WO2008059770A1 - Method for collecting metal - Google Patents
Method for collecting metal Download PDFInfo
- Publication number
- WO2008059770A1 WO2008059770A1 PCT/JP2007/071866 JP2007071866W WO2008059770A1 WO 2008059770 A1 WO2008059770 A1 WO 2008059770A1 JP 2007071866 W JP2007071866 W JP 2007071866W WO 2008059770 A1 WO2008059770 A1 WO 2008059770A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- metal
- solution
- organic
- collecting
- light
- Prior art date
Links
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 146
- 239000002184 metal Substances 0.000 title claims abstract description 145
- 238000000034 method Methods 0.000 title claims abstract description 69
- 150000002736 metal compounds Chemical class 0.000 claims abstract description 104
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000002904 solvent Substances 0.000 claims abstract description 37
- 230000005281 excited state Effects 0.000 claims abstract description 35
- 239000002253 acid Substances 0.000 claims abstract description 28
- 150000004696 coordination complex Chemical class 0.000 claims description 46
- 239000013110 organic ligand Substances 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 36
- 239000000725 suspension Substances 0.000 claims description 31
- 238000010438 heat treatment Methods 0.000 claims description 26
- 229910044991 metal oxide Inorganic materials 0.000 claims description 21
- 150000004706 metal oxides Chemical class 0.000 claims description 21
- 239000012298 atmosphere Substances 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 230000001678 irradiating effect Effects 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 abstract description 30
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 abstract description 27
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract description 20
- 150000002739 metals Chemical class 0.000 abstract description 12
- 229910052697 platinum Inorganic materials 0.000 abstract description 9
- -1 iridium or platinum Chemical class 0.000 abstract description 7
- 239000000243 solution Substances 0.000 description 87
- 150000001875 compounds Chemical class 0.000 description 55
- 229910052761 rare earth metal Inorganic materials 0.000 description 26
- 150000002910 rare earth metals Chemical class 0.000 description 26
- 125000003118 aryl group Chemical group 0.000 description 25
- 230000005283 ground state Effects 0.000 description 25
- 239000001257 hydrogen Substances 0.000 description 25
- 229910052739 hydrogen Inorganic materials 0.000 description 25
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 25
- 125000000217 alkyl group Chemical group 0.000 description 24
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 24
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 24
- 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 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
- 125000001624 naphthyl group Chemical group 0.000 description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 150000002894 organic compounds Chemical class 0.000 description 18
- 239000000463 material Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 238000005868 electrolysis reaction Methods 0.000 description 15
- 229910052723 transition metal Inorganic materials 0.000 description 15
- 150000003624 transition metals Chemical class 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 230000003647 oxidation Effects 0.000 description 12
- 238000007254 oxidation reaction Methods 0.000 description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 9
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 8
- 239000003513 alkali Substances 0.000 description 7
- 150000003863 ammonium salts Chemical class 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 150000004714 phosphonium salts Chemical class 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 5
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 5
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 230000000737 periodic effect Effects 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 4
- 229910002651 NO3 Inorganic materials 0.000 description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910000510 noble metal Inorganic materials 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- AFINAILKDBCXMX-PBHICJAKSA-N (2s,3r)-2-amino-3-hydroxy-n-(4-octylphenyl)butanamide Chemical compound CCCCCCCCC1=CC=C(NC(=O)[C@@H](N)[C@@H](C)O)C=C1 AFINAILKDBCXMX-PBHICJAKSA-N 0.000 description 3
- 0 *NCCN(*)C=S Chemical compound *NCCN(*)C=S 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 3
- 229910052769 Ytterbium Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 150000004292 cyclic ethers Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- QAWTYRYXDYHQNU-UHFFFAOYSA-N diazathiane Chemical class NSN QAWTYRYXDYHQNU-UHFFFAOYSA-N 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000008442 polyphenolic compounds Chemical class 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- 150000003585 thioureas Chemical class 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical class C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910052691 Erbium Inorganic materials 0.000 description 2
- 229910052693 Europium Inorganic materials 0.000 description 2
- 229910052779 Neodymium Inorganic materials 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229940006460 bromide ion Drugs 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004453 electron probe microanalysis Methods 0.000 description 2
- 230000005274 electronic transitions Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 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
- 239000011777 magnesium Substances 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- XGCDBGRZEKYHNV-UHFFFAOYSA-N 1,1-bis(diphenylphosphino)methane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)C1=CC=CC=C1 XGCDBGRZEKYHNV-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- NSKAVCQOVDGECI-UHFFFAOYSA-N 2-(4-fluorophenyl)quinoxaline Chemical compound C1=CC(F)=CC=C1C1=CN=C(C=CC=C2)C2=N1 NSKAVCQOVDGECI-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- 229910017073 AlLi Inorganic materials 0.000 description 1
- OAJNZFCPJVBYHB-UHFFFAOYSA-N C1OCCOc(cccc2)c2OCCOC1 Chemical compound C1OCCOc(cccc2)c2OCCOC1 OAJNZFCPJVBYHB-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
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- 206010039509 Scab Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000004380 ashing Methods 0.000 description 1
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- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000011243 crosslinked material Substances 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
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- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001290 polyvinyl ester Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B7/00—Working up raw materials other than ores, e.g. scrap, to produce non-ferrous metals and compounds thereof; Methods of a general interest or applied to the winning of more than two metals
- C22B7/006—Wet processes
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B11/00—Obtaining noble metals
- C22B11/04—Obtaining noble metals by wet processes
- C22B11/042—Recovery of noble metals from waste materials
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B3/00—Extraction of metal compounds from ores or concentrates by wet processes
- C22B3/04—Extraction of metal compounds from ores or concentrates by wet processes by leaching
- C22B3/06—Extraction of metal compounds from ores or concentrates by wet processes by leaching in inorganic acid solutions, e.g. with acids generated in situ; in inorganic salt solutions other than ammonium salt solutions
- C22B3/10—Hydrochloric acid, other halogenated acids or salts thereof
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B60/00—Obtaining metals of atomic number 87 or higher, i.e. radioactive metals
- C22B60/02—Obtaining thorium, uranium, or other actinides
- C22B60/0204—Obtaining thorium, uranium, or other actinides obtaining uranium
- C22B60/0217—Obtaining thorium, uranium, or other actinides obtaining uranium by wet processes
- C22B60/0221—Obtaining thorium, uranium, or other actinides obtaining uranium by wet processes by leaching
- C22B60/0226—Obtaining thorium, uranium, or other actinides obtaining uranium by wet processes by leaching using acidic solutions or liquors
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B61/00—Obtaining metals not elsewhere provided for in this subclass
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/40—Thermal treatment, e.g. annealing in the presence of a solvent vapour
-
- 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
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/01—Chemical elements
- H01L2924/01078—Platinum [Pt]
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P10/00—Technologies related to metal processing
- Y02P10/20—Recycling
Definitions
- the present invention relates to a method for collecting a metal contained in an electroluminescent light-emitting element.
- a basic structure of these light-emitting elements is that a light-emitting substance is sandwiched between a pair of electrodes. The application of voltage to this element enables the light-emitting substance to emit light.
- Such light-emitting elements are of a self-luminous type, they have advantages such as having higher visibility compared with liquid crystal displays and no need of back lights. Therefore, these light-emitting elements are suitable for flat panel display elements. Another significant advantage is that such light-emitting elements can be manufactured to be thin and light-weight. Another feature is that these light-emitting elements have extremely high response speed. [0004] Since these light-emitting elements can be formed in a film form, planar light emission can easily be obtained by forming elements with large areas. Planar light emission is hard to obtain from point-light sources such as incandescent lamps and LEDs, or line sources such as fluorescent lights. Therefore, these light-emitting elements have a high utility value as surface illuminants. The surface illuminants can be applied to lighting and the like. [0005]
- Electroluminescent light-emitting elements are largely classified into two types according to whether the light-emitting substance is an organic compound or an inorganic compound. Here the light-emitting substance which is the organic compound is described. [0006]
- the application of voltage to the light-emitting element makes electrons injected from an electrode into a layer containing the light-emitting organic compound, holes injected from the other electrode into the layer containing the light-emitting organic compound, and then electric current flows. Then, the recombination of these carriers (electrons and holes) excites the light-emitting organic compound.
- the light-emitting organic compound emits light in returning to a ground state. Because of such mechanism, such a light-emitting element is referred to as a light-emitting element of a current excitation type.
- Excitation states of an organic compound can be classified into two types: a singlet excited state (S * ) and a triplet excited state (T * ).
- S * singlet excited state
- T * triplet excited state
- a ground state of a light-emitting organic compound is usually a singlet state. Therefore, light emission in returning to a singlet ground state from a singlet excited state (S * ) is referred to as fluorescence since it is caused by electronic transition between the same multiplets. On the other hand, light emission in returning to a singlet ground state from a triplet excited state (T ) is referred to as phosphorescence since it is caused by electronic transition between different multiplets. In most of the compounds which emit fluorescence (hereinafter referred to as "fluorescent compounds”), only fluorescence is observed and phosphorescence is not at room temperature.
- Non-Patent Document 1 a complex containing iridium (Ir) as a central metal is used in general as in Non-Patent Document 1.
- iridium is a noble metal and exists in crusts in extremely small amounts. Accordingly, there arises a problem of resource depletion of iridium, as light-emitting devices and electronic appliances using light-emitting elements come into wide use. In addition, in order to reduce adverse impact on the environment, methods for reusing iridium are needed.
- An object of the present invention is to provide a method for collecting a scarce metal such as iridium from a light-emitting element no longer needed.
- An aspect of the present invention is a method for collecting metal from an organic metal compound, including a step of ashing an EL layer of a light-emitting element containing an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature through heat treatment.
- the EL layer denotes a layer provided between a pair of electrodes in a light-emitting element.
- Another aspect of the present invention is a method for collecting a metal from an organic metal compound, including a step of performing a heat treatment at a temperature of 800 0 C or higher on an EL layer of a light-emitting element containing an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature.
- Another aspect of the present invention is a method for collecting a metal from an organic metal compound, including a step of performing a heat treatment at a temperature of 800 0 C or higher under atmospheric air or an oxygen atmosphere on an
- Another aspect of the present invention is a method for collecting a metal from an organic metal compound, including a step of performing a heat treatment on an EL layer of a light-emitting element containing an organic metal compound at a temperature of 800 0 C or higher under a reducing atmosphere or with a reducing agent, and collecting a metal oxide which remains after the heat treatment.
- the remaining metal or the remaining metal oxide may be treated with acid water after the heat treatment, and a solution in which a metal compound containing the metal which constitutes the organic metal compound is dissolved may be obtained.
- acid water water containing any of the following can be used: hydrogen chloride, hydrogen bromide, hydrogen fluoride, hydrogen iodide, sulfuric acid, nitric acid, nitrous acid, and acetic acid.
- a step of oxidizing the solution in which the metal compound is dissolved may be included.
- a step of reacting the metal contained in the solution in which the metal compound is dissolved and an organic ligand to form a metal complex may be included.
- a step of reacting the metal contained in the solution in which the metal compound is dissolved and an organic ligand to form a metal complex, and a step of extracting the metal complex with a solvent which dissolves the metal complex may be included. In this case, it is preferable that the solvent be not uniformly mixed with water.
- Another aspect of the present invention is a method for collecting a metal from an organic metal compound, including a first step of exposing an EL layer by detaching one in a pair of electrodes included in a light-emitting element from the light-emitting element in which the EL layer containing an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature is formed between the pair of electrodes, and a second step of irradiating a solution in which the EL layer is dissolved in a solvent with microwaves.
- Another aspect of the present invention is a method for collecting a metal from an organic metal compound, including a first step of exposing an EL layer by detaching one in a pair of electrodes included in a light-emitting element from the light-emitting element in which the EL layer containing an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature is formed between the pair of electrodes, and a second step of adding an organic compound to a solution in which the EL layer is dissolved in a solvent and performing microwave irradiation.
- a third step may be included in which a solution in which the metal compound containing the metal which constitutes the organic metal compound is dissolved or a suspension in which the metal compound is suspended is formed by treating the solution irradiated with the microwaves with a solvent containing acid water.
- Another aspect of the present invention is a method for collecting a metal from an organic metal compound, including a first step of exposing an EL layer by detaching one in a pair of electrodes included in a light-emitting element from the light-emitting element in which the EL layer containing an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature is formed between the pair of electrodes, and a second step of forming a solution in which the metal compound containing the metal which constitutes the organic metal compound is dissolved or a suspension in which the metal compound is suspended, by treating the EL layer of the light-emitting element with a solvent containing acid water.
- water containing any of the following can be used: hydrogen chloride, hydrogen bromide, hydrogen fluoride, hydrogen iodide, sulfuric acid, nitric acid, nitrous acid, and acetic acid.
- a step of oxidizing the solution in which the metal compound is dissolved or the suspension in which the metal complex is suspended may be included.
- a step of forming a metal complex by reacting the metal contained in the solution in which the metal compound is dissolved or the suspension in which the metal complex is suspended and an organic ligand may be included.
- a step of forming a metal complex by reacting the metal contained in the solution in which the metal compound is dissolved or the suspension in which the metal complex is suspended and an organic ligand, and a step of extracting the metal complex using a solvent which dissolves the metal complex may be included.
- the organic ligand is supported by a high molecular compound
- the metal complex may be formed by mixing the organic ligand supported by the high molecular compound and the solution or a mixture containing the metal compound.
- the organic ligand be any of the following: an amine derivative, an ethylenediamine derivative, a triethylenediamine derivative, an ethylenediaminethiocarboaldehyde derivative, a phenol derivative, a polyphenol derivative, a thiol derivative, a cyclic thiol derivative, an ether derivative, a cyclic ether derivative, a uracil derivative, an amide derivative, ammonium salt, a pyridine derivative, an amino sulfide derivative, an aniline derivative, a phosphoric acid derivative, phosphonium salt, a phosphine oxide derivative, a thiourea derivative, a benzothiazole derivative, or a thiocarbonyl derivative.
- the metal belong to any of the groups
- the metal be Ir, Pt, Ru, or Re. Furthermore, it is preferable that the metal be a rare earth metal.
- FIG 1 is a diagram illustrating a light-emitting element.
- This embodiment mode describes a method for collecting a metal atom from a light-emitting element containing an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature.
- FIG 1 shows a structure of a general light-emitting element.
- the light-emitting element shown in FIG 1 is formed over a substrate 201 and includes a first electrode 202, an EL layer 203, and a second electrode 204.
- the EL layer 203 is sandwiched between the first electrode 202 and the second electrode 204, and contains an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature.
- the EL layer 203 contains a metal belonging to any of the groups 7 to 11 in the periodic table or a rare earth metal. It is preferable in particular that the metal be Ir, Pt, Ru, or Re, which is used often in light-emitting elements. These metals are noble metals.
- noble metals exist in extremely small amounts and are expensive, collecting them from light-emitting elements can significantly contribute to reduction in cost.
- Ir, Pt, Ru, and Re are commonly used as organic metal compounds which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature, and can be utilized efficiently by collecting them from light-emitting elements.
- the organic metal compounds shown above include a metal belonging to any of the groups 7 to 11 in the periodic table or a rare earth metal. Resources can be utilized efficiently by collecting the metal belonging to any of the groups 7 to 11 in the periodic table or the rare earth metal from light-emitting elements containing these organic metal compounds.
- organic metal compounds containing Ir as a central metal are commonly used in light-emitting elements.
- organic metal compounds having the following partial structures are given as examples.
- organic metal compounds having the above partial structures and the following ligand are also commonly used.
- the first electrode 202 and the second electrode 204 contain various metals, alloys, conductive compounds, and mixtures thereof, and the like.
- a transparent conductive film made of indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide (IZO), or the like can be used for an electrode through which light is extracted.
- various conductive materials such as gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), or aluminum (Al) can be used.
- an element belonging to the group 1 or 2 in the periodic table i.e.
- an alkali metal such as lithium (Li) and cesium (Cs)
- an alkaline earth metal such as magnesium (Mg), calcium (Ca), and strontium (Sr)
- an alloy containing these elements MgAg, AlLi, or the like
- a rare earth metal such as europium (Eu), and ytterbium (Yb); alloys containing these elements; or the like can be used.
- a material which emits visible light in returning to a singlet ground state from a triplet excited state at room temperature is extracted from a light-emitting element having such a structure described above. First, the first electrode 202 or the second electrode 204 is detached from the light-emitting element.
- the electrode can be detached by, for example, putting adhesive tape on the electrode and peeling off the tape afterwards. In particular, the electrode which is formed on a region smaller than the EL layer, can easily be detached.
- a versatile resin such as an epoxy resin, a polyimide resin, or a phenol resin can be used as the resin.
- the electrode may be removed by acid treatment or alkaline treatment when the electrode contains a material which is reactive with acid or alkali, such as aluminum (Al).
- the EL layer is extracted.
- Various methods can be used to take out the EL layer.
- an organic compound contained in the EL layer may be extracted in a state of solution after being dissolved in a solvent.
- a solvent of aromatic hydrocarbon such as toluene, xylene, and tetralin; aromatic hydrocarbon containing halogen, such as dichlorobenzene and chlorobenzene; aliphatic halogenated hydrocarbon series such as dichloromethane and chloroform; or the like are given as examples of the solvent which can dissolve the organic compound contained in the EL layer.
- aromatic hydrocarbon containing halogen such as dichlorobenzene and chlorobenzene
- aliphatic halogenated hydrocarbon series such as dichloromethane and chloroform
- a solvent of ether series such as tetrahydrofuran and diethyl ether may also be used.
- the EL layer need not completely be dissolved in the solvent and may be extracted, dissolved partially in a state of a mixture.
- a metal atom which constitutes an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature is collected from the solution or the mixture containing various compounds which constitute the EL layer.
- a first method is as follows: the solution or the mixture containing various compounds which constitute the EL layer is subjected to heat treatment and ashed.
- the heat treatment may be carried out under any of the following: atmospheric air, an oxygen atmosphere, or a reducing atmosphere. Further, the heat treatment may be carried out with a reducing agent. When the heat treatment is carried out under atmospheric air or an oxygen atmosphere, a metal oxide can be obtained. When the heat treatment is carried out under a reducing atmosphere, e.g. a H 2 gas atmosphere, a metal can be obtained. Furthermore, when the heat treatment is carried out with a reducing agent such as palladium carbon (PdC) or aluminum (Al), a metal can be obtained.
- a reducing agent such as palladium carbon (PdC) or aluminum (Al)
- the heat treatment be carried out under a reducing atmosphere since metals can be separated with more ease compared with metal oxides by utilizing the difference in melting points.
- the heat treatment be carried out at a temperature of 800 0 C or higher, more preferably 1000 0 C or higher, in order to prevent an organic matter from remaining.
- the metal or the metal oxide obtained by the above method is separated.
- the metal or the metal oxide can be separated by utilizing the difference in melting points of the metals, for example.
- the targeted metal atom can be collected: i.e., the metal atom can be collected from the organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature.
- the targeted metal atom can also be collected by using the following method.
- the metal or the metal oxide obtained by the above method is treated with acid water: that is to say, it is mixed with acid water and stirred.
- the metal or the metal oxide obtained by the above heat treatment is reacted with water containing hydrogen chloride, hydrogen bromide, hydrogen fluoride, acetic acid, nitric acid, nitrous acid, sulfuric acid, hydrogen iodide, or the like.
- Heat treatment or oxidation treatment may be carried out if necessary.
- Oxidation treatment may be carried out with oxygen by introducing air, for example.
- oxidation treatment may be carried out by mixing the metal or the metal oxide with hydrogen peroxide, whereby the metal or the metal oxide is oxidized.
- oxidation treatment may be carried out with halogen such as iodine, chlorine, or bromine.
- a metal compound of a transition metal belonging to any of the groups 7 to 11 or that of a rare earth metal can be obtained.
- a solution of chloride, bromide, fluoride, iodide, sulfate, sulfide, nitrate, nitrite, acetate, or oxide can be obtained.
- Chloride, bromide, fluoride, iodide, sulfate, sulfide, nitrate, nitrite, and acetate are preferable since the solubility thereof is high.
- the solution which is obtained in this manner and in which the metal compound is dissolved may be subjected to alkali treatment. Through the alkali treatment, a hydroxide, ammonium salt, phosphonium salt, and sulfonium salt of the metal can be produced, and a solution thereof can be obtained. Ammonium salt, phosphonium salt, and sulfonium salt are preferable since the solubility thereof is high. [0076] After forming the solution of the metal compound which contains a transition metal belonging to any of the groups 7 to 11 or a rare earth metal as a central metal, the metal compound is separated from the solution. In concrete terms, there are a method in which electrolysis is carried out and a method in which the solution is treated with a solution containing an organic ligand. [0077]
- the transition metal belonging to any of the groups 7 to 11 or the rare earth metal is deposited on or near an electrode by connecting the solution of the metal compound containing the transition metal belonging to any of the groups 7 to 11 or the rare earth metal as a central metal to a DC power source. Even if another kind of metal is contained in the solution, it is possible to separate only the targeted metal with ease by carrying out the electrolysis since each metal has a different ionization tendency.
- various solvents can be used, e.g. water, acetonitrile, or molten salt.
- the organic ligand mentioned here is a molecule which can form a plurality of coordinate bonds with the metal, and is also referred to as a chelate ligand.
- the following substances can be given as examples: an amine derivative, an ethylenediamine derivative, a triethylenediamine derivative, an ethylenediaminethiocarboaldehyde derivative, a phenol derivative, a polyphenol derivative, a thiol derivative, a cyclic thiol derivative, an ether derivative, a cyclic ether derivative, a uracil derivative, an amide derivative, ammonium salt, a pyridine derivative, an amino sulfide derivative, an aniline derivative, a phosphoric acid derivative, phosphonium salt, a phosphine oxide derivative, a thiourea derivative, a benzothiazole derivative, a thiocarbonyl derivative, and the like.
- These compounds may be supported by polymer compounds.
- polymer compounds those which contain polystyrene, polyacrylic acid ester, polymethacrylic acid ester, polyvinyl ether, polyvinyl ester, or the like as a principal chain can be used.
- the organic ligand described above may be incorporated into a side chain of a cross-linked material of these polymer compounds.
- a compound represented by General Formula (1), a compound represented by General Formula (2), and a compound represented by General Formula (3) are given as an amine derivative, an ethylenediamine derivative, and a triethylenediamine derivative, respectively.
- R to R each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- R 1 to R 4 each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- R 1 to R 5 each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- R 1 to R 3 each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- a compound represented by General Formula (5), a compound represented by General Formula (6), and a compound represented by General Formula (7) are given as a phenol derivative and a polyphenol derivative.
- R 1 represents hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- R 1 represents hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given examples.
- a compound represented by General Formula (10), a compound represented by General Formula (11), and a compound represented by General Formula (12) are given as an ether derivative and a cyclic ether derivative.
- R 1 represents hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- R 1 represents hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- R 1 and R 2 each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- R 1 to R 3 each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- R 1 to R 6 each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- B Cl, SO 4 , CIO 4 , CH 3 CO 2 , Br, I, CO 3 , HCO 3 , HSO 4
- R 1 to R 4 each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- B " represents any of the following: a chloride ion, a sulfate ion, a perchlorate ion, an acetate ion, a bromide ion, an iodide ion, a carbonate ion, a hydrogen carbonate ion, and a sulfite ion.
- R 1 and R 2 each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- R 1 represents hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- R 1 represents hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- R 1 to R 3 each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- a compound represented by General Formula (23), a compound represented by General Formula (24), and a compound represented by General Formula (25) are given as a phosphoric acid derivative, phosphonium salt, and a phosphine oxide derivative.
- R 1 to R 3 each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- R 1 to R 3 each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- B Cl, SO 4 , CIO 4 , CH 3 CO 2 , Br 1 I 1 CO 3 , HCO 3 , HSO 4
- R 1 to R 4 each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- B " represents any of the following: a chloride ion, a sulfate ion, a perchlorate ion, an acetate ion, a bromide ion, an iodide ion, a carbonate ion, a hydrogen carbonate ion, and a sulfite ion.
- R 1 to R 4 each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- R 1 represents hydrogen, an aryl group, or an alkoxy group.
- R 1 and R 2 each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- R 1 to R 3 each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- R 1 and R 2 each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- R 1 to R 3 each independently represent hydrogen, an alkyl group, or an aryl group.
- a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
- the method described above makes it possible to separate a central metal which constitutes a material that emits visible light in returning to a singlet ground state from a triplet excited state at room temperature and is contained in a light-emitting element, i.e. a metal belonging to any of the groups 7 to 11 or a rare earth metal.
- resources of the metal belonging to any of the groups 7 to 11 or the rare earth metal such as iridium (Ir) and platinum (Pt), which are scarce metals, can be utilized efficiently.
- a central metal which constitutes a material that emits visible light in returning to a singlet ground state from a triplet excited state at room temperature can be collected also from a light-emitting element in which a plurality of EL layers are stacked with a charge-generating layer interposed therebetween/thereamong.
- This embodiment mode explains a method for collecting a metal atom, which is different from the method described in Embodiment Mode 1.
- the solution in which the EL layer is dissolved in a solvent, or a mixture in which the EL layer is partially dissolved in a solvent is irradiated with microwaves.
- the microwaves may be adjusted so that the organic metal compound which is contained in the EL layer and can emit visible light in returning to a singlet ground state to a triplet excited state at room temperature can decompose.
- the solution or the mixture can also be irradiated with light in microwave irradiation.
- the light irradiation makes the organic metal compound in an excited state and can promote further decomposition.
- an organic compound may be added in microwave irradiation. Acetylacetone, picolinic acid, pyridine, and the like are given as the organic compound.
- Adding the organic compound can promote the decomposition of the organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature. It is preferable that a solvent used in microwave irradiation have high polarity. Using the high-polar solvent enables the efficient decomposition of the organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature since the value of generated heat increases in microwave irradiation. Glycerol, 2-ethoxyethanol, ethylene glycol, dichloromethane, or the like can be given as the high-polar solvent.
- ionic liquid of 1 -butyl-3 -methylimidazoliumhexafluorophosphate, l-butyl-3-methylimidazoliumtetrafluoroborate, or the like may be used. Furthermore, water may be added to these solvents as well.
- the solution or the mixture containing the decomposed matter which is obtained as described above is treated with acid water. That is to say, the solution or the mixture is mixed with acid water and stirred.
- the solution or the mixture containing the decomposed matter is reacted with water containing hydrogen chloride, hydrogen bromide, hydrogen fluoride, acetic acid, nitric acid, nitrous acid, sulfuric acid, hydrogen iodide, or the like.
- Heat treatment or oxidation treatment may be carried out if necessary. Oxidation treatment may be carried out with oxygen by introducing air, for example. Further, oxidation treatment may be carried out by mixing the solution or the mixture with hydrogen peroxide, whereby the solution or the mixture is oxidized.
- oxidation treatment may be carried out with halogen such as iodine, chlorine, and bromine.
- halogen such as iodine, chlorine, and bromine.
- a metal compound which contains a transition metal belonging to any of the groups 7 to 11 or that of a rare earth metal as a central metal can be obtained.
- chloride, bromide, fluoride, iodide, sulfate, sulfide, nitrate, nitrite, acetate, or oxide can be obtained.
- the solution which is obtained in this manner and in which the metal compound is dissolved or a suspension which is obtained in this manner and in which the metal compound is suspended may be treated with alkali. Through the alkali treatment, a hydroxide, ammonium salt, phosphonium salt, and sulfonium salt of the metal can be produced, and a solution thereof or a suspension thereof can be obtained.
- the metal compound After forming the solution or the suspension containing the metal compound which contains a transition metal belonging to any of the groups 7 to 11 or a rare earth metal as a central metal, the metal compound is separated from the solution or the suspension.
- electrolysis there are a method in which electrolysis is carried out and a method in which the solution or the suspension is treated with a solution containing an organic ligand. Electrolysis can preferably be employed for the solution. Treatment with a solution containing an organic ligand can be preferably employed both for the solution and the suspension.
- the transition metal belonging to any of the groups 7 to 11 or the rare earth metal is deposited on or near an electrode by connecting the solution of the metal compound containing the transition metal belonging to any of the groups 7 to 11 or the rare earth metal as a central metal to a DC power source. Even if another kind of metal is contained in the solution, it is possible to separate only the targeted metal with ease by carrying out the electrolysis since each metal has a different ionization tendency.
- various solvents can be used, e.g. water, acetonitrile, and molten salt.
- the solution or the suspension containing the metal compound which contains the transition metal belonging to any of the groups 7 to 11 or the rare earth metal as a central metal is treated with the solution containing the organic ligand
- a method can be given in which the solution containing the organic ligand is added to the solution or the suspension containing the metal compound, whereby the metal compound and the organic ligand are reacted with each other to form a metal complex, and then the metal complex is extracted with a solvent which dissolves the metal complex.
- the solvent which dissolves the metal complex be not uniformly mixed with water.
- the organic ligand the organic ligand described in Embodiment Mode 1 can be used.
- the targeted metal can be separated.
- a solution containing an organic ligand to the solution or the mixture containing the decomposed matter
- the metal contained in the decomposed matter and the organic ligand are reacted with each other to form a metal complex, so that the metal complex can be extracted with a solvent which dissolves the metal complex.
- the organic ligand the organic ligand described in Embodiment Mode 1 can be used.
- the method described above makes it possible to separate a central metal which constitutes a material that emits visible light in returning to a singlet ground state from a triplet excited state at room temperature and is contained in a light-emitting element, i.e. a metal belonging to any of the groups 7 to 11 or a rare earth metal.
- resources of the metal belonging to any of the groups 7 to 11 or the rare earth metal such as indium (Ir) and platinum (Pt), which are scarce metals, can be utilized efficiently.
- This embodiment mode explains a method for collecting a metal atom, which is different from the methods described in Embodiment Mode 1 and Embodiment Mode 2.
- an EL layer is extracted and then a solution or a mixture containing various compounds which constitute the EL layer is formed.
- the solution in which the EL layer is dissolved in a solvent, or the mixture in which the EL layer is partially dissolved in a solvent is treated with acid water. That is to say, the solution or the mixture is mixed with acid water and stirred.
- the organic compounds which constitute the EL layer is reacted with water containing hydrogen chloride, hydrogen bromide, hydrogen fluoride, acetic acid, nitric acid, nitrous acid, sulfuric acid, hydrogen iodide, or the like.
- Heat treatment or oxidation treatment may be carried out if necessary. Oxidation treatment may be carried out with oxygen by introducing air, for example. Further, oxidation treatment may be carried out by mixing the solution or the metal mixture with hydrogen peroxide, whereby the solution or the mixture is oxidized. Furthermore, oxidation treatment may be carried out with halogen such as iodine, chlorine, and bromine. Still furthermore, microwave irradiation may be carried out as the heat treatment.
- a metal compound of a transition metal belonging to any of the groups 7 to 11 or that of a rare earth metal can be obtained.
- chloride, bromide, fluoride, iodide, sulfate, sulfide, nitrate, nitrite, acetate, or oxide can be obtained.
- the solution which is obtained in this manner and in which the metal compound is dissolved or a suspension which is obtained in this manner and in which the metal compound is suspended may be treated with alkali.
- alkali treatment a hydroxide, ammonium salt, phosphonium salt, and sulfonium salt of the metal can be produced, and a solution thereof or a suspension thereof can be obtained.
- the transition metal belonging to any of the groups 7 to 11 or the rare earth metal is deposited on or near an electrode by connecting the solution of the metal compound containing the transition metal belonging to any of the groups 7 to 11 or the rare earth metal as a central metal to a DC power source. Even if another kind of metal is contained in the solution, it is possible to separate only the targeted metal with ease by carrying out the electrolysis since each metal has a different ionization tendency.
- various solutions can be used, e.g. water, acetonitrile, and molten salt.
- the metal compound and the organic ligand are reacted with each other to form metal complex, and then the metal complex can be extracted with a solvent which dissolves the metal complex.
- the solvent which dissolves the metal complex it is preferable that the solvent which dissolves the metal complex be not uniformly mixed with water.
- the organic ligand the organic ligand described in Embodiment Mode 1 can be used.
- the method described above makes it possible to separate a central metal which constitutes a material that emits visible light in returning to a singlet ground state from a triplet excited state at room temperature and is contained in a light-emitting element, i.e. a metal belonging to any of the groups 7 to 11 or a rare earth metal.
- resources of the metal belonging to any of the groups 7 to 11 or the rare earth metal such as iridium (Ir) and platinum (Pt), which are scarce metals, can be utilized efficiently.
- An iridium complex is often used for a light-emitting element because it can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature and can accomplish high light emission efficiency.
- iridium which is a noble metal
- an electrode of the light-emitting element may be detached using tape or the like, and then an EL layer of the light-emitting element may be dissolved in an organic solvent.
- organic compounds can be contained in addition to the iridium complex because materials other than a light-emitting material (e.g. a hole transport material, an electron transport material, a host material for dispersing dopant, and the like) are also usually used for a light-emitting element.
- a compound containing iridium can be separated from a mixed solution in which three kinds of substances are dissolved: the dissolved substances are an iridium complex, a substance that can be used as a hole transport material or a host material, and a substance that can be used as an electron transport material or a host material [0182] ⁇ Step 1: Making a mixed solution> 20 mg of
- NPB 4,4'-bis[iV-(l-naphthyl)-N-phenylamino]biphenyl
- AIq 3 tris(8-quinolinolato)aluminum(III)
- the microwave irradiation is carried out using a microwave synthesis apparatus (Discover: made by CEM Corporation).
- the black powder obtained in the step 2 is analyzed by electron probe X-ray microanalysis (EPMA).
- EPMA electron probe X-ray microanalysis
- elements detected are carbon (C), iridium (Ir), fluorine (F), nitrogen (N), chlorine (Cl), and oxygen (O) (in descending order of detected amounts). From this result, it is confirmed that iridium is able to be collected from the mixed solution containing [Ir(Fdpq) 2 (acac)], NPB and AIq 3 .
- iridium is able to be separated from the solution containing aluminum deriving from AIq 3 and iridium deriving from [Ir(Fdpq) 2 (acac)] as metal elements by the above method. [0185]
Abstract
It is an object of the present invention to collect a scarce metal such as iridium from a light-emitting element which is no longer used. A method for collecting a metal is provided in which an organic metal compound which can emit visible light from a triplet excited state at room temperature is heated, or an EL layer of a light-emitting layer containing an organic metal compound which can emit visible light from a triplet excited state at room temperature is dissolved in a solvent to form a solution, and the solution is heated, irradiated with microwaves or treated with acid water. According to the above method, resources of metals such as iridium or platinum, which are scarce metals, can be utilized efficiently.
Description
DESCRIPTION
METHOD FOR COLLECTING METAL
TECHNICALFIELD [0001]
The present invention relates to a method for collecting a metal contained in an electroluminescent light-emitting element.
BACKGROUND ART [0002]
In recent years, research and development have been carried out actively for electroluminescent light-emitting elements. A basic structure of these light-emitting elements is that a light-emitting substance is sandwiched between a pair of electrodes. The application of voltage to this element enables the light-emitting substance to emit light. [0003]
Since such light-emitting elements are of a self-luminous type, they have advantages such as having higher visibility compared with liquid crystal displays and no need of back lights. Therefore, these light-emitting elements are suitable for flat panel display elements. Another significant advantage is that such light-emitting elements can be manufactured to be thin and light-weight. Another feature is that these light-emitting elements have extremely high response speed. [0004] Since these light-emitting elements can be formed in a film form, planar light emission can easily be obtained by forming elements with large areas. Planar light emission is hard to obtain from point-light sources such as incandescent lamps and LEDs, or line sources such as fluorescent lights. Therefore, these light-emitting elements have a high utility value as surface illuminants. The surface illuminants can be applied to lighting and the like.
[0005]
Electroluminescent light-emitting elements are largely classified into two types according to whether the light-emitting substance is an organic compound or an inorganic compound. Here the light-emitting substance which is the organic compound is described. [0006]
When the light-emitting substance is an organic compound, the application of voltage to the light-emitting element makes electrons injected from an electrode into a layer containing the light-emitting organic compound, holes injected from the other electrode into the layer containing the light-emitting organic compound, and then electric current flows. Then, the recombination of these carriers (electrons and holes) excites the light-emitting organic compound. The light-emitting organic compound emits light in returning to a ground state. Because of such mechanism, such a light-emitting element is referred to as a light-emitting element of a current excitation type. [0007]
Excitation states of an organic compound can be classified into two types: a singlet excited state (S*) and a triplet excited state (T*). The statistical generation ratio of the singlet excited state (S*) and the triplet excited state (T*) in a light-emitting element is considered to be S : T = 1 : 3. [0008]
A ground state of a light-emitting organic compound is usually a singlet state. Therefore, light emission in returning to a singlet ground state from a singlet excited state (S*) is referred to as fluorescence since it is caused by electronic transition between the same multiplets. On the other hand, light emission in returning to a singlet ground state from a triplet excited state (T ) is referred to as phosphorescence since it is caused by electronic transition between different multiplets. In most of the compounds which emit fluorescence (hereinafter referred to as "fluorescent compounds"), only fluorescence is observed and phosphorescence is not at room temperature. Therefore, the maximum value of the internal quantum efficiency (the ratio of photons to be
generated with respect to injected carriers) of a light-emitting element containing a fluorescent compound is said to be theoretically 25 %, on grounds that S* : T* = 1 : 3. [0009]
On the other hand, by using a compound which emits phosphorescence (hereinafter referred to as a "phosphorescent compound"), an internal quantum efficiency of 75 to 100 % is possible in theory. In other words, it is possible to achieve light emission efficiency which is three to four times that of a fluorescent compound. For such a reason, a light-emitting element using a phosphorescent compound is proposed in order to achieve a highly efficient light-emitting element (for example, refer to Non-Patent Document 1: Tetsuo TSUTSUI et al., "Japanese Journal of Applied Physics" vol. 38, 1999, pp. L1502 - L1504) [0010]
As a phosphorescent compound, a complex containing iridium (Ir) as a central metal is used in general as in Non-Patent Document 1. However, iridium is a noble metal and exists in crusts in extremely small amounts. Accordingly, there arises a problem of resource depletion of iridium, as light-emitting devices and electronic appliances using light-emitting elements come into wide use. In addition, in order to reduce adverse impact on the environment, methods for reusing iridium are needed.
DISCLOSURE OF INVENTION [0011]
The present invention has been devised in view of the above problems. An object of the present invention is to provide a method for collecting a scarce metal such as iridium from a light-emitting element no longer needed. [0012]
An aspect of the present invention is a method for collecting metal from an organic metal compound, including a step of ashing an EL layer of a light-emitting element containing an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature through heat treatment. In this specification, the EL layer denotes a layer provided between a pair
of electrodes in a light-emitting element. [0013]
Another aspect of the present invention is a method for collecting a metal from an organic metal compound, including a step of performing a heat treatment at a temperature of 800 0C or higher on an EL layer of a light-emitting element containing an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature.
[0014]
Another aspect of the present invention is a method for collecting a metal from an organic metal compound, including a step of performing a heat treatment at a temperature of 800 0C or higher under atmospheric air or an oxygen atmosphere on an
EL layer of a light-emitting element containing an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature, and collecting a metal oxide which remains after the heat treatment. [0015]
Another aspect of the present invention is a method for collecting a metal from an organic metal compound, including a step of performing a heat treatment on an EL layer of a light-emitting element containing an organic metal compound at a temperature of 800 0C or higher under a reducing atmosphere or with a reducing agent, and collecting a metal oxide which remains after the heat treatment.
[0016]
In the above structure, the remaining metal or the remaining metal oxide may be treated with acid water after the heat treatment, and a solution in which a metal compound containing the metal which constitutes the organic metal compound is dissolved may be obtained. As the acid water, water containing any of the following can be used: hydrogen chloride, hydrogen bromide, hydrogen fluoride, hydrogen iodide, sulfuric acid, nitric acid, nitrous acid, and acetic acid.
[0017]
In the above structure, a step of oxidizing the solution in which the metal
compound is dissolved may be included. [0018]
In the above structure, a step of electrolyzing the solution in which the metal compound is dissolved may be included. [0019]
In the above structure, a step of reacting the metal contained in the solution in which the metal compound is dissolved and an organic ligand to form a metal complex may be included. [0020] In the above structure, a step of reacting the metal contained in the solution in which the metal compound is dissolved and an organic ligand to form a metal complex, and a step of extracting the metal complex with a solvent which dissolves the metal complex may be included. In this case, it is preferable that the solvent be not uniformly mixed with water. [0021]
Another aspect of the present invention is a method for collecting a metal from an organic metal compound, including a first step of exposing an EL layer by detaching one in a pair of electrodes included in a light-emitting element from the light-emitting element in which the EL layer containing an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature is formed between the pair of electrodes, and a second step of irradiating a solution in which the EL layer is dissolved in a solvent with microwaves. [0022]
Another aspect of the present invention is a method for collecting a metal from an organic metal compound, including a first step of exposing an EL layer by detaching one in a pair of electrodes included in a light-emitting element from the light-emitting element in which the EL layer containing an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature is formed between the pair of electrodes, and a second step of adding an organic compound to a solution in which the EL layer is dissolved in a solvent and
performing microwave irradiation.
[0023]
In the above structure, a third step may be included in which a solution in which the metal compound containing the metal which constitutes the organic metal compound is dissolved or a suspension in which the metal compound is suspended is formed by treating the solution irradiated with the microwaves with a solvent containing acid water.
[0024]
Another aspect of the present invention is a method for collecting a metal from an organic metal compound, including a first step of exposing an EL layer by detaching one in a pair of electrodes included in a light-emitting element from the light-emitting element in which the EL layer containing an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature is formed between the pair of electrodes, and a second step of forming a solution in which the metal compound containing the metal which constitutes the organic metal compound is dissolved or a suspension in which the metal compound is suspended, by treating the EL layer of the light-emitting element with a solvent containing acid water.
[0025] In the above structure, as the acid water, water containing any of the following can be used: hydrogen chloride, hydrogen bromide, hydrogen fluoride, hydrogen iodide, sulfuric acid, nitric acid, nitrous acid, and acetic acid.
[0026]
In the above method, a step of oxidizing the solution in which the metal compound is dissolved or the suspension in which the metal complex is suspended may be included.
[0027]
In the above structure, a step of electrolyzing the solution in which the metal compound is dissolved may be included.
[0028]
In the above structure, a step of forming a metal complex by reacting the metal contained in the solution in which the metal compound is dissolved or the suspension in which the metal complex is suspended and an organic ligand may be included. [0029]
In the above structure, a step of forming a metal complex by reacting the metal contained in the solution in which the metal compound is dissolved or the suspension in which the metal complex is suspended and an organic ligand, and a step of extracting the metal complex using a solvent which dissolves the metal complex may be included. [0030]
In the above structure, the organic ligand is supported by a high molecular compound, and the metal complex may be formed by mixing the organic ligand supported by the high molecular compound and the solution or a mixture containing the metal compound. [0031]
In the above structure, it is preferable that the organic ligand be any of the following: an amine derivative, an ethylenediamine derivative, a triethylenediamine derivative, an ethylenediaminethiocarboaldehyde derivative, a phenol derivative, a polyphenol derivative, a thiol derivative, a cyclic thiol derivative, an ether derivative, a cyclic ether derivative, a uracil derivative, an amide derivative, ammonium salt, a pyridine derivative, an amino sulfide derivative, an aniline derivative, a phosphoric acid derivative, phosphonium salt, a phosphine oxide derivative, a thiourea derivative, a benzothiazole derivative, or a thiocarbonyl derivative. [0032] In the above structure, it is preferable that the metal belong to any of the groups
7 to 11 in the periodic table. Further, it is preferable that the metal be Ir, Pt, Ru, or Re. Furthermore, it is preferable that the metal be a rare earth metal. [0033]
According to the present invention, resources of metals such as iridium (Ir) and platinum (Pt), which are scarce metals, can be utilized efficiently.
BRIEF DESCRIPTION OF DRAWINGS [0034]
FIG 1 is a diagram illustrating a light-emitting element.
BEST MODE FOR CARRYING OUTTHE INVENTION [0035]
Embodiment modes of the present invention are described in detail hereinafter with reference to the diagram. Note that the present invention is not limited to the following description and it is easily understood by those skilled in the art that the modes and details disclosed herein can be modified in various ways without departing from the spirit and the scope of the present invention. Therefore, the present invention should not be interpreted as being limited to the description of the embodiment modes to be given below. [0036]
(Embodiment Mode 1)
This embodiment mode describes a method for collecting a metal atom from a light-emitting element containing an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature. [0037]
FIG 1 shows a structure of a general light-emitting element. The light-emitting element shown in FIG 1 is formed over a substrate 201 and includes a first electrode 202, an EL layer 203, and a second electrode 204. The EL layer 203 is sandwiched between the first electrode 202 and the second electrode 204, and contains an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature. To be more specific, the EL layer 203 contains a metal belonging to any of the groups 7 to 11 in the periodic table or a rare earth metal. It is preferable in particular that the metal be Ir, Pt, Ru, or Re, which is used often in light-emitting elements. These metals are noble metals. Since
noble metals exist in extremely small amounts and are expensive, collecting them from light-emitting elements can significantly contribute to reduction in cost. In particular, Ir, Pt, Ru, and Re are commonly used as organic metal compounds which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature, and can be utilized efficiently by collecting them from light-emitting elements. [0038]
For example, compounds represented by structural formulae shown below are given as organic metal compounds which can emit visible light and are contained in EL layers. Note that the present invention is not limited to these. [0039]
[0040]
PtOEP
[0041]
[Ru(bpy)3](CIO4)2
[0042]
X:n-C3F7CO2- [0043]
Phen-Re
[0044]
Tb(acac)3
[0045]
Eu(tta)3phen
[0046]
[0047]
Lnq3 (Ln : Yb, Nd, Er)
[0048]
Au2(dppm)CI2 [0049]
The organic metal compounds shown above include a metal belonging to any of the groups 7 to 11 in the periodic table or a rare earth metal. Resources can be utilized efficiently by collecting the metal belonging to any of the groups 7 to 11 in the periodic table or the rare earth metal from light-emitting elements containing these organic metal compounds. [0050]
In addition to the above organic metal compounds, in particular, organic metal compounds containing Ir as a central metal are commonly used in light-emitting elements. For example, organic metal compounds having the following partial
structures are given as examples. [0051]
[0052]
bt bon
[0054]
In addition, organic metal compounds having the above partial structures and the following ligand are also commonly used.
[0055]
[0056]
As organic metal compounds having the above partial structures, for example, compounds represented by the following structural formulae are given.
[0057]
Ppylr(acac)
[0058]
Bt2lr(acac) [0059]
Btp2lr(acac)
[0060]
In addition, compounds represented by the following formulae are commonly used in light-emitting elements.
[0061]
(CF3ppy)2lr(pic)
[0062]
[0063]
Flr6
[0064]
The first electrode 202 and the second electrode 204 contain various metals, alloys, conductive compounds, and mixtures thereof, and the like. For example, a transparent conductive film made of indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide (IZO), or the like can be used for
an electrode through which light is extracted. Further, various conductive materials such as gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), or aluminum (Al) can be used. Furthermore, an element belonging to the group 1 or 2 in the periodic table, i.e. an alkali metal such as lithium (Li) and cesium (Cs), an alkaline earth metal such as magnesium (Mg), calcium (Ca), and strontium (Sr); an alloy containing these elements (MgAg, AlLi, or the like); a rare earth metal such as europium (Eu), and ytterbium (Yb); alloys containing these elements; or the like can be used. [0065] A material which emits visible light in returning to a singlet ground state from a triplet excited state at room temperature is extracted from a light-emitting element having such a structure described above. First, the first electrode 202 or the second electrode 204 is detached from the light-emitting element. It is acceptable as long as at least one in the pair of electrodes is detached, but it is easier to detach an electrode that is formed after forming the EL layer. It is relatively easy to detach the electrode since an electrode made of an inorganic compound generally has low adhesion to an organic compound. The electrode can be detached by, for example, putting adhesive tape on the electrode and peeling off the tape afterwards. In particular, the electrode which is formed on a region smaller than the EL layer, can easily be detached. [0066]
In addition to adhesive tape, it is also possible to detach the electrode by applying a light curing resin, a heat curing resin, or the like and peeling it afterwards. A versatile resin such as an epoxy resin, a polyimide resin, or a phenol resin can be used as the resin. [0067]
Furthermore, the electrode may be removed by acid treatment or alkaline treatment when the electrode contains a material which is reactive with acid or alkali, such as aluminum (Al). [0068] Thereafter, the EL layer is extracted. Various methods can be used to take out
the EL layer. For example, an organic compound contained in the EL layer may be extracted in a state of solution after being dissolved in a solvent. A solvent of aromatic hydrocarbon such as toluene, xylene, and tetralin; aromatic hydrocarbon containing halogen, such as dichlorobenzene and chlorobenzene; aliphatic halogenated hydrocarbon series such as dichloromethane and chloroform; or the like are given as examples of the solvent which can dissolve the organic compound contained in the EL layer. Further, a solvent of ether series such as tetrahydrofuran and diethyl ether may also be used. Here, the EL layer need not completely be dissolved in the solvent and may be extracted, dissolved partially in a state of a mixture. [0069]
Next, a metal atom which constitutes an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature is collected from the solution or the mixture containing various compounds which constitute the EL layer. [0070]
A first method is as follows: the solution or the mixture containing various compounds which constitute the EL layer is subjected to heat treatment and ashed. The heat treatment may be carried out under any of the following: atmospheric air, an oxygen atmosphere, or a reducing atmosphere. Further, the heat treatment may be carried out with a reducing agent. When the heat treatment is carried out under atmospheric air or an oxygen atmosphere, a metal oxide can be obtained. When the heat treatment is carried out under a reducing atmosphere, e.g. a H2 gas atmosphere, a metal can be obtained. Furthermore, when the heat treatment is carried out with a reducing agent such as palladium carbon (PdC) or aluminum (Al), a metal can be obtained. When a variety of metals are contained in the EL layer, it is preferable that the heat treatment be carried out under a reducing atmosphere since metals can be separated with more ease compared with metal oxides by utilizing the difference in melting points. In addition, it is preferable that the heat treatment be carried out at a temperature of 800 0C or higher, more preferably 1000 0C or higher, in order to prevent an organic matter from remaining.
[0071]
Next, the metal or the metal oxide obtained by the above method is separated. The metal or the metal oxide can be separated by utilizing the difference in melting points of the metals, for example. By utilizing the difference in melting points, the targeted metal atom can be collected: i.e., the metal atom can be collected from the organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature. [0072]
In addition to utilizing the difference in melting points, the targeted metal atom can also be collected by using the following method. [0073]
First, the metal or the metal oxide obtained by the above method is treated with acid water: that is to say, it is mixed with acid water and stirred. In concrete terms, the metal or the metal oxide obtained by the above heat treatment is reacted with water containing hydrogen chloride, hydrogen bromide, hydrogen fluoride, acetic acid, nitric acid, nitrous acid, sulfuric acid, hydrogen iodide, or the like. Heat treatment or oxidation treatment may be carried out if necessary. Oxidation treatment may be carried out with oxygen by introducing air, for example. Further, oxidation treatment may be carried out by mixing the metal or the metal oxide with hydrogen peroxide, whereby the metal or the metal oxide is oxidized. Furthermore, oxidation treatment may be carried out with halogen such as iodine, chlorine, or bromine. [0074]
Thus, a metal compound of a transition metal belonging to any of the groups 7 to 11 or that of a rare earth metal can be obtained. To be specific, a solution of chloride, bromide, fluoride, iodide, sulfate, sulfide, nitrate, nitrite, acetate, or oxide can be obtained. Chloride, bromide, fluoride, iodide, sulfate, sulfide, nitrate, nitrite, and acetate are preferable since the solubility thereof is high. [0075]
The solution which is obtained in this manner and in which the metal compound is dissolved may be subjected to alkali treatment. Through the alkali
treatment, a hydroxide, ammonium salt, phosphonium salt, and sulfonium salt of the metal can be produced, and a solution thereof can be obtained. Ammonium salt, phosphonium salt, and sulfonium salt are preferable since the solubility thereof is high. [0076] After forming the solution of the metal compound which contains a transition metal belonging to any of the groups 7 to 11 or a rare earth metal as a central metal, the metal compound is separated from the solution. In concrete terms, there are a method in which electrolysis is carried out and a method in which the solution is treated with a solution containing an organic ligand. [0077]
In the electrolysis method, the transition metal belonging to any of the groups 7 to 11 or the rare earth metal is deposited on or near an electrode by connecting the solution of the metal compound containing the transition metal belonging to any of the groups 7 to 11 or the rare earth metal as a central metal to a DC power source. Even if another kind of metal is contained in the solution, it is possible to separate only the targeted metal with ease by carrying out the electrolysis since each metal has a different ionization tendency. For the electrolysis, various solvents can be used, e.g. water, acetonitrile, or molten salt. [0078] As a method in which the solution containing the metal compound which contains the transition metal belonging to any of the groups 7 to 11 or the rare earth metal as a central metal is treated with the solution containing an organic ligand, a method can be given in which the solution containing the organic ligand is added to the solution containing the metal compound, whereby the metal compound and the organic ligand are reacted with each other to form a metal complex, and then the metal complex is extracted using a solvent which dissolves the metal complex. In this method, it is preferable that the solvent which dissolves the metal complex be not uniformly mixed with water. [0079] The organic ligand mentioned here is a molecule which can form a plurality of
coordinate bonds with the metal, and is also referred to as a chelate ligand. To be specific, the following substances can be given as examples: an amine derivative, an ethylenediamine derivative, a triethylenediamine derivative, an ethylenediaminethiocarboaldehyde derivative, a phenol derivative, a polyphenol derivative, a thiol derivative, a cyclic thiol derivative, an ether derivative, a cyclic ether derivative, a uracil derivative, an amide derivative, ammonium salt, a pyridine derivative, an amino sulfide derivative, an aniline derivative, a phosphoric acid derivative, phosphonium salt, a phosphine oxide derivative, a thiourea derivative, a benzothiazole derivative, a thiocarbonyl derivative, and the like. These compounds may be supported by polymer compounds. In such a case, as the polymer compounds, those which contain polystyrene, polyacrylic acid ester, polymethacrylic acid ester, polyvinyl ether, polyvinyl ester, or the like as a principal chain can be used. Alternatively, the organic ligand described above may be incorporated into a side chain of a cross-linked material of these polymer compounds. [0080]
For example, a compound represented by General Formula (1), a compound represented by General Formula (2), and a compound represented by General Formula (3) are given as an amine derivative, an ethylenediamine derivative, and a triethylenediamine derivative, respectively. [0081]
N (1 )
R3
[0082]
1 "\
In General Formula (1), R to R each independently represent hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
[0083]
[0084]
In General Formula (2), R1 to R4 each independently represent hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples. [0085]
In General Formula (3), R1 to R5 each independently represent hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples. [0087]
For example, a compound represented by General Formula (4) is given as an ethylenediaminethiocarboaldehyde derivative. [0088]
In General Formula (4), R1 to R3 each independently represent hydrogen, an
alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples. [0090]
For example, a compound represented by General Formula (5), a compound represented by General Formula (6), and a compound represented by General Formula (7) are given as a phenol derivative and a polyphenol derivative. [0091]
In General Formula (5), R1 represents hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples. [0093]
[0094]
[0095]
For example, a compound represented by General Formula (8) and a compound represented by General Formula (9) are given as a thiol derivative and a cyclic thiol
[0097]
In General Formula (8), R1 represents hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given examples. [0098]
For example, a compound represented by General Formula (10), a compound represented by General Formula (11), and a compound represented by General Formula (12) are given as an ether derivative and a cyclic ether derivative. [0100]
[0101]
(1 1)
[0102]
[0103]
For example, a compound represented by General Formula (13) and a compound represented by General Formula (14) are given as a uracil derivative. [0104]
[0105]
In General Formula (13), R1 represents hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples. [0106]
[0107] In General Formula (14), R1 represents hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
[0108]
For example, a compound represented by General Formula (15), a compound represented by General Formula (16), and a compound represented by General Formula
(17) are given as an amide derivative.
[0109]
[0110]
In General Formula (15), R1 and R2 each independently represent hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples. [0111]
In General Formula (16), R1 to R3 each independently represent hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples. [0113]
[0114]
In General Formula (17), R1 to R6 each independently represent hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples. [0115]
For example, a compound represented by General Formula (18) is given as
ammonium salt. [0116]
R1 R4_N +_R2 B- (1 8)
R3
B = Cl, SO4, CIO4, CH3CO2, Br, I, CO3, HCO3, HSO4
[0117] In General Formula (18), R1 to R4 each independently represent hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples. Further, B" represents any of the following: a chloride ion, a sulfate ion, a perchlorate ion, an acetate ion, a bromide ion, an iodide ion, a carbonate ion, a hydrogen carbonate ion, and a sulfite ion. [0118]
For example, a compound represented by General Formula (19) and a compound represented by Formula (20) are given as a pyridine derivative. [0119]
[0120]
In General Formula (19), R1 and R2 each independently represent hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
[0121]
[0122]
In General Formula (20), R1 represents hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples. [0123]
For example, a compound represented by General Formula (21) is given as an amino sulfide derivative. [0124]
[0125]
In General Formula (21), R1 represents hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples. [0126]
For example, a compound represented by General Formula (22) is given as an aniline derivative. [0127]
[0128]
In General Formula (22), R1 to R3 each independently represent hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a
hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
[0129]
For example, a compound represented by General Formula (23), a compound represented by General Formula (24), and a compound represented by General Formula (25) are given as a phosphoric acid derivative, phosphonium salt, and a phosphine oxide derivative. [0130]
R1 O
R2-O-P=O (23)
O
I
R3 [0131]
In General Formula (23), R1 to R3 each independently represent hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples. ^ [0132]
R1
R2-P=O (24)
I
R3 [0133]
In General Formula (24), R1 to R3 each independently represent hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
[0134]
B = Cl, SO4, CIO4, CH3CO2, Br1 I1 CO3, HCO3, HSO4
[0135]
In General Formula (25), R1 to R4 each independently represent hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples. Further, B" represents any of the following: a chloride ion, a sulfate ion, a perchlorate ion, an acetate ion, a bromide ion, an iodide ion, a carbonate ion, a hydrogen carbonate ion, and a sulfite ion. [0136]
For example, a compound represented by General Formula (26) is given as a thiourea derivative. [0137]
In General Formula (26), R1 to R4 each independently represent hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples. [0139]
For example, a compound represented by General Formula (27) is given as a benzothiazole derivative.
[0140]
[0141]
In General Formula (27), R1 represents hydrogen, an aryl group, or an alkoxy group. [0142]
For example, a compound represented by General Formula (28), a compound represented by General Formula (29), a compound represented by General Formula (30), and a compound represented by General Formula (31) are given as a thiocarbonyl derivative. [0143]
[0144]
In General Formula (28), R1 and R2 each independently represent hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples. [0145]
In General Formula (29), R1 to R3 each independently represent hydrogen, an
alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples. [0147]
[0148]
In General Formula (30), R1 and R2 each independently represent hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples. [0149]
[0150]
In General Formula (31), R1 to R3 each independently represent hydrogen, an alkyl group, or an aryl group. In concrete terms, a methyl group, a butyl group, a hexyl group, a decyl group, a phenyl group, a naphthyl group, and the like are given as examples.
[0151]
The method described above makes it possible to separate a central metal which constitutes a material that emits visible light in returning to a singlet ground state from a triplet excited state at room temperature and is contained in a light-emitting element, i.e. a metal belonging to any of the groups 7 to 11 or a rare earth metal.
According to the method described in this embodiment mode, resources of the metal belonging to any of the groups 7 to 11 or the rare earth metal such as iridium (Ir) and platinum (Pt), which are scarce metals, can be utilized efficiently.
[0152]
Similarly, a central metal which constitutes a material that emits visible light in returning to a singlet ground state from a triplet excited state at room temperature can be collected also from a light-emitting element in which a plurality of EL layers are stacked with a charge-generating layer interposed therebetween/thereamong. [0153]
This embodiment mode can appropriately be combined with other embodiment modes. [0154] (Embodiment Mode 2)
This embodiment mode explains a method for collecting a metal atom, which is different from the method described in Embodiment Mode 1. [0155]
In a similar manner with Embodiment Mode 1, an EL layer is extracted and then a solution or a mixture containing various compounds which constitute the EL layer is formed. [0156]
Next, the solution in which the EL layer is dissolved in a solvent, or a mixture in which the EL layer is partially dissolved in a solvent is irradiated with microwaves. The microwaves may be adjusted so that the organic metal compound which is contained in the EL layer and can emit visible light in returning to a singlet ground state to a triplet excited state at room temperature can decompose. Further, the solution or the mixture can also be irradiated with light in microwave irradiation. The light irradiation makes the organic metal compound in an excited state and can promote further decomposition. Furthermore, an organic compound may be added in microwave irradiation. Acetylacetone, picolinic acid, pyridine, and the like are given as the organic compound. Adding the organic compound can promote the decomposition of the organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature. It is preferable that a solvent used in microwave irradiation have high polarity. Using the
high-polar solvent enables the efficient decomposition of the organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature since the value of generated heat increases in microwave irradiation. Glycerol, 2-ethoxyethanol, ethylene glycol, dichloromethane, or the like can be given as the high-polar solvent. Further, ionic liquid of 1 -butyl-3 -methylimidazoliumhexafluorophosphate, l-butyl-3-methylimidazoliumtetrafluoroborate, or the like may be used. Furthermore, water may be added to these solvents as well. [0157] After the microwave irradiation, an operation of separating the targeted metal from the solution or the mixture containing the decomposed matter is carried out, if necessary. As a method for separating the targeted metal, the following methods are given: after treating the solution or the mixture with acid water, electrolysis is carried out; after treating the solution or the mixture with acid, an organic ligand is added and a metal complex is extracted; or an organic ligand is added to the solution or the mixture containing the decomposed matter and a metal complex is extracted directly. [0158]
The solution or the mixture containing the decomposed matter which is obtained as described above is treated with acid water. That is to say, the solution or the mixture is mixed with acid water and stirred. In concrete terms, the solution or the mixture containing the decomposed matter is reacted with water containing hydrogen chloride, hydrogen bromide, hydrogen fluoride, acetic acid, nitric acid, nitrous acid, sulfuric acid, hydrogen iodide, or the like. Heat treatment or oxidation treatment may be carried out if necessary. Oxidation treatment may be carried out with oxygen by introducing air, for example. Further, oxidation treatment may be carried out by mixing the solution or the mixture with hydrogen peroxide, whereby the solution or the mixture is oxidized. Furthermore, oxidation treatment may be carried out with halogen such as iodine, chlorine, and bromine. [0159] Accordingly, a metal compound which contains a transition metal belonging to
any of the groups 7 to 11 or that of a rare earth metal as a central metal can be obtained. To be specific, chloride, bromide, fluoride, iodide, sulfate, sulfide, nitrate, nitrite, acetate, or oxide can be obtained. [0160] The solution which is obtained in this manner and in which the metal compound is dissolved or a suspension which is obtained in this manner and in which the metal compound is suspended may be treated with alkali. Through the alkali treatment, a hydroxide, ammonium salt, phosphonium salt, and sulfonium salt of the metal can be produced, and a solution thereof or a suspension thereof can be obtained. [0161]
After forming the solution or the suspension containing the metal compound which contains a transition metal belonging to any of the groups 7 to 11 or a rare earth metal as a central metal, the metal compound is separated from the solution or the suspension. In concrete terms, there are a method in which electrolysis is carried out and a method in which the solution or the suspension is treated with a solution containing an organic ligand. Electrolysis can preferably be employed for the solution. Treatment with a solution containing an organic ligand can be preferably employed both for the solution and the suspension. [0162] In the electrolysis method, the transition metal belonging to any of the groups 7 to 11 or the rare earth metal is deposited on or near an electrode by connecting the solution of the metal compound containing the transition metal belonging to any of the groups 7 to 11 or the rare earth metal as a central metal to a DC power source. Even if another kind of metal is contained in the solution, it is possible to separate only the targeted metal with ease by carrying out the electrolysis since each metal has a different ionization tendency. For the electrolysis, various solvents can be used, e.g. water, acetonitrile, and molten salt. [0163]
As a method in which the solution or the suspension containing the metal compound which contains the transition metal belonging to any of the groups 7 to 11 or
the rare earth metal as a central metal is treated with the solution containing the organic ligand, a method can be given in which the solution containing the organic ligand is added to the solution or the suspension containing the metal compound, whereby the metal compound and the organic ligand are reacted with each other to form a metal complex, and then the metal complex is extracted with a solvent which dissolves the metal complex. In this method, it is preferable that the solvent which dissolves the metal complex be not uniformly mixed with water. As the organic ligand, the organic ligand described in Embodiment Mode 1 can be used. [0164] Further, by adding an organic ligand to the solution or the mixture containing the decomposed matter to extract a metal complex directly, the targeted metal can be separated. Also in the case of direct extraction, by adding a solution containing an organic ligand to the solution or the mixture containing the decomposed matter, the metal contained in the decomposed matter and the organic ligand are reacted with each other to form a metal complex, so that the metal complex can be extracted with a solvent which dissolves the metal complex. In this case, as the organic ligand, the organic ligand described in Embodiment Mode 1 can be used. [0165]
The method described above makes it possible to separate a central metal which constitutes a material that emits visible light in returning to a singlet ground state from a triplet excited state at room temperature and is contained in a light-emitting element, i.e. a metal belonging to any of the groups 7 to 11 or a rare earth metal. [0166]
According to the method described in this embodiment mode, resources of the metal belonging to any of the groups 7 to 11 or the rare earth metal such as indium (Ir) and platinum (Pt), which are scarce metals, can be utilized efficiently. [0167]
This embodiment mode can appropriately be combined with other embodiment modes.
[0168]
(Embodiment Mode 3)
This embodiment mode explains a method for collecting a metal atom, which is different from the methods described in Embodiment Mode 1 and Embodiment Mode 2. [0169]
In a similar manner with Embodiment Mode 1, an EL layer is extracted and then a solution or a mixture containing various compounds which constitute the EL layer is formed.
[0170] Next, the solution in which the EL layer is dissolved in a solvent, or the mixture in which the EL layer is partially dissolved in a solvent is treated with acid water. That is to say, the solution or the mixture is mixed with acid water and stirred.
In concrete terms, the organic compounds which constitute the EL layer is reacted with water containing hydrogen chloride, hydrogen bromide, hydrogen fluoride, acetic acid, nitric acid, nitrous acid, sulfuric acid, hydrogen iodide, or the like. Heat treatment or oxidation treatment may be carried out if necessary. Oxidation treatment may be carried out with oxygen by introducing air, for example. Further, oxidation treatment may be carried out by mixing the solution or the metal mixture with hydrogen peroxide, whereby the solution or the mixture is oxidized. Furthermore, oxidation treatment may be carried out with halogen such as iodine, chlorine, and bromine. Still furthermore, microwave irradiation may be carried out as the heat treatment.
[0171]
Accordingly, a metal compound of a transition metal belonging to any of the groups 7 to 11 or that of a rare earth metal can be obtained. To be specific, chloride, bromide, fluoride, iodide, sulfate, sulfide, nitrate, nitrite, acetate, or oxide can be obtained.
[0172]
The solution which is obtained in this manner and in which the metal compound is dissolved or a suspension which is obtained in this manner and in which the metal compound is suspended may be treated with alkali. Through the alkali
treatment, a hydroxide, ammonium salt, phosphonium salt, and sulfonium salt of the metal can be produced, and a solution thereof or a suspension thereof can be obtained. [0173]
After forming the solution or a suspension containing the metal compound which contains a transition metal belonging to any of the groups 7 to 11 or a rare earth metal as a central metal, an operation of separating the metal compound from the solution or the suspension is carried out, if necessary. In concrete terms, there are a method in which electrolysis is carried out and a method in which the solution or the suspension is treated with a solution containing an organic ligand. Electrolysis can preferably be employed for the solution. Treatment with a solution containing an organic ligand can be preferably employed both for the solution and the suspension. [0174]
In the electrolysis method, as explained in Embodiment Mode 1 and Embodiment Mode 2, the transition metal belonging to any of the groups 7 to 11 or the rare earth metal is deposited on or near an electrode by connecting the solution of the metal compound containing the transition metal belonging to any of the groups 7 to 11 or the rare earth metal as a central metal to a DC power source. Even if another kind of metal is contained in the solution, it is possible to separate only the targeted metal with ease by carrying out the electrolysis since each metal has a different ionization tendency. For the electrolysis, various solutions can be used, e.g. water, acetonitrile, and molten salt. [0175]
Further, by adding the solution containing the organic ligand to the solution or the suspension containing the metal compound which contains the transition metal belonging to any of the groups 7 to 11 or the rare earth metal as a central metal, the metal compound and the organic ligand are reacted with each other to form metal complex, and then the metal complex can be extracted with a solvent which dissolves the metal complex. In this method, it is preferable that the solvent which dissolves the metal complex be not uniformly mixed with water. As the organic ligand, the organic ligand described in Embodiment Mode 1 can be used.
[0176]
The method described above makes it possible to separate a central metal which constitutes a material that emits visible light in returning to a singlet ground state from a triplet excited state at room temperature and is contained in a light-emitting element, i.e. a metal belonging to any of the groups 7 to 11 or a rare earth metal. [0177]
According to the method described in this embodiment mode, resources of the metal belonging to any of the groups 7 to 11 or the rare earth metal such as iridium (Ir) and platinum (Pt), which are scarce metals, can be utilized efficiently. [0178]
This embodiment mode can appropriately be combined with other embodiment modes. [0179] [Embodiment 1] Hereinafter, an example where a metal is collected from an organic metal compound which can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature according to a method of the present invention is illustrated specifically. In concrete terms, an example where iridium is collected from an organic metal compound containing iridium is illustrated specifically. [0180]
An iridium complex is often used for a light-emitting element because it can emit visible light in returning to a singlet ground state from a triplet excited state at room temperature and can accomplish high light emission efficiency. When iridium, which is a noble metal, contained in an iridium complex is collected from a light-emitting element, an electrode of the light-emitting element may be detached using tape or the like, and then an EL layer of the light-emitting element may be dissolved in an organic solvent. However, in the solvent in which the EL layer is dissolved, several kinds of organic compounds can be contained in addition to the iridium complex because materials other than a light-emitting material (e.g. a hole transport material, an electron transport material, a host material for dispersing dopant, and the like) are also
usually used for a light-emitting element. [0181]
In this embodiment, on the assumption of such a situation, it is demonstrated that a compound containing iridium can be separated from a mixed solution in which three kinds of substances are dissolved: the dissolved substances are an iridium complex, a substance that can be used as a hole transport material or a host material, and a substance that can be used as an electron transport material or a host material [0182] <Step 1: Making a mixed solution> 20 mg of
(acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]), which is an iridium complex,
4,4'-bis[iV-(l-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), which is a hole transport material, tris(8-quinolinolato)aluminum(III) (abbreviation: AIq3), which is an electron transport material, are each weighed out, and they are dissolved in 3 ml of toluene to make a solution. [0183] <Step 2: Separating and collecting the compound containing iridium>
Next, 3 ml of 5 M hydrochloric acid solution is added to the mixed solution which is made through the step 1, and the mixed solution to which 3 ml of 5 M hydrochloric acid solution is added is irradiated with microwaves (2.45 GHz, 0 to 250 W, 0 to 250 psi) for 30 minutes to be reacted. After the reaction, black powder is deposited and the reacted solution is separated into a light brown toluene layer and a light yellow hydrochloric acid solution layer. It is observed that (4-fluorophenyl)quinoxaline, which is a ligand of an iridium complex, and NPB are dissolved in the toluene layer by carrying out thin layer chromatography to the toluene layer, which is an upper layer. Further, the hydrochloric acid solution, which is a lower layer, is light yellow and it is probable that 8-quinolinol, which is a ligand of AIq3, is dissolved therein. Therefore, it is probable that the compound containing iridium is able to be separated by being deposited selectively. The deposited compound
containing iridium is filtered, washed with toluene and then with dichloromethane, and is collected. The microwave irradiation is carried out using a microwave synthesis apparatus (Discover: made by CEM Corporation). [0184] The black powder obtained in the step 2 is analyzed by electron probe X-ray microanalysis (EPMA). As a result of the analysis, it is found that elements detected are carbon (C), iridium (Ir), fluorine (F), nitrogen (N), chlorine (Cl), and oxygen (O) (in descending order of detected amounts). From this result, it is confirmed that iridium is able to be collected from the mixed solution containing [Ir(Fdpq)2(acac)], NPB and AIq3. Further, it is confirmed that iridium is able to be separated from the solution containing aluminum deriving from AIq3 and iridium deriving from [Ir(Fdpq)2(acac)] as metal elements by the above method. [0185]
This application is based on Japanese Patent Application serial no. 2006-308730 filed with Japan Patent office on November 15, 2006, the entire contents of which are hereby incorporated by reference.
Claims
1. A method for collecting a metal from an organic metal compound, comprising the steps of: heating an organic metal compound capable of emitting visible light from a triplet excited state; and collecting a metal oxide or a metal which remains after the heating.
2. A method for collecting a metal from an organic metal compound according to Claim 1, wherein the organic metal compound is heated at a temperature of 800 0C or higher under atmospheric air, an oxygen atmosphere, a reducing atmosphere or with a reducing agent.
3. A method for collecting a metal from an organic metal compound, comprising the steps of: exposing an EL layer by detaching at least one of a pair of electrodes from a light-emitting element, wherein the EL layer contains an organic metal compound capable of emitting visible light from a triplet excited state, and the light-emitting element comprises the pair of electrodes and the EL layer formed between the pair of electrodes; dissolving the EL layer in a solvent to form a solution or a mixture; heating the solution or the mixture at a temperature of 800 0C or higher under atmospheric air or an oxygen atmosphere; and collecting a metal oxide which remains after the heating.
4. A method for collecting a metal from an organic metal compound according to Claim 3, further comprising the step of: treating the metal oxide with acid water to form a second solution in which the metal oxide is dissolved.
5. A method for collecting a metal from an organic metal compound according to Claim 3, further comprising the steps of: treating the metal oxide with acid water to form a second solution in which the metal oxide is dissolved; and electrolyzing the second solution.
6. A method for collecting a metal from an organic metal compound according to Claim 3, further comprising the steps of: treating the metal oxide with acid water to form a second solution in which the metal oxide is dissolved; and reacting a metal contained in the second solution and an organic ligand to form a metal complex.
7. A method for collecting a metal from an organic metal compound according to Claim 3, further comprising the steps of: treating the metal oxide with acid water to form a second solution in which the metal oxide is dissolved; reacting a metal contained in the second solution and an organic ligand to form a metal complex; and extracting the metal complex using a solvent to dissolve the metal complex.
8. A method for collecting a metal from an organic metal compound, comprising the steps of: exposing an EL layer by detaching at least one of a pair of electrodes from a light-emitting element, wherein the EL layer contains an organic metal compound capable of emitting visible light from a triplet excited state, and the light-emitting element comprises the pair of electrodes and the EL layer formed between the pair of electrodes; dissolving the EL layer in a solvent to form a solution or a mixture; heating the solution or the mixture at a temperature of 800 0C or higher under a reducing atmosphere or with a reducing agent; and collecting a metal which remains after the heating.
9. A method for collecting a metal from an organic metal compound according to Claim 8, further comprising the step of: treating the metal with acid water to form a second solution in which the metal is dissolved.
10. A method for collecting a metal from an organic metal compound according to Claim 8, further comprising the steps of: treating the metal with acid water to form a second solution in which the metal is dissolved; and electrolyzing the second solution.
11. A method for collecting a metal from an organic metal compound according to Claim 8, further comprising the steps of: treating the metal with acid water to form a second solution in which the metal is dissolved; and reacting the metal contained in the second solution and an organic ligand to form a metal complex.
12. A method for collecting a metal from an organic metal compound according to Claim 8, further comprising the steps of: treating the metal with acid water to form a second solution in which the metal is dissolved; reacting the metal contained in the second solution and an organic ligand to form a metal complex; and extracting the metal complex using a solvent to dissolve the metal complex.
13. A method for collecting a metal from an organic metal compound, comprising the steps of: exposing an EL layer by detaching at least one of a pair of electrodes from a light-emitting element, wherein the EL layer contains an organic metal compound capable of emitting visible light from a triplet excited state, and the light-emitting layer comprises the pair of electrodes and the EL layer formed between the pair of electrodes; dissolving the EL layer in a solvent to form a solution or a mixture; and irradiating the solution or the mixture with a microwave.
14. A method for collecting a metal from an organic metal compound according to Claim 13, further comprising the step of: treating the solution or the mixture with acid water to form a second solution containing a metal or a suspension containing the metal.
15. A method for collecting a metal from an organic metal compound according to Claim 13, further comprising the steps of: treating the solution or the mixture with acid water to form a second solution containing a metal or a suspension containing the metal; and electrolyzing the second solution or the suspension.
16. A method for collecting a metal from an organic metal compound according to Claim 13, further comprising the steps of: treating the solution or the mixture with acid water to form a second solution containing a metal or a suspension containing the metal; and reacting the metal contained in the second solution or the suspension and an organic ligand to form a metal complex.
17. A method for collecting a metal from an organic metal compound according to Claim 13, further comprising the steps of: treating the solution or the mixture with acid water to form a second solution containing a metal or a suspension containing the metal, reacting the metal contained in the second solution or the suspension and an organic ligand to form a metal complex, and extracting the metal complex using a solvent to dissolve the metal complex.
18. A method for collecting a metal from an organic metal compound, comprising the steps of: exposing an EL layer by detaching at least one of a pair of electrodes from a light-emitting element, wherein the EL layer contains an organic metal compound capable of emitting visible light from a triplet excited state, and the light-emitting layer comprises the pair of electrodes and the EL layer formed between the pair of electrodes; dissolving the EL layer in a solvent to form a first solution or a mixture; and treating the first solution or the mixture with acid water to form a second solution containing a metal or a suspension containing the metal.
19. A method for collecting a metal from an organic metal compound according to Claim 18, further comprising the step of: electrolyzing the second solution or the suspension.
20. A method for collecting a metal from an organic metal compound according to Claim 18, further comprising the step of: reacting the metal contained in the second solution or the suspension and an organic ligand to form a metal complex.
21. A method for collecting a metal from an organic metal compound according to Claim 18, further comprising the steps of: reacting the metal contained in the second solution or the suspension and an organic ligand to form a metal complex, and extracting the metal complex using a solvent to dissolve the metal complex.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020097012008A KR101455305B1 (en) | 2006-11-15 | 2007-11-06 | Method for collecting metal |
| CN2007800419992A CN101535510B (en) | 2006-11-15 | 2007-11-06 | Method for collecting metal |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006-308730 | 2006-11-15 | ||
| JP2006308730 | 2006-11-15 |
Publications (1)
| Publication Number | Publication Date |
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| WO2008059770A1 true WO2008059770A1 (en) | 2008-05-22 |
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ID=39401577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2007/071866 WO2008059770A1 (en) | 2006-11-15 | 2007-11-06 | Method for collecting metal |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US8128727B2 (en) |
| JP (1) | JP5300245B2 (en) |
| KR (1) | KR101455305B1 (en) |
| CN (1) | CN101535510B (en) |
| WO (1) | WO2008059770A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11408053B2 (en) | 2015-04-21 | 2022-08-09 | Excir Works Corp. | Methods for selective leaching and extraction of precious metals in organic solvents |
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| JP5398369B2 (en) * | 2009-06-15 | 2014-01-29 | 株式会社東芝 | Rare metal production method and system |
| JP5424809B2 (en) * | 2009-10-16 | 2014-02-26 | 国立大学法人茨城大学 | Gold and / or silver recovery methods |
| US8404500B2 (en) * | 2009-11-02 | 2013-03-26 | Semiconductor Energy Laboratory Co., Ltd. | Method for manufacturing light-emitting element, light-emitting element, light-emitting device, lighting device, and electronic appliance |
| CN102441553B (en) * | 2010-10-12 | 2014-07-02 | 深圳市格林美高新技术股份有限公司 | Method and device for recovering precious metals from precious metal electronic scraps |
| WO2012063616A1 (en) | 2010-11-08 | 2012-05-18 | Ｎｅｃライティング株式会社 | Collection and recycling system for organic el lighting apparatus |
| JP5791036B2 (en) * | 2011-01-19 | 2015-10-07 | 住友大阪セメント株式会社 | Organic-inorganic composite, organic-inorganic composite composition, and ink |
| TWI727297B (en) | 2011-08-25 | 2021-05-11 | 日商半導體能源研究所股份有限公司 | Light-emitting element, light-emitting device, electronic device, lighting device, and novel organic compound |
| US9059411B2 (en) | 2012-02-29 | 2015-06-16 | Semiconductor Energy Laboratory Co., Ltd. | Fluorene compound, light-emitting element, light-emitting device, electronic device, and lighting device |
| JP6312960B2 (en) | 2012-08-03 | 2018-04-18 | 株式会社半導体エネルギー研究所 | Light emitting element, light emitting device, electronic device, lighting device, and heterocyclic compound |
| KR102457008B1 (en) | 2014-05-23 | 2022-10-19 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device |
| US9806337B2 (en) | 2015-01-15 | 2017-10-31 | Nissan North America, Inc. | Electrode structure having alternating composite layers |
| PL3085796T3 (en) | 2015-04-21 | 2017-12-29 | Heraeus Deutschland GmbH & Co. KG | Extraction method for a metallic, iridium and/or iridium oxide comprising mixture of solid particles |
| CN110885987B (en) * | 2019-12-23 | 2020-12-29 | 厦门金玺燕贵金属科技有限公司 | Preparation method of high-purity platinum |
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2008144269A (en) | 2008-06-26 |
| JP5300245B2 (en) | 2013-09-25 |
| US20120125853A1 (en) | 2012-05-24 |
| US8128727B2 (en) | 2012-03-06 |
| KR20090082919A (en) | 2009-07-31 |
| KR101455305B1 (en) | 2014-10-27 |
| US20080261477A1 (en) | 2008-10-23 |
| CN101535510A (en) | 2009-09-16 |
| CN101535510B (en) | 2012-09-05 |
| US8435793B2 (en) | 2013-05-07 |
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