WO2020130509A1 - Composé organique et élément électroluminescent organique le comprenant - Google Patents

Composé organique et élément électroluminescent organique le comprenant Download PDF

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WO2020130509A1
WO2020130509A1 PCT/KR2019/017699 KR2019017699W WO2020130509A1 WO 2020130509 A1 WO2020130509 A1 WO 2020130509A1 KR 2019017699 W KR2019017699 W KR 2019017699W WO 2020130509 A1 WO2020130509 A1 WO 2020130509A1
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group
alkyl
aryl
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손효석
엄민식
홍진석
심재의
박정근
이용환
박우재
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Solus Advanced Materials Co Ltd
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Doosan Solus Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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

Definitions

  • the present invention relates to a novel organic compound that can be used as a material for an organic electroluminescent device and an organic electroluminescent device comprising the same.
  • the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground state, light is emitted.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to its function.
  • the luminescent material may be divided into blue, green, and red luminescent materials, and yellow and orange luminescent materials for realizing a better natural color according to the luminous color.
  • a host/dopant system may be used as a light emitting material to increase color purity and increase light emission efficiency through energy transfer.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • NPB, BCP, and Alq 3 are widely known as the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer material, and anthracene derivatives have been reported as the light emitting layer material.
  • metal complex compounds containing Ir such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2, etc., which have advantages in terms of efficiency improvement among light emitting layer materials, are blue, green, and red. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.
  • the present invention can be applied to an organic electroluminescent device, and has an object to provide a novel organic compound having excellent holes, electron injection and transport ability, and luminescence ability.
  • Another object of the present invention is to provide an organic electroluminescent device that exhibits low driving voltage and high luminous efficiency and improves life, including the novel organic compound.
  • X 1 , X 3 are each independently N or C(R 1 ), but at least one is N,
  • L 1 to L 3 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C 6 to C 40 arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 40 nuclear atoms;
  • Ar 1 is a substituent represented by the following formula (2),
  • Ar 2 is a substituent represented by the following formula (3),
  • Ar 3 is a C 6 ⁇ C 18 aryl group or a heteroaryl group having 5 to 18 nuclear atoms
  • Y 1 and Y 2 are each independently O or S,
  • Z 1 and Z 2 are each independently a single bond, group consisting of N(R 2 ), C(R 3 )(R 4 ), O, S, P(R 5 ) and Si(R 6 )(R 7 ) Selected from Z 1 and Z 2 are not single bonds,
  • a and b are each independently an integer from 0 to 4
  • R 1 to R 7 are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 Alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyl Oxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl Boron group, C 6 ⁇ C 60 arylphosphanyl group, C 6 ⁇ C 60 mono or diarylphosphinyl group and C 6 ⁇ C 60 arylamine group selected from the group consisting of, or
  • the arylene group and heteroarylene group of L 1 to L 3, the alkyl group of the R 1 to R 5 , alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocyclo Alkyl group, arylamine group, alkyl silyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ alkyl group of C 40, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ aryl of C 60 Oxy group, C 1 ⁇ C 40 alkyloxy group, C 6
  • the present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the organic material layers of the one or more layers comprises the compound of Formula 1 .
  • Alkyl in the present invention is a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl And the like, but is not limited thereto.
  • Alkenyl in the present invention is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms, having one or more carbon-carbon double bonds, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
  • Alkynyl in the present invention is a monovalent substituent derived from a straight chain or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms, having one or more carbon-carbon triple bonds, for example, ethynyl , 2-propynyl, and the like, but is not limited thereto.
  • Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings.
  • two or more rings are condensed with each other, and contain only carbon as a ring forming atom (for example, the number of carbon atoms may be 8 to 60), and the entire molecule is monovalent with non-aromacity.
  • Substituents may also be included. Examples of such aryl include phenyl, naphthyl, phenanthryl, anthryl, and fluorenyl, but are not limited thereto.
  • Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon in the ring, preferably 1 to 3 carbons is substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply attached to or condensed with each other, and as ring-forming atoms, hetero atoms selected from among N, O, P, S, and Se other than carbon are included, and the whole molecule is non-aromatic (non-aromatic). It is interpreted as including a monovalent group having aromacity).
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl; Polycyclics such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
  • Aryloxy in the present invention is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like, but are not limited thereto.
  • Alkyloxy in the present invention is a monovalent substituent represented by R O-, wherein R means 1 to 40 alkyl, and includes a linear, branched or cyclic structure. It is interpreted as. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • Cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, It is substituted with a hetero atom such as S or Se.
  • heterocycloalkyl include morpholine, piperazine, and the like, but are not limited thereto.
  • Alkylsilyl in the present invention means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 5 to 60 carbon atoms.
  • Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
  • the compound of the present invention is excellent in thermal stability, carrier transport ability, luminescence ability, and the like, it can be usefully applied as an organic material layer material of an organic electroluminescent device.
  • the organic electroluminescent device including the compound of the present invention in the organic material layer has significantly improved aspects such as luminescence performance, driving voltage, life, efficiency, and can be effectively applied to a full color display panel.
  • FIG. 1 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • FIG. 2 is a sectional view showing an organic electroluminescent device according to an embodiment of the present invention.
  • the novel compound of the present invention has a form in which bis-dibenzomoiety and an azine-based compound are combined as a basic skeleton, and is specifically characterized by being represented by the following Chemical Formula 1.
  • X 1 , X 3 are each independently N or C(R 1 ), but at least one is N,
  • L 1 to L 3 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C 6 to C 40 arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 40 nuclear atoms;
  • Ar 1 is a substituent represented by the following formula (2),
  • Ar 2 is a substituent represented by the following formula (3),
  • Ar 3 is a C 6 ⁇ C 18 aryl group or a heteroaryl group having 5 to 18 nuclear atoms
  • Y 1 and Y 2 are each independently O or S,
  • Z 1 and Z 2 are each independently a single bond, group consisting of N(R 2 ), C(R 3 )(R 4 ), O, S, P(R 5 ) and Si(R 6 )(R 7 ) Selected from Z 1 and Z 2 are not single bonds,
  • a and b are each independently an integer from 0 to 4
  • R 1 to R 7 are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 Alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyl Oxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl Boron group, C 6 ⁇ C 60 arylphosphanyl group, C 6 ⁇ C 60 mono or diarylphosphinyl group and C 6 ⁇ C 60 arylamine group selected from the group consisting of, or
  • the arylene group and heteroarylene group of L 1 to L 3, the alkyl group of the R 1 to R 5 , alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocyclo Alkyl group, arylamine group, alkyl silyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ alkyl group of C 40, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ aryl of C 60 Oxy group, C 1 ⁇ C 40 alkyloxy group, C 6
  • Bis-dibenzomoiety is combined with an electron withdrawing group (EWG) having high electron absorption, such as a nitrogen-containing heterocycle (eg, pyridine group, pyrimidine group, triazine group, etc.).
  • EWG electron withdrawing group
  • a nitrogen-containing heterocycle eg, pyridine group, pyrimidine group, triazine group, etc.
  • the compound represented by Formula 1 of the present invention is an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (green or red phosphorescent host material), an electron transport layer/injection layer material, a light emitting layer material, an electron transport auxiliary layer material, More preferably, it can be used as a light emitting layer material, an electron transport layer material, or an electron transport auxiliary layer material.
  • the performance of the organic electroluminescent device including the compound of Formula 1 can be greatly improved, and the performance of a full color organic light emitting panel to which the organic electroluminescent device is applied can be maximized.
  • Ar 1 may be a substituent represented by any one of the following A-1 to A-10.
  • Y1 and Y2 are as defined in Chemical Formula 1.
  • Ar 2 may be a substituent represented by any one of the following B-1 to B-9.
  • Ring A is a 5-6 membered cycloalkyl, phenyl or a 5-6 membered heteroaryl,
  • R 2 to R 4 are as defined in Formula 1 of claim 1,
  • Y 3 and Y 4 are each independently O or S.
  • Ar 3 may be a substituent represented by any one of the following C-1 to C-6.
  • Y 5 and Y 6 are each independently selected from the group consisting of a single bond, N(R 10 ), C(R 11 )(R 12 ), O and S, but both Y 5 and Y 6 are not single bonds,
  • R 8 to R 12 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 Alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyl Oxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl Boron group, C 6 ⁇ C 60 arylphosphanyl group, C 6 ⁇ C 60 mono or diarylphosphinyl group and C 6 ⁇ C 60 arylamine group is selected from the group consisting of
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of R 8 to R 12 Boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C Alkynyl group of 2 ⁇ C 40 , aryl group of C 6 ⁇ C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 ⁇ C 60 , alkyloxy group of C 1 ⁇ C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalky
  • the compound of the present invention may be specifically represented by compounds having the structure illustrated below, but is not limited thereto.
  • the compound of Formula 1 of the present invention can be synthesized according to general synthetic methods ( Chem. Rev. , 60 :313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995 ) Etc.). The detailed synthesis process for the compounds of the present invention will be described in detail in the synthesis examples described later.
  • organic electroluminescent device comprising the compound represented by Chemical Formula 1 according to the present invention.
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is It includes a compound represented by the formula (1). At this time, the compound may be used alone or in combination of two or more.
  • the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, wherein at least one organic material layer includes a compound represented by Formula 1 Can.
  • the structure of the organic electroluminescent device according to the present invention is not particularly limited, but referring to FIG. 1 as an example, for example, the positive electrode 10 and the negative electrode 20 facing each other, and the positive electrode 10 and the negative electrode ( 20) includes an organic layer 30 located between.
  • the organic layer 30 may include a hole transport layer 31, a light emitting layer 32 and an electron transport layer 34.
  • a hole transport auxiliary layer 33 may be included between the hole transport layer 31 and the light emitting layer 32
  • an electron transport auxiliary layer 35 may be included between the electron transport layer 34 and the light emitting layer 32. can do.
  • the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, the electron transport layer 34 and the cathode Between 20, the electron injection layer 36 may be further included.
  • the hole injection layer 37 stacked between the hole transport layer 31 and the anode 10 improves the interfacial properties between ITO used as the anode and the organic material used as the hole transport layer 31.
  • it is a layer that functions to make the surface of ITO smooth by being applied to the top of ITO where the surface is not flat, and can be used without particular limitation as long as it is commonly used in the art, for example, an amine compound can be used. It is not limited to this.
  • the electron injection layer 36 is a layer that is stacked on top of the electron transport layer 34 to facilitate electron injection from the cathode to ultimately improve power efficiency, and is commonly used in the art. If it can be used can be used without particular limitation, for example, LiF, Liq, NaCl, CsF, Li 2 O, BaO and the like can be used.
  • a hole transport auxiliary layer 33 may be further included between the hole transport layer 31 and the light emitting layer 32.
  • the hole transport auxiliary layer 33 may serve to transport holes to the light emitting layer 32 while adjusting the thickness of the organic layer 30.
  • the hole transport auxiliary layer 33 may include a hole transport material, and may be made of the same material as the hole transport layer 31.
  • an electron transport auxiliary layer 35 may be further included between the electron transport layer 34 and the light emitting layer 32. Holes moving through the ionization potential level in the organic light emitting device to the light emitting layer 32 are blocked by the high energy barrier of the electron transport auxiliary layer 35 and do not diffuse or move to the electron transport layer 34, resulting in holes. It functions to limit the light emitting layer 32. The function of limiting holes to the light-emitting layer 32 prevents holes from being diffused into the electron transport layer 34 that transfers electrons by reduction, thereby suppressing a decrease in lifespan through irreversible decomposition reaction due to oxidation, and organic light emission. It can contribute to improving the life of the device.
  • Bis-dibenzomoiety is combined with an electron withdrawing group (EWG) having high electron absorption, such as a nitrogen-containing heterocycle (eg, pyridine group, pyrimidine group, triazine group, etc.).
  • EWG electron withdrawing group
  • a nitrogen-containing heterocycle eg, pyridine group, pyrimidine group, triazine group, etc.
  • the compound represented by Chemical Formula 1 which is the representative claim structure of the present invention, has excellent light emission properties
  • the hole injection layer 37, the hole transport layer 31, the light emitting layer 32, and the electron as the organic material layer of the organic electroluminescent device It can be used as a material of any one of the transport layer 34 and the electron injection layer 36.
  • it can be used as the material for the electron transport layer 34 and the electron auxiliary transport layer 35.
  • the organic electroluminescent device may include an anode, one or more organic material layers, and a cathode sequentially stacked as described above, and may further include an insulating layer or an adhesive layer at the interface between the electrode and the organic material layer.
  • the organic electroluminescent device of the present invention is a material and method known in the art, except that at least one (eg, electron transport auxiliary layer) of the organic material layer is formed to contain the compound represented by the formula (1) It may be manufactured by forming another organic material layer and an electrode.
  • at least one (eg, electron transport auxiliary layer) of the organic material layer is formed to contain the compound represented by the formula (1) It may be manufactured by forming another organic material layer and an electrode.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution application method include spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer, but are not limited thereto.
  • the substrate usable in the present invention is not particularly limited, and a silicon wafer, quartz, glass plate, metal plate, plastic film and sheet may be used.
  • the positive electrode material may be made of a conductor having a high work function to facilitate hole injection, for example, a metal such as vanadium, chromium, copper, zinc, or gold, or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SnO 2 :Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but is not limited thereto.
  • a conductor having a high work function to facilitate hole injection for example, a metal such as vanadium, chromium, copper, zinc, or gold, or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide
  • the negative electrode material may be made of a conductor having a low work function to facilitate electron injection, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. The same metal or alloys thereof; And a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • a green organic electroluminescent device was prepared as follows.
  • the glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone or methanol
  • UV ozone cleaner Power sonic 405, Hwashin Tech
  • Example B-1 When forming the green light emitting layer in Example B-1, an organic EL device was manufactured in the same manner as Compound A-10 used as a green light emitting material.
  • a green organic electroluminescent device was manufactured in the same manner as in Example A-1, except that Compound A-10 was not used in Example A-1.
  • the green organic electroluminescent devices green organic electroluminescent devices manufactured in Examples A-1 to A-32, respectively using the compound according to the present invention as a luminescent material, only CBP of the conventional light emitting layer It can be seen that it exhibits better performance in terms of current efficiency and driving voltage than the green organic electroluminescent element used as a material (the organic electroluminescent element of Comparative Example 1).
  • the glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone or methanol
  • UV ozone cleaner Power sonic 405, Hwashin Tech
  • Example B-1 When forming the electron transport layer in Example B-1, an organic EL device was manufactured by performing the same procedure instead of Compound A-10 used as the electron transport layer material.
  • An organic EL device was manufactured in the same manner as in Example B-1, except that Alq3 was used as the electron transporting layer material instead of Compound A-10 used as the electron transporting layer material when forming the electron transporting layer in Example B-1.
  • DS-205 and DS-405 used for device fabrication are products of Doosan Electronics BG Co., Ltd., and the structures of NPB, ADN and Alq3 are as follows.
  • the organic EL devices using the compound according to the present invention as an electron transport layer are organic EL devices using conventional Alq (comparison) It can be seen that it exhibits better performance in terms of current efficiency and driving voltage than the organic EL device of Example 2).
  • the present invention relates to a novel organic compound that can be used as a material for an organic electroluminescent device and an organic electroluminescent device comprising the same.

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Abstract

La présente invention concerne un nouveau composé et un élément électroluminescent organique le comprenant. Le composé selon la présente invention est utilisé pour une couche de matériau organique d'un élément électroluminescent organique, de préférence pour une couche électroluminescente, de façon à améliorer l'efficacité lumineuse, la tension de commande, la durée de vie, etc. de l'élément électroluminescent organique.
PCT/KR2019/017699 2018-12-18 2019-12-13 Composé organique et élément électroluminescent organique le comprenant Ceased WO2020130509A1 (fr)

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KR10-2018-0164479 2018-12-18
KR1020180164479A KR102746510B1 (ko) 2018-12-18 2018-12-18 유기 화합물 및 이를 포함하는 유기 전계 발광 소자

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WO2020130509A1 true WO2020130509A1 (fr) 2020-06-25

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WO2024121133A1 (fr) 2022-12-08 2024-06-13 Merck Patent Gmbh Dispositif électronique organique et matériaux spéciaux pour dispositifs électroniques organiques
WO2024132993A1 (fr) 2022-12-19 2024-06-27 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2024194264A1 (fr) 2023-03-20 2024-09-26 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045843A1 (fr) 2023-08-30 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045851A1 (fr) 2023-08-30 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045842A1 (fr) 2023-08-30 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045816A1 (fr) 2023-08-29 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025073675A1 (fr) 2023-10-04 2025-04-10 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025104058A1 (fr) 2023-11-16 2025-05-22 Merck Patent Gmbh Matériaux pour dispositifs électroniques organiques
WO2025119821A1 (fr) 2023-12-05 2025-06-12 Merck Patent Gmbh Composition de matériau pour dispositifs électroluminescents organiques
WO2025168515A1 (fr) 2024-02-06 2025-08-14 Merck Patent Gmbh Matériaux pour dispositifs électroniques organiques
WO2025195961A1 (fr) 2024-03-19 2025-09-25 Merck Patent Gmbh Dispositifs électroluminescents organiques
WO2025228800A1 (fr) 2024-04-30 2025-11-06 Merck Patent Gmbh Matériaux pour dispositifs électroniques organiques
WO2026017612A1 (fr) 2024-07-15 2026-01-22 Merck Patent Gmbh Dispositif électroluminescent organique
WO2026017608A1 (fr) 2024-07-15 2026-01-22 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2026017607A1 (fr) 2024-07-15 2026-01-22 Merck Patent Gmbh Dispositif électroluminescent organique
WO2026017611A1 (fr) 2024-07-15 2026-01-22 Merck Patent Gmbh Dispositif électroluminescent organique
WO2026162564A1 (fr) 2025-01-31 2026-08-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques

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Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024121133A1 (fr) 2022-12-08 2024-06-13 Merck Patent Gmbh Dispositif électronique organique et matériaux spéciaux pour dispositifs électroniques organiques
WO2024132993A1 (fr) 2022-12-19 2024-06-27 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2024194264A1 (fr) 2023-03-20 2024-09-26 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045816A1 (fr) 2023-08-29 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045843A1 (fr) 2023-08-30 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045851A1 (fr) 2023-08-30 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025045842A1 (fr) 2023-08-30 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025073675A1 (fr) 2023-10-04 2025-04-10 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025104058A1 (fr) 2023-11-16 2025-05-22 Merck Patent Gmbh Matériaux pour dispositifs électroniques organiques
WO2025119821A1 (fr) 2023-12-05 2025-06-12 Merck Patent Gmbh Composition de matériau pour dispositifs électroluminescents organiques
WO2025168515A1 (fr) 2024-02-06 2025-08-14 Merck Patent Gmbh Matériaux pour dispositifs électroniques organiques
WO2025195961A1 (fr) 2024-03-19 2025-09-25 Merck Patent Gmbh Dispositifs électroluminescents organiques
WO2025228800A1 (fr) 2024-04-30 2025-11-06 Merck Patent Gmbh Matériaux pour dispositifs électroniques organiques
WO2026017612A1 (fr) 2024-07-15 2026-01-22 Merck Patent Gmbh Dispositif électroluminescent organique
WO2026017608A1 (fr) 2024-07-15 2026-01-22 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2026017607A1 (fr) 2024-07-15 2026-01-22 Merck Patent Gmbh Dispositif électroluminescent organique
WO2026017611A1 (fr) 2024-07-15 2026-01-22 Merck Patent Gmbh Dispositif électroluminescent organique
WO2026162564A1 (fr) 2025-01-31 2026-08-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques

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