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WO2007034900A1 - Procédé de production de dispositif luminescent organique, dispositif luminescent organique, et appareil électronique - Google Patents

Procédé de production de dispositif luminescent organique, dispositif luminescent organique, et appareil électronique Download PDF

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Publication number
WO2007034900A1
WO2007034900A1 PCT/JP2006/318786 JP2006318786W WO2007034900A1 WO 2007034900 A1 WO2007034900 A1 WO 2007034900A1 JP 2006318786 W JP2006318786 W JP 2006318786W WO 2007034900 A1 WO2007034900 A1 WO 2007034900A1
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WO
WIPO (PCT)
Prior art keywords
substrate
protrusion
hole
organic light
layer
Prior art date
Application number
PCT/JP2006/318786
Other languages
English (en)
Japanese (ja)
Inventor
Keiichi Inoue
Yuzuru Sato
Koichi Terao
Original Assignee
Seiko Epson Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Seiko Epson Corporation filed Critical Seiko Epson Corporation
Priority to JP2007536564A priority Critical patent/JPWO2007034900A1/ja
Publication of WO2007034900A1 publication Critical patent/WO2007034900A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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]
    • H10K50/14—Carrier transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10—OLED displays
    • H10K59/12—Active-matrix OLED [AMOLED] displays
    • H10K59/127—Active-matrix OLED [AMOLED] displays comprising two substrates, e.g. display comprising OLED array and TFT driving circuitry on different substrates
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1416—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1425—Non-condensed systems

Definitions

  • the present invention relates to a method for manufacturing an organic light emitting device, an organic light emitting device, and an electronic device.
  • An organic EL (electric-mouth luminescence) element (organic light-emitting element) has a configuration in which an organic layer including a thin film (light-emitting layer) containing at least a fluorescent organic compound is sandwiched between a cathode and an anode. In this film, electrons and holes are injected and recombined to generate excitons, and light emission (fluorescence / phosphorescence) when the excitons are deactivated is used. Element that emits light.
  • This organic EL device is capable of surface emission with a high luminance of about 100 to 100,000 cdZm 2 at a low voltage of 10 V or less, and by selecting the type of fluorescent material, from blue to red It is attracting attention as an element that can realize a large-area full-color display at low cost.
  • this organic EL device has been conventionally used in various vapor deposition methods such as vacuum deposition and chemical vapor deposition (CVD), casting, spin coating, and inkjet.
  • various vapor deposition methods such as vacuum deposition and chemical vapor deposition (CVD), casting, spin coating, and inkjet.
  • CVD chemical vapor deposition
  • an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are laminated in this order on a single substrate.
  • An object of the present invention is to provide at least one carrier transport layer, and one of the carrier transport layers is not limited to a solid carrier transport material, but also a liquid or semi-solid carrier transport material.
  • An object of the present invention is to provide a method for manufacturing an organic light emitting device including an organic light emitting element that can be configured, an organic light emitting device that is manufactured by the method for manufacturing an organic light emitting device, has high characteristics, and a highly reliable electronic device.
  • a method for manufacturing an organic light-emitting device of the present invention includes:
  • a layer is formed by a liquid phase film formation method or a gas phase film formation method, and the carrier transport layer composed of the predetermined carrier transport material is formed by another method, thereby forming the organic light emitting element having a laminated structure.
  • the carrier transport layer is formed by injecting the predetermined carrier transport material into the gap from the first liquid injection part.
  • an organic light emitting device includes an organic light emitting element that includes at least one carrier transport layer, and one of the carrier transport layers can also be configured by a liquid or semi-solid carrier transport material. can do.
  • the first liquid injection part is the first base. It is preferably a hole formed in the plate or the second substrate.
  • the first liquid injection part can be formed at a desired position, it is possible to reliably inject a predetermined carrier transport material into the target gap position.
  • the hole is provided so as not to overlap with a region where the light-emitting layer is formed.
  • the hole is subjected to a liquid repellent treatment around the hole.
  • the hole is formed after a liquid repellent treatment is performed on a region including the region where the hole is formed on the first substrate or the second substrate. This is preferred.
  • a lyophilic treatment is performed on the inside of the hole.
  • the hole communicates with the first hole on the gap side and the first hole, and is smaller than the cross section of the first hole.
  • it is constituted by two holes.
  • the predetermined carrier transporting material supplied to the hole can be reliably held in the first hole.
  • the predetermined carrier transport material is supplied so as to fill the first hole.
  • the contact angle of the predetermined carrier transport material in the region where the liquid repellent treatment is performed on the first substrate or the second substrate is set to A [°]. And the relationship of AB ⁇ 15 ° is preferably satisfied, where B [°] is the contact angle of the predetermined carrier transport material in the first hole.
  • the predetermined carrier transport material is supplied so as to fill the first hole by satisfying the strong relationship, the predetermined carrier transport is performed on the substrate side on which the hole is formed. It is possible to more reliably prevent the material from moving.
  • the hole is formed after the layers other than the carrier transport layer are formed and before the first substrate and the second substrate are bonded. .
  • the hole is formed after the first substrate and the second substrate are bonded.
  • the hole can be formed more accurately in the target region.
  • the thickness of the gap is controlled by a spacer.
  • the first substrate and the second substrate can be bonded in a state where the width of the gap in the thickness direction of the first substrate is substantially constant.
  • the spacer is constituted by a protrusion formed along an outer periphery of a region where the carrier transport layer is formed,
  • the protrusion is provided with a second liquid injection part for injecting the predetermined carrier transporting material injected from the first liquid injection part into the gap.
  • the function as a spacer can be exerted, and the predetermined carrier transporting material can be prevented from flowing out of the organic light emitting device.
  • the function as a barrier layer can be exhibited.
  • the protrusion includes a first protrusion provided on the first substrate side and a second protrusion provided on the second substrate side. Formed by contact,
  • the second liquid injecting unit lowers the height of a part of the first protrusion and the height of Z or the part of the second protrusion, and the first protrusion and the second protrusion It is preferably obtained by bringing them into contact with each other.
  • the protrusion includes a first protrusion provided on the first substrate side and a second protrusion provided on the second substrate side. Formed by contact,
  • the second liquid injection part is preferably a through hole provided in one of the first protrusion and the second protrusion.
  • the spacer is preferably composed of particles.
  • the particles are preferably disposed in the gap.
  • the width of the gap formed in the thickness direction of the first substrate can be made substantially constant.
  • the predetermined carrier transport material it is preferable to supply the predetermined carrier transport material to the first liquid injection part using an ink jet method.
  • the inkjet method it is possible to selectively block each first liquid injection portion with a predetermined carrier transport material, so that waste of the predetermined carrier transport material can be omitted.
  • a predetermined carrier transport material can be injected into the gap to form a carrier transport layer composed of this carrier transport material.
  • the pressure difference between the atmospheric pressure and the gap is 1
  • the carrier transport material can be reliably injected into the gap. .
  • the predetermined carrier transport material is heated by heating one or both of the first substrate and the second substrate. It is preferable.
  • the predetermined carrier transport material can be heated, and the viscosity of the carrier transport material can be reliably reduced.
  • the predetermined carrier transport material is preferably a hole transport material.
  • the predetermined carrier transport material includes a hole transport portion having a function of transporting holes and at least one straight chain connected to the hole transport portion. It is preferable to use a hole transport material composed of an alkyl group as a main material.
  • the powerful compound is a liquid and a hole transporting material having an excellent hole transporting ability
  • an organic light-emitting device to be obtained can be obtained by forming a hole transporting layer with the powerful compound. It can be excellent in characteristics.
  • the method for producing an organic light-emitting device of the present invention includes a cathode, an anode, a light-emitting layer, a hole transport layer, and an electron transport layer constituting an organic light-emitting element sandwiched between a first substrate and a second substrate.
  • a layer other than the hole transport layer is formed by a liquid phase film formation method or a gas phase film formation method, and the hole transport layer formed of a hole transport material is formed by another method, thereby forming a laminated structure.
  • Forming a first liquid injection part by providing a hole in the first substrate so as not to overlap with a region where the light emitting layer is formed in the first substrate;
  • the step of supplying the hole transport material so as to block the first liquid injection part, and the difference in pressure between the pressure of the gap and the atmospheric pressure is used to remove the hole transport material from the gap.
  • a hole transport layer is provided, and the hole transport layer is not limited to a solid hole transport material, and includes an organic light emitting device that can be configured by a liquid or semi-solid hole transport material. An organic light emitting device can be manufactured.
  • the method for producing an organic light-emitting device of the present invention includes a cathode, an anode, a light-emitting layer, a hole transport layer, and an electron transport layer constituting an organic light-emitting element sandwiched between a first substrate and a second substrate.
  • the layers other than the electron transport layer are formed by a liquid phase film formation method or a gas phase film formation method, and the electron transport layer made of an electron transport material is formed by another method, thereby forming the above-mentioned layered structure.
  • the hole transport layer and the light emitting layer are formed in this order on the anode exposed inside the first protrusion, and on the second substrate exposed inside the second protrusion. Forming the cathode; and
  • a gap is provided between the first substrate and the second substrate, and a second liquid injection section for injecting the electron transport material into the gap between the first protrusion and the second protrusion.
  • Forming a first liquid injection part by providing a hole in the first substrate so as not to overlap with a region where the light emitting layer is formed in the first substrate;
  • the step of supplying the electron transport material so as to block the first liquid injection portion, and the difference in pressure between the pressure of the gap and the atmospheric pressure is used to inject the electron transport material into the gap.
  • an organic light-emitting device including an electron transport layer and an organic light-emitting element that can be configured not only by a solid electron transport material but also by a liquid or semi-solid electron transport material. Can be manufactured.
  • the method for producing an organic light-emitting device of the present invention includes a cathode, an anode, a light-emitting layer, a hole-transporting layer, and an electron-transporting layer constituting an organic light-emitting element sandwiched between a first substrate and a second substrate.
  • a layer other than the hole transport layer is formed by a liquid phase film formation method or a gas phase film formation method, and the hole transport layer formed of a hole transport material is formed by another method, thereby forming a laminated structure.
  • the step of supplying the hole transport material so as to block the first liquid injection part, and the difference in pressure between the pressure of the gap and the atmospheric pressure is used to remove the hole transport material from the gap. Forming the hole transport layer by injecting, and Sealing the first liquid injection part.
  • a hole transport layer is provided, and the hole transport layer is not limited to a solid hole transport material, and includes an organic light-emitting element that can be configured by a liquid or semi-solid hole transport material.
  • An organic light emitting device can be manufactured.
  • the method for producing an organic light-emitting device of the present invention includes a cathode, an anode, a light-emitting layer, a hole transport layer, and an electron transport layer constituting an organic light-emitting element sandwiched between a first substrate and a second substrate.
  • the layers other than the electron transport layer are formed by a liquid phase film formation method or a gas phase film formation method, and the electron transport layer made of an electron transport material is formed by another method, thereby forming the above-mentioned layered structure.
  • the hole transport layer and the light emitting layer are formed in this order on the anode exposed inside the first protrusion, and on the second substrate exposed inside the second protrusion. Forming the cathode; and
  • a gap is provided between the first substrate and the second substrate, and a second liquid injection section for injecting the electron transport material into the gap between the first protrusion and the second protrusion.
  • an organic light-emitting device including an electron-transporting layer, and including an organic light-emitting element that can be configured not only by a solid electron-transporting material but also by a liquid or semi-solid electron-transporting material. Can be manufactured.
  • a carrier transport layer can be formed.
  • the carrier transport layer constituting the organic light-emitting element is formed integrally with the plurality of organic light-emitting elements.
  • the organic light-emitting device of the present invention is manufactured by the method for manufacturing an organic light-emitting device of the present invention.
  • An electronic apparatus of the present invention includes the organic light-emitting device of the present invention.
  • FIG. 1 is a longitudinal sectional view showing a first embodiment of an active matrix display device to which the light emitting device of the present invention is applied.
  • FIG. 2 is a perspective view showing a first embodiment of an active matrix display device to which the light emitting device of the present invention is applied.
  • FIG. 3 is a diagram for explaining a method of manufacturing the active matrix display device shown in FIG. 1.
  • FIG. 3 is a diagram for explaining a method of manufacturing the active matrix display device shown in FIG. 1.
  • FIG. 4 is a diagram for explaining a method of manufacturing the active matrix display device shown in FIG. 1.
  • FIG. 5 is a view for explaining a method of manufacturing the active matrix display device shown in FIG. 1.
  • FIG. 5 is a view for explaining a method of manufacturing the active matrix display device shown in FIG. 1.
  • FIG. 6 is a longitudinal sectional view showing a second embodiment of an active matrix display device to which the organic light-emitting device of the present invention is applied.
  • FIG. 7 is a perspective view showing a second embodiment of an active matrix display device to which the organic light-emitting device of the present invention is applied.
  • FIG. 8 is a plan view showing a second embodiment of an active matrix display device to which the organic light-emitting device of the present invention is applied.
  • FIG. 9 is a diagram for explaining a method of manufacturing the active matrix display device shown in FIG. 6.
  • FIG. 10 is a diagram for explaining a method of manufacturing the active matrix display device shown in FIG. 6.
  • FIG. 11 is a diagram for explaining a method of manufacturing the active matrix display device shown in FIG. 6.
  • FIG. 12 is a longitudinal sectional view showing a third embodiment of an active matrix display device to which the light emitting device of the present invention is applied.
  • FIG. 13 is a longitudinal sectional view showing a fourth embodiment of an active matrix display device to which the light emitting device of the present invention is applied.
  • FIG. 14 is a perspective view showing a configuration of a mopile type (or notebook type) personal computer to which the electronic apparatus of the invention is applied.
  • FIG. 15 is a perspective view showing a configuration of a mobile phone (including PHS) to which the electronic apparatus of the invention is applied.
  • FIG. 16 is a perspective view showing a configuration of a digital still camera to which the electronic apparatus of the invention is applied.
  • the hole transport layer 6 is provided so as to correspond to the shape of each organic EL element 1, that is, the hole transport layer 6 is provided individually for each organic EL element 1. I will explain it if it is.
  • FIGS. 1 and 2 are views showing a first embodiment of an active matrix display device to which the organic light-emitting device of the present invention is applied.
  • FIG. 1 is a longitudinal sectional view
  • FIG. 2 is a perspective view.
  • It is. 3 to 5 are diagrams for explaining a method of manufacturing the active matrix display device shown in FIGS. 1 and 2.
  • FIG. 2 is shown upside down with respect to the display device of FIG. 1 for convenience of explanation, and the description of the substrate 20 and the sealing portion 74 is omitted.
  • the upper side in FIGS. 1 to 5 is referred to as “upper” and the lower side is referred to as “lower”.
  • An active matrix display device 10 shown in FIGS. 1 and 2 includes a TFT circuit substrate (counter substrate) 20 and organic light emission provided on the substrate 20. It has an element 1 and an upper substrate 9 (first substrate) facing the TFT circuit substrate 20 (second substrate).
  • the TFT circuit substrate 20 includes a substrate 21 and a circuit unit 22 formed on the substrate 21.
  • the substrate 21 serves as a support for each part of the display device 10, and the upper substrate 9 functions as, for example, a protective layer for protecting the organic light emitting element 1.
  • the display device 10 of the present embodiment is configured to extract light from the substrate 21 side (bottom emission type), the substrate 21 is substantially transparent (colorless transparent, colored transparent, translucent).
  • the upper substrate 9 is not particularly required to be transparent.
  • a substrate 21 For such a substrate 21, various types of glass material substrates can be used. Various high hardness resin substrates can also be used.
  • the upper substrate 9 is not limited to those listed as the constituent materials of the substrate 21, but may be, for example, a polyimide resin, a polyester resin, a polyamide resin, a polyether ether ketone, or a polyethersulfone.
  • a substrate composed mainly of a polyether-based resin may be used.
  • the substrate mainly made of the polyimide-based resin can keep the heat shrinkage rate low.
  • a substrate composed mainly of polyester-based resin has the advantage of good dimensional stability. is there.
  • a carbon-based material such as a ceramic material, a metal material, carbon fiber, or the like can be used.
  • the average thickness of the substrate 21 is not particularly limited, but is preferably about 0.1 to 30 mm, more preferably about 0.5 to 2 Omm.
  • the average thickness of the upper substrate 9 is not particularly limited, but is preferably about 0.1 to 30 mm, more preferably about 0.1 to about LOmm.
  • the circuit unit 22 includes a base protective layer 23 formed on the substrate 21, a driving TFT (switching element) 24 formed on the base protective layer 23, a first interlayer insulating layer 25, 2 interlayer insulation layer 26.
  • the driving TFT 24 includes a semiconductor layer 241 and a gate insulating layer 2 formed on the semiconductor layer 241.
  • Adjacent organic light emitting devices 1 are separated by protrusions (banks) 7.
  • the cathode 3 of each organic light emitting element 1 constitutes a pixel electrode, and is electrically connected to the drain electrode 245 of each driving TFT 24 by the wiring 27.
  • the organic semiconductor layer composed of the electron transport layer 4, the light emitting layer 5, and the hole transport layer 6 is individually formed for each organic light emitting element 1, and among these layers, the hole transport layer 6 is in a liquid, semi-solid state. It can also be constituted by a solid or solid hole transport material.
  • the anode 8 is regarded as a common electrode.
  • the display device 10 selects a light emitting material used for each organic light emitting element 1 that may be monochromatic display, that is, a light emitting material used for the light emitting layer 5 for each organic light emitting element 1.
  • color display is also possible by appropriately selecting any one of a red light emitting material, a green light emitting material, and a blue light emitting material.
  • the organic light emitting device 1 will be described in detail.
  • the organic light emitting device 1 includes an electron transport layer 4, a light emitting layer 5, and a positive electrode between a cathode 3, an anode 8, and a cathode 3 and an anode 8 in order from the cathode 3 side.
  • the hole transport layer 6 is inserted.
  • the cathode 3 is an electrode that injects electrons into the electron transport layer 4.
  • the constituent material (cathode material) of the cathode 3 it is preferable to use a material having a small work function.
  • cathode materials include Li, Mg, Ca, Sr, La, Ce, Er, Eu, Sc, Y, Yb, Ag, Cu, Al, Cs, Rb, and alloys containing these. And at least one of these can be used.
  • an alloy when used as the cathode material, it is preferable to use an alloy containing a stable metal element such as Ag, Al, or Cu, specifically, an alloy such as MgAg, AlLi, or CuLi.
  • an alloy such as MgAg, AlLi, or CuLi.
  • the average thickness of the cathode 3 is not particularly limited, but is preferably about 100 nm to 3000 nm, more preferably about 500 to 2000 nm. If the thickness of the cathode 3 is too thin, the functions of the cathode 3 may not be sufficiently exhibited. On the other hand, if the cathode 3 is too thick, the light transmittance may be significantly reduced depending on the type of cathode material. If the configuration of the organic EL element 1 is a bottom emission type, it may not be suitable for practical use.
  • the anode 8 is an electrode for injecting holes into the hole transport layer 6.
  • anode material As the constituent material of the anode 8 (anode material), it is preferable to use a material having a large work function and excellent conductivity.
  • an anode material for example, ITO (composite of indium oxide and zinc oxide), SnO, Sb-containing SnO, A1-containing oxide such as ZnO, Au, Pt, Ag, Cu or these
  • the average thickness of the anode 8 is not particularly limited, but is preferably about 10 to 200 nm, more preferably about 50 to 150 nm. If the thickness of the anode 8 is too thin, the function as the anode 8 may not be sufficiently exhibited. On the other hand, if the anode 8 is too thick, the light emission efficiency of the organic EL element 1 may be reduced.
  • a conductive resin material such as polythiophene or polypyrrole can be used.
  • an electron transport layer 4 is provided as organic semiconductor layers, and these are formed on the cathode 3 in this order.
  • the electron transport layer 4 is a layer having a function of transporting electrons injected from the cathode 3 to the light emitting layer 5.
  • the constituent material (electron transport material) of the electron transport layer 4 is, for example, 1, 3, 5 tris [(3-Ferro 6 trifluoromethyl) quinoxaline 2-yl] benzene (TPQ1), 1, 3,, 5-tris [ ⁇ 3-— (4-t-butylphenol) 6-trisfluoromethyl ⁇ quinoxaline-2-yl] benzene compounds such as benzene (TPQ2) (starburst compounds ), Naphthalene compounds such as naphthalene, phenanthrene compounds such as phenanthrene, talycene compounds such as talycene, perylene compounds such as perylene, anthracene compounds such as anthracene, pyrene compounds such as pyrene , Acridine compounds such as atalidine, stilbene compounds such as stilbene, thiophene compounds such as BBOT, and butadiene compounds such as butadiene Products, coumarin compounds such as
  • Examples include various metal complexes such as complexes having thiazole as a ligand.
  • electron transport materials include polymer materials such as oxadiazole polymer (polyoxadiazole) and triazole polymer (polytriazole). Can also be used.
  • the average thickness of the electron transport layer 4 is not particularly limited, but is preferably about 1: LOOnm, more preferably about 20-50 nm.
  • an electron injection layer for improving the electron injection efficiency from the cathode 3 may be provided between the electron transport layer 4 and the cathode 3, for example.
  • this electron injection layer for example, 8-hydroxyquinoline, oxadiazole, or derivatives thereof (for example, metal chelate oxinoid compounds containing 8-hydroxyquinoline)
  • 8-hydroxyquinoline, oxadiazole, or derivatives thereof for example, metal chelate oxinoid compounds containing 8-hydroxyquinoline
  • these can be used in combination of one or more of these (for example, as a multi-layer laminate, etc.), various inorganic insulating materials, various inorganic semiconductor materials, etc. Can be used.
  • the electron injection layer using an inorganic insulating material or an inorganic semiconductor material as a main material, it is possible to effectively prevent leakage of current, improve electron injection properties, and improve durability. it can.
  • Examples of such inorganic insulating materials include alkali metal chalcogenides (acids, sulfides, selenides, tellurides), alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal. Halides, etc., of which
  • One or a combination of two or more can be used. By configuring the electron injection layer using these as main materials, the electron injection property can be further improved.
  • alkali metal chalcogenide examples include Li 0, LiO, Na S, Na Se, NaO and the like.
  • alkaline earth metal chalcogenide examples include CaO, BaO, SrO, BeO, and BaS.
  • alkali metal halides include CsF, LiF, NaF, KF, LiCl, and KC1. , NaCl and the like.
  • alkaline earth metal halides include CaF, BaF, SrF, MgF, B
  • the inorganic semiconductor material for example, at least one element of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb and Zn is used.
  • examples thereof include oxides, nitrides, and oxynitrides, and one or more of these can be used in combination.
  • the inorganic material is preferably microcrystalline or amorphous. Thereby, since the electron injection layer becomes more homogeneous, pixel defects such as dark spots can be reduced.
  • the hole transport layer 6 has a function of transporting holes injected from the anode 8 to the light emitting layer 5.
  • the hole transport layer is limited to a solid hole transport material by applying the method for manufacturing an organic light-emitting device of the present invention described below to manufacture the display device 10. It can also be constituted by a liquid or semi-solid hole transport material that is not specified.
  • those solid at room temperature include, for example, 1, 1-bis (4 diparatriaminophenol) cyclohexane, 1 , 1, 1bis (4-diparatriaminophenol) 4-aryl-cycloalkane compounds such as 4-phenyl-cyclohexane, 4, 4 ', 4 "trimethyltriphenylamine, N, N, ⁇ ', ⁇ , —Tetrafenyl 1, 1, 1, Biphenyl 1, 4, 4, One Diamine, ⁇ , ⁇ , One Diphenyl One ⁇ , ⁇ ⁇ , —Bis (3-methylphenol) 1, 1, One Biphenyl 4, one diamine (TPD1), N, N, one diphenyl one N, N, one bis (4-methoxyphenyl) one 1, 1, one biphenyl one 4, 4, one diamine (TPD2), N, N, ⁇ ', ⁇ , 1 tetrakis (4-methoxyphenol) 1, 1, 1
  • a phosphorus compound such as polyarine, silane compound, 1,4-dithioketoto 3, 6—diphenol-pyrrolopyrrole (3, 4-c) pyrrole compound such as pyrrolopyrrole, florene, etc.
  • the hole transport material that is liquid or semi-solid at room temperature is not particularly limited, but the above-described hole transport material (low molecular weight compound) that is solid at room temperature is used as the hole transport part.
  • Those having at least one linear alkyl group connected to the hole transporting portion are preferably used.
  • the melting point and the glass transition temperature can be controlled by a relatively easy method of adjusting the chain length (molecular weight) of the straight-chain alkyl group and the number to be introduced, the organic light-emitting device of the present invention described later is used. Depending on the method for manufacturing the device, it can be suitably used as a hole transport material that is liquid or semi-solid at room temperature.
  • a hole transport material that is liquid or semi-solid at room temperature
  • a compound represented by the following general formula (A1) hereinafter, this compound is referred to as “compound (Al)”.
  • X 1 , X 2 , X 3 and X 4 each independently represent a hydrogen atom or a linear alkyl group, and may be the same or different.
  • at least one of X 1 , X 2 , X 3 and X 4 represents a linear alkyl group having 3 to 8 carbon atoms, and the other represents a hydrogen atom, a methyl group or an ethyl group.
  • Eight R's each independently represent a hydrogen atom, a methyl group or an ethyl group, and they may be the same or different.
  • Y is a substituted or unsubstituted aromatic hydrocarbon ring. Represents a group containing at least one of ]
  • Such a compound (A1) has an excellent hole transport ability and forms a liquid or semi-solid form at room temperature.
  • the substituent X 1 , the substituent X 2 , the substituent X 3 and the substituent X 4 (hereinafter these are collectively referred to as “substituent X”) Is at least one, preferably 2, more preferably 3, and even more preferably 4 of these are straight-chain alkyl groups having 3 to 8 carbon atoms.
  • substituted X By introducing a linear alkyl group having 3 to 8 carbon atoms and increasing the number thereof, the melting point and glass transition temperature of the compound (A1) are lowered.
  • crystallization of this compound is suppressed, and an amorphous state is likely to occur. As a result, the viscosity of the compound (A1) can be reliably reduced.
  • the main skeleton of the compound (A1) since the main skeleton of the compound (A1) has a conjugated chemical structure, carriers are smoothly transferred between the compounds due to the spread of its unique electron cloud. Thereby, the compound (A1) exhibits an excellent carrier transport ability.
  • the number of carbon atoms of the linear alkyl group is more preferably 3-6. If the straight-chain alkyl group has too few carbon atoms, the interaction between the substituents X becomes small, and there is a possibility that the compound (A1) is less likely to be amorphous. As a result, the compound (A1) may be in a solid state.
  • the substituent X 1 and the substituent X 3 are linear alkyl groups having 3 to 8 carbon atoms. Is preferred. As a result, the interaction between the substituents X occurs more reliably, so that the viscosity of the compound (A1) can be reliably reduced.
  • each substituent X has substantially the same carbon number. It is more preferable that the number of carbon atoms is. Thereby, it is possible to prevent or suppress the occurrence of variations in the distance between the compounds (A1), that is, the main skeletons. As a result, it is possible to suitably prevent the occurrence of bias in the delivery of holes in each part of the hole transport material. In other words, the hole transport capability in each part of the hole transport layer 6 becomes more uniform.
  • the substituent X may be bonded to any position from the 2-position to the 6-position of the benzene ring, and in particular, is bonded to any of the 3-position, 4-position or 5-position. Is preferred. As a result, the interaction between the substituents X occurs more reliably, and the compounds (A1) Can be separated at a more appropriate distance. Thereby, it is possible to reliably prevent the hole transport from being reduced while lowering the viscosity of the hole transport material.
  • those other than a straight-chain alkyl group having 3 to 8 carbon atoms represent a hydrogen atom, a methyl group or an ethyl group. It may be carried out according to the number of carbon atoms of the substituent X representing the straight-chain alkyl group. For example, when the substituent X representing a linear alkyl group having 3 to 8 carbon atoms has a large number of carbon atoms, other than that, a hydrogen atom is selected and a linear alkyl group having 3 to 8 carbon atoms is represented. If the substituent X has a small number of carbon atoms, the other group may be selected from a methyl group or an ethyl group.
  • the substituent R is a hydrogen atom, a methyl group or an ethyl group, and the substituent R may be selected according to the number of carbons in the substituent X. For example, when the carbon number of the substituent X is large, a hydrogen atom is selected as the substituent R, and when the carbon number of the substituent X is small, a methyl group or an ethyl group is used as the substituent R. Make a choice!
  • the group Y only needs to contain at least one substituted or unsubstituted aromatic hydrocarbon ring, but is preferably composed of a carbon atom and a hydrogen atom. Thereby, since the transfer of holes between the compounds (A1) is reliably performed, the compound (A1) exhibits an excellent hole transport ability.
  • examples of the structure containing at least one aromatic hydrocarbon ring include those represented by the following chemical formulas (B1) to (B17).
  • the total number of carbon atoms in the group Y is preferably 6-30, more preferably 10-25, and even more preferably 10-20.
  • the number of aromatic hydrocarbon rings is preferably 1 to 5, more preferably 2 to 5, and even more preferably 2 or 3.
  • the base is biphenylene group. Or its derivatives are particularly preferred, the structure.
  • the hole transport material has a more excellent hole transport ability.
  • the substituent when a substituent is introduced into the aromatic hydrocarbon ring, the substituent is not particularly limited as long as the planarity of the group Y can be maintained. It is more preferably a methyl group or an ethyl group, preferably a straight chain alkyl group of 1 to 3.
  • a hole transport material when it is a low molecule (monomer or oligomer), it is liquid or semi-solid at room temperature. By doing so, those that become solid can also be used.
  • the hole transport material is formed in a liquid or semi-solid (low molecular weight) state when forming the hole transport layer 6 in the method of manufacturing the light emitting device 10 described later.
  • the solid hole transport layer 6 By injecting into the gap 76 from the first liquid injection section 77 and polymerizing (curing) this hole transport material, the solid hole transport layer 6 can be formed in the gap 76.
  • the heat resistance of the hole transport material can be improved.
  • diffusion of the hole transport material (low molecule) into the light emitting layer 5 can be suitably prevented.
  • Such a hole transport material is not particularly limited.
  • a polymerizable group is added to the terminal of the linear alkyl group of the above-described normal or liquid or semi-solid hole transport material. What is provided is used suitably.
  • the polymerizable group is not particularly limited as long as it undergoes a polymerization reaction between the polymerizable groups so that adjacent hole transport materials can be linked to each other by performing a predetermined treatment.
  • Examples include xetane group, (meth) attalyloyl group, burether group, and burbendylether group, and one or more of these can be used in combination.
  • the substituent X 1 , the substituent X 2 , the substituent X 3 and the substituent X 4 are each independently a hydrogen atom, a methyl group, an ethyl group or the following general formula (B1) to the following general formula: Represented by (B4)
  • at least one of the substituent X 1 , the substituent X 2 , the substituent X 3 and the substituent X 4 is a substituent represented by the following general formula (B1) to the following general formula (B4). Of which represents the deviation.
  • H 2 C G— c— ⁇ ⁇ -, ( ⁇ 1) H Z C ⁇ —, CH-CH Z — 0- cH 2 (B 2)
  • n 1 represents an integer of 2 to 8.
  • n 2 represents an integer of 3 to 8
  • m represents an integer of 0 to 3.
  • Z 1 represents a hydrogen atom or a methyl group
  • Z 2 represents a hydrogen atom, a methyl group or an ethyl group.
  • the average thickness of the hole transport layer 6 is not particularly limited, but is preferably about 10 to 150 nm, and more preferably about 50 to LOOnm.
  • a hole injection layer for improving the hole injection efficiency from the anode 8 may be provided between the anode 8 and the hole transport layer 6, for example!
  • this hole injection layer for example, copper phthalocyanine or
  • excitons (excitons) are generated in the light-emitting layer 5, and energy (fluorescence or phosphorescence) is emitted (emitted) when the excitons return to the ground state.
  • a constituent material (light emitting material) of the light emitting layer 5 various polymer materials and various low molecular materials can be used alone or in combination.
  • Examples of the polymer light-emitting material include trans-type polyacetylene, cis-type polyacetylene, poly (di-phenylacetylene) (PDPA), poly (alkyl, phenylacetylene) (P Polyacetylene compounds such as APA), poly (para-phenbiene) (PPV), poly (2,5-dialkoxy-para-para-lenbi-lene) (RO—PPV), cyano-substituted monopoly (nora) Monophenbiylene) (CN—PPV), poly (2-dimethyloctylsilyl monoparadiphenyl dilembiene) (DMOS—PPV), poly (2-methoxy, 5- (2,1ethinorehexoxy) -Para-phenylene-vinylene compounds such as (para-phenylene vinylene) (MEH-PPV), polythiophenes such as poly (3-alkylthiophene) (PAT)
  • examples of low-molecular light emitting materials include benzene compounds such as distyrylbenzene (DSB) and diaminodistyrylbenzene (DADSB), naphthalene compounds such as naphthalene and nile red, and phenanthrene compounds such as phenanthrene.
  • benzene compounds such as distyrylbenzene (DSB) and diaminodistyrylbenzene (DADSB)
  • naphthalene compounds such as naphthalene and nile red
  • phenanthrene compounds such as phenanthrene.
  • Talycene, Talycene compounds such as 6-trotalicene, perylene, N, N, monobis (2,5 di-t-butylphenol) — 3, 4, 9, 10 perylene-di-carboximide (BPPC)
  • Perylene compounds such as coronene, coronene compounds such as coronene, anthracene compounds such as anthracene and bisstyrylanthracene, pyrene compounds such as pyrene, 4 (dicyanomethylene) 2-methyl 6- (para-dimethylaminostyryl) ) Pyran compounds such as 4H pyran (DC M) and atalidine compounds such as atalidine
  • Stilbene compounds such as stilbene, 2, 5 thiophene compounds such as dibenzoxazole thiophene, benzoxazole compounds such as benzoxazole, benzoimidazole compounds such as benzimidazole, 2, 2 , One (Parafene-diylene
  • fluorene compounds such as florene, 8-hydroxyquinoline aluminum (Alq), tris (4-methyl 8-quinolinolate) aluminum (III) (Almq), 8-
  • Luorro 1 1 (2 chael) Butane 1, 3 Zionate) Europium (III) (Eu (T TA) (phen)), Factory (2 ferrubiridine) Iridium (Ir (ppy)), 2, 3, 7, 8
  • the average thickness of the light-emitting layer 5 is not particularly limited, but is preferably about 10 to 150 nm, more preferably about 50 to about LOOnm.
  • the anode 8 is formed on the inner surface side of the upper substrate 9 (first substrate), the cathode 3 and the electron transport are formed on the inner surface side of the TFT circuit substrate 20.
  • the upper substrate 9 and the TFT circuit substrate 20 are joined so that a gap 76 is formed between them, and then, hole transport is performed from the first liquid injection unit 77. It is manufactured by injecting material into gap 76 to form hole transport layer 6.
  • an upper substrate (first substrate) 9 and a TFT circuit substrate (second substrate) 20 are prepared.
  • a substrate 21 is prepared, and an average thickness of about 21 is formed on the substrate 21 by, for example, a plasma CVD method using TEOS (tetraethoxysilane) or oxygen gas as a source gas.
  • a base protective layer 23 composed of silicon oxide of 200 to 500 nm as a main material is formed.
  • the driving TFT 24 is formed on the base protective layer 23.
  • an amorphous silicon having an average thickness of about 30 to 70 nm is mainly formed on the base protective layer 23 by, for example, a plasma CVD method.
  • a semiconductor film is formed.
  • the semiconductor film is crystallized by laser annealing, solid phase growth, or the like to change the amorphous silicon into polysilicon.
  • a line beam having a beam length of 400 mm is used with an excimer laser, and its output intensity is set to about 200 miZcm 2 , for example.
  • the line beam is scanned so that a portion corresponding to 90% of the peak value of the laser intensity in the short dimension direction overlaps each region.
  • the semiconductor film is patterned to form islands, and for example, a plasma C VD method or the like using TEOS (tetraethoxysilane) or oxygen gas as a source gas so as to cover each island-shaped semiconductor film 241.
  • TEOS tetraethoxysilane
  • oxygen gas as a source gas
  • a conductive film composed mainly of a metal such as aluminum, tantalum, molybdenum, titanium, or tungsten is formed on the gate insulating layer by sputtering, for example, and then patterned to form a gate electrode. 243 is formed.
  • a contact hole is formed.
  • a source electrode 244 and a drain electrode 245 are formed in the contact hole.
  • a wiring (relay electrode) 27 that electrically connects the drain electrode 245 and the anode 8 is formed.
  • wiring 27 is formed in the contact hole.
  • a TFT circuit substrate (second substrate) 20 is obtained.
  • the anode 8 is formed on the upper substrate (first substrate) 9.
  • the anode 8 can be formed by, for example, a vapor deposition method such as sputtering, vacuum deposition, and chemical vapor deposition (CVD), spin coating (pyrosol), casting, micro Liquids such as gravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing, offset printing, and inkjet printing It can be formed using a phase deposition method.
  • a vapor deposition method such as sputtering, vacuum deposition, and chemical vapor deposition (CVD), spin coating (pyrosol), casting, micro Liquids such as gravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing, offset printing, and inkjet printing It can be formed using a phase deposition method.
  • the anode 8 is formed on the entire surface of the upper substrate 9, it is not necessary to use a mask.
  • a vapor deposition method such as a vacuum deposition method is used. Is preferably used.
  • each of the first protrusions 71 has a frame shape (rectangular annular shape), and the height of one side 711 of the four sides of the quadrilateral is higher than the heights of the other sides. It is formed to be low. At this time, the adjacent first protrusions 71 are integrally formed.
  • wide ridges (ribs) 71a are formed at substantially constant intervals along the x-axis direction and are substantially orthogonal to the ridges 71a. As shown (along the y-axis direction), ridges (ribs) 71b and 71c that are narrower than the ridge 71a are formed alternately. The height of the ridge 71b The height of the ridge 71c, which is substantially equal to the height of the ridge 71a, is formed lower than the height of the ridge 71a. The ridges 71b and the ridges 71c are formed so that a first pitch and a second pitch narrower than the first pitch are repeated in order.
  • the shape of the space 712 is not limited to the square shape as in the present embodiment, for example, any shape such as a polygon such as a circle, an ellipse, a triangle, a hexagon, May be.
  • the corner is preferably rounded. As a result, the hole transport material can be reliably supplied to every corner of the space inside the first protrusion 71.
  • Such a first protrusion 71 can be formed by forming an insulating film over almost the entire anode 8, and then patterning the insulating film.
  • the constituent material of the insulating film is selected in consideration of heat resistance, liquid repellency, ink solvent resistance, adhesion to the underlayer, and the like.
  • Examples of such materials include organic materials such as acrylic resin and polyimide resin, and inorganic materials such as SiO.
  • the anode 8 when the anode 8 is composed of an oxide material as a main material, it is preferable to use SiO as the constituent material of the first protrusion 71. As a result, the anode 8 and the first protrusion 71
  • Adhesion can be improved.
  • the first protrusion 71 exhibiting liquid repellency can be obtained, for example, by using a fluorine-based resin, or by subjecting the surface of the first protrusion 71 to a fluorine plasma treatment. it can.
  • the thickness of the hole transport layer 6 can be easily set by appropriately setting the height of the first protrusion 71. ⁇ u can control.
  • the height of the first protrusion 71 is preferably about 10 to 150 nm. With such a height, the hole transport layer 6 having a desired film thickness can be obtained, and the first protrusion 71 and the second protrusion 72 can be brought into contact with each other in the subsequent step [6A].
  • the projection 7 can sufficiently function as a spacer.
  • each of the second protrusions 72 is formed so as to form a frame shape (square ring shape). At this time, the second protrusion 72 is formed so that the upper end portion of the wiring 27 is exposed in the space 722, and the adjacent second protrusions 72 are integrally formed.
  • the ridges (ribs) 72a are formed in the x-axis direction so as to be separated from each other by a certain distance, so that they are substantially perpendicular to the ridges 72a.
  • Convex ridges (ribs) 72b and 71c are formed at regular intervals (along the y-axis direction).
  • the height of the ridges 72a and the height of the ridges 71b are formed to be substantially equal.
  • Such a second protrusion 72 can be formed in the same manner as described for the first protrusion 71.
  • the height of the second protrusion 72 is appropriately set according to the total thickness of the cathode 3, the electron transport layer 4 and the light emitting layer 5, and is not particularly limited, but is preferably about 20 to 300 nm. . Because of this height, in the post-process [6A], the protrusion 7 obtained by bringing the first protrusion 71 and the second protrusion 72 into contact with each other sufficiently functions as a spacer. It can be demonstrated.
  • a cathode 3 As shown in FIG. 3 (c), a cathode 3, an electron transport layer 4 and a light emitting layer 5 are formed on a TFT circuit substrate (second substrate) 20 exposed inside the space 722. Are formed in this order.
  • the cathode (pixel electrode) 3 is formed on the TFT circuit substrate 20 exposed inside the space 722, that is, on the second interlayer insulating layer 26 so as to be in contact with the wiring 27.
  • the cathode 3 can be formed by using the vapor phase film formation method or the liquid phase film formation method as described above. Among them, the ink jet method (droplet discharge method) is used to form the cathode. Supply materials, It is preferably formed using an electroless plating method. By using a powerful method, the cathode
  • the cathode 3 can be formed as follows.
  • Ni, Cu, Co, Pd, and Pt can be used as the catalyst.
  • a colloidal solution of a Pd alloy such as Sn-Pd or a solution of an ionic Pd catalyst such as sodium chloride palladium is used in the space 722 using an inkjet method.
  • the Pd alloy or the ionic Pd catalyst is adsorbed on the TFT circuit substrate 20. Thereafter, Pd is exposed on the TFT circuit substrate 20 by removing elements not involved in the catalyst.
  • Examples of the acid solution include a solution containing an acid such as HBF and a reducing agent such as glucose.
  • a metal solution mainly composed of a metal salt and a reducing agent is supplied onto the TFT circuit substrate 20 on which the catalyst is adsorbed by using an ink jet method, and the metal element in the space 722 is supplied.
  • the cathode 3 is formed by depositing element.
  • metal salt for example, sulfate, nitrate and the like are preferably used.
  • Examples of the reducing agent include hydrazine, ammonium hypophosphite, sodium hypophosphite and the like. Among these, at least one of hydrazine and ammonium hypophosphite is mainly used. What is made into a component is preferable. By using these as reducing agents, the deposition rate of the cathode 3 becomes appropriate, and the thickness of the cathode 3 can be controlled relatively easily.
  • the content of the metal salt in the plating solution (the amount of the metal salt added to the solvent) is preferably about 1 to 50 gZL, more preferably about 5 to 25 gZL.
  • Metal salt content is If the amount is too small, it may take a long time to form the cathode 3. On the other hand, even if the content of the metal salt is increased beyond the upper limit, no further increase in effect can be expected.
  • the content of the reducing agent in the plating solution (the amount of the reducing agent added to the solvent) is preferably about 10 to 200 gZL, more preferably about 50 to 150 gZL. If the content of the reducing agent is too small, efficient reduction of metal ions may be difficult depending on the type of reducing agent. On the other hand, even if the content of the reducing agent is increased beyond the upper limit, no further increase in effect can be expected.
  • the pH adjuster there are various powers. At least one of ammonia water, trimethyl ammonium hydride, sodium hydroxide, sodium carbonate, and ammonium sulfate ammonium is mainly used. The component is preferable. Since these have an excellent buffering effect, the above-described effects can be exerted more remarkably by using these as pH adjusters.
  • the electron transport layer 4 can be formed by using the vapor phase film formation method or the liquid phase film formation method as described above, and above all, it is formed by using the ink jet method (droplet discharge method). I prefer to do it.
  • the ink jet method By using the inkjet method, the electron transport layer 4 can be made thinner and the pixel size can be reduced. Further, since the liquid electron transport layer forming material can be selectively supplied to the inside of the second protrusion 72, waste of the electron transport material can be omitted.
  • the material for forming the electron transport layer is discharged from the head of the ink jet printing apparatus, supplied onto each cathode 3, removed from the solvent or dedispersed medium, and then at 150 ° C as necessary. Apply heat treatment for a short time.
  • the desolvation or dedispersion medium is a method of leaving in a reduced pressure atmosphere, heat treatment (for example, 50 to
  • the residual solvent is removed by additional heat treatment (approximately 150 ° C for a short time). Leave.
  • the electron transport layer forming material to be used is prepared by dissolving or dispersing the electron transport material as described above in a solvent or a dispersion medium.
  • examples of the solvent or dispersion medium used for the preparation of the electron transport layer forming material include various types such as nitric acid, sulfuric acid, ammonia, hydrogen peroxide, water, carbon disulfide, carbon tetrachloride, and ethylene power sulfonate.
  • ketone solvents such as methyl ethyl ketone (MEK), acetone, jetyl ketone, methyl isobutyl ketone (MIBK), methyl isopropyl ketone (MIPK), cyclohexanone, methanol, ethanol, isopropanol, ethylene glycol , Alcohol solvents such as diethylene glycol (DEG) and glycerin, jetyl ether, diisopropyl ether, 1,2-dimethoxyethane (DME), 1,4-dioxane, tetrahydrofuran (THF), tetrahydropyran (THP), alcohol , Diethylene glycol dimethyl ether (diglyme), diethylene glycol Ether solvents such as rucetyl ether (carbitol), cellosolve solvents such as methyl cetosolve, ethylcetosolve, and ferrous solvate, aliphatic hydrocarbon
  • the material for forming an electron transport layer supplied on the cathode 3 has high fluidity (low viscosity) and a force for spreading in the horizontal direction (plane direction). Therefore, spreading outside the predetermined region is prevented, and the outline shape of the hole transport layer 6 (organic EL element 1) is accurately defined.
  • the light-emitting layer 5 can also be formed by using a vapor phase film formation method or a liquid phase film formation method, but for the same reason as described above, an ink jet method (droplet discharge method) is used. It is preferable to form.
  • an ink jet method droplet discharge method
  • the inkjet method when providing the light emitting layer 5 of a plurality of colors, there is an advantage that the pattern can be easily applied for each color.
  • the light emitting layer 5 is formed so as to be slightly lower than the height of the second protrusion 72 so that the upper surface force of the second protrusion 72 does not protrude. preferable.
  • the hole transport material can be injected into the gap 76 relatively easily in the post-process [11A].
  • the first liquid injection part 77 is formed so as to communicate with the space 713 as described above, the second liquid injection part 75, corresponding to each gap 76, The space 713 and the first liquid injection portion 77 communicate with each other in this order, and a supply path for injecting the hole transport material into the gap 76 is formed in the post-process [11A].
  • alignment marks are formed in advance on both the substrates, and these alignment marks coincide with each other. Such alignment can be performed relatively easily.
  • the second liquid injection part 75 can be formed by lowering the height of a part of the first protrusion 71 as in the present embodiment, and the height of a part of the second protrusion 72. It may be formed by reducing the height, or may be formed by reducing the height of a part of both. In addition, the second liquid injection part 75 may be a through-hole provided in one of the first protrusion 71 and the second protrusion 72.
  • the shape of the second liquid injection section 75 may be any shape such as a polygon such as a semicircle, an ellipse, a triangle, and a hexagon other than the quadrangle as in the present embodiment. Good.
  • the upper substrate 9 (first substrate) and the TFT circuit substrate 20 (second substrate) are separated by a gap 76 at their edges. Bonding is performed by forming a sealing portion 74 to be sealed.
  • the sealing portion 74 is made of, for example, a liquid sealing portion forming material containing an organic material such as an acrylic resin, a polyimide resin, or an epoxy resin, or a precursor thereof. After supplying to the region where the sealing portion 74 is to be formed using a liquid phase film forming method such as a jet method, it can be formed by drying.
  • the first protrusion 71 and the second protrusion 72 were brought into contact with each other to form the protrusion 7 as described in the step [6A]. This is done in a state, ie via a spacer.
  • the upper substrate 9 and the TFT circuit substrate 20 can be bonded in a state where the width of the upper substrate 9 in the gap 76 formed in the step [6A] is substantially constant in the thickness direction. .
  • the liquid injection part 77 is formed so as to communicate with the space 713, so that the second liquid injection part 75, the space 713, and the first liquid correspond to each gap 76.
  • the injection section 77 communicates in this order, and a supply path for injecting the hole transport material into the gap 76 is formed in the post-process [11A].
  • a method of forming the first liquid injection portion 77 that is, a method of removing a part of the upper substrate 9 and forming a hole by force in the thickness direction, for example, plasma etching, reactive ions, etc.
  • plasma etching reactive ions
  • One or more of physical etching methods such as etching, beam etching, and light-assisted etching can be used in combination.
  • the first liquid injection portion 77 is formed by providing a hole in the upper substrate 9. Accordingly, the first liquid injection part 77 can be formed at a desired position, and the hole transport material can be reliably supplied (injected) to the target gap 76 position. .
  • the TFT circuit board 20 When the TFT circuit board 20 is formed relatively thin, the TFT circuit board 20 You can make a hole on the plate 20 side!
  • this hole is provided so as not to overlap with a region where the light emitting layer 5 is formed, that is, a region where the organic EL element 1 is formed. Thereby, it is possible to reliably prevent the emission luminance of the organic EL element 1 from being lowered in the region where the hole is provided.
  • the hole (first liquid injection portion 77) is formed after the upper substrate 9 and the TFT circuit substrate 20 are joined.
  • the first liquid injection portion 77 can be reliably formed so as to correspond to the position of the formed second liquid injection portion 75. That is, the first liquid injection part 77 can be accurately formed in the target region.
  • the hole transport material supplied so as to close the first liquid injection portion 77 in the subsequent step [11A] is more reliably injected into the gap 76.
  • the holes may be formed prior to forming a layer other than the hole transport layer, for example. Thereby, it is possible to reliably prevent the influence of heat or the like generated when forming holes in the upper substrate 9 from reaching each layer.
  • the holes may be formed prior to bonding the upper substrate 9 and the TFT circuit substrate 20 after forming a layer other than the hole transport layer. As a result, it is possible to reliably prevent or suppress the removal product generated when the hole is formed in the upper substrate 9 from remaining (attached) in the gap 76. The deterioration of the characteristics of the organic EL element 1 can be surely prevented.
  • the method of depressurizing the gap 76 is not particularly limited !, but for example, the upper substrate 9 that has undergone the steps [1A] to [8A] in a depressurizable channel (not shown) and After installing the joined body with the TFT circuit board 20, a method of reducing the pressure can be used.
  • a hole transport material is supplied so as to close the first liquid injection portion 77 in a state where the inside of the gap 76 is decompressed.
  • the hole transport material is supplied to the first liquid injection section 77 by an inkjet method (droplet discharge method), among the forces that can be supplied using the liquid phase film formation method as described above. It is preferable to use and supply.
  • each hole transport material is Since the liquid injection part 77 can be selectively closed, waste of the hole transport material can be omitted.
  • a hole transport material suitable for the light emitting layer 5 for each color is easily supplied to the first liquid injection part 77 (painting). There are other advantages.
  • the hole transport material when a solid hole transport material is used, the hole transport material is heated to be in a molten state, as in the case of using a liquid or semi-solid hole transport material.
  • the hole transport material can be supplied to the first liquid injection section 77 by using various liquid phase film forming methods. In addition to these methods, for example, a hole transport material that is larger than the cross section of the first liquid injection portion 77 can be disposed in the first liquid injection portion 77. .
  • the hole transport material supplied to the first liquid injection section 77 in the molten state may be solidified by heat dissipation prior to performing the next step [11 A], or may be in a molten state. It may be that maintaining the above.
  • the hole transport material is injected into the gap 76 by utilizing the difference between the pressure of the gap 76 and the atmospheric pressure.
  • a transport layer 6 is formed.
  • the protrusion 7 is formed along the outer periphery of the region where the hole transport layer 6 is formed. On the side surface of the protrusion 7, the hole transport injected from the first liquid injection portion 77 is transported. A second liquid injection part 75 for injecting the material into the gap 76 through the space 713 is provided. This allows the hole transport material to be injected inside the protrusion 7, that is, in the gap 76.
  • the hole transport layer 6 corresponds to the shape of each organic EL element 1. Can be formed. That is, an individual hole transport layer 6 can be formed corresponding to each organic EL element 1.
  • the width of the gap 76 in the thickness direction of the upper substrate 9 between the upper substrate 9 and the TFT circuit substrate 20 through the protrusion (spacer) 7 is substantially constant. It is joined while maintaining a stable state. Therefore, in this step, the hole transport layer 6 having a uniform thickness can be obtained by injecting the hole transport material into the gap 76.
  • the thickness of the hole transport layer 6 should be set to a desired thickness without being affected by physical properties such as the viscosity of the hole transport material by appropriately setting the height of the protrusion 7. Can do.
  • the pressure difference between the pressure of atmospheric pressure and the gap 76 is a hole transport material is not particularly limited Yogu be set so as to be injected into the space 76, 1. 0 X 10- 4 ⁇ 1.0 X 10 12 Pa is preferred 1. OX lC ⁇ l. 0 X 10 5 Pa is more preferred.
  • Pressure difference force When the pressure difference is less than the lower limit, the hole transport material may not be injected into the gap 76 depending on the viscosity of the hole transport material. Further, if the pressure difference is increased beyond the upper limit, gas in the atmosphere other than the hole transport material is injected into the gap 76, and bubbles may be mixed in the hole transport material. .
  • the hole transport material supplied so as to close the first liquid injection part 77 is poured into the gap 76, the hole transport material is transferred from the first liquid injection part 77 to the gap 76.
  • the hole transport material needs to be in a liquid or semi-solid state and have a low viscosity.
  • the hole transport material I: a semi-solid material having a high viscosity at room temperature!
  • the hole transport material supplied so as to close the first liquid injection section 77 is injected into the gap 76 prior to injection. Therefore, it is necessary to heat the hole transport material. As a result, the viscosity of the semi-solid material is lowered, and the viscosity of the solid material is lowered after being melted in the same manner as the semi-solid material.
  • the hole transport material whose viscosity has been reduced passes smoothly through the supply path and is injected into the gap 76. It becomes.
  • These hole transport materials are solidified or increased in viscosity by heat dissipation after being injected into the gap 76, and constitute a solid or semi-solid hole transport layer 6.
  • Such a hole transport material can be heated, for example, by heating one or both of the upper substrate 9 and the TFT circuit substrate 20. As a result, the hole transport material can be heated to reliably reduce the viscosity of the hole transport material.
  • a heating means eg, a heater
  • it can be performed by providing a heating means (eg, a heater) (not shown) on the surface opposite to the upper substrate 9 of the TFT circuit substrate 20.
  • the hole transport material is a liquid, low viscosity, or semi-solid
  • heating of the hole transport material as described above can be omitted, and the hole transport material can be used as a gap. This eliminates the trouble of injecting into 76, so that the manufacturing cost can be reduced. Since these hole transport materials maintain a liquid or semi-solid state at room temperature even after being injected into the gap 76, the liquid or semi-solid hole transport material 6 is constituted. Become.
  • the hole transport material supplied so as to close the first liquid injection part 77 is If injection into the gap 76 without using a pressure difference is possible, the hole transport layer 6 may be formed by omitting the step [9A] and the step [11A]. .
  • a hole transporting material in the case of a low molecular weight, when it is a liquid or semi-solid state at room temperature, and becomes a solid state by polymerizing, it is in a low molecular state. After injecting the hole transport material into the gap 76 from the first liquid injection part 77, the hole transport material is polymerized by light irradiation to form a solid hole transport material 6 Can do.
  • the solid hole transport layer 6 is formed using the covert hole transport material, it is preferable to add a polymerization initiator to the hole transport material.
  • the polymerization initiator is not particularly limited, and examples thereof include a photopolymerization initiator such as a photoradical polymerization initiator and a photopower chain polymerization initiator, and the polymerization property of the hole transport material.
  • a photopolymerization initiator such as a photoradical polymerization initiator and a photopower chain polymerization initiator
  • the group for example, when using a (meth) atalyloyl group and a bulbendyl ether group, it is preferable to use a photo radical polymerization initiator.
  • an epoxy group, an oxetane group, a vinyl ether group, or the like is used.
  • light power thione polymerization initiator It is preferable to use it.
  • photoradical polymerization initiator various photoradical polymerization initiators can be used.
  • benzophenone, benzoin, acetophenone, benziketal, Michler's ketone, acylphosphine oxide, ketocoumarin Photo radical polymerization initiators such as those based on xanthene, thixanthone and thixanthone can be used.
  • various light-power thione polymerization initiators can be used.
  • an aromatic sulfo-sulfate salt, an aromatic iodine salt, and an aromatic diazo salt salt-based photodynamic cation polymerization initiators such as pyridinium salts and aromatic phospho- um salts
  • nonionic photopower thione polymerization initiators such as iron arene complexes and sulfonate esters Can be used.
  • Examples of light to be irradiated include infrared rays, visible rays, ultraviolet rays, and X-rays.
  • ultraviolet rays can be used in combination of one or more of them. Is preferably used. As a result, the polymerization reaction between the compounds can easily and reliably proceed.
  • the hole transport material may be present in the gap 76, but a part of the hole transport material is present in the second liquid injection part 75 or the space 713. Even if it seems to exist. Selection of the position and amount of such a hole transport material can be easily performed by adjusting the supply amount and viscosity of the hole transport material.
  • the first liquid injection section 77 can be sealed in the same manner as the sealing section 74 is formed using the sealing section forming material described in the step [7A], for example. .
  • the display device 10 including a plurality of organic EL elements 1 can be formed through the above-described steps.
  • the anode 8 is formed on the upper substrate (first substrate) 9 side, and the cathode 3, the electron transport layer 4 and the light emitting layer 5 are formed on the TFT circuit substrate (second substrate) 20 side.
  • the present invention is not limited to such a case.
  • the cathode 3, the electron transport layer 4 and the light emitting layer 5 are provided on the upper substrate (first substrate) 9 side, and the TFT circuit substrate (second substrate) is provided. (Substrate) Anode 8 is formed on the 20 side You may do it.
  • the anode 8 is a common electrode, that is, integrally formed as in the present embodiment, the anode 8 is individually provided to correspond to each organic EL element 1 similarly to the cathode 3. May be formed.
  • the hole transport layer 6 is individually formed corresponding to each organic EL element 1 .
  • the present invention is not limited to such a case.
  • a common hole transport layer 6 may be formed in the EL element 1.
  • Such a hole transport layer 6 corresponds to, for example, the organic EL element 1 that forms the common hole transport layer 6 so that the hole transport material can be supplied to both the adjacent gaps 76. Can be obtained by forming the protrusion 71b of the first protrusion 71 to be the same as the height of the protrusion 71c.
  • FIGS. 6 to 8 are views showing a second embodiment of an active matrix display device to which the organic light-emitting device of the present invention is applied.
  • FIG. 6 is a longitudinal sectional view
  • FIG. 7 is a perspective view
  • FIG. 8 is a plan view.
  • FIG. 9: L 1 is a diagram for explaining a method of manufacturing the active matrix display device shown in FIGS. 6-8. 7 is shown upside down with respect to the display device of FIG. 6 for convenience of explanation, and the description of the substrate 20 and the sealing portion 74 is omitted.
  • the upper side in FIGS. 6 and 9 to 11 is referred to as “upper”, and the lower side is referred to as “lower”.
  • the upper substrate 9 is composed of the base substrate 91 and the resin layer 92, and the surface of the upper substrate 9 is subjected to a liquid repellent treatment. Except that the first liquid injection part 77 provided in the upper substrate 9 is constituted by the first hole 771 and the second hole 772 smaller than the cross section of the first hole 771. This is the same as the display device 10 of the first embodiment. Since the liquid repellent treatment is applied to the periphery of the upper substrate 9 where the first liquid injection portion 77 is formed, the hole transport material supplied to the first liquid injection portion 77 is used as the upper substrate 9.
  • the hole transport material can be reliably injected into the gap 76 from the first liquid injection portion 77.
  • the hole transport material can be stored in the first hole 771 by providing the first hole 771 having a larger cross-sectional area than the second hole 772 on the upper side.
  • the upper substrate 9 functions as a protective layer or the like that protects the organic light emitting element 1, and in this embodiment, the base substrate 91 and the base substrate 91 are arranged on the base substrate 91. And a resin layer 92 provided on the surface.
  • the constituent material of the base substrate 91 in addition to various glass material substrates and various hard resin substrates, carbon materials such as ceramic materials, metal materials, carbon fibers, etc. are used! be able to.
  • the constituent material of the resin layer 92 for example, a polyimide resin, a polyester resin, a polyamide resin, a polyether ether ketone, a polyether resin such as a polyether sulfone, etc.
  • a polyimide resin has a small coefficient of thermal expansion and heat shrinkage
  • the heat shrinkage rate of the resin layer 92 can be increased by forming the resin layer 92 with the polyimide resin as a main material. It can be kept low.
  • the liquid repellency can be imparted to the upper surface of the resin layer 92 relatively easily by the liquid repellency treatment performed in the step [4B] described in the method for manufacturing the display device 10.
  • the average thickness of the base substrate 91 is not particularly limited, but is preferably about 0.1 to 30 mm, and more preferably about 0.5 to 2 Omm. Further, the thickness of the resin layer 92 is not particularly limited, but is preferably about 1 to: about 10 to 30 m, more preferably about LOO m.
  • an upper substrate (first substrate) 9 and a TFT circuit substrate (second substrate) 20 are prepared.
  • IB— A First, a base substrate 91 is prepared, and a liquid resin layer forming material containing the above-described resin material or its precursor is supplied (coated) on the base substrate 91. The resin layer 92 is formed by drying and solidifying. As a result, an upper substrate (first substrate) 9 provided with the resin layer 92 on the base substrate 91 is obtained.
  • the supply of the resin layer forming material onto the base substrate 91 can be performed by using the liquid phase film forming method described in the step [2A], and the resin layer forming material is prepared.
  • the solvent or dispersant used in this case the same solvent or dispersant as described in the above step [5A] can be used.
  • TFT circuit substrate (second substrate) 20 is obtained in the same manner as in Steps 1A-B to 1A-E.
  • the anode 8 is formed on the surface opposite to the resin layer 92 of the upper substrate (first substrate) 9 in the same manner as in the step [2A].
  • Examples of the liquid repellent treatment include a method of forming a liquid repellent film by supplying a liquid repellent material to the upper surface of the resin layer 92, and a fluorine plasma treatment method of irradiating fluorine plasma. Among these, it is preferable to use a fluorine plasma treatment method.
  • a gas containing fluorine is introduced into a discharge region that generates fluorine plasma, and the fluorine plasma generated in this discharge region is incident on the upper surface of the resin layer 92. It imparts liquid repellency to the area where this fluorine plasma is incident
  • the top surface of the resin layer 92 is uniformly fluorinated over the entire surface, that is, the liquid repellent property is uniformly (evenly uniform) on the top surface of the resin layer 92. Can be granted.
  • gas species containing fluorine atoms include tetrafluoromethane (CF) and tetrafluoride.
  • Tylene (CF) propylene hexafluoride
  • CF butylene octafluoride
  • the flow rate of the gas containing fluorine atoms is preferably about 10 to 500 sccm, more preferably about 50 to 400 sccm! / ⁇ .
  • the RF power is preferably about 0.005 to 0.2 WZcm 2 , more preferably about 0.05 to 0.1 lW / cm 2 .
  • the pressure at this time is preferably under atmospheric pressure.
  • a chamber, a decompression means, or the like can be eliminated, and processing can be performed with low energy and low cost.
  • the liquid repellent treatment may be performed over almost the entire surface of the resin layer 92 as in the present embodiment, or the first liquid injection formed in the next step [5B] It may be applied locally so as to surround the region where the portion 77 (first hole 771) is provided. Even when the liquid repellent treatment is applied to the region where the liquid repellent treatment is applied, the liquid repellent property should be surely imparted to the region surrounding at least the first liquid injection portion 77 on the upper surface of the upper substrate 9, that is, the upper surface of the resin layer 92 Can do.
  • the first liquid injection section 77 is composed of a first hole 771 and a second hole 772.
  • the second hole 772 whose cross section is smaller than the cross section of the first hole 771 connects the first hole 771 and the space 713 formed in the subsequent step [8B].
  • the first hole 771 and the second hole 772 have a circular cross section as shown in FIG. 8 in the present embodiment, but are not limited to such a shape.
  • any shape such as an ellipse, a triangle, a rectangle, a polygon such as a hexagon, and the like may be used.
  • the method of forming such a first liquid injection part 77 is not particularly limited, and examples thereof include the following.
  • a first hole 771 to be formed later is formed by removing a part of the resin layer 92 and the base substrate 91 by applying force in the thickness direction of the upper substrate 9.
  • the second hole 772 is formed so as to be smaller than the cross section of the first hole 772.
  • the second hole 772 is formed so as to communicate with the space 713.
  • a part of the resin layer 92 is applied by force in the thickness direction of the upper substrate 9 so as to communicate with the previously formed second hole 772.
  • the first hole 771 larger than the cross section of the second hole 772 is formed by removing.
  • the first liquid injection part 77 constituted by the first hole 771 and the second hole 772 can be obtained.
  • the first hole 771 has the second hole 772 in addition to the resin layer 92.
  • the base substrate 91 may be formed by removing a part of the base substrate 91 in the thickness direction of the upper substrate 9.
  • a lyophilic process may be performed on the inside of the first liquid injection unit 77.
  • the ability to improve the lyophilicity inside the first liquid injection part 77 (particularly the first hole 771), the first liquid injection part in the post-process [11B] The hole transport material supplied so as to close 77 can be reliably held in the first hole 771.
  • this lyophilic treatment for example, a method of irradiating the inside of the first liquid injection section 77 with ultraviolet rays and Z or infrared rays in an oxygen-containing atmosphere, and an oxygen plasma treatment method of irradiating oxygen plasma. Among these, it is preferable to use an oxygen plasma treatment method.
  • a gas containing oxygen is introduced into a discharge region for generating oxygen plasma, and the oxygen plasma generated in this discharge region is incident on the inner side of the first liquid injection unit 77. By making it, lyophilicity is imparted.
  • lyophilicity can be easily and reliably imparted to the inside of the first liquid injection portion 77, particularly to the inside of the first hole 771.
  • the gas containing oxygen gas typically, pure oxygen gas is used. It is preferable to use a mixed gas of oxygen gas and fluorocarbon gas (for example, tetrafluoromethane gas). As a result, the time during which the oxygen plasma is maintained is lengthened, and the inside of the first liquid injection portion 77 can be reliably reached in the state of oxygen plasma.
  • fluorocarbon gas for example, tetrafluoromethane gas
  • the oxygen gas concentration (content) in the mixed gas is preferably about 60 to 90 vol%, and more preferably about 65 to 80 vol%.
  • the flow rate of the gas containing oxygen gas is preferably about 10 to 500 sccm.
  • More preferred is around 400sccm! / Cm.
  • the RF power is preferably about 0.005 to 0.2 WZcm 2 .
  • WZcm 2 is more preferable.
  • the pressure at this time is preferably atmospheric pressure.
  • the use of a chamber, decompression means, etc. can be eliminated, and processing can be performed with low energy and low cost.
  • the first liquid injection section 77 is a region where the light emitting layer 5 is formed, that is, an organic EL element.
  • the first liquid injection portion 77 is formed prior to the formation of the electron transport layer 4 and the light emitting layer 5 other than the hole transport layer 6. With such a structure, it is possible to reliably prevent the influence of heat and the like generated when the first liquid injection portion 77 is formed on the upper substrate 9 from reaching each layer.
  • the hole (first liquid injection portion 77) is formed after the upper substrate 9 and the TFT circuit substrate 20 are joined in addition to those formed in the process as described in the present embodiment, for example. It may be the one.
  • the hole can be reliably formed so as to correspond to the position of the liquid injection portion formed in the post-process [8B]. That is, the hole can be formed with higher accuracy in the target region.
  • the hole transport material supplied so as to close the first liquid injection part 77 in the post-process [12B] can be more reliably injected into the gap.
  • the hole may be formed, for example, prior to joining the upper substrate 9 and the TFT circuit substrate 20 after forming a layer other than the hole transport layer. As a result, it is possible to reliably prevent or suppress the removal product generated when the hole is formed in the upper substrate 9 from remaining (attached) in the gap 76. The deterioration of the characteristics of the organic EL element 1 can be surely prevented.
  • the first liquid injecting portion 77 is formed by the first hole 771 in addition to the first hole 771 and the second hole 772 as in the present embodiment, for example. It may be omitted, that is, a structure like the second hole 772 as shown in FIG. 9 (c). In this case, the lyophilic treatment is performed on the region corresponding to the omitted first hole 771 in the upper surface of the resin layer 92, and the lyophobic treatment is performed so as to surround the region. .
  • the first liquid injection section 77 connects the first hole 771, the first hole 771, and the space 713, and the first hole 771.
  • the second hole 772 is smaller than the transverse cross section. Therefore, the hole transport material supplied to the first liquid injection part 77 can be reliably held (stored) in the first hole 771.
  • the upper substrate Since the liquid repellent treatment is applied to the upper surface of 9, that is, the upper surface of the resin layer 92 in this embodiment, the liquid repellent property of the resin layer 92 to the hole transport material Is higher than the liquid repellency of the inner surface of the first hole 771. Therefore, the hole transport material is prevented from transferring to the upper surface of the resin layer 92. This reliably prevents the hole transport materials supplied to the adjacent first liquid injection portions 77 from being mixed on the resin layer 92, thereby preventing the hole transport material from being mixed.
  • the first hole 771 can be reliably held (stored) in the region where the first hole 771 is formed.
  • the hole transport material can be reliably transferred into the gap 76.
  • Such a configuration includes the light-emitting layer 5 made of a different light-emitting material between adjacent organic EL elements 1, and a hole transport material suitable for these light-emitting layers 5 is used for each organic EL element 1. It is particularly effective.
  • the first hole 771 is provided, even if a droplet of the hole transport material is supplied to a position away from the second hole 772, the first hole 771 can The hole transport material can be stored in the first hole 711 so as to block the second hole 772 by restricting the droplets from spreading and spreading.
  • the next step [12B] since the hole transport material that does not leave the hole transport material on the resin layer 92 can be injected into the gap 76, the injection efficiency of the hole transport material is improved. be able to.
  • the difference in the degree of liquid repellency between the upper surface of the resin layer 92 and the inner surface of the first hole 771 (first liquid injection portion 77) can be expressed by various indicators. It can be expressed favorably using the contact angle.
  • the contact angle of the hole transport material on the upper surface of the resin layer 92 is A [°]
  • the contact angle of the hole transport material in the first hole 771 is B [°].
  • AB ⁇ 15 ° It is more preferable to satisfy the relationship A—B ⁇ 30 °.
  • the hole transport material was supplied so as to be thicker than the thickness of the resin layer 92 (first hole 771), that is, to fill the first hole 771.
  • diffusion (migration) to the upper surface of the resin layer 92 can be more reliably prevented.
  • the hole transport material is supplied to the first liquid injection section 77 by an inkjet method (droplet discharge method), among the forces that can be supplied using the liquid phase film formation method as described above. It is preferable to use and supply. According to the ink jet method, the hole transport material can be reliably supplied to the inner surface of the first hole 771, and the diffusion to the resin layer 92 can be more reliably prevented. In addition, when forming the organic EL element 1 including the light emitting layer 5 of multiple colors, a hole transport material suitable for the light emitting layer 5 for each color is easily supplied to the first liquid injection portion 77 (painting). If you can! There are merits.
  • the hole transport material when a solid hole transport material is used, the hole transport material is heated to be in a molten state, which is the same as when a liquid or semi-solid hole transport material is used.
  • the hole transport material in a molten state can be supplied to the first liquid injection section 77 using various liquid phase film forming methods. In addition to these methods, for example, a massive hole transport material larger than the transverse plane of the second hole 772 is placed in the first liquid injection part 77 (in the first hole 771). You can do it.
  • the hole transport material supplied to the first liquid injection section 77 in the molten state may be solidified by heat dissipation prior to performing the next step [12B], or may be in a molten state. It may be that maintaining the above.
  • hole transport is performed using the difference between the pressure of the gap 76 and the atmospheric pressure.
  • the hole transport layer 6 is formed by injecting material into the gap 76.
  • the display device 10 in which the liquid repellent treatment is performed on the surface of the upper substrate 9 can be formed.
  • first liquid injection portion 77 is provided corresponding to one gap 76.
  • a plurality of first liquid injection portions 77 are provided corresponding to one gap 76. You may do it.
  • FIG. 12 is a longitudinal sectional view showing a third embodiment of an active matrix display device to which the organic light-emitting device of the present invention is applied.
  • the upper side in FIG. 12 is referred to as “upper” and the lower side is referred to as “lower”.
  • an electron transport layer 4 is formed by injecting an electron transport material into the gap from the first liquid injection section 77 instead of the hole transport layer 6, and the third liquid Except that the injection portion is provided so as to correspond to the electron transport layer 4, it is the same as the display device 10 of the first embodiment.
  • the electron transporting material constituting the electron transporting layer 4 a material that is solid at room temperature and a material that is liquid or semi-solid at room temperature can be used, as with the above-described hole transporting material.
  • examples of the electron transport material that is solid at room temperature include those described in the first embodiment.
  • the electron transport material that is liquid or semi-solid at room temperature similarly to the hole transport material, at least a solid electron transport material at room temperature is provided as an electron transport portion, and at least connected to the electron transport portion.
  • Those having one linear alkyl group are preferably used.
  • examples of the electron transport material that is liquid or semi-solid at room temperature include compounds represented by the following general formula (A2) to general formula (A4).
  • X 1, X 2 and X 3 each independently represents a hydrogen atom or a straight-chain alkyl group, may be the same or may be different. However, at least one of X 1 , X 2 and X 3 represents a linear alkyl group having 3 to 8 carbon atoms, and the other represents a hydrogen atom, a methyl group or an ethyl group. ]
  • Such compounds (A2) to (A4) have an excellent electron transport ability and are in a liquid or semi-solid form at ordinary temperature.
  • the electron transport material when it is a low molecule (a monomer or oligomer), it is liquid or semi-solid at room temperature.
  • a polymer that is polymerized by polymerizing the same can also be used.
  • the electron transport material when the electron transport layer 4 is formed, the electron transport material is in a liquid or semi-solid state (low molecule) in the first state.
  • the solid electron transport layer 4 can be formed in the gap 76 by injecting into the gap 76 from the liquid injection section 77 and polymerizing (curing) this electron transport material.
  • the heat resistance of the electron transport material can be improved by polymerizing the electron transport material. Further, it suitably prevents diffusion of the electron transport material (small molecule) into the light emitting layer 5. be able to.
  • Such an electron transport material is not particularly limited.
  • the electron transport material having a polymerizable group at the terminal of a linear alkyl group included in the electron transport material that is liquid or semi-solid at normal temperature as described above. are preferably used.
  • the same groups as those described for the polymerizable group provided in the hole transport material can be used.
  • the constituent material (hole transport material) of the hole transport layer 6 has, for example, an arylamine skeleton such as polyarylamine in addition to the low molecular weight compounds mentioned in the above hole transport portion.
  • arylamine skeleton such as polyarylamine in addition to the low molecular weight compounds mentioned in the above hole transport portion.
  • a polymer having a fluorene skeleton such as a fluorene-bithiophene copolymer, a polymer having both an arylamine skeleton and a fluorene skeleton such as a fluorene-arylamine copolymer, and poly (N-butylcarbazole).
  • Polybutylene polyvinylanthracene, polythiophene, polyalkylthiophene, polyhexylthiophene, poly ( ⁇ -phenylenevinylene), polytinylenevinylene, pyreneformaldehyde resin, ethylcarbazole formaldehyde resin or its derivatives, etc. High molecular compounds.
  • the anode 8, the hole transport layer 6 and the light emitting layer 5 are formed on the inner surface side of the upper substrate 9 (first substrate), and the inner surface side of the TFT circuit substrate 20 is formed.
  • the cathode 3 is formed, the upper substrate 9 and the TFT circuit substrate 20 are joined so that a gap 76 is formed between them, and then an electron transport material is injected into the gap 76 to thereby form an electron transport layer.
  • the first protrusion 71 is formed according to the total thickness of the hole transport layer 6 and the light emitting layer 5.
  • the third protrusion 72 is formed according to the total thickness of the cathode 3 and the electron transport layer 4.
  • the cathode 3 is formed on the TFT circuit substrate (third substrate) 20 exposed inside the space 722, and the anode 8 exposed inside the space 712 is formed. , Hole transport Layer 6 and light emitting layer 5 are formed in this order.
  • the gap 76 and the second number corresponding to the position where the electron transport layer 4 is formed When forming the protrusion 7, the gap 76 and the second number corresponding to the position where the electron transport layer 4 is formed.
  • an electron transport material is supplied so as to block the first liquid injection part 77.
  • the pressure between the pressure of the gap 76 and the atmospheric pressure is supplied.
  • the electron transport layer 4 can be formed in the gap 76 by injecting the electron transport material into the gap 76 using the difference.
  • FIG. 13 is a longitudinal sectional view showing a fourth embodiment of an active matrix display device to which the organic light-emitting device of the present invention is applied.
  • the upper side in FIG. 13 is referred to as “upper” and the lower side is referred to as “lower”.
  • the particles 78 are used as a spacer instead of the protrusions 7, and the hole transport layer 6 is physically provided, that is, common to all the organic EL elements 1. Except for this, it is the same as the display device 10 of the first embodiment. Even when the particles 78 are used as the spacers, the thickness of the voids can be controlled easily and reliably, as in the case where the protrusions 7 are used.
  • the sealing portion 74 functions as a barrier layer that prevents the hole transport material from flowing out of the organic EL element 1.
  • the display device 10 of the present embodiment can be manufactured by changing the manufacturing method described in the display device 10 of the first embodiment as follows.
  • the formation of the second protrusion 72 is omitted.
  • a gap between the upper substrate 9 and the TFT circuit substrate 20 is formed.
  • the particles 78 are interposed (arranged) between the anode 8 and the light emitting layer 5.
  • the function as a spacer can be exerted on the particles 78, and the width of the gap formed in the thickness direction of the upper substrate 9 can be made substantially constant.
  • the average particle diameter of the particles 78 is appropriately set according to the thickness of the hole transport layer 6, and is not particularly limited, but is preferably about 10 to 150 nm. As a result, the function as a spacer capable of obtaining the target thickness of the hole transport layer 6 can be reliably exerted on the particles 78.
  • the constituent material of such particles 78 is not particularly limited, but for example, the same material as described for the constituent material of the first protrusion 71 is preferably used. As a result, it is possible to suitably prevent or suppress a decrease in the efficiency of hole injection into the light emitting layer 5 of the hole transport layer 6.
  • the hole transport material is injected over almost the entire gap, whereby the hole transport layer 6 Can be formed integrally.
  • the carrier for example, hole or electron
  • the carrier transport layer formed by injecting into the gap formed between the substrates. It will be formed at the end of the process for the other layers that make up the stack. Therefore, as a result of forming the light-emitting layer and other carrier transport layers formed by the liquid phase film formation method or the gas phase film formation method so that the characteristics are suitably exhibited, each organic EL element (each pixel ) Even if the thickness of the layers varies in 1), the carrier transport material is poured into the gap to eliminate the variation and make the layer thickness uniform. be able to.
  • the carrier transport material is poured into the gap to eliminate the variation and make the layer thickness uniform. be able to.
  • the carrier transport layer formed by injecting into the gap to the layer is the first embodiment, the second embodiment, and the fourth embodiment.
  • the carrier transport layer formed by injecting a predetermined carrier transport material into the gap 76 from the first liquid injection section 77 is the first embodiment, the second embodiment, and the fourth embodiment.
  • the present invention is applied to the electron transport layer.
  • the organic EL element 1 includes a plurality of hole transport layers. Or an electron transport layer, or a carrier injection layer such as an electron injection layer or a hole injection layer, these layers are formed by the method for producing the organic light-emitting device of the present invention. Let's apply the law.
  • Such a display device (organic light-emitting device of the present invention) 10 can be incorporated into various electronic devices.
  • FIG. 14 is a perspective view showing the configuration of a mopile type (or notebook type) personal computer to which the electronic apparatus of the present invention is applied.
  • a personal computer 1100 includes a main body 1104 provided with a keyboard 1102 and a display unit 1106 provided with a display.
  • the display unit 1106 is connected to the main body 1104 via a hinge structure. It is rotatably supported.
  • the display unit included in the display unit 1106 includes the display device 10 described above.
  • FIG. 15 is a perspective view showing a configuration of a mobile phone (including PHS) to which the electronic apparatus of the invention is applied.
  • mobile phone 1200 includes a plurality of operation buttons 1202, earpiece 1204, and mouthpiece 1206, and a display unit.
  • this display unit is configured by display device 10 described above.
  • FIG. 16 is a perspective view showing the configuration of a digital still camera to which the electronic apparatus of the invention is applied. In this figure, connection with an external device is also simply shown.
  • a normal camera sensitizes a silver halide photographic film with a light image of a subject
  • a digital still camera 1300 photoelectrically converts a light image of a subject with an imaging device such as a CCD (Charge Coupled Device).
  • the image signal (image signal) is generated by conversion.
  • a display unit On the back of the case (body) 1302 of the digital still camera 1300, there is a display unit that is configured to display based on the image signal from the CCD, and functions as a viewfinder that displays the subject as an electronic image. To do.
  • the display unit is configured by the display device 10 described above.
  • a circuit board 1308 is installed inside the case.
  • the circuit board 1308 is provided with a memory capable of storing (storing) an imaging signal.
  • a light receiving unit 1304 including an optical lens (imaging optical system), a CCD, and the like is provided on the front side of the case 1302 (on the back side in the illustrated configuration).
  • a video signal output terminal 1312 and an input / output terminal 1314 for data communication are provided on the side surface of the case 1302.
  • a television monitor 1430 is connected to the video signal output terminal 1312 and a personal computer 1440 is connected to the input / output terminal 1314 for data communication as necessary.
  • the imaging signal power stored in the memory of the circuit board 1308 is output to the television monitor 1430 or the personal computer 1440 by a predetermined operation.
  • the electronic apparatus of the present invention includes, for example, a television and a video camera in addition to the personal computer (mopile personal computer) in FIG. 14, the mobile phone in FIG. 15, and the digital still camera in FIG. , Viewfinder type, monitor direct view type video tape recorder, laptop personal computer, car navigation device, pager, electronic notebook (including communication function), electronic dictionary, calculator, electronic game device, word processor, Workstations, videophones, security TV monitors, electronic binoculars, POS terminals, devices with touch panels (for example, cash dispensers and vending machines for financial institutions), medical devices (for example, electronic thermometers, blood pressure monitors, blood glucose meters, heart (Electric display device, ultrasonic diagnostic device, display device for endoscope), fish detector, various measuring instruments Gauges (for example, vehicle, aircraft It can be applied to a projection display device such as a ship instrument), a flight simulator, various other monitors, and a projector.
  • a television and a video camera in addition to the personal computer (mopile personal computer) in FIG
  • the method for manufacturing the organic light-emitting device, the organic light-emitting device, and the electronic device of the present invention based on the illustrated embodiment is not limited thereto.
  • the organic light-emitting device of the present invention may be a combination of any two or more configurations (features) of the above-described embodiments.
  • each part of the organic light-emitting device of the present invention can be replaced with an arbitrary one that can exhibit the same function, or an arbitrary configuration can be added.
  • the compound obtained there was mixed with 130 mmol, 4,4, -Jodobiphenyl 62 mmol, palladium acetate 1.3 mmol, t-butylphosphine 5.2 mmol, t-butoxynatrim 260 mmol, xylene 700 mL, and 120 ° Stir with C. Thereafter, the mixture was allowed to cool and crystallized to obtain a compound.
  • ⁇ 1A> First, a polyimide substrate having an average thickness of 0.5 mm and a transparent glass substrate having an average thickness of 5 mm were prepared. Then, a circuit portion was formed on the glass substrate as described above.
  • an ITO film having an average thickness of 150 nm was formed on the polyimide substrate by a vacuum deposition method to obtain an anode.
  • the compound (A) was supplied by an inkjet method so as to close the hole provided in the polyimide substrate.
  • a first glass substrate having an average thickness of 0.5 mm and a transparent second glass substrate having an average thickness of 0.5 mm were prepared.
  • a polyimide (insulating photosensitive resin) was applied on the first glass substrate, and then exposed to form a polyimide layer having an average thickness of 10 m.
  • anode film is obtained by forming an ITO film with an average thickness of 150 nm on the surface of the first glass substrate on which the polyimide layer is not formed (the surface opposite to that) by vacuum deposition. It was.
  • liquid repellent treatment fluorine plasma treatment
  • FIG. 9 (d) that is, the first glass substrate on which the polyimide layer is formed by plasma etching so as not to overlap with the region where the light emitting layer is formed.
  • a cord provided with a first hole and a second hole having a smaller cross section than the first hole is provided in the thickness direction.
  • a Cu layer having an average thickness of 50 nm was formed on the circuit portion inside the second protrusion by an electroless plating method to obtain a cathode.
  • the composite (A) was supplied by an inkjet method so as to close the hole provided on the first glass substrate side.
  • Example 1 For these display devices of Example 1 and Example 2, the current density (mAZcm 2 ), emission luminance (cdZm 2 ), and maximum emission efficiency (lmZW) were measured, and the emission luminance was half of the initial value. The measurement time (half-life) was measured, but the results showed excellent results.
  • mAZcm 2 current density
  • cdZm 2 emission luminance
  • lmZW maximum emission efficiency
  • the organic light emitting device includes a first substrate and a second substrate, and the first substrate and Z or the inner surface of the second substrate other than the carrier transport layer. After the layer is formed by the liquid phase film formation method or the gas phase film formation method, the first substrate and the second substrate are bonded so that a gap is formed between them, and then the first liquid By injecting the carrier transport material into the gap from the injection part to form the carrier transport layer. Manufactured.
  • the carrier transport layer is composed not only of a solid carrier transport material but also of a liquid or semi-solid carrier transport material.
  • an electronic device including the organic light emitting device manufactured by the method for manufacturing the organic light emitting device has high reliability. Therefore, it has industrial applicability.

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Manufacturing & Machinery (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Cette invention concerne un procédé destiné à produire un dispositif luminescent organique comprenant au moins une couche de transport de porteurs, l’une de ces couches pouvant être formée à la fois d’un matériau solide de transport de porteurs et d’un tel matériau liquide ou semi-solide, un dispositif luminescent organique présentant un niveau élevé de caractéristiques obtenu par le procédé de production décrit, et un appareil électronique de haute fiabilité. Le dispositif luminescent organique (dispositif d’affichage de type matrice active) comprend une pluralité d’éléments électroluminescents organiques comportant une cathode, une couche de transport d’électrons, une couche luminescente, une couche de transport de trous et une anode. Le dispositif luminescent organique est produit par formation d’une anode sur un substrat supérieur et d’une cathode, d’une couche de transport d’électrons et d’une couche luminescente sur un substrat de circuit TFT, au moyen d’un procédé de formation de film en phase liquide ou en phase gazeuse, puis par assemblage du substrat supérieur et du substrat de circuit TFT avec maintien d’un espace entre eux, et enfin coulage d’un matériau de transport de trous dans l’espace pour obtenir une couche de transport de trous afin de former un élément électroluminescent organique.
PCT/JP2006/318786 2005-09-22 2006-09-21 Procédé de production de dispositif luminescent organique, dispositif luminescent organique, et appareil électronique WO2007034900A1 (fr)

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KR20120042938A (ko) 2009-07-21 2012-05-03 닛산 가가쿠 고교 가부시키 가이샤 유기 전계 발광 소자
CN110828683A (zh) * 2019-10-28 2020-02-21 深圳市华星光电半导体显示技术有限公司 Oled器件及其制备方法
US20220093896A1 (en) * 2020-09-22 2022-03-24 Boe Technology Group Co., Ltd. Display panel and method for manufacturing the same, and display device

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JPH0711247A (ja) * 1993-06-28 1995-01-13 Idemitsu Kosan Co Ltd 有機ｅｌ素子の封止方法およびこの封止方法により得られた発光装置
JP2001185352A (ja) * 1999-12-27 2001-07-06 Sharp Corp 有機ｅｌ表示装置の発光層の形成方法
JP2003308970A (ja) * 2002-04-17 2003-10-31 Seiko Instruments Inc 有機ｅｌ素子及びその製造方法
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JPS5880295A (ja) * 1981-11-06 1983-05-14 株式会社日立製作所 Ｅｌ素子の製造方法
JPH01313892A (ja) * 1988-06-13 1989-12-19 Matsushita Electric Ind Co Ltd 画像表示装置及びその製造方法
JPH0711247A (ja) * 1993-06-28 1995-01-13 Idemitsu Kosan Co Ltd 有機ｅｌ素子の封止方法およびこの封止方法により得られた発光装置
JP2001185352A (ja) * 1999-12-27 2001-07-06 Sharp Corp 有機ｅｌ表示装置の発光層の形成方法
JP2003535445A (ja) * 2000-06-01 2003-11-25 マイクロエミッシブ ディスプレイズ リミティド カラー光電子デバイスの作製方法
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120042938A (ko) 2009-07-21 2012-05-03 닛산 가가쿠 고교 가부시키 가이샤 유기 전계 발광 소자
CN110828683A (zh) * 2019-10-28 2020-02-21 深圳市华星光电半导体显示技术有限公司 Oled器件及其制备方法
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US20220093896A1 (en) * 2020-09-22 2022-03-24 Boe Technology Group Co., Ltd. Display panel and method for manufacturing the same, and display device
US11793027B2 (en) * 2020-09-22 2023-10-17 Boe Technology Group Co., Ltd. Display panel and method for manufacturing the same, and display device

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