[go: up one dir, main page]

WO2011139129A2 - Compose à base de triphénylène comprenant une amine aromatique et élément électroluminescent le comprenant - Google Patents

Compose à base de triphénylène comprenant une amine aromatique et élément électroluminescent le comprenant Download PDF

Info

Publication number
WO2011139129A2
WO2011139129A2 PCT/KR2011/003416 KR2011003416W WO2011139129A2 WO 2011139129 A2 WO2011139129 A2 WO 2011139129A2 KR 2011003416 W KR2011003416 W KR 2011003416W WO 2011139129 A2 WO2011139129 A2 WO 2011139129A2
Authority
WO
WIPO (PCT)
Prior art keywords
compound
formula
mmol
organic
aryl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2011/003416
Other languages
English (en)
Korean (ko)
Other versions
WO2011139129A3 (fr
Inventor
김신한
홍진석
이은정
김경수
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Doosan Corp
Original Assignee
Doosan Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Doosan Corp filed Critical Doosan Corp
Publication of WO2011139129A2 publication Critical patent/WO2011139129A2/fr
Publication of WO2011139129A3 publication Critical patent/WO2011139129A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—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

Definitions

  • the present invention includes a novel triphenylene compound having excellent electron transport ability, hole injection and / or transport ability, and / or luminous ability, and the triphenylene compound in at least one organic layer, thereby providing luminous efficiency, brightness, thermal stability, driving voltage,
  • the present invention relates to an organic electroluminescent device having improved characteristics such as lifetime.
  • organic light emitting phenomenon refers to a phenomenon in which light appears when electric energy is applied to an organic material.
  • a voltage is applied between the two electrodes, and holes are injected into the organic layer and electrons are injected into the cathode.
  • excitons are formed, and when the excitons fall back to the ground, they shine.
  • Such organic EL devices include an indium tin oxide (ITO) substrate, an anode, a hole injection layer that selectively receives holes from an anode, a hole transport layer that selectively transfers holes, a light emitting layer where holes and electrons recombine to emit light, and optionally an electron It consists of an electron transporting layer for transferring the electrons, optionally an electron injection layer for receiving electrons from the cathode and the cathode.
  • ITO indium tin oxide
  • the hole and the electrons in the device are balanced to improve the luminous efficiency. Electrons injected from the electron injection layer and holes transferred from the hole injection layer recombine in the emission layer to form excitons, and fall from the singlet excited state to the ground state and are called fluorescence, and fall from the triplet excited state to the ground state. Luminescence is called phosphorescence. Theoretically, when the exciton is generated when the carrier is recombined in the emission layer, the ratio of singlet and triplet excitons is generated at a ratio of 1: 3, and when phosphorescence is used, the internal quantum efficiency may be 100%.
  • CBP carbazole compound
  • a metal complex compound containing heavy atoms such as Ir and Pt
  • T g glass transition temperature
  • An object of the present invention is to include a triphenylene-based compound having excellent electron transporting ability, hole injection and / or transporting ability and / or light emitting ability (fluorescence or phosphorescence) in at least one organic layer, thereby providing luminous efficiency, brightness, thermal stability, driving It is to provide an organic EL device having improved characteristics such as voltage and lifetime.
  • the present invention provides a compound represented by the following formula (1):
  • A is a single bond, phenyl, naphthyl, substituted or unsubstituted heteroaryl having 6 to 10 nuclear atoms, wherein the substituent introduced into the hetero aryl is a halogen atom, an alkyl group having 1 to 3 carbon atoms, and 6 carbon atoms To 10 aryl groups;
  • B is substituted or unsubstituted aryl between C6 and C10, substituted or unsubstituted heteroaryl having 6 to 10 nuclear atoms, wherein the substituent introduced into the aryl or heteroaryl is a halogen atom, an alkyl group having 1 to 3 carbon atoms And an aryl group having 6 to 10 carbon atoms;
  • a and B may be the same as or different from each other independently,
  • X is one of N, O, S,
  • l, m are each independently 0 or 1, where X is O or S, then one of l and m is 0,
  • n is an integer of 1 or 2
  • Ar 1 to Ar 4 is substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted heteroaryl having 5 to 20 nuclear atoms, wherein the substituents introduced into aryl, heteroaryl are deuterium or halogen atoms, carbon atoms 1 It is selected from the group consisting of an alkyl group of ⁇ 3, an aryl group having 6 to 10 carbon atoms, each may be the same or different independently.
  • Ar 1 and Ar 2 may be bonded to adjacent substituents and / or A to each other to form a condensed ring
  • Ar 3 and Ar 4 may be bonded to adjacent substituents and / or B to each other to form a condensed ring.
  • the condensed ring refers to forming a ring by combining a substituent with a substituent.
  • the atom included in the hetero aryl may be a nitrogen atom, but is not limited thereto.
  • the present invention the anode; cathode; And at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes the compound of Formula 1 described above.
  • the compound of Chemical Formula 1 according to the present invention is used as the material for the organic EL device can exhibit the power efficiency and luminous efficiency improvement through a high hole injection and transport ability compared to the conventional NPB used as a hole injection and transport material Can be.
  • the triphenylene compound having a wide singlet energy level and a high triplet energy level has an effect on the aryl amine substituent which is an electron donating group (EDG) and the singlet and triplet energy levels of the compound. It is characterized by the introduction of less influent linkers (A, B).
  • the singlet energy is regulated by introducing a functional group such as aryl amine, and the phenyl or naphthyl, having 6 to 10 nuclear atoms.
  • a functional group such as aryl amine, and the phenyl or naphthyl, having 6 to 10 nuclear atoms.
  • substituents and linkers can be effectively used as a hole injection layer and hole transport layer material of an organic EL device by effectively adjusting the energy level of triphenylene, maximizing the hole blocking ability and the hole injection / transport ability.
  • substituents and linkers when used as a light emitting layer material of the phosphorescent organic EL device through the conversion of the linking group, it is possible to provide a compound exhibiting improved light emission characteristics.
  • the fluorescent or phosphorescent organic EL device including the compound of the present invention can provide a full color display panel and the like which are greatly improved in light emission performance and lifetime.
  • A, B, Ar 1 to Ar 4 and n are the same as defined in Chemical Formula 1.
  • a or B when A or B is a hetero aryl having 6 to 10 nuclear atoms, it may be selected from a substituent group consisting of the following Chemical Formula 5.
  • a plurality of Z introduced into the substituent group of the formula (5) are each independently and may be the same or different from each other, even if they are the same, at least one of the plurality of Z is a nitrogen atom, the remainder is a carbon atom.
  • Ar 1 and Ar 2 may be bonded to adjacent substituents and / or A to form a condensed ring, and Ar 3 and Ar 4 may be bonded to adjacent substituents and / or B to be condensed. Can be formed.
  • the compound represented by Formula 1 of the present invention may be synthesized according to a general synthetic method ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995)). Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
  • Another aspect of the present invention relates to an organic electroluminescent device comprising the compound represented by Formula 1 according to the present invention.
  • the present invention is an anode (anode); Cathode; And at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer includes a compound represented by Chemical Formula 1.
  • the compound of Formula 1 may be included alone or in plurality.
  • the organic layer including the compound represented by Formula 1 of the present invention may be any one or more of a hole injection layer, a hole transport layer, an electron transport layer and a light emitting layer.
  • the compound represented by Formula 1 may be included in the organic EL device as a hole injection layer and a hole transport layer material, in which case the organic EL device may maximize the hole blocking ability and the hole injection / transport ability.
  • the compound represented by Chemical Formula 1 may be used as a light emitting layer material of the organic EL device, thereby providing improved efficiency.
  • the light emitting layer may include a phosphorescent dopant material or a fluorescent dopant material.
  • the compound represented by Formula 1 of the present invention may be included in the organic EL device as a blue, green, and / or red phosphorescent host, a fluorescent host, a hole transport material, a hole injection material, and / or an electron transport material. .
  • the compound represented by Formula 1 according to the present invention has a high glass transition temperature of 150 °C or more. Therefore, when the compound is used as the organic layer of the organic EL device, since the crystallization is minimized in the organic EL device, the driving voltage of the device can be lowered, and the luminous efficiency, luminance, thermal stability, and lifetime characteristics can be improved.
  • a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode may be sequentially stacked.
  • at least one of the light emitting layer, the hole injection layer, the hole transport layer, and the electron transport layer may include a compound represented by Chemical Formula 1.
  • An electron injection layer may be positioned on the electron transport layer.
  • the organic EL device according to the present invention may not only have a structure in which an anode, at least one organic layer, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at the interface between the electrode and the organic layer.
  • the organic layer including the compound of Formula 1 may be formed by vacuum deposition or solution coating.
  • the solution application include spin coating, dip coating, doctor blading, inkjet printing or thermal transfer method, but is not limited thereto.
  • the organic EL device of the present invention forms an organic layer and an electrode using materials and methods known in the art, except that at least one layer of the organic layer in the device includes the compound represented by Formula 1 of the present invention. Can be prepared.
  • a silicon wafer, quartz, glass plate, metal plate, plastic film or sheet may be used as the substrate.
  • the anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals 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 and polyaniline; Or carbon black, but is not limited thereto.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals 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),
  • Cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer, the hole transport layer, the electron transport layer and the electron injection layer is not particularly limited, and conventional materials known in the art may be used.
  • a glass substrate coated with ITO (Indium tin oxide) 1500 thin film was washed by distilled water ultrasonic. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then cleaned the substrate using UV for 5 minutes. The substrate was transferred to a vacuum depositor.
  • ITO Indium tin oxide
  • An organic EL device was manufactured in the order of / LiF (1 nm) / Al (200 nm).
  • DS-H522 and DS-501 used in device fabrication are manufactured by Doosan Corporation BG, and the structures of m-MTDATA, TCTA, CBP, Ir (ppy) 3 , and BCP are as follows.
  • An organic EL device was manufactured in the same manner as in Example 1, except that NPB was used as a light emitting host material instead of the compound prepared in Synthesis Example, when forming the hole transport layer.
  • An organic EL device was manufactured in the same manner as in Example 1, except that CBP was used as a light emitting host material, instead of the compound prepared in Synthesis Example, to form an emission layer.
  • the compound of Chemical Formula 1 according to the present invention is used as the material for the organic EL device can exhibit the power efficiency and luminous efficiency improvement through a high hole injection and transport ability compared to the conventional NPB used as a hole injection and transport material Can be.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Manufacturing & Machinery (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un composé à base de triphénylène ainsi qu'un élément électroluminescent organique le comprenant. Plus spécifiquement, un matériau utilisé pour un élément électroluminescent organique phosphorescent ou fluorescent est un nouveau composé à base de triphénylène possédant des propriétés de transport d'électrons et/ou d'émission de lumière grâce à l'introduction d'un groupe de liaison et d'un groupe de substitution arylamine. Ainsi, un élément électroluminescent organique de l'invention possédant des caractérisques améliorées telles que le rendement d'émission de lumière, la luminosité, la tension d'attaque et la durée de vie, peut être produit.
PCT/KR2011/003416 2010-05-06 2011-05-06 Compose à base de triphénylène comprenant une amine aromatique et élément électroluminescent le comprenant Ceased WO2011139129A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020100042665A KR101218029B1 (ko) 2010-05-06 2010-05-06 방향족 아민을 포함하는 트리페닐렌계 화합물 및 이를 포함하는 유기 전계 발광 소자
KR10-2010-0042665 2010-05-06

Publications (2)

Publication Number Publication Date
WO2011139129A2 true WO2011139129A2 (fr) 2011-11-10
WO2011139129A3 WO2011139129A3 (fr) 2012-04-19

Family

ID=44904254

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2011/003416 Ceased WO2011139129A2 (fr) 2010-05-06 2011-05-06 Compose à base de triphénylène comprenant une amine aromatique et élément électroluminescent le comprenant

Country Status (2)

Country Link
KR (1) KR101218029B1 (fr)
WO (1) WO2011139129A2 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012176674A1 (fr) * 2011-06-23 2012-12-27 東レ株式会社 Élément électroluminescent
JP2014001327A (ja) * 2012-06-20 2014-01-09 Sumitomo Chemical Co Ltd 高分子化合物およびそれを用いた発光素子
JP2014509306A (ja) * 2010-12-29 2014-04-17 エルジー・ケム・リミテッド 新規な化合物およびこれを用いた有機発光素子
US20150034924A1 (en) * 2011-10-24 2015-02-05 Hodogaya Chemical Co., Ltd. Novel triphenylene derivatives and organic electroluminescent devices using said derivatives
EP2924753A1 (fr) * 2014-03-25 2015-09-30 Novaled GmbH Dispositifs émettant de la lumière polychromatique et matrice de transport de trou polyvalent pour ceux-ci
CN105073718A (zh) * 2013-05-16 2015-11-18 第一毛织株式会社 有机化合物、有机光电元件及显示元件
US20160028014A1 (en) * 2014-07-22 2016-01-28 Samsung Display Co., Ltd. Organic light-emitting device
JP2016526029A (ja) * 2013-05-16 2016-09-01 チェイル インダストリーズ インコーポレイテッド 有機化合物、有機光電子素子および表示装置
WO2017069258A1 (fr) * 2015-10-21 2017-04-27 出光興産株式会社 Nouveau composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
CN113214174A (zh) * 2014-05-27 2021-08-06 环球展览公司 有机电致发光材料及其用途

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140135525A (ko) 2013-05-16 2014-11-26 제일모직주식회사 유기 광전자 소자용 발광 재료, 유기 광전자 소자 및 표시 장치
KR101433822B1 (ko) 2013-06-17 2014-08-27 삼성디스플레이 주식회사 유기 발광 장치
KR101627761B1 (ko) 2013-07-10 2016-06-07 제일모직 주식회사 유기 화합물, 유기 광전자 소자 및 표시 장치
KR102227046B1 (ko) * 2018-06-14 2021-03-12 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006143845A (ja) * 2004-11-18 2006-06-08 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置
KR100753454B1 (ko) * 2006-02-03 2007-08-31 주식회사 이엘엠 고성능 유기 발광 재료 및 유기 발광 다이오드
US8628862B2 (en) * 2007-09-20 2014-01-14 Basf Se Electroluminescent device
JP5353069B2 (ja) * 2008-06-04 2013-11-27 三菱化学株式会社 トリフェニレン系化合物、トリフェニレン系化合物を含有する有機電界発光素子及び有機ｅｌディスプレイ

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014509306A (ja) * 2010-12-29 2014-04-17 エルジー・ケム・リミテッド 新規な化合物およびこれを用いた有機発光素子
US8946695B2 (en) 2010-12-29 2015-02-03 Lg Chem, Ltd. Compound, and organic light-emitting device using same
WO2012176674A1 (fr) * 2011-06-23 2012-12-27 東レ株式会社 Élément électroluminescent
US20150034924A1 (en) * 2011-10-24 2015-02-05 Hodogaya Chemical Co., Ltd. Novel triphenylene derivatives and organic electroluminescent devices using said derivatives
JP2014001327A (ja) * 2012-06-20 2014-01-09 Sumitomo Chemical Co Ltd 高分子化合物およびそれを用いた発光素子
US9735369B2 (en) 2013-05-16 2017-08-15 Cheil Industries, Inc. Luminescent material for organic optoelectric device and organic optoelectric device and display device
CN105073718A (zh) * 2013-05-16 2015-11-18 第一毛织株式会社 有机化合物、有机光电元件及显示元件
JP2016526029A (ja) * 2013-05-16 2016-09-01 チェイル インダストリーズ インコーポレイテッド 有機化合物、有機光電子素子および表示装置
CN105073718B (zh) * 2013-05-16 2018-03-09 第一毛织株式会社 有机化合物、有机光电元件及显示元件
WO2015144633A1 (fr) * 2014-03-25 2015-10-01 Novaled Gmbh Dispositifs électroluminescents polychromatiques et matrice de transport de trous polyvalente pour lesdits dispositifs
CN106414394A (zh) * 2014-03-25 2017-02-15 诺瓦尔德股份有限公司 多色发光器件及其通用空穴传输基质
EP2924753A1 (fr) * 2014-03-25 2015-09-30 Novaled GmbH Dispositifs émettant de la lumière polychromatique et matrice de transport de trou polyvalent pour ceux-ci
CN106414394B (zh) * 2014-03-25 2018-11-23 诺瓦尔德股份有限公司 多色发光器件及其通用空穴传输基质
CN113214174A (zh) * 2014-05-27 2021-08-06 环球展览公司 有机电致发光材料及其用途
US20160028014A1 (en) * 2014-07-22 2016-01-28 Samsung Display Co., Ltd. Organic light-emitting device
WO2017069258A1 (fr) * 2015-10-21 2017-04-27 出光興産株式会社 Nouveau composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique

Also Published As

Publication number Publication date
KR20110123172A (ko) 2011-11-14
KR101218029B1 (ko) 2013-01-02
WO2011139129A3 (fr) 2012-04-19

Similar Documents

Publication Publication Date Title
WO2011139129A2 (fr) Compose à base de triphénylène comprenant une amine aromatique et élément électroluminescent le comprenant
WO2020027389A1 (fr) Composé électroluminescent organique et élément électroluminescent organique le comprenant
WO2014010823A1 (fr) Composé hétérocyclique et élément électronique organique comprenant ce composé
WO2013009079A1 (fr) Composé à base de triphénylène et diode électroluminescente organique l'utilisant
WO2011139125A2 (fr) Composé de phénanthrocarbazole, et dispositif électroluminescent organique utilisant ce composé
WO2013002509A2 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2011149240A2 (fr) Composé à base de triphénylène bipolaire et élément électroluminescent organique le comprenant
WO2012099376A2 (fr) Nouveau composé et dispositif électroluminescent organique comprenant ledit composé
WO2011081431A2 (fr) Composé émetteur de lumière organique, et dispositif électroluminescent organique l'utilisant
WO2011059271A2 (fr) Nouveau composé comprenant un anneau condensé, et dispositif électronique organique qui utilise celui-ci
WO2020040514A1 (fr) Diode électroluminescente organique
WO2019164301A1 (fr) Composé et diode électroluminescente organique le comprenant
WO2014098455A1 (fr) Nouveau composé organique et élément électroluminescent organique le comprenant
WO2017061779A1 (fr) Composé amine et dispositif électroluminescent organique le comprenant
WO2017061832A1 (fr) Nouveau composé et diode électroluminescente organique comprenant celui-ci
WO2020111733A1 (fr) Dispositif électroluminescent organique
WO2019013526A1 (fr) Nouveau composé et dispositif électroluminescent organique le contenant
WO2019045405A1 (fr) Composé hétérocyclique et élément électroluminescent organique l'utilisant
WO2020009492A9 (fr) Composé polycyclique et diode électroluminescente organique le comprenant
WO2014123391A1 (fr) Composé hétérocyclique et élément électroluminescent organique l'utilisant
WO2020111586A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2019160315A1 (fr) Composé hétérocyclique et dispositif électroluminescent organique le comprenant
WO2010058946A2 (fr) Nouveaux dérivés de chrysène et dispositif électrique organique utilisant ces dérivés
WO2024112021A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2012115394A2 (fr) Composé, dispositif électronique organique utilisant celui-ci et dispositif électronique associé

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11777610

Country of ref document: EP

Kind code of ref document: A2

NENP Non-entry into the national phase

Ref country code: DE

32PN Ep: public notification in the ep bulletin as address of the adressee cannot be established

Free format text: NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1) EPC (EPO FORM 1205A DATED 18.02.2013)

122 Ep: pct application non-entry in european phase

Ref document number: 11777610

Country of ref document: EP

Kind code of ref document: A2