JP5491419B2 - 高分子吸光係数金属色素 - Google Patents
高分子吸光係数金属色素 Download PDFInfo
- Publication number
- JP5491419B2 JP5491419B2 JP2010548237A JP2010548237A JP5491419B2 JP 5491419 B2 JP5491419 B2 JP 5491419B2 JP 2010548237 A JP2010548237 A JP 2010548237A JP 2010548237 A JP2010548237 A JP 2010548237A JP 5491419 B2 JP5491419 B2 JP 5491419B2
- Authority
- JP
- Japan
- Prior art keywords
- dye
- layer
- compound
- general formula
- ligand
- 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.)
- Expired - Fee Related
Links
- 229910052751 metal Inorganic materials 0.000 title claims description 10
- 239000002184 metal Substances 0.000 title claims description 10
- 230000008033 biological extinction Effects 0.000 title description 3
- 229920000642 polymer Polymers 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 51
- 239000003446 ligand Substances 0.000 claims description 42
- 239000004065 semiconductor Substances 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 22
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 239000003792 electrolyte Substances 0.000 claims description 12
- 150000002902 organometallic compounds Chemical class 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 230000031700 light absorption Effects 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002608 ionic liquid Substances 0.000 claims description 8
- 230000001235 sensitizing effect Effects 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000000049 pigment Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 238000004873 anchoring Methods 0.000 claims description 6
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 5
- 150000001350 alkyl halides Chemical class 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 239000013522 chelant Substances 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 3
- 229960001860 salicylate Drugs 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 238000003763 carbonization Methods 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000000975 dye Substances 0.000 description 105
- 239000010410 layer Substances 0.000 description 71
- 125000005842 heteroatom Chemical group 0.000 description 26
- 125000003342 alkenyl group Chemical group 0.000 description 22
- 125000000304 alkynyl group Chemical group 0.000 description 22
- 229910010413 TiO 2 Inorganic materials 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 229910052707 ruthenium Inorganic materials 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000002105 nanoparticle Substances 0.000 description 8
- -1 thieno [3,2-b] thiophenyl Chemical group 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- 0 CC(*1)C(*)C(B2)=C1C(*)=C2[Al]C Chemical compound CC(*1)C(*)C(B2)=C1C(*)=C2[Al]C 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 description 2
- MOZHJALYAPTCFZ-UHFFFAOYSA-N 1-thieno[3,2-b]thiophen-5-yloctan-1-one Chemical compound S1C=CC2=C1C=C(C(=O)CCCCCCC)S2 MOZHJALYAPTCFZ-UHFFFAOYSA-N 0.000 description 2
- XBLCAKKYMZVLPU-UHFFFAOYSA-N 2-hexylfuran Chemical compound CCCCCCC1=CC=CO1 XBLCAKKYMZVLPU-UHFFFAOYSA-N 0.000 description 2
- QNOZTNXXLYQRPC-UHFFFAOYSA-N 4-(2-octylthieno[3,2-b]thiophen-5-yl)-2-[4-(2-octylthieno[3,2-b]thiophen-5-yl)pyridin-2-yl]pyridine Chemical compound C=1C(C=2SC=3C=C(CCCCCCCC)SC=3C=2)=CC=NC=1C1=CC(C=2SC=3C=C(SC=3C=2)CCCCCCCC)=CC=N1 QNOZTNXXLYQRPC-UHFFFAOYSA-N 0.000 description 2
- GNCHJLGLCHMRCV-UHFFFAOYSA-N 4-(5-hexylfuran-2-yl)-2-[4-(5-hexylfuran-2-yl)pyridin-2-yl]pyridine Chemical compound O1C(CCCCCC)=CC=C1C1=CC=NC(C=2N=CC=C(C=2)C=2OC(CCCCCC)=CC=2)=C1 GNCHJLGLCHMRCV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 229910006404 SnO 2 Inorganic materials 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229910052745 lead Inorganic materials 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- SKRWFPLZQAAQSU-UHFFFAOYSA-N stibanylidynetin;hydrate Chemical compound O.[Sn].[Sb] SKRWFPLZQAAQSU-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- ARSMIBSHEYKMJT-UHFFFAOYSA-M 1,3-dimethylimidazolium iodide Chemical compound [I-].CN1C=C[N+](C)=C1 ARSMIBSHEYKMJT-UHFFFAOYSA-M 0.000 description 1
- MVDKKZZVTWHVMC-UHFFFAOYSA-N 2-hexadecylpropanedioic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C(O)=O MVDKKZZVTWHVMC-UHFFFAOYSA-N 0.000 description 1
- UUIMDJFBHNDZOW-UHFFFAOYSA-N 2-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC=N1 UUIMDJFBHNDZOW-UHFFFAOYSA-N 0.000 description 1
- KIIHBDSNVJRWFY-UHFFFAOYSA-N 4-bromo-2-(4-bromopyridin-2-yl)pyridine Chemical compound BrC1=CC=NC(C=2N=CC=C(Br)C=2)=C1 KIIHBDSNVJRWFY-UHFFFAOYSA-N 0.000 description 1
- GKCDKORPLHNARQ-UHFFFAOYSA-N 5-octylthieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=C(CCCCCCCC)S2 GKCDKORPLHNARQ-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229910016467 AlCl 4 Inorganic materials 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910020366 ClO 4 Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229910005191 Ga 2 O 3 Inorganic materials 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
- 229920012266 Poly(ether sulfone) PES Polymers 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- ASIIQTABPIPDFG-UHFFFAOYSA-L [Sn+2]=O.[F-].[F-] Chemical compound [Sn+2]=O.[F-].[F-] ASIIQTABPIPDFG-UHFFFAOYSA-L 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- ZJYYHGLJYGJLLN-UHFFFAOYSA-N guanidinium thiocyanate Chemical compound SC#N.NC(N)=N ZJYYHGLJYGJLLN-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000002159 nanocrystal Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- ZGNSERLDKONJKL-UHFFFAOYSA-N thieno[3,2-b]thiophene;thiophene Chemical compound C=1C=CSC=1.S1C=CC2=C1C=CS2 ZGNSERLDKONJKL-UHFFFAOYSA-N 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
- 238000004448 titration Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- OGZAPKLCAUALTI-UHFFFAOYSA-N tributyl-(2-octylthieno[3,2-b]thiophen-5-yl)stannane Chemical compound S1C([Sn](CCCC)(CCCC)CCCC)=CC2=C1C=C(CCCCCCCC)S2 OGZAPKLCAUALTI-UHFFFAOYSA-N 0.000 description 1
- JGMWITPXIMSEKS-UHFFFAOYSA-N tributyl-(5-hexylfuran-2-yl)stannane Chemical compound CCCCCCC1=CC=C([Sn](CCCC)(CCCC)CCCC)O1 JGMWITPXIMSEKS-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/344—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising ruthenium
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
-
- 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
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Hybrid Cells (AREA)
- Photovoltaic Devices (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008100504012A CN101235214B (zh) | 2008-02-27 | 2008-02-27 | 有机钌染料及染料敏化太阳能电池 |
| CN200810050401.2 | 2008-02-27 | ||
| PCT/IB2009/050800 WO2009107100A2 (en) | 2008-02-27 | 2009-02-27 | High molecular extinction coefficient metal dyes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011513530A JP2011513530A (ja) | 2011-04-28 |
| JP2011513530A5 JP2011513530A5 (enExample) | 2012-03-15 |
| JP5491419B2 true JP5491419B2 (ja) | 2014-05-14 |
Family
ID=39919136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010548237A Expired - Fee Related JP5491419B2 (ja) | 2008-02-27 | 2009-02-27 | 高分子吸光係数金属色素 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9716240B2 (enExample) |
| EP (1) | EP2257601B1 (enExample) |
| JP (1) | JP5491419B2 (enExample) |
| KR (1) | KR20100132508A (enExample) |
| CN (1) | CN101235214B (enExample) |
| WO (1) | WO2009107100A2 (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110265876A1 (en) * | 2008-11-11 | 2011-11-03 | Universität Ulm | Novel anchoring ligands for sensitizers of dye-sensitized photovoltaic devices |
| CN101412855B (zh) * | 2008-12-04 | 2011-09-28 | 中国科学院长春应用化学研究所 | 含推S,Se或Te电子基团的联吡啶钌染料及其在染料敏化太阳电池中的应用 |
| WO2011125024A1 (en) | 2010-04-05 | 2011-10-13 | Ecole Polytechnique Federale De Lausanne (Epfl) | Improved electrode |
| KR101050470B1 (ko) * | 2010-04-05 | 2011-07-20 | 삼성에스디아이 주식회사 | 루테늄 착체 및 이를 이용한 염료감응 태양전지 |
| JP5590552B2 (ja) * | 2010-04-13 | 2014-09-17 | 国立大学法人広島大学 | 色素増感型光電変換素子 |
| KR101175207B1 (ko) | 2010-05-18 | 2012-08-20 | 에스에프씨 주식회사 | 유기염료 및 이를 이용한 염료감응 태양전지 |
| KR101181262B1 (ko) * | 2010-05-18 | 2012-09-10 | 에스에프씨 주식회사 | 유기염료 및 이를 이용한 염료감응 태양전지 |
| KR101188803B1 (ko) | 2010-05-20 | 2012-10-09 | (주)씨에스엘쏠라 | 염료 감응 태양 전지용 루테늄계 염료 및 이로부터 제조된 염료 감응 태양 전지 |
| DE102010046412B4 (de) | 2010-09-23 | 2022-01-13 | Merck Patent Gmbh | Metall-Ligand Koordinationsverbindungen |
| DE102010054525A1 (de) | 2010-12-15 | 2012-04-26 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
| DE102010055902A1 (de) | 2010-12-23 | 2012-06-28 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
| JP6356060B2 (ja) | 2011-03-24 | 2018-07-11 | メルク パテント ゲーエムベーハー | 有機イオン性機能材料 |
| CN102201539A (zh) * | 2011-04-22 | 2011-09-28 | 华北电力大学 | 一种反向结构聚合物太阳电池及其制备方法 |
| KR101323866B1 (ko) * | 2011-04-29 | 2013-10-31 | (주)씨에스엘쏠라 | 신규한 염료 감응 태양 전지용 염료 및 이로부터 제조된 염료 감응 태양 전지 |
| EP2707911B1 (en) | 2011-05-12 | 2017-07-05 | Merck Patent GmbH | Compositions and electronic devices |
| TWI462916B (zh) * | 2011-05-16 | 2014-12-01 | Univ Nat Chiao Tung | 用於染料敏化太陽能電池的釕錯合物光敏染料 |
| DE102012016192A1 (de) | 2011-08-19 | 2013-02-21 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
| CN102417511B (zh) * | 2011-09-22 | 2013-08-21 | 西北师范大学 | 酰腙锌卟啉及其配合物的合成和应用 |
| WO2013084029A1 (en) | 2011-12-08 | 2013-06-13 | Ecole Polytechnique Federale De Lausanne (Epfl) | Semiconductor electrode comprising a blocking layer |
| US9394446B2 (en) | 2012-11-16 | 2016-07-19 | Tanaka Kikinzoku Kogyo K.K. | Method for recovering Ru complex dye from used dye solution |
| WO2014079532A1 (de) | 2012-11-20 | 2014-05-30 | Merck Patent Gmbh | Formulierung in hochreinem l?sungsmittel zur herstellung elektronischer vorrichtungen |
| EP2822009A1 (en) | 2013-07-01 | 2015-01-07 | Ecole Polytechnique Fédérale de Lausanne (EPFL) | Solar cell and process for producing the same |
| EP2846371A1 (en) | 2013-09-10 | 2015-03-11 | Ecole Polytechnique Fédérale de Lausanne (EPFL) | Inverted solar cell and process for producing the same |
| CN103554996B (zh) * | 2013-10-11 | 2016-03-02 | 华中科技大学 | 含阳离子的钌络合物染料及其制备的染料敏化太阳能电池 |
| EP2896660A1 (en) | 2014-01-16 | 2015-07-22 | Ecole Polytechnique Federale De Lausanne (Epfl) | Hole transporting and light absorbing material for solid state solar cells |
| EP2903047A1 (en) | 2014-01-31 | 2015-08-05 | Ecole Polytechnique Fédérale de Lausanne (EPFL) | Hole transporting and light absorbing material for solid state solar cells |
| EP2966703A1 (en) | 2014-07-11 | 2016-01-13 | Ecole Polytechnique Fédérale de Lausanne (EPFL) | Template enhanced organic inorganic perovskite heterojunction photovoltaic device |
| US20170301479A1 (en) | 2014-09-10 | 2017-10-19 | Ecole Polytechnique Federale De Lausanne (Epfl) | Photodetector |
| EP3065190A1 (en) | 2015-03-02 | 2016-09-07 | Ecole Polytechnique Fédérale de Lausanne (EPFL) | Small molecule hole transporting material for optoelectronic and photoelectrochemical devices |
| EP3157025A1 (en) | 2015-10-15 | 2017-04-19 | g2e glass2energy SA | Porphyrin-based sensitizer for dye-sensitized solar cell |
| LT6540B (lt) | 2016-09-19 | 2018-06-25 | Kauno technologijos universitetas | Skyles transportuojančios organinės molekulės, turinčios enamino grupių, skirtos optoelektroniniams bei fotoelektroniniams prietaisams |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2895409A1 (fr) * | 2005-12-23 | 2007-06-29 | Commissariat Energie Atomique | Complexes sensibilisateurs, leur procede de preparation, materiau hybride inorganique-organique semiconducteur les comprenant, et cellule photovoltaique comprenant ce materiau |
| JP4576494B2 (ja) | 2006-02-08 | 2010-11-10 | 島根県 | 光増感色素 |
| TWI319424B (en) * | 2006-05-11 | 2010-01-11 | Univ Nat Central | Photosensitizer dye |
| JP5466943B2 (ja) | 2007-08-08 | 2014-04-09 | 日本化薬株式会社 | パイ電子共役系を拡張した色素増感型太陽電池用増感色素 |
| EP2053618A1 (en) * | 2007-10-25 | 2009-04-29 | Sony Corporation | A dye including an anchoring group in its molecular structure |
| CN101910322A (zh) * | 2007-12-26 | 2010-12-08 | 株式会社东进世美肯 | 新型Ru-型敏化剂及其制备方法 |
-
2008
- 2008-02-27 CN CN2008100504012A patent/CN101235214B/zh not_active Expired - Fee Related
-
2009
- 2009-02-27 JP JP2010548237A patent/JP5491419B2/ja not_active Expired - Fee Related
- 2009-02-27 KR KR1020107021375A patent/KR20100132508A/ko not_active Ceased
- 2009-02-27 US US12/735,942 patent/US9716240B2/en not_active Expired - Fee Related
- 2009-02-27 WO PCT/IB2009/050800 patent/WO2009107100A2/en not_active Ceased
- 2009-02-27 EP EP09714128.7A patent/EP2257601B1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20110062541A1 (en) | 2011-03-17 |
| CN101235214B (zh) | 2012-07-04 |
| EP2257601B1 (en) | 2019-04-10 |
| EP2257601A2 (en) | 2010-12-08 |
| US9716240B2 (en) | 2017-07-25 |
| WO2009107100A2 (en) | 2009-09-03 |
| JP2011513530A (ja) | 2011-04-28 |
| CN101235214A (zh) | 2008-08-06 |
| WO2009107100A3 (en) | 2010-04-22 |
| KR20100132508A (ko) | 2010-12-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5491419B2 (ja) | 高分子吸光係数金属色素 | |
| JP5576298B2 (ja) | 有機増感剤 | |
| US8445697B2 (en) | Squarylium dyes including an anchoring group | |
| KR20110095307A (ko) | 염료-감응형 태양광 소자의 감응제를 위한 신규한 고정 리간드 | |
| Zou et al. | Molecular model of dye sensitized titanium oxides based on aryl-amine dye anchored titanium oxo clusters | |
| TW201112469A (en) | Novel organic dye and preparation thereof | |
| CN105980484B (zh) | 用于染料敏化太阳能电池的基于卟啉的敏化剂 | |
| US7964790B2 (en) | Dye for photoelectric device and photoelectric device comprising the dye | |
| CN101950674A (zh) | 染料敏化太阳能电池用染料及含其的染料敏化太阳能电池 | |
| JP5794589B2 (ja) | 色素増感太陽電池及び増感色素 | |
| TW201114844A (en) | Novel organic dye and preparation thereof | |
| US7863448B2 (en) | Dye for photoelectronic device, photoanode comprising the dye and photoelectronic device employing the photoanode | |
| KR100969676B1 (ko) | 신규한 줄로리딘계 염료 및 이의 제조방법 | |
| CN101412855B (zh) | 含推S,Se或Te电子基团的联吡啶钌染料及其在染料敏化太阳电池中的应用 | |
| CN101663360A (zh) | 贵金属钌型敏化剂及其制备方法 | |
| JP7653270B2 (ja) | 増感色素、光電変換用増感色素組成物、光電変換素子および色素増感太陽電池 | |
| El Bitar Nehme | Co-adsorption of complementary pyridyl and carboxylic acid based dyes in dye-sensitized solar cells. | |
| TWI470034B (zh) | 染料化合物及用此染料化合物製作之光電元件 | |
| TWI503320B (zh) | 光敏染料及其應用 | |
| Bisht | NIR active squaraine dyes for dye-sensitized solar cells: modulating aggregation, orientation and electronic properties of the dyes | |
| KR20070072214A (ko) | 루테늄 착화합물 및 이를 채용한 염료감응 태양전지 | |
| MIDYA | DESIGN AND SYNTHESIS OF DONOR ACCEPTOR HYBRIDIZED SMALL MOLECULES AND GRAPHENE DERIVATIVES FOR PHOTOVOLTAIC AND OPTICAL STUDIES | |
| JP2012104428A (ja) | 色素増感太陽電池及びその光陽極 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120125 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120125 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130917 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20131216 |
|
| 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: 20140128 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140227 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5491419 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |