US20140225100A1 - Organic electroluminescent device - Google Patents

Organic electroluminescent device Download PDF

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US20140225100A1
US20140225100A1 US14/343,530 US201214343530A US2014225100A1 US 20140225100 A1 US20140225100 A1 US 20140225100A1 US 201214343530 A US201214343530 A US 201214343530A US 2014225100 A1 US2014225100 A1 US 2014225100A1
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capping layer
substituted
organic electroluminescent
electroluminescent device
carbon atoms
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Norimasa Yokoyama
Shuichi Hayashi
Shigeru Kusano
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Hodogaya Chemical Co Ltd
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Definitions

  • the present invention relates to an organic electroluminescent device (hereinafter referred to as an organic EL device) which is a preferred self-luminous device for various display devices. Specifically, this invention relates to an organic EL device using a specific arylamine derivative, particularly an organic EL device greatly improved in light extraction efficiency.
  • the organic EL device is a self-luminous device and has been actively studied for their brighter, superior visibility and the ability to display clearer images in comparison with liquid crystal devices.
  • an electroluminescence device that includes an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode successively formed on a substrate, wherein high efficiency and durability are achieved by a light emitting device of bottom emission structure that emits light from the bottom (refer to Non-Patent Document. 1, for example).
  • Light emitting devices of op emission structure that emit light from die top using metal with a high work function as an anode have been used in recent years. Unlike the light emitting device of bottom emission structure restricted in the area of a light emitting part by a pixel circuit, the light emitting device of top emission structure has an advantage of having a wide light emitting part.
  • a semitransparent electrode of LiF/Al/Ag (refer to Non-patent document 2, for example), Ca/Mg (refer to Non-patent document 3, for example), LiF/MgAg, or the like is used as a cathode.
  • the capping layer in the light emitting device of top emission structure has an effect that the light emitting device using Ir(ppy) 3 as a light emitting material has a current efficiency of 38 cd/A in the case of having no capping layer, while a light emitting device using ZnSe with a film thickness of 60 nm as the capping layer has a current efficiency of 64 cd/A, that the efficiency improvement of about 1.7 times is recognized. It is also indicated that the maximum point of transmittance of the semitransparent electrode and the capping layer does not necessarily coincide with the maximum point of efficiency, and it is indicated that the maximum point of light extraction efficiency is determined by an interference effect (refer to Non-patent document for example).
  • the use of a metal mask of high definition is proposed for the formation of the capping layer.
  • a metal mask of high definition there has been a problem of worsening alignment accuracy due to distortion caused by heat. That is, ZnSe has a high melting point of 1,100° C. or higher (refer to Non-patent document 3, for example), and vapor deposition in an accurate position is impeded in the mask of high definition.
  • Many inorganic substances have high vapor deposition temperatures and are unsuitable for the use of the mask of high definition, and there is a possibility of damaging the light emitting device itself. Further, since the light emitting device is damaged in film formation by a sputtering method, the capping layer containing an inorganic substance as a constitutive material cannot be used.
  • Alq 3 tris(8-hydroxyquinoline) aluminum
  • Alq 3 is known as an organic EL material generally used as a green light emitting material or an electron transport material, it has weak absorption in the vicinity of 450 nm used for a blue light emitting device. In consequence, there has been a problem of causing a decrease in color purity and a decrease in light extraction efficiency in the case of the blue light emitting device.
  • a material having a high refractive index and excelling in thin film stability and durability is demanded as a material for the capping layer to improve device characteristics of the organic EL device, particularly to greatly improve light extraction efficiency.
  • An object of the present invention is to provide an organic EL device having a capping layer composed of a material having a high refractive index, excelling in thin film stability and durability and having no absorption in the respective wavelength regions of blue, green and red colors to improve device characteristics of the organic EL device, particularly to greatly improve light extraction efficiency.
  • Physical properties of the material of the capping layer suitable for the present invention include (1) a high refractive index, (2) vapor deposition ability without causing thermal decomposition, (3) a stable thin film state, and (4) a high glass transition temperature.
  • Physical properties of the device suitable for the present invention include (1) high light extraction efficiency, (2) no decrease in color purity, (3) light transmission without changes with the lapse of time, and (4) a lona life.
  • an arylamine-based material excels in thin film stability and durability, selected a specific arylamine compound with a high refractive index, produced an organic EL device using the specific arylamine compound as a material for composing a capping layer, and completed the present invention after thorough evaluations of the device characteristics.
  • the following organic EL device is provided according to the present invention.
  • An organic EL device including at least an anode electrode, a hole transport layer, a light emitting layer, an electron transport layer, a cathode electrode and a capping layer in this order, wherein the capping layer includes an arylamine compound (X) having a structure in which two triphenylamine structures are joined within molecule via a single bond or a divalent group that does not contain a heteroatom.
  • X arylamine compound having a structure in which two triphenylamine structures are joined within molecule via a single bond or a divalent group that does not contain a heteroatom.
  • R 1 to R 28 may be the same or different, and each represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano, trifluoromethyl, nitro, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic: group, a substituted or unsubstituted condensed polycyclic aromatic group, or substituted or unsubstituted aryloxy.
  • R 1 to R 10 and R 19 to R 28 may form rings by binding to benzene rings to which the respective groups bind.
  • A represents a divalent group represented by the following structural formulae (B) to (F), or a single bond, where when A is a single bond, at least one of R 1 to R a is a substituted or unsubstituted aromatic hydrocarbon group.
  • R 29 to R 32 may be the same or different, and each represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano, trifluoromethyl, linear or branched alkyl of 1 to 6 carbon atoms, linear or branched alkenyl of 2 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.
  • R 29 to R 32 may be the same or different.
  • R 33 to R 42 may be the same or different, and each represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano, trifluoromethyl, linear or branched alkyl of 1 to 6 carbon atoms, linear or branched alkenyl of 2 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group. These substituents may bind to each other to form a ring.
  • R 43 to R 50 may be the same or different, and each represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano, trifluoromethyl, linear or branched alkyl of 1 to 6 carbon atoms, linear or branched alkenyl of 2 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group. These substituents may bind to each other to form a ring.
  • R 51 to R 5s may be the same or different, and each represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano, trifluoromethyl, linear or branched alkyl of 1 to 6 carbon atoms, linear or branched alkenyl of 2 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group. These substituents may bind to each other to form a ring.
  • linear or branched alkyl of 1 to 6 carbon atoms examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, vinyl,
  • R 1 to R 10 and R 19 to R 28 may form rings by binding to benzene rings to which the respective groups bind, via a single bond, substituted or unsubstituted methylene, an oxygen atom, a sulfur atom, or N—Ar.
  • N in “N—Ar” represents a nitrogen atom
  • “Ar” represents a “substituted or unsubstituted aromatic hydrocarbon group”, a “substituted or unsubstituted aromatic heterocyclic group”, or a “substituted or unsubstituted condensed polycyclic aromatic group”, and can be the same groups exemplified as the aromatic hydrocarbon group, the aromatic heterocyclic group or the condensed polycyclic aromatic group in R 1 to R 28 below. Substituents that these groups may have can be the same substituents exemplified for the same groups in R 1 to R 2e below.
  • the “substituent” in the “linear or branched alkyl of 1 to 6 carbon atoms that has a substituent”, the “cycloalkyl of 5 to 10 carbon atoms that has a substituent”, or the “linear or branched alkenyl of 2 to 6 carbon atoms that has a substituent” represented by R 1 to R 28 in the general formula (1) include a deuterium atom; trifluoromethyl; cyano; nitro; halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; linear or branched alkyls of 1 to 6 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl; linear
  • R 1 to R 10 and R 19 to R 2e may form rings by binding to benzene rings to which the respective groups bind, via a single bond, substituted or unsubstituted methylene, an oxygen atom, a sulfur atom, or N—Ar.
  • N in “N—Ar” represents a nitrogen atom
  • “Ar” represents a “substituted or unsubstituted aromatic hydrocarbon group”, a “substituted or unsubstituted aromatic heterocyclic group”, or a “substituted or unsubstituted condensed polycyclic aromatic group”, and can be the same groups exemplified as the aromatic hydrocarbon group, the aromatic heterocyclic group or the condensed polycyclic aromatic group in R 1 to R 28 below. Substituents that these groups may have can be the same substituents exemplified for the same groups in R 1 to R 28 below.
  • substituted in the “linear or branched alkyloxy of 1 to 6 carbon atoms that has a substituent” or the “cycloalkyloxy of 5 to 10 carbon atoms that has a substituent” represented by R 1 to R 28 in the general formula (1) include a deuterium atom; trifluoromethyl; cyano; nitro; halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; linear or branched alkyls of 1 to 6 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl; linear or branched alkyloxys of 1 to 6 carbon atoms such as methyloxy, ethyl, n-propy
  • aromatic hydrocarbon group the “aromatic heterocyclic group”, or the “condensed polycyclic aromatic group” in the “substituted or unsubstituted aromatic hydrocarbon group”, the “substituted or unsubstituted aromatic heterocyclic group”, or the “substituted or unsubstituted condensed polycyclic aromatic group” represented by R 1 to R 2e in the general formula (1)
  • R 1 to R 10 and R 19 to R 28 may form rings by binding to benzene rings to which the respective groups bind, via a single bond, substituted or unsubstituted methylene, an oxygen atom, a sulfur atom, or N—Ar.
  • N in “N—Ar” represents a nitrogen atom
  • Ar represents a “substituted or unsubstituted aromatic hydrocarbon group”, a “substituted or unsubstituted aromatic heterocyclic group”, or a “substituted or unsubstituted condensed polycyclic aromatic group”, and can be the same groups as exemplified above.
  • Substituents that these groups may have can be the same substituents as exemplified below.
  • substituted aromatic hydrocarbon group examples include a deuterium atom; cyano; trifluoromethyl; nitro; halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; linear or branched alkyls of 1 to 6 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl; cycloalkyls of 5 to 10 carbon atoms such as cyclopentyl and cyclohexyl; linear or branched alkyls of 1 to 6 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl
  • aryloxy in the “substituted or unsubstituted aryloxy” represented by R 1 to R 28 in general formula (1) include phenyloxy, tolyloxy, biphenylyloxy, terphenylyloxy, naphthyloxy, anthryloxy, phenanthryloxy, fluorenyloxy, indenyloxy, pyrenyloxy, and perylenyloxy. These substituents may bind to each other to form a ring.
  • R 1 to R 10 and R 19 to R 28 may form rings by binding to benzene rings to which the respective groups bind, via a single bond, substituted or unsubstituted methylene, an oxygen atom, a sulfur atom, or N—Ar.
  • N in “N—Ar” represents a nitrogen atom
  • “Ar” represents a “substituted or unsubstituted aromatic hydrocarbon group”, a “substituted or unsubstituted aromatic heterocyclic group”, or a “substituted or unsubstituted condensed polycyclic aromatic group”, and can be the same groups exemplified as the aromatic hydrocarbon group, the aromatic heterocyclic group or the condensed polycyclic aromatic group in R 1 to R 28 above. Substituents that these groups may have can be the same substituents exemplified for the same groups in R 1 to R 28 above.
  • substituted aryloxy represented by R 1 to R 2e in general formula (1)
  • substituents include a deuterium atom; cyano; trifluoromethyl; nitro; halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; linear or branched alkyls of 1 to 6 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl; cycloalkyls of 5 to 10 carbon atoms such as cyclopentyl and cyclohexyl; linear or branched alkenyls of 2 to 6 carbon atoms such as vinyl, allyl, 2-butenyl, and
  • linear or branched alkyls of 1 to 6 carbon atoms or the “linear or branched alkenyls of 2 to 6 carbon atoms” represented by R 29 to R 55 in structural formulae (B) to (D) and (F), corresponding to A in general formula (1), include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, vinyl, allyl, isopropenyl, and 2-butenyl.
  • substituents may form a ring by binding to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom. In the case of forming the ring, it is preferable that the substituents bind to each other via a single bond or dimethylmethylene to form the ring.
  • aromatic hydrocarbon group the “aromatic heterocyclic group”, or the “condensed polycyclic aromatic group” in the “substituted or unsubstituted aromatic hydrocarbon group”, the “substituted or unsubstituted aromatic heterocyclic group”, or the “substituted or unsubstituted condensed polycyclic aromatic group” represented by R 29 to R 55 in structural formulae (B) to (D) and (F), corresponding to A in general formula (1), include phenyl, biphenylyl, terphenylyl, tetrakisphenyl, styryl, naphthyl, anthryl, acenaphthenyl, fluorenyl, phenanthryl, indenyl, pyrenyl, pyridyl, pyrimidyl, furanyl, pyrrolyl, thienyl, quinolyl, isoquinolyl, benzofuranyl,
  • substituents may form a ring by binding to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom when a plurality of these substituents bind to the same benzene ring.
  • substituents bind to each other via a single bond or dimethylmethylene to form the ring.
  • substituted aromatic hydrocarbon group “substituted aromatic heterocyclic group”, or “substituted condensed polycyclic aromatic group” represented by R 29 to R 55 in structural formulae (B) to (D) and (F), corresponding to A in general formula (1), include a deuterium atom, a fluorine atom, a chlorine atom, trifluoromethyl, linear or branched alkyl of 1 to 6 carbon atoms, phenyl, biphenylyl, terphenylyl, tetrakisphenyl, styryl, naphthyl, fluorenyl, phenanthryl, indenyl, and pyrenyl.
  • substituents may be further substituted. These substituents may form a ring by binding to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom. In the case of forming the ring, it is preferable that the substituents bind to each other via a single bond or dimethylmethylene to form the ring.
  • the arylamine compound (X) having a structure in which two triphenylamine structures are joined within a molecule via a single bond or a divalent group that does not contain a heteroatom for use in the organic EL device of the present invention, can be used as a constitutive material of a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, or a capping layer of an organic EL device.
  • the thickness of the capping layer is preferably in a range of 30 nm to 120 nm, further preferably in a range of 40 nm to 80 nm.
  • the refractive index of the capping layer when the wavelength of light transmitted through the capping layer is within a range of 530 nm to 750 nm is preferably 1.75 or more, further preferably 1.80 or more.
  • the capping layer may be prepared by laminating two or more kinds of different constitutive materials.
  • the organic EL device of the present invention can be greatly improved in light extraction efficiency because of having the capping layer that is provided outside the transparent or semitransparent electrode and that has a refractive index higher than that of the semitransparent electrode. Since a specific arylamine compound having a structure in which two triphenylamine structures are joined within a molecule via a single bond or a divalent group that does not contain a heteroatom, is used for the capping layer, a film can be formed at a temperature of 400° C. or lower to prevent the damage of a light emitting device. Further, a high-definition mask is used to optimize the extraction efficiency of light of each color, and the organic EL device can be suitably applied to a full-color display to permit the display of a clear, light image with high color purity.
  • the organic EL device of the present invention since a material for the organic EL device having a high refractive index and excelling in thin film stability and durability is used as the material for the capping layer, light extraction efficiency can be greatly improved in comparison with conventional organic EL devices. Further, the organic EL device of high efficiency with a long life can be achieved.
  • FIG. 1 is a diagram illustrating the configuration of the organic EL devices of Examples 3 to 10 and Comparative Example 1.
  • the arylamine compound having a structure in which two triphenylamine structures are joined within a molecule via a single bond or a divalent group that does not contain a heteroatom represented by the general formula (1) and suitably used for the organic EL device of the present invention, may be synthesized by a known method (refer to Patent documents 3 to 5, for example).
  • arylamine compounds (X′) each having a structure in which two triphenylamine structures are joined within a molecule via a single bond or a divalent group that does not contain a heteroatom, represented by the general formula (1) and suitably used for the organic EL device of the present invention.
  • the present invention is not restricted to these compounds.
  • arylamine compounds (X′) each having a structure in which two triphenylamine structures are joined within a molecule via a single bond or a divalent group that does not contain a heteroatom, represented by the general formula (1) in the arylamine compounds (X) each having a structure in which two triphenylamine structures are joined within a molecule via a single bond or a divalent group that does not contain a heteroatom, suitably used for the organic EL device of the present invention.
  • the present invention is not restricted to these compounds.
  • These compounds were purified by methods such as column chromatography, adsorption using silica gel, activated carbon, activated clay, or the like, and recrystallization or crystallization using a solvent, and purified by sublimation or the like in the end.
  • Melting points, glass transition points (Tg), and refractive indexes were measured as physical values.
  • the melting point can be used as an index of vapor deposition property, the glass transition point (Tg) as an index of stability in a thin film state, and the refractive index as an index in regard to the improvement of light extraction efficiency.
  • the melting points and the glass transition points (Tg) were measured using powder, with a high-sensitive differential scanning calorimeter (DSC3100S made by Bruker AXS).
  • a thin film of 60 nm was fabricated on a silicon substrate, and a compact high-speed spectroscopic ellipsometer (UNECS-2000 made by Ulvac, Inc.) was used.
  • the organic EL device of the present invention may have a structure including an anode made of metal, a hole transport layer, a light emitting layer, an electron transport layer, a semitransparent cathode, and a capping layer successively formed on a glass substrate in a light emitting device of top emission structure, optionally with a hole injection layer between the anode and the hole transport layer, an electron blocking layer between the hole transport layer and the light emitting layer, a hole blocking layer between the light emitting layer and the electron transport layer, and an electron injection layer between the electron transport layer and the cathode.
  • Some of the organic layers in this multilayer structure may be omitted or combined.
  • the organic EL device may be configured to combine the hole transport layer with the electron blocking layer and to combine the electron transport layer with the hole blocking layer.
  • the total of film thickness of the respective layers of the organic EL device is preferably about 200 nm to 750 nm, further preferably about 350 nm to 600 nm.
  • the film thickness of the capping layer is preferably 30 nm to 120 nm, for example, and further preferably 40 nm to 80 nm. In this case, excellent light extraction efficiency can be obtained.
  • the film thickness of the capping layer may be suitably changed according to the kind of a light emitting material used for the light emitting device, the thickness of the organic EL device excluding the capping layer, and the like.
  • An electrode material with a large work function such as ITO or gold is used for the anode of the organic EL device of the present invention.
  • the hole injection layer of the organic EL device of the present invention may be made of materials, the examples of which include an arylamine compound having a structure in which three or more triphenylamine structures are joined within a molecule via a single bond or a divalent group that does not contain a heteroatom, such as starburst-type triphenylamine derivatives and various triphenylamine tetramers; porphyrin compounds represented by copper phthalocyanine; accepting heterocyclic compounds such as hexacyano azatriphenylene; and coating-type polymer materials.
  • an arylamine compound having a structure in which three or more triphenylamine structures are joined within a molecule via a single bond or a divalent group that does not contain a heteroatom such as starburst-type triphenylamine derivatives and various triphenylamine tetramers
  • porphyrin compounds represented by copper phthalocyanine accepting heterocyclic compounds such as hexacyano azatriphenylene
  • These materials may be individually formed into films, or may be used as a single layer formed into a film as a mixture with other materials, or may be formed into a laminated structure of individually formed layers, a laminated structure of mixedly formed layers, or a laminated structure of the individually formed layer and the mixedly formed layer. These materials may be formed into a thin film by a vapor deposition method or other known methods such as a spin coating method and an inkjet method.
  • Preferred examples of material used for the hole transport layer of the organic EL device of the present invention include N,N′-diphenyl-N,N′-di(m-tolyl)benzidine (hereinafter referred to as TPD), N,N′-diphenyl-N,N′-di( ⁇ -naphthyl)benzidine (hereinafter referred to as NPD), 1,1-bis[4-(di-4-tolylamino)phenyl]cyclohexane (hereinafter referred to as TAPC), particularly an arylamine compound having a structure in which two triphenylamine structures are joined within a molecule via a single bond or a divalent group that does not contain a heteroatom, represented by the general formula (1), such as N,N,N′,N′-tetrabiphenylylbenzidine, and an arylamine compound having a structure in which three or more triphenylamine structures are joined within a molecule via a single bond or
  • These materials may be individually formed into films, or may be used as a single layer formed into a film as a mixture with other materials, or may be formed into a laminated structure of individually formed layers, a laminated structure of mixedly formed layers, or a laminated structure of the individually formed layer and the mixedly formed layer. These materials may be formed into a thin film by a vapor deposition method or other known methods such as a spin coating method and an inkjet method.
  • Material used for the hole injection layer or the hole transport layer may be obtained by p-doping trisbromophenylamine hexachloroantimony or the like into the material commonly used for these layers, or may be, for example, polymer compounds each having a TPD structure as a part of the compound structure.
  • Examples of material used for the electron blocking layer of the organic EL device of the present invention can be compounds having an electron blocking effect, including carbazole derivatives such as 4,4′,4′′-tri(N-carbazolyl)triphenylamine (hereinafter referred to as TCTA), 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene, 1,3-bis(carbazol-9-yl)benzene (hereinafter referred to as mCP), and 2,2-bis(4-carbazol-9-ylphenyl)adamantane (hereinafter referred to as Ad-Cz); and compounds having a triphenylsilyl group and a triarylamine structure, as represented by 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene.
  • carbazole derivatives such as 4,4′,4′′-tri(N-carbazolyl)
  • These materials may be individually formed into films, or may be used as a single layer formed into a film as a mixture with other materials, or may be formed into a laminated structure of individually formed layers, a laminated structure of mixedly formed layers, or a laminated structure of the individually formed layer and the mixedly formed layer. These materials may be formed into a thin film by a vapor deposition method or other known methods such as a spin coating method and an inkjet method.
  • Examples of material used for the light emitting layer of the organic EL device of the present invention can be quinolinol derivative metal complexes such as Alq 3 , various metal complexes, anthracene derivatives, bis(styryl)benzene derivatives, pyrene derivatives, oxazole derivatives, and polyparaphenylene vinylene derivatives.
  • the light emitting layer may include a host material and a dopant material. Examples of the host material can be thiazole derivatives, benzimidazole derivatives, and polydialkyl fluorene derivatives, in addition to the above light-emitting materials.
  • Examples of the dopant material can be quinacridone, coumarin, rubrene, perylene, derivatives thereof, benzopyran derivatives, rhodamine derivatives, and aminostyryl derivatives. These materials may be individually formed into films, or may be used as a single layer formed into a film as a mixture with other materials, or may be formed into a laminated structure of individually formed layers, a laminated structure of mixedly formed layers, or a laminated structure of the individually formed layer and the mixedly formed layer.
  • the light-emitting material may be a phosphorescent light-emitting material.
  • Phosphorescent materials as metal complexes of metals such as iridium and platinum may be used as the phosphorescent light-emitting material.
  • Examples of the phosphorescent materials can be green phosphorescent materials such as Ir(ppy) 3 , blue phosphorescent materials such as FIrpic and FIr6, and red phosphorescent materials such as Btp 2 Ir(acac).
  • the host material In order to avoid concentration quenching, it is preferable to dope the host material with the phosphorescent light-emitting material by co-evaporation in a range of 1 to 30 weight percent to the whole light emitting layer.
  • the electron transport layer of the organic EL device of the present invention may be formed by using metal complexes of quinolinol derivatives such as Alq 3 and BAlq, various metal complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, thiadiazole derivatives, pyridoindole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, and silole derivatives.
  • quinolinol derivatives such as Alq 3 and BAlq
  • the electron injection layer of the organic EL device of the present invention may be formed by using alkali metal salts such as lithium fluoride and cesium fluoride; alkaline earth metal salts such as magnesium fluoride; and metal oxides such as aluminum oxide.
  • alkali metal salts such as lithium fluoride and cesium fluoride
  • alkaline earth metal salts such as magnesium fluoride
  • metal oxides such as aluminum oxide.
  • the electron injection layer may be omitted in the preferred selection of the electron transport layer and the cathode.
  • the capping layer of the organic EL device of the present invention is preferably made of an arylamine compound having a structure in which two triphenylamine structures are joined within a molecule via a single bond or a divalent group that does not contain a heteroatom, represented by the general formula (1), such as N,N,N′,N′-tetrabiphenylylbenzidine.
  • These materials may be individually formed into films, or may be used as a single layer formed into a film as a mixture with other materials, or may be formed into a laminated structure of individually formed layers, a laminated structure of mixedly formed layers, or a laminated structure of the individually formed layer and the mixedly formed layer.
  • These materials may be formed into a thin film by a vapor deposition method or other known methods such as a spin coating method and an inkjet method.
  • FIG. 1 shows the organic EL device of top emission structure.
  • the present invention is not restricted to the organic EL device of top emission structure but is also applicable to an organic EL device of bottom emission structure and an organic EL device of dual emission structure that emits light from both top and bottom directions.
  • an electrode present in a direction to extract light from a light emitting device to the exterior is required to be transparent or semitransparent.
  • the refractive index of the material that composes the capping layer is larger than that of an adjacent electrode. That is, light extraction efficiency in the organic EL device is improved by the capping layer. Its effect, however, is valid because the effect of light interference is larger when the reflectance at an interface between the capping layer and material in contact with the capping layer is larger. Consequently, the refractive index of the material that composes the capping layer is preferably larger than that of the adjacent electrode, and the refractive index is required to be 1.70 or more, further preferably 1.75 or more, and particularly preferably 1.80 or more.
  • the melting points and the glass transition points of the compounds of the present invention were determined using a high-sensitive differential scanning calorimeter (DSC 3100S made by Bruker AXS).
  • the compounds of the present invention have the glass transition points of 100° C. or higher. This indicates that the compounds of the present invention have a stable thin-film state.
  • a vapor-deposited film with a film thickness of 60 nm was fabricated on a silicon substrate using the compounds of the present invention, and the refractive indexes of 633 nm were measured using the compact high-speed spectroscopic ellipsometer (UNECS-2000 made by Ulvac, Inc.).
  • the compounds of the present invention thus pave values larger than the refractive index 1.70 of Comparative Compound (Alq 3 ), and large improvement of light extraction efficiency in an organic EL device can be expected.
  • the organic EL device was fabricated by vapor-depositing a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7, a cathode 8 and a capping layer 9 in this order on a glass substrate 1 on which a reflecting ITO electrode was formed as a metal anode 2 beforehand as shown in FIG. 1 .
  • the hole transport layer 4 was then formed on the hole injection layer 3 by forming Exemplified Compound (1-13) of the structural formula above in a film thickness of 40 nm at a vapor deposition rate of 6 nm/min.
  • the electron transport layer 6 was formed on the light emitting layer 5 by forming Compound 5 of the structural formula below in a film thickness of 30 nm at a vapor deposition rate of 6 nm/min.
  • the electron injection layer 7 was formed on the electron transport layer 6 by forming lithium fluoride in a film thickness of 0.5 nm at a vapor deposition rate of 0.6 nm/min.
  • the cathode 8 was formed on the electron injection layer 7 by forming a magnesium silver alloy in a film thickness of 10 nm.
  • Exemplified Compound (1-13) was formed as the capping layer 9 in a film thickness of 60 nm at a vapor deposition rate of 6 nm/min. The characteristics of the thus fabricated organic EL device were measured in the atmosphere at an ordinary temperature.
  • Table 1 summarizes the results of emission characteristics measurements performed by applying DC voltage to the fabricated organic EL device.
  • An organic EL device was fabricated under the same conditions used in Example 3, except that the capping layer 9 was formed by forming Exemplified Compound (1-17) in a thickness of 60 nm, instead of using Exemplified Compound (1-13).
  • the characteristics of the fabricated organic EL device were measured in the atmosphere at an ordinary temperature. Table 1 summarizes the results of the emission characteristics measurements performed by applying DC voltage to the fabricated organic EL device.
  • An organic EL device was fabricated under the same conditions used in Example 3, except that the capping layer 9 was formed by forming Exemplified Compound (1-18) in a thickness of 60 nm, instead of using Exemplified Compound (1-13).
  • the characteristics of the fabricated organic EL device were measured in the atmosphere at an ordinary temperature. Table 1 summarizes the results of the emission characteristics measurements performed by applying DC voltage to the fabricated organic EL device.
  • An organic EL device was fabricated under the same conditions used in Example 3, except that the capping layer 9 was formed by forming Exemplified Compound (1-27) in a thickness of 60 nm, instead of using Exemplified Compound (1-13).
  • the characteristics of the fabricated organic EL device were measured in the atmosphere at an ordinary temperature. Table 1 summarizes the results of the emission characteristics measurements performed by applying DC voltage to the fabricated organic EL device.
  • An organic EL device was fabricated under the same conditions used in Example 3, except that the capping layer 9 was formed by forming Exemplified Compound (1-32) in a thickness of 60 nm, instead of using Exemplified Compound (1-13).
  • the characteristics of the fabricated organic EL device were measured in the atmosphere at an ordinary temperature. Table 1 summarizes the results of the emission characteristics measurements performed by applying DC voltage to the fabricated organic EL device.
  • An organic EL device was fabricated under the same conditions used in Example 3, except that the capping layer 9 was formed by forming Exemplified Compound (1-33) in a thickness of 60 nm, instead of using Exemplified Compound (1-13).
  • the characteristics of the fabricated organic EL device were measured in the atmosphere at an ordinary temperature. Table 1 summarizes the results of the emission characteristics measurements performed by applying DC voltage to the fabricated organic EL device.
  • An organic EL device was fabricated under the same conditions used in Example 3, except that the capping layer 9 was formed by forming Exemplified Compound (1-36) in a thickness of 60 nm, instead of using Exemplified Compound (1-13).
  • the characteristics of the fabricated organic EL device were measured in the atmosphere at an ordinary temperature. Table 1 summarizes the results of the emission characteristics measurements performed by applying DC voltage to the fabricated organic EL device.
  • An organic EL device was fabricated under the same conditions used in Example 3, except that the capping layer 9 was formed by forming Exemplified Compound (1-37) in a thickness of 60 nm, instead of using Exemplified Compound (1-13).
  • the characteristics of the fabricated organic EL device were measured in the atmosphere at an ordinary temperature. Table 1 summarizes the results of the emission characteristics measurements performed by applying DC voltage to the fabricated organic EL device.
  • An organic EL device was fabricated under the same conditions used in Example 3, except that the capping layer 9 was formed by forming Alq 3 in a thickness of 60 nm, instead of using Exemplified Compound (1-13).
  • the characteristics of the fabricated organic EL device were measured in the atmosphere at an ordinary temperature. Table 1 summarizes the results of the emission characteristics measurements performed by applying DC voltage to the fabricated organic EL device.
  • the driving voltage at a current density of 10 mA/cm 2 in Examples 3 to 10 was substantially equivalent to that in Comparative Example 1 using Alq 3 , while luminance, current efficiency and power efficiency were all improved. Further, a great improvement in external quantum efficiency could be confirmed. This indicates that light extraction efficiency can be greatly improved by containing, in the capping layer, a material having a high refractive index and suitably used for the organic EL device of the present invention.
  • the arylamine compound having a structure in which two triphenylamine structures are joined within a molecule via a single bond or a divalent group that does not contain a heteroatom excels as the compound for the organic EL device because of having a high refractive index, attaining a great improvement in light extraction efficiency and having a stable thin-film state. High efficiency can be obtained, and durability can be improved by fabricating the organic EL device using this compound.
  • the use of this compound having no absorption in the respective wavelength ranges of blue, green, and red is particularly suitable in the case of displaying a clear, light image with high color purity. For example, development to application of domestic electrical appliances and illumination can be achieved.

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US9269749B2 (en) * 2014-07-07 2016-02-23 Au Optronics Corporation Organic electroluminescence display panel
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US20170263884A1 (en) * 2017-03-22 2017-09-14 Shanghai Tianma AM-OLED Co., Ltd. Organic light-emitting diode display panel, fabrication method, and electronic apparatus
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CN115141106B (zh) * 2022-06-30 2024-03-22 山东钥熠材料科技有限公司 化合物、有机材料和有机光电器件
CN115548235B (zh) * 2022-10-13 2024-05-28 京东方科技集团股份有限公司 光取出膜、发光器组件和显示装置

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020182439A1 (en) * 2001-05-01 2002-12-05 Yu-Tai Tao Fluorene compounds
JP3398548B2 (ja) * 1996-09-11 2003-04-21 シャープ株式会社 有機電界発光素子
US20070296331A1 (en) * 2006-06-27 2007-12-27 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescence device using the same
US20090115315A1 (en) * 2005-06-30 2009-05-07 Canon Kabushiki Kaisha Multi-color display apparatus
WO2011043083A1 (ja) * 2009-10-09 2011-04-14 出光興産株式会社 有機エレクトロルミネッセンス素子
US20110112275A1 (en) * 2008-10-31 2011-05-12 Merck Patent Gmbh Novel materials for organic electroluminescence devices

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3194657B2 (ja) 1993-11-01 2001-07-30 松下電器産業株式会社 電界発光素子
JP3828595B2 (ja) 1994-02-08 2006-10-04 Ｔｄｋ株式会社 有機ｅｌ素子
EP0666298A3 (en) * 1994-02-08 1995-11-15 Tdk Corp Organic electroluminescent element and compound used therein.
US6548956B2 (en) * 1994-12-13 2003-04-15 The Trustees Of Princeton University Transparent contacts for organic devices
JP4320811B2 (ja) * 1998-12-07 2009-08-26 コニカミノルタホールディングス株式会社 有機エレクトロルミネッセンス素子
JP4487587B2 (ja) 2003-05-27 2010-06-23 株式会社デンソー 有機ｅｌ素子およびその製造方法
US20060021647A1 (en) * 2004-07-28 2006-02-02 Gui John Y Molecular photovoltaics, method of manufacture and articles derived therefrom
KR100700013B1 (ko) * 2004-11-26 2007-03-26 삼성에스디아이 주식회사 유기전계발광소자 및 그의 제조 방법
KR100721562B1 (ko) * 2004-12-03 2007-05-23 삼성에스디아이 주식회사 마그네슘-칼슘 막인 캐소드를 구비하는 유기전계발광소자및 그의 제조방법
JP4927423B2 (ja) * 2005-03-24 2012-05-09 エルジー ディスプレイ カンパニー リミテッド 発光装置及びその製造方法
JP5258166B2 (ja) * 2005-03-24 2013-08-07 エルジー ディスプレイ カンパニー リミテッド 発光素子、その発光素子を備えた発光装置及びその製造方法
KR100883306B1 (ko) * 2005-03-24 2009-02-11 쿄세라 코포레이션 발광 소자, 그 발광 소자를 구비한 발광 장치 및 그 제조방법
JP4809186B2 (ja) * 2006-10-26 2011-11-09 京セラ株式会社 有機ｅｌディスプレイおよびその製造方法
JP5014971B2 (ja) * 2007-12-19 2012-08-29 ソニーモバイルディスプレイ株式会社 ディスプレイ装置
KR100894627B1 (ko) * 2008-01-15 2009-04-24 삼성모바일디스플레이주식회사 유기전계발광소자 및 그의 제조방법
WO2009104148A1 (en) * 2008-02-22 2009-08-27 Philips Intellectual Property & Standards Gmbh Double sided organic light emitting diode (oled)
WO2009151039A1 (ja) * 2008-06-11 2009-12-17 保土谷化学工業株式会社 有機エレクトロルミネッセンス素子
EP2145936A3 (en) * 2008-07-14 2010-03-17 Gracel Display Inc. Fluorene and pyrene derivatives and organic electroluminescent device using the same
KR101094287B1 (ko) * 2009-10-09 2011-12-19 삼성모바일디스플레이주식회사 유기 발광 표시 장치
KR20120112672A (ko) * 2010-01-26 2012-10-11 호도가야 가가쿠 고교 가부시키가이샤 트리페닐아민 구조를 가지는 화합물 및 유기 일렉트로 루미네센스 소자
JP3194657U (ja) 2014-09-19 2014-12-04 恵美子 青柳 温熱首巻

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3398548B2 (ja) * 1996-09-11 2003-04-21 シャープ株式会社 有機電界発光素子
US20020182439A1 (en) * 2001-05-01 2002-12-05 Yu-Tai Tao Fluorene compounds
US20090115315A1 (en) * 2005-06-30 2009-05-07 Canon Kabushiki Kaisha Multi-color display apparatus
US20070296331A1 (en) * 2006-06-27 2007-12-27 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescence device using the same
US20110112275A1 (en) * 2008-10-31 2011-05-12 Merck Patent Gmbh Novel materials for organic electroluminescence devices
WO2011043083A1 (ja) * 2009-10-09 2011-04-14 出光興産株式会社 有機エレクトロルミネッセンス素子

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Aonuma et al., “Material design of hole transport materials capable of thick-film formation in organic light emitting diodes”, 2007, Applied Physics Letters, vol. 90, article 183503, pp. 1-3. *
Machine translation of JP 3398548 B2, Date of Japanese Language Document: 04-2003, pp. 1-11. *
Shirota et al., “Thermally stable organic light-emitting diodes using new families of hole-transporting amorphous molecular materials”, 2000, Synthetic Metals, vol. 111-112, pp. 387-391. *

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9748493B2 (en) 2012-03-15 2017-08-29 Novaled Gmbh Aromatic amine-terphenyl compounds and use thereof in organic semiconducting components
US9882136B2 (en) 2012-05-31 2018-01-30 Hodogaya Chemical Co., Ltd. Organic electroluminescent device
US9269749B2 (en) * 2014-07-07 2016-02-23 Au Optronics Corporation Organic electroluminescence display panel
US10121987B2 (en) 2014-11-24 2018-11-06 Samsung Display Co., Ltd. Organic light emitting diode display including capping layer having high refractive index
US10985340B2 (en) 2014-11-24 2021-04-20 Samsung Display Co., Ltd. Organic light emitting diode display including capping layer having high refractive index
US11362283B2 (en) 2015-09-09 2022-06-14 Lg Chem, Ltd. Organic electroluminescent element
US11569484B2 (en) 2016-04-07 2023-01-31 Samsung Display Co., Ltd. Organic light emitting diode
CN107275370A (zh) * 2016-04-07 2017-10-20 三星显示有限公司 有机发光二极管和发光二极管显示器
US11056653B2 (en) 2016-04-22 2021-07-06 Hodogaya Chemical Co., Ltd. Organic electroluminescence device
US10510981B2 (en) * 2017-03-22 2019-12-17 Shanghai Tianma AM-OLED Co., Ltd. Organic light-emitting diode display panel, fabrication method, and electronic apparatus
US20170263884A1 (en) * 2017-03-22 2017-09-14 Shanghai Tianma AM-OLED Co., Ltd. Organic light-emitting diode display panel, fabrication method, and electronic apparatus
US11997870B2 (en) 2017-12-21 2024-05-28 Hodogaya Chemical Co., Ltd. Organic electroluminescent element and method for producing same
US11706943B2 (en) 2017-12-21 2023-07-18 Hodogaya Chemical Co., Ltd. Organic electroluminescent element and method for producing same
US11974499B2 (en) 2018-01-10 2024-04-30 Hodogaya Chemical Co., Ltd. Organic EL device, amine compound having benzazole ring structure, and method in which said amine compound is used in capping layer of organic EL device
US11985891B2 (en) 2018-11-30 2024-05-14 Sfc Co., Ltd. Polycyclic aromatic compounds and organic electroluminescent devices using the same
US20220102635A1 (en) * 2018-11-30 2022-03-31 Sfc Co., Ltd. Organic light-emitting element using polycyclic aromatic derivative compound
US11950447B2 (en) 2018-12-10 2024-04-02 Semiconductor Energy Laboratory Co., Ltd. Light-emitting device, light-emitting apparatus, electronic device, and lighting device
US12004400B2 (en) 2018-12-28 2024-06-04 Semiconductor Energy Laboratory Co., Ltd. Light-emitting apparatus, lighting device, display device, module, and electronic device
WO2020171221A1 (ja) 2019-02-22 2020-08-27 保土谷化学工業株式会社 ベンゾアゾール環構造を有するアリールアミン化合物および有機エレクトロルミネッセンス素子
KR20210131321A (ko) 2019-02-22 2021-11-02 호도가야 가가쿠 고교 가부시키가이샤 벤조아졸 고리 구조를 갖는 아릴아민 화합물 및 유기 일렉트로 루미네선스 소자
US11903232B2 (en) 2019-03-07 2024-02-13 Semiconductor Energy Laboratory Co., Ltd. Light-emitting device comprising charge-generation layer between light-emitting units
KR20230147044A (ko) 2021-02-15 2023-10-20 호도가야 가가쿠 고교 가부시키가이샤 화합물 및 그 화합물을 사용한 유기 일렉트로루미네선스소자
WO2022264974A1 (ja) 2021-06-15 2022-12-22 保土谷化学工業株式会社 アザベンゾオキサゾール環構造を有するアミン化合物およびそれを用いた有機エレクトロルミネッセンス素子
KR20240021752A (ko) 2021-06-15 2024-02-19 호도가야 가가쿠 고교 가부시키가이샤 아자벤조옥사졸 고리 구조를 갖는 아민 화합물 및 그것을 사용한 유기 일렉트로 루미네선스 소자
WO2023048118A1 (ja) 2021-09-21 2023-03-30 保土谷化学工業株式会社 化合物および有機エレクトロルミネッセンス素子
WO2023074767A1 (ja) 2021-10-28 2023-05-04 保土谷化学工業株式会社 アミン化合物およびそれを用いた有機エレクトロルミネッセンス素子

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