CN117651466A - Organic mixture, composition and application thereof - Google Patents
Organic mixture, composition and application thereof Download PDFInfo
- Publication number
- CN117651466A CN117651466A CN202311635895.1A CN202311635895A CN117651466A CN 117651466 A CN117651466 A CN 117651466A CN 202311635895 A CN202311635895 A CN 202311635895A CN 117651466 A CN117651466 A CN 117651466A
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- Prior art keywords
- carbon atoms
- group
- linear
- branched
- alkyl group
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 51
- 239000000463 material Substances 0.000 claims abstract description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims description 181
- 125000000217 alkyl group Chemical group 0.000 claims description 135
- 150000002894 organic compounds Chemical class 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- 125000004414 alkyl thio group Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 125000006413 ring segment Chemical group 0.000 claims description 20
- 239000003960 organic solvent Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 26
- 239000002131 composite material Substances 0.000 abstract description 4
- 238000010521 absorption reaction Methods 0.000 abstract description 3
- 229910000905 alloy phase Inorganic materials 0.000 abstract description 3
- 230000005540 biological transmission Effects 0.000 abstract description 3
- 238000010494 dissociation reaction Methods 0.000 abstract description 3
- 230000005593 dissociations Effects 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 description 83
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 239000010410 layer Substances 0.000 description 46
- 125000004429 atom Chemical group 0.000 description 38
- 238000003786 synthesis reaction Methods 0.000 description 29
- 230000015572 biosynthetic process Effects 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 239000004698 Polyethylene Substances 0.000 description 21
- 239000003480 eluent Substances 0.000 description 18
- -1 monocyclic compound Chemical class 0.000 description 18
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000005303 weighing Methods 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000004528 spin coating Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 238000010189 synthetic method Methods 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 125000006165 cyclic alkyl group Chemical group 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
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- 238000005086 pumping Methods 0.000 description 5
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 239000004696 Poly ether ether ketone Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910000480 nickel oxide Inorganic materials 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920002530 polyetherether ketone Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UJCFZCTTZWHRNL-UHFFFAOYSA-N 2,4-Dimethylanisole Chemical compound COC1=CC=C(C)C=C1C UJCFZCTTZWHRNL-UHFFFAOYSA-N 0.000 description 1
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 1
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- OXMIDRBAFOEOQT-UHFFFAOYSA-N Me2THF Natural products CC1CCC(C)O1 OXMIDRBAFOEOQT-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- REAYFGLASQTHKB-UHFFFAOYSA-N [2-[3-(1H-pyrazol-4-yl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1N=CC(=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 REAYFGLASQTHKB-UHFFFAOYSA-N 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001717 carbocyclic compounds Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000002720 diazolyl group Chemical group 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000007606 doctor blade method Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HYCOYJYBHKAKGQ-UHFFFAOYSA-N ethylmesitylene Natural products CCC1=C(C)C=C(C)C=C1C HYCOYJYBHKAKGQ-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 238000007647 flexography Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 238000007644 letterpress printing Methods 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- Photovoltaic Devices (AREA)
Abstract
The invention relates to an organic mixture, which comprises two small molecular donor materials, wherein the two small molecular donor materials have the same skeleton structure, the two donor materials with similar structures form a composite material similar to an alloy phase, and compared with a single molecular donor material, the composite material is matched with a proper acceptor material, has more continuous energy level, stronger and wider absorption and more proper crystallinity, further can obtain more ideal interpenetrating network morphology, ensures effective exciton dissociation and charge transmission, and can improve the photoelectric conversion efficiency of the device when applied to an organic solar cell device.
Description
Technical Field
The invention relates to the field of organic solar cell materials, in particular to an organic mixture, a composition and application thereof.
Background
Organic solar cells, which are an emerging photovoltaic technology for converting solar energy into electrical energy, have the advantages of light weight, low cost, translucency, flexibility, large-area printing preparation and the like, and are widely paid attention to and studied.
The photoactive layer of the organic solar cell consists of a donor material and an acceptor material, and at present, the donor material is divided into a polymer and a small molecule, the device efficiency based on the polymer as the donor material under laboratory conditions is over 19 percent, but the development of the device is limited to a certain extent due to the large batch difference of the polymer material. The small molecular donor material has a definite molecular structure and excellent material and device repeatability, and is favorable for realizing industrial application.
At present, development of donor materials based on small molecule systems has made great progress, for example: wei Zhixiang the subject group designs and develops a novel small molecule donor material BDTF-CA, and combines with a small molecule acceptor material IDIC-2F to realize the photoelectric efficiency of more than 9 percent (DOI: 10.1007/s 11426-018-9437-7); liu Shirong the subject group designs and develops a novel small molecule donor material BITHR, and the combination of the novel small molecule donor material BITHR and a small molecule acceptor material Y6 realizes the photoelectric conversion effect of more than 12 percent (DOI: 10.1002/solr.201900326).
However, current small molecule donor material systems are mainly based on binary organic solar systems, i.e. the photoactive layer contains only one donor and one acceptor. There is less research on collocation between small molecule donor materials, i.e., less research on ternary or quaternary blending. By selecting proper small molecular donor materials for blending, the morphology of the photoactive layer is improved, and the method is an effective strategy for further improving the photoelectric conversion efficiency of the device.
Disclosure of Invention
Based on the problems existing in the prior art, the invention aims to provide an organic mixture which comprises two small molecular donor materials, and can improve the photoelectric conversion efficiency of the device when the organic mixture is applied to an organic solar cell device.
In order to achieve the purpose of the invention, the following technical scheme is provided:
an organic mixture comprising an organic compound H1 and an organic compound H2, wherein the organic compound H1 is selected from structures represented by general formula (I), and the organic compound H2 is selected from structures represented by general formula (II):
wherein R is 1 、R 2 Independently selected for each occurrence from the group consisting of straight chain alkyl groups having 1 to 20 carbon atoms, branched chain alkyl groups having 3 to 20 carbon atoms, straight chain alkoxy groups having 1 to 20 carbon atoms, branched chain alkoxy groups having 3 to 20 carbon atoms, straight chain alkylthio groups having 1 to 20 carbon atoms, branched chain alkylthio groups having 3 to 20 carbon atoms, unsubstituted or substituted with R * Substituted aromatic groups having 6-20 carbon atoms, or unsubstituted or substituted by R * Substituted heteroaromatic groups having 5 to 20 ring atoms, or a combination of the above;
R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 each occurrence is independently selected from the group consisting of-H, -D, -F, -Cl, -Br, -I, -CN, -NO 2 A linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a linear alkylthio group having 1 to 20 carbon atoms, a branched alkylthio group having 3 to 20 carbon atoms, or a combination thereof;
R 11 、R 12 Independently for each occurrence a group selected from the group consisting of straight chain alkyl groups having 1 to 20 carbon atoms, branched alkyl groups having 3 to 20 carbon atoms, and combinations of these groups;
R * each occurrence is independently selected from: -D, -F, -Cl, -Br, -I, -CN, -NO 2 A linear alkyl group having 1 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a linear alkylthio group having 1 to 20 carbon atoms, a linear alkoxycarboxyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a branched alkylthio group having 3 to 20 carbon atoms-a branched alkoxycarboxyl group of 20 carbon atoms, an aromatic group of 6 to 20 carbon atoms, or a heteroaromatic group of 5 to 20 ring atoms, or a combination of the above.
The invention further relates to a composition comprising the above organic mixture and at least one organic solvent.
The invention further relates to an organic electronic device comprising at least one photoactive layer, the photoactive layer material comprising an organic mixture as described above, or being prepared from a composition as described above.
The beneficial effects are that:
the organic mixture according to the invention comprises two small molecule donor materials, and the two small molecule donor materials have the same framework structure (both take BDT units as cores) with the difference that the end-capped electron withdrawing unit groups are selected differently. The two donor materials with similar structures form a composite material similar to an alloy phase, and compared with a single-molecule donor material, the organic mixture provided by the invention has more continuous energy level, stronger and wider absorption and more proper crystallinity when matched with a proper acceptor material, so that more ideal interpenetrating network morphology is further obtained, effective exciton dissociation and charge transmission are ensured, and the photoelectric conversion efficiency of the device is improved.
Drawings
Fig. 1 is a schematic structural view of an organic solar device according to an embodiment of the device of the present invention.
Wherein 101 is a substrate, 102 is an anode, 103 is an anode buffer layer, 104 is a photoactive layer, 105 is a cathode buffer layer, and 106 is a cathode.
Detailed Description
In order to make the objects, technical solutions and effects of the present application clearer and more specific, the present application will be described in further detail below. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the present application.
The term "and/or," "and/or," as used herein, includes any one of two or more of the listed items in relation to each other, as well as any and all combinations of the listed items in relation to each other, including any two of the listed items in relation to each other, any more of the listed items in relation to each other, or all combinations of the listed items in relation to each other. It should be noted that, when at least three items are connected by a combination of at least two conjunctions selected from "and/or", "or/and", "and/or", it should be understood that, in this application, the technical solutions certainly include technical solutions that all use "logical and" connection, and also certainly include technical solutions that all use "logical or" connection. For example, "a and/or B" includes three parallel schemes A, B and a+b. For another example, the technical schemes of "a, and/or B, and/or C, and/or D" include any one of A, B, C, D (i.e., the technical scheme of "logical or" connection), and also include any and all combinations of A, B, C, D, i.e., any two or three of A, B, C, D, and also include four combinations of A, B, C, D (i.e., the technical scheme of "logical and" connection).
In the present invention, the organic photovoltaic device, the organic solar cell, the OPV, OSC have the same meaning and are interchangeable.
In the present invention, the photoactive layer and the active layer have the same meaning and are interchangeable.
In the present invention, aromatic groups and aromatic ring systems have the same meaning and can be interchanged.
In the present invention, the heteroaromatic groups, heteroaromatic groups and heteroaromatic ring systems have the same meaning and can be interchanged.
In the present invention, the "heteroatom" is a non-carbon atom, and may be an N atom, an O atom, an S atom, or the like.
In the present invention, "substituted" means that one or more hydrogen atoms in the substituted group are substituted with the substituent.
In the present invention, when the same substituent appears multiple times, it means that it can be independently selected from different groups, for example, the formula contains multiple R * R is then * May be independently selected from different groups.
In the present invention, the "number of ring atoms" means the number of atoms among atoms constituting the ring itself of a structural compound (for example, a monocyclic compound, a condensed ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below, unless otherwise specified. In the aromatic group, the number of ring atoms is the same as the number of carbon atoms; in the heteroaromatic group, the number of ring atoms is the number of carbon atoms plus the number of heteroatoms; for example, the number of ring atoms of the benzene ring is 6, the number of ring atoms of the naphthalene ring is 10, the number of ring atoms of the quinoline is 10, the number of ring atoms of the thienyl group is 5, and the number of ring atoms of the thienothiophene is 8.
In the present invention, "aromatic group" refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aromatic group may be a monocyclic aromatic group (e.g., phenyl) or a polycyclic aromatic group, in other words, the aromatic group may be a monocyclic aromatic group, a condensed ring aromatic group, two or more monocyclic aromatic groups connected by a carbon-carbon bond conjugate, a monocyclic aromatic group and a condensed ring aromatic group connected by a carbon-carbon bond conjugate, two or more condensed ring aromatic groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered aromatic groups herein unless otherwise indicated. Preferably, said aromatic group is selected from aromatic groups having 6 to 30C atoms; further, an aromatic group selected from the group consisting of having 6 to 20C atoms; further, an aromatic group selected from the group consisting of having 6 to 10C atoms; aromatic groups include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluoranthryl, triphenylenyl, pyrenyl, perylenyl, tetracenyl, fluorenyl, perylenyl, acenaphthylenyl and derivatives thereof.
In the present invention, the "heteroaromatic group" means a monovalent aromatic ring containing 1, 2, 3, 4, 5, 6 or more heteroatoms in the ring or a derivative thereof, and the heteroatoms may be at least one of B, O, N, P, si, se and S. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or may be a plurality of aromatic ring systems connected by carbon-carbon bond conjugation, and either aromatic ring system is an aromatic monocyclic ring or an aromatic condensed ring. Preferably, the said heteroaromatic group is selected from the group consisting of heteroaromatic groups having 6 to 30 ring atoms; further, a heteroaromatic group selected from the group consisting of having 6 to 20 ring atoms; further, it is selected from heteroaromatic groups having 6 to 10 ring atoms. Heteroaromatic groups include, but are not limited to: thienyl, furyl, pyrrolyl, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiophenoyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, phthalazinyl, phenanthridinyl, primary pyridyl, quinazolinonyl, dibenzothienyl, dibenzofuranyl, carbazolyl, and derivatives thereof.
In the present invention, "alkyl" may denote a linear, branched and/or cyclic alkyl group. The carbon number of the linear alkyl group may be 1 to 20, 1 to 16, or 1 to 6; the branched alkyl group may have a carbon number of 3 to 20, 3 to 16, or 3 to 6; the cyclic alkyl group may have a carbon number of 3 to 20, 3 to 16, or 3 to 6. Non-limiting examples of straight chain alkyl groups include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, -C 10 H 21 、-C 11 H 23 、-C 12 H 25 、-C 13 H 27 、-C 14 H 29 、-C 15 H 31 、-C 16 H 33 . Non-limiting examples of branched alkyl groups include: isopropyl, branched alkyl having 4C atoms, branched alkyl having 5C atoms, branched alkyl having 6C atoms, branched alkyl having 7C atoms, branched alkyl having 8C atoms, branched alkyl having 9C atoms, branched alkyl having 10C atoms, branched alkyl having 11C atomsAlkyl, branched alkyl having 12C atoms, branched alkyl having 13C atoms, branched alkyl having 14C atoms, branched alkyl having 15C atoms, branched alkyl having 16C atoms.
The term "alkoxy" refers to a group of the structure "-O-alkyl", wherein alkyl is as defined above.
The term "alkylthio" refers to a group of the structure "-S-alkyl", wherein alkyl is as defined above.
The term "alkoxycarboxyl" refers to a compound of the structureWherein alkyl is as defined above.
In the present invention, when no attachment site is specified in a group, an optionally attachable site in the group is represented as an attachment site.
In the present invention, when the same group contains a plurality of substituents of the same symbol, each substituent may be the same or different from each other, for exampleThe 6R groups on the benzene ring may be the same or different from each other.
In the present invention, the "independently selected" group or groups means that when one or more groups are present at the same time and at a plurality of places in the compound, they are independently selected, and may be the same or different.
As used in the present invention, "a combination thereof", "any combination thereof", "combination", and the like include all suitable combinations of any two, any three, or any three or more of the listed groups.
In the present invention, "further", "still further", "particularly" and the like are used for descriptive purposes to indicate differences in content but should not be construed as limiting the scope of the invention.
In the present invention, "optional" means optional or not, that is, means any one selected from two parallel schemes of "with" or "without". If multiple "alternatives" occur in a technical solution, if no particular description exists and there is no contradiction or mutual constraint, then each "alternative" is independent.
In the invention, the technical characteristics described in an open mode comprise a closed technical scheme composed of the listed characteristics and also comprise an open technical scheme comprising the listed characteristics.
The invention relates to an organic mixture, which comprises an organic compound H1 and an organic compound H2, wherein the organic compound H1 is selected from structures shown in a general formula (I), and the organic compound H2 is selected from structures shown in a general formula (II):
wherein,
R 1 、R 2 independently selected for each occurrence from the group consisting of straight chain alkyl groups having 1 to 20 carbon atoms, branched chain alkyl groups having 3 to 20 carbon atoms, straight chain alkoxy groups having 1 to 20 carbon atoms, branched chain alkoxy groups having 3 to 20 carbon atoms, straight chain alkylthio groups having 1 to 20 carbon atoms, branched chain alkylthio groups having 3 to 20 carbon atoms, unsubstituted or substituted with R * Substituted aromatic groups having 6-20 carbon atoms, or unsubstituted or substituted by R * Substituted heteroaromatic groups having 5 to 20 ring atoms, or a combination of the above;
R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 each occurrence is independently selected from the group consisting of-H, -D, -F, -Cl, -Br, -I, -CN, -NO 2 A linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a linear alkylthio group having 1 to 20 carbon atoms, a branched alkylthio group having 3 to 20 carbon atoms, or a combination thereof;
R 11 、R 12 Each occurrence is independently selected from the group consisting of having 1 to 20 carbon atomsA linear alkyl group of a child, a branched alkyl group having 3 to 20 carbon atoms, or a combination of these groups;
R * each occurrence is independently selected from: -D, -F, -Cl, -Br, -I, -CN, -NO 2 A linear alkyl group having 1 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a linear alkylthio group having 1 to 20 carbon atoms, a linear alkoxycarboxyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a branched alkylthio group having 3 to 20 carbon atoms, a branched alkoxycarboxyl group having 3 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms, or a heteroaromatic group having 5 to 20 ring atoms, or a combination thereof.
In the present invention, the "unsubstituted or R * Substituted "means that the defined group is unsubstituted or substituted by one or more substituents R * And (3) substitution.
Preferably, R * Each occurrence is independently selected from: -D, -F, -Cl, -Br, -I, -CN, -NO 2 A linear alkyl group having 1 to 16 carbon atoms, a linear alkoxy group having 1 to 16 carbon atoms, a linear alkylthio group having 1 to 16 carbon atoms, a linear alkoxycarboxyl group having 1 to 16 carbon atoms, a branched alkyl group having 3 to 16 carbon atoms, a branched alkoxy group having 3 to 16 carbon atoms, a branched alkylthio group having 3 to 16 carbon atoms, a branched alkoxycarboxyl group having 3 to 16 carbon atoms, an aromatic group having 6 to 10 carbon atoms, or a heteroaromatic group having 5 to 10 ring atoms, or a combination thereof.
In one embodiment, R 1 、R 2 Independently selected from the group consisting of, for each occurrence, a linear alkyl group having 1 to 16 carbon atoms, a linear alkoxy group having 1 to 16 carbon atoms, a linear alkylthio group having 1 to 16 carbon atoms, a linear alkoxycarboxyl group having 1 to 16 carbon atoms, a branched alkyl group having 3 to 16 carbon atoms, a branched alkoxy group having 3 to 16 carbon atoms, a branched alkylthio group having 3 to 16 carbon atoms, a branched alkoxycarboxyl group having 3 to 16 carbon atoms, and a cyclic alkyl group having 1 to 16 carbon atoms, a cyclic alkyl group having 3 to 16 carbon atoms, a cyclic alkyl group having 1 to 16 carbon atoms, a cyclic alkyl group having R * Substituted or unsubstituted phenyl, or by R * Substituted or not takenSubstituted heteroaromatic groups having 5 to 6 ring atoms, or combinations of the foregoing.
Preferably, R 1 、R 2 Each occurrence is independently selected from a straight chain alkyl group having 1 to 16 carbon atoms, a branched alkyl group having 3 to 16 carbon atoms, or any of the following structures:
wherein,
R 13 independently for each occurrence a straight chain alkyl group having 1 to 16 carbon atoms, or a branched alkyl group having 3 to 16 carbon atoms;
R 14 、R 15 、R 16 each occurrence is independently selected from: -H, -D, -F, -Cl, -Br, -I, -CN, -NO 2 A linear alkyl group having 1 to 16 carbon atoms, a linear alkoxy group having 1 to 16 carbon atoms, a linear alkylthio group having 1 to 16 carbon atoms, a linear alkoxycarboxyl group having 1 to 16 carbon atoms, a branched alkyl group having 3 to 16 carbon atoms, a branched alkoxy group having 3 to 16 carbon atoms, a branched alkylthio group having 3 to 16 carbon atoms, a branched alkoxycarboxyl group having 3 to 16 carbon atoms, or a combination thereof;
* Representing the ligation site.
In one embodiment, the R 13 Each occurrence is independently selected from the group consisting of a linear or branched alkyl group having 6 carbon atoms, a linear or branched alkyl group having 7 carbon atoms, a linear or branched alkyl group having 8 carbon atoms, a linear or branched alkyl group having 9 carbon atoms, a linear or branched alkyl group having 10 carbon atoms, a linear or branched alkyl group having 11 carbon atoms, a linear or branched alkyl group having 12 carbon atoms, a linear or branched alkyl group having 13 carbon atoms, a linear or branched alkyl group having 14 carbon atoms, a linear or branched alkyl group having 15 carbon atoms, a linear or branched alkyl group having 16 carbon atoms.
Further, R 13 Each occurrence is independently selected from
In one embodiment of the present invention, in one embodiment,each occurrence is independently selected from->R 17 Each occurrence is independently selected from a straight chain alkyl group having 1 to 16 carbon atoms, or a branched alkyl group having 3 to 16 carbon atoms.
Further, the method comprises the steps of,each occurrence is independently selected from->
The R is 17 Each occurrence is independently selected from the group consisting of a linear or branched alkyl group having 6 carbon atoms, a linear or branched alkyl group having 7 carbon atoms, a linear or branched alkyl group having 8 carbon atoms, a linear or branched alkyl group having 9 carbon atoms, a linear or branched alkyl group having 10 carbon atoms, a linear or branched alkyl group having 11 carbon atoms, a linear or branched alkyl group having 12 carbon atoms, a linear or branched alkyl group having 13 carbon atoms, a linear or branched alkyl group having 14 carbon atoms, a linear or branched alkyl group having 15 carbon atoms, a linear or branched alkyl group having 16 carbon atoms.
Further, R 17 Independently for each occurrence a branched alkyl group having 8 carbon atoms. Further, R 17 Selected from the group consisting of
In one embodiment, R 15 Independently at each occurrence is selected from the group consisting of a linear alkyl group having 1 to 16 carbon atoms, a linear alkoxy group having 1 to 16 carbon atoms, a linear alkylthio group having 1 to 16 carbon atoms,A straight chain alkoxycarboxyl group having 1 to 16 carbon atoms, a branched alkyl group having 3 to 16 carbon atoms, a branched alkoxy group having 3 to 16 carbon atoms, or a branched alkylthio group having 3 to 16 carbon atoms.
Further, R 15 Independently for each occurrence a branched alkyl group having 3 to 16 carbon atoms, a branched alkylthio group having 3 to 16 carbon atoms.
Further, R 15 Each occurrence is independently selected from any one of the following groups:
in one embodiment, R 16 Each occurrence is independently selected from: -H, -D, -F, -Cl, -Br, -I, -CN, -NO 2 A linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, or a combination of the above.
Further, R 16 Each occurrence is independently selected from: -H, -D, -F, -Cl, -C 6 H 13 。
Specifically, R 1 、R 2 Each occurrence is independently selected from the following structures:
further, R in the general formula (I) or the general formula (II) 1 、R 2 Selected from the same groups.
In one embodiment, R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 Each occurrence is independently selected from: -H, -D, -F, -Cl, -Br, -I, -CN, -NO 2 A linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, or a combination thereof.
Further, R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 Each occurrence is independently selected from: -H, -D, -F, -Cl, -Br, -I, -CN, -NO 2 A linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, or a combination of the above.
Preferably, the structural units (a) comprised in the general formula (I) and the general formula (II) are selected from the same structures:
wherein: * Representing a linking group.
Namely R in the general formula (I) and the general formula (II) 1 Selected from the same groups; r in the general formula (I) and the general formula (II) 2 Selected from the same groups; r in the general formula (I) and the general formula (II) 3 Selected from the same groups; r in the general formula (I) and the general formula (II) 4 Selected from the same groups; r in the general formula (I) and the general formula (II) 5 Selected from the same groups; r in the general formula (I) and the general formula (II) 6 Selected from the same groups; r in the general formula (I) and the general formula (II) 7 Selected from the same groups; r in the general formula (I) and the general formula (II) 8 Selected from the same groups; r in the general formula (I) and the general formula (II) 9 Selected from the same groups; r in the general formula (I) and the general formula (II) 10 Selected from the same groups.
In a preferred embodiment, structural unit (A) is selected from (A-1) or (A-2):
wherein: r in (A-1) 4 、R 6 、R 8 、R 10 Each occurrence is independently selected from: -F, -Cl, -Br, -I, -CN, -NO 2 A linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, or a combination thereof;
r in (A-2) 3 、R 5 、R 7 、R 9 Each occurrence is independently selected from: -F, -Cl, -Br, -I, -CN, -NO 2 A linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, or a combination of the above.
In one embodiment, R 11 、R 12 Each occurrence is independently selected from: a linear alkyl group having 1 to 16 carbon atoms, a branched alkyl group having 3 to 16 carbon atoms, or a combination of the above.
Further, R 11 Each occurrence is independently selected from: a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, or a combination of the above.
In a specific embodiment, theSelected from any one of the following structures:
in a specific embodiment, the Selected from the following structures:
preferably, the saidSelected from->And/or +.>Selected from->
In a specific embodiment, the organic compound H1 according to the present invention is selected from the following structures, but is not limited thereto:
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in a specific embodiment, the organic compound H2 according to the present invention is selected from the following structures, but is not limited thereto:
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in the organic mixture provided by the invention, the mass ratio of the organic compound H1 to the organic compound H2 is 9:1 to 1:9; further, the mass ratio of the organic compound H1 to the organic compound H2 is 8:2 to 2:8; further, the mass ratio of the organic compound H1 to the organic compound H2 is 5:5.
In one embodiment, the organic mixture according to the present invention may further include an organic compound H3, wherein the organic compound H3 is selected from non-fullerene small molecule acceptor materials.
Preferably, the organic compound H3 is selected from the structures of the following general formula (III):
wherein R is 101 、R 102 、R 103 、R 104 Independently selected from-H, -D, a linear alkyl group having 1-20 carbon atoms, a linear alkoxy group having 1-20 carbon atoms, a linear alkylthio group having 1-20 carbon atoms, a branched alkyl group having 3-20 carbon atoms, a branched alkoxy group having 3-20 carbon atoms, a branched alkylthio group having 3-20 carbon atoms, a phenyl group substituted with a linear or linear alkyl group having 6-12C atoms, a thienyl group substituted with a linear or linear alkyl group having 6-12C atoms, or a combination thereof;
R 105 、R 106 、R 107 、R 108 Each occurrence is independently selected from: -H, -D, -CH 3 、-F、-CF 3 -Cl, -Br, -I, -CN, or-NO 2 。
In a preferred embodiment, the R 101 、R 102 Selected from the group consisting of 9C atomsA linear or branched alkyl group having 10C atoms, a linear or branched alkyl group having 11C atoms, a linear or branched alkyl group having 12C atoms, a linear or branched alkoxy group having 10C atoms, a linear or branched alkoxy group having 11C atoms, a linear or branched alkoxy group having 12C atoms, a linear or branched alkylthio group having 10C atoms, a linear or branched alkylthio group having 11C atoms, a linear or branched alkylthio group having 12C atoms, a phenyl group substituted with a linear or linear alkyl group having 6 to 12C atoms, a thienyl group substituted with a linear or linear alkyl group having 6 to 12C atoms.
In a more preferred embodiment, the R 101 、R 102 Selected from the group consisting of a linear alkyl group having 9C atoms, a linear alkyl group having 11C atoms, a linear alkoxy group having 12C atoms, a linear alkylthio group having 11C atoms, a branched alkyl group having 12C atoms,
In a preferred embodiment, the R 103 、R 104 Each occurrence is independently selected from the group consisting of a linear or branched alkyl group having 8C atoms, a linear or branched alkyl group having 9C atoms, a linear or branched alkyl group having 10C atoms, a linear or branched alkyl group having 11C atoms, a linear or branched alkyl group having 12C atoms, a linear or branched alkyl group having 13C atoms, a linear or branched alkyl group having 14C atoms, a linear or branched alkyl group having 15C atoms, a linear or branched alkyl group having 16C atoms.
In a more preferred embodiment, the R 103 、R 104 Each occurrence is independently selected from the group consisting of branched alkyl groups having 8C atoms, straight chain alkyl groups having 11C atoms, branched alkyl groups having 12C atoms, branched alkyl groups having 16C atoms.
In a more preferred embodiment, the R 101 、R 102 Selected from the same groups; r is R 103 、R 104 Selected from the same groups.
Specifically, the organic compound H3 is selected from the following structures:
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in a preferred embodiment, the mass ratio of the sum of the organic compound H1 and the organic compound H2 to the organic compound H3 in the organic mixture is from 1:1 to 1:1.5; further, the mass ratio is 1:1 to 1:1.2; further, the mass ratio is 1:1 to 1:1.1.
The invention also relates to a composition comprising at least one organic mixture as described above and at least one organic solvent. The organic solvent is selected from aliphatic hydrocarbon, chlorinated hydrocarbon, aromatic hydrocarbon, ketone, ether and mixture of any two or more of the above organic solvents. In one embodiment, the organic solvent is selected from the group consisting of methylene chloride, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, 2, 4-dimethyl anisole, 1-methylnaphthalene, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1, 4-dioxane, acetone, methyl ethyl ketone, 1, 2-dichloroethane, 1-trichloroethane, 1, 2-tetrachloroethane, ethyl acetate, N-butyl acetate, N, N-dimethylformamide, dimethylacetamide, dimethylsulfoxide 1, 5-dimethyltetrahydrofuran, acetophenone, tetrahydronaphthalene, 2-methylthiophene, 3-methylthiophene, decalin, indane, methyl benzoate, ethyl benzoate, mesitylene or mixtures thereof.
In a preferred embodiment, the organic solvent may be selected from chlorobenzene, toluene, o-xylene, or chloroform, but is not limited thereto.
In one embodiment, the organic mixture is present in the composition at a concentration of 10-40mg/mL.
It is understood that the organic solvent may be evaporated from the solvent system to form a film comprising the organic compound.
In one embodiment, the composition is a solution. In other embodiments, the composition is a suspension. The solution or suspension may additionally include additives for adjusting viscosity, adjusting film forming properties, improving adhesion, etc. The additive may be selected from at least one of, but not limited to, a surface active compound, a lubricant, a wetting agent, a dispersing agent, a hydrophobizing agent, and a binder.
The invention also relates to the use of said composition as a coating or printing ink in the preparation of an organic electronic device. In one embodiment, the composition is used in the preparation of organic electronic devices by a print or coating preparation method. The printing or coating may be prepared by, but is not limited to, ink jet printing, gravure printing, spray printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roll printing, twist roller printing, offset printing, flexography, rotary printing, spray coating, brush coating, pad printing, slot die coating, and the like. Preferred are slot coating, spin coating and ink jet printing.
The invention further relates to the use of an organic mixture or composition as described above in an organic electronic device. The organic electronic device may be selected from, but not limited to, organic solar cells (OPV), organic Light Emitting Diodes (OLED), organic light emitting cells (OLEEC), organic Field Effect Transistors (OFET), organic Photodetectors (OPD), etc., and particularly preferably organic solar cells (OPV).
The invention also relates to an organic electronic device comprising at least one photoactive layer, characterized in that: the photoactive layer materials comprise or are prepared from the organic mixtures described above.
Further, according to the present invention, an organic electronic device comprises at least a first electrode, a second electrode and a photoactive layer between the first electrode and the second electrode, the photoactive layer material comprising or being prepared from an organic mixture as described above.
In one embodiment, the first electrode is an anode and the second electrode is a cathode; in another embodiment, the first electrode may be a cathode and the second electrode may be an anode.
In one embodiment, the organic electronic device further comprises an anode buffer layer and a cathode buffer layer; wherein the anode buffer layer is located between the anode and the photoactive layer; the cathode buffer layer is located between the cathode and the photoactive layer.
It should be noted that, in order to improve the performance of the organic solar cell device, the organic solar cell device may further include other functional layers, including, but not limited to, a charge injection layer and/or a charge blocking layer.
In an embodiment, the organic electronic device is selected from an organic solar cell (OPV).
Further, the organic solar cell further comprises a substrate. In particular, the substrate may be disposed at the bottom of the first electrode.
In one embodiment, as the substrate, a substrate having excellent transparency, surface smoothness, ease of handling, and water repellency may be used. Specifically, a glass substrate, a thin film glass substrate, or a transparent plastic substrate may be used. The plastic substrate may further include a film in the form of a single layer or a plurality of layers, such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyetheretherketone (PEEK), polyimide (PI), etc., but is not limited thereto, and a substrate commonly used for an organic solar cell may also be used.
At least one of the first electrode and the second electrode is transparent or translucent to facilitate light incidence. The material used for preparing the electrode may be selected from metals such as vanadium (V), chromium (Cr), zinc (Zn), silver (Ag), aluminum (Al), platinum (Pt), tungsten (W), copper (Cu), molybdenum (Mo), gold (Au), nickel (Ni), palladium (Pd), or alloys of the above metals, etc.; metal oxides such as zinc oxide, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), and the like; combinations of metals and oxides, e.g. ZnO: al or SnO 2 Sb, etc.; and a conductive polymer, poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDOT), polypyrrole, polyaniline, and the like; or materials having a multilayer structure, e.g. LiF/Al, liO 2 /Al、LiF/Ag、MoO 3 /Al/MoO 3 、MoO 3 /Ag/MoO 3 ，ITO/Ag/ITO，Al∶Li、Al∶BaF 2 Al: baF 2 Such as Ba, but not limited thereto.
The anode buffer layer material may be selected from PEDOT of poly (styrenesulfonic acid): PSS (poly (3, 4-ethylenedioxythiophene)), molybdenum oxide (MoOx), vanadium oxide (V) 2 O 5 ) Nickel oxide (NiO), tungsten oxide (WO x， Preferably, x is selected from 2 or 3), etc., but is not limited thereto.
The cathode buffer layer material can be electron-withdrawing metal oxide or polymer, and the metal oxide can be metal complex containing 8-hydroxyquinoline and Alq 3 Metal complex containing Liq, liF, ca, titanium oxide (TiOx), zinc oxide (ZnO), cesium carbonate (Cs 2 CO 3 ) And the like, the polymer may be PFN-Br, PFN or the like, but is not limited thereto.
The provided organic solar cell according to the present invention may be applied in various devices, for example, automobile and Building Integrated Photovoltaic (BIPV), electronic price tag, indoor photovoltaic, internet of things, smart agriculture, etc.
The invention will be described in detail below in connection with the mixture preparation examples and the organic electronic device preparation examples, but the invention is not limited to the following examples, it being understood that the appended claims summarize the scope of the invention and those skilled in the art who have the benefit of the inventive concepts herein understand that certain changes may be made to the various embodiments of the invention which are intended to be covered by the spirit and scope of the claims herein.
Synthesis of organic compound H1 and organic compound H2:
example 1: synthesis of Compound (H1-24):
synthesis of Compounds 1-3:
accurately weighing 1-1 (9.4 g,10 mmol) and 1-2 (6.1 g,20 mmol) of bis (triphenylphosphine) palladium dichloride Pd (PPh) 3 ) 2 Cl 2 (0.42, 0.6 mmol) is added into a 250mL three-neck flask in sequence, about 100mL of anhydrous toluene is added, nitrogen is pumped in for three times, the temperature is raised to 100 ℃ for reaction for 4 hours, after the raw materials are completely reacted, the excessive solvent is removed by reduced pressure distillation, silica gel is stirred with column chromatography, eluting agent is PE, EA=20:1 (volume ratio) to obtain about 8.8g of compound 1-3, and the yield: 83%. MS-Synthesis of 1060.32 Compounds 1-4:
accurately weighing the compounds 1-3 (8.8 g,8.3 mmol) and adding the compounds into a 500mL three-neck flask, adding 90mL of dichloromethane, pumping nitrogen for three times, cooling to about 10 ℃ in an ice salt bath, slowly dropwise adding a dichloromethane solution of NBS (3.3 g,18.3mmol dissolved in 80mL of dichloromethane) into a reaction system, heating to room temperature for reaction overnight after the dropwise addition, washing with water, extracting with dichloromethane, combining organic phases, drying with anhydrous sodium sulfate, removing redundant solvent by reduced pressure distillation, and carrying out silica gel column chromatography, wherein the eluent is PE: EA=20:1 (volume ratio) to obtain the compounds 1-4 of about 8.5g, wherein the yield: 84.1%. Synthesis of MALDI-TOF MS 1218.34 Compounds 1-6:
Accurately weighing 1-4 (8.5 g,7 mmol), 1-5 (4.7 g,14 mmol), pd (PPh) 3 ) 2 Cl 2 (0.20 g,0.28 mmol) is added into a 250mL three-neck flask in sequence, about 100mL of anhydrous toluene is added, nitrogen is pumped in for three times, the temperature is raised to 100 ℃ for reaction for 4 hours, after the raw materials are completely reacted, the excessive solvent is removed by reduced pressure distillation, silica gel is stirred with column chromatography, eluting agent is PE, EA=20:1 (volume ratio) to obtain about 8.3g of compound 1-6, and the yield: 87.2%. MALDI-TOF MS 1392.52
Synthesis of Compounds 1-7:
accurately weighing 1-6 (8.3 g,6 mmol) of the compound into a 250mL three-necked flask, adding about 80mL of anhydrous DMF, pumping nitrogen for three times, slowly adding 10mL of phosphorus oxychloride into the reaction system at room temperature, and then heating to 90 ℃ for reaction for 2 hours. After the raw materials are completely reacted, cooling to room temperature, slowly pouring the reaction solution into an ice bath added with hydrochloric acid, extracting with ethyl acetate, combining organic phases, drying with anhydrous sodium sulfate, distilling under reduced pressure to remove redundant solvent, and carrying out silica gel sample column chromatography, wherein the eluting agent is PE (polyethylene) EA=10:1 (volume ratio) to obtain about 7.3g of a compound 1-7. Yield: 84%. MALDI-TOF MS: synthesis of 1448.35 compound (H1-24):
compounds 1 to 7 (1.45 g,1 mmol), 1 to 8 (0.59 g,3 mmol) were added to a 100mL three-necked flask, 30mL chloroform was added to replace three times of nitrogen, then 4mL pyridine was added to raise the temperature to 70 ℃ to react overnight, after the raw materials were completely reacted, cooled to room temperature, washed with water, extracted with DCM, dried over anhydrous sodium sulfate after combining the organic phases, silica gel stirred column chromatography, and eluent DCM: PE=2:1 (volume ratio) was used as eluent to give approximately 1.2g of compound (H1-24) with a yield of 66.4%. MALDI-TOFMS:1806.57.
Example 2: synthesis of Compound (H2-30)
Synthesis of Compound (H2-30):
the product of compound 1-7 (1.45 g,1 mmol), compound 2-1 (0.74 g,3 mmol) was prepared by the synthetic method of compound (H1-24) and was chromatographed on a silica gel column, eluting with DCM: PE=2:1 (volume ratio) as eluent to give compound (H2-30) in a yield of 57.8%. MALDI-TOF-MS:1903.49.
example 3: synthesis of Compound (H2-32)
Synthesis of Compound (H2-32):
the product of compound 1-7 (1.45 g,1 mmol), compound 3-1 (0.48 g,3 mmol) was prepared by the synthetic method of compound (H1-24), silica gel column chromatography with eluent DCM: pe=2:1 (volume ratio) as eluent, giving compound (H2-32) about 0.9g in 51.9% yield. MALDI-TOF-MS:1734.77.
example 4: synthesis of Compound (H1-20)
Synthesis of Compound 4-2:
accurately weighing compound 4-1 (10.7 g,10 mmol), compound 1-2 (6.1 g,20 mmol), preparing a product according to the synthesis method of compound 1-3, and performing silica gel sample column chromatography, wherein the eluting agent is PE (polyethylene) with EA=20:1 (volume ratio) to obtain compound 4-2 with the yield of about 9.6 g: 80.5%. MALDI-TOF-MS 1192.56
Synthesis of Compound 4-3:
accurately weighing compound 4-2 (9.6 g,8 mmol), adding into a 500mL three-neck flask, adding 90mL of dichloromethane, pumping nitrogen for three times, cooling to about-10 ℃ in an ice salt bath, slowly dropwise adding a dichloromethane solution of NBS (3.1 g,17.6mmol dissolved in 80mL of dichloromethane) into a reaction system, heating to room temperature for reaction overnight after the dropwise addition is finished, washing with water, extracting dichloromethane, combining organic phases, drying with anhydrous sodium sulfate, distilling under reduced pressure to remove multiple solvents, and performing silica gel column chromatography, wherein the eluent is PE: EA=20:1 (volume ratio) to obtain compound 4-3 of about 9.5g, and the yield: 88%. Synthesis of MALDI-TOF-MS/1349.97 Compound 4-4:
Accurately weighing compound 4-3 (9.5 g,7 mmol), compound 1-5 (4.7 g,14 mmol), pd (PPh) 3 ) 2 Cl 2 (0.20 g,0.28 mmol) is added into a 250mL three-neck flask in sequence, about 100mL of anhydrous toluene is added, nitrogen is pumped in for three times, the temperature is raised to 100 ℃ for reaction for 4 hours, after the raw materials are completely reacted, the excessive solvent is removed by reduced pressure distillation, silica gel is stirred with column chromatography, eluting agent is PE, EA=20:1 (volume ratio) to obtain about 8.1g of compound 4-4, and the yield: 75.9%. MALDI-TOF-MS: synthesis of 1524.69 Compound 4-5:
accurately weighing the compound 4-4 (8.1 g,5.3 mmol) into a 250mL three-necked flask, adding about 80mL of anhydrous DMF, preparing a product by using a synthesis method of the compound 1-7, and performing silica gel sample mixing column chromatography, wherein the eluting agent is PE (polyethylene) with EA=10:1 (volume ratio) to obtain the compound 4-5 of about 6.9g. Yield: 82.4%. MALDI-TOF-MS:1580.64
Synthesis of Compound (H1-20):
the product of compound 4-5 (1.58 g,1 mmol), compound 1-8 (0.59 g,3 mmol) was prepared by the synthetic method of compound (H1-24), silica gel column chromatography with eluent DCM: pe=2:1 (volume ratio) as eluent, giving compound (H1-20) about 1.2g in 61.9% yield. MALDI-TOF-MS:1939.17
Example 5: synthesis of Compound (H2-22)
Synthesis of Compound (H2-22):
the product of compound 4-5 (1.58 g,1 mmol), compound 2-1 (0.74 g,3 mmol) was prepared by the synthetic method of compound (H1-24), silica gel column chromatography with eluent DCM: pe=2:1 (volume ratio) as eluent, giving compound (H2-22) about 1.3g in 63.9% yield. MALDI-TOF-MS:2035.48
Example 6: synthesis of Compound (H2-24)
Synthesis of Compound (H2-24):
the product of compound 4-5 (1.58 g,1 mmol), compound 6-1 (0.65 g,3 mmol) was prepared by the synthetic method of compound (H1-24), silica gel column chromatography with eluent DCM: pe=2:1 (volume ratio) as eluent, giving compound (H2-24) about 1.2g in 60.6% yield. MALDI-TOF-MS:1979.34
Example 7: synthesis of Compound (H2-53)
Synthesis of Compound 7-3:
accurately weighing compound 7-1 (10 g,10 mmol), compound 7-2 (6.6 g,20 mmol), preparing a product according to the synthesis method of compound 1-3, and performing silica gel sample column chromatography, wherein the eluting agent is PE (polyethylene) with EA=20:1 (volume ratio) to obtain compound 7-3 with about 8.8g, and the yield: 81.5%. MS 1080.28
Synthesis of Compound 7-4:
accurately weighing compound 7-3 (8.8 g,8.1 mmol) and adding into a 500mL three-neck flask, adding 90mL of dichloromethane, pumping nitrogen for three times, cooling to about-10 ℃ in an ice salt bath, slowly dropwise adding a dichloromethane solution of NBS (3.5 g,19.4mmol dissolved in 80mL of dichloromethane) into a reaction system, heating to room temperature for reaction overnight after the dropwise addition, washing with water after the raw materials are completely reacted, extracting with dichloromethane, combining organic phases, drying with anhydrous sodium sulfate, removing multiple solvents by reduced pressure distillation, and carrying out silica gel column chromatography, wherein the eluent is PE: EA=20:1 (volume ratio) to obtain compound 7-4 with about 8.9g, and the yield: 81.6%. MS: synthesis of 1338.56 Compound 7-6:
Accurately weighing 7-4 (9.5 g,6.7 mmol) and 7-5 (4.8 g,13.3 mmol) according to the synthesis method of 1-6, obtaining the product, and performing silica gel column chromatography, wherein the eluting agent is PE (polyethylene) and EA=20:1 (volume ratio) to obtain 7-6 with the yield of about 8.1 g: 77.1%. MALDI-TOF-MS:1568.69
Synthesis of Compounds 7-7:
accurately weighing 7-6 (8.1 g,5.2 mmol) of the compound into a 250mL three-necked flask, adding about 80mL of anhydrous DMF, pumping nitrogen for three times, slowly adding 8mL of phosphorus oxychloride into the reaction system at room temperature, and then heating to 90 ℃ for reaction for 2 hours. After the raw materials are completely reacted, cooling to room temperature, slowly pouring the reaction solution into an ice bath added with hydrochloric acid, extracting with ethyl acetate, combining organic phases, drying with anhydrous sodium sulfate, distilling under reduced pressure to remove redundant solvent, and carrying out silica gel sample column chromatography, wherein the eluting agent is PE (polyethylene) EA=10:1 (volume ratio) to obtain about 6.8g of a compound 7-7. Yield: 81.1%. MALDI-TOF-MS: synthesis of 1624.62 compound (H2-53):
the product of compound 7-7 (1.58 g,1 mmol), compound 7-8 (0.74 g,3 mmol) was prepared by the synthetic method of compound (H1-24), silica gel column chromatography with eluent DCM: pe=2:1 (volume ratio) as eluent, giving compound (H2-53) about 1.4g in 67.3% yield. MALDI-TOF-MS:2079.46
Example 8: synthesis of Compound (H1-39)
Synthesis of Compound (H1-39):
the product was prepared by the synthetic method of compound 7-7 (1.58 g,1 mmol), compound 1-8 (0.59 g,3 mmol), compound (H1-24), silica gel column chromatography with eluent DCM: PE=2:1 (volume ratio) as eluent to give compound H1-39 about 1.2g in 60.5% yield. MALDI-TOF-MS:1983.18
Preparation and characterization of OPV devices
The process of preparing an organic mixture for an OPV device is described in detail below with specific device examples. The OPV device structure is as follows: indium tin oxide ITO/PEDOT PSS/active layer/PDINN/Ag
Device example 1 was prepared by the steps of:
(1) Firstly, cleaning ITO conductive glass by using a detergent, after the ITO conductive glass is cleaned cleanly, ultrasonically cleaning the ITO conductive glass by using deionized water, acetone and isopropanol for 15 minutes, and then drying the ITO conductive glass by using nitrogen and treating the ITO conductive glass in a plasma cleaner for 5 minutes so as to further clean the surface and improve the wettability;
(2) Spin-coating an anode buffer layer on ITO conductive glass by taking PEDOT:PSS as an anode buffer layer material, and specifically comprises the following steps: uniformly spin-coating PEDOT PSS on ITO in air, wherein the spin-coating speed is 3000-4000rpm/min, and drying at 150 ℃ for 15min to obtain an anode buffer layer with the thickness of 20 nm;
(3) A photoactive layer is spin-coated onto the anode buffer layer, wherein the active layer material comprises a donor material selected from the group consisting of organic compounds (H1-24) and (H2-30) and an acceptor material selected from the group consisting of (H3-11). Wherein the organic compound (H1-24): (H2-30): (H3-11) mass ratio of 0.5:0.5:1.05; the method comprises the following steps of uniformly spin-coating a photoactive layer material (the concentration of a mixture of a donor material and a receptor material in chloroform is 22 mg/mL) on an anode buffer layer in a glove box (inert gas atmosphere), wherein the spin-coating speed is 2000-4000rpm/min, and a photoactive layer with the thickness of 100nm is obtained;
(4) Spin-coating a PDINN serving as a cathode buffer layer material on the photoactive layer, wherein the specific operation steps are that after thermal annealing is performed on a hot table at 100 ℃ for 10min, the cathode buffer layer material PDINN is uniformly spin-coated on the active layer, and the spin-coating rotating speed is 1800-4000rpm/min, so that a cathode buffer layer with the thickness of 5nm is obtained;
(5) The preparation of the cathode layer with Ag as cathode material on the cathode buffer layer comprises the steps of high vacuum (1×10 -6 Millibar) Ag was evaporated onto the cathode buffer layer to form a cathode layer with a thickness of 100 nm;
(6) Finally, the device is encapsulated with ultraviolet hardening resin in a nitrogen glove box.
Device examples 2-5 were prepared as in device example 1, except that the photoactive layer materials were selected differently and the specific materials are shown in table 1.
Device comparative examples 1-4 the preparation method was the same as device example 1, except that the photoactive layer materials were selected and the mass ratios were different, and specific materials are shown in table 1.
TABLE 1 organic solar cell device structure
The prepared organic solar cell device is subjected to performance test, a cell current-voltage curve is tested under the irradiation of standard light of a sunlight simulator (SS-F5-3A) AM 1.5G, the photoelectric conversion efficiency of each device is calculated, and the result is shown in Table 2.
TABLE 2 photoelectric conversion efficiency of organic solar cells
As can be seen from the data in table 2, the photoelectric conversion efficiency of the device example 1 and the device example 2 was greatly improved relative to the device comparative example 1 and the device comparative example 2, the device example 3 and the device example 4 relative to the device comparative example 3, and the device example 5 relative to the device comparative example 4, respectively, because: the organic mixture provided by the invention comprises two small molecular materials, and the two small molecular materials have the same skeleton structure, and the difference is mainly that the end-capped electron-withdrawing unit groups are selected differently. Two donor materials with similar structures form a composite material like an alloy phase, and the bimolecular mixed phase helps to suppress charge recombination and reduce non-radiative capacity loss. Meanwhile, compared with a single-molecule donor material, the material has more continuous energy level, stronger and wider spectral absorption and more proper crystallinity when being matched with a proper acceptor material, so that more ideal interpenetrating network morphology is further obtained, exciton dissociation and charge transmission are further improved, and the photoelectric conversion efficiency of the device is further improved.
The reason why the photoelectric conversion efficiency of device example 1 was improved with respect to device example 2 and device example 3 with respect to device example 4 is that: the capped electron withdrawing units in the organic compound H1 and the organic compound H2 contain the same alkyl chain (R 11 、R 12 ) The photoelectric conversion efficiency of the device is improved by enabling the device to have better pi-pi accumulation.
The above examples further illustrate the content of the present application but should not be construed as limiting the present application. Modifications and substitutions to methods, procedures, or conditions of the present application without departing from the spirit and substance of the present application are intended to be within the scope of the present application. The technical means used in the examples are conventional means well known to those skilled in the art unless otherwise indicated.
Claims (10)
1. An organic mixture characterized by: comprises an organic compound H1 and an organic compound H2, wherein the organic compound H1 is selected from structures shown in a general formula (I), and the organic compound H2 is selected from structures shown in a general formula (II):
wherein,
R 1 、R 2 each occurrence is independently selected from the group consisting of straight chain alkyl groups having 1 to 20 carbon atomsBranched alkyl having 3 to 20 carbon atoms, straight-chain alkoxy having 1 to 20 carbon atoms, branched alkoxy having 3 to 20 carbon atoms, straight-chain alkylthio having 1 to 20 carbon atoms, branched alkylthio having 3 to 20 carbon atoms, unsubstituted or substituted by R * Substituted aromatic groups having 6-20 carbon atoms, or unsubstituted or substituted by R * Substituted heteroaromatic groups having 5 to 20 ring atoms, or a combination of the above;
R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 each occurrence is independently selected from the group consisting of-H, -D, -F, -Cl, -Br, -I, -CN, -NO 2 A linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a linear alkylthio group having 1 to 20 carbon atoms, a branched alkylthio group having 3 to 20 carbon atoms, or a combination thereof;
R 11 、R 12 independently for each occurrence a group selected from the group consisting of straight chain alkyl groups having 1 to 20 carbon atoms, branched alkyl groups having 3 to 20 carbon atoms, and combinations of these groups;
R * each occurrence is independently selected from: -D, -F, -Cl, -Br, -I, -CN, -NO 2 A linear alkyl group having 1 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a linear alkylthio group having 1 to 20 carbon atoms, a linear alkoxycarboxyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a branched alkylthio group having 3 to 20 carbon atoms, a branched alkoxycarboxyl group having 3 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms, or a heteroaromatic group having 5 to 20 ring atoms, or a combination thereof.
2. The organic mixture of claim 1, wherein: the structural units (A) contained in the general formula (I) and the general formula (II) are selected from the same structures,
* Representing the ligation site.
3. The organic mixture according to claim 2, characterized in that: r is R 1 、R 2 Each occurrence is independently selected from a straight chain alkyl group having 1 to 16 carbon atoms, a branched alkyl group having 3 to 16 carbon atoms, or any of the following structures:
wherein,
R 13 independently for each occurrence a straight chain alkyl group having 1 to 16 carbon atoms, or a branched alkyl group having 3 to 16 carbon atoms;
R 14 、R 15 、R 16 each occurrence is independently selected from: -H, -D, -F, -Cl, -Br, -I, -CN, -NO 2 A linear alkyl group having 1 to 16 carbon atoms, a linear alkoxy group having 1 to 16 carbon atoms, a linear alkylthio group having 1 to 16 carbon atoms, a linear alkoxycarboxyl group having 1 to 16 carbon atoms, a branched alkyl group having 3 to 16 carbon atoms, a branched alkoxy group having 3 to 16 carbon atoms, a branched alkylthio group having 3 to 16 carbon atoms, a branched alkoxycarboxyl group having 3 to 16 carbon atoms, or a combination thereof.
4. The organic mixture according to claim 2, characterized in that: r is R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 Each occurrence is independently selected from: -H, -D, -F, -Cl, -Br, -I, -CN, -NO 2 A linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a linear alkoxy group having 1 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, or a combination thereofA bolus.
5. The organic mixture according to claim 2, characterized in that:selected from any one of the following structures:
and/or the number of the groups of groups,selected from the following structures:
6. the organic mixture according to any one of claims 1 to 5, wherein: the saidSelected from the group consisting ofAnd->Selected from->
7. The organic mixture of claim 1, wherein: the organic compound H1 is selected from the following structures:
and/or the organic compound H2 is selected from the following structures:
/>
/>
8. the organic mixture according to any one of claims 1 to 7, wherein: the organic mixture further comprises an organic compound H3, wherein the organic compound H3 is selected from structures shown in a general formula (III):
wherein R is 101 、R 102 、R 103 、R 104 Independently selected from-H, -D, a linear alkyl group having 1-20 carbon atoms, a linear alkoxy group having 1-20 carbon atoms, a linear alkylthio group having 1-20 carbon atoms, a branched alkyl group having 3-20 carbon atoms, a branched alkoxy group having 3-20 carbon atoms, a branched alkylthio group having 3-20 carbon atoms, a phenyl group substituted with a linear or linear alkyl group having 6-12C atoms, a thienyl group substituted with a linear or linear alkyl group having 6-12C atoms, or a combination thereof;
R 105 、R 106 、R 107 、R 108 Each occurrence is independently selected from: -H, -D, -CH 3 、-F、-CF 3 -Cl, -Br, -I, -CN, or-NO 2 。
9. A composition characterized by: comprising the organic mixture according to any one of claims 1 to 8 and at least one organic solvent.
10. An organic electronic device comprising at least one photoactive layer, characterized in that: the photoactive layer material comprises the organic mixture according to any one of claims 1 to 8, or is prepared from the composition according to claim 9.
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