CN1829724B - 金属络合化合物和使用了该化合物的有机电致发光元件 - Google Patents
金属络合化合物和使用了该化合物的有机电致发光元件 Download PDFInfo
- Publication number
- CN1829724B CN1829724B CN2004800206564A CN200480020656A CN1829724B CN 1829724 B CN1829724 B CN 1829724B CN 2004800206564 A CN2004800206564 A CN 2004800206564A CN 200480020656 A CN200480020656 A CN 200480020656A CN 1829724 B CN1829724 B CN 1829724B
- Authority
- CN
- China
- Prior art keywords
- basic framework
- metal complex
- layer
- complex compounds
- carbonatoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- -1 Metal complex compound Chemical class 0.000 title claims abstract description 70
- 229910052751 metal Inorganic materials 0.000 claims abstract description 18
- 239000002184 metal Substances 0.000 claims abstract description 18
- 239000010409 thin film Substances 0.000 claims abstract description 11
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 7
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000010408 film Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 238000000576 coating method Methods 0.000 claims description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 239000010948 rhodium Substances 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 68
- 239000010410 layer Substances 0.000 description 61
- 239000000463 material Substances 0.000 description 32
- 101100321960 Arabidopsis thaliana ABCI17 gene Proteins 0.000 description 28
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 28
- 101000973997 Homo sapiens Nucleosome assembly protein 1-like 4 Proteins 0.000 description 28
- 108090001007 Interleukin-8 Proteins 0.000 description 28
- 102100022389 Nucleosome assembly protein 1-like 1 Human genes 0.000 description 28
- 102100022396 Nucleosome assembly protein 1-like 4 Human genes 0.000 description 28
- 238000005406 washing Methods 0.000 description 25
- 239000000243 solution Substances 0.000 description 23
- 0 CCCC=C([C@](*)C(C)(**)NCC*)N Chemical compound CCCC=C([C@](*)C(C)(**)NCC*)N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 19
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 229910052786 argon Inorganic materials 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 239000013078 crystal Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000013076 target substance Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229960001866 silicon dioxide Drugs 0.000 description 8
- 239000004411 aluminium Substances 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 230000005540 biological transmission Effects 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 229910000474 mercury oxide Inorganic materials 0.000 description 7
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000027756 respiratory electron transport chain Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- XHLKOHSAWQPOFO-UHFFFAOYSA-N 5-phenyl-1h-imidazole Chemical compound N1C=NC=C1C1=CC=CC=C1 XHLKOHSAWQPOFO-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229910000737 Duralumin Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 2
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 150000008376 fluorenones Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- OQJQPIWVCBJVAZ-UHFFFAOYSA-N 1-methyl-2-phenylimidazole Chemical compound CN1C=CN=C1C1=CC=CC=C1 OQJQPIWVCBJVAZ-UHFFFAOYSA-N 0.000 description 1
- KTGYDKACJATEDM-UHFFFAOYSA-N 1-methyl-4-phenylimidazole Chemical compound CN1C=NC(C=2C=CC=CC=2)=C1 KTGYDKACJATEDM-UHFFFAOYSA-N 0.000 description 1
- ZNRHVRLVJFJFAF-UHFFFAOYSA-N 2-(2,4-difluorophenyl)imidazo[1,2-a]pyridine Chemical compound FC1=CC(F)=CC=C1C1=CN(C=CC=C2)C2=N1 ZNRHVRLVJFJFAF-UHFFFAOYSA-N 0.000 description 1
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
- FGIHSZXDNYRAKQ-UHFFFAOYSA-N 2-benzyl-1-methyl-4,5-dihydroimidazole Chemical compound CN1CCN=C1CC1=CC=CC=C1 FGIHSZXDNYRAKQ-UHFFFAOYSA-N 0.000 description 1
- JMUWGFTVJQKUHU-UHFFFAOYSA-N 3,4-diphenylcyclohexa-3,5-diene-1,2-dione Chemical class C1(=CC=CC=C1)C1=C(C(C(C=C1)=O)=O)C1=CC=CC=C1 JMUWGFTVJQKUHU-UHFFFAOYSA-N 0.000 description 1
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical class CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
- 101100512896 Arabidopsis thaliana MES2 gene Proteins 0.000 description 1
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N C=CC1CCCC1 Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- OFKVKFOVQFXLJS-XHUCQOSOSA-N CCC(C)[C@@H]1C(C2)CC=CC2C1 Chemical compound CCC(C)[C@@H]1C(C2)CC=CC2C1 OFKVKFOVQFXLJS-XHUCQOSOSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 235000007466 Corylus avellana Nutrition 0.000 description 1
- 240000003211 Corylus maxima Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101000617536 Homo sapiens Presenilin-1 Proteins 0.000 description 1
- 101000617546 Homo sapiens Presenilin-2 Proteins 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 101150037847 MES1 gene Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229910000574 NaK Inorganic materials 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 101000612288 Pinus strobus Putative oxygen-evolving enhancer protein 1 Proteins 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101100097991 Schizosaccharomyces pombe (strain 972 / ATCC 24843) rar1 gene Proteins 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
- NSIKFNOYIGGILA-UHFFFAOYSA-N [Na].[Na].[K] Chemical compound [Na].[Na].[K] NSIKFNOYIGGILA-UHFFFAOYSA-N 0.000 description 1
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- MQMJQPYOEGFMAZ-UHFFFAOYSA-N anthracene;styrene Chemical compound C=CC1=CC=CC=C1.C1=CC=CC2=CC3=CC=CC=C3C=C21 MQMJQPYOEGFMAZ-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000004646 arylidenes Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 150000004054 benzoquinones Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- BWFPGXWASODCHM-UHFFFAOYSA-N copper monosulfide Chemical compound [Cu]=S BWFPGXWASODCHM-UHFFFAOYSA-N 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical group 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
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical group [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 description 1
- HMRCBLAEVOMPHP-UHFFFAOYSA-N oxadiazole quinoline Chemical compound C1=CON=N1.N1=CC=CC2=CC=CC=C21 HMRCBLAEVOMPHP-UHFFFAOYSA-N 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- JIVZKJJQOZQXQB-UHFFFAOYSA-N tolazoline Chemical compound C=1C=CC=CC=1CC1=NCCN1 JIVZKJJQOZQXQB-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0046—Ruthenium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/006—Palladium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0073—Rhodium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0086—Platinum compounds
-
- 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
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- 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
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Abstract
本发明提供含有铱等金属的特定结构的金属络合化合物以及发光效率高、寿命长的有机电致发光元件和用于制造该元件的金属络合化合物,所述有机电致发光元件是在一对电极间夹持着至少具有发光层的由一层或多层构成的有机薄膜层,该有机薄膜层中的至少1层含有上述金属络合化合物,通过在两极间施加电压而使其发光。
Description
技术领域
本发明涉及新型金属络合化合物和使用了该化合物的有机电致发光(EL)元件,特别是涉及发光效率高、寿命长的有机EL元件和用于实现该元件的新型金属络合化合物。
背景技术
近年来,有机EL元件作为代替液晶的彩色显示器用显示装置的研究日趋活跃,但是,实现大屏幕化还存在着发光元件性能的不足。为了提高所述有机EL元件的性能,有人提出在发光材料中使用磷光发光材料原金属化铱络合物(面-三(2-苯基吡啶)合铱)的绿色发光元件的方案(例如参照D.F.O’Brien和M.A.Baldo等的“Improved energytransferin electrophosphorescent devices”,发表于Physics Letters Vol.74No.3,442-444页,1999年1月18日;M.A.Baldo等的“Very high-efficiencygreen organic light-emitting devices based onelectrophosphorescence”,发表于Physics Letters Vol.75 No.1,4-6页,1999年7月5日)。
由于利用磷光发光的有机EL元件目前只限于绿色发光,作为彩色显示器的应用范围窄,所以期待着开发出其它色彩的发光特性也得到改善的元件。特别是蓝色发光元件,外部量子收率超过5%的还没有报道,如果蓝色发光元件能够得到改善,则有望实现全彩色化和白色化,磷光EL元件的实用化将有更大的进步。
此外,国际公开WO02/15645号公报公开了如下所示的配体结构式(A)和(B),但未公开使用该配体的实际络合物的合成例。
(式中,R1-R5各自独立表示氢原子、卤素原子、烷基、芳基、亚芳基,R1’和R2’各自独立表示芳基,也可以相互结合。)
发明内容
本发明致力于解决上述问题,目的在于提供发光效率高、寿命长的有机EL元件和实现该元件的新型金属络合化合物。
本发明人为实现上述目的进行了深入的研究,结果发现:当上述配体(A)和(B)中的R为H时,不会产生专利文献1所描述的Ir络合物,无法进行稳定的分离,所以将与金属不形成配位键的N上的原子用氢原子以外的基团进行置换,这一点对于稳定地分离Ir络合物很重要,于是设计了N上具有各种取代基的配体,首次成功合成了Ir络合物。由此制成了采用具有下述通式(I)所示部分结构的金属络合化合物的有机EL元件,这种EL元件的外部量子收率达到8%,以蓝色区域为首的各种磷光发光的发光效率高、寿命长,从而完成了本发明。
即,本发明提供具有下述通式(I)所示部分结构的金属络合化合物。
[式中,R1-R5各自独立表示氢原子、氰基、硝基、卤素原子、取代或无取代的碳原子数为1-20的烷基、取代或无取代的氨基、取代或无取代的碳原子数为1-20的烷氧基、取代或无取代的碳原子数为1-20的烷基甲硅烷基、取代或无取代的碳原子数为1-20的酰基、或者取代或无取代的碳原子数为1-30的芳基,并且,R1和R2、R3和R4、R4和R5可以相互结合形成环结构。
p和q分别为0-3的整数,p+q为2或3。并且,当p为2以上的整数时,多个R3可以相互结合形成环结构,q为2以上的整数时,多个R5可以相互结合形成环结构。
M为铱(Ir)、铑(Rh)、铂(Pt)或钯(Pd)的金属原子。]
另外,本发明提供一种有机EL元件,该元件是在一对电极间夹持着至少具有发光层的由一层或多层构成的有机薄膜层,该有机薄膜层中至少一层含有上述金属络合化合物,通过在两极间施加电压而使其发光。
实施发明的最佳方式
本发明的金属络合化合物具有下述通式(I)所示部分结构。
通式(I)中,R1-R5各自独立表示氢原子、氰基、硝基、卤素原子、取代或无取代的碳原子数为1-20的烷基、取代或无取代的氨基、取代或无取代的碳原子数为1-20的烷氧基、取代或无取代的碳原子数为1-20的烷基甲硅烷基、取代或无取代的碳原子数为1-20的酰基、或者取代或无取代的碳原子数为1-30的芳基,并且,R1和R2、R3 和R4、R4和R5可以相互结合形成环结构。
上述卤素原子的例子有:氟、氯、溴、碘。
上述烷基的例子有:甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、正己基、正庚基、正辛基等。
上述烷氧基由-OY表示,Y的例子和上述烷基的例子相同。
上述烷基甲硅烷基的例子有三甲基甲硅烷基、叔丁基二甲基甲硅烷基等。
上述酰基的例子有乙酰基、丙酰基、丁酰基、异丁酰基等。
上述芳基的例子有:苯、萘、蒽、菲、芘、晕苯、联苯、联三苯、吡咯、呋喃、噻吩、苯并噻吩、噁二唑啉、二苯基蒽、二氢吲哚、咔唑、吡啶、苯醌、荧蒽、苊并荧蒽等。
另外,上述各基团的取代基的例子有:氰基、羟基、硝基、卤素原子、取代或无取代的烷基、取代或无取代的氨基、取代或无取代的烷氧基、取代或无取代的烷基甲硅烷基、取代或无取代的酰基、或者取代或无取代的芳基、取代或无取代的烯基、取代或无取代的环烷基、取代或无取代的杂环基、取代或无取代的芳基烷基、取代 或无取代的芳氧基、取代或无取代的烷氧基羰基、羧基等。
R1和R2、R3和R4、R4和R5相互结合形成的环结构例如分别独立为苯、吡啶、萘、苯并噻唑、喹啉等。
优选R1-R5各自独立为氢原子、氰基、硝基、氟原子、三氟甲基、二甲氨基、甲氧基、叔丁基、三甲基甲硅烷基、乙酰基。
p和q分别为0-3(优选0-2)的整数,p+q为2或3。并且,当p为2以上的整数时,多个R3可以相互结合形成环结构,q为2以上的整数时,多个R5可以相互结合形成环结构。
多个R3以及多个R5形成的环结构例如分别独立为苯、吡啶等。
通式(I)中,结构A表示含有至少1个碳-氮双键的碳原子数为3-20的环结构,可以有取代基,可以形成含有上述R4的环结构。
通式(I)中,M代表铱(Ir)、铑(Rh)、铂(Pt)或钯(Pd)的金属原子,优选Ir、Pt,更优选Ir。
另外,优选通式(I)所示部分结构为下述(i)-(vii)中的任意一种结构,或者为下述(i’)-(vii’)中的任意一种结构,更优选(i)-(iii)。
进一步优选本发明的金属络合化合物为具有下述通式1-7和1’-7’中任意一种所示基本骨架的化合物。
通式1-7和1’-7’式中,T5-T9各自独立表示氢原子、氰基、硝基、卤素原子、取代或无取代的碳原子数为1-20的烷基、取代或无取代的氨基、取代或无取代的碳原子数为1-20的烷氧基、取代或无取代的碳原子数为1-20的烷基甲硅烷基、取代或无取代的碳原子数为1-20的酰基、或者取代或无取代的碳原子数为1-30的芳基,并且,T5和T6、T6和T7、T7和T8、T8和T9可以相互结合形成环结构。
上述卤素原子、烷基、烷氧基、烷基甲硅烷基、酰基、芳基和它们的取代基的例子与上述通式(I)中R1-R5的例子相同,优选的例子也相同。
T5和T6、T6和T7、T7和T8、T8和T9相互结合形成的环结构例如各自独立为苯、吡啶等。
通式1-7和1’-7’中,M与上述相同。
通式1-7和1’-7’中,L1和L2表示下示结构中的任意一种。
通式1-7和1’-7’中,n为0-2的整数,优选为0-1,m为0-1的整数。
G表示下示基团中的任意一种基团。
(...表示与上述M的共价键)。
Ph和OL中的T1-T4可各自独立表示氰基、硝基、卤素原子、取代或无取代的碳原子数为1-20的烷基、取代或无取代的氨基、取代或无取代的碳原子数为1-20的烷氧基、取代或无取代的碳原子数为1-20的烷基甲硅烷基、取代或无取代的碳原子数为1-20的酰基、或者取代或无取代的碳原子数为1-30的芳基,所述基团和所述取代基的例子与上述通式(I)的R1-R5中的描述一样,优选的例子也一样。
Ph中,T1和T2、T2和T3或者T3和T4结合形成环结构的取代基的例子有下述任一式所表示二价基团,优选BL、MES1、MES2、PS1、PS2。
但是,这些二价基团的左边与T1-T4中编号小的结合,同样右边 则与编号大的结合。
本发明的具有通式1-7和1’-7’所示基本骨架的金属络合化合物的具体例子列于下面的表中,但并不限于这些例示化合物。
各表第一行的基本骨架的右侧记载了T1-T9、L1、L2(基本骨架1-4和1’-4’的情况)或T1-T7、L1、L2(基本骨架5-7和5’-7’的情况)。
表1
表2
表3
表4
表5
表6
表7
基本骨架1,G:NAP1 基本骨架1,G:NAP2 基本骨架1,G:NAP3
基本骨架1,G:TB 基本骨架1,G:TF 基本骨架1,G:OB
基本骨架1,G:Fu 基本骨架1,G:Fl 基本骨架1,G:Bz
基本骨架1,G:Qu 基本骨架1,G:OL
表8
基本骨架2,G:NAP1 基本骨架2,G:NAP2 基本骨架2,G:NAP3
基本骨架2,G:TB 基本骨架2,G:TF 基本骨架2,G:OB
基本骨架2,G:Fu 基本骨架2,G:Fl 基本骨架2,G:Bz
基本骨架2,G:Qu 基本骨架2,G:OL
表9
基本骨架3,G:NAP1 基本骨架3,G:NAP2 基本骨架3,G:NAP3
基本骨架3,G:TB 基本骨架3,G:TF 基本骨架3,G:OB
基本骨架3,G:Fu 基本骨架3,G:Fl 基本骨架3,G:Bz
基本骨架3,G:Qu 基本骨架3,G:OL
表10
基本骨架4,G:NAP1 基本骨架4,G:NAP2 基本骨架4,G:NAP3
基本骨架4,G:TB 基本骨架4,G:TF 基本骨架4,G:OB
基本骨架4,G:Fu 基本骨架4,G:Fl 基本骨架4,G:Bz
基本骨架4,G:Qu 基本骨架4,G:OL
表11
基本骨架5,G:NAP1 基本骨架5,G:NAP2 基本骨架5,G:NAP3
基本骨架5,G:TB 基本骨架5,G:TF 基本骨架5,G:OB
基本骨架5,G:Fu 基本骨架5,G:Fl 基本骨架5,G:Bz
基本骨架5,G:Qu 基本骨架5,G:OL
表12
基本骨架6,G:NAP1 基本骨架6,G:NAP2 基本骨架6,G:NAP3
基本骨架6,G:TB 基本骨架6,G:TF 基本骨架6,G:OB
基本骨架6,G:Fu 基本骨架6,G:Fl 基本骨架6,G:Bz
基本骨架6,G:Qu 基本骨架6,G:OL
表13
基本骨架7,G:NAP1 基本骨架7,G:NAP2 基本骨架7,G:NAP3
基本骨架7,G:TB 基本骨架7,G:TF 基本骨架7,G:OB
基本骨架7,G:Fu 基本骨架7,G:Fl 基本骨架7,G:Bz
基本骨架7,G:Qu 基本骨架7,G:OL
表14
表15
表16
表17
表18
表19
表20
表21
基本骨架1,G:NAP1 基本骨架1,G:NAP2 基本骨架1,G:NAP3
基本骨架1,G:TB 基本骨架1,G:TF 基本骨架1,G:OB
基本骨架1,G:Fu 基本骨架1,G:Fl 基本骨架1,G:Bz
基本骨架1,G:Qu 基本骨架1,G:OL
表22
基本骨架2,G:NAP1 基本骨架2,G:NAP2 基本骨架2,G:NAP3
基本骨架2,G:TB 基本骨架2,G:TF 基本骨架2,G:OB
基本骨架2,G:Fu 基本骨架2,G:Fl 基本骨架2,G:Bz
基本骨架2,G:Qu 基本骨架2,G:OL
表23
基本骨架3,G:NAP1 基本骨架3,G:NAP2 基本骨架3,G:NAP3
基本骨架3,G:TB 基本骨架3,G:TF 基本骨架3,G:OB
基本骨架3,G:Fu 基本骨架3,G:Fl 基本骨架3,G:Bz
基本骨架3,G:Qu 基本骨架3,G:OL
表24
基本骨架4,G:NAP1 基本骨架4,G:NAP2 基本骨架4,G:NAP3
基本骨架4,G:TB 基本骨架4,G:TF 基本骨架4,G:OB
基本骨架4,G:Fu 基本骨架4,G:Fl 基本骨架4,G:Bz
基本骨架4,G:Qu 基本骨架4,G:OL
表25
基本骨架5,G:NAP1 基本骨架5,G:NAP2 基本骨架5,G:NAP3
基本骨架5,G:TB 基本骨架5,G:TF 基本骨架5,G:OB
基本骨架5,G:Fu 基本骨架5,G:Fl 基本骨架5,G:Bz
基本骨架5,G:Qu 基本骨架5,G:OL
表26
基本骨架6,G:NAP1 基本骨架6,G:NAP2 基本骨架6,G:NAP3
基本骨架6,G:TB 基本骨架6,G:TF 基本骨架6,G:OB
基本骨架6,G:Fu 基本骨架6,G:Fl 基本骨架6,G:Bz
基本骨架6,G:Qu 基本骨架6,G:OL
表27
基本骨架7,G:NAP1 基本骨架7,G:NAP2 基本骨架7,G:NAP3
基本骨架7,G:TB 基本骨架7,G:TF 基本骨架7,G:OB
基本骨架7,G:Fu 基本骨架7,G:Fl 基本骨架7,G:Bz
基本骨架7,G:Qu 基本骨架7,G:OL
表28
表29
表30
表31
表32
表33
Pt基本骨架6’Ph
表34
表35
基本骨架1’,G:NAP1 基本骨架1’,G:NAP2 基本骨架1’,G:NAP3
基本骨架1’,G:TB 基本骨架1’,G:TF 基本骨架1’,G:OB
基本骨架1’,G:Fu 基本骨架1’,G:Fl 基本骨架1’,G:Bz
基本骨架1’,G:Qu 基本骨架1’,G:OL
表36
基本骨架2’,G:NAP1 基本骨架2’,G:NAP2 基本骨架2’,G:NAP3
基本骨架2’,G:TB 基本骨架2’,G:TF 基本骨架2’,G:OB
基本骨架2’,G:Fu 基本骨架2’,G:Fl 基本骨架2’,G:Bz
基本骨架2’,G:Qu 基本骨架2’,G:OL
表37
基本骨架3’,G:NAP1 基本骨架3’,G:NAP2 基本骨架3’,G:NAP3
基本骨架3’,G:TB 基本骨架3’,G:TF 基本骨架3’,G:OB
基本骨架3’,G:Fu 基本骨架3’,G:Fl 基本骨架3’,G:Bz
基本骨架3’,G:Qu 基本骨架3’,G:OL
表38
基本骨架4’,G:NAP1 基本骨架4’,G:NAP2 基本骨架4’,G:NAP3
基本骨架4’,G:TB 基本骨架4’,G:TF 基本骨架4’,G:OB
基本骨架4’,G:Fu 基本骨架4’,G:Fl 基本骨架4’,G:Bz
基本骨架4’,G:Qu 基本骨架4’,G:OL
表39
基本骨架5’,G:NAP1 基本骨架5’,G:NAP2 基本骨架5’,G:NAP3
基本骨架5’,G:TB 基本骨架5’,G:TF 基本骨架5’,G:OB
基本骨架5’,G:Fu 基本骨架5’,G:Fl 基本骨架5’,G:Bz
基本骨架5’,G:Qu 基本骨架5’,G:OL
表40
基本骨架6’,G:NAP1 基本骨架6’,G:NAP2 基本骨架6’,G:NAP3
基本骨架6’,G:TB 基本骨架6’,G:TF 基本骨架6’,G:OB
基本骨架6’,G:Fu 基本骨架6’,G:Fl 基本骨架6’,G:Bz
基本骨架6’,G:Qu 基本骨架6’,G:OL
表41
基本骨架7’,G:NAP1 基本骨架7’,G:NAP2 基本骨架7’,G:NAP3
基本骨架7’,G:TB 基本骨架7’,G:TF 基本骨架7’,G:OB
基本骨架7’,G:Fu 基本骨架7’,G:Fl 基本骨架7’,G:Bz
基本骨架7’,G:Qu 基本骨架7’,G:OL
表42
表43
表44
表45
表46
表47
表48
表49
基本骨架1’,G:NAP1 基本骨架1’,G:NAP2 基本骨架1’,G:NAP3
基本骨架1’,G:TB 基本骨架1’,G:TF 基本骨架1’,G:OB
基本骨架1’,G:Fu 基本骨架1’,G:Fl 基本骨架1’,G:Bz
基本骨架1’,G:Qu 基本骨架1’,G:OL
表50
基本骨架2’,G:NAP1 基本骨架2’,G:NAP2 基本骨架2’,G:NAP3
基本骨架2’,G:TB 基本骨架2’,G:TF 基本骨架2’,G:OB
基本骨架2’,G:Fu 基本骨架2’,G:Fl 基本骨架2’,G:Bz
基本骨架2’,G:Qu 基本骨架2’,G:OL
表51
基本骨架3’,G:NAP1 基本骨架3’,G:NAP2 基本骨架3’,G:NAP3
基本骨架3’,G:TB 基本骨架3’,G:TF 基本骨架3’,G:OB
基本骨架3’,G:Fu 基本骨架3’,G:Fl 基本骨架3’,G:Bz
基本骨架3’,G:Qu 基本骨架3’,G:OL
表52
基本骨架4’,G:NAP1 基本骨架4’,G:NAP2 基本骨架4’,G:NAP3
基本骨架4’,G:TB 基本骨架4’,G:TF 基本骨架4’,G:OB
基本骨架4’,G:Fu 基本骨架4’,G:Fl 基本骨架4’,G:Bz
基本骨架4’,G:Qu 基本骨架4’,G:OL
表53
基本骨架5’,G:NAP1 基本骨架5’,G:NAP2 基本骨架5’,G:NAP3
基本骨架5’,G:TB 基本骨架5’,G:TF 基本骨架5’,G:OB
基本骨架5’,G:Fu 基本骨架5’,G:Fl 基本骨架5’,G:Bz
基本骨架5’,G:Qu 基本骨架5’,G:OL
表54
基本骨架6’,G:NAP1 基本骨架6’,G:NAP2 基本骨架6’,G:NAP3
基本骨架6’,G:TB 基本骨架6’,G:TF 基本骨架6’,G:OB
基本骨架6’,G:Fu 基本骨架6’,G:Fl 基本骨架6’,G:Bz
基本骨架6’,G:Qu 基本骨架6’,G:OL
表55
基本骨架6’,G:NAP1 基本骨架6’,G:NAP2 基本骨架6’,G:NAP3
基本骨架7’,G:TB 基本骨架7’,G:TF 基本骨架7’,G:OB
基本骨架7’,G:Fu 基本骨架7’,G:Fl 基本骨架7’,G:Bz
基本骨架7’,G:Qu 基本骨架7’,G:OL
表56
本发明的上述金属络合化合物优选为用于发光元件的材料,特别优选为用于有机EL元件的材料。
本发明的有机EL元件是在由阳极和阴极构成的一对电极间夹持着至少具有发光层的由一层或多层构成的有机薄膜层,该有机薄膜层中至少1层含有本发明的金属络合化合物,通过在两极间施加电压而使其发光。
上述有机薄膜层中的本发明的金属络合化合物的含量,相对于发光层全体的质量,通常为0.1-100%重量,优选为1-30%重量。
优选本发明的有机EL元件中的上述发光层含有本发明的金属络合化合物。另外,通常上述发光层利用真空蒸镀或涂布方法形成薄膜,因为涂布的方法可以使制造过程简化,所以优选含有本发明的金属络合化合物的层利用涂布方法形成膜。
本发明的有机EL元件中,有机薄膜层如果是单层的则有机薄膜层为发光层,该发光层含有本发明的金属络合化合物。另外,多层的有机EL元件的例子有:(阳极/空穴注入层(空穴传输层)/发光层/阴极)、(阳极/发光层/电子注入层(电子传输层)/阴极)、(阳极/空穴注入层(空穴传输层)/发光层/电子注入层(电子传输层)/阴极)等。
本发明的有机EL元件的阳极为空穴注入层、空穴传输层、发光层等提供空穴。阳极材料可以使用金属、合金、金属氧化物、导电性化合物或它们的混合物等。阳极材料的具体例子有:氧化锡、氧化锌、氧化铟、氧化铟锡(ITO)等导电性金属氧化物,或金、银、铬、镍等金属,进一步的例子有:上述导电性金属氧化物与金属的混合物或层合物、碘化铜、硫化铜等无机导电性物质,聚苯胺、聚噻唑、 聚吡咯等有机导电性材料,以及所述材料与ITO的层合物等,优选导电性金属氧化物,从生产性、高导电性、透明性等角度考虑特别优选使用ITO。阳极的膜厚可以根据材料适当选择。
本发明的有机EL元件的阴极为电子注入层、电子传输层、发光层等提供电子,阴极的材料可以使用金属、合金、金属卤化物、金属氧化物、导电性化合物或它们的混合物。阴极材料的具体例子有:碱金属(例如锂、钠、钾等)及其氟化物或氧化物,碱土金属(例如镁、钙等)及其氟化物或氧化物,金、银、铅、铝、钠-钾合金或钠-钾混合金属、锂-铝合金或锂-铝混合金属、镁-银合金或镁-银混合金属或者铟、镱等稀土类金属等。其中优选铝、锂-铝合金或锂-铝混合金属、镁-银合金或镁-银混合金属等。阴极可以是上述材料的单层结构,也可以是含有上述材料层的层合结构。例如,优选为铝/氟化锂、铝/氧化锂的层合结构。阴极的膜厚可以根据材料适当选择。
本发明的有机EL元件的空穴注入层和空穴传输层只要是具有从阳极注入空穴的功能、传输空穴的功能、阻碍从阴极注入的电子的功能的任意一种功能的物质即可。其具体例子有:咔唑衍生物、三唑衍生物、噁唑衍生物、噁二唑衍生物、咪唑衍生物、聚芳基链烷衍生物、吡唑啉衍生物、吡唑啉-5-酮衍生物、苯二胺衍生物、芳胺衍生物、氨基取代苯丙烯酰苯衍生物、苯乙烯蒽衍生物、9-芴酮衍生物、腙衍生物、1,2-二苯乙烯衍生物、硅氨烷衍生物、芳族叔胺化合物、苯乙烯胺化合物、芳族二次甲基系化合物、卟啉系化合物、聚硅烷系化合物、聚(N-乙烯基咔唑)衍生物、苯胺系共聚物、噻吩低聚物、聚噻吩等导电性高分子低聚物、有机硅烷衍生物、本发明的金属络合化合物等。而且,上述空穴注入层和上述空穴传输层可以是由一种或多种上述材料构成的单层结构,也可以是由相同组成或不同组成的复数层构成的多层结构。
本发明的有机EL元件的电子注入层和电子传输层只要是具有从阴极注入电子的功能、传输电子的功能、阻碍从阳极注入的空穴的 功能的任意一种功能的物质即可。其具体例子有:三唑衍生物、噁唑衍生物、噁二唑衍生物、咪唑衍生物、9-芴酮衍生物、anthraquinodimethane、蒽酮衍生物、二苯基苯醌衍生物、噻喃二氧化物衍生物、碳化二亚胺衍生物、亚芴基甲烷衍生物、二苯乙烯基吡嗪衍生物、萘、二苯嵌蒽等芳环四羧酸酐、酞菁衍生物、8-羟基喹啉衍生物的金属络合物或金属酞菁、以其配位体为苯并噁唑或苯并噻唑的金属络合物为代表的各种金属络合物、有机硅烷衍生物、本发明的金属络合化合物等。而且,上述电子注入层和上述电子传输层可以是由一种或多种上述材料构成的单层结构,也可以是由相同组成或不同组成的复数层构成的多层结构。
本发明的有机EL元件的发光层具有以下功能:施加电场时可以由阳极或空穴注入层注入空穴,可以由阴极或电子注入层注入电子的功能;通过电场的力使注入的电荷(电子和空穴)移动的功能;提供电子和空穴复合的场所,将其与发光相连的功能。本发明的有机EL元件的发光层最好至少含有本发明的金属络合化合物,也可以使其含有以该金属络合化合物为客体材料的基质材料。上述基质材料的例子有:具有咔唑骨架的材料、具有二芳基胺骨架的材料、具有吡啶骨架的材料、具有吡嗪骨架的材料、具有三嗪骨架的材料以及具有芳基硅烷骨架的材料等。优选上述基质材料的T1(最低三重激态的能量水平)比客体材料的T1水平高。上述基质材料可以是低分子化合物,也可以是高分子化合物。而且,上述基质材料和上述金属络合化合物等发光材料通过共同蒸镀等处理,可以形成上述发光材料掺杂到上述基质材料的发光层。
本发明的有机EL元件中,对上述各层的形成方法并没有特别限定,可利用真空蒸镀法、LB法、电阻加热蒸镀法、电子射束法、溅镀法、分子层叠法、涂布法(旋涂法、流延法、浸渍涂布法等)、喷墨法、印刷法等各种方法,本发明优选涂布法。
上述涂布法可以通过将本发明的金属络合化合物溶解于溶剂中 调制成涂布液,在所希望的层(或者电极)上涂布、干燥该涂布液而形成膜。涂布液中可以含有树脂,树脂在溶剂中可以是溶解状态,也可以是分散状态。上述树脂可以使用非共轭系高分子(例如聚乙烯基咔唑)、共轭系高分子(例如聚烯烃系高分子)。更具体的例子有:聚氯乙烯、聚碳酸酯、聚苯乙烯、聚甲基丙烯酸甲酯、聚甲基丙烯酸丁酯、聚酯、聚砜、聚苯醚、聚丁二烯、聚(N-乙烯基咔唑)、烃类树脂、酮类树脂、苯氧基树脂、聚酰胺、乙基纤维素、醋酸乙烯酯、ABS树脂、聚氨基甲酸酯、三聚氰胺树脂、不饱和聚酯树脂、醇酸树脂、环氧树脂、硅树脂等。
以下通过实施例更进一步详细地说明本发明,但本发明并不受这些例子的任何限定。
实施例1(金属络合化合物1-1的合成)
金属络合化合物1-1的合成途径如下所示。
※中间体1-1a的化学结构式表示二聚物结构。
(1)中间体1-1b的合成
在烧瓶内装入3.5g(36mmol)2-氨基吡啶、7.2g(36mmol)α-溴代苯乙酮和3.6g(43mmol)碳酸氢钠,在120 ml乙醇中,于室温下反应4小时,然后在回流条件下反应2小时。滤出不溶物质,浓缩滤液。用150ml二氯甲烷萃取,用200ml水洗涤3次。用硫酸镁干燥有机层,然后除去溶剂,得到茶色结晶。通过硅胶柱(己烷/二氯甲烷)进行纯化,得到6.3g为白色结晶的2-苯基咪唑并[1,2-a]吡啶中间体1-1b(收率90%)。通过1H-NMR确认为目标物质。其测定结果如 下所示。
1H-NMR(CDCl3):δ7.8-8.3(m,4H),δ7.0-8.3(m,5H),δ.6-6.9(m,1H)
(2)中间体1-1a的合成
在烧瓶内装入5.0g(25.7mmol)中间体1-1b、1.9g(6.4mmol)IrCl3 水合物(strem制),用氩气置换后,加入40ml 2-乙氧基乙醇,使其在回流下反应15小时。滤出所得的黄色沉淀,用5ml乙醇洗涤2次。再将其溶解于150ml二氯甲烷中,依次用HCl水溶液洗涤3次,用水洗涤2次。用硫酸镁干燥所得溶液后,馏去溶剂,得到1.39g为黄色结晶的中间体1-1a(收率35%)。
(3)金属络合化合物1-1的合成
在烧瓶内装入1.39g(1.13mmol)中间体1-1a、0.55g(4.52mmol)2-吡啶甲酸,用氩气置换后,加入20ml 1,2-二氯乙烷,使其在回流下反应17小时。滤出所得黄色沉淀,将其溶解于400ml二氯甲烷,用150ml水洗涤3次。将溶液用硫酸镁干燥,然后馏去溶剂,用少量的二氯甲烷进行洗涤,得到0.85g为黄色结晶的金属络合化合物1-1(收率54%)。通过FD-MS(场解析质谱分析)确认为目标物质。
测定结果如下所示。
FD-MS:m/z=701
测定所得金属络合化合物1-1的磷光(二氯甲烷溶液),得知磷光的λmax(最大发光强度的波长)为580nm。
实施例2(金属络合化合物1-2的合成)
金属络合化合物1-2的合成途径如下所示。
※中间体1-2a的化学结构式表示二聚物结构。
(1)中间体1-2c的合成
一边将25g(160.1mmol)2,4-二氟苯基苯乙酮的50ml乙酸溶液冷却至10℃以下,一边滴加25.5g(160.1mmol)溴,使其反应7小时。将形成的溶液加入300ml水中,用二氯甲烷萃取。用硫酸镁干燥有机层,然后除去溶剂。将所得残余物通过硅胶柱纯化(己烷),得到23.4g为褐色油状物的α-溴-2,4-二氟苯基苯乙酮中间体1-2c(收率62%)。通过1H-NMR确认为目标物质。其测定结果如下所示。
1H-NMR(CDCl3):δ7.87-8.14(m,1H),δ6.8-7.13(m,2H),δ4.49(d,2H)
(2)中间体1-2b的合成
在烧瓶内装入3.3g(35.5mmol)2-氨基吡啶、8.4g(35.5mmol)中间体1-2c和3.6g(43mmol)碳酸氢钠,在120 ml乙醇中,于室温下反应4小时,然后在回流条件下反应2小时。滤出不溶物质,浓缩滤液。用150ml二氯甲烷萃取,用200ml水洗涤3次。用硫酸镁干燥有机层,然后除去溶剂,得到茶色结晶。通过硅胶柱(己烷/二氯甲烷)进行纯化,得到7.3 g为2-(2’,4’-二氟苯基)咪唑并[1,2-a]吡啶中间体1-2b(收率89%)。通过1H-NMR确认为目标物质。其测定结果如下所示。
1H-NMR(CDCl3):δ7.9-8.45(m,3H),δ7.5-7.7(m,1H),δ6.7-7.28(m,4H)
(3)中间体1-2a的合成
在烧瓶内装入4.7g(20.6mmol)中间体1-2b、1.53g(5.1mmol)IrCl3 水合物(strem制),用氩气置换后,加入25ml 2-乙氧基乙醇,使其在回流下反应15小时。滤出所得的淡黄色沉淀,用5ml乙醇洗涤2次。再将其溶解于150ml二氯甲烷中,依次用HCl水溶液洗涤3次,用水洗涤2次。用硫酸镁干燥所得溶液后,馏去溶剂,得到1.39g为黄色结晶的中间体1-2a(收率35%)。
(4)金属络合化合物1-2的合成
在烧瓶内装入1.39g(1.13mmol)中间体1-2a、0.55g(4.52mmol)2-吡啶甲酸,用氩气置换后,加入20ml 1,2-二氯乙烷,使其在回流下反应17小时。滤出所得黄色沉淀,将其溶解于400 ml二氯甲烷,用150ml水洗涤3次。将溶液用硫酸镁干燥,然后馏去溶剂,用少量的二氯甲烷进行洗涤,得到0.85g为黄色结晶的金属络合化合物1-2(收率54%)。通过1H-NMR和FD-MS确认为目标物质。测定结果如下所示。
1H-NMR(CDCl3):δ7.84-8.30(m,7H),δ7.2-7.47(m,2H),δ6.7-7.0(m,3H),δ6.2-6.6(m,2H),δ5.44-5.88(m,4H)
FD-MS:m/z=773
测定所得金属络合化合物1-2的磷光(二氯甲烷溶液),得知磷光的λmax为529nm。
实施例3(金属络合化合物6-1的合成)
金属络合化合物6-1的合成途径如下所示。
※中间体6-1a的化学结构式表示二聚物结构。
(1)中间体6-1b的合成
在装有滴液漏斗的烧瓶内装入8.6g(60mmol)2-苯基咪唑,用氩气置换后,加入180ml四氢呋喃。在冰冷却下,用约30分钟滴加39.1ml(61mmol)1.56mol/l的正丁基锂,然后滴加8.6g(61mmol)溶解于10ml四氢呋喃中的碘代甲烷。滴加结束后,使其在室温下反应3小时。浓缩反应溶液,之后用150ml二氯甲烷萃取所得固体,用150ml水洗涤3次。用硫酸镁干燥有机层,然后除去溶剂。通过硅胶柱(己烷/二氯甲烷)进行纯化,得到6.1g为白色结晶的1-甲基-2-苯基咪唑中间体6-1b(收率69%)。通过1H-NMR确认为目标物质。其测定结果如下所示。
1H-NMR(CDCl3):δ7.29-7.67(m,5H),δ6.93-7.10(m,2H),δ3.69(s,3H)
(2)中间体6-1a的合成
在烧瓶内装入4.1g(26.2mmol)中间体6-1b、1.95g(6.5mmol)IrCl3 水合物(strem制),用氩气置换后,加入30ml 2-乙氧基乙醇,使其在回流下反应11小时。滤出所得的黄色沉淀,用5ml乙醇洗涤2次。再将其溶解于600ml二氯甲烷中,用200ml水洗涤3次。用硫酸镁干燥所得溶液后,馏去溶剂,得到1.35g为淡黄色结晶的中间体6-1a(收率38%)。
1H-NMR(CD2Cl2):δ7.26-7.42(m,2H),δ6.47-6.94(m,3H),δ6.0-6.09(m,1H),δ4.13(s,3H)
(3)金属络合化合物6-1的合成
在烧瓶内装入1.32g(1.21mmol)中间体6-1a、0.59g(4.87mmol)2-吡啶甲酸,用氩气置换后,加入15ml 1,2-二氯乙烷,使其在回流下反应8小时。滤出所得黄色沉淀,将其溶解于200ml二氯甲烷,用150ml水洗涤4次。将溶液用硫酸镁干燥,然后馏去溶剂,用二氯甲烷/己烷进行重结晶。得到1.17g为黄色结晶的金属络合化合物6-1(收率78%)。通过1H-NMR确认为目标物质。测定结果如下所示。
1H-NMR(CDCl3):δ8.1-8.2(m,1H),δ7.75-7.90(m,2H),δ7.2-7.51(m,3H),δ6.3-7.0(m,9H),δ6.13(d,1H),δ4.06(s,3H)
测定所得金属络合化合物6-1的磷光(二氯甲烷溶液),得知磷光的λmax为562nm。
比较例1
在烧瓶内装入3.8g(26.3mmol)4-苯基咪唑、1.96g(6.6mmol)IrCl3 水合物(strem制),用氩气置换后,加入30ml 2-乙氧基乙醇,使其在回流下反应18小时后,没有沉淀物,成为均匀的黑褐色溶液。馏去溶剂,对溶液进行处理后,得到黑色固体,未能确认是目标物质Ir金属络合化合物(下述Q)。与实施例3进行比较,如下所示,若咪唑的N位上存在H,则难以合成Ir络合物,需要甲基等一些取代基。
实施例4(金属络合化合物7-1的合成)
金属络合化合物7-1的合成途径如下所示。
※中间体7-1a的化学结构式表示二聚物结构。
(1)中间体7-1b的合成
在装有滴液漏斗的烧瓶内装入8.9g(60.8mmol)2-苯基咪唑啉,用氩气置换后,加入210ml四氢呋喃。在冰冷却下,用约30分钟滴加39.3ml(61.2mmol)1.56mol/l的正丁基锂,然后滴加8.7g(61.3mmol)溶解于10ml四氢呋喃中的碘代甲烷。滴加结束后,使其在室温下反应3小时。浓缩反应溶液,之后用150ml二氯甲烷萃取所得固体,用150ml水洗涤3次。用硫酸镁干燥有机层,然后除去溶剂。通过硅胶柱(己烷/二氯甲烷)进行纯化,得到8.0g为白色结晶的1-甲基-2-苯基咪唑啉中间体7-1b(收率83%)。通过1H-NMR确认为目标物质。其测定结果如下所示。
1H-NMR(CDCl3):δ7.33-7.60(m,5H),δ3.27-3.98(m,4H),δ2.76(s,3H)
(2)中间体7-1a的合成
在烧瓶内装入4.4g(27.5mmol)中间体7-1b、2.1g(6.9mmol)IrCl3 水合物(strem制),用氩气置换。加入30ml 2-乙氧基乙醇,使其在回流下反应16小时。滤出所得的黄色沉淀,用5ml乙醇洗涤2次。再将其溶解于200ml二氯甲烷中,用200ml水洗涤4次。用硫酸镁干燥所得溶液后,馏去溶剂,得到2.1g为橙色结晶的中间体7-1a(收率57%)。通过1H-NMR确认为目标物质。其测定结果如下所示。
1H-NMR(DMSO-d6):δ7.51-7.61(m,1H),δ6.69-6.97(m,3H),δ3.60-4.1(m,4H),δ3.33(s,3H)
(3)金属络合化合物7-1的合成
在烧瓶内装入1.95g(1.78mmol)中间体7-1a、0.88g(7.14mmol)2-吡啶甲酸,用氩气置换。加入20ml 1,2-二氯乙烷,使其在回流下反应17小时。从反应溶液中除去溶剂,将所得褐色固体溶解于150ml二氯甲烷中,用200ml水洗涤5次。将溶液用硫酸镁干燥,然后馏去溶剂,通过硅胶柱(二氯甲烷/甲醇)进行纯化。得到1.2g为茶色结晶的7-1(收率53%)。通过FD-MS确认为目标物质。测定结果如下所示。
FD-MS:m/z=632
测定所得金属络合化合物7-1的磷光(二氯甲烷溶液),得知磷光的λmax为562nm。
实施例5(金属络合化合物5-1的合成)
金属络合化合物5-1的合成途径如下所示。
(1)中间体5-1b的合成
在装有滴液漏斗的烧瓶内装入9.6g(67mmol)4-苯基咪唑,用氩气置换后,加入50ml二甲基亚砜。向该溶液中一点点加入2.8gNaH(油中60%,相当于70mmol),全部添加后,在80℃加热2小时。随后,滴加9.6 g(68mmol)溶解于15ml甲基亚砜中的碘代甲烷,再在80℃加热15小时。
将反应溶液加入200ml水中,用200ml二氯甲烷萃取。分离有机层,然后用200ml水洗涤5次,用硫酸镁干燥。浓缩溶液,将所得淡褐色固体通过硅胶柱(二氯甲烷)纯化,得到5.5g为白色结晶的1-甲基-4-苯基咪唑中间体5-1b(收率52%)。
(2)中间体5-1a的合成
在烧瓶内装入3.0g(18.9mmol)中间体5-1b、1.41g(4.7mmol)IrCl3 水合物(strem制),用氩气置换。加入15ml 2-乙氧基乙醇,使其在回流下反应13小时。滤出所得的白色沉淀,用5ml乙醇洗涤2次。再将其溶解于500ml二氯甲烷中,用150ml水洗涤3次。用硫酸镁干燥所得溶液后,馏去溶剂,得到1.77g为白色结晶的中间体5-1a(收率69%)。
(3)金属络合化合物5-1的合成
在烧瓶内装入1.38g(1.27mmol)中间体5-1a、0.62g(5.1mmol)2-吡啶甲酸,用氩气置换。加入20ml 1,2-二氯乙烷,使其在回流下反应12小时。滤出所得黄色沉淀,将其溶解于300ml二氯甲烷中,用200ml水洗涤4次。将溶液用硫酸镁干燥,然后馏去溶剂。将所得黄色结晶通过硅胶柱(二氯甲烷/甲醇)进行纯化。得到0.4g为淡黄色结晶的5-1(收率26%)。
测定所得金属络合化合物5-1的磷光(二氯甲烷溶液),得知磷光的λmax为453nm。
实施例6(有机EL元件的制作)
将25mm×75mm×0.7mm厚的带ITO透明电极的玻璃基板在异丙醇中进行5分钟的超声波洗涤后,用UV臭氧洗涤30分钟。将洗涤后的带透明电极的玻璃基板设置于真空蒸镀装置的基板架上,首先在形成透明电极的一侧的面上形成膜厚为40nm的下述4,4’-二[N-(4-联苯基)-N-(4-联苯基)氨基]联苯膜,使该膜覆盖上述透明电极。该膜发挥空穴传输层的功能。再将下述基质材料(CBP)和同时作为掺杂剂添加的磷光发光材料的Ir金属络合化合物1-2进行蒸镀,形成厚30nm的膜。该膜发挥发光层的功能。在发光层中化合物1-1的浓度为5%重量。该膜上形成膜厚为10nm的(1,1’-联苯基)-4-酚根)二(2-甲基-8-羟基喹啉根)合铝(BAlq)。该BAlq膜发挥空穴障壁层的功能。
进一步在该膜上形成膜厚为30nm的8-羟基喹啉的铝络合物(Alq)膜。该Alq膜发挥电子注入层的功能。此后,蒸镀卤化碱金属LiF,使其厚度为0.15nm,接着蒸镀厚铝,使其厚度为150nm。该Al/LiF发挥阴极的功能。由此制成了有机EL元件。
对所制元件进行通电试验,在电压为6.7V、电流密度为2.79mA/cm2的条件下得到103cd/m2的黄绿色发光,色度坐标为(0.347,0.494),发光效率为3.7cd/A。而且,发光的λmax为533nm。
4,4’-双[N-(4-联苯基)-N-(4-联苯基)氨基]联苯
产业实用性
综上所述,利用本发明的新型金属络合化合物制成的有机EL元件,其发光效率高,寿命长,可用作以蓝色为首的各色磷光有机EL用材料,适用于各种显示元件、显示器、背景灯、照明光源、标识、看板、室内装饰等领域,特别适用于彩色显示器的显示元件。
Claims (4)
1.下式中任何一项所示金属络合化合物:
下式1、2、1’和2’:
其中T5至T9各自独立代表氢原子或具有1-20个碳原子的烷基;
M为任何一种选自铱、铑、铂和钯的金属,
L1和L2代表任何一个选自以下化学结构的结构:
n代表0-2的整数,m代表0或1的整数;和
G代表任何一个选自以下结构的结构:
其中,虚线“- - -”表示与上述M的共价键;和
Ph中的T1-T4可各自独立表示氰基、硝基、卤素原子、碳原子数为1-20的烷基、氨基、碳原子数为1-20的烷氧基、碳原子数为1-20的烷基甲硅烷基、碳原子数为1-20的酰基或碳原子数为1-30的芳基;
下式5和5’:
其中T5和T7各自独立代表氢原子或具有1-20个碳原子的烷基;T6代表具有1-20个碳原子的烷基;一对T5和T6以及一对T6和T7彼此键接或不键接形成环结构;以及M、L1、L2、n、m和G的定义同上;
下式:
其中M、n、T1至T4、T5至T9、L1和L2如下表中的定义,
下式:
其中M、n、T1至T4、T5至T9、L1和L2如下表中的定义,
下式:
其中M、n、T1至T4、T5至T7、L1和L2如下表中的定义,
下式:
2.通过在两极间施加电压而使其发光的有机电致发光元件,该元件是在一对电极间夹持着至少具有发光层的由一层或多层构成的有机薄膜层,该有机薄膜层中的至少1层含有权利要求1的金属络合化合物。
3.权利要求2的有机电致发光元件,其中所述发光层含有权利要求1的金属络合化合物。
4.权利要求2的有机电致发光元件,其中含有金属络合化合物的层是通过涂布法成膜的。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP199995/2003 | 2003-07-22 | ||
JP2003199995 | 2003-07-22 | ||
PCT/JP2004/010687 WO2005007767A2 (ja) | 2003-07-22 | 2004-07-21 | 金属錯体化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2011103508712A Division CN102516312A (zh) | 2003-07-22 | 2004-07-21 | 金属络合化合物和使用了该化合物的有机电致发光元件 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1829724A CN1829724A (zh) | 2006-09-06 |
CN1829724B true CN1829724B (zh) | 2012-10-10 |
Family
ID=34074444
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2004800206564A Expired - Fee Related CN1829724B (zh) | 2003-07-22 | 2004-07-21 | 金属络合化合物和使用了该化合物的有机电致发光元件 |
CN2011103508712A Pending CN102516312A (zh) | 2003-07-22 | 2004-07-21 | 金属络合化合物和使用了该化合物的有机电致发光元件 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2011103508712A Pending CN102516312A (zh) | 2003-07-22 | 2004-07-21 | 金属络合化合物和使用了该化合物的有机电致发光元件 |
Country Status (8)
Country | Link |
---|---|
US (4) | US7667228B2 (zh) |
EP (2) | EP1647554B1 (zh) |
JP (2) | JP4891615B2 (zh) |
KR (1) | KR101046847B1 (zh) |
CN (2) | CN1829724B (zh) |
AT (1) | ATE522539T1 (zh) |
TW (1) | TW200504183A (zh) |
WO (1) | WO2005007767A2 (zh) |
Families Citing this family (101)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1829724B (zh) * | 2003-07-22 | 2012-10-10 | 出光兴产株式会社 | 金属络合化合物和使用了该化合物的有机电致发光元件 |
US7147937B2 (en) * | 2003-12-05 | 2006-12-12 | Eastman Kodak Company | Organic element for electroluminescent devices |
JP4894513B2 (ja) * | 2004-06-17 | 2012-03-14 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
US20060008670A1 (en) * | 2004-07-06 | 2006-01-12 | Chun Lin | Organic light emitting materials and devices |
US8586204B2 (en) * | 2007-12-28 | 2013-11-19 | Universal Display Corporation | Phosphorescent emitters and host materials with improved stability |
US9051344B2 (en) | 2005-05-06 | 2015-06-09 | Universal Display Corporation | Stability OLED materials and devices |
US7902374B2 (en) | 2005-05-06 | 2011-03-08 | Universal Display Corporation | Stability OLED materials and devices |
WO2006132012A1 (ja) * | 2005-06-09 | 2006-12-14 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
GB2475647B (en) * | 2005-06-09 | 2011-07-13 | Konica Minolta Holdings Inc | Organic electroluminescent element, illuminator and display |
JP4904727B2 (ja) * | 2005-06-23 | 2012-03-28 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP5130913B2 (ja) * | 2005-08-25 | 2013-01-30 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
WO2007043321A1 (ja) * | 2005-10-11 | 2007-04-19 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、液晶表示装置及び照明装置 |
US7807839B2 (en) | 2005-10-18 | 2010-10-05 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, and light-emitting element and light-emitting device using the same |
JP4887731B2 (ja) * | 2005-10-26 | 2012-02-29 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
EP1947911B1 (en) * | 2005-11-09 | 2017-06-21 | Konica Minolta Holdings, Inc. | Organic electroluminescent device, display and illuminating device |
JPWO2007069539A1 (ja) * | 2005-12-15 | 2009-05-21 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置および照明装置 |
US7935434B2 (en) | 2006-01-05 | 2011-05-03 | Konica Minolta Holdings, Inc. | Organic electroluminescent device, display, and illuminating device |
KR20210130847A (ko) * | 2006-02-10 | 2021-11-01 | 유니버셜 디스플레이 코포레이션 | 시클로금속화 이미다조[1,2-f]페난트리딘 및 디이미다조[1,2-a:1',2'-c]퀴나졸린 리간드, 및 이의 등전자성 및 벤즈고리화된 유사체의 금속 착체 |
EP1988143A4 (en) | 2006-02-20 | 2009-11-25 | Konica Minolta Holdings Inc | ORGANIC ELECTROLUMINESCENT ELEMENT, WHITE LIGHT EMITTING ELEMENT, DISPLAY DEVICE, AND LIGHTING DEVICE |
US20090091253A1 (en) * | 2006-03-17 | 2009-04-09 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, display device and lighting device |
EP2615153B1 (en) * | 2006-03-23 | 2017-03-01 | Konica Minolta Holdings, Inc. | Organic electroluminescent device, display and illuminating device |
JP2007269735A (ja) * | 2006-03-31 | 2007-10-18 | Canon Inc | 金属錯体、発光素子及び表示装置 |
JP5181448B2 (ja) * | 2006-09-13 | 2013-04-10 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料 |
WO2008035595A1 (fr) * | 2006-09-19 | 2008-03-27 | Konica Minolta Holdings, Inc. | Dispositifs électroluminescents organiques |
JP5556014B2 (ja) * | 2006-09-20 | 2014-07-23 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子 |
JP5644050B2 (ja) * | 2006-09-20 | 2014-12-24 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子材料 |
EP1918349A1 (en) * | 2006-10-12 | 2008-05-07 | SOLVAY (Société Anonyme) | Light-emitting material |
WO2008072596A1 (ja) | 2006-12-13 | 2008-06-19 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP5493358B2 (ja) * | 2007-02-01 | 2014-05-14 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP5294242B2 (ja) * | 2007-05-10 | 2013-09-18 | 独立行政法人産業技術総合研究所 | 金属配位化合物ならびにこれを用いた発光材料 |
WO2008156879A1 (en) | 2007-06-20 | 2008-12-24 | Universal Display Corporation | Blue phosphorescent imidazophenanthridine materials |
JP5438941B2 (ja) | 2007-09-25 | 2014-03-12 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子 |
EP2202818B1 (en) * | 2007-09-28 | 2014-11-12 | Idemitsu Kosan Co., Ltd. | Organic el device |
WO2012111580A1 (en) * | 2011-02-16 | 2012-08-23 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
DE202012013737U1 (de) | 2011-03-23 | 2020-09-30 | Semiconductor Energy Laboratory Co., Ltd. | Lichtemittierendes Element |
JP2013147490A (ja) | 2011-12-23 | 2013-08-01 | Semiconductor Energy Lab Co Ltd | イリジウム錯体、発光素子、発光装置、電子機器、及び照明装置 |
US9929361B2 (en) | 2015-02-16 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11056657B2 (en) | 2015-02-27 | 2021-07-06 | University Display Corporation | Organic electroluminescent materials and devices |
US9859510B2 (en) | 2015-05-15 | 2018-01-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10418568B2 (en) | 2015-06-01 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11127905B2 (en) | 2015-07-29 | 2021-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10361381B2 (en) | 2015-09-03 | 2019-07-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20170229663A1 (en) | 2016-02-09 | 2017-08-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10236456B2 (en) | 2016-04-11 | 2019-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10672997B2 (en) | 2016-06-20 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11482683B2 (en) | 2016-06-20 | 2022-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10862054B2 (en) | 2016-06-20 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10608186B2 (en) | 2016-09-14 | 2020-03-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10680187B2 (en) | 2016-09-23 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11196010B2 (en) | 2016-10-03 | 2021-12-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11011709B2 (en) | 2016-10-07 | 2021-05-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102186093B1 (ko) * | 2016-11-07 | 2020-12-03 | 주식회사 엘지화학 | 코팅 조성물 및 이를 포함하는 유기전계 발광소자 |
US20180130956A1 (en) | 2016-11-09 | 2018-05-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10680188B2 (en) | 2016-11-11 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11780865B2 (en) | 2017-01-09 | 2023-10-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10844085B2 (en) | 2017-03-29 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10944060B2 (en) | 2017-05-11 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20180370999A1 (en) | 2017-06-23 | 2018-12-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11228010B2 (en) | 2017-07-26 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11744142B2 (en) | 2017-08-10 | 2023-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20190161504A1 (en) | 2017-11-28 | 2019-05-30 | University Of Southern California | Carbene compounds and organic electroluminescent devices |
EP3492480B1 (en) | 2017-11-29 | 2021-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11937503B2 (en) | 2017-11-30 | 2024-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11542289B2 (en) | 2018-01-26 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20200075870A1 (en) | 2018-08-22 | 2020-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11737349B2 (en) | 2018-12-12 | 2023-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11780829B2 (en) | 2019-01-30 | 2023-10-10 | The University Of Southern California | Organic electroluminescent materials and devices |
US20200251664A1 (en) | 2019-02-01 | 2020-08-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP2020158491A (ja) | 2019-03-26 | 2020-10-01 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
US20210032278A1 (en) | 2019-07-30 | 2021-02-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20210047354A1 (en) | 2019-08-16 | 2021-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20210135130A1 (en) | 2019-11-04 | 2021-05-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20210217969A1 (en) | 2020-01-06 | 2021-07-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220336759A1 (en) | 2020-01-28 | 2022-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20210103864A (ko) | 2020-02-14 | 2021-08-24 | 삼성전자주식회사 | 유기금속 화합물, 이를 포함한 유기 발광 소자 및 상기 유기 발광 소자를 포함한 전자 장치 |
EP3937268A1 (en) | 2020-07-10 | 2022-01-12 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
JP2023542011A (ja) | 2020-09-18 | 2023-10-04 | 三星ディスプレイ株式會社 | 有機エレクトロルミネッセンス素子 |
US20220158096A1 (en) | 2020-11-16 | 2022-05-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220162243A1 (en) | 2020-11-24 | 2022-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220165967A1 (en) | 2020-11-24 | 2022-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220271241A1 (en) | 2021-02-03 | 2022-08-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4060758A3 (en) | 2021-02-26 | 2023-03-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4059915A3 (en) | 2021-02-26 | 2022-12-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298192A1 (en) | 2021-03-05 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298190A1 (en) | 2021-03-12 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298193A1 (en) | 2021-03-15 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220340607A1 (en) | 2021-04-05 | 2022-10-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4075531A1 (en) | 2021-04-13 | 2022-10-19 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
US20220352478A1 (en) | 2021-04-14 | 2022-11-03 | Universal Display Corporation | Organic eletroluminescent materials and devices |
US20220407020A1 (en) | 2021-04-23 | 2022-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230006149A1 (en) | 2021-04-23 | 2023-01-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230133787A1 (en) | 2021-06-08 | 2023-05-04 | University Of Southern California | Molecular Alignment of Homoleptic Iridium Phosphors |
EP4151699A1 (en) | 2021-09-17 | 2023-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4212539A1 (en) | 2021-12-16 | 2023-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4231804A3 (en) | 2022-02-16 | 2023-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230292592A1 (en) | 2022-03-09 | 2023-09-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230337516A1 (en) | 2022-04-18 | 2023-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230389421A1 (en) | 2022-05-24 | 2023-11-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4293001A1 (en) | 2022-06-08 | 2023-12-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240016051A1 (en) | 2022-06-28 | 2024-01-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240107880A1 (en) | 2022-08-17 | 2024-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
Family Cites Families (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5465185A (en) * | 1977-11-04 | 1979-05-25 | Fuji Photo Film Co Ltd | Stablizing method for organic basic substance to light |
US4923638A (en) * | 1985-09-30 | 1990-05-08 | Fuji Photo Film Co., Ltd. | Near infrared absorbing composition |
US5182186A (en) * | 1987-09-29 | 1993-01-26 | Fuji Photo Film Co., Ltd. | Optical information recording medium |
GB8830182D0 (en) * | 1988-12-23 | 1989-02-22 | Shell Int Research | Heterocyclic herbicides |
DE69505312T2 (de) * | 1994-02-02 | 1999-04-08 | Novartis Ag | Verfahren zur hydrierung von iminen |
US6461747B1 (en) * | 1999-07-22 | 2002-10-08 | Fuji Photo Co., Ltd. | Heterocyclic compounds, materials for light emitting devices and light emitting devices using the same |
KR100794975B1 (ko) * | 1999-12-01 | 2008-01-16 | 더 트러스티즈 오브 프린스턴 유니버시티 | 유기 led용 인광성 도펀트로서 l2mx 형태의 착물 |
US6821645B2 (en) * | 1999-12-27 | 2004-11-23 | Fuji Photo Film Co., Ltd. | Light-emitting material comprising orthometalated iridium complex, light-emitting device, high efficiency red light-emitting device, and novel iridium complex |
JP3929690B2 (ja) * | 1999-12-27 | 2007-06-13 | 富士フイルム株式会社 | オルトメタル化イリジウム錯体からなる発光素子材料、発光素子および新規イリジウム錯体 |
KR100884039B1 (ko) | 2000-08-11 | 2009-02-19 | 더 트러스티즈 오브 프린스턴 유니버시티 | 유기 금속 화합물 및 방사-이동 유기 전기인광 |
JP4154139B2 (ja) * | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 発光素子 |
JP4154138B2 (ja) * | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 発光素子、表示装置及び金属配位化合物 |
JP4154140B2 (ja) * | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 金属配位化合物 |
US7053255B2 (en) * | 2000-11-08 | 2006-05-30 | Idemitsu Kosan Co., Ltd. | Substituted diphenylanthracene compounds for organic electroluminescence devices |
JP4086499B2 (ja) * | 2000-11-29 | 2008-05-14 | キヤノン株式会社 | 金属配位化合物、発光素子及び表示装置 |
JP4086498B2 (ja) * | 2000-11-29 | 2008-05-14 | キヤノン株式会社 | 金属配位化合物、発光素子及び表示装置 |
JP4006335B2 (ja) | 2000-11-30 | 2007-11-14 | キヤノン株式会社 | 発光素子及び表示装置 |
JP4438042B2 (ja) * | 2001-03-08 | 2010-03-24 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
US6933673B2 (en) * | 2001-04-27 | 2005-08-23 | Semiconductor Energy Laboratory Co., Ltd. | Luminescent device and process of manufacturing the same |
JP4310077B2 (ja) * | 2001-06-19 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物及び有機発光素子 |
JP2003090801A (ja) * | 2001-09-19 | 2003-03-28 | Dainippon Printing Co Ltd | 検査対象パターンの端部検出方法、装置、及び、検査方法、装置 |
JP5135660B2 (ja) * | 2001-09-27 | 2013-02-06 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
JP2003167828A (ja) * | 2001-11-29 | 2003-06-13 | Toppan Printing Co Ltd | 電子メール装置、電子メール管理方法、電子メールプログラム |
US6911671B2 (en) * | 2002-09-23 | 2005-06-28 | Eastman Kodak Company | Device for depositing patterned layers in OLED displays |
US6687266B1 (en) * | 2002-11-08 | 2004-02-03 | Universal Display Corporation | Organic light emitting materials and devices |
US20040131881A1 (en) * | 2002-12-31 | 2004-07-08 | Eastman Kodak Company | Complex fluorene-containing compounds for use in OLED devices |
JP2004319438A (ja) * | 2003-03-28 | 2004-11-11 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、表示装置、照明装置及びロジウム錯体化合物 |
JP4203732B2 (ja) | 2003-06-12 | 2009-01-07 | ソニー株式会社 | 有機電界発光材料、有機電界発光素子および含複素環イリジウム錯体化合物 |
CN1829724B (zh) * | 2003-07-22 | 2012-10-10 | 出光兴产株式会社 | 金属络合化合物和使用了该化合物的有机电致发光元件 |
US7147937B2 (en) * | 2003-12-05 | 2006-12-12 | Eastman Kodak Company | Organic element for electroluminescent devices |
WO2006098120A1 (ja) * | 2005-03-16 | 2006-09-21 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子 |
JP4904727B2 (ja) * | 2005-06-23 | 2012-03-28 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP4967284B2 (ja) * | 2005-09-13 | 2012-07-04 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
-
2004
- 2004-07-21 CN CN2004800206564A patent/CN1829724B/zh not_active Expired - Fee Related
- 2004-07-21 EP EP04747999A patent/EP1647554B1/en not_active Not-in-force
- 2004-07-21 KR KR1020067001402A patent/KR101046847B1/ko active IP Right Grant
- 2004-07-21 WO PCT/JP2004/010687 patent/WO2005007767A2/ja active Application Filing
- 2004-07-21 JP JP2005511940A patent/JP4891615B2/ja not_active Expired - Fee Related
- 2004-07-21 US US10/565,274 patent/US7667228B2/en not_active Expired - Fee Related
- 2004-07-21 CN CN2011103508712A patent/CN102516312A/zh active Pending
- 2004-07-21 EP EP10182596.6A patent/EP2336142B1/en not_active Not-in-force
- 2004-07-21 AT AT04747999T patent/ATE522539T1/de not_active IP Right Cessation
- 2004-07-22 TW TW093121962A patent/TW200504183A/zh unknown
-
2010
- 2010-02-18 US US12/656,892 patent/US8106390B2/en not_active Expired - Fee Related
- 2010-09-06 JP JP2010199428A patent/JP5491330B2/ja not_active Expired - Fee Related
- 2010-09-30 US US12/923,633 patent/US8178874B2/en active Active
-
2012
- 2012-03-05 US US13/412,276 patent/US20120169219A1/en not_active Abandoned
Non-Patent Citations (2)
Title |
---|
ALONSO M.T. ET AL..Palladium(II) coordiantion and cyclometalated complexesderived from 3- and 5-aryl-substituted pyrazoles.JOURNAL OF ORGANOMETALLIC CHEMISTRY430 3.1992,430(3),335-347, 特别是第337、339页. |
ALONSO M.T. ET AL..Palladium(II) coordiantion and cyclometalated complexesderived from 3- and 5-aryl-substituted pyrazoles.JOURNAL OF ORGANOMETALLIC CHEMISTRY430 3.1992,430(3),335-347, 特别是第337、339页. * |
Also Published As
Publication number | Publication date |
---|---|
JPWO2005007767A1 (ja) | 2006-08-31 |
EP1647554B1 (en) | 2011-08-31 |
JP5491330B2 (ja) | 2014-05-14 |
EP2336142A2 (en) | 2011-06-22 |
US7667228B2 (en) | 2010-02-23 |
EP2336142B1 (en) | 2013-09-04 |
KR20060059969A (ko) | 2006-06-02 |
US20120169219A1 (en) | 2012-07-05 |
JP4891615B2 (ja) | 2012-03-07 |
WO2005007767A3 (ja) | 2005-03-31 |
ATE522539T1 (de) | 2011-09-15 |
TWI332977B (zh) | 2010-11-11 |
US20110017984A1 (en) | 2011-01-27 |
CN102516312A (zh) | 2012-06-27 |
EP2336142A3 (en) | 2011-12-21 |
KR101046847B1 (ko) | 2011-07-06 |
EP1647554A4 (en) | 2008-02-20 |
US20100155713A1 (en) | 2010-06-24 |
CN1829724A (zh) | 2006-09-06 |
JP2011029647A (ja) | 2011-02-10 |
US8178874B2 (en) | 2012-05-15 |
US8106390B2 (en) | 2012-01-31 |
US20060197077A1 (en) | 2006-09-07 |
TW200504183A (en) | 2005-02-01 |
EP1647554A2 (en) | 2006-04-19 |
WO2005007767A2 (ja) | 2005-01-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1829724B (zh) | 金属络合化合物和使用了该化合物的有机电致发光元件 | |
JP6316351B2 (ja) | ピリジルカルベンリン光発光体 | |
TWI580680B (zh) | 以咪唑并〔1,2-f〕啡啶銥錯合物為主之高效能藍光發射體 | |
US7381479B2 (en) | Organometallic compounds and emission-shifting organic electrophosphorescence | |
CN102603803B (zh) | 改进的电致发光稳定性 | |
EP2770036B1 (en) | Material for organic electroluminescent devices and organic electroluminescent devices made by using the same | |
EP2429997B1 (en) | 2-azatriphenylene materials for organic light emitting diodes | |
US8461580B2 (en) | Light-emitting element and light-emitting device | |
EP3178831A1 (en) | Heteroleptic iridium complex | |
EP2566302A1 (en) | Organometallic compounds and emission-shifting organic electrophosphorence | |
EP2493269A1 (en) | Organometallic compounds and emmission-shifting organic electrophosphorence | |
KR20080081277A (ko) | 금속 착체 화합물 및 그것을 이용한 유기 전기 발광 소자 | |
US7320835B2 (en) | Phosphorescent material | |
JP2005089367A (ja) | 金属錯体化合物及びそれを用いた有機エレクトロルミネッセンス素子 | |
CN101331145A (zh) | 金属配位化合物以及应用该化合物的有机电致发光元件 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20121010 Termination date: 20210721 |
|
CF01 | Termination of patent right due to non-payment of annual fee |