JP2020516706A - 重合体およびこれを含む有機太陽電池 - Google Patents
重合体およびこれを含む有機太陽電池 Download PDFInfo
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- JP2020516706A JP2020516706A JP2019554381A JP2019554381A JP2020516706A JP 2020516706 A JP2020516706 A JP 2020516706A JP 2019554381 A JP2019554381 A JP 2019554381A JP 2019554381 A JP2019554381 A JP 2019554381A JP 2020516706 A JP2020516706 A JP 2020516706A
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- 229920000642 polymer Polymers 0.000 title claims abstract description 111
- 239000000126 substance Substances 0.000 claims abstract description 250
- -1 GeRR′ Inorganic materials 0.000 claims description 91
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229910052711 selenium Inorganic materials 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229910003472 fullerene Inorganic materials 0.000 claims description 9
- 125000005110 aryl thio group Chemical group 0.000 claims description 8
- 239000011368 organic material Substances 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000005332 alkyl sulfoxy group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 36
- 238000004519 manufacturing process Methods 0.000 description 33
- 238000000034 method Methods 0.000 description 31
- 125000001424 substituent group Chemical group 0.000 description 20
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- 239000000243 solution Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 12
- 238000005227 gel permeation chromatography Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 11
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 10
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000001425 triazolyl group Chemical group 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 125000003373 pyrazinyl group Chemical group 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 0 CC(C)(C)c1c(*)c(*)c(-c(c([*-])c2)cc(*)c2-c2c(*)c(*)c(C(C)(C)C)[s]2)[s]1 Chemical compound CC(C)(C)c1c(*)c(*)c(-c(c([*-])c2)cc(*)c2-c2c(*)c(*)c(C(C)(C)C)[s]2)[s]1 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
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- 238000009826 distribution Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 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 4
- 230000001590 oxidative effect Effects 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 238000006619 Stille reaction Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 229910016036 BaF 2 Inorganic materials 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000011112 polyethylene naphthalate Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- BUOKUWQCVSZNCF-UHFFFAOYSA-N selenadiazole Chemical group C1=C[se]N=N1 BUOKUWQCVSZNCF-UHFFFAOYSA-N 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances 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
- 238000010626 work up procedure Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- AJKNNUJQFALRIK-UHFFFAOYSA-N 1,2,3-trifluorobenzene Chemical group FC1=CC=CC(F)=C1F AJKNNUJQFALRIK-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
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
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- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical group BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 1
- JTMODJXOTWYBOZ-UHFFFAOYSA-N 2-methyl-n-phenylaniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1 JTMODJXOTWYBOZ-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- QXDWMAODKPOTKK-UHFFFAOYSA-N 9-methylanthracen-1-amine Chemical group C1=CC(N)=C2C(C)=C(C=CC=C3)C3=CC2=C1 QXDWMAODKPOTKK-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- QSUHHQRSZOMZBB-UHFFFAOYSA-N C(C)C(CC=1SC=CC1F)CCCC.C(C)C(CC=1SC=CC1F)CCCC Chemical compound C(C)C(CC=1SC=CC1F)CCCC.C(C)C(CC=1SC=CC1F)CCCC QSUHHQRSZOMZBB-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical group C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
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- 239000004642 Polyimide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical group C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
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- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 1
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- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
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- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 238000004544 sputter deposition Methods 0.000 description 1
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- 229910052719 titanium Inorganic materials 0.000 description 1
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
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- 238000004506 ultrasonic cleaning Methods 0.000 description 1
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- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
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- 239000011701 zinc Substances 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
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- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/0248—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by their semiconductor bodies
- H01L31/0256—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by their semiconductor bodies characterised by the material
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Abstract
Description
下記化学式1で表される第1単位;
下記化学式2で表される第2単位;および
下記化学式3または4で表される第3単位を含む重合体を提供する。
[化学式1]
X1〜X6は、互いに同一または異なり、それぞれ独立に、CRR'、NR、O、SiRR'、PR、S、GeRR'、Se、またはTeであり、
A1〜A4は、互いに同一または異なり、それぞれ独立に、ハロゲン基であり、
Cy1〜Cy3は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のヘテロ環基であり、
Q1およびQ2は、互いに同一または異なり、それぞれ独立に、OまたはSであり、
R、R'、R"およびR1〜R8は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアルキルチオ基;置換もしくは非置換のアリールチオ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
R11およびR12は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;または置換もしくは非置換のアルキルチオ基である。
第1電極と、
前記第1電極に対向して備えられる第2電極と、
前記第1電極と前記第2電極との間に備えられ、光活性層を含む1層以上の有機物層とを含み、
前記光活性層は、前記重合体を含むものである有機太陽電池を提供する。
[化学式1−1]
R1、R2、R11、R12、X1、X2、A1およびA2は、前記化学式1で定義したものと同じであり、
X7およびX8は、互いに同一または異なり、それぞれ独立に、NR、O、SiRR'、PR、S、GeRR'、Se、またはTeである。
[化学式1−2]
R11、R12、A1およびA2は、前記化学式1で定義したものと同じである。
[化学式1−2−1]
[化学式2−1]
R3〜R6、A3およびA4は、前記化学式2で定義したものと同じである。
[化学式3−1]
R7、R8、Q1およびQ2は、前記化学式3および4で定義したものと同じであり、
X9は、CRR'、NR、O、SiRR'、PR、S、GeRR'、Se、またはTeであり、
Y1〜Y4は、互いに同一または異なり、それぞれ独立に、CR"、N、SiR"、P、またはGeR"であり、
R、R'、R"、R9、R10およびR19は、互いに同一または異なり、それぞれ独立に、水素;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアルキルチオ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアリールチオ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基である。
[化学式3−4]
R7〜R10およびR19は、前記化学式3−1〜3−3で定義したものと同じである。
[化学式5]
lは、モル分率であって、0<l<1の実数であり、
mは、モル分率であって、0<m<1の実数であり、
l+m=1であり、
Aは、前記化学式1で表される第1単位であり、
Bは、前記化学式2で表される第2単位であり、
CおよびC'は、互いに同一または異なり、それぞれ独立に、前記化学式3または化学式4で表される第3単位であり、
nは、単位の繰り返し数であって、1〜10,000の整数である。
[化学式5−1]
X1〜X6は、A1〜A4、Cy1〜Cy3、Q1、Q2、R、R'、R"、R1〜R8、R11およびR12は、前記化学式1〜4で定義したものと同じであり、
1、mおよびnは、前記化学式5で定義したものと同じであり、
X15およびX16は、互いに同一または異なり、それぞれ独立に、CRR'、NR、O、SiRR'、PR、S、GeRR'、Se、またはTeであり、
Cy13は、置換もしくは非置換のヘテロ環基であり、
Q11およびQ12は、互いに同一または異なり、それぞれ独立に、OまたはSであり、
R17およびR18は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアルキルチオ基;置換もしくは非置換のアリールチオ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基である。
[化学式5−3]
A1、A2、R11およびR12は、前記化学式1で定義したものと同じであり、
R107およびR108は、互いに同一または異なり、それぞれ水素;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基またはハロゲン基であり、R109、R110およびR119は、互いに同一または異なり、それぞれ水素;または置換もしくは非置換のアルキル基であり、
lは、モル分率であって、0<l<1の実数であり、
mは、モル分率であって、0<m<1の実数であり、
l+m=1であり、
nは、単位の繰り返し数であって、1〜10,000の整数である。
[化学式6−1]
lは、モル分率であって、0<l<1の実数であり、
mは、モル分率であって、0<m<1の実数であり、
l+m=1であり、
nは、単位の繰り返し数であって、1〜10,000の整数である。
[化学式A]
Ra〜Rfは、互いに同一または異なり、それぞれ独立に、水素;または置換もしくは非置換のアルキル基であり、
La〜Ldは、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリーレン基;または置換もしくは非置換の2価のヘテロ環基であり、
MaおよびMbは、互いに同一または異なり、それぞれ独立に、ハロゲン基;または置換もしくは非置換のアルキル基であり、
pおよびqは、互いに同一または異なり、それぞれ独立に、0〜2の整数であり、
pまたはqが2の場合、括弧内の構造は、互いに同一である。
[化学式A−1]
製造例1.重合体1の合成
(1)化学式Kの合成
100mLのテトラヒドロフラン(THF)に前記化学式Mの化合物3gを入れて溶かした後、0℃まで温度を下げた。この温度でヘキサン(hexane)に溶けている1.6M n−ブチルリチウム(n−BuLi)2.1当量をゆっくり入れて、1時間常温で撹拌した。この溶液にTHFに溶けている1Mトリメチルチンクロライド(1M Trimethyltinchloride in THF)3当量を一度に入れて、2時間撹拌した。この溶液に水を注ぎ込み、ジエチルエーテル(Diethyl ether)で2回抽出した後、水で2回洗い、硫酸マグネシウム(MgSO4、Magnesium sulfate)で残留水を除去した。残りの溶液を減圧して溶媒を除去し、エタノール(ethanol)で再結晶化して、薄黄色結晶の形態で化学式M−1を得た。(収率:60%)
前記で合成した化学式K−1、LおよびM−1の単量体を、クロロベンゼンを溶媒として、Pd2(dba)3およびP(o−tolyl)3と共に入れて、マイクロウェーブ反応器で重合して、下記の重合体1を製造した。製造された重合体1のGPC(Gel Permeation Chromatography)分析の結果、数平均分子量(Mn)は59,800g/mol、重量平均分子量(Mw)は70,330g/mol、HOMOおよびLUMOエネルギー準位はそれぞれ5.3、3.45であり、UV edgeは670nmであった。
[重合体1]
前記製造例1の(4)において反応物として下記の化合物を用いたことを除けば、前記製造例1と同様の過程で重合体2を製造した。製造された重合体2のGPC分析の結果、数平均分子量(Mn)は49,200g/mol、重量平均分子量(Mw)は65,980g/mol、HOMOおよびLUMOエネルギー準位はそれぞれ5.31、3.46であり、UV edgeは671nmであった。
前記製造例2の(3)においてC12H25Brの代わりにC8H17Brを用いたことを除けば、前記製造例2と同様の過程で重合体3を製造した。製造された重合体3のGPC分析の結果、数平均分子量(Mn)は54,670g/mol、重量平均分子量(Mw)は68,990g/mol、HOMOおよびLUMOエネルギー準位はそれぞれ5.31、3.46であり、UV edgeは670nmであった。
[重合体3]
前記製造例1の(3)においてC12H25Brの代わりに
前記製造例1の(3)においてC12H25Brの代わりに
[重合体5]
(1)化学式Nの合成
[重合体6]
[重合体7]
前記製造例1において
実施例1.
(1)複合溶液の製造
前記重合体1と化学式A−1(Solarmer Materials社)とを1:2の質量比でクロロベンゼン(Chlorobenzene、CB)2mLに溶かして、2.0wt%濃度の複合溶液(composit solution)を製造した。
[化学式A−1]
基板上に第1電極としてITOを形成し、ITO基板は蒸留水、アセトン、および2−プロパノールを用いて超音波洗浄し、ITO表面を10分間オゾン処理した。
実施例1において重合体1の代わりに前記重合体2を用いたことを除けば、前記実施例1と同様の過程で有機太陽電池を製造した。
実施例1において重合体1の代わりに前記重合体3を用いたことを除けば、前記実施例1と同様の過程で有機太陽電池を製造した。
実施例1において重合体1の代わりに前記重合体4を用いたことを除けば、前記実施例1と同様の過程で有機太陽電池を製造した。
実施例1において重合体1の代わりに前記重合体5を用いたことを除けば、前記実施例1と同様の過程で有機太陽電池を製造した。
実施例1において重合体1の代わりに前記重合体6を用いたことを除けば、前記実施例1と同様の過程で有機太陽電池を製造した。
実施例1において重合体1の代わりに前記重合体7を用いたことを除けば、前記実施例1と同様の過程で有機太陽電池を製造した。
実施例1において化学式A−1の代わりに下記化学式A−6(Solarmer Materials社)を用いたことを除けば、前記実施例1と同様の過程で有機太陽電池を製造した。
[化学式A−6]
実施例8において重合体1の代わりに前記重合体8を用いたことを除けば、前記実施例8と同様の過程で有機太陽電池を製造した。
実施例1において前記重合体1の代わりに下記の比較重合体1を用いたことを除けば、前記実施例1と同様の方法で有機太陽電池を製造した。
[比較重合体1]
実施例2において前記重合体1の代わりに前記比較重合体1を用いたことを除けば、前記実施例8と同様の方法で有機太陽電池を製造した。
実施例1において化学式A−1の代わりにPC71BMを用いたことを除けば、前記実施例1と同様の過程で有機太陽電池を製造した。
102:電子輸送層
103:光活性層
104:正孔輸送層
105:第2電極
Claims (16)
- 下記化学式1で表される第1単位;
下記化学式2で表される第2単位;および
下記化学式3または4で表される第3単位を含む重合体:
[化学式1]
X1〜X6は、互いに同一または異なり、それぞれ独立に、CRR'、NR、O、SiRR'、PR、S、GeRR'、Se、またはTeであり、
A1〜A4は、互いに同一または異なり、それぞれ独立に、ハロゲン基であり、
Cy1〜Cy3は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のヘテロ環基であり、
Q1およびQ2は、互いに同一または異なり、それぞれ独立に、OまたはSであり、
R、R'、およびR1〜R8は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアルキルチオ基;置換もしくは非置換のアリールチオ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
R11およびR12は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;または置換もしくは非置換のアルキルチオ基である。 - 前記第1単位は、下記化学式1−1で表されるものである、請求項1に記載の重合体:
[化学式1−1]
R、R'、R1、R2、R11、R12、X1、X2、A1およびA2は、前記化学式1で定義したものと同じであり、
X7およびX8は、互いに同一または異なり、それぞれ独立に、NR、O、SiRR'、PR、S、GeRR'、Se、またはTeである。 - 前記第1単位は、下記化学式1−2で表されるものである、請求項1に記載の重合体:
[化学式1−2]
R11、R12、A1およびA2は、前記化学式1で定義したものと同じである。 - 前記第2単位は、下記化学式2−1で表されるものである、請求項1または2に記載の重合体:
[化学式2−1]
R3〜R6、A3およびA4は、前記化学式2で定義したものと同じである。 - 前記第3単位は、下記化学式3−1〜3−3のうちのいずれか1つで表されるものである、請求項1から4のいずれか一項に記載の重合体:
[化学式3−1]
R7、R8、Q1およびQ2は、前記化学式3および4で定義したものと同じであり、
X9は、CRR'、NR、O、SiRR'、PR、S、GeRR'、Se、またはTeであり、
Y1〜Y4は、互いに同一または異なり、それぞれ独立に、CR"、N、SiR"、P、またはGeR"であり、
R、R'、R"、R9、R10およびR19は、互いに同一または異なり、それぞれ独立に、水素;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアルキルチオ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアリールチオ基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基である。 - 前記第3単位は、下記化学式3−4〜3−9のうちのいずれか1つで表されるものである、請求項5に記載の重合体:
[化学式3−4]
R7〜R10およびR19は、前記化学式3−1〜3−3で定義したものと同じである。 - 前記重合体は、下記化学式5で表される単位を含むものである、請求項1から6のいずれか一項に記載の重合体:
[化学式5]
lは、モル分率であって、0<l<1の実数であり、
mは、モル分率であって、0<m<1の実数であり、
l+m=1であり、
Aは、前記化学式1で表される第1単位であり、
Bは、前記化学式2で表される第2単位であり、
CおよびC'は、互いに同一または異なり、それぞれ独立に、前記化学式3または化学式4で表される第3単位であり、
nは、単位の繰り返し数であって、1〜10,000の整数である。 - 前記重合体は、下記化学式5−1または5−2で表される単位を含むものである、請求項7に記載の重合体:
[化学式5−1]
X1〜X6は、A1〜A4、Cy1〜Cy3、Q1、Q2、R、R'、R1〜R8、R11およびR12は、前記化学式1〜4で定義したものと同じであり、
1、mおよびnは、前記化学式5で定義したものと同じであり、
X15およびX16は、互いに同一または異なり、それぞれ独立に、CRR'、NR、O、SiRR'、PR、S、GeRR'、Se、またはTeであり、
Cy13は、置換もしくは非置換のヘテロ環基であり、
Q11およびQ12は、互いに同一または異なり、それぞれ独立に、OまたはSであり、
R17およびR18は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアルキルチオ基;置換もしくは非置換のアリールチオ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基である。 - 前記重合体は、下記化学式5−3〜5−9のうちのいずれか1つである、請求項1から6のいずれか一項に記載の重合体:
[化学式5−3]
A1、A2、R11およびR12は、前記化学式1で定義したものと同じであり、
R107およびR108は、互いに同一または異なり、それぞれ水素;置換もしくは非置換のアルキル基;置換もしくは非置換のアルコキシ基またはハロゲン基であり、R109、R110およびR119は、互いに同一または異なり、それぞれ水素;または置換もしくは非置換のアルキル基であり、
lは、モル分率であって、0<l<1の実数であり、
mは、モル分率であって、0<m<1の実数であり、
l+m=1であり、
nは、単位の繰り返し数であって、1〜10,000の整数である。 - 前記重合体は、下記化学式6−1〜6−30のうちのいずれか1つである、請求項1から6のいずれか一項に記載の重合体:
[化学式6−1]
lは、モル分率であって、0<l<1の実数であり、
mは、モル分率であって、0<m<1の実数であり、
l+m=1であり、
nは、単位の繰り返し数であって、1〜10,000の整数である。 - 第1電極と、
前記第1電極に対向して備えられる第2電極と、
前記第1電極と前記第2電極との間に備えられ、光活性層を含む1層以上の有機物層とを含み、
前記光活性層は、請求項1〜10のいずれか1項に記載の重合体を含むものである有機太陽電池。 - 前記光活性層は、電子供与体および電子受容体を含み、
前記電子供与体は、前記重合体を含むものである、請求項11に記載の有機太陽電池。 - 前記電子受容体は、非フラーレン(non−fullerene)系化合物を含むものである、請求項12に記載の有機太陽電池。
- 前記非フラーレン系化合物は、下記化学式Aで表されるものである、請求項13に記載の有機太陽電池:
[化学式A]
Ra〜Rfは、互いに同一または異なり、それぞれ独立に、水素;または置換もしくは非置換のアルキル基であり、
La〜Ldは、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリーレン基;または置換もしくは非置換の2価のヘテロ環基であり、
MaおよびMbは、互いに同一または異なり、それぞれ独立に、ハロゲン基;または置換もしくは非置換のアルキル基であり、
pおよびqは、互いに同一または異なり、それぞれ独立に、0〜2の整数であり、
pまたはqが2の場合、括弧内の構造は、互いに同一である。 - 前記電子受容体は、下記化学式A−1〜A−6のうちのいずれか1つである、請求項12から14のいずれか一項に記載の有機太陽電池:
[化学式A−1]
- 前記電子供与体と前記電子受容体との質量比は、2:1〜1:5である、請求項12から15のいずれか一項に記載の有機太陽電池。
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