JP4271238B2 - 有機発光ダイオード(oled)におけるルミネセンス材料としての白金(ii)錯体の使用 - Google Patents
有機発光ダイオード(oled)におけるルミネセンス材料としての白金(ii)錯体の使用 Download PDFInfo
- Publication number
- JP4271238B2 JP4271238B2 JP2006543464A JP2006543464A JP4271238B2 JP 4271238 B2 JP4271238 B2 JP 4271238B2 JP 2006543464 A JP2006543464 A JP 2006543464A JP 2006543464 A JP2006543464 A JP 2006543464A JP 4271238 B2 JP4271238 B2 JP 4271238B2
- Authority
- JP
- Japan
- Prior art keywords
- platinum
- group
- formula
- complex
- light emitting
- 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
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical class [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 239000000463 material Substances 0.000 title description 36
- -1 naphthalene diyl group Chemical group 0.000 claims description 72
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 29
- 125000004437 phosphorous atom Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 230000000007 visual effect Effects 0.000 claims description 12
- 125000005549 heteroarylene group Chemical group 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 claims description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
- AWYLBFMYPUUBDN-UHFFFAOYSA-N platinum(2+);2-pyridin-2-ylpyridine Chemical group [Pt+2].N1=CC=CC=C1C1=CC=CC=N1 AWYLBFMYPUUBDN-UHFFFAOYSA-N 0.000 claims description 3
- ZGINBABICSIURJ-UHFFFAOYSA-N phosphane;platinum(2+) Chemical compound P.[Pt+2] ZGINBABICSIURJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000005286 illumination Methods 0.000 claims 1
- 239000010410 layer Substances 0.000 description 95
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- 125000001424 substituent group Chemical group 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 16
- 239000003446 ligand Substances 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 230000005525 hole transport Effects 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 150000005840 aryl radicals Chemical class 0.000 description 13
- 230000032258 transport Effects 0.000 description 13
- 238000005401 electroluminescence Methods 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000009471 action Effects 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 7
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 description 6
- 238000004020 luminiscence type Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- 150000003624 transition metals Chemical class 0.000 description 5
- 239000002800 charge carrier Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 description 3
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- XYZNIJOLUAUPAL-UHFFFAOYSA-N [Pt+2].[C-]#[C-] Chemical class [Pt+2].[C-]#[C-] XYZNIJOLUAUPAL-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007850 fluorescent dye Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 150000003057 platinum Chemical class 0.000 description 3
- 239000003880 polar aprotic solvent Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000012552 review Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000000476 acetylides Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000548 poly(silane) polymer Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000004149 thio group Chemical group *S* 0.000 description 2
- 150000003623 transition metal compounds Chemical class 0.000 description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- NFRYVRNCDXULEX-UHFFFAOYSA-N (2-diphenylphosphanylphenyl)-diphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C(=CC=CC=1)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 NFRYVRNCDXULEX-UHFFFAOYSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- KLFRPGNCEJNEKU-FDGPNNRMSA-L (z)-4-oxopent-2-en-2-olate;platinum(2+) Chemical class [Pt+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O KLFRPGNCEJNEKU-FDGPNNRMSA-L 0.000 description 1
- XGCDBGRZEKYHNV-UHFFFAOYSA-N 1,1-bis(diphenylphosphino)methane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)C1=CC=CC=C1 XGCDBGRZEKYHNV-UHFFFAOYSA-N 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalene Chemical group C1=CC=C2C(C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- NRSBAUDUBWMTGL-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)pyridine Chemical compound S1C2=CC=CC=C2C=C1C1=CC=CC=N1 NRSBAUDUBWMTGL-UHFFFAOYSA-N 0.000 description 1
- RIKNNBBGYSDYAX-UHFFFAOYSA-N 2-[1-[2-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]-n,n-bis(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C(=CC=CC=1)C1(CCCCC1)C=1C(=CC=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 RIKNNBBGYSDYAX-UHFFFAOYSA-N 0.000 description 1
- KAJMDIRNTNSOLE-UHFFFAOYSA-N 2-naphthalen-1-yl-1,3-benzoxazole Chemical compound C1=CC=C2C(C=3OC4=CC=CC=C4N=3)=CC=CC2=C1 KAJMDIRNTNSOLE-UHFFFAOYSA-N 0.000 description 1
- XBHOUXSGHYZCNH-UHFFFAOYSA-N 2-phenyl-1,3-benzothiazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2S1 XBHOUXSGHYZCNH-UHFFFAOYSA-N 0.000 description 1
- FIISKTXZUZBTRC-UHFFFAOYSA-N 2-phenyl-1,3-benzoxazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2O1 FIISKTXZUZBTRC-UHFFFAOYSA-N 0.000 description 1
- QLPKTAFPRRIFQX-UHFFFAOYSA-N 2-thiophen-2-ylpyridine Chemical compound C1=CSC(C=2N=CC=CC=2)=C1 QLPKTAFPRRIFQX-UHFFFAOYSA-N 0.000 description 1
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 1
- VJHVLELNDFVKMS-UHFFFAOYSA-N 3-methoxy-2-phenylpyridine Chemical compound COC1=CC=CN=C1C1=CC=CC=C1 VJHVLELNDFVKMS-UHFFFAOYSA-N 0.000 description 1
- DNTVTBIKSZRANH-UHFFFAOYSA-N 4-(4-aminophenyl)-3-(3-methylphenyl)aniline Chemical compound CC1=CC=CC(C=2C(=CC=C(N)C=2)C=2C=CC(N)=CC=2)=C1 DNTVTBIKSZRANH-UHFFFAOYSA-N 0.000 description 1
- KBXXZTIBAVBLPP-UHFFFAOYSA-N 4-[[4-(diethylamino)-2-methylphenyl]-(4-methylphenyl)methyl]-n,n-diethyl-3-methylaniline Chemical compound CC1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)N(CC)CC)C)C1=CC=C(C)C=C1 KBXXZTIBAVBLPP-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- MVIXNQZIMMIGEL-UHFFFAOYSA-N 4-methyl-n-[4-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 MVIXNQZIMMIGEL-UHFFFAOYSA-N 0.000 description 1
- OEXNTAFMVQAGHV-UHFFFAOYSA-N 4-tert-butyl-2-pyridin-2-ylpyridine Chemical compound CC(C)(C)C1=CC=NC(C=2N=CC=CC=2)=C1 OEXNTAFMVQAGHV-UHFFFAOYSA-N 0.000 description 1
- UHBIKXOBLZWFKM-UHFFFAOYSA-N 8-hydroxy-2-quinolinecarboxylic acid Chemical compound C1=CC=C(O)C2=NC(C(=O)O)=CC=C21 UHBIKXOBLZWFKM-UHFFFAOYSA-N 0.000 description 1
- SFBHJDZYFDQEEY-UHFFFAOYSA-N 9-cyclobutylcarbazole Chemical compound C1CCC1N1C2=CC=CC=C2C2=CC=CC=C21 SFBHJDZYFDQEEY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- DEUYCYIBUSRJFZ-UHFFFAOYSA-N N#C[Pt]C#N Chemical class N#C[Pt]C#N DEUYCYIBUSRJFZ-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 229910052768 actinide Inorganic materials 0.000 description 1
- 150000001255 actinides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- IATCQARUYGGFOT-UHFFFAOYSA-N copper(1+);platinum(2+) Chemical compound [Cu+].[Pt+2] IATCQARUYGGFOT-UHFFFAOYSA-N 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 description 1
- 229960000452 diethylstilbestrol Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- KZXVOMYVNQPCKX-UHFFFAOYSA-N ethyne;mercury(1+) Chemical compound [Hg+].[C-]#C KZXVOMYVNQPCKX-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- ZPQKWGRIAJXEFX-UHFFFAOYSA-N iridium;2-phenyl-1,3-benzothiazole Chemical compound [Ir].C1=CC=CC=C1C1=NC2=CC=CC=C2S1.C1=CC=CC=C1C1=NC2=CC=CC=C2S1 ZPQKWGRIAJXEFX-UHFFFAOYSA-N 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000002908 osmium compounds Chemical class 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000005560 phenanthrenylene group Chemical group 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical class Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- NLVXBUYJNVGTNB-UHFFFAOYSA-N silver;platinum(2+) Chemical compound [Ag+].[Pt+2] NLVXBUYJNVGTNB-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000005580 triphenylene group Chemical group 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
-
- 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
- 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
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
- Y02B20/30—Semiconductor lamps, e.g. solid state lamps [SSL] light emitting diodes [LED] or organic LED [OLED]
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
式(I)
[上記式中、符号は次の意味を有する:
R1、R2、R7、
R8、R12、R13は互いに独立してCN、アセチリド、チオシアナート又はイソシアナート、好ましくはCN又はアセチリドを表し、その際にアルキルラジカル、特にt−ブチルラジカルを有するアセチリド並びに芳香族ラジカルを有するアセチリドが適しており;特に好ましくはCNであり;
R3、R4、R5、R6、
R9、R10、R14、R15は互いに独立してアリール基、アルキル基、ヘテロアリール基又はアルケニル基、好ましくはアリール基又はアルキル基を表し;
Xはアリーレン基又はヘテロアリーレン基を表し;
oは0〜2、好ましくは0を表し;
p、qは互いに独立して0〜4、好ましくは0又は1であり、特に好ましくはp及びqが1を表す場合に基R14及びR15はビピリジル−配位子の4及び7位に存在し;
n、mは互いに独立して0〜3、好ましくは0又は1であり、特に好ましくはn及びmが1を表す場合に基R9及びR10はバソフェン−配位子の4及び7位に存在し、
その際にm、n、o、pもしくはqが0である場合には、バソフェン−もしくはビピリジル−配位子の相応する部分は水素原子を有し、すなわち非置換である]
からなる群から選択される中性の白金(II)錯体の使用により解決される。
アリールラジカル(又はアリール基)は、芳香族環又は複数の縮合芳香族環から構成されており、炭素原子6〜30個、好ましくは炭素原子6〜18個を有する基本骨格を有するラジカルであると理解されるべきである。適している基本骨格は例えばフェニル、ナフチル、アントラセニル又はフェナントレニルである。この基本骨格は非置換であってよい(すなわち、置換可能である炭素原子の全てが水素原子を有する)か、又は前記基本骨格の1つの、複数の又は全ての置換可能な位置で置換されていてよい。適している置換基は例えばアルキルラジカル、好ましくは炭素原子1〜8個を有するアルキルラジカル、特に好ましくはメチル、エチル、イソプロピル又はt−ブチル、アリールラジカル、好ましくはそしてまた置換又は非置換であってよいC6−アリールラジカル、ヘテロアリールラジカル、好ましくは少なくとも1つの窒素原子を有するヘテロアリールラジカル、特に好ましくはピリジルラジカル、アルケニルラジカル、好ましくは1つの二重結合を有するアルケニルラジカル、特に好ましくは二重結合及び炭素原子1〜8個を有するアルケニルラジカル、又はドナー−又はアクセプター作用を有する基である。ドナー作用を有する基は+I−及び/又は+M−効果を有する基であると理解されるべきであり、かつアクセプター作用を有する基は−I−及び/又は−M−効果を有する基であると理解されるべきである。ドナー−又はアクセプター作用を有している適している基は、ハロゲンラジカル、好ましくはF、Cl、Br、特に好ましくはF、アルコキシラジカル、カルボニルラジカル、エステルラジカル、アミンラジカル、アミドラジカル、CH2F基、CHF2基、CF3基、CN基、チオ基又はSCN基である。極めて特に好ましくはアリールラジカルはメチル、F、Cl及びアルコキシからなる群から選択される置換基を有するか、又はアリールラジカルは非置換である。好ましくはアリールラジカル又はアリール基は場合により前記で挙げた置換基の少なくとも1つで置換されているC6−アリールラジカルである。特に好ましくはC6−アリールラジカルは前記で挙げた置換基の0、1つ又2つを有し、その際に1つの置換基は好ましくはアリールラジカルの別の結合位置に対してp−位に配置されており、かつ − 2つの置換基の場合に − これらはその都度アリールラジカルの別の結合位置に対してm−位に配置されている。極めて特に好ましくはC6−アリールラジカルは非置換のフェニルラジカルである。
1.アノード
2.正孔輸送層
3.発光層
4.電子輸送層
5.カソード。
・アノード(1)と正孔輸送層(2)との間に正孔注入層;
・正孔輸送層(2)と発光層(3)との間に電子のための障壁層;
・発光層(3)と電子輸送層(4)との間に正孔のための障壁層;
・電子輸送層(4)とカソード(5)との間に電子注入層。
1.白金(II)錯体の製造
一般
分光学的測定に使用される全ての溶剤は、相応して分光学的測定に適している品質を有する。Pt(CN)2、dppb(1,2−ビス(ジフェニルホスフィノ)ベンゼン)及びbinap(1,1′−ビナフチル)並びにバソフェン(4,7−ジフェニル−1,10−フェナントロリン)及びt−Bu2bpy(4,4′−t−ブチル−2,2′−ビピリジン)は商業的に入手可能であり、かつさらに精製することなく使用される。
Pt(CN)2(0.76g、3mmol)及びdppb(1.38g、3mmol)からなる混合物をジメチルホルムアミド70ml中に溶解させ、還流下に6時間加熱する。ゆっくりと白色の粉末状沈殿物が形成される。沈殿物をろ過により捕集し、ジエチルエーテルで洗浄し、シリカゲル上で減圧下に乾燥させる。得られた白色の材料をジクロロエタン/ジエチルエーテルからの再結晶により精製し、0.92g(43%)の収量で得られる。
元素分析:
C 55.42、
H 3.49、
N 4.04;
実測値:
C 55.06、
H 3.60、
N 3.94。
ジメチルホルムアミド40ml中のPt(CN)2(0.25g、1mmol)及びbinap(0.63g、1mmol)の混合物を還流下に20時間加熱する。混合物のろ過後に、ジエチルエーテルを得られた溶液に添加する。その際に淡黄色の粉末が沈殿する。前記の黄色粉末を、ろ過により捕集し、ジエチルエーテルで洗浄し、シリカゲル上で減圧で乾燥させる。得られた淡黄色の材料をジクロロメタン/ジエチルエーテルから再結晶させ、その際に所望の生成物0.58g(65%)が得られる。
元素分析:
C 62.23、
H 3.86、
N 3.16;
実測値:
C 62.68、
H 3.90、
N 3.07。
[Pt(バソフェン)(CN)2×H2O]の製造はJ. Am. Chem. Soc., 第112巻, 1990年, p. 5625-5627に開示されている。
Pt(CN)2 0.99g(4.0mmol)及び4,4′−ジ−t−ブチル−2,2′−ジピリジル(4,4′−Bu2bpy)1.10g(4.0mmol)を、DMF 70ml中で還流下に84h加熱した。帯緑色の沈殿物を有する薄い黄色の溶液が生じた。これをろ別し、ろ液をジエチルエーテルと混合した。微細な薄い黄色の沈殿物が沈殿し、これを吸引ろ過し、ジエチルエーテルで洗浄し、シリカゲル上で乾燥させた。収量:0.94g(理論の46%)。得られた物質をDMF/ジエチルエーテルから再結晶させた。
C20H24N4Pt(515.53):計算値 C 46.76、H 4.69、N 10.87;実測値 C 45.34、H 4.54、N 11.18。
MS(ESI):515(77%)、516(MH+、100%)、517(82%)
* 製造は、Che, C.-M., Wan, K.-T., He, L.-Y., Poon, C.-K., Yam, V.W.-W., J. Chem. Soc., Chem. Commun., 1989年, p. 943の[Pt(CN)2(5,5′−Me2bpy)]に類似して行った。
Claims (8)
- エミッタ分子として、式(I)
式(II)
式(III)
[上記式中、符号は次の意味を有する:
R1、R2、R7、
R8、R12、R13 はCNを表し;
R3、R4、R5、R6、
R9、R10、R14、R15は互いに独立してアリール基、アルキル基、ヘテロアリール基又はアルケニル基を表し、
Xはアリーレン基又はヘテロアリーレン基を表し、
oは0〜2を表し、
p、qは互いに独立して0〜4を表し、
n、mは互いに独立して0〜3を表す]
からなる群から選択されている中性の白金(II)錯体を含有している、有機発光ダイオード。 - 式Iの白金(II)−ホスフィン錯体中でR1及びR2がCNを表し、かつR3、R4、R5及びR6 が非置換のフェニルを表し、かつXが、1及び2位で式Iの双方のリン原子のその都度1つに結合されており、かつ非置換であるフェニレン基、2及び3位で又は4及び5位で式Iの双方のリン原子のその都度1つに結合されており、かつ非置換であるナフタレンジイル基、2及び3位で又は4及び5位で式Iの双方のリン原子のその都度1つに結合されており、かつ非置換であるフェナントレンジイル基、2及び2′位で式Iの双方のリン原子のその都度1つに結合されており、かつ非置換である1,1′−ビフェニレン基、2及び2′位で式Iの双方のリン原子のその都度1つに結合されており、かつ非置換である1,1′−ビナフチレン基から選択されている、請求項1記載の有機発光ダイオード。
- 式IIの白金(II)錯体及び式IIIの白金(II)錯体中でR7、R8、R12及びR13がCNを表し、m、n、p、qは0又は1を表し、かつoは0を表し、かつ − m、n=1を表す場合には − R9及びR10が非置換フェニルを表し、かつ − p、qが1を表す場合には − R14及びR15はt−Buを表す、請求項1記載の有機発光ダイオード。
- 発光層として、請求項1から3までのいずれか1項記載の白金(II)錯体を含有している有機発光ダイオード。
- エミッタ分子として請求項1から3までのいずれか1項記載の少なくとも1つの白金(II)錯体を含有している、発光層。
- エミッタ分子として請求項1から3までのいずれか1項記載の少なくとも1つの白金(II)錯体からなる、発光層。
- 請求項5又は6記載の発光層を含有している、OLED。
- 請求項1から4までのいずれか1項又は請求項7記載のOLEDを含有している、コンピューターの視覚表示装置、テレビ、プリンター、調理具における視覚表示装置並びに広告パネル、照明、指示パネルからなる群から選択されている固定式視覚表示装置又は携帯電話(Handys)、ラップトップ、車両における視覚表示装置並びにバス及び鉄道の行先表示からなる群から選択されている移動式視覚表示装置。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10358665A DE10358665A1 (de) | 2003-12-12 | 2003-12-12 | Verwendung von Platin(II)-Komplexen als lumineszierende Materialien in organischen Licht-emittierenden Dioden (OLEDs) |
PCT/EP2004/013944 WO2005056712A1 (de) | 2003-12-12 | 2004-12-08 | Verwendung von platin(ii)-komplexen als lumineszierende materialien in organischen licht-emittierenden dioden (oleds) |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007514029A JP2007514029A (ja) | 2007-05-31 |
JP4271238B2 true JP4271238B2 (ja) | 2009-06-03 |
Family
ID=34638698
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006543464A Expired - Fee Related JP4271238B2 (ja) | 2003-12-12 | 2004-12-08 | 有機発光ダイオード(oled)におけるルミネセンス材料としての白金(ii)錯体の使用 |
Country Status (8)
Country | Link |
---|---|
US (1) | US20070111025A1 (ja) |
EP (1) | EP1692244B1 (ja) |
JP (1) | JP4271238B2 (ja) |
KR (1) | KR20060103954A (ja) |
CN (1) | CN1890347A (ja) |
AT (1) | ATE359340T1 (ja) |
DE (2) | DE10358665A1 (ja) |
WO (1) | WO2005056712A1 (ja) |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3812730B2 (ja) * | 2001-02-01 | 2006-08-23 | 富士写真フイルム株式会社 | 遷移金属錯体及び発光素子 |
JP5080038B2 (ja) * | 2005-08-15 | 2012-11-21 | 学校法人成蹊学園 | 金属錯体を含む発光材料及びそれを用いた光電素子 |
EP1803789A1 (de) | 2005-12-28 | 2007-07-04 | Novaled AG | Verwendung von Metallkomplexen als Emitter in einem elektronischen Bauelement und elektronisches Bauelement |
WO2007115540A1 (de) | 2006-03-30 | 2007-10-18 | Novaled Ag | Verwendung von bora-tetraazapentalenen |
DE102006017485B4 (de) * | 2006-04-13 | 2014-06-05 | Merck Patent Gmbh | Biphenyl-Metallkomplexe - Monomere und Oligomere Triplett-Emitter für OLED-Anwendungen |
EP1860709B1 (de) | 2006-05-24 | 2012-08-08 | Novaled AG | Verwendung von quadratisch planaren Übergangsmetallkomplexen als Dotand |
DE102006030860A1 (de) | 2006-07-04 | 2008-01-10 | Universität Regensburg | Oligomere von Isonitril-Metallkomplexen als Triplett-Emitter für OLED-Anwendungen |
DE102006035018B4 (de) | 2006-07-28 | 2009-07-23 | Novaled Ag | Oxazol-Triplett-Emitter für OLED-Anwendungen |
DE102006048202A1 (de) * | 2006-10-11 | 2008-04-17 | Universität Regensburg | Lanthanoid-Emitter für OLED-Anwendungen |
DE102006051975B4 (de) | 2006-11-03 | 2012-04-19 | Merck Patent Gmbh | Photophysikalische OLED-Effizienz-Steigerung |
DE102007002420A1 (de) | 2007-01-17 | 2008-07-24 | Universität Regensburg | Polymere Anionen/Kationen |
US8106199B2 (en) * | 2007-02-13 | 2012-01-31 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Organometallic materials for optical emission, optical absorption, and devices including organometallic materials |
CN104250269B (zh) | 2007-05-21 | 2018-01-05 | 欧司朗Oled股份有限公司 | 磷光金属配位化合物,含其的发射辐射元件和其制备方法 |
DE102007031261A1 (de) * | 2007-07-05 | 2009-01-08 | Universtität Regensburg | Lumineszierende Metallkomplexe mit sperrigen Hilfsliganden |
CN101809118B (zh) * | 2007-09-28 | 2014-07-30 | 奥斯兰姆奥普托半导体有限责任公司 | 有机辐射发射构件 |
DE102007046445A1 (de) | 2007-09-28 | 2009-04-16 | Osram Opto Semiconductors Gmbh | Organisches selbstemittierendes Bauteil |
WO2009086209A2 (en) | 2007-12-21 | 2009-07-09 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Platinum(ii) di(2-pyrazolyl)benzene chloride analogs and uses |
WO2009111299A2 (en) | 2008-02-29 | 2009-09-11 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Tridentate platinum (ii) complexes |
DE102008013691A1 (de) | 2008-03-11 | 2009-09-17 | Merck Patent Gmbh | Verwendung von Zusammensetzungen neutraler Übergangsmetallkomplexe in opto-elektronischen Bauelementen |
DE102008033563A1 (de) * | 2008-07-17 | 2010-01-21 | Merck Patent Gmbh | Komplexe mit kleinen Singulett-Triplett-Energie-Abständen zur Verwendung in opto-elektronischen Bauteilen (Singulett-Harvesting-Effekt) |
DE102008033929A1 (de) | 2008-07-18 | 2010-01-21 | Siemens Aktiengesellschaft | Phosphoreszente Metallkomplexverbindung, Verfahren zur Herstellung dazu und strahlungsemittierendes Bauelement |
EP2161272A1 (en) | 2008-09-05 | 2010-03-10 | Basf Se | Phenanthrolines |
DE102008048336A1 (de) | 2008-09-22 | 2010-03-25 | Merck Patent Gmbh | Einkernige neutrale Kupfer(I)-Komplexe und deren Verwendung zur Herstellung von optoelektronischen Bauelementen |
US8119037B2 (en) | 2008-10-16 | 2012-02-21 | Novaled Ag | Square planar transition metal complexes and organic semiconductive materials using them as well as electronic or optoelectric components |
DE102008053121A1 (de) * | 2008-10-24 | 2010-04-29 | Merck Patent Gmbh | Doppelkomplex-Salze als Emitter in OLED-Vorrichtungen |
DE102009030475A1 (de) | 2009-06-24 | 2011-01-05 | Hartmut Prof. Dr. Yersin | Kupfer-Komplexe für optoelektronische Anwendungen |
DE102009031683A1 (de) | 2009-07-03 | 2011-03-24 | Siemens Aktiengesellschaft | Phophoreszente Metallkomplexverbindung, Verfahren zur Herstellung dazu und strahlungsemittierendes Bauelement |
DE102010005632A1 (de) | 2010-01-25 | 2011-07-28 | Siemens Aktiengesellschaft, 80333 | Phosphoreszente Metallkomplexverbindung, Verfahren zur Herstellung und lichtemittierendes Bauelement |
DE102010005634A1 (de) | 2010-01-25 | 2011-07-28 | Siemens Aktiengesellschaft, 80333 | Neuartige Verwendung des Guanidinium-Kations und lichtemittierendes Bauelement |
EP2594571A1 (de) | 2011-11-16 | 2013-05-22 | Cynora GmbH | Kupfer-Komplexe für optoelektronische Anwendungen |
US10056567B2 (en) | 2014-02-28 | 2018-08-21 | Arizona Board Of Regents On Behalf Of Arizona State University | Chiral metal complexes as emitters for organic polarized electroluminescent devices |
US9502671B2 (en) | 2014-07-28 | 2016-11-22 | Arizona Board Of Regents On Behalf Of Arizona State University | Tridentate cyclometalated metal complexes with six-membered coordination rings |
US9818959B2 (en) | 2014-07-29 | 2017-11-14 | Arizona Board of Regents on behlaf of Arizona State University | Metal-assisted delayed fluorescent emitters containing tridentate ligands |
WO2016055557A1 (de) | 2014-10-08 | 2016-04-14 | Cynora Gmbh | Metall-komplexe mit tridentaten liganden für optoelektronische anwendungen |
US9865825B2 (en) | 2014-11-10 | 2018-01-09 | Arizona Board Of Regents On Behalf Of Arizona State University | Emitters based on octahedral metal complexes |
JP5952460B1 (ja) * | 2015-05-12 | 2016-07-13 | 田中貴金属工業株式会社 | 有機白金化合物からなる化学蒸着用原料及び該化学蒸着用原料を用いた化学蒸着法 |
CN109503668B (zh) * | 2018-12-28 | 2020-07-28 | 西安交通大学 | 含骨架结构的双金属中心有机铂配合物能源转化材料 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5648270A (en) * | 1995-02-06 | 1997-07-15 | Molecular Probes, Inc. | Methods of sensing with fluorescent conjugates of metal-chelating nitrogen heterocycles |
US6548836B1 (en) * | 1999-04-29 | 2003-04-15 | Massachusetts Institute Of Technology | Solid state light-emitting device |
WO2003014257A2 (en) * | 2001-04-13 | 2003-02-20 | Semiconductor Energy Laboratory Co., Ltd. | Organic light-emitting device and light-emitting apparatus comprising the device |
TW565604B (en) * | 2001-04-25 | 2003-12-11 | Toray Industries | Pyrromethene metal complex, material of luminescent element using it and luminescent element |
US6653654B1 (en) * | 2002-05-01 | 2003-11-25 | The University Of Hong Kong | Electroluminescent materials |
-
2003
- 2003-12-12 DE DE10358665A patent/DE10358665A1/de not_active Withdrawn
-
2004
- 2004-12-08 KR KR1020067014024A patent/KR20060103954A/ko not_active Application Discontinuation
- 2004-12-08 AT AT04803620T patent/ATE359340T1/de not_active IP Right Cessation
- 2004-12-08 JP JP2006543464A patent/JP4271238B2/ja not_active Expired - Fee Related
- 2004-12-08 DE DE502004003504T patent/DE502004003504D1/de not_active Expired - Fee Related
- 2004-12-08 WO PCT/EP2004/013944 patent/WO2005056712A1/de active IP Right Grant
- 2004-12-08 CN CNA2004800368944A patent/CN1890347A/zh active Pending
- 2004-12-08 EP EP04803620A patent/EP1692244B1/de not_active Not-in-force
- 2004-12-08 US US10/580,836 patent/US20070111025A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
EP1692244B1 (de) | 2007-04-11 |
CN1890347A (zh) | 2007-01-03 |
EP1692244A1 (de) | 2006-08-23 |
DE10358665A1 (de) | 2005-07-07 |
US20070111025A1 (en) | 2007-05-17 |
JP2007514029A (ja) | 2007-05-31 |
DE502004003504D1 (de) | 2007-05-24 |
WO2005056712A1 (de) | 2005-06-23 |
KR20060103954A (ko) | 2006-10-04 |
ATE359340T1 (de) | 2007-05-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4271238B2 (ja) | 有機発光ダイオード(oled)におけるルミネセンス材料としての白金(ii)錯体の使用 | |
KR101698154B1 (ko) | 중수소화된 전이 금속 착물 및 이의 유기 발광 다이오드에서의 용도 ⅴ | |
KR101656793B1 (ko) | 신규한 전이 금속 착물 및 이의 유기 발광 다이오드에서의 용도 - ⅲ | |
JP5553758B2 (ja) | Oledにおけるマトリックス材料および/または電子遮断体としてのアクリジン誘導体の使用 | |
US8940904B2 (en) | Use of transition metal-carbene complexes which do not comprise any cyclometallation via non-carbenes in OLEDs | |
JP6486355B2 (ja) | Oled等の電子デバイスで使用するための発光性のジアザ−モノアザ−およびベンゾイミダゾール金属カルベン錯体 | |
US8247574B2 (en) | Use of PT -and PD-BIS- and tetra-carbon complexes with bridged carbon ligands in OLEDs | |
US7858208B2 (en) | Use of a copper (I) complexes for organic luminescent diodes | |
JP5153161B2 (ja) | 有機金属錯体およびそれを利用した有機el素子 | |
KR20100061831A (ko) | 세자리 리간드를 갖는 착체 | |
KR20110031387A (ko) | 다핵 착물을 포함하는 발광 물질 | |
KR20060108127A (ko) | 실릴 치환된 시클로메탈화 전이금속 착물 및 이를 이용한유기 전계 발광 소자 | |
Wang et al. | Carbazole and arylamine functionalized iridium complexes for efficient electro-phosphorescent light-emitting diodes | |
JP2013543864A (ja) | リン光物質 | |
Rai et al. | Substituent effect on the electroluminescence efficiency of amidinate-ligated bis (pyridylphenyl) iridium (III) complexes | |
US7198730B2 (en) | Phosphorescent material | |
JP2017031208A (ja) | 高効率リン光材料 | |
JP2009057304A (ja) | 金属錯体及び有機電界発光素子 | |
JP4488243B2 (ja) | トリス−オルト−メタル化有機金属錯体の製法およびoledにおける該錯体の使用 | |
EP1953844A1 (en) | Organic electroluminescent device | |
JP4380433B2 (ja) | 金属配位化合物を含有する高分子共重合体およびこれを用いた有機エレクトロルミネセンス素子 | |
US20110114933A1 (en) | Novel transition metal complexes and use thereof in organic light-emitting diodes - iv | |
JP2013142088A (ja) | 高効率リン光材料 | |
Yu et al. | Synthesis, photo-and electro-luminescence of novel red phosphorescent Ir (III) complexes with a silsesquioxane core | |
KR101601394B1 (ko) | 카보레인을 함유하는 인광 화합물 및 이를 이용하는 인광 유기 발광 소자 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20080227 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20080312 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080610 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20080723 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20090130 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20090224 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120306 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
LAPS | Cancellation because of no payment of annual fees |