JP5661282B2 - Oled用途のためのランタノイドエミッター - Google Patents
Oled用途のためのランタノイドエミッター Download PDFInfo
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- JP5661282B2 JP5661282B2 JP2009531780A JP2009531780A JP5661282B2 JP 5661282 B2 JP5661282 B2 JP 5661282B2 JP 2009531780 A JP2009531780 A JP 2009531780A JP 2009531780 A JP2009531780 A JP 2009531780A JP 5661282 B2 JP5661282 B2 JP 5661282B2
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- 229910052747 lanthanoid Inorganic materials 0.000 title claims description 7
- 150000002602 lanthanoids Chemical class 0.000 title claims description 5
- 239000011159 matrix material Substances 0.000 claims description 32
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000001425 triazolyl group Chemical group 0.000 claims description 12
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000003368 amide group Chemical group 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims description 7
- 229940031826 phenolate Drugs 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 230000000903 blocking effect Effects 0.000 claims description 6
- 239000011521 glass Substances 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000002061 vacuum sublimation Methods 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 239000010410 layer Substances 0.000 description 96
- 239000000463 material Substances 0.000 description 35
- 150000001875 compounds Chemical class 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 125000004429 atom Chemical group 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 230000008901 benefit Effects 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- BYSUYBCCLCSGPR-UHFFFAOYSA-N 1h-pyrazol-5-yloxyboronic acid Chemical compound OB(O)OC1=CC=NN1 BYSUYBCCLCSGPR-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound 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 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 150000002601 lanthanoid compounds Chemical class 0.000 description 4
- 230000007774 longterm Effects 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000000295 emission spectrum Methods 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- -1 lanthanoid cation Chemical class 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000012780 transparent material Substances 0.000 description 3
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- KJDWHOKNQFHFCC-UHFFFAOYSA-N 2h-triazol-4-yloxyboronic acid Chemical compound OB(O)OC=1C=NNN=1 KJDWHOKNQFHFCC-UHFFFAOYSA-N 0.000 description 2
- YYONJAQDTXLPIG-UHFFFAOYSA-N 4-(4-amino-1-methylcyclohexa-2,4-dien-1-yl)aniline Chemical compound CC1(CC=C(C=C1)N)C1=CC=C(C=C1)N YYONJAQDTXLPIG-UHFFFAOYSA-N 0.000 description 2
- 229910052684 Cerium Inorganic materials 0.000 description 2
- 229910052688 Gadolinium Inorganic materials 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000003086 colorant Substances 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
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound 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
- 239000002798 polar solvent Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 150000003852 triazoles Chemical group 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CDQOABYRNMVQRK-UHFFFAOYSA-N CC(C=CC1=CC=C2)(C(O)=O)NC1=C2O.OC(C=C1)=CC=C1C1=CC=CC=C1 Chemical compound CC(C=CC1=CC=C2)(C(O)=O)NC1=C2O.OC(C=C1)=CC=C1C1=CC=CC=C1 CDQOABYRNMVQRK-UHFFFAOYSA-N 0.000 description 1
- 229910000882 Ca alloy Inorganic materials 0.000 description 1
- 0 Cc1c(*)c(*)n[n]1C(B*)(*)C* Chemical compound Cc1c(*)c(*)n[n]1C(B*)(*)C* 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- XQTIWNLDFPPCIU-UHFFFAOYSA-N cerium(3+) Chemical compound [Ce+3] XQTIWNLDFPPCIU-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 238000012993 chemical processing Methods 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000011532 electronic conductor Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005283 ground state Effects 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
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- HKCRVXUAKWXBLE-UHFFFAOYSA-N terbium(3+) Chemical compound [Tb+3] HKCRVXUAKWXBLE-UHFFFAOYSA-N 0.000 description 1
- MJYTZAQGBQAGAG-UHFFFAOYSA-N tris(triazol-1-yl) borate Chemical compound C1=CN=NN1OB(ON1N=NC=C1)ON1C=CN=N1 MJYTZAQGBQAGAG-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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- 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]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- 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
- 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
- H10K85/351—Metal complexes comprising lanthanides or actinides, e.g. comprising europium
-
- 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
- H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- 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
- C09K2211/182—Metal complexes of the rare earth metals, i.e. Sc, Y or lanthanide
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- 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
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- 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
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- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
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- 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
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Inorganic Chemistry (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- High Energy & Nuclear Physics (AREA)
- Electroluminescent Light Sources (AREA)
Description
Ln=Ce3+、Ce4+、Pr3+、Pr4+、Nd3+、Nd4+、Pm3+、Sm3+、Eu3+、Eu2+、Gd3+、Tb3+、Tb4+、Dy3+、Dy4+、Ho3+、Er3+、Tm3+、Tm2+、Yb3+、Yb2+若しくはLu3+であり、
R1=置換されても、非置換でもよいピラゾリル、トリアゾリル、ヘテロアリール、アルキル、アリール、アルコキシ、フェノラート、アミン若しくはアミド基又は
R5=R1若しくはH、及び
R2、R3、R4、R6、R7=H、ハロゲン若しくは随意にヘテロ原子を含んでもよい炭化水素基、特に、アルキル、アリール若しくはヘテロアリールである。化合物の揮発性を増加するために、基R2−R7は、フッ素化されてよい。
・高い熱安定性、
・高い長期的安定性、
・酸素及び水に対する良好な化学的安定性、
・極性溶媒での良好な溶解性と、それゆえの種々のポリマーマトリックス材料でのドープのための高度の適合性(エミッター層への良好な組み込み)、
・スピンコートプロセス、印刷プロセス及びインクジェット印刷プロセスによる簡単な適用、
・前記プロセスのための種々の溶媒の広範な選択、それゆえの下に在る層の溶解発生の回避、
・種々のランタノイドイオンの均衡した混合物の使用による白色発光色の簡単な達成、
・顕著な製造上の利点、
・極度に短い発光減衰時間(約60ns)を有するCe錯体の青色発光。こうして、高い電流密度を使用することができる。
・ユウロピウム(III)テトラキス(ピラゾリル)ボラート、
・テルビウム(III)テトラキス(ピラゾリル)ボラート、及び
・ネオジミウム(III)テトラキス(ピラゾリル)ボラート。
好ましくは、ETLと陰極との間に適用される。この中間層は、電子注入バリヤを減少し、ETLを保護する。この層は、一般的に蒸着により適用される。中間層は、好ましくは、非常に薄く、特に、0.5〜2nm、より好ましくは、0.8〜1.0nmの厚さである。最後に、電導性陰極層は、蒸着により適用され、特に、50〜500nm、より好ましくは、100〜250nmの厚さを有する。陰極層は、好ましくは、Al、Mg/Ag(特に、10:1の比で)若しくは他の金属から成る。3〜15Vの電圧が、好ましくは、本発明による昇華可能なエミッターのために記載されるOLED構造に適用される
したがって、本発明は、さらに、式(I)若しくは(II)の錯体を含む正孔障ブロックに関する。
Ln=Ce3+若しくはGd3+、
R1=置換されても、非置換でもよいピラゾリル、トリアゾリル、ヘテロアリール、アルキル、アリール、アルコキシ、フェノラート、アミン若しくはアミド基又は
R5=R1若しくはH及び
R2、R3、R4、R6、R7=H、ハロゲン若しくはヘテロ原子を含んでもよく又は/及び置換されてもよい炭化水素基である。
Ln=Ce3+若しくはGd3+、
R1=置換されても、非置換でもよいピラゾリル、トリアゾリル、ヘテロアリール、アルキル、アリール、アルコキシ、フェノラート、アミン若しくはアミド基又は
R5=R1若しくはH及び
R2、R3、R4、R6、R7=H、ハロゲン若しくはヘテロ原子を含んでもよく又は/及び置換されてもよい炭化水素基である。
(i)少なくとも一つの式(I)若しくは(II)の錯体を含むマトリックス材料、
Ln=Gd3+、
R1=置換されても、非置換でもよいピラゾリル、トリアゾリル、ヘテロアリール、アルキル、アリール、アルコキシ、フェノラート、アミン若しくはアミド基又は
R5=R1若しくはH及び
R2、R3、R4、R6、R7=H、ハロゲン若しくはヘテロ原子を含んでもよく又は/及び置換されてもよい炭化水素基。)及び
(ii)エミッターとして、少なくとも一つの式(I)若しくは(II)の錯体
Ln=Ce3+、
R1=置換されても、非置換でもよいピラゾリル、トリアゾリル、ヘテロアリール、アルキル、アリール、アルコキシ、フェノラート、アミン若しくはアミド基又は
R5=R1若しくはH及び
R2、R3、R4、R6、R7=H、ハロゲン若しくはヘテロ原子を含んでもよく又は/及び置換されてもよい炭化水素基。)
を含む、エミッター層、特に、発光素子のためのエミッター層に関する。
カリウム テトラキス(ピラゾリル)ボラートは、Acrosから入手可能であり、カリウム ヒドロ[トリス(トリアゾリル)]ボラートとカリウム テトラキス(トリアゾリル)ボラートは、KBH4とトリアゾールから調製され、式(I)及び式(II)にしたがうボラート誘導体配位子は、種々の合成戦略によって、得ることができる。
Claims (26)
- 更に、正孔伝導層又は/及び電子伝導層を含むことを特徴とする、請求項1記載の発光素子。
- 更に、CsF若しくはLiF中間層を含むことを特徴とする、請求項1又は2記載の発光素子。
- 基板上、特に、ガラス基板上に配置されることを特徴とする、請求項1〜3何れか1項記載の発光素子。
- エミッター層中に存在する錯体が、ランタノイドエミッターであることを特徴とする、請求項1〜4何れか1項記載の発光素子。
- R2、R3、R4、R6及びR7は、夫々、互いに独立して、水素若しくはハロゲンを表すことを特徴とする、請求項1〜5何れか1項記載の発光素子。
- エミッター層が、エミッター層の合計重量を基礎として、1〜100重量%の濃度で、式(I)又は/及び(II)の錯体を含むことを特徴とする、請求項1〜6何れか1項記載の発光素子。
- エミッター層中の式(I)又は/及び(II)の錯体の割合は、エミッター層の合計重量を基礎として、80重量%より大であることを特徴とする、請求項1〜7何れか1項記載の発光素子。
- エミッター層中の式(I)又は/及び(II)の錯体の割合は、エミッター層の合計重量を基礎として、10重量%より大であり、80重量%までであることを特徴とする、請求項1〜8何れか1項記載の発光素子。
- エミッター層中の式(I)又は/及び(II)の錯体の割合は、エミッター層の合計重量を基礎として、2重量%より大であり、10重量%までであることを特徴とする、請求項1〜7何れか1項記載の発光素子。
- エミッター層中の式(I)若しくは(II)の錯体は、モノマーの形態であることを特徴とする、請求項10記載の発光素子。
- 式(I)若しくは(II)の錯体を含む結晶性又は/及び準結晶性層を有することを特徴とする、請求項1〜11何れか1項記載の発光素子。
- 表示素子及び/又は照明素子であることを特徴とする、請求項1〜12何れか1項記載の発光素子。
- 請求項1で定義されるとおりの式(I)若しくは(II)の錯体の、発光素子でのエミッターとしての使用。
- Ln=Ce3+である式(I)若しくは(II)の錯体の、短い発光減衰時間を有する蛍光エミッターとしての、請求項14記載の使用。
- 少なくとも一つの式(I)若しくは(II)の錯体が、真空昇華によりエミッター層中に導入されることを特徴とする、請求項1〜13何れか1項記載の発光素子の製造方法。
- 少なくとも一つの式(I)若しくは(II)の錯体が、湿式化学法によりエミッター層中に導入されることを特徴とする、請求項1〜13何れか1項記載の発光素子の製造方法。
- 白色光生成のための、同じエミッター層中での、2或いは3以上の異なる請求項1で定義されるとおりの式(I)若しくは(II)のエミッター錯体の使用。
- 青色発光OLEDの製造のための請求項1で定義されるとおりの式(I)若しくは(II)のCe(III)錯体の使用。
- 赤外発光OLEDの製造のための請求項1で定義されるとおりの式(I)若しくは(II)のNd(III)錯体の使用。
- 高い電流密度で低損失でそれゆえまた高効率でOLEDを駆動することができるように、非常に短い発光減衰時間を有する請求項1で定義されるとおりの式(I)若しくは(II)のCe(III)錯体の使用。
- エミッター錯体でドープされた、請求項23記載のマトリックス材料。
- (i)少なくとも一つの式(I)若しくは(II)の錯体を含むマトリックス材料、
Ln=Ce3+若しくはGd3+、R1=置換されても、非置換でもよいピラゾリル、トリアゾリル及びヘテロアリール基又は
R5=R1及び
R2、R3、R4、R6、R7=H、ハロゲン若しくはヘテロ原子を含んでもよく又は/及び置換されてもよい炭化水素基。)及び
(ii)エミッターとして、少なくとも一つの式(I)若しくは(II)の錯体
Ln=Ce3+若しくはGd3+、R1=置換されても、非置換でもよいピラゾリル、トリアゾリル及びヘテロアリール基又は
R5=R1及び
R2、R3、R4、R6、R7=H、ハロゲン若しくはヘテロ原子を含んでもよく又は/及び置換されてもよい炭化水素基。)
を含む、特に、発光素子のためのエミッター層、
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DE102006048202A DE102006048202A1 (de) | 2006-10-11 | 2006-10-11 | Lanthanoid-Emitter für OLED-Anwendungen |
DE102006048202.6 | 2006-10-11 | ||
PCT/EP2007/008856 WO2008043562A1 (de) | 2006-10-11 | 2007-10-11 | Lanthanoid-emitter für oled-anwendungen |
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GB0423506D0 (en) * | 2004-10-22 | 2004-11-24 | Univ Belfast | Light emitting complex salts |
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WO2013079676A1 (en) | 2011-11-30 | 2013-06-06 | Novaled Ag | Organic electronic device |
DE102011089687A1 (de) | 2011-12-22 | 2013-06-27 | Hartmut Yersin | Singulett-Harvesting mit speziellen organischen Molekülen ohne Metallzentren für opto-elektronische Vorrichtungen |
CN102867921B (zh) * | 2012-09-13 | 2015-11-25 | 深圳市华星光电技术有限公司 | 有机显示装置 |
CN103247666A (zh) * | 2013-04-25 | 2013-08-14 | 深圳市华星光电技术有限公司 | 一种红外oled显示装置及其制造方法 |
RU2663671C2 (ru) * | 2017-01-11 | 2018-08-08 | Сиа Эволед | Пиразолкарбоксилаты лантанидов, проявляющие люминесцентные свойства в видимом диапазоне |
DE102020103268B8 (de) * | 2020-02-10 | 2023-04-20 | Sichuan Knowledge Express Institute For Innovative Technologies Co., Ltd. | Ce(III)-Komplexe, Zusammensetzung aufweisend Ce(III)-Komplexe, optoelektronische Vorrichtung, Verfahren zu deren Herstellung, Verfahren zum Dublett-Harvesting und Verfahren für Hyperfluoreszenz mit sehr kurzer Abklingzeit |
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US5128587A (en) * | 1989-12-26 | 1992-07-07 | Moltech Corporation | Electroluminescent device based on organometallic membrane |
US6358631B1 (en) * | 1994-12-13 | 2002-03-19 | The Trustees Of Princeton University | Mixed vapor deposited films for electroluminescent devices |
GB9711237D0 (en) * | 1997-06-02 | 1997-07-23 | Isis Innovation | Organomettallic Complexes |
US6392250B1 (en) * | 2000-06-30 | 2002-05-21 | Xerox Corporation | Organic light emitting devices having improved performance |
TWI243197B (en) * | 2001-03-08 | 2005-11-11 | Univ Hong Kong | Organometallic light-emitting material |
KR100888424B1 (ko) * | 2001-05-16 | 2009-03-11 | 더 트러스티즈 오브 프린스턴 유니버시티 | 고효율 다칼라 전기 유기 발광 장치 |
US20030020397A1 (en) * | 2001-06-28 | 2003-01-30 | Lite Array Inc. | Enhancement of luminance and life in electroluminescent devices |
EP1426399A4 (en) * | 2001-09-04 | 2005-07-13 | Canon Kk | HIGHLY MOLECULAR COMPOUNDS AND ORGANIC LUMINESCENT DEVICES |
GB0202997D0 (en) * | 2002-02-08 | 2002-03-27 | Elam T Ltd | Method for forming electroluminescent devices |
US6653654B1 (en) * | 2002-05-01 | 2003-11-25 | The University Of Hong Kong | Electroluminescent materials |
EP1578886A2 (en) * | 2002-12-24 | 2005-09-28 | Elam-T Limited | Electroluminescent materials and devices |
DE10338550A1 (de) * | 2003-08-19 | 2005-03-31 | Basf Ag | Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs) |
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DE10358665A1 (de) * | 2003-12-12 | 2005-07-07 | Basf Ag | Verwendung von Platin(II)-Komplexen als lumineszierende Materialien in organischen Licht-emittierenden Dioden (OLEDs) |
DE102004018145A1 (de) * | 2004-04-08 | 2005-10-27 | Basf Ag | Verwendung von Metallocenkomplexen von Metallen der 4. Nebengruppe des Periodensystems als Triplettemitter in organischen Leuchtdioden (OLEDs) |
US7393599B2 (en) * | 2004-05-18 | 2008-07-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
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