WO2011013959A2 - Nouveau composé à base de phénanthrène, et dispositif émetteur de lumière organique le comprenant - Google Patents

Nouveau composé à base de phénanthrène, et dispositif émetteur de lumière organique le comprenant Download PDF

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Publication number
WO2011013959A2
WO2011013959A2 PCT/KR2010/004878 KR2010004878W WO2011013959A2 WO 2011013959 A2 WO2011013959 A2 WO 2011013959A2 KR 2010004878 W KR2010004878 W KR 2010004878W WO 2011013959 A2 WO2011013959 A2 WO 2011013959A2
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Prior art keywords
compound
light emitting
layer
emitting device
organic light
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PCT/KR2010/004878
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English (en)
Korean (ko)
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WO2011013959A3 (fr
Inventor
배호기
안현철
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주식회사 동진쎄미켐
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Priority claimed from KR1020100071718A external-priority patent/KR101786498B1/ko
Publication of WO2011013959A2 publication Critical patent/WO2011013959A2/fr
Publication of WO2011013959A3 publication Critical patent/WO2011013959A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/27—Polycyclic condensed hydrocarbons containing three rings
    • C07C15/30—Phenanthrenes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • 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
    • 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]
    • H10K50/11—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
    • H10K85/615—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24—Anthracenes; Hydrogenated anthracenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
    • 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

Definitions

  • the present invention relates to a novel phenanthrene-based compound having excellent blue light emission characteristics and an organic light emitting device including the same in the light emitting layer.
  • an organic light emitting device capable of low voltage driving with a self-luminous type has a superior viewing angle, contrast ratio, and the like, and is lighter and thinner than a liquid crystal display (LCD), which is the mainstream of flat panel display devices.
  • LCD liquid crystal display
  • the organic light emitting device has a structure including a cathode (electron injection electrode) and an anode (hole injection electrode), and an organic layer between the two electrodes.
  • the organic layer may include a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection layer (EIL) in addition to the light emitting layer (EML).
  • an electron injection layer and may further include an electron blocking layer (EBL) or a hole blocking layer (HBL) due to the light emission characteristics of the light emitting layer.
  • a light emitting dye may be doped into the light emitting layer (host).
  • the present invention provides a compound represented by any one of the following Chemical Formulas 1 to 3:
  • Ar 1 is anthryl substituted with Ar 2 ,
  • Ar 3 is C 6-30 aryl, optionally substituted with Ar 4 ,
  • Ar 2 and Ar 4 is a C 6-30 aryl are each independently optionally substituted with one or more C 1-4 alkyl or C 6-30 aryl or substituted.
  • the present invention provides an organic light emitting device comprising a compound represented by any one of Formulas 1 to 3 or a mixture of two or more in the light emitting layer as a light emitting material.
  • the compound of the present invention Since the compound of the present invention has excellent blue light emission characteristics and excellent hole transport characteristics and electron transport characteristics compared to the existing materials, the compound of the present invention is used as a light emitting material of an organic light emitting device, thereby significantly improving driving voltage, luminous efficiency and lifetime characteristics of the organic light emitting device. You can.
  • the compound of the present invention represented by any one of Formulas 1 to 3 is characterized in that it has a specific substituent at positions 1, 6, 1, 8 or 1,9 of phenanthrene.
  • Ar 3 is Ar 4 is phenyl, naphthyl, phenanthryl or anthryl optionally substituted by, Ar 2 and Ar 4 are each independently a phenyl, methylphenyl, dimethylphenyl, Trimethylphenyl, butylphenyl, naphthyl, phenanthryl, phenylphenanthryl or naphthylphenanthryl.
  • the compound of any one of Formulas 1 to 3 according to the present invention may be prepared based on the well-known Suzuki-coupling reaction of the aromatic boron compound and the aromatic halogen compound in the carbon-carbon coupling reaction.
  • each of the compounds of Formulas 1, 2, 3, 2a, and 3a of the present invention can be prepared as shown in Schemes 1-5 below.
  • Ar 2 and Ar 3 are as defined above.
  • the present invention provides an organic light emitting device comprising a compound represented by any one of Formulas 1 to 3 or a mixture of two or more in the light emitting layer as a light emitting material.
  • the organic light emitting device of the present invention includes one or more organic thin film layers including a compound represented by any one of Formulas 1 to 3 or a mixture of two or more, and the method of manufacturing the organic light emitting device is as follows.
  • the organic light emitting device includes an organic thin film layer, such as a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (EML), an electron transport layer (ETL), an electron injection layer (EIL), between an anode and a cathode. It may include one or more.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML emission layer
  • ETL electron transport layer
  • EIL electron injection layer
  • an anode is formed by depositing a material for an anode electrode having a high work function on the substrate.
  • the substrate may be a substrate used in a conventional organic light emitting device, in particular, it is preferable to use a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproof.
  • the anode electrode material transparent and excellent indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and the like may be used.
  • the anode electrode material may be deposited by a conventional anode forming method, and specifically, may be deposited by a deposition method or a sputtering method.
  • HIL hole injection layer
  • LB Langmuir-Blodgett
  • the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal characteristics of the desired hole injection layer, and generally, a deposition temperature of 50 to 500 ° C., It is preferable to select appropriately from a vacuum degree of 10 -8 to 10 -3 torr, a deposition rate of 0.01 to 100 kPa / sec, and a layer thickness of 10 kPa to 5 mu m.
  • the hole injection layer material is not particularly limited, and TCTA (4,4 ′, 4 ′′ -tri (N-carbazolyl) tree, which is a phthalocyanine compound or starburst type amine derivative such as copper phthalocyanine disclosed in US Pat. No. 4,356,429.
  • a hole transport layer (HTL) material may be formed on the hole injection layer by a vacuum deposition method, a spin coating method, a cast method, an LB method, etc., but it is easy to obtain a uniform film quality and difficult to generate pin holes. It is preferable to form by the vacuum deposition method at the point.
  • the deposition conditions vary depending on the compound used, but in general, the hole transport layer is preferably selected in the same condition range as the formation of the hole injection layer.
  • the hole transport layer material is not particularly limited, and may be arbitrarily selected and used from conventionally known materials used in the hole transport layer.
  • the hole transport layer material is carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-ratio Ordinary amines having aromatic condensed rings such as phenyl] -4,4'-diamine (TPD), N.N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine ( ⁇ -NPD) Derivatives and the like can be used.
  • carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-ratio Ordinary amines having aromatic condensed rings such as phenyl] -4
  • the light emitting layer (EML) material may be formed on the hole transport layer by a method such as vacuum deposition, spin coating, casting, LB, etc., but it is easy to obtain a uniform film quality and hard to generate pin holes. It is preferable to form by the vacuum deposition method. In the case of forming the light emitting layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but in general, it is preferable to select within the same condition range as the formation of the hole injection layer. In addition, the light emitting layer material may be used alone or as a host, a compound represented by any one of formulas 1 to 3 of the present invention or a mixture represented by two or more mixtures.
  • a light emitting layer may be formed using a phosphorescent or fluorescent dopant together.
  • the fluorescent dopant may be IDE102 or IDE105, or BD142 (N 6 , N 12 -bis (3,4-dimethylphenyl) -N 6 , N 12 -dimethyrylcrisne- which can be purchased from Idemitsu Co., Ltd.).
  • 6,12-diamine can be used, green phosphorescent dopant Ir (ppy) 3 (tris (2-phenylpyridine) iridium), blue phosphorescent dopant F2Irpic (iridium (III) bis [4,6] -Difluorophenyl) -pyridinato-N, C2 '] picolinate), red phosphorescent dopant RD61 from UDC, and the like can be co-vacuum-deposited (doped).
  • the doping concentration of the dopant is not particularly limited, but the dopant is preferably doped at 0.01 to 15 parts by weight based on 100 parts by weight of the host.
  • the content of the dopant is less than 0.01 parts by weight, there is a problem in that the color development is not performed properly because the amount of the dopant is not sufficient, and if it exceeds 15 parts by weight, the efficiency is drastically reduced due to the concentration quenching phenomenon.
  • the hole blocking material (HBL) is further laminated by vacuum deposition or spin coating.
  • the hole-suppressing material that can be used at this time is not particularly limited, but any one of the well-known ones used as the hole-inhibiting material can be selected and used.
  • an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or the hole-inhibiting material described in Japanese Patent Laid-Open No. 11-329734 (A1) can be cited.
  • Oxy-2-methylquinolinolato) -aluminum biphenoxide) a phenanthrolines-based compound (e.g., BCP (vasocuproin) from UDC) can be used.
  • An electron transport layer is formed on the light emitting layer formed as described above, wherein the electron transport layer is formed by a vacuum deposition method, a spin coating method, a casting method, or the like, and is preferably formed by a vacuum deposition method.
  • the electron transport layer material functions to stably transport electrons injected from an electron injection electrode, and the type thereof is not particularly limited.
  • quinoline derivatives especially tris (8-quinolinolato) aluminum (Alq 3 ), or ET4 (6,6 '-(3,4-dimethyl-1,1-dimethyl-1H-silol-2,5-diyl) di-2,2'-bipyridine)
  • EIL electron injection layer
  • the electron injection layer material may be LiF, NaCl, CsF, Li 2 O, BaO, or the like. The substance of can be used.
  • the deposition conditions of the electron transport layer are different depending on the compound used, it is generally preferable to select within the same condition range as the formation of the hole injection layer.
  • an electron injection layer (EIL) material may be formed on the electron transport layer, wherein the electron transport layer is formed of a conventional electron injection layer material by a vacuum deposition method, a spin coating method, a casting method, and the like. It is preferable to form by the vacuum deposition method.
  • EIL electron injection layer
  • the cathode forming metal is formed on the electron injection layer by a method such as vacuum deposition or sputtering and used as a cathode.
  • the cathode forming metal may be a metal having low work function, an alloy, an electrically conductive compound, and a mixture thereof. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. There is this.
  • a transmissive cathode using ITO and IZO may be used to obtain a top emitting element.
  • the organic light emitting device of the present invention has an organic structure of an anode, a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), an electron injection layer (EIL), a cathode (cathode) structure
  • HIL hole injection layer
  • HTL hole transport layer
  • EML electron transport layer
  • EIL electron injection layer
  • cathode cathode
  • each organic thin film layer formed according to the present invention as described above can be adjusted according to the required degree, preferably 10 to 1,000 nm, more preferably 20 to 150 nm.
  • the present invention has an advantage that the organic thin film layer including the compound represented by any one of Formulas 1 to 3 or a mixture of two or more thereof has a uniform surface and excellent shape stability because the thickness of the organic thin film layer can be adjusted in molecular units.
  • the light emitting material of the present invention is excellent in electrical stability, has a high luminous efficiency and luminous luminance and can be implemented long life, it can be usefully used as a light emitting material of the organic light emitting device.
  • reaction product was recrystallized from toluene and n-hexane to obtain 5.3 g (49%) of 10- (naphthalen-2-yl) anthracene-9-yl boronic acid as a white crystal.
  • Triphenylphosphine 3.14 g (12 mmol) was mixed with 3.0 g (12 mmol) of 2-bromobenzyl bromide to obtain 5.8 g of phosphonium salt, followed by Wittig reaction with 2.09 (11.3 mmol) of 2-bromobenzaldehyde.
  • the obtained product was then recrystallized from ethanol to obtain 3.74 g (98%) of (E) -2,2'-dibromotytilbene.
  • Example 1 to 6 was repeated using 1-bromobenzene instead of 2-bromonaphthalene in Example 1 to obtain compound (2) having the following structure.
  • Example 1 to 6 was repeated using 1-bromo-4-methylbenzene instead of 2-bromonaphthalene in Example 1 to obtain compound (3) having the following structure.
  • Example 1-6 was repeated using 4-bromo-1,2-dimethylbenzene instead of 2-bromonaphthalene in Example 1 to obtain compound (4) having the following structure.
  • Example 1-6 was repeated using 4-bromo-1,2-dimethylbenzene instead of 2-bromonaphthalene in Example 1 to obtain compound (5) having the following structure.
  • Example 1-6 was repeated using 1-bromonaphthalene instead of 2-bromonaphthalene in Example 1 to obtain compound (6) having the following structure.
  • Example 1 the method of Example 12 was repeated using 1-bromobenzene instead of 2-bromonaphthalene to obtain Compound (8) having the following structure.
  • Example 1 the method of Example 12 was repeated using 1-bromo-4-methylbenzene instead of 2-bromonaphthalene to obtain Compound (9) having the following structure.
  • Example 1 the method of Example 12 was repeated using 4-bromo-1,2-dimethylbenzene instead of 2-bromonaphthalene to obtain a compound (10) having the following structure.
  • Example 1 the method of Example 12 was repeated using 1-bromo-4-tert-butylbenzene instead of 2-bromonaphthalene to obtain Compound (11) having the following structure.
  • An organic light emitting diode was manufactured according to a conventional method using the compound (1) to compound (12) obtained in Examples 6 to 17 as a light emitting host material. First, a 650 ⁇ hole injection layer (hole injection layer material: HI-406 (N 1 , N 1 '-(biphenyl-4,4'-diyl) on a 1500 ⁇ thick ITO layer (anode) formed on a glass substrate.
  • hole injection layer material: HI-406 N 1 , N 1 '-(biphenyl-4,4'-diyl
  • the luminous efficiency of the prepared organic light emitting device was measured and shown in Table 1 below.
  • the compound of the present invention is excellent in electrical stability, has a high luminous efficiency and luminous luminance and can be implemented long life, it is used as a light emitting material of the organic light emitting device to improve the luminous efficiency and life of the organic light emitting device Can be significantly improved.
  • the compound of the present invention Since the compound of the present invention has excellent blue light emission characteristics and excellent hole transport characteristics and electron transport characteristics compared to the existing materials, the compound of the present invention is used as a light emitting material of an organic light emitting device, thereby significantly improving driving voltage, luminous efficiency and lifetime characteristics of the organic light emitting device. You can.

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

Abstract

La présente invention concerne un composé à base de phénanthrène, ainsi qu'un dispositif émetteur de lumière organique le comprenant. Plus particulièrement, le composé de la présente invention présente des caractéristiques d'émission de couleur bleue supérieures, des caractéristiques de transport de trous et des caractéristiques de transport d'électrons, et peut être ainsi utilisé comme matériau émetteur de lumière pour un dispositif émetteur de lumière organique afin de produire un dispositif émetteur de lumière organique présentant des caractéristiques de commande de faible tension, une haute luminance et une longue durée de vie.
PCT/KR2010/004878 2009-07-28 2010-07-26 Nouveau composé à base de phénanthrène, et dispositif émetteur de lumière organique le comprenant WO2011013959A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20090068734 2009-07-28
KR10-2009-0068734 2009-07-28
KR10-2010-0071718 2010-07-26
KR1020100071718A KR101786498B1 (ko) 2009-07-28 2010-07-26 신규한 페난트렌계 화합물 및 이를 포함하는 유기발광소자

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WO2011013959A2 true WO2011013959A2 (fr) 2011-02-03
WO2011013959A3 WO2011013959A3 (fr) 2011-07-21

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015509954A (ja) * 2012-07-13 2015-04-02 エルジー・ケム・リミテッド ヘテロ環化合物およびこれを含む有機電子素子
CN107641070A (zh) * 2017-06-19 2018-01-30 赛洛普（武汉）科技有限公司 一种9,10‑不对称二取代蒽衍生物的制备方法
CN110041159A (zh) * 2019-04-24 2019-07-23 北京诚志永华显示科技有限公司 新型化合物、有机电致发光材料、有机电致发光元件、电子装置
WO2022017998A1 (fr) * 2020-07-22 2022-01-27 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques

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US20080079356A1 (en) * 2006-09-29 2008-04-03 Sang-Hoon Park Organoelectroluminescent compound and organoelectroluminescent device employing the same
WO2008094399A1 (fr) * 2007-01-30 2008-08-07 Eastman Kodak Company Diodes électroluminescentes organiques (oled) à efficacité élevée et excellente durée de vie
US20080303003A1 (en) * 2005-12-08 2008-12-11 Merck Patent Gmbh Novel Materials for Organic Electroluminescent Devices
US20090026919A1 (en) * 2004-10-11 2009-01-29 Merck Paten Gmbh Patents & Scientific Information Phenanthrene derivative

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Publication number Priority date Publication date Assignee Title
US20090026919A1 (en) * 2004-10-11 2009-01-29 Merck Paten Gmbh Patents & Scientific Information Phenanthrene derivative
US20080303003A1 (en) * 2005-12-08 2008-12-11 Merck Patent Gmbh Novel Materials for Organic Electroluminescent Devices
US20080079356A1 (en) * 2006-09-29 2008-04-03 Sang-Hoon Park Organoelectroluminescent compound and organoelectroluminescent device employing the same
WO2008094399A1 (fr) * 2007-01-30 2008-08-07 Eastman Kodak Company Diodes électroluminescentes organiques (oled) à efficacité élevée et excellente durée de vie

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015509954A (ja) * 2012-07-13 2015-04-02 エルジー・ケム・リミテッド ヘテロ環化合物およびこれを含む有機電子素子
US9391281B2 (en) 2012-07-13 2016-07-12 Lg Chem, Ltd. Heterocyclic compound and organic electronic element containing same
US9412954B2 (en) 2012-07-13 2016-08-09 Lg Chem, Ltd. Heterocyclic compound and organic electronic element containing same
US9882146B2 (en) 2012-07-13 2018-01-30 Lg Chem, Ltd. Heterocyclic compound and organic electronic element containing same
CN107641070A (zh) * 2017-06-19 2018-01-30 赛洛普（武汉）科技有限公司 一种9,10‑不对称二取代蒽衍生物的制备方法
CN110041159A (zh) * 2019-04-24 2019-07-23 北京诚志永华显示科技有限公司 新型化合物、有机电致发光材料、有机电致发光元件、电子装置
WO2022017998A1 (fr) * 2020-07-22 2022-01-27 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques

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