WO2008041642A1 - Dispositif électroluminescent organique et dispositif d'affichage - Google Patents

Dispositif électroluminescent organique et dispositif d'affichage Download PDF

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Publication number
WO2008041642A1
WO2008041642A1 PCT/JP2007/069026 JP2007069026W WO2008041642A1 WO 2008041642 A1 WO2008041642 A1 WO 2008041642A1 JP 2007069026 W JP2007069026 W JP 2007069026W WO 2008041642 A1 WO2008041642 A1 WO 2008041642A1
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Prior art keywords
organic electroluminescent
layer
organic
light emitting
emitting layer
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PCT/JP2007/069026
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English (en)
Japanese (ja)
Inventor
Emiko Kambe
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Sony Corporation
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Publication of WO2008041642A1 publication Critical patent/WO2008041642A1/fr

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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
    • H10K50/10—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
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/652—Cyanine dyes
    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes

Definitions

  • the present invention relates to an organic electroluminescent element (so-called organic EL element) and a display device, and more particularly to an organic electroluminescent element and a display device in which a light emitting layer contains a luminescent dopant.
  • organic EL element organic electroluminescent element
  • a display device in which a light emitting layer contains a luminescent dopant.
  • Organic electroluminescence devices (so-called organic EL devices) using electroluminescence (hereinafter referred to as EL) of organic materials have organic hole transport layers and organic light emitting layers between the anode and cathode. It is attracting attention as a light-emitting element that is provided with a laminated organic layer and can emit high-intensity light by low-voltage direct current drive.
  • FIG. 2 is a cross-sectional view showing a configuration example of such an organic electroluminescent element.
  • An organic electroluminescent device 101 shown in this figure is provided on a transparent substrate 102 made of glass or the like, for example, an anode 103 provided on the substrate 102, an organic layer 104 provided on the anode 103, and The cathode 105 is provided on the organic layer 104.
  • the organic layer 104 has a configuration in which a hole injection layer 104a, a hole transport layer 104b, a light emitting layer 104c, and an electron transport layer 104d are sequentially stacked from the anode 103 side.
  • this organic electroluminescent element 101 electrons injected from the negative electrode 105 and holes injected from the anode 103 are recombined in the light emitting layer 104c, and light generated during this recombination is generated by the anode 103 or the cathode 105. Is taken out through.
  • an organic electroluminescent element there is a structure in which a cathode, an organic layer, and an anode are sequentially laminated in this order from the substrate side.
  • Alq3 8-hydroxyquinoline aluminum
  • P197_199 Silole derivatives (eg Applied Physics Letter (US) 14th January 2002, Vol. 80) , No.2, P189_ 191) have been reported.
  • an organic electroluminescent device in which hosts having different carrier mobilities are mixed is disclosed (for example, see Japanese Patent No. 3743005 and Japanese Patent Laid-Open No. 2000-106277).
  • organic electroluminescence devices using assist dopants that assist the energy transfer of the light emitting layer are disclosed (see, for example, JP-A-2005-108727 and JP-A-3370011).
  • the organic electroluminescent device described in JP-A-2006-66872 has a long lifetime of the device because the electron injection limiting layer is arranged to limit the electron injection into the light emitting layer.
  • the luminous efficiency in the recombination region of electrons and holes is lowered.
  • the organic electroluminescence devices described in JP-A-2002-43063, JP-A-3239057, JP-A-3743005, JP-A-2000-106277, JP-A-2005-108727 Since the recombination region of this region widens, there is a problem that the light emission efficiency is lowered.
  • 3370011 discloses that rubrene for promoting energy transfer is added to a host dopant that does not easily generate energy transfer. Mixing is described. This is a technique limited to extracting red light emission from a host having a large excitation energy that is difficult to transfer energy, and the problem of efficiency reduction due to dopant concentration quenching still remains.
  • an object of the present invention is to provide an organic electroluminescence device capable of realizing both high efficiency and long life.
  • An organic electroluminescent device of the present invention for achieving such an object is an organic electroluminescent device in which an organic layer having at least a luminescent layer is sandwiched between an anode and a cathode. It is characterized by containing two or more dopants that emit light of similar colors.
  • the display device of the present invention is a display device in which organic electroluminescent elements each having an organic layer having at least a light emitting layer sandwiched between an anode and a cathode are arranged on a substrate.
  • organic electroluminescent elements each having an organic layer having at least a light emitting layer sandwiched between an anode and a cathode are arranged on a substrate.
  • the light emitting layer of the light emitting element contains two or more dopants that emit light of similar colors.
  • the light emitting layer contains two or more kinds of dopants that emit light of the same color
  • the light emitting layer contains one kind of dopant.
  • the luminous efficiency is increased.
  • different types of dopants are contained in the light emitting layer, stacking is suppressed, so that the total content of dopant can be increased without causing concentration quenching. As a result, the power S can be increased by extending the luminous life.
  • FIG. 1 is a cross-sectional view showing a configuration of an organic electroluminescent element according to an embodiment of the present invention.
  • FIG. 2 is a cross-sectional view showing a configuration of a conventional organic electroluminescent element.
  • FIG. 1 is a cross-sectional view showing a structural example of an organic electroluminescent element of the present invention.
  • An organic electroluminescent element 11 shown in this figure includes an anode 13 provided on a substrate 12, an organic layer 14 provided on the anode 13, and a cathode 15 provided on the organic layer 14. Yes.
  • the emitted light generated when the holes injected from the anode 13 and the electrons generated in the cathode 15 are combined in the light emitting layer 14c is expressed as the cathode 15 side force opposite to the substrate 12.
  • the configuration of the organic light emitting element 11 of the top emission type that is taken out will be described.
  • the substrate 12 on which the organic electroluminescent element 11 is provided is appropriately selected from a transparent substrate such as glass, a silicon substrate, a film-like flexible substrate, and the like.
  • a TFT substrate in which a TFT is provided for each pixel is used as the substrate 12.
  • the display device has a structure in which the top surface emission type organic electroluminescent element 11 is driven using a TFT.
  • the anode 13 provided as a lower electrode on the substrate 12 has a high work function from the vacuum level of the electrode material in order to efficiently inject holes, for example, chromium (Cr), gold (Au), tin oxide (SnO) and antimony (Sb) alloys, zinc oxide (ZnO) and aluminum (A1) alloys, silver (Ag) alloys, and oxidation of these metals and alloys Objects can be used alone or in a mixed state.
  • the anode 13 is made of a high reflectance material, so that it is possible to improve the light extraction efficiency to the outside due to the interference effect and the high reflectance effect.
  • an electrode material it is preferable to use, for example, an electrode mainly composed of Al, Ag or the like. Carrier injection efficiency can be increased by providing a transparent electrode material layer having a large work function such as ITO on these high reflectivity material layers.
  • the driving method of the display device configured using the organic electroluminescent element 11 is an active matrix method, the anode 13 is patterned for each pixel provided with a TFT. I will do it. An insulating film (not shown) is provided on the upper layer of the anode 13, and the surface of the anode 13 of each pixel is exposed from the opening of the insulating film.
  • the organic layer 14 is formed by laminating a hole injection layer 14a, a hole transport layer 14b, a light emitting layer 14c, and an electron transport layer 14d in this order from the anode 13 side.
  • Each of these layers consists of an organic layer formed by other methods such as vacuum deposition, for example, spin coating.
  • common materials are used for the hole injection layer 14a, the hole transport layer 14b, and the electron transport layer 14d.
  • the light emitting layer 14c contains two or more kinds of dopants that emit light of similar colors.
  • Examples of the luminescent dopant include laser dyes such as styrylbenzene dyes, oxazole dyes, perylene dyes, coumarin dyes, and atalidine dyes, anthracene derivatives, naphthacene derivatives, pentacene derivatives, and tarisene derivatives.
  • laser dyes such as styrylbenzene dyes, oxazole dyes, perylene dyes, coumarin dyes, and atalidine dyes, anthracene derivatives, naphthacene derivatives, pentacene derivatives, and tarisene derivatives.
  • Fluorescent materials are listed, and two or more types that emit light of the same color are selected from these materials. As a result, concentration quenching due to stacking when the dopant content is increased is suppressed as compared with the case where only one type of dopant is contained in the light emitting layer 14c.
  • the two or more dopants contained in the light emitting layer 14c preferably have a difference in fluorescence peak wavelength within 40 nm, preferably within 10 nm, when measured under the same conditions. S is more preferable. By using two or more dopants within this range, the same emission wavelength is exhibited, so that the generation of exciplex with a small energy level difference is suppressed. Moreover, when two or more kinds of dopants exhibit the same emission wavelength, an organic electroluminescence device having excellent visibility can be obtained.
  • Each dopant in the light emitting layer 14c The film thickness ratio is 0.5% to 15% in terms of film thickness ratio.
  • the blue emission wavelength range is 435 nm and 475 nm.
  • the blue emission dopant include boron compounds represented by the following structural formula (1) 5 and styrylbenzene represented by the following structural formula (2) —; System dyes, talycene derivatives represented by the following structural formula (3), and naphthacene derivatives represented by the following structural formula (4).
  • red emission wavelength range is 595 nm to 635 nm.
  • red emission dopants boron compounds represented by the following structural formulas (5)-!!-6, di-silanes represented by the following structural formulas (6)-!!-5 Examples include nomethylenepyran derivatives.
  • the green emission wavelength range is 495 nm to 535 nm
  • the electron transport layer 14d has, for example, an anthracene derivative, a phenantorin derivative, a silole derivative, or an azaal skeleton, and an alkali metal and an alkaline earth metal, or a lanthanoid (La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu) and metal oxides, composite oxides, and fluoride materials can be used.
  • lanthanoid La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu
  • an anthracene derivative, a phenantorin derivative, and a silole derivative which have particularly strong electron injection properties, can be used to efficiently generate a sufficient amount of electrons. This is preferable because it can be injected into 14c. This enables the recombination region to be localized when combined with the light-emitting layer 14c having the above-described configuration, and the injection factor (injection balance of electrons and holes into the light-emitting layer 14c) ⁇ is close to 1 and highly effective. In addition, the lifetime can be further increased.
  • each of the layers 14a to 14d constituting the organic layer 14 may have other requirements.
  • the light-emitting layer 14c is an electron-transporting light-emitting layer that also serves as the electron transport layer 14d. In other words, it may be a hole transporting light emitting layer that also serves as the hole transporting layer 14b.
  • each of the layers 14a to 14d may have a laminated structure.
  • the light emitting layer 14c may be formed of a laminated structure of a blue light emitting layer, a green light emitting layer, and a red light emitting layer to constitute an organic electroluminescent element that emits white light.
  • the cathode 15 only needs to have a structure in which a layer in contact with the organic layer 14 is formed using a material having a low work function and the light transmittance is good.
  • the cathode 15 has a structure in which a first layer 15a, a second layer 15b, and, in some cases, a third layer (not shown) are laminated in order from the anode 13 side.
  • the first layer 15a is configured using a material having a small work function and good light transmittance.
  • materials include alkali metal oxides such as Li 0, Cs 0, LiF, and CaF, alkali metal fluorides, alkaline earth metal oxides, and alkaline earth fluorides.
  • the second layer 15b is made of a material having optical transparency and good conductivity, such as a thin-film MgAg electrode or Ca electrode.
  • the organic electroluminescent element 11 is a top-surface light emitting element having a cavity structure in which emitted light is resonated and extracted between the anode 13 and the cathode 15 in particular, for example, transflective material such as Mg-Ag.
  • the second layer 15b is formed using a reflective material.
  • the third layer further laminated as necessary is made of, for example, a transparent lanthanide-based oxide, and is formed as a sealing electrode for suppressing electrode deterioration.
  • the first layer 15a, the second layer 15b, and the third layer described above are formed by a technique such as a vacuum evaporation method, a sputtering method, or a plasma CVD method.
  • the cathode 15 includes an insulating film and an organic layer 1 covering the periphery of the anode 13 (not shown here). 4 is formed as a solid film on the substrate 12 in a state of being insulated from the anode 13, and may be used as a common electrode for each pixel.
  • a display device in which such organic electroluminescent elements 11 are arranged on a substrate 12 has a scanning line and a signal for causing each of the organic electroluminescent elements 11 to emit light to the anode 13 and the cathode 15.
  • the line is connected.
  • the cathode 15 as the upper electrode is used as a common electrode, and the scanning line and the signal line are connected to the anode 13 via the TFT.
  • the organic electroluminescent element 11 is sealed between the sealing can that covers the display area in which the organic electroluminescent elements 11 are arranged and the substrate 12, or The organic electroluminescent element 11 is sealed in a resin filled between the substrate 12 and the counter substrate, thereby preventing deterioration of the organic material constituting the display element.
  • a light-transmitting resin is filled between the light-transmitting counter substrate and the substrate 12 and the organic electroluminescent element 11. It is preferable to have a structure that seals.
  • the light emitting layer 14c contains two or more dopants that emit light of the same color, only one type of dopant is contained in the light emitting layer 14c. Luminous efficiency becomes higher compared to the case where is contained. In addition, since the light emitting layer 14c contains a different kind of dopant, stacking is suppressed, so that the total content of the dopant can be increased. This can increase the light emission life. Therefore, it is possible to realize a display with low power consumption and excellent long-term reliability.
  • the organic electroluminescent element of the present invention is not limited to the organic electroluminescent element used in an active matrix type display device using a TFT substrate, and the organic electroluminescent element used in a passive type display device. The same effect can be obtained.
  • a passive display device one of the cathode 15 or the anode 13 is configured as a signal line and the other is configured as a scanning line.
  • the present invention can also be applied to a “transmission type” organic electroluminescence device that extracts light emission from the substrate 12 side by forming the substrate 12 from a transparent material.
  • the anode 13 on the substrate 12 made of a transparent material is configured using a transparent electrode material having a high work function such as ITO. Thereby, emitted light is extracted from both the substrate 12 side and the opposite side of the substrate 12.
  • the cathode 15 is made of a reflective material, so that emitted light is extracted only from the substrate 12 side.
  • a sealing electrode such as AuGe, Au, or Pt may be attached to the uppermost layer of the cathode 15.
  • the emitted light is emitted from the substrate 12 side.
  • a “transmission-type” organic electroluminescent element can be formed. Also in this case, the emitted light is extracted from both the substrate 12 side and the opposite side of the substrate 12 by changing the anode 13 serving as the upper electrode to a transparent electrode.
  • the organic electroluminescent element of the present invention described in the above embodiment can also be applied to a stack type organic electroluminescent element formed by laminating units of an organic layer having a light emitting layer.
  • the stack type is a multi-photon emission element (MPE element).
  • MPE element multi-photon emission element
  • a plurality of organic light emitting elements are electrically connected in series via an intermediate conductive layer.
  • the device is characterized by being bonded to.
  • Japanese Patent Application Laid-Open No. 2003-45676 and Japanese Patent Application Laid-Open No. 2003-272860 have disclosed a device configuration and a detailed example for realizing a manolet photon emission device. Has been. According to these, when 2 units of organic layers are stacked, ideally, lm / W does not change, cd / A is doubled, and when 3 layers are stacked, ideally It is stated that lm / W can triple cd / A without change.
  • the present invention when used in a stack type, the long life due to the improvement in efficiency by the stack type and the long life effect in the present invention have a synergistic effect, and the life is extremely long. An element can be obtained.
  • the organic electroluminescent element 1 having the configuration described with reference to FIG.
  • neodymium is formed as an anode 13 on a substrate 12 made of a glass plate of 30 mm ⁇ 30 mm.
  • An aluminum alloy layer containing 10 wt% (Nd) was formed with a thickness of 120 nm.
  • SiO A cell for an organic electroluminescent device was prepared by masking an area other than the light emitting region of 2 mm ⁇ 2 mm with an insulating film (not shown) by vapor deposition.
  • HI-406 manufactured by Idemitsu Kosan Co., Ltd. was formed as a hole injection layer 14a on the anode 13 by a vacuum evaporation method with a film thickness of 10 nm (deposition rate 0.2 to 0.4 nm / sec). .
  • HI-406 is a hole injecting material.
  • HT-320 manufactured by Idemitsu Kosan Co., Ltd. was formed at a thickness of 10 nm (deposition rate: 0.2 to 0.4 nm / sec) on the top thereof.
  • HT-320 is a hole transporting material.
  • a film having a 10 nm (deposition rate: O. lnm / sec) film is formed on the light-emitting layer 14c by a vacuum evaporation method using a phenantorin phosphorus derivative that also has a bathocuproine force as the electron transport layer 14d. Formed with thickness.
  • LiF was deposited as a first layer 15a of the cathode 15 by about 0.3 nm (deposition rate) by vacuum deposition.
  • MgAg was formed as a second layer 15b with a thickness of 10 nm by a vacuum deposition method, and a cathode 15 having a two-layer structure was provided.
  • an organic electroluminescent element was produced in the same manner as in Example 1 except that Alq3 was used instead of bathocuproine as the electron transport layer 14d.
  • Example 1 As Comparative Example 1 with respect to Examples 1 and 2 described above, an organic electroluminescence device was produced in the same manner as in Example 1 except that the light emitting layer 14c of Example 1 was changed.
  • the light-emitting layer 14c contains ADN shown in the structural formula (10) as a host, and contains only the styryl derivative shown in the structural formula (11) described above as a blue light-emitting dopant in a film thickness ratio of 5%. .
  • Example 2 As Comparative Example 2 with respect to Examples 1 and 2 described above, an organic electroluminescent device was produced in the same manner as in Example 1 except that the light emitting layer 14c of Example 1 was changed.
  • the light-emitting layer 14c uses the ADN shown in the structural formula (10) as a host and the blue light-emitting dopant as a structural formula (1
  • Example 3 As Comparative Example 3 with respect to Examples 1 and 2 described above, an organic electroluminescent device was produced in the same manner as in Example 1 except that the light emitting layer 14c of Example 1 was changed.
  • the light-emitting layer 14c uses the ADN shown in the structural formula (10) as a host and uses the above structural formula (
  • the organic electroluminescent elements of Examples 1 and 2 in which two or more kinds of blue luminescent dopants are contained in the light emitting layer 14c are comparative examples; compared with the organic electroluminescent elements of! As a result, it was confirmed that the voltage rise with a long emission lifetime of 400h or more was also suppressed to 0. IV or less.
  • the organic electroluminescent device of Example 1 using a phenantorin phosphorus derivative consisting of Basque mouth in the electron transport layer 14d is compared with the organic electroluminescent device of Example 2 using Alq3 for the electron transport layer 14d. As the electron injection efficiency increases, it is confirmed that the current efficiency increases as the voltage decreases. From the above, it was confirmed that high efficiency and long life can be realized by including two kinds of blue light emitting dopants in the light emitting layer 14c.

Abstract

L'invention concerne un dispositif électroluminescent organique et un dispositif d'affichage réalisant à la fois un haut rendement et une longue durée de vie. L'invention concerne de manière spécifique un dispositif électroluminescent organique (11) dans lequel une couche organique (14) est interposée entre une anode (13) et une cathode (15), et la couche organique (14) est constituée d'une couche d'injection de trous (14a), d'une couche de transport de trous (14b), d'une couche d'émission de lumière (14c), et d'une couche de transport d'électrons (14d) agencées dans cet ordre à partir du côté de l'anode (13). Ce dispositif électroluminescent organique (11) est caractérisé par le fait que la couche d'émission de lumière (14c) contient deux ou plusieurs types de dopants émettant des couleurs similaires. L'invention concerne également un dispositif d'affichage utilisant un tel dispositif électroluminescent organique.
PCT/JP2007/069026 2006-10-02 2007-09-28 Dispositif électroluminescent organique et dispositif d'affichage WO2008041642A1 (fr)

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JP2006-270358 2006-10-02
JP2006270358 2006-10-02
JP2007-230975 2007-09-06
JP2007230975A JP2008112976A (ja) 2006-10-02 2007-09-06 有機電界発光素子、表示装置、および電子機器

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JP2008091860A (ja) * 2006-09-06 2008-04-17 Fujifilm Corp 有機電界発光素子および表示装置

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