulfoxide acceptor units
Under the protection of nitrogen, a double-tin compound of pi-B-pi and a double-bromine monomer of dibenzothiophene sulfoxide are subjected to Stille polymerization reaction in a polar solvent under the action of a catalyst to obtain the polymer. After the reaction is finished and cooled, the mixture is poured into a large amount of methanol, pumped and filtered, purified by a Soxhlet extractor, dissolved in a solvent, settled by the methanol and dried to obtain the polymer. The polymer is the photosensitive active layer donor material of the solar cell.
Preferably, the molar ratio of the double tin compound of pi-B-pi to the double bromine compound of dibenzothiophene sulfoxide is 1:1. the catalyst is tetra (triphenylphosphine) palladium or tri (dibenzylideneacetone) dipalladium taking triphenylphosphine as a ligand. The polar solvent is one or two mixed solvents of toluene, chlorobenzene and N, N-dimethylformamide, and the proportion is 1: 10-20: 1.
the conjugated polymer donor material prepared by the method is characterized by gel permeation chromatography, the number average molecular weight is 10000-100000, and the molecular weight distribution is 1.1-5; the band gap of the polymer is 1.8-2.5 eV; the ultraviolet-visible light absorption range is 300-800 nm, and the ultraviolet-visible light absorption range is wider; the polymer has excellent solubility and film forming property.
The application of the invention is as follows: the designed and synthesized photosensitive active layer donor material containing the dibenzothiophene sulfoxide polymer is blended with condensed ring non-fullerene small molecular receptors in different proportions to prepare a bulk heterojunction organic solar cell device, so that the high-efficiency photoelectric conversion of the device is realized.
The organic solar cell device comprises an Indium Tin Oxide (ITO) conductive glass anode, an anode modification layer, a photosensitive active layer, a cathode modification layer and a cathode. The active layer material is the polymer donor material containing dibenzothiophene sulfoxide and condensed ring non-fullerene small molecule acceptor material.
Compared with the prior art, the invention has the following advantages:
(1) The oxidation treatment effectively reduces the HOMO and LUMO energy levels of molecules while improving the oxidation resistance of the dibenzothiophene. The polymer donor material based on dibenzothiophene sulfoxide has a medium band gap, and the absorption spectrum and the fused ring non-fullerene small molecule can form complementation.
(2) The dibenzothiophene sulfoxide has a rigid planar structure, the stronger polarity of the sulfoxide can enhance intermolecular dipole action, improve the crystallization performance of the polymer, improve the appearance of an active layer and improve the carrier mobility.
(3) The polymer donor material containing dibenzothiophene sulfoxide units can be dissolved in common organic solvents such as dichloromethane, chloroform, toluene, chlorobenzene or dichlorobenzene. The higher light absorption coefficient and hole mobility lead the nano-structure to show excellent performance and wide application prospect in NF-OSC devices.
(4) The polymer donor material is constructed by using dibenzothiophene sulfoxide, and the method has the advantages of wide raw material sources, simple and feasible synthesis method, mild reaction conditions and contribution to large-scale production.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of 3, 7-dibromo-2, 8-dioctyl dibenzothiophene sulfoxide prepared in example 1 of the present invention.
FIG. 2 shows the nuclear magnetic resonance hydrogen spectrum of the polymer obtained in example 1 of the present invention
FIG. 3 shows the nuclear magnetic resonance hydrogen spectrum of the polymer obtained in example 2 of the present invention
FIG. 4 is an ultraviolet-visible absorption spectrum of a chloroform solution of a polymer and a solid film in example 1 of the present invention
FIG. 5 is an ultraviolet-visible absorption spectrum of a chloroform solution of a polymer and a solid film in example 2 of the present invention
FIG. 6 shows the cyclic voltammogram of the polymer in example 1 of the present invention
Detailed Description
The present invention will be further described by way of examples below, but the present invention is not limited to the examples listed.
Example 1
In this example, the polymer has the following structural formula:
the preparation of the polymer comprises the following steps:
(1) Preparation of dibenzothiophene sulfoxide acceptor units
Into a 500mL round bottom flask was added 2, 8-dibromodibenzothiophene (5 g,14.6 mmol), 1, 3-bis (dibenzo) in sequence
Nickel dichloride (396.2 mg,0.73 mmol) and anhydrous tetrahydrofuran (200 mL), nitrogen-protected, was slowly added dropwise 2mol/L of n-octylmagnesium bromide (29.2 mL,58.4 mmol) at 0deg.C, warmed to room temperature, and reacted for 6h. Quenching the reaction with aqueous ammonium chloride solution, rotary evaporating the majorityAfter separation of the solution, extraction with dichloromethane, combining the organic phases and using anhydrous MgSO 4 And (5) drying. After the organic solvent was removed by distillation under the reduced pressure, the residue was subjected to column chromatography using petroleum ether as an eluent to give a colorless oily liquid (4.8 g, yield 80%). 1 H NMR(300MHz,CDCl 3 )δ7.95(s,2H),7.73(d,J＝8.1Hz,2H),7.28(s,J＝9Hz,2H),2.77(s,4H),1.71(s,4H),1.27(s,20H),0.88(s,6H)。
Into a 250mL round bottom flask, 2, 8-dioctyl-dibenzothiophene (4 g,9.8 mmol), zirconium tetrachloride (6.85 g,29.4 mmol) were added sequentially, dissolved in a mixed solvent of 125mL of methanol and 20mL of dichloromethane, and hydrogen peroxide (3 mL) was slowly added dropwise at 0deg.C. Reacting for 4 hours at room temperature, adding NaHSO 3 Quenching with water solution. After rotary evaporation of the majority of the solution, extraction with dichloromethane, combining the organic phases and using anhydrous MgSO 4 And (5) drying. After the organic solvent was removed by distillation under the reduced pressure, column chromatography was performed on the residue with petroleum ether/dichloromethane (2:1) as eluent to give a white solid (2.6 g, yield 60%). 1 H NMR(400MHz,CDCl 3 )δ7.88(d,J＝7.9Hz,2H),7.62(s,2H),7.31(d,J＝9.1Hz,2H),2.74(s,4H),1.70(d,J＝6.9Hz,4H),1.34(s,20H),0.90(s,6H)。
To a 100mL single-necked flask, 2, 8-dioctyl dibenzothiophene sulfoxide (1 g,2.4 mmol) and trifluoroacetic acid (12 mL) were successively added, and after the raw materials were sufficiently dissolved, N-bromosuccinimide (1.68 g,9.4 mmol) was added in portions at 0℃and reacted at room temperature for 12 hours. After completion of the reaction, most of the solution was rotary evaporated, extracted with dichloromethane, the organic phases combined and dried over anhydrous MgSO 4 And (5) drying. After the organic solvent was removed by distillation under the reduced pressure, column chromatography was performed on the residue with petroleum ether/dichloromethane (1:2) as an eluent to give a white solid (0.44 g, yield 32%). 1 H NMR(400MHz,CDCl 3 )δ8.09(s,2H),7.60(s,2H),2.83(s,4H),1.66(s,4H),1.29(s,20H),0.89(s,6H)。
(2) Preparation of polymeric donor materials
To a 50mL single-necked flask, 3, 7-dibromo-2, 8-dioctyl dibenzothiophene sulfoxide (100 mg,1.7 mmol), 2, 5-bis (2-ethylhexyl) -3, 6-bis (5- (trimethylstannyl) thiophen-2-yl) -2, 5-dihydropyrrolo [3,4-c ] pyrrole-1, 4-dione (146 mg,1.7 mmol), tris (dibenzylideneacetone) dipalladium (4.7 mg,0.005 mmol), tris (o-methylphenyl) phosphorus (9.4 mg,0.03 mmol) and toluene (6 mL) were sequentially added, and the mixture was refluxed under a nitrogen atmosphere at 110℃for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction mixture was settled in methanol. Sequentially performing Soxhlet extraction with methanol and acetone, dissolving with chloroform, settling with methanol, and drying to obtain blue-violet solid 128mg with 76% yield.
The nuclear magnetic hydrogen spectrum of the polymer prepared by the method is characterized in that: 1 H NMR(400MHz,CDCl 3 ) δ9.05 (s, 2H), 8.04 (s, 2H), 7.80 (s, 2H), 7.31 (s, 2H), 4.08 (s, 4H), 2.92 (s, 4H), 1.95 (s, 2H), 1.66 (s, 4H), 1.32 (d, j=41.7hz, 18H), 0.87 (s, 9H). The solid film has light absorption range of 320-720 nm, optical band gap of 1.8eV, HOMO energy level of-5.37 eV, LUMO energy level of-3.56 eV, good solubility and film forming performance.
Example 2
In this example, the polymer has the following structural formula:
the preparation of the polymer comprises the following steps:
to a 50mL single-necked flask, 3, 7-dibromo-2, 8-dioctyl dibenzothiophene sulfoxide (100 mg,0.17 mmol), 5 '-bistrimethyltin-2, 2' -bithiophene (84.4 mg,0.17 mmol), tris (dibenzylideneacetone) dipalladium (4.8 mg, 0.003mmol), tris (o-methylphenyl) phosphorus (9.4 mg,0.02 mmol) and toluene (6 mL) were sequentially added, and the mixture was refluxed at 110℃for 24 hours under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction mixture was settled in methanol. Sequentially performing Soxhlet extraction with methanol and acetone, dissolving with chloroform, and drying to obtain orange yellow solid 50mg with 48% yield.
The nuclear magnetic hydrogen spectrum of the polymer prepared by the method is characterized in that: 1 H NMR(400MHz,CDCl 3 ) δ8.01 (s, 2H), 7.75 (s, 2H), 7.24 (d, j=3.2 hz, 2H), 7.07 (d, j=3.1 hz, 2H), 2.92 (d, j=7.9 hz, 4H), 1.68 (s, 4H), 1.28 (s, 20H), 0.88 (s, 6H). The solid film has light absorption range of 300-530 nm, optical band gap of 2.3eV, good solubility and film forming performance.
The conjugated polymer prepared by the embodiment can be used as a donor material to be blended with non-fullerene small molecules or polymer acceptor materials to prepare a photosensitive active layer of the organic solar cell. The organic solar cell may employ a formal or trans device structure. When the organic solar cell is in a formal structure, the device sequentially comprises an anode of Indium Tin Oxide (ITO) conductive glass, an anode modification layer, a photosensitive active layer, a cathode modification layer and a cathode; when the organic solar cell is of a trans-type structure, the device sequentially comprises an ITO conductive glass anode, a cathode modification layer, a photosensitive active layer, an anode modification layer and a cathode.
The foregoing embodiments have been described in some detail for purposes of clarity of understanding, it will be appreciated that the invention is not limited to the specific embodiments described above, but is intended to cover modifications, additions and substitutions within the scope of the principles of the invention.
Claims (1)
1. A polymer donor material comprising dibenzothiophene sulfoxide units, having the chemical structural formula:
wherein n represents the degree of polymerization;
the preparation method of the polymer donor material containing the dibenzothiophene sulfoxide unit comprises the following steps:
(1) Synthesis of dibenzothiophene sulfoxide acceptor units
Dispersing a compound M1 and zirconium tetrachloride in methanol, dropwise adding hydrogen peroxide at 0 ℃, stirring at room temperature, performing oxidation reaction, extracting a product by using methylene dichloride after the reaction is finished, drying, performing silica gel column chromatography to obtain dibenzothiophene sulfoxide, and performing bromination reaction on the product and quantitative N-bromosuccinimide to obtain a dibromo product of a receptor unit dibenzothiophene sulfoxide;
(2) Synthesis of polymer donor materials containing dibenzothiophene sulfoxide units
Under the protection of nitrogen, 2, 5-bis (2-ethylhexyl) -3, 6-bis (5- (trimethylstannyl) thiophene-2-yl) -2, 5-dihydropyrrolo [3,4-c ] pyrrole-1, 4-dione and dibenzothiophene sulfoxide dibromo monomer react in polar solvent under the action of catalyst to obtain polymer, after the reaction is finished and cooled, the polymer is poured into a large amount of methanol, suction filtration, purification by a Soxhlet extractor, solvent dissolution, and drying after sedimentation by methanol to obtain the polymer, wherein the polymer is the donor material of the photosensitive active layer of the solar cell;
the polymer donor material containing the dibenzothiophene sulfoxide unit is used as an organic solar cell donor material, and is blended with the condensed ring non-fullerene small molecule acceptor material to prepare a photosensitive active layer of a solar cell and the organic solar cell thereof.
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|---|---|---|---|---|
| US4965284A (en) * | 1988-05-19 | 1990-10-23 | American Cyanamid Company | Substituted dibenzothiophenes |
| CN104004165A (en) * | 2014-05-07 | 2014-08-27 | 华南理工大学 | S,S-dioxo-dibenzothiophene unit-containing electron donor polymer and use thereof |
| CN106905514A (en) * | 2017-03-31 | 2017-06-30 | 中国科学院宁波材料技术与工程研究所 | Polymer comprising benzo disulfoxide fen group or small molecule material, its preparation method and application in molecular backbone |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4965284A (en) * | 1988-05-19 | 1990-10-23 | American Cyanamid Company | Substituted dibenzothiophenes |
| CN104004165A (en) * | 2014-05-07 | 2014-08-27 | 华南理工大学 | S,S-dioxo-dibenzothiophene unit-containing electron donor polymer and use thereof |
| CN106905514A (en) * | 2017-03-31 | 2017-06-30 | 中国科学院宁波材料技术与工程研究所 | Polymer comprising benzo disulfoxide fen group or small molecule material, its preparation method and application in molecular backbone |
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