WO2011101810A1 - Use of indanthrene compounds in organic photovoltaics - Google Patents
Use of indanthrene compounds in organic photovoltaics Download PDFInfo
- Publication number
- WO2011101810A1 WO2011101810A1 PCT/IB2011/050677 IB2011050677W WO2011101810A1 WO 2011101810 A1 WO2011101810 A1 WO 2011101810A1 IB 2011050677 W IB2011050677 W IB 2011050677W WO 2011101810 A1 WO2011101810 A1 WO 2011101810A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- solar cell
- compound
- hydrogen
- phenyl
- Prior art date
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- 238000013086 organic photovoltaic Methods 0.000 title claims abstract description 10
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical class C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 title abstract description 38
- -1 indanthrene compound Chemical class 0.000 claims abstract description 659
- 235000019239 indanthrene blue RS Nutrition 0.000 claims abstract description 41
- 229910003472 fullerene Inorganic materials 0.000 claims abstract description 29
- 239000000463 material Substances 0.000 claims description 86
- 150000001875 compounds Chemical class 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 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 32
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000003184 C60 fullerene group Chemical group 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- MCEWYIDBDVPMES-UHFFFAOYSA-N [60]pcbm Chemical compound C123C(C4=C5C6=C7C8=C9C%10=C%11C%12=C%13C%14=C%15C%16=C%17C%18=C(C=%19C=%20C%18=C%18C%16=C%13C%13=C%11C9=C9C7=C(C=%20C9=C%13%18)C(C7=%19)=C96)C6=C%11C%17=C%15C%13=C%15C%14=C%12C%12=C%10C%10=C85)=C9C7=C6C2=C%11C%13=C2C%15=C%12C%10=C4C23C1(CCCC(=O)OC)C1=CC=CC=C1 MCEWYIDBDVPMES-UHFFFAOYSA-N 0.000 claims description 11
- 150000007942 carboxylates Chemical class 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 229910006069 SO3H Inorganic materials 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 8
- 125000005110 aryl thio group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 4
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- 230000007704 transition Effects 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 2
- 239000010410 layer Substances 0.000 description 160
- 239000000370 acceptor Substances 0.000 description 55
- 239000004065 semiconductor Substances 0.000 description 49
- 239000004020 conductor Substances 0.000 description 26
- 239000000203 mixture Substances 0.000 description 24
- 150000003254 radicals Chemical class 0.000 description 19
- 238000000034 method Methods 0.000 description 18
- 239000002019 doping agent Substances 0.000 description 16
- 229910052731 fluorine Inorganic materials 0.000 description 16
- 239000011737 fluorine Substances 0.000 description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 15
- 229910052801 chlorine Inorganic materials 0.000 description 15
- 238000000151 deposition Methods 0.000 description 14
- 230000008021 deposition Effects 0.000 description 14
- 239000011368 organic material Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000000859 sublimation Methods 0.000 description 12
- 230000008022 sublimation Effects 0.000 description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 10
- 125000004093 cyano group Chemical group *C#N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 229910052725 zinc Inorganic materials 0.000 description 8
- 239000011701 zinc Substances 0.000 description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 7
- 239000002800 charge carrier Substances 0.000 description 7
- 229910052802 copper Inorganic materials 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 7
- CXZRDVVUVDYSCQ-UHFFFAOYSA-M pyronin B Chemical compound [Cl-].C1=CC(=[N+](CC)CC)C=C2OC3=CC(N(CC)CC)=CC=C3C=C21 CXZRDVVUVDYSCQ-UHFFFAOYSA-M 0.000 description 7
- 229910052709 silver Inorganic materials 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 230000032258 transport Effects 0.000 description 7
- 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 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 6
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 229910052737 gold Inorganic materials 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 6
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 6
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical class C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 230000031700 light absorption Effects 0.000 description 5
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 4
- 229920003026 Acene Polymers 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000000295 complement effect Effects 0.000 description 4
- 238000005137 deposition process Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 239000011147 inorganic material Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 238000001906 matrix-assisted laser desorption--ionisation mass spectrometry Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 238000005215 recombination Methods 0.000 description 4
- 230000006798 recombination Effects 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
- ACNUVXZPCIABEX-UHFFFAOYSA-N 3',6'-diaminospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical class O1C(=O)C2=CC=CC=C2C21C1=CC=C(N)C=C1OC1=CC(N)=CC=C21 ACNUVXZPCIABEX-UHFFFAOYSA-N 0.000 description 3
- ZCAPDAJQDNCVAE-UHFFFAOYSA-N 5,6,7,8,14,15,16,17,23,24,25,26,32,33,34,35-hexadecafluoro-2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1,3,5,7,9,11,13(18),14,16,19,21(38),22(27),23,25,28,30(37),31(36),32,34-nonadecaene Chemical compound C12=C(F)C(F)=C(F)C(F)=C2C(N=C2NC(C3=C(F)C(F)=C(F)C(F)=C32)=N2)=NC1=NC([C]1C(F)=C(F)C(F)=C(F)C1=1)=NC=1N=C1[C]3C(F)=C(F)C(F)=C(F)C3=C2N1 ZCAPDAJQDNCVAE-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-ZSJDYOACSA-N Sulfuric acid-d2 Chemical compound [2H]OS(=O)(=O)O[2H] QAOWNCQODCNURD-ZSJDYOACSA-N 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- ILZSSCVGGYJLOG-UHFFFAOYSA-N cobaltocene Chemical class [Co+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 ILZSSCVGGYJLOG-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000002178 crystalline material Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000000260 fractional sublimation Methods 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000005240 physical vapour deposition Methods 0.000 description 3
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000010129 solution processing Methods 0.000 description 3
- 150000003577 thiophenes Chemical class 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- KXOGXZAXERYOTC-UHFFFAOYSA-N 1-amino-4-methoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2OC KXOGXZAXERYOTC-UHFFFAOYSA-N 0.000 description 2
- QCRQDGXGTSBWFK-UHFFFAOYSA-N 1-methoxy-4-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2OC QCRQDGXGTSBWFK-UHFFFAOYSA-N 0.000 description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
- 125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- XDXWNHPWWKGTKO-UHFFFAOYSA-N 207739-72-8 Chemical compound C1=CC(OC)=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C2=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC(=CC=C1C1=CC=C(C=C13)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 XDXWNHPWWKGTKO-UHFFFAOYSA-N 0.000 description 2
- DDCBCMPRTJJARO-UHFFFAOYSA-N 3,6-bis(dicyanomethylidene)-2,5-difluorocyclohexa-1,4-diene-1,4-dicarbonitrile Chemical compound FC1=C(C#N)C(=C(C#N)C#N)C(F)=C(C#N)C1=C(C#N)C#N DDCBCMPRTJJARO-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 2
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 2
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- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical class C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
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- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/44—Azines of the anthracene series
- C09B5/46—Para-diazines
- C09B5/48—Bis-anthraquinonediazines (indanthrone)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/20—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions
- H10K30/211—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions comprising multiple junctions, e.g. double heterojunctions
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
- H10K30/353—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains comprising blocking layers, e.g. exciton blocking layers
-
- 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
Definitions
- the present invention relates to an organic solar cell which comprises at least one photoactive region which comprises at least one indanthrene compound which is in contact with at least one fullerene compound, and to the use of indanthrene
- Photovoltaics is understood to mean the direct conversion of radiative energy, principally solar energy, to electrical energy.
- excitons In contrast to inorganic solar cells, the light does not directly generate free charge carriers in organic solar cells, but rather excitons are formed first, i.e. electrically neutral excited states in the form of electron-hole pairs. These excitons can be separated only by very high electrical fields or at suitable interfaces. In organic solar cells, sufficiently high fields are unavailable, and so all existing concepts for organic solar cells are based on exciton separation at photoactive interfaces (organic donor-acceptor interfaces or interfaces to an inorganic semiconductor). For this purpose, it is necessary that excitons which have been generated in the volume of the organic material can diffuse to this photoactive interface. The diffusion of excitons to the active interface thus plays a critical role in organic solar cells.
- the exciton diffusion length in a good organic solar cell must at least be in the order of magnitude of the typical penetration depth of light, in order that the predominant portion of the light can be utilized.
- the efficiency of an organic solar cell is characterized by its open-circuit voltage Voc. Further important characteristics are the short-circuit current Isc, the fill factor FF and the resulting efficiency ⁇ .
- the first organic solar cell with an efficiency in the percent range was described by Tang et al. in 1986 (CW. Tang et al., Appl. Phys. Lett. 48, 183 (1986)). It consisted of a two-layer system with copper phthalocyanine (CuPc) as the donor material
- a current aim in organic photovoltaics is to provide a new generation of solar cells which are significantly less expensive than solar cells composed of silicon or other inorganic semiconductors such as cadmium indium selenide or cadmium telluride. For this purpose, there is additionally a need for suitable semiconductive light-absorbing materials.
- One means of absorbing a large amount of light and of achieving good efficiencies is to use a pair of semiconductor materials which are complementary with regard to light absorption, for example comprising a short-wave-absorbing n- semiconductor and a long-wave-absorbing p-semiconductor.
- This concept is also the basis of the aforementioned first organic solar cell, known as the Tang cell.
- fullerene compounds absorb the light only weakly, it has been found that efficient solar cells can be produced when fullerenes or fullerene derivatives, such as C60 or C72, are used as n-semiconductors. It is additionally known, when using weakly absorbing semiconductor materials, to build two solar cells one on top of another.
- one cell comprises a combination of the weakly absorbing semiconductor with a semiconductor complementary thereto, which absorbs the short-wave radiation
- the other cell a combination of the weakly absorbing semiconductor with a semiconductor complementary thereto, which absorbs the long-wave radiation.
- two suitable p-semiconductors are required, one of which absorbs the short-wave radiation and one the long-wave radiation.
- the discovery of suitable semiconductor combinations is not trivial.
- the open-circuit voltages Voc of the individual components are additive. The total current is limited by the component cell with the lowest short-circuit current Isc.
- the two semiconductor materials of the individual cells thus have to be adjusted exactly with respect to one another.
- the first indanthrene dye Indanthrene Blue RS, was synthesized in 1901 by Bohn at BASF, and was the first representative of the anthraquinone vat dyes. Indanthrene is also referred to as indanthrone or C.I. Pigment Blue 60.
- JP 5102506 A describes a photovoltaic cell which has a photoactive region, in which a layer which comprises an organic donor material is in contact with a layer which comprises an organic acceptor material.
- the photoactive region comprises at least one indanthrene dye and/or an anthraquinoneacridone dye, but exclusively as an electron acceptor (n-semiconductor, electron conductor).
- Suitable indanthrene dyes described are dyes of the general formula (A) in which m and n are each 0 to 4,
- R 1 and R 2 are each halogen, alkyl, alkoxy, hydroxyl, amino, acetyl, carboxyl, nitro or cyano, and
- R 3 and R 4 are each hydrogen or alkyl.
- phthalocyanines and polymers with conjugated ⁇ -systems, such as polyacetylenes.
- indanthrene compounds are advantageously suitable as electron donors (p-semiconductors, hole conductors) in organic photovoltaics. They are especially suitable for a combination with at least one fullerene compound, such as C60, as an electron acceptor (n-semiconductor, electron conductor). It has especially been found that indanthrene compounds are suitable for use in tandem cells, since they have a long-wave absorption and exhibit a high open- circuit voltage in combination with a fullerene compound, such as C60.
- the invention firstly provides an organic solar cell comprising at least one photoactive region which comprises at least one indanthrene compound which is in contact with at least one fullerene compound, wherein the indanthrene compound is selected from compounds of the general formula (I) in which
- R a and R b are each independently selected from hydrogen, deuterium, unsubstituted or substituted alkyl, unsubstituted or substituted cycloalkyl and unsubstituted or substituted aryl
- the R 1 to R 12 radicals are each independently selected from hydrogen, halogen, nitro, cyano, hydroxyl, carboxyl, carboxylates, SO3H, sulfonate, Ne a E b
- E a and E b are each independently hydrogen, alkyl, cycloalkyl or aryl.
- the invention further provides for
- the invention further provides novel compounds of the formula I, i.e. compounds of the formula I in which R 1 to R 12 are all hydrogen and R a and R b are both deuterium.
- the invention further provides novel compounds of the formula I, i.e. compounds of the formula I in which R 1 and R 9 are both phenoxy and the R a , R b , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 10 , R 11 and R 12 radicals are all hydrogen, or R 5 and R 8 are both methoxy and the R a , R , R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 9 , R 10 , R 11 and R 12 radicals are all hydrogen.
- Figure 1 shows a solar cell which is suitable for the use of indanthrene compounds and has normal structure:
- Figure 2 shows a solar cell with inverse structure.
- Figure 3 shows the structure of a solar cell with normal structure and with a donor- acceptor interface in the form of a bulk heterojunction.
- Figure 4 shows the structure of a solar cell with inverse structure and with a donor- acceptor interface in the form of a bulk heterojunction.
- Figure 5 shows the structure of a tandem cell.
- Figure 6 shows the structure of a solar cell with a donor-acceptor interface in the form of a bulk heterojunction configured as a gradient.
- Figure 7 shows the absorption spectrum of a vapor-deposited film of indanthrene blue.
- Figure 8 shows the absorption spectrum of a vapor-deposited film of 4,4' - dimethoxyindanthrone.
- Figure 9 shows the absorption spectrum of a vapor-deposited film of 5,5' - diphenoxyindanthrone.
- photoactive region represents a photoactive heterojunction formed by at least one electron-conducting organic material and at least one hole-conducting organic material.
- an organic material is referred to as "hole- conducting” when the charge carriers which are formed as a result of light absorption and charge separation at a heterojunction ("photogenerated charge carriers") are transported within the material in the form of holes. Accordingly, an organic material is referred to as “electron-conducting” when photogenerated charge carriers are transported within the material in the form of electrons.
- a “heterojunction” refers to an interface region between the electron-conducting and the hole-conducting material.
- a “photoactive heterojunction” refers to a heterojunction between the electron- conducting and the hole-conducting material when excited states formed by light absorption in the electron-conducting and/or the hole-conducting material ("excitons") which are separated in the region of the heterojunction into the individual charge carriers, namely electrons and holes, which are then in turn transported through the electron-conducting material/the hole-conducting material to electrical contacts, where electrical energy can be drawn off.
- a “flat heterojunction” refers to a heterojunction between the electron-conducting and the hole-conducting material when the interface between the electron-conducting and the hole-conducting material is formed as an essentially cohesive surface between the two material regions, namely one region of the electron-conducting material and one region of the hole-conducting material (cf. C. W. Tang, Appl. Phys. Lett, 48 (2), 183-185 (1986) or N. Karl et al., Mol. Cryst. Liq. Cryst, 252, 243-258 (1994)).
- a “bulk heterojunction” refers to a heterojunction between the electron-conducting and the hole-conducting material when the electron-conducting material and the hole- conducting material are at least partly mixed with one another, such that the interface between the electron-conducting and the hole-conducting material comprises a multitude of interface sections distributed over the volume of the material mixture (cf., for example, C.J. Brabec et al., Adv. Funct. Mater., 1 1 (1 ), 15 (2001 )).
- the terms indanthrene compound and indanthrene compound are used synonymously.
- the indanthrene compounds used in accordance with the invention are photoactive materials having a high absorption coefficient in the long-wavelength range of the solar spectrum. They are especially suitable for use in a component cell of a tandem cell, in order to achieve a maximum light yield combined with a high voltage. It is thus possible to further improve the efficiency of organic solar cells.
- the expression "unsubstituted or substituted alkyl, alkoxy, alkylthio, cycloalkyi, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio, oligo(het)aryl, oligo(het)aryloxy and oligo(het)alkylthio" represents unsubstituted or substituted alkyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted cycloalkyi, unsubstituted or substituted aryl, unsubstituted or substituted aryloxy, unsubstituted or substituted arylthio, unsubstituted or substituted hetaryl, unsubstituted or substituted hetaryloxy, unsubstituted or substituted hetaryloxy, unsubstit
- alkyl comprises straight-chain or branched alkyl.
- Alkyl is preferably Ci-C3o-alkyl, especially Ci-C2o-alkyl and most preferably Ci-Ci2-alkyl.
- alkyl groups are especially methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n- nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-hexadecyl, n-octadecyl and n-eicosyl.
- R c is preferably hydrogen, alkyl, cycloalkyi, heterocycloalkyi, aryl or hetaryl.
- Substituted alkyl groups may, depending on the length of the alkyl chain, have one or more (e.g. 1 , 2, 3, 4, 5 or more than 5) substituents.
- Cycloalkyi, heterocycloalkyi, aryl and hetaryl substituents of the alkyl groups may in turn be unsubstituted or substituted; suitable substituents are the substituents mentioned below for these groups.
- Carboxylate and sulfonate respectively represent a derivative of a carboxylic acid function and a sulfonic acid function, especially a metal carboxylate or sulfonate, a carboxylic ester or sulfonic ester function or a carboxamide or sulfonamide function.
- Aryl-substituted alkyl radicals (“aralkyl”, also referred to hereinafter as arylalkyl) have at least one unsubstituted or substituted aryl group, as defined below.
- R d is preferably hydrogen, alkyl, cycloalkyi, heterocycloalkyi, aryl or hetaryl.
- Aralkyl is preferably phenyl-Ci-Cio-alkyl, more preferably phenyl-Ci-C4-alkyl, for example benzyl, 1 -phenethyl, 2-phenethyl, 1 -phenprop-1 -yl, 2-phenprop-1 -yl, 3-phenprop-1 -yl,
- Halogen-substituted alkyl groups comprise a straight-chain or branched alkyl group in which at least one hydrogen atom or all hydrogen atoms are replaced by halogen.
- the halogen atoms are preferably selected from fluorine, chlorine and bromine, especially fluorine and chlorine.
- Examples of haloalkyi groups are especially chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl,
- unsubstituted or substituted alkyl also apply to unsubstituted or substituted alkoxy, unsubstituted or substituted alkylamino, unsubstituted or substituted alkylthio (alkylsulfanyl), etc.
- cycloalkyi denotes a cycloaliphatic radical having preferably 3 to 10, more preferably 5 to 8, carbon atoms.
- Examples of cycloalkyi groups are especially cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
- Substituted cycloalkyi groups may, depending on the ring size, have one or more (e.g. 1 , 2, 3, 4, 5 or more than 5) substituents. These are preferably each independently selected from alkyl, alkoxy, alkylthio, cycloalkyi, heterocycloalkyi, aryl, hetaryl, fluorine, chlorine, bromine, hydroxyl, mercapto, cyano, nitro, nitroso, formyl, acyl, COOH, carboxylate, alkylcarbonyloxy, carbamoyl, SO3H , sulfonate, sulfamino, sulfamide, amidino, NE 3 E 4 where E 3 and E 4 are each independently hydrogen, alkyl, cycloalkyi, heterocycloalkyi, aryl or hetaryl.
- the cycloalkyi groups preferably bear one or more, for example one, two, three, four or five, Ci-C6-alkyl groups.
- substituted cycloalkyl groups are especially 2- and 3-methyl- cyclopentyl, 2- and 3-ethylcyclopentyl, 2-, 3- and 4-methylcyclohexyl, 2-, 3- and 4-ethylcyclohexyl, 2-, 3- and 4-propylcyclohexyl, 2-, 3- and 4-isopropylcyclohexyl, 2-, 3- and 4-butylcyclohexyl, 2-, 3- and 4-sec.-butylcyclohexyl, 2-, 3- and 4-tert- butylcyclohexyl, 2-, 3- and 4-methylcycloheptyl, 2-, 3- and 4-ethylcycloheptyl, 2-, 3- and 4-propylcycloheptyl, 2-, 3- and 4-isopropylcycloheptyl, 2-
- aryl comprises mono- or polycyclic aromatic hydrocarbon radicals having 6 to 18, preferably 6 to 14, more preferably 6 to 10, carbon atoms.
- aryl are especially phenyl, naphthyl, indenyl, fluorenyl, anthracenyl, phenanthrenyl, naphthacenyl, chrysenyl, pyrenyl, etc., and especially phenyl or naphthyl.
- Substituted aryls may, depending on the number and size of their ring systems, have one or more (e.g. 1 , 2, 3, 4, 5 or more than 5) substituents. These are preferably each independently selected from alkyl, alkoxy, alkylthio, cycloalkyl, heterocycloalkyl, aryl, hetaryl, fluorine, chlorine, bromine, hydroxyl, mercapto, cyano, nitro, nitroso, formyl, acyl, COOH, carboxylate, alkylcarbonyloxy, carbamoyl, SO3H, sulfonate, sulfamino, sulfamide, amidino, NE 5 E 6 where E 5 and E 6 are each independently hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl.
- alkyl, alkoxy, alkylamino, alkylthio, cycloalkyl, heterocycloalkyl, aryl and hetaryl substituents on the aryl may in turn be unsubstituted or substituted. Reference is made to the substituents mentioned above for these groups.
- the substituents on the aryl are preferably selected from alkyl, alkoxy, haloalkyl, haloalkoxy, aryl, fluorine, chlorine, bromine, cyano and nitro.
- Substituted aryl is more preferably substituted phenyl which generally bears 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, substituents.
- Substituted aryl is preferably aryl substituted by at least one alkyl group ("alkaryl", also referred to hereinafter as alkylaryl).
- Alkaryl groups may, depending on the size of the aromatic ring system, have one or more (e.g. 1 , 2, 3, 4, 5, 6, 7, 8, 9 or more than 9) alkyl substituents.
- the alkyl substituents may be unsubstituted or substituted. In this regard, reference is made to the above statements regarding unsubstituted and substituted alkyl.
- the alkaryl groups have exclusively unsubstituted alkyl substituents.
- Alkaryl is preferably phenyl which bears 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, more preferably 1 or 2, alkyl substituents.
- Aryl which bears one or more radicals is, for example, 2-, 3- and 4-methylphenyl, 2,4-, 2,5-, 3,5- and 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 2-, 3- and 4-ethylphenyl, 2,4-, 2,5-, 3,5- and 2,6-diethylphenyl, 2,4,6-triethylphenyl, 2-, 3- and 4-propylphenyl, 2,4-, 2.5- , 3,5- and 2,6- dipropylphenyl, 2,4,6-tripropylphenyl, 2-, 3- and 4-isopropylphenyl, 2,4-, 2,5-, 3,5- and 2,6-diisopropylphenyl, 2,4,6-triisopropylphenyl, 2-, 3- and 4- buty
- aryloxy is phenoxy, naphthyloxy or anthracenyloxy.
- arylthio are phenylthio, naphthylthio or anthracenylthio.
- heterocycloalkyi comprises nonaromatic, unsaturated or fully saturated, cycloaliphatic groups having generally 5 to 8 ring atoms, preferably 5 or 6 ring atoms.
- the heterocycloalkyi groups compared to the corresponding cycloalkyi groups, 1 , 2, 3, 4 or more than 4 of the ring carbon atoms are replaced by heteroatoms or heteroatom-containing groups.
- R e is preferably hydrogen, alkyl, cycloalkyi, heterocycloalkyi, aryl or hetaryl.
- Heterocycloalkyi is unsubstituted or optionally bears one or more, e.g. 1 , 2, 3, 4, 5, 6 or 7, identical or different radicals. These are preferably each
- alkyl independently selected from alkyl, alkoxy, alkylamino, alkylthio, cycloalkyi,
- heterocycloalkyi aryl, hetaryl, fluorine, chlorine, bromine, hydroxyl, mercapto, cyano, nitro, nitroso, formyl, acyl, COOH, carboxylate, alkylcarbonyloxy, carbamoyl, SO3H, sulfonate, sulfamino, sulfamide, amidino, NE 5 E 6 where E 5 and E 6 are each
- heterocycloalkyi groups are especially pyrrolidinyl, piperidinyl, 2,2,6,6- tetramethylpiperidinyl, imidazolidinyl, pyrazolidinyl, oxazolidinyl, morpholidinyl, thiazolidinyl, isothiazolidinyl, isoxazolidinyl, piperazinyl, tetrahydrothiophenyl, dihydrothien-2-yl, tetrahydrofuranyl, dihydrofuran-2-yl, tetrahydropyranyl, 1 ,2-oxazolin- 5-yl, 1 ,3-oxazolin-2-yl and dioxanyl.
- Substituted heterocycloalkyi groups may, depending on the ring size, have one or more (e.g. 1 , 2, 3, 4, 5 or more than 5) substituents. These are preferably each
- heterocycloalkyl groups preferably bear one or more, for example one, two, three, four or five, Ci-C6-alkyl groups.
- heteroaryl comprises heteroaromatic, mono- or polycydic groups. In addition to the ring carbon atoms, these have 1 , 2, 3, 4 or more than 4 of the ring heteroatoms.
- the heteroatoms are preferably selected from oxygen, nitrogen, selenium and sulfur.
- the hetaryl groups have preferably 5 to 18, e.g. 5, 6, 8, 9, 10, 1 1 , 12, 13 or 14, ring atoms.
- Monocyclic hetaryl groups are preferably 5- or 6-membered hetaryl groups, such as 2- furyl (furan-2-yl), 3-furyl (furan-3-yl), 2-thienyl (thiophen-2-yl), 3-thienyl (thiophen-3-yl), selenophen-2-yl, selenophen-3-yl, 1 H-pyrrol-2-yl, 1 H-pyrrol-3-yl, pyrrol-1 -yl, imidazol-2- yl, imidazol-1 -yl, imidazol-4-yl, pyrazol-1 -yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, 3- isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2- oxazolyl, 4-oxazoly
- Polycydic hetaryl groups have 2, 3, 4 or more than 4 fused rings.
- the fused-on rings may be aromatic, saturated or partly unsaturated.
- Examples of polycydic hetaryl groups are quinolinyl, isoquinolinyl, indolyl, isoindolyl, indolizinyl, benzofuranyl, isobenzofuranyl, benzothiophenyl, benzoxazolyl, benzisoxazolyl, benzthiazolyl, benzoxadiazolyl; benzothiadiazolyl, benzoxazinyl, benzopyrazolyl, benzimidazolyl, benzotriazolyl, benzotriazinyl, benzoselenophenyl, thienothiophenyl, thienopyrimidyl, thiazolothiazolyl, dibenzopyrrolyl (carbazolyl), dibenzofuranyl, dibenzo
- Substituted hetaryl groups may, depending on the number and size of their ring systems, have one or more (e.g. 1 , 2, 3, 4, 5 or more than 5) substituents. These are preferably each independently selected from alkyl, alkoxy, alkylthio, cycloalkyl, heterocycloalkyl, aryl, hetaryl, fluorine, chlorine, bromine, hydroxyl, mercapto, cyano, nitro, nitroso, formyl, acyl, COOH, carboxylate, alkylcarbonyloxy, carbamoyl, SO3H, sulfonate, sulfamino, sulfamide, amidino, NE 9 E 10 where E 9 and E 10 are each
- Halogen substituents are preferably fluorine, chlorine or bromine.
- the substituents are preferably selected from Ci-C6-alkyl, Ci-C6-alkoxy, hydroxyl, carboxyl, halogen and cyano.
- unsubstituted or substituted hetaryl also apply to unsubstituted or substituted hetaryloxy and unsubstituted or substituted hetarylthio.
- oligo(het)aryl denotes unsubstituted or substituted groups having at least two repeat units.
- the repeat units may all have the same definition, some of the repeat units may have different definitions or all repeat units may have different definitions.
- the repeat unit is selected from aryldiyl groups, hetaryldiyl groups and combinations thereof.
- the aryldiyl group is a divalent group derived from an aromatic, preferably a group derived from benzene or naphthalene, such as 1 ,2-phenylene (o-phenylene), 1 ,3-phenylene (m-phenylene), 1 ,4-phenylene (p-phenylene), 1 ,2-naphthylene, 2,3-naphthylene, 1 ,4-naphthylene, etc.
- the hetaryldiyl group is a divalent group derived from a heteroaromatic, preferably a group derived from thiophene or furan.
- the terminal group of the oligo(het)aryl groups is a monovalent group.
- the oligo(het)aryl groups may be unsubstituted or substituted.
- Substituted oligo(het)aryls may, depending on the number and size of their ring systems, have one or more (e.g. 1 , 2, 3, 4, 5, 6, 7, 8, 9 or more than 9) substituents. These substituents are preferably each independently selected from unsubstituted alkyl, haloalkyl, fluorine or chlorine.
- Suitable repeat units are as follows:
- R f radicals are each independently alkyl, alkoxy, haloalkyl, fluorine or chlorine, y is 0, 1 , 2, 3 or 4 and x is 0, 1 or 2.
- Preferred oligoaryl groups are biphenylyl, p-terphenylyl, m-terphenylyl, o-terphenylyl, quaterphenylyl, e.g. p-quaterphenylyl, quinquephenylyl, e.g. p-quinquephenylyl.
- Preferred oligohetaryl groups are:
- # represents a bonding site to the rest of the molecule
- a is 1 , 2, 3, 4, 5, 6, 7 or 8
- n is 1 to 12, preferably 1 to 6.
- a is preferably 1 or 2.
- the CnH2n+i radical is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl or n-hexyl.
- oligohetaryl groups are 2,2 -bithiophen-5-yl and 5"-hexyl-2 ,2"-bithiophen- 5-yl.
- Halogen represents fluorine, chlorine, bromine or iodine.
- Halogen preferably represents fluorine or chlorine.
- R 1 to R 12 radicals and, in accordance with the above definition, also R a and R b , specified in the above formula (I) and the formulae which follow are: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl,
- n-tetradecyl n-hexadecyl, n-octadecyl and n-eicosyl
- 2-methoxyethyl 2-ethoxyethyl, 2- propoxyethyl, 2-butoxyethyl, 3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 3-butoxypropyl, 4-methoxybutyl, 4-ethoxybutyl, 4-propoxybutyl, 3,6-dioxaheptyl,
- N,N-bis(4-chlorophenyl)aminosulfonyl methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl hexoxycarbonyl
- R a , R b and R 1 to R 12 radicals are as follows:
- R a , R b and R 1 to R 12 radicals specified in the above formula (I) and the formulae which follow are additionally:
- the R a and R b radicals are preferably each independently selected from hydrogen, deuterium, unsubstituted alkyl, aralkyl, cycloalkyl, unsubstituted aryl and alkaryl.
- the R a and R b radicals are more preferably each independently selected from hydrogen, deuterium, Ci-Ci2-alkyl, C7-C22-aralkyl, C4-C7-cycloalkyl, C6-Cio-aryl and C7-C22-alkaryl.
- R a and R b radicals preferably have the same definition.
- the R a and R b radicals are both hydrogen. In a further specific embodiment, in the compounds of the general formula (I), the R a and R b radicals are both deuterium.
- the R a and R b radicals are both Ci-C6-alkyl, more specifically both methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl or n-hexyl.
- the R a and R b radicals are both phenyl, or both Ci-Ci2-alkylphenyl, especially
- the R 1 to R 12 radicals are each independently selected from hydrogen, F, CI, hydroxyl, Ci-Cis-alkyl, Ci-Ci2-alkoxy, Ci-C6-alkylthio, C7-C22-aralkyl, C7-C22-aralkyloxy, C7-C22-aralkylthio, C4-C7-cycloalkyl, C6-Cio-aryl, C7-C22-alkaryl, C7-C22-alkaryloxy, C7-C22-alkarylthio, amino,
- the R 1 to R 12 radicals are preferably each independently selected from hydrogen, Ci-Ci2-alkyl, Ci-Ci2-alkoxy, phenyl, naphthyl, phenyloxy, naphthyloxy and oligothiophenyl, where phenyl, naphthyl, phenyloxy, naphthyloxy and oligothiophenyl are unsubstituted or have 1 or 2 substituents which are selected from Ci-Ci2-alkyl and Ci-Ci2-alkoxy.
- 0, 1 , 2, 3 or 4 of the R 1 to R 12 radicals preferably have a definition other than hydrogen.
- 2 of the R 1 to R 12 radicals have a definition other than hydrogen.
- At least one of the R 1 , R 5 , R 8 and R 9 radicals has a definition other than hydrogen.
- R a and R b are each independently selected from hydrogen, deuterium, Ci-C6-alkyl, phenyl and naphthyl,
- R 1 and R 9 are each independently selected from phenyl, phenyloxy, phenylthio,
- R 5 and R 8 are each independently selected from hydrogen, hydroxyl and Ci-Ci 2 -alkoxy.
- indanthrene compounds (I) which are preferentially suitable for use in organic solar cells are shown below:
- the indanthrene compounds (I) used in the inventive solar cells can be prepared by customary processes known to those skilled in the art.
- indanthrene blue indanthrone blue
- Paliogen® Blue L 6480 name from BASF SE.
- Many other indanthrene derivatives are also commercially available.
- alkylating agents customary for this purpose, such as alkylhalides, alkylsulfates or alkylsulfonates (e.g. tosylates).
- a suitable process for arylating the corresponding protonated compounds works by catalytic coupling with aryl halides in the manner of a C-N Ullmann coupling. For instance, it is possible to arylate indanthrene compounds with aryl bromides such as bromobenzene.
- Suitable catalysts are copper catalysts, such as Cul and Cu(l) acetate.
- the indanthrene compound Before use in an organic solar cell, the indanthrene compound can be subjected to purification.
- the purification can be effected by customary methods known to those skilled in the art, such as separation on suitable stationary phases, sublimation, extraction, distillation, recrystallization or a combination of at least two of these measures.
- Each purification may have a one-stage or multistage configuration.
- the purification comprises a column chromatography method.
- the starting material present in a solvent or solvent mixture can be subjected to a separation or filtration on silica gel.
- the solvent is removed, for example by evaporation under reduced pressure.
- Suitable solvents are aromatics such as benzene, toluene, xylene, mesitylene, chlorobenzene or dichlorobenzene, hydrocarbons and hydrocarbon mixtures, such as pentane, hexane, ligroin and petroleum ether, halogenated hydrocarbons such as chloroform or dichloromethane, and mixtures of the solvents mentioned.
- aromatics such as benzene, toluene, xylene, mesitylene, chlorobenzene or dichlorobenzene
- hydrocarbons and hydrocarbon mixtures such as pentane, hexane, ligroin and petroleum ether, halogenated hydrocarbons such as chloroform or dichloromethane, and mixtures of the solvents mentioned.
- hydrocarbons and hydrocarbon mixtures such as pentane, hexane, ligroin and petroleum ether, halogenated hydrocarbons such as chloroform or dichloromethane
- the purification comprises a sublimation.
- This may preferably be a fractional sublimation.
- the purification can be effected by sublimation with the aid of a carrier gas stream.
- Suitable carrier gases are inert gases, for example nitrogen, argon or helium.
- the gas stream laden with the compound can subsequently be passed into a separating chamber.
- Suitable separating chambers may have a plurality of separation zones which can be operated at different temperatures. Preference is given, for example, to a so-called three-zone sublimation apparatus.
- a further process and an apparatus for fractional sublimation are described in US 4,036,594.
- Organic solar cells generally have a layer structure and generally comprise at least the following layers: anode, photoactive layer and cathode. These layers are generally applied to a substrate suitable for this purpose.
- the structure of organic solar cells is described, for example, in US 2005/0098726 and US 2005/0224905.
- the invention provides an organic solar cell which comprises a substrate with at least one cathode and at least one anode, and at least one compound of the general formula (I) as defined above as a photoactive material.
- the inventive organic solar cell comprises at least one photoactive region.
- a photoactive region may comprise two layers, each of which has a homogeneous composition and forms a flat donor-acceptor heterojunction.
- a photoactive region may also comprise a mixed layer and form a donor-acceptor heterojunction in the form of a donor-acceptor bulk heterojunction.
- Organic solar cells with photoactive donor-acceptor transitions in the form of a bulk heterojunction are a preferred embodiment of the invention.
- Suitable substrates for organic solar cells are, for example, oxidic materials, polymers and combinations thereof.
- Preferred oxidic materials are selected from glass, ceramic, S1O2, quartz, etc.
- Preferred polymers are selected from polyethylene terephthalates, polyolefins (such as polyethylene and polypropylene), polyesters, fluoropolymers, polyamides, polyurethanes, polyalkyl (meth)acrylates, polystyrenes, polyvinyl chlorides and mixtures and composites.
- Suitable electrodes are in principle semiconductors, metal alloys, semiconductor alloys and combinations thereof.
- Preferred metals are those of groups 2, 8, 9, 10, 1 1 or 13 of the periodic table, e.g. Pt, Au, Ag, Cu, Al, In, Mg or Ca.
- Preferred semiconductors are, for example, doped Si, doped Ge, indium tin oxide (ITO), fluorinated tin oxide (FTO), gallium indium tin oxide (GITO), zinc indium tin oxide (ZITO), etc.
- Preferred metal alloys are for example alloys based on Pt, Au, Ag, Cu, etc. A specific embodiment is Mg/Ag alloys.
- the material used for the electrode facing the light is preferably a material at least partly transparent to the incident light.
- This preferably includes electrodes which have glass and/or a transparent polymer as a carrier material.
- Transparent polymers suitable as carriers are those mentioned above, such as polyethylene terephthalate.
- the electrical contact connection is generally effected by means of metal layers and/or transparent conductive oxides (TCOs). These preferably include ITO, doped ITO, FTO (fluorine doped tin oxide), AZO (aluminum doped tin oxide), ZnO, T1O2, Ag, Au, Pt. Particular preference is given to ITO for contact connection.
- a conductive polymer for example a poly-3,4-alkylenedioxy- thiophene, e.g. poly-3,4-ethyleneoxythiophene (PEDOT).
- the electrode facing the light is configured such that it is sufficiently thin to bring about only minimal light absorption but thick enough to enable good charge transport of the extracted charge carriers.
- the thickness of the electrode layer (without carrier material) is preferably within a range from 20 to 200 nm.
- the material used for the electrode facing away from the light is a material which at least partly reflects the incident light.
- the thickness of the electrode layer is preferably within a range from 50 to 300 nm.
- the photoactive region comprises or consists of at least one layer which comprises at least one indanthrene compound of the general formula (I) as defined above.
- the photoactive region may have one or more further layer(s). These are, for example, selected from - layers with electron-conducting properties (electron transport layer, ETL),
- HTL hole transport layer
- exciton- and hole-blocking layers e.g. EBLs
- EBLs exciton- and hole-blocking layers
- Suitable materials for these layers are described in detail hereinafter.
- Suitable exciton- and hole-blocking layers are described, for example, in US 6,451 ,415.
- Suitable materials for exciton-blocking layers are, for example, bathocuproin (BCP), 4,4',4"-tris[3-methylphenyl-N-phenylamino]triphenylamine (m-MTDATA) or
- PEDOT polyethylenedioxythiophene
- the inventive solar cells comprise at least one photoactive donor-acceptor
- the electron-hole pair has to be separated, typically at a donor-acceptor interface between two unlike contact materials. At such an interface, the donor material forms a heterojunction with an acceptor material.
- the charges can recombine in a process also known as "quenching", either radiatively by the emission of light of a lower energy than the incident light or nonradiatively by generation of heat. Both processes are undesired.
- at least one substituted indanthrene of the general formula (I) can be used as a charge generator (donor).
- ETM electron transport material
- radiative excitation is followed by a rapid electron transfer to the ETM.
- Inventive ETMs are C60 and other fullerenes.
- the heterojunction has a flat configuration (see: Two layer organic photovoltaic cell, C. W. Tang, Appl. Phys. Lett., 48 (2), 183-185 (1986) or N. Karl, A. Bauer, J. Holzapfel, J. Natanner, M. Mobus, F. Stolzle, Mol. Cryst. Liq.
- the heterojunction is configured as a bulk (mixed) heterojunction, also referred to as an interpenetrating donor-acceptor network.
- Organic photovoltaic cells with a bulk heterojunction are described, for example, by C. J.
- the compounds of the formula (I) can be used as a photoactive material in cells with MiM, pin, pn, Mip or Min structure
- M metal
- p p-doped organic or inorganic semiconductor
- n n-doped organic or inorganic semiconductor
- i intrinsically conductive system of organic layers; see, for example, J. Drechsel et al., Org.
- the compounds of the formula (I) can also be used as a photoactive material in tandem cells. Suitable tandem cells are described, for example, by P. Peumans, A. Yakimov, S. R. Forrest in J. Appl. Phys, 93 (7), 3693-3723 (2003) (see also US
- the compounds of the formula (I) can also be used as a photoactive material in tandem cells which are constructed from two or more than two stacked MiM, pin, Mip or Min structures (see DE 103 13 232.5 and J. Drechsel et al., Thin Solid Films, 451452, 515-517 (2004)).
- the layer thickness M, n, i and p layers is typically within a range from 10 to 1000 nm, more preferably from 10 to 400 nm.
- the layers which form the solar cell can be produced by customary processes known to those skilled in the art. These include vapor deposition under reduced pressure or in an inert gas atmosphere, laser ablation or solution or dispersion processing methods such as spincoating, knifecoating, casting methods, spray application, dipcoating or printing (e.g. inkjet, flexographic, offset, gravure; intaglio, nanoimprinting). In a specific embodiment, the entire solar cell is produced by a gas phase deposition process.
- the photoactive donor-acceptor transitions in the form of a bulk heterojunction are produced by a gas phase deposition process (physical vapor deposition, PVD).
- PVD processes are performed under high-vacuum conditions and comprise the following steps: evaporation, transport, deposition.
- the deposition is effected preferably at a pressure within a range from about 10 "2 mbar to 10 "7 mbar, for example from 10 "5 to 10 "7 mbar.
- the deposition rate is preferably within a range from 0.01 to 10 nm/s.
- the deposition can be effected in an inert gas atmosphere, for example under nitrogen, helium or argon.
- the temperature of the substrate during the deposition is preferably within a range from -100 to 300°C, more preferably from -50 to 250°C.
- the other layers of the organic solar cell can be produced by known processes. These include vapor deposition under reduced pressure or in an inert gas atmosphere, laser ablation, or solution or dispersion processing methods such as spincoating, knifecoating, casting methods, spray application, dipcoating or printing (e.g. inkjet, flexographic, offset, gravure; intaglio, nanoimprinting). In a specific embodiment, the entire solar cell is produced by a gas phase deposition process.
- the photoactive layer (homogeneous layer or mixed layer) can be subjected to a thermal treatment directly after production thereof or after production of further layers which form the solar cell. Such a heat treatment can in many cases further improve the morphology of the photoactive layer.
- the temperature is preferably within a range from about 60°C to 300°C.
- the treatment time is preferably within a range from 1 minute to 3 hours.
- the photoactive layer (mixed layer) can be subjected to a treatment with a solvent-containing gas directly after production thereof or after production of further layers which form the solar cell.
- saturated solvent vapors in air are used at ambient temperature. Suitable solvents are toluene, xylene, chloroform, N-methylpyrrolidone,
- the treatment time is preferably within a range from 1 minute to 3 hours.
- the inventive solar cells are present as an individual cell with flat heterojunction normal structure.
- Figure 1 shows an inventive solar cell with normal structure.
- the cell has the following structure: an at least partly transparent conductive layer (top electrode, anode) (1 1 ) a hole-conducting layer (hole transport layer, HTL) (12)
- the donor material preferably comprises at least one compound of the formula (I) or consists of a compound of the formula (I).
- the acceptor material comprises at least one fullerene or fullerene derivative, or consists of a fullerene or fullerene derivative.
- the acceptor material preferably comprises C60 or PCBM ([6,6]-phenyl-C61 -butyric acid methyl ester).
- the essentially transparent conductive layer (1 1 ) (anode) comprises a carrier, such as glass or a polymer (e.g. polyethylene terephthalate) and a conductive material, as described above. Examples include ITO, doped ITO, FTO, ZnO, AZO, etc.
- the anode material can be subjected to a surface treatment, for example with UV light, ozone, oxygen plasma, Br2, etc.
- the layer (1 1 ) should be sufficiently thin to enable maximum light absorption, but also sufficiently thick to ensure good charge transport.
- the layer thickness of the transparent conductive layer (1 1 ) is preferably within a range from 20 to 200 nm.
- the solar cell with normal structure according to figure 1 optionally has a hole- conducting layer (HTL).
- This layer comprises at least one hole-conducting material (hole transport material, HTM).
- HTM hole transport material
- Layer (12) may be an individual layer of essentially homogeneous composition or may comprise two or more than two sublayers.
- Hole-conducting materials (HTM) suitable for forming layers with hole-conducting properties (HTL) preferably comprise at least one material with high ionization energy.
- the ionization energy is preferably at least 5.0 eV, more preferably at least 5.5 eV.
- the materials may be organic or inorganic materials.
- Organic materials suitable for use in a layer with hole-conducting properties are preferably selected from poly(3,4- ethylenedioxythiophene) poly(styrenesulfonate) (PEDOT-PSS), Ir-DPBIC (tris-N.N - diphenylbenzimidazol-2-ylideneiridium(lll)), N,N'-diphenyl-N,N'-bis(3-methylphenyl)- 1 ,1 '-diphenyl-4,4'-diamine (a-NPD), 2,2',7,7'-tetrakis(N,N-di-p-methoxyphenylamine)- 9,9'-spirobifluorene (spiro-MeOTAD), etc.
- PEDOT-PSS poly(3,4- ethylenedioxythiophene) poly(styrenesulfonate)
- Ir-DPBIC tris-N.N - diphenylbenz
- the organic materials may, if desired, be doped with a p-dopant which has a LUMO within the same range as or lower than the HOMO of the hole-conducting material.
- Suitable dopants are, for example, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), WO3, M0O3, etc.
- Inorganic materials suitable for use in a layer with hole-conducting properties are preferably selected from WO3, M0O3, etc.
- the thickness of the layers with hole-conducting properties is preferably within a range from 5 to 200 nm, more preferably 10 to 100 nm.
- Layer (13) comprises at least one compound of the general formula (I).
- the thickness of the layer should be sufficient to absorb a maximum amount of light, but thin enough to enable effective dissipation of the charge.
- the thickness of the layer (13) is preferably within a range from 5 nm to 1 ⁇ , more preferably from 5 to 80 nm.
- Layer (14) comprises at least one acceptor material.
- the acceptor material comprises at least one fullerene or fullerene derivative.
- the thickness of the layer should be sufficient to absorb a maximum amount of light, but thin enough to enable effective dissipation of the charge.
- the thickness of the layer (14) is preferably within a range from 5 nm to 1 ⁇ , more preferably from 5 to 80 nm.
- the solar cell with normal structure according to figure 1 optionally comprises an exciton-blocking and/or electron-conducting layer (15) (EBL/ETL).
- Suitable materials for exciton-blocking layers generally have a greater band gap than the materials of layer (13) and/or (14). They are firstly capable of reflecting excitons and secondly enable good electron transport through the layer.
- the materials for the layer (15) may comprise organic or inorganic materials. Suitable organic materials are preferably selected from 2,9-dimethyl-4,7-diphenyl-1 ,10-phenanthroline (BCP), 4,7-diphenyl-1 ,10- phenanthroline (Bphen), 1 ,3-bis[2-(2,2 ' -bipyridin-6-yl)-1 ,3,4-oxadiazo-5-yl]benzene (BPY-OXD), etc.
- the organic materials may, if desired, be doped with an n-dopant which has a HOMO within the same range as or lower than the LUMO of the electron- conducting material.
- Suitable dopants are, for example, CS2CO3, Pyronin B (PyB), Rhodamine B, cobaltocenes, etc.
- Inorganic materials suitable for use in a layer with electron-conducting properties are preferably selected from ZnO, etc. If present, the thickness of the layer (15) is preferably within a range from 5 to 500 nm, more preferably 10 to 100 nm.
- Layer 16 is the cathode and preferably comprises at least one compound with low work function, more preferably a metal such as Ag, Al, Mg, Ca, etc.
- the thickness of the layer (16) is preferably within a range from about 10 nm to 10 ⁇ , e.g. 10 nm to 60 nm.
- the inventive solar cells are present as an individual cell with a flat heterojunction and inverse structure.
- Figure 2 shows a solar cell with inverse structure.
- the cell has the following structure: an at least partly transparent conductive layer (cathode) (1 1 )
- HTL hole transport layer
- the inventive solar cells are present as an individual cell with normal structure and have a bulk heterojunction.
- Figure 3 shows a solar cell with a bulk heterojunction.
- the cell has the following structure: an at least partly transparent conductive layer (anode) (21 )
- HTL hole transport layer
- a mixed layer which comprises a donor material and an acceptor material, which form a donor-acceptor heterojunction in the form of a bulk heterojunction (23) an electron-conducting layer (24) an exciton-blocking and/or electron-conducting layer (25)
- the layer (23) comprises at least one indanthrene compound of the general formula (I) as a photoactive material, especially as a donor material.
- the layer (23) additionally comprises preferably at least one fullerene or fullerene derivative as an acceptor material.
- the layer (23) comprises especially C60 or PCBM ([6, 6]-phenyl-C61 -butyric acid methyl ester) as an acceptor material.
- Layer (23) is a mixed layer which comprises at least one compound of the general formula (I) as a donor material, i.e. fullerene or a fullerene derivative.
- layer (23) comprises at least one acceptor material.
- the layer (23) can be produced by coevaporation or by solution processing using customary solvents.
- the mixed layer comprises preferably 10 to 90% by weight, more preferably 20 to 80% by weight, of at least one compound of the general formula (I), based on the total weight of the mixed layer.
- the mixed layer comprises preferably 10 to 90% by weight, more preferably 20 to 80% by weight, of at least one acceptor material, based on the total weight of the mixed layer.
- the thickness of the layer (23) should be sufficient to absorb a maximum amount of light, but thin enough to enable effective dissipation of the charge.
- the thickness of the layer (23) is preferably within a range from 5 nm to 1 ⁇ , more preferably from 5 to 200 nm, especially 5 to 80 nm.
- the solar cell with a bulk heterojunction according to figure 3 comprises an electron- conducting layer (24) (ETL).
- This layer comprises at least one electron transport material (ETM).
- Layer (24) may be a single layer of essentially homogeneous composition or may comprise two or more than two sublayers. Suitable materials for electron-conducting layers generally have a low work function or ionization energy. The ionization energy is preferably not more than 3.5 eV.
- Suitable organic materials are preferably selected from the aforementioned fullerenes and fullerene derivatives, 2,9-dimethyl-4,7-diphenyl-1 ,10-phenanthroline (BCP), 4,7-diphenyl-1 ,10- phenanthroline (Bphen), 1 ,3-bis[2-(2,2 ' -bipyridin-6-yl)-1 ,3,4-oxadiazo-5-yl]benzene (BPY-OXD), etc.
- the organic materials used in layer (24) may, if desired, be doped with an n-dopant which has a HOMO within the same range as or lower than the LUMO of the electron-conducting material. Suitable dopants are, for example, CS2CO3,
- the thickness of the layer (23) is, if present, preferably within a range from 1 nm to 1 ⁇ , particularly 5 to 60 nm.
- layer (25) reference is made completely to the above remarks regarding layer (15).
- layer (26) reference is made completely to the above remarks regarding layer (16).
- the solar cell with a donor-acceptor heterojunction in the form of a bulk heterojunction can be produced by a gas phase deposition process as described above.
- deposition rates substrate temperature during the deposition and thermal aftertreatment, reference is made to the above remarks.
- inventive solar cells are present as an individual cell with inverse structure and have a bulk heterojunction.
- Figure 4 shows a solar cell with a bulk heterojunction and inverse structure.
- the inventive solar cell is a tandem cell.
- a tandem cell consists of two or more than two (e.g. 3, 4, 5, etc.) subcells.
- a single subcell, some of the subcells or all subcells may have photoactive donor-acceptor heterojunctions.
- Each donor-acceptor-heterojunction may be in the form of a flat heterojunction or in the form of a bulk heterojunction.
- at least one of the donor-acceptor heterojunctions is in the form of a bulk heterojunction.
- the photoactive layer of at least one subcell comprises an indanthrene compound of the general formula (I).
- the photoactive layer of at least one subcell comprises an indanthrene compound of the general formula (I) and at least one fullerene or fullerene derivative. More preferably, the semiconductor mixture used in the photoactive layer of at least one subcell consists of an indanthrene compound of the general formula (I) and Ceo or [6, 6]-phenyl-C61 -butyric acid methyl ester.
- the subcells which form the tandem cell may be connected in parallel or in series.
- the subcells which form the tandem cell are preferably connected in series. There is preferably an additional recombination layer in each case between the individual subcells.
- the individual subcells have the same polarity, i.e. generally either only cells with normal structure or only cells with inverse structure are combined with one another.
- FIG. 5 shows the basic structure of an inventive tandem cell.
- Layer 31 is a transparent conductive layer. Suitable materials are those specified above for the individual cells.
- Layers 32 and 34 constitute subcells.
- “Subcell” refers here to a cell as defined above without cathode and anode.
- the subcells may, for example, either all have an indanthrene compound of the general formula (I) used in accordance with the invention in the photoactive layer (preferably in combination with a fullerene or fullerene derivative, especially C60) or have other combinations of semiconductor materials, for example C60 with zinc phthalocyanine, C60 with oligothiophene (such as DCV5T).
- individual subcells may also be configured as dye-sensitized solar cells or polymer cells. In all cases, preference is given to a combination of materials which exploit different regions of the spectrum of the incident light, for example of natural sunlight.
- the combination of indanthrene compound of the general formula (I) and fullerene or fullerene derivative used in accordance with the invention absorbs in the long-wave region of sunlight.
- Dibenzoperiflanthene(DBP)-C60 absorbs primarily in the range from 400 nm to 600 nm.
- Zinc phthalocyanine-C60 cells absorb primarily in the range from 600 nm to 800 nm.
- a tandem cell composed of a combination of these subcells should absorb radiation in the range from 400 nm to 800 nm. Suitable combination of subcells should thus allow the spectral range utilized to be extended.
- optical interference should be considered.
- subcells which absorb at relatively short wavelengths should be arranged closer to the metal top contact than subcells with longer-wave absorption.
- Layer 33 is a recombination layer. Recombination layers enable the charge carriers from one subcell to recombine with those of an adjacent subcell. Small metal clusters are suitable, such as Ag, Au or combinations of highly n- and p-doped layers. In the case of metal clusters, the layer thickness is preferably within a range from 0.5 to 5 nm. In the case of highly n- and p-doped layers, the layer thickness is preferably within a range from 5 to 40 nm.
- the recombination layer generally connects the electron- conducting layer of a subcell to the hole-conducting layer of an adjacent subcell. In this way, further cells can be combined to form the tandem cell.
- Layer 36 is the top electrode.
- the material depends on the polarity of the subcells. For subcells with normal structure, preference is given to using metals with a low work function, such as Ag, Al, Mg, Ca, etc. For subcells with inverse structure, preference is given to using metals with a high work function, such as Au or Pt, or PEDOT-PSS.
- the overall voltage corresponds to the sum of the individual voltages of all subcells.
- the overall current in contrast, is limited by the lowest current of one subcell. For this reason, the thickness of each subcell should be optimized such that all subcells have essentially the same current.
- donor-acceptor heterojunctions examples include a donor-acceptor double layer with a flat heterojunction, or the heterojunction is configured as a hybrid planar-mixed heterojunction or gradient bulk heterojunction or annealed bulk heterojunction.
- the donor-acceptor-heterojunction is in the form of a gradient bulk heterojunction.
- the donor-acceptor ratio changes gradually.
- the form of the gradient may be stepwise (figure 6(a)) or linear (figure 6(b)).
- the layer 01 consists of 100% donor material
- layer 02 has a donor/acceptor ratio > 1
- layer 04 has a donor/acceptor ratio ⁇ 1
- layer 05 consists of 100% acceptor material.
- layer 01 consists of 100% donor material
- layer 02 has a decreasing ratio of donor/acceptor, i.e.
- the proportion of donor material decreases in a linear manner in the direction of layer 03, and layer 03 consists of 100% acceptor material.
- the different donor-acceptor ratios can be controlled by means of the deposition rate of each and every material. Such structures can promote the percolation path for charges.
- the donor-acceptor- heterojunction is configured as an annealed bulk heterojunction; see, for example, Nature 425, 158-162, 2003.
- the process for producing such a solar cell comprises an annealing step before or after the metal deposition. As a result of the annealing, donor and acceptor materials can separate, which leads to more extended percolation paths.
- the organic solar cells are produced by organic vapor phase deposition, either with a flat or a controlled heterojunction architecture. Solar cells of this type are described in Materials, 4, 2005, 37.
- At least one substituted indanthrene of the general formula (I) is used as the sole electron donor material.
- the inventive organic solar cells comprise at least one photoactive region which comprises at least one indanthrene compound as a donor, which is in contact with at least one fullerene compound as an acceptor.
- Fullerenes and fullerene derivatives preferably selected from Ceo, C70, Cs4, phenyl-C6i-butyric acid methyl ester ([60]PCBM), phenyl-C7i-butyric acid methyl ester ([71]PCBM), phenyl-C84-butyric acid methyl ester ([84]PCBM), phenyl-Cerbutyric acid butyl ester ([60]PCBB), phenyl-Cerbutyric acid octyl ester ([60]PCBO), thienyl-C6i-butyric acid methyl ester ([60]ThCBM) and mixtures thereof. Particular preference is given to Ceo, [60]PCBM and mixtures thereof.
- the semiconductor materials listed hereinafter are suitable in principle for use in the inventive solar cells. They serve as donors or acceptors for subcells of a tandem cell, which are combined with an indanthrene/fullerene subcell used in accordance with the invention.
- Suitable further semiconductors are phthalocyanines. These include phthalocyanines which are nonhalogenated or which bear 1 to 16 halogen atoms.
- the phthalocyanines may be metal-free or contain a divalent metal or a metal atom-containing group.
- phthalocyanines based on zinc, copper, iron, titanyloxy, vanadyloxy, etc. Particular preference is given to copper phthalocyanines, zinc phthalocyanines, metal-free phthalocyanines. In a specific embodiment, a halogenated phthalocyanine is used. These include:
- 2,6,10,14-tetrafluorophthalocyanines e.g. copper 2,6, 10,14-tetrafluorophthalocyanine and zinc 2,6,10,14-tetrafluorophthalocyanine;
- 2,3,6,7,10,1 1 ,14,15-octafluorophthalocyanine e.g. copper 2,3,6, 7,10,1 1 ,14,15- octafluorophthalocyanine and zinc 2,3,6,7,10,1 1 ,14,15-octafluorophthalocyanine;
- phthalocyanines which are suitable as acceptors are, for example, hexadecachloro- phthalocyanines and hexadecafluorophthalocyanines, such as copper hexadeca- chlorophthalocyanine, zinc hexadecachlorophthalocyanine, metal-free
- Suitable further semiconductors which are predominantly suitable as acceptors, are rylenes.
- Y 1 is O or NR a where R a is hydrogen or an organyl radical
- Y 2 is O or NR b where R b is hydrogen or an organyl radical
- Z 1 , Z 2 , Z 3 and Z 4 are each O, where, in the case that Y 1 is NR a , one of the Z 1 and Z 2 radicals may also be NR C , where the R a and R c radicals together are a bridging group having 2 to 5 atoms between the flanking bonds, and where, in the case that Y 2 is NR b , one of the Z 3 and Z 4 radicals may also be NR d , where the R b and R d radicals together are a bridging group having 2 to 5 atoms between the flanking bonds.
- Suitable rylenes are, for example, described in WO 2007/074137, WO 2007/093643 and WO 2007/1 16001 , to which reference is made here. Also suitable are the following donor-semiconductor materials, which can be used, for example, in a tandem cell, as described hereinafter, in a further subcell instead of the indanthrene compounds (I).
- porphyrins for example 5,10,15,20-tetra(3- pyridyl)porphyrin (TpyP), or else tetrabenzoporphyrins, for example metal-free tetrabenzoporphyrin, copper tetrabenzoporphyrin or zinc tetrabenzoporphyrin.
- TpyP 5,10,15,20-tetra(3- pyridyl)porphyrin
- tetrabenzoporphyrins for example metal-free tetrabenzoporphyrin, copper tetrabenzoporphyrin or zinc tetrabenzoporphyrin.
- tetrabenzoporphyrins are Especially preferred. These can be processed from solution as soluble precursors and converted to the photoactive component by thermolysis on the substrate.
- Further semiconductors suitable as donors are acenes. These are preferably selected from in each case unsubstituted or substituted anthracene, tetracene or pentacene.
- Substituted acenes comprise preferably at least one substituent which is selected from electron-donating substituents, electron-withdrawing substituents and combinations thereof. Suitable electron-donating substituents are, for example, alkyl, alkoxy, ester, carboxylate or thioalkoxy. Suitable electron-withdrawing substituents are, for example, halogen, nitro or cyano.
- Preferred acenes are selected from 2,9-dialkylpentacenes, 2,10-dialkylpentacenes, 2,10-dialkoxypentacenes, 1 ,4,8,1 1 -tetraalkoxypentacenes and rubrene (5,6,1 1 ,12-tetraphenylnaphthacene).
- Suitable substituted pentacenes are described in US 2003/0100779 and US 6,864,396, to which reference is made here.
- a particularly preferred acene is rubrene.
- liquid-crystalline materials are preferably selected from coronenes and triphenylenes.
- Preferred liquid-crystalline materials are hexabenzocoronene (HBC-PhCi2), coronenediimides, 2,3,6,7,10,1 1 -hexahexylthiotriphenylene (HTT 6 ), 2,3,6,7,10,1 1 -hexakis-(4-n- nonylphenyl)triphenylene (PTPg) or 2,3,6,7,10,1 1 -hexakis(undecyloxy)triphenylene (HAT11).
- HBC-PhCi2 hexabenzocoronene
- HTT 6 2,3,6,7,10,1 1 -hexahexylthiotriphenylene
- PTPg 2,3,6,7,10,1 1 -hexakis(undecyloxy)triphenylene
- HAT11 liquid-crystalline materials which are discotic.
- thiophene compounds suitable as donors are thiophene compounds. These are preferably selected from thiophenes, oligothiophenes and substituted derivatives thereof. Suitable oligothiophenes are quaterthiophenes, quinquethiophenes, sexithiophenes, a,co-di(Ci-C8)-alkyloligothiophenes, such
- ⁇ , ⁇ -dihexylsexithiophenes poly(alkylthiophenes) such as poly(3-hexylthiophene), bis(dithienothiophenes), anthradithiophenes and dialkylanthradithiophenes such as dihexylanthradithiophene, phenylene-thiophene (P-T) oligomers and derivatives thereof, especially ⁇ , ⁇ -alkyl-substituted phenylene-thiophene oligomers.
- poly(alkylthiophenes) such as poly(3-hexylthiophene), bis(dithienothiophenes), anthradithiophenes and dialkylanthradithiophenes such as dihexylanthradithiophene, phenylene-thiophene (P-T) oligomers and derivatives thereof, especially ⁇ , ⁇ -alkyl-substitute
- thiophene compounds suitable as semiconductors are preferably selected from compounds like
- DCV5T a,a'-bis(2,2-dicyanovinyl)quinquethiophene
- POPT (3-(4-octylphenyl)-2,2'-bithiophene)
- POPT poly-3-(4'-(1 ,4,7-trioxaoctyl)-phenyl)thiophene
- PCPDTBT poly[2,6-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1 b;3,4 b']dithiophene)- 4,7-(2,1 ,3-benzothiadiazole) (PCPDTBT), and also
- poly(pyridopyrazinevinylene)-polythiophene blends such as EHH-PpyPz, PTPTB copolymers, BBL, F 8 BT, PFMO (see Brabec C, Adv. Mater., 2996, 18, 2884).
- paraphenylenevinylene and oligomers or polymers comprising paraphenylenevinylene units are preferably selected from polyparaphenylenevinylene, MEH-PPV (poly(2-methoxy-5-(2'-ethylhexyloxy)-1 ,4- phenylenevinylene, MDMO-PPV (poly(2-methoxy-5-(3',7'-dimethyloctyloxy)- 1 ,4-phenylenevinylene)), PPV, CN-PPV (with various alkoxy derivatives), and also phenyleneethynylene/phenylenevinylene hybrid polymers (PPE-PPV).
- MEH-PPV poly(2-methoxy-5-(2'-ethylhexyloxy)-1 ,4- phenylenevinylene
- MDMO-PPV poly(2-methoxy-5-(3',7'-dimethyloctyloxy)- 1 ,4-phen
- Such semiconductors suitable as donors are polyfluorenes and alternating polyfluorene copolymers. These are preferably selected from
- Such semiconductors suitable as donors are polycarbazoles, i.e. oligomers and polymers comprising carbazole.
- Such semiconductors suitable as donors are polyanilines, i.e. oligomers and polymers comprising aniline.
- Further semiconductors suitable as donors are triarylamines, polytriarylamines, polycyclopentadienes, polypyrroles, polyfurans, polysiloles, polyphospholes, TPD, CBP, spiro-MeOTAD.
- the inventive solar cell has the following layers: ITO
- the inventive solar cell is more preferably a tandem cell, wherein one subcell has a photoactive region which comprises at least one indanthrene compound of the formula (I) and C60.
- All aforementioned semiconductors may be doped.
- the conductivity of semiconductors can be increased by chemical doping techniques using dopants.
- An organic semiconductor material may be doped with an n-dopant which has a HOMO energy level which is close to or higher than the LUMO energy level of the electron-conducting material.
- An organic semiconductor material may also be doped with a p-dopant which has a LUMO energy level which is close to or higher than the HOMO energy level of the hole-conducting material.
- n-doping an electron is released from the dopant, which acts as the donor, whereas in the case of p-doping the dopant acts as an acceptor which accepts an electron.
- Suitable dopants for the indanthrene compounds used in accordance with the invention and for p-semiconductors in general are, for example, selected from WO3, M0O3, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), 3,6-difluoro- 2,5,7,7,8,8-hexacyanoquinodimethane, dichlorodicyanoquinone (DDQ) or
- tetracyanoquinodimethane TCNQ
- a preferred dopant is 3,6-difluoro-2,5,7,7,8,8- hexacyanoquinodimethane.
- Suitable dopants for the p-semiconductors used in accordance with the invention are, for example, selected from CS2CO3, LiF, pyronin B (PyB), rhodamin derivatives, cobaltocenes, etc.
- Preferred dopants are pyronin B and rhodamin derivatives, especially rhodamin B.
- the dopants are typically used in an amount of up to 10 mol%, preferably up to 5 mol%, based on the amount of the semiconductor to be doped.
- Example 1 Deuterated indanthrene blue
- the title compound was synthesized as described in example 4.3.
- the title compound was purified by means of Soxhlet extraction from ethanol and chlorobenzene, and fractional crystallization from sulfuric acid.
- the title compound was identified on the basis of its solid-state spectrum (see figure 9) and by MALDI-MS.
- Figure 7 shows the absorption spectrum of a vapor-deposited film of indanthrene blue. A long-wave absorption is observed, which is coupled with a good voltage V oc .
- ITO ITO was sputtered onto the glass substrate in a thickness of 100 nm.
- the specific resistivity was 200 ⁇ ⁇ cm, and the mean roughness (RMS; root mean square) was less than 5 nm.
- RMS root mean square
- the substrate was treated with ozone under UV light for 20 minutes (UV-ozone cleaning). Production of the cells:
- Bilayer cells (cells of two-layer construction) and bulk heterojunction cells (BHJ cells) were produced under high vacuum (pressure ⁇ 10 -6 mbar).
- Bilayer cell ITO/indanthrene compound/C6o/Bphen/Ag:
- the bilayer cell was produced by successive deposition of an indanthrene compound and C 6 o onto the ITO substrate.
- the deposition rate for both layers was 0.1 nm/second
- the evaporation temperatures of the indanthrene compound are reproduced in table 1 below. Table 1 :
- C 6 o was deposited at 410°C. Once the Bphen layer (layer thickness 6 nm) had been applied, a 100 nm-thick Ag layer was finally applied by vapor deposition as the top electrode. The cell had an area of 0.031 cm 2 .
- the Bphen and Ag layers were applied by vapor deposition as described for the bilayer cell.
- the layer thicknesses were 6 nm for BPhen and 100 nm for Ag.
- the solar simulator used was an AM 1 .5 Simulator from Solar Light Co. Inc. with a xenon lamp (model 16S-150 V3).
- the UV range below 415 nm was filtered and the current-voltage measurements were made under ambient conditions.
- the intensity of the solar simulator was calibrated with a monocrystalline FZ solar cell (Fraunhofer ISE), and the deviation factor was determined to be approximately 1.0.
- Cells comprising the combination of C60 with the indanthrene compounds A, B, C and D have high open-circuit voltages.
- the indanthrene compounds are suitable especially for use in tandem cells owing to their long-wave absorption.
Abstract
Description
Claims
Priority Applications (6)
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JP2012553437A JP2013520791A (en) | 2010-02-19 | 2011-02-18 | Use of indanthrene compounds in organic photovoltaic devices. |
KR1020127023855A KR20130004907A (en) | 2010-02-19 | 2011-02-18 | Use of indanthrene compounds in organic photovoltaics |
EP11744344.0A EP2537186A4 (en) | 2010-02-19 | 2011-02-18 | Use of indanthrene compounds in organic photovoltaics |
AU2011216899A AU2011216899B2 (en) | 2010-02-19 | 2011-02-18 | Use of indanthrene compounds in organic photovoltaics |
CN2011800196312A CN102844886A (en) | 2010-02-19 | 2011-02-18 | Use of indanthrene compounds in organic photovoltaics |
ZA2012/06949A ZA201206949B (en) | 2010-02-19 | 2012-09-17 | Use of indanthrene compounds in organic photovoltaics |
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EP (1) | EP2537186A4 (en) |
JP (1) | JP2013520791A (en) |
KR (1) | KR20130004907A (en) |
CN (1) | CN102844886A (en) |
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Cited By (6)
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WO2013156563A1 (en) * | 2012-04-20 | 2013-10-24 | Rhodia Operations | Quinone acceptors for photovoltaic use |
WO2013176180A1 (en) * | 2012-05-23 | 2013-11-28 | 東レ株式会社 | Photovoltaic power element and method for manufacturing photovoltaic power element |
CN104025330A (en) * | 2011-11-28 | 2014-09-03 | 海洋王照明科技股份有限公司 | Polymer Solar Cell And Method For Preparing Same |
US9087991B2 (en) | 2011-02-01 | 2015-07-21 | Basf Se | Photovoltaic element |
US9406848B2 (en) | 2011-06-10 | 2016-08-02 | Basf Se | Color converter |
US9711665B2 (en) | 2011-05-10 | 2017-07-18 | Basf Se | Color converters |
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CN103850890B (en) * | 2014-03-05 | 2016-08-24 | 广东明阳风电产业集团有限公司 | A kind of anti-torsion cable structure excessively in tower barrel of wind generating set |
US20180231376A1 (en) * | 2015-08-10 | 2018-08-16 | Trinamix Gmbh | Detector for an optical detection of at least one object |
TWI791690B (en) * | 2017-12-14 | 2023-02-11 | 日商迪愛生股份有限公司 | Coloring composition and color filter |
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JP4243237B2 (en) * | 2003-11-10 | 2009-03-25 | 淳二 城戸 | Organic element, organic EL element, organic solar cell, organic FET structure, and organic element manufacturing method |
GB0516800D0 (en) * | 2005-08-16 | 2005-09-21 | Kontrakt Technologies Ltd | Organic compound, semiconductor crystal film and method of producing thereof |
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KR20080103076A (en) * | 2006-02-17 | 2008-11-26 | 바스프 에스이 | Fluorinated rylenetetracarboxylic acid derivatives and use thereof |
KR101197505B1 (en) * | 2006-05-02 | 2012-11-09 | 미쓰비시 가가꾸 가부시키가이샤 | Process for producing organic photo-electric converting element and organic photo-electric converting element |
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JP5645666B2 (en) * | 2007-10-31 | 2014-12-24 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | Use of halogenated phthalocyanines |
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- 2011-02-18 EP EP11744344.0A patent/EP2537186A4/en not_active Withdrawn
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- 2011-02-18 AU AU2011216899A patent/AU2011216899B2/en not_active Ceased
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- 2011-02-18 CN CN2011800196312A patent/CN102844886A/en active Pending
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JPH05102506A (en) * | 1991-10-03 | 1993-04-23 | Ricoh Co Ltd | Photovoltaic element |
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Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
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US9087991B2 (en) | 2011-02-01 | 2015-07-21 | Basf Se | Photovoltaic element |
US9711665B2 (en) | 2011-05-10 | 2017-07-18 | Basf Se | Color converters |
US9406848B2 (en) | 2011-06-10 | 2016-08-02 | Basf Se | Color converter |
US10230023B2 (en) | 2011-06-10 | 2019-03-12 | Basf Se | Color converter |
CN104025330A (en) * | 2011-11-28 | 2014-09-03 | 海洋王照明科技股份有限公司 | Polymer Solar Cell And Method For Preparing Same |
EP2787547A4 (en) * | 2011-11-28 | 2015-07-08 | Oceans King Lighting Science | Polymer solar cell and method for preparing same |
WO2013156563A1 (en) * | 2012-04-20 | 2013-10-24 | Rhodia Operations | Quinone acceptors for photovoltaic use |
FR2989834A1 (en) * | 2012-04-20 | 2013-10-25 | Rhodia Operations | ACCEPTORS QUINONES FOR PHOTOVOLTAIC APPLICATION |
WO2013176180A1 (en) * | 2012-05-23 | 2013-11-28 | 東レ株式会社 | Photovoltaic power element and method for manufacturing photovoltaic power element |
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JP2013520791A (en) | 2013-06-06 |
AU2011216899B2 (en) | 2015-08-20 |
CN102844886A (en) | 2012-12-26 |
AU2011216899A1 (en) | 2012-09-06 |
KR20130004907A (en) | 2013-01-14 |
EP2537186A1 (en) | 2012-12-26 |
EP2537186A4 (en) | 2013-08-28 |
ZA201206949B (en) | 2017-11-29 |
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