JP2011524865A - 金属錯体を含む電子デバイス - Google Patents
金属錯体を含む電子デバイス Download PDFInfo
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- JP2011524865A JP2011524865A JP2011511992A JP2011511992A JP2011524865A JP 2011524865 A JP2011524865 A JP 2011524865A JP 2011511992 A JP2011511992 A JP 2011511992A JP 2011511992 A JP2011511992 A JP 2011511992A JP 2011524865 A JP2011524865 A JP 2011524865A
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- 229910052751 metal Inorganic materials 0.000 title claims description 97
- 239000002184 metal Substances 0.000 title claims description 97
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 110
- 239000003446 ligand Substances 0.000 claims description 96
- 125000003118 aryl group Chemical group 0.000 claims description 71
- -1 aromatic isonitrile Chemical class 0.000 claims description 66
- 125000004429 atom Chemical group 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 125000004122 cyclic group Chemical group 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 239000000463 material Substances 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 230000007935 neutral effect Effects 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 239000011159 matrix material Substances 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000000129 anionic group Chemical group 0.000 claims description 16
- 230000000903 blocking effect Effects 0.000 claims description 16
- 229910052698 phosphorus Inorganic materials 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 229920000642 polymer Polymers 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical class [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 11
- 229910052723 transition metal Inorganic materials 0.000 claims description 11
- 150000003624 transition metals Chemical class 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- 150000002466 imines Chemical class 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 8
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 8
- 239000000412 dendrimer Substances 0.000 claims description 8
- 229920000736 dendritic polymer Polymers 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229910052741 iridium Inorganic materials 0.000 claims description 8
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical group [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 150000007942 carboxylates Chemical class 0.000 claims description 7
- 239000010931 gold Chemical group 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 239000010949 copper Chemical group 0.000 claims description 6
- 230000005525 hole transport Effects 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 239000010948 rhodium Chemical group 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 5
- 150000002602 lanthanoids Chemical class 0.000 claims description 5
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical group [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 229910052733 gallium Inorganic materials 0.000 claims description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical group [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052737 gold Inorganic materials 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052738 indium Inorganic materials 0.000 claims description 4
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N isonitrile group Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 4
- 150000002527 isonitriles Chemical class 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 239000011733 molybdenum Chemical group 0.000 claims description 4
- 229910052762 osmium Inorganic materials 0.000 claims description 4
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical group [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 229910052702 rhenium Inorganic materials 0.000 claims description 4
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical group [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical group [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 239000010937 tungsten Chemical group 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical group [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- 125000004986 diarylamino group Chemical group 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 3
- 150000003949 imides Chemical class 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical group [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- 239000004332 silver Chemical group 0.000 claims description 3
- 150000007944 thiolates Chemical class 0.000 claims description 3
- IPRROFRGPQGDOX-UHFFFAOYSA-K 1,2,3,4,5-pentamethylcyclopenta-1,3-diene;trichlorotitanium Chemical group Cl[Ti](Cl)Cl.CC=1C(C)=C(C)[C-](C)C=1C IPRROFRGPQGDOX-UHFFFAOYSA-K 0.000 claims description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 229910000074 antimony hydride Inorganic materials 0.000 claims description 2
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- 150000008378 aryl ethers Chemical class 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- 150000004294 cyclic thioethers Chemical class 0.000 claims description 2
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims description 2
- 229910000071 diazene Inorganic materials 0.000 claims description 2
- VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 229910052746 lanthanum Inorganic materials 0.000 claims description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 2
- 229910001507 metal halide Inorganic materials 0.000 claims description 2
- 150000005309 metal halides Chemical class 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 150000002923 oximes Chemical class 0.000 claims description 2
- 150000004707 phenolate Chemical class 0.000 claims description 2
- 235000021317 phosphate Nutrition 0.000 claims description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 229910052706 scandium Inorganic materials 0.000 claims description 2
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical group [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 150000004760 silicates Chemical class 0.000 claims description 2
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical compound [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003375 sulfoxide group Chemical group 0.000 claims description 2
- 229910052714 tellurium Inorganic materials 0.000 claims description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 2
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims 2
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 claims 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 1
- MUCRYNWJQNHDJH-OADIDDRXSA-N Ursonic acid Chemical compound C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C MUCRYNWJQNHDJH-OADIDDRXSA-N 0.000 claims 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 1
- 238000005899 aromatization reaction Methods 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- 229910052735 hafnium Inorganic materials 0.000 claims 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- OKQKDCXVLPGWPO-UHFFFAOYSA-N sulfanylidenephosphane Chemical compound S=P OKQKDCXVLPGWPO-UHFFFAOYSA-N 0.000 claims 1
- 229910052726 zirconium Inorganic materials 0.000 claims 1
- 239000010410 layer Substances 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- 238000000034 method Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- 230000006872 improvement Effects 0.000 description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 239000011651 chromium Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
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- PMZLFYBZWYRRAZ-UHFFFAOYSA-N tricyclohexylarsane Chemical compound C1CCCCC1[As](C1CCCCC1)C1CCCCC1 PMZLFYBZWYRRAZ-UHFFFAOYSA-N 0.000 description 1
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- AVYPTBDUFIEJDP-UHFFFAOYSA-N tricyclohexylstibane Chemical compound C1CCCCC1[Sb](C1CCCCC1)C1CCCCC1 AVYPTBDUFIEJDP-UHFFFAOYSA-N 0.000 description 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- PORFVJURJXKREL-UHFFFAOYSA-N trimethylstibine Chemical compound C[Sb](C)C PORFVJURJXKREL-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
- QZBJYTDDWVXFDF-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)arsane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1[As](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F QZBJYTDDWVXFDF-UHFFFAOYSA-N 0.000 description 1
- FQLSDFNKTNBQLC-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)phosphane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1P(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F FQLSDFNKTNBQLC-UHFFFAOYSA-N 0.000 description 1
- QYWFCUVQKBNIRJ-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)stibane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1[Sb](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F QYWFCUVQKBNIRJ-UHFFFAOYSA-N 0.000 description 1
- YSPBORFVJLIOMX-UHFFFAOYSA-N tritert-butylarsane Chemical compound CC(C)(C)[As](C(C)(C)C)C(C)(C)C YSPBORFVJLIOMX-UHFFFAOYSA-N 0.000 description 1
- NZJQTVDLVPHKGY-UHFFFAOYSA-N tritert-butylstibane Chemical compound CC(C)(C)[Sb](C(C)(C)C)C(C)(C)C NZJQTVDLVPHKGY-UHFFFAOYSA-N 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
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Abstract
Description
Yは各々の存在について同じまたは異なり、第3、第4、第5または第6主族の置換または非置換の原子であり、各々の場合2つの基Lに連結する;
L1は各々の存在について同じまたは異なり、金属Mに結合する単座、二座、三座、四座、五座または六座配位子である;
nは各々の存在について同じまたは異なり、0、1、2、3、4、5または6であり、n=0は、基Yが存在せず、2つの基Lの間に単結合が存在することを意味する;
pは0、1、2、3、4、5、6、7、8または9である。
Dは各々の存在について同じまたは異なり、C、N、P、C−O−、C−S−、C−NR2またはC−PR2であり、上述の最後の4つの基は環外のドナー原子としてO、S、NもしくはPまたはC−NΞCを介して金属に結合し、この基は環外のイソニトリル基の炭素を介して金属に結合する;
Eは各々の存在について同じまたは異なり、CまたはNである;
Arは各々の存在について同じまたは異なり、基E−D−Eと共に5〜40の芳香環原子を有するアリールまたはヘテロアリール基を形成し、且つ1以上の基Rにより置換されてもよく;またはDがカルベン炭素原子を表わす場合、Arは基E−D−Eと共に5〜10の環原子を有する環状飽和基を形成する基である;
Yは各々の存在について同じまたは異なり、BR1、B(R1)2 −、C(R1)−、C(R1)2、Si(R1)−、Si(R1)2、C(=O)、C(=NR)、N−、NR1、N(R1)2 +、PR1、P(R1)2 +、AsR1、As(R1)2 +、P(=O)R1、As(=O)R1、P(=S)R1、As(=S)R1、O、S、S(R1)+、Se、Te、S(=O)、S(=O)2、Se(=O)、Se(=O)2、Te(=O)またはTe(=O)2である;
Rは各々の存在について同じまたは異なり、H、重水素、F、Cl、Br、I、N(R2)2、CN、NO2、Si(R2)3、B(OR2)2、C(=O)R2、P(=O)(R2)2、S(=O)R2、S(=O)2R2、OSO2R2、1〜40のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、または2〜40のC原子を有する直鎖アルケニルもしくはアルキニル基、または3〜40のC原子を有する分枝または環状アルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基、その各々が1以上の基R2により置換されてよく、1以上の非隣接CH2基がR2C=CR2、CΞC、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SまたはCONR2により置換されてよく、1以上のH原子がF、Cl、Br、I、CNもしくはNO2により置換されてよい、または5〜60の芳香環原子を有する芳香族もしくは芳香族複素環系、これは各々の場合1以上の基R2により置換されてよい、または5〜60の芳香族原子を有するアリールオキシもしくはヘテロアリールオキシ、これは1以上の基R2により置換されてよい、または10〜40の芳香環原子を有するジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基、これは1以上の基R2により置換されてよい、またはこれらの系の組合せである;これらの置換基Rのうち2以上が互いに、単環もしくは多環、脂肪族、芳香族および/またはベンゾ縮合環系を形成する;
R1は各々の存在について同じまたは異なり、Rまたは基L2である;
R2は各々の存在について同じまたは異なり、H、Fもしくは1〜20のC原子を有する脂肪族、芳香族および/または芳香族複素環炭化水素であり、ここでさらに1以上のH原子がFにより置換されてよい;ここで2以上の置換基R2は単環または多環の脂肪族もしくは芳香族環系を互いに形成してもよい;
L2は各々の存在について同じまたは異なり、1〜40のC原子を有するドナー基であり、これは金属Mに対してさらなる結合または配位を形成し、1以上の基Rにより置換されてよい;
nは各々の存在について同じまたは異なり、0、1、2、3、4、5または6であり、n=0は、基Yが存在せず、2つの基Lの間に単結合が存在することを意味し、但し全ての指数nは同時に0を表わさない。
Dは各々の存在について同じまたは異なり、C、NまたはC−O−を表わす。
Halは各々の存在について同じまたは異なり、F、Cl、BrまたはIである;
Ligは各々の存在について同じまたは異なり、中性または一価陰イオン性の単座もしくは二座配位子であり、例えばハライドまたは水酸化物である;
qは各々の存在について同じまたは異なり、0、1、2、3または4、好ましくは0、1または2である;
rは各々の存在について同じまたは異なり、1、2、3、4または5であり、式(66)および(68)においてrは金属Mの原子価を示す;
式(67)の化合物もまた荷電し、イオンを含んでいてもよく;式(66)−(68)の化合物、特に式(68)の化合物はさらに水和物の形態であってよい。
1.昇華の際に部分的または完全な熱分解を経る先行技術に従う多くの金属錯体とは対照的に、本発明に従う化合物は高い熱安定性を有する。
以下の合成は他に示さない限り、保護ガス環境下、乾燥溶媒中で行われる。溶媒および試薬はALDRICHまたはABCRから購入することができる。以下の配位子1−4の合成は示される文献に従って行われる:
配位子1:
LEDを以下で概説する一般的方法により製造する。もちろんこれは個々のケースにおいて特定の環境に適合させなければならない(例えば、最適効率または色を達成するための層の厚さのバリエーション)。
ITOをコーティングした基板(例えばガラス基板、PET薄膜)を適切な大きさに切った後、それらを超音波槽中で多くの洗浄工程で洗浄する(例えば、せっけん水、ミリポア水、イソプロパノール)。乾燥のため、それらをN2ガン(gun)により送風し、デシケータに保存する。有機層による蒸気コーティングの前に、それらを約20分オゾンプラズマデバイスにより処理する。第一有機層として高分子正孔注入層を用いることが望ましい。これは一般に共役した導電性高分子、例えばポリアニリン誘導体(PANI)またはポリチオフェン誘導体(例えばBAYERからのPEDOT、BAYTRON(商標)である)などである。次にこれをスピンコーティングにより適用する。高真空ユニット中で蒸着により有機層を連続的に適用する。各層の厚さおよび蒸着速度をモニターし、水晶振動子により調節する。個々の層が1以上の化合物からなることも可能である、即ち一般にホスト材料がゲスト材料によりドープされてもよい。これは2以上の原料からの共蒸着(co−evaporation)により達成される。電極もまた有機層に適用される。これは一般に熱蒸発により行われる(Balzer BA360またはPfeiffer PL S 500)。続いて透明ITO電極を陽極として、金属電極を陰極として接触させ、デバイスパラメータを決定する。
PEDOT 20 nm(水からスピンコーティングされる;BAYER AGから購入したPEDOT;ポリ[3,4−エチレンジオキシ−2,5−チオフェン]
HIM1 20 nmの2,2’,7,7’−テトラキス(ジ−p−トリルアミノ)スピロ−9,9’−ビフルオレン(蒸着される)
NPB 20 nmの4,4’−ビス(1−ナフチルフェニルアミノ)ビフェニル(蒸着される)
mCP 本発明に従う三重項発光体10%によりドープされる20 nmの1,3−ビス(N−カルバゾリル)ベンゼン(蒸着される)、表を参照されたい
BCP 5 nmの2,9−ジメチル−4,7−ジフェニル−1,10−フェナントロリン(蒸着される)
AlQ3 30 nm(蒸着される)
Li/Al 5 nmのLiF、上部に陰極として150 nmのAl。
PVK 60 nm(クロロベンゼンからスピンコーティングされる、Aldrichから購入したPVK Mw=1,100,000、例4に従う5重量%の発光体を含む溶液)
Ba/Ag 陰極としての10 nmのBa/150 nmのAg。
Claims (16)
- 式(2)の配位子に配位する金属Mを含む式(1)の金属錯体を少なくとも1つ含む電子デバイス
Lは各々の存在について同じまたは異なり、置換または非置換環状基であり、各々の場合に環中に少なくとも1つのドナー原子もしくはC原子または環外ドナー原子を含み、これを介して環状基が金属Mに結合し;基Lが基Yを介して互いに連結する;
Yは各々の存在について同じまたは異なり、第3、4、5または6主族の置換または非置換原子であり、各々の場合2つの基Lに連結する;
L1は各々の存在について同じまたは異なり、金属Mに結合する単座、二座、三座、四座、五座または六座配位子である;
nは各々の存在について同じまたは異なり、0、1、2、3、4、5または6であり、n=0は、基Yが存在せず、2つの基Lの間に単結合が存在することを意味する;
pは0、1、2、3、4、5、6、7、8または9である。 - 陽極、陰極、および少なくとも1つの式(1)の化合物を含む少なくとも1つの層を含む請求項1に記載の電子デバイスであって、有機エレクトロルミネセントデバイス(OLED、PLED)、有機集積回路(O−IC)、有機電界効果トランジスタ(O−FET)、有機薄層トランジスタ(O−TFT)、有機発光トランジスタ(O−LET)、有機太陽電池(O−SC)、有機光学検出器、有機光受容体、有機電界クエンチ(quench)デバイス、発光電気化学電池(LEC)および有機レーザーダイオード(O−laser)、好ましくは有機エレクトロルミネセントデバイスからなる群より選択される電子デバイス。
- 請求項1または2に記載の電子デバイスであって、環状基Lが置換または非置換アリールもしくはヘテロアリール基または環状飽和もしくは不飽和カルベンを示すことを特徴とする電子デバイス。
- 請求項1〜3のいずれか1項以上に記載の電子デバイスであって、式(3)の化合物を少なくとも1つ含む電子デバイス
Mは遷移金属、ランタニド、アルカリ金属、アルカリ土類金属または第3または4主族の主族金属である;
Dは各々の存在について同じまたは異なり、C、N、P、C−O−、C−S−、C−NR2またはC−PR2であり、上述の最後の4つの基はO、S、NもしくはPまたはC−NΞCを介して環外のドナー原子として金属に結合し、この基は環外のイソニトリル基の炭素を介して金属に結合する;
Eは各々の存在について同じまたは異なり、CまたはNである;
Arは各々の存在について同じまたは異なり、基E−D−Eと共に5〜40の芳香環原子を有するアリールまたはヘテロアリール基を形成し、1以上の基Rにより置換されてよく;またはDがカルベン炭素原子を表わす場合、Arは基E−D−Eと共に5〜10の環原子を有する環状飽和基を形成する基である;
Yは各々の存在について同じまたは異なり、BR1、B(R1)2 −、C(R1)−、C(R1)2、Si(R1)−、Si(R1)2、C(=O)、C(=NR)、N−、NR1、N(R1)2 +、PR1、P(R1)2 +、AsR1、As(R1)2 +、P(=O)R1、As(=O)R1、P(=S)R1、As(=S)R1、O、S、S(R1)+、Se、Te、S(=O)、S(=O)2、Se(=O)、Se(=O)2、Te(=O)またはTe(=O)2である;
Rは各々の存在について同じまたは異なり、H、重水素、F、Cl、Br、I、N(R2)2、CN、NO2、Si(R2)3、B(OR2)2、C(=O)R2、P(=O)(R2)2、S(=O)R2、S(=O)2R2、OSO2R2、1〜40のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、2〜40のC原子を有する直鎖アルケニルもしくはアルキニル基、または3〜40のC原子を有する分枝もしくは環状アルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基、その各々は1以上の基R2により置換されてよく、1以上の非隣接CH2基はR2C=CR2、CΞC、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SまたはCONR2により置換されてよく、1以上のH原子はF、Cl、Br、I、CNもしくはNO2により置換されてよい、または5〜60の芳香環原子を有する芳香族もしくは芳香族複素環系、これは各々の場合1以上の基R2により置換されてよい、または5〜60の芳香環原子を有するアリールオキシもしくはヘテロアリールオキシ基、これは1以上の基R2により置換されてよい、または10〜40の芳香環原子を有するジアリールアミノ基、ジヘテロアリールアミノ基もしくはアリールヘテロアリールアミノ基、これは1以上の基R2により置換されてよい、またはこれらの系の組合せである;これらの置換基Rのうち2以上もまた互いに単環または多環の脂肪族、芳香族および/またはベンゾ縮合環系を形成してよい;
R1は各々の存在について同じまたは異なり、Rまたは基L2である;
R2は各々の存在について同じまたは異なり、H、Fまたは1〜20のC原子を有する脂肪族、芳香族および/または芳香族複素炭化水素基であり、1以上のH原子がさらにFにより置換されてよい;ここで2以上の置換基R2は互いに単環または多環の脂肪族もしくは芳香環系を形成してもよい;
L2は各々の存在について同じまたは異なり、1〜40のC原子を有するドナー基であり、金属Mに対してさらなる結合または配位を形成してよく、1以上の基Rにより置換されてよい;
nは各々の存在について同じまたは異なり、0、1、2、3、4、5または6であり、n=0は、基Yが存在せず、単結合が2つの基Lの間に存在することを意味し、但しすべての指数は同時に0を表わさない。 - 請求項1〜4の何れか1項以上に記載の電子デバイスであって、Mがジルコニウム、ハフニウム、モリブデン、タングステン、レニウム、ルテニウム、オスミウム、ロジウム、イリジウム、パラジウム、白金、銅、銀、金、スカンジウム、イットリウム、ランタン、アルミニウム、ガリウムまたはインジウムを表わすことを特徴とする電子デバイス。
- 請求項1〜7の何れか1項以上に記載の有機電子デバイスであって、基L2がアリールまたはヘテロアリール基を示し、式(21)−(49)の基から選択され、各々の場合において破線の結合が配位子中のこの基の結合、即ち基Zへの結合を示し、各々の場合において*は金属Mへの配位の位置を示し、用いられる記号は請求項1および3で示される意味を有することを特徴とするか:
- 請求項1〜8のいずれか1項以上に記載の電子デバイスであって、配位子L1が一酸化炭素、イソニトリル、アミン、イミン、ジイミン、ホスフィン、ホスファイト、アルシン、スチビン、窒素含有複素環化合物、ヒドリド、重水素化物、ハライドF、Cl、BrおよびI、アルキルアセチリド、アリールアセチリド、シアニド、シアネート、イソシアネート、チオシアネート、イソチオシアネート、脂肪族もしくは芳香族アルコレート、脂肪族もしくは芳香族チオアルコレート、アミド、カルボキシレート、陰イオン性窒素含有複素環化合物、O2−、S2−、ニトレン、N3−、ジアミン、2つの窒素原子を含むヘテロ環化合物、ジホスフィン、1,3−ジケトン由来の1,3−ジケトネート、3−ケトエステル由来の3−ケトネート、アミノカルボン酸由来のカルボキシレート、サリチルイミン由来のサリチルイミネート、ジアルコール由来のジアルコレート、窒素含有複素環化合物のボレート、一価陰イオン性二座配位子、これは金属とともに少なくとも1つの金属−炭素結合を含むシクロメタレート化五員環を形成する、η5−シクロペンタジエニル、η5−ペンタメチルシクロペンタジエニル、η6−ベンゼン、η7−シクロヘプタトリエニル、各々はRにより置換されてよい、1,3,5−シス−シクロヘキサン誘導体、1,1,1−トリ(メチレン)メタン誘導体および1,1,1−三置換メタンから選択されることを特徴とする電子デバイス。
- 請求項1〜10の何れか1項以上に記載の電子デバイスであって、それが陰極、陽極、および少なくとも1つの発光層、および各々の場合、任意に1以上の正孔注入層、正孔輸送層、正孔阻止層、電子輸送層、電子注入層、励起子阻止層、電荷発生層および/または有機もしくは無機p/n接合部から選択されるさらなる層を含む有機エレクトルミネセントデバイスであることを特徴とする電子デバイス。
- 請求項11に記載の有機エレクトロルミネセントデバイスであって、式(1)または式(3)−(7)の化合物を発光層中の発光化合物として、好ましくは1以上のマトリクス材料と組み合わせて用いるか、式(1)または式(3)−(7)の化合物を発光層中の発光化合物のためのマトリクス材料として用いるか、式(1)または式(3)−(7)の化合物を正孔阻止層中の正孔阻止材料および/または電子輸送層中の電子輸送材料として用いるか、または式(1)または式(3)−(7)の化合物を正孔輸送層中の正孔輸送材料および/または励起子阻止層中の励起子阻止材料として用いることを特徴とする有機エレクトロルミネセントデバイス。
- 式(2)の配位子および任意のさらなる配位子L1を式(66)の金属アルコキシド、式(67)の金属ケトケトネート、または式(68)の金属ハライドと反応させることにより請求項13に記載の化合物を製造する方法:
Halは各々の存在について同じまたは異なり、F、Cl、BrまたはIである;
Ligは各々の存在について同じまたは異なり、中性または1価陰イオン性の単座もしくは二座配位子である;
qは各々の存在について同じまたは異なり、0、1、2、3または4、好ましくは0、1または2である;
rは各々の存在について同じまたは異なり、1、2、3、4または5であり、式(66)および(68)中のrは金属Mの原子価を示す;
式(67)の化合物もまた荷電していてよく、対イオンを含んでもよい;式(66)−(68)、特に式(68)の化合物はさらに水和物の形態であってもよい。 - 1以上の結合が、式(1)もしくは式(3)−(7)の錯体からポリマー、オリゴマーまたはデンドリマーに存在する、式(1)もしくは式(3)−(7)の1以上の化合物を含むオリゴマー、ポリマーまたはデンドリマー。
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JP7139013B2 (ja) | 2019-05-21 | 2022-09-20 | エルジー・ケム・リミテッド | 硬化性組成物およびその硬化物を含む光学部材 |
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WO2009146770A3 (de) | 2010-04-29 |
JP5744724B2 (ja) | 2015-07-08 |
US10538698B2 (en) | 2020-01-21 |
EP2294160A2 (de) | 2011-03-16 |
EP2294160B1 (de) | 2018-10-17 |
KR20110015463A (ko) | 2011-02-15 |
US9481826B2 (en) | 2016-11-01 |
US20160024119A1 (en) | 2016-01-28 |
CN102057014B (zh) | 2015-05-06 |
US20110089410A1 (en) | 2011-04-21 |
DE102008027005A1 (de) | 2009-12-10 |
CN102057014A (zh) | 2011-05-11 |
WO2009146770A2 (de) | 2009-12-10 |
TW201012825A (en) | 2010-04-01 |
KR101677305B1 (ko) | 2016-11-17 |
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