US20020004146A1 - Organic electroluminescent devices - Google Patents

Organic electroluminescent devices Download PDF

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US20020004146A1
US20020004146A1 US09/250,205 US25020599A US2002004146A1 US 20020004146 A1 US20020004146 A1 US 20020004146A1 US 25020599 A US25020599 A US 25020599A US 2002004146 A1 US2002004146 A1 US 2002004146A1
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cathode electrode
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Junji Kido
Tokio Mizukami
Jun Endoh
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Assigned to INTERNATIONAL MANUFACTURING AND ENGINEERING SERVICES CO., LTD. (UNDIVIDED ONE-HALF INTEREST), KIDO, JUNJI (UNDIVIDED ONE-HALF INTEREST) reassignment INTERNATIONAL MANUFACTURING AND ENGINEERING SERVICES CO., LTD. (UNDIVIDED ONE-HALF INTEREST) SAID RECEIVING PARTIES TO RECEIVE UNDIVIDED ONE-HALF INTEREST. SEE RECORD FOR DETAILS. Assignors: ENDOH, JUN, KIDO, JUNJI, MIZUKAMI, TOKIO
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    • 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
    • H10K50/80—Constructional details
    • H10K50/805—Electrodes
    • H10K50/82—Cathodes
    • 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 [2D] radiating surfaces
    • H05B33/26—Light sources with substantially two-dimensional [2D] radiating surfaces characterised by the composition or arrangement of the conductive material used as an electrode
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • 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
    • H10K50/80—Constructional details
    • H10K50/805—Electrodes
    • H10K50/81—Anodes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/26—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31678—Of metal

Definitions

  • the present invention relates to an organic electroluminescent device or element (hereinafter, also referred to as an “organic EL device”) which can be advantageously, for example, utilized as a planar light source or in display devices.
  • organic EL device organic electroluminescent device or element
  • the EL device can exhibit a high luminance and efficiency sufficient in practical use, that is, a luminance of about 1,000 cd/M 2 and an external quantum efficiency of about 1% at an applied voltage of not more than about 10 volts.
  • Tang et al. used a magnesium (Mg) having a low work function in combination with the organic compound which is basically considered to be an electrically insulating material, in order to reduce an energy barrier which can cause a problem during injection of electrons from a metal-made electrode.
  • Mg magnesium
  • the magnesium is liable to be oxidized and is instable, and also exhibits only a poor adhesion to a surface of the organic layers, magnesium was used after alloying, i.e., by the co-deposition of the same with silver (Ag) which is relatively stable and exhibits good adhesion to a surface of the organic layers.
  • a driving voltage of the EL device can be reduced by doping an alkali metal such as lithium and the like, an alkali earth metal such as strontium and the like or a rare earth metal such as samarium and the like to an organic layer adjacent to the cathode electrode (cf. SID 97, Digest, P.775). It was believed that such reduction of the driving voltage could be obtained because a barrier in the electron injection from the cathode electrode can be notably reduced due to a radical anion state in the organic layer adjacent to the electrode produced by metal doping therein.
  • Electron Devices., 40, 1342 (1993) suffers from a low reproducibility problem in the device production, because there is a difficulty in the control of the layer thickness, when the Li layer is deposited at a remarkably reduced thickness in the order of about 10 ⁇ .
  • the in-situ doping method developed by Pei et al. in which the Li salt is added to the luminescent layer to cause their dissociation in the electric field, there is a problem with the transfer time of the dissociated ions to the close vicinity of the electrodes having a controlled velocity, thereby causing a remarkable retardation of the response speed of the devices.
  • the present invention has been made to solve the above-described problems of the prior art EL devices, and accordingly one object of the present invention is to reduce an energy barrier in the electron injection of from a cathode electrode to an organic compound layer in accordance with the simple and reliable method, thereby ensuring a low-voltage driving regardless of the work function of the cathode material.
  • Another object of the present invention is to provide a device (organic electroluminescent device) capable of ensuring satisfactory characteristics which are similar to or higher than those obtained using the above-described alloy as the electrode material, when aluminum or other low-cost and stable metals which are conventionally used as the wiring material in the prior art are used alone as the cathode material.
  • an organic electroluminescent (EL) device comprising:
  • the organic layer is constituted from an organic metal complex compound containing at least one member selected from the group consisting of an alkali metal ion, an alkali earth metal ion and a rare earth metal ion, and
  • the cathode electrode comprises a metal capable of reducing the metal ion contained in the complex compound, in vacuum, to the corresponding metal.
  • the metal used in the formation of the cathode electrode is not restricted to the specific one, insofar as it can reduce the metal ion contained in the organic metal complex compound constituting the organic layer, in vacuum, to the corresponding metal, and preferably the metal includes, for example, aluminum (Al), zirconium (Zr), titanium (Ti), yttrium (Y), scandium (Sc) and silicon (Si). These metals may be used alone in the formation of the cathode electrode, or alternatively their alloy containing one metal or two or more metals of the above-described Al, Zr, Ti, Y, Sc and Si may be used.
  • cathode metals and alloys thereof have a high melting point and, under the vacuum conditions, they can act to reduce a metal ion in the organic metal complex compound to the corresponding metal.
  • alkali metals, alkali earth metals and rare earth metals can exhibit a higher saturated vapour pressure than that of the high melting point metals such as aluminum, and therefore any compounds containing such alkali metals or the like can be reduced with the high melting point metals such as aluminum, silicon, zirconium and the like.
  • calcium oxide can be reduced with aluminum to form a liberated metal calcium (cf. Chemical Handbook, “Applied Chemistry Section I”, edited by the Chemical Society of Japan, Maruzen Co., p.369)
  • rubidium oxide and strontium oxide cf. Metal Handbook, edited by the Japan Institute of Metals, Maruzen Co., pp.88-89
  • the production of metal electrodes in the organic EL devices is carried out in a vacuum of not more than 10 ⁇ 5 Torr to deposit an atomic metal on a substrate upon melting and volatilization of the metal. Therefore, when a thermally reducible metal such as aluminum, silicon, zirconium and the like in an atomic state is applied onto the alkali metals, alkali earth metals or rare earth metals, the above-described reduction reaction in vacuum is resulted to produce a reduced and liberated metal from the corresponding metal compounds.
  • a thermally reducible metal such as aluminum, silicon, zirconium and the like in an atomic state
  • the compound used is an organic metal compound (metal complex)
  • the compound itself can be doped (reduced) by the liberated metal, or, if a layer of the compound is thin and has a thickness of not more than 100 ⁇ , the liberated metal can act on the adjacent layer of the organic compound, thereby reducing organic compounds in an interfacial area between the two adjacent layers with its strong reduction power.
  • the alkali metal, alkali earth metal or rare earth metal compounds to be reduced are inorganic compounds such as oxides, fluorides and the like thereof, it is sometimes difficult to deposit their metal onto an organic layer, because the inorganic compounds have a high evaporation temperature due to their good stability. Further, due to their high electrical insulation property, the inorganic compounds can be deposited only at a highly restricted layer thickness of at most 20 ⁇ (cf. IEEE Trans. Electron Devices., 44, 1245 (1997).
  • the present invention is based on the above findings, and, to reduce an evaporation temperature and at the same time, to obtain a good layer formation property, the alkali metal, alkali earth metal or rare earth metal compounds in the form of an organic metal complex are used in place of the inorganic compounds. Further, selection and use of a suitable ligand compound as the organic metal complex enables to give a carrier transportation property including electron transportation property and hole transportation property to the resulting devices, thereby providing an advantage that a limitation concerning the thickness of the metal compound layer itself can be moderated in comparison with use of the inorganic compounds.
  • an organic layer (electron injection layer) adjacent to the cathode electrode is constituted from an organic metal complex compound containing at least one ion selected from the group consisting of an alkali metal ion, an alkali earth metal ion and a rare earth metal ion, and at the same time, a metal capable of reducing in vacuum the metal ion contained in the metal complex compound which is a material constituting the organic layer is used as the electrode material in the formation of the cathode electrode.
  • a metal of the organic metal complex compound of the organic layer is liberated, and then an organic compound is reduced with the liberated metal.
  • the present inventors have thus succeeded to diminish an electron injection barrier, thereby reducing a driving voltage of the devices.
  • the organic metal complex compound used in the formation of the organic layer adjacent to the cathode metal is not restricted to the specific one, insofar as it contains, as a metal ion thereof, at least one metal ion of the alkali metal ions, alkali earth metal ions and rare earth metal ions.
  • ligand compound for the metal complex compound although they are not restricted to the below-described, quinolinol, benzoquinolinol, acrydinol, phenanethridinol, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole, hydroxydiaryldiazole, hydroxyphenylpyridine, hydroxyphenylbenzoimidazole, hydroxybenzotriazole, hydroxyfurborane, bipyridyl, phenanethroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines and derivatives thereof can be preferably used.
  • FIG. 1 is a cross-sectional view illustrating a lamination structure of the organic EL device according one preferred embodiment of the present invention
  • FIG. 2 is a graph showing the relationship between the bias voltage and the luminance for the organic EL device according the present invention and the comparative organic EL device.
  • FIG. 3 is a graph showing the relationship between the current density and the luminance for the organic EL device according the present invention and the comparative organic EL device.
  • FIG. 1 is a simplified cross-sectional view illustrating the organic EL device according one preferred embodiment of the present invention.
  • a glass substrate (transparent substrate) 1 has, laminated in the following order on a surface thereof, a transparent electrode 2 constituting an anode electrode, a hole transportation layer 3 having a hole-transporting property, a luminescent layer 4 , an organic layer 5 and a back electrode 6 constituting a cathode electrode.
  • the glass substrate (transparent substrate) 1 , the transparent electrode 2 , the hole transportation layer 3 , and the luminescent layer 4 are the well-known components, and the organic layer 5 and the back electrode 6 each has specific features suggested by the present invention.
  • the organic EL device of the present invention may include other lamination structures such as anode/luminescent layer/organic layer/cathode, anode/hole transportation layer/luminescent layer/organic layer /cathode, anode/hole transportation layer/luminescent layer/electron transportation layer/organic layer/cathode, anode/hole injection layer/luminescent layer/organic layer/cathode, anode/hole injection layer/hole transportation layer/luminescent layer/organic layer/cathode, anode/hole injection layer/hole transportation layer/luminescent layer/electron transportation layer/organic layer/cathode, and others.
  • it may have any desired lamination structure, as long as a combination of the organic layer 5 and the cathode electrode 6 both included therein can satisfy the above-described requirements of the present invention.
  • the formation of the organic layer 5 may be carried out by using any desired methods for forming thin films including, for example, a vapour deposition method and a sputtering method. In addition to these methods, if its layer can be formed from a coating solution, the organic layer 5 may be formed from the coating solution by using any desired coating methods such as a spin coating method and a dip coating method.
  • the formation of the cathode electrode 6 may be carried out by using the vapour deposition method and the sputtering method, however, any other methods may be used, if desired, as long as such methods are based on the film formation in vacuum.
  • the organic compounds which can be used in the formation of the luminescent layer and the electron transportation layer are not restricted to the specific compounds.
  • suitable organic compounds include polycyclic compounds such as p-terphenyl and quaterphenyl as well as derivatives thereof; condensed polycyclic hydrocarbon compounds such as naphthalene, tetracene, pyrene, coronene, chrysene, anthracene, diphenylanthracene, naphthacene and phenanthrene as well as derivatives thereof; condensed heterocyclic compounds such as phenanthroline, bathophenanthroline, phenanthridine, acridine, quinoline, quinoxaline, phenazine and the like as well as derivatives thereof; and fluoresceine, perylene, phthaloperylene, naphthaloperylene, perynone, phthaloperynone
  • metal-chelated complex compounds described in Japanese Unexamined Patent Publication (Kokai) Nos.63-295695, 8-22557, 8-81472, 5-9470 and 5-17764 can be suitably used as the organic compounds.
  • metal-chelated oxanoide compounds for example, metal complexes which contain, as a ligand thereof, at least one member selected from 8-quinolinolato such as tris(8-quinolinolato)aluminum, bis(8-quinolinolato)magnesium, bis[benzo(f)-8-quinolinolato] zinc, bis(2-methyl-8-quinolinolato)aluminum, tri(8-quinolinolato)indium, tris(5-methyl-8-quinolinolato)aluminum, 8-quinolinolatolithium, tris(5-chloro-8-quinolinolato)gallium and bis(5-chloro-8-quinolinolato)calcium as well as derivatives thereof can be particularly suitably used.
  • 8-quinolinolato such as tris(8-quinolinolato)aluminum, bis(8-quinolinolato)magnesium,
  • oxadiazoles disclosed in Japanese Patent Kokai Nos.5-202011, 7-179394, 7-278124 and 7-228579, triazines disclosed in Japanese Patent Kokai No.7-157473, stilbene derivatives and distyrylarylene derivatives disclosed in Japanese Patent Kokai No.6-203963, styryl derivatives disclosed in Japanese Patent Kokai Nos.6-132080 and 6-88072, and diolefin derivatives disclosed in Japanese Patent Kokai Nos.6-100857 and 6-207170 are preferably used in the formation of the luminescent layer and the electron transportation layer.
  • a fluorescent whitening agent such as benzoxazoles, benzothiazoles and benzoimidazoles may be used as the organic compounds, and it includes, for example, those described in Japanese Patent Kokai No.59-194393.
  • Typical examples of the fluorescent whitening agent include the fluorescent whitening agents classified under the group of benzoxazoles such as 2,5-bis(5,7-di-t-pentyl-2-benzoxazolyl)-1,3,4-thiadiazole, 4,4′-bis(5,7-t-pentyl-2-benzoxazolyl)stilbene, 4,4′-bis[5,7-di(2-methyl-2-butyl)-2-benzoxazolyl]stilbene, 2,5-bis(5,7-di-t-pentyl-2-benzoxazolyl)thiophene, 2,5-bis[5-( ⁇ , ⁇ -dimethylbenzyl)-2-benzoxazolyl]thiophene, 2,5-bis[5,7
  • distyrylbenzene compound the compounds disclosed in European Patent No.373,582 may be used, for example.
  • Typical examples of the distyrylbenzene compound include 1,4-bis(2-methylstyryl)benzene, 1,4-bis(3-methylstyryl)benzene, 1,4-bis(4-methylstyryl)benzene, distyrylbenzene, 1,4-bis(2-ethylstyryl)benzene, 1,4-bis(3-ethylstyryl)benzene, 1,4-bis(2-methylstyryl)-2-methylbenzene and 1,4-bis(2-methylstyryl)-2-ethylbenzene.
  • distyrylpyrazine derivatives disclosed in Japanese Patent Kokai No.2-252793 may also be used in the formation of the luminescent layer and the electron transportation layer.
  • Typical examples of the distyrylpyrazine derivatives include 2,5-bis(4-methylstyryl) pyrazine, 2,5-bis(4-ethylstyryl)pyrazine, 2,5-bis[2-(1-naphthyl)vinyl]pyrazine, 2,5-bis(4-methoxystyryl)pyrazine, 2,5-bis[2-(4-biphenyl)vinyl]pyrazine and 2,5-bis[2-(1-pyrenyl)vinyl]pyrazine.
  • dimethylidine derivatives disclosed in European Patent No.388,768 and Japanese Patent Kokai No.3-231970 may also be used as the material of the luminescent layer and the electron transportation layer.
  • Typical examples of the dimethylidine derivatives include 1,4-phenylenedimethylidine, 4,4′-phenylenedimethylidine, 2,5-xylylenedimethylidine, 2,6-naphthylenedimethylidine, 1,4-biphenylenedimethylidine, 1,4-p-terephenylenedimethylidine, 9,10-anthracenediyldimethylidine, 4,4′-(2,2-di-t-butylphenyl vinyl)biphenyl and 4,4′-(2,2-diphenylvinyl)biphenyl as well as derivatives thereof; silanamine derivatives disclosed in Japanese Patent Kokai Nos.6-49079 and 6-293778; polyfunctional styryl compounds disclosed in Japanese Patent Kokai Nos.6-27932
  • any well-known compounds which are conventional in the production of the prior art organic EL devices may be suitably used, if desired.
  • the arylamine compounds used in the formation of the hole injection layer, the hole transportation layer and the hole-transporting luminescent layer preferably include those disclosed in Japanese Patent Kokai Nos.6-25659, 6-203963, 6-215874, 7-145116, 7-224012, 7-157473, 8-48656, 7-126226, 7-188130, 8-40995, 8-40996, 8-40997, 7-126225, 7-101911 and 7-97355.
  • Suitable arylamine compounds include, for example, N,N,N′,N′-tetraphenyl-4,4′-diaminophenyl, N,N′-diphenyl-N,N′-di(3-methylphenyl)-4,4′-diaminobiphenyl, 2,2-bis(4-di-p-tolylaminophenyl)propane, N,N,N′,N′-tetra-p-tolyl-4,4′-diaminobiphenyl, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N′-diphenyl-N,N′-di(4-methoxyphenyl)-4,4′-diaminobiphenyl, N,N,N′,N′-tetraphenyl-4,4′-diaminodiphenylether, 4,4′-bis(diphenylamino)quadrip
  • a dispersion of the above-described organic compounds in a polymer or a polymerized product of such organic compounds may be used as the layer-forming layer.
  • so-called “ ⁇ -conjugated polymers” such as polyparaphenylene vinylene and its derivatives, hole-transporting non-conjugated polymers, typically poly(N-vinylcarbazole), and ⁇ -conjugated polymers of polysilanes may be used as the layer-forming material.
  • the material of the hole injection layer to be deposited over the ITO (indium-tin oxide) electrode is not restricted to the specific one, however, metal phthalocyanines such as copper phthalocyanine as well as non-metal phthalocyanines, carbon films and electrically conductive polymers such as polyanilines may be preferably used in the formation of the hole injection layer.
  • the hole injection layer may be formed by reacting the above-described arylamine compounds with a Lewis acid as an oxidizing agent to generate radical cations.
  • an organic layer adjacent to the cathode is constituted from an organic metal complex compound containing at least one of the alkali metal ions, alkali earth metal ions and rare earth metal ions, and the cathode is constituted from a metal capable of reducing, in vacuum, the metal ion of the metal complex compound constituting the organic layer, it becomes possible to utilize low cost and stable metals, which are conventional as a wiring material in the prior art devices, as a cathode material in the production of the organic EL devices.
  • the present invention it becomes possible to produce the EL devices having a diminished electron injection barrier and a reduced driving voltage as well as a high efficiency and high luminance. Accordingly, the EL devices of the present invention can exhibit a high utility in practical use, and ensures their effective utilization as display devices, light sources and others.
  • vapour deposition of the organic compound and that of the metal each was carried out by using the vapour deposition apparatus “VPC-400” commercially available from Shinkuu Kikou Co.
  • the thickness of the deposited layers was determined by using the profilometer “DekTak3ST” commercially available from Sloan Co.
  • the characteristics of the organic EL device were determined by using the source meter 2400 commercially available from Keithley & Co. and the luminance meter BM-8 commercially available from Topcon Co.
  • a DC voltage was stepwise applied at an increasing rate of one volt per 2 seconds to the EL device having an ITO anode and an aluminum (Al) cathode, and the luminance and the electric current were determined after one second had passed from the completion of each increase of the voltage.
  • the EL spectrum was determined by using the optical multichannel analyzer PMA-10, commercially available from Hamamatsu Photonics Co., driven at a constant electric current.
  • a glass substrate 1 was coated with an ITO (indium-tin oxide) layer having a sheet resistance of about 25 ⁇ / ⁇ , commercially available as an electron beam deposition product from Sanyo Shinku Co., to form a transparent anode electrode 2 .
  • ITO indium-tin oxide
  • Alpha ( ⁇ )-NPD having a hole transporting property represented by the following formula (1), was deposited onto the ITO-coated glass substrate 1 under the vacuum vapour deposition conditions of about 10 ⁇ 6 Torr and about 2 ⁇ /sec to form a hole transportation layer 3 having a thickness of about 500 ⁇ .
  • Alq tris(8-quinolinolato)
  • Liq lithium complex of mono(8-quinolinolato) (briefly referred to as “Liq”) represented by the following formula (3) was deposited under the pressure of about 10 ⁇ 6 Torr and at the deposition speed of about 1 ⁇ /sec onto the layer 4 to form an organic layer (electron injection layer) 5 having a thickness of about 10 ⁇ .
  • Example 1 The procedure of Example 1 was repeated with the proviso that, for the purpose of comparison, an organic layer (electron injection layer) was omitted from the organic EL device. That is, ⁇ -NPD was first deposited onto the ITO-coated glass substrate to form a hole transportation layer having a thickness of about 500 ⁇ , and then Alq was lo deposited under the same vacuum deposition conditions as in the deposition of the hole transportation layer to form a luminescent Alq layer having a thickness of about 700 ⁇ .
  • ⁇ -NPD was first deposited onto the ITO-coated glass substrate to form a hole transportation layer having a thickness of about 500 ⁇
  • Alq was lo deposited under the same vacuum deposition conditions as in the deposition of the hole transportation layer to form a luminescent Alq layer having a thickness of about 700 ⁇ .
  • the luminance of the green luminescence from the luminescent Alq layer was determined as in Example 1.
  • the results were plotted with triangular marks in each of FIG. 2 and FIG. 3. These results indicate that only a luminance of at most about 1,600 cd/m 2 could be obtained at the applied bias voltage of 16 volts, and an application of the voltage of about 14.5 volts was required to obtain a luminance of 1,000 cd/m 2 . It is appreciated from these results that the presence of the organic layer which is essential to the organic EL device of the present invention is effective to reduce the driving voltage of the EL device.
  • Example 1 The procedure of Example 1 was repeated with the proviso that in this example, ⁇ -NPD was first deposited onto the ITO-coated glass substrate 1 to form a hole transportation layer 3 having a thickness of about 500 ⁇ , followed by vacuum deposition of Alq to form a luminescent layer 4 having a thickness of about 700 ⁇ . Thereafter, a sodium complex of mono(8-quinolinolato) (briefly referred to as “Naq”), represented by the following formula (4), was deposited under the pressure of about 10 ⁇ 6 Torr and at the deposition speed of about 1 ⁇ /sec onto the luminescent layer 4 to form an organic layer (electron injection layer) 5 having a thickness of about 10 ⁇ .
  • Naq sodium complex of mono(8-quinolinolato)
  • a maximum luminance of about 31,500 cd/m 2 could be obtained at the applied bias voltage of 13 volts, along with the current density of about 319 mA/cm 2 . That is, in this example, a highly increased luminance which is comparable to that of the above-described Example 1 could be obtained at a low driving voltage.
  • Example 1 The procedure of Example 1 was repeated with the proviso that in this example, ⁇ -NPD was first deposited onto the ITO-coated glass substrate 1 to form a hole transportation layer 3 having a thickness of about 500 ⁇ , followed by vacuum deposition of Alq to form a luminescent layer 4 having a thickness of about 700 ⁇ .
  • Li(dpm) lithium complex of mono(2,2,6,6-tetramethyl-3,5-heptanediona to)
  • Li(dpm) lithium complex of mono(2,2,6,6-tetramethyl-3,5-heptanediona to)
  • a maximum luminance of about 18,000 cd/m 2 could be obtained at the applied bias voltage of 15 volts, along with the current density of about 327 mA/cm 2 . That is, in this example, a highly increased luminance which is comparable to that of the above-described Example 1 could be obtained at a low driving voltage.
  • Example 1 The procedure of Example 1 was repeated with the proviso that in this example, ⁇ -NPD was first deposited onto the ITO-coated glass substrate 1 to form a hole transportation layer 3 having a thickness of about 500 ⁇ , followed by vacuum deposition of Alq to form a luminescent layer 4 having a thickness of about 700 ⁇ .
  • Na(dpm) sodium complex of mono(2,2,6,6-tetramethyl-3,5-heptane-dionato)
  • Na(dpm) mono(2,2,6,6-tetramethyl-3,5-heptane-dionato)
  • a maximum luminance of about 21,000 cd/m 2 could be obtained at the applied bias voltage of 14 volts, along with the current density of about 433 mA/CM 2 . That is, in this example, a highly increased luminance which is comparable to that of the above-described Example 1 could be obtained at a low driving voltage.
  • Example 1 The procedure of Example 1 was repeated with the proviso that in this example, ⁇ -NPD was first deposited onto the ITO-coated glass substrate 1 to form a hole transportation layer 3 having a thickness of about 500 ⁇ , followed by vacuum deposition of Alq to form a luminescent layer 4 having a thickness of about 700 ⁇ .
  • Rb(dpm) mono(2,2,6,6-tetramethyl-3,5-heptane-dionato)
  • a maximum luminance of about 25,000 cd/m 2 could be obtained at the applied bias voltage of 13 volts, along with the current density of about 504 mA/cm 2 . That is, in this example, a highly increased luminance which is comparable to that of the above-described Example 1 could be obtained at a low driving voltage.
  • Example 1 The procedure of Example 1 was repeated with the proviso that in this example, ⁇ -NPD was first deposited onto the ITO-coated glass substrate 1 to form a hole transportation layer 3 having a thickness of about 500 ⁇ , followed by vacuum deposition of Alq to form a luminescent layer 4 having a thickness of about 700 ⁇ .
  • Mg(dpm)2 di(2,2,6,6-tetramethyl-3,5-heptanediona to)
  • a maximum luminance of about 3,400 cd/m 2 could be obtained at the applied bias voltage of 17 volts, along with the current density of about 120 mA/cm 2 . That is, in this example, a highly increased luminance which is comparable to that of the above-described Example 1 could be obtained at a low driving voltage.
  • Example 1 The procedure of Example 1 was repeated with the proviso that in this example, ⁇ -NPD was first deposited onto the ITO-coated glass substrate 1 to form a hole transportation layer 3 having a thickness of about 500 ⁇ , followed by vacuum deposition of Alq to form a luminescent layer 4 having a thickness of about 700 ⁇ .
  • Ca(dpm)2 a calcium complex of di(2,2,6,6-tetramethyl-3,5-heptanedionato(briefly referred to as “Ca(dpm)2 ”), represented by the following formula (9), was deposited under the pressure of about 10 ⁇ 6 Torr and at the deposition speed of about 1 ⁇ /sec onto the luminescent layer 4 to form an organic layer (electron injection layer) 5 having a thickness of about 10 ⁇ .
  • a maximum luminance of about 14,300 cd/m 2 could be obtained at the applied bias voltage of 18 volts, along with the current density of about 168 mA/cm 2 . That is, in this example, a highly increased luminance which is comparable to that of the above-described Example 1 could be obtained at a low driving voltage.
  • Example 1 The procedure of Example 1 was repeated with the proviso that in this example, ⁇ -NPD was first deposited onto the ITO-coated glass substrate 1 to form a hole transportation layer 3 having a thickness of about 500 ⁇ , followed by vacuum deposition of Alq to form a luminescent layer 4 having a thickness of about 700 ⁇ . Thereafter, an europium complex of tri(1,3-phenyl-1,3-propanedionato)mono (bathophenanthoroline) (briefly referred to as “Eu(dpm) 3.
  • Bphen represented by the following formula (10), was deposited under the pressure of about 10 ⁇ 6 Torr and at the deposition speed of about 1 ⁇ /sec onto the luminescent layer 4 to form an organic layer (electron injection layer) 5 having a thickness of about 10 ⁇ .
  • a maximum luminance of about 12,000 cd/m 2 could be obtained at the applied bias voltage of 13 volts, along with the current density of about 230 mA/cm 2 . That is, in this example, a highly increased luminance which is comparable to that of the above-described Example 1 could be obtained at a low driving voltage.

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CN100372143C (zh) 2008-02-27
DE69914000D1 (de) 2004-02-12
EP0936844A2 (fr) 1999-08-18
KR100533341B1 (ko) 2005-12-05
US20030072967A1 (en) 2003-04-17
DE69914000T2 (de) 2004-10-21
TW427098B (en) 2001-03-21
EP0936844A3 (fr) 2000-12-13
KR19990072663A (ko) 1999-09-27
ATE257638T1 (de) 2004-01-15
EP0936844B1 (fr) 2004-01-07
CN1238655A (zh) 1999-12-15
US7326473B2 (en) 2008-02-05
JPH11233262A (ja) 1999-08-27
JP4514841B2 (ja) 2010-07-28

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