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WO2004026989A1 - Melanges luminescents - Google Patents

Melanges luminescents Download PDF

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WO2004026989A1
WO2004026989A1 PCT/EP2003/008190 EP0308190W WO2004026989A1 WO 2004026989 A1 WO2004026989 A1 WO 2004026989A1 EP 0308190 W EP0308190 W EP 0308190W WO 2004026989 A1 WO2004026989 A1 WO 2004026989A1
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compounds
heavy metal
group
luminescent
metals
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English (en)
Inventor
Thomas Gessner
Yvonne Heischkel
Reinhold Schwalm
Günther Seybold
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BASF SE
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BASF SE
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    • 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
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    • 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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    • 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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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • 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
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    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
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    • 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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    • 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
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    • 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
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    • 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
    • H10K85/114—Poly-phenylenevinylene; Derivatives thereof
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    • 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
    • H10K85/115—Polyfluorene; Derivatives thereof
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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    • 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
    • H10K85/348—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising osmium
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom

Definitions

  • the present invention relates to new luminescent mixtures containing at least one organic polymer selected from the group consisting of polyfluorene compounds (A), poly (p-phenylene vinylene) compounds (B), poly (p-phenylene) compounds
  • LEDs are well known and e.g. in Angew. Chem. 1998, 110, 25 416-443. They are applicable in many areas, e.g. in monochrome, multicolor or full-color screens (for example in applications in automobiles, mobile phones or notebooks).
  • WO 01/96454 describes photoluminescent and electroluminescent compositions with an aromatic matrix and 40 luminescent metal ions or luminescent metal complexes.
  • the object of the present invention was to provide new mixtures which are advantageously suitable for the production of organic LEDs. 45 Accordingly, the mixtures identified at the outset were found.
  • the luminescent mixtures according to the invention contain at least one organic, preferably electroluminescent, organic polymer selected from the group consisting of polyfluorene compounds (A), poly (p-phenylene vinylene) compounds (B), poly (p-phenylene) compounds (C) and Polythiophene compounds (D).
  • organic polymer selected from the group consisting of polyfluorene compounds (A), poly (p-phenylene vinylene) compounds (B), poly (p-phenylene) compounds (C) and Polythiophene compounds (D).
  • the organic polymers contained in the mixtures according to the invention generally have an average molecular weight of 10 3 to 10 7 g / mol, based on polystyrene standards, determined by gel permeation chromatography.
  • Ar ic 6 -C 2 o-arylene preferably C ⁇ -Cio-arylene, CC 2 o _ heteroarylene, preferably C 4 -C ⁇ n-heteroarylene, or a divalent radical of a triarylamine having 18 to 60, preferably 18 to 30 carbon atoms, which is linked via carbon-carbon bonds.
  • R 1 and R 2 are each independently of one another C 1 -C 3 -alkyl, which can be interrupted by one or more oxygen or sulfur atoms or by one or more imino or C 1 -C 4 -alkylimino groups, or C 2 -Ci 3 -Alko y, and
  • n and n each represent 0 to 1, with the proviso that the sum of m and n is 1;
  • a 1 and A 2 are each independently hydrogen or cyano
  • Ar 2 Cg-C 2 o ⁇ ar len, preferably C ⁇ -C IO arylene, C 4 -C 2 o heteroarylene, preferably C 4 -C ⁇ o heteroarylene, or a divalent radical of a triarylamine with 18 to 60, preferably 18 to 30 carbon atoms which are linked via carbon-carbon bonds,
  • R 3 and R 4 are each independently of one another C 1 -C 3 -alkyl, which can be interrupted by one or more oxygen or sulfur atoms or by one or more imino or C 1 -C 4 -alkylimino groups, C ⁇ -Ci 3 -alkoxy , i-Cig-Acyl or Tri (C-C ⁇ 6 -alkyl) siloxy, and
  • p and g each represent 0 to 1, with the proviso that the sum of p and q is 1;
  • Ar 3 Cg-C 2 o-arylene, preferably C ß -Cio-arylene, C 4 -C 2 o-heteroarylene, preferably C 4 -C ⁇ o-heteroarylene or a divalent radical of a triarylamine with 18 to 60, preferably 18 to 30 carbon atoms linked by carbon-carbon bonds
  • R 5 and R 6 are each independently of one another C 1 -C 3 -alkyl which can be interrupted by one or more oxygen or sulfur atoms or by one or more imino or C 1 -C 4 -alkylimino groups, C 1 -C 3 - Alkoxy, C 4 -C 6 -acyl or tri (Cj-Ci ß- alkyl) siloxy, and
  • r and s each represent 0 to 1, with the proviso that the sum of r and s is 1;
  • Ar 4 is C 6 -C 20 -A ylene, preferably C ö -Cio-arylene, CC 2 o-heteroarylene, C 4 -C ⁇ o heteroarylene, or a divalent radical of a triarylamine preferably 18 to 60, preferably 18 to 30 Carbon atoms linked by carbon-carbon bonds,
  • R 7 and R 8 are each independently of the other C ⁇ -Ci 3 alkyl, which can be interrupted by one or more oxygen or sulfur atoms or by one or more imino or C 1 -C 4 alkylimino groups, C 1 -C 3 alkoxy , C-C ⁇ 6 -acyl or tri (C 4 -C ⁇ 6 -alkyl) siloxy, and
  • t and u ' each represent 0 to 1, with the proviso that the sum of t and u is 1.
  • Important organic polymers are, for example, polyfluorene compounds (A) which have structural elements of the formula I, poly (p-phenylene vinylene) compounds (B) which have structural elements of the formula II, poly (p-phenylene) compounds (C), the structural elements of Have formula III, and polythiophene compounds (D) which have structural elements of formula IV.
  • the polymers of the formula I, II, III and IV can be both homopolymers and copolymers.
  • Organic polymers which are selected from the group consisting of polyfluorene compounds (A), in particular those which have structural elements of the formula I, and poly- (p-phenylene vinylene) compounds (B), in particular those which have structural elements of the formula II, are preferred have, with poly (p-phenylene-vinylene) compounds (B), in particular those which have structural elements of the formula II, to be particularly emphasized.
  • Organic polymers which may be mentioned are, in particular, homopolymers which have structural elements of the formula I in which R 1 and R 2 are each, independently of one another, C 1 -C 6 -alkyl, in particular butyl, hexyl or 2-ethylhexyl, and the copolymers analogous thereto Formula I in which Ar 1 is a divalent radical of a triphenylamine, a thiophene or a carbazole, and homopolymers of the formula II in which R 3 and R 4 in each case Ci-Cs-alkoxy, in particular methoxy and 2-ethylhexyloxy, or Tri (Ci-Cs-alkyl) - silyl mean, as well as the copolymers of analog
  • Ar 2 is a divalent residue of a triphenylamine, a thiophene or a carbazole.
  • the organic polymers used generally have an electrical conductivity of at least 10 ⁇ 9 S / cm, preferably at least 10 ⁇ 7 S / cm and in particular at least 10 ⁇ 6 S / cm.
  • the luminescent mixtures according to the invention can also have mixtures of the organic polymers described in more detail above with one another.
  • the organic polymers contained in the luminescent mixtures according to the invention are generally compounds known per se, such as those e.g. in Adv. Mater, 2000, 12, 1737, and Angew. Chem., 1998, 110, 416-443.
  • the luminescent mixtures according to the invention further contain at least one heavy metal compound with a heavy metal whose atomic weight is at least 50, preferably at least 63.
  • the heavy metal is selected from the group consisting of the 1st to 3rd row of transition metals, the metals of the 3rd, 4th and 5th main group of the 5th and 6th period of the periodic table Elements and the lanthanides, with the exception of platinum compounds.
  • the heavy metal is selected from the group consisting of copper, zinc and the metals of the 3rd, 4th and 5th main group of the 6th period of the Periodic Table of the Elements.
  • preferred heavy metals are those selected from the group consisting of the lanthanides, copper, rhenium, osmium, iridium, gold, thallium, lead and bismuth, with europium, terbium, copper, rhenium, iridium , Gold, lead and bismuth are particularly noteworthy.
  • preferred heavy metals are those which are selected from the group consisting of copper, zinc, thallium, lead and bismuth, copper, lead and bismuth being particularly mentioned.
  • Organic heavy metal complexes are to be mentioned in particular as heavy metal compounds.
  • Complexing agents for such heavy metal complexes are preferably derived from compounds which are selected from the group consisting of 2, 2 '-bipyridyl, 1, 10-phenanthroline, 2-pyridinecarboxylate (pic), 2-carbaldehydimino-phenolate (sal) and from 1,3-dicarbonyl compounds, especially those of formula V
  • T 1 , T 2 and T 3 are each independently of one another C 1 -C 3 -alkyl
  • complexing agents are selected from the group consisting of 2-phenylpyridine (ppy), 2- (4-tolyl) pyridine (tpy), 1-phenanthridine (bzq), 2- (2-thienyl) pyridine (thp), 2- (2-benzo [b] thiophenyl) pyridine (btp), 2, 5-diphenyloxazole (dpo), 2- (2-oxo-7-diethylamino-3-benzo [b] pyranyl) benzothiazole (C6) , 2-phenylbenzoxazole (bo), 2-phenylbenzthiazole (bt), 2- (l-naphthyl) benzoxazole (bon), 2-phenyl-4,5-dihydrooxazole (op), 2- (l-naphthyl) benzothiazole ( ⁇ bsn), 2- (2-naphthyl) benzthiazole (ßbsn), 2- (2-thienyl) benzothiazo
  • E i to E 8 each independently of one another are hydrogen, C 1 -C 3 -alkyl, C 6 -Ci 2 -aryl or C 4 ⁇ -CC-heteroaryl,
  • E 9 and Ei ° independently of one another are each C 1 -C 3 alkyl, C 6 -C 2 aryl, C 4 -C 4o heteroaryl, Cx-Cis-alkoxy, halogen, cyano or thiocyanato,
  • EU and E i2 independently of one another each C 1 -C 3 -alkyl, C 6 -Ci 2 ⁇ aryl or C 4 -C ⁇ o-heteroaryl,
  • E x3 , E X4 and E X5 independently of one another are each C 1 -C 3 -alkyl
  • L l is a bidentate ligand, in particular 2,2'-bipyridy1 or 1,10-phenanthro1in,
  • M is a heavy metal defined in more detail above,
  • X and Y each independently of one another oxygen, sulfur imino, -CC-alkylimino or C 6 -C 12 arylamino,
  • w is 1 to 3.
  • complex ligands and metal complexes are known per se and, for example, in J. Am. Chem. Soc. 123, 2001, 4304-4312, Inorg. Che. 40, 2001, 1704-1712, Adv. Mater. 2000, 12, 1591-1594, Adv. Mater. 2001, 13, 1245, WO 99/53724, WO 00/57676, WO 01/08230, WO 01/39234 and WO 01/41512.
  • alkyl radicals are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl , Isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl or isotridecyl.
  • Alkyl radicals which are interrupted by one or more oxygen or sulfur atoms or by one or more imino or C 1 -C 4 -alkylimino groups are, for example, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or 3-propoxypropyl, 2- or 4-methoxybutyl, 2- or 4-ethoxybutyl, 3, 6-dioxaheptyl, 3, 6-dioxaoctyl, 3, 7-dioxaoctyl , 4, 7-dioxaoctyl, 2- or 3-butoxypropyl or 2- or 4-butoxybutyl or the corresponding radicals which have sulfur atoms, imino or, for example, methyl or ethylimino groups instead of the oxygen atoms.
  • Alkoxy residues are e.g. Methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy tert-butyl, pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, hexyloxy, 2-methyloxypentyloxy, heptyloxy, octyloxy, 2-ethyloxyhexyloxy, isooctyloxy, nonyl - oxy, isononyloxy, decyloxy, isodecyloxy, ündecyloxy, dodecyloxy, tridecyloxy or isotridecyloxy.
  • Aryl residues are e.g. Phenyl, 2-, 3- or 4-methylphenyl, 2-, 3- or 4-ethylphenyl, 2, 4-dimethylphenyl, naphthyl or 2-methylnaphthyl.
  • Arylene residues are e.g. Phenylene, 2-, 3- or 4-methylphenylene, 2-, 3- or 4-ethylphenylene, 2,4-dimethylphenylene, naphthylene or 2-methylnaphthylene.
  • Heteroaryl or heteroarylene residues are derived, for example, from the following heterocycles: pyrrole, furan, thiophene, pyridine, pyrimidine, triazine, indole, benzofuran, benzoxazole, benzothiazole, quinoline or isoquinoline.
  • Acyl residues are e.g. Butanoyl, isobutanoyl, sec-butanoyl, pentanoyl, isopentanoyl, neopentanoyl, hexanoyl, 2-methylpentanoyl, heptanoyl, octanoyl, 2-ethylhexanoyl, isooctanoyl, nonanoyl, isononanoyl, decanoyoyl, decanoyoyl, decanoyoyl Pentadecanoyl or Hexadecanoyl.
  • the ligands 2, 2 '-bipyridyl, 1, 10-phenanthroline, 2-phenylpyridine, 2-phenylbenzoxazole (bo) and 1,3-dicarbonyl compounds, in particular those of the formula V, are of particular importance.
  • the luminescent mixtures according to the invention can also have mixtures of the heavy metal compounds specified above.
  • luminescent mixtures comprising at least one heavy metal complex with a heavy metal defined in more detail above and a complexing agent which is derived from an organic compound selected from the group consisting of 2,2'-bipyridyl, 1, 10-phenanthroline, 2- phenylpyridine,
  • ingredients that may be contained in the luminescent mixtures according to the invention are e.g. B. dopants, such as fluorescent dyes, for example the dyes of the formulas XIX and XX mentioned below.
  • the proportion of organic polymers in the luminescent mixtures according to the invention is generally 70 to 99.999% by weight, preferably 85 to 99.99% by weight and especially 95 to '99.9 wt .-%, each based on the total weight of the mixture.
  • the proportion of the heavy metal compounds in the luminescent mixtures according to the invention is generally 0.01 to 30% by weight, preferably 0.1 to 20% by weight and in particular 0.5 to 15% by weight, in each case based on the total weight of the mixture.
  • the proportion of the above-mentioned further constituents in the luminescent mixtures according to the invention is generally 0 to 5.0% by weight, preferably 0 to 2.0% by weight, in each case based on the total weight of the mixture.
  • the luminescent mixtures according to the invention can be obtained in a manner known per se. For example, by customary mixing of the organic polymers with the heavy metal complexes and, if appropriate, with the further constituents described in more detail above.
  • the mixtures according to the invention containing at least one organic polymer and at least one heavy metal complex, are luent. This means that after energetic stimulation e.g. to emit light through light and electricity.
  • Another object of the present invention is the use of the luminescent mixtures according to the invention as organic LEDs.
  • Organic LEDs are generally constructed in such a way that an organic electroluminescent layer containing a thickness of 20 to 200 nm is located between an anode and a cathode.
  • the mixture according to the invention is preferably located between the two electrodes.
  • the mixture according to the invention is particularly preferably located between a hole-transporting layer and an electron-transporting layer.

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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne des mélanges luminescents contenant au moins un polymère organique, choisi dans le groupe formé par des composés de polyfluorène (A), des composés de poly-(p-phénylènevinylène) (B), des composés de poly(p-phénylène) (C) et des composés de polythiophène (D), ainsi qu'au moins un composé de métal lourd contenant, dans le cas de la classe de composé (B), un métal lourd dont le poids atomique s'élève à au moins 50 et qui est choisi dans le groupe formé par la série 1 à 3 des métaux de transition, les métaux des groupes principaux 3, 4 et 5 de la période 5 et 6 du système de classification périodique des éléments et les lanthanides, les composés de platine étant exclus, et, dans le cas de la classe de composé (A), (C) et (D), un métal lourd dont le poids atomique s'élève à au moins 50 et qui est choisi dans le groupe formé par le cuivre, le zinc et les métaux des groupes principaux 3, 4 et 5 de la période 6 du système de classification périodique des éléments, ainsi que l'utilisation de ces mélanges pour produire des diodes électroluminescentes organiques.
PCT/EP2003/008190 2002-08-23 2003-07-25 Melanges luminescents Ceased WO2004026989A1 (fr)

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AU2003253321A AU2003253321A1 (en) 2002-08-23 2003-07-25 Luminescent mixtures

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DE10239549A DE10239549A1 (de) 2002-08-23 2002-08-23 Lumineszente Mischungen
DE10239549.7 2002-08-23

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EP1487029B1 (fr) * 2003-06-13 2011-09-21 Semiconductor Energy Laboratory Co., Ltd. Composition d'injection d'électrons pour un dispositif organique luminescent

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01104659A (ja) * 1987-10-19 1989-04-21 Matsushita Electric Ind Co Ltd 高分子超伝導体組成物
EP1138746A1 (fr) * 2000-03-31 2001-10-04 Sumitomo Chemical Company, Limited Substance fluorescente polymérique, procédé pour sa fabrication, ainsi qu' appareillage à polymères luminescent utilisant ladite substance
WO2001096454A1 (fr) * 2000-06-12 2001-12-20 Maxdem Incorporated Dispositifs et materiaux electroluminescents a matrice polymere
EP1231251A1 (fr) * 2001-02-07 2002-08-14 Agfa-Gevaert Diode inorganique électroluminescente à couche mince

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01104659A (ja) * 1987-10-19 1989-04-21 Matsushita Electric Ind Co Ltd 高分子超伝導体組成物
EP1138746A1 (fr) * 2000-03-31 2001-10-04 Sumitomo Chemical Company, Limited Substance fluorescente polymérique, procédé pour sa fabrication, ainsi qu' appareillage à polymères luminescent utilisant ladite substance
WO2001096454A1 (fr) * 2000-06-12 2001-12-20 Maxdem Incorporated Dispositifs et materiaux electroluminescents a matrice polymere
EP1231251A1 (fr) * 2001-02-07 2002-08-14 Agfa-Gevaert Diode inorganique électroluminescente à couche mince

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 013, no. 326 (C - 620) 24 July 1989 (1989-07-24) *

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