WO2014037847A2 - Nouveaux composés spiro et leur utilisation dans des applications et dispositifs électroniques organiques - Google Patents
Nouveaux composés spiro et leur utilisation dans des applications et dispositifs électroniques organiques Download PDFInfo
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- WO2014037847A2 WO2014037847A2 PCT/IB2013/058018 IB2013058018W WO2014037847A2 WO 2014037847 A2 WO2014037847 A2 WO 2014037847A2 IB 2013058018 W IB2013058018 W IB 2013058018W WO 2014037847 A2 WO2014037847 A2 WO 2014037847A2
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- 150000003413 spiro compounds Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 125000003118 aryl group Chemical group 0.000 claims abstract description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 21
- 230000005669 field effect Effects 0.000 claims abstract description 9
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical class C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
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- 239000000203 mixture Substances 0.000 description 25
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
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- 101100457453 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) MNL1 gene Proteins 0.000 description 6
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 5
- MASXXNUEJVMYML-UHFFFAOYSA-N 2,2',7,7'-tetrabromo-9,9'-spirobi[fluorene] Chemical compound C12=CC(Br)=CC=C2C2=CC=C(Br)C=C2C11C2=CC(Br)=CC=C2C2=CC=C(Br)C=C21 MASXXNUEJVMYML-UHFFFAOYSA-N 0.000 description 4
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
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- SPXOTSHWBDUUMT-UHFFFAOYSA-M 4-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-M 0.000 description 3
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
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- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 102100034033 Alpha-adducin Human genes 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RSMQZCBRDKTDEH-UHFFFAOYSA-N Cc(cc(cc1)Nc(cc2)ccc2OC)c1OC Chemical compound Cc(cc(cc1)Nc(cc2)ccc2OC)c1OC RSMQZCBRDKTDEH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 101000799076 Homo sapiens Alpha-adducin Proteins 0.000 description 1
- 241000409201 Luina Species 0.000 description 1
- RYAHYXHXCGXUOK-UHFFFAOYSA-N N-ethenylbutan-2-imine Chemical group CCC(C)=NC=C RYAHYXHXCGXUOK-UHFFFAOYSA-N 0.000 description 1
- 101100513046 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) eth-1 gene Proteins 0.000 description 1
- 229920000280 Poly(3-octylthiophene) Polymers 0.000 description 1
- 101000629598 Rattus norvegicus Sterol regulatory element-binding protein 1 Proteins 0.000 description 1
- 239000012327 Ruthenium complex Substances 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910010165 TiCu Inorganic materials 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- PDZKZMQQDCHTNF-UHFFFAOYSA-M copper(1+);thiocyanate Chemical compound [Cu+].[S-]C#N PDZKZMQQDCHTNF-UHFFFAOYSA-M 0.000 description 1
- IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000006342 heptafluoro i-propyl group Chemical group FC(F)(F)C(F)(*)C(F)(F)F 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000005368 heteroarylthio group Chemical group 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000011244 liquid electrolyte Substances 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- JIQNWFBLYKVZFY-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=C[C]=CC=C1 JIQNWFBLYKVZFY-UHFFFAOYSA-N 0.000 description 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- HAGWGWQUZPWZER-UHFFFAOYSA-N n-prop-1-enylbutan-2-imine Chemical group CCC(C)=NC=CC HAGWGWQUZPWZER-UHFFFAOYSA-N 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 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
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 229920000620 organic polymer Polymers 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
- 230000035515 penetration Effects 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 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
- 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
- 239000010453 quartz Substances 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000007789 sealing Methods 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
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- CMJDSHGPZPMYQN-UHFFFAOYSA-N sodium;2-(4-butoxyphenyl)-n-oxidoacetamide Chemical compound [Na+].CCCCOC1=CC=C(CC(=O)N[O-])C=C1 CMJDSHGPZPMYQN-UHFFFAOYSA-N 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005118 spray pyrolysis Methods 0.000 description 1
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical compound F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 description 1
- 229960002799 stannous fluoride Drugs 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/92—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
-
- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/94—Spiro compounds containing "free" spiro atoms
-
- 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
- Y02E10/542—Dye sensitized solar cells
-
- 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
- variables R 11 , R 12 , R 21 , R 22 , R 31 , R 32 , R 41 and R 42 independently of each other have the meaning of aryl or hetaryl, with the proviso that not all of the radicals R 11 , R 12 , R 21 , R 22 , R 31 , R 32 , R 41 and R 42 are identical, to the use of compounds of general formula I in organic electronics applications, especially in organic field effect transistors, in organic photodetectors and organic solar cells, specifically in dye-sensitized solar cells and bulk heterojunction solar cells, and to an organic field effect transistor, a dye-sensitized solar cell and a bulk heterojunction solar cell comprising compounds of general formula I.
- DSCs Dye-sensitized solar cells
- the construction of a DSC is generally based on a glass substrate, which is coated with a transparent conductive layer, the working electrode.
- An n-conductive metal oxide is generally applied to this electrode or in the vicinity thereof, for example an approx. 2-20 ⁇ -thick nanoporous titanium dioxide layer (T1O2).
- T1O2 ⁇ -thick nanoporous titanium dioxide layer
- a monolayer of a light- sensitive dye for example a ruthenium complex
- the counterelectrode may optionally have a catalytic layer of a metal, for example platinum, with a thickness of a few ⁇ .
- the area between the two electrodes is filled with a redox electrolyte, for example a solution of iodine ( ) and lithium iodide (Lil).
- the function of the DSC is based on the fact that light is absorbed by the dye, and electrons are transferred from the excited dye to the n-semiconductive metal oxide semiconductor and migrate thereon to the anode, whereas the electrolyte ensures that the charges are balanced via the cathode.
- the n-semiconductive metal oxide, the dye and the (usually liquid) electrolyte are thus the most important constituents of the DSC, though cells comprising liquid electrolyte in many cases suffer from nonoptimal sealing, which leads to stability problems.
- Various materials have therefore been studied for their suitability as solid electrolytes/p-semiconductors.
- Solid DSCs comprising fluorine and tin difluoride doped CsSn as hole conducting material and displaying efficiencies of around 10% were reported by In Chung et al. (Nature Vol. 485, May 24, 2012, 486-490)
- Organic polymers are also used as solid p-semiconductors.
- examples thereof include polypyrrole, poly(3,4-ethylenedioxythiophene), carbazole-based polymers, polyaniline, poly(4- undecyl-2,2'-bithiophene), poly(3-octylthiophene), poly(triphenyldiamine) and poly(N- vinylcarbazole).
- poly(N-vinylcarbazole) the efficiencies reach up to 2%; with a PEDOT (poly(3,4-ethylenedioxythiophene), polymerized in situ, an efficiency of 2.9% was even achieved (Xia et al. J. Phys. Chem.
- WO 98/48433 A1 reports the use of the organic compound 2,2',7,7'-tetrakis(N,N-di-p- methoxyphenyl-amine)-9,9'-spirobifluorene ("spiro-MeOTAD") in DSCs as hole transporting material.
- spiro-MeOTAD 2,2',7,7'-tetrakis(N,N-di-p- methoxyphenyl-amine)-9,9'-spirobifluorene
- Spiro-MeOTAD is likewise examined by Snaith, H. J.; Moule, A. J.; Klein, C; Meerholz, K.; Friend, R. H.; Gratzel (M. Nano Lett.; (Letter); 2007; 7(1 1 ); 3372-3376) as hole transporting material in DSCs.
- solubility in customary process solvents is relatively low, which leads to a correspondingly low degree of pore filling.
- photocurrent is directly dependent on the yield in the hole transition from the oxidized dye to the solid p-conductor. This depends essentially on two factors: first on the degree of penetration of the p-semiconductor into the oxide pores, and second on the thermodynamic driving force for the charge transfer, i.e. especially on the difference in the free enthalpy ⁇ between dye and p- conductor.
- the photoactive layer comprises the acceptor and donor compound(s) as a bicontinuous phase.
- the acceptor compound As a result of photoinduced charge transfer from the excited state of the donor compound to the acceptor compound, owing to the spatial proximity of the compounds, a rapid charge separation compared to other relaxation procedures takes place, and the holes and electrons which arise are removed via the corresponding electrodes.
- further layers for example hole or electron transport layers, are often applied in order to increase the efficiency of such cells.
- the donor materials used in such BHJ cells have usually been polymers, for example polyvinylphenylenes or polythiophenes, or dyes from the class of the phthalocyanines, e.g. zinc phthalocyanine or vanadyl phthalocyanine, and the acceptor materials used have been fullerene and fullerene derivatives and also various perylenes.
- Photoactive layers composed of the donor/acceptor pairs poly(3-hexyl-thiophene) (“P3HT”)/ [6,6]-phenyl-C6i-butyric acid methyl ester (“PCBM”), poly(2-methoxy-5-(3,7-dimethyloctyloxy)-1 ,4-phenylenevinylene) (“OC1C10- PPV”)/PCBM and zinc phthalocyanine/fullerene have been and are being researched intensively.
- P3HT poly(3-hexyl-thiophene)
- PCBM poly(2-methoxy-5-(3,7-dimethyloctyloxy)-1 ,4-phenylenevinylene)
- OC1C10- PPV poly(2-methoxy-5-(3,7-dimethyloctyloxy)-1 ,4-phenylenevinylene)
- PCBM poly(2-methoxy-5-(3,7-dimethyloctyloxy)-1
- R 11 , R 12 , R 21 , R 22 , R 31 , R 32 , R 41 and R 42 independently of each other have the meaning of aryl or hetaryl, with the proviso that not all of the radicals R 11 , R 12 , R 21 , R 22 , R 31 , R 32 , R 41 and R 42 are identical.
- X C(R 8 R 9 ) 2 NR 10 , oxygen or sulfur, and R 6 to R 10 hydrogen, alkyl, cycloalkyl, aryl or hetaryl.
- Lg leaving group In general, the leaving group Lg can be any group known to a person skilled in the art as being prone to easily leave the molecule. Typically, Lg consists of or comprises strongly electron- withdrawing atoms or moieties and, thus, is normally split off as anionic species.
- Lg are chlorine, bromine, iodine, brosylate, nosylate, tosylate, mesylate and triflate which, in view of the aforesaid, leave the molecule as chloride, bromide, iodide, brosylate, nosylate, tosylate, mesylate or triflate anion.
- brosylate nosylate and tosylate are, in respective order, as follows:
- R 5 hydrogen, alkyl, aryl, alkoxy, alkylthio or -NR 6 R 7 , where in case of two or more substituents (p equal or greater than 2) these may be identical or different, p 0, 1 , 2, 3, 4 or 5,
- R 6 to R 10 hydrogen, alkyl, cycloalkyl, aryl or hetaryl.
- the Buchwald-Hartwig amination reaction is a well established synthetic route and the reaction conditions can easily be determined by a person skilled in the art. Conversion of aryl bromides to arylamines is specifically addressed in the publication by Guram, A.S.; Rennels, R.A.; Buchwald, S.L. (1995), "A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines", Angewandte Chemie International Edition 34 (12): 1348-1350.
- the abovementioned compounds of general formula I and II and their preferred embodiments are particularly suited for organic electronics applications, especially in organic field effect transistors, dye-sensitized solar cells and bulk heterojunction solar cells with generally low tendency of crystallization and thus enhanced long term stability of the resulting organic electronic devices.
- these compounds typically function as hole transporting materials.
- Another objective of the instant invention is the use of compounds of general formula I and their preferred embodiments in organic electronics applications. Specifically, the
- Another preffered objective of the instant invention is the use of compounds of general formula I and their preferred embodiments in dye-sensitized solar cells and bulk heterojunction solar cells. Further objectives of the instant invention pertain to field effect transistor, dye-sensitized solar cells and bulk heterojunction solar cells comprising compounds of general formula I and their preferred embodiments.
- alkyl, aryl or heteroaryl represents unsubstituted or substituted alkyl, unsubstituted or substituted aryl or unsubstituted or substituted heteroaryl.
- Alkyl comprises straight-chain or branched alkyl.
- Alkyl is preferably Ci-C3o-alkyl, especially Ci- C2o-alkyl and most preferably Ci-Ci2-alkyl.
- alkyl groups are especially methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n- octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-hexadecyl, n-octadecyl and n-eicosyl.
- branched alkyl groups can be represented by the following formula in which
- R a is selected from Ci- to C28-alkyl, where the sum of the carbon atoms of the Rs
- R a radicals is an integer from 2 to 29.
- the R a radicals are preferably selected from Ci- to Ci2-alkyl, especially Ci- to Cs-alkyl.
- Preferred branched alkyl radicals of the above formula are, for example:
- AlkyI also comprises alkyl radicals whose carbon chains may be interrupted by one or more nonadjacent groups selected from oxygen, sulfur, -CO-, -NR b -, -SO- and/or
- R b is preferably hydrogen, unsubstituted straight-chain or branched alkyl as described before or unsubstituted aryl as described below.
- Substituted alkyl groups may, depending on the length of the alkyl chain, have one or more (e.g. 1 , 2, 3, 4, 5 or more than 5) substituents. These are preferably each independently selected from cycloalkyl, heterocycloalkyl, aryl, hetaryl, fluorine, chlorine, bromine, cyano and nitro.
- Aryl-substituted alkyl radicals have at least one unsubstituted or substituted aryl group, as defined below.
- the alkyl group of the aralkyi radical may bear at least one further substituent and/or be interrupted by one or more nonadjacent groups selected from oxygen, sulfur, -CO-, - NR b -, -SO- and/or -SO2- where R b is preferably hydrogen, unsubstituted straight-chain or branched alkyl as described before or unsubstituted aryl as described below.
- Arylalkyl is preferably phenyl-Ci-Cio-alkyl, more preferably phenyl-Ci-C4-alkyl, for example benzyl,
- Halogen-substituted alkyl groups comprise a straight-chain or branched alkyl group in which at least one hydrogen atom or all hydrogen atoms are replaced by halogen.
- the halogen atoms are preferably selected from fluorine, chlorine and bromine, especially fluorine and chlorine.
- haloalkyl groups are especially chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2- difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl,
- unsubstituted and substituted alkyl radicals which may be interrupted by one or more nonadjacent groups selected from oxygen, sulfur, -NR b -, -CO-, -SO- and/or -
- dicyclopentylamino dicyclohexylamino, dicycloheptylamino, diphenylamino and dibenzylamino; formylamino, acetylamino, propionylamino and benzoylamino; carbamoyl, methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, butyl- aminocarbonyl, pentylaminocarbonyl, hexylaminocarbonyl, heptylaminocarbonyl,
- octylaminocarbonyl nonylaminocarbonyl, decylaminocarbonyl and phenylamino-carbonyl; aminosulfonyl, n-dodecylaminosulfonyl, ⁇ , ⁇ -diphenylaminosulfonyl, and
- N,N-bis(4-chlorophenyl)aminosulfonyl methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl hexoxycarbonyl, dodecyloxycarbonyl, octadecyloxycarbonyl, phenoxycarbonyl, (4-tert-butylphenoxy)carbonyl and
- 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.
- cycloalkyi groups preferably bear one or more, for example one, two, three, four or five, Ci-C6-alkyl groups.
- substituted cycloalkyi groups are especially 2- and 3-methylcyclopentyl, 2- and 3-ethylcyclopentyl, 2-, 3- and 4-methylcyclohexyl, 2-, 3- and 4-ethylcyclohexyl, 2-, 3- and 4-propylcyclohexyl, 2-, 3- and 4-isopropylcyclohexyl, 2-, 3- and 4-butylcyclohexyl, 2-, 3- and 4-sec.
- substituted and unsubstituted cycloalkyi groups are cyclopropyl, cyclobutyl, cyclopentyl, 2- and 3-methylcyclopentyl, 2- and 3-ethylcyclo-pentyl, cyclohexyl, 2-, 3- and 4-methylcyclohexyl, 2-, 3- and 4-ethylcyclohexyl, 3- and 4-propylcyclohexyl, 3- and 4- isopropylcyclohexyl, 3- and 4-butylcyclohexyl, 3- and 4-sec-butylcyclohexyl, 3- and 4-tert- butylcyclohexyl, cycloheptyl, 2-, 3- and 4-methyl-cycloheptyl, 2-, 3- and 4-ethylcycloheptyl, 3- and 4-propylcycloheptyl, 3- and 4-iso-propylcycloheptyl, 3- and 4-butylcycloheptyl,
- aryl comprises mono- or polycyclic aromatic hydrocarbon radicals and monocyclic aromatic hydrocarbon radicals which may be fused to one or more unfused or fused saturated or unsaturated carbocyclic or heterocyclic five or six membered rings.
- Aryl has preferably 6 to 14, more preferably 6 to 10, carbon atoms. Examples of aryl are especially phenyl, naphthyl, indenyl, fluorenyl, anthracenyl, phenanthrenyl, naphthacenyl, chrysenyl and pyrenyl, especially phenyl, naphthyl and fluorenyl.
- 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, cycloalkyi, heterocycloalkyl, aryl, hetaryl, fluorine, chlorine, bromine, cyano and nitro.
- the alkyl, alkoxy, alkylamino, alkylthio, cycloalkyi, heterocycloalkyl, aryl and hetaryl substituents on the aryl may in turn be unsubstituted or substituted.
- 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 alkyi 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) alkyi substituents.
- alkyi substituents may be unsubstituted or substituted.
- the alkaryl groups have exclusively unsubstituted alkyi substituents.
- Alkaryl is preferably phenyl which bears 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, more preferably 1 or 2, alkyi substituents.
- Aryl which bears one or more radicals is, for example, 2-, 3- and 4-methylphenyl, 2,4-, 2,5-, 3,5- and 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 2-, 3- and 4-ethylphenyl, 2,4-, 2,5-, 3,5- and 2,6- diethylphenyl, 2,4,6-triethylphenyl, 2-, 3- and 4-propylphenyl, 2,4-, 2,5-, 3,5- and 2,6- dipropylphenyl, 2,4,6-tripropylphenyl, 2-, 3- and 4-isopropylphenyl, 2,4-, 2,5-, 3,5- and
- unsubstituted or substituted aryl also apply to unsubstituted or substituted aryloxy and unsubstituted or substituted arylthio.
- aryloxy are phenoxy and naphthyloxy.
- hetaryl comprises heteroaromatic, mono- or polycyclic groups and monocyclic groups which may be fused to one or more unfused or fused saturated or unsaturated carbocyclic or heterocyclic five or six membered rings.
- ring carbon atoms these have 1 , 2, 3, 4 or more than 4 of the ring heteroatoms.
- the heteroatoms are preferably selected from oxygen, nitrogen, selenium and sulfur.
- the hetaryl groups have preferably 5 to 18, e.g. 5, 6, 8, 9, 10, 1 1 , 12, 13 or 14, ring atoms.
- Monocyclic hetaryl groups are preferably 5- or 6-membered hetaryl groups, such as 2-furyl (furan-2-yl), 3-furyl (furan-3-yl), 2-thienyl (thiophen-2-yl), 3-thienyl (thiophen-3-yl), selenophen-2- yl, selenophen-3-yl, 1 H-pyrrol-2-yl, 1 H-pyrrol-3-yl, pyrrol-1 -yl, imidazol-2-yl, imidazol-1 -yl, imidazol-4-yl, pyrazol-1 -yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, 3-isoxazolyl, 4-isoxazolyl, 5- isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-oxazolyl, 4-oxazoly
- Polycyclic hetaryl has 2, 3, 4 or more than 4 fused rings.
- the fused-on rings may be aromatic, saturated or partly unsaturated.
- polycyclic 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,
- 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.
- DSCs generally comprise the following elements: an electrically conductive layer (being part of or forming the working electrode or anode), a photosensitive layer generally comprising a semi- conductive metal oxide and a photosensitive dye, a charge transfer layer and another electrically conductive layer (being part of or forming the counter electrode or cathode).
- ⁇ ⁇ 2 blocking layer was prepared on a fluorine-doped tin oxide (FTO)-covered glass substrate using spray pyrolysis (cf. B. Peng, G. Jungmann, C. Jager, D. Haarer, H. W. Schmidt, M. Thelakkat, Coord. Chem. Rev. 2004, 248, 1479).
- a ⁇ 2 paste (Dyesol), diluted with terpineol, was applied by screen printing, resulting in a film thickness of 1.7 ⁇ .
- the hole transporting material spiro- MeOTAD (commercially availble from Merck KGaA, Darmstadt as SHT-263 livilux ® ) and compounds HTM1 , HTM2 and HTM3 were applied by spin-coating from a solution in DCM (200 mg/mL) also containing 20 mM Li(CFsS02)2N . Fabrication of the device was completed by evaporation of 200 nm of silver as the counter electrode. The active area of the sDSC was defined by the size of these contacts (0.13 cm 2 ), and the cells were masked by an aperture of the same area for measurements.
- the samples were illuminated with monochromatic light from the quartz monochromator with deuterium lamp.
- the power of the incident light beam was (2-5) ⁇ 10 -8 W.
- the negative voltage of -300 V was supplied to the sample substrate.
- the counter-electrode with the 4.5x15 mm 2 slit for illumination was placed at 8 mm distance from the sample surface.
- the counter-electrode was connected to the input of the BK2-16 type electrometer, working in the open input regime, for the photocurrent measurement.
- the 10 "15 - 10 "12 A strong photocurrent was flowing in the circuit under illumination.
- the photocurrent J is strongly dependent on the incident light photon energy hv.
- the J 0 5 f(hv) dependence was plotted.
- Figure 1 Comparison of the lifetime of DSCs comprising hole transporting materials HTM1 , HTM2 and HTM3 according to the instant invention versus a DSC comprising spiro-MeOTAD.
- HTM1 , HTM2 and HTM3 the long term stability of the corresponding DSCs is significantly enhanced over the DSC comprising spiro-MeOTAD. All DSCs were sealed and constantly kept at 60°C and 30% humidity after fabrication.
- Figure 2 Exemplification of the initial condition, i.e. at 25°C after fabrication and before heat treatment, of the the spiro-MeOTAD coating on the silver back electrode of the cells. No spiro- MeOTAD crystals were visible under an optical microscope with crossed polarizers.
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Abstract
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AU2013311273A AU2013311273A1 (en) | 2012-09-04 | 2013-08-27 | New spiro compounds and their use in organic electronics applications and devices |
CN201380046133.6A CN104603099A (zh) | 2012-09-04 | 2013-08-27 | 新螺环化合物及其在有机电子应用和器件中的用途 |
JP2015530524A JP2015534545A (ja) | 2012-09-04 | 2013-08-27 | 新規スピロ化合物並びに有機エレクトロニクス用途及びデバイスにおけるその使用 |
EP13836057.3A EP2892875A2 (fr) | 2012-09-04 | 2013-08-27 | Nouveaux composés spiro et leur utilisation dans des applications et dispositifs électroniques organiques |
KR1020157008482A KR20150047623A (ko) | 2012-09-04 | 2013-08-27 | 새로운 스파이로 화합물 및 이의 유기 전자 제품 및 장치에서의 용도 |
ZA2015/02260A ZA201502260B (en) | 2012-09-04 | 2015-04-07 | New spiro compounds and their use in organic electronics applications and devices |
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WO2016012274A1 (fr) | 2014-07-21 | 2016-01-28 | Basf Se | Cellule solaire en tandem organique-inorganique |
US20190288207A1 (en) * | 2016-11-09 | 2019-09-19 | Korea Research Institute Of Chemical Technology | Spirobifluorene compound and perovskite solar cell comprising same |
CN111848422A (zh) * | 2020-06-09 | 2020-10-30 | 山西美意呈科技有限公司 | 一种空穴传输材料及其在钙钛矿太阳能电池中的应用 |
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WO2002051958A1 (fr) * | 2000-12-23 | 2002-07-04 | Johnson Matthey Public Limited Company | Compositions electroactives de type polyarylamine |
US6747287B1 (en) * | 2001-10-18 | 2004-06-08 | Nec Corporation | Organic thin film transistor |
EP2180029A1 (fr) * | 2008-10-23 | 2010-04-28 | Novaled AG | Composés de Radialène et leur utilisation |
JP2010135467A (ja) * | 2008-12-03 | 2010-06-17 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、該素子を備えた照明装置及び表示装置 |
US20100289006A1 (en) * | 2007-05-18 | 2010-11-18 | Chin-Hsin Chen | Novel blue organic compound and organic electroluminescent device using the same |
US20110100466A1 (en) * | 2009-11-05 | 2011-05-05 | National Taiwan University | Organic solar cell and method for forming the same |
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- 2013-08-27 AU AU2013311273A patent/AU2013311273A1/en not_active Abandoned
- 2013-08-27 WO PCT/IB2013/058018 patent/WO2014037847A2/fr active Application Filing
- 2013-08-27 CN CN201380046133.6A patent/CN104603099A/zh active Pending
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- 2013-08-27 EP EP13836057.3A patent/EP2892875A2/fr not_active Withdrawn
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Patent Citations (6)
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WO2002051958A1 (fr) * | 2000-12-23 | 2002-07-04 | Johnson Matthey Public Limited Company | Compositions electroactives de type polyarylamine |
US6747287B1 (en) * | 2001-10-18 | 2004-06-08 | Nec Corporation | Organic thin film transistor |
US20100289006A1 (en) * | 2007-05-18 | 2010-11-18 | Chin-Hsin Chen | Novel blue organic compound and organic electroluminescent device using the same |
EP2180029A1 (fr) * | 2008-10-23 | 2010-04-28 | Novaled AG | Composés de Radialène et leur utilisation |
JP2010135467A (ja) * | 2008-12-03 | 2010-06-17 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、該素子を備えた照明装置及び表示装置 |
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WO2016012274A1 (fr) | 2014-07-21 | 2016-01-28 | Basf Se | Cellule solaire en tandem organique-inorganique |
US20190288207A1 (en) * | 2016-11-09 | 2019-09-19 | Korea Research Institute Of Chemical Technology | Spirobifluorene compound and perovskite solar cell comprising same |
US11563180B2 (en) * | 2016-11-09 | 2023-01-24 | Korea Research Institute Of Checmical Technology | Spirobifluorene compound and perovskite solar cell comprising same |
CN111848422A (zh) * | 2020-06-09 | 2020-10-30 | 山西美意呈科技有限公司 | 一种空穴传输材料及其在钙钛矿太阳能电池中的应用 |
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