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WO2009148269A9 - Derive de benzofluoranthene et element luminescent organique a base de ce derive - Google Patents

Derive de benzofluoranthene et element luminescent organique a base de ce derive Download PDF

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Publication number
WO2009148269A9
WO2009148269A9 PCT/KR2009/002968 KR2009002968W WO2009148269A9 WO 2009148269 A9 WO2009148269 A9 WO 2009148269A9 KR 2009002968 W KR2009002968 W KR 2009002968W WO 2009148269 A9 WO2009148269 A9 WO 2009148269A9
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group
light emitting
organic
present
compound represented
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PCT/KR2009/002968
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English (en)
Korean (ko)
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WO2009148269A2 (fr
WO2009148269A3 (fr
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신창주
김태형
김경수
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주식회사 두산
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Publication of WO2009148269A2 publication Critical patent/WO2009148269A2/fr
Publication of WO2009148269A3 publication Critical patent/WO2009148269A3/fr
Publication of WO2009148269A9 publication Critical patent/WO2009148269A9/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
    • 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
    • H10K50/16—Electron 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
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
    • 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
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring

Definitions

  • the present invention relates to a novel benzofluoranthene derivative and an organic electroluminescent device using the same. More specifically, a benzimidazole group, a benzothiazole group, The present invention relates to an organic light emitting device including a benzofluoranthene derivative including at least one substituent selected from the group consisting of benzoxazole groups, and an organic material layer containing the benzofluoranthene derivative.
  • organic light emitting phenomenon refers to a phenomenon in which light appears when electric energy is applied to an organic material. That is, when the organic material layer is positioned between the anode and the cathode and a voltage is applied between the two electrodes, electrons and holes are injected and an excited state of the organic material is generated. The excited carrier then returns to its original stable state and emits the unique light of the material itself.
  • organic light emitting devices used in the present invention include a hole injection layer that receives holes from a substrate, an anode, and an anode, a hole transport layer for transferring holes, a light emitting layer for recombining holes and electrons to emit light, an electron transport layer for transferring electrons, It consists of an electron injection layer and a cathode which receive an electron from a cathode.
  • the reason why the EL device is manufactured in multiple layers is that the movement speeds of the holes and the electrons are different. Therefore, if the appropriate hole injection layer, the transport layer, the electron transport layer, and the electron injection layer are made, holes and electrons can be effectively transferred. This is because the light emission efficiency can be improved by balancing the electrons.
  • TPBI published by Kodak in 1996 and described in US Pat. No. 5,645,948, is known as a representative electron transporting material having an imidazole group, and its structure is three N-phenyl benz at 1,3,5 substitution position of benzene. It contains an imidazole group and functionally blocks electrons from the light emitting layer as well as its ability to transfer electrons, but has a problem of low thermal stability for practical application.
  • the electron transport materials disclosed in Japanese Patent Application Laid-Open No. 11-345686 report that they contain oxazole groups and thiazole groups and can be applied to the light emitting layer, but have reached practical use in terms of driving voltage, luminance, and lifetime of the device. I can't.
  • An object of the present invention is to provide a novel compound which is substituted with a substituent having an electron transfer capability to benzofluoranthene, which can be applied to an organic light emitting device to improve luminous efficiency, stability and device life. .
  • an object of this invention is to provide the organic light emitting element using the said compound.
  • the present invention provides a compound represented by the following formula (1).
  • the compound represented by the following formula (1) is a benzofluoranthene derivative.
  • X is selected from the group consisting of NR 6 , S and O;
  • R 1 to R 6 are the same as or different from each other, and are each independently H, a C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group , C 3 ⁇ C 40 heterocycloalkyl group, C 6 ⁇ C 40 arylalkyl group, C 1 ⁇ C 40 alkyloxy group, C 5 ⁇ C 40 aryloxy group, C 5 ⁇ C 40 aryl group and C 5 to C 40 heteroaryl group;
  • A is selected from the group consisting of single bond, heteroarylene, C 5 ⁇ C 40 arylene group and a C 5 ⁇ C 40 of.
  • the present invention also provides an organic light emitting device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode.
  • At least one organic material layer of the one or more organic material layer provides an organic light emitting device characterized in that it comprises a compound represented by the formula (1).
  • the organic material layer including the compound represented by Formula 1 is preferably an electron transport layer.
  • the compound represented by Chemical Formula 1 according to the present invention Since the compound represented by Chemical Formula 1 according to the present invention has excellent electron transporting performance, the compound represented by Chemical Formula 1 exhibits superior performance in terms of voltage and efficiency than when Alq3 is used as the electron transporting layer material of the organic light emitting device. Therefore, the compound represented by Chemical Formula 1 according to the present invention can greatly contribute to improving EL performance and lifespan of an organic EL device. In particular, the improvement of electron transport performance has a great effect on maximizing performance in a full color organic EL panel.
  • FIG. 1 is a cross-sectional view showing an example of an organic light emitting device structure according to the present invention
  • Example 2 is a TGA graph of Inv-14 prepared in Example 2;
  • the compound represented by Chemical Formula 1 according to the present invention has benzofluoranthene as a core, and is a benzimidazole group, a benzothiazole group, and a benzoxazole as a substituent having an electron transfer ability. It is a benzofluoranthene derivative characterized by including one or more substituents selected from (benzoxazole) groups.
  • the compound represented by Chemical Formula 1 has a structure in which benzofluoranthene is the core, and a benzimidazole group, a benzothiazole group, or a benzoxazole group is substituted at the third carbon position of the benzofluoranthene. It is characteristic to have.
  • the benzofluoranthene moiety (C) is an alkyl group of C 1 ⁇ C 40 , C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C in addition to a hydrogen atom 40 alkynyl group, C 3 to C 40 cycloalkyl group, C 3 to C 40 heterocycloalkyl group, C 6 to C 40 arylalkyl group, C 1 to C 40 alkyloxy group, C 5 to C 40 aryl At least one substituent selected from the group consisting of an oxy group, a C 5 to C 40 aryl group and a C 5 to C 40 heteroaryl group may be introduced.
  • the benzimidazole group, benzothiazole group and benzoxazole group are each independently C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 6 ⁇ C 40 aryl group, C 1 ⁇ alkyloxy group of C 40 of the, C 5 ⁇ C 40
  • One or more substituents selected from the group consisting of an aryloxy group, C 5 ⁇ C 40 aryl group and C 5 ⁇ C 40 heteroaryl group may be substituted.
  • A is selected from the group consisting of single bond, heteroarylene, C 5 ⁇ C 40 arylene group and a C 5 ⁇ C 40 of.
  • Examples of the C 5 to C 40 arylene group and the C 5 to C 40 heteroarylene group of A are as follows, but are not limited thereto.
  • the compound represented by Formula 1 according to the present invention is the same as those of Table 1 below, but the compounds according to the present invention are not limited to those illustrated below.
  • the method for preparing the compound represented by Chemical Formula 1 according to the present invention is not particularly limited, and reactions known in the art may be appropriately applied.
  • the present invention provides an organic light emitting device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer
  • the organic material layer provides an organic light emitting device comprising the compound represented by Chemical Formula 1.
  • the compound represented by Formula 1 may be used one kind or two or more kinds.
  • the compound represented by Chemical Formula 1 may be included as a material for an electron transport layer, in which case the luminous efficiency, stability and device life of the organic light emitting device can be improved. Therefore, the organic material layer including the compound represented by Formula 1 is preferably an electron transport layer.
  • an organic material layer other than the organic material layer including the compound represented by Formula 1 of the present invention may be a hole injection layer, a hole transport layer, a light emitting layer, and / or an electron transport layer.
  • the electron transport layer includes a compound represented by Chemical Formula 1.
  • the electron injection layer may be positioned on the electron transport layer 106.
  • the organic light emitting device of the present invention may not only have a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at an interface between the electrode and the organic material layer.
  • the organic material layer including the compound represented by Chemical Formula 1 may be formed by a vacuum deposition method or a solution coating method, but is not limited thereto.
  • the organic light emitting device of the present invention uses an organic material layer and an electrode using materials and methods known in the art, except that one or more organic material layers of the organic material layer are formed to include the compound represented by Chemical Formula 1 of the present invention. By forming.
  • the substrate 101 may be a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet.
  • the anode 102 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 metals and oxides 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 metals and oxides such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (
  • Cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and 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 103, the hole transport layer 104 and the light emitting layer 105 is not particularly limited, conventional materials known in the art may be used.
  • the glass substrate coated with ITO Indium tin oxide having a thickness of 1500 ⁇ was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol and the like was dried and transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum depositor.
  • ITO Indium tin oxide
  • DS-205 Doosan Corp. was vacuum-deposited to a thickness of 600 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • NPB which is a material for transporting holes, was deposited thereon to form a hole transport layer, and then DS-H45 (Doosan) and DS-405 (Doosan), which acted as light emitting layers, were deposited at 300 ⁇ .
  • Example 3 Compound Inv-1 prepared in Example 1 (Example 3), Compound Inv-14 prepared in Example 2 (Example 4), or Comparative material Alq3 ( Comparative Example 1) was deposited to a thickness of 250 mm 3.
  • LiF an electron injection material
  • aluminum cathode
  • the organic light emitting diode structures of Examples 3 and 4 are listed in Table 2, and the organic light emitting diode structures of Comparative Example 1 are described in Table 3.
  • the properties of the organic light emitting device of Example 3 are described in Table 4
  • the properties of the organic light emitting device of Example 4 are described in Table 5
  • the properties of the organic light emitting device of Comparative Example 1 are described in Table 6 below. It was.
  • organic light emitting diodes (Examples 3 and 4) using the compound according to the present invention exhibited superior performance in terms of voltage and efficiency than organic light emitting diodes (Comparative Example 1) using Alq3. I could confirm it.
  • FIG. 2 is a TGA graph of Inv-14, an electron transporting compound prepared in Example 2
  • FIG. 3 is a TGA graph of Alq3, a known electron transporting material.
  • the Td value of Inv-14 of the present invention is about 80 ° C. higher than that of Alq3, and accordingly, the compound of the present invention can be used to improve the thermal characteristics of the device.
  • the compounds according to the present invention may not only improve the EL performance of the organic EL device, but also greatly contribute to the improvement of the lifetime.
  • the improvement of the electron transport performance is expected to have a great effect in maximizing the performance in the full color organic EL panel.

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

Abstract

L’invention concerne un dérivé de benzofluoranthène et un élément électroluminescent organique à base de ce dérivé. L’invention concerne plus particulièrement un dérivé de benzofluoranthène contenant au moins un groupe substituant sélectionné parmi un groupe benzimidazole, un groupe benzothiazole et un groupe benzoxazole qui sont des groupes substituants ayant une capacité de transfert d’électrons. L’invention concerne également un élément luminescent organique comprenant une couche organique contenant ce dérivé de benzofluoranthène.
PCT/KR2009/002968 2008-06-04 2009-06-04 Derive de benzofluoranthene et element luminescent organique a base de ce derive WO2009148269A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2008-0052678 2008-06-04
KR1020080052678A KR101011857B1 (ko) 2008-06-04 2008-06-04 벤조플루오란센 유도체 및 이를 이용한 유기 발광 소자

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WO2009148269A2 WO2009148269A2 (fr) 2009-12-10
WO2009148269A3 WO2009148269A3 (fr) 2010-03-04
WO2009148269A9 true WO2009148269A9 (fr) 2010-04-22

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JP2014177440A (ja) * 2013-03-15 2014-09-25 Idemitsu Kosan Co Ltd フルオランテン化合物、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、および電子機器
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US20240247017A1 (en) 2022-12-14 2024-07-25 Universal Display Corporation Organic electroluminescent materials and devices

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TWI314947B (en) * 2002-04-24 2009-09-21 Eastman Kodak Compan Organic light emitting diode devices with improved operational stability
KR101528241B1 (ko) * 2007-12-07 2015-06-15 삼성디스플레이 주식회사 방향족 복소환 화합물, 이를 포함한 유기막을 구비한 유기발광 소자 및 상기 유기발광 소자의 제조 방법

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KR20090126539A (ko) 2009-12-09
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WO2009148269A3 (fr) 2010-03-04

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