WO2017026727A1 - Dispositif luminescent organique - Google Patents

Dispositif luminescent organique Download PDF

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WO2017026727A1
WO2017026727A1 PCT/KR2016/008532 KR2016008532W WO2017026727A1 WO 2017026727 A1 WO2017026727 A1 WO 2017026727A1 KR 2016008532 W KR2016008532 W KR 2016008532W WO 2017026727 A1 WO2017026727 A1 WO 2017026727A1
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group
formula
organic
layer
light emitting
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PCT/KR2016/008532
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Korean (ko)
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이동훈
김진성
정인경
이순창
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머티어리얼사이언스 주식회사
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Priority claimed from KR1020160046519A external-priority patent/KR101879232B1/ko
Application filed by 머티어리얼사이언스 주식회사 filed Critical 머티어리얼사이언스 주식회사
Priority to CN201680002340.5A priority Critical patent/CN106796996B/zh
Publication of WO2017026727A1 publication Critical patent/WO2017026727A1/fr

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/72—Spiro hydrocarbons
    • 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
    • C07C211/54—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 two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
    • 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 an organic electroluminescent device. More particularly, the present invention relates to an organic light emitting display device comprising a specific hole transport material and a specific electron blocking material.
  • an organic light emitting display device is composed of a light emitting layer and a pair of counter electrodes sandwiching the layer. That is, in the organic electroluminescent device, when an electric field is applied between both electrodes, electrons are injected from the cathode, holes are injected from the anode, and they recombine in the emission layer to emit light.
  • More detailed structure of the organic light emitting device is a substrate, an anode, a hole injection layer for receiving holes in the anode, a hole transport layer for transporting holes, an electron blocking layer for blocking the entry of electrons from the light emitting layer to the hole transport layer, the hole and the electron coupling It consists of a light emitting layer that emits light, a hole blocking layer that blocks the entrance of holes from the light emitting layer to the electron transport layer, an electron transport layer that accepts electrons from the cathode and transports them to the light emitting layer, an electron injection layer that accepts electrons from the cathode, and a cathode.
  • a light emitting layer may be formed by doping a small amount of fluorescent or phosphorescent dye into an electron transport layer or a hole transport layer without a separate light emitting layer.
  • a single polymer generally serves as a hole transport layer, a light emitting layer, and an electron transport layer. You can also do this at the same time.
  • the organic thin film layers between the two electrodes are formed by vacuum deposition or spin coating, inkjet printing, laser thermal transfer, or the like. The reason why the organic light emitting diode is manufactured in a multilayer thin film structure is to stabilize the interface between the electrode and the organic material.
  • the hole and the electron transport layer have a large difference in the movement speed of holes and electrons. This is because luminous efficiency can be increased by effectively transferring electrons and electrons to the light emitting layer to balance the density of holes and electrons.
  • the driving principle of the organic light emitting display device is as follows. When a voltage is applied between the anode and the cathode, holes injected from the anode are moved to the light emitting layer via the hole injection layer and the hole transport layer. On the other hand, electrons are injected into the light emitting layer from the cathode via the electron injection layer and the electron transport layer, and carriers are recombined in the light emitting layer to generate excitons. The excitons change from the excited state to the ground state, whereby the fluorescent molecules in the light emitting layer emit light to form an image.
  • the light emitted while the excited state falls to the ground state through the singlet excited state is called “fluorescence”
  • the light emitted while falling to the ground state through the triplet excited state is called “phosphorescence”.
  • fluorescence the probability of singlet excited state is 25% (triple state 75%), and there is a limit of luminous efficiency, while phosphorescence is used to emit up to 75% of triplet state and 25% of singlet excited state.
  • the internal quantum efficiency can be up to 100%.
  • the biggest problem for the organic light emitting device is life and efficiency. As the display becomes larger, such efficiency and life problems must be solved.
  • the properties of the components included in each layer of the organic thin film layer including one or more layers including a light emitting layer between the anode and the cathode have a great influence on the driving voltage, the luminous efficiency, the luminance, and the lifetime of the device. Crazy Therefore, studies on the components included in each layer of the organic thin film layer are actively conducted.
  • Patent Document 1 Korean Unexamined Patent Publication No. 10-2015-0034379, Japanese Patent No. 2395088, Japanese Patent No. 3828595 and Korean Patent Publication No. 10-2013-0099098.
  • An object of the present invention is to provide an organic light emitting display device in which the luminous efficiency is remarkably improved by using a specific hole transport material and a specific electron blocking material.
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic film between the anode and the cathode, the organic film comprises a light emitting layer, between the anode and the light emitting layer
  • An organic electroluminescent device comprising an organic film comprising a compound represented by Formula 1 and an organic film comprising a compound represented by Formula 2 is provided:
  • n are each an integer of 0 to 5;
  • p, q and r are each an integer of 0 to 4.
  • Ar 1 is a single bond, an arylene group having 6 to 18 carbon atoms or a heteroarylene group having 5 to 18 nuclear atoms;
  • the Ar 2 to Ar 5 are the same or group different and each is independently selected from amines with each other, C 1 ⁇ C 10 alkyl group, C 2 ⁇ C 10 alkenyl group, C 2 ⁇ C 10 alkynyl group, C 3 ⁇ C 10 of the A cycloalkyl group, a nuclear atom having 3 to 10 heterocycloalkyl groups, a C 4 to C 60 aryl group and a nuclear atom having 5 to 20 heteroaryl groups;
  • R 1 to R 3 are each other the same or different, each independently represent hydrogen, deuterium (D), halogen, cyano, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the Alkynyl group, C 6 ⁇ C 60 Aryl group, Nucleotide 5 to 40 heteroaryl group, C 6 ⁇ C 60 Aryloxy group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryl An amine group, a C 3 to C 40 cycloalkyl group and a nuclear atom having 3 to 40 heterocycloalkyl groups;
  • L 1 to L 3 is the same as or different from each other, and is each independently a single bond, an arylene group having 6 to 40 carbon atoms, or a heteroarylene group having 5 to 40 nuclear atoms;
  • the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryloxy group, alkyloxy group, arylamine group, aryl group and heteroaryl group of Ar 2 to Ar 5 and R 1 to R 3 are each independently deuterium , Halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, halogen, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 Aryl group, heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 ⁇ C 60 , alkyloxy group of C 1 ⁇ C 40 , arylamine group of C 6 ⁇ C 60 , C 3 ⁇ C 40 Cycloalkyl group of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40
  • the compound represented by Formula 2 may be represented by the following formula (3):
  • R 1 , R 2 , R 3 , Ar 4 , Ar 5 , p, q, and r are each as defined in Formula 2.
  • the compound represented by Formula 2 may be represented by the following formula (4):
  • R 1 , R 2 , R 3 , Ar 4 , Ar 5 , L 3 , p, q, and r are each as defined in Formula 2.
  • Alkyl as used herein means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
  • alkenyl refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
  • alkynyl refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
  • Aryl in the present invention means a monovalent substituent derived from a C6 to C60 aromatic hydrocarbon combined with a single ring or two or more rings.
  • a form in which two or more rings are attached to each other (pendant) or condensed may also be included.
  • Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl as used herein means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form in which the two or more rings are condensed with an aryl group.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazole, carbazolyl (carbazoleyl) and 2-furanyl, N-imidazolyl, 2-iso Sazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, be
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms.
  • R means aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means an alkyl having 1 to 40 carbon atoms, and linear, branched or cyclic structure It may include.
  • 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 is meant herein monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons 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 as used herein means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se.
  • heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
  • alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.
  • condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the organic electroluminescent device of the present invention provides significantly improved driving voltage characteristics, luminous efficiency, and luminance by using a specific hole transport material and a specific electron blocking material.
  • the present invention provides an organic electroluminescent device comprising an anode, a cathode, and at least one organic film between the anode and the cathode, wherein the organic film includes a light emitting layer, and a compound represented by the following Chemical Formula 1 between the anode and the light emitting layer: It relates to an organic electroluminescent device comprising an organic film comprising and an organic film comprising a compound represented by Formula 2 below:
  • n are each an integer of 0 to 5
  • p, q and r are each an integer of 0 to 4,
  • Ar 1 is a single bond, an arylene group having 6 to 18 carbon atoms or a heteroarylene group having 5 to 18 nuclear atoms,
  • the Ar 2 to Ar 5 are the same or group different and each is independently selected from amines with each other, C 1 ⁇ C 10 alkyl group, C 2 ⁇ C 10 alkenyl group, C 2 ⁇ C 10 alkynyl group, C 3 ⁇ C 10 of the It is selected from the group consisting of a cycloalkyl group, a heterocycloalkyl group of 3 to 10 nuclear atoms, an aryl group of C 4 ⁇ C 60 and a heteroaryl group of 5 to 20 nuclear atoms,
  • R 1 to R 3 are each other the same or different, each independently represent hydrogen, deuterium (D), halogen, cyano, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the Alkynyl group, C 6 ⁇ C 60 Aryl group, Nucleotide 5 to 40 heteroaryl group, C 6 ⁇ C 60 Aryloxy group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryl An amine group, a C 3 to C 40 cycloalkyl group and a nuclear atom having 3 to 40 heterocycloalkyl groups;
  • L 1 to L 3 is the same as or different from each other, and each independently a single bond, an arylene group having 6 to 40 carbon atoms, or a heteroarylene group having 5 to 40 nuclear atoms,
  • the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryloxy group, alkyloxy group, arylamine group, aryl group and heteroaryl group of Ar 2 to Ar 5 and R 1 to R 3 are each independently deuterium , Halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, halogen C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60
  • the compound represented by Formula 2 may be represented by the following formula (3):
  • R 1 , R 2 , R 3 , Ar 4 , Ar 5 , p, q and r are each as defined in Chemical Formula 2.
  • the compound represented by Formula 2 may be represented by the following formula (4):
  • R 1 , R 2 , R 3 , Ar 4 , Ar 5 , L 3 , p, q and r are each as defined in Formula 2.
  • Ar 1 is a single bond or an arylene group of C 6 to C 19
  • Ar 4 is an aryl group of C 4 to C 60 or a heteroaryl group of 5 to 20 nuclear atoms
  • Ar 5 is an aryl group of C 4 to C 60 , but is not limited thereto.
  • the compound represented by Formula 1 of the present invention may be more specifically selected from the group consisting of the following compounds, but is not limited thereto.
  • the compound represented by Formula 1 of the present invention may be more preferably selected from the group consisting of the following compounds:
  • the compound represented by Formula 2 of the present invention may be more specifically selected from the group consisting of the following compounds, but is not limited thereto.
  • an organic electroluminescent device comprising an anode, a cathode, and at least one organic film between the anode and the cathode, wherein the organic film includes a light emitting layer, and is represented by the formula (1) between the anode and the light emitting layer It may include an organic film containing a compound and an organic film containing a compound represented by the formula (2).
  • the organic film including the compound represented by Chemical Formula 1 is a hole transport layer
  • the organic film including the compound represented by Chemical Formula 2 is an electron blocking layer, but is not limited thereto.
  • the hole transport layer may further include a hole transport material known in the art, in addition to the compound represented by Formula 1, and the electron blocking layer further includes a hole transport material known in the art, in addition to the compound represented by Formula 2 Can be.
  • the organic thin film layer further includes a hole injection layer, each layer included in the organic thin film layer is a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), and an emission layer (EML) Can be stacked in the order of.
  • HIL hole injection layer
  • HTL hole transport layer
  • EBL electron blocking layer
  • EML emission layer
  • the organic thin film layer further includes a hole injection layer, a light emitting layer, an electron transport layer, and an electron injection layer, and each layer included in the organic thin film layer includes a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL). ), An emission layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL).
  • HIL hole injection layer
  • HTL hole transport layer
  • EBL electron blocking layer
  • EML emission layer
  • ETL electron transport layer
  • EIL electron injection layer
  • the organic thin film layer may have a structure in which layers having various functions known in the art (not limited to organic layers) are stacked in addition to the laminated structure as described above for efficient light emission and long life of the device. .
  • the organic electroluminescent device of the present invention will be described by way of example.
  • the contents exemplified below do not limit the organic light emitting device of the present invention.
  • a positive electrode is coated on a surface of a substrate by a conventional method to form a positive electrode.
  • the substrate used is preferably a glass substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling and waterproof.
  • the positive electrode material indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, may be used.
  • a hole injection layer is formed on the surface of the anode by vacuum thermal evaporation or spin coating of a hole injection layer (HIL) material in a conventional manner.
  • hole injection layer materials include copper phthalocyanine (CuPc), 4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine (m-MTDATA), 4,4', 4" -tris (3-methylphenyl Amino) phenoxybenzene (m-MTDAPB), starburst amines 4,4 ', 4 "-tri (N-carbazolyl) triphenylamine (TCTA), 4,4', 4" -tris Examples include (N- (2-naphthyl) -N-phenylamino) -triphenylamine (2-TNATA) or IDE406 available from Idemitsu.
  • a hole transport layer is formed on the surface of the hole injection layer by vacuum thermal evaporation or spin coating of a hole transport layer (HTL) material in a conventional manner.
  • the hole transport layer may be formed by stacking the compound represented by Chemical Formula 1.
  • the light emitting layer (EML) material on the surface of the hole transport layer by vacuum thermal evaporation or spin coating in a conventional manner to form a light emitting layer.
  • EML light emitting layer
  • tris (8-hydroxyquinolinolato) aluminum (Alq3), etc. may be used as the sole light emitting material or the light emitting host material among the light emitting layer materials, and in the case of blue, Balq (8-hydroxyquinolineberyllium) may be used.
  • DPVBi 4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl) series, spiro (spiro) substance, spiro-DPVBi (spiro-4, 4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzooxazolyl) -phenol lithium salt), bis (biphenylvinyl) benzene, aluminum -Quinoline metal complexes, metal complexes of imidazole, thiazole and oxazole and the like can be used.
  • An electron blocking layer is formed on the surface of the hole transport layer by vacuum thermal evaporation or spin coating of an electron blocking layer (EBL) material in a conventional manner.
  • EBL electron blocking layer
  • a compound represented by Chemical Formula 2 may be used as the electron blocking layer material.
  • IDE102 In the case of a dopant which can be used together with a light emitting host in the light emitting layer material, IDE102, IDE105, which is available from Idemitsu as a fluorescent dopant, and tris (2-phenylpyridine) iridium (III) (Ir (ppy) as a phosphorescent dopant. 3), iridium (III) bis [(4,6-difluorophenyl) pyridinato-N, C-2 '] picolinate (FIrpic) (Chihaya Adachi et al., Appl. Phys Lett., 2001, 79, 3082-3084), platinum (II) octaethyl porphyrin (PtOEP), TBE002 (Kobiion) and the like can be used.
  • FIrpic ihaya Adachi et al., Appl. Phys Lett., 2001, 79, 3082-3084
  • An electron transport layer is formed on the surface of the light emitting layer by vacuum thermal evaporation or spin coating of an electron transport layer (ETL) material in a conventional manner.
  • ETL electron transport layer
  • the electron transport layer material used is not particularly limited, and preferably tris (8-hydroxyquinolinolato) aluminum (Alq 3) may be used.
  • HBL hole blocking layer
  • the hole blocking layer may be formed by vacuum thermal evaporation and spin coating of the hole blocking layer material in a conventional manner, and the hole blocking layer material is not particularly limited, but is preferably (8-hydroxyquinolinol).
  • Earth) lithium (Liq) bis (8-hydroxy-2-methylquinolinolato) -aluminum biphenoxide (BAlq), bathocuproine (BCP), LiF and the like can be used.
  • An electron injection layer is formed on the surface of the electron transport layer by vacuum thermal evaporation or spin coating of an electron injection layer (EIL) material in a conventional manner.
  • EIL electron injection layer
  • the material of the electron injection layer may be a material such as LiF, Liq, Li 2 O, BaO, NaCl, CsF, etc.
  • the negative electrode is vacuum-deposited on the surface of the electron injection layer by a conventional method Form.
  • the negative electrode material used is lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and the like can be used.
  • indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode through which light can pass.
  • the capping layer CPL may be formed on the surface of the cathode by the composition for capping layer formation of the present invention.
  • the organic light emitting device may be manufactured in the order described above, that is, in the order of anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode, and vice versa.
  • the electron injection layer, the electron transport layer, the light emitting layer, the electron blocking layer, the hole transport layer, the hole injection layer and the anode may be manufactured in the order.
  • HAT-CN hole injection layer
  • HTL hole transport layer
  • EBL electron blocking layer
  • 10-Bis (2-naphthyl) anthraces (ADN) was doped with 25 nm of 2,5,8,11-Tetra-butyl-Perylene (t-Bu-Perylene) as a dopant.
  • Anthracene derivative and LiQ were mixed 1: 1 to deposit an electron transport layer (ETL) with a thickness of 30 nm, and LiQ was deposited with an electron injection layer (EIL) on a thickness of 10 nm. Thereafter, a mixture of magnesium and silver (Ag) in a 9: 1 mixture was deposited to a thickness of 15 nm, and N4, N4'-bis [4- [bis () was formed as a capping layer on the cathode.
  • ETL electron transport layer
  • EIL electron injection layer
  • An organic electroluminescent device was manufactured by bonding a seal cap containing a hygroscopic agent with a UV curable adhesive to protect the organic electroluminescent device from O 2 or moisture in the air.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the electron blocking material 2-2 to 2-11 instead of the compound 2-1 in Example 1.
  • Example 1 the compound 1-1 was used instead of compound 1-1, and the electron blocking material was used compound 2-3, compound 2-4, and compound 2-8 instead of compound 2-1.
  • An organic light emitting display device was manufactured in the same manner as in Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound 1-1 and NPB instead of the compound 2-1 as the electron blocking material in Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using NPB instead of the compound 1-1 as the hole transport material in Example 8.
  • the present invention relates to an organic electroluminescent device. More particularly, the present invention relates to an organic light emitting display device comprising a specific hole transport material and a specific electron blocking material.

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Abstract

La présente invention concerne un dispositif luminescent organique comprenant une cathode, une anode et au moins une couche de film organique entre la cathode et l'anode, et elle concerne plus particulièrement un dispositif luminescent organique comprenant, entre la cathode et une couche d'émission de lumière, un film organique comprenant un ou plusieurs types de composés représentés par la formule chimique 1 et un film organique comprenant un ou plusieurs types de composés représentés par la formule chimique 2, présentant ainsi des caractéristiques de grande efficacité.
PCT/KR2016/008532 2015-08-07 2016-08-02 Dispositif luminescent organique WO2017026727A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017144150A3 (fr) * 2016-02-23 2017-10-12 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
JP2020528445A (ja) * 2017-07-28 2020-09-24 メルク パテント ゲーエムベーハー 電子デバイスに使用するためのスピロビフルオレン誘導体
US20200308129A1 (en) * 2017-12-15 2020-10-01 Merck Patent Gmbh Substituted aromatic amines for use in organic electroluminescent devices

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002241352A (ja) * 2001-02-13 2002-08-28 Konica Corp 新規化合物、それを用いる有機エレクトロルミネッセンス素子材料及び有機エレクトロルミネッセンス素子
KR20130099263A (ko) * 2008-05-16 2013-09-05 호도가야 가가쿠 고교 가부시키가이샤 아릴아민 화합물
WO2014129201A1 (fr) * 2013-02-22 2014-08-28 保土谷化学工業株式会社 Élément électroluminescent organique
KR20140133572A (ko) * 2012-02-14 2014-11-19 메르크 파텐트 게엠베하 유기 전계발광 소자용 스피로비플루오렌 화합물
KR20150044592A (ko) * 2013-10-17 2015-04-27 (주)위델소재 아민 화합물의 제조방법

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002241352A (ja) * 2001-02-13 2002-08-28 Konica Corp 新規化合物、それを用いる有機エレクトロルミネッセンス素子材料及び有機エレクトロルミネッセンス素子
KR20130099263A (ko) * 2008-05-16 2013-09-05 호도가야 가가쿠 고교 가부시키가이샤 아릴아민 화합물
KR20140133572A (ko) * 2012-02-14 2014-11-19 메르크 파텐트 게엠베하 유기 전계발광 소자용 스피로비플루오렌 화합물
WO2014129201A1 (fr) * 2013-02-22 2014-08-28 保土谷化学工業株式会社 Élément électroluminescent organique
KR20150044592A (ko) * 2013-10-17 2015-04-27 (주)위델소재 아민 화합물의 제조방법

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017144150A3 (fr) * 2016-02-23 2017-10-12 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
US10454041B2 (en) 2016-02-23 2019-10-22 Merck Patent Gmbh Materials for organic electroluminescent devices
US11538996B2 (en) 2016-02-23 2022-12-27 Merck Patent Gmbh Materials for organic electroluminescent devices
JP2020528445A (ja) * 2017-07-28 2020-09-24 メルク パテント ゲーエムベーハー 電子デバイスに使用するためのスピロビフルオレン誘導体
JP7413252B2 (ja) 2017-07-28 2024-01-15 メルク パテント ゲーエムベーハー 電子デバイスに使用するためのスピロビフルオレン誘導体
US20200308129A1 (en) * 2017-12-15 2020-10-01 Merck Patent Gmbh Substituted aromatic amines for use in organic electroluminescent devices

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