WO2010126233A1 - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDF

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WO2010126233A1
WO2010126233A1 PCT/KR2010/002167 KR2010002167W WO2010126233A1 WO 2010126233 A1 WO2010126233 A1 WO 2010126233A1 KR 2010002167 W KR2010002167 W KR 2010002167W WO 2010126233 A1 WO2010126233 A1 WO 2010126233A1
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substituent
organic electroluminescent
alkyl
aryl
independently
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PCT/KR2010/002167
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English (en)
French (fr)
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Hyo Jung Lee
Young Jun Cho
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
Seung Soo Yoon
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Dow Advanced Display Materials,Ltd.
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Priority to JP2012508382A priority Critical patent/JP2012525378A/ja
Priority to CN2010800287232A priority patent/CN102574871A/zh
Publication of WO2010126233A1 publication Critical patent/WO2010126233A1/en

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
    • 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
    • H10K85/631—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
    • 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
    • H10K85/658—Organoboranes
    • 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
    • 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
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene

Definitions

  • the present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices including the same.
  • the organic electroluminescent compounds according to the present invention are represented by Chemical Formula 1 :
  • electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices.
  • Eastman Kodak first developed an organic EL device using low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [Appl. Phys. Lett. 51, 913, 1987].
  • an organic EL device when a charge is applied to an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole are paired to form an exciton. As the exciton is deactivated, light is emitted by phosphorescence or fluorescence.
  • the organic EL device is advantageous in that it can be formed on a flexible transparent substrate such as plastic, is operable with relatively low voltage (10 V or lower) as compared to plasma display panels or inorganic EL displays, consumes less power and provides excellent color. Since the organic EL device may exhibit green, blue and red colors, it is drawing a lot of attentions as a full-color display device of the next generation.
  • the electroluminescent material In an organic EL device, the most important factor that determines its performance including luminescence efficiency and operation life is the electroluminescent material. Some requirements of the electroluminescent material include high electroluminescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
  • the organic EL device commonly has a configuration of anode/ HIL/HTL/EML/ETL/EIL/cathode.
  • Organic electroluminescent devices emitting blue, green or red light may be created depending on how to form the electroluminescent layer (EML).
  • the electroluminescent materials may be divided into host materials and dopant materials.
  • an electroluminescent layer prepared by doping a dopant in a host is known to provide superior EL property. Recently, development of an organic EL device having high efficiency and long operation life is becoming an imminent task.
  • the existing materials comprise a single layer, rather than a host-dopant layer, and are inappropriate for commercialization in aspects of color purity and efficiency. Also, they do not ensure reliable long operation life. Disclosure of Invention Technical Problem
  • an object of the present invention is to provide an organic electroluminescent compound having luminescence efficiency and device operation life improved over existing materials and having superior backbone with appropriate color coordinates.
  • Another object of the present invention is to provide an organic electronic device with high efficiency and long operation life, employing the organic electroluminescent compound as an electroluminescent material.
  • the present invention provides an organic electroluminescent compound represented by Chemical Formula 1 and an organic electronic device including the same. Since the organic electroluminescent compound according to the present invention has superior luminescence efficiency and excellent color purity and life property, it may be used to manufacture an OLED device having very superior operation life.
  • a ⁇ i and Ar 2 are independently -Li-L 2 -;
  • Li and L 2 are independently a chemical bond, (C6-C30)arylene with or without sub- stituent(s), (C3-C30)heteroarylene with or without substituent(s), 5- to 7-membered heterocycloalkylene with or without substituent(s), 5- to 7-membered heterocy- cloalkylene fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkylene with or without substituent(s), (C3-C30)cycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), adamantylene with or without substituent(s), (C7-C30)bicycloalkylene with or without substituent(s), (C2-C30)alkenylene with or without substituent(s), (C2-C30)alkynylene with or without substituent(s), (C6-C30)ar(Cl-C30)alkylene
  • Ri, R 2 and Ar 3 to Ar 6 are independentlyhydrogen, deuterium, halogen, (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C6-C30)aryl with or without substituent(s) fused with one or more (C3-C30)cycloalkyl(s) with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without sub- stituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s),(C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s),(C3-C30)cycloalkyl with or without substituent(s
  • R 21 to R 23 and R 31 to R 38 are the same as defined in R 1 , R 2 and Ar 3 to Ar 6 ;
  • m is an integer 1 or 2.
  • R 23 and R 3 i through R 38 are independently (Cl-C30)alkyl with or without substituent(s), (Cl-C30)aryl with or without substituent(s) or (Cl-C30)heteroaryl with or without substituent(s)aryl, or each of R 3! through R 38 may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an aliphatic ring or a monocyclic or polycyclic aromatic ring.
  • alkyl In the present invention, “alkyl”, “alkoxy” and other substituents containing “alkyl” moiety include both linear and branched species.
  • aryl means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring, including a plurality of aryls linked by single bond(s).
  • the naphthyl includes 1 -naphthyl and 2-naphthyl
  • the anthryl includes 1 -anthryl, 2-anthryl and 9-anthryl
  • the fluorenyl includes 1 -fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
  • monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isoben- zofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, ben- zoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quino
  • the alkyl moiety of " (C 1 -C30)alkyl, tri(C 1 -C30)alkylsilyl, di(Cl-C30)alkyl(C6-C30)arylsilyl, (C6-C30)ar(Cl-C30)alkyl, (Cl-C30)alkyloxy or (Cl-C30)alkylthio" may have 1 to 30 carbon atoms, specifically 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms.
  • the aryl alkyl moiety of "(C6-C30)aryl, di(Cl-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(Cl-C30)alkyl, (C6-C30)aryloxy or (C6-C30)arylthio” may have 6 to 30 carbon atoms, specifically 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms.
  • the "(C3-C30)heteroaryl” may have 3 to 30 carbon atoms, specifically 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms.
  • the "(C3-C30)cycloalkyl” may have 3 to 30 carbon atoms, specifically 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms.
  • the "(C2-C30)alkenyl or alkynyl” may have 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
  • the phrase "with or without substituent(s)" means that the substituents of L 1 , L 2 , Ri, R 2 and Ar 3 through Ar 6 may be independently substituted with one or more substituent(s) selected from a group consisting of deuterium, halogen, (Cl-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituent(s), 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic ring(s), tri(Cl-C30)alkylsilyl, di(Cl-C30)alkyl(C6-C30)arylsilyl, tri(C
  • Ar 1 and Ar 2 are independently (C6-C30)arylene with or without sub- stituent(s), (C3-C30)heteroarylene with or without substituent(s), or -L 1 -L 2 -;
  • L 1 and L 2 are independently (C6-C30)arylene with or without substituent(s) or (C3-C30)heteroarylene with or without substituent(s);
  • R 1 and R 2 are independently hydrogen, deuterium, (Cl-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s) or (C3-C30)cycloalkyl with or without substituent(s);
  • Ar 3 to Ar 6 are independently (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s), or Ar 3 to Ar 6 are independently
  • Ar 1 and Ar 2 may be independently selected from arylene such as phenylene, naphthylene, anthracenylene, biphenylene, fluorenylene, triphenylene, fluoran- thenylene, chrysenylene, terphenylene, phenanthrylene, pyrenylene, perylenylene, in- denofluorene, etc., heteroarylarylene such as pyridinylene, pyrazinylene, furylene, thienylene, selenophenylene, dibenzothienylene, dibenzofurylene, quinolinylene, quinoxalinylene, phenanthrolinylene, etc., or -L 1 -L 2 -, but are not limited thereto. They may be further substituted as in Chemical Formula 1.
  • arylene such as phenylene, naphthylene, anthracenylene, biphenylene, fluorenylene, triphenylene, fluor
  • L 1 and L 2 may be independently selected from arylene such as phenylene, naphthylene, anthracenylene, biphenylene, fluorenylene, triphenylene, fluoran- thenylene, chrysenylene, terphenylene, phenanthrylene, pyrenylene, perylenylene, in- denofluorene, etc., or heteroarylarylene such as pyridinylene, pyrazinylene, furylene, thienylene, selenophenylene, dibenzothienylene, dibenzofurylene, quinolinylene, quinoxalinylene, phenanthrolinylene, etc., but are not limited thereto. They may be further substituted as in Chemical Formula 1.
  • arylene such as phenylene, naphthylene, anthracenylene, biphenylene, fluorenylene, triphenylene, fluoran- thenylene, chrysen
  • R 1 and R 2 may be independently selected from hydrogen, deuterium, halogen, alkyl such as methyl, ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, etc., aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl, etc., heteroarylaryl such as dibenzothienyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, etc.
  • Ar 3 through Ar 6 may be independently selected from aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluo- ranthenyl, chrysenyl, triphenylenyl, etc., or heteroarylaryl such as dibenzothienyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, but are not limited thereto.
  • aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl,
  • Ar 5 and Ar 6 are linked via alkylene with or without aromatic ring(s) with or without substituent(s) to form a ring, may be selected from the following structures, but is not limited thereto:.
  • R 51 through R 55 are independently hydrogen, (Cl-C30)alkyl or (C6-C30)aryl, or R 51 and R 52 may be linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form a fused ring.
  • organic electroluminescent compound according to the present invention may be exemplified by the following compounds, but the following compounds do not limit the present invention:
  • organic electroluminescent compound according to the present invention may be prepared according to Scheme 1 :
  • the present invention provides an organic electroluminescent device including a first electrode; a second electrode; and at least one organic layer(s) interposed between the first electrode and the second electrode.
  • the organic layer includes one or more of the organic electroluminescent compound(s) represented by Chemical Formula 1.
  • the organic electroluminescent compound is used as a dopant material in an electroluminescent layer.
  • the organic layer may include an electroluminescent layer which further includes one or more host(s) in addition to one or more of the organic electroluminescent compound(s) represented by Chemical Formula 1.
  • the host used in the organic electronic device of the present invention is not particularly limited.
  • the host used in the organic electronic device of the present invention is selected from the compounds represented by Chemical Formulas 2 and 3:
  • Y is (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);
  • Z is anthracenylene with or without substituent(s);
  • a, b, c and d are independently an integer from 0 to 4.
  • the host compound represented by Chemical Formula 2 or 3 ay be exemplified by the following compounds, but is not limited thereto:
  • the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, at the same time.
  • the arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more metal or complex compound(s) selected from a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d- transition elements.
  • the organic layer may include an electroluminescent layer and a charge generating layer.
  • the organic layer may include, in addition to the organic electroluminescent compound, one or more organic electroluminescent layer(s) emitting blue, red and green light at the same time, to provide a white light-emitting organic electroluminescent device.
  • the compounds emitting blue, red or green light are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but are not limited thereto.
  • a layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. A driving stability may be attained therefrom.
  • the metal halide may be, for example, LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.
  • the metal oxide may be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant may be placed on the inner surface of one or both electrode(s) among the pair of electrodes.
  • oxidative dopant include various Lewis acids and acceptor compounds.
  • reductive dopant include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof.
  • a white light-emitting organic electroluminescent device having two or more electroluminescent layers may be prepared by using a reductive dopant layer as the charge generating layer.
  • the organic electroluminescent compound according to the present invention exhibits good luminescence efficiency and excellent life property, it may be used to manufacture an OLED device having very good operation life.
  • Example 1 Manufacture of OLED device using the organic electroluminescent compound according to the present invention
  • An OLED device was manufactured using the organic electroluminescent compound of the present invention.
  • a transparent electrode ITO film (15 ⁇ /D) prepared from a glass substrate for an OLED (Samsung Corning) was subjected to ultrasonic washing sequentially using trichloroethylene, acetone, ethanol and distilled water, and stored in isopropanol for later use.
  • the ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus.
  • 2-TNATA 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine
  • 2-TNATA was evaporated by applying electrical current to the cell to form a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • NPB ⁇ f,./V-bis( ⁇ -naphthyl)-/V,./V '- diphenyl-4,4'-diamine
  • An electroluminescent layer was formed on the hole transport layer as follows. Di- naphthylanthracene (DNA) was added in a cell of a vacuum deposition apparatus as a host, and Compound 1 according to the present invention was added in another cell as a dopant. The two cells were heated together such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on DNA.
  • DNA Di- naphthylanthracene
  • Compound 1 according to the present invention was added in another cell as a dopant. The two cells were heated together such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on DNA.
  • Each electroluminescent material used in the OLED device had been purified by vacuum sublimation at 10 ⁇ 6 torr.
  • a hole injection layer and a hole transport layer were formed in the same manner as Example 1. Then, after adding DNA in a cell of a vacuum deposition apparatus as an electroluminescent host material and adding Compound A, a blue-emitting material,in another cell, the two materials were evaporated at a rate of 100: 1 such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer.
  • the organic electroluminescent compounds according to the present invention exhibit remarkably improved luminescence efficiency while maintaining comparable or better color purity as compared to Comparative Example 1.

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PCT/KR2010/002167 2009-04-28 2010-04-08 Novel organic electroluminescent compounds and organic electroluminescent device using the same WO2010126233A1 (en)

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JP2012508382A JP2012525378A (ja) 2009-04-28 2010-04-08 新規有機電界発光化合物およびこれを使用する有機電界発光素子
CN2010800287232A CN102574871A (zh) 2009-04-28 2010-04-08 新颖的有机电致发光化合物和使用该化合物的有机电致发光器件

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CN103086942A (zh) * 2011-11-03 2013-05-08 三星显示有限公司 杂环化合物和包含该杂环化合物的有机发光二极管
CN103102232A (zh) * 2011-11-10 2013-05-15 三星显示有限公司 苯乙烯基类化合物、包含其的组合物和有机发光二极管
WO2015049030A2 (de) * 2013-10-02 2015-04-09 Merck Patent Gmbh Borenthaltende verbindungen
US9178162B2 (en) 2012-07-11 2015-11-03 Samsung Display Co., Ltd. Compound for organic light-emitting device and organic light-emitting device including the same

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