JP2017525158A - 固体正孔輸送材料 - Google Patents
固体正孔輸送材料 Download PDFInfo
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- JP2017525158A JP2017525158A JP2017507826A JP2017507826A JP2017525158A JP 2017525158 A JP2017525158 A JP 2017525158A JP 2017507826 A JP2017507826 A JP 2017507826A JP 2017507826 A JP2017507826 A JP 2017507826A JP 2017525158 A JP2017525158 A JP 2017525158A
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- 239000007787 solid Substances 0.000 title claims abstract description 72
- 239000000463 material Substances 0.000 title claims abstract description 32
- 230000005525 hole transport Effects 0.000 title claims abstract description 21
- 239000010949 copper Substances 0.000 claims abstract description 39
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 22
- -1 2,9 disubstituted 1,10-phenanthroline Chemical class 0.000 claims abstract description 20
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000010931 gold Substances 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 229910052802 copper Inorganic materials 0.000 claims abstract description 11
- 229910052737 gold Inorganic materials 0.000 claims abstract description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052709 silver Inorganic materials 0.000 claims abstract description 9
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 7
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims abstract description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 5
- 239000010941 cobalt Substances 0.000 claims abstract description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 5
- 239000004332 silver Substances 0.000 claims abstract description 5
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 5
- RFVHVYKVRGKLNK-UHFFFAOYSA-N bis(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1 RFVHVYKVRGKLNK-UHFFFAOYSA-N 0.000 claims description 5
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 claims description 4
- OHJPGUSXUGHOGE-UHFFFAOYSA-N 2-methyl-6-(6-methylpyridin-2-yl)pyridine Chemical compound CC1=CC=CC(C=2N=C(C)C=CC=2)=N1 OHJPGUSXUGHOGE-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- IYRGXJIJGHOCFS-UHFFFAOYSA-N neocuproine Chemical compound C1=C(C)N=C2C3=NC(C)=CC=C3C=CC2=C1 IYRGXJIJGHOCFS-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 239000010944 silver (metal) Substances 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical class N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 abstract description 3
- 210000004027 cell Anatomy 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 239000004020 conductor Substances 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 229910044991 metal oxide Inorganic materials 0.000 description 12
- 150000004706 metal oxides Chemical class 0.000 description 12
- 239000003504 photosensitizing agent Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 9
- 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 8
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229910010413 TiO 2 Inorganic materials 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- YSHMQTRICHYLGF-UHFFFAOYSA-N 4-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=NC=C1 YSHMQTRICHYLGF-UHFFFAOYSA-N 0.000 description 4
- QBWOHOMSJGLYTA-UHFFFAOYSA-N CC=1C(=NC2=C3N=CC=CC3=CC=C2C1)C.[Cu] Chemical compound CC=1C(=NC2=C3N=CC=CC3=CC=C2C1)C.[Cu] QBWOHOMSJGLYTA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229960005070 ascorbic acid Drugs 0.000 description 4
- 235000010323 ascorbic acid Nutrition 0.000 description 4
- 239000011668 ascorbic acid Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 4
- 239000002105 nanoparticle Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 229920003182 Surlyn® Polymers 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 239000010439 graphite Substances 0.000 description 3
- 229910002804 graphite Inorganic materials 0.000 description 3
- 239000011244 liquid electrolyte Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- INWFLBXPENDFJW-UHFFFAOYSA-N 3,4-dimethyl-2-pyridin-2-ylpyridine Chemical compound CC1=CC=NC(C=2N=CC=CC=2)=C1C INWFLBXPENDFJW-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- QAMPZQXPFWAZFD-UHFFFAOYSA-N CC1=C(C(=NC=C1)C1=NC=CC=C1)C.[Cu] Chemical compound CC1=C(C(=NC=C1)C1=NC=CC=C1)C.[Cu] QAMPZQXPFWAZFD-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- 229910006404 SnO 2 Inorganic materials 0.000 description 2
- 229910002367 SrTiO Inorganic materials 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 150000004699 copper complex Chemical class 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 description 2
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 description 2
- 239000002071 nanotube Substances 0.000 description 2
- 239000002070 nanowire Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007784 solid electrolyte Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- SHPPDRZENGVOOR-UHFFFAOYSA-N 1-butylbenzimidazole Chemical compound C1=CC=C2N(CCCC)C=NC2=C1 SHPPDRZENGVOOR-UHFFFAOYSA-N 0.000 description 1
- FGYADSCZTQOAFK-UHFFFAOYSA-N 1-methylbenzimidazole Chemical compound C1=CC=C2N(C)C=NC2=C1 FGYADSCZTQOAFK-UHFFFAOYSA-N 0.000 description 1
- MFZBSWSCIWCRKS-UHFFFAOYSA-N 2,9-dimethyl-1,10-phenanthroline;hydrate Chemical compound O.C1=C(C)N=C2C3=NC(C)=CC=C3C=CC2=C1 MFZBSWSCIWCRKS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000002482 conductive additive Substances 0.000 description 1
- PDZKZMQQDCHTNF-UHFFFAOYSA-M copper(1+);thiocyanate Chemical compound [Cu+].[S-]C#N PDZKZMQQDCHTNF-UHFFFAOYSA-M 0.000 description 1
- WTNXLMHVEJFZAQ-UHFFFAOYSA-N copper;2,9-dimethyl-1,10-phenanthroline Chemical compound [Cu].C1=C(C)N=C2C3=NC(C)=CC=C3C=CC2=C1.C1=C(C)N=C2C3=NC(C)=CC=C3C=CC2=C1 WTNXLMHVEJFZAQ-UHFFFAOYSA-N 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- FZHSXDYFFIMBIB-UHFFFAOYSA-L diiodolead;methanamine Chemical compound NC.I[Pb]I FZHSXDYFFIMBIB-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008570 general process Effects 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
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000004754 hybrid cell Anatomy 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000010416 ion conductor Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 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 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 230000002165 photosensitisation Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000005036 potential barrier Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000010129 solution processing Methods 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
- 239000002226 superionic conductor Substances 0.000 description 1
- 238000001308 synthesis method Methods 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
- 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
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- WRTMQOHKMFDUKX-UHFFFAOYSA-N triiodide Chemical compound I[I-]I WRTMQOHKMFDUKX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2027—Light-sensitive devices comprising an oxide semiconductor electrode
- H01G9/2031—Light-sensitive devices comprising an oxide semiconductor electrode comprising titanium oxide, e.g. TiO2
-
- 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
- H10K30/10—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising heterojunctions between organic semiconductors and inorganic semiconductors
- H10K30/15—Sensitised wide-bandgap semiconductor devices, e.g. dye-sensitised TiO2
- H10K30/151—Sensitised wide-bandgap semiconductor devices, e.g. dye-sensitised TiO2 the wide bandgap semiconductor comprising titanium oxide, e.g. TiO2
-
- 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
- H10K85/30—Coordination compounds
- H10K85/371—Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver
-
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
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Abstract
Description
色素増感太陽電池(DSC、時にはDSSCまたはDYSCとも称される)、正孔輸送材料(HTM)が有用であることを認めることのできる特定のタイプの太陽電池である。DSCは、シリコン系光起電力デバイスの費用対効果の高い代替品として大きな関心を集めている。DSCにおいて、光は、メソポーラスワイドバンドギャップ半導体、通常はTiO2、に固定された色素分子により吸収される。光吸収によって、光励起された色素が半導体の伝導帯に電子を注入し、その得られた酸化状態は周囲の電解質中のレドックスメディエータにより再生される。これまでのところ、ルテニウム系色素およびヨウ化物/三ヨウ化物酸化還元対を用いて得られたDSCの最高セル性能は、約11%の変換効率である。
Fukuzumiおよび共同研究者(Journal of the American Chemical Society, 2005, 127(26):9648-9654)は、従来のI3 -/I- 対を使用したものの光電化学応答と比較するために、酸化還元対として銅錯体を用いた最初の色素増感太陽電池を構築した。達成された最大η値は、強度20mW/cm2の弱太陽光照射下で、[Cu(dmp)2]2+/+ を使用したDSCの場合に2.2%であった。
各構造体
により表される錯体を含む固体(solid state)または準固体(quasisolid state)正孔輸送材料(HTM)の提供により達成される。いくつかの実施形態において、HTMは、式Iの2種以上の錯体の混合物を含む。好ましい一実施形態において、式Iの錯体、または式Iの2種以上の錯体の混合物が、HTMにおける主たる正孔伝導化合物である。
いくつかの実施形態において、錯体は、式II:
により表される。
により表される。
すべての化学物質および溶媒は、特に明記していない場合は、Sigma-Aldrich社から購入し、さらに精製することなく使用した。
Cu(II)dmp 2 Cl 2 (1):窒素雰囲気下、エタノール中で1当量のCuCl2を4当量のネオクプロイン水和物と室温で2時間混合した。錯体(1)を濾過により回収し、水およびジエチルエーテルで洗浄した。収率は80%(モル)であった。
Cu(II)dmp 2 Cl−TFSI(2):錯体(1)を1:2エタノール/水混合物中に溶解させた。この溶液に5当量のLi−TFSIを加えた。溶液を、窒素雰囲気下、室温で2時間撹拌した。錯体(2)を濾過により回収し、水およびジエチルエーテルで洗浄した。収率は92%(モル)であった。
Cu(I)dmp 2 TFSI(3):錯体(2)をアセトニトリル中に溶解させた。この溶液に10当量のアスコルビン酸を加えた。溶液を、窒素雰囲気下、ジエチルエーテル中で、室温で2時間撹拌した。残りのアスコルビン酸の濾過後、溶媒を蒸発させると、暗赤色粉末の粗生成物として錯体(3)がもたらされた。さらに精製後、錯体(3)を、強赤色粉末として得た。収率は90%(モル)であった。
すべての化学物質および溶媒は、特に明記していない場合は、Sigma-Aldrich社から購入し、さらに精製することなく使用した。
Cu(II)dmbp 2 Cl 2 (4):窒素雰囲気下、エタノールと水(1:1)中で、1当量のCuCl2を2.2当量の2,2’−ジメチルビピリジンと室温で2時間混合した。錯体(4)を濾過により回収し、水およびジエチルエーテルで洗浄した。収率は80%(モル)であった。
Cu(II)dmp 2 Cl−TFSI(5):錯体(4)を1:2エタノール/水混合物中に溶解させた。この溶液に5当量のLi−TFSIを加えた。溶液を、窒素雰囲気下、室温で2時間撹拌した。錯体(5)を濾過により回収し、水およびジエチルエーテルで洗浄した。収率は92%(モル)であった。
Cu(I)dmbp 2 TFSI(6):錯体(5)をアセトニトリル中に溶解させた。この溶液に10当量のアスコルビン酸を加えた。溶液を、窒素雰囲気下、室温で2時間撹拌した。残留アスコルビン酸の濾過後、溶媒を蒸発させると、暗赤色粉末として錯体(6)の粗生成物を得た。さらに精製後、錯体(6)を、強赤色粉末として得た。収率は60%(モル)であった。
吸収層として光増感剤またはペロブスカイト層が付着した金属酸化物ナノ粒子を使用してssDSCデバイスを作製した。図1(デバイスAおよびB)を参照。
この例では、クロロベンゼン(CB)またはアセトニトリル(CH3CN)中にCudmp2またはCudmbp2(Cu(I)0.2MおよびCu(II)0.05M)、4−tert−ブチルピリジン(TBP、0.5M)、リチウムビス(トリフルオロメタンスルホニル)イミド(LiTFSI、0.1M)を含むHTM組成物を使用した。使用した様々なHTM/電解質を表1に列挙する。
Claims (14)
- 固体または準固体正孔輸送材料(HTM)であって、式I:
各構造体
により表される錯体を含み、前記式Iにより表される錯体が当該HTMの主たる正孔伝導化合物である、固体または準固体正孔輸送材料(HTM)。 - 前記錯体が、式II:
R2〜R7およびR10〜R15の各々は、独立に、Hを表す。)
により表される、請求項1に記載の固体または準固体HTM。 - 前記錯体が、式III:
R2〜R7およびR10〜R15の各々は、独立に、Hを表す。)
により表される、請求項1に記載の固体または準固体HTM。 - R1、R8、R9およびR16は、互いに独立に、置換および非置換の分岐および非分岐のアルキルおよびアリール基からなる群から選ばれ、好ましくは低級アルキルであり、より好ましくはメチルである、請求項2または3に記載の固体または準固体HTM。
- MがCu、Pd、Au、AgおよびVから選ばれ、Mは好ましくはCuである、請求項1〜4のいずれか一項に記載の固体または準固体HTM。
- 前記錯体が、M−(2,9−ジメチル−1,10−フェナントロリン)2、好ましくはCu−(2,9−ジメチル−1,10−フェナントロリン)2である、請求項2に記載の固体または準固体HTM。
- 前記錯体が、M−(6,6’−ジメチル−2,2’−ビピリジン)2(M(dmbp)2)、好ましくはCu−(6,6’−ジメチル−2,2’−ビピリジン)2である、請求項3に記載の固体または準固体HTM。
- さらに、PF6 −(ヘキサフルオロホスフェート)、TFSI−(ビス(トリフルオロメタン)スルホンイミド)、Cl−(塩化物)およびBF4 −(テトラフルオロボレート)からなる群から選ばれた負の対イオンを含む、請求項1〜7のいずれか一項に記載の固体または準固体HTM。
- 前記錯体が固体状態にある、請求項1〜8のいずれか一項に記載の固体または準固体HTM。
- 請求項1〜9のいずれか一項に記載の固体または準固体正孔輸送材料(HTM)を含む電子デバイス。
- 前記デバイスが、例えば有機発光ダイオード(OLED)または有機トランジスタなどの有機電子デバイスである、請求項10に記載の電子デバイス。
- 前記デバイスが、例えばハイブリッド太陽電池、有機太陽電池または色素増感太陽電池(DSC)などの太陽電池である、請求項10に記載の電子デバイス。
- 前記デバイスが、固体色素増感太陽電池(ssDSC)である、請求項10に記載の電子デバイス。
- 式I:
各構造体
により表される錯体の固体電子デバイスにおける主たる正孔輸送材料としての使用。
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EP14180515.0 | 2014-08-11 | ||
EP14180515.0A EP2985799A1 (en) | 2014-08-11 | 2014-08-11 | Solid state hole transport material |
PCT/EP2015/058501 WO2016023644A1 (en) | 2014-08-11 | 2015-04-20 | Solid state hole transport material |
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EP3407361A1 (en) * | 2017-05-24 | 2018-11-28 | Ecole Polytechnique Fédérale de Lausanne (EPFL) | Redox melts formed by copper (i)/(ii) complexes as charge transfer and charge storage materials |
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