EP2181096A1 - Utilisation de derivés de rylène en tant que composants actifs dans des cellules solaires et des photodétecteurs - Google Patents
Utilisation de derivés de rylène en tant que composants actifs dans des cellules solaires et des photodétecteursInfo
- Publication number
- EP2181096A1 EP2181096A1 EP08775231A EP08775231A EP2181096A1 EP 2181096 A1 EP2181096 A1 EP 2181096A1 EP 08775231 A EP08775231 A EP 08775231A EP 08775231 A EP08775231 A EP 08775231A EP 2181096 A1 EP2181096 A1 EP 2181096A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- polysubstituted
- alkoxy
- radicals
- mono
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- 239000011149 active material Substances 0.000 claims abstract description 8
- -1 hydroxy, mercapto Chemical class 0.000 claims description 429
- 150000003254 radicals Chemical class 0.000 claims description 190
- 125000003118 aryl group Chemical group 0.000 claims description 79
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 72
- 125000001424 substituent group Chemical group 0.000 claims description 56
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 51
- 229910052736 halogen Inorganic materials 0.000 claims description 46
- 150000002367 halogens Chemical class 0.000 claims description 46
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
- 125000004122 cyclic group Chemical group 0.000 claims description 42
- 229920006395 saturated elastomer Polymers 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 28
- 239000000370 acceptor Substances 0.000 claims description 28
- 150000005840 aryl radicals Chemical class 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 22
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 15
- 125000005110 aryl thio group Chemical group 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 10
- 125000005936 piperidyl group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000003504 photosensitizing agent Substances 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 3
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 48
- 239000000463 material Substances 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000004065 semiconductor Substances 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 239000000975 dye Substances 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 15
- 239000007787 solid Substances 0.000 description 12
- 230000008033 biological extinction Effects 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 10
- 125000003277 amino group Chemical group 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 238000013459 approach Methods 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000004020 conductor Substances 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 238000004611 spectroscopical analysis Methods 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 6
- 238000010926 purge Methods 0.000 description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 230000005281 excited state Effects 0.000 description 5
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 239000004408 titanium dioxide Substances 0.000 description 5
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 4
- XDXWNHPWWKGTKO-UHFFFAOYSA-N 207739-72-8 Chemical compound C1=CC(OC)=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C2=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC(=CC=C1C1=CC=C(C=C13)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 XDXWNHPWWKGTKO-UHFFFAOYSA-N 0.000 description 4
- 229910010413 TiO 2 Inorganic materials 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 description 4
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical class C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000011244 liquid electrolyte Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000005486 sulfidation Methods 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical class C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
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- 206010070834 Sensitisation Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
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- 150000004984 aromatic diamines Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
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- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- PDZKZMQQDCHTNF-UHFFFAOYSA-M copper(1+);thiocyanate Chemical compound [Cu+].[S-]C#N PDZKZMQQDCHTNF-UHFFFAOYSA-M 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical group [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
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- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 2
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
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- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000001451 molecular beam epitaxy Methods 0.000 description 1
- 125000005322 morpholin-1-yl group Chemical group 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 239000002073 nanorod Substances 0.000 description 1
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- YRZZLAGRKZIJJI-UHFFFAOYSA-N oxyvanadium phthalocyanine Chemical compound [V+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 YRZZLAGRKZIJJI-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical compound C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- LBOJSACZVLWUHN-UHFFFAOYSA-N perylene-3,4-dicarboximide Chemical class C=12C3=CC=CC2=CC=CC=1C1=CC=C2C(=O)NC(=O)C4=CC=C3C1=C42 LBOJSACZVLWUHN-UHFFFAOYSA-N 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- OOBHFESNSZDWIU-UHFFFAOYSA-N phenmetrazine Chemical compound CC1NCCOC1C1=CC=CC=C1 OOBHFESNSZDWIU-UHFFFAOYSA-N 0.000 description 1
- 229960003209 phenmetrazine Drugs 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical compound O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
- HBDDRESWUAFAHY-UHFFFAOYSA-N thiomorpholin-3-one Chemical compound O=C1CSCCN1 HBDDRESWUAFAHY-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 238000007280 thionation reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- CYHOMWAPJJPNMW-JIGDXULJSA-N tropine Chemical compound C1[C@@H](O)C[C@H]2CC[C@@H]1N2C CYHOMWAPJJPNMW-JIGDXULJSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D471/06—Peri-condensed systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/008—Triarylamine dyes containing no other chromophores
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/20—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
-
- 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 the use of compounds of general formula (I)
- Y is one of the two radicals either a radical of the formula (y1)
- W is independently O or S
- a radical -U-aryl which may be mono- or polysubstituted by the abovementioned radicals which are mentioned as substituents for the aryl radicals (iii), where U is a grouping -O-, -S-, -NR 4 -, -CO-, -SO- or -SO 2 - means;
- Ci-Ci 2 -alkoxy, d-Ce-alkylthio, -C ⁇ CR 4 , -CR 4 CR 4 2 , hydroxy, mercapto, halogen, cyano, nitro, -NR 9 R 10 , -NR 5 COR 6 , -CONR 5 R 6 , -SO 2 NR 5 R 6 , -COOR 7 , -SO 3 R 7 , -PR 7 2 and / or -POR 7 R 7 ;
- P is an amino radical -NR 1 R 2 ;
- B is Ci-C ⁇ -alkylene, phenylene or combinations of these bridge members, wherein the phenylene radicals may be mono- or polysubstituted by Ci-Ci 2 alkyl, nitro, cyano and / or halogen;
- A is -COOM, -SO 3 M or -PO 3 M 2 ;
- D 1, 2-phenylene, 1, 2- or 2,3-naphthylene or 2,3- or 3,4-pyridylene, each of which mono- or polysubstituted by Ci-Ci 2 -alkyl, Ci-C 2 alkoxy, Hydroxy, nitro and / or halogen may be substituted;
- M is hydrogen, alkali metal cation or [NR 5 J 4 + ;
- L is a chemical bond or an arylene or hetarylene radical of the formulas bonded directly or via ethenylene or ethynylene to the rylene skeleton
- the (het) arylene radicals Ar may be identical or different, may contain heteroatoms as ring atoms and / or may have fused saturated or unsaturated 5- to 7-membered rings, which may also contain heteroatoms, wherein the entire ring system - or multiple times
- Phenyl, Ci-Ci 5 R 6 may be substituted 2 alkyl, Ci-Ci2 alkoxy, Ci-Ci 2 alkylthio and / or -NR;
- Z is -O- or -S-;
- R 3 is one of the substituents for the radicals R mentioned alkyl radicals (i) or (Het) aryl radicals (iii);
- R ' is hydrogen
- Radicals R mentioned radicals (i), (ii), (iii), (iv), (v) and / or aryl and / or hetaryl azo, each represented by Ci-Cio-alkyl, d-C ⁇ -alkoxy and or cyano may be substituted;
- R 4 is hydrogen or C 1 -C 6 -alkyl, where the radicals R 4 may be identical or different if they occur more than once;
- R 5 , R 6 independently of one another: hydrogen; C 1 -C 6 -alkyl whose carbon chain may be interrupted by one or more nonadjacent groups -O-, -S-, -CO-, -SO- and / or -SO 2 - and which is mono- or polysubstituted by C 1 -C 12 -alkyl Alkoxy, C 1 -C 6 -alkylthio, hydroxy, mercapto, halogen, cyano, nitro and / or -COOR 8 may be substituted; Aryl or hetaryl to which in each case further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more non-adjacent groups -O-, -S-, -CO- and / or -SO2-, fused may be substituted, wherein the entire ring system may be mono- or polysubstituted by Ci-Ci2-alkyl and / or the above
- R 7 is C 1 -C 6 -alkyl whose carbon chain may be interrupted by one or more nonadjacent groups -O-, -S-, -CO-, -SO- and / or -SO 2 - and which may be mono- or polysubstituted by C 12 -alkoxy, C 1 -C 6 -alkylthio, hydroxy, mercapto, halogen, cyano, nitro and / or -COOR 8 may be substituted;
- Aryl or hetaryl to which in each case further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more non-adjacent groups -O-, -S-, -CO- and / or -SO2-, fused may be substituted, wherein the entire ring system may be mono- or polysubstituted by Ci-Ci2-alkyl and / or the above mentioned as substituents for alkyl radicals, wherein the radicals R 7 may be identical or different, if they occur multiple times;
- R 8 is Ci-Ci ⁇ -alkyl
- Het Aryl which may be mono- or polysubstituted by C 1 -C 6 -alkyl and / or the abovementioned radicals mentioned as substituents for alkyl, C 1 -C 18 -alkoxy, C 1 -C 18 -alkylthio and / or -NR 5 R 6 ;
- n 1, 2, 3 or 4;
- the present invention relates to the use of mixtures containing as components K1) Compounds of the general formula (I) as electron donors or electron acceptors
- K2 one or more compounds which act accordingly to component K1 as electron acceptors or electron donors
- the present invention relates to the use of compounds of general formula (I) as photosensitizers in solar cells or photodetectors.
- the present invention relates to solar cells and photodetectors containing compounds of formula (I) or the aforementioned mixtures, as well as compounds of general formula (I) and the aforementioned mixtures.
- Direct conversion of solar energy into electrical energy in solar cells relies on the internal photoelectric effect of a semiconductor material, i. H. the generation of electron-hole pairs by absorption of photons and the separation of the negative and positive charge carriers at a p-n junction or a Schottky contact.
- the photovoltaic voltage thus generated can cause a photocurrent in an external circuit, through which the solar cell gives off its power.
- the semiconductor can absorb only those photons that have an energy that is greater than its band gap.
- the size of the semiconductor band gap thus determines the proportion of sunlight that can be converted into electrical energy.
- DSSCs Dye Sensitized Solar Cells
- metal oxides are inexpensive solid semiconductors (n-type semiconductors), but their absorption due to large band gaps is usually not in the visible range of the electromagnetic spectrum.
- the metal oxides must therefore be combined with a photosensitizer, which absorbs in the wavelength range of sunlight, ie at 300 to 2000 nm, and in the electronically excited state injects electrons into the conduction band of the semiconductor.
- a photosensitizer which absorbs in the wavelength range of sunlight, ie at 300 to 2000 nm
- an additionally present in the cell redox system which is reduced at the counter electrode, electrons are returned to the sensitizer and this regenerated.
- DSSCs are one of the most efficient alternative solar cell technologies to date. Efficiencies of up to 11% are currently achieved in a liquid variant of this technology (see, for example, Grätzel M. et al., J. Photochem., Photobio C, 2003, 4, 145; Chiba et al., Japanese Journal of Appl. Phys., 2006, 45, L638-L640).
- the DSSCs prepared with liquid electrolyte often suffer from a non-optimal seal, which can lead to stability problems.
- the liquid electrolyte can be replaced by a solid p-type semiconductor.
- the efficiency of the solid variant of the dye-sensitized solar cell is currently about 4.6 to 4.7% (Snaith, H., Angew Chem. Int. Ed., 2005, 44, 6413-6417).
- p-semiconductors such as CuI, CuBr • or CuSCN have heretofore been used in solid colorant solar cells. In nature, too, it is the Cu (I) enzyme plastocyanin that reduces the oxidized chlorophyll dimer in photosystem I again.
- Such p-type semiconductors can be processed by at least three different methods, namely: from solution, by electrode position or by laser deposition.
- Crystallization inhibitor In this case, various crystallization inhibitors can be used (mostly thiocyanate salts), whereby efficiencies of up to 3.75% could be achieved.
- Other research has used a ZnO-covered nanoporous TiO 2 layer in combination with CuI and 1-methyl-3-ethylimidazolium thiocyanate (MEISCN). These dye solar cells showed an efficiency of 3.8%. If TiO 2 is covered with MgO and CuI (as p-conductor) with triethylamine hydrothiocyanate (as crystallization inhibitor) is used, efficiencies of up to 4.7% can be achieved. len. CuSCN can also be used from a solution as a solid p-type semiconductor and shows an efficiency of about 2%.
- Electrochemical deposition should allow better penetration into the mesoporous pores when the p-type semiconductor can be deposited at negative potentials.
- solid dye solar cells provide efficiencies of 1.5%, although typically only about 12% of the incident light is absorbed due to a relatively thin ZnO layer.
- relatively small grains are produced by laser deposition, resulting in a very good short-circuit current Isc of about 12.2 mA / cm 2 , despite an approximately 10 micron thick Ti ⁇ 2 layer, and an efficiency of about 2.8% at a active area of about 1 cm 2 .
- Organic polymers have also been used as solid p-type semiconductors.
- examples thereof include polypyrrole, poly (3,4-ethylenedioxythiophene), carbazole-based polymers, polyaniline, poly (4-undecyl-2,2'-bithiophene), poly (3-octylthiophene), poly (triphenyl-diamine), and poly (N-vinylcarbazole).
- the efficiencies reach up to 2% in the case of poly (N-vinylcarbazole).
- An in-situ polymerized PEDOT poly (3,4-ethylenedioxythiophene
- the polymers described here are typically not used in their pure form but with additives.
- Low molecular weight organic p-type semiconductors can also be used.
- the first use of a low-molecular-weight p-type semiconductor in solid-color dye solar cells replaced the liquid electrolyte by a vapor-deposited layer of triphenylamine (TPD).
- TPD triphenylamine
- the use of the organic compound 2,2'7,7'-tetrakis (N, N-di-p-methoxyphenylamine) -9,9'-spirobifluorene (spiro-MeOTAD) in dye-sensitized solar cells was reported in 1998. It can be brought in from a solution and has a relatively high glass transition temperature, which prevents unwanted crystallization and poor contact with the dye.
- the methoxy groups adjust the oxidation potential of the Spiro-MeOTAD so that the Ru complex can be efficiently regenerated.
- IPCE maximum incident photocon to current conversion efficiency
- DSSCs based on titanium dioxide as a semiconductor material are, for.
- US-A DSSCs based on titanium dioxide as a semiconductor material
- JP-A 10-189065, 2000-243463, 2001-093589, 2000-100484 and 10-334954 describe various perylene skeleton unsubstituted perylene-3,4: 9,10-tetracarboxylic acid derivatives for use in semiconductor solar cells.
- perylenetetracarboxylic diimides which carry carboxyalkyl, carboxyaryl, carboxyarylalkyl or carboxyalkylaryl radicals on the imide nitrogen atoms and / or are imidated with p-diaminobenzene derivatives in which the nitrogen atom of the amino group is in the p position by two further phenyl radicals substituted or is part of a heteroaromatic tricyclic system
- Perylene-3,4 9,10-tetracarboxylic acid monoanhydride monoimides bearing on the imide nitrogen atom the abovementioned radicals or nonfunctionalized alkyl or aryl radicals, or semicondensates of perylene-3,4: 9,10-tetracarboxylic dianhydride with 1, 2 Diamino- benzenes or 1, 8-diaminonaphthalenes, which are converted by further reaction with primary amine in the corresponding diimides or double condensates;
- a disadvantage of the DSSCs is that the amount of light that can be used by the dye is limited by the energetic distance between the Fermi energies of the n and p conductors used. The photovoltage is also limited by this distance.
- the DSSCs must be made relatively thin (1 - 2.5 microns) and therefore do not always exploit the entire spectral range of sunlight.
- Photovoltaic elements based on a pn junction in which some or even all of the photoactive materials are organic have been known for almost 50 years (see, eg, Kearns, K, Calvin, M., J., Chem. Phys 1958, 29, 950-951). Such elements are designed in such a way that at least one of the semiconductors (n-type semiconductor and / or p-type semiconductor) absorbs a photon, with the resulting exciton being transported to the pn junction and from there one or both of the two charges - Is transported to the electrode or be.
- Organic solar cells can be composed of low molecular weight compounds (also referred to below as “low molecular weight cells”), of polymers (also referred to below as “polymer cells”), of oligomers or of combinations of some or more of these materials.
- Organic solar cells have at least one acceptor material, in which the n-charge transport (electron transport) dominates and which thus represents the organic analogue to an n-type semiconductor and at least one donor material in which the p-charge transport (hole transport) dominates and which thus the organic Represents analog to a p-type semiconductor.
- acceptor material in which the n-charge transport (electron transport) dominates and which thus represents the organic analogue to an n-type semiconductor
- donor material in which the p-charge transport (hole transport) dominates and which thus the organic Represents analog to a p-type semiconductor.
- inorganic nanoparticles can also be used as the acceptor (see, for example, Alivisatos A., Science, 2002, 2
- organic photovoltaic concepts can be arranged according to processing methods.
- the materials are typically applied in vacuum (eg, by physical vapor deposition, PVD, chemical vapor deposition, CVD, molecular beam epitaxy, or other methods or combinations of techniques) and / or solution (e.g., by spin coating, printing, or other wet chemical technologies).
- vacuum e.g., by physical vapor deposition, PVD, chemical vapor deposition, CVD, molecular beam epitaxy, or other methods or combinations of techniques
- solution e.g., by spin coating, printing, or other wet chemical technologies.
- cell types and deposition methods for example cells with low molecular weight, vacuum applied layers and polymeric, wet-chemically applied layers.
- the photoactive layer contains the acceptor and donor compound (s) as a bicontinuous phase.
- acceptor and donor compound s
- rapid charge separation occurs compared to other relaxation processes, and the resulting holes and electrons are dissipated via the corresponding electrodes.
- the electrodes and the photoactive layer are often other layers, such. Hole or electron transport layers, to increase the efficiency of such cells.
- MPP doped perylenetetracarboxylic acid N, N '-di- methyldiimide
- an exciton blocking layer (EBL) is used between the acceptor layer and the cathode. This layer should cause the excitons do not migrate to the cathode, where they would decay unused at the transition between metal and organic layers. Furthermore, these blocking layers also serve as diffusion barrier against penetration of the electrode into the photoactive material.
- EBL exciton blocking layer
- Another concept is to covalently bond the donor material and the acceptor material in a molecule.
- a cell type has hitherto shown comparatively low efficiencies (see Maggini, M., Chem. Commun., 2002, 2028 to 2029).
- Polymer cells function on the same principle as the low molecular weight cells described above. The difference is that at least one of the two absorbers (ie, acceptor material and / or donor material) is a polymer and therefore is typically processed from the solution.
- useful polymers are the derivatives of poly (p-phenylene-vinylene) (PPV), among which, depending on the substituents, find both donor materials and acceptor materials.
- PPV poly (p-phenylene-vinylene)
- a typical example of a donor material polymer is MEH-PPV (methylethylhexyl), whereas cyano-substituted PPV (CN-PPV) can act as an acceptor material. Efficiencies of such constructed polymer cells were in the range of 1%.
- the systems that have shown the best performance to date consist of P3HT (poly (3-hexylthiophene)) as the donor material and PCBM ([6,6] -phenyl C6i-butyric acid methyl ester) as the acceptor material.
- Solar cells with efficiencies up to between 4.8 and 5.0% are known.
- Low band gap polymers are also used and show improved absorption overlap with solar spectrum.
- PCBM efficiencies of about 3.2% can be achieved.
- Partial optical spacers were also used to maximize light absorption in the active layer.
- the effect on the efficiency depends on the processing (eg, the solvent used, etc.).
- new materials are used, such.
- polymers with a small band gap poly [2,6- (4,4-bis (2-ethylhexyl) -4 H -cyclopenta [2,1-b; 3,4-b ' ] -dithiphene) -ALT-4, 7- (2,1,3-benzothiadiazole)] together with C71-PCBM, which show an efficiency of up to 5.5%
- Polymers are also used as donor materials with, inter alia, perylenes or with inorganic nanorods as acceptor materials, with an efficiency of up to to 1, 7% in the latter case.
- Organic solution-processed solar cells have the advantage of enabling a variety of low-cost manufacturing processes that are suitable for high throughput.
- printing processes for the production for example ink-jet printing processes, which also enable structuring of the organic layers.
- the invention therefore an object of the invention to provide organic compounds which are characterized by advantageous application properties, in particular strong light absorption and high stability, and can be used as active materials in solar cells.
- the absorption spectrum should be as broad as possible, easily adaptable to the requirements and also include the NIR range.
- X in the general formula (I) has the meaning of a -CWWM radical
- this is a (sulfated) acid radical -CWWH or a corresponding salt of an alkali metal cation or an NH 4 + - or [NR 5 4 ] + salt with the same or different radicals R 5 .
- Suitable bridge members B are C 1 -C 6 -alkylene radicals and phenylene radicals and combinations of these radicals, eg. B. Alkylenphenylen-, Phenylenalkylen- and Alkylenphenylen- alkylene radicals.
- the phenylene radicals may be substituted one or more times by Ci-Ci2-alkyl, Ci-C ⁇ -alkoxy, hydroxy, nitro, cyano and / or halogen, but are preferably unsubstituted.
- the acid groups A are carboxyl, sulfo or phosphonic acid groups, which may also be present as free acid or in salt form.
- radicals of the formula (x3) which are selected from the radicals of the formula (x3 ' ) in the condensation of the dicarboxylic acid anhydride with an acid group-containing o-phenylenediamine, 1,8-diaminonaphthalene or else 3,4-diaminopyridine and subsequent sulfidation arise, the acid group A, which in turn may be present in salt form, bound to the aromatic ring system D.
- the ring system D is otherwise preferably unsubstituted, but may also carry Ci-Ci2-alkyl, Ci-C ⁇ -alkoxy, hydroxy, nitro and / or halogen as substituents.
- Preferred compounds of the formula (I) have a radical of the formula (x1) or the corresponding dicarboxylic acid salt in the 3,4-position.
- the compounds of general formula (I) may be unsubstituted at the other end of the molecule (both Y radicals hydrogen) or in peri-position either by a radical of formula (y1)
- the two radicals Y are here correspondingly connected to each other to form a six-membered ring.
- the bridge member L may be a chemical bond, ie the amino group of the radical (y1) or the group -ZR 3 of the radical (y2) is bonded directly to the rylene skeleton, or L may be a direct or ethenylene or ethynylene to the rylene skeleton bonded (het) arylene radical of the formulas
- the (het) arylene radicals Ar can contain heteroatoms as ring atoms and / or have annealed saturated or unsaturated 5- to 7-membered rings, which can likewise contain heteroatoms.
- the bonds to the rylene skeleton and to the functional group can both originate from the same ring or from different rings.
- the whole ring system can additionally mono- or polysubstituted by phenyl, C 1 -C 12 -alkyl, C 1 -C 12 -alkoxy, C 1 -C 12 -alkylthio and / or -NR 5 R 6 , where C 1 -C 12 -alkyl, C 1 -C 12 -alkoxy and / or -NR 5 R 6 are preferred as substituents.
- the bridge member L contains two (Het) aryl radicals Ar, these are preferably identical, but they can also be different.
- the link E preferably denotes a chemical bond or a grouping -O-, -S-, -NR 4 - or -C ⁇ C-.
- bridge members L As examples of suitable bridge members L may be mentioned:
- R is hydrogen, methyl, ethyl or phenyl.
- Very particularly preferred bridge members L are a chemical bond, 1,4-phenylene, 2,3-thienylene and 4,4'-di (2,2 ', 6,6'-tetramethyl) phenylene.
- radicals R 1 and R 2 in the amino group of the radical (y1) independently of one another may be any of the radicals (i), cycloalkyl radicals (ii) or (het) aryl radicals (iii) mentioned initially in the definition of the variable R as substituents.
- the radicals R 1 and R 2 preferably in particular denote identical phenyl radicals which are C 1 -C 6 -alkyl, C 1 -C 12 -alkoxy, C 1 -C 6 -alkylthio, -NR 5 R 6 and / or phenoxy and / or phenylthio, which may each be mono- or polysubstituted by C 1 -C 6 -alkyl, C 1 -C 2 -alkoxy, C 1 -C 6 -alkylthio, -NR 5 R 6 may be substituted as substituents.
- C 4 -C 18 -alkyl in particular branched C 4 -C 18 -alkyl, for example tert-octyl, C 1 -C -alkoxy, eg. For example, methoxy, or di (Ci-Ci8-alkyl) amino, z.
- dimethylamino substituted or unsubstituted.
- Examples of preferred unsubstituted cyclic amino radicals are piperidyl, pyrrolidyl, piperazyl, morpholinyl, thiomorpholinyl, pyrryl, dibenzopyrryl (carbazyl), dibenzo-1, 4-oxiranyl (phenoxazinyl), dibenzo-1, 4-thiazinyl (phenothiazinyl) , Dibenzo-1, 4-pyrazyl (phenazinyl) and dibenzopiperidyl, with piperidyl, pyrrolidinyl, dibenzopyrryl, dibenzo-1, 4-oxiranyl, dibenzo-1, 4-thiazinyl, dibenzo-1, 4-pyrazyl and dibenzopiperidyl being particularly preferred Phenothiazinyl, piperidyl and pyrrolidyl are very particularly preferred.
- Suitable starting materials for these cyclic amino radicals are the corresponding cyclic amines or their salts.
- suitable substituted and unsubstituted amines may be mentioned:
- Piperidine 2- or 3-methylpiperidine, 6-ethylpiperidine, 2,6- or 3,5-dimethylpiperidine, 2,2,6,6-tetramethylpiperidine, 4-benzylpiperidine, 4-phenylpiperidine, piperidin-4-ol, 2, 2,6,6-tetramethylpiperidin-4-ylamine, decahydroquinoline and decahydroisoquinoline;
- Pyrrolidine 2-methylpyrrolidine, 2,5-dimethylpyrrolidine, 2,5-diethylpyrrolidine, tropanol, pyrrolidin-3-ylamine, (2,6-dimethylphenyl) pyrrolidin-2-ylmethylamine, (2,6-diisopropylphenyl) pyrrolidine 2-ylmethylamine and dodecahydrocarbazole;
- Piperazine diketopiperazine, 1-benzylpiperazine, 1-phenethylpiperazine, 1-cyclohexylpiperazine, 1-phenylpiperazine, 1- (2,4-dimethylphenyl) piperazine, 1- (2-, 3- or 4-methoxyphenyl) -piperazine, 1- (2-, 3- or 4-ethoxyphenyl) piperazine, 1- (2-, 3- or 4-fluorophenyl) piperazine, 1- (2-, 3- or 4-chlorophenyl) piperazine, 1- ( 2-, 3- or 4-bromophenyl) -piperazine, 1-, 2- or 3-pyridin-2-ylpiperazine and 1-benzo [1,3] dioxol-4-ylmethylpiperazine; Morpholine, 2,6-dimethylmorpholine, 3,3,5,5-tetramethylmorpholine, morpholine-2- or 3-ylmethanol, 3-benzylmorpholine, 3-methyl-2-phenylmorpholine,
- R 8 ' is Ci-Ci ⁇ -alkyl
- R 1 is C 4 -C 18 -alkyl, C 1 -C 18 -alkoxy, (hetero) aryl or -NR 5 R 6
- Very particularly preferred amino groups in the radicals (y1) are the diphenylaminophenylene radicals listed above and in particular the diphenylamino radicals.
- bridge members L a chemical bond
- 1, 4-phenylene and 2,5-thienylene are particularly preferred.
- Very particularly preferred bridge member L is the chemical bond.
- the radical R 3 in the grouping -ZR 3 of the radical (y 2) may be one of the alkyl radicals (i) or (het) aryl radicals (iii) mentioned initially in the definition of the variable R.
- R 3 means :
- Ci-C3o-alkyl whose carbon chain may be interrupted by one or more non-adjacent groups -O-, -S- and / or -NR 4 - and which may be mono- or polysubstituted by: Ci-Ci2-alkoxy, hydroxy and / or aryl which may be mono- or polysubstituted by C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy; Phenyl, which may be mono- or polysubstituted by: Ci-Cis-alkyl, C1-C12 alkoxy, Ci-C ⁇ -alkylthio, -NR 5 R 6 and / or phenoxy and / or phenylthio, each one or more times may be substituted by C 1 -C 6 -alkyl, C 1 -C 2 -alkoxy, C 1 -C 6 -alkylthio and / or -NR 5 R 6 .
- R' may, in addition to hydrogen, the initially defined alkyl radicals (i), cycloalkyl radicals (ii) or (Het) aryl radicals (iii).
- R ' has the following meaning:
- C 6 -C 30 -alkyl whose carbon chain may be interrupted by one or more nonadjacent groups -O-, -S- and / or -NR 4 - and which may be monosubstituted or polysubstituted by: C 1 -C 6 -alkoxy, Ci -C ⁇ -alkylthio, -NR 9 R 10 and / or aryl, which may be monosubstituted or polysubstituted by Ci-Cis-alkyl or Ci-C ⁇ -alkoxy, wherein C ⁇ -Cso-alkyl, which in ⁇ -position by - NR 9 R 10 is substituted, especially preferred; (Het) aryl, in particular phenyl, naphthyl, pyridyl or pyrimidyl, especially phenyl, which may each be mono- or polysubstituted by: Ci-Cis-alkyl, Ci-C ⁇ -alkoxy, halogen, cyano
- R ' is a phenyl radical which is mono- or polysubstituted by C 1 -C 6 -alkyl or -NR 9 R 10 .
- radicals R 5 and R 6 have the meaning given above. Preferably, they independently of one another mean:
- C 1 -C 6 -alkyl which may be mono- or polysubstituted by C 1 -C 6 -alkoxy, hydroxyl, halogen and / or cyano;
- Aryl or hetaryl which may each be mono- or polysubstituted by Ci-C ⁇ -alkyl and / or the above, as substituents for alkyl radicals may be substituted.
- Particularly suitable substituents are the alkyl radicals and especially the amino groups -NR 9 R 10 .
- radicals R 9 and R 10 are also given at the outset. Preferably, they independently of one another mean:
- Ci-C3o-alkyl whose carbon chain by one or more non-adjacent
- Dibenzo-1, 4-oxiranyl, dibenzo-1, 4-thiazinyl, dibenzo-1, 4-pyrazyl or dibenzopiperi dylringsystem which may each be mono- or polysubstituted by Ci-C24-alkyl which may be substituted by Ci-Cis-alkoxy, Ci-Cis-alkylthio and / or -NR 5 R 6 .
- the amino groups -NR 9 R 10 are preferably di (het) arylamino groups or cyclic amino groups. Particular preference is given to diphenylamino groups in which the phenyl radicals may be unsubstituted or may have the abovementioned substituents, in particular the alkyl radicals, preferably in the p position.
- Preferred substitution patterns for the phenyl radicals R ' are ortho, ortho'-disubstitution (eg alkyl radicals with secondary carbon atom in position 1) and para substitution (eg alkyl radicals with tertiary carbon atom in position 1 and at least 5 carbon atoms or Amino groups -NR 9 R 10 ).
- R v is Cs-Cs-alkyl with secondary carbon atom in 1-position
- R v is C 4 -C 18 -alkyl or C 1 -C 8 -alkoxy; R 1 'is Ci-Ci ⁇ -alkyl;
- R 3 ' is phenyl when L' is a chemical bond
- R ' are the Diphenylaminophenylenreste.
- radicals of the formula (y4 ' ) in the starting compounds are obtained by condensation of the anhydride with optionally substituted aromatic diamines, in particular with o-phenylenediamine or 1, 8-diaminonaphthalene or else 3,4-diaminopyridine, and subsequent sulfidation into radicals of the formula (y4 ).
- the perylene and terrylene derivatives also have a disubstitution in the 1, 6 and / or 1, 7-position or 1, 6 or 9, 14-position and in the case of the quaterrylene derivatives a hexa-substitution in 1, 6, 8, 11, 16,18,19 position possible.
- the counting always begins here at the molecular end with the radicals X.
- the compounds of the formula (I) are to be deposited in vacuo, which is usually the case in the production of organic solar cells, they may also be unsubstituted in the skeleton, ie. H. both n and p in the general formula (I) are each 0.
- the starting compounds substituted in the skeleton are present in the form of mixtures of products with different degrees of substitution for the compounds of the formula (I) in which the tetra- or di- or hexasubstituted products make up the main constituent. Since the substituents are usually by nucleophilic Substitution of halogenated, in particular brominated, compounds or correspondingly halogenated precursors are introduced into the aromatic skeleton, the starting compounds to the compounds of formula (I) and thus of course the compounds of general formula (I) may contain traces of halogen, which if desired, can be removed by transition metal-catalyzed reductive or base-induced dehalogenation.
- Suitable substituents R are, in particular, the (het) aryloxy and (het) arylthio radicals defined at the outset. Particularly suitable are phenoxy, thiophenoxy, pyridyloxy, pyrimidyloxy, pyridylthio and pyrimidylthio radicals.
- the radicals R can correspond to radicals of the formula (y2).
- Preferred radicals R are phenoxy or thiophenoxy radicals which may each be monosubstituted or polysubstituted by identical or different radicals (i), (ii), (iii), (iv) and / or (v):
- C 1 -C 30 -alkyl whose carbon chain is replaced by one or more nonadjacent groups -O-, -S-, -NR 4 -, -C ⁇ C-, -CR 4 CRCR 4 - and / or -CO- and / or -SO 2 - may be interrupted and may be mono- or polysubstituted by: C 1 -C 12 alkoxy, hydroxy, halogen, cyano and / or aryl which is mono- or polysubstituted by C 1 -C 18 -alkyl or C 1 -C 4 -alkyl -C ⁇ -alkoxy may be substituted;
- the (thio) phenoxy radicals R can be unsubstituted or simply substituted in the ortho, meta or preferably para position. They can also be substituted by two, three, four or five times, all substitution patterns being conceivable.
- radicals R are ortho, ortho'-disubstituted (thio) phenoxy radicals of the formula
- the radicals R "in the two ortho positions may be the same or different, but they are preferably the same.
- the (thio) phenoxy radicals R can also be substituted in one, two or all three other ring positions by identical or different radicals R '"which are different from hydrogen.
- the (thio) phenoxy radicals R are substituted only in the ortho and ortho position or additionally in the para position.
- Z is -O- or -S-, preferably -O-; R "same or different radicals:
- C 1 -C 18 -alkyl whose carbon chain may be interrupted by one or more groups -O-, -S-, -NR 4 - and / or -CO- and which is mono- or polysubstituted by C 1 -C 12 -alkoxy, Hydroxy and / or halogen may be substituted, wherein at most one of the radicals R "in 1-position may have a tertiary carbon atom;
- aryl or hetaryl which may each be mono- or polysubstituted by Ci-Cis-alkyl, Ci-Ci2-alkoxy, hydroxy and / or halogen;
- a radical -U-aryl which may be mono- or polysubstituted by the abovementioned radicals which are mentioned as substituents for the aryl radicals (iii), where U is a grouping -O-, -S- or -NR 4 - means;
- R '" are identical or different radicals: hydrogen, one of the radicals R (i), (ii), (iii), (iv) and (v), preferably C 4 -C ⁇ -alkyl radicals, which in the 1 Position may contain a tertiary carbon atom or whose carbon chain may be interrupted one or more times by -O-, -S- and /
- Alkylthio and / or -NR 5 R 6 may be substituted; R 4 is hydrogen or Ci-Ce-alkyl.
- butyl) thiophenoxy 2,6-diisopropyl-4- (tert-butyl) thiophenoxy, 2,6-di (2-butyl) -4- (tert-butyl) thiophenoxy, 2,6-di- ( n-butyl) -4- (tert-butyl) thiophenoxy, 2,6-di (2-hexyl) -4- (tert-butyl) thiophenoxy, 2,6-di (n-hexyl) -4- ( tert-butyl) thiophenoxy, 2,6-di (2-dodecyl) -4- (tert-butyl) thiophenoxy, 2,6-di (n-dodecyl) -4- (tert-butyl) thiophenoxy, 2 , 6-dicyclohexyl-4- (tert-butyl) thiophenoxy, 2,6-dimethyl-4- (ter
- radicals P are amino radicals -NR 1 R 2 .
- the radicals P therefore correspond to radicals (y1) in which L represents a chemical bond.
- the compounds of the formula (I) may be substituted at the same time by (Het) aryloxy or thioreste R and cyclic amino groups P or either by radicals R or by radicals P. However, they are preferably substituted by radicals R.
- Carboxymethyl 2-carboxyethyl, 3-carboxypropyl, 4-carboxybutyl, 5-carboxypentyl, 6-carboxyhexyl, 8-carboxyctyl, 10-carboxydecyl, 12-carboxydodecyl and 14-carboxytetradecyl;
- Sulfomethyl 2-sulfoethyl, 3-sulfopropyl, 4-sulfobutyl, 5-sulfopentyl, 6-sulfohexyl, 8-sulfooctyl, 10-sulfodecyl, 12-sulfododecyl and 14-sulfotetradecyl;
- Carbamoyl methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, butylaminocarbonyl, pentylaminocarbonyl, hexylaminocarbonyl, heptylaminocarbonyl, octylaminocarbonyl, nonylaminocarbonyl, decylaminocarbonyl and phenylaminocarbonyl;
- Aminosulfonyl N, N-dimethylaminosulfonyl, N, N-diethylaminosulfonyl, N-methyl-N-ethylaminosulfonyl, N-methyl-N-dodecylaminosulfonyl, N-dodecylaminosulfonyl, (N, N-dimethylamino) ethylaminosulfonyl, N, N- (propoxyethyl) dodecylaminosulfonyl, N, N-diphenylaminosulfonyl, N, N- (4-tert-butylphenyl) octadecylaminosulfonyl and N, N-bis (4-chlorophenyl) aminosulfonyl;
- 2-dioxanyl 1-morpholinyl, 1-thiomorpholinyl, 2- and 3-tetrahydrofuryl, 1-, 2- and 3-pyrrolidinyl, 1-piperazyl, 1-diketopiperazyl and 1-, 2-, 3- and 4-piperidyl;
- the use of the compounds of the general formula (I) as active materials in solar cells and photodetectors includes, for example, their use, optionally with the addition of dopants, as charge transport materials in organic solar cells.
- the compounds of the formula (I) usually function as electron transport materials, but in individual cases they can also act as hole transport materials.
- a radical of formula (x1) with W ' meaning oxygen or sulfur a radical of Formula (x2) or a radical of formula (x3) and one Y corresponds to either one radical of formula (y1) or (y2) and the other Y to a hydrogen, or both Y together correspond either to a radical (y3) with W ' meaning oxygen or sulfur or a radical
- the sensitizers used are usually compounds of the formula (I) in which both X are each either a radical CWWM or together form a radical of the formula (x1) with W ' meaning oxygen or sulfur, a radical of the formula (x2) or a Corresponding to one radical of the formula (y1) or (y2) and the other Y is a hydrogen.
- Another object of the present invention is accordingly the use of mixtures containing as components
- component K2 one or more compounds corresponding to component K1 correspondingly acting as electron acceptors or electron donors,
- Preferred use according to the invention are mixtures which are characterized in that component K1 is present in a proportion of 30 to 70% by mass and component K2 in a proportion of 70 to 30% by mass, the proportions of components K1 and K2, in each case based on the total mass of components K1 and K2, to 100% by mass.
- Particularly preferred uses are mixtures, which are characterized in that component K1 is present in a proportion of 40 to 60% by mass and component K2 in a proportion of 60 to 40% by mass, the proportions of components K1 and K2 , in each case based on the total mass of the components K1 and K2, in turn add to 100% by mass.
- Organic solar cells are usually layered and usually comprise at least the following layers: electrode, photoactive layer and counter electrode. These layers are usually on a conventional substrate. Suitable substrates are for. For example, oxidic materials such as glass, quartz, ceramic, SiÜ2, etc., polymers such as polyvinyl chloride, polyolefins, z. Polyethylene and polypropylene, polyesters, fluoropolymers, polyamides, polyurethanes, polyalkyl (meth) acrylates, polystyrene, and mixtures and composites thereof, and combinations of the aforementioned substrates.
- oxidic materials such as glass, quartz, ceramic, SiÜ2, etc.
- polymers such as polyvinyl chloride, polyolefins, z. Polyethylene and polypropylene, polyesters, fluoropolymers, polyamides, polyurethanes, polyalkyl (meth) acrylates, polystyrene, and mixtures and composites thereof, and combinations of the aforementioned substrate
- Suitable materials for the one electrode are in particular metals, such as.
- the alkali metals Li, Na, K, Rb and Cs the alkaline earth metals Mg, Ca and Ba, Pt, Au, Ag, Cu, Al, In, metal alloys, eg. Based on Pt, Au, Ag, Cu, etc. and special Mg / Ag Alloys, but also alkali metal fluorides, such as LiF, NaF, KF, RbF and CsF, and mixtures of alkali metal fluorides and alkali metals.
- the electrode used is preferably a material that essentially reflects the incident light. These include, for example, metal films of Al, Ag, Au, In, Mg, Mg / Al, Ca, etc.
- the counter electrode consists of a material substantially transparent to incident light, e.g. As ITO, doped ITO, FTO, ZnO, TiO 2 , Cu, Ag, Au and Pt, the latter metals are present in correspondingly thin layers.
- an electrode / counterelectrode should be regarded as "transparent” if at least 50% of the radiation intensity is transmitted in the wavelength range in which the photoactive layer absorbs radiation. In the case of several photoactive layers, an electrode / counterelectrode should be considered “transparent” if at least 50% of the radiation intensity is transmitted in the wavelength ranges in which the photoactive layers absorb radiation.
- the component K1 can take over the role of the electron donor, and accordingly the component K2 assumes the role of the electron acceptor. Alternatively, however, component K1 can also assume the role of the electron acceptor, and component K2 accordingly functions as an electron donor.
- the way in which the respective component acts depends on the energy of the HOMO or LUMO of the component K1 in relation to the energy of the HOMO or LUMO of the component K2.
- the compounds of component K1 usually appear as electron acceptors. In particular, this is to be expected if, as component K2, merocyanines of the construction D-A are used, as described in the earlier European patent application 07 1 12 153.7, and in which D stands for a donor unit and A stands for an acceptor unit in the molecule.
- component K2 can also obey the structural definition of component K1 so that a compound of general formula (I) can take on the role of the electron donor and another compound of general formula (I) the role of the electron acceptor.
- component K2 for example, the phthalocyanines already described above, z. Zn or vanadyl phthalocyanine, or polymers, such as. Poly (3-hexylthiophene) (“P3HT”), poly (2-methoxy-5- (3,7-dimethyloctyloxy) -1, 4-phenylenevinylene) ("OC1C10-PPV”).
- P3HT Poly (3-hexylthiophene)
- O1C10-PPV 4-phenylenevinylene
- the compounds of the formula (I) as component K1 usually also act as electron acceptors.
- one or more further layers may be present in the organic solar cells and photodetectors of the invention, e.g.
- ETL electron transporting layers
- HTL hole transporting layers
- blocking layers for example, exciton-blocking layers
- EBL exciton blocking layers
- the ETL and HTL may also be doped to yield pin-type cells, as described, for example, in the publication by J. Drechsel et al., Thin Solid Films 451-452 (2004), 515-517 are.
- Photodetectors essentially have a construction analogous to organic solar cells, but they are operated with a suitable bias voltage which, when exposed to radiation energy, generates a corresponding current flow as a measurement response.
- the processing of the photoactive layers takes place, for example, from solution.
- the components K1 and K2 can already be solved together, but also separately as a solution of the component K1 and solution of the component K2, the mixing of the corresponding solutions takes place in the latter case shortly before application to the underlying layer.
- the concentrations of components K1 and K2 are typically about a few g / l to tens of g / l of solvent.
- Suitable solvents are all liquids which evaporate without residue and have sufficient solubility for the components K1 and K2.
- suitable compounds are aromatic compounds such as benzene, toluene, xylene, mesitylene, chlorobenzene or dichlorobenzene, trialkylamines, nitrogen-containing heterocycles, N, N-disubstituted aliphatic carboxylic acid amides such as dimethylformamide, diethylformamide, dimethylacetamide or dimethylbutyramide, N -Alkyllactams, such as N-methylpyrrolidone, linear and cyclic ketones, such as methyl ethyl ketone, cyclopentanone or cyclohexanone, cyclic ethers, such as tetrahydrofuran, or alcohols, such as methanol, ethanol, propanol, isopropanol or butanol.
- Deweiteren can also find mixtures of the aforementioned solvents use.
- Suitable methods for applying the photoactive layers of the invention of the liquid phase are known in the art.
- the processing by means of spin coating is advantageous, since the thickness of the photoactive layer can be controlled in a simple manner by the amount and / or concentration of the solution used and the rotational speed and / or rotation time.
- the processing of the solution is usually carried out at room temperature.
- Another object of the present invention is the use of compounds of general formula (I) and their preferred embodiments as photosensitizers in solar cells or photodetectors.
- the present invention further relates to solar cells and photodetectors containing compounds of the general formula (I) and their preferred embodiments or mixtures comprising the abovementioned components K1 and K2.
- Another object of the present invention are compounds of general formula (I) and their preferred embodiments mentioned above within the scope of their use according to the invention.
- Y one of the two radicals is a radical of the formula (y1) or (y2) and the other radical is hydrogen or with one another to form a six-membered ring to form a radical of the formula (y3);
- Phenoxy or thiophenoxy which may each be monosubstituted or polysubstituted by identical or different radicals (i), (ii), (iii), (iv) and / or (v):
- a radical -U-aryl which may be mono- or polysubstituted by the abovementioned radicals which are mentioned as substituents for the aryl radicals (iii), where U is a grouping -O-, -S-, -NR 4 -, -CO-, -SO- or -SO 2 - means;
- Ci-C 2 alkoxy, Ci-C 6 alkylthio, -C ⁇ CR 4, -CR 4 CR 4 2, hydroxy, mercapto, halogen, cyano, nitro, -NR 9 R 10, -NR 5 COR 6 , -CONR 5 R 6 , -SO 2 NR 5 R 6 , -COOR 7 and / or -SO 3 R 7 ;
- M is hydrogen, alkali metal cation or [NR 5 J 4 + ;
- L is a chemical bond or phenylene
- R 1 , R 2 are identical or different phenyl radicals, which may each be mono- or polysubstituted by C 1 -C 6 -alkyl, C 1 -C 2 -alkoxy, C 1 -C 6 -alkyl-thio, -NR 5 R 6 and / or Phenoxy and / or phenylthio, each one or more times by
- C 1 -C 18 -alkyl, C 1 -C 12 -alkoxy, C 1 -C 6 -alkylthio and / or -NR 5 R 6 may be substituted; with the nitrogen atom to give a piperidyl, pyrrolidinyl, dibenzopyrryl, dibenzo-1, 4-oxiranyl, dibenzo-1, 4-thiazinyl, dibenzo-1, 4-pyrazyl or dibenzopiperidyl ring system, each of which has a or polysubstituted by: C 1 -C 4 -alkyl which may be substituted by C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio and / or -NR 5 R 6 , (Het) aryl, which may be mono- or polysubstituted C 1 -C 6 -alkyl and / or the abovementioned radicals which are mentioned as substituents for alkyl, C 1 -C
- Z is -O- or -S-;
- Phenyl which may be mono- or polysubstituted by: Ci-Cis-alkyl, d-Ci2-alkoxy, Ci-C 6 -alkylthio, -NR 5 R 6 and / or phenoxy and / or phenylthio, each one or multiple R 6 may be substituted by Ci-cis-alkyl, Ci-Ci2-alkoxy, Ci-C ⁇ alkylthio and / or NR 5;
- R 'C ⁇ -Cso-alkyl whose carbon chain may be interrupted by one or more non-adjacent groupings -O-, -S- and / or -NR 4 - and which may be mono- or polysubstituted by: Ci-C ⁇ -alkoxy , C 1 -C 6 -alkylthio, -NR 9 R 10 and / or aryl which may be mono- or polysubstituted by C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy;
- Phenyl, naphthyl, pyridyl or pyrimidyl which may each be monosubstituted or polysubstituted by: C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, halogen, cyano, nitro, -NR 9 R 10 , -CONR 5 R 6 , - SO 2 NR 5 R 6 and / or phenoxy, phenylthio, phenylazo and / or naphthylazo, each of which may be substituted by Ci-Cio-alkyl, Ci-C ⁇ -alkoxy and / or cyano;
- R 4 is hydrogen or C 1 -C 6 -alkyl
- R 5 , R 6 independently of one another: hydrogen
- C 1 -C 6 -alkyl which may be mono- or polysubstituted by C 1 -C 6 -alkoxy, hydroxyl, halogen and / or cyano;
- Aryl or hetaryl which may each be monosubstituted or polysubstituted by C 1 -C 6 -alkyl and / or the abovementioned radicals mentioned as substituents for alkyl, it being possible for the radicals R 5 to be identical or different if they occur more than once;
- R 7 is C 1 -C 6 -alkyl which may be mono- or polysubstituted by C 1 -C 6 -alkoxy, hydroxyl, halogen and / or cyano; Aryl or hetaryl, which may each be mono- or polysubstituted by Ci-C ⁇ -alkyl and / or the above, as substituents for alkyl radicals may be substituted
- Another object of the present invention are mixtures containing as components
- component K2 one or more compounds corresponding to component K1 accordingly act as electron acceptors or electron donors.
- mixtures according to the invention find use in the form of a bicontinuous phase ("bulk heterojunction") in photoactive layers of organic solar cells.
- a bicontinuous phase (bulk heterojunction) in photoactive layers of organic solar cells.
- the starting compound showed an absorbance maximum at 567 nm.
- the degree of sufing increases, the wavelength of the extinction maximum increases, and the degree of sulfation therefore allows the absorption behavior of the compounds of the formula (I) to be adapted precisely to the respective requirements.
- UV-Vis (CHCl 3 ): 676 nm
- the wavelength of the extinction peak also increases significantly.
- UV-Vis (CHCl 3 ): 780 nm
- the wavelength of the extinction peak also increases significantly.
- UV-Vis (CH 2 Cl 2 ): 608 nm
- UV-Vis (CH 2 Cl 2 ): 588 nm
- UV-Vis (CH 2 Cl 2 ): 578 nm
- UV-Vis (CH 2 Cl 2 ): 568 nm
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Abstract
L'invention concerne des composés de forme générale (I) et leur utilisation en tant que matériaux actifs dans des cellules solaires et des photodétecteurs. Les variables figurant dans la formule (I) sont définies dans la description. La formule (I) comprend entre autres l'exemple suivant.
Priority Applications (1)
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EP08775231A EP2181096A1 (fr) | 2007-07-23 | 2008-07-21 | Utilisation de derivés de rylène en tant que composants actifs dans des cellules solaires et des photodétecteurs |
Applications Claiming Priority (3)
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EP07112969 | 2007-07-23 | ||
PCT/EP2008/059502 WO2009013258A1 (fr) | 2007-07-23 | 2008-07-21 | Utilisation de derivés de rylène en tant que composants actifs dans des cellules solaires et des photodétecteurs |
EP08775231A EP2181096A1 (fr) | 2007-07-23 | 2008-07-21 | Utilisation de derivés de rylène en tant que composants actifs dans des cellules solaires et des photodétecteurs |
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EP08775231A Withdrawn EP2181096A1 (fr) | 2007-07-23 | 2008-07-21 | Utilisation de derivés de rylène en tant que composants actifs dans des cellules solaires et des photodétecteurs |
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US (1) | US8083971B2 (fr) |
EP (1) | EP2181096A1 (fr) |
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EP2519523A1 (fr) * | 2009-12-29 | 2012-11-07 | Polyera Corporation | Bisimides aromatiques thionés en tant que semi-conducteurs organiques et dispositifs incorporant ceux-ci |
US9246106B2 (en) | 2011-04-05 | 2016-01-26 | The Board Of Trustees Of The Leland Stanford Junior University | Electron deficient molecules and their use in organic electronic applications |
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US4254108A (en) * | 1979-11-08 | 1981-03-03 | Ayerst, Mckenna & Harrison Inc. | Thioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid derivatives and antidiabetic use thereof |
CH674596A5 (fr) * | 1988-02-12 | 1990-06-15 | Sulzer Ag | |
ATE131953T1 (de) * | 1990-04-17 | 1996-01-15 | Ecole Polytech | Photovoltaische zellen |
JP2938149B2 (ja) | 1990-06-12 | 1999-08-23 | 三田工業株式会社 | アゾ系化合物およびそれを用いた電子写真感光体 |
DE59407520D1 (de) * | 1993-08-13 | 1999-02-04 | Ciba Geigy Ag | Perylenamidinimid-Farbstoffe, ein Verfahren zu deren Herstellung und deren Verwendung |
JP3968809B2 (ja) | 1996-12-19 | 2007-08-29 | 富士ゼロックス株式会社 | 湿式太陽電池用光半導体電極、湿式太陽電池及び光電変換方法 |
JP3968819B2 (ja) | 1997-06-02 | 2007-08-29 | 富士ゼロックス株式会社 | 湿式太陽電池用光半導体電極、湿式太陽電池及び光電変換方法 |
JP2000100484A (ja) | 1998-09-24 | 2000-04-07 | Fuji Xerox Co Ltd | 光半導体電極、光電変換装置及び光電変換方法 |
JP4211120B2 (ja) | 1999-02-19 | 2009-01-21 | 富士ゼロックス株式会社 | 光半導体電極、光電変換装置及び光電変換方法 |
US6359211B1 (en) * | 1999-06-17 | 2002-03-19 | Chemmotif, Inc. | Spectral sensitization of nanocrystalline solar cells |
EP1176646A1 (fr) | 2000-07-28 | 2002-01-30 | Ecole Polytechnique Féderale de Lausanne (EPFL) | Hétérojonction à l'état solide et cellule photovoltaique sensibilisé à l'état solide |
DE102004014046B4 (de) | 2003-03-19 | 2013-04-25 | Heliatek Gmbh | Photoaktives Bauelement mit organischen Schichten |
US7592539B2 (en) * | 2003-11-07 | 2009-09-22 | The Trustees Of Princeton University | Solid state photosensitive devices which employ isolated photosynthetic complexes |
US20050224905A1 (en) * | 2004-04-13 | 2005-10-13 | Forrest Stephen R | High efficiency organic photovoltaic cells employing hybridized mixed-planar heterojunctions |
DE102005021362A1 (de) | 2005-05-04 | 2006-11-09 | Basf Ag | Terrylen- und Quaterrylenderivate |
DE102005032583A1 (de) | 2005-07-11 | 2007-01-25 | Basf Ag | Substituierte Rylenderivate |
DE102005053995A1 (de) * | 2005-11-10 | 2007-05-24 | Basf Ag | Verwendung von Rylenderivaten als Photosensibilisatoren in Solarzellen |
CN101573414B (zh) * | 2006-11-02 | 2014-01-15 | 巴斯夫欧洲公司 | 五并苯四羧酸二酰亚胺和六并苯四羧酸二酰亚胺以及它们的制备方法 |
WO2008052927A1 (fr) * | 2006-11-02 | 2008-05-08 | Basf Se | Diimides d'acide heptarylène-tétracarboxylique et d'acide octarylène-tétracarboxylique et leur production |
-
2008
- 2008-07-21 US US12/668,975 patent/US8083971B2/en not_active Expired - Fee Related
- 2008-07-21 WO PCT/EP2008/059502 patent/WO2009013258A1/fr active Application Filing
- 2008-07-21 EP EP08775231A patent/EP2181096A1/fr not_active Withdrawn
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WO2009013258A1 (fr) | 2009-01-29 |
US20100207072A1 (en) | 2010-08-19 |
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