CN115873024A - Condensed ring organic compound and application thereof in organic electronic device - Google Patents
Condensed ring organic compound and application thereof in organic electronic device Download PDFInfo
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- CN115873024A CN115873024A CN202211595793.7A CN202211595793A CN115873024A CN 115873024 A CN115873024 A CN 115873024A CN 202211595793 A CN202211595793 A CN 202211595793A CN 115873024 A CN115873024 A CN 115873024A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 32
- 239000000463 material Substances 0.000 claims abstract description 79
- 239000010410 layer Substances 0.000 claims description 62
- 125000006413 ring segment Chemical group 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- SPKSOWKQTVDRTK-UHFFFAOYSA-N 2-hydroxy-4-(4-methyl-1,3-dioxoisoindol-2-yl)benzoic acid Chemical group O=C1C=2C(C)=CC=CC=2C(=O)N1C1=CC=C(C(O)=O)C(O)=C1 SPKSOWKQTVDRTK-UHFFFAOYSA-N 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- -1 cyano, carbamoyl Chemical group 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 239000000872 buffer Substances 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 239000002346 layers by function Substances 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000005067 haloformyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 230000004927 fusion Effects 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 3
- 229930194542 Keto Natural products 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 2
- VINBVOMNIBDIPH-UHFFFAOYSA-N isocyanoimino(oxo)methane Chemical compound O=C=N[N+]#[C-] VINBVOMNIBDIPH-UHFFFAOYSA-N 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 66
- 238000009825 accumulation Methods 0.000 abstract description 3
- 230000005540 biological transmission Effects 0.000 abstract description 3
- 230000001737 promoting effect Effects 0.000 abstract description 2
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 167
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 137
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 71
- 230000015572 biosynthetic process Effects 0.000 description 50
- 238000003786 synthesis reaction Methods 0.000 description 50
- 239000002904 solvent Substances 0.000 description 48
- 239000012074 organic phase Substances 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 36
- 238000010438 heat treatment Methods 0.000 description 36
- 239000000741 silica gel Substances 0.000 description 36
- 229910002027 silica gel Inorganic materials 0.000 description 36
- 238000004440 column chromatography Methods 0.000 description 35
- 239000003480 eluent Substances 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000002994 raw material Substances 0.000 description 33
- 238000005303 weighing Methods 0.000 description 33
- 238000001035 drying Methods 0.000 description 32
- 238000001816 cooling Methods 0.000 description 31
- 239000004698 Polyethylene Substances 0.000 description 27
- 238000004821 distillation Methods 0.000 description 26
- 238000005086 pumping Methods 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 21
- 238000005406 washing Methods 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 238000002156 mixing Methods 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 15
- 229910001873 dinitrogen Inorganic materials 0.000 description 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 12
- 238000010790 dilution Methods 0.000 description 11
- 239000012895 dilution Substances 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000011777 magnesium Substances 0.000 description 9
- 238000013086 organic photovoltaic Methods 0.000 description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 229910052749 magnesium Inorganic materials 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000010791 quenching Methods 0.000 description 8
- 230000000171 quenching effect Effects 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- NZWIYPLSXWYKLH-UHFFFAOYSA-N 3-(bromomethyl)heptane Chemical compound CCCCC(CC)CBr NZWIYPLSXWYKLH-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910003472 fullerene Inorganic materials 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 239000011521 glass Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 4
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 4
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 229940125877 compound 31 Drugs 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 4
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 210000002706 plastid Anatomy 0.000 description 4
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000005997 bromomethyl group Chemical group 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000004431 deuterium atom Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000004537 pulping Methods 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910016036 BaF 2 Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000004696 Poly ether ether ketone Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical class 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
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000010949 copper 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 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
- 239000002245 particle Substances 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
- 229920003023 plastic Polymers 0.000 description 2
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 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
- 239000002861 polymer material Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 1
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical class C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-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
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 1
- GDSLUYKCPYECNN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[(4-fluorophenyl)methyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC=C(C=C2)F)C=CC=1 GDSLUYKCPYECNN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- IHXWECHPYNPJRR-UHFFFAOYSA-N 3-hydroxycyclobut-2-en-1-one Chemical compound OC1=CC(=O)C1 IHXWECHPYNPJRR-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
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- 229920000767 polyaniline Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000004587 thienothienyl group Chemical group S1C(=CC2=C1C=CS2)* 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
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- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention relates to a condensed ring organic compound and application thereof in an organic electronic device. The molecule core of the condensed ring organic compound has a larger condensed ring core, which is beneficial to the accumulation among molecules, thereby promoting the effective transmission and collection of charges, and being capable of helping the organic electronic device to improve the photoelectric conversion efficiency when being used as an electron acceptor material.
Description
Technical Field
The invention relates to the field of organic electronic device materials, in particular to a condensed ring organic compound and application thereof in an organic electronic device.
Background
Organic solar cells (OPVs) are receiving wide global attention due to their advantages of low cost, light weight, simple fabrication process, and large-area flexible fabrication. Organic Photovoltaic (OPV) cells generally consist of five parts: anode, anode buffer layer, active layer, cathode buffer layer and cathode. Wherein the active layer generally comprises a donor material and an acceptor material. The working principle is as follows: when sunlight is incident on the active layer through the transparent substrate and the electrodes, photons having energies greater than their band gap energies are absorbed by the acceptor material, and electrons are excited from a Highest Occupied Molecular Orbital (HOMO) to a Lowest Unoccupied Molecular Orbital (LUMO), with corresponding holes being generated at the HOMO. Since the relative dielectric constant of the organic material is small, electrons and holes exist in an exciton state in a bound state. Then, the excitons diffuse to the donor-acceptor interface, and under the drive of the energy level difference, the excitons are dissociated, so that the charge separation is realized. Then, under the action of the built-in electric field, free holes and electrons are transmitted to the anode and the cathode along the continuous channels of the donor and acceptor materials respectively, and are collected by the electrodes and output to an external circuit to form current. From the above, the selection of the active layer material is crucial for the efficiency of the organic solar cell device.
In the early stage of development of organic solar cells, fullerenes and derivatives thereof, represented by PC61BM and PC71BM, dominate electron acceptor materials due to their high electron affinity, isotropic electron transport ability, and high electron mobility, which is commonly referred to as the fullerene era. However, due to the limitation of the molecular structure of the fullerene acceptor, the absorption of the visible light region is weak, the energy level adjustability is poor, and the efficiency improvement of the organic solar cell is limited. Compared with the traditional fullerene receptor, the non-fullerene receptor is widely concerned by the scientific community by virtue of the advantages of strong absorption in visible and near infrared regions, easy regulation and control of spectral energy level and the like. Therefore, in order to further improve the efficiency and stability of organic solar cells, it is important to develop a high-performance novel non-fullerene acceptor material.
Disclosure of Invention
The invention aims to provide a condensed ring organic compound which is used as a micromolecular acceptor material applied to an organic solar cell and can help an organic photovoltaic device to improve photoelectric conversion efficiency.
In order to realize the purpose of the invention, the technical scheme is as follows:
a fused ring organic compound having a structure represented by general formula (I):
wherein:
Ar 1 、Ar 2 independently selected from a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms;
x is independently selected for each occurrence from O or C (CN) 2 ；
Y is selected from O, S, se or NR 9 ；
Each occurrence of Z is independently selected from N or CR 10 ；
R 1 -R 10 Each independently selected from: -H, -D, a linear alkyl group having 1 to 20C atoms, a linear alkoxy group having 1 to 20C atoms, a linear alkylthio group having 1 to 20C atoms, a branched or cyclic alkyl group having 3 to 20C atoms, a branched or cyclic alkoxy group having 3 to 20C atoms, a branched or cyclic alkylthio group having 3 to 20C atoms, a silyl group, a ketone group having 1 to 20C atoms, an alkoxycarbonyl group having 2 to 20C atoms, an aryloxycarbonyl group having 7 to 20C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amine group, -CF 3 、-OCF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted alkenyl group having 2-20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 50 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 50 ring atoms, an aryloxy group having 6 to 50 ring atoms, a heteroaryloxy group having 5 to 50 ring atoms, or a combination thereof;
wherein R is 1 -R 4 Wherein adjacent two groups form a ring or do not form a ring.
Correspondingly, the invention also provides a mixture which comprises the condensed ring organic compound and at least one organic functional material, wherein the organic functional material is selected from an anode buffer layer material, a cathode buffer layer material, an active layer donor material or an active layer acceptor material.
Accordingly, the present invention also provides an electron acceptor material selected from the fused ring organic compounds or mixtures as described above.
Correspondingly, the invention also provides an organic electronic device which comprises at least one functional layer, wherein the functional layer material is the fused ring organic compound or the mixture.
Compared with the prior art, the invention has the following remarkable advantages: the core of the condensed ring organic compound provided by the invention has a larger condensed ring core, and is more favorable for intermolecular accumulation, so that effective transmission and collection of electric charges are promoted, and the photoelectric conversion efficiency of a device is improved.
Detailed Description
The condensed ring organic compound and the application thereof in an organic electronic device provided by the present application are further described in detail below in order to make the purpose, technical scheme and effect of the present application clearer and clearer. It should be understood that the specific embodiments described herein are merely illustrative of the present application and are not intended to limit the present application.
As used herein, the term "and/or", "and/or" is selected to encompass any of two or more of the associated listed items, as well as any and all combinations of the associated listed items, including any two of the associated listed items, any more of the associated listed items, or all combinations of the associated listed items. It should be noted that when at least three items are connected by at least two conjunctive combinations selected from "and/or", "or/and", "and/or", it should be understood that, in the present application, the technical solutions definitely include the technical solutions all connected by "logic and", and also the technical solutions all connected by "logic or". For example, "A and/or B" includes three parallel schemes A, B and A + B. For example, a reference to "a, and/or, B, and/or, C, and/or, D" includes any one of a, B, C, and D (i.e., all connected by "logical or"), any and all combinations of a, B, C, and D (i.e., any two or any three of a, B, C, and D), and any four combinations of a, B, C, and D (i.e., all connected by "logical and").
In the present invention, the organic photovoltaic device and the organic solar cell have the same meaning and may be interchanged.
In the present invention, the aromatic groups, aromatic groups and aromatic ring systems have the same meaning and are interchangeable.
In the context of the present invention, heteroaromatic groups, heteroaromatic and heteroaromatic ring systems have the same meaning and are interchangeable.
In the present invention, the "heteroatom" is a non-carbon atom, and may be a N atom, an O atom, an S atom or the like.
In the present invention, "substituted" means that one or more hydrogen atoms in a substituent are substituted by a substituent.
In the present invention, when the same substituent is present in multiple times, it may be independently selected from different groups. If the general formula contains a plurality of R, R can be independently selected from different groups.
In the present invention, "substituted or unsubstituted" means that the defined group may or may not be substituted. When a defined group is substituted, it is understood that the defined group may be substituted with one or more substituents R selected from, but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1 to 20C atoms, heterocyclic group containing 3 to 20 ring atoms, aromatic group containing 6 to 20 ring atoms, heteroaromatic group containing 5 to 20 ring atoms, -NR' R ", silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may be further substituted with art-acceptable substituents; understandably, -NR 'R "wherein R' and R" are each independently selected from, but not limited to: H. deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1 to 10C atoms, heterocyclic group containing 3 to 20 ring atoms, aromatic group containing 6 to 20 ring atoms, heteroaromatic group containing 5 to 20 ring atoms. Preferably, R is selected from, but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group having 1 to 10C atoms, heterocyclic group having 3 to 10 ring atoms, aromatic group having 6 to 20 ring atoms, heteroaromatic group having 5 to 20 ring atoms, silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may be further substituted with substituents acceptable in the art.
In the present invention, the "number of ring atoms" represents 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, and a heterocyclic compound) in which atoms are bonded in a ring shape. When the ring is substituted with a substituent, the atom included in the substituent is not included in the ring-forming atoms. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of the benzene ring is 6, the number of ring atoms of the naphthalene ring is 10, and the number of ring atoms of the thienyl group is 5.
The "aryl group or aromatic group" means an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, and may be a monocyclic aryl group, or a condensed ring aryl group, or a polycyclic aryl group, at least one of which is an aromatic ring system for a polycyclic ring species. For example, "substituted or unsubstituted aryl group having 6 to 40 ring atoms" means an aryl group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, tetracenyl, fluorenyl, perylenyl, acenaphthenyl and derivatives thereof. It will be appreciated that a plurality of aryl groups may also be interrupted by short non-aromatic units (e.g. <10% of non-H atoms, such as C, N or O atoms), such as in particular acenaphthene, fluorene, or 9, 9-diarylfluorene, triarylamine, diarylether systems should also be included in the definition of aryl groups.
"heteroaryl or heteroaromatic group" means that on the basis of an aryl group at least one carbon atom is replaced by a non-carbon atom which may be a N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" refers to heteroaryl having 5 to 40 ring atoms, preferably substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, particularly preferably substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and heteroaryl is optionally further substituted, suitable examples including but not limited to: thienyl, furyl, pyrrolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-diazonaphthyl, phenanthridinyl, primidinyl, quinazolinone, dibenzothienyl, dibenzofuranyl, carbazolyl, and derivatives thereof.
In the present invention, "alkyl" may mean a linear, branched and/or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 15, or 1 to 6. Phrases encompassing this term, such as "C1-9 alkyl" refer to an alkyl group containing from 1 to 9 carbon atoms, which at each occurrence can be independently C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl. <xnotran> , , , , , , , ,2- ,3,3- , , , , , , 1- ,3- ,2- ,4- -2- , , 1- ,2- ,2- , ,4- ,4- , , 1- ,2,2- ,2- ,2- , , ,2- ,2- ,2- ,3,7- , , , , ,2- ,2- ,2- ,2- , , ,2- ,2- ,2- ,2- , , , , ,2- ,2- ,2- ,2- , , , , ,2- ,2- ,2- ,2- , </xnotran> N-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.
"amino" refers to a derivative of an amine having the formula-N (X) 2 Wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, or the like. Non-limiting types of amine groups include-NH 2 -N (alkyl) 2 NH (alkyl), -N (cycloalkyl) 2 NH (cycloalkyl), -N (heterocyclyl) 2 NH (heterocyclyl), -N (aryl) 2 NH (aryl), -N (alkyl) (heterocyclyl), -N (cycloalkyl) (heterocyclyl), -N (aryl) (heteroaryl), -N (alkyl) (heteroaryl) and the like.
In the present invention, unless otherwise specified, a hydroxyl group means-OH, a carboxyl group means-COOH, carbonyl means-C (= O) -, amino means-NH 2, formyl means-C (= O) H, a haloformyl group means-C (= O) Z (wherein Z means halogen), a carbamoyl group means-C (= O) NH2, an isocyanate group means-NCO, and an isothiocyanate group means-NCS.
The term "alkoxy" refers to a group of the structure "-O-alkyl", i.e. an alkyl group as defined above is attached to another group via an oxygen atom. Phrases encompassing this term, suitable examples include, but are not limited to: methoxy (-O-CH 3 or-OMe) ethoxy (-O-CH 2CH3 or-OEt) and tert-butyl butoxy (-O-C (CH 3) 3 or-OtBu).
The term "alkylthio" refers to a group of the structure "-S-alkyl", i.e. an alkyl group as defined above is connected to other groups via a sulfur atom. Phrases encompassing this term, suitable examples include, but are not limited to: methylthio (-S-CH 3 or-SMe) ethylthio (-S-CH 2CH3 or-SEt) and tert-butyl butylthio (-S-C (CH 3) 3 or-StBu).
In the present invention, "+" attached to a single bond represents a connection or a fusion site;
in the present invention, when the attachment site is not specified in the group, it means that an optional attachment site in the group is used as the attachment site;
in the present invention, when the same group contains a plurality of substituents of the same symbol, the substituents may be the same or different from each other, for example
The 6R's on the phenyl rings may be the same or different from each other.
The terms "combination thereof", "any combination thereof", "combination" and the like as used herein include all suitable combinations of any two or more items of the listed groups.
In the present invention, "further", "still", "specifically", etc. are used for descriptive purposes to indicate differences in content, but should not be construed as limiting the scope of the present invention.
In the present invention, "optionally", "optional" and "optional" refer to the presence or absence, i.e., to any one selected from the two juxtapositions "present" or "absent". If multiple optional parts appear in one technical scheme, if no special description exists, and no contradiction or mutual constraint relation exists, each optional part is independent.
In the present invention, the technical features described in the open type include a closed technical solution including the listed features, and also include an open technical solution including the listed features.
A fused ring organic compound having a structure represented by general formula (I):
wherein:
Ar 1 、Ar 2 independently selected from a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms;
x is independently selected for each occurrence from O or C (CN) 2 ；
Y is selected from O, S, se or NR 9 ；
Each occurrence of Z is independently selected from N or CR 10 ；
R 1 -R 10 Each independently selected from: -H, -D, linear alkyl having 1 to 20C atoms, linear alkoxy having 1 to 20C atoms, linear alkylthio having 1 to 20C atoms, branched or cyclic alkyl having 3 to 20C atoms, branched or cyclic alkoxy having 3 to 20C atoms, branched or cyclic alkylthio having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF 3 、-OCF 3 -Cl, -Br, -F, -I, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aromatic radical having 6 to 50 ring atoms, substituted or unsubstituted heteroaromatic radical having 5 to 50 ring atoms, aryloxy having 6 to 50 ring atoms, heteroaryloxy having 5 to 50 ring atoms, or a combination of the aforementioned radicalsA synthetically formed group;
wherein R is 1 -R 4 Wherein adjacent two groups form a ring or do not form a ring.
In one embodiment, R 1 -R 10 Each independently selected from: -H, -D, straight-chain alkyl having 1 to 20C atoms, straight-chain alkoxy having 1 to 10C atoms, straight-chain alkylthio having 1 to 10C atoms, branched or cyclic alkyl having 3 to 20C atoms, branched or cyclic alkoxy having 3 to 20C atoms, branched or cyclic alkylthio having 3 to 10C atoms, cyano, isocyano, hydroxy, nitro, -CF 3 、-OCF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, an aryloxy group having 6 to 30 ring atoms, a heteroaryloxy group having 5 to 30 ring atoms, or a combination thereof; wherein R is 1 -R 4 Wherein adjacent two groups form a ring or do not form a ring.
In one embodiment, ar 1 、Ar 2 Independently selected from a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms. Specifically, ar 1 、Ar 2 Independently selected from the group consisting of:
wherein:
* Represents a fusion site;
each occurrence of V is independently selected from N or CR 11 ；
Each occurrence of W is independently selected from O, S, se, CR 11 R 12 Or NR 12 ；
R 11 -R 12 Independently selected from: -H, -D, linear alkyl having 1 to 20C atoms, linear alkoxy having 1 to 20C atoms, linear alkylthio having 1 to 20C atoms, branched or cyclic alkane having 3 to 20C atomsA group, a branched or cyclic alkoxy group having 3 to 20C atoms, a branched or cyclic alkylthio group having 3 to 20C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination thereof.
In one embodiment, R 11 -R 12 Independently selected from: -H, -D, a straight chain alkyl group having 1 to 10C atoms, or a branched chain alkyl group having 3 to 10C atoms.
In one embodiment, formula (I) is selected from formula (II-1), (II-2) or (II-3):
in one embodiment, Z is independently selected from CH or N; further, each occurrence of Z in the formula (I), the formula (II-1), (II-2) or (II-3) is selected from the same group.
In a more preferred embodiment, formula (I) is selected from the following structures of formulae (III-1) to (III-6):
in one embodiment, if R 1 -R 4 Wherein two adjacent groups form a ring with each other, preferably a 6-membered ring; further R 1 -R 4 Wherein adjacent two groups form a substituted or unsubstituted 6-membered benzene ring with each other.
In one embodiment of the present invention, the substrate is,
independently selected for each occurrence from structural formula (B-1), (B-2) or (B-3):
* Indicates the attachment site.
In one embodiment, R 1 -R 4 Each independently selected from: -H, -D, straight-chain alkyl having 1 to 10C atoms, branched or cyclic alkyl having 3 to 10C atoms, cyano, isocyano, hydroxy, nitro, -CF 3 -Cl, -Br, -F, -I, or combinations thereof.
In one embodiment, R 1 -R 4 Each independently selected from: -H, -D, straight chain alkyl having 1 to 6C atoms, branched alkyl having 3 to 6C atoms, cyano, isocyano, hydroxy, nitro, -CF 3 -Cl, -Br, -F, or-I, or a combination thereof.
In a particular embodiment of the method of the invention,
(iii) independently for each occurrence, (C-1) to (C-60) the following structural formula:
wherein: * Indicates the attachment site.
Preferably, R 5 -R 8 Independently selected from-H, -D, or a straight chain alkyl group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atoms, or combinations thereof. More preferably, R 5 And R 6 Are selected from the same group; r is 7 -R 8 Selected from the same group.
In one embodiment, R 9 Selected from a linear alkyl group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atoms.
In one embodiment, the "straight chain alkyl group having 1 to 20C atoms" is selected from methyl, ethyl, C 8 H 17 、C 6 H 13 、C 5 H 11 、C 11 H 23 、C 12 H 25 (ii) a The "branched alkyl group having 3 to 20C atoms" is selected from the group consisting of t-butyl group, C-alkyl group an isopropyl group,
In one embodiment, the "straight chain alkyl group having 1 to 10C atoms" is selected from methyl, ethyl, C 8 H 17 、C 6 H 13 、C 5 H 11 (ii) a The "branched alkyl group having 3 to 20C atoms" is selected from the group consisting of a t-butyl group, a an isopropyl group,
More specifically, the fused ring organic compounds according to the present application may be selected from, but are not limited to, the following structural formulas:
the condensed ring organic compound can be used as an active layer material to be applied to an organic electronic device; preferably, the organic compounds according to the present invention can be applied as active layer acceptor materials in organic solar devices.
The invention also relates to a mixture containing at least one organic compound and at least another organic functional material, wherein the at least another organic functional material can be selected from an anode buffer layer material, a cathode buffer layer material, an active layer donor material or an active layer acceptor material. The weight ratio of the carbon black to another acceptor material is from 1. In one embodiment, the photoactive layer comprises a donor material and an acceptor material in a weight ratio of donor material/acceptor material =1/1.2.
In an embodiment, the further organic functional material is selected from an active layer donor material or an active layer acceptor material.
The application further relates to an electron acceptor material selected from the group consisting of fused ring organic compounds or mixtures as described above.
The application further relates to the use of a fused ring organic compound or mixture as described above in an organic electronic device. The Organic electronic device can be selected from, but not limited to, an Organic solar cell (OPV), an Organic Light Emitting Diode (OLED), an Organic light Emitting cell (OLEEC), an Organic Field Effect Transistor (OFET), an Organic light Emitting field effect transistor (fet), an Organic laser, an Organic spintronic device, an Organic sensor, an Organic Plasmon Emitting Diode (Organic plasma Emitting Diode), and the like, and is particularly preferably an OPV.
The present application also relates to an organic electronic device comprising at least one functional layer comprising the above-mentioned fused ring organic compounds or the above-mentioned mixtures. Preferably, the functional layer is selected from an anode buffer layer, an active layer or a cathode buffer layer.
In an embodiment, the organic electronic device comprises at least a first electrode, a second electrode and one or more functional layers between the first electrode and the second electrode. Preferably, the one or more functional layers are selected from active layers; more preferably, the one or more functional layers are selected from the group consisting of an anode buffer layer, an active layer and a cathode buffer layer.
Further, the organic solar cell further includes a substrate. Specifically, the substrate may be disposed at a lower portion of the first electrode.
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, as the substrate, a substrate having excellent transparency, surface smoothness, ease of handling, and water resistance can be used. Specifically, a glass substrate, a thin-film glass substrate, or a transparent plastic substrate may be used. The plastic substrate may include a film in a single layer or a multi-layer form such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyetheretherketone (PEEK), polyimide (PI), and the like, but is not limited thereto, and a substrate generally used for an organic solar cell may also be used.
At least one of the anode electrode and the cathode electrode is made of a transparent or translucent material. The electrode material may include a metal, such as silver (Ag), aluminum (Al), platinum (Pt), tungsten (W), copper (Cu), molybdenum (Mo), gold (A)u), nickel (Ni), palladium (Pd), magnesium (Mg), vanadium (V), chromium (Cr), zinc (Zn), or alloys thereof, etc.; materials having a multilayer structure, e.g. Al/Li, al/BaF 2 And Al/BaF 2 Ba, al/Yb, etc.; conductive nanomaterials such as metal nanowires, nanoparticle slurry, graphene, carbon nanotubes, etc.; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, such as ZnO: al or SnO 2: sb; and conductive polymers such as poly (styrenesulfonic acid) PEDOT: PSS (poly (3, 4-ethylenedioxythiophene)), polypyrrole, polyaniline, and the like, but are not limited thereto.
The active layer includes an electron donor material and an electron acceptor material. In the present specification, the active layer material may mean an electron donor material and an electron acceptor material.
In particular, the electron donor material can be a variety of polymeric or small molecule materials. The polymer material may be selected from polythiophene material systems, such as P3AT, P3HT, P3OT, P3DDT, and the like; fluorene-containing polymeric material systems, such as PF8BT, etc.; the novel narrow-band-gap polymer material system with the structure is formed by copolymerizing benzothiadiazoles (BT, BBT), quinoxalines (QU, PQ), pyrazines (TP, PQ) and electron-rich groups (such as thiophene derivatives), such as PCDTBT, PCPDTBT, PFO-DBT, PTB7, PM6, J52 and the like. The small molecule material may be selected from one or more of the following: copper (II) phthalocyanine, zinc phthalocyanine, tris [4- (5-dicyanomethylene methyl-2-thienyl) phenyl ] amine, 2, 4-bis [4- (N, N-dibenzylamino) -2, 6-dihydroxyphenyl ] squaraine, benzo [ B ] anthracene and pentacene, B8, B10, and the like.
The photoactive layer may be formed by: the photoactive material, such as an electron donor and/or an electron acceptor, is dissolved in an organic solvent, and then the resulting solution is applied by a method such as spin coating, dip coating, screen printing, gravure printing, spray coating, doctor blade, slit coating, and inkjet printing, but is not limited thereto.
The anode buffer layer material may be selected from materials with higher work functions, such as PEDOT of poly (styrene sulfonic acid): PSS (poly (3, 4-ethylenedioxythiophene)), molybdenum oxide (MoOx), vanadium oxide (V) 2 O 5 ) Nickel oxide (NiO), tungsten oxideCompound (WO) x， Preferably, x is selected from 2 or 3), etc., but is not limited thereto.
The cathode buffer layer material may be a low work function material, such as a metal complex containing 8-hydroxyquinoline, liQ, liF, titanium oxide (TiOx), zinc oxide (ZnO), cesium carbonate (Cs) 2 CO 3 ) And polymers such as PFN-Br or PFN, but not limited thereto.
The invention also relates to the use of the organic solar cell according to the invention in various devices, including, but not limited to, automotive and Building Integrated Photovoltaics (BIPV), electronic price tags, indoor photovoltaics, internet of things, smart agriculture, and the like.
The present invention will be described in connection with preferred embodiments, but the present invention is not limited to the following embodiments, and it should be understood that the appended claims outline the scope of the present invention and those skilled in the art, guided by the inventive concept, will appreciate that certain changes may be made to the embodiments of the invention, which are intended to be covered by the spirit and scope of the appended claims.
The present invention will now be described by way of examples of preferred compounds, but the invention is not limited to the examples described below, it being understood that the appended claims outline the scope of the invention and are intended to cover by those skilled in the art, in light of the teachings of the present invention, certain changes which may be made to the embodiments of the invention without departing from the spirit and scope of the invention as defined in the appended claims.
Example 1: synthesis of Compound 4:
synthesis of Compound 1-1:
accurately weighing a compound 6, 7-dinitroquinoxaline-2, 3-diamine (25g, 100mmol) and triethylamine (20.2g, 200mmol), sequentially adding the compound into a 1000mL three-neck flask, adding 350mL of anhydrous dichloromethane, pumping and introducing nitrogen for three times, stirring at room temperature for half an hour, then cooling the reaction system to 0 ℃, slowly dropwise adding thionyl chloride (14.3 g is dissolved in 150mL of dichloromethane), and keeping the temperature at 0 ℃. After the completion of the dropwise addition, the mixture was refluxed for 3 hours. After the reaction is finished, slowly pouring the reaction liquid into dilute hydrochloric acid, extracting for three times by using dichloromethane, combining organic phases, drying by using anhydrous sodium sulfate, then removing redundant solvent by reduced pressure distillation, and pulping crude products by using petroleum ether to obtain about 19g of compounds 1-2. Yield: 68.3 percent. Ms 278.02
Synthesis of Compounds 1-2:
accurately weighing a compound 1-1 (19g, 68mmol) and adding the compound into a 500mL three-neck flask, adding 200mL of ethyl acetate, pumping in nitrogen gas for three times, adding stannous chloride dihydrate (31g, 136mmol), heating and refluxing for 2 hours, washing after the raw materials completely react, extracting with ethyl acetate, combining organic phases, drying with anhydrous sodium sulfate, and removing redundant solvent by reduced pressure distillation to obtain the compound 1-2 with the yield of about 10.8 g: 72.8 percent. Ms 218.42 synthesis of compounds 1-4:
accurately weighing a compound 5- (bromomethyl) -11-alkane (49.8g, 200mmol), magnesium chips (7.2g, 300mmol), sequentially adding the magnesium chips (7.2g, 300mmol) into a 1000mL three-neck flask, adding about 300mL of anhydrous tetrahydrofuran, pumping and charging nitrogen for three times, adding a particle of iodine simple substance, heating the reaction system to 60 ℃, placing the reaction system at room temperature for reaction after obvious bubbles are generated on the surface of the magnesium chips, slowly dropwise adding the compound 1-3 (29.8g, 100mmol dissolved in 150mL of anhydrous tetrahydrofuran) into the reaction system after the raw materials are completely reacted, heating to 60 ℃ for reaction after the dropwise adding is completed, adding water for quenching after the reaction is completed, extracting ethyl acetate, combining organic phases, drying anhydrous sodium sulfate, then carrying out reduced pressure distillation to remove redundant solvent, carrying out silica gel column chromatography, and eluting to obtain about 19.3g of the compound 1-4 by using normal hexane. Yield: 49.8 percent. Ms:388.37
Synthesis of Compounds 1-5:
accurately weighing compounds 1-2 (4.4g, 20mmol), compounds 1-4 (15.5g, 40mmol), tris (dibenzylideneacetone) dipalladium (0.2g, 0.4mmol) and sodium tert-butoxide (5.8g, 60mmol), sequentially adding the mixture into a 500mL three-neck flask, adding about 200mL of anhydrous toluene, pumping and charging nitrogen for three times, adding 0.34mL of toluene (with the mass ratio of 10 percent, namely assuming that 10g of tri-tert-butylphosphine is contained in each 100mL of toluene) solution of tri-tert-butylphosphine, heating to 100 ℃ for reaction for 12 hours, cooling to room temperature after the reaction is finished, adding water for dilution, extracting with ethyl acetate, combining organic phases of anhydrous sodium sulfate, drying, distilling under reduced pressure to remove excessive solvent, carrying out silica gel column chromatography, and eluting with the volume ratio of an eluent to 1-5 about 10.6g of compounds, wherein the volume ratio is PE: EA =10 (volume ratio).
The yield thereof was found to be 63.8%. Ms:832.05
Synthesis of Compounds 1-6:
accurately weighing 1-5 (10g, 12mmol) of the compound, adding the compound into a 500mL three-neck flask, adding about 50mL of anhydrous dichloromethane, introducing nitrogen for three times, cooling to about 0 ℃, slowly dropwise adding a dichloromethane solution of NBS (8.9g, 50mmol dissolved in 200mL of dichloromethane) into the reaction system, and heating and refluxing for 3 hours after dropwise adding. Cooling to room temperature after the raw materials completely react, washing with water, extracting with dichloromethane for three times, combining organic phases, drying with anhydrous sodium sulfate, distilling under reduced pressure to remove redundant solvent, carrying out silica gel sample mixing column chromatography, and obtaining about 11.5g of the compound by using n-hexane as eluent. The yield thereof was found to be 83.6%. Ms:1147.51
Synthesis of Compounds 1-7:
accurately weighing the compounds 1-6 (11.5g, 10mmol) and adding the compounds into a 250mL three-neck flask, adding about 100mL of anhydrous dimethylbenzene, adding palladium acetate (0.13g, 0.5mmol) and potassium carbonate (4.13g, 30mmol), pumping nitrogen gas for three times, and heating to 30 ℃ for reacting for 6 hours. Cooling to room temperature after the raw materials completely react, washing with water, extracting with ethyl acetate, combining organic phases, drying with anhydrous sodium sulfate, distilling under reduced pressure to remove redundant solvent, carrying out silica gel sample mixing column chromatography, wherein the eluent is PE: EA =10 (volume ratio), and obtaining about 7.8g of the compound 1-7. Yield: 79.2 percent. Ms:986.16
Synthesis of Compounds 1-8:
compound 1 to 7 (6.9g, 7mmol) was weighed accurately, charged into a 250mL three-necked flask, anhydrous DMF was added to the flask in an amount of about 80mL, nitrogen gas was introduced thereinto three times, sodium hydride (60% to 0.8g) was added slowly to the reaction system, the mixture was reacted at room temperature for half an hour, bromoisooctane (4.1g, 21mmol) was added, and the mixture was heated to 60 ℃ and reacted for 3 hours. After the raw materials are completely reacted, adding water for dilution, and extracting by ethyl acetate. After the organic phases are combined and dried by anhydrous sodium sulfate, excess solvent is removed by distillation under reduced pressure, silica gel is subjected to column chromatography, and the eluent is PE: EA =30 (volume ratio) to obtain about 7.3g of the compound 1-8, and the yield is as follows: 86.2 percent. Ms 1210.31
Synthesis of Compounds 1-9:
accurately weighing 1-8 (7.3g, 6 mmol) of a compound, adding the compound into a 250mL three-neck flask, adding about 80mL of anhydrous THF, pumping nitrogen gas for three times, cooling to-80 ℃, then dropwise adding n-butyl lithium (2.5M 7.2mL) into the reaction system, slowly dropwise adding about 2mL of anhydrous DMF into the reaction system after reacting at a low temperature for 2 hours, naturally heating to room temperature, and reacting for 1 hour. Adding water for quenching after the raw materials completely react. Extracting with ethyl acetate for three times after separating liquid, combining organic phases, distilling under reduced pressure to remove redundant solvent, carrying out silica gel sample mixing and column chromatography, wherein the eluent is PE; EA =20 (volume ratio) gives about 5.2g of compound 1-9. Yield: and (4) 78.2 percent. Ms:1108.51
Synthesis of Compound 4:
accurately weighing compounds 1-9 (4.4g, 4mmol) and compounds 1-10 (2.8g, 12mmol), sequentially adding the compounds into a 100mL three-neck flask, adding 60mL of tert-butyl alcohol and 2mL of piperidine, pumping in nitrogen for three times, heating to 80 ℃ for reacting overnight, removing excessive solvent by reduced pressure distillation after the raw materials are completely reacted, extracting with dichloromethane for three times after water washing, combining organic phases, drying with anhydrous sodium sulfate, removing the excessive solvent by reduced pressure distillation, carrying out silica gel dressing column chromatography, wherein an eluent is PE: DCM =10 (volume ratio), and obtaining about 3.3g of compound 4: 53.9 percent. Ms:1532.24
Example 2: synthesis of Compound 8
Synthesis of compound 8:
accurately weighing compounds 1-9 (4.4g, 4mmol) and compounds 2-1 (3.1g, 12mmol), sequentially adding the materials into a 100mL three-neck flask, adding 60mL of tert-butyl alcohol and 2mL of piperidine, introducing nitrogen for three times, heating to 80 ℃ for reaction overnight, removing excessive solvent by reduced pressure distillation after the materials are completely reacted, extracting by dichloromethane for three times after water washing, combining organic phases, drying by anhydrous sodium sulfate, removing excessive solvent by reduced pressure distillation, carrying out silica gel dressing column chromatography, and obtaining about 3.5g of compounds 8 by an eluent of PE: DCM =10 (volume ratio): 55.2 percent. Ms:1584.06
Example 3: synthesis of Compound 31
Synthesis of Compound 3-2:
accurately weighing the compound 3-1 (18.8g, 100mmol) triethylamine (20.2g, 200mmol), sequentially adding the triethylamine (20.2g, 200mmol) into a 1000mL three-neck flask, adding 350mL anhydrous dichloromethane, pumping in nitrogen for three times, stirring at room temperature for half an hour, then cooling the reaction system to 0 ℃, slowly adding thionyl chloride (14.3 g dissolved in 150mL dichloromethane) dropwise, and keeping the temperature at 0 ℃. After the addition, the mixture was refluxed for 3 hours. After the reaction is finished, slowly pouring the reaction liquid into dilute hydrochloric acid, extracting for three times by using dichloromethane, combining organic phases, drying by using anhydrous sodium sulfate, then removing redundant solvent by reduced pressure distillation, and pulping crude products by using petroleum ether to obtain about 15.6g of a compound 3-2. Yield: 72.1 percent. Ms 217.24
Synthesis of Compounds 3-3:
accurately weighing the compounds 3-2 (4.3 g, 20mmol), the compounds 1-4 (15.5 g, 40mmol), the bis (dibenzylideneacetone) palladium (0.2 g,0.4 mmol) and the sodium tert-butoxide (5.8g, 60mmol), sequentially adding the materials into a 500mL three-neck flask, adding about 200mL of anhydrous toluene, pumping and introducing nitrogen for three times, adding 0.34mL of toluene (plastid ratio is 10%) solution of tri-tert-butylphosphine, heating to 100 ℃, reacting for 12 hours, cooling to room temperature after the reaction is finished, adding water for dilution, extracting with ethyl acetate, combining organic phases, drying with anhydrous sodium sulfate, distilling under reduced pressure to remove excessive solvent, carrying out silica gel sample stirring and column chromatography, wherein an eluent is PE: EA =10:1 to obtain the compound 3-3 about 10.3g. The yield thereof was found to be 62.1%. Ms:830.13
Synthesis of Compounds 3-4:
accurately weighing the compound 3-3 (10g, 12mmol), adding the compound into a 500mL three-neck flask, adding about 50mL of anhydrous dichloromethane, introducing nitrogen for three times, cooling to about 0 ℃, slowly dropwise adding a dichloromethane solution of NBS (8.9g, 50mmol and dissolving in 200mL of dichloromethane) into the reaction system, and heating and refluxing for 3 hours after dropwise adding. Cooling to room temperature after the raw materials completely react, washing with water, extracting with dichloromethane for three times, combining organic phases, drying with anhydrous sodium sulfate, distilling under reduced pressure to remove redundant solvent, mixing silica gel with a sample, and performing column chromatography, wherein the eluent is n-hexane to obtain about 11.6g of the compound 3-4. The yield thereof was found to be 84.4%. Ms:1145.81
Synthesis of Compounds 3-5:
accurately weighing the compound 3-4 (11.5g, 10mmol), adding the compound into a 250mL three-neck flask, adding about 100mL of anhydrous dimethylbenzene, adding palladium acetate (0.13g, 0.5mmol) and potassium carbonate (4.13g, 30mmol), pumping nitrogen gas, charging three times, and heating to 30 ℃ for reaction for 6 hours. Cooling to room temperature after the raw materials completely react, washing with water, extracting with ethyl acetate, combining organic phases, drying with anhydrous sodium sulfate, distilling under reduced pressure to remove redundant solvent, carrying out silica gel sample mixing column chromatography, wherein the eluent is PE: EA =10 (volume ratio), and obtaining about 7.5g of the compound 3-5. Yield: 76.3 percent. Ms:984.05
Synthesis of Compounds 3-6:
compound 3-5 (6.9g, 7mmol) was weighed accurately, charged into a 250mL three-necked flask, anhydrous DMF was added to the flask in an amount of about 80mL, nitrogen gas was introduced thereinto three times, sodium hydride (60% to 0.8g) was added slowly to the reaction system, the mixture was reacted at room temperature for half an hour, bromoisooctane (4.1g, 21mmol) was added, and the mixture was heated to 60 ℃ and reacted for 3 hours. After the raw materials are completely reacted, adding water for dilution, and extracting by ethyl acetate. After the organic phases are combined and dried by anhydrous sodium sulfate, excess solvent is removed by distillation under reduced pressure, silica gel is subjected to column chromatography, and the eluent is PE: EA =30 (volume ratio) to obtain about 7.1g of the compound 3-6, and the yield is as follows: 84 percent.
Ms:1208.42
Synthesis of Compounds 3-7:
accurately weighing 3-6 (7.3g, 6 mmol) of a compound, adding the compound into a 250mL three-neck flask, adding about 80mL of anhydrous THF, pumping and charging nitrogen for three times, cooling to-80 ℃, then dropwise adding n-butyl lithium (2.5M 7.2mL) into a reaction system, slowly dropwise adding about 2mL of anhydrous DMF into the reaction system after reacting at a low temperature for 2 hours, naturally heating to room temperature, and reacting for 1 hour. After the raw materials are completely reacted, adding water for quenching. Extracting with ethyl acetate for three times after separating liquid, combining organic phases, distilling under reduced pressure to remove redundant solvent, mixing silica gel with a sample, and performing column chromatography, wherein the eluent is PE; EA =20 (volume ratio) gave about 5.2g of compound 3-7. Yield: 78.4 percent. Ms 1106.50
Synthesis of compound 31:
accurately weighing compounds 3-7 (4.4g, 4mmol), compounds 3-8 (2g, 12mmol), sequentially adding into a 100mL three-neck flask, adding 60mL of tert-butyl alcohol and 2mL of piperidine, introducing nitrogen for three times, heating to 80 ℃ for reaction overnight, removing excessive solvent by reduced pressure distillation after the raw materials are completely reacted, extracting for three times by dichloromethane after water washing, combining organic phases, drying by anhydrous sodium sulfate, removing excessive solvent by reduced pressure distillation, carrying out silica gel dressing column chromatography, and obtaining about 3.3g of compound 31 by an eluent which is PE: DCM =10 (volume ratio): and 59 percent of the total weight of the solution. Ms of 1398.71
Example 4: synthesis of Compound 35
Synthesis of compound 35:
accurately weighing a compound 3-7 (4.4g, 4mmol), a compound 4-1 (3.2g, 12mmol), sequentially adding the mixture into a 100mL three-neck flask, adding 60mL of tert-butyl alcohol and 2mL of piperidine, pumping in nitrogen for three times, heating to 80 ℃ for reacting overnight, removing excessive solvent by reduced pressure distillation after the raw materials are completely reacted, extracting with dichloromethane for three times after water washing, combining organic phases, drying with anhydrous sodium sulfate, removing the excessive solvent by reduced pressure distillation, carrying out silica gel dressing column chromatography, and obtaining about 3.8g of a compound 35 by an eluent, namely DCM =10 (volume ratio): and (4) 59.5%. Ms:1595.80
Example 5: synthesis of Compound 54
Synthesis of Compound 5-1:
accurately weighing the compound 3-1 (18.8g, 100mmol), adding the compound into a 500mL three-neck flask, adding about 200mL of glacial acetic acid, cooling to 0 ℃, slowly dropwise adding an aqueous solution of sodium nitrite (8.28g, 120mmol dissolved in 20mL of water) into the system, stirring for half an hour at room temperature after the addition is finished, and performing suction filtration to obtain 18.5g of a crude product of the compound 5-1. Ms:199.87
Synthesis of Compound 5-2:
compound 5-1 (18.5 g) was weighed accurately, and charged into a 500mL three-necked flask, and about 200mL of DMF was added, followed by addition of sodium hydroxide (6 g, 150mmol) and bromoisooctane (23.2 g, 120mmol), purging with nitrogen gas three times, and then heating to 60 ℃ for reaction at 4 hours. And after the raw materials completely react, adding water for dilution, extracting for three times by ethyl acetate, drying by anhydrous sodium sulfate, distilling under reduced pressure to remove redundant solvent, mixing silica gel with a sample, and performing column chromatography to obtain a compound 5-2 about 17.5g, wherein the volume ratio of the eluent is PE: EA = 3. Yield: 60.5 percent. Ms 312.33
Synthesis of Compounds 5-4:
accurately weighing the compound 5-2 (6.2 g, 20mmol), the compound 5-3 (14.9g, 40mmol), the tris (dibenzylideneacetone) dipalladium (0.2g, 0.4mmol) and the sodium tert-butoxide (5.8g, 60mmol), sequentially adding the mixture into a 500mL three-neck flask, adding about 200mL of anhydrous toluene, pumping and introducing nitrogen for three times, adding 0.34mL of toluene (plastid ratio is 10%) solution of tri-tert-butylphosphine, heating to 100 ℃, reacting for 12 hours, cooling to room temperature after the reaction is finished, adding water for dilution, extracting with ethyl acetate, combining organic phases, drying with anhydrous sodium sulfate, carrying out reduced pressure distillation to remove excess solvent, carrying out silica gel sample stirring and column chromatography, and obtaining the compound 5-4 with the volume ratio of PE: EA =10 to 11.7g of the compound 5-4. The yield thereof was found to be 65.1%. Ms:897.32
Synthesis of Compounds 5-5:
compound 5-4 (10.8g, 12mmol) was weighed accurately, charged into a 500mL three-necked flask, and then added with about 50mL of anhydrous dichloromethane, and after introducing nitrogen gas three times, the temperature was lowered to about 0 ℃ and a dichloromethane solution of NBS (8.9g, 50mmol in 200mL of dichloromethane) was slowly added dropwise to the reaction system, and after completion of the dropwise addition, the mixture was refluxed for 3 hours. Cooling to room temperature after the raw materials completely react, washing with water, extracting with dichloromethane for three times, combining organic phases, drying with anhydrous sodium sulfate, distilling under reduced pressure to remove excessive solvent, carrying out silica gel sample mixing column chromatography, and eluting with n-hexane to obtain 5-5 about 12.0g of compound. The yield thereof was found to be 82.7%. Ms 1212.89
Synthesis of Compounds 5-6:
compound 5-5 (12.1g, 10mmol) was accurately weighed, and was charged in a 250mL three-necked flask, and about 100mL of anhydrous xylene was added, and palladium acetate (0.13g, 0.5mmol) and potassium carbonate (4.13g, 30mmol) were added, and after purging nitrogen gas three times, the temperature was raised to 30 ℃ and reacted for 6 hours. And (2) cooling to room temperature after the raw materials completely react, washing, extracting with ethyl acetate, combining organic phases, drying with anhydrous sodium sulfate, distilling under reduced pressure to remove redundant solvent, carrying out silica gel stirring column chromatography, wherein the eluent is PE: EA =10 (volume ratio), and obtaining about 8.4g of the compound 5-6. Yield: 79.6 percent. Ms:1051.17 synthesis of compounds 5-7:
compound 5-6 (7.3g, 7mmol) was weighed accurately and charged into a 250mL three-necked flask, anhydrous DMF was added in about 80mL, nitrogen gas was introduced three times and then sodium hydride (60% 0.8g) was added slowly to the reaction system, and after reacting at room temperature for half an hour, bromoisooctane (4.1g, 21mmol) was added, and then the mixture was heated to 60 ℃ and reacted for 3 hours. After the raw materials completely react, adding water for dilution, and extracting by ethyl acetate. After the organic phases are combined and dried by anhydrous sodium sulfate, excess solvent is removed by distillation under reduced pressure, silica gel is subjected to column chromatography, and the eluent is PE: EA =30 (volume ratio) to obtain 5-7.1 g of the compound, and the yield is as follows: 80.1 percent. Ms:1275.56
Synthesis of Compounds 5-8:
accurately weighing 5-7 (6.4g, 5 mmol) of a compound, adding the compound into a 250mL three-neck flask, adding about 80mL of anhydrous THF, pumping and charging nitrogen for three times, cooling to-80 ℃, then dropwise adding n-butyllithium (2.5M 6 mL) into a reaction system, slowly dropwise adding about 2mL of anhydrous DMF into the reaction system after reacting at a low temperature for 2 hours, naturally heating to room temperature, and reacting for 1 hour. Adding water for quenching after the raw materials completely react. Extracting with ethyl acetate for three times after separating liquid, combining organic phases, distilling under reduced pressure to remove redundant solvent, mixing silica gel with a sample, and performing column chromatography, wherein the eluent is PE; EA =20 (volume ratio) gave about 4.7g of compound 5-8. Yield: 79.9 percent. Ms:1173.26
Synthesis of compound 54:
accurately weighing 5-8 (4.7g, 4mmol) compounds 5-8 (2.3g, 12mmol), sequentially adding the materials into a 100mL three-neck flask, adding 60mL of tert-butyl alcohol and 2mL of piperidine, introducing nitrogen for three times, heating to 80 ℃ for reaction overnight, removing excessive solvent by reduced pressure distillation after the materials are completely reacted, extracting by dichloromethane for three times after water washing, combining organic phases, drying by anhydrous sodium sulfate, removing the excessive solvent by reduced pressure distillation, carrying out silica gel dressing column chromatography, and obtaining 54.6 g of the compound by an eluent of PE: DCM =10 (volume ratio): and (5) 59.6%. Ms:1525.32
Example 6: synthesis of Compound 108
Synthesis of Compound 6-2:
accurately weighing the compound 3-2 (4.3g, 20mmol), the compound 6-1 (9.9g, 40mmol), the tris (dibenzylideneacetone) dipalladium (0.2g, 0.4mmol) and the sodium tert-butoxide (5.8g, 60mmol), sequentially adding the mixture into a 500mL three-neck flask, adding about 200mL of anhydrous toluene, pumping and introducing nitrogen for three times, adding 0.34mL of toluene (plastid ratio is 10%) solution of tri-tert-butylphosphine, heating to 100 ℃, reacting for 12 hours, cooling to room temperature after the reaction is finished, adding water for dilution, extracting with ethyl acetate, combining organic phases, drying with anhydrous sodium sulfate, distilling under reduced pressure to remove redundant solvent, stirring the silica gel into a sample, and carrying out column chromatography by using an eluent with the volume ratio of PE: EA =10 to obtain about 8.5g of the compound 6-2. The yield thereof was found to be 77.3%. Ms 550.41
Synthesis of Compound 6-3:
accurately weighing the compound 6-2 (8.3g, 15mmol), adding the compound into a 250mL three-neck flask, adding about 100mL anhydrous xylene, adding palladium acetate (0.13g, 0.5mmol) and potassium carbonate (4.11g, 30mmol), pumping nitrogen gas for three times, and heating to 30 ℃ for reaction for 6 hours. Cooling to room temperature after the raw materials completely react, washing with water, extracting with ethyl acetate, combining organic phases, drying with anhydrous sodium sulfate, distilling under reduced pressure to remove redundant solvent, carrying out silica gel sample mixing column chromatography, wherein the eluent is PE: EA =10 (volume ratio), and obtaining about 6.3g of the compound 6-3. Yield: 88.1 percent. Ms:477.63
Synthesis of Compounds 6-4:
compound 6-3 (5.7 g, 12mmol) was weighed accurately, charged into a 250mL three-necked flask, and about 80mL of anhydrous DMF was added, and after introducing nitrogen gas three times, sodium hydrogen (60% 0.9 g) was added slowly to the reaction system, and after reacting at room temperature for half an hour, bromoisooctane (4.6 g, 24mmol) was added, followed by heating to 60 ℃ and reacting for 3 hours. After the raw materials completely react, adding water for dilution, and extracting by ethyl acetate. After the organic phases are combined and dried by anhydrous sodium sulfate, excessive solvent is removed by distillation under reduced pressure, and column chromatography is carried out on silica gel with stirring, wherein the eluent is PE: EA =30 (volume ratio) to obtain about 6.6g of compound 6-4, and the yield is as follows: 78.5 percent. Ms:702.01
Synthesis of Compounds 6-5:
compound 6-4 (6.3 g, 9mmol) is accurately weighed and added into a 500mL three-neck flask, about 50mL of anhydrous dichloromethane is added, nitrogen is pumped in and filled three times, then the temperature is reduced to about 0 ℃, a dichloromethane solution of NBS (3.2 g,18mmol dissolved in 200mL of dichloromethane) is slowly added into the reaction system, and after the dropwise addition is finished, the heating reflux is carried out for 3 hours. Cooling to room temperature after the raw materials completely react, washing with water, extracting with dichloromethane for three times, combining organic phases, drying with anhydrous sodium sulfate, distilling under reduced pressure to remove excessive solvent, mixing silica gel with a sample, and performing column chromatography, wherein the eluent is n-hexane to obtain 6-5 about 6.3g of the compound. The yield thereof was found to be 81.5%. Ms:859.60
Synthesis of Compounds 6-6:
accurately weighing a compound 5- (bromomethyl) -11-alkane (3.5g, 14mmol), magnesium chips (0.5g, 21mmol), sequentially adding into a 1000mL three-necked flask, adding about 300mL of anhydrous tetrahydrofuran, pumping and charging nitrogen for three times, adding a single iodine substance, heating the reaction system to 60 ℃, placing the reaction system at room temperature for reaction after obvious bubbles are generated on the magnesium chips, slowly dropwise adding a compound 6-5 (6 g,7mmol and dissolving in 150mL of anhydrous tetrahydrofuran) into the reaction system after the basic reaction of the raw materials is completed, heating to 60 ℃ for reaction after the dropwise adding is completed, adding water for quenching after the reaction is completed, extracting by ethyl acetate, combining an organic phase, drying anhydrous sodium sulfate, then carrying out reduced pressure distillation to remove redundant solvent, carrying out silica gel stirring column chromatography, and obtaining about 4.3g of the compound 6-6 by using n-hexane as an eluent. Yield: and (5) 59.2%. Ms:1038.53
Synthesis of Compounds 6-7:
accurately weighing 6-6 (4.2g, 4 mmol) of a compound, adding the compound into a 500mL three-neck flask, adding about 50mL of anhydrous dichloromethane, introducing nitrogen for three times, cooling to about 0 ℃, slowly dropwise adding a dichloromethane solution of NBS (2.1g, 12mmol dissolved in 200mL of dichloromethane) into the reaction system, and heating and refluxing for 3 hours after dropwise adding. Cooling to room temperature after the raw materials completely react, washing with water, extracting with dichloromethane for three times, combining organic phases, drying with anhydrous sodium sulfate, distilling under reduced pressure to remove redundant solvent, carrying out silica gel sample mixing column chromatography, and obtaining about 4.3g of compound 6-7 with eluent being n-hexane. The yield thereof was found to be 89.9%. Ms:1196.22
Synthesis of Compounds 6-8:
accurately weighing 6-7 (3.6g, 3 mmol) of a compound, adding the compound into a 100mL three-neck flask, adding about 40mL of anhydrous THF, pumping nitrogen gas for three times, cooling to-80 ℃, then dropwise adding n-butyl lithium (2.5M 1.8mL) into a reaction system, slowly dropwise adding about 2mL of anhydrous DMF into the reaction system after reacting at a low temperature for 2 hours, naturally heating to room temperature, and reacting for 1 hour. After the raw materials are completely reacted, adding water for quenching. Extracting with ethyl acetate for three times after separating liquid, combining organic phases, distilling under reduced pressure to remove redundant solvent, mixing silica gel with a sample, and performing column chromatography, wherein the eluent is PE; EA =20 (volume ratio) gave about 2.6g of compound 6-8. Yield: 79.2 percent. Ms 1094.57
Synthesis of compound 108:
accurately weighing compounds 6-8 (2.2g, 2mmol), 1-10 (1.4g, 6mmol), sequentially adding into a 100mL three-neck flask, adding 40mL of tert-butyl alcohol and 1mL of piperidine, introducing nitrogen for three times, heating to 80 ℃ for reaction overnight, removing excessive solvent by reduced pressure distillation after the raw materials are completely reacted, extracting for three times by dichloromethane after water washing, combining organic phases, drying by anhydrous sodium sulfate, removing excessive solvent by reduced pressure distillation, carrying out silica gel sample-mixing column chromatography, and obtaining the compound 108 of about 1.8g by an eluent of PE: DCM =10 (volume ratio): and (4) 59.3%. Ms:1518.35
Example 7: synthesis of Compound 136
Synthesis of Compound 7-1:
accurately weighing the compound 3-1 (18.8g, 100mmol) and the selenium dioxide (111g, 100mmol), sequentially adding the compound and the selenium dioxide into a 1000mL three-neck flask, adding 300mL of absolute ethyl alcohol, pumping and charging nitrogen for three times, heating to 80 ℃, reacting for 2 hours, cooling to room temperature after the raw materials are completely reacted, pumping and filtering, and pulping a filter cake by using petroleum ether to obtain about 15.6g of the compound 7-1. Yield: and 59.3 percent. Ms:263.87
Synthesis of Compound 7-2:
accurately weighing compound 7-1 (10.5g, 40mmol), compound 6-1 (19.8g, 80mmol), tris (dibenzylideneacetone) dipalladium (0.2g, 0.4mmol) and sodium tert-butoxide (11.5g, 120mmol), sequentially adding the mixture into a 500mL three-neck flask, adding about 200mL of anhydrous toluene, pumping and charging nitrogen for three times, adding 0.34mL of toluene (plastid ratio is 10%) solution of tri-tert-butylphosphine, heating to 100 ℃ for reaction for 12 hours, cooling to room temperature after the reaction is finished, adding water for dilution, extracting with ethyl acetate, drying the combined organic phase anhydrous sodium sulfate, distilling under reduced pressure to remove excessive solvent, stirring with silica gel, and eluting with PE: EA =10 to compound 7-2 about 16.8g. The yield thereof was found to be 70.4%. Ms 597.23
Synthesis of Compound 7-3:
compound 7-2 (11.9g, 20mmol) was weighed accurately, and charged into a 250mL three-necked flask, and about 100mL of anhydrous xylene was added, and palladium acetate (0.26g, 1mmol) and potassium carbonate (8.3g, 60mmol) were added, and after purging with nitrogen gas three times, the mixture was warmed to 30 ℃ to react for 6 hours. And (2) cooling to room temperature after the raw materials completely react, washing, extracting with ethyl acetate, combining organic phases, drying with anhydrous sodium sulfate, distilling under reduced pressure to remove redundant solvent, carrying out silica gel stirring column chromatography, wherein the eluent is PE: EA =10 (volume ratio), and obtaining about 8.3g of the compound 7-3. Yield: 79.3 percent. Ms 524.38
Synthesis of Compounds 7-4:
the compound 7-3 (7.9g, 15mmol) was weighed accurately, added to a 250mL three-necked flask, anhydrous DMF (about 80 mL) was added, nitrogen gas was pumped in three times, sodium hydride (60%: 1.7g) was slowly added to the reaction system, the reaction was carried out at room temperature for half an hour, then bromoisooctane (5.8g, 30mmol) was added, and the mixture was heated to 60 ℃ and reacted for 3 hours. After the raw materials are completely reacted, adding water for dilution, and extracting by ethyl acetate. After the organic phases are combined and dried by anhydrous sodium sulfate, excess solvent is removed by distillation under reduced pressure, silica gel is subjected to column chromatography, and the eluent is PE: EA =30 (volume ratio) to obtain about 8.6g of the compound 7-4, and the yield is as follows: 76.7 percent. Ms 748.88
Synthesis of Compounds 7-5:
accurately weighing 7-4 (7.5g, 10mmol) of the compound, adding the compound into a 500mL three-neck flask, adding about 50mL of anhydrous dichloromethane, introducing nitrogen for three times, cooling to about 0 ℃, slowly dropwise adding a dichloromethane solution of NBS (3.6g, 20mmol dissolved in 200mL of dichloromethane) into the reaction system, and heating and refluxing for 3 hours after dropwise adding. Cooling to room temperature after the raw materials completely react, washing with water, extracting with dichloromethane for three times, combining organic phases, drying with anhydrous sodium sulfate, distilling under reduced pressure to remove redundant solvent, mixing silica gel with a sample, and performing column chromatography, wherein the eluent is n-hexane to obtain 7-5 about 6.3g of the compound. The yield thereof was found to be 69.6%. Ms:906.51
Synthesis of Compounds 7-6:
accurately weighing a compound 5- (bromomethyl) -11-alkane (3.5g, 14mmol), magnesium chips (0.5g, 21mmol), sequentially adding into a 1000mL three-neck flask, adding about 300mL anhydrous tetrahydrofuran, pumping and charging nitrogen for three times, then adding a particle of iodine simple substance, then heating the reaction system to 60 ℃, placing the reaction system at room temperature after obvious bubbles are generated on the surface of the magnesium chips, reacting after the basic reaction of the raw materials is completed, slowly dropwise adding a compound 7-5 (6.3g, 7mmol) in 150mL anhydrous tetrahydrofuran, heating to 60 ℃ for reaction after dropwise adding, adding water for quenching after the reaction is completed, extracting by ethyl acetate, combining organic phases, drying anhydrous sodium sulfate, removing excess column chromatography solvent by reduced pressure distillation, stirring a silica gel sample, and obtaining a compound 7-6 about 4.5g by using an eluent as n-hexane. Yield: and 59.3 percent. Ms:1085.44
Synthesis of Compounds 7-7:
accurately weighing the compound 7-6 (4.3g, 4 mmol), adding the compound into a 500mL three-neck flask, adding about 50mL of anhydrous dichloromethane, introducing nitrogen for three times, cooling to about 0 ℃, slowly dropwise adding a dichloromethane solution of NBS (2.1g, 12mmol dissolved in 200mL of dichloromethane) into the reaction system, and heating and refluxing for 3 hours after dropwise adding. Cooling to room temperature after the raw materials completely react, washing with water, extracting with dichloromethane for three times, combining organic phases, drying with anhydrous sodium sulfate, distilling under reduced pressure to remove redundant solvent, carrying out silica gel sample mixing column chromatography, and obtaining about 4.3g of compound 7-7 with eluent being n-hexane. The yield thereof was found to be 86.5%. Ms:1242.04
Synthesis of Compounds 7-8:
accurately weighing a compound 7-7 (3.7g, 3mmol), adding the compound into a 100mL three-neck flask, adding about 40mL of anhydrous THF, pumping and charging nitrogen for three times, cooling to-80 ℃, then dropwise adding n-butyl lithium (2.5M 1.8mL) into a reaction system, reacting at a low temperature for 2 hours, slowly dropwise adding about 2mL of anhydrous DMF into the reaction system, naturally heating to room temperature, and reacting for 1 hour. After the raw materials are completely reacted, adding water for quenching. Extracting with ethyl acetate for three times after separating liquid, combining organic phases, distilling under reduced pressure to remove redundant solvent, mixing silica gel with a sample, and performing column chromatography, wherein the eluent is PE; EA =20 (volume ratio) to give about 2.7g of compound 7-8. Yield: 78.9 percent. Ms:1140.50
Synthesis of compound 136:
accurately weighing compounds 7-8 (2.3 g, 2mmol), 5-9 (1.2g, 6mmol), sequentially adding the compounds into a 100mL three-neck flask, adding 40mL of tert-butyl alcohol and 1mL of piperidine, introducing nitrogen for three times, heating to 80 ℃ for reaction overnight, removing excessive solvent by reduced pressure distillation after the raw materials are completely reacted, extracting by dichloromethane for three times after washing, combining organic phases, drying by anhydrous sodium sulfate, removing the excessive solvent by reduced pressure distillation, carrying out silica gel sample-mixing column chromatography, wherein an eluent is PE: DCM =10 (volume ratio) to obtain about 1.5g of a compound 136, and the yield is as follows: 50.2 percent. Preparation and characterization of Ms:1492.59OPV device
The preparation of OPV devices comprising the above compounds is detailed below by means of specific device examples. The OPV device structure is as follows: indium tin oxide ITO/PEDOT PSS/active layer/PFN-Br/Ag
The device 1 is prepared as follows:
1) Cleaning an ITO substrate:
and cleaning the ITO conductive glass anode layer by using a detergent, then ultrasonically cleaning the ITO conductive glass anode layer by using deionized water, acetone and isopropanol for 15 minutes, and then treating the ITO conductive glass anode layer in a plasma cleaner for 5 minutes to improve the surface wettability.
2) Anode buffer layer preparation
Uniformly spin-coating PEDOT (PSS) on ITO (indium tin oxide) in the air at the rotating speed of 3000-4000rpm, and drying at 150 ℃ for 15min to obtain an anode modification layer with the thickness of 20 nm.
3) Preparation of photoactive layer
Uniformly spin-coating an optical active layer material on the anode buffer layer in a glove box (inert gas atmosphere) at the rotating speed of 1800-4000rpm to obtain an active material layer with the thickness of 100 nm; wherein the donor material in the photoactive layer material is selected from PM6; the acceptor material is selected from compound 4; the mass ratio of the donor material to the acceptor material is 1.2.
4) Cathode buffer layer preparation
And (3) after thermal annealing is carried out on a hot table at the temperature of 100 ℃ for 10min, uniformly spin-coating the cathode buffer layer material PFN-Br on the active layer at the rotating speed of 1800-4000rpm to obtain the cathode buffer layer with the thickness of 5 nm.
5) Cathode layer preparation
Under high vacuum (1X 10) -6 Mbar) was evaporated onto the cathode buffer layer to form a cathode layer with a thickness of 100 nm.
6) Package with a metal layer
The devices were encapsulated with uv curable resin in a nitrogen glove box.
Compound REF:
the synthetic route is referred to CN 109134513A.
Device 2:
the same method of fabrication as device 1, except: the donor material in the active layer is selected from the compound 8.
Device 3:
the same method of fabrication as device 1, except: the donor material in the active layer is selected from compound 31.
Device 4:
the same method of fabrication as device 1, except: the donor material in the active layer is selected from compound 35.
Device 5:
the same method as for the preparation of device 1, with the difference that: the donor material in the active layer is selected from compound 54.
Device 6:
the same method of fabrication as device 1, except: the donor material in the active layer is selected from compound 108.
The device 7:
the same method of fabrication as device 1, except: the donor material in the active layer is selected from the compound 136.
The REF:
the same method as for the preparation of device 1, with the difference that: the donor material in the active layer is selected from a compound REF.
And (3) carrying out performance test on the prepared organic solar cell device, testing a cell current-voltage curve under the irradiation of standard light of a solar simulator (SS-F5-3A) AM 1.5G, and calculating the photoelectric conversion efficiency:
as can be seen from the device example device characterization described above, the compound claimed herein exhibits more excellent photoelectric conversion efficiency due to: compared with a comparative compound Ref, the core of the compound has a larger condensed ring core, and is more favorable for intermolecular accumulation, thereby promoting effective charge transmission and collection, and helping the device to improve the photoelectric conversion efficiency
The foregoing examples further illustrate the content of the present application but are not to be construed as limiting the present application. Modifications and substitutions to methods, steps or conditions of the present application are intended to be within the scope of the present application without departing from the spirit and substance of the present application. Unless otherwise specified, the technical means used in the examples are conventional means well known to those skilled in the art.
Claims (10)
1. A fused ring organic compound characterized by: the condensed ring organic compound has a structure represented by general formula (I):
wherein:
Ar 1 、Ar 2 independently selected from substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms;
x is independently selected for each occurrence from O or C (CN) 2 ；
Y is selected from O, S, se or NR 9 ；
Z is independently selected from N or CR at each occurrence 10 ；
R 1 -R 10 Each independently selected from: -H, -D, linear alkyl having 1 to 20C atoms, linear alkoxy having 1 to 20C atoms, linear alkylthio having 1 to 20C atoms, branched or cyclic alkyl having 3 to 20C atoms, branched or cyclic alkoxy having 3 to 20C atoms, branched or cyclic alkylthio having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF 3 、-OCF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted alkenyl group having 2-20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 50 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 50 ring atoms, an aryloxy group having 6 to 50 ring atoms, a heteroaryloxy group having 5 to 50 ring atoms, or a combination thereof;
wherein R is 1 -R 4 Wherein two adjacent groups form a ring or do not form a ring。
2. A fused ring organic compound according to claim 1, wherein: ar (Ar) 1 、Ar 2 Independently selected from the group consisting of:
wherein:
* Represents a fusion site;
each occurrence of V is independently selected from N or CR 11 ；
Each occurrence of W is independently selected from O, S, se, CR 11 R 12 Or NR 12 ；
R 11 -R 12 Independently selected from: -H, -D, a straight chain alkyl group having 1 to 20C atoms, a straight chain alkoxy group having 1 to 20C atoms, a straight chain alkylthio group having 1 to 20C atoms, a branched or cyclic alkyl group having 3 to 20C atoms, a branched or cyclic alkoxy group having 3 to 20C atoms, a branched or cyclic alkylthio group having 3 to 20C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination thereof.
3. A fused ring organic compound according to claim 2, wherein: the general formula (I) is selected from the general formula (II-1), (II-2) or (II-3):
4. a fused ring organic compound according to claim 1, wherein: z is independently selected from CH or N.
5. A fused ring organic compound according to claim 1, whereinIn the following steps: in the general formula (I)
Independently selected for each occurrence from structural formula (B-1), (B-2) or (B-3):
* Represents a linking site;
preferably, R 1 -R 4 Each independently selected from: -H, -D, linear alkyl having 1 to 10C atoms, branched or cyclic alkyl having 3 to 10C atoms, cyano, isocyano, hydroxy, nitro, -CF 3 -Cl, -Br, -F, -I, or combinations thereof.
6. A fused ring organic compound according to claim 1, wherein: r is 5 -R 8 Independently selected from H, D, or a straight chain alkyl group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atoms, or combinations thereof.
7. A fused ring organic compound according to claim 1, wherein: the fused ring organic compound is selected from the following structures:
8. a mixture, characterized by: the mixture includes the fused ring organic compound of any one of claims 1-7 and at least one organic functional material selected from an anode buffer layer material, a cathode buffer layer material, an active layer donor material, or an active layer acceptor material.
9. An electron acceptor material, characterized by: the electron acceptor material is selected from the fused ring organic compounds of any one of claims 1 to 7 or the mixtures of claim 8.
10. An organic electronic device comprising at least one functional layer, characterized in that: the functional layer material is selected from a fused ring organic compound according to any one of claims 1 to 7 or a mixture according to claim 8.
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| CN114163300A (en) * | 2020-09-11 | 2022-03-11 | 广州华睿光电材料有限公司 | Fused ring compounds and their use in organic electronic devices |
| CN114560882A (en) * | 2022-04-11 | 2022-05-31 | 广州追光科技有限公司 | Organic compound and organic electronic device comprising same |
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| CN114163300A (en) * | 2020-09-11 | 2022-03-11 | 广州华睿光电材料有限公司 | Fused ring compounds and their use in organic electronic devices |
| CN114560882A (en) * | 2022-04-11 | 2022-05-31 | 广州追光科技有限公司 | Organic compound and organic electronic device comprising same |
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