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CA2487118A1 - Complexes d'osmium et de ruthenium phosphorescents et leur utilisation - Google Patents

Complexes d'osmium et de ruthenium phosphorescents et leur utilisation Download PDF

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Publication number
CA2487118A1
CA2487118A1 CA002487118A CA2487118A CA2487118A1 CA 2487118 A1 CA2487118 A1 CA 2487118A1 CA 002487118 A CA002487118 A CA 002487118A CA 2487118 A CA2487118 A CA 2487118A CA 2487118 A1 CA2487118 A1 CA 2487118A1
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CA
Canada
Prior art keywords
compound
light
emitting device
ligand
bis
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.)
Granted
Application number
CA002487118A
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English (en)
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CA2487118C (fr
Inventor
Ye Tao
Arthur J. Carty
Yun Chi
Yung-Liang Tung
Pi-Tai Chou
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Samsung Display Co Ltd
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Individual
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Priority claimed from CA002448718A external-priority patent/CA2448718A1/fr
Application filed by Individual filed Critical Individual
Priority to CA2487118A priority Critical patent/CA2487118C/fr
Publication of CA2487118A1 publication Critical patent/CA2487118A1/fr
Application granted granted Critical
Publication of CA2487118C publication Critical patent/CA2487118C/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/002—Osmium compounds
    • C07F15/0026—Osmium compounds without a metal-carbon linkage
    • 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
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/348—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising osmium
    • 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
    • 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
    • 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
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • 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
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne des composés phosphorescents, leurs utilisations et des dispositifs qui comprennent des diodes électroluminescentes organiques (DELO) qui comprennent de tels composés. Les composés dintérêt comprennent : (voir la formule I) dans laquelle A représente un atome Os ou Ru. Les chromophores de chélation anioniques N~N, qui sont formés en connectant une structure de noyau pentagonale contenant au moins deux atomes dazote à un fragment de type pyridine hexagonale par une liaison carbone-carbone directe. L représente un ligand donneur neutre; lexemple type comprend un groupe carbonyle, pyridine, phosphine, arsine et isocyanure; deux L neutres peuvent également se combiner pour produire ce quon appelle un ligand de chélation tel que la 2,2-bipyridine, la 1,10-phénanthroline et le ligand de carbène N-hétérocyclique (NHC), ou des ligands bidentés de phosphore tels que le 1,2- bis(diphénylphosphino)éthane et le 1,2-bis(diphénylphosphino)benzène. L peut être orienté soit en cis ou en trans. Lorsque L occupe la position trans, la structure préférée contient à la fois le fragment hexagonal de N~N ainsi que son fragment pentagonal situé à la position trans par rapport à leur contrepartie du second chromophore N~N. Lorsque L occupe la position cis, la structure préférée est constituée de lunité pentagonale des chromophores N~N qui résident à lopposée du L. X1, X2 et X3 sont indépendamment un atome C ou N; quand X2 représente un atome de N, R1 est omis, quand X3 représente un atome N, R2 est omis, R1 représente un atome H, un groupe alkyle de C1 à C8, un groupe phényle substitué de C1 à C8 ou un groupe perfluoroalkyle de C1 à C4, R2 représente un atome H, F ou un substituant cyano, X4 représente soit un atome C ou N; X4 peut se situer à tout emplacement sur le noyau hexagonal, quand X4 représente un atome N et R3 et R4 ne sont pas liés à X4, R3 représente un atome H, un groupe méthyle ou un petit groupe alkyle de C1 à C3, R4 représente un atome H, un groupe méthyle ou un petit groupe alkyle de C1 à C3, ou R3 et R4 forment ensemble une unité conjuguée supplémentaire avec une structure
CA2487118A 2003-11-07 2004-11-05 Complexes d'osmium et de ruthenium phosphorescents et leur utilisation Expired - Lifetime CA2487118C (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA2487118A CA2487118C (fr) 2003-11-07 2004-11-05 Complexes d'osmium et de ruthenium phosphorescents et leur utilisation

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CA002448718A CA2448718A1 (fr) 2003-11-07 2003-11-07 Complexes d'osmium (ii) phosphorescents, et utilisations connexes
CA2,448,718 2003-11-07
CA2487118A CA2487118C (fr) 2003-11-07 2004-11-05 Complexes d'osmium et de ruthenium phosphorescents et leur utilisation

Publications (2)

Publication Number Publication Date
CA2487118A1 true CA2487118A1 (fr) 2005-05-07
CA2487118C CA2487118C (fr) 2016-09-27

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102844402A (zh) * 2010-01-25 2012-12-26 欧司朗股份有限公司 磷光性的金属络合化合物、用于制造其的方法和发光器件

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111384273B (zh) * 2018-12-29 2021-07-16 Tcl科技集团股份有限公司 一种量子点发光二极管及其制备方法

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102844402A (zh) * 2010-01-25 2012-12-26 欧司朗股份有限公司 磷光性的金属络合化合物、用于制造其的方法和发光器件
CN102844402B (zh) * 2010-01-25 2016-06-22 欧司朗股份有限公司 磷光性的金属络合化合物、用于制造其的方法和发光器件

Also Published As

Publication number Publication date
CA2487118C (fr) 2016-09-27

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