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WO2005048315A2 - Dispositifs electroluminescents et materiaux contenus dans lesdits dispositifs - Google Patents

Dispositifs electroluminescents et materiaux contenus dans lesdits dispositifs Download PDF

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Publication number
WO2005048315A2
WO2005048315A2 PCT/US2004/037843 US2004037843W WO2005048315A2 WO 2005048315 A2 WO2005048315 A2 WO 2005048315A2 US 2004037843 W US2004037843 W US 2004037843W WO 2005048315 A2 WO2005048315 A2 WO 2005048315A2
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WO
WIPO (PCT)
Prior art keywords
materials
complexes
luminescence
found
compounds
Prior art date
Application number
PCT/US2004/037843
Other languages
English (en)
Other versions
WO2005048315A3 (fr
Inventor
Fred Wudl
Teruyuki Mitsumori
Yoshiharu Sato
Hideki Sato
Takeshi Shioya
Original Assignee
University Of California, Los Angeles (Ucla)
Mitsubishi Chemical Corporation
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by University Of California, Los Angeles (Ucla), Mitsubishi Chemical Corporation filed Critical University Of California, Los Angeles (Ucla)
Publication of WO2005048315A2 publication Critical patent/WO2005048315A2/fr
Publication of WO2005048315A3 publication Critical patent/WO2005048315A3/fr

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Classifications

    • 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
    • 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
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • C09K2211/18—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
    • 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
    • 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
    • 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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/658—Organoboranes

Definitions

  • the present invention relates to organic light emitting materials and their use in organic light emitting devices (OLED) capable of converting electric energy to light.
  • FIG. 1 has previously been reported in the literature. See, for example, Kajigaesh, S.;
  • Materials A materials containing indolizino[3,4,5-ab]isoindole with the structure B shown in FIG. 1 (hereinafter referred to as Materials A) have excellent luminescence.
  • Another of the discoveries of the present invention is a series of novel organic materials, which include the structure of compound B. Each of these materials has also been found to have high luminescence. In addition, such materials have been found to have high luminescence at room temperature not only in solution, but also in the solid states.
  • Materials A it has been found that compounds with structures C and D and complexes with structure E shown in FIG. 1 have high luminescence quantum efficiencies and emit from blue to red light. Consequently, these compounds and complexes have high potentials for several optoelectronic devices, such as OLEDs, laser, sensor, and other semiconductor devices. It has also been found that the luminescence of complexes having the E structure include highly efficient phosphorescence at room temperature.
  • FIG. 1 shows Materials A formulae including structure B and the novel structures C, D and E of the organic light emitting materials of the present invention
  • FIG. 2 shows the structures of the compounds and complexes of the present invention that have been synthesized, Cl, C2, Dl, D2, D3, El, E2, E3, E4, E5, E6, E7, and E8;
  • FIG. 3A shows the schematic structure for the one embodiment of the device of the present invention, OLED SI, and the structures for ⁇ -NPD and Alq 3 used in two of the layers in SI;
  • FIG. 3B show a schematic structure for another embodiment of the device of the present invention, OLED S2, and the structure for CuPc used in one of the layers of S2;
  • FIG. 4 shows the materials used in the hole blocking layer and hole injection layers of OLEDs of the present invention for SI;
  • FIG. 5 shows the EL (electroluminence) spectra as a function of wavelength to compare the complex of the present invention, El, with a phosphorescence compound of the prior art;
  • FIG. 6 shows the structures for the compounds of the hole injection material; and
  • FIG. 7 shows the EL spectra as a function of wavelength to compare a compound of the present invention, Cl, with a prior art blue dopant, Coumarin-30 compound of the prior art (the coordinates for FIG. 7 are the same as those for FIG. 5);
  • FIG. 2 shows the chemical structures of compounds and complexes of the present invention that have been synthesized using techniques well known in the art. They includes compounds of the present invention having structures Cl, C2, Dl, D2, and D3, and complexes of the present invention having structures El, E2, E3, E4, E5, E6, E7, and E8. It is noted from FIG. 2 that the only respective differences between E4 and E7 and E6 and E8 are the introduction of either Pt or Pd. Luminescence quantum efficiencies were obtained for the compounds of Cl, C2, Dl, D2, and D3, Cl, C2, Dl, D2, and D3, and for the complexes of El, E2, E3, E4, E5,and E6 and are shown in Table 1 below: Table 1
  • OLED device structures were prepared in accordance with layering techniques well known in the art; see U.S. Patent Application Publication No. 2001/0019782.
  • the resulting OLED structures, SI and S2 are shown in FIG. 3A and 3B.
  • the layers were sandwiched between an anode in the form of indium tin oxide (ITO) and a cathode as shown in FIGS. 3A and 3B.
  • Materials A that incorporate the structure B as dopants were used in the emission layer referred to in FIGS. 3A and 3B.
  • The. emissive layer comprises a charge carrying, host material and the dopant of compound A.
  • Compound CBP the structure of which is shown below, was chosen as an appropriate host material for these compounds, after the oxidation and the reduction potentials of each compound
  • CBP were measured.
  • CBP had the best matching of HOMO/ LUMO (highest occupied or lowest unoccupied molecular orbital) with these compounds.
  • structure SI was found to be particularly good for the complexes of the present invention having structure E as the dopant layer, and structure S2 was particularly good for compounds of the present invention having structures C and D as the dopant layer.
  • Example 1 Device SI Device SI was prepared with a special hole blocking material, Ml, the structure of which is shown in FIG. 4 and a special hole injection layer.
  • the hole injection layer that was used for SI included a polymer M2 and an acceptor M3, the structures of which are also shown in FIG. 4.
  • the devices SI have the following 5 advantages in performance: (1) The brightness is quite high because complexes E have highly efficient phosphorescence at room temperature, and compound Ml confines excitations within the emission layer effectively. (2) Emitting light has narrow spectrum. (3) The emission color was tunable from green to red. (4) The lifetime becomes longer with compound Ml. (5) The efficiency of hole injection is improved considerably in the hole injection layer (M2, M3), such that the active voltage decreased.
  • Example 2 Device S2
  • Device S2 was prepared using the special hole blocking material Ml (FIG. 4), the same material as device SI. It was found the Ml also improves device performance and confines excitations effectively.
  • the devices S2 have the following 4 advantages in performance: (1) The devices give quite bright electroluminescence because compounds C, D have highly efficient photoluminescence even in solid state and the compound Ml confines excitations within the emission layer effectively. (2) The devices give sharp emission spectra. (3) Materials A containing structure B allow the lifetime of the device to be longer. (4) The emission color was tunable from blue to green
  • the electroluminescence devices of the present which include compounds A have high efficiency, longer lifetime and lower driving voltages.
  • the colors emitted from Materials A are tunable from blue to red with moderately narrow wavelengths.
  • one will be able to obtain bright, economic, long-lifetime and beautiful full-color displays with true color pixels.
  • one of ordinary skill in the art can make various changes and modifications to the materials and devices of the present invention to adapt it to various usages and conditions. As such, these changes and modifications are properly, equitably, and intended to be, within the full range of equivalents of the following claims.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La présente invention concerne des matériaux contenant de l'indolizino[3,4,5-ab] isoindol, doté de la structure B, qui présentent une luminescence excellente. L'invention a également trait à une série de nouveaux matériaux organiques dotés de la structure du composé B. Il a été constaté que chacun desdits matériaux présentait une forte luminescence. Il a été constaté en outre que de tels matériaux présentaient une forte luminescence à température ambiante non seulement en solution, mais également à l'état solide. Parmi les matériaux A, il a été constaté que les composés dotés des structures C et D et les complexes dotés de la structure E présentaient des rendements quantiques de luminescence élevés et émettaient une lumière allant du bleu au rouge. Par conséquent, lesdits composés et complexes présentent un potentiel élevé pour plusieurs dispositifs opto-électroniques, tels que les OLED, les lasers, les capteurs et d'autres dispositifs semi-conducteurs. Il a également été constaté que la luminescence des complexes dotés de la structure E incluait une phosphorescence très efficace à température ambiante. Cela signifie que les complexes dotés de la structure E présentent un fort potentiel pour des OLED faisant appel aux états triplets excités. Par ailleurs, il a été découvert que les OLED qui contiennent des composés et des complexes dotés de la structure B, c'est-à-dire des matériaux A, ont un bon rendement en matière de luminance, de tension d'attaque, de durée de vie et de saturation pure.
PCT/US2004/037843 2003-11-10 2004-11-10 Dispositifs electroluminescents et materiaux contenus dans lesdits dispositifs WO2005048315A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US51898603P 2003-11-10 2003-11-10
US60/518,986 2003-11-10

Publications (2)

Publication Number Publication Date
WO2005048315A2 true WO2005048315A2 (fr) 2005-05-26
WO2005048315A3 WO2005048315A3 (fr) 2006-07-06

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011024761A1 (fr) 2009-08-27 2011-03-03 住友化学株式会社 Composition de complexe métallique et polymère complexe
WO2011024737A1 (fr) 2009-08-27 2011-03-03 独立行政法人産業技術総合研究所 Complexe d'iridium et matériau luminescent formé à partir de celui-ci
WO2013183327A1 (fr) * 2012-06-07 2013-12-12 国立大学法人奈良先端科学技術大学院大学 Procédé pour la production d'un composé ayant une structure cyclique condensée, composé ayant une structure cyclique condensée et dispositif électroluminescent organique l'utilisant
WO2018215318A1 (fr) 2017-05-22 2018-11-29 Merck Patent Gmbh Composés hétéroaromatiques hexacycliques destinés à des dispositifs électroniques

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6303238B1 (en) * 1997-12-01 2001-10-16 The Trustees Of Princeton University OLEDs doped with phosphorescent compounds

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6303238B1 (en) * 1997-12-01 2001-10-16 The Trustees Of Princeton University OLEDs doped with phosphorescent compounds

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011024761A1 (fr) 2009-08-27 2011-03-03 住友化学株式会社 Composition de complexe métallique et polymère complexe
WO2011024737A1 (fr) 2009-08-27 2011-03-03 独立行政法人産業技術総合研究所 Complexe d'iridium et matériau luminescent formé à partir de celui-ci
WO2013183327A1 (fr) * 2012-06-07 2013-12-12 国立大学法人奈良先端科学技術大学院大学 Procédé pour la production d'un composé ayant une structure cyclique condensée, composé ayant une structure cyclique condensée et dispositif électroluminescent organique l'utilisant
WO2018215318A1 (fr) 2017-05-22 2018-11-29 Merck Patent Gmbh Composés hétéroaromatiques hexacycliques destinés à des dispositifs électroniques
CN110637017A (zh) * 2017-05-22 2019-12-31 默克专利有限公司 用于电子器件的六环杂芳族化合物
US11535619B2 (en) 2017-05-22 2022-12-27 Merck Patent Gmbh Hexacyclic heteroaromatic compounds for electronic devices

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