JP2009070811A - 光電変換素子用電解質組成物及びそれを用いた光電変換素子 - Google Patents
光電変換素子用電解質組成物及びそれを用いた光電変換素子 Download PDFInfo
- Publication number
- JP2009070811A JP2009070811A JP2008208598A JP2008208598A JP2009070811A JP 2009070811 A JP2009070811 A JP 2009070811A JP 2008208598 A JP2008208598 A JP 2008208598A JP 2008208598 A JP2008208598 A JP 2008208598A JP 2009070811 A JP2009070811 A JP 2009070811A
- Authority
- JP
- Japan
- Prior art keywords
- photoelectric conversion
- conversion element
- electrolyte composition
- dye
- quaternary phosphonium
- 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.)
- Granted
Links
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 54
- 239000003792 electrolyte Substances 0.000 title claims abstract description 53
- 239000000203 mixture Substances 0.000 title claims abstract description 44
- 239000002608 ionic liquid Substances 0.000 claims abstract description 41
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 150000004714 phosphonium salts Chemical group 0.000 claims description 36
- 239000004065 semiconductor Substances 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 8
- YSHMQTRICHYLGF-UHFFFAOYSA-N 4-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=NC=C1 YSHMQTRICHYLGF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract description 12
- 125000000217 alkyl group Chemical group 0.000 abstract description 10
- 239000007788 liquid Substances 0.000 abstract description 7
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 abstract description 2
- 206010061218 Inflammation Diseases 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- -1 phosphonium cations Chemical class 0.000 description 38
- 239000000047 product Substances 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- 238000005259 measurement Methods 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 230000000704 physical effect Effects 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- 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 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 150000001450 anions Chemical class 0.000 description 7
- 238000001291 vacuum drying Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000005979 thermal decomposition reaction Methods 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- FXGODHYYGPSUPL-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide triethyl(methoxymethyl)phosphanium Chemical compound CC[P+](CC)(CC)COC.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F FXGODHYYGPSUPL-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 239000008151 electrolyte solution Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 238000010248 power generation Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- YPSWTNNSEIWYKQ-UHFFFAOYSA-N cyanoiminomethylideneazanide;triethyl(methoxymethyl)phosphanium Chemical compound N#C[N-]C#N.CC[P+](CC)(CC)COC YPSWTNNSEIWYKQ-UHFFFAOYSA-N 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- 229910001887 tin oxide Inorganic materials 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- OXCAXCAGYKWNEQ-UHFFFAOYSA-N cyanoiminomethylideneazanide triethyl(2-methoxyethyl)phosphanium Chemical compound N#C[N-]C#N.CC[P+](CC)(CC)CCOC OXCAXCAGYKWNEQ-UHFFFAOYSA-N 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 230000001235 sensitizing effect Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- PFXZBXXDSUFWLV-UHFFFAOYSA-M triethyl(methoxymethyl)phosphanium;bromide Chemical compound [Br-].CC[P+](CC)(CC)COC PFXZBXXDSUFWLV-UHFFFAOYSA-M 0.000 description 3
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FAKLYVOSFOCNGL-UHFFFAOYSA-N N#C[N-]C#N.CCCC[P+](CCCC)(CCCC)COC Chemical compound N#C[N-]C#N.CCCC[P+](CCCC)(CCCC)COC FAKLYVOSFOCNGL-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- 229910006404 SnO 2 Inorganic materials 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000005349 anion exchange Methods 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 229940006460 bromide ion Drugs 0.000 description 2
- JAMFGQBENKSWOF-UHFFFAOYSA-N bromo(methoxy)methane Chemical compound COCBr JAMFGQBENKSWOF-UHFFFAOYSA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- FMJNRWZOZLKBDF-UHFFFAOYSA-N cyanoiminomethylideneazanide tributyl(2-methoxyethyl)phosphanium Chemical compound N#C[N-]C#N.CCCC[P+](CCCC)(CCCC)CCOC FMJNRWZOZLKBDF-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 150000004693 imidazolium salts Chemical class 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 2
- 229940006461 iodide ion Drugs 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- IXBPPZBJIFNGJJ-UHFFFAOYSA-N sodium;cyanoiminomethylideneazanide Chemical compound [Na+].N#C[N-]C#N IXBPPZBJIFNGJJ-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- ISLMUNSNHGLMCV-UHFFFAOYSA-N tributyl(2-methoxyethyl)phosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCOC ISLMUNSNHGLMCV-UHFFFAOYSA-N 0.000 description 2
- UFDFBNXYCRGTHH-UHFFFAOYSA-M triethyl(2-methoxyethyl)phosphanium;bromide Chemical compound [Br-].CC[P+](CC)(CC)CCOC UFDFBNXYCRGTHH-UHFFFAOYSA-M 0.000 description 2
- NBFLCNFVUMEVOJ-UHFFFAOYSA-M triethyl(methoxymethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)COC NBFLCNFVUMEVOJ-UHFFFAOYSA-M 0.000 description 2
- HESQQIOZXPMZKL-UHFFFAOYSA-M triethyl(pentyl)phosphanium;bromide Chemical compound [Br-].CCCCC[P+](CC)(CC)CC HESQQIOZXPMZKL-UHFFFAOYSA-M 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical group N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 1
- ZZTDEFHCSZAWMD-UHFFFAOYSA-L 2-(4-carboxylatopyridin-2-yl)pyridine-4-carboxylate;ruthenium(2+) Chemical compound [Ru+2].[O-]C(=O)C1=CC=NC(C=2N=CC=C(C=2)C([O-])=O)=C1 ZZTDEFHCSZAWMD-UHFFFAOYSA-L 0.000 description 1
- LTNAYKNIZNSHQA-UHFFFAOYSA-L 2-(4-carboxypyridin-2-yl)pyridine-4-carboxylic acid;ruthenium(2+);dithiocyanate Chemical compound N#CS[Ru]SC#N.OC(=O)C1=CC=NC(C=2N=CC=C(C=2)C(O)=O)=C1.OC(=O)C1=CC=NC(C=2N=CC=C(C=2)C(O)=O)=C1 LTNAYKNIZNSHQA-UHFFFAOYSA-L 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- XTDZSZWPRFOZHV-UHFFFAOYSA-N 2-methoxyethyl(tripentyl)phosphanium Chemical compound CCCCC[P+](CCCCC)(CCCCC)CCOC XTDZSZWPRFOZHV-UHFFFAOYSA-N 0.000 description 1
- KRKIEAVBQZHMBA-UHFFFAOYSA-N 2-methoxyethyl(tripropyl)phosphanium Chemical compound CCC[P+](CCC)(CCC)CCOC KRKIEAVBQZHMBA-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical group S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- XWSVWXSRRXJJNT-UHFFFAOYSA-N N#C[N-]C#N.CCCCC[P+](CC)(CC)CC Chemical compound N#C[N-]C#N.CCCCC[P+](CC)(CC)CC XWSVWXSRRXJJNT-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 239000012327 Ruthenium complex Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- KOMJLZBDIKGQIY-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide triethyl(2-methoxyethyl)phosphanium Chemical compound CC[P+](CC)(CC)CCOC.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F KOMJLZBDIKGQIY-UHFFFAOYSA-N 0.000 description 1
- GLGIWRJFYIZIPE-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide triethyl(methoxymethyl)azanium Chemical compound CC[N+](CC)(CC)COC.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F GLGIWRJFYIZIPE-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 238000010438 heat treatment Methods 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
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000004698 iron complex Chemical class 0.000 description 1
- 230000001678 irradiating effect Effects 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- DDDSDKIGWBBGLG-UHFFFAOYSA-N methoxymethyl(tripentyl)phosphanium Chemical compound CCCCC[P+](CCCCC)(CCCCC)COC DDDSDKIGWBBGLG-UHFFFAOYSA-N 0.000 description 1
- SWQWQUPVBQZTAR-UHFFFAOYSA-N methoxymethyl(tripropyl)phosphanium Chemical compound CCC[P+](CCC)(CCC)COC SWQWQUPVBQZTAR-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000001443 photoexcitation Effects 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- FSOLARXXBUNELG-UHFFFAOYSA-N tributyl(methoxymethyl)phosphanium Chemical compound CCCC[P+](CCCC)(CCCC)COC FSOLARXXBUNELG-UHFFFAOYSA-N 0.000 description 1
- KZEXVNKGDKTRPC-UHFFFAOYSA-N triethyl(2-methoxyethyl)phosphanium Chemical compound CC[P+](CC)(CC)CCOC KZEXVNKGDKTRPC-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- WRQUCXJNDIJUTE-UHFFFAOYSA-N trihexyl(2-methoxyethyl)phosphanium Chemical compound CCCCCC[P+](CCCCCC)(CCCCCC)CCOC WRQUCXJNDIJUTE-UHFFFAOYSA-N 0.000 description 1
- AMZYICFZAGXQIR-UHFFFAOYSA-N trihexyl(methoxymethyl)phosphanium Chemical compound CCCCCC[P+](CCCCCC)(CCCCCC)COC AMZYICFZAGXQIR-UHFFFAOYSA-N 0.000 description 1
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N—ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N10/00—Thermoelectric devices comprising a junction of dissimilar materials, i.e. devices exhibiting Seebeck or Peltier effects
- H10N10/80—Constructional details
- H10N10/85—Thermoelectric active materials
- H10N10/856—Thermoelectric active materials comprising organic compositions
-
- 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
- H01G9/2004—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte
- H01G9/2013—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte the electrolyte comprising ionic liquids, e.g. alkyl imidazolium iodide
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M14/00—Electrochemical current or voltage generators not provided for in groups H01M6/00 - H01M12/00; Manufacture thereof
-
- 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
- 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
- H01G9/2059—Light-sensitive devices comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution
-
- 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
Landscapes
- Power Engineering (AREA)
- Electrochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Physics & Mathematics (AREA)
- Computer Hardware Design (AREA)
- General Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Chemical & Material Sciences (AREA)
- Hybrid Cells (AREA)
- Photovoltaic Devices (AREA)
Abstract
【解決手段】下記一般式(1)で表される四級ホスホニウム塩イオン液体を含有することを特徴とする光電変換素子用電解質組成物である。このイオン液体の25℃における粘度は200mPa・sec以下であることが好ましい。一般式(1)において、アルコキシアルキル基がメトキシメチル基であり、アルキル基がすべてエチル基であることが好ましい。
【選択図】図1
Description
半導体層;
該半導体層の一方の面に設けられた色素層;
該色素層に対向して配された対極;及び
該色素層と該対極との間に配された、前記の電解質組成物からなる電解質層;
を具備することを特徴とする光電変換素子を提供するものである。
少ない目的物を得ることができるため好ましい。また、四級ホスホニウムハライドのハロゲンが臭素やヨウ素であると、四級ホスホニウムハライドを再結晶により精製することができるので好ましい。この観点から、ハロゲン化アルコキシアルキルとして、臭化アルコキシアルキルやヨウ化アルコキシアルキルを用いることが好ましい。なお、四級ホスホニウムハライドにおけるハロゲンが臭素及びヨウ素以外の元素である場合、例えば塩化物等であっても、ヨウ化ナトリウム等を用いることで、塩素をヨウ素又は臭素に置換することができる。
トリエチル(メトキシメチル)ホスホニウムビス(トリフルオロメチルスルホニル)イミドの合成及び物性測定
(1)合成
トリエチルホスフィン25%トルエン溶液(日本化学工業株式会社製品名:ヒシコーリン(登録商標)P−2)236g(0.5mol)に、ブロモメチルメチルエーテル(東京化成工業株式会社試薬)62g(0.5mol)を滴下し、70〜80℃で6時間反応させた。反応終了後ヘキサンを加えて晶析させ、トリエチル(メトキシメチル)ホスホニウムブロミドの結晶を97g得た(収率80%)。このトリエチル(メトキシメチル)ホスホニウムブロミド73g(0.3mol)に、リチウムビス(トリフルオロメチルスルホニル)イミド(関東化学株式会社試薬)86g(0.3mol)を加えて水系で反応させた。次いで室温で3時間攪拌して熟成させた。攪拌終了後、下層(生成物)を分離した。分離した生成物に対して純水洗浄を4回行い、続いてヘキサン洗浄を4回行った。洗浄終了後、100℃、真空度0.5kPaにて5時間真空乾燥した。このようにして得られた生成物の確認を、1H−NMR、13C−NMR、31P−NMR、19F−NMRにて行っ
た。生成物(無色透明液体)の収量は104g(収率78%)であり、31P−NMRより純度98%以上であることを確認した。
生成物の融点を示差走査熱量分析(セイコーインストルメンタル株式会社、DSC6200)により測定した。また粘度を、振動式粘度計(CBC株式会社、VM−10A)を用いて測定した。なお、粘度は測定条件により、±5%程度の誤差が生じる。更に熱分解温度(10%重量減少)を熱重量分析装置(セイコーインストルメンタル株式会社、TG/DTA6300)を用いて測定した。測定結果を以下の表1に示す。以上の測定はすべて窒素雰囲気下にて行った。
トリエチル(メトキシメチル)ホスホニウムジシアナミドの合成及び物性測定
(1)合成
合成例1と同様にして合成したトリエチル(メトキシメチル)ホスホニウムブロミド73g(0.3mol)に、ナトリウムジシアナミド(和光純薬工業株式会社試薬)27g(0.3mol)を加えて水系で反応させた。次いで室温で3時間攪拌して熟成させた。攪拌終了後、ジクロロメタンで生成物を抽出し、シリカゲルカラムに通して精製してから溶剤留去し、100℃、真空度0.5kPaにて5時間真空乾燥した。このようにして得られた生成物の確認を、1H−NMR、13C−NMR、31P−NMRにて行った。生成物
(淡黄色透明液体)の収量は34g(収率50%)であり、31P−NMRより純度98%以上であることを確認した。
生成物の融点、粘度及び熱分解温度を合成例1と同様に測定した。測定結果を以下の表1に示す。
トリエチルペンチルホスホニウムジシアナミドの合成及び物性測定
(1)合成
トリエチルホスフィン25%トルエン溶液(日本化学工業株式会社製品名:ヒシコーリン(登録商標)P−2)236g(0.5mol)に、1−ブロモペンタン(東京化成工業株式会社試薬)77g(0.5mol)を滴下し、70〜80℃で6時間反応させた。反応終了後ヘキサンを加えて晶析させ、トリエチルペンチルホスホニウムブロミドの結晶を113g得た(収率84%)。このトリエチルペンチルホスホニウムブロミド81g(0.3mol)に、ナトリウムジシアナミド(和光純薬工業株式会社試薬)27g(0.3mol)を加えて水系で反応させた。次いで室温で3時間攪拌して熟成させた。攪拌終了後、ジクロロメタンで生成物を抽出し、シリカゲルカラムに通して精製してから溶剤留去し、100℃、真空度0.5kPaにて5時間真空乾燥した。このようにして得られた生成物の確認を、1H−NMR、13C−NMR、31P−NMRにて行った。生
成物(淡黄色透明液体)の収量は77g(収率69%)であり、31P−NMRより純度98%以上であることを確認した。
生成物の融点、粘度及び熱分解温度を合成例1と同様に測定した。測定結果を以下の表1に示す。
トリエチル(2−メトキシエチル)ホスホニウム テトラフルオロボレートの合成及び物
性測定
(1)合成
トリエチルホスフィン25%トルエン溶液(日本化学工業株式会社製品名:ヒシコーリン(登録商標)P−2)236g(0.5mol)に,2−ブロモエチルメチルエーテル
(東京化成工業株式会社試薬)73g(0.5mol)を滴下し、70〜80℃で6時間反応させた。反応終了後ヘキサンを加えて晶析させ、トリエチル(2−メトキシエチル)ホスホニウムブロミドの結晶を125g得た(収率97%)。このトリエチル(2−メトキシエチル)ホスホニウムブロミド77g(0.3mol)に、ホウフッ化ナトリウム(関東化学株式会社試薬)33g(0.3mol)を加えて水系で反応させた。次いで室温で3時間攪拌して熟成させた。攪拌終了後、100℃、真空度0.5kPaにて完全に脱水し、更に乾燥塩化メチレンを100ml加えて、沈殿をろ過した。この濾液を濃縮し、100℃、真空度0.5kPaにて5時間真空乾燥した。このようにして得られた生成物の確認を、1H−NMR、13C−NMR、31P−NMR、19F−NMRにて行った。生成
物(無色透明液体)の収量は60g(収率76%)であり、31P−NMRより純度98%以上であることを確認した。
生成物の融点、粘度及び熱分解温度を合成例1と同様に測定した。測定結果を以下の表1に示す。
トリエチル(メトキシメチル)アンモニウムビス(トリフルオロメチルスルホニル)イミドの合成及び物性測定
(1)合成
トリエチルアミン(東京化成工業株式会社試薬)51g(0.5mol)に、ブロモメチルメチルエーテル(東京化成工業株式会社試薬)77g(0.6mol)を滴下し、60〜70℃で6時間反応させた。反応終了後ヘキサンを加えて晶析させ、トリエチル(メトキシメチル)アンモニウムブロミドの結晶を96g得た(収率85%)。このトリエチル(メトキシメチル)アンモニウムブロミド34g(0.15mol)に、リチウムビス(トリフルオロメチルスルホニル)イミド(関東化学株式会社試薬)52g(0.18m
ol)を加えて水系で反応させた。次いで室温で3時間攪拌して熟成させた。攪拌終了後、下層(生成物)を分離した。分離した生成物に対し純水洗浄を4回行い、続いてヘキサン洗浄を4回行った。洗浄終了後、100℃、真空度0.5kPaにて5時間真空乾燥した。このようにして得られた生成物の確認を、1H−NMR、13C−NMR、19F−NM
Rにて行った。生成物(無色透明液体)の収量は59g(収率93%)であった。
生成物の融点、粘度及び熱分解温度を合成例1と同様に測定した。測定結果を以下の表1に示す。
表2に示すように、各合成例で得られた化合物からなるイオン液体、レドックス対及び必要に応じて添加剤を混合して電解質組成物を調製した。
11 半導体層
12 色素層
13 透明電極層
14 対極
15 電解質層
Claims (8)
- 25℃における粘度が200mPa・sec以下である請求項1記載の光電変換素子用電解質組成物。
- R1がエチル基であり、nが1である請求項1又は2記載の光電変換素子用電解質組成物。
- XがN(CN)2で表される請求項1ないし3の何れかに記載の光電変換素子用電解質組成物。
- ハロゲン化物イオンと、ポリハロゲン化物イオンとからなる含ハロゲン系レドックス対を0.05〜4.0M含む請求項1ないし4の何れかに記載の光電変換素子用電解質組成物。
- 4−tert−ブチルピリジン又は水を0.01〜4.0M含む請求項1ないし5の何れかに記載の光電変換素子用電解質組成物。
- 半導体層;
該半導体層の一方の面に設けられた色素層;
該色素層に対向して配された対極;及び
該色素層と該対極との間に配された、請求項1記載の電解質組成物からなる電解質層;
を具備することを特徴とする光電変換素子。 - 色素増感型太陽電池である請求項7記載の光電変換素子。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008208598A JP5261068B2 (ja) | 2007-08-23 | 2008-08-13 | 光電変換素子用電解質組成物及びそれを用いた光電変換素子 |
KR1020080082514A KR20090020527A (ko) | 2007-08-23 | 2008-08-22 | 광전 변환 소자용 전해질 조성물 및 그것을 이용한 광전 변환 소자 |
TW097132047A TW200926485A (en) | 2007-08-23 | 2008-08-22 | Electrolyte composition for photoelectric conversion device, and photoelectric conversion device using the same |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007217123 | 2007-08-23 | ||
JP2007217123 | 2007-08-23 | ||
JP2008208598A JP5261068B2 (ja) | 2007-08-23 | 2008-08-13 | 光電変換素子用電解質組成物及びそれを用いた光電変換素子 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2009070811A true JP2009070811A (ja) | 2009-04-02 |
JP5261068B2 JP5261068B2 (ja) | 2013-08-14 |
Family
ID=40430554
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008208598A Expired - Fee Related JP5261068B2 (ja) | 2007-08-23 | 2008-08-13 | 光電変換素子用電解質組成物及びそれを用いた光電変換素子 |
Country Status (4)
Country | Link |
---|---|
US (1) | US8088995B2 (ja) |
JP (1) | JP5261068B2 (ja) |
KR (1) | KR20090020527A (ja) |
TW (1) | TW200926485A (ja) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010013435A (ja) * | 2008-06-03 | 2010-01-21 | Nissan Motor Co Ltd | イオン伝導体 |
JP2011122242A (ja) * | 2009-11-16 | 2011-06-23 | Yokohama National Univ | 白金族元素及び/又は希土類元素の回収方法、並びに白金族元素及び希土類元素の回収装置 |
JP2012129089A (ja) * | 2010-12-16 | 2012-07-05 | Nippon Chem Ind Co Ltd | 光電変換素子用電解質組成物及び光電変換素子 |
JP2013047217A (ja) * | 2011-07-27 | 2013-03-07 | Nichia Corp | イオン液体 |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4961111B2 (ja) * | 2005-02-28 | 2012-06-27 | 富士フイルム株式会社 | 光電変換膜積層型固体撮像素子とその製造方法 |
US20090084443A1 (en) * | 2007-08-23 | 2009-04-02 | Tokai University Educational System | Electrolyte composition for photoelectric conversion device and photoelectric conversion device using the same |
CN103069645B (zh) * | 2010-09-16 | 2016-01-20 | 株式会社艾迪科 | 电解质组合物用添加剂及使用了该添加剂的电解质组合物以及染料敏化太阳能电池 |
KR101691946B1 (ko) | 2014-04-17 | 2017-01-02 | 부산대학교 산학협력단 | 열전 장치용 전해질 용액 및 이를 포함하는 열전 장치 |
WO2015160150A1 (ko) * | 2014-04-17 | 2015-10-22 | 부산대학교 산학협력단 | 열전 장치용 전해질 용액 및 이를 포함하는 열전 장치 |
WO2017011759A1 (en) * | 2015-07-15 | 2017-01-19 | Trustees Of Boston University | Ionic liquid electrolytes and electrochemical devices comprising same |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006012848A (ja) * | 2004-06-26 | 2006-01-12 | Samsung Sdi Co Ltd | 電解液組成物及びそれを利用した太陽電池 |
JP2008222592A (ja) * | 2007-03-09 | 2008-09-25 | Nippon Chem Ind Co Ltd | 新規ホスホニウム塩イオン液体、それを用いた反応溶媒 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2441981C (en) * | 2001-03-26 | 2012-05-15 | Nisshinbo Industries, Inc. | Ionic liquids, electrolyte salts for electrical storage devices, liquid electrolytes for electrical storage devices, electrical double-layer capacitors, and secondary batteries |
CN101090952A (zh) * | 2004-12-13 | 2007-12-19 | 特拉斯福特普拉斯公司 | 组合物,氧化还原对及其应用 |
EP1819005A1 (en) * | 2006-02-13 | 2007-08-15 | Ecole Polytechnique Fédérale de Lausanne (EPFL) | Ionic liquid electrolyte |
US20070215865A1 (en) * | 2006-03-20 | 2007-09-20 | General Electric Company | Opto-electronic devices exhibiting enhanced efficiency |
JP5143476B2 (ja) * | 2006-06-09 | 2013-02-13 | 第一工業製薬株式会社 | 光電変換素子 |
US20090084443A1 (en) * | 2007-08-23 | 2009-04-02 | Tokai University Educational System | Electrolyte composition for photoelectric conversion device and photoelectric conversion device using the same |
JP5242973B2 (ja) * | 2007-08-23 | 2013-07-24 | 日本化学工業株式会社 | 蓄電デバイス用電解質組成物及びそれを用いた蓄電デバイス |
-
2008
- 2008-08-13 JP JP2008208598A patent/JP5261068B2/ja not_active Expired - Fee Related
- 2008-08-22 US US12/196,568 patent/US8088995B2/en not_active Expired - Fee Related
- 2008-08-22 KR KR1020080082514A patent/KR20090020527A/ko not_active Application Discontinuation
- 2008-08-22 TW TW097132047A patent/TW200926485A/zh unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006012848A (ja) * | 2004-06-26 | 2006-01-12 | Samsung Sdi Co Ltd | 電解液組成物及びそれを利用した太陽電池 |
JP2008222592A (ja) * | 2007-03-09 | 2008-09-25 | Nippon Chem Ind Co Ltd | 新規ホスホニウム塩イオン液体、それを用いた反応溶媒 |
Non-Patent Citations (1)
Title |
---|
JPN6013007316; Tsunashima K,: 'Physical and electrochemical properties of low-viscosity phosphonium ionic liquids as potential elec' Electrochemistry Communications 9(9), 20070712, 2353-58 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010013435A (ja) * | 2008-06-03 | 2010-01-21 | Nissan Motor Co Ltd | イオン伝導体 |
JP2011122242A (ja) * | 2009-11-16 | 2011-06-23 | Yokohama National Univ | 白金族元素及び/又は希土類元素の回収方法、並びに白金族元素及び希土類元素の回収装置 |
JP2012129089A (ja) * | 2010-12-16 | 2012-07-05 | Nippon Chem Ind Co Ltd | 光電変換素子用電解質組成物及び光電変換素子 |
JP2013047217A (ja) * | 2011-07-27 | 2013-03-07 | Nichia Corp | イオン液体 |
Also Published As
Publication number | Publication date |
---|---|
US20090065058A1 (en) | 2009-03-12 |
US20110083744A9 (en) | 2011-04-14 |
KR20090020527A (ko) | 2009-02-26 |
JP5261068B2 (ja) | 2013-08-14 |
TW200926485A (en) | 2009-06-16 |
US8088995B2 (en) | 2012-01-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5261068B2 (ja) | 光電変換素子用電解質組成物及びそれを用いた光電変換素子 | |
JP5003871B2 (ja) | 二核金属錯体、金属錯体色素、光電変換素子、及び光化学電池 | |
JP5590025B2 (ja) | 光電変換素子およびその製造方法、光センサならびに太陽電池 | |
JP2007311336A (ja) | リン酸塩を含有する半導体電極及びこれを採用した太陽電池 | |
JP5350851B2 (ja) | 光電変換素子用組成物及びそれを用いた光電変換素子 | |
Dhar et al. | Systematic study of mono-and tri-TEMPO-based electrolytes for highly efficient next-generation dye-sensitised photo harvesting | |
JP5584447B2 (ja) | 光電気素子 | |
US20090084443A1 (en) | Electrolyte composition for photoelectric conversion device and photoelectric conversion device using the same | |
KR20060090002A (ko) | 겔형 전해질 및 이를 채용한 염료감응 태양전지 | |
JP5614807B2 (ja) | 光電変換素子用電解質組成物及び光電変換素子 | |
JP2005112733A (ja) | オニウム塩 | |
KR20120007172A (ko) | 신규한 이미다졸륨 염 및 이를 함유하는 염료감응 태양전지용 전해질 조성물 | |
KR101048172B1 (ko) | 유기 금속 염료, 이를 구비하는 광감성 기판, 및 염료 감응태양전지 | |
Prasad et al. | Above 800 mV open-circuit voltage in solid-state photovoltaic devices using phosphonium cation-based solid ionic conductors | |
KR101465454B1 (ko) | 염료감응 태양전지용 유기염료 및 이를 포함하는 염료감응 태양전지 | |
JP2011165423A (ja) | 光電変換素子 | |
JP2007200833A (ja) | 色素増感型太陽電池用電解液、色素増感型太陽電池用酸化物半導体電極及び色素増感型太陽電池 | |
JP2011150883A (ja) | 光電変換素子、光センサ、および、太陽電池 | |
JP2011150881A (ja) | 光電変換素子、光センサ、および、太陽電池 | |
WO2005104291A1 (ja) | 色素増感型太陽電池用電解液、色素増感型太陽電池用酸化物半導体電極及び色素増感型太陽電池 | |
Hong et al. | Salicylic acid-based organic dyes acting as the photosensitizer for solar cells | |
JP4294934B2 (ja) | 光電気化学電池用イオン導電性組成物 | |
JP6568354B2 (ja) | 電解質、光電変換素子用電解質、光電変換素子及び色素増感太陽電池 | |
JP2015222808A (ja) | 光電変換素子 | |
JP2005126382A (ja) | オニウム塩 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110421 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130219 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130325 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130423 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130426 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20160502 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
LAPS | Cancellation because of no payment of annual fees |