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US5141671A Expired / Lapsed US ⏱️ 0.0 years remaining

Mixed ligand 8-quinolinolato aluminum chelate luminophors

Assignee: Siemens Healthcare Diagnostics GmbH Germany
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Filing: 1991-08-01
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Granted: 1992-08-25
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Expires: 2011-08-01
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Abstract

Abstract A blue-emitting luminescent composition is disclosed comprised of an aluminum chelate containing a phenolato ligand and two R<S>-8-quinolinolato ligands, where R<S> substituents are chosen to block the attachment of more than two substituted 8-quinolinolato ligands to the aluminum atom. The presence of the phenolato ligand shifts emission to the blue region of the spectrum. Emission can be shifted to even shorter blue wavelengths by the incorporation of a pentacarbocyclic aromatic fluorescent dye. <IMAGE>

Inventors

  • 👤 Philip S. Bryan
  • 👤 Frank V. Lovecchio
  • 👤 Steven A. VanSlyke

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 22:12
CPC Classifications
C; C09; C09K; C09K11/00; C09K11/06; C07; C07F; C07F5/00; C07F5/06; C07F5/069; H; H10; H10K; H10K85/00; H10K85/30; H10K85/321; H10K50/00; H10K50/10; H10K50/11

Claims Analysis

Total Claims: 32
Claim 1
Independent Claim 76 words
A blue emitting luminescent composition comprised of an aluminum chelate of the formula: (R.sup.S --Q).sub.2 --Al--O--L where Q in each occurrence represents a substituted 8-quinolinolato ligand, R S represents an 8-quinolinolato ring substituent chosen to block sterically the attachment of more than two substituted 8-quinolinolato ligands to the aluminum atom, and L is a phenyl or aromatic fused-ring moiety which can be substituted with hydrocarbon groups such that L has from 6 to 24 carbon atoms.
Claim 2
Dependent Claim 76 words
A blue emitting luminescent composition comprised of an aluminum chelate of the formula: (R.sup.S --Q).sub.2 --Al--O--L where Q in each occurrence represents a substituted 8-quinolinolato ligand, R S represents an 8-quinolinolato ring substituent chosen to block sterically the attachment of more than two substituted 8-quinolinolato ligands to the aluminum atom, and L is a phenyl or aromatic fused-ring moiety which can be substituted with hydrocarbon groups such that L has from 6 to 24 carbon atoms.
Claim 3
Dependent Claim 23 words
A blue emitting luminescent composition according to claim 1 further characterized in that R S is a 2-position substituent of the 8-quinolinolato ring
Claim 4
Dependent Claim 20 words
A blue emitting luminescent composition according to claim 2 further characterized in that R S is an electron donating substituent.
Claim 5
Dependent Claim 33 words
A blue emitting luminescent composition according to claim 3 further characterized in that R S is chosen from the group consisting of amino, oxy and hydrocarbon groups containing up to 10 carbon atoms.
Claim 6
Dependent Claim 25 words
A blue emitting luminescent composition according to claim 4 further characterized in that R S is a hydrocarbon containing from 1 to 6 carbon atoms.
Claim 7
Dependent Claim 26 words
A blue emitting luminescent composition according to claim 1 further characterized in that the 8-quinololato ring nucleus includes a 4-position ring substituent that is electron donating.
Claim 8
Dependent Claim 32 words
A blue emitting luminescent composition according to claim 6 further characterized in that the 4-position ring substituent is chosen from among amino, oxy and hydrocarbon groups containing up to 10 carbon atoms.
Claim 9
Dependent Claim 36 words
A blue emitting luminescent composition according to claim 1 further characterized in that the 8-quinolinolato ring nucleus includes in at least one of its 5, 6 and 7 ring positions a substituent that is electron accepting.
Claim 10
Dependent Claim 49 words
A blue emitting luminescent composition according to claim 8 further characterized in that each of the 5, 6 and 7 ring position electron accepting substituents is chosen from among electron accepting cyano, halogen, and α-haloalkyl, α-haloalkoxy, amido, sulfonyl, carbonyl, carbonyloxy and oxycarbonyl substituents containing up to 10 carbon atoms.
Claim 11
Dependent Claim 85 words
A blue emitting luminescent composition according to claim 1 further characterized in that the aluminum chelate satisfies the formula: ##STR27## where R 2 represents an electron donating substituent, R 3 and R 4 each independently represent hydrogen or an electron donating substituent, R 5 , R 6 and R 7 each independently represent hydrogen or an electron accepting substituent, and L is a phenyl or aromatic fused-ring moiety which can be substituted with hydrocarbon groups such that L has from 7 to 18 carbon atoms.
Claim 12
Dependent Claim 77 words
A blue emitting luminescent composition according to claim 10 further characterized in that the electron donating substituents are independently chosen from the group consisting of --R', --OR' and --N(R")R', where R' is a hydrocarbon containing up to 6 carbon atoms and R" is hydrogen or R' and the electron accepting substituents are each independently chosen from among electron accepting cyano, halogen, and α-haloalkyl, α-haloalkoxy, amido, sulfonyl, carbonyl, carbonyloxy and oxycarbonyl substituents containing up to 6 carbon atoms.
Claim 13
Dependent Claim 25 words
A blue emitting luminescent composition according to claim 1 further characterized in that the hydrocarbon includes at least one aliphatic substituent of the phenyl moiety.
Claim 14
Dependent Claim 23 words
A blue emitting luminescent composition according to claim 12 further characterized in that the aliphatic substituent contains from 1 to 10 carbon atoms.
Claim 15
Dependent Claim 25 words
A blue emitting luminescent composition according to claim 13 further characterized in that the hydrocarbon includes at least one alkyl substituent of the phenyl moiety.
Claim 16
Dependent Claim 25 words
A blue emitting luminescent composition according to claim 13 further characterized in that the hydrocarbon includes at least two alkyl substituents of the phenyl moiety.
Claim 17
Dependent Claim 23 words
A blue emitting luminescent composition according to claim 14 further characterized in that the aliphatic substituent contains from 1 to 3 carbon atoms.
Claim 18
Dependent Claim 28 words
A blue emitting luminescent composition An internal junction organic electroluminescent device according to claim 1 further characterized in that a benzo ring is fused with the phenyl moiety.
Claim 19
Dependent Claim 25 words
A blue emitting luminescent composition according to claim 1 further characterized in that the hydrocarbon includes at least one aromatic substituent of the phenyl moiety.
Claim 20
Dependent Claim 22 words
A blue emitting luminescent composition according to claim 18 further characterized in that the aromatic substituent is comprised of a phenyl ring.
Claim 21
Dependent Claim 107 words
A blue emitting luminescent composition according to claim 1 further characterized in that the aluminum chelate satisfies the formula: ##STR28## where Q in each occurrence represents a substituted 8-quinolinolato ring nucleus, R 2 in each occurrence represents a 2-position electron donating substituent of the 8-quinolinolato ring nucleus, and L 1 , L 2 , L 3 , L 4 and L 5 collectively contain 12 or fewer carbon atoms and each independently represent hydrogen or hydrocarbon groups of from 1 to 12 carbon atoms, with the proviso that L 1 and L 2 together or L 2 and L 3 together can form a fused benzo ring.
Claim 22
Dependent Claim 20 words
A blue emitting luminescent composition according to claim 1 further characterized in that the luminescent layer additionally includes a fluorescent
Claim 23
Dependent Claim 32 words
A blue emitting luminescent composition according to claim 21 further characterized in that the fluorescent dye is chosen to provide a favored recombination site for holes and electrons and is blue emitting.
Claim 24
Dependent Claim 28 words
A blue emitting luminescent composition according to claim 22 further characterized in that the blue emitting fluorescent dye exhibits a shorter wavelength emission peak than the aluminum chelate.
Claim 25
Dependent Claim 32 words
A blue emitting luminescent composition according to claim 22 further characterized in that the blue emitting fluorescent dye contains a stabilizing aromatic chromophoric unit containing at least 5 fused carbocyclic aromatic rings.
Claim 26
Dependent Claim 24 words
A blue emitting luminescent composition according to claim 24 further characterized in that the chromophoric unit contains from 20 to 40 ring carbon atoms.
Claim 27
Dependent Claim 36 words
A blue emitting luminescent composition according to claim 25 further characterized in that the fluorescent dye chromophoric unit is chosen from among those containing a perylene, benzopyrene, benzochrysene, benzonaphthacene, picene, pentaphene, pentacene, hexacene or anthanthrene nucleus.
Claim 28
Dependent Claim 28 words
A blue emitting luminescent composition according to claim 24 further characterized in that the fluorescent dye is present in a concentration ranging from 0.05 to 5 mole percent.
Claim 29
Dependent Claim 28 words
A blue emitting luminescent composition according to claim 27 further characterized in that the fluorescent dye is present in a concentration ranging from 0.2 to 3 mole percent.
Claim 30
Dependent Claim 28 words
A blue emitting luminescent composition according to claim 27 further characterized in that the fluorescent dye is present in a concentration ranging from 0.5 to 2 mole percent.
Claim 31
Dependent Claim 40 words
A blue emitting luminescent composition comprised of an aluminum chelate chosen from the group consisting of bis(2-methyl-8-quinolinato)(phenolato)-aluminum(III); bis(2-methyl-8-quinolinato)(ortho-cresolato)-aluminumn(III); bis(2-methyl-8-quinolinato)(meta-cresolato)-aluminum(III); bis(2-methyl-8-quinolinato)(para-cresolato)-aluminum(III); bis(2-methyl-8-quinolinato)(ortho-phenylphenolato)-aluminum(III); bis(2-methyl-8-quinolinato)(meta-phenylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(para-phenylphenolato)-aluminum(III); bis(2-methyl-8-quinolinato)(2,3-dimethylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(2,6-dimethylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(3,4-dimethylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(3,5-dimethylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(3,5-di-tert.-butylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(2,6-diphenylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(2,4,6-tri-phenylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(2,3,6-tri-methylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(2,3,5,6-tetramethylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum(III); bis(2-methyl-8-quinolinato)(2-naphtholato)aluminum(III); bis(2,4-dimethyl-8-quinolinato)(ortho-phenylphenolato)aluminum(III); bis(2,4-dimethyl-8-quinolinato)(para-phenylphenolato)aluminum(III); bis(2,4-dimethyl-8-quinolinato)(meta-phenylphenolato)aluminum(III); bis(2,4-dimethyl-8-quinolinato)(3,5-dimethylphenolato)aluminum(III); and bis(2,4-dimethyl-8-quinolinato)(3,5-di-tert-butylphenolato)aluminum(III).
Claim 32
Dependent Claim 40 words
A blue emitting luminescent composition comprised of an aluminum chelate chosen from the group consisting of bis(2-methyl-8-quinolinato)(phenolato)-aluminum(III); bis(2-methyl-8-quinolinato)(ortho-cresolato)-aluminumn(III); bis(2-methyl-8-quinolinato)(meta-cresolato)-aluminum(III); bis(2-methyl-8-quinolinato)(para-cresolato)-aluminum(III); bis(2-methyl-8-quinolinato)(ortho-phenylphenolato)-aluminum(III); bis(2-methyl-8-quinolinato)(meta-phenylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(para-phenylphenolato)-aluminum(III); bis(2-methyl-8-quinolinato)(2,3-dimethylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(2,6-dimethylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(3,4-dimethylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(3,5-dimethylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(3,5-di-tert.-butylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(2,6-diphenylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(2,4,6-tri-phenylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(2,3,6-tri-methylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(2,3,5,6-tetramethylphenolato)aluminum(III); bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum(III); bis(2-methyl-8-quinolinato)(2-naphtholato)aluminum(III); bis(2,4-dimethyl-8-quinolinato)(ortho-phenylphenolato)aluminum(III); bis(2,4-dimethyl-8-quinolinato)(para-phenylphenolato)aluminum(III); bis(2,4-dimethyl-8-quinolinato)(meta-phenylphenolato)aluminum(III); bis(2,4-dimethyl-8-quinolinato)(3,5-dimethylphenolato)aluminum(III); and bis(2,4-dimethyl-8-quinolinato)(3,5-di-tert-butylphenolato)aluminum(III).

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Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1995-08-25 1996-02-24 1996-08-25 $2000.00 Window Closed / Lapsed
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