JP3445315B2 - アルミニウムキレート化合物及び内部接合型有機電界発光素子 - Google Patents
アルミニウムキレート化合物及び内部接合型有機電界発光素子Info
- Publication number
- JP3445315B2 JP3445315B2 JP17155293A JP17155293A JP3445315B2 JP 3445315 B2 JP3445315 B2 JP 3445315B2 JP 17155293 A JP17155293 A JP 17155293A JP 17155293 A JP17155293 A JP 17155293A JP 3445315 B2 JP3445315 B2 JP 3445315B2
- Authority
- JP
- Japan
- Prior art keywords
- organic
- compound
- ligand
- transport zone
- quinolinolato
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims description 55
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 title claims description 23
- 229910052782 aluminium Inorganic materials 0.000 title claims description 18
- 239000013522 chelant Substances 0.000 title claims description 14
- 238000002347 injection Methods 0.000 claims description 46
- 239000007924 injection Substances 0.000 claims description 46
- 239000003446 ligand Substances 0.000 claims description 46
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 241001024304 Mino Species 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 230000002452 interceptive effect Effects 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 81
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 50
- 239000010410 layer Substances 0.000 description 45
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 26
- 229910052786 argon Inorganic materials 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 21
- 239000002244 precipitate Substances 0.000 description 20
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 19
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 16
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 14
- 229960003540 oxyquinoline Drugs 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 238000001914 filtration Methods 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- -1 hydroxy hydrocarbons Chemical class 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000005711 Benzoic acid Substances 0.000 description 8
- 235000010233 benzoic acid Nutrition 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229960003742 phenol Drugs 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 6
- 230000000737 periodic effect Effects 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000006071 cream Substances 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 4
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 4
- 150000004032 porphyrins Chemical class 0.000 description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 229910052715 tantalum Inorganic materials 0.000 description 4
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- AJBHBBKGBVIOBK-UHFFFAOYSA-N 1,1'-biphenyl hydroxysilane Chemical compound [SiH3]O.C1=CC=C(C=C1)C1=CC=CC=C1.C1=CC=C(C=C1)C1=CC=CC=C1.C1=CC=C(C=C1)C1=CC=CC=C1 AJBHBBKGBVIOBK-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- JKYPBYBOZSIRFW-UHFFFAOYSA-N 3-(4-chlorophenyl)oxolane-2,5-dione Chemical compound C1=CC(Cl)=CC=C1C1C(=O)OC(=O)C1 JKYPBYBOZSIRFW-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical group 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004305 biphenyl Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000002923 metal particle Substances 0.000 description 2
- 239000013081 microcrystal Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910052761 rare earth metal Chemical group 0.000 description 2
- 150000002910 rare earth metals Chemical group 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000003512 tertiary amines Chemical group 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- YWBHROUQJYHSOR-UHFFFAOYSA-N $l^{1}-selanylbenzene Chemical compound [Se]C1=CC=CC=C1 YWBHROUQJYHSOR-UHFFFAOYSA-N 0.000 description 1
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-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
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 1
- VOXXGUAZBWSUSS-UHFFFAOYSA-N 2,4,6-triphenyl-1,3,5,2,4,6-trioxatriborinane Chemical compound O1B(C=2C=CC=CC=2)OB(C=2C=CC=CC=2)OB1C1=CC=CC=C1 VOXXGUAZBWSUSS-UHFFFAOYSA-N 0.000 description 1
- MVVGSPCXHRFDDR-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC2=CC=CC=C2S1 MVVGSPCXHRFDDR-UHFFFAOYSA-N 0.000 description 1
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- YDIYEOMDOWUDTJ-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(C(O)=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-N 0.000 description 1
- XUDQSFMBCQRHAX-UHFFFAOYSA-N 4-(n-phenylanilino)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 XUDQSFMBCQRHAX-UHFFFAOYSA-N 0.000 description 1
- ADCUEPOHPCPMCE-UHFFFAOYSA-N 4-cyanobenzoic acid Chemical compound OC(=O)C1=CC=C(C#N)C=C1 ADCUEPOHPCPMCE-UHFFFAOYSA-N 0.000 description 1
- XGWFJBFNAQHLEF-UHFFFAOYSA-N 9-anthroic acid Chemical compound C1=CC=C2C(C(=O)O)=C(C=CC=C3)C3=CC2=C1 XGWFJBFNAQHLEF-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- CBQYNPHHHJTCJS-UHFFFAOYSA-N Alline Chemical compound C1=CC=C2C3(O)CCN(C)C3NC2=C1 CBQYNPHHHJTCJS-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000283984 Rodentia Species 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
- XRKIHUXCUIFHAS-UHFFFAOYSA-N [4-(3-methoxy-3-oxopropyl)phenyl]boronic acid Chemical compound COC(=O)CCC1=CC=C(B(O)O)C=C1 XRKIHUXCUIFHAS-UHFFFAOYSA-N 0.000 description 1
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
- 239000002253 acid Substances 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
- 125000000217 alkyl group Chemical group 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- VRLFOXMNTSYGMX-UHFFFAOYSA-N diphenyl ditelluride Chemical compound C=1C=CC=CC=1[Te][Te]C1=CC=CC=C1 VRLFOXMNTSYGMX-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 1
- 229960002297 fenofibrate Drugs 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 150000005204 hydroxybenzenes Chemical class 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 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
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 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 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- CDXVUROVRIFQMV-UHFFFAOYSA-N oxo(diphenoxy)phosphanium Chemical compound C=1C=CC=CC=1O[P+](=O)OC1=CC=CC=C1 CDXVUROVRIFQMV-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 238000001228 spectrum 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
- 239000000725 suspension Substances 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- XSOKHXFFCGXDJZ-UHFFFAOYSA-N telluride(2-) Chemical compound [Te-2] XSOKHXFFCGXDJZ-UHFFFAOYSA-N 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- JQPMDTQDAXRDGS-UHFFFAOYSA-N triphenylalumane Chemical compound C1=CC=CC=C1[Al](C=1C=CC=CC=1)C1=CC=CC=C1 JQPMDTQDAXRDGS-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91237692A | 1992-07-13 | 1992-07-13 | |
| US912376 | 1992-07-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06172751A JPH06172751A (ja) | 1994-06-21 |
| JP3445315B2 true JP3445315B2 (ja) | 2003-09-08 |
Family
ID=25431811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17155293A Expired - Lifetime JP3445315B2 (ja) | 1992-07-13 | 1993-07-12 | アルミニウムキレート化合物及び内部接合型有機電界発光素子 |
Country Status (4)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7781072B2 (en) | 2002-03-29 | 2010-08-24 | Pioneer Corporation | Organic electroluminescence device |
Families Citing this family (124)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5466392A (en) * | 1993-06-02 | 1995-11-14 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and compound having an aluminum complex structure |
| DE69526614T2 (de) * | 1994-09-12 | 2002-09-19 | Motorola, Inc. | Lichtemittierende Vorrichtungen die Organometallische Komplexe enthalten. |
| US5707745A (en) | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
| US5703436A (en) | 1994-12-13 | 1997-12-30 | The Trustees Of Princeton University | Transparent contacts for organic devices |
| US6358631B1 (en) | 1994-12-13 | 2002-03-19 | The Trustees Of Princeton University | Mixed vapor deposited films for electroluminescent devices |
| US5552547A (en) * | 1995-02-13 | 1996-09-03 | Shi; Song Q. | Organometallic complexes with built-in fluorescent dyes for use in light emitting devices |
| US5837390A (en) * | 1995-05-10 | 1998-11-17 | Sony Corporation | Metal complex, method for producing the same and optical device |
| US5779937A (en) * | 1995-05-16 | 1998-07-14 | Sanyo Electric Co., Ltd. | Organic electroluminescent device |
| JP3752734B2 (ja) * | 1996-07-12 | 2006-03-08 | 双葉電子工業株式会社 | 有機エレクトロルミネッセンス素子および有機エレクトロルミネッセンス素子材料 |
| US6312835B1 (en) * | 1997-02-13 | 2001-11-06 | Queen's University At Kingston | Luminescent compounds and methods of making and using same |
| WO1998051131A1 (en) | 1997-05-08 | 1998-11-12 | Sanyo Electric Co., Ltd. | Organic electroluminescent device |
| JP3525034B2 (ja) | 1997-07-31 | 2004-05-10 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
| DE19735653A1 (de) * | 1997-08-16 | 1999-02-18 | Bosch Gmbh Robert | Elektrolumineszierende Verbindung und organische elektrolumineszierende Anordnung diese enthaltend |
| JP2914361B2 (ja) * | 1997-10-09 | 1999-06-28 | 日本電気株式会社 | 有機薄膜ｅｌ素子 |
| US6451455B1 (en) * | 1998-04-01 | 2002-09-17 | The Trustees Of Princeton University | Metal complexes bearing both electron transporting and hole transporting moieties |
| JP4090100B2 (ja) * | 1998-02-27 | 2008-05-28 | 出光興産株式会社 | アルミニウム化合物およびその製造方法、オレフィン重合体製造用触媒並びにオレフィン重合体の製造方法 |
| US6406804B1 (en) | 1998-04-09 | 2002-06-18 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
| JP3825564B2 (ja) * | 1998-05-25 | 2006-09-27 | 三洋電機株式会社 | 有機エレクトロルミネッセンス素子 |
| US6368731B2 (en) | 1998-07-04 | 2002-04-09 | Bayer Aktiengesellschaft | Electroluminescent assemblies using boron chelates of 8-aminoquinoline derivatives |
| DE19829947A1 (de) * | 1998-07-04 | 2000-01-05 | Bayer Ag | Elektrolumineszierende Anordnungen mit Bor-Chelaten |
| DE19829949A1 (de) * | 1998-07-04 | 2000-01-05 | Bayer Ag | Elektrolumineszierende Anordnungen unter Verwendung von Bor-Chelaten von 8-Aminochinolin-Derivaten |
| EP0975027A2 (en) * | 1998-07-23 | 2000-01-26 | Sony Corporation | Light emitting device and process for producing the same |
| DE19839946A1 (de) * | 1998-09-02 | 2000-03-09 | Bayer Ag | Elektrolumineszierende Anordnungen mit mehrkernigen Metallkomplexen |
| TW538114B (en) * | 1999-07-12 | 2003-06-21 | Ibm | Material for use in a light emitting device and highly efficient electroluminescent device |
| KR100721656B1 (ko) * | 2005-11-01 | 2007-05-23 | 주식회사 엘지화학 | 유기 전기 소자 |
| JP3822029B2 (ja) | 2000-06-07 | 2006-09-13 | シャープ株式会社 | 発光器、発光装置、及び表示パネル |
| US7306856B2 (en) * | 2000-07-17 | 2007-12-11 | Fujifilm Corporation | Light-emitting element and iridium complex |
| US6939624B2 (en) | 2000-08-11 | 2005-09-06 | Universal Display Corporation | Organometallic compounds and emission-shifting organic electrophosphorescence |
| US6911271B1 (en) * | 2000-08-11 | 2005-06-28 | The University Of Southern California | Organometallic platinum complexes for phosphorescence based organic light emitting devices |
| 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 |
| DE10109027A1 (de) * | 2001-02-24 | 2002-09-05 | Covion Organic Semiconductors | Rhodium- und Iridium-Komplexe |
| GB0104700D0 (en) * | 2001-02-26 | 2001-04-11 | Isis Innovation | Luminescent polymers |
| GB0109757D0 (en) * | 2001-04-20 | 2001-06-13 | Elam T Ltd | White light emitting electroluminescent material |
| US6597012B2 (en) * | 2001-05-02 | 2003-07-22 | Junji Kido | Organic electroluminescent device |
| US6603150B2 (en) | 2001-09-28 | 2003-08-05 | Eastman Kodak Company | Organic light-emitting diode having an interface layer between the hole-transporting layer and the light-emitting layer |
| US6610455B1 (en) | 2002-01-30 | 2003-08-26 | Eastman Kodak Company | Making electroluminscent display devices |
| US6872472B2 (en) | 2002-02-15 | 2005-03-29 | Eastman Kodak Company | Providing an organic electroluminescent device having stacked electroluminescent units |
| US6770502B2 (en) * | 2002-04-04 | 2004-08-03 | Eastman Kodak Company | Method of manufacturing a top-emitting OLED display device with desiccant structures |
| DE10215010A1 (de) * | 2002-04-05 | 2003-10-23 | Covion Organic Semiconductors | Rhodium- und Iridium-Komplexe |
| JP2004026749A (ja) * | 2002-06-27 | 2004-01-29 | Tokyo Inst Of Technol | ＡｌＲｑ′２型アルミニウム化合物およびその製法ならびにその誘導体 |
| TW200402012A (en) * | 2002-07-23 | 2004-02-01 | Eastman Kodak Co | OLED displays with fiber-optic faceplates |
| US6939660B2 (en) * | 2002-08-02 | 2005-09-06 | Eastman Kodak Company | Laser thermal transfer donor including a separate dopant layer |
| US6890627B2 (en) | 2002-08-02 | 2005-05-10 | Eastman Kodak Company | Laser thermal transfer from a donor element containing a hole-transporting layer |
| KR20050052473A (ko) * | 2002-08-16 | 2005-06-02 | 더 유니버시티 오브 써던 캘리포니아 | 유기 발광 물질 및 장치 |
| US6747618B2 (en) | 2002-08-20 | 2004-06-08 | Eastman Kodak Company | Color organic light emitting diode display with improved lifetime |
| KR20040017065A (ko) * | 2002-08-20 | 2004-02-26 | 학교법인 인하학원 | 청색 유기 전계 발광 소자용 알루미늄 착 화합물, 그제조방법 및 이를 이용한 유기 전계 발광소자 |
| US20040043140A1 (en) * | 2002-08-21 | 2004-03-04 | Ramesh Jagannathan | Solid state lighting using compressed fluid coatings |
| US20040043138A1 (en) * | 2002-08-21 | 2004-03-04 | Ramesh Jagannathan | Solid state lighting using compressed fluid coatings |
| US6765349B2 (en) * | 2002-09-30 | 2004-07-20 | Eastman Kodak Company | High work function metal alloy cathode used in organic electroluminescent devices |
| US7230594B2 (en) | 2002-12-16 | 2007-06-12 | Eastman Kodak Company | Color OLED display with improved power efficiency |
| US20040142206A1 (en) | 2003-01-17 | 2004-07-22 | Bazan Guillermo C. | Binaphthol based chromophores for the fabrication of blue organic light emitting diodes |
| 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 |
| TWI390006B (zh) * | 2003-08-07 | 2013-03-21 | Nippon Steel Chemical Co | Organic EL materials with aluminum clamps |
| JP4822687B2 (ja) * | 2003-11-21 | 2011-11-24 | 富士フイルム株式会社 | 有機電界発光素子 |
| US7221332B2 (en) * | 2003-12-19 | 2007-05-22 | Eastman Kodak Company | 3D stereo OLED display |
| US8084145B2 (en) * | 2004-04-02 | 2011-12-27 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light emitting element using the complex, light emitting device using the element, and electric apparatus using the device |
| US20060017055A1 (en) * | 2004-07-23 | 2006-01-26 | Eastman Kodak Company | Method for manufacturing a display device with low temperature diamond coatings |
| US7316756B2 (en) | 2004-07-27 | 2008-01-08 | Eastman Kodak Company | Desiccant for top-emitting OLED |
| US7579090B2 (en) * | 2004-09-20 | 2009-08-25 | Eastman Kodak Company | Organic element for electroluminescent devices |
| US9040170B2 (en) * | 2004-09-20 | 2015-05-26 | Global Oled Technology Llc | Electroluminescent device with quinazoline complex emitter |
| US7501152B2 (en) | 2004-09-21 | 2009-03-10 | Eastman Kodak Company | Delivering particulate material to a vaporization zone |
| ITMN20040024A1 (it) * | 2004-09-24 | 2004-12-24 | Pe Srl | Macchina etichettatrice per etichette destinate a termoretrazione |
| KR100880220B1 (ko) * | 2004-10-04 | 2009-01-28 | 엘지디스플레이 주식회사 | 유기 실리콘을 갖는 페닐 피리딘기를 포함하는 이리듐화합물계 발광 화합물 및 이를 발색 재료로서 사용하는유기전계발광소자 |
| TWI260339B (en) * | 2004-10-07 | 2006-08-21 | Au Optronics Corp | Organometallic compound and organic electroluminescent device including the same |
| DE102004057072A1 (de) * | 2004-11-25 | 2006-06-01 | Basf Ag | Verwendung von Übergangsmetall-Carbenkomplexen in organischen Licht-emittierenden Dioden (OLEDs) |
| EP1869059B1 (en) * | 2005-03-17 | 2014-04-23 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, and light-emitting element, light-emitting device and electronic device using the organometallic complex |
| US7473477B2 (en) * | 2005-03-31 | 2009-01-06 | Eastman Kodak Company | Phosphorescent iridium complexes |
| KR101223717B1 (ko) * | 2005-04-12 | 2013-01-18 | 삼성디스플레이 주식회사 | 실릴 치환된 시클로메탈화 전이금속 착물 및 이를 이용한 유기 전계 발광 소자 |
| US8057916B2 (en) * | 2005-04-20 | 2011-11-15 | Global Oled Technology, Llc. | OLED device with improved performance |
| US20060240281A1 (en) * | 2005-04-21 | 2006-10-26 | Eastman Kodak Company | Contaminant-scavenging layer on OLED anodes |
| US20070048545A1 (en) * | 2005-08-31 | 2007-03-01 | Eastman Kodak Company | Electron-transporting layer for white OLED device |
| 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 |
| US8956738B2 (en) * | 2005-10-26 | 2015-02-17 | Global Oled Technology Llc | Organic element for low voltage electroluminescent devices |
| US9666826B2 (en) * | 2005-11-30 | 2017-05-30 | Global Oled Technology Llc | Electroluminescent device including an anthracene derivative |
| US20070122657A1 (en) * | 2005-11-30 | 2007-05-31 | Eastman Kodak Company | Electroluminescent device containing a phenanthroline derivative |
| EP1963346B1 (en) * | 2005-12-05 | 2012-08-22 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex and light-emitting element, light-emitting device and electronic device using the same |
| CN101371619B (zh) * | 2006-01-18 | 2013-11-13 | Lg化学株式会社 | 具有堆叠式有机发光单元的oled |
| US20070207345A1 (en) * | 2006-03-01 | 2007-09-06 | Eastman Kodak Company | Electroluminescent device including gallium complexes |
| EP1873163B1 (en) | 2006-03-21 | 2010-08-25 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex and light emitting element, light emitting device, and electronic device using the organometallic complex |
| EP2355198B1 (en) | 2006-05-08 | 2015-09-09 | Global OLED Technology LLC | OLED electron-injecting layer |
| DE102006025777A1 (de) * | 2006-05-31 | 2007-12-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
| US7667391B2 (en) * | 2006-08-04 | 2010-02-23 | Eastman Kodak Company | Electrically excited organic light-emitting diodes with spatial and spectral coherence |
| WO2008029670A1 (fr) * | 2006-08-31 | 2008-03-13 | Nippon Steel Chemical Co., Ltd. | Matériau de dispositif électroluminescent organique et dispositif électroluminescent organique |
| US20080176099A1 (en) * | 2007-01-18 | 2008-07-24 | Hatwar Tukaram K | White oled device with improved functions |
| US7911133B2 (en) * | 2007-05-10 | 2011-03-22 | Global Oled Technology Llc | Electroluminescent device having improved light output |
| US20080284318A1 (en) * | 2007-05-17 | 2008-11-20 | Deaton Joseph C | Hybrid fluorescent/phosphorescent oleds |
| US20080284317A1 (en) * | 2007-05-17 | 2008-11-20 | Liang-Sheng Liao | Hybrid oled having improved efficiency |
| KR20100018036A (ko) * | 2007-06-05 | 2010-02-16 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기금속 착체, 및 발광 재료, 발광 소자, 발광 장치 및 전자 기기 |
| US20090004485A1 (en) * | 2007-06-27 | 2009-01-01 | Shiying Zheng | 6-member ring structure used in electroluminescent devices |
| EP2019108A3 (en) | 2007-07-24 | 2009-04-08 | Gracel Display Inc. | Novel red electroluminescent compounds and organic electronluminescent device using same |
| US7812531B2 (en) | 2007-07-25 | 2010-10-12 | Global Oled Technology Llc | Preventing stress transfer in OLED display components |
| KR100963378B1 (ko) * | 2007-08-31 | 2010-06-14 | 주식회사 엘지화학 | 유기 금속 착물 유도체 및 이를 이용하는 유기발광소자 |
| KR101625235B1 (ko) * | 2007-09-20 | 2016-05-27 | 바스프 에스이 | 전계발광 소자 |
| US20090091242A1 (en) * | 2007-10-05 | 2009-04-09 | Liang-Sheng Liao | Hole-injecting layer in oleds |
| US8076009B2 (en) | 2007-10-26 | 2011-12-13 | Global Oled Technology, Llc. | OLED device with fluoranthene electron transport materials |
| US8431242B2 (en) * | 2007-10-26 | 2013-04-30 | Global Oled Technology, Llc. | OLED device with certain fluoranthene host |
| US20090110956A1 (en) * | 2007-10-26 | 2009-04-30 | Begley William J | Oled device with electron transport material combination |
| US8129039B2 (en) | 2007-10-26 | 2012-03-06 | Global Oled Technology, Llc | Phosphorescent OLED device with certain fluoranthene host |
| US8420229B2 (en) * | 2007-10-26 | 2013-04-16 | Global OLED Technologies LLC | OLED device with certain fluoranthene light-emitting dopants |
| US8016631B2 (en) * | 2007-11-16 | 2011-09-13 | Global Oled Technology Llc | Desiccant sealing arrangement for OLED devices |
| US8900722B2 (en) | 2007-11-29 | 2014-12-02 | Global Oled Technology Llc | OLED device employing alkali metal cluster compounds |
| US8877350B2 (en) * | 2007-12-11 | 2014-11-04 | Global Oled Technology Llc | White OLED with two blue light-emitting layers |
| US20090162612A1 (en) * | 2007-12-19 | 2009-06-25 | Hatwar Tukaram K | Oled device having two electron-transport layers |
| US7534635B1 (en) | 2008-03-24 | 2009-05-19 | General Electric Company | Getter precursors for hermetically sealed packaging |
| US7947974B2 (en) * | 2008-03-25 | 2011-05-24 | Global Oled Technology Llc | OLED device with hole-transport and electron-transport materials |
| US8247088B2 (en) * | 2008-08-28 | 2012-08-21 | Global Oled Technology Llc | Emitting complex for electroluminescent devices |
| EP2161272A1 (en) | 2008-09-05 | 2010-03-10 | Basf Se | Phenanthrolines |
| US7931975B2 (en) * | 2008-11-07 | 2011-04-26 | Global Oled Technology Llc | Electroluminescent device containing a flouranthene compound |
| US8088500B2 (en) * | 2008-11-12 | 2012-01-03 | Global Oled Technology Llc | OLED device with fluoranthene electron injection materials |
| US7968215B2 (en) * | 2008-12-09 | 2011-06-28 | Global Oled Technology Llc | OLED device with cyclobutene electron injection materials |
| WO2010090362A1 (en) * | 2009-02-06 | 2010-08-12 | Pusan National University Industry-University Cooperation Foundation | Phosphorescent light-emitting iridium complex containing pyridyltriazole ligand |
| US8216697B2 (en) * | 2009-02-13 | 2012-07-10 | Global Oled Technology Llc | OLED with fluoranthene-macrocyclic materials |
| US8147989B2 (en) * | 2009-02-27 | 2012-04-03 | Global Oled Technology Llc | OLED device with stabilized green light-emitting layer |
| US20100244677A1 (en) * | 2009-03-31 | 2010-09-30 | Begley William J | Oled device containing a silyl-fluoranthene derivative |
| US8283054B2 (en) | 2009-04-03 | 2012-10-09 | Global Oled Technology Llc | Tandem white OLED with efficient electron transfer |
| US8206842B2 (en) * | 2009-04-06 | 2012-06-26 | Global Oled Technology Llc | Organic element for electroluminescent devices |
| EP2443213B1 (en) | 2009-06-18 | 2014-04-23 | Basf Se | Phenanthroazole compounds as hole transporting materials for electro luminescent devices |
| JP5242648B2 (ja) * | 2010-09-07 | 2013-07-24 | 株式会社東芝 | 新規化合物ならびにそれを使用した有機電界発光素子、表示装置および照明装置 |
| CN104170110B (zh) * | 2012-02-15 | 2016-11-02 | 国立大学法人山形大学 | 有机电致发光元件 |
| US10400163B2 (en) * | 2013-02-08 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10593886B2 (en) | 2013-08-25 | 2020-03-17 | Molecular Glasses, Inc. | OLED devices with improved lifetime using non-crystallizable molecular glass mixture hosts |
| DE102014114231A1 (de) | 2014-09-30 | 2016-03-31 | Osram Oled Gmbh | Verfahren zur Herstellung eines organischen elektronischen Bauteils und ein organisches elektronisches Bauteil |
| US10153441B2 (en) * | 2015-03-30 | 2018-12-11 | Industrial Technology Research Institute | Organic metal compound, organic light-emitting device, and lighting device employing the same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3149991B2 (ja) | 1991-08-01 | 2001-03-26 | イーストマン コダック カンパニー | ブルー放出性発光組成物 |
| JP3213063B2 (ja) | 1991-08-01 | 2001-09-25 | イーストマン コダック カンパニー | 内部接合形有機エレクトロルミネセント素子 |
| JP3215510B2 (ja) | 1991-08-01 | 2001-10-09 | イーストマン コダック カンパニー | 内部接合形有機エレクトロルミネセント素子 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL250330A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1959-04-09 | |||
| US3658520A (en) * | 1968-02-20 | 1972-04-25 | Eastman Kodak Co | Photoconductive elements containing as photoconductors triarylamines substituted by active hydrogen-containing groups |
| US3567450A (en) * | 1968-02-20 | 1971-03-02 | Eastman Kodak Co | Photoconductive elements containing substituted triarylamine photoconductors |
| US3935031A (en) * | 1973-05-07 | 1976-01-27 | New England Institute, Inc. | Photovoltaic cell with enhanced power output |
| US4175960A (en) * | 1974-12-20 | 1979-11-27 | Eastman Kodak Company | Multi-active photoconductive element having an aggregate charge generating layer |
| US4356429A (en) * | 1980-07-17 | 1982-10-26 | Eastman Kodak Company | Organic electroluminescent cell |
| US4539507A (en) * | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
| US4885211A (en) * | 1987-02-11 | 1989-12-05 | Eastman Kodak Company | Electroluminescent device with improved cathode |
| US4720432A (en) * | 1987-02-11 | 1988-01-19 | Eastman Kodak Company | Electroluminescent device with organic luminescent medium |
| US4769292A (en) * | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
| US4950950A (en) * | 1989-05-18 | 1990-08-21 | Eastman Kodak Company | Electroluminescent device with silazane-containing luminescent zone |
| US5047687A (en) * | 1990-07-26 | 1991-09-10 | Eastman Kodak Company | Organic electroluminescent device with stabilized cathode |
| US5294870A (en) * | 1991-12-30 | 1994-03-15 | Eastman Kodak Company | Organic electroluminescent multicolor image display device |
-
1993
- 1993-07-12 DE DE69305262T patent/DE69305262T2/de not_active Expired - Lifetime
- 1993-07-12 JP JP17155293A patent/JP3445315B2/ja not_active Expired - Lifetime
- 1993-07-12 EP EP93111129A patent/EP0579151B1/en not_active Expired - Lifetime
-
1994
- 1994-02-14 US US08/195,805 patent/US5484922A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3149991B2 (ja) | 1991-08-01 | 2001-03-26 | イーストマン コダック カンパニー | ブルー放出性発光組成物 |
| JP3213063B2 (ja) | 1991-08-01 | 2001-09-25 | イーストマン コダック カンパニー | 内部接合形有機エレクトロルミネセント素子 |
| JP3215510B2 (ja) | 1991-08-01 | 2001-10-09 | イーストマン コダック カンパニー | 内部接合形有機エレクトロルミネセント素子 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7781072B2 (en) | 2002-03-29 | 2010-08-24 | Pioneer Corporation | Organic electroluminescence device |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0579151A2 (en) | 1994-01-19 |
| DE69305262T2 (de) | 1997-04-30 |
| DE69305262D1 (de) | 1996-11-14 |
| JPH06172751A (ja) | 1994-06-21 |
| US5484922A (en) | 1996-01-16 |
| EP0579151B1 (en) | 1996-10-09 |
| EP0579151A3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1994-02-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3445315B2 (ja) | アルミニウムキレート化合物及び内部接合型有機電界発光素子 | |
| JP4247764B2 (ja) | インドロカルバゾールを用いたエレクトロルミネセントデバイス | |
| EP0534510B1 (en) | Improved blue emitting internal junction organic electroluminescent device | |
| EP0525904B1 (en) | Mixed ligand aluminum chelate luminophors | |
| JP4243876B2 (ja) | エレクトロルミネセントデバイス | |
| US6057048A (en) | Electroluminescent (EL) devices | |
| US6562485B2 (en) | Electroluminescent (EL) devices | |
| KR100687666B1 (ko) | 전계발광 재료, 전계발광 소자 및 색전환 필터 | |
| KR101338343B1 (ko) | 유기 전계발광 소자 재료 및 유기 전계발광 소자 | |
| JP2000208265A (ja) | 発光素子 | |
| KR20040106236A (ko) | 유기 전계 발광재료, 유기 전계 발광소자 및 함복소환이리듐 착체 화합물 | |
| JP2003151773A (ja) | 発光素子 | |
| JP4710268B2 (ja) | ピロメテン化合物、それを用いた発光素子材料ならびに発光素子 | |
| JP4524901B2 (ja) | 発光素子 | |
| JP3490879B2 (ja) | 有機エレクトロルミネッセンス素子 | |
| JP4061969B2 (ja) | 発光素子 | |
| JP4308560B2 (ja) | 有機金属錯体、その配位子、および有機ｅｌ素子 | |
| JP2000208273A (ja) | 発光素子 | |
| KR100564918B1 (ko) | 아릴피리딘-이리듐 금속 착체화합물을 사용한 유기 전계발광 소자 | |
| JP4076709B2 (ja) | 発光素子材料、スチリルアミン化合物およびそれを使用した発光素子 | |
| JP2000208267A (ja) | 発光素子 | |
| KR20050005084A (ko) | 유기 전계 발광 소자용 녹색 발광 화합물, 이의 제조방법및 이를 사용한 유기 전계 발광 소자 | |
| JPH11288784A (ja) | 発光素子 | |
| JP2000123972A (ja) | 発光素子 | |
| JP2000208268A (ja) | 発光素子 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080627 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090627 Year of fee payment: 6 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090627 Year of fee payment: 6 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100627 Year of fee payment: 7 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100627 Year of fee payment: 7 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110627 Year of fee payment: 8 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110627 Year of fee payment: 8 |
|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110627 Year of fee payment: 8 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110627 Year of fee payment: 8 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120627 Year of fee payment: 9 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120627 Year of fee payment: 9 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130627 Year of fee payment: 10 |
|
| EXPY | Cancellation because of completion of term |