WO2005048315A2 - Light emitting devices and materials for use in the devices - Google Patents

Light emitting devices and materials for use in the devices Download PDF

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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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materials
complexes
luminescence
found
compounds
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PCT/US2004/037843
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WO2005048315A3 (en
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Fred Wudl
Teruyuki Mitsumori
Yoshiharu Sato
Hideki Sato
Takeshi Shioya
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University Of California, Los Angeles (Ucla)
Mitsubishi Chemical Corporation
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    • 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

The present invention illustrates that materials containing indolizino[3,4,5-ab] isoindole with the structure B have excellent luminescence. The invention also shows 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. Among Materials A, it has been found that compounds with structures C and D and complexes with structure E 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. This means the complexes of the E structure have high potential for OLEDs that use triplet excited states. Still another discovery is that OLEDs that include compounds and complexes that incorporate structure B, i.e., Materials A, show good performance in brightness, driving voltage, lifetime and pure chroma.

Description

LIGHT EMITTING DEVICES AND MATERIALS FOR USE IN THE DEVICES
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] The present application claims the benefit of priority from pending U.S. Provisional Patent Application No. 60/518,986, entitled "Light Emitting Devices and Materials For Use In Devices", filed on November 10, 2003, which is herein incorporated by reference in its entirety.
FD2LD OF THE INVENTION [0002] 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.
BACKGROUND OF THE INVENTION [0003] U.S. Patent No. 6,303,238 and U.S. Patent Application Publication No.
2001/0019782 disclose OLEDs for use in various display devices. The '238 patent describes a heterostructure of an emissive layer containing a phosphorescent dopant compound for producing electroluminescence. The 19782 published application describes an OLED having a light-emitting layer of an orthometalated iridium complex or a plurality of such thin organic compound layers. The descriptions of each of these references are incorporated herein by reference.
[0004] Indolizino[3,4,5-ab]isoindole, with a chemical structure B as shown in
FIG. 1 has previously been reported in the literature. See, for example, Kajigaesh, S.;
Mori, S.; Fujisaki, S.; Kanemasa, S. Bull. Chem. Soc. Jpn. 1985, 58, 3547. (b) Matsumoto, K.; Uchida, T.; Kato, T.; Toda, M.; Aoyama, K.; Konishi, H.
Heterocycles 1990, 31, 593. (c) Tominaga, Y.; Shiroshita, Y.; Gotou, H.; Matsuda, Y.
Heterocycles 1986, 24, 3071. (d) Castle, L.W.; Tominaga, Y.; Castle, R.N. J.
Heterocyclic. Chem. 1995, 32, 1033. (e) Tominaga, Y.; Shigematsu, Y.; Saeki, K. J.
Heterocyclic. Chem. 2002, 39, 571. (f) Yamauchi, J.; Uchida, T.; Matsumoto, K. Heterocycles 1990, 31, 1785. (g) Matsumoto, K.; Yamauchi, J. Uchida, T.
Heterocycles 1985, 23 2773. (h) Uchida, T.; Aoyama, K.; Nishikawa, M.; Kuroda, T.;
Okamoto, T. J. Heterocyclic. Chem. 1988, 25, 1793. (i) Matsumoto, K.; Uchida, T.;
Sugi, T.; Yagi,. Y. Chem. Lett. 1982, 869. (j) Matsumoto, K.; Katsura, H.; Uchida, T.;
Aoyama, K.; Machiguchi, T. J. Chem. Soc. Perkin Trans. 1 1996, 21, 2599. (k) Matsumoto, K.; Katsura, H.; Yamauchi, J.; Uchida, T.; Aoyama, K.; Machiguchi, T. Bull. Soc. Chim. Fr. 1996, 133, 891. Nothing in the literature suggests using such a compound as a light emitting material.
[0005] Because of the myriad of uses for OLEDs, there is a growing demand for improved light emitting materials.
SUMMARY OF THE INVENTION
[0006] One of the discoveries of the present invention is that 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.
[0007] 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. Among 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. This means the complexes of the E structure have high potential for OLEDs that use triplet excited states. [0008] Still another discovery is that OLEDs that include compounds and complexes that incorporate structure B, i.e., Materials A, show good performance in brightness, driving voltage, lifetime and pure chroma.
BRIEF DESCRIPTION OF THE DRAWINGS
[0009] The foregoing aspects and the attendant advantages of the present invention will become more readily appreciated by reference to the following detailed description, when taken in conjunction with the accompanying drawings, wherein: [0010] 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; [0011] 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;
[0012] FIG. 3A shows the schematic structure for the one embodiment of the device of the present invention, OLED SI, and the structures for α-NPD and Alq3 used in two of the layers in SI;
[0013] 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; [0014] FIG. 4 shows the materials used in the hole blocking layer and hole injection layers of OLEDs of the present invention for SI; [0015] 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; [0016] FIG. 6 shows the structures for the compounds of the hole injection material; and
[0017] 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);
[0018] Reference symbols or names are used in the figures to indicate certain components or features shown therein, with reference symbols common to more than one figure indicating like components or features shown therein. DETAILED DESCRIPTION OF THE INVENTION
[0019] 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
Figure imgf000006_0002
[0020] Relative quantum efficiency (Q.E.) (%) and λ max (nm) of luminescence ismeasured in DMSO at room temperature; reference perylene in degassed cyclohexane as 94%.
[0021] 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. In both of these structures, 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
Figure imgf000006_0001
CBP were measured. [0022] Among conventional host materials, CBP had the best matching of HOMO/ LUMO (highest occupied or lowest unoccupied molecular orbital) with these compounds. Specifically, 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.
[0023] Examples of the two embodiment of the OLEDs of the present invention that follows illustrates the unexpected results from practicing the teachings of the present invention over that of the prior art. The examples are for illustrative purposes only and are not meant to limit the scope of the claims in any way.
EXAMPLES 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. [0024] There are a lot of articles that report phosphorescent materials; see (a) Baldo, M. A.; Brien, D. F.; You, Y.; Shoustikov, A.; Sibley, S.; Thompson, M. E.; Forest, S. R. Nature 1998, 395, 151; and (b) Lamansky, S.; Djurovich, P.; Murphy, D.; Abdel Razzaq, F.; Lee, H. E.; Adachi, C; Burrows, P. E.; Forrest, S. R.;
Thompson, M. E. J. Am. Chem. Soc. 2001, 123, 4304. There are also a number of devices including these materiasl that are reported in the literature; see (a) Baldo, M A.; Lamansky, S.; Burrows, P. E.; Thompson, M. E.; Forrest, S. R. Appl. Phys. Lett. 1999, 75, 4; (b) Lee, C. L.; Lee, K. B.; Kim, J. J. Appl. Phys. Lett. 2000, 77, 2280; (c) Baldo, M. A.; Thompson, M. E.; Forest, S. R. Nature 2000, 403, 750; (d) Lcai, M.; Tokito, Appl. Phys. Lett. 2001, 79, 156; (e) Forrest, S. R.; Thompson, M. E.; Baldo, M A.; U. S. Patent No. 5189136; and (f) Sato, H.; Fugono, M.; Sato, Y. U. S. Patent 2002, No.l25818. [0025] However, among the materials reported in the prior art, the complexes E of the present invention have relatively high quantum efficiencies and surprisingly, have narrow-band luminescence spectra; see Table 1 above. As shown in FIG. 5, the electroluminescence spectrum of invented compound El (line with triangle data points) was much narrower than that of conventional phosphorescence compound Ir(ppy)3 (lien with square data points). This means, with the OLEDs of the present invention, one will be able to obtain brighter and more beautiful displays that have pure colors.
Example 2: Device S2 [0026] 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. [0027] 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
[0028] There are a lot of dopant dyes for blue OLEDs: Coumarin 30 derivatives, aromatic hydrocarbons such as perylene, pyrene, and anthracene, stilbene derivatives, oligophenylene derivatives, furan derivatives, and oxazole derivatives. However, compounds C, D of the present invention have relatively high quantum efficiencies (Table 1) and interestingly have narrow band luminescence. As shown in Figure 7, the electroluminescence spectrum of the invented compound Cl (triangle data points) was much narrower than that of conventional blue dopant Coumarin 30 (square data points). This means that the invented devices are applicable to brighter and more beautiful displays that have pure colors. [0029] The Materials A of the present have been found to have quite high luminescence quantum efficiencies even in the solid states, which means there are little self quenching in the systems using these materials.
[0030] 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. In short, by applying the present inventions, one will be able to obtain bright, economic, long-lifetime and beautiful full-color displays with true color pixels. [0031] Without departing from the spirit and scope of this invention, 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.

Claims

CLAIMS[0032] We claim:
1. A light-emitting material selected from the group consisting of materials (l)-(4) having a structure represented by the following formulae:
Figure imgf000010_0001
Figure imgf000010_0002
wherein Z\ represents an aromatic ring which has a nitrogen atom,
Figure imgf000010_0003
wherein Z2 represents a fused ring,
Figure imgf000010_0004
wherein M represents a metal selected from the group consisting of Ir,
Pt, and Pd. A compound having the structure:
Figure imgf000011_0001
wherein Z\ represents an aromatic ring which has a nitrogen atom. A compound having the structure:
Figure imgf000011_0002
wherein Z2 represents an fused ring. A compound having the structure:
Figure imgf000011_0003
wherein M represents a metal selected from the group consisting of Ir, Pt, and Pd. 5. An organic light-emitting device comprising at least one light-emitting layer interposed between a pair of electrodes, said layer contains a light-emitting material selected from the group consisting of materials (l)-(4) represented by the following formula:
Figure imgf000011_0004
wherein Zλ represents an aromatic ring which has a nitrogen atom,
Figure imgf000012_0001
wherein Z2 represents a fused ring,
Figure imgf000012_0002
wherein M represents a metal selected from the group consisting of Ir, Pt, and Pd.
Figure imgf000012_0003
PCT/US2004/037843 2003-11-10 2004-11-10 Light emitting devices and materials for use in the devices WO2005048315A2 (en)

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WO2011024737A1 (en) 2009-08-27 2011-03-03 独立行政法人産業技術総合研究所 Iridium complex and light emitting material formed from same
WO2011024761A1 (en) 2009-08-27 2011-03-03 住友化学株式会社 Metal complex composition and complex polymer
WO2013183327A1 (en) * 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 Method for producing compound having condensed ring structure, compound having condensed ring structure, and organic light-emitting device using same
WO2018215318A1 (en) 2017-05-22 2018-11-29 Merck Patent Gmbh Hexacyclic heteroaromatic compounds for electronic devices

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011024737A1 (en) 2009-08-27 2011-03-03 独立行政法人産業技術総合研究所 Iridium complex and light emitting material formed from same
WO2011024761A1 (en) 2009-08-27 2011-03-03 住友化学株式会社 Metal complex composition and complex polymer
WO2013183327A1 (en) * 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 Method for producing compound having condensed ring structure, compound having condensed ring structure, and organic light-emitting device using same
WO2018215318A1 (en) 2017-05-22 2018-11-29 Merck Patent Gmbh Hexacyclic heteroaromatic compounds for electronic devices
CN110637017A (en) * 2017-05-22 2019-12-31 默克专利有限公司 Hexacyclo heteroaromatic compounds for electronic devices
US11535619B2 (en) 2017-05-22 2022-12-27 Merck Patent Gmbh Hexacyclic heteroaromatic compounds for electronic devices

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