WO2011007849A1 - Encre de revêtement de colonne de liquide, procédé de production d'élément électroluminescent organique et dispositif électroluminescent organique muni dudit élément - Google Patents

Encre de revêtement de colonne de liquide, procédé de production d'élément électroluminescent organique et dispositif électroluminescent organique muni dudit élément Download PDF

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Publication number
WO2011007849A1
WO2011007849A1 PCT/JP2010/062021 JP2010062021W WO2011007849A1 WO 2011007849 A1 WO2011007849 A1 WO 2011007849A1 JP 2010062021 W JP2010062021 W JP 2010062021W WO 2011007849 A1 WO2011007849 A1 WO 2011007849A1
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ink
organic
layer
solvent
liquid column
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PCT/JP2010/062021
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English (en)
Japanese (ja)
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合田匡志
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住友化学株式会社
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    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
    • 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
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
    • H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/115—Polyfluorene; Derivatives thereof

Definitions

  • the present invention relates to a liquid column coating ink used for manufacturing an organic electroluminescence (hereinafter referred to as “organic EL”) element, a method for manufacturing the organic EL element, and an organic EL having the organic EL element. Relates to the device.
  • organic EL organic electroluminescence
  • Organic EL elements and organic EL devices equipped with the organic EL elements have already been commercialized as displays for mobile phones and the like.
  • the organic EL element is a laminate having an anode and a cathode and one or more organic EL layers including a light emitting layer sandwiched between these electrodes.
  • the light emitting layer is formed of an organic compound that emits light when a voltage is applied and a current flows.
  • Organic EL elements have various characteristics. Since the organic EL element can be formed by stacking thin films, an organic EL device such as an organic EL display device on which the organic EL element is mounted is extremely thin, and this is one of the major features of the organic EL device. .
  • the organic EL element is usually produced by laminating an electrode and one or more organic EL layers including a light emitting layer in a predetermined order on a support substrate.
  • An organic EL layer in an organic EL element that has already been commercialized is formed using a vacuum deposition method.
  • a coating method is also exemplified.
  • the coating method is a method of forming an organic EL layer by applying an ink containing a constituent component of the organic EL layer, that is, an ink containing an organic EL material, and curing the ink by drying or the like.
  • the coating method include an inkjet method (droplet coating method).
  • the ink jet method the coating amount of the organic EL material can be precisely controlled, and precise position control in units of several microns is possible.
  • the ink jet method has been developed as a technology for increasing the screen size. However, in the ink jet method, since the ink is ejected as droplets from the nozzle, the nozzle hole is likely to be blocked.
  • the nozzle printing method is a method in which ink is ejected as a continuous liquid column from the ejection nozzle and the ink is applied onto the substrate.
  • the nozzle printing method It has an advantage that the hole is hardly blocked.
  • the formation region of each display pixel arranged on the insulating substrate A substrate having a panel structure in which (pixel region) is defined and a continuous partition wall protruding between the pixel regions is provided is known.
  • the shape of the partition wall suitable for the liquid column coating method is a stripe shape, and is described in, for example, Patent Documents 1 and 2.
  • the substrate used in the organic EL device is provided with various wirings such as signal lines and gate lines, and the partition serves as a black matrix that suppresses reflection of external light from the wiring insulating layer and wiring. In some cases, it is not a stripe shape but a box shape.
  • a box-shaped partition is described in Patent Document 3, for example.
  • JP 2002-75640 A JP 2004-119351 A JP-A-10-153967
  • the present inventors have found that the viscosity of the ink during drying is important in order to suppress the nonuniformity of the film shape in the pixel and the occurrence of unevenness between pixels.
  • the viscosity of the ink is too high, a large amount of ink adheres to the partition walls and does not sufficiently fall between the partition walls, and the film shape formed by drying the ink becomes a mortar shape riding on the partition walls.
  • the viscosity of the ink is too low, the surface tension of the ink dominates whether the ink falls to the left or right side of the partition wall, and is affected by subtle unevenness of the surface on the partition wall.
  • the thickness of the layer varies from pixel to pixel, resulting in unevenness between pixels.
  • Patent Document 2 includes a first aromatic solvent having a first boiling point and a first viscosity, and a second boiling point higher than the first boiling point and a second aromatic solvent having a second viscosity higher than the first viscosity.
  • An ink using a mixed solvent in which a plurality of aromatic solvents are mixed is disclosed, for example, tetralin (boiling point 207.2 ° C., viscosity 2 cP) and mesitylene (boiling point 164.7 ° C., viscosity 0.77 cP). Combinations are listed.
  • the present invention has a liquid column coating ink and a method for manufacturing an organic EL element, which are used for manufacturing a high-quality organic EL element in which unevenness between pixels and unevenness in a pixel is suppressed, and the organic EL element.
  • An organic EL device is provided. Means for Solving the Problems The present invention provides the following means. ⁇ 1> A liquid column coating ink comprising an organic EL material and a solvent (A) having a viscosity of 2.5 to 10 cP and a boiling point of 210 to 290 ° C.
  • ⁇ 2> The ink according to ⁇ 1>, further comprising a solvent (B) having a boiling point of 90 ° C. or higher and 160 ° C. or lower.
  • ⁇ 3> The ink according to ⁇ 1> or ⁇ 2>, wherein the volume ratio of the solvent (A) to the total volume of the ink is 5% or more and 40% or less.
  • ⁇ 4> The ink according to any one of ⁇ 1> to ⁇ 3>, wherein the viscosity of the ink itself is 15 cP or less.
  • ⁇ 5> The ink according to any one of ⁇ 1> to ⁇ 4>, wherein the difference between the surface tension of the ink itself and the surface tension of the solvent (A) is 10 mN / m or less.
  • a method for producing an organic EL element comprising: applying the ink according to any one of ⁇ 1> to ⁇ 5> to a pixel region partitioned by a partition wall by liquid column application, and drying the applied ink. .
  • FIG. 1 shows the movement of nozzles and panels in the coating process of an embodiment of the present invention.
  • FIG. 2 shows the nozzle trajectory in the coating process.
  • FIG. 3A is a plan view schematically showing two pixel regions and their surroundings in the process of drying ink after application.
  • 3-2 is a longitudinal sectional view of FIG. 3-1.
  • FIG. 4 shows the cross-sectional position II ′ of the panel.
  • FIG. 5 is a cross-sectional view immediately after ink application along the line II ′ of FIG. 6 is a cross-sectional view after ink drying in Example 1.
  • FIG. FIG. 7 is a cross-sectional view after ink drying in Comparative Example 1.
  • the present invention relates to a liquid column coating ink (hereinafter referred to as “the ink of the present invention”) comprising an organic EL material and a solvent (A) having a viscosity in the range of 2.5 cP to 10 cP and a boiling point of 210 ° C. to 290 ° C. ").
  • the viscosity value and the surface tension value are values at 25 ° C.
  • the ink of the present invention can be suitably used as a liquid column coating ink, and is preferably used for producing an organic EL element by liquid column coating such as a nozzle printing method.
  • the ink of the present invention can be suitably used particularly for an organic EL element substrate having a box-shaped partition.
  • the ink of the present invention is a solution or suspension containing an organic EL material and an ink solvent.
  • solvent is used as a concept including both a liquid for dissolving an organic EL material and a liquid for dispersing an organic EL material, unless otherwise specified.
  • the organic EL material is a material constituting each layer such as a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • at least one solvent is a solvent having a viscosity of 2.5 cP or more and 10 cP or less and a boiling point of 210 ° C. or more and 290 ° C. or less (preferably 220 ° C. or more and 260 ° C. or less).
  • A) (hereinafter referred to as “solvent (A)”).
  • Such a solvent include butyl benzoate, cyclohexylbenzene, bicyclohexyl, o-nitroanisole, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether, triethylene glycol butyl methyl ether, and tetraethylene glycol dimethyl ether. .
  • 1 type may be used and 2 or more types may be mixed and used.
  • butyl benzoate is preferable from the viewpoint of solubility of the organic EL material. Since the ink starts drying immediately after it is applied, the drying of the ink and the drop between the partition walls occur in parallel. Since the solvent (A) has a boiling point as high as 210 ° C.
  • the solvent (A) in the ink of the present invention has a boiling point in the range of 210 ° C. or higher and 290 ° C. or lower (preferably 220 ° C. or higher and 260 ° C. or lower).
  • the applied ink is dried while gradually falling into the pixel area without rapidly evaporating, thereby suppressing the occurrence of uneven thickness of the layer after drying due to uneven drying of the ink. Can do.
  • the ink of the present invention preferably further contains a solvent (B) having a boiling point of 90 ° C. or higher and 160 ° C. or lower, and the solvent (A) and the solvent (B) are preferably mixed.
  • the viscosity of the ink itself is preferably 15 cP or less (preferably 10 cP or less).
  • the viscosity of the ink itself can be adjusted by mixing the solvent (A) and the solvent (B).
  • the lower limit of the ink viscosity is usually 1 cP or more.
  • the viscosity of the ink can be adjusted by appropriately selecting the type of the organic EL material and the solvent used in the ink.
  • the solvent (B) can be appropriately selected in consideration of the solubility, dispersibility, volatility, etc. of the organic EL material, and specifically, the solvent (B) is toluene, xylene, mesitylene, anisole, water. 1-propanol, 1-butanol, 1-ethoxy-2-propanol. Among these, 1 type may be used and 2 or more types may be mixed and used. Among these, from the viewpoint of solubility of the organic EL material, the solvent (B) preferably contains anisole.
  • the evaporation rate of the ink itself is particularly suitable when the ratio of the volume of the solvent (A) to the total volume of the ink is 5 to 40%. A higher quality layer with higher uniformity is formed.
  • the drying process after the application of the ink the drying of the high boiling point solvent is slow, so that the concentration of the high boiling point solvent gradually increases. If surface tension distribution occurs during this drying process, liquid movement (Marangoni convection) occurs due to surface tension difference, and there is a concern that the film thickness distribution of the layer after drying becomes remarkable.
  • the difference between the surface tension of the ink itself of the present invention and the surface tension of the solvent (A) is preferably 10 mN / m or less. Thereby, the film thickness uniformity of a layer increases more.
  • Manufacturing method of organic EL element A method for producing an organic EL device according to an embodiment of the present invention using the ink of the present invention will be described with reference to the drawings.
  • a laminate including at least a pair of electrodes and a light emitting layer sandwiched between the electrodes is defined as an “organic EL element”, and a flat display device in which the organic EL elements are two-dimensionally arranged is referred to as “organic It is defined as “EL device”.
  • each member in the drawings may be different from the actual scale.
  • the present invention is not limited by the following description, and can be appropriately changed without departing from the gist of the present invention.
  • members such as electric wiring and a driving thin film transistor may be mounted.
  • various modes based on ordinary knowledge in the technical field such as a light-emitting element and a display device are used. However, detailed descriptions are omitted because they are not directly related to the description of the present invention. .
  • the organic EL device manufactured according to the embodiment of the present invention is provided with a plurality of pixels.
  • a region where a pixel is formed that is, a pixel region is partitioned by a partition wall surrounding the region, and a planar shape thereof is a shape such as a circle, an ellipse, an ellipse, or a rectangle.
  • Each pixel is composed of an organic EL element that is a laminate including at least a pair of electrodes and a light emitting layer sandwiched between the electrodes.
  • a laminate constituting the organic EL element is produced by sequentially laminating various layers on a support substrate. At least one of the layers constituting the laminate is produced using the ink of the present invention. 1 and 2 show the coating process.
  • the panel 1 provided with four matrix portions (display area portions) 40 on the support substrate 30 is transported in the Dd direction.
  • Ink for forming the layer of the laminate is ejected from the nozzle 20 of the nozzle printing apparatus (main body not shown).
  • the nozzle 20 repeatedly moves in a direction Nm orthogonal to the transport direction Dd of the panel 1.
  • the matrix section 40 is provided with a plurality of pixel regions 41 that are surrounded by partition walls 42. Therefore, when the panel 1 is conveyed under the nozzle 20 and the nozzle repeatedly moves in the Nm direction, the nozzle 20 relatively moves on the panel so as to draw a trajectory Ip.
  • the nozzle 20 moves by one line in the longitudinal direction of the pixel area 41 along the trajectory Ip, then moves to the next line, and newly moves relatively in the longitudinal direction of the pixel area 41.
  • ink is ejected from the nozzle 20, and ink is applied to the pixel region 41 one after another while drawing a locus as shown in FIG. Since the ink is continuously ejected from the nozzle 20 in a liquid column state, the ink is intermittently not only on the partition in the longitudinal direction of the pixel region 41 but also the pixel region 41 as indicated by the trajectory Ip. It is applied continuously. The ink is applied in a non-intermittent linear manner on the plurality of pixel regions 41 and the partition walls 42 arranged in the longitudinal direction of the pixel region 41.
  • FIG. 3A is a plan view schematically showing two pixel regions and their surroundings in the process of drying ink after application
  • FIG. 3B is a longitudinal sectional view thereof.
  • the ink is gradually dried after being ejected from the nozzle. After the application is completed, the ink is placed in a predetermined atmosphere in the drying process, and the solvent is evaporated from the ink and cured to form a layer. The ink applied from the nozzles shrinks while drying.
  • the partition wall 42 may be subjected to a process of repelling ink (a liquid repellent process). In this way, the ink 51 applied onto the partition wall 42 is pulled toward the pixel region 41 from the partition wall 42 so as to be pulled in the direction M into the pixel region 41 during drying. Specifically, a part of the layer is formed in the pixel region 41.
  • the ink of the present invention is continuously ejected as a non-intermittent liquid column, and is continuously and intermittently applied onto the pixel region 41 and the partition wall 42 in the longitudinal direction of the pixel region 41.
  • the ink is applied linearly on the plurality of pixel regions 41 and the partition walls 42 arranged in the longitudinal direction of the pixel region 41.
  • the ink is applied in a non-intermittent linear shape in the longitudinal direction, and the ink on the partition wall 42 is pulled by being connected to the ink in the pixel region 41, so that it does not easily flow in the short direction in the pixel region. Therefore, the ink 51 applied on the partition wall 42 falls into the left or right pixel region 41 in the longitudinal direction.
  • the ink of the present invention contains the solvent (A) having a viscosity of 2.5 cP or more and 10 cP or less and a boiling point of 210 ° C. or more and 290 ° C. or less (preferably 220 ° C. or more and 260 ° C. or less).
  • the viscosity of the ink itself is preferably 15 cP or less (more preferably 10 cP or less).
  • the surface of the partition wall 42 may have a property of repelling ink (liquid repellency) so that the ink hardly remains.
  • a method for imparting liquid repellency to the partition wall 42 include a method of mixing a liquid repellent component with a component constituting the partition wall, and a method of providing a liquid repellent film on the surface of the partition wall.
  • the ink containing the organic EL material is ejected continuously as a liquid column intermittently.
  • the apparatus that continuously ejects ink include a nozzle printing apparatus.
  • the nozzle printing apparatus can continuously eject ink from minute nozzle holes.
  • the nozzle printing apparatus is suitable for coating in a non-intermittent continuous line stably with a fine line width.
  • the solvent is distilled off from the ink, and the organic EL layer is fixed to the pixel region 41.
  • the drying time and drying temperature are appropriately determined in consideration of the organic EL material to be used, the solvent, the thickness of the layer to be set, and the like.
  • a step of baking the ink after drying may be provided.
  • the laminate constituting the organic EL element may be provided with various types of layers in addition to the electrodes and the light emitting layer.
  • the layer stacking order and the like can take various modifications.
  • the organic EL device produced by the method for producing an organic EL device of the present invention is not limited to the following organic EL device.
  • the method for producing an organic EL element of the present invention at least one organic EL layer of the laminate constituting the organic EL element is formed using the ink of the present invention, as shown in the above embodiment and the like. It is a layer formed by a process including predetermined application and drying. Other layers may be formed by other methods. In general, each layer constituting the organic EL element is extremely thin, and various film forming methods can be adopted for layer formation.
  • the organic EL element can have other layers between the anode and the light emitting layer and / or between the light emitting layer and the cathode, in addition to making the anode, the light emitting layer and the cathode essential.
  • a transparent electrode capable of transmitting light is preferable from the viewpoint of manufacturing an element that emits light through the anode. Examples of such transparent electrodes include metal oxides, metal sulfides, and metal thin films having high electrical conductivity.
  • a material having a high light transmittance is suitable as the material for the anode, and it may be appropriately selected and used corresponding to the organic EL layer.
  • the material for the anode include metal oxides selected from the group consisting of indium oxide, zinc oxide, tin oxide, ITO, and indium zinc oxide (abbreviated as IZO), gold, platinum, silver, and copper. And metals selected from the group consisting of aluminum and alloys containing at least one of these metals.
  • a material for the cathode a material having a small work function and capable of easily injecting electrons into the light emitting layer, a material having a high electrical conductivity, and a material having a high visible light reflectivity are suitable. May be appropriately selected and used.
  • the material for the cathode include metals selected from the group consisting of alkali metals, alkaline earth metals, transition metals, Group III-B metals, and alloys containing at least one of these metals.
  • the light emitting layer contains an organic compound. Usually, the light emitting layer contains organic compounds (low molecular compounds and high molecular compounds) that emit fluorescence or phosphorescence.
  • the light emitting layer may further contain a dopant material or the like. Examples of the material constituting the light emitting layer include the following dye materials, metal complex materials, polymer materials, and dopant materials.
  • dye-based materials include cyclopentamine derivatives, tetraphenylbutadiene derivative compounds, triphenylamine derivatives, oxadiazole derivatives, pyrazoloquinoline derivatives, distyrylbenzene derivatives, distyrylarylene derivatives, pyrrole derivatives, thiophene ring compounds. Pyridine ring compounds, perinone derivatives, perylene derivatives, oligothiophene derivatives, trifumanylamine derivatives, oxadiazole dimers, pyrazoline dimers, and the like.
  • the metal complex material examples include metal complexes that emit light from triplet excited states such as iridium complexes and platinum complexes, aluminum quinolinol complexes, benzoquinolinol beryllium complexes, benzoxazolyl zinc complexes, benzothiazole zinc complexes, azomethyls. It has a metal such as Al, Zn or Be as a central metal such as zinc complex, porphyrin zinc complex or europium complex, or a rare earth metal such as Tb, Eu or Dy, and oxadiazole, thiadiazole, phenylpyridine or phenyl as a ligand Examples thereof include metal complexes having benzimidazole, quinoline structure, and the like.
  • polymer materials include polyparaphenylene vinylene derivatives, polythiophene derivatives, polyparaphenylene derivatives, polysilane derivatives, polyacetylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives, and materials obtained by polymerizing the above dye materials or metal complex materials.
  • Etc. The light emitting layer can contain a dopant material for the purpose of improving the light emission efficiency and changing the light emission wavelength.
  • Examples of the dopant material include perylene derivatives, coumarin derivatives, rubrene derivatives, quinacridone derivatives, squalium derivatives, porphyrin derivatives, styryl dyes, tetracene derivatives, pyrazolone derivatives, decacyclene, phenoxazone, and the like.
  • the thickness of the light emitting layer is usually about 2 nm to 2000 nm.
  • one light emitting layer is usually provided, and two or more light emitting layers can be provided. Two or more light-emitting layers can be stacked adjacent to each other, or a layer other than the light-emitting layer can be provided between the light-emitting layers.
  • the layer that can be provided between the anode and the light emitting layer examples include a hole injection layer, a hole transport layer, and an electron block layer.
  • the layer close to the anode is the hole injection layer
  • the layer close to the light emitting layer is the hole transport layer.
  • the hole injection layer or the hole transport layer has a function of blocking electron transport, these layers may also serve as the electron block layer.
  • the hole injection layer can be provided between the anode and the hole transport layer or between the anode and the light emitting layer.
  • hole injection layer material which comprises a hole injection layer
  • a well-known material can be used suitably.
  • the hole injection layer material include phenylamine materials, starburst amine materials, phthalocyanine materials, hydrazone derivatives, carbazole derivatives, triazole derivatives, imidazole derivatives, oxadiazole derivatives having amino groups, vanadium oxide, oxidation Examples thereof include oxides such as tantalum, tungsten oxide, molybdenum oxide, ruthenium oxide, and aluminum oxide, amorphous carbon, polyaniline, and polythiophene derivatives.
  • the hole transport layer material constituting the hole transport layer is not particularly limited.
  • a derivative thereof, poly (2,5-thienylene vinylene), a derivative thereof, or the like can be given.
  • Examples of the layer that can be provided between the cathode and the light emitting layer include an electron injection layer, an electron transport layer, and a hole blocking layer.
  • the layer close to the cathode is the electron injection layer
  • the layer close to the light emitting layer is the electron transport layer.
  • these layers may also serve as the hole blocking layer.
  • the electron injection layer material constituting the electron injection layer can be appropriately selected according to the type of the light emitting layer.
  • the electron injection layer material examples include an alkali metal, an alkaline earth metal, an alloy containing at least one alkali metal and an alkaline earth metal, a metal oxide containing at least one alkali metal and an alkaline earth metal, an alkali metal, and Examples thereof include halides containing at least one alkaline earth metal, carbonates containing at least one alkali metal and alkaline earth metal, and mixtures thereof.
  • the electron transport layer material constituting the electron transport layer is not particularly limited, and known materials can be used.
  • Examples of the electron transport layer material include oxadiazole derivatives, anthraquinodimethane or derivatives thereof, benzoquinone or derivatives thereof, naphthoquinone or derivatives thereof, anthraquinones or derivatives thereof, tetracyanoanthraquinodimethane or derivatives thereof, fluorenone derivatives, Examples include diphenyldicyanoethylene or a derivative thereof, a diphenoquinone derivative, or a metal complex of 8-hydroxyquinoline or a derivative thereof, polyquinoline or a derivative thereof, polyquinoxaline or a derivative thereof, polyfluorene or a derivative thereof, and the like.
  • the following layer structure is mentioned as a more specific layer structure of the organic EL layer in an organic EL element: a) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode b) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode c) Anode / hole injection layer / hole transport layer / emission layer / electron injection layer / cathode d) anode / hole injection layer / hole transport layer / emission layer / cathode e) anode / hole injection layer / emission layer / Electron transport layer / electron injection layer / cathode f) anode / hole injection layer / light emitting layer / electron transport layer / cathode g) anode / hole injection layer / light emitting layer / electron injection layer / cathode h) anode / hole injection Layer
  • the organic EL device that can be manufactured by the method for manufacturing an organic EL element of the present invention can be used as a backlight for a planar light source, a segment display device, a dot matrix display device, and a liquid crystal display device.
  • the planar anode and cathode may be arranged so as to overlap each other.
  • a method of obtaining pattern-like light emission a method of installing a mask provided with a pattern-like window on the surface of the planar light-emitting element, an organic layer of a non-light-emitting portion is formed extremely thick and substantially non-light-emitting. And a method of forming either the anode or the cathode or both electrodes in a pattern. By forming a pattern by any of these methods and arranging several electrodes so that they can be turned on and off independently, a segment type display device capable of displaying numbers, letters, simple symbols, and the like can be obtained.
  • a passive matrix substrate in which anodes and cathodes are both formed in stripes and arranged orthogonally, or an active matrix substrate in which thin film transistors are arranged and controlled in pixel units may be used.
  • Partial color display and multi-color display can be achieved by using a method in which light emitting materials having different emission colors are separately applied or a method using a color filter or a fluorescence conversion filter.
  • These display devices can be used as computers, televisions, portable terminals, cellular phones, car navigation systems, video camera viewfinders, and the like.
  • the planar light-emitting device is a self-luminous thin type and can be suitably used as a planar light source for a backlight of a liquid crystal display device or a planar illumination light source. If a flexible substrate is used, it can be used as a curved light source or a curved display device.
  • Example 1 (1) Preparation of ink S1 Anisole (boiling point 153.7 ° C., viscosity 1.2 cP, surface tension 35.2 mN / m, solvent (B)) 70% by volume and butyl benzoate (boiling point 250.3 ° C., viscosity 3) .17 cP, surface tension 33.6 mN / m, solvent (A)) 30% by volume is mixed to prepare 100 ml of a mixed solvent, and 100 ml of this mixed solvent is an organic EL material (material constituting the light emitting layer).
  • Ink S1 was prepared by adding 1 g of a polyfluorene derivative. Ink S1 had a surface tension of 34.5 mN / m and a viscosity of 10.5 cP.
  • (2) Production of Organic EL Element A substrate shown in FIG. 2 having a matrix in which a large number of pixel regions 41 partitioned by box-shaped partition walls 42 was formed was prepared.
  • FIG. 4 is a diagram showing a part of the matrix in which the pixel region 41 is formed. In the pixel region 41, an anode made of ITO is formed.
  • This substrate was subjected to oxygen plasma treatment (conditions: 3 Pa, 30 W, 30 SCCM, 3 minutes) and CF 4 plasma treatment (conditions: 20 Pa, 20 W, 20 SCCM, 2 minutes) using an RIE apparatus (SAMCO, RIE-200L).
  • RIE apparatus SAMCO, RIE-200L
  • a liquid repellent treatment was selectively performed on the partition wall 42 of the substrate.
  • Ink S1 was applied on the anode of the pixel region 41 with a liquid column using a nozzle printing apparatus (NP-300G, manufactured by Dainippon Screen). A plurality of pixel regions forming a row on the substrate by moving the substrate so that the nozzle relatively moves in the longitudinal direction of the pixel region 41 while continuously ejecting ink from the nozzles of the nozzle printing apparatus without interruption.
  • FIG. 5 is a cross-sectional view immediately after ink application along the line II ′ of FIG. 4, and FIG. 6 is a cross-sectional view after the ink has dropped into the pixel region and dried.
  • the ink 53 was applied intermittently and continuously in the pixel region 41 and on the partition wall 42, but the ink applied on the partition wall shrinks due to drying over time.
  • the organic EL layer was uniformly dropped into the pixel region, and a uniform organic EL layer with small unevenness between pixels and unevenness within the pixels could be formed as shown in FIG. When the matrix was visually confirmed from the upper surface, no unpainted portion was found in each pixel region.
  • Comparative Example 1 (1) Preparation of Ink Anisole alone was used as a solvent, and 1 g of a polyfluorene derivative as an organic EL material was added to 100 ml of anisole to prepare an ink R1 as a comparative example. Ink R1 had a surface tension of 35.2 mN / m and a viscosity of 9 cP. (2) Preparation of organic EL element Ink R1 was used in place of ink S1, and ink R1 was applied onto the substrate by the same process as in Example 1 described above. The organic EL element of Comparative Example 1 was produced by drying the ink 53 after application in the same manner as in Example 1. When the matrix was visually confirmed from the upper surface, it was confirmed that there was unevenness between pixels.
  • FIG. 7 shows a cross-sectional shape after drying based on the measurement result of the visual and palpation type step gauge. As shown in FIG. 7, the dried ink 54 (formed layer) had uneven film thickness within the pixel area 41, and uneven film thickness between pixels.
  • the ink for applying a liquid column of the present invention is suitably used for producing an organic EL element by applying a liquid column such as a nozzle printing method.
  • a liquid column such as a nozzle printing method.
  • the ink it is possible to form a favorable organic EL layer in which unevenness between pixels and unevenness in pixels is suppressed even when a liquid column is applied to a substrate having a general box-shaped partition wall.
  • a high-quality organic EL element and an organic EL device having the organic EL element can be obtained, it is extremely useful industrially.

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  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne une encre de revêtement de colonne de liquide qui comprend des matériaux électroluminescents organiques et un solvant dont la viscosité se situe dans la plage comprise entre 2,5 cP et 10 cP et présentent un point d'ébullition figurant dans la plage comprise entre 210 °C et 290 °C. La formation d'une couche électroluminescente organique optimum est possible grâce à l'utilisation de l'encre pour réaliser un revêtement de colonne de liquide, comme dans le procédé d'impression par buse, notamment sur des cloisonnages en forme de boîte. La couche électroluminescente organique formée permet de réduire le manque d'uniformité de l'épaisseur du film dans les pixels et d'assurer une forte uniformité de l'épaisseur du film dans les pixels. Par conséquent, l'absence d'uniformité de l'affichage est supprimée et un élément électroluminescent organique haute qualité présentant des propriétés de luminescence supérieures est obtenu.
PCT/JP2010/062021 2009-07-17 2010-07-09 Encre de revêtement de colonne de liquide, procédé de production d'élément électroluminescent organique et dispositif électroluminescent organique muni dudit élément WO2011007849A1 (fr)

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JP2009-169403 2009-07-17
JP2009169403A JP2011023668A (ja) 2009-07-17 2009-07-17 液柱塗布用インクおよび有機ｅｌ素子の製造方法、並びに該有機ｅｌ素子を有する有機ｅｌ表示装置

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JP6015073B2 (ja) * 2012-04-02 2016-10-26 セイコーエプソン株式会社 機能層形成用インク、発光素子の製造方法
US9865816B2 (en) 2014-03-17 2018-01-09 Joled Inc. Solution for forming function layer contained in organic light emitting element and method for manufacturing organic light emitting element
CN108400259B (zh) * 2018-03-20 2020-05-01 京东方科技集团股份有限公司 Oled器件的制备方法及显示面板的制备方法
CN110406266B (zh) * 2019-08-30 2020-08-25 昆山国显光电有限公司 喷墨打印装置和喷墨打印方法

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JP2008198365A (ja) * 2007-02-08 2008-08-28 Mitsubishi Chemicals Corp 有機電界発光素子の製造方法
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