WO2016193256A1 - Composant électroluminescent organique et procédé de fabrication d'un composant électroluminescent organique - Google Patents

Composant électroluminescent organique et procédé de fabrication d'un composant électroluminescent organique Download PDF

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Publication number
WO2016193256A1
WO2016193256A1 PCT/EP2016/062255 EP2016062255W WO2016193256A1 WO 2016193256 A1 WO2016193256 A1 WO 2016193256A1 EP 2016062255 W EP2016062255 W EP 2016062255W WO 2016193256 A1 WO2016193256 A1 WO 2016193256A1
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Prior art keywords
layer
organic
conducting
organic light
light
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PCT/EP2016/062255
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German (de)
English (en)
Inventor
Dominik Pentlehner
Andreas Rausch
Daniel Riedel
Ulrich Niedermeier
Carola Diez
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Osram Oled Gmbh
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Publication of WO2016193256A1 publication Critical patent/WO2016193256A1/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]
    • H10K50/19—Tandem OLEDs

Definitions

  • An organic light-emitting component is specified. Furthermore, a method for producing an organic light-emitting component is specified. An object to be solved is to provide an organic light emitting device, the
  • the organic light-emitting component has an organically functional layer stack.
  • the Organic functional layer stack is arranged between two electrodes.
  • the organic functional layer stack has at least two organic light-emitting layers and at least one charge carrier generation layer.
  • Carrier generation layer is between the two
  • the carrier generation layer has a hole-conducting and electron-conducting organic layer, in particular a p- and an n-doped organic layer. Between the hole-conducting and electron-conducting organic layer, in particular the p- and n-doped organic layer, an intermediate layer is arranged.
  • the intermediate layer comprises or consists of a connecting material
  • the bonding material is oriented or oriented in the intermediate layer.
  • Connecting material has molecules.
  • the molecules point in each case at least one transition dipole moment for the light emitted by the component.
  • ⁇ cos 2 6> is greater than 1/3, so that absorption of the light emitted by the component light in the intermediate layer is reduced, where ⁇ is the angle between the respective
  • Transient dipole moment of the molecules of the bonding material and a layer normal N is.
  • Transition dipole moments are arranged parallel to the slice normal N with a maximum deviation of +/- 89 ° or +/- 45 ° from this parallel orientation.
  • IUPAC IUPAC Recommendation factor
  • Connecting materials preferably have an anisotropic orientation in the sum, in particular means that the orientation factor ⁇ ⁇ is not equal to 1/3.
  • the transition dipole moment is preferably aligned along the layer normal N.
  • the angle ⁇ is the angle between the respective transition dipole moment of the molecules of the bonding material and the layer normal N, wherein the layer normal N is arranged perpendicular to the intermediate layer.
  • the orientation factor ⁇ ⁇ is over all
  • ⁇ cos 2 6> is greater than 0.4; 0.5; 0.6; 0.7; 0.8; 0.9 or 0.95 or 1.
  • the larger ⁇ ⁇ the smaller the probability of absorption.
  • the organic light-emitting component is an organic
  • OLED light emitting diode
  • the light-emitting component has at least two organic light-emitting layers. This organic
  • light-emitting layers may be stacked vertically.
  • a higher vertically stacked organic light-emitting layers a higher vertically stacked organic light-emitting layers
  • the stacked organic light-emitting layers are separated by a carrier generation layer (CGL: "Charge Generation
  • Carrier generation layers such as internal anodes and
  • the organic light-emitting component has an organic functional layer stack.
  • the organic functional layer stack may include layers of organic polymers, organic oligomers,
  • organic monomers organic small, non-polymeric Have molecules ("small molecules") or combinations thereof.
  • the organic functional layer stack may be in addition to the at least two organic layers
  • light emitting layers have at least one functional layer, which is designed as a hole transport layer to allow an effective hole injection into at least one of the light emitting layers.
  • a functional layer which is designed as a hole transport layer to allow an effective hole injection into at least one of the light emitting layers.
  • tertiary amines, carbazole derivatives, polyaniline doped with camphorsulfonic acid, or polyethylenedioxythiophene doped with polystyrenesulfonic acid may prove advantageous as materials for a hole transport layer.
  • the organic functional layer stack can furthermore have at least one functional layer which can be used as a
  • Electron transport layer is formed.
  • the organic functional layer stack may comprise a plurality of organic functional layers selected from hole injection layers,
  • Electron transport layers hole blocking layers and
  • an organic light-emitting component has at least two electrodes, between which an organically functional layer stack is arranged.
  • At least one of the electrodes is transparent.
  • transparent here and below a layer is called, which is permeable to visible light.
  • the transparent layer may be transparent or at least partially light-scattering and / or partially light-absorbing, so that the transparent layer may also be diffuse or milky translucent, for example.
  • Particularly preferred is a layer designated here as transparent as possible
  • Layer stack of generated light is as low as possible.
  • both electrodes are transparent.
  • the light generated in the at least two light-emitting layers can be in both
  • one of the two electrodes, between which the organic functional layer stack is arranged is not selected to be transparent and preferably reflective, such that the light generated in the at least two light-emitting layers between the two electrodes only in one
  • TCO Transparent conductive oxides
  • metal oxides such as zinc oxide
  • Tin oxide Tin oxide, cadmium oxide, titanium oxide, indium oxide, indium tin oxide (ITO) or aluminum zinc oxide (AZO).
  • ITO indium oxide
  • AZO aluminum zinc oxide
  • Metal-oxygen compounds such as ZnO, Sn0 2 or ⁇ 2 ⁇ 3, ternary metal-oxygen compounds, such as Zn 2 Sn0 4, CdSn03, ZnSn03, Mgln 2 0 4, Galn03, ⁇ 2 ⁇ 2 ⁇ 5 or 4, Sn30i 2 or mixtures of different transparent conductive oxides to the group of TCOs.
  • TCOs do not necessarily correspond to one
  • stoichiometric composition and may also be p- or n-doped.
  • the organic light-emitting component has a substrate.
  • one of the two electrodes is arranged on the substrate.
  • the substrate may comprise, for example, one or more materials in the form of a layer, a plate, a foil or a laminate, which are selected from glass, quartz, plastic, metal, silicon wafers.
  • the substrate comprises or consists of glass.
  • the organic light-emitting component has a
  • Carrier generation layer is between the two
  • the Charge generating layer also known as
  • Charge generation layer (CGL) can be referred to, is in particular formed as a tunnel junction forming pn junction, which is operated in the reverse direction and which can be used for an effective charge separation and thus for the generation of charge carriers.
  • the carrier generation layer connects at least the two organic light emitting layers to each other.
  • the stability of the device can be increased.
  • the carrier generation layer may be formed of insulating materials such as alumina.
  • the charge carrier generation layer constitutes a tunneling barrier for the charge carriers.
  • the charge carrier generation layer separates the hole-conducting and electron-conducting organic layers, in particular the p- and n-doped organic layers, which otherwise
  • Phthalocyanines have intermediate states that increase the tunneling probability.
  • the charge carriers can be between the
  • the transport of cargo is possible not only by tunneling but also by hopping. This can increase the efficiency of the device.
  • the hopping mechanism of intermediate state to intermediate state of the phthalocyanines move.
  • Charge generating layer a hole-conducting
  • electron-conducting organic layer in particular a p- and n-doped organic layer.
  • p- and / or n-doped organic layer is here and below
  • Charge carrier type is different, which is different from the organic layer.
  • p-doped means that the organic layer is electron-conducting.
  • n-doping means that the organic layer is hole-conducting.
  • Suitable materials for a hole-conducting and electron-conducting organic layer, in particular a p- and / or n-doped organic layer, are any materials which are electron-conducting and / or hole-conducting.
  • Charge generating layer between the hole-conducting and electron-conducting organic layer, in particular the p- and n-doped organic layer an intermediate layer.
  • the hole-conducting and electron-conducting organic layer, in particular the p- and n-doped organic layer are connected to one another via this intermediate layer. This means that the interlayer in
  • electron-conducting organic layer in particular p- and n-doped organic layer is arranged.
  • the intermediate layer is formed of the bonding material, that is, consists of the bonding material.
  • Connecting material is oriented or oriented in the intermediate layer.
  • oriented or aligned here and hereinafter means that the bonding material and / or the molecules of the bonding material and / or the transitional dipole moment of the molecules occupy a preferred direction in the intermediate layer.
  • the bonding material has molecules.
  • the molecules have a transitional dipole moment, especially several transition dipole moments.
  • the molecules have at least one transition dipole moment for the light emitted and / or generated by the device.
  • transition dipole moments are arranged parallel to the layer normal.
  • the transition dipole moments of the molecules may alternatively or additionally be deviated by up to +/- 89 °, for example +/- 85 °, 80 °, 70 °, 60 °, 50 °, 40 °, 35 °, 30 °, 25 °, 20 °, 15 °, 10 ° or 5 ° from this parallel orientation.
  • all transition dipole moments of the molecules have a parallel arrangement +/- 45 ° to the layer normal.
  • ⁇ cos 2 6> is greater than 0.4; 0.5; 0.6; 0.7; 0.8; 0.9 or 0.95 or equal to 1.
  • the transitional dipole moment has a fixed direction in the
  • transition dipole moment is referred to in particular: "IUPAC Compendium of Chemical Terminology, Second Edition (The” Gold Book "), 1997 and IUPAC Compendium of Chemical
  • all molecules of the bonding material have a transitional dipole moment which is parallel to the layer normal with a maximum deviation of +/- 45 ° therefrom
  • Alignment for example, 30 °, are arranged.
  • At least 50% or 60% or 70% or 80% or 90% or 95% of all molecules of the bonding material have a transitional dipole moment parallel to the layer normal N with a maximum deviation of +/- 45 ° from this parallel orientation is arranged.
  • ⁇ cos 2 6> is greater than 0.4; 0.5; 0.6; 0.7; 0.8; 0.9 or 0.95 or 1.
  • the transition dipole moments have a certain orientation in the intermediate layer. This is relevant because the absorption and / or emission process is a dipole transition.
  • the absorption of the light emitted by the device in the intermediate layer can be reduced compared to a device having transition dipole moments perpendicular to the layer
  • the interlayer of the device of the invention absorbs less light generated by the device. This allows more light emitted from the device so that the efficiency of the light extraction from the organic light emitting device can be increased.
  • Isotropically oriented bonding material may absorb the light generated by the device due to intermediate states. By orienting the bonding material in the intermediate layer, the absorption can be reduced. According to at least one embodiment, the
  • Charge generating layer in addition to a metal layer.
  • the metal layer has a surface.
  • the metal layer may adjoin the intermediate layer.
  • the metal layer is directly on the
  • the intermediate layer which is the
  • Compound material is in particular covalently bonded to the surface of the metal layer.
  • Connecting material forms a self-organizing
  • SAM Monolayer
  • the metal layer comprises or consists of the metal selected from the group consisting of copper, silver, gold, and aluminum includes.
  • the metal layer is a thin one
  • the metal layer for example with a thickness of greater than or equal to 0.1 nm and less than or equal to 5 nm.
  • the metal layer has a layer thickness of less than 1 nm, for example 0.4 or 0.8 nm.
  • the metal layer is selected from a metal comprising copper, silver or gold, wherein the metal layer has a layer thickness smaller than 1 nm and wherein the compound material comprises sulfur and wherein the sulfur is in contact with the surface of the
  • Metal layer is covalently connected via a metal-sulfur bond.
  • the metal layer is directly arranged on the hole-conducting and / or electron-conducting organic layer, in particular p- and / or n-doped organic layer.
  • the compound material has a sulfur-containing functional group, for example a thiol group.
  • the metal layer is formed of gold with a gold-sulfur covalent bond joining the metal layer and the intermediate layer.
  • self-assembled monolayer so-called self-assembly monolayers or SAMs.
  • SAMs self-assembly monolayers
  • materials for the compound material there may be used common organic materials, for example, phthalocyanines.
  • the materials may be conjugated, that is aromatic, or unconjugated, that is non-aromatic.
  • the molecular chain length of the material can be different.
  • the phthalocyanines may be substituted with thiol groups. Due to the molecular structure of the phthalocyanines and the hybridization of the phthalocyanines, the thiol groups are always oriented in the molecular level of the compound material. Also, the transition dipole moment for that of the device
  • the compound material may have multiple thiol groups.
  • the thiol groups act here as anchor groups which covalently bond to the metal layer.
  • strong covalent bonding results when the metal layer is a gold layer.
  • the connecting material may be a symmetrical or
  • asymmetric here and below is meant that the bonding material has a permanent electric dipole moment due to the molecular structure.
  • Symmetric means that the molecule has no permanent electrical dipole moment.
  • An asymmetric compound material can be obtained, for example, by unilateral attachment of sulfur-containing groups
  • Phthalocyanines are produced. In accordance with at least one embodiment, this is
  • Compound material is a substituted phthalocyanine, a substituted aromatic, octylphosphonic acid and / or a substituted heteroaromatic.
  • Phthalocyanine a sulfur-substituted aromatic
  • Vanadyl phthalocyanine or a sulfur-substituted titanyl phthalocyanine have
  • octylphosphonic acid is used as the compound material.
  • Octylphosphonic acid forms, in particular, self-assembling monolayers.
  • Octylphosphonic acid can be separated from the gas phase.
  • Carrier generation layer can reduce the absorption losses in the device and the efficiency can be increased. At the same time, these intermediate layers have a high
  • the metal layers can be used as seed layers.
  • the metal layers can simultaneously serve as a source of charge carriers in the charge generation layer
  • the charge carrier generating layer may be used, so that it may be possible to dispense with a doping in the charge carrier generating layer.
  • Carrier generation layer has a layer thickness between 1 nm and 8 nm, in particular between 4 nm and 5 nm,
  • the intermediate layer can be a
  • Layer thickness between 1 nm and 3 nm, for example, 2 nm.
  • Charge generating layer has a layer thickness of less than 5 nm.
  • the permanent dipole moments are predominantly parallel to the layer normal N with a maximum deviation of +/- 45 °, 30 °, 20 ° or 15 ° from this parallel
  • Transient dipole moments predominantly parallel, in particular parallel, arranged to the permanent dipole moment.
  • Amphiphile is here and hereinafter referred to that the bonding material is both a hydrophilic, so
  • ⁇ cos 2 6> is greater than 1/3; 0.4; 0.5; 0.6; 0.7; 0.8; 0.9 or 0.95 or equal to 1. According to at least one embodiment, this is
  • Dipole moment wherein the permanent dipole moment is arranged mainly parallel to the Schichtnormalen with a maximum deviation of +/- 30 ° or 45 ° from this parallel orientation.
  • the hole-conducting and / or electron-conducting organic layer in particular p- and / or n-doped organic layer may be a hydrophilic
  • the connecting material has
  • hydrophilic and hydrophobic areas hydrophilic and hydrophobic areas.
  • the absorption can be minimized and thus the efficiency can be increased.
  • the transition dipole moment and the permanent dipole moment of a molecule are arranged parallel to each other.
  • Bonding materials may be selected from a group including carboxylate groups, hydroxyls, amines, primary
  • the hole-conducting and / or electron-conducting organic layer in particular p- and / or n-doped organic layer, has a hydrophobic surface.
  • the hydrophobic surface may in particular be aliphatic saturated radicals, methyl groups or
  • the bonding material has a hydrophilic and hydrophobic area.
  • the hydrophobic region of the bonding material is oriented to the hydrophobic surface of the hole-conducting and / or
  • Connecting material can be generated in the intermediate layer.
  • the amphiphilic molecules organize themselves in the layer due to entropic effects and their
  • organic light-emitting device also for that
  • the method for producing an organic light-emitting component comprises the following method steps:
  • Transition dipole moment for the emitted light from the device wherein: ⁇ cos 2 6> greater than 1/3, so that absorption of the light emitted by the device light is reduced in the intermediate layer, where ⁇ is the angle between the respective transition dipole moment of the molecules of the
  • the organic layer applied in step C) is a hole-conducting organic layer and that in the
  • organic layer a hole-conducting organic layer.
  • the one layer is arranged directly in direct mechanical and / or electrical contact with the other layer. It can also continue
  • the one layer is arranged indirectly above another layer. In this case, further layers can then be arranged between the one and the other layer.
  • step D1) applying a metal layer of copper, silver or gold to the organic layer produced under step C) by means of vacuum evaporation, wherein a metal layer having a layer thickness of less than 5 nm, in particular less than 1 nm is produced.
  • the bonding material can be applied to the metal layer.
  • the bonding material may comprise sulfur and then covalently bonds to the metal layer via a metal-sulfur bond, in particular to the surface of the metal layer, for example gold.
  • the transition dipole moments of the molecules of the bonding material in this intermediate layer can in particular be a parallel arrangement to the layer normal with a maximum deviation of +/- 30 ° from this parallel arrangement.
  • ⁇ cos 2 6> is greater than 1/3 or greater than 0.8.
  • an oriented intermediate layer can be produced without additional process steps
  • Intermediate layer in step D) generated from the gas phase. This can be done by means of vacuum evaporation. In this case, an oriented intermediate layer can be produced during the production without additional process steps being necessary. This saves time and costs.
  • Connecting material can be selected.
  • Additional materials may also be blended into the interlayer to adjust viscosity or surface energy. Above all, additional solvents or further fillers with polar and / or nonpolar serve
  • fillers may be added which have functional groups selected from: -COO (carboxylate), -SO 3 (sulfonate) or -SO 4 (sulfate).
  • the alignment of the bonding material in step D) takes place at low Temperatures, for example, temperatures less than 50 ° C. At such low temperatures, alignment with external fields can not be achieved, therefore, according to the present invention, self-assembly of the molecules of the bonding material is resorted to.
  • the inventors have realized that by using an oriented intermediate layer in the
  • a charge generation layer (charge generation layer), an organic light-emitting device can be provided, which absorbs little and thus the efficiency of the device can be increased. This can be done by the
  • the connecting material then has a
  • Influence on the morphology can be done by the orientation of the connecting material.
  • a device which has a potential increased stability through the uniform
  • Alignment of the molecules can be generated in the intermediate layer.
  • the intermediate layer can be homogeneous.
  • FIG. 1 shows a schematic representation of an organic light-emitting component according to an exemplary embodiment
  • FIGS. 2A to 2C show the schematic representation of a FIG
  • Figures 3A and 3B is a schematic representation of a
  • Embodiment, and Figures 4A and 4B is a schematic representation of a
  • FIG. 1 shows a schematic representation of an organic light-emitting component 100 in accordance with FIG. 1
  • Embodiment comprising a substrate 1, for example made of glass.
  • a substrate 1 for example made of glass.
  • an organically functional layer stack 9 between two electrodes 2 and 8 is optionally functional layer stack 9 between two electrodes 2 and 8.
  • the organic functional layer stack 9 has at least two organic light-emitting layers 4 and 6.
  • the organic light-emitting layers 4 and 6 can be any organic light-emitting layers 4 and 6.
  • the carrier generation layer 5 has a hole-conducting and electron-conducting organic layer, in particular a p- and an n-doped organic layer 51, 53. Between these two layers is one
  • the lower electrode 2 may be formed as an anode and the upper electrode 8 as a cathode.
  • the lower electrode 2 may be formed as a cathode and the upper electrode 8 as an anode.
  • the upper electrode 8 may be formed as a cathode and the upper electrode 8 as an anode.
  • the organic layer 51 p- or n-doped. If the organic layer is n-doped, for example, then the organic layer 52 is p-doped and vice versa.
  • the organic functional layer stack 9 may also be possible for the organic functional layer stack 9 to have more than two organic light-emitting layers, in each case one between each two directly adjacent organic light-emitting layers
  • Charge carrier generating layer may be arranged.
  • the organic functional layer stack 9 may have, in addition to the described organic functional layers 4 and 6, further organic functional layers. In the embodiment shown are purely exemplary
  • Charge carrier injection and / or transport layers 3 and 7 are shown which, depending on the polarity of the electrodes 2, 7, are hole- or electron-conducting.
  • an encapsulation arrangement preferably in the form of a thin-layer encapsulation, may be applied over the electrodes 2, 8 and the organic functional layer stack 9 (not shown), around the organic light-emitting component 100 and in particular the layers of the organic functional layer stack 9 and the electrodes 2, 8 to protect against harmful environmental materials such as moisture and / or oxygen and / or other corrosive substances such as hydrogen sulfide.
  • FIGS. 2A to 2C each show a section of an organic light-emitting component 100 according to an embodiment.
  • FIGS. 2A to 2C each show an intermediate layer 52 which has the bonding material 11.
  • the bonding material 11 has molecules each having at least one transition dipole moment 13 for the light emitted by the device.
  • Figures 2A and 2B show that the transition dipole moments parallel to
  • FIGS. 2A to 2C show that the transition dipole moments 13 of the bonding material 11 has a deviation of about 10 ° from the parallel arrangement to the layer normal.
  • FIGS. 3A and 3B show a section of an organic light-emitting component 100 according to one each
  • FIG. 3A shows a hole-conducting and electron-conducting organic layer, in particular p- and n-doped organic layer 51, 53.
  • a metal layer 13 is arranged directly on at least one organic layer 51, 53.
  • the metal layer 13 is in particular made of gold.
  • the metal layer 13 is arranged directly downstream of a
  • the organic layer 51 may be n-doped and the organic layer 53 may be p-doped.
  • the metal layer 13 may also be attached to the organic layer 51
  • the organic layer 51 may be n-doped and the organic layer 53 may be p-doped or vice versa.
  • Figures 4A and 4B show a section of a
  • organic light-emitting device 100 according to one embodiment. Between the hole-leading and
  • an intermediate layer 52 may be arranged.
  • the intermediate layer 52 has a
  • Amphiphile means here that the compound material has a hydrophilic region IIa and a hydrophobic region IIb.
  • the organic layer 53 which may be p- or n-doped, has a hydrophilic surface.
  • the surface of the other organic layer 51 may be hydrophobic. Thereby, that the surfaces of the hole-conducting and / or
  • Area IIa is oriented to the hydrophilic surface of the hole-conducting or electron-conducting organic layer, in particular p- or n-doped organic layer 53 and that the hydrophobic region IIb of the bonding material 11 in the direction of the hydrophobic surface of the other hole-conducting or electron-conducting organic layer, in particular p - or n-doped organic layer 51 oriented. This can be an orientation of the
  • the organic layer 51 may be p-doped and the organic layer 53 may be n-doped or
  • FIG. 4B shows the opposite case to FIG. 4A.
  • FIG. 4B shows that the organic layer 51 has a
  • hydrophilic surface has hydrophilic surface and the organic layer 53 has a hydrophobic surface. This can be a
  • Embodiments and their features can also be combined with each other according to further embodiments, even if such combinations are not explicitly shown in the figures. Furthermore, the embodiments described in connection with FIGS additional or have alternative features as described in the general part.

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un composant électroluminescent organique (100) présentant une pile de couches fonctionnelles organiques (9) entre deux électrodes (2, 8). La pile de couches fonctionnelles organiques (9) comprend au moins deux couches électroluminescentes organiques (4, 6) et au moins une couche génératrice de porteurs de charge (5) qui est disposée entre les deux couches électroluminescentes organiques (4, 6); la couche génératrice de porteurs de charge (5) comprend une couche organique conductrice de trous et une couche organique conductrice d'électrons (51,53), entre lesquelles est disposée une couche intermédiaire (52); la couche intermédiaire (52) comporte un matériau de liaison (11), qui est orienté dans la couche intermédiaire (52); des molécules du matériau de liaison (11) comprennent chacune au moins un moment dipolaire de transition (13) pour la lumière émise par le composant, <cos2ϴ> étant supérieur à 1/3 de sorte qu'une absorption de la lumière émise par le composant est réduite dans la couche intermédiaire (52), ϴ étant l'angle entre le moment dipolaire de transition (13) de chaque molécule du matériau de liaison (11) et une normale aux couches (N).
PCT/EP2016/062255 2015-06-03 2016-05-31 Composant électroluminescent organique et procédé de fabrication d'un composant électroluminescent organique WO2016193256A1 (fr)

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