WO2013183851A1 - Nouveau composé d'élément électroluminescent organique et élément électroluminescent organique le comprenant - Google Patents

Nouveau composé d'élément électroluminescent organique et élément électroluminescent organique le comprenant Download PDF

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WO2013183851A1
WO2013183851A1 PCT/KR2013/002321 KR2013002321W WO2013183851A1 WO 2013183851 A1 WO2013183851 A1 WO 2013183851A1 KR 2013002321 W KR2013002321 W KR 2013002321W WO 2013183851 A1 WO2013183851 A1 WO 2013183851A1
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현서용
윤용호
송정한
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(주)피엔에이치테크
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Priority claimed from KR1020120118447A external-priority patent/KR20130136359A/ko
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Priority to CN201380038179.3A priority Critical patent/CN104471021B/zh
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    • C07D471/12—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 three hetero rings
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    • 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
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    • 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
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    • 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
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    • 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
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    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

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 high molecular and low molecular forms, and low molecules may be divided into pure organic materials and metal complexes forming 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 characteristics, 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 an anode and a cathode, thereby emitting a light emitting layer.
  • the exciton can be easily formed and the luminous efficiency can be increased.
  • Luminescent materials can be broadly divided into host materials and luminescent materials (dopant) materials, and luminescent materials are classified into fluorescence and phosphorescence according to the 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.
  • the present invention has excellent electrical stability and electron and hole transport ability, and the triplet state energy is high, the compound for an organic light emitting device that can be used in the light emitting layer as a host that can improve the luminous efficiency of the phosphorescent material and an organic electric field comprising 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 the following Structural Formula 1 or 2 may be provided.
  • R 4 to R 6 may be the same as or different from each other, R 4 to R 6 are each independently a hydrogen atom,
  • R 4 to R 6 is a fused C 3 to C 30 cycloalkyl group further bonded with a neighboring carbon atom of the carbon atom to which one is bonded, A substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or
  • X 1 to X 37 may be the same as or different from each other, X 1 to X 37 are each independently a nitrogen atom, or ego,
  • Y 1 to Y 13 may be the same or different from each other, Y 1 to Y 13 are each independently an oxygen atom, a sulfur atom, , or ego,
  • R 8 to R 70 may be the same as or different from each other, R 8 to R 70 are each independently a hydrogen atom, , , , , 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 Or a C1 to C30 heteroaryl group, or at least one of R 8 to R 70 is a fused C3 to C30 cycloalkyl group which is further substituted with an adjacent carbon atom of the carbon atom to which one is bonded, or substituted or unsubstituted, A substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group
  • Ar 3 to Ar 7 may be the same as or different from each other, Ar 3 to Ar 7 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,
  • Ar 1 and Ar 2 may be the same as or different from each other, and Ar 1 and Ar 2 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, substituted or unsubstituted Or a C1 to C30 heteroaryl group, or Ar 1 and Ar 2 are bonded to each other and form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, together with a nitrogen atom therebetween. Can do it,
  • X 38 to X 40 may be the same or different from each other, X 38 to X 40 are each independently a nitrogen atom, or ego,
  • Y 14 to Y 17 may be the same or different from each other, Y 14 to Y 17 are each independently an oxygen atom, a sulfur atom, , or ego,
  • R 71 to R 116 may be the same as or different from each other, R 71 to R 116 may be independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to A C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
  • Ar 8 is a substituted or unsubstituted C1 to C30 alkyl group, 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 group,
  • R 1 to R 3 , and R 7 may be the same or different from each other, R 1 to R 3 , and R 7 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to A 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 to R 3 , and R At least one of 7 is a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, further bonded to a neighboring carbon atom of the carbon atom to which one is bonded, Substituted or unsubstitute
  • 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 organic light emitting device compound may be a compound for an organic light emitting device, characterized in that any one selected from compounds 1 to 92 represented by the following structural 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, 1 selected from the single or plurality of organic material layer
  • At least one organic material layer may include the compound for an organic light emitting 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 is excellent in electrical stability and electron and hole transport ability, high triplet energy, host, hole injection material, hole transport material, electron transport material, electron injection material and the like which can improve the luminous efficiency of phosphorescent material
  • a compound for an organic light emitting device that can be used as a sealing material having excellent refractive index in a top emission method, and an organic light emitting device including the same can be provided.
  • 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 among the alkoxy group, C1 to C10 trifluoroalkyl group or 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 of at least one carbon-carbon double bond
  • alkynylene group means at least two carbon atoms of 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:
  • the alkyl group is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, ethenyl, propenyl, butenyl, cyclopropyl, 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 a monocyclic or fused ring polycyclic (ie, a ring that divides 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 photoluminescent 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.
  • NPB N, N'-Bis (naphthalen-1-yl) -N, N'-bis (phenyl) benzidine
  • NPB was deposited on a glass substrate coated with ITO to form a hole transport layer having a thickness of 120 nm.
  • Ir (ppy) 3 was used as a dopant, and compound 1 was deposited at 9% rate, that is, the deposition rate of compound 1 was 0.1 nm / sec.
  • Ir (ppy) 3 was deposited at 0.009nm / sec to dope Ir (ppy) 3 to a deposition rate of 8% to form a light emitting layer 30nm thick on the hole transport layer.
  • Balq was deposited thereon to form a hole blocking layer that prevents holes from moving through the light emitting layer to the electron transport layer, and Alq 3 was deposited thereon to form an electron transport layer having a thickness of 40 nm. By depositing, an electron injection layer having a thickness of 1 nm 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.
  • each material is an organic material
  • Compound 1, NPB, Alq 3 , Balq was deposited at a rate of 0.1 nm / sec
  • lithium fluoride is deposited at a rate of 0.01 nm / sec
  • aluminum is 0.5 nm / sec It was.
  • An organic electroluminescent device of Device Examples 2 to 14 was manufactured by the same method as Device Example 1, except that Compound 1 was used as the light emitting material shown in Table 1 below.
  • An organic light emitting display device was manufactured in the same manner as in Example 1, except that CBP ((4,4-N, N-dicarbazole) biphenyl) was used instead of Compound 1 and Compound 6 was used instead of NPB as the hole transport material. Was prepared.
  • An organic light emitting diode was manufactured according to the same method as Device Example 27, except that Compound 6 was used as the hole transport material shown in Table 1 below.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using (4,4-N, N-dicarbazole) biphenyl (CBP) as a light emitting material instead of Compound 1.
  • the organic light emitting element made from above (substrate size: 25x25mm 2 / deposition area: 2x2mm 2) an IVL measuring set (CS-2000 + fixture + IVL program) and then fixed to the raises the current by 1mA / m 2 light emission luminance of the deposition surface (cd / m 2 ), driving voltage (V), current density (A / m 2 ), and luminous efficiency (cd / A), and the driving voltage and luminous efficiency are shown in Table 1 above when the luminance is 1000 cd / m 2 . Indicated.
  • the present invention is excellent in electrical stability and electron and hole transport ability, high triplet energy, host, hole injection material, hole transport material, electron transport material, electron injection material and the like which can improve the luminous efficiency of phosphorescent material
  • a compound for an organic light emitting device that can be used as a sealing material having excellent refractive index in a top emission method, and an organic light emitting device including the same can be provided.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne : un composé d'élément électroluminescent organique représenté par la formule structurale 1 ou 2 ci-après ; et un élément électroluminescent organique le comprenant. De cette manière, il est possible de proposer un composé d'élément électroluminescent organique qui peut être utilisé comme hôte, matière de transport de trous et matière de transport d'électrons qui a une stabilité électrique exceptionnelle et une capacité de transport d'électrons et de trous exceptionnelle, un niveau élevé d'énergie à l'état triplet et est apte à améliorer le rendement d'émission de lumière de matières émettant de la lumière phosphorescente, et il est également possible de proposer un élément électroluminescent organique.
PCT/KR2013/002321 2012-06-04 2013-03-21 Nouveau composé d'élément électroluminescent organique et élément électroluminescent organique le comprenant WO2013183851A1 (fr)

Priority Applications (1)

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CN201380038179.3A CN104471021B (zh) 2012-06-04 2013-03-21 新的有机电致发光器件用化合物及包含该化合物的有机电致发光器件

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KR10-2012-0059643 2012-06-04
KR20120059643 2012-06-04
KR1020120118447A KR20130136359A (ko) 2012-06-04 2012-10-24 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
KR10-2012-0118447 2012-10-24
KR10-2012-0151964 2012-12-24
KR1020120151964A KR101527181B1 (ko) 2012-06-04 2012-12-24 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자

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CN104650076A (zh) * 2013-12-26 2015-05-27 北京鼎材科技有限公司 含有咪唑并吡啶基团的化合物及在有机电致发光中的应用
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JP2016113397A (ja) * 2014-12-15 2016-06-23 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． カルバゾール化合物、有機エレクトロルミネッセンス素子用材料、および有機エレクトロルミネッセンス素子
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WO2017150380A1 (fr) * 2016-02-29 2017-09-08 東ソー株式会社 Composé de quinoxaline et utilisation de celui-ci
CN107337680A (zh) * 2017-07-17 2017-11-10 江苏三月光电科技有限公司 一种以芴为核心的有机化合物及其在oled器件上的应用
CN109516980A (zh) * 2017-09-20 2019-03-26 邱天隆 双极性材料以及有机发光二极管元件
JP2021020912A (ja) * 2016-02-29 2021-02-18 東ソー株式会社 キノキサリン化合物及びその用途
CN114805373A (zh) * 2022-02-25 2022-07-29 京东方科技集团股份有限公司 一种空穴传输材料、发光器件、显示面板及显示装置
KR20220127802A (ko) 2020-01-15 2022-09-20 이데미쓰 고산 가부시키가이샤 화합물, 유기 전기발광 소자용 재료, 유기 전기발광 소자 및 전자 기기
US11495749B2 (en) 2015-04-06 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11581487B2 (en) 2017-04-26 2023-02-14 Oti Lumionics Inc. Patterned conductive coating for surface of an opto-electronic device
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
US11818949B2 (en) 2015-04-06 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US11834459B2 (en) 2018-12-12 2023-12-05 Universal Display Corporation Host materials for electroluminescent devices
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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CN104650089B (zh) * 2013-12-26 2017-10-03 固安鼎材科技有限公司 一种含咔唑‑9‑基基团的芴类衍生物及其应用
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CN104650090A (zh) * 2013-12-26 2015-05-27 北京鼎材科技有限公司 一种含咔唑-3-基基团的芴类衍生物及其应用
CN104650076A (zh) * 2013-12-26 2015-05-27 北京鼎材科技有限公司 含有咪唑并吡啶基团的化合物及在有机电致发光中的应用
CN104650088A (zh) * 2013-12-26 2015-05-27 北京鼎材科技有限公司 一种含咔唑基的衍生物及其在有机电致发光器件中的应用
JP2015157808A (ja) * 2014-02-24 2015-09-03 ユニバーサル ディスプレイ コーポレイション 有機エレクトロルミネセンス材料、及びデバイス
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EP2910555A1 (fr) * 2014-02-24 2015-08-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
WO2015142040A1 (fr) 2014-03-17 2015-09-24 Rohm And Haas Electronic Materials Korea Ltd. Matériau tampon d'électrons et dispositif électroluminescent organique
CN106068261B (zh) * 2014-03-17 2019-08-23 罗门哈斯电子材料韩国有限公司 电子缓冲材料和有机电致发光装置
EP3415508A1 (fr) * 2014-03-17 2018-12-19 Rohm And Haas Electronic Materials Korea Ltd. Matériau tampon d'électrons et dispositif électroluminescent organique
EP3119751A4 (fr) * 2014-03-17 2017-12-27 Rohm And Haas Electronic Materials Korea Ltd. Matériau tampon d'électrons et dispositif électroluminescent organique
CN106068261A (zh) * 2014-03-17 2016-11-02 罗门哈斯电子材料韩国有限公司 电子缓冲材料和有机电致发光装置
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US10818846B2 (en) 2014-04-29 2020-10-27 Rohm And Haas Electronic Materials Korea Ltd. Electron transport material and organic electroluminescent device comprising the same
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US10084142B2 (en) 2014-12-15 2018-09-25 Samsung Display Co., Ltd. Carbazole compound, material for organic electroluminescent device, and organic electroluminescent device
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