CN115819365A - Organic compound, solar cell and preparation method thereof - Google Patents
Organic compound, solar cell and preparation method thereof Download PDFInfo
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- CN115819365A CN115819365A CN202211563180.5A CN202211563180A CN115819365A CN 115819365 A CN115819365 A CN 115819365A CN 202211563180 A CN202211563180 A CN 202211563180A CN 115819365 A CN115819365 A CN 115819365A
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- Prior art keywords
- hole transport
- solar cell
- independently
- transport layer
- organic compound
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title abstract description 13
- 239000010410 layer Substances 0.000 claims abstract description 129
- 230000005525 hole transport Effects 0.000 claims abstract description 83
- 239000000463 material Substances 0.000 claims abstract description 65
- 238000004770 highest occupied molecular orbital Methods 0.000 claims abstract description 25
- 239000000758 substrate Substances 0.000 claims abstract description 22
- 230000031700 light absorption Effects 0.000 claims abstract description 19
- 239000002346 layers by function Substances 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 150000004982 aromatic amines Chemical class 0.000 claims description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 229910052711 selenium Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- 239000000243 solution Substances 0.000 description 20
- 239000000654 additive Substances 0.000 description 17
- 239000011521 glass Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 230000000996 additive effect Effects 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000012043 crude product Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- -1 aromatic ring compound Chemical class 0.000 description 8
- XDXWNHPWWKGTKO-UHFFFAOYSA-N 207739-72-8 Chemical compound C1=CC(OC)=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C2=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC(=CC=C1C1=CC=C(C=C13)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 XDXWNHPWWKGTKO-UHFFFAOYSA-N 0.000 description 7
- 230000007774 longterm Effects 0.000 description 7
- 125000003003 spiro group Chemical group 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- YSHMQTRICHYLGF-UHFFFAOYSA-N 4-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=NC=C1 YSHMQTRICHYLGF-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- JEHMPNUQSJNJDL-OWOJBTEDSA-N 1-bromo-4-[(e)-2-(4-bromophenyl)ethenyl]benzene Chemical compound C1=CC(Br)=CC=C1\C=C\C1=CC=C(Br)C=C1 JEHMPNUQSJNJDL-OWOJBTEDSA-N 0.000 description 4
- NSEMERYXZLFBKN-UHFFFAOYSA-N 2,5-bis(4-bromophenyl)thiophene Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C=2C=CC(Br)=CC=2)S1 NSEMERYXZLFBKN-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 238000000137 annealing Methods 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 2
- VOJRFGKKQMVGPH-UHFFFAOYSA-N 1,4-bis(4-bromophenyl)butane-1,4-dione Chemical compound C1=CC(Br)=CC=C1C(=O)CCC(=O)C1=CC=C(Br)C=C1 VOJRFGKKQMVGPH-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- VOWZMDUIGSNERP-UHFFFAOYSA-N carbamimidoyl iodide Chemical compound NC(I)=N VOWZMDUIGSNERP-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical compound C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 230000009545 invasion Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-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
- 239000002243 precursor Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 238000001894 space-charge-limited current method Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 125000006617 triphenylamine group Chemical group 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- AOVCGMIQXVVCPS-UHFFFAOYSA-N BrC1(CC=C(C=C1)C=1C(=CC=CC=1)C1=CC=CC=C1)Br Chemical group BrC1(CC=C(C=C1)C=1C(=CC=CC=1)C1=CC=CC=C1)Br AOVCGMIQXVVCPS-UHFFFAOYSA-N 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
- ATLMFJTZZPOKLC-UHFFFAOYSA-N C70 fullerene Chemical compound C12=C(C3=C4C5=C67)C8=C9C%10=C%11C%12=C%13C(C%14=C%15C%16=%17)=C%18C%19=C%20C%21=C%22C%23=C%24C%21=C%21C(C=%25%26)=C%20C%18=C%12C%26=C%10C8=C4C=%25C%21=C5C%24=C6C(C4=C56)=C%23C5=C5C%22=C%19C%14=C5C=%17C6=C5C6=C4C7=C3C1=C6C1=C5C%16=C3C%15=C%13C%11=C4C9=C2C1=C34 ATLMFJTZZPOKLC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000662429 Fenerbahce Species 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
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- 229940006429 bismuth cation Drugs 0.000 description 1
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- 238000005893 bromination reaction Methods 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
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- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
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- 230000000694 effects Effects 0.000 description 1
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- ZTYYDUBWJTUMHW-UHFFFAOYSA-N furo[3,2-b]furan Chemical compound O1C=CC2=C1C=CO2 ZTYYDUBWJTUMHW-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- RJMMFJHMVBOLGY-UHFFFAOYSA-N indium(3+) Chemical compound [In+3] RJMMFJHMVBOLGY-UHFFFAOYSA-N 0.000 description 1
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- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
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- 229910052744 lithium Inorganic materials 0.000 description 1
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
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- 125000005561 phenanthryl group Chemical group 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- MHOZZUICEDXVGD-UHFFFAOYSA-N pyrrolo[2,3-d]imidazole Chemical compound C1=NC2=CC=NC2=N1 MHOZZUICEDXVGD-UHFFFAOYSA-N 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- ONCNIMLKGZSAJT-UHFFFAOYSA-N thieno[3,2-b]furan Chemical compound S1C=CC2=C1C=CO2 ONCNIMLKGZSAJT-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 238000004402 ultra-violet photoelectron spectroscopy Methods 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- 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
- Photovoltaic Devices (AREA)
Abstract
The application relates to an organic compound, a solar cell and a preparation method thereof. The solar cell comprises a conductive substrate, and a functional layer and an electrode layer which are sequentially stacked on the conductive substrate, wherein the functional layer comprises a perovskite light absorption layer and a hole transport layer; the material of the hole transport layer comprises one or more organic compounds, the organic compounds have the structural characteristics shown in the following formula (II), and the HOMO energy level of the hole transport layer is matched with the top energy level of the valence band of the perovskite light absorption layer. The solar cell is characterized in that the hole transport layer has a specific structureThe organic compound can effectively improve the photoelectric conversion efficiency.
Description
Technical Field
The application relates to the technical field of solar cells, in particular to an organic compound, a solar cell and a preparation method thereof.
Background
Perovskite solar cells (perovskite solar cells) are solar cells using perovskite type organic metal halide semiconductors as light absorbing materials, and belong to the third generation solar cells, which are also called new concept solar cells.
However, the photoelectric conversion efficiency of the conventional perovskite solar cell needs to be further improved, and an additive is usually required to be additionally added in the hole transport layer of the conventional perovskite solar cell to ensure the photoelectric conversion efficiency, which is not favorable for the long-term stability of the device.
Disclosure of Invention
Accordingly, the present application provides a solar cell having high photoelectric conversion efficiency and good stability, a method for manufacturing the same, and an organic compound.
In a first aspect of the present application, a solar cell is provided, which includes a conductive substrate, and a functional layer and an electrode layer sequentially stacked on the conductive substrate, wherein the functional layer includes a perovskite light-absorbing layer and a hole-transporting layer;
the material of the hole transport layer includes one or more of organic compounds having structural features as shown in the following formula (II):
wherein R is 1 、R 2 、R 3 And R 4 Each independently is a single bond, C2-C10 alkenyl, C6-C15 aryl, C4-C13 heteroaryl, or any of the foregoing groupsA combination of two or any three;
A 1 、A 2 、A 3 and A 4 Are each independently at least one S 1 Substituted or unsubstituted C6-C30 aromatic amine; s 1 Selected from: C1-C5 alkoxy;
and the HOMO energy level of the hole transport layer is matched with the top energy level of the valence band of the perovskite light absorption layer.
In one embodiment, the difference between the HOMO energy level of the hole transport layer and the top valence band energy level of the perovskite light absorbing layer is less than or equal to 0.3eV.
In one embodiment, the HOMO energy level of the hole transport layer is-5.5 eV to-5.1 eV; optionally, the HOMO energy level of the hole transport layer is between-5.3 eV and-5.1 eV.
In one embodiment, A 1 、A 2 、A 3 And A 4 Are each independently at least one S 1 Substituted C15-C20 aromatic amine; alternatively, S 1 Selected from the group consisting of: C1-C2 alkoxy.
In one embodiment, the organic compound has the structural features shown in formula (I) below:
wherein R is 1 、R 2 、R 3 And R 4 Each independently is a single bond, C2-C6 alkenyl, C6-C10 aryl, C4-C8 heteroaryl, or a combination of any two or any three of the foregoing groups.
In one embodiment, R 1 、R 2 、R 3 And R 4 Each independently is a single bond or one of the following groups:
wherein X is O, S or Se.
In one of which is implementedIn the examples, R 1 、R 2 、R 3 And R 4 Each independently is a single bond or one of the following groups:
in one embodiment, the organic compound is one or more of the following compounds:
in one embodiment, the hole transport layer has a hole mobility of 2 × 10 -4 ～6x10 -4 cm 2 V -1 s -1 . In a second aspect of the present application, there is provided a method for manufacturing a solar cell according to the first aspect, comprising the steps of: and sequentially preparing the functional layer and the electrode layer on the conductive substrate.
In one embodiment, the method of preparing the hole transport layer includes:
dissolving the organic compound in an organic solvent to prepare a hole transport solution;
performing film forming treatment on the hole transport solution;
optionally, the organic solvent is one or more of toluene, chlorobenzene and dichloromethane;
optionally, the concentration of the hole transport solution is 1 to 100mg/mL.
In a third aspect of the present application, there is provided an organic compound having a structural feature shown by the following formula (II):
R 1 、R 2 、R 3 and R 4 Each independently is a single bond, C2-C10 alkenyl, C6-C15 aryl, C4-C13 heteroaryl, or a combination of any two or any three of the foregoing groups;
A 1 、A 2 、A 3 and A 4 Are each independently at least one S 1 Substituted C6-C30 arylamines; s 1 Selected from: C1-C5 alkoxy.
In one embodiment, A 1 、A 2 、A 3 And A 4 Are each independently at least one S 1 Substituted C15-C20 arylamine; alternatively, S 1 Selected from: C1-C2 alkoxy.
In one embodiment, the organic compound has the structural features shown in formula (I) below:
wherein R is 1 、R 2 、R 3 And R 4 Each independently is a single bond, C2-C6 alkenyl, C6-C10 aryl, C4-C8 heteroaryl, or a combination of any two or any three of the foregoing groups.
In one embodiment, R 1 、R 2 、R 3 And R 4 Each independently is a single bond or one of the following groups:
wherein X is O, S or Se.
In one embodiment, R 1 、R 2 、R 3 And R 4 Each independently is a single bond or one of the following groups:
in one embodiment, the organic compound is one of the following compounds:
the solar cell adopts the organic compound with the specific structure on the hole transport layer, the organic compound is of a ring structure, the macromolecular skeleton of the traditional hole transport layer material is changed, and the R is adjusted 1 、R 2 、R 3 And R 4 The structure of the hole transport layer is matched with the aromatic amine group, so that the HOMO energy level of the hole transport layer is matched with the top energy level of the valence band of the perovskite light absorption layer, and the photoelectric conversion efficiency is effectively improved.
Detailed Description
The organic compound, the solar cell, and the method for manufacturing the same according to the present invention will be described in further detail with reference to specific examples. This application may be embodied in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used herein in the description of the present application is for the purpose of describing particular embodiments only and is not intended to be limiting of the application.
The "ranges" disclosed herein are defined in terms of lower limits and upper limits, with a given range being defined by a selection of one lower limit and one upper limit that define the boundaries of the particular range. Ranges defined in this manner may or may not include endpoints and may be arbitrarily combined, i.e., any lower limit may be combined with any upper limit to form a range. For example, if ranges of 60-120 and 80-110 are listed for a particular parameter, it is understood that ranges of 60-110 and 80-120 are also contemplated. Furthermore, if the minimum range values 1 and 2 are listed, and if the maximum range values 3,4, and 5 are listed, the following ranges are all contemplated: 1-3, 1-4, 1-5, 2-3, 2-4 and 2-5. In this application, unless otherwise stated, the numerical range "a-b" represents a shorthand representation of any combination of real numbers between a and b, where a and b are both real numbers. For example, a numerical range of "0 to 5" indicates that all real numbers between "0 to 5" have been listed herein, and "0 to 5" is simply an abbreviated representation of the combination of these numbers. In addition, when a parameter is an integer of 2 or more, it is equivalent to disclose that the parameter is, for example, an integer of 2, 3,4, 5, 6, 7, 8, 9, 10, 11, 12, or the like.
All embodiments and alternative embodiments of the present application may be combined with each other to form new solutions, if not specifically stated.
All technical and optional features of the present application may be combined with each other to form new solutions, if not otherwise specified.
All steps of the present application may be performed sequentially or randomly, preferably sequentially, if not specifically stated. For example, the method comprises steps (a) and (b), meaning that the method may comprise steps (a) and (b) performed sequentially, and may also comprise steps (b) and (a) performed sequentially. For example, reference to the process further comprising step (c) means that step (c) may be added to the process in any order, for example, the process may comprise steps (a), (b) and (c), may also comprise steps (a), (c) and (b), may also comprise steps (c), (a) and (b), etc.
The terms "comprises" and "comprising" as used herein mean either open or closed unless otherwise specified. For example, the terms "comprising" and "comprises" may mean that additional components not listed may also be included or included, or that only listed components may be included or included.
In this application, the term "or" is inclusive, unless otherwise specified. For example, the phrase "a or B" means "a, B, or both a and B. More specifically, either of the following conditions satisfies the condition "a or B": a is true (or present) and B is false (or not present); a is false (or not present) and B is true (or present); or both a and B are true (or present).
In the present application, the term "alkenyl" is meant to encompass a compound having at least one site of unsaturation, i.e., a carbon-carbon sp 2 The hydrocarbon of the double bond loses a hydrogen atom to form a monovalent residue. Phrases comprising this term, such as "C2 to C6 alkenyl" refer to alkenyl groups comprising 2 to 6 carbon atoms, which at each occurrence may be independently C2, C3, C4, C5 or C6 alkenyl. Suitable examples include, but are not limited to: vinyl (-CH = CH) 2 ) Allyl (-CH) 2 CH＝CH 2 ) Cyclopentenyl (-C) 5 H 7 ) And 5-hexenyl (-CH) 2 CH 2 CH 2 CH 2 CH＝CH 2 )。
In the present application, the term "aryl" refers to an aromatic hydrocarbon group derived by removing one hydrogen atom from the aromatic ring compound, and may be a monocyclic aryl group, or a fused ring aryl group, or a polycyclic aryl group, at least one of which is an aromatic ring system for polycyclic ring species. For example, "C6-C10 aryl" refers to an aryl group containing 6 to 20 carbon atoms, which at each occurrence, may be independently C6, C7, C8, C9, or C10 aryl. It is understood that the aryl group is short for an aromatic group and may include monocyclic aryl groups, fused ring aryl groups (e.g., naphthyl, anthryl, phenanthryl) or polycyclic aryl groups (e.g., biphenyl, triphenylamine, triphenylmethane).
In the present application, "heteroaryl" means that at least one carbon atom is replaced with a non-carbon atom, which may be a N atom, an O atom, an S atom, a Se atom, or the like, in addition to an aryl group. For example, "C4-C8 heteroaryl" refers to heteroaryl groups containing 3 to 10 carbon atoms, which at each occurrence, may be independently of each other, C4 heteroaryl, C5 heteroaryl, C6 heteroaryl, C7 heteroaryl, or C8 heteroaryl. Suitable examples include, but are not limited to: furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrole, furofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, phthalazine, quinoxaline, phenanthridine, primadine, quinazoline, quinazolinone, or selenophene.
In the present application, "aromatic amine" means an amine substituted with at least one aryl group, wherein the definition of aryl group is the same as above, and the number of aryl groups may be, without limitation, 1, 2 or 3. "C6-C30 aryl" means that the total number of carbon atoms in the "aromatic amine" is 6 to 30.
In the present application, "a combination of any two or any three" means that any two or any three groups are connected by a single bond. Examples are as follows: r 1 、R 2 、R 3 And R 4 Are each independently-R 01 -R 02 -or-R 03 -R 04 -R 05 -, in which R 01 、R 02 、R 03 、R 04 And R 05 Each independently is a C2-C10 alkenyl group, a C6-C15 aryl group, or a C4-C13 heteroaryl group.
Currently, the most commonly used hole transport layer material (HTM) in perovskite solar cells is Spiro-OMeTAD, whose structure is shown below:
however, the preparation process of the Spiro-OMeTAD is complex and high in cost, and meanwhile, additives such as Li salt and tBP are required to be used in the Spiro-OMeTAD hole transport layer to improve the mobility of the hole transport layer, and the Li salt can infiltrate into the perovskite light absorption layer to finally degrade the light absorption layer material, so that the long-term operation stability of the device of the perovskite solar cell is not facilitated. Therefore, developing a high hole mobility and low cost hole transport layer material that can be energy level matched with perovskite is a focus of attention in the field, and is a great challenge for the future perovskite solar cell industrialization.
One method involves a hole transport material for perovskite solar cells, which has the following structure:
the hole transport material of the perovskite solar cell takes tetraphenylethylene as a core structure, then diphenylamine is substituted at para positions of four benzene rings, and the expansion of a molecular structure is realized by changing the position substitution of methoxyl on peripheral benzene rings. However, the overall structure of the molecule is very similar to that of a Spiro-OMeTAD, and the HOMO level (-5.09 eV) of the hole transport layer is above the top level (-5.40 eV) of the valence band of the perovskite, and the energy level difference is large (-0.3 eV). This indicates that the energy levels of the two are not perfectly matched, which makes the photoelectric conversion efficiency of the device low (around 11%). Meanwhile, the additive still needs to be added into the hole transport layer in the process of preparing the device by using the hole transport material of the perovskite solar cell, which is not favorable for the long-term stability of the device.
In view of this, some examples of the present application provide a solar cell including an electrically conductive substrate, and a functional layer and an electrode layer sequentially stacked on the electrically conductive substrate, the functional layer including a perovskite light-absorbing layer and a hole-transporting layer;
the material of the hole transport layer includes one or more of organic compounds having structural features as shown in the following formula (II):
wherein R is 1 、R 2 、R 3 And R 4 Each independently is a single bond, C2-C10 alkenyl, C6-C15 aryl, C4-C13 heteroaryl, or a combination of any two or any three of the foregoing groups;
A 1 、A 2 、A 3 and A 4 Are respectively and independently at least oneA S 1 Substituted or unsubstituted C6-C30 aromatic amine; s 1 Selected from: C1-C5 alkoxy;
and the HOMO energy level of the hole transport layer is matched with the top energy level of the valence band of the perovskite light absorption layer. As will be appreciated, "matched" means that the HOMO level of the hole transport layer is close to the top valence band level of the perovskite light absorbing layer, e.g., by 0.3eV or less.
The solar cell adopts the organic compound with a specific structure in the hole transport layer, changes the macromolecular skeleton of the hole transport layer material, and adjusts R 1 、R 2 、R 3 And R 4 The structure of (2) is matched with the aromatic amine group, so that nitrogen atoms are hybridized to a certain degree, the regulation and control of the energy level of the hole transport layer are realized, the HOMO energy level of the hole transport layer is matched with the top energy level of the valence band of the perovskite light absorption layer, and the photoelectric conversion efficiency is further improved. Meanwhile, the hole transport layer has higher mobility, so that the solar cell has higher device efficiency and open-circuit voltage.
In addition, the hole transport layer does not need to be additionally added with additives, so that the influence of the additives on the long-term operation stability of the solar cell is avoided. Meanwhile, the hydrophobic property of the material is strong, so that the material not only can play a role in extracting and transmitting holes, but also is favorable for blocking the invasion of external water and oxygen, thereby being favorable for improving the long-term operation stability of the device.
In some of these examples, the difference between the HOMO level of the hole transport layer and the top valence band level of the perovskite light absorbing layer is ≦ 0.3eV. Specifically, the difference between the HOMO energy level of the hole transport layer and the top energy level of the valence band of the perovskite light absorbing layer includes, but is not limited to: 0.05eV, 0.08eV, 0.1eV, 0.13eV, 0.15eV, 0.16eV, 0.18eV, 0.2eV, 0.22eV, 0.24eV, 0.26eV, 0.3eV.
In some of these examples, the hole transport layer has a HOMO energy level in the range of-5.5 eV to-5.1 eV. Specifically, the HOMO energy level of the hole transport layer includes, but is not limited to: -5.5eV, -5.45eV, -5.4eV, -5.35eV, -5.32eV, -5.3eV, -5.29eV, -5.27eV, -5.25eV, -5.23eV, -5.21eV, -5.15eV, -5.1eV. Further, the HOMO energy level of the hole transport layer is-5.3 eV to-5.1 eV.
In some of these examples, A 1 、A 2 、A 3 And A 4 Are each independently at least one S 1 Substituted C15-C20 aromatic amine groups. Further, S 1 Selected from: C1-C2 alkoxy.
In some of these examples, A 1 、A 2 、A 3 And A 4 Each independently is triphenylamine.
In some of these examples, S 1 Selected from methoxy.
In some of these examples, the organic compound has the structural features shown in formula (I) below:
wherein R is 1 、R 2 、R 3 And R 4 Each independently is a single bond, C2-C6 alkenyl, C6-C10 aryl, C4-C8 heteroaryl, or a combination of any two or any three of the foregoing groups.
In some of these examples, R in the structures shown in formula (I) 1 、R 2 、R 3 And R 4 The same is true.
In some of these examples, R 1 、R 2 、R 3 And R 4 Each independently is a single bond or one of the following groups:
wherein X is O, S or Se.
In some of these examples, R 1 、R 2 、R 3 And R 4 Each independently is a single bond or one of the following groups:
in some of these examples, R 1 、R 2 、R 3 And R 4 Each independently is a single bond or one of the following groups:
further, R 1 、R 2 、R 3 And R 4 Is composed of
The HOMO energy level of the material obtained in the way can be better matched with a light absorption layer of a solar cell, and the mobility is higher. In some other examples, R 1 、R 2 、R 3 And R 4 Each independently a single bond or one of the following groups:
in some other examples, R 1 、R 2 、R 3 And R 4 Each independently is one of the following groups:
further, R 1 、R 2 、R 3 And R 4 Is composed of
Therefore, the photoelectric conversion efficiency of the battery device adopting the material is higher, and the stability is better.
In some of these examples, the organic compound is one or more of the following compounds:
in some of these examples, the hole transport layer has a hole mobility of 2 × 10 -4 ～6×10 -4 cm 2 V -1 s -1 . Further, the hole mobility was 2 × 10 -4 ～3.5×10 -4 cm 2 V -1 s -1 。
In some of these examples, no additive is included in the hole transport layer. It is understood that the additive means an additive used to enhance the mobility of the hole transport layer in the conventional method. Without limitation, the additive includes one or more of lithium bis (trifluoromethane) sulfonimide (Li-TFSI), cobalt-based (III) bis (trifluoromethane) sulfonimide (FK 209), and 4-tert-butylpyridine (tBP).
Without limitation, the solar cell may include a formal and a trans form. For formality, the solar cell includes a conductive substrate, and an electron transport layer, a light absorbing layer, a hole transport layer, and an electrode layer sequentially stacked on the substrate. For the trans form, the solar cell includes a conductive substrate, and a hole transport layer, a light absorbing layer, an electron transport layer, and an electrode layer sequentially stacked on the substrate.
In some of these examples, the hole transport layer has a thickness of 5nm to 100nm.
In some of these examples, the light absorbing layer is a perovskite light absorbing layer. Specifically, the perovskite light absorption layer has a chemical formula satisfying ABX 3 Or A 2 CDX 6 A is inorganic or organic-inorganic mixed cation and can be at least one of MA, FA and Cs; b is inorganic or organic-inorganic mixed cation, and can be at least one of Pb and Sn; c is inorganic or organic-inorganic mixed cation, usually Ag + (ii) a D is inorganic or organic-inorganic mixed cation, and can be bismuth cation Bi 3+ Antimony cation Sb 3+ And indium cation In 3+ At least one of; x is inorganic or organic-inorganic mixed anionAnd Br or I. The band gap of the perovskite light absorption layer is 1.20-2.30 eV, and the thickness is 200-1000 nm.
Without limitation, the conductive substrate is a transparent conductive glass substrate, and the conductive material may be, for example: FTO, ITO, AZO, BZO, IZO, and the like.
Without limitation, the electron transport layer material may be at least one of the following materials and their derivatives and their doped or passivated materials: [6,6]-phenyl radical C 61 Butyric acid methyl ester (PC) 61 BM)、[6,6]-phenyl radical C 71 Butyric acid methyl ester (PC) 71 BM), fullerene C60 (C60), fullerene C70 (C70), and tin dioxide (SnO) 2 ) Zinc oxide (ZnO), and the like.
Without limitation, the material of the electrode layer may be an organic or inorganic or organic-inorganic hybrid conductive material, such as: ag. Cu, C, au, al, etc.
The application also provides a preparation method of the solar cell, wherein the functional layer and the electrode layer are sequentially prepared on the conductive substrate.
In some of these examples, the method of making the hole transport layer comprises:
dissolving the organic compound in an organic solvent to prepare a hole transport solution;
and carrying out film forming treatment on the hole transport solution.
In some examples, the organic solvent is one or more of toluene, chlorobenzene, and dichloromethane;
in some examples, the concentration of the hole transport solution is 1 to 100mg/mL.
Without limitation, the film forming process is a sol-gel method, a knife coating method, a slit coating method, or the like, and then the organic solvent may be removed by means such as annealing or vacuum.
Specifically, the solar cell is formal, and the preparation method comprises the following steps:
step 1: etching and cleaning the transparent conductive glass substrate, and drying;
step 2: preparing an electron transport layer on the transparent conductive glass electrode;
and step 3: preparing a perovskite light absorption layer on the electron transport layer;
and 4, step 4: preparing a hole transport layer on the perovskite light absorption layer;
and 5: and preparing an electrode layer on the hole transport layer.
Specifically, the solar cell is in a trans-form, and the preparation method comprises the following steps: step 1: preparing a novel hole transport layer material;
step 1: etching and cleaning the transparent conductive glass substrate, and drying;
step 2: preparing a hole transport layer on the transparent conductive glass electrode;
and step 3: preparing a perovskite light absorption layer on the hole transport layer;
and 4, step 4: preparing an electron transport layer on the perovskite light absorption layer;
and 5: and preparing an electrode layer on the electron transport layer.
In some examples of the present application, there is provided an organic compound having a structural feature as shown in the following formula (II):
R 1 、R 2 、R 3 and R 4 Each independently is a single bond, C2-C10 alkenyl, C6-C15 aryl, C4-C13 heteroaryl, or a combination of any two or any three of the foregoing groups;
A 1 、A 2 、A 3 and A 4 Are each independently at least one S 1 Substituted C6-C30 arylamine; s 1 Selected from: C1-C5 alkoxy.
The organic compound forms a cyclic organic compound by changing the whole macromolecular skeleton, and is provided with a proper intermediate connecting group R 1 、R 2 、R 3 And R 4 The nitrogen atoms in the aromatic amine groups are hybridized to a certain degree, and research shows that the hole transport layer can be realized on one handThe energy level is regulated and controlled to be adaptive to a light absorption layer of the solar cell, and on the other hand, the mobility of the hole transport layer film can be effectively improved. Therefore, when the organic silicon solar cell is applied to a solar cell, the organic silicon solar cell has higher device efficiency and open-circuit voltage.
In addition, when the organic compound is used as a hole transport layer of the solar cell, no additive is required to be added additionally, and the influence of the additive on the long-term operation stability of the solar cell is avoided. Meanwhile, the hydrophobic property is strong, so that the cavity extracting and transmitting function can be achieved, and the invasion of external water and oxygen can be blocked, so that the long-term operation stability of the device can be improved.
In some of these examples, A 1 、A 2 、A 3 And A 4 Are each independently at least one S 1 Substituted C15-C20 aromatic amine; alternatively, S 1 Selected from: C1-C2 alkoxy.
In some of these examples, A 1 、A 2 、A 3 And A 4 Each independently is triphenylamine.
In some of these examples, S 1 Selected from methoxy.
In some of these examples, the organic compound has the structural features shown in formula (I) below:
wherein R is 1 、R 2 、R 3 And R 4 Each independently is a single bond, C2-C6 alkenyl, C6-C10 aryl, C4-C8 heteroaryl, or a combination of any two or any three of the foregoing groups.
In some of these examples, R in the structures shown in formula (I) 1 、R 2 、R 3 And R 4 The same is true.
In some of these examples, R 1 、R 2 、R 3 And R 4 Each independently is a single bond or one of the following groups:
wherein X is O, S or Se.
In some of these examples, R 1 、R 2 、R 3 And R 4 Each independently is a single bond or one of the following groups:
in some of these examples, R 1 、R 2 、R 3 And R 4 Each independently is a single bond or one of the following groups:
further, R 1 、R 2 、R 3 And R 4 Is composed of
The HOMO energy level of the material obtained in the way can be better matched with a light absorption layer of a solar cell, and the mobility is higher. In some other examples, R 1 、R 2 、R 3 And R 4 Each independently is a single bond or one of the following groups:
in some other examples, R 1 、R 2 、R 3 And R 4 Each independently is one of the following groups:
further, R 1 、R 2 、R 3 And R 4 Is composed of
Therefore, the photoelectric conversion efficiency of the battery device adopting the material is higher, and the stability is better.
In some of these examples, the organic compound is one of the following:
without limitation, R 1 、R 2 、R 3 And R 4 Same (with R) 0 Represented by (a), the method for preparing the organic compound may include the steps of:
s400: reacting compound 3 with compound 5 to prepare the organic compound;
R 0 is as defined for R 1 、R 2 、R 3 And R 4 。
The preparation method of the organic compound has simple steps, is easy to control, and can be suitable for industrial production.
In one example, the preparation method of compound 5 comprises the following steps:
s100: reacting the compound 1 with methyl chlorosilane to prepare a compound 2;
s200: reacting the compound 2 with the compound 3 to prepare a compound 4;
s300: carrying out bromination reaction on the compound 4 to prepare a compound 5;
examples
Hereinafter, examples of the present application will be described. The following description of the embodiments is merely exemplary in nature and is in no way intended to limit the present disclosure. The examples, where specific techniques or conditions are not indicated, are to be construed according to the techniques or conditions described in the literature in the art or according to the product specifications. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products commercially available.
Materials synthesis example:
example a (synthesis of material a):
s1: (E) Synthesis of- (4- (4-bromostyryl) phenyl) trimethylsilane:
1.0g (3 mmol) of trans-4, 4' -dibromostilbene are dissolved in 250mL of dry THF, cooled to-78 ℃ and protected with nitrogen. 3.0mL (6 mmol) of butyllithium was added dropwise to the cooled solution using a syringe, and a yellow precipitate was observed. After stirring the solution for 45 minutes, 1.2g (7 mmol) of methylchlorosilane were slowly added, brought to room temperature and stirred overnight. After quenching with 10mL of water, the crude product was extracted with 80mL of ether and 30mL of water, the organic phase was collected and washed with saturated ammonium chloride, dried over anhydrous magnesium sulfate and filtered. After concentrating the solution on a rotary evaporator, the reaction mixture was concentrated with THF: gradient column chromatography of n-hexane was performed to obtain 3g of product 1 (yield: 60%).
S2: synthesis of 4-methoxy-N, N-bis (4- ((E) -4- (trimethylsilyl) styryl) phenyl) aniline:
6.0g (48.7 mmol) of p-anisidine, 32.3g (97.4 mmol) of the product 1,0.3g (0.3 mmol) of Pd 2 (dba) 3 0.3g (0.4 mmol) of DPPF and 6g (63.4 mmol) of sodium tert-butoxide are dissolved in 120mL of toluene, stirred and rapidly quenchedThe temperature was raised to 70 ℃ and then slowly heated to 110 ℃ for reflux. After stirring and heating for 24 hours, the mixture was cooled to room temperature. The crude product was washed with 50mL of toluene and filtered, and the resulting filtrate was concentrated using a rotary evaporator. Subsequent recrystallization from 75mL heptane yielded the crude product. Filtration through silica gel with 120mL of cyclohexane yielded a purified product that yielded a white flaky solid after standing at 20 ℃ for three days. The solid was washed with 50mL of n-hexane and naturally air-dried to obtain 19.4g of product 2 (yield: 64%).
S3: synthesis of 4- ((E) -4-bromostyryl) -N- (4- ((E) -4-bromostyryl) phenyl) -N- (4-methoxyphenyl) aniline:
3.1g (5 mmol) of product 2 and 1.1g (6 mmol) of NBS are dissolved in 50mL of acetic acid, and after stirring at room temperature for 2 hours, the solution is poured into water and extracted 3 times with 10mL of n-hexane. The organic phase was washed with saturated sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated on a rotary evaporator to give a crude product. The crude product was purified by column chromatography (mobile phase: n-hexane) to obtain 3.9g (yield: 90%) of a colorless oily product.
S4: synthesis of Material A:
1.0g (8.1 mmol) of p-anisidine, 5.0g (8.0 mmol) of the product 3,0.05g (0.05 mmol) of Pd 2 (dba) 3 0.05g (0.07 mmol) of DPPF and 1g (10.6 mmol) of sodium tert-butoxide are dissolved in 20mL of toluene, stirred and rapidly warmed to 70 ℃ and then slowly heated to 110 ℃ for reflux. After stirring and heating for 24 hours, the mixture was cooled to room temperature. The crude product was washed with 10mL of toluene and filtered, and the filtrate was concentrated using a rotary evaporator. Subsequent recrystallization from 15mL heptane yielded the crude product. After filtration through silica gel using 20mL of cyclohexane, the solid was washed with 10mL of n-hexane and air-dried to obtain 5.7g of product 4, i.e., material A (yield: 60%).
Nuclear magnetic resonance testing (CDCl) of Material A 3 ，400MHz)：
1 H NMR:δ3.75(12H,s),6.83(8H,ddd,J＝8.7,2.7,0.5Hz),7.31(16H,ddd,J＝8.8,1.7,0.5Hz),7.46-7.71(24H,7.52(ddd,J＝8.8,1.6,0.5Hz),7.65(ddd,J＝8.7,1.5,0.5Hz))。
Example B (Synthesis of Material B)
Material B differs from material A in that material B replaces trans-4, 4' -dibromostilbene in step S1 with 4, 4-dibromoterphenyl (manufacturer: adamas, CAS 17788-94-2), and the remaining steps are the same as material A.
Nuclear magnetic testing (CDCl) of Material B 3 ，400MHz)：
1 H NMR:δ3.75(12H,s),6.38(16H,ddd,J＝8.7,2.7,0.5Hz),7.56(16H,ddd,J＝8.8,1.7,0.5Hz),7.71(16H,ddd,J＝8.8,1.7,0.5Hz),7.81-7.92(16H,7.52(ddd,J＝8.8,1.6,0.5Hz))。
Example C (Synthesis of Material C)
Material C differs from material a in that material C replaces trans-4, 4' -dibromostilbene in step S1 with 2, 5-bis (4-bromophenyl) thiophene, and the remaining steps are the same as material a.
Wherein, the synthesis process of the 2, 5-bis (4-bromophenyl) thiophene is as follows:
1, 4-bis (4-bromophenyl) butane-1, 4-dione (4.023gmg, 10mmol, available from Bide medicine, CAS: 2461-83-8) and Lawesson's reagent (6.362g, 15mmol, available from Bide medicine, CAS: 19172-47-5) were charged in a round bottom flask. Then, the operation of evacuating and introducing argon gas into the Schlenk tube was repeated 3 times to keep the Schlenk tube filled with argon gas. 60mL hexafluoroisopropanol (from Bide medicine, CAS: 920-66-1) was added under argon. The reaction mixture was reacted at reflux for 18h. After the reaction is finished, evaporating to dryness to obtain a crude product. The crude product was separated by column chromatography (200-300 particle size silica gel as a stationary phase, 1 volume ratio of ethyl acetate and n-hexane as mobile phases) to give 3.85g of 2, 5-bis (4-bromophenyl) thiophene in 98.21% yield.
Nuclear magnetic testing (CDCl) of 2, 5-bis (4-bromophenyl) thiophene 3 ，400MHz)：
1 HNMR：δ7.26-7.42(6H,7.33(ddd,J＝8.7,1.5,0.5Hz),7.36(d,J＝8.8Hz)),7.53(4H,ddd,J＝8.7,1.5,0.5Hz)。
Nuclear magnetic testing (CDCl) of Material C 3 ，400MHz)：
1 H NMR:δ3.28(12H,s),6.26(16H,ddd,J＝8.7,2.7,0.5Hz),7.28(16H,ddd,J＝8.8,1.7,0.5Hz),7.33(16H,ddd,J＝8.8,1.7,0.5Hz),7.56-7.88(8H,7.52(ddd,J＝8.8,1.6,0.5Hz))。
Example D (Synthesis of Material D)
Material D differs from material a in that material D replaces trans-4, 4' -dibromostilbene in step S1 with 1, 4-dibromobenzene, and the remaining steps are the same as material a.
Nuclear magnetic testing (CDCl) of Material D 3 ，400MHz)：
1 H NMR:δ3.75(12H,s),6.83(8H,ddd,J＝8.7,2.7,0.5Hz),7.30(16H,ddd,J＝8.8,1.8,0.5Hz),7.46-7.71(24H,7.52(ddd,J＝8.8,1.6,0.5Hz),7.65(ddd,J＝8.7,1.5,0.5Hz))。
Perovskite solar cell fabrication example:
example 1
1) Taking 20 pieces of FTO conductive glass with the specification of 2.0 x 2.0cm, removing FTO with the specification of 0.35cm at two ends respectively through laser etching, and exposing a glass substrate;
2) Ultrasonically cleaning the etched FTO conductive glass for a plurality of times by using water, acetone and isopropanol in sequence;
3) Blowing the FTO conductive glass to dry the solvent under a nitrogen gun, and further cleaning the FTO conductive glass in an ultraviolet ozone machine;
4) Mixing water with SnO 2 According to the following steps: 1, filtering with a filter membrane, taking 70 mu L on FTO, and rotating SnO at 3000rpm 2 And annealing at 100 ℃ for 30min after the spin coating is finished, and cooling to room temperature.
5) Weighing 223mg of lead iodide (PbI) 2 ) 80mg iodoformamidine (FAI) and 15mg chloromethane (MACl) are dissolved in a mixed solution of 0.8mL of DMF and 0.2mL of DMSO, stirred for 3h, filtered by a 0.22-micron organic filter membrane to obtain a perovskite precursor solution, the perovskite precursor solution is spin-coated on a passivation layer at 3000rpm/s, annealed at 100 ℃ for 30min, and cooled to room temperature to form a perovskite layer (the top energy level of the valence band is-5.45 eV), wherein an active substance in the perovskite layer is a CsFAMA system, and the thickness is 500nm.
6) Weighing 20mg of the material A, dissolving the material A in 1mL of chlorobenzene to obtain a hole transport layer solution, spin-coating the hole transport layer solution on the perovskite absorption layer at 3000rpm/s, and aging in dry air for 12 hours after the spin-coating is finished.
7) The obtained sheet is put into an evaporator, and metal electrodes Ag are evaporated to obtain the perovskite solar cell which is recorded as a cell device 1.
Example 2
The only difference from example 1 is that in step 6) material B is used instead of material a as the hole transport layer. A perovskite solar cell is obtained, denoted as cell device 2.
Example 3
The only difference from example 1 is that in step 6) material C is used instead of material a as the hole transport layer. A perovskite solar cell is obtained, denoted as cell device 3.
Example 4
The only difference from example 1 is that instead of material a, material D is used as the hole transport layer in step 6). A perovskite solar cell is obtained, denoted as cell device 4.
Comparative example 1
The same as example 1, except that in step 6) spiro was used instead of material a as the hole transport layer. A perovskite solar cell was obtained and designated as cell device D-1.
Comparative example 2
The same as example 1 except that a mixed solution of Spiro-OMeTAD and additives was used in step 6) instead of the hole transport layer solution of the material A to prepare a hole transport layer. A perovskite solar cell was obtained and designated as cell device D-2.
The preparation method of the mixed solution of the Spiro-OMeTAD and the additive comprises the following steps: to 1mL of a solution of Spiro-OMeTAD (73 mg) in chlorobenzene was added a solution of lithium bis (trifluoromethylsulfonyl) in Li-TFSI (18. Mu.L, 520mg/mL in acetonitrile), 30. Mu.g of 4-tert-butylpyridine (TBP) and 29. Mu.L of FK209 (29. Mu.L, 300mg/mL in acetonitrile), and the mixture was stirred for 1h and filtered for further use.
Test examples:
(1) Testing HOMO energy level of the material:
the preparation method of the sample comprises the following steps: the cleaned glass sheets were taken, and the material to be tested was spin-coated on the glass sheets (not on the perovskite absorption layer) according to step 6) of examples 1 to 4 and comparative examples 1 to 2, and annealed to obtain thin films of the test material.
The sample prepared above was measured by ultraviolet photoelectron spectroscopy UPS (AXIS ULTRA DLD from Kratos corporation) to obtain the HOMO level of the material to be tested, that is, the HOMO level of the hole transport layer.
(2) Testing of hole mobility of materials:
the hole mobility of the tested material is measured by a Space Charge Limited Current (SCLC) method, i.e. the hole mobility of the hole transport layer. The structure of the test device is ITO/PEDOT, PSS/hole transport layer/Au.
The preparation process of the test device is as follows:
ultrasonic cleaning ITO glass in water solution of detergent, secondary water, isopropanol and acetone for 20min, and cleaning with high purity N 2 Air drying, and treating in ultraviolet-ozone cleaning machine for 30min. PSS was then spin-coated onto the cleaned ITO substrate using a spin coater to a layer thickness of approximately 30nmAnd (3) placing the ITO glass sheet spin-coated with PEDOT (Poly ethylene glycol Ether-butyl ether) (PSS) on a hot table at 150 ℃ in an atmospheric environment and baking for 15min to ensure that no moisture remains in the film. The prepared ITO substrate was transferred into a glove box and a hole transport layer (prepared according to step 6 of examples 1-4 and comparative examples 1-2) was spin-coated on the PEDOT: PSS interface. Finally, the prepared glass sheet is put into a vacuum coating machine, and the thickness of the glass sheet is less than 5 multiplied by 10 -4 And depositing a metal Au electrode with the thickness of 30nm in a high vacuum environment of Pa. And annealing to obtain the test device.
The test results are shown in table 1 below:
TABLE 1
As can be seen from table 1, the HOMO levels of the materials a to D provided in the examples are higher than those of the conventional spiro and the spiro after the addition of the additive, and can be better matched with the light absorbing layer of the solar cell. Meanwhile, the materials A to D provided by the embodiment have obviously higher mobility than the traditional spiro under the condition of not adding additives, and are equivalent to the spiro added with the additives.
(3) Battery device performance testing
The test method comprises the following steps: the solar simulator with the light edge is adopted to test according with the national standard IEC61215, the crystalline silicon solar cell is adopted to correct the light intensity to reach the solar intensity AM 1.5, the cell device is connected with the digital source meter, and the photoelectric conversion efficiency of the cell device is measured under illumination.
The test results are shown in table 2 below:
TABLE 2
| Battery device | Day 3 efficiency | Day 30 efficiency | |
| Example 1 | Battery device 1 | 21.28％ | 20.09％ |
| Example 2 | Battery device 2 | 21.82％ | 20.34％ |
| Example 3 | Battery device 3 | 22.24％ | 20.71％ |
| Example 4 | Battery device 4 | 21.56％ | 20.11％ |
| Comparative example 1 | Battery device D-1 | 18.45％ | 16.37％ |
| Comparative example 2 | Battery device D-2 | 20.14％ | 11.79％ |
As can be seen from table 1, the photoelectric conversion efficiency of the battery devices made of the materials a to D provided in the examples is higher than that of the conventional spiro and the spiro with the additive added thereto, and the stability is better, and the high photoelectric conversion efficiency can be maintained even after 30 days.
The present application is not limited to the above embodiments. The above embodiments are merely examples, and embodiments having substantially the same configuration as the technical idea and exhibiting the same operation and effect within the technical scope of the present application are included in the technical scope of the present application. In addition, various modifications that can be conceived by those skilled in the art are applied to the embodiments and other embodiments are also included in the scope of the present application, in which some of the constituent elements in the embodiments are combined and constructed, without departing from the scope of the present application.
Claims (17)
1. The solar cell is characterized by comprising a conductive substrate, and a functional layer and an electrode layer which are sequentially laminated on the conductive substrate, wherein the functional layer comprises a perovskite light absorption layer and a hole transport layer;
the material of the hole transport layer includes an organic compound having a structural feature as shown in the following formula (II):
wherein R is 1 、R 2 、R 3 And R 4 Each independently is a single bond, C2-C10 alkenyl, C6-C15 aryl, C4-C13 heteroaryl, or a combination of any two or any three of the foregoing groups;
A 1 、A 2 、A 3 and A 4 Are each independently at least one S 1 Substituted or unsubstituted C6-C30 aromaticAn amine group; s 1 Selected from: C1-C5 alkoxy;
and the HOMO energy level of the hole transport layer is matched with the top energy level of the valence band of the perovskite light absorption layer.
2. The solar cell of claim 1, wherein the difference between the HOMO level of the hole transport layer and the top valence band level of the perovskite light absorbing layer is ≦ 0.3eV.
3. The solar cell according to claim 1, wherein the hole transport layer has a HOMO level of-5.5 eV to-5.1 eV; optionally, the HOMO energy level of the hole transport layer is between-5.3 eV and-5.1 eV.
4. The solar cell according to any one of claims 1 to 3, wherein A is 1 、A 2 、A 3 And A 4 Are each independently at least one S 1 Substituted C15-C20 aromatic amine; alternatively, S 1 Selected from the group consisting of: C1-C2 alkoxy.
5. The solar cell according to claim 4, wherein the organic compound has a structural feature represented by the following formula (I):
wherein R is 1 、R 2 、R 3 And R 4 Each independently is a single bond, C2-C6 alkenyl, C6-C10 aryl, C4-C8 heteroaryl, or a combination of any two or any three of the foregoing groups.
6. The solar cell according to any one of claims 1 to 3 and 5, wherein R is 1 、R 2 、R 3 And R 4 Each independently is a single bond or one of the following groups:
wherein X is O, S or Se.
7. The solar cell of claim 6, wherein R is 1 、R 2 、R 3 And R 4 Each independently is a single bond or one of the following groups:
8. a solar cell according to any of claims 1 to 3, characterized in that the organic compound is one or more of the following compounds:
9. the solar cell according to any one of claims 1 to 3, wherein the hole transport layer has a hole mobility of 2 x 10 -4 ～6×10 -4 cm 2 V -1 s -1 。
10. The method for manufacturing a solar cell according to any one of claims 1 to 9, comprising the steps of:
and sequentially preparing the functional layer and the electrode layer on the conductive substrate.
11. The method for manufacturing a solar cell according to claim 10, wherein the method for manufacturing the hole transport layer comprises:
dissolving the organic compound in an organic solvent to prepare a hole transport solution;
performing film forming treatment on the hole transport solution;
optionally, the organic solvent is one or more of toluene, chlorobenzene and dichloromethane;
optionally, the concentration of the hole transport solution is 1 to 100mg/mL.
12. An organic compound characterized by having a structural feature represented by the following formula (II):
R 1 、R 2 、R 3 and R 4 Each independently is a single bond, C2-C10 alkenyl, C6-C15 aryl, C4-C13 heteroaryl, or a combination of any two or any three of the foregoing groups;
A 1 、A 2 、A 3 and A 4 Are each independently at least one S 1 Substituted C6-C30 arylamine; s 1 Selected from: C1-C5 alkoxy.
13. An organic compound according to claim 12, wherein a is 1 、A 2 、A 3 And A 4 Are each independently at least one S 1 Substituted C15-C20 aromatic amine; alternatively, S 1 Selected from: C1-C2 alkoxy.
14. The organic compound of claim 13, having the structural features shown in formula (I) below:
wherein R is 1 、R 2 、R 3 And R 4 Each independently is a single bond, C2-C6 alkenyl, C6-C10 aryl, C4-C8 heteroaryl, or a combination of any two or any three of the foregoing groups.
15. The organic compound according to any one of claims 12 to 14, wherein R is 1 、R 2 、R 3 And R 4 Each independently is a single bond or one of the following groups:
wherein X is O, S or Se.
16. An organic compound according to claim 15, wherein R is 1 、R 2 、R 3 And R 4 Each independently is a single bond or one of the following groups:
17. the organic compound according to any one of claims 12 to 14, wherein the organic compound is one of the following compounds:
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| WO2019004781A1 (en) * | 2017-06-30 | 2019-01-03 | 한국화학연구원 | Perovskite solar cell |
| CN111138440A (en) * | 2020-01-03 | 2020-05-12 | 南京林业大学 | Preparation and application of organic hole transport material taking triptycene and tripeptidine as cores |
| CN113402439A (en) * | 2021-04-12 | 2021-09-17 | 南京邮电大学 | Isoindigo compound-containing hole transport material and preparation method and application thereof |
| CN114031571A (en) * | 2020-11-02 | 2022-02-11 | 广东聚华印刷显示技术有限公司 | Cyclic organic compound, composition, hole transport layer, and light-emitting device |
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| WO2019004781A1 (en) * | 2017-06-30 | 2019-01-03 | 한국화학연구원 | Perovskite solar cell |
| CN111138440A (en) * | 2020-01-03 | 2020-05-12 | 南京林业大学 | Preparation and application of organic hole transport material taking triptycene and tripeptidine as cores |
| CN114031571A (en) * | 2020-11-02 | 2022-02-11 | 广东聚华印刷显示技术有限公司 | Cyclic organic compound, composition, hole transport layer, and light-emitting device |
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