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WO2006033563A1 - Dispositif emetteur de lumiere organique - Google Patents

Dispositif emetteur de lumiere organique Download PDF

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WO2006033563A1
WO2006033563A1 PCT/KR2005/003168 KR2005003168W WO2006033563A1 WO 2006033563 A1 WO2006033563 A1 WO 2006033563A1 KR 2005003168 W KR2005003168 W KR 2005003168W WO 2006033563 A1 WO2006033563 A1 WO 2006033563A1
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group
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compound
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PCT/KR2005/003168
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Seok Hee Yoon
Jae Min Moon
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Lg Chem. Ltd.
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Publication of WO2006033563A1 publication Critical patent/WO2006033563A1/fr

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/14—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/06—Peri-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/10—Transparent electrodes, e.g. using graphene
    • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3

Definitions

  • the present invention relates to a compound that is usable in an organic light emitting device and an organic light emitting device using the same.
  • An organic light emission phenomenon is an example of a conversion of current into visible rays through an internal process of a specific organic molecule.
  • the organic light emission phenomenon is based on the following mechanism.
  • organic material layers are interposed between an anode and a cathode, if voltage is applied between the two electrodes, electrons and holes respectively from the cathode and the anode are injected into the organic material layer.
  • the electrons and the holes which are injected into the organic material layer are recombined to form an exciton, and the exciton is reduced to a bottom state to emit light.
  • An organic light emitting device which is based on the above mechanism typically comprises a cathode, an anode, and organic material layer(s), for example, organic material layers including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, interposed between the anode and the cathode.
  • organic material layer(s) for example, organic material layers including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, interposed between the anode and the cathode.
  • the materials used in the organic light emitting device are mostly pure organic materials or complexes of organic material and metal.
  • the material used in the organic light emitting device may be classified as a hole injection material, a hole transport material, a light emitting material, an electron transport material, or an electron injection material, according to its use.
  • an organic material having a p-type property which is easily oxidized and is electrochemically stable when it is oxidized, is used as the hole injection material or the hole transport material.
  • an organic material having an n-type property which is easily reduced and is electrochemically stable when it is reduced, is used as the electron injection material or the electron transport material.
  • the light emitting layer material an organic material having both p-type and n-type properties is preferable, which is stable when it is oxidized and when it is reduced. Also a material having high light emission efficiency for conversion of the exciton into light when the exciton is formed is preferable.
  • the material used in the organic light emitting device further have the following properties.
  • the material used in the organic light emitting device have excellent thermal stability. It is because of joule heating produced as a result of a movement of charged particles in the organic light emitting device.
  • NPB which has recently been widely used as the hole transport layer material of the organic light emitting device, has a glass transition temperature of 100 0 C or lower, thus it is difficult to apply to an organic light emitting device requiring a high current.
  • the material used in the organic light emitting device must have excellent chemical stability, electric charge mobility, and interfacial characteristic with an electrode or an adjacent layer. That is to say, the material used in the organic light emitting device must be little deformed by moisture or oxygen. Furthermore, proper hole or electron mobility must be assured so as to balance density of the holes and that of the electrons in the light emitting layer of the organic light emitting device to maximize the formation of excitons. Additionally, it has to be able to have a good interface with an electrode including metal or metal oxides so as to assure stability of the device.
  • the present inventors have found an organic compound which is capable of satisfying conditions required of a material which can be used in an organic light emitting device, for example, a proper energy level, electrochemical stability, and thermal stability, and which has a chemical structure capable of playing various roles required in the organic light emitting device depending on a substituent group.
  • an object of the present invention is to provide the organic compound found by the present inventors, and an organic light emitting device using the organic compound.
  • Technical Solution [14] The present invention provides a novel compound represented by the following Formula 1, a compound of Formula 1 into which a thermosetting or photo- crosslinkable functional group is introduced, and an organic light emitting device.
  • the organic light emitting device comprises a first electrode, organic material layer(s) comprising a light emitting layer, and a second electrode, wherein the first electrode, the organic material layer(s), and the second electrode form a layered structure.
  • At least one layer of the organic material layer(s) includes a compound of Formula 1 or a compound of Formula 1 into which a thermosetting or photo-crosslinkable functional group is introduced:
  • ArI to Ar6 are each indepe substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a substituted or unsubstituted arylamine group, a substituted or un ⁇ substituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, a nitro group, and an acetylene group; or a heterocyclic group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a substituted or unsubstit
  • R3 and R4, and R7 and R8 each independently or collectively may be connected to form condensation rings or may form the condensation rings along with a group selected from the group consisting of O, S, NR, PR, CRR', and SiRR', wherein R and R' are each independently or collectively selected from the group consisting of hydrogen, oxygen, a substituted or unsubstituted alkyl group, a substituted or un- substituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, an amino group, a nitrile group, a nitro group, a halogen group, an amide group, and an ester group.
  • RI l and R 12 are each independently or collectively selected from the group consisting of an alkyl group; an alkoxy group; an aryl group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a thioalkoxy group, a substituted or unsubstituted arylamine group, a substituted or un ⁇ substituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, a nitro group, and an acetylene group; a heterocyclic group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group
  • the substituent group for the alkyl, alkenyl, alkoxy, aryl, and heterocyclic groups are a halogen, alkyl, alkenyl, alkoxy, arylamine, aryl, arylalkyl, arylalkenyl, heterocyclic, nitrile, or acetylene group.
  • FIG. 1 illustrates an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4;
  • FIG. 2 illustrates an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron injection layer 8, and a cathode 4.
  • Y and Y' are each selected from the group consisting of hydrogen, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, an arylamine group, an aryl group, a heterocyclic group, a nitrile group, and an acetylene group, and may be connected to each other to form a condensation ring.
  • Illustrative, but non-limiting, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
  • Illustrative, but non-limiting, examples of the arylamine group include a diphenylamine group, a phetylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a carbazolyl group, and a triphenylamine group.
  • Il ⁇ lustrative, but non-limiting, examples of the aryl group include a phenyl group, a naphthyl group, an anthranyl group, and a biphenyl group.
  • heterocyclic group examples include a pyridyl group, an acridyl group, a thiophenyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, and a quinolinyl group.
  • the alkyl group, the alkoxy group, and the alkenyl group of Rl to R12 of Formula 1 have a carbon number of 1 to 20.
  • Illustrative, but non-limiting, examples of the aryl group of Rl to R12 of Formula 1 are as follows. [34]
  • n of a thiophenyl group is 1 - 6; and R is an alkyl group, or a substituted or unsubstituted aryl group.
  • the halogen group of Rl to R12 of Formula 1 is exemplified by fluorine, chlorine, bromine, or iodine.
  • Z is selected from the group consisting of hydrogen, a C1-C20 alkyl group, a C1-C20 alkenyl group, a C1-C20 alkynyl group, an alkoxy group, an arylamine group, an aryl group, a heterocyclic group, a nitrile group, and an acetylene group.
  • Examples of the arylamine group, the aryl group, and the heterocyclic group of Z are as shown in the examples of the above-mentioned substituent groups of Rl to R12.
  • a compound preferable in the present invention is a compound in which X is C or Si, and R3 and R4 are hydrogen, or R3 and R4 are directly bonded to each other or form a condensation ring along with a group selected from the group consisting of O, S, NR, PR, CRR', and SiRR' in Formula 1 (wherein, R and R' are as defined in Formula 1).
  • Another compound preferable in the present invention is a compound in which X is C or Si, and R3 and R4, and R7 and R8 are each independently or collectively bonded, or form condensation rings along with groups selected from the group consisting of O, S, NR, PR, CRR', and SiRR' in Formula 1 (wherein, R and R' are as defined in Formula 1).
  • Still another compound preferable in the present invention is a compound represented by the following Formula 2.
  • the compound of Formula 1 has a core structure in which the basic frame of acridine is substituted with diarylamine and phenyl substituted with arylamine at a para-position thereof.
  • a plane constituting the acridine frame is perpendicular to another plane which include RI l and R 12, thus conjugation does not occur between the two above-mentioned planes. Due to the structural characteristic described above, the core structure of the compound of Formula 1 has limited conjugation.
  • the conjugation length of the compound has a close relationship with an energy band gap.
  • an energy band gap is reduced as a conjugation length of a compound increases.
  • the core structure since a conjugation structure is limited in the core structure of the compound of Formula 1, the core structure has a large energy band gap.
  • substituent groups which are frequently applied to hole injection layer materials, hole transport layer materials, light emitting layer materials, and electron transport layer materials which are used during the production of the organic light emitting device, are introduced into the core structure so as to produce substances capable of satisfying requirements of each organic material layer.
  • substituent groups which are frequently applied to hole injection layer materials, hole transport layer materials, light emitting layer materials, and electron transport layer materials which are used during the production of the organic light emitting device, are introduced into the core structure so as to produce substances capable of satisfying requirements of each organic material layer.
  • the core structure of the compound of Formula 1 includes the arylamine structure, it can have an energy level suitable for the hole injection and/or hole transport materials in the organic light emitting device.
  • the compound having the proper energy level is selected depending on the substituent group among the compounds expressed by Formula 1 to be used in the organic light emitting device, thereby it is possible to realize a device having low actuating voltage and high light efficiency.
  • the compounds of Formula 1-18 have HOMO of 5.24 eV, they have an energy level suitable for the hole injection layer or the hole transport layer. Meanwhile, the compounds of Formula 1-18 have the band gap of 3.3 eV, which is still larger than that of NPB, typically used as the hole transport layer material, thus they have a LUMO value of about 1.94 eV, which is very high. If a compound having a high LUMO value is used as the hole transport layer, it increases the energy wall of LUMO of the material constituting the light emitting layer to prevent the movement of electrons from the light emitting layer to the hole transport layer.
  • the above-mentioned compound improves the light emission efficiency of the organic light emitting device so that efficiency is higher than that of conventionally used NPB (HOMO 5.4 eV, LUMO 2.3 eV, and energy band gap 3.1 eV).
  • the energy band gap is calculated by a typical method using a UV-VIS spectrum.
  • the compound of Formula 1 has stable redox characteristics.
  • Redox stability is estimated using a CV (cyclovoltammetry) method. For example, if oxidation voltage is repeatedly applied to the compounds of Formula 1-18, oxidation repeatedly occurs at the same voltage and the current amount is the same. This means that the compound has excellent stability to oxidation.
  • the compound of Formula 1 since the compound of Formula 1 has a high glass transition temperature (Tg), it has excellent thermal stability.
  • Tg glass transition temperature
  • the glass transition temperature of the compound of Formula 1-18 is 12O 0 C, which is still higher than that of conventionally used NPB (Tg: 96 0 C).
  • the excellent thermal stability of the compound is an important factor providing actuating stability to the device.
  • the compound of Formula 1 may be used to form the organic material layer using a vacuum deposition process or a solution coating process during the production of the organic light emitting device.
  • a solution coating process include a spin coating process, a dip coating process, an inkjet printing process, a screen printing process, a spray process, and a roll coating process.
  • the compound of Formula 1-18 has excellent solubility to a polar solvent, such as xylene, dichloro ethane, or NMP, which is used during the production of the device, and forms a thin film very well through the process using a solution, thus the solution coating process may be applied to produce the device.
  • a light emitting wavelength of a thin film or a solid formed using the solution coating process is typically shifted to a longer wavelength due to interaction between molecules, in comparison with a light emitting wavelength in a solution state. However, less shift in the wavelength occurs in the compound having the structure shown in Formula 1.
  • a lithiated alkyl or aryl group is reacted with a carbonyl group of an ester group to produce tertiary alcohol, and the resulting alcohol is heated in the presence of an acid catalyst to form a hexagonal cyclic compound while water is removed, thereby producing the compound of Formula 1.
  • the above-mentioned procedure for producing the compound is well known in the art, and those skilled in the art can change the production conditions during the production of the compound of Formula 1. The production will be described in detail in the preparation examples as described later.
  • a compound, in which a thermosetting or photo-crosslinkable group is introduced into the compound of Formula 1 may be used instead of the compound of Formula 1.
  • This compound has the basic physical properties of the compound of Formula 1, and may be used to form a thin film using a solution coating process and then be cured so as to form an organic material layer during the production of the device.
  • thermosetting or photo-crosslinkable functional group may be a vinyl or an acryl group.
  • the organic light emitting device of the present invention can be produced using known materials through a known process, modified only in that at least one layer of organic material layer(s) include the compound of the present invention, the compound of Formula 1.
  • the organic material layer(s) of the organic light emitting device according to the present invention may have a single layer structure, or alternatively, a multi-layered structure in which two or more organic material layers are layered.
  • the organic light emitting device of the present invention may comprise a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer as the organic material layer.
  • the structure of the organic light emitting device is not limited to this, but may comprise a smaller number of organic material layers.
  • the organic light emitting device of the present invention may be produced, for example, by sequentially layering a first electrode, organic material layer(s), and a second electrode on a substrate.
  • a physical vapor deposition (PVD) method such as a sputtering method or an e-beam evaporation method, may be used, but the method is not limited to these.
  • a glass substrate (corning 7059 glass), on which ITO (indium tin oxide) was applied to a thickness of 1000 A to form a thin film, was put in distilled water, in which a detergent was dissolved, and washed using ultrasonic waves.
  • a product manufactured by Fischer Inc. was used as the detergent, and distilled water was produced by filtering twice using a filter manufactured by Millipore Inc.
  • ultrasonic washing was conducted twice using distilled water for 10 min.
  • ultrasonic washing was conducted using isopropyl alcohol, acetone, and methanol solvents, and drying was then conducted. Next, it was transported to a plasma washing machine.
  • the substrate was dry washed using nitrogen plasma under a pressure of 14 mtorr at 85 W for 5 min, and then transported to a vacuum evaporator.
  • Hexanitrile hexaazatriphenylene (hereinafter, referred to as "HAT") of the following Formula was vacuum deposited to a thickness of 500 A by heating on a transparent ITO electrode, which was prepared through the above procedure, so as to form an anode including an ITO conductive layer and an n-type organic material.
  • the compound of Formula 1-18 (400 A) was vacuum deposited thereon to form hole injection and transport layers.
  • Alq3 was vacuum deposited to a thickness of 300 A on the hole transport layer to form a light emitting layer.
  • An electron transport layer material of the following Formula was deposited to a thickness of 200 A on the light emitting layer to form an electron transport layer.
  • Lithium fluoride (LiF) having a thickness of 12 A and aluminum having a thickness of 2000 A were sequentially deposited on the electron transport layer to form a cathode.
  • the deposition speed of an organic material was maintained at 0.3 - 0.8 A/sec. Furthermore, lithium fluoride and aluminum were deposited at speeds of 0.3 A/sec and 1.5 - 2.5 A/sec, respectively, at the cathode. During the deposition, a vacuum was maintained at 1 ⁇ 3 x 10 . [193] The resulting device had an electric field of 8.14 V at a forward current density of
  • the operation and light emission of the device at the above-mentioned actuating voltage mean that the compound of Formula 1-18 which formed the layer between the hole injection layer and the light emitting layer functions to transport holes.
  • HAT was deposited to a thickness of 80 A on an ITO substrate, which was prepared through the same procedure as example 1, so as to form an anode including an ITO conductive layer and an n-type organic material. Subsequently, the compound of
  • Formula 1-18 was deposited to a thickness of 800 A on the anode to form a hole injection layer.
  • NPB was deposited to a thickness of 300 A on the hole injection layer to form a hole transport layer
  • Alq3 was deposited to a thickness of 300 A thereon to form a light emitting layer.
  • An electron transport layer and a cathode were formed on the light emitting layer through the same procedure as in example 1.
  • the resulting device had an electric field of 9.94 V at a forward current density of
  • the operation and light emission of the device at the above-mentioned actuating voltage mean that the compound of Formula 1-18 forming the layer between the thin film formed on the substrate and the hole transport layer functions to inject holes.
  • the compound of the present invention can be used as an organic material layer material, particularly, hole injection and/or transport materials in an organic light emitting device, and when applied to an organic light emitting device it is possible to reduce the actuating voltage of the device, to improve the light efficiency thereof, and to improve the lifespan of the device through the thermal stability of the compound.

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Abstract

L'invention concerne un composé de la formule I et un dispositif émetteur de lumière organique contenant le composé de la formule I ou le composé de la formule I dans lequel est introduit un groupe fonctionnel thermodurcissable ou photo-réticulable.
PCT/KR2005/003168 2004-09-24 2005-09-23 Dispositif emetteur de lumiere organique WO2006033563A1 (fr)

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Cited By (37)

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JP2007314509A (ja) * 2006-04-24 2007-12-06 Hitachi Chem Co Ltd アミン誘導体及びこれを用いた有機エレクトロルミネッセンス素子
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