WO2014163228A1 - Nouveau composé d'élément électroluminescent organique et élément électroluminescent organique comprenant celui-ci - Google Patents

Nouveau composé d'élément électroluminescent organique et élément électroluminescent organique comprenant celui-ci Download PDF

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WO2014163228A1
WO2014163228A1 PCT/KR2013/003358 KR2013003358W WO2014163228A1 WO 2014163228 A1 WO2014163228 A1 WO 2014163228A1 KR 2013003358 W KR2013003358 W KR 2013003358W WO 2014163228 A1 WO2014163228 A1 WO 2014163228A1
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substituted
unsubstituted
group
compound
light emitting
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현서용
박성준
김하연
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(주)피엔에이치테크
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
    • H—ELECTRICITY
    • 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
    • H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission

Definitions

  • the present invention relates to a compound for an organic light emitting device and an organic light emitting device comprising the same, and more particularly, a compound for an organic light emitting device that can improve the luminous efficiency of the organic light emitting device and an organic light emitting device comprising the same. It relates to an element.
  • liquid crystal display As the movement to the information society accelerates, the proportion of flat panel displays is gradually increasing.
  • LCD liquid crystal display
  • OLED organic light emitting diodes
  • Organic EL is a phenomenon in which electrons and holes injected through an anode and an anode into an organic thin film are recombined to form excitons, and light of a specific wavelength is generated from the formed excitons from a single crystal of anthracene by Pope et al. In 1963. It has been discovered for the first time and has been actively studied since it was reported by CW Tang et al. (CW Tang, SA Vanslyke, Applied physics Letters. 51, 913p, 1987).
  • Organic materials used in organic electroluminescent devices are largely divided into polymer and low molecular forms, and low molecules can be divided into pure organic materials and metal complexes formed with metals and chelates.
  • High molecular materials can produce multifunctional materials by combining various functional units with polymer chains, but there are difficulties in refining composites and forming devices, and low molecular materials can synthesize materials of different properties, but There is a limit to the material synthesis.
  • the organic light emitting diode can be formed in a stacked structure.
  • the advantage of the laminated structure is that the material can be selected and used according to each function.
  • the device structure forms a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer between the anode and the cathode, The exciton can be easily formed and the luminous efficiency can be increased.
  • the light emitting material can be divided into a host material and a light emitting material (dopant) material, and the light emitting material is classified into fluorescence and phosphorescence according to the light emission mechanism.
  • the excited state of the former in the compound is 1: 3 with singlet to triplet ratios and three times more triplet states. Therefore, the internal quantum efficiency of fluorescence falling from the singlet state to the ground state is only 25%, while the internal quantum efficiency of phosphorescence falling from the triplet state to the ground state is 75%. In addition, the theoretical limit of the internal quantum efficiency reaches 100% in the case of a quarterly transition from singlet to triplet.
  • Phosphorescent light emitting material is a light emitting material that improved the luminous efficiency by using this point.
  • Phosphorescent light emission is difficult due to the nature of the organic material.
  • a transition metal iridium
  • an organic material is used as a host material to assist this.
  • Substances (hosts) that support phosphorescent materials must have a wide bandgap and high triplet state energy. Phosphors with excellent current and luminous efficiencies are in the spotlight, but organic electroluminescent devices with excellent electron transporting capacity are maintained until electrons and hole transporting capacity, thermally and electrically stable host materials and holes form excitons. There is a need for the development of a compound.
  • the present invention has excellent electrical stability and electron and hole transport ability, and has a triplet state energy, which can improve the luminous efficiency of the phosphorescent material, and a compound for an organic light emitting device, which can be used in a light emitting layer, and an organic electric field including the same.
  • a light emitting device can be provided.
  • the present invention can provide an electron transport material or an organic light emitting device compound that can be used in the hole transport material and an organic electroluminescent device comprising the same.
  • a compound for an organic light emitting device represented by Structural Formula 1 may be provided.
  • n 0 or 1
  • Ar 1 to Ar 4 may be the same or different from each other, Ar 1 to Ar 4 are each independently , , Substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C1 to C30 heteroaryl group,
  • X 1 and X 2 may be the same or different from each other, X 1 and X 2 are each independently an oxygen atom, a sulfur atom, , or ego,
  • Ar 5 are each independently , Substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C1 to C30 heterocycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C1 to C30 heteroaryl group,
  • R 31 and R 32 may be the same as or different from each other, R 31 and R 32 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted A C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R 31 and R 32 are bonded to each other and with a carbon atom therebetween Form a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl
  • R 1 to R 30 , and R 33 to R 36 may be the same as or different from each other, R 1 to R 30 , and R 33 to R 36 are each independently a hydrogen atom, a substituted or unsubstituted C 1 to C 30 alkyl group, substituted Or an unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R 1 At least one of R to R 30 , and R 33 to R 36 is a fused C3 to C30 cycloalkyl group which is further substituted or unsubstituted by further bonding with a neighboring carbon atom of the carbon atom to which one is bonded, substituted or unsubstituted Fused C1 to C30 heterocycloalkyl groups, substitute
  • substituted or unsubstituted C6 to C30 aryl group examples include substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthalenyl group, substituted or unsubstituted Anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted spirofluorenyl group, substituted or unsubstituted pyrenyl group, or substituted or unsubstituted phenyl It may be a rillenyl group.
  • substituted or unsubstituted C2 to C30 heteroaryl group examples include substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted thiophenyl group , Substituted or unsubstituted pyrrolyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted imidazo [1,2-a] pyridinyl group, substituted or unsubstituted Benzimidazolyl group, substituted or unsubstituted indazolyl group, substituted or unsubstituted phenothiazinyl group, substituted or unsubstituted phenazinyl group, substituted or unsubstituted carbazolyl group, substituted or
  • the compound for an organic light emitting device may be any one selected from compounds 1 to 160 represented by the following formula.
  • an organic electroluminescent device comprising the compound for an organic electroluminescent device may be provided.
  • the organic light emitting device comprising a single electrode or a plurality of organic material layer between the first electrode, the second electrode and the first electrode and the second electrode, selected from the single or plurality of organic material layer
  • One or more organic material layers may be provided with an organic electroluminescent device comprising the compound for an organic electroluminescent device.
  • the singular or plural organic material layers may include a light emitting layer.
  • the plurality of organic material layers may include a light emitting layer, and the plurality of organic material layers may further include at least one selected from an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, and a hole injection layer.
  • the emission layer may include a host and a dopant.
  • the present invention has excellent electrical stability, electron and hole transport ability, and has a triplet state energy, which can improve the luminous efficiency of the phosphorescent material, and a compound for an organic light emitting device that can be used in a light emitting layer, and comprising the same An organic electroluminescent device can be provided.
  • the present invention can provide an electron transport material of the organic electroluminescent device, a compound for an organic electroluminescent device that can be used in the hole transport material and an organic electroluminescent device comprising the same.
  • FIG. 1 is a cross-sectional view showing a cross section of an organic light emitting display device according to an embodiment of the present invention.
  • FIG. 2 is a cross-sectional view showing a cross section of an organic light emitting display device according to another embodiment of the present invention.
  • first and second to be used below may be used to describe various components, but the components are not limited by the terms. The terms are used only for the purpose of distinguishing one component from another.
  • first component may be referred to as the second component, and similarly, the second component may also be referred to as the first component.
  • a component when referred to as being “formed” or “laminated” on another component, it may be directly attached to, or laminated to, the front or one side on the surface of the other component, It will be understood that other components may exist in the.
  • atom bond means a single bond, a double bond or a triple bond unless otherwise defined.
  • substituted means that at least one hydrogen in a substituent or compound is deuterium, a halogen group, a hydroxy group, an amino group, a C1 to C30 amine group, a nitro group, a C1 to C30 silyl group, a C1 to C30 Alkyl group, C1 to C30 alkylsilyl group, C3 to C30 cycloalkyl group, C1 to C30 heterocycloalkyl group, C6 to C30 aryl group, C1 to C30 heteroaryl group, C1 to C20 alkoxy group, C1 to C10 trifluoroalkyl group or cyan It means what is substituted by a nog.
  • Two adjacent substituents of an alkoxy group, a C1 to C10 trifluoroalkyl group or a cyano group may be fused to form a ring.
  • hetero means one to four heteroatoms selected from the group consisting of N, O, S, and P in one functional group, and the remainder is carbon unless otherwise defined.
  • hydrogen means monotium, dihydrogen, or tritium unless otherwise defined.
  • an "alkyl group” means an aliphatic hydrocarbon group.
  • the alkyl group may be a "saturated alkyl group" that does not contain any double or triple bonds.
  • the alkyl group may be an "unsaturated alkyl group" containing at least one double or triple bond.
  • alkenylene group means a functional group consisting of at least two carbon atoms with at least one carbon-carbon double bond
  • alkynylene group means at least two carbon atoms with at least one carbon-carbon triplet It means a functional group consisting of a bond.
  • the alkyl group, whether saturated or unsaturated, may be branched, straight chain or cyclic.
  • the alkyl group may be a C1 to C30 alkyl group. More specifically, the alkyl group may be a C1 to C20 alkyl group, a C1 to C10 alkyl group, or a C1 to C6 alkyl group.
  • a C1 to C4 alkyl group has 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain is methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl Selected from the group consisting of:
  • alkyl group examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, ethenyl, propenyl, butenyl, cyclopropyl and cyclo
  • a butyl group, a cyclopentyl group, a cyclohexyl group, etc. are meant.
  • Amine group includes an arylamine group, an alkylamine group, an arylalkylamine group, or an alkylarylamine group.
  • a "cycloalkyl group” includes monocyclic or fused polycyclic (ie, rings that divide adjacent pairs of carbon atoms) functional groups.
  • Heterocycloalkyl group means containing 1 to 4 heteroatoms selected from the group consisting of N, O, S and P in the cycloalkyl group, and the rest are carbon. When the heterocycloalkyl group is a fused ring, each ring may include 1 to 4 heteroatoms.
  • Aromatic group means a functional group in which all elements of the functional group in the ring form have p-orbitals, and these p-orbitals form conjugation. Specific examples include an aryl group and a heteroaryl group.
  • aryl group includes monocyclic or fused ring polycyclic (ie, rings that divide adjacent pairs of carbon atoms) functional groups.
  • Heteroaryl group means containing 1 to 4 heteroatoms selected from the group consisting of N, O, S and P in the aryl group, the rest being carbon. When the heteroaryl group is a fused ring, each ring may include 1 to 4 heteroatoms.
  • the number of atoms of the ring in the aryl group and heteroaryl group is the sum of the number of carbon atoms and non-carbon atoms.
  • alkylaryl group When used in combination with an "alkylaryl group” or an “arylalkyl group”, the terms of each of the above alkyl and aryl have the meanings and content indicated above.
  • arylalkyl group means an aryl substituted alkyl radical such as benzyl and is included in the alkyl group.
  • alkylaryl group means an alkyl substituted aryl radical and is included in an aryl group.
  • an organic light emitting display device 1 including the compound for an organic light emitting display device according to the present invention may be provided.
  • the organic light emitting device includes a first electrode (110); Second electrode 150; And a single or plurality of organic material layers 130 between the first electrode and the second electrode, and at least one organic material layer selected from the single or plurality of organic material layers 130 includes a compound for an organic light emitting device according to the present invention. can do.
  • the singular or plural organic layer 130 may include a light emitting layer 134.
  • the organic layer 130 includes a light emitting layer 134, and the organic layer includes an electron injection layer 131, an electron transport layer 132, a hole blocking layer 133, an electron blocking layer 135, a hole At least one selected from the transport layer 136 and the hole injection layer 137 may be further included.
  • the emission layer 134 may include a host and a dopant.
  • the organic electroluminescent device is preferably supported by a transparent substrate.
  • the material of the transparent substrate is not particularly limited as long as it has good mechanical strength, thermal stability and transparency.
  • glass, a transparent plastic film, etc. can be used.
  • anode material of the organic electroluminescent device of the present invention a metal, an alloy, an electrically conductive compound having a work function of 4 eV or more, or a mixture thereof can be used.
  • transparent conductive materials such as Au or CuI, ITO (indium tin oxide), SnO 2 and ZnO which are metals are mentioned.
  • the thickness of the positive electrode film is preferably 10 to 200 nm.
  • the negative electrode material of the organic electroluminescent device of the present invention a metal, an alloy, an electrically conductive compound or a mixture thereof having a work function of less than 4 eV can be used.
  • a metal, an alloy, an electrically conductive compound or a mixture thereof having a work function of less than 4 eV can be used.
  • Na, Na-K alloy, calcium, magnesium, lithium, lithium alloy, indium, aluminum, magnesium alloy, aluminum alloy is mentioned.
  • aluminum / AlO 2 , aluminum / lithium, magnesium / silver or magnesium / indium may be used.
  • the thickness of the negative electrode film is preferably 10 to 200 nm.
  • At least one electrode preferably has a light transmittance of 10% or more.
  • the sheet resistance of the electrode is preferably several hundred ⁇ / mm or less.
  • the thickness of the electrode is 10 nm to 1 m, more preferably 10 to 400 nm.
  • Such an electrode may be manufactured by forming the above electrode material into a thin film through vapor deposition or sputtering such as chemical vapor deposition (CVD), physical vapor deposition (PVD), or the like.
  • the compound for an organic electroluminescent device of the present invention when used to suit the purpose of the present invention, a known hole transport material, a hole injection material, a light emitting layer material, a host material of the light emitting layer, an electron transport material, and an electron injection material, respectively, It may be used alone or in combination with the compound for an organic electroluminescent device of the present invention.
  • diphenylphosphine oxide-4- (triphenylsilyl) phenyl (TSPO1), Alq 3 , 2,5-diaryl silol derivative (PyPySPyPy), perfluorinated compound (PF-6P), Octasubstituted cyclooctatetraene compound (COTs) can be mentioned.
  • the electron injection layer, the electron transport layer, the hole transport layer and the hole injection layer may be formed of a single layer containing one or more kinds of the above-mentioned compounds, or may be stacked with different kinds of compounds. It may consist of a plurality of layers to contain.
  • the light emitting material examples include phosphorescent fluorescent materials, fluorescent brighteners, laser dyes, organic scintillators, and reagents for fluorescence analysis.
  • Each layer constituting the organic EL device of the present invention can be formed into a thin film through a known method such as vacuum deposition, spin coating or casting, or can be produced using a material used in each layer.
  • a material used in each layer There is no particular limitation on the film thickness of each layer, and it can be appropriately selected depending on the properties of the material, but can usually be determined in the range of 2 nm to 5,000 nm.
  • the compound for an organic light emitting device according to the present invention can be formed by a vacuum deposition method, there is an advantage that the thin film forming process is simple and can be easily obtained as a homogeneous thin film with little pin hole.
  • N-phenylnaphthalen-2-amine (8.0g, 0.036mol / sigma aldrich), Pd (pph3) 4 (2.0g, 0.0018mol), potassium carbonate (14.5g, 0.105) in intermediate 1-1 (12.4g, 0.040mol) mol) TOL 400ml was added and stirred at 95 °C for 2 hours to react. After the completion of the reaction, the mixture was cooled and H 2 O: MC was separated and the column was purified (n-Hexane: MC) to give 12.4 g (yield 77%) of compound 4.
  • naphthalen-2-amine (6.8 g, 0.0471 mol / sigma aldrich), 4-bromobiphenyl (10.0 g, 0.0429 mol), Pd 2 (dba) 3 (2.0 g, 0.0021 mol), NaOtBu (11.9 g, 0.1242 mol / sigma aldrich) 300 ml of TOL was added thereto and stirred at 95 ° C. for 2 hours to react. After the completion of the reaction, the mixture was cooled and H 2 O: MC was separated and column purified (n-Hexane: MC) to obtain 9.0g (yield 71%) of intermediate 15-1.
  • 1,4-diiodobenzene (18.3 g, 0.0555 mol / sigma aldrich), 4-bromophenylboronic acid (10.0 g, 0.050 mol / sigma aldrich), Pd (pph3) 4 (2.9 g, 0.0025 mol), potassium carbonate (20.9 g, 0.1515mol) was added to THF 400ml: Water 150ml and stirred at 65 °C for 2 hours. After the completion of the reaction, the mixture was cooled and H 2 O: MC was separated and column purified (n-Hexane: MC) to obtain 17.4 g (yield 90%) of the intermediate 107-1.
  • N-phenylnaphthalen-2-amine (16.9 g, 0.077 mol / sigma aldrich), Pd (pph3) 4 (2.0 g, 0.0018 mol), potassium carbonate (14.5 g, 0.105) in intermediate 134-1 (13.6 g, 0.035 mol) mol) to 500 ml of TOL and stirred at 95 °C for 2 hours to react. After the completion of the reaction, the mixture was cooled and H 2 O: MC was separated and the column was purified (n-Hexane: MC) to give 17.9 g (yield 77%) of compound 137.
  • NPB N, N'-Bis (naphthalen-1-yl) -N, N'-bis (phenyl) benzidine
  • Compound 1 was deposited on a glass substrate coated with ITO to form a hole transport layer having a thickness of 120 nm, and then doped with Ir (ppy) 3 so that the deposition rate was 9% using CBP as a host and Ir (ppy) 3 as a dopant.
  • An emission layer was formed to a thickness of 30 nm on the hole transport layer.
  • Balq was deposited thereon to a thickness of 10 nm to form a hole blocking layer that prevents holes from passing through the light emitting layer to the electron transport layer, and Alq 3 was deposited thereon to form a 40 nm electron transport layer, and lithium fluoride was deposited thereon. 1 nm of the electron injection layer was formed. Aluminum was deposited on the electron injection layer to form a cathode of 120 nm, thereby manufacturing an organic light emitting display device.
  • the deposition rate of each material was 0.1 nm / sec for compound 1, CBP, Alq 3 , Balq, which is an organic material, 0.01 nm / sec for lithium fluoride, and 0.5 nm / sec for aluminum.
  • An organic electroluminescent device of Device Examples 2 to 20 was manufactured by the same method as Device Example 1, except that the hole transport material described in Table 1 was used instead of Compound 1.
  • An organic electroluminescent device of Comparative Example 1 was manufactured in the same manner as in Example 1, except that NPB was used as a hole transport material instead of the compound 1.
  • the organic light emitting device (substrate size: 25 * 25mm 2 / deposition area: 2 * 2mm 2 ) made above is fixed to the IVL measurement set (CS-2000 + jig + IVL program), and then the current is increased by 1mA / m 2.
  • the present invention has excellent electrical stability and electron and hole transport ability, and has a triplet state energy, which can improve the luminous efficiency of the phosphorescent material, and a compound for an organic light emitting device that can be used in the light emitting layer, and including the same An organic electroluminescent device can be provided.
  • the present invention can provide an electron transport material of the organic electroluminescent device, a compound for an organic electroluminescent device that can be used in the hole transport material and an organic electroluminescent device comprising the same.

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Abstract

La présente invention concerne : un composé d'élément électroluminescent organique représenté par la formule structurale 1 ci-dessous ; et un élément électroluminescent organique comprenant celui-ci. La présente invention permet de produire : un élément électroluminescent organique qui peut être utilisé en tant que matériau de transport d'électron et un hôte ayant une stabilité électrique remarquable et des capacités de transport d'électron et de trou remarquables, ayant une énergie d'état triplet et capable d'améliorer l'efficacité lumineuse de matériaux phosphorescents.
PCT/KR2013/003358 2013-04-04 2013-04-19 Nouveau composé d'élément électroluminescent organique et élément électroluminescent organique comprenant celui-ci WO2014163228A1 (fr)

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KR20130036812 2013-04-04

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US20150236267A1 (en) * 2014-02-17 2015-08-20 Samsung Display Co., Ltd. Organic electroluminescence device
US20170324038A1 (en) * 2014-11-21 2017-11-09 Merck Patent Gmbh Heterocyclic compounds for use in electronic devices
WO2018101492A3 (fr) * 2018-03-19 2018-08-09 出光興産株式会社 Élément électroluminescent organique et dispositif électronique
JP2020158528A (ja) * 2007-12-03 2020-10-01 株式会社半導体エネルギー研究所 化合物、発光素子、発光装置、電子機器、および照明装置
US11217754B2 (en) * 2014-07-29 2022-01-04 Hodogaya Chemical Co., Ltd. Organic electroluminescence device
KR20220127802A (ko) 2020-01-15 2022-09-20 이데미쓰 고산 가부시키가이샤 화합물, 유기 전기발광 소자용 재료, 유기 전기발광 소자 및 전자 기기
US11581487B2 (en) 2017-04-26 2023-02-14 Oti Lumionics Inc. Patterned conductive coating for surface of an opto-electronic device
US11678569B2 (en) 2020-03-31 2023-06-13 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
US11730054B2 (en) 2018-01-29 2023-08-15 Idemitsu Kosan Co., Ltd. Compound having dibenzofuran and naphthalene structures, and organic electroluminescent element using same
US11730012B2 (en) 2019-03-07 2023-08-15 Oti Lumionics Inc. Materials for forming a nucleation-inhibiting coating and devices incorporating same
US11751415B2 (en) 2018-02-02 2023-09-05 Oti Lumionics Inc. Materials for forming a nucleation-inhibiting coating and devices incorporating same
US11985841B2 (en) 2020-12-07 2024-05-14 Oti Lumionics Inc. Patterning a conductive deposited layer using a nucleation inhibiting coating and an underlying metallic coating

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020158528A (ja) * 2007-12-03 2020-10-01 株式会社半導体エネルギー研究所 化合物、発光素子、発光装置、電子機器、および照明装置
US20150236267A1 (en) * 2014-02-17 2015-08-20 Samsung Display Co., Ltd. Organic electroluminescence device
US11217754B2 (en) * 2014-07-29 2022-01-04 Hodogaya Chemical Co., Ltd. Organic electroluminescence device
US20170324038A1 (en) * 2014-11-21 2017-11-09 Merck Patent Gmbh Heterocyclic compounds for use in electronic devices
US10957859B2 (en) * 2014-11-21 2021-03-23 Merck Patent Gmbh Heterocyclic compounds for use in electronic devices
US11581487B2 (en) 2017-04-26 2023-02-14 Oti Lumionics Inc. Patterned conductive coating for surface of an opto-electronic device
US11730054B2 (en) 2018-01-29 2023-08-15 Idemitsu Kosan Co., Ltd. Compound having dibenzofuran and naphthalene structures, and organic electroluminescent element using same
US11751415B2 (en) 2018-02-02 2023-09-05 Oti Lumionics Inc. Materials for forming a nucleation-inhibiting coating and devices incorporating same
WO2018101492A3 (fr) * 2018-03-19 2018-08-09 出光興産株式会社 Élément électroluminescent organique et dispositif électronique
US11730012B2 (en) 2019-03-07 2023-08-15 Oti Lumionics Inc. Materials for forming a nucleation-inhibiting coating and devices incorporating same
KR20220127802A (ko) 2020-01-15 2022-09-20 이데미쓰 고산 가부시키가이샤 화합물, 유기 전기발광 소자용 재료, 유기 전기발광 소자 및 전자 기기
US11678569B2 (en) 2020-03-31 2023-06-13 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
US11985841B2 (en) 2020-12-07 2024-05-14 Oti Lumionics Inc. Patterning a conductive deposited layer using a nucleation inhibiting coating and an underlying metallic coating

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