WO2011158211A1 - Use of substituted perylenes in organic solar cells - Google Patents
Use of substituted perylenes in organic solar cells Download PDFInfo
- Publication number
- WO2011158211A1 WO2011158211A1 PCT/IB2011/052640 IB2011052640W WO2011158211A1 WO 2011158211 A1 WO2011158211 A1 WO 2011158211A1 IB 2011052640 W IB2011052640 W IB 2011052640W WO 2011158211 A1 WO2011158211 A1 WO 2011158211A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- hydrogen
- phenyl
- unsubstituted
- radicals
- Prior art date
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- 150000002979 perylenes Chemical class 0.000 title 1
- 239000000463 material Substances 0.000 claims abstract description 103
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims abstract description 38
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims abstract description 31
- -1 Ci-C2o-alkyl Inorganic materials 0.000 claims description 878
- 239000001257 hydrogen Substances 0.000 claims description 116
- 229910052739 hydrogen Inorganic materials 0.000 claims description 116
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 99
- 150000001875 compounds Chemical class 0.000 claims description 94
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 77
- 125000003118 aryl group Chemical group 0.000 claims description 68
- 239000004065 semiconductor Substances 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 29
- 229910052731 fluorine Inorganic materials 0.000 claims description 28
- 239000011737 fluorine Substances 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 27
- 239000000460 chlorine Substances 0.000 claims description 27
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- 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 26
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000003107 substituted aryl group Chemical group 0.000 claims description 16
- 229910003472 fullerene Inorganic materials 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 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 10
- 238000010521 absorption reaction Methods 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 230000007704 transition Effects 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 230000003595 spectral effect Effects 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- LFMFPKKYRXFHHZ-UHFFFAOYSA-N R24 Chemical compound C1=C(Cl)C(C)=CC=C1NC1=NC(N)=C(C=CC=C2)C2=N1 LFMFPKKYRXFHHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 description 172
- 150000003254 radicals Chemical group 0.000 description 138
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 132
- 239000000370 acceptor Substances 0.000 description 71
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- 239000000203 mixture Substances 0.000 description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 17
- 229910052794 bromium Inorganic materials 0.000 description 17
- 239000002019 doping agent Substances 0.000 description 17
- 239000003208 petroleum Substances 0.000 description 17
- 238000000151 deposition Methods 0.000 description 16
- 230000008021 deposition Effects 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 230000032258 transport Effects 0.000 description 11
- 229910052725 zinc Inorganic materials 0.000 description 11
- 239000011701 zinc Substances 0.000 description 11
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 10
- 239000004020 conductor Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000011368 organic material Substances 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- 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 7
- 239000007789 gas Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000000746 purification Methods 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
- 238000010992 reflux Methods 0.000 description 7
- 229910052709 silver Inorganic materials 0.000 description 7
- 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 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 125000003282 alkyl amino group Chemical group 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical class C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 229910052737 gold Inorganic materials 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 229930192474 thiophene Natural products 0.000 description 6
- 0 *c1c(*=C)c(*=C)c(*=C)c2c(*=C)c(c(*=C)c(*=C)c(*=C)c3*=C)c3c(*=C)c12 Chemical compound *c1c(*=C)c(*=C)c(*=C)c2c(*=C)c(c(*=C)c(*=C)c(*=C)c3*=C)c3c(*=C)c12 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 125000001544 thienyl group Chemical group 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 229920003026 Acene Polymers 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 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
- 229960000583 acetic acid Drugs 0.000 description 4
- 229910000085 borane Inorganic materials 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000002800 charge carrier Substances 0.000 description 4
- 238000005137 deposition process Methods 0.000 description 4
- BKMIWBZIQAAZBD-UHFFFAOYSA-N diindenoperylene Chemical class C12=C3C4=CC=C2C2=CC=CC=C2C1=CC=C3C1=CC=C2C3=CC=CC=C3C3=CC=C4C1=C32 BKMIWBZIQAAZBD-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000000592 heterocycloalkyl group Chemical group 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
- 239000011630 iodine Chemical group 0.000 description 4
- 229910052740 iodine Chemical group 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- 238000005215 recombination Methods 0.000 description 4
- 230000006798 recombination Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
- 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 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
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- 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
- 239000002178 crystalline material Substances 0.000 description 3
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000000260 fractional sublimation Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000005325 percolation Methods 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
- 238000002360 preparation method Methods 0.000 description 3
- 229940043267 rhodamine b Drugs 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000010129 solution processing Methods 0.000 description 3
- 150000003577 thiophenes Chemical class 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- SCZNXLWKYFICFV-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-b]diazepine Chemical compound C1CCCNN2CCCC=C21 SCZNXLWKYFICFV-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- DABFKTHTXOELJF-UHFFFAOYSA-N 1-propylpyrrole-2,5-dione Chemical compound CCCN1C(=O)C=CC1=O DABFKTHTXOELJF-UHFFFAOYSA-N 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
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- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 1
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 150000003643 triphenylenes Chemical class 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/62—Naphtho [c] pyrroles; Hydrogenated naphtho [c] pyrroles
- C07D209/64—Naphtho [c] pyrroles; Hydrogenated naphtho [c] pyrroles with an oxygen atom in position 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/62—Naphtho [c] pyrroles; Hydrogenated naphtho [c] pyrroles
- C07D209/66—Naphtho [c] pyrroles; Hydrogenated naphtho [c] pyrroles with oxygen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- 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
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
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- C09B57/00—Other synthetic dyes of known constitution
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- 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
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
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- 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
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
- H10K30/57—Photovoltaic [PV] devices comprising multiple junctions, e.g. tandem PV cells
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/211—Fullerenes, e.g. C60
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- 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 with a photoactive region which comprises at least one organic donor material in contact with at least one organic acceptor material, wherein the donor material and the acceptor material form a donor- acceptor heterojunction and wherein the photoactive region comprises at least one substituted perylene.
- Periflanthene derivatives i.e. compounds with a diindeno[1 ,2,3-cd:1 ',2',3'-lm]perylene base skeleton:
- OLEDs organic light-emitting diodes
- Photovoltaics is understood to mean the direct conversion of radiative energy, principally solar energy, to electrical energy.
- 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).
- 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 p-semiconductor and perylene-3,4:9,10-tetracarboxylic acid bisimidazole (PTCBI) as the n-semiconductor.
- CuPc copper phthalocyanine
- PTCBI perylene-3,4:9,10-tetracarboxylic acid bisimidazole
- One of the contact metals used has a large work function and the other a small work function, such that a Schottky barrier is formed by the organic layer.
- Various dopants serve, inter alia, to improve the transport properties.
- JP 2008-135540 describes the use of perylene derivatives of the general formula where R 1 and R 2 are each fused rings which may be substituted by alkyl, alkenyl, aryl, aralkyl or heterocyclyl, and AR 1 - AR 8 may each be alkyl, alkenyl, aryl, aralkyl or heterocyclyl, as an electron donor material for producing organic solar cells.
- R 1 and R 2 are each fused rings which may be substituted by alkyl, alkenyl, aryl, aralkyl or heterocyclyl
- AR 1 - AR 8 may each be alkyl, alkenyl, aryl, aralkyl or heterocyclyl, as an electron donor material for producing organic solar cells.
- exclusively dibenzotetraphenylperiflanthene is used to produce an organic solar cell with photoactive donor-acceptor transitions in the form of a flat heterojunction.
- the use of differently substituted periflanthenes is not demonstrated,
- WO2010/031833 describes the use of dibenzotetraphenylperiflanthene of the formula
- European patent application 09164587.9 (WO 201 1/000939), which was yet to be published at the priority date of the present application, describes an organic solar cell with a photoactive region which comprises at least one organic donor material in contact with at least one organic acceptor material, wherein the donor material and the acceptor material form a donor-acceptor heterojunction and wherein the photoactive region comprises at least one substituted periflanthene of the formula (A)
- X is independently selected from hydrogen and in each case unsubstituted or substituted alkyl, aryl, heteroaryl or oligo(het)aryl,
- Y is independently selected from in each case unsubstituted or substituted alkyl, aryl, heteroaryl or oligo(het)aryl, where in each case at least two adjacent radicals, selected from the X and Y radicals, together with the carbon atoms of the benzene ring to which they are bonded, may also be a fused ring system having 1 , 2, 3, 4, 5, 6, 7 or 8 further rings.
- substituted periflanthenes are particularly advantageously suitable as semiconductor materials for producing organic solar cells with photoactive donor-acceptor transitions, especially with photoactive donor-acceptor transitions in the form of a bulk heterojunction. They serve here especially as donor materials (p-semiconductors).
- the invention first provides an organic solar cell with a photoactive region which comprises at least one organic donor material in contact with at least one organic acceptor material, wherein the donor material and the acceptor material form a donor- acceptor heterojunction and wherein the photoactive region comprises at least one substituted perylene of the formula (I) in which R 1 and R 4 are independently selected from hydrogen and in each case unsubstituted alkyl, substituted alkyl, unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted oligo(het)aryl and substituted oligo(het)aryl; R 2 and R 3 are independently selected from hydrogen and in each case unsubstituted alkyl, substituted alkyl, unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted oligo(het)aryl and substituted oligo(het)
- a together with the carbon atoms to which it is bonded is a fused monocyclic, dicyclic, tricyclic, tetracyclic, pentacyclic or hexacyclic ring system having at least one exocyclic keto group, where the ring system optionally bears one or more substituents bonded via a single bond.
- Figure 1 shows a solar cell suitable for the use of substituted perylenes of the formula (I) and having 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. DESCRIPTION OF THE INVENTION
- unsubstituted or substituted alkyi, aryl, heteroaryl or oligo(het)aryl represents unsubstituted or substituted alkyi, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl or unsubstituted or substituted oligo(het)aryl.
- alkyi comprises straight-chain or branched alkyi.
- Alkyi is preferably Ci-C3o-alkyl, especially Ci-C2o-alkyl and most preferably Ci-Ci2-alkyl.
- alkyi 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 d is preferably hydrogen, alkyi, cycloalkyi, heterocycloalkyi, aryl or hetaryl.
- Substituted alkyi groups may, depending on the length of the alkyi chain, have one or more (e.g. 1 , 2, 3, 4, 5 or more than 5) substituents. These are preferably each independently selected from cycloalkyi, heterocycloalkyi, aryl, hetaryl, fluorine, chlorine, bromine, cyano and nitro.
- Aryl-substituted alkyi radicals (“aralkyl” or arylalkyl) have at least one unsubstituted or substituted aryl group, as defined below.
- R e is preferably hydrogen, alkyi, cycloalkyi, heterocycloalkyi, aryl or hetaryl.
- Arylalkyl is preferably phenyl-Ci-Cio-alkyl, more preferably phenyl-Ci-C4-alkyl, for example benzyl,
- Halogen-substituted alkyi groups comprise a straight-chain or branched alkyi 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, 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, alkylamino, alkylthio, cycloalkyi, heterocycloalkyl, aryl, hetaryl, fluorine, chlorine, bromine, cyano and nitro.
- the cycloalkyi groups preferably bear one or more, for example one, two, three, four or five, Ci-C6-alkyl groups. Examples of substituted cycloalkyi groups are especially 2- and
- aryl comprises mono- or polycyclic aromatic hydrocarbon radicals, having 6 to 18, preferably 6 to 14, more preferably 6 to 10, carbon atoms.
- aryl examples include 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, alkylamino, alkylthio, cycloalkyl,
- heterocycloalkyl aryl, hetaryl, fluorine, chlorine, bromine, cyano and nitro.
- the 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").
- 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. Each alkyl substituent may have 1 to 30 carbon atoms. 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 having 1 to 30 carbon atoms.
- 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-,
- heterocycloalkyi comprises nonaromatic, unsaturated or fully saturated, cycloaliphatic groups having generally 5 to 8 ring atoms, preferably 5 or 6 ring atoms. In the heterocycloalkyi groups, compared to the corresponding cycloalkyl groups, 1 , 2, 3, 4 or more than 4 of the ring carbon atoms are replaced by heteroatoms or heteroatom-containing groups.
- R f is preferably hydrogen, alkyl, cycloalkyl, heterocycloalkyi, aryl or hetaryl.
- heterocycloalkyi groups are especially pyrrolidinyl, piperidinyl, 2,2,6,6-tetramethylpiperidinyl, imidazolidinyl, pyrazolidinyl, oxazolidinyl, morpholidinyl, thiazolidinyl, isothiazolidinyl, isoxazolidinyl, piperazinyl,
- 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
- alkyl independently selected from alkyl, alkoxy, alkylamino, alkylthio, cycloalkyl,
- heterocycloalkyi aryl, hetaryl, fluorine, chlorine, bromine, cyano and nitro.
- the heterocycloalkyi groups preferably bear one or more, for example one, two, three, four or five, Ci-C6-alkyl groups, e.g. 2,2,6,6-tetramethylpiperidinyl.
- 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 ring 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 has 2, 3, 4 or more than 4 fused rings.
- the fused-on rings may be aromatic, saturated or partly unsaturated.
- 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, dibenzothiophenyl, naphtho[2,3-b]- thiophenyl, naphtha[2,3-b]furyl, dihydroindolyl, dihydroindolizinyl, dihydroisoindolyl, dihydroquinolinyl, dihydroisoquinolinyl.
- Substituted heteroaryls 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, alkylamino, alkylthio, cycloalkyl, heterocycloalkyl, aryl, hetaryl, fluorine, chlorine, bromine, cyano and nitro.
- 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.
- heteroarylthio 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 h radicals are each independently unsubstituted alkyl, haloalkyi, fluorine or chlorine, w 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.
- oligohetaryl groups are examples of oligohetaryl groups.
- n 1 , 2, 3, 4, 5, 6, 7 or 8.
- Halogen represents fluorine, chlorine, bromine or iodine.
- R 1 ,R 2 , R 3 , R 4 , R', R", and R 5 to R 29 radicals 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,
- N,N-bis(4-chlorophenyl)aminosulfonyl methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl hexoxycarbonyl, dodecyloxycarbonyl, octadecyloxycarbonyl, phenoxycarbonyl,
- R 1 , R 2 , R 3 , R 4 , R', R", and R 5 to R 29 radicals are as follows:
- 2- fluoro-4-carboxyphenyl 4-bromo-2,5-difluorophenyl, 2,5-dibromo-3,4,6-trifluoro- phenyl, 2-fluoro-5-methylsulfonylphenyl, 5-bromo-2-fluorophenyl, 2-fluoro-4- hydroxymethylphenyl, 3-fluoro-4-bromomethylphenyl, 2-nitro-4-trifluoromethylphenyl,
- a specific embodiment of the invention relates to compounds in which at least one of the R 1 , R 2 , R 3 , R 4 , R', R", and R 5 to R 29 radicals specified in the formula (I) and the formulae which follow is a Ci-C3o-alkyl radical in the form of a so-called swallowtail radical.
- the R 1 , R 2 , R 3 , R 4 , R', R", and R 5 to R 29 radicals are then preferably a radical of the general formula (II)
- R9 radicals are selected from Ci- to C28-alkyl, where the sum of the carbon atoms of the R9 radicals is an integer from 2 to 29.
- the Rs radicals are preferably selected from Ci- to Ci2-alkyl, especially Ci- to Cs-alkyl.
- Preferred radicals of the formula (II) are, for example:
- 1-nonyltetracosanyl 1-octyltetracosanyl, 1-heptyltetracosanyl, 1-hexyltetracosanyl, 1-pentyltetracosanyl, 1-butyltetracosanyl, 1-propyltetracosanyl, 1-ethyltetracosanyl, 1 -methyltetracosanyl, 1 -heptacosanyloctacosanyl, 1 -hexacosanyloctacosanyl,
- R 1 and R 4 radicals may both have the same or a different definition.
- R 1 and R 4 preferably have the same definition.
- R 1 and R 4 are each independently selected are from hydrogen,
- R 1 and R 4 may also be selected from thiophenyl (thienyl) and oligothiophenyl where the two last-mentioned radicals may carry one or more C1-C30 alkyl radicals, in particular C1-C12 alkyl.
- R 1 and/or R 4 are each unsubstituted or substituted Ci- to C3o-alkyl.
- R 1 and/or R 4 are each unsubstituted or substituted Ci- to
- Ci2-alkyl More preferably, R 1 and/or R 4 are each unsubstituted linear Ci- to Ci2-alkyl, especially unsubstituted linear C 4 - to Ci2-alkyl, such as n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl. R 1 and R 4 are especially each unsubstituted or substituted Ci- to Ci2-alkyl or unsubstituted or substituted Ci- to Ci2-alkoxy, more especially
- R 1 and/or R 4 are each a radical of the general formula (II)
- R 9 radicals are selected from Ci- to C28-alkyl, where the sum of the carbon atoms of the R d radicals is an integer from 2 to 29.
- R 1 and/or R 4 is a radical of the general formula (II)
- R 1 and/or R 4 are each substituted alkyl
- the alkyl radicals depending on their chain length, have preferably 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10 or more than 10 substituents.
- the substituents of the alkyl radicals are preferably selected independently from aryl, fluorine, chlorine and nitro.
- R 1 and/or R 4 are each thienyl which may be unsubstituted or may carry one or more, e.g. 1 , 2 or 3, Ci-Ci2-alkyl radicals.
- R 1 and/or R 4 are each oligothiophenyl where each thiophene unit may be unsubstituted or may carry one or more, e.g. 1 or 2, Ci-Ci2-alkyl radicals.
- R 1 and/or R 4 are each alkaryl or aryl, where aryl and the aryl moiety of alkaryl is preferably phenyl, naphthyl, anthracyl or phenanthryl.
- R 1 and R 4 are preferably each selected from hydrogen and groups of the general formulae (III.1 ) to (111.12)
- R' are each independently selected from hydrogen, fluorine, chlorine, unsubstituted alkyl and substituted alkyl.
- R' radicals in the groups of the formula (111.1 ) have a definition other than hydrogen.
- Monosubstituted groups of the formula (111.1 ) preferably have an R' radical in the 4 position.
- Disubstituted groups of the formula (111.1 ) preferably have two R' radicals in the 3 position and in the 5 position.
- R' radicals in the groups of the formula (III.2) have a definition other than hydrogen. More preferably, 0 or 1 of the R' radicals in the groups of the formula (III.2) have a definition other than hydrogen.
- Monosubstituted groups of the formula (III.2) preferably have an R' radical in the 4 position.
- 0, 1 , 2, 3 or 4 of the R' radicals in the groups of the formula (III.3) have a definition other than hydrogen. More preferably, 0 or 1 of the R' radicals in the groups of the formula (III.3) have a definition other than hydrogen.
- 0, 1 , 2, 3, 4, 5 or 6 of the R' radicals in the groups of the formula (III.4) have a definition other than hydrogen. More preferably, 0 or 1 of the R' radicals in the groups of the formula (III.4) have a definition other than hydrogen.
- 0, 1 , 2, 3, 4, 5 or 6 of the R' radicals in the groups of the formula (III.5) have a definition other than hydrogen. More preferably, 0 or 1 of the R' radicals in the groups of the formula (III.5) have a definition other than hydrogen.
- 0, 1 , 2, 3, 4, 5 or 6 of the R' radicals in the groups of the formula (III.6) have a definition other than hydrogen. More preferably, 0 or 1 of the R' radicals in the groups of the formula (III.6) have a definition other than hydrogen.
- 0, 1 or 2 of the R' radicals in the groups of the formula (III.7) have a definition other than hydrogen. More preferably, 0 or 1 of the R' radicals in the groups of the formula (III.7) have a definition other than hydrogen.
- 0, 1 or 2 of the R' radicals in the groups of the formula (III.8) have a definition other than hydrogen. More preferably, 0 or 1 of the R' radicals in the groups of the formula (III.8) have a definition other than hydrogen.
- 0, 1 , 2, 3 or 4 of the R' radicals in the groups of the formulae (III.9) to (111.12) have a definition other than hydrogen.
- 0, 1 or 2 of the R' radicals on each thiophene ring have a definition other than hydrogen.
- 0 or 1 of the R' radicals in the groups of the formulae (III.9) to (111.12) have a definition other than hydrogen.
- the R' radicals in the (111.1 ) to (111.12) groups are each independently selected from hydrogen, Ci-C2o-alkyl, fluorine and chlorine.
- the R' radicals in the (111.1 ) to (111.12) groups are each independently selected from hydrogen and Ci- to Ci2-alkyl.
- the R' radicals which have a definition other than hydrogen in the (111.1 ) to (111.12) groups are selected from unsubstituted Ci- to C 4 -alkyl groups, such as methyl, ethyl, n-propyl, isopropyl, n-butyl and tert-butyl.
- the R' radicals which have a definition other than hydrogen in the (111.1 ) to (111.12) groups are selected from unsubstituted linear C 4 - to Ci2-alkyl groups, especially unsubstituted linear C8-Ci2-alkyl, such as n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl.
- the R' radicals which have a definition other than hydrogen in the (111.1 ) to (111.12) groups are selected from radicals of the general formula (II)
- R9 radicals are selected from Ci- to C28-alkyl, where the sum of the carbon atoms of the R9 radicals is an integer from 2 to 29.
- R' is a radical of the general formula (II)
- R 1 and R 4 may be independently of each other selected from phenyl, naphthyl, anthracyl, thiophen-2-yl, thiopheny-3-yl and oligothiophenyl, where phenyl, naphthyl, anthracyl, thiophen-2-yl and thiopheny-3-yl may be unsubstituted or may carry one or two C1-C12 alkyl radicals and where oligothiophenyl may carry one or two C1-C12 alkyl radical on each thiophene unit.
- a special embodiment relates to compounds of the formula I, wherein R 1 and/or R 4 are thiophen-2-yl, thiopheny-3-yl or oligothiophenyl, where thiophen-2-yl and thiopheny-3-yl may be unsubstituted or may carry one C1-C12 alkyl radical and where oligothiophenyl may carry one C1-C12 alkyl radical on each thiophene unit.
- R 1 and R 4 are each independently selected from hydrogen and groups of the general formulae (111.1 a), (111.1 b), (111.1 c), (lll.l d), (lll.2a), (lll.4a), (lll.7a), (lll.7b), (lll.8a), (I II .8b), (lll.9a), (II 1.9b), (lll.9c), (lll.9d), (III.10a), (III.10b), (111.10c), (IIM Od), (111.1 1 a), (111.1 1 b), (111.1 1 c), (lll.1 1 d), (111.12a), (111.12b), (111.12c) and (111.12d):
- # is the bonding site to the benzene ring
- R' is d-Cs-alkyl.
- the R 1 and R 4 groups are each independently selected from hydrogen and phenyl.
- the R 1 and R 4 groups are each independently selected from hydrogen, phenyl, thiophen-2-yl, thiophen-3-yl and 5-methylthiophen-2-yl.
- R 1 and R 4 are especially both hydrogen or are both phenyl.
- R 1 and R 4 are especially both thiophen-2-yl or both 5-methylthiophen-2-yl.
- R 2 and R 3 radicals In the compounds of the general formula (I), the R 2 and R 3 radicals may both have the same definition or each have a different definition. R 2 and R 3 preferably have the same definition.
- R 2 and R 3 are preferably each independently selected from hydrogen, unsubstituted alkyl, aralkyl, unsubstituted aryl, alkaryl and halogen-substituted aryl.
- R 2 and R 3 may also be selected from thiophenyl and oligothiophenyl where the two last-mentioned radicals may carry one or more C1-C30 alkyl, in particular C1-C12 alkyl, radicals.
- R 2 and/or R 3 are each unsubstituted or substituted Ci- to C3o-alkyl.
- R 2 and/or R 3 are preferably each unsubstituted or substituted Ci- to Ci2-alkyl.
- R 2 and/or R 3 are more preferably each unsubstituted linear Ci- to Ci2-alkyl, especially unsubstituted linear C 4 - to Ci2-alkyl, such as n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl.
- R 2 and R 3 are especially each unsubstituted or substituted Ci- to Ci2-alkyl or unsubstituted or substituted Ci- to Ci2-alkoxy, more especially unsubstituted linear Ci- to Ci2-alkyl, even more especially unsubstituted linear C 4 - to Ci2-alkyl, such as n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl.
- R 2 and/or R 3 are each a radical of the general formula (II)
- R9 radicals are selected from Ci- to C28-alkyl, where the sum of the carbon atoms of the R9 radicals is an integer from 2 to 29.
- R 2 and/or R 3 is a radical of the general formula (II)
- R 2 and/or R 3 groups in the compounds of the general formula (I) are substituted alkyi
- the alkyi radicals depending on their chain length, have preferably 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10 or more than 10 substituents.
- the substituents of the alkyi radicals are preferably each independently selected from aryl, fluorine, chlorine and nitro.
- R 2 and/or R 3 are selected from thienyl which may be unsubstituted or may carry one or more, e.g. 1 , 2 or 3, Ci-Ci2-alkyl radicals.
- R 2 and/or R 3 are selected from oligothiophenyl where each thiophene unit may be unsubstituted or may carry one or more, e.g. 1 or 2, Ci-Ci2-alkyl radicals.
- R 2 and/or R 3 are selected from alkaryl and aryl, where aryl and the aryl moiety of alkaryl is preferably phenyl, naphthyl, anthracyl or phenanthryl.
- R 2 and R 3 groups in the compounds of the general formula (I) are each independently selected from hydrogen and groups of the general formulae (IV.1 ) to (IV.12)
- R" are each independently selected from hydrogen, fluorine, chlorine, unsubstituted alkyl and substituted alkyl.
- R" radicals in the groups of the formula (IV.1 ) have a definition other than hydrogen.
- Monosubstituted groups of the formula (IV.1 ) preferably have an R" radical in the 4 position.
- Disubstituted groups of the formula (IV.1 ) preferably have two R" radicals in the 3 position and in the 5 position.
- R" radicals in the groups of the formula (IV.2) have a definition other than hydrogen. More preferably, 0 or 1 of the R" radicals in the groups of the formula (IV.2) have a definition other than hydrogen.
- Monosubstituted groups of the formula (IV.2) preferably have an R" radical in the 4 position.
- 0, 1 , 2, 3 or 4 of the R" radicals in the groups of the formula (IV.3) have a definition other than hydrogen. More preferably, 0 or 1 of the R" radicals in the groups of the formula (IV.3) have a definition other than hydrogen.
- 0, 1 , 2, 3, 4, 5 or 6 of the R" radicals in the groups of the formula (IV.4) have a definition other than hydrogen. More preferably, 0 or 1 of the R" radicals in the groups of the formula (IV.4) have a definition other than hydrogen.
- 0, 1 , 2, 3, 4, 5 or 6 of the R" radicals in the groups of the formula (IV.5) have a definition other than hydrogen. More preferably, 0 or 1 of the R" radicals in the groups of the formula (IV.5) have a definition other than hydrogen.
- 0, 1 , 2, 3, 4, 5 or 6 of the R" radicals in the groups of the formula (IV.6) have a definition other than hydrogen. More preferably, 0 or 1 of the R" radicals in the groups of the formula (IV.6) have a definition other than hydrogen.
- 0, 1 or 2 of the R" radicals in the groups of the formula (IV.7) have a definition other than hydrogen. More preferably, 0 or 1 of the R" radicals in the groups of the formula (IV.7) have a definition other than hydrogen.
- 0, 1 or 2 of the R" radicals in the groups of the formula (IV.8) have a definition other than hydrogen. More preferably, 0 or 1 of the R" radicals in the groups of the formula (IV.8) have a definition other than hydrogen.
- 0, 1 , 2, 3 or 4 of the R" radicals in the groups of the formulae (IV.9) to (IV.12) have a definition other than hydrogen.
- 0, 1 or 2 of the R" radicals on each thiophene ring have a definition other than hydrogen. More preferably, 0 or 1 of the R" radicals in the groups of the formulae (IV.9) to (IV.12) have a definition other than hydrogen.
- the R" radicals which have a definition other than hydrogen in the (IV.1 ) to (IV.12) groups are selected from unsubstituted Ci- to C 4 -alkyl groups, such as methyl, ethyl, n-propyl, isopropyl, n-butyl and tert-butyl.
- the R" radicals which have a definition other than hydrogen in the (IV.1 ) to (IV.12) groups are selected from unsubstituted linear C 4 - to Ci2-alkyl groups, especially unsubstituted linear C8-Ci2-alkyl such as n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl.
- R" radicals which have a definition other than hydrogen in the (IV.1 ) to (IV.12) groups are selected from radicals of the general formula (II)
- R9 radicals are selected from Ci- to C28-alkyl, where the sum of the carbon atoms of the R9 radicals is an integer from 2 to 29.
- R" is a radical of the general formula (II)
- R 2 and R 3 may be independently of each other selected from phenyl, naphthyl, anthracyl, thiophen-2-yl, thiopheny-3-yl and oligothiophenyl, where phenyl, naphthyl, anthracyl, thiophen-2-yl and thiopheny-3-yl may be unsubstituted or may carry one or two C1-C12 alkyl radicals and where oligothiophenyl may carry one C1-C12 alkyl radical on each thiophene unit.
- a special embodiment relates to compounds of the formula I, wherein R 2 and/or R 3 are thiophen-2-yl, thiopheny-3-yl or oligothiophenyl, where thiophen-2-yl and thiopheny-3-yl may be unsubstituted or may carry one C1-C12 alkyl radical and where oligothiophenyl may carry one C1-C12 alkyl radical on each thiophene unit.
- R 2 and R 3 are each independently selected from hydrogen and groups of the general formulae (IV.1 a), (IV.1 b), (IV.1 c), (IV.1 d), (IV.2a), (IV.4a), (IV.7a), (IV.7b), (IV.8a), (IV.8b), (IV.9a), (IV.9b), (IV.9c), (IV.9d), (IV.10a), (IV.10b), (IV.10c), (IV.10d), (IV.1 1 a), (IV.1 1 b), (IV.1 1 c), (IV.1 1 d), (IV.12a), (IV.12b), (IV.12c) and (IV.1 1 d):
- R" is d-Cs-alkyl.
- the R 2 and R 3 groups are especially each independently selected from hydrogen and phenyl.
- R 2 and R 3 are especially both hydrogen or both phenyl.
- the two R 2 and R 3 radicals in the compounds of the general formula (I), together with the carbon atoms of the benzene ring to which they are bonded, are a fused ring system having 1 , 2, 3 or 4 further rings.
- R 2 and R 3 in the compounds of the general formula (I) together are a group which is selected from groups of the general formulae (V.1 ), (V.2) and (V.3)
- R 5 , R 6 , R 7 and R 8 are each independently hydrogen, Ci-C2o-alkyl, halogen or phenyl, where phenyl may be unsubstituted or may bear 1 , 2 or 3 R a radicals;
- R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are each independently hydrogen, Ci-C 2 o-alkyl, halogen or phenyl, where phenyl may be unsubstituted or may bear 1 , 2 or 3 R a radicals; and
- R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 and R 22 are each independently hydrogen, Ci-C 20 -alkyl, halogen or phenyl, where phenyl may be unsubstituted or may bear 1 , 2 or 3 R a radicals, in which
- R a is Ci-Cio-alkyl or Ci-C 6 -alkoxy. More preferably, R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 and R a independently of one another and preferably in combination preferably have the meanings given below:
- R 5 , R 6 , R 7 and R 8 are each independently hydrogen, Ci-C2o-alkyl, or phenyl, where phenyl may be unsubstituted or may bear 1 , 2 or 3 R a radicals;
- R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are each independently hydrogen, Ci-C 2 o-alkyl, or phenyl, where phenyl may be unsubstituted or may bear 1 , 2 or 3 R a radicals; and R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 and R 22 are each independently hydrogen, Ci-C 20 -alkyl, or phenyl, where phenyl may be unsubstituted or may bear 1 , 2 or 3 R a radicals, in which
- R a is Ci-Cio-alkyl.
- R 2 and R 3 together are a group of the formula (V.1 ).
- R 5 , R 6 , R 7 and R 8 in the groups (V.1 ) are each hydrogen.
- 0, 1 , 2, 3 or 4 of the R 3 radicals in the groups of the formulae (V.2) and (V.3) have a definition other than hydrogen.
- the R 5 to R 22 radicals in the (V.2) and (V.3) groups are each independently selected from hydrogen, Ci- to C2o-alkyl, fluorine, chlorine and phenyl.
- R 5 to R 22 radicals in the (V.1 ) to (V.3) groups are each
- the R 5 to R 22 radicals in the (V.1 ) to (V.3) groups are each independently selected from hydrogen, Ci- to Ci2-alkyl and phenyl.
- the R 5 to R 22 radicals which have a definition other than hydrogen in the (V.1 ) to (V.3) groups are selected from unsubstituted Ci- to C 4 -alkyl groups, such as methyl, ethyl, n-propyl, isopropyl, n-butyl and tert-butyl.
- the R 5 to R 22 radicals which have a definition other than hydrogen in the (V.1 ) to (V.3) groups are selected from unsubstituted linear C 4 - to Ci2-alkyl groups, such as n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl.
- the R 5 to R 22 radicals which have a definition other than hydrogen in the (V.1 ) to (V.3) groups are selected from radicals of the general formula (II)
- R9 radicals are selected from Ci- to C28-alkyl, where the sum of the carbon atoms of the R9 radicals is an integer from 2 to 29.
- R 5 to R 22 is a radical of the general formula (I I), reference is made completely to the suitable and preferred Rs radicals specified above.
- R 2 and R 3 together are a (V.1 ), (V.2) or (V.3) group in which the R 5 to R 22 radicals are all hydrogen.
- the A groups in the compounds of the general formula (I) are selected from groups of the general formulae (VI.1 ), (VI.2), (VI.3), (VI.4) and (VI.5)
- R 23 is hydrogen, and in each case unsubstituted or substituted alkyi, cycloalkyl,
- R 24 , R 25 are each independently halogen, unsubstituted alkyi, substituted alkyi,
- unsubstituted aryl or substituted aryl and where two R 24 and/or R 25 radicals bonded to adjacent carbon atoms may also be a fused-on benzene ring, is halogen, unsubstituted alkyi, substituted alkyi, unsubstituted aryl or substituted aryl, and where two R 26 radicals bonded to adjacent carbon atoms may be a fused-on benzene ring,
- R 28 are each independently halogen, unsubstituted alkyi, substituted alkyi, unsubstituted aryl or substituted aryl, and where two R 27 and/or R 28 radicals bonded to adjacent carbon atoms may also be a fused-on benzene ring, is halogen, unsubstituted alkyi, substituted alkyi, unsubstituted aryl or substituted aryl, and where two R 29 radicals bonded to adjacent carbon atoms may be a fused-on benzene ring, m, n are each independently 0, 1 , 2 or 3, are each 0, 1 or 2.
- the A group is more preferably selected from groups of the general formulae (VI.1 ), (VI.2), (VI.3), (VI.4) and (VI.5) in which
- R 23 is hydrogen, Ci-C2o-alkyl, C3-C7-cycloalkyl, C3-C7-heterocyclyl, C6-Ci4-aryl-Ci-C2o- alkyl, C6-Ci4-aryl, Ci-C2o-alkyl-C6-Ci4-aryl, or a 5- or 6-membered heteroaromatic radical which has 1 , 2 or 3 heteroatoms selected from O, S and N as ring members, and in which the heteroaromatic radical may have a fused-on benzene ring or naphthalene ring and may have 1 , 2, 3, 4, 5 or 6 R b substituents, and the aryl group in C6-Ci4-aryl-Ci-C2o-alkyl, C6-Ci4-aryl, Ci-C2o-alkyl-C6-Ci4-aryl may have 1 , 2, 3, 4, 5 or 6 R b substituents,
- R 24 , R 25 are each independently Ci-C2o-alkyl, halogen or phenyl, where phenyl may be unsubstituted or may bear 1 , 2 or 3 R c radicals, and where two R 24 and/or R 25 radicals bonded to adjacent carbon atoms may also be a fused-on benzene ring
- R 26 is Ci-C2o-alkyl, halogen or phenyl, where phenyl may be unsubstituted or may bear 1 , 2 or 3 R c radicals, and where two R 26 radicals bonded to adjacent carbon atoms may be a fused-on benzene ring
- R 27 , R 28 are each independently Ci-C2o-alkyl, halogen or phenyl, where phenyl may be unsubstituted or may bear 1 , 2 or 3 R c radicals, and where two R 27 and/or R 28 radicals bonded to adjacent carbon atoms may also be
- R 29 is Ci-C2o-alkyl, halogen or phenyl, where phenyl may be unsubstituted or may bear 1 , 2 or 3 R c radicals, and where two R 29 radicals bonded to adjacent carbon atoms may be a fused-on benzene ring, m, n are each independently 0, 1 , 2 or 3, o, p, q, r are each 0, 1 or 2,
- R b is fluorine, chlorine, cyano, nitro or Ci-C2o-alkoxy
- R c is fluorine, chlorine, cyano, nitro, Ci-C2o-alkyl or Ci-C2o-alkoxy.
- A is more preferably a group of the formula (VI.1 ) in which R 23 is phenyl, Ci-C6-alkyl or hydrogen.
- a specific embodiment is a perylene compound of the formula (I) in which
- R 1 and R 4 are both phenyl
- R 2 and R 3 together are a radical of the formula (V.1 ) in which R 5 , R 6 , R 7 and R 8 are each hydrogen, and
- A is a radical of the formula (VI.1 ) in which R 23 is phenyl or hydrogen.
- a further specific embodiment is a perylene compound of the formula (I) in which R 1 and R 4 are both phenyl;
- R 2 and R 3 together are a radical of the formula (V.1 ) in which R 5 , R 6 , R 7 and R 8 are each hydrogen or R 2 and R 3 together are a radical of the formula (V.2) in which R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are each hydrogen; and
- A is a radical of the formula (VI.1 ) in which R 23 is Ci-C4-alkyl.
- a further specific embodiment is a perylene compound of the formula (I) in which R 1 and R 4 are both phenyl;
- R 2 and R 3 together are a radical of the formula (V.1 ) in which R 5 , R 6 , R 7 and R 8 are each hydrogen or R 2 and R 3 together are a radical of the formula (V.2) in which R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are each hydrogen; and
- A is a radical of the formula (VI .4) in which p is 0 and q is 0.
- a further specific embodiment is a perylene compound of the formula (I) in which R 1 and R 4 are both phenyl;
- R 2 and R 3 together are a radical of the formula (V.1 ) in which R 5 , R 6 , R 7 and R 8 are each hydrogen or R 2 and R 3 together are a radical of the formula (V.2) in which R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are each hydrogen; and
- A is a radical of the formula (VI.5) in which r is 0.
- R is hydrogen, Ci-Cis-alkyl, C3-C7-cycloalkyl, C3-C7-heterocyclyl, C6-Ci4-aryl-Ci-C2o- alkyl, C6-Ci4-aryl, Ci-C2o-alkyl-C6-Ci4-aryl, or a 5- or 6-membered heteroaromatic radical which has 1 , 2 or 3 heteroatoms selected from O, S and N as ring members, and in which the heteroaromatic radical may have a fused-on benzene ring or naphthalene ring and may have 1 , 2, 3, 4, 5 or 6 R b substituents, and the aryl group in C6-Ci4-aryl-Ci-C2o-alkyl, C6-Ci4-aryl, Ci-C2o-alkyl-C6-Ci4-aryl may have 1 , 2, 3, 4, 5 or 6 R b substituents, and
- R b is fluorine, chlorine, cyano, nitro or Ci-C6-alkoxy. Especially, R is hydrogen, Ci-C4-alkyl or phenyl.
- the perylenes used in the inventive solar cells can be prepared by customary processes known to those skilled in the art. These include the buildup of the molecular skeleton from a bromaryl compound with an arylboronic acid derivative under the conditions of a Suzuki coupling, i.e. in the presence of a platinum metal catalyst and especially in the presence of a palladium catalyst, under reaction conditions known per se, as known, for example, from Acc. Chem. Res. 15, p. 178-184 (1982), Chem. Rev. 95, p. 2457-2483 (1995), and the literature cited therein, and also from J. Org. Chem. 68, p. 9412 (2003).
- Suitable catalysts are especially tetrakis(triphenyl- phosphine)palladium(O), bis(triphenylphosphine)palladium(ll) chloride, bis(acetonitrile)- palladium(ll) chloride, the [1 ,1 '-bis(diphenylphosphino)ferrocene]palladium(ll) chloride- dichloromethane complex, bis[1 ,2-bis(diphenylphosphine)ethane]palladium(0) and [1 ,4-bis(diphenylphosphine)butane]palladium(ll) chloride.
- the amount of catalyst is typically 0.1 to 10 mol%.
- the perylene compound Before use in an organic solar cell, the perylene 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.
- Individual purifying operations can be repeated twice or more. Different purifying operations can be combined with one another.
- 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.
- a gradient of at least two different solvents for example a toluene/petroleum ether gradient.
- 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.
- 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 perylene 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, polystyrene, polyvinyl chlorides and mixtures and composites.
- Suitable electrodes (cathode, anode) are in principle metals, 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.
- Preferred semiconductors are e.g. 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 that of 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 the 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 electrical contact connection 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. This includes metal films, preferably of Ag, Au, Al, Ca, Mg, In, and mixtures thereof. Preferred mixtures are Mg/AI.
- 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 perylene 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), - layers which comprise a hole-conducting material (hole transport layer, HTL), which need not absorb any radiation,
- 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 polyethylenedioxy- thiophene (PEDOT).
- BCP bathocuproin
- m-MTDATA 4,4',4"-tris- [3-methylphenyl-N-phenylamino]triphenylamine
- PEDOT polyethylenedioxy- thiophene
- the inventive solar cells comprise at least one photoactive donor-acceptor
- At least one substituted perylene of the general formula (I) can be used as a charge generator (donor).
- ETM electron acceptor material
- Suitable ETMs are, for example, C60 and other fullerenes, perylene-3,4;9,10-bis(dicarboximides) (PTCDIs), etc. (as described hereinafter).
- Preferred ETMs are C60 and other fullerenes which are discussed below.
- 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. Cryst, 252, 243-258 (1994).).
- 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
- perylene compounds of the general formula (I) in tandem cells is a preferred embodiment of the invention.
- 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).
- a gas phase deposition process physical vapor deposition, PVD
- a perylene compound of the general formula (I) and a complementary semiconductor material can be subjected to a gas phase deposition in the manner of a cosublimation.
- 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 spin-coating, knife- coating, casting processes, spray application, dip-coating or printing (e.g. inkjet, flexographic, offset, gravure; intaglio printing, nanoimprinting).
- laser ablation or solution or dispersion processing methods such as spin-coating, knife- coating, casting processes, spray application, dip-coating or printing (e.g. inkjet, flexographic, offset, gravure; intaglio printing, nanoimprinting).
- 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 a flat heterojunction and 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 preferably 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-ethylene- dioxythiophene) poly(styrenesulfonate) (PEDOT-PSS), Ir-DPBIC (tris-N,N'-diphenyl- benzimidazol-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-ethylene- dioxythiophene) poly(styrenesulfonate)
- Ir-DPBIC tris-N,N'-diphenyl-
- 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 preferably comprises at least one fullerene or fullerene derivative. Alternatively or additionally suitable acceptor materials are specified hereinafter.
- 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).
- EBL/ETL exciton-blocking and/or electron-conducting layer
- 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.
- BCP 2,9-dimethyl-4,7-diphenyl-1 ,10-phenanthroline
- Bphen 4,7-diphenyl- 1 ,10-phenanthroline
- BPY-OXD 1,3-bis[2-(2,2'-bipyridin-6-yl)-1 ,3,4-oxadiazo-5-yl]benzene
- 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 is preferably within a range from 5 to 500 nm, more preferably 10 to l OO 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 )
- 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)
- the layer (23) comprises at least one perylene 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.
- 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-phen- anthroline (Bphen), 1 ,3-bis[2-(2,2 ' -bipyridin-6-yl)-1 ,3,4-oxadiazo-5-yl]benzene
- 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, Pyronin B (PyB), Rhodamine B, cobaltocenes, etc.
- the thickness of the layer (23) is, if present, preferably within a range from 1 nm to 1 ⁇ , particularly 5 to 60 nm. With regard to layer (25), reference is made completely to the above remarks regarding layer (15).
- 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 hetero-junction.
- 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 a perylene compound periflanthene of the general formula (I).
- the photoactive layer of at least one subcell comprises a perylene 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 a perylene 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 a perylene 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 perylene compound of the general formula (I) and fullerene or fullerene derivative used in accordance with the invention absorbs in the short-wave range of sunlight, e.g. in the range from 400 to 600 nm.
- the tandem cell comprises at least one subcell with an absorption maximum in the relatively long-wave spectral region, e.g. in the range from 600 nm to 800 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 about 400 nm to 800 nm.
- the tandem cell comprises at least one subcell with an absorption maximum in the range from 400 to 600 nm and at least one subcell with an absorption maximum in the range from 600 to 850 nm. According to a further preferred embodiment, the tandem cell comprises at least one subcell with an absorption maximum in the range from 400 to 550 nm and at least one subcell with an absorption maximum in the range from 550 to 900 nm. According to a further preferred embodiment, the tandem cell comprises at least one subcell with an absorption maximum in the range from 400 to 650 nm and at least one subcell with an absorption maximum in the range from 650 to 900 nm. Suitable combination of subcells should thus allow the spectral range utilized to be extended.
- the tandem cell additionally comprises at least one subcell with an absorption maximum in the relatively long-wave spectral region, preferably in the range from 600 to 900 nm.
- 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 perylene 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 perylene compound as a donor which is in contact with at least one acceptor.
- Preferred acceptors are 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.
- Ceo [60]PCBM
- C70 phenyl-C6i-butyric acid methyl ester
- the semiconductor materials listed hereinafter are suitable in principle for use in the inventive solar cells. They serve especially as donors or acceptors for subcells of a tandem cell, which are combined with a perylene/fullerene subcell used in accordance with the invention.
- Suitable further semiconductors are phthalocyanines. These include phthalocyanines which are unhalogenated or which bear 1 to 16 halogen atoms.
- the phthalocyanines may be metal-free or comprise a divalent metal or a metal atom-containing group. Preference is given to phthalocyanines based on zinc, copper, iron, titanyloxy, vanadyloxy, etc. Particular preference is given to copper phthalocyanines, zinc phthalocyanines and metal-free phthalocyanines.
- 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-octa- fluorophthalocyanine 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 hexadecachlorophthalocyanine, zinc hexadecachlorophthalocyanine, metal-free hexadecachlorophthalocyanine, copper hexadecafluorophthalocyanine, zinc hexadecafluorophthalo- cyanine or metal-free hexadecafluorophthalocyanine.
- hexadecachlorophthalocyanine such as copper hexadecachlorophthalocyanine, zinc hexadecachlorophthalocyanine, metal-free hexadecachlorophthalocyanine, copper hexadecafluorophthalocyanine, zinc hexadecafluorophthalo- cyanine or metal-free hexadecafluorophthal
- 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.
- donor semiconductor materials which can be used, for example, in a tandem cell as described hereinafter, in a further subcell in place of the perylene 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.
- tetrabenzoporphyrins are especially preferred. These can be processed from solution as soluble precursors and are converted to the photoactive component by thermolysis on the substrate.
- acenes are preferably selected from anthracene, tetracene, pentacene, each of which may be unsubstituted or substituted.
- Substituted acenes preferably comprise 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, cabroxylate or thioalkoxy.
- Suitable electron-withdrawing substituents are, for example, halogen, nitro or cyano.
- Preferred acenes are selected from 2,9-dialkyl- pentacenes and 2,10-dialkylpentacenes, 2,10-dialkoxypentacenes, 1 ,4,8,1 1 -tetra- alkoxypentacenes 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-nonyl- phenyl)triphenylene (PTPg) or 2,3,6,7,10,1 1 -hexakis(undecyloxy)triphenylene (HATu).
- HBC-PhCi2 hexabenzocoronene
- HTT 6 2,3,6,7,10,1 1 -hexahexylthiotriphenylene
- PTPg 2,3,6,7,10,1 1 -hexakis(undecyloxy)triphenylene
- HCTu liquid-crystalline materials which are discotic.
- thiophene compounds are preferably selected from thiophenes, oligothiophenes and substituted derivatives thereof.
- Suitable oligothiophenes are quaterthiophenes, quinquethiophenes, sexithiophenes, a,co-di(Ci-C8)-alkyloligothiophenes, such as ⁇ , ⁇ -dihexylquarter- thiophenes, ⁇ , ⁇ -dihexylquinquethiophenes and ⁇ , ⁇ -dihexylsexithiophenes, poly(alkylthiophenes) such as poly(3-hexylthiophene), bis(dithienothiophenes), anthradithiophenes and dialkylanthradithiophenes such as dihexylanthradithiophene, phenylene-thiophene (P-T)
- thiophene compounds suitable as semiconductors are preferably selected from compounds of the type
- DCV5T a,a'-bis(2,2-dicyanovinyl)quinquethiophene
- PCPDTBT poly[2,6-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1 b;3,4 b']dithiophene)- 4,7-(2,1 ,3-benzothiadiazole)
- poly(pyridopyrazinevinylene)-polythiophene blends such as EHH-PpyPz, PTPTB copolymers, BBL, F 8 BT, PFMO (see Brabec C, Adv. Mater., 2996, 18, 2884).
- Further semiconductors suitable as donors are paraphenylenevinylene and oligomers or polymers comprising paraphenylenevinylene units.
- the latter 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 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'-dimethyloct
- polyfluorenes and alternating polyfluorene copolymers are polyfluorenes and alternating polyfluorene copolymers. These are preferably selected from 4,7-dithien-2'-yl- 2,1 ,3-benzothiadiazole, poly(9,9'-dioctylfluorene-co-benzothiadiazole) (FeBT), and
- Further 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.
- inventive solar cell has the following layers:
- the inventive solar cell is more preferably a tandem cell.
- one subcell preferably has a photoactive region which comprises at least one perylene compound of the formula (I) and C60.
- one subcell preferably has a photoactive region which comprises at least one perylene compound of the formula (I) and C70.
- the subcell has a photoactive region which comprises at least one perylene 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 can 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-conductive material.
- n-doping an electron is released from the dopant which acts as a donor, whereas, in the case of p-doping, the dopant acts as an acceptor which absorbs an electron.
- Suitable dopants for the perylene 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 tetra- cyanoquinodimethane (TCNQ).
- a preferred dopant is 3,6-difluoro-2,5,7,7,8,8-hexa- cyanoquinodimethane.
- Suitable dopants for the p-semiconductors used in accordance with the invention are, for example, selected from CS2CO3, LiF, pyronin B (PyB), rhodamine derivatives, cobaltocenes, etc.
- Preferred dopants are pyronin B and rhodamine derivatives, especially rhodamine B.
- the dopants are used in an amount of up to 10 mol%, preferably up to 5 mol%, based on the amount of the semiconductor to be doped.
- NMP N-methylpyrrolidone
- dichloromethane 10.0 g (25 mmol) of 7,14-diphenylbenzofluoranthene (prepared as described in
- 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; roughness mean square) was less than 5 nm.
- RMS mean roughness
- the substrate was treated with ozone under UV light for 20 minutes (UV-ozone cleaning).
- 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/MoOs/inventive compound of the formula 1/Ceo/Bphen/Ag:
- the bilayer cell was produced by successive deposition of an inventive compound of the formula I and C 6 o (layer thickness 40 nm) onto Mo03-coated ITO substrate.
- the deposition rate for both layers was 0.1 nm/second.
- the evaporation temperature of the inventive compound of the formula (I) is reproduced in table 1 below.
- 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 0.04 cm 2 .
- BHJ cell ITO/Mo03/(inventive compound of the formula (l):C6o)/C6o/Bphen/Ag:
- an inventive compound of the formula (I) and Ceo were coevaporated.
- the Bphen and Ag layers were deposited 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 380 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.
- ITO was sputtered onto the glass substrate in a thickness of 120 nm.
- the specific resistivity was 15 ⁇ cm, and the mean roughness (RMS; roughness mean square) was less than 2 nm.
- RMS mean roughness
- the substrate was treated with ozone under UV light for 15 minutes (UV-ozone cleaning).
- Bilayer cells (cells of two-layer construction) and bulk heterojunction cells (BHJ cells) were produced under high vacuum (pressure : ca 2 x 10 -6 mbar).
- Bilayer cell ITO/MoOs/inventive compound of the formula 1/Ceo/Bphen/Ag:
- the bilayer cell was produced by successive deposition of an inventive compound of the formula I and C 6 o onto Mo03-coated ITO substrate. The deposition rate for both layers was 0.3 nm/second. C60 was evaporated at 340°C (compound from example 3) and 380°C (compound from example 4), respectively. The evaporation temperature of the inventive compound of the formula (I) is reproduced in table 4 below. Bphen was evaporated at 1 50°C (compound from example 3) and 130°C (compound from example 4), respectively. Finally 1 00 nm of Ag was evaporated for the top contact. The device had an area of 0.04 cm 2 . The cell structure of the bilayer cell is shown in table 5. The compound of the formula I is either the compound of example 3 or of example 4
- BHJ cell bulk heterojunction cell
- inventive compound of the formula (I) and Ceo were coevaporated.
- inventive compound of the formula (I) to C60 weight ratio was 1 : 1 .5.
- the Bphen and Ag layers were deposited as described for the bilayer cell. The layer thicknesses were 5 nm for BPhen and 1 00 nm for Ag.
- the cell structure of the BHJ cell is shown in table 6.
- the compound of the formula I is either the compound of example 3 or of example 4.
- Table 6 cell structure of the BHJ cell
- 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 380 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.
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Abstract
Description
Claims
Priority Applications (6)
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AU2011266640A AU2011266640A1 (en) | 2010-06-18 | 2011-06-17 | Use of substituted perylenes in organic solar cells |
CN2011800300369A CN102947964A (en) | 2010-06-18 | 2011-06-17 | Use of substituted perylenes in organic solar cells |
KR1020137001189A KR20130143540A (en) | 2010-06-18 | 2011-06-17 | Use of substituted perylenes in organic solar cells |
EP11795283.8A EP2583326A1 (en) | 2010-06-18 | 2011-06-17 | Use of substituted perylenes in organic solar cells |
JP2013514833A JP2013531892A (en) | 2010-06-18 | 2011-06-17 | Use of substituted perylenes in organic solar cells. |
ZA2013/00414A ZA201300414B (en) | 2010-06-18 | 2013-01-16 | Use of substituted perylenes in organic solar cells |
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Cited By (11)
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EP2680336A1 (en) * | 2012-06-25 | 2014-01-01 | Tata Steel Nederland Technology B.V. | Photoactive material having an imide based conjugated backbone |
WO2016083914A1 (en) | 2014-11-26 | 2016-06-02 | Basf Se | 4-oxoquinoline compounds |
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EP2976316A4 (en) * | 2013-03-18 | 2016-11-16 | Basf Se | Perylenemonoimide and naphthalenemonoimide derivatives and their use in dye-sensitized solar cells |
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- 2011-06-17 JP JP2013514833A patent/JP2013531892A/en not_active Withdrawn
- 2011-06-17 WO PCT/IB2011/052640 patent/WO2011158211A1/en active Application Filing
- 2011-06-17 EP EP11795283.8A patent/EP2583326A1/en not_active Withdrawn
- 2011-06-17 CN CN2011800300369A patent/CN102947964A/en active Pending
- 2011-06-17 AU AU2011266640A patent/AU2011266640A1/en not_active Abandoned
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JP2013531892A (en) | 2013-08-08 |
KR20130143540A (en) | 2013-12-31 |
AU2011266640A1 (en) | 2012-12-20 |
CN102947964A (en) | 2013-02-27 |
EP2583326A1 (en) | 2013-04-24 |
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