WO2013055132A2 - Compound for organic electrical device, organic electrical device using same, and electronic device thereof - Google Patents

Compound for organic electrical device, organic electrical device using same, and electronic device thereof Download PDF

Info

Publication number
WO2013055132A2
WO2013055132A2 PCT/KR2012/008278 KR2012008278W WO2013055132A2 WO 2013055132 A2 WO2013055132 A2 WO 2013055132A2 KR 2012008278 W KR2012008278 W KR 2012008278W WO 2013055132 A2 WO2013055132 A2 WO 2013055132A2
Authority
WO
WIPO (PCT)
Prior art keywords
group
formula
organic
aryl
compound
Prior art date
Application number
PCT/KR2012/008278
Other languages
French (fr)
Korean (ko)
Other versions
WO2013055132A3 (en
Inventor
박정환
이선희
문성윤
김대성
정화순
김원삼
변지훈
이범성
최대혁
김동하
Original Assignee
덕산하이메탈(주)
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 덕산하이메탈(주) filed Critical 덕산하이메탈(주)
Publication of WO2013055132A2 publication Critical patent/WO2013055132A2/en
Publication of WO2013055132A3 publication Critical patent/WO2013055132A3/en

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/008—Triarylamine dyes containing no other chromophores
    • 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
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • 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
    • H10K85/649—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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K99/00—Subject matter not provided for in other groups of this subclass
    • 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
    • C09K2211/1092—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
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electrical device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions.
  • the light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be.
  • the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.
  • the deposition method is the mainstream in the formation of the OLED device, a situation that requires a material that can withstand a long time, that is, a material having a strong heat resistance characteristics.
  • a host / dopant system may be used. The principle is that when a small amount of dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • a material constituting the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material.
  • a stable and efficient organic material layer for an organic electric device has not been made sufficiently, and therefore, the development of new materials is still required.
  • An object of the present invention is to provide a compound capable of improving high luminous efficiency, low driving voltage, color purity, and lifetime of an element, an organic electric element using the same, and an electronic device thereof.
  • the present invention provides a compound represented by the following formula.
  • the present invention provides an organic electric device comprising the formula (1) and an electronic device using the same.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to an embodiment of the present invention.
  • halo or halogen includes fluorine, chlorine, bromine, and iodine unless otherwise noted.
  • alkyl or “alkyl group” has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.
  • alkenyl or “alkynyl” has a double bond or a triple bond having 2 to 60 carbon atoms, respectively, unless otherwise specified, but is not limited thereto.
  • cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
  • alkoxy group used in the present invention has a carbon number of 1 to 60 unless otherwise stated, it is not limited thereto.
  • aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
  • an aryl group or an arylene group means a monocyclic or heterocyclic aromatic, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction.
  • the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.
  • heteroalkyl means an alkyl including one or more heteroatoms unless otherwise indicated.
  • heteroaryl group or “heteroarylene group” means an aryl group or arylene group having 3 to 60 carbon atoms, each of which includes one or more heteroatoms, unless otherwise specified. In addition, it includes not only a single ring but also a heterocycle, and adjacent groups may be formed by bonding.
  • heterocycloalkyl and “heterocyclic group” include one or more heteroatoms, unless otherwise specified, have a carbon number from 2 to 60, and include heterocycles as well as monocycles. Adjacent groups may be formed in combination.
  • heterocyclic group may mean an alicyclic and / or aromatic including a heteroatom.
  • heteroatom refers to N, O, S, P, and Si unless otherwise indicated.
  • aliphatic as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms
  • aliphatic ring means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
  • saturated or unsaturated ring as used herein means a saturated or unsaturated aliphatic ring or an aromatic ring or heterocyclic ring having 6 to 60 carbon atoms.
  • heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
  • substituted in the term “substituted or unsubstituted” as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 1 ⁇ C 20 alkoxy groups, C 1 to C 20 alkylamine groups, C 1 to C 20 alkylthiophene groups, C 6 to C 20 arylthiophene groups, C 2 to C 20 alkenyl groups, C 2 to C 20 alkynyl group, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 60 aryl group, C 6 ⁇ C 20 aryl group substituted with deuterium, C 8 ⁇ C 20 aryl alkenyl group, silane group, boron Group, germanium group, and C 5 ⁇ C 20 It is meant to be substituted with one or more substituents selected from the group consisting of, but not limited to these substituents.
  • FIG. 1 is an exemplary view of an organic electric device according to an embodiment of the present invention.
  • the organic electric device 100 includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110.
  • An organic material layer containing a compound represented by the formula (1) between) is provided.
  • the first electrode 120 may be an anode (anode)
  • the second electrode 180 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. At this time, the remaining layers except for the light emitting layer 150 may not be formed.
  • the hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.
  • the organic electronic device according to the present invention may further include a protective layer formed on one surface of the first electrode and the second electrode opposite to the organic material layer.
  • the compound according to the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, the electron injection layer 170, the host of the light emitting layer 150 or the material of the dopant or capping layer Can be used as Preferably, the compound according to the present invention may be used as a host material of the light emitting layer 150 or a material for forming the hole transport layer 140.
  • the organic electroluminescent device can be manufactured using a PVD (physical vapor deposition) method.
  • the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon.
  • the organic material layer including the 160 and the electron injection layer 170 it can be prepared by depositing a material that can be used as the cathode 180 thereon.
  • the organic layer may be prepared by using a variety of polymer materials, but not by a deposition process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer. It can be prepared in a number of layers. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.
  • the organic electric element according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.
  • OLED organic electroluminescent device
  • OPC organic photoconductor
  • organic TFT organic transistor
  • Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
  • An organic electric device includes an anode, a cathode, and an organic material layer formed between the anode and the cathode.
  • the emission layer may be formed of a compound represented by the following Chemical Formula 1.
  • a ring is C 6 ⁇ C 60
  • R 1 to R 11 are each independently hydrogen, deuterium, halogen, nitrile group, nitro group, -LN (Ar 1 ) (Ar 2 ), C 6 ⁇ C 60 aryl group, fluorenyl group, C 2 ⁇ C 60 heterocyclic group, C 1 ⁇ C 30 Alkoxy group, C 6 ⁇ C 30 It may be selected from the group consisting of aryloxy group and C 1 ⁇ C 50 Alkyl group, X is S, SO or SO 2 to be.
  • L is a direct bond (that is, absent), C 6 ⁇ C 60 arylene group, fluorenylene group, C 6 ⁇ C 60 aromatic ring and C 3 ⁇ C 60 of aliphatic and may be selected from the group consisting of fused rings, C 2 ⁇ C 60 heterocyclic group or a divalent aliphatic hydrocarbon group,
  • Ar 1 and Ar 2 are each independently of the C 6 ⁇ C 60 aryl group, C 2 ⁇ C 60 heterocyclic group, fluorenyl group, C 1 ⁇ C 30 alkoxy group, C 6 ⁇ C 30 aryloxy group And it is selected from the group consisting of C 1 ⁇ C 50 Alkyl group.
  • Y, R 1 to R 11 , L, Ar 1, and Ar 2 may be further substituted with specific substituents.
  • Y, R 1 to R 11 , Ar 1 and Ar 2 is a C 6 ⁇ C 60 aryl group
  • Y, R 1 to R 11 , Ar 1 and Ar 2 is a fluorenyl group
  • these are deuterium, halogen, silane group, boron group, germanium group, C 1 ⁇ C 20 Alkylthio group, C 6 ⁇ C 20 arylthio group, C 1 -C 20 alkoxy group, -N (Ar 1 ) (Ar 2 ), C 1 -C 20 alkyl group, C7-C20 arylalkyl group, C 2 -C 20 alkenyl group , C 8 ⁇ C 20 aryl alkenyl group, C 2 ⁇ C 20 alkynyl group, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 20
  • the C 6 ⁇ C 60 heterocyclic group of the Y, R 1 to R 11 , L, Ar 1 and Ar 2 includes at least one hetero atom of O, N, S, Si and P, deuterium, halogen Group, -N (Ar 1 ) (Ar 2 ), C 1 -C 20 alkyl group, C 7 -C 20 arylalkyl group, C 2 -C 20 alkenyl group, C 8 -C 20 arylalkenyl group, C It may be substituted with one or more substituents selected from the group consisting of 1 to C 20 alkoxy group, C 6 ⁇ C 60 aryl group, C 6 ⁇ C 20 aryl group substituted with deuterium, a nitrile group and an acetylene group.
  • the C 1 to C 30 alkoxy group and the C 6 to C 30 aryloxy group of the Y, R 1 to R 11 , Ar 1 and Ar 2 may be deuterium, halogen, amino, nitrile, nitro or C 1.
  • the C 1 to C 50 alkyl group of Y, R 1 to R 11 , r 1, and Ar 2 may be C 2 to C 20 alkenyl group, C 1 to C 20 alkoxy group, C 6 to C 20 aryl A C 6 to C 20 aryl group, a C 7 to C 20 arylalkyl group, a C 8 to C 20 arylalkenyl group, a C 2 to C 20 heterocyclic group, a nitrile group and an acetylene group It may be substituted with one or more substituents selected from the group.
  • Formula 1 may be represented by one of the following formula.
  • R 1 ⁇ R 11 and X are as defined in formula (1).
  • Y may be selected from the group of monovalent substituents in the definition of Y in Formula 1
  • Y may be a direct bond or may be selected from the group of divalent substituents in the definition of Y in Formula 1.
  • L, Ar 1 and Ar 2 are the same as defined in Chemical Formula 1.
  • Formula 1 when A ring is a benzene ring, Formula 1 may be represented by one of the following Formulas 5 to 7.
  • R 1 to R 8 and X are the same as defined in Chemical Formula 1.
  • Y in Formula 5 may be selected from the group of monovalent substituents in the Y definition of Formula 1
  • Y in Formula 6 may be a direct bond, or may be selected from a divalent substituent group in the Y definition of Formula 1
  • Formula 7 L, Ar 1 and Ar 2 are as defined in formula (1).
  • Formula 1 may be one of the following compounds, but is not limited to these compounds, any compound satisfying Formula 1 will belong to the present invention.
  • Chemical Formula 1 may be synthesized by the following Chemical Formula 1.
  • Sub 1-6 may be synthesized by Scheme 2 below.
  • Sub 1-1 to Sub 1-6 of Scheme 2 may be synthesized by the following synthesis method, but is not limited thereto.
  • Sub 1-1 (36.0 g, 140 mmol) obtained in the above synthesis was dissolved in 980 mL of DMF, followed by bispinacolborate (39.1 g, 154 mmol), PdCl 2 (dppf) catalyst (3.43 g, 4.2 mmol), KOAc (41.3 g, 420 mmol) was added sequentially, followed by stirring for 24 hours to synthesize the borate compound.
  • the obtained compound was separated through a silica gel column and recrystallized, and then the borate compound was 29.81 g (70%) of Sub 1-2.
  • Sub 1-3 was dissolved in dichloromethane, 30% aqueous hydroxyperoxide solution and acetic acid were added, followed by stirring at 30 ° C. for 4 hours. After the reaction was completed, extracted with chloroform and water, the organic layer was dried, silicagel column and recrystallization to obtain Sub 1-4 76%.
  • Sub 1-5 was dissolved in 600 mL of methylene chloride, and then 0.05 equivalent of BPO (Benzoyl peroxide) and NBS (N-bromosuccinimide) (35.60 g, 200 mmol) were added slowly, followed by stirring at room temperature for 24 hours. After the reaction was completed, 300 mL of 5% HCl was added, followed by 300 mL of water to remove residual NBS, and extracted with ether and water. The organic layer was dried over MgSO 4 and concentrated. The resulting organic material was silicagel column and recrystallized to obtain Sub 1-6 78%.
  • BPO Benzoyl peroxide
  • NBS N-bromosuccinimide
  • Sub 2 in Scheme 1 may be one of the following compounds, but is not limited thereto.
  • the final compound of the present invention can be prepared by the following scheme 3.
  • Sub 3 may be one of the following compounds, but is not necessarily limited thereto.
  • Sub 1-7 compound (1 equivalent) was added to a round bottom flask, and the amine compound Sub 3 (1.1 equivalent), Pd (PPh 3 ) 4 (0.03 to 0.05 equivalent), NaOH (3 equivalent), THF (3 mL / 1 mmol), water (1.5 mL / 1 mmol) is added. Thereafter, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, distilled water is diluted at room temperature and extracted with methylene chloride and water. The organic layer was dried over MgSO 4 , concentrated, and the resulting compound was recrystallized from a silicagel column. FD-MS of the final compound thus synthesized is shown in Table 4 below.
  • each of the substituents of the compounds represented by the formula (1) has a broad relationship, exemplarily described the synthesis examples of the representative compounds, the compounds represented by the formula (1) not illustrated by way of example as a synthesis example Can be configured.
  • the compound which has the intrinsic property of the introduced substituent can be synthesize
  • substituents used in the hole injection layer material, the hole transport layer material, the light emitting layer material, and the electron transport layer material used in the manufacture of the organic electric device, including the organic light emitting device to satisfy the conditions required for each organic material layer Materials can be prepared.
  • the compound according to the present invention may be used in various applications in the organic electroluminescent device according to the type and nature of the substituent. That is, the compound of the present invention can be applied to various layers other than the host of the phosphorescent or fluorescent light emitting layer because it is free to be controlled by the core and the substituent.
  • a copper phthalocyanine (CuPc) film was vacuum deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 10 nm.
  • a hole injection layer having a thickness of 10 nm.
  • 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl was vacuum deposited to a thickness of 30 nm on the hole injection layer to form a hole transport layer.
  • a light emitting layer having a thickness of 30 nm was formed on the hole transport layer by doping at 95: 5 weight using a compound of the present invention as a host material and Ir (ppy) 3 [tris (2-phenylpyridine) -iridium] as a dopant material.
  • Ir (ppy) 3 tris (2-phenylpyridine) -iridium]
  • ((1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer
  • Tris (8-quinolinol) aluminum was deposited to a thickness of 40 nm on the hole blocking layer to form an electron injection layer.
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm
  • an organic light emitting diode was manufactured by forming an Al / LiF cathode.
  • An organic electroluminescent device was manufactured in the same manner as in Experiment 1, except that the compound represented by Comparative Compound 2 was used as a host material instead of the compound of the present invention when forming the emission layer.
  • a 4,4'4 "-tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine (hereinafter abbreviated as 2T-NATA) film was formed on an ITO layer (anode) formed on a glass substrate. Vacuum deposition was performed to form a 10 nm thick hole injection layer. Subsequently, the compound of the present invention was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 30 nm. In addition, a 45 nm-thick light emitting layer doped with BD-052X (Idemitus, Inc.) 7% was formed on the hole transport layer. 2-anthracene (AND))).
  • An organic light emitting display device was manufactured in the same manner as in Experiment 2, except that the compound represented by Comparative Compound 2 was used instead of the compound of the present invention when forming the hole injection layer.
  • the driving voltage of the organic light emitting device can be lowered, and color purity, luminous efficiency and lifespan can be remarkably improved. Can be. Even if the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer, it is obvious that the same effect can be obtained.

Landscapes

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

Abstract

The present invention provides a novel compound capable of improving lighting efficiency, stability, and lifetime of a device, and an organic electrical device using the same, and an electronic device thereof.

Description

유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치Compound for organic electric device, organic electric device using same and electronic device thereof
본 발명은 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치에 관한 것이다.The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛 에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기전기소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물 층은 유기전기소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 등으로 이루어질 수 있다. In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. The organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electrical device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
유기전기소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하 수송 재료, 예컨대 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. 그리고, 상기 발광 재료는 분자량에 따라 고분자형과 저분자형으로 분류될 수 있고, 발광 메커니즘에 따라 전자의 일중항 여기상태로부터 유래되는 형광 재료와 전자의 삼중항 여기상태로부터 유래되는 인광 재료로 분류될 수 있다. 또한, 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다.Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions. The light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be. In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.
특히, 유기전기소자의 우수한 수명 특성을 위해 정공 수송층 또는 완충층(buffer layer)으로 삽입되는 유기물질에 관해 여러 연구가 진행되고 있으며, 이를 위해 양극으로부터 유기층으로의 높은 정공 이동 특성을 부여하면서 증착 후 박막 형성시 균일도가 높고 결정화도가 낮은 정공 주입층 재료가 요구되고 있다.In particular, various studies have been conducted on organic materials inserted into a hole transporting layer or a buffer layer for excellent life characteristics of the organic electric device, and for this, a thin film after deposition while giving high hole transporting characteristics from the anode to the organic layer There is a need for a hole injection layer material having high uniformity and low crystallinity in forming.
유기전기소자의 수명단축의 원인 중 하나인 양극전극(ITO)으로부터 금속 산화물이 유기층으로 침투 확산되는 것을 지연시키며, 소자 구동시 발생되는 주울열(Joule heating)에 대해서도 안정된 특성, 즉 높은 유리 전이 온도를 갖는 정공 주입층 재료에 대한 개발이 필요하다. 또한 정공 수송층 재료의 낮은 유리전이 온도는 소자 구동시에 박막 표면의 균일도가 무너지는 특성에 따라 소자수명에 큰 영향을 미치는 것으로 보고되고 있다. 또한, OLED 소자의 형성에 있어서 증착방법이 주류를 이루고 있으며, 이러한 증착방법에 오랫동안 견딜 수 있는 재료 즉 내열성 특성이 강한 재료가 필요한 실정이다. Delays penetration of metal oxide into the organic layer from the anode electrode (ITO), which is one of the causes of the shortening of the life of the organic electric device, and stable properties for Joule heating generated when driving the device, that is, high glass transition temperature. There is a need for development of a hole injection layer material having In addition, the low glass transition temperature of the hole transport layer material has been reported to have a significant effect on the device life, depending on the characteristics of the uniformity of the surface of the thin film when driving the device. In addition, the deposition method is the mainstream in the formation of the OLED device, a situation that requires a material that can withstand a long time, that is, a material having a strong heat resistance characteristics.
한편, 발광 재료로서 하나의 물질만 사용하는 경우 분자간 상호 작용에 의하여 최대 발광 파장이 장파장으로 이동하고 색순도가 떨어지거나 발광 감쇄 효과로 소자의 효율이 감소되는 문제가 발생하므로, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여 발광 재료로서 호스트/도판트계를 사용할 수 있다. 그 원리는 발광층을 형성하는 호스트보다 에너지 대역 간극이 작은 도판트를 발광층에 소량 혼합하면, 발광층에서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이때 호스트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다. On the other hand, when only one material is used as the light emitting material, the maximum light emission wavelength is shifted to the long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the light emission attenuation effect. In order to increase the light emitting efficiency through the light emitting material, a host / dopant system may be used. The principle is that when a small amount of dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
전술한 유기전기소자가 갖는 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지 안정하고 효율적인 유기전기소자용 유기물층 재료의 개발이 충분히 이루어지지 않은 상태이며, 따라서 새로운 재료의 개발이 계속 요구되고 있다.In order to fully exhibit the excellent characteristics of the above-described organic electroluminescent device, a material constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. Although this should be preceded, the development of a stable and efficient organic material layer for an organic electric device has not been made sufficiently, and therefore, the development of new materials is still required.
본 발명은 소자의 높은 발광효율, 낮은 구동전압, 색순도, 및 수명을 향상시킬 수 있는 화합물 및 이를 이용한 유기전기소자, 그 전자 장치를 제공하는 것을 목적으로 한다.An object of the present invention is to provide a compound capable of improving high luminous efficiency, low driving voltage, color purity, and lifetime of an element, an organic electric element using the same, and an electronic device thereof.
본 발명의 일측면에 따르면, 본 발명은 하기 화학식으로 표시되는 화합물을 제공한다.According to one aspect of the present invention, the present invention provides a compound represented by the following formula.
Figure PCTKR2012008278-appb-I000001
Figure PCTKR2012008278-appb-I000001
본 발명의 다른 측면에 따르면, 본 발명은 상기 화학식 1을 포함하는 유기전기소자 및 이를 이용한 전자장치를 제공한다.According to another aspect of the invention, the present invention provides an organic electric device comprising the formula (1) and an electronic device using the same.
본 발명에 따르는 신규 화합물을 이용함으로써 소자의 높은 발광효율, 낮은 구동전압, 색순도, 및 수명을 크게 향상시킬 수 있는 효과를 나타낸다.By using the novel compound according to the present invention, it is possible to greatly improve the device's high luminous efficiency, low driving voltage, color purity, and lifetime.
도 1은 본 발명의 일실시예에 따른 유기전기발광소자의 예시도이다. 1 is an exemplary view of an organic electroluminescent device according to an embodiment of the present invention.
이하에서 본 발명의 일부 실시예들을 예시적인 도면을 통해 상세하게 설명한다.Hereinafter, some embodiments of the present invention will be described in detail through exemplary drawings.
각 도면의 구성요소들에 참조부호를 부가함에 있어서, 동일한 구성요소들에 대해서는 비록 다른 도면상에 표시되더라도 가능한 한 동일한 부호를 가지도록 하고 있음에 유의해야 한다. 또한, 본 발명을 설명함에 있어, 관련된 공지 구성 또는 기능에 대한 구체적인 설명이 본 발명의 요지를 흐릴 수 있다고 판단되는 경우에는 그 상세한 설명은 생략한다.In adding reference numerals to the components of each drawing, it should be noted that the same reference numerals are assigned to the same components as much as possible even though they are shown in different drawings. In addition, in describing the present invention, when it is determined that the detailed description of the related well-known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.
또한, 본 발명의 구성 요소를 설명하는 데 있어서, 제 1, 제 2, A, B, (a),(b) 등의 용어를 사용할 수 있다. 이러한 용어는 그 구성 요소를 다른 구성 요소와 구별하기 위한 것일 뿐, 그 용어에 의해 해당 구성 요소의 본질이나 차례 또는 순서 등이 한정되지 않는다. 어떤 구성 요소가 다른 구성요소에 "연결", "결합" 또는 "접속"된다고 기재된 경우, 그 구성 요소는 그 다른 구성요소에 직접적으로 연결되거나 또는 접속될 수 있지만, 각 구성 요소 사이에 또 다른 구성 요소가 "연결", "결합" 또는 "접속"될 수도 있다고 이해되어야 할 것이다.In addition, in describing the component of this invention, terms, such as 1st, 2nd, A, B, (a), (b), can be used. These terms are only for distinguishing the components from other components, and the nature, order or order of the components are not limited by the terms. If a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It is to be understood that the elements may be "connected", "coupled" or "connected".
본 명세서에서 사용된 용어 "할로" 또는 "할로겐"은 다른 설명이 없는 한 불소, 염소, 브롬, 및 요오드를 포함한다. As used herein, the term "halo" or "halogen" includes fluorine, chlorine, bromine, and iodine unless otherwise noted.
본 발명에 사용된 용어 "알킬" 또는 "알킬기"는 다른 설명이 없는 한 1 내지 60의 탄소수를 가지며, 여기에 제한되는 것은 아니다. As used herein, the term "alkyl" or "alkyl group" has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.
본 발명에 사용된 용어 "알케닐" 또는 "알키닐"은 다른 설명이 없는 한 각각 2 내지 60의 탄소수의 이중결합 또는 삼중결합을 가지며, 여기에 제한되는 것은 아니다. As used herein, the term "alkenyl" or "alkynyl" has a double bond or a triple bond having 2 to 60 carbon atoms, respectively, unless otherwise specified, but is not limited thereto.
본 발명에 사용된 용어 "시클로알킬"은 다른 설명이 없는 한 3 내지 60의 탄소수를 갖는 고리를 형성하는 알킬을 의미하며, 여기에 제한되는 것은 아니다. The term "cycloalkyl" as used herein, unless otherwise stated, refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
본 발명에 사용된 용어 "알콕시기"는 다른 설명이 없는 한 1 내지 60의 탄소수를 가지며, 여기에 제한되는 것은 아니다. The term "alkoxy group" used in the present invention has a carbon number of 1 to 60 unless otherwise stated, it is not limited thereto.
본 발명에 사용된 용어 "아릴기" 및 "아릴렌기"는 다른 설명이 없는 한 각각 6 내지 60의 탄소수를 가지며, 이에 제한되는 것은 아니다. As used herein, the terms "aryl group" and "arylene group" have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
본 발명에서 아릴기 또는 아릴렌기는 단일환 또는 복소환의 방향족을 의미하며, 이웃한 치환기가 결합 또는 반응에 참여하여 형성된 방향족 링을 포함한다. 예컨대, 아릴기는 페닐기, 비페닐기, 플루오렌기, 스파이로플루오렌기일 수 있다. In the present invention, an aryl group or an arylene group means a monocyclic or heterocyclic aromatic, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.
본 명세서에서 사용된 용어 "헤테로알킬"은 다른 설명이 없는 한 하나 이상의 헤테로원자를 포함하는 알킬을 의미한다. 본 발명에 사용된 용어 "헤테로아릴기" 또는 "헤테로아릴렌기"는 다른 설명이 없는 한 각각 하나 이상의 헤테로원자를 포함하는 탄소수 3 내지 60의 아릴기 또는 아릴렌기를 의미하며, 여기에 제한되는 것은 아니며, 단일환뿐만 아니라 복소환을 포함하며, 이웃한 기가 결합하여 형성될 수도 있다.As used herein, the term “heteroalkyl” means an alkyl including one or more heteroatoms unless otherwise indicated. As used herein, the term "heteroaryl group" or "heteroarylene group" means an aryl group or arylene group having 3 to 60 carbon atoms, each of which includes one or more heteroatoms, unless otherwise specified. In addition, it includes not only a single ring but also a heterocycle, and adjacent groups may be formed by bonding.
본 발명에 사용된 용어 "헤테로시클로알킬", "헤테로고리기"는 다른 설명이 없는 한 하나 또는 그 이상의 헤테로원자를 포함하고, 2 내지 60의 탄소수를 가지며, 단일환뿐만 아니라 복소환을 포함하며, 이웃한 기가 결합하여 형성될 수도 있다. 또한, "헤테로고리기"는 헤테로원자를 포함하는 지환족 및/또는 방향족을 의미할 수 있다.As used herein, the terms "heterocycloalkyl" and "heterocyclic group" include one or more heteroatoms, unless otherwise specified, have a carbon number from 2 to 60, and include heterocycles as well as monocycles. Adjacent groups may be formed in combination. In addition, "heterocyclic group" may mean an alicyclic and / or aromatic including a heteroatom.
본 명세서에서 사용된 용어 "헤테로원자"는 다른 설명이 없는 한 N, O, S, P 및 Si를 나타낸다. As used herein, the term “heteroatom” refers to N, O, S, P, and Si unless otherwise indicated.
다른 설명이 없는 한, 본 발명에 사용된 용어 "지방족"은 탄소수 1 내지 60의 지방족 탄화수소를 의미하며, "지방족고리"는 탄소수 3 내지 60의 지방족 탄화수소 고리를 의미한다. Unless otherwise stated, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
다른 설명이 없는 한, 본 발명에 사용된 용어 "포화 또는 불포화 고리"는 포화 또는 불포화 지방족고리 또는 탄소수 6 내지 60의 방향족고리 또는 헤테로고리를 의미한다.Unless otherwise stated, the term "saturated or unsaturated ring" as used herein means a saturated or unsaturated aliphatic ring or an aromatic ring or heterocyclic ring having 6 to 60 carbon atoms.
전술한 헤테로화합물 이외의 그 밖의 다른 헤테로화합물 또는 헤테로라디칼은 하나 이상의 헤테로원자를 포함하며, 여기에 제한되는 것은 아니다. Other heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
또한 명시적인 설명이 없는 한, 본 발명에서 사용된 용어 "치환 또는 비치환된"에서 "치환"은 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1~C20의 알킬기, C1~C20의 알콕시기, C1~C20의 알킬아민기, C1~C20의 알킬티오펜기, C6~C20의 아릴티오펜기, C2~C20의 알케닐기, C2~C20의 알키닐기, C3~C20의 시클로알킬기, C6~C60의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C8~C20의 아릴알케닐기, 실란기, 붕소기, 게르마늄기, 및 C5~C20의 헤테로고리기로 이루어진 군으로부터 선택되는 1개 이상의 치환기로 치환됨을 의미하며, 이들 치환기에 제한되는 것은 아니다. Also, unless stated otherwise, the term "substituted" in the term "substituted or unsubstituted" as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ~ C 20 alkyl group, C 1 ~ C 20 alkoxy groups, C 1 to C 20 alkylamine groups, C 1 to C 20 alkylthiophene groups, C 6 to C 20 arylthiophene groups, C 2 to C 20 alkenyl groups, C 2 to C 20 alkynyl group, C 3 ~ C 20 cycloalkyl group, C 6 ~ C 60 aryl group, C 6 ~ C 20 aryl group substituted with deuterium, C 8 ~ C 20 aryl alkenyl group, silane group, boron Group, germanium group, and C 5 ~ C 20 It is meant to be substituted with one or more substituents selected from the group consisting of, but not limited to these substituents.
도 1은 본 발명에 일 실시예에 따른 유기전기소자의 예시도이다.1 is an exemplary view of an organic electric device according to an embodiment of the present invention.
도 1을 참조하면, 본 발명에 따른 유기전기소자(100)는 기판(110) 상에 형성된 제 1전극(120), 제 2전극(180) 및 제 1전극(110)과 제 2전극(180) 사이에 화학식 1로 표시되는 화합물을 포함하는 유기물층을 구비한다. 이때, 제 1전극(120)은 애노드(양극)이고, 제 2전극(180)은 캐소드(음극)일 수 있으며, 인버트형의 경우에는 제 1전극이 캐소드이고 제 2전극이 애노드일 수 있다.Referring to FIG. 1, the organic electric device 100 according to the present invention includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110. An organic material layer containing a compound represented by the formula (1) between) is provided. In this case, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.
유기물층은 제 1전극(120) 상에 순차적으로 정공주입층(130), 정공수송층(140), 발광층(150), 전자수송층(160) 및 전자주입층(170)을 포함할 수 있다. 이때, 발광층(150)을 제외한 나머지 층들이 형성되지 않을 수 있다. 정공저지층, 전자저지층, 발광보조층(151), 버퍼층(141) 등을 더 포함할 수도 있고, 전자수송층(160) 등이 정공저지층의 역할을 할 수도 있을 것이다. The organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. At this time, the remaining layers except for the light emitting layer 150 may not be formed. The hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.
또한, 미도시하였지만, 본 발명에 따른 유기전기소자는 제 1전극과 제 2전극 중 적어도 일면 중 상기 유기물층과 반대되는 일면에 형성된 보호층을 더 포함할 수 있다. In addition, although not shown, the organic electronic device according to the present invention may further include a protective layer formed on one surface of the first electrode and the second electrode opposite to the organic material layer.
상기 유기물층에 적용되는 본 발명에 따른 화합물은 정공주입층(130), 정공수송층(140), 전자수송층(160), 전자주입층(170), 발광층(150)의 호스트 또는 도펀트 또는 캐핑층의 재료로 사용될 수 있을 것이다. 바람직하게는, 본 발명에 따른 화합물은 발광층(150)의 호스트 물질 또는 정공수송층(140) 형성 물질로 사용될 수 있다.The compound according to the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, the electron injection layer 170, the host of the light emitting layer 150 or the material of the dopant or capping layer Can be used as Preferably, the compound according to the present invention may be used as a host material of the light emitting layer 150 or a material for forming the hole transport layer 140.
한편, 본 발명의 일 실시예에 따른 유기전기발광소자는 PVD(physical vapor deposition) 방법을 이용하여 제조될 수 있다. 예컨대, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극(120)을 형성하고, 그 위에 정공주입층(130), 정공수송층(140), 발광층(150), 전자수송층(160) 및 전자주입층(170)을 포함하는 유기물층을 형성한 후, 그 위에 음극(180)으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다.On the other hand, the organic electroluminescent device according to an embodiment of the present invention can be manufactured using a PVD (physical vapor deposition) method. For example, the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon. After forming the organic material layer including the 160 and the electron injection layer 170, it can be prepared by depositing a material that can be used as the cathode 180 thereon.
또한, 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용액 공정 또는 솔벤트 프로세스(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다. 본 발명에 따른 유기물층은 다양한 방법으로 형성될 수 있으므로, 그 형성방법에 의해 본 발명의 권리범위가 제한되는 것은 아니다.In addition, the organic layer may be prepared by using a variety of polymer materials, but not by a deposition process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer. It can be prepared in a number of layers. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.
본 발명에 따른 유기전기소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic electric element according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
또한, 본 발명에 따른 유기전기소자는 유기전기발광소자(OLED), 유기태양전지, 유기감광체(OPC), 유기트랜지스터(유기 TFT), 단색 또는 백색 조명용 소자 중 하나일 수 있다.In addition, the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.
본 발명의 다른 실시예는 상술한 본 발명의 유기전기소자를 포함하는 디스플레이장치와, 이 디스플레이장치를 제어하는 제어부를 포함하는 전자장치를 포함할 수 있다. 이때, 전자장치는 현재 또는 장래의 유무선 통신단말일 수 있으며, 휴대폰 등의 이동 통신 단말기, PDA, 전자사전, PMP, 리모콘, 네비게이션, 게임기, 각종 TV, 각종 컴퓨터 등 모든 전자장치를 포함한다.Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device. In this case, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
이하, 본 발명의 일측면에 따른 유기전기소자의 유기물층에 함유된 화합물에 대하여 상세히 설명한다.Hereinafter, the compound contained in the organic material layer of the organic electric device according to an aspect of the present invention will be described in detail.
본 발명의 일측면에 따른 유기전기소자는 양극, 음극, 및 상기 양극과 음극 사이에 형성된 유기물층을 포함한다. 이때, 상기 발광층은 하기 화학식 1로 표시되는 화합물로 형성될 수 있다.An organic electric device according to an aspect of the present invention includes an anode, a cathode, and an organic material layer formed between the anode and the cathode. In this case, the emission layer may be formed of a compound represented by the following Chemical Formula 1.
<화학식 1><Formula 1>
Figure PCTKR2012008278-appb-I000002
Figure PCTKR2012008278-appb-I000002
상기 화학식 1에서, A환은 C6~C60의 단일 또는 다환의 방향족 또는 헤테로고리이며, n은 1 또는 2이다.In Formula 1, A ring is C 6 ~ C 60 A single or polycyclic aromatic or heterocyclic ring, n is 1 or 2.
그리고, 상기 화학식 1에서, Y는 직접결합(n=2인 경우에 한함); 수소, 중수소, 할로겐, 니트릴기, 니트로기, -L-N(Ar1)(Ar2), C6~C60의 아릴기, 플루오렌일기, C2~C60의 헤테로고리기, C1~C30의 알콕시기, C6~C30의 아릴옥시기 및 C1~C50의 알킬기로 이루어진 1가의 치환기 군에서 선택되거나; 또는 C6~C60의 아릴렌기, 플루오렌일렌기, C6~C60의 방향족환과 C3~C60의 지환족이 융합된 고리, C2~C60의 헤테로고리기 또는 2가의 지방족탄화수소기로 이루어진 2가의 치환기 군에서 선택될 수 있고,And, in the formula 1, Y is a direct bond (only when n = 2); Hydrogen, deuterium, halogen, nitrile group, nitro group, -LN (Ar 1 ) (Ar 2 ), C 6 ~ C 60 aryl group, fluorenyl group, C 2 ~ C 60 heterocyclic group, C 1 ~ C 30 alkoxy group, C 6 ~ C 30 aryloxy and C 1 ~ C 50 monovalent substituent selected from the group consisting of an alkyl group or a; Or a C 6 to C 60 arylene group, a fluorenylene group, a C 6 to C 60 aromatic ring and a C 3 to C 60 alicyclic fused ring, a C 2 to C 60 heterocyclic group or a divalent aliphatic hydrocarbon May be selected from the group of divalent substituents consisting of groups,
상기 R1 내지 R11은 서로 독립적으로 수소, 중수소, 할로겐, 니트릴기, 니트로기, -L-N(Ar1)(Ar2), C6~C60의 아릴기, 플루오렌일기, C2~C60의 헤테로고리기, C1~C30의 알콕시기, C6~C30의 아릴옥시기 및 C1~C50의 알킬기로 이루어진 군에서 선택될 수 있 있으며, X는 S, SO 또는 SO2 이다.R 1 to R 11 are each independently hydrogen, deuterium, halogen, nitrile group, nitro group, -LN (Ar 1 ) (Ar 2 ), C 6 ~ C 60 aryl group, fluorenyl group, C 2 ~ C 60 heterocyclic group, C 1 ~ C 30 Alkoxy group, C 6 ~ C 30 It may be selected from the group consisting of aryloxy group and C 1 ~ C 50 Alkyl group, X is S, SO or SO 2 to be.
이때, -L-N(Ar1)(Ar2)에서, L은 직접결합이거나(즉, 부존재함), C6~C60의 아릴렌기, 플루오렌일렌기, C6~C60의 방향족환과 C3~C60의 지환족이 융합된 고리, C2~C60의 헤테로고리기 또는 2가의 지방족탄화수소로 이루어진 군에서 선택될 수 있으며,In this case, in -LN (Ar 1 ) (Ar 2 ), L is a direct bond (that is, absent), C 6 ~ C 60 arylene group, fluorenylene group, C 6 ~ C 60 aromatic ring and C 3 ~ C 60 of aliphatic and may be selected from the group consisting of fused rings, C 2 ~ C 60 heterocyclic group or a divalent aliphatic hydrocarbon group,
Ar1과 Ar2는 서로 독립적으로 C6~C60의 아릴기, C2~C60의 헤테로고리기, 플루오렌일기, C1~C30의 알콕시기, C6~C30의 아릴옥시기 및 C1~C50의 알킬기로 이루어진 군에서 선택된다.Ar 1 and Ar 2 are each independently of the C 6 ~ C 60 aryl group, C 2 ~ C 60 heterocyclic group, fluorenyl group, C 1 ~ C 30 alkoxy group, C 6 ~ C 30 aryloxy group And it is selected from the group consisting of C 1 ~ C 50 Alkyl group.
한편, 상기 Y, R1 내지 R11, L, Ar1 및 Ar2 등은 특정 치환기로 더 치환될 수 있다.Meanwhile, Y, R 1 to R 11 , L, Ar 1, and Ar 2 may be further substituted with specific substituents.
예시적으로, Y, R1 내지 R11, Ar1 및 Ar2 가 C6~C60의 아릴기 경우와, 상기 Y, R1 내지 R11, Ar1 및 Ar2 가 플루오렌일기인 경우와, 상기 Y 및 L의 아릴렌기인 경우와, 상기 Y 및 L이 플루오렌일렌기인 경우, 이들은 중수소, 할로겐, 실란기, 붕소기, 게르마늄기, C1~C20 의 알킬싸이오기, C6~C20의 아릴싸이오기, C1~C20의 알콕시기, -N(Ar1)(Ar2), C1~C20의 알킬기, C7~C20의 아릴알킬기, C2~C20의 알케닐기, C8~C20의 아릴알케닐기, C2~C20의 알키닐기, C3~C20의 시클로알킬기, 중수소로 치환된 C6~C20의 아릴기 및 C2~C20의 헤테로고리기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있다.By way of example, when Y, R 1 to R 11 , Ar 1 and Ar 2 is a C 6 ~ C 60 aryl group, and when Y, R 1 to R 11 , Ar 1 and Ar 2 is a fluorenyl group and In the case of the arylene group of the Y and L, and the Y and L is a fluorenylene group, these are deuterium, halogen, silane group, boron group, germanium group, C 1 ~ C 20 Alkylthio group, C 6 ~ C 20 arylthio group, C 1 -C 20 alkoxy group, -N (Ar 1 ) (Ar 2 ), C 1 -C 20 alkyl group, C7-C20 arylalkyl group, C 2 -C 20 alkenyl group , C 8 ~ C 20 aryl alkenyl group, C 2 ~ C 20 alkynyl group, C 3 ~ C 20 cycloalkyl group, C 6 ~ C 20 aryl group substituted with deuterium and C 2 ~ C 20 heterocyclic ring It may be substituted with one or more substituents selected from the group consisting of groups.
또한, 상기 Y, R1 내지 R11, L, Ar1 및 Ar2 의 C6~C60의 헤테로고리기는 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하며, 중수소, 할로겐기, -N(Ar1)(Ar2), C1~C20의 알킬기, C7~C20의 아릴알킬기, C2~C20의 알케닐기, C8~C20의 아릴알케닐기, C1~C20의 알콕시기, C6~C60의 아릴기, 중수소로 치환된 C6~C20의 아릴기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있다.In addition, the C 6 ~ C 60 heterocyclic group of the Y, R 1 to R 11 , L, Ar 1 and Ar 2 includes at least one hetero atom of O, N, S, Si and P, deuterium, halogen Group, -N (Ar 1 ) (Ar 2 ), C 1 -C 20 alkyl group, C 7 -C 20 arylalkyl group, C 2 -C 20 alkenyl group, C 8 -C 20 arylalkenyl group, C It may be substituted with one or more substituents selected from the group consisting of 1 to C 20 alkoxy group, C 6 ~ C 60 aryl group, C 6 ~ C 20 aryl group substituted with deuterium, a nitrile group and an acetylene group.
또한, 상기 Y, R1 내지 R11, Ar1 및 Ar2의 C1~C30의 알콕시기 및 C6~C30의 아릴옥시기는 중수소, 할로겐기, 아미노기, 니트릴기, 니트로기, C1~C20 의 알킬기, C2~C20의 알케닐기, C1~C20의 알콕시기, C3~C30의 시클로알킬기, C6~C60의 아릴기, 중수소로 치환된 C6~C20의 아릴기 및 C2~C60의 헤테로고리기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있다.Further, the C 1 to C 30 alkoxy group and the C 6 to C 30 aryloxy group of the Y, R 1 to R 11 , Ar 1 and Ar 2 may be deuterium, halogen, amino, nitrile, nitro or C 1. ~ C 20 alkyl group, C 2 ~ C 20 alkenyl group, C 1 ~ C 20 alkoxy group, C 3 ~ C 30 cycloalkyl group, C 6 ~ C 60 aryl group, a C 6 ~ C substituted with deuterium It may be substituted with one or more substituents selected from the group consisting of an aryl group of 20 and a heterocyclic group of C 2 ~ C 60 .
또한, 상기 Y, R1 내지 R11, r1 및 Ar2의 C1~C50의 알킬기는 C2~C20의 알케닐기, C1~C20의 알콕시기, C6~C20의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C7~C20의 아릴알킬기, C8~C20의 아릴알케닐기, C2~C20의 헤테로고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있다.In addition, the C 1 to C 50 alkyl group of Y, R 1 to R 11 , r 1, and Ar 2 may be C 2 to C 20 alkenyl group, C 1 to C 20 alkoxy group, C 6 to C 20 aryl A C 6 to C 20 aryl group, a C 7 to C 20 arylalkyl group, a C 8 to C 20 arylalkenyl group, a C 2 to C 20 heterocyclic group, a nitrile group and an acetylene group It may be substituted with one or more substituents selected from the group.
구체적으로, 상기 화학식 1은 하기 화학식 중 하나로 표시될 수 있을 것이다. 하기 화학식 2는 화학식 1에서 n=1인 경우에 해당하며, 화학식 3은 n=2인 경우에 해당한다. 또한 화학식 4는, 화학식 1에서 n=1이고, Y가 1가의 치환기 중 -L-N(Ar1)(Ar2)인 경우에 해당한다.Specifically, Formula 1 may be represented by one of the following formula. Formula 2 corresponds to the case of n = 1 in Formula 1, and Formula 3 corresponds to the case of n = 2. In addition, Formula 4 corresponds to the case where n = 1 in Formula 1 and Y is -L-N (Ar1) (Ar2) among monovalent substituents.
<화학식 2><Formula 2>
Figure PCTKR2012008278-appb-I000003
Figure PCTKR2012008278-appb-I000003
<화학식 3><Formula 3>
Figure PCTKR2012008278-appb-I000004
Figure PCTKR2012008278-appb-I000004
<화학식 4><Formula 4>
Figure PCTKR2012008278-appb-I000005
Figure PCTKR2012008278-appb-I000005
상기 화학식 2 내지 화학식 4에서, A환, R1~R11 및 X는 화학식 1에서 정의된 것과 같다. 그리고, 화학식 2에서 Y는 화학식 1의 Y 정의 중 1가 치환기 군에서 선택될 수 있으며, 화학식 3에서 Y는 직접결합이거나, 화학식 1의 Y 정의 중 2가 치환기 군에서 선택될 수 있을 것이다. 또한, 화학식 4에서, L, Ar1 및 Ar2는 화학식 1에 정의된 것과 같다.In Formula 2 to Formula 4, A ring, R 1 ~ R 11 and X are as defined in formula (1). In Formula 2, Y may be selected from the group of monovalent substituents in the definition of Y in Formula 1, and in Formula 3, Y may be a direct bond or may be selected from the group of divalent substituents in the definition of Y in Formula 1. In addition, in Chemical Formula 4, L, Ar 1 and Ar 2 are the same as defined in Chemical Formula 1.
또한, A환이 벤젠링인 경우 화학식 1은 하기 화학식 5 내지 7 중 하나로 표시될 수 있을 것이다.In addition, when A ring is a benzene ring, Formula 1 may be represented by one of the following Formulas 5 to 7.
<화학식 5> <Formula 5>
Figure PCTKR2012008278-appb-I000006
Figure PCTKR2012008278-appb-I000006
<화학식 6> <Formula 6>
Figure PCTKR2012008278-appb-I000007
Figure PCTKR2012008278-appb-I000007
<화학식 7><Formula 7>
Figure PCTKR2012008278-appb-I000008
Figure PCTKR2012008278-appb-I000008
상기 화학식 5 내지 화학식 7에서, R1~R8 및 X는 화학식 1에서 정의된 것과 같다. 그리고, 화학식 5의 Y는 화학식 1의 Y 정의 중 1가 치환기 군 중에서 선택될 수 있으며, 화학식 6의 Y는 직접결합이거나, 화학식 1의 Y 정의 중 2가 치환기 군에서 선택될 수 있으며, 화학식 7의 L, Ar1 및 Ar2는 화학식 1에 정의된 것과 같다.In Chemical Formulas 5 to 7, R 1 to R 8 and X are the same as defined in Chemical Formula 1. In addition, Y in Formula 5 may be selected from the group of monovalent substituents in the Y definition of Formula 1, Y in Formula 6 may be a direct bond, or may be selected from a divalent substituent group in the Y definition of Formula 1, Formula 7 L, Ar 1 and Ar 2 are as defined in formula (1).
더욱 구체적으로, 상기 화학식 1은 하기 화합물 중 하나일 수 있으나, 이들 화합물로 제한되는 것은 아니며, 화학식 1을 만족하는 화합물이라면 본 발명에 속한다 할 것이다.More specifically, Formula 1 may be one of the following compounds, but is not limited to these compounds, any compound satisfying Formula 1 will belong to the present invention.
Figure PCTKR2012008278-appb-I000009
Figure PCTKR2012008278-appb-I000009
Figure PCTKR2012008278-appb-I000010
Figure PCTKR2012008278-appb-I000010
Figure PCTKR2012008278-appb-I000011
Figure PCTKR2012008278-appb-I000011
Figure PCTKR2012008278-appb-I000012
Figure PCTKR2012008278-appb-I000012
Figure PCTKR2012008278-appb-I000013
Figure PCTKR2012008278-appb-I000013
Figure PCTKR2012008278-appb-I000014
Figure PCTKR2012008278-appb-I000014
Figure PCTKR2012008278-appb-I000015
Figure PCTKR2012008278-appb-I000015
Figure PCTKR2012008278-appb-I000016
Figure PCTKR2012008278-appb-I000016
Figure PCTKR2012008278-appb-I000017
Figure PCTKR2012008278-appb-I000017
Figure PCTKR2012008278-appb-I000018
Figure PCTKR2012008278-appb-I000018
Figure PCTKR2012008278-appb-I000019
Figure PCTKR2012008278-appb-I000019
Figure PCTKR2012008278-appb-I000020
Figure PCTKR2012008278-appb-I000020
Figure PCTKR2012008278-appb-I000021
Figure PCTKR2012008278-appb-I000021
Figure PCTKR2012008278-appb-I000022
Figure PCTKR2012008278-appb-I000022
Figure PCTKR2012008278-appb-I000023
Figure PCTKR2012008278-appb-I000023
Figure PCTKR2012008278-appb-I000024
Figure PCTKR2012008278-appb-I000024
Figure PCTKR2012008278-appb-I000025
Figure PCTKR2012008278-appb-I000025
Figure PCTKR2012008278-appb-I000026
Figure PCTKR2012008278-appb-I000026
Figure PCTKR2012008278-appb-I000027
Figure PCTKR2012008278-appb-I000027
Figure PCTKR2012008278-appb-I000028
Figure PCTKR2012008278-appb-I000028
Figure PCTKR2012008278-appb-I000029
Figure PCTKR2012008278-appb-I000029
Figure PCTKR2012008278-appb-I000030
Figure PCTKR2012008278-appb-I000030
Figure PCTKR2012008278-appb-I000031
Figure PCTKR2012008278-appb-I000031
Figure PCTKR2012008278-appb-I000032
Figure PCTKR2012008278-appb-I000032
Figure PCTKR2012008278-appb-I000033
Figure PCTKR2012008278-appb-I000033
Figure PCTKR2012008278-appb-I000034
Figure PCTKR2012008278-appb-I000034
이하, 본 발명의 화학식 1로 표시되는 화합물의 합성예 및 유기전기소자의 제조예에 관하여 실시예를 들어 구체적으로 설명하지만, 본 발명이 하기의 실시예로 한정되는 것은 아니다.Hereinafter, the synthesis examples of the compounds represented by the general formula (1) of the present invention and the production examples of the organic electric device will be described in detail with reference to Examples, but the present invention is not limited to the following Examples.
예시적으로, 상기 화학식 1은 하기 반응식 1 또는 화학식 3의 반응경로에 의해 합성될 수 있다.In exemplary embodiments, Chemical Formula 1 may be synthesized by the following Chemical Formula 1.
<반응식 1><Scheme 1>
Figure PCTKR2012008278-appb-I000035
Figure PCTKR2012008278-appb-I000035
상기 반응식 1에서, Sub 1-6은 하기 반응식 2에 의하여 합성될 수 있을 것이다.In Scheme 1, Sub 1-6 may be synthesized by Scheme 2 below.
<반응식 2><Scheme 2>
Figure PCTKR2012008278-appb-I000036
Figure PCTKR2012008278-appb-I000036
상기 반응식 2의 Sub 1-1 내지 Sub 1-6은 다음 합성 방법에 의해 합성될 수 있을 것이나 이에 제한되는 것은 아니다.Sub 1-1 to Sub 1-6 of Scheme 2 may be synthesized by the following synthesis method, but is not limited thereto.
Sub 1-1 합성법Sub 1-1 Synthesis
Phenanthrene (35.65 g, 200 mmol) 을 메틸렌클로라이드 600 mL 에 녹인 후, BPO(Benzoyl peroxide) 0.05당량과 NBS(N-bromosuccinimide) (35.60 g, 200 mmol)을 서서히 첨가한 뒤, 상온에서 24시간 교반시킨다. 반응이 종료되면 5% 농도의 HCl 300 mL 을 첨가한 뒤, 물 300 mL 을 첨가하여, 잔존 NBS 를 제거하고, ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한다. 그 후 생성된 유기물을 silicagel column 및 재결정하여 Sub 1-1을 38.57 g(75%) 얻었다.After dissolving Phenanthrene (35.65 g, 200 mmol) in 600 mL of methylene chloride, 0.05 equivalent of BPO (Benzoyl peroxide) and NBS (N-bromosuccinimide) (35.60 g, 200 mmol) were slowly added, followed by stirring at room temperature for 24 hours. . After the reaction was completed, 300 mL of 5% HCl was added, followed by 300 mL of water to remove residual NBS, and extracted with ether and water. The organic layer was dried over MgSO 4 and concentrated. Thereafter, the resultant organic material was recrystallized from a silicagel column to obtain 38.57 g (75%) of Sub 1-1.
Sub 1-2 합성법Sub 1-2 synthesis
상기 합성에서 얻어진 Sub 1-1 (36.0 g, 140 mmol) 을 DMF 980mL 에 녹인 후에, 비스피나콜보레이트를 (39.1 g, 154 mmol), PdCl2(dppf) 촉매 (3.43 g, 4.2 mmol), KOAc (41.3 g, 420 mmol)을 순서대로 첨가한 후 24 시간 교반하여 보레이트 화합물을 합성한 후에, 얻어진 화합물을 실리카겔 칼럼 및 재결정을 걸쳐서 분리한 후 보레이트 화합물을 Sub 1-2를 29.81 g (70 %)얻는다. Sub 1-1 (36.0 g, 140 mmol) obtained in the above synthesis was dissolved in 980 mL of DMF, followed by bispinacolborate (39.1 g, 154 mmol), PdCl 2 (dppf) catalyst (3.43 g, 4.2 mmol), KOAc (41.3 g, 420 mmol) was added sequentially, followed by stirring for 24 hours to synthesize the borate compound. The obtained compound was separated through a silica gel column and recrystallized, and then the borate compound was 29.81 g (70%) of Sub 1-2. Get
Sub 1-3 합성법Sub 1-3 Synthesis
상기 합성에서 얻어진 Sub 1-2 1당량과 2-bromothioanisole 1당량을 THF 200ml에 녹인 후, Tetrakis(triphenylphosphine)palladium 1.1당량과 2M의 aqueous sodium carbonate solution을 첨가하며, 70℃에서 18시간 교반시킨다. 반응이 종료되면 diethyl ehter와 물로 추출한 후 유기층을 건조하고 silicagel column 및 재결정하여 Sub 1-3을 80% 얻었다.After dissolving 1 equivalent of Sub 1-2 obtained in the synthesis and 1 equivalent of 2-bromothioanisole in 200 ml of THF, 1.1 equivalent of Tetrakis (triphenylphosphine) palladium and 2M aqueous sodium carbonate solution were added thereto, and the mixture was stirred at 70 ° C for 18 hours. After the reaction was completed, extracted with diethyl ehter and water, the organic layer was dried, silicagel column and recrystallization to obtain Sub 1-3 80%.
Sub 1-4 합성법Sub 1-4 Synthesis
Sub 1-3을 디클로로메탄에 녹인 후, 30% aqueous hydroxyperoxide solution과 acetic acid를 첨가 후, 30℃에서 4시간 교반시킨다. 반응이 종료되면 chloroform과 물로 추출한 후, 유기층을 건조하고 silicagel column 및 재결정하여 Sub 1-4을 76% 얻었다.Sub 1-3 was dissolved in dichloromethane, 30% aqueous hydroxyperoxide solution and acetic acid were added, followed by stirring at 30 ° C. for 4 hours. After the reaction was completed, extracted with chloroform and water, the organic layer was dried, silicagel column and recrystallization to obtain Sub 1-4 76%.
Sub 1-5 합성법Sub 1-5 synthesis
Sub 1-4에 triflic acid를 넣고, 72시간동안 상온에서 교반시킨다. 반응이 종료되면 diethyl ehter를 첨가하고, 생성되는 하얀 고체 침전물을 필터하고, 건조시키켜 Sub 1-5를 78% 얻었다. Add triflic acid to Sub 1-4 and stir at room temperature for 72 hours. After the reaction was completed, diethyl ehter was added, and the resulting white solid precipitate was filtered and dried to obtain 78% of Sub 1-5.
Sub 1-6 합성법Sub 1-6 Synthesis
Sub 1-5를 메틸렌 크로라이드 600 mL 에 녹인 후, BPO(Benzoyl peroxide) 0.05당량과 NBS(N-bromosuccinimide) (35.60 g, 200 mmol)을 서서히 첨가한 뒤, 상온에서 24시간 교반시킨다. 반응이 종료되면 5% 농도의 HCl 300 mL 을 첨가한 뒤, 물 300 mL 을 첨가하여, 잔존 NBS 를 제거하고, ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한다. 그 후 생성된 유기물을 silicagel column 및 재결정하여 Sub 1-6을 78% 얻었다.Sub 1-5 was dissolved in 600 mL of methylene chloride, and then 0.05 equivalent of BPO (Benzoyl peroxide) and NBS (N-bromosuccinimide) (35.60 g, 200 mmol) were added slowly, followed by stirring at room temperature for 24 hours. After the reaction was completed, 300 mL of 5% HCl was added, followed by 300 mL of water to remove residual NBS, and extracted with ether and water. The organic layer was dried over MgSO 4 and concentrated. The resulting organic material was silicagel column and recrystallized to obtain Sub 1-6 78%.
한편, 상기 반응식 1에서 Sub 2는 하기 화합물 중 하나일 수 있으나, 이에 한정되는 것은 아니다.Meanwhile, Sub 2 in Scheme 1 may be one of the following compounds, but is not limited thereto.
Figure PCTKR2012008278-appb-I000037
Figure PCTKR2012008278-appb-I000037
Figure PCTKR2012008278-appb-I000038
Figure PCTKR2012008278-appb-I000038
Figure PCTKR2012008278-appb-I000039
Figure PCTKR2012008278-appb-I000039
Figure PCTKR2012008278-appb-I000040
Figure PCTKR2012008278-appb-I000040
Figure PCTKR2012008278-appb-I000041
Figure PCTKR2012008278-appb-I000041
상기 Sub 2-1 내지 Sub 2-24의 FD-MS 값은 하기 표 1과 같다. The FD-MS values of Sub 2-1 to Sub 2-24 are shown in Table 1 below.
표 1
Figure PCTKR2012008278-appb-T000001
 Table 1
Figure PCTKR2012008278-appb-T000001
<< 실시예EXAMPLE 1> 최종 화합물( 1> final compound ( ProductProduct 1)의 합성 예시  Synthesis example of 1)
둥근바닥플라스크에 Sub 1-6의 화합물 (1당량), Sub 2 화합물 (1당량), Pd2(dba)3 (0.03~0.5 mmol), PPh3 (0.1당량), NaOt-Bu (3당량), toluene (10.5 mL / 1 mmol)을 넣은 후에 100 ℃에서 반응을 진행한다. 반응이 완료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한 후 생성된 유기물을 silicagel column 및 재결정하였다. 생성된 최종 화합물의 FD-MS는 하기 표 2와 같다.Compounds of Sub 1-6 (1 equiv), Sub 2 compounds (1 equiv), Pd 2 (dba) 3 (0.03-0.5 mmol), PPh 3 (0.1 equiv), NaO t -Bu (3 equiv. ), add toluene (10.5 mL / 1 mmol) and proceed with the reaction at 100 ° C. After the reaction was completed, the mixture was extracted with ether and water, and the organic layer was dried over MgSO 4 , concentrated, and the resulting organic material was silicagel column and recrystallized. FD-MS of the resulting final compound is shown in Table 2 below.
표 2
Figure PCTKR2012008278-appb-T000002
 TABLE 2
Figure PCTKR2012008278-appb-T000002
다른 예로서, 본 발명의 최종 화합물은 하기 반응식 3에 의해 제조될 수 있다.As another example, the final compound of the present invention can be prepared by the following scheme 3.
<반응식 3><Scheme 3>
Figure PCTKR2012008278-appb-I000042
Figure PCTKR2012008278-appb-I000042
상기 반응식 3에서, Sub 3은 다음 화합물 중 하나일 수 있으나, 반드시 이들로 한정되는 것은 아니다.In Scheme 3, Sub 3 may be one of the following compounds, but is not necessarily limited thereto.
Figure PCTKR2012008278-appb-I000043
Figure PCTKR2012008278-appb-I000043
Figure PCTKR2012008278-appb-I000044
Figure PCTKR2012008278-appb-I000044
Figure PCTKR2012008278-appb-I000045
Figure PCTKR2012008278-appb-I000045
Figure PCTKR2012008278-appb-I000046
Figure PCTKR2012008278-appb-I000046
Figure PCTKR2012008278-appb-I000047
Figure PCTKR2012008278-appb-I000047
Figure PCTKR2012008278-appb-I000048
Figure PCTKR2012008278-appb-I000048
Figure PCTKR2012008278-appb-I000049
Figure PCTKR2012008278-appb-I000049
Figure PCTKR2012008278-appb-I000050
Figure PCTKR2012008278-appb-I000050
Figure PCTKR2012008278-appb-I000051
Figure PCTKR2012008278-appb-I000051
상기 Sub 3-1 내지 Sub 3-66의 FD-MS는 하기 표 3과 같다.The FD-MS of Sub 3-1 to Sub 3-66 is shown in Table 3 below.
표 3
Figure PCTKR2012008278-appb-T000003
 TABLE 3
Figure PCTKR2012008278-appb-T000003
Figure PCTKR2012008278-appb-I000052
Figure PCTKR2012008278-appb-I000052
<< 실시예EXAMPLE 2> 최종 화합물( 2> final compound ( ProductProduct 2) 합성 예시 2) Synthesis Example
둥근바닥플라스크에 Sub 1-7 화합물(1당량)을 넣고, 아민화합물 Sub 3을 (1.1당량), Pd(PPh3)4 (0.03~0.05당량), NaOH (3당량), THF (3 mL / 1 mmol), 물 (1.5 mL / 1 mmol)을 넣는다. 이후, 80℃~90℃ 상태에서 가열 환류시킨다. 반응이 완료되면 상온에서 증류수를 넣어 희석시키고 메틸렌클로라이드와 물로 추출한다. 유기층을 MgSO4로 건조하여 농축한 후 생성된 화합물을 silicagel column 및 재결정하였다. 이와 같이 합성한 최종 화합물의 FD-MS는 하기 표 4와 같다.Sub 1-7 compound (1 equivalent) was added to a round bottom flask, and the amine compound Sub 3 (1.1 equivalent), Pd (PPh 3 ) 4 (0.03 to 0.05 equivalent), NaOH (3 equivalent), THF (3 mL / 1 mmol), water (1.5 mL / 1 mmol) is added. Thereafter, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, distilled water is diluted at room temperature and extracted with methylene chloride and water. The organic layer was dried over MgSO 4 , concentrated, and the resulting compound was recrystallized from a silicagel column. FD-MS of the final compound thus synthesized is shown in Table 4 below.
표 4
Figure PCTKR2012008278-appb-T000004
 Table 4
Figure PCTKR2012008278-appb-T000004
Figure PCTKR2012008278-appb-I000053
Figure PCTKR2012008278-appb-I000053
한편, 화학식 1로 표시되는 화합물들의 각 치환기들은 광범위한 관계로, 대표적인 화합물들의 합성예를 예시적으로 설명하였으나, 합성예로 예시적으로 설명하지 않은 화학식 1로 표시되는 화합물들도 본 명세서의 일부를 구성할 수 있다.On the other hand, each of the substituents of the compounds represented by the formula (1) has a broad relationship, exemplarily described the synthesis examples of the representative compounds, the compounds represented by the formula (1) not illustrated by way of example as a synthesis example Can be configured.
또한, 상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 도입된 치환기의 고유 특성을 갖는 화합물을 합성할 수 있다. 예컨대, 유기발광소자를 비롯한 유기전기소자의 제조시 사용되는 정공주입층 물질, 정공수송층 물질, 발광층 물질, 및 전자 수송층 물질에 사용되는 치환기를 상기 구조에 도입함으로써 각 유기물층에서 요구하는 조건들을 충족시키는 물질을 제조할 수 있다.Moreover, the compound which has the intrinsic property of the introduced substituent can be synthesize | combined by introducing various substituents into the core structure of the above structure. For example, by introducing substituents used in the hole injection layer material, the hole transport layer material, the light emitting layer material, and the electron transport layer material used in the manufacture of the organic electric device, including the organic light emitting device to satisfy the conditions required for each organic material layer Materials can be prepared.
본 발명에 따른 화합물은 치환기의 종류 및 성질에 따라 유기전기발광소자에서 다양한 용도로 사용될 수 있을 것이다. 즉, 본 발명의 화합물은 코어와 치환체에 의해 조절이 자유롭기 때문에 인광 또는 형광 발광층의 호스트 이외의 다양한 층에 적용될 수 있다.The compound according to the present invention may be used in various applications in the organic electroluminescent device according to the type and nature of the substituent. That is, the compound of the present invention can be applied to various layers other than the host of the phosphorescent or fluorescent light emitting layer because it is free to be controlled by the core and the substituent.
유기전기소자의 제조평가Manufacturing Evaluation of Organic Electrical Device
<< 실험예Experimental Example 1> 1>
먼저, 유리 기판에 형성된 ITO층(양극) 위에 구리프탈로사이아닌(CuPc)막을 진공증착하여 10 nm 두께의 정공주입층을 형성하였다. 이어서, 정공주입층 상에 4,4-비스[N-(1-나프틸)-N-페닐아미노]비페닐을 30 nm 두께로 진공 증착하여 정공수송층을 형성하였다. 그리고, 정공 수송층 상부에 본 발명의 화합물을 호스트 물질로, Ir(ppy)3[tris(2-phenylpyridine)-iridium] 를 도펀트 물질로 사용하여 95:5 중량으로 도핑함으로써 30nm 두께의 발광층을 형성하였다. 이어서, 상기 발광층 상에 ((1,1'-비스페닐)-4-올레이토)비스(2-메틸-8-퀴놀린올레이토)알루미늄을 10 nm 두께로 진공증착하여 정공저지층을 형성하고, 정공저지층 상에 트리스(8-퀴놀리놀)알루미늄을 40 nm 두께로 성막하여 전자주입층을 형성하였다. 이후, 할로겐화 알칼리 금속인 LiF를 0.2 nm 두께로 증착하고, Al을 150 nm의 두께로 증착하여, Al/LiF 음극을 형성함으로써 유기전계발광소자를 제작하였다.First, a copper phthalocyanine (CuPc) film was vacuum deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 10 nm. Subsequently, 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl was vacuum deposited to a thickness of 30 nm on the hole injection layer to form a hole transport layer. In addition, a light emitting layer having a thickness of 30 nm was formed on the hole transport layer by doping at 95: 5 weight using a compound of the present invention as a host material and Ir (ppy) 3 [tris (2-phenylpyridine) -iridium] as a dopant material. . Subsequently, ((1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, Tris (8-quinolinol) aluminum was deposited to a thickness of 40 nm on the hole blocking layer to form an electron injection layer. Subsequently, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, Al was deposited to a thickness of 150 nm, and an organic light emitting diode was manufactured by forming an Al / LiF cathode.
<< 비교예Comparative example 1> 1>
발광층 형성시 본 발명의 화합물 대신 하기 비교화합물 2으로 표시되는 화합물을 호스트 물질로 사용한 점을 제외하고, 실험예 1과 동일하게 유기전계발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Experiment 1, except that the compound represented by Comparative Compound 2 was used as a host material instead of the compound of the present invention when forming the emission layer.
<비교 화합물 1>          <Comparative Compound 1>
Figure PCTKR2012008278-appb-I000054
Figure PCTKR2012008278-appb-I000054
본 발명의 실험예 1 및 비교예 1에 의하여 제작된 유기전계발광소자에 대한 소자 성능, 즉 구동전압, 전류밀도, 밝기, 효율, 수명, 색좌표 등에 대한 측정 결과는 하기 표 5와 같다. 표 5에서, 본 발명의 실험예에 따라 제작된 유기전계발광소자를 실시예 1 내지 실험예 145로 표시하였다.Measurement results of device performance, that is, driving voltage, current density, brightness, efficiency, lifetime, and color coordinates of the organic light emitting diodes manufactured by Experimental Example 1 and Comparative Example 1 of the present invention are shown in Table 5 below. In Table 5, the organic light emitting display device manufactured according to the experimental example of the present invention is represented by Examples 1 to 145.
표 5
Figure PCTKR2012008278-appb-T000005
 Table 5
Figure PCTKR2012008278-appb-T000005
Figure PCTKR2012008278-appb-I000055
Figure PCTKR2012008278-appb-I000055
Figure PCTKR2012008278-appb-I000056
Figure PCTKR2012008278-appb-I000056
Figure PCTKR2012008278-appb-I000057
Figure PCTKR2012008278-appb-I000057
<< 실험예Experimental Example 2> 2>
먼저, 유리 기판에 형성된 ITO층(양극) 상에 4,4'4”-트리스(N-(2-나프틸)-N-페닐아미노)-트리페닐아민 (이하 2T-NATA로 약기함)막을 진공증착하여 10 nm 두께의 정공주입층을 형성하였다. 이어서, 정공주입층 상에 본 발명의 화합물을 진공증착하여 30 nm 두께의 정공수송층을 형성하였다. 그리고, 정공수송층 상부에 BD-052X(Idemitus사)가 7% 도핑된 45nm두께의 발광층을 형성하였다(이때, BD-052X는 청색 형광 도펀트이고, 발광 호스트 물질로는 9,10-다이(나프탈렌-2-안트라센(AND))을 사용하였다). 이어서, 상기 발광층 상에 ((1,1'-비스페닐)-4-올레이토)비스(2-메틸-8-퀴놀린올레이토)알루미늄을 10 nm 두께로 진공증착하여 정공저지층을 형성하고, 정공저지층 상에 트리스(8-퀴놀리놀)알루미늄을 40 nm 두께로 성막하여 전자주입층을 형성하였다. 이후, 할로겐화 알칼리 금속인 LiF를 0.2 nm 두께로 증착하고, Al을 150 nm의 두께로 증착하여, Al/LiF 음극을 형성함으로써 유기전계발광소자를 제작하였다.First, a 4,4'4 "-tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine (hereinafter abbreviated as 2T-NATA) film was formed on an ITO layer (anode) formed on a glass substrate. Vacuum deposition was performed to form a 10 nm thick hole injection layer. Subsequently, the compound of the present invention was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 30 nm. In addition, a 45 nm-thick light emitting layer doped with BD-052X (Idemitus, Inc.) 7% was formed on the hole transport layer. 2-anthracene (AND))). Subsequently, ((1,1'-bisphenyl) -4-oleato) bis (2-methyl-8-quinolinolato) aluminum was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, Tris (8-quinolinol) aluminum was deposited to a thickness of 40 nm on the hole blocking layer to form an electron injection layer. Thereafter, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, Al was deposited to a thickness of 150 nm, and an organic light emitting display device was fabricated by forming an Al / LiF cathode.
<< 비교예Comparative example 2> 2>
정공주입층 형성시 본 발명의 화합물 대신 하기 비교화합물 2로 표시되는 화합물을 사용한 점을 제외하고, 실험예 2와 동일하게 유기전계발광소자를 제작하였다. An organic light emitting display device was manufactured in the same manner as in Experiment 2, except that the compound represented by Comparative Compound 2 was used instead of the compound of the present invention when forming the hole injection layer.
<비교 화합물 2><Comparative Compound 2>
Figure PCTKR2012008278-appb-I000058
Figure PCTKR2012008278-appb-I000058
본 발명의 실험예 2 및 비교예 2에 의하여 제작된 유기전계발광소자에 대한 소자 성능, 즉 구동전압, 전류밀도, 밝기, 효율, 수명, 색좌표 등에 대한 측정 결과는 하기 표 6과 같다. 하기 표 6에서, 본 발명의 실험예 2에 따라 제작된 유기전계발광소자를 실시예 146 내지 실험예 157로 표시하였다.Measurement results of device performance, that is, driving voltage, current density, brightness, efficiency, lifespan, and color coordinates of the organic light emitting diodes manufactured by Experimental Example 2 and Comparative Example 2 of the present invention are shown in Table 6 below. In Table 6 below, the organic light emitting display device manufactured according to Experimental Example 2 of the present invention is represented by Examples 146 to 157.
표 6
Figure PCTKR2012008278-appb-T000006
 Table 6
Figure PCTKR2012008278-appb-T000006
상기 표 5 및 표 6에서 확인할 수 있는 것과 같이, 본 발명에 따른 화합물을 발광 호스트 또는 정공수송층 재료로 사용시, 유기전계발광소자의 구동전압을 낮출 수 있고, 색순도, 발광효율 및 수명을 현저히 개선시킬 수 있다. 본 발명의 화합물들을 유기전계발광소자의 다른 유기물층들, 예를 들어 발광 보조층, 전자주입층, 전자수송층, 및 정공주입층 등에 사용되더라도 동일한 효과를 얻을 수 있는 것은 자명하다.As can be seen in Table 5 and Table 6, when the compound according to the present invention is used as a light emitting host or hole transport layer material, the driving voltage of the organic light emitting device can be lowered, and color purity, luminous efficiency and lifespan can be remarkably improved. Can be. Even if the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer, it is obvious that the same effect can be obtained.
이상의 설명은 본 발명을 예시적으로 설명한 것에 불과한 것으로, 본 발명이 속하는 기술분야에서 통상의 지식을 가지는 자라면 본 발명의 본질적인 특성에서 벗어나지 않는 범위에서 다양한 변형이 가능할 것이다. 따라서, 본 명세서에 개시된 실시예들은 본 발명을 한정하기 위한 것이 아니라 설명 하기 위한 것이고, 이러한 실시예에 의하여 본 발명의 사상과 범위가 한정되는 것은 아니다. 본 발명의 보호범위는 아래의 청구범위에 의하여 해석되어야 하며, 그와 동등한 범위 내에 있는 모든 기술은 본 발명의 권리범위에 포함하는 것으로 해석되어야 할 것이다.The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains may various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention but to describe the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The protection scope of the present invention should be interpreted by the following claims, and all the technologies within the equivalent scope should be interpreted as being included in the scope of the present invention.
CROSS-REFERENCE TO RELATED APPLICATIONCROSS-REFERENCE TO RELATED APPLICATION
본 특허출원은 2011년 10월 13일 한국에 출원한 특허출원번호 제 10-2011-0104787 호에 대해 미국 특허법 119(a)조 (35 U.S.C § 119(a))에 따라 우선권을 주장하며, 그 모든 내용은 참고문헌으로 본 특허출원에 병합된다. 아울러, 본 특허출원은 미국 이외에 국가에 대해서도 위와 동일한 이유로 우선권을 주장하면 그 모든 내용은 참고문헌으로 본 특허출원에 병합된다.This patent application claims priority under No. 119 (a) (35 USC § 119 (a)) of the Patent Application No. 10-2011-0104787, filed with South Korea on October 13, 2011. All content is incorporated by reference in this patent application. In addition, if this patent application claims priority for the same reason for countries other than the United States, all its contents are incorporated into this patent application by reference.

Claims (9)

  1. 하기 화학식으로 표시되는 화합물.Compound represented by the following formula.
    Figure PCTKR2012008278-appb-I000059
    Figure PCTKR2012008278-appb-I000059
    상기 화학식에서,In the above formula,
    A환은 C6~C60의 단일 또는 다환의 방향족 또는 헤테로고리이며,A ring is a C 6 ~ C 60 single or polycyclic aromatic or heterocyclic ring,
    Y는 직접결합(단, n=2인 경우에 한함)이거나; 수소, 중수소, 할로겐, 니트릴기, 니트로기, -L-N(Ar1)(Ar2), C6~C60의 아릴기, 플루오렌일기, C2~C60의 헤테로고리기, C1~C30의 알콕시기, C6~C30의 아릴옥시기 및 C1~C50의 알킬기로 이루어진 1가의 치환기 군에서 선택되거나; 또는 C6~C60의 아릴렌기, 플루오렌일렌기, C6~C60의 방향족환과 C3~C60의 지환족이 융합된 고리, C2~C60의 헤테로고리기 또는 2가의 지방족탄화수소기로 이루어진 2가의 치환기 군에서 선택되며, n은 1 또는 2이고,Y is a direct bond, provided that n = 2; Hydrogen, deuterium, halogen, nitrile group, nitro group, -LN (Ar 1 ) (Ar 2 ), C 6 ~ C 60 aryl group, fluorenyl group, C 2 ~ C 60 heterocyclic group, C 1 ~ C 30 alkoxy group, C 6 ~ C 30 aryloxy and C 1 ~ C 50 monovalent substituent selected from the group consisting of an alkyl group or a; Or a C 6 to C 60 arylene group, a fluorenylene group, a C 6 to C 60 aromatic ring and a C 3 to C 60 alicyclic fused ring, a C 2 to C 60 heterocyclic group or a divalent aliphatic hydrocarbon Is selected from the group of divalent substituents consisting of groups, n is 1 or 2,
    R1 내지 R11은 서로 독립적으로 수소, 중수소, 할로겐, 니트릴기, 니트로기, -L-N(Ar1)(Ar2), C6~C60의 아릴기, 플루오렌일기, C2~C60의 헤테로고리기, C1~C30의 알콕시기, C6~C30의 아릴옥시기 및 C1~C50의 알킬기로 이루어진 군에서 선택되며, R 1 to R 11 are each independently hydrogen, deuterium, halogen, nitrile group, nitro group, -LN (Ar 1 ) (Ar 2 ), C 6 ~ C 60 aryl group, fluorenyl group, C 2 ~ C 60 Heterocyclic group, C 1 ~ C 30 Alkoxy group, C 6 ~ C 30 It is selected from the group consisting of aryloxy group and C 1 ~ C 50 Alkyl group,
    X는 S, SO 또는 SO2 이고,X is S, SO or SO 2 ,
    상기 L은 직접결합, C6~C60의 아릴렌기, 플루오렌일렌기, C6~C60의 방향족환과 C3~C60의 지환족이 융합된 고리, C2~C60의 헤테로고리기 또는 2가의 지방족탄화수소로 이루어진 군에서 선택되며, 상기 Ar1과 Ar2는 서로 독립적으로 C6~C60의 아릴기, C2~C60의 헤테로고리기, 플루오렌일기, C1~C30의 알콕시기, C6~C30의 아릴옥시기 및 C1~C50의 알킬기로 이루어진 군에서 선택된다.L is a direct bond, C 6 ~ C 60 arylene group, fluorenylene group, C 6 ~ C 60 aromatic ring and C 3 ~ C 60 alicyclic fused ring, C 2 ~ C 60 heterocyclic group Or divalent aliphatic hydrocarbon, wherein Ar 1 and Ar 2 are each independently C 6 -C 60 aryl group, C 2 -C 60 heterocyclic group, fluorenyl group, C 1 -C 30 Is selected from the group consisting of an alkoxy group, a C 6 -C 30 aryloxy group and a C 1 -C 50 alkyl group.
    (상기 Y, R1 내지 R11, Ar1 및 Ar2 의 C6~C60의 아릴기와, 상기 Y, R1 내지 R11, Ar1 및 Ar2 의 플루오렌일기와, 상기 Y 및 L의 아릴렌기와, 상기 Y 및 L의 플루오렌일렌기는, 중수소, 할로겐, 실란기, 붕소기, 게르마늄기, C1~C20 의 알킬싸이오기, C6~C20의 아릴싸이오기, C1~C20의 알콕시기, -N(Ar1)(Ar2), C1~C20의 알킬기, C7~C20의 아릴알킬기, C2~C20의 알케닐기, C8~C20의 아릴알케닐기, C2~C20의 알키닐기, C3~C20의 시클로알킬기, 중수소로 치환된 C6~C20의 아릴기 및 C2~C20의 헤테로고리기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있고,(In the Y, R 1 to R 11, Ar 1 and Ar 2 of C 6 ~ C 60 aryl group, wherein Y, R 1 to R 11, a fluorene group, and the Y and L of Ar 1 and Ar 2 The arylene group and the Y and L fluorenylene groups are deuterium, halogen, silane group, boron group, germanium group, C 1 ~ C 20 alkylthio group, C 6 ~ C 20 arylthio group, C 1 ~ C 20 alkoxy group, -N (Ar 1 ) (Ar 2 ), C 1 -C 20 alkyl group, C7-C20 arylalkyl group, C 2 -C 20 alkenyl group, C 8 -C 20 arylalkenyl group , substituted with one or more substituents selected from the alkynyl group, C 3 ~ C 20 cycloalkyl group, a C 6 ~ C 20 aryl group, and a hetero group, ring C 2 ~ C 20 substituted by deuterium of C 2 ~ C 20 Can be,
    상기 Y, R1 내지 R11, L, Ar1 및 Ar2 의 C6~C60의 헤테로고리기는 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하며, 중수소, 할로겐기, -N(Ar1)(Ar2), C1~C20의 알킬기, C7~C20의 아릴알킬기, C2~C20의 알케닐기, C8~C20의 아릴알케닐기, C1~C20의 알콕시기, C6~C60의 아릴기, 중수소로 치환된 C6~C20의 아릴기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있으며,The C 6 ~ C 60 heterocyclic group of Y, R 1 to R 11 , L, Ar 1, and Ar 2 include at least one heteroatom of O, N, S, Si, and P, deuterium, a halogen group, -N (Ar 1 ) (Ar 2 ), C 1 -C 20 alkyl group, C 7 -C 20 arylalkyl group, C 2 -C 20 alkenyl group, C 8 -C 20 arylalkenyl group, C 1- It may be substituted with one or more substituents selected from the group consisting of C 20 alkoxy group, C 6 ~ C 60 aryl group, C 6 ~ C 20 aryl group substituted with deuterium, a nitrile group and an acetylene group,
    상기 Y, R1 내지 R11, Ar1 및 Ar2의 C1~C30의 알콕시기 및 C6~C30의 아릴옥시기는 중수소, 할로겐기, 아미노기, 니트릴기, 니트로기, C1~C20 의 알킬기, C2~C20의 알케닐기, C1~C20의 알콕시기, C3~C30의 시클로알킬기, C6~C60의 아릴기, 중수소로 치환된 C6~C20의 아릴기 및 C2~C60의 헤테로고리기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있으며,The C 1 to C 30 alkoxy group and C 6 to C 30 aryloxy group of Y, R 1 to R 11 , Ar 1 and Ar 2 are deuterium, halogen, amino, nitrile, nitro, C 1 to C 20 alkyl groups, C 2 to C 20 alkenyl groups, C 1 to C 20 alkoxy groups, C 3 to C 30 cycloalkyl groups, C 6 to C 60 aryl groups, deuterium substituted with C 6 to C 20 It may be substituted with one or more substituents selected from the group consisting of an aryl group and a C 2 ~ C 60 heterocyclic group,
    상기 Y, R1 내지 R11, r1 및 Ar2의 C1~C50의 알킬기는 C2~C20의 알케닐기, C1~C20의 알콕시기, C6~C20의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C7~C20의 아릴알킬기, C8~C20의 아릴알케닐기, C2~C20의 헤테로고리기, 니트릴기 및 아세틸렌기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있다)The C 1 to C 50 alkyl group of Y, R 1 to R 11 , r 1 and Ar 2 may be C 2 to C 20 alkenyl group, C 1 to C 20 alkoxy group, C 6 to C 20 aryl group, In the group consisting of C 6 ~ C 20 aryl group, C 7 ~ C 20 arylalkyl group, C 8 ~ C 20 aryl alkenyl group, C 2 ~ C 20 heterocyclic group, nitrile group and acetylene group May be substituted with one or more substituents selected)
  2. 제 1항에 있어서,The method of claim 1,
    하기 화학식 중 하나로 표시되는 것을 특징으로 하는 화합물.Compound represented by one of the following formula.
    <화학식 2><Formula 2>
    Figure PCTKR2012008278-appb-I000060
    Figure PCTKR2012008278-appb-I000060
    <화학식 3><Formula 3>
    Figure PCTKR2012008278-appb-I000061
    Figure PCTKR2012008278-appb-I000061
    <화학식 4><Formula 4>
    Figure PCTKR2012008278-appb-I000062
    Figure PCTKR2012008278-appb-I000062
    (상기 화학식 2 내지 화학식 4에서 A환, R1~R11 및 X는 화학식 1에서 정의된 것과 동일하며, 화학식 2의 Y는 화학식 1의 Y 정의 중 1가 치환기 군에서 선택되며, 화학식 3의 Y는 직접결합이거나 화학식 1의 Y 정의 중 2가 치환기 군에서 선택되고, 화학식 4의 L, Ar1 및 Ar2는 화학식 1에서 정의된 것과 같다)(In Formula 2 to Formula 4, A ring, R 1 to R 11 and X are the same as defined in Formula 1, Y in Formula 2 is selected from the group of monovalent substituents in the Y definition of Formula 1, Y is a direct bond or is selected from the group of divalent substituents in the definition of Y in Formula 1, and L, Ar 1 and Ar 2 in Formula 4 are the same as defined in Formula 1)
  3. 제 1항에 있어서,The method of claim 1,
    하기 화학식 중 하나로 표시되는 것을 특징으로 하는 화합물.Compound represented by one of the following formula.
    <화학식 5><Formula 5>
    Figure PCTKR2012008278-appb-I000063
    Figure PCTKR2012008278-appb-I000063
    <화학식 6><Formula 6>
    Figure PCTKR2012008278-appb-I000064
    Figure PCTKR2012008278-appb-I000064
    <화학식 7><Formula 7>
    Figure PCTKR2012008278-appb-I000065
    Figure PCTKR2012008278-appb-I000065
    (상기 화학식 5 내지 화학식 7에서 R1~R8 및 X는 화학식 1에서 정의된 것과 같으며, 화학식 5의 Y는 화학식 1의 Y의 정의 중 1가 치환기 군에서 선택되며, 화학식 6의 Y는 직접결합이거나 화학식 1의 Y의 정의 중 2가 치환기 군에서 선택되며, 화학식 7의 L, Ar1 및 Ar2는 화학식 1에서 정의된 것과 같다)(R 1 to R 8 and X in Formula 5 to Formula 7 are the same as defined in Formula 1, Y in Formula 5 is selected from the monovalent substituent group in the definition of Y in Formula 1, Y in Formula 6 is Or a divalent substituent in the definition of Y in Formula 1, wherein L, Ar 1 and Ar 2 in Formula 7 are as defined in Formula 1)
  4. 제 1항에 있어서,The method of claim 1,
    하기 화합물 중 하나인 것을 특징으로 하는 화합물.Compound which is one of the following compounds.
    Figure PCTKR2012008278-appb-I000066
    Figure PCTKR2012008278-appb-I000066
    Figure PCTKR2012008278-appb-I000067
    Figure PCTKR2012008278-appb-I000067
    Figure PCTKR2012008278-appb-I000068
    Figure PCTKR2012008278-appb-I000068
    Figure PCTKR2012008278-appb-I000069
    Figure PCTKR2012008278-appb-I000069
    Figure PCTKR2012008278-appb-I000070
    Figure PCTKR2012008278-appb-I000070
    Figure PCTKR2012008278-appb-I000071
    Figure PCTKR2012008278-appb-I000072
    Figure PCTKR2012008278-appb-I000073
    Figure PCTKR2012008278-appb-I000071
    Figure PCTKR2012008278-appb-I000072
    Figure PCTKR2012008278-appb-I000073
    Figure PCTKR2012008278-appb-I000074
    Figure PCTKR2012008278-appb-I000074
    Figure PCTKR2012008278-appb-I000075
    Figure PCTKR2012008278-appb-I000075
    Figure PCTKR2012008278-appb-I000076
    Figure PCTKR2012008278-appb-I000076
    Figure PCTKR2012008278-appb-I000077
    Figure PCTKR2012008278-appb-I000077
    Figure PCTKR2012008278-appb-I000078
    Figure PCTKR2012008278-appb-I000078
    Figure PCTKR2012008278-appb-I000079
    Figure PCTKR2012008278-appb-I000079
    Figure PCTKR2012008278-appb-I000080
    Figure PCTKR2012008278-appb-I000080
    Figure PCTKR2012008278-appb-I000081
    Figure PCTKR2012008278-appb-I000081
    Figure PCTKR2012008278-appb-I000082
    Figure PCTKR2012008278-appb-I000082
    Figure PCTKR2012008278-appb-I000083
    Figure PCTKR2012008278-appb-I000083
    Figure PCTKR2012008278-appb-I000084
    Figure PCTKR2012008278-appb-I000084
    Figure PCTKR2012008278-appb-I000085
    Figure PCTKR2012008278-appb-I000085
    Figure PCTKR2012008278-appb-I000086
    Figure PCTKR2012008278-appb-I000086
    Figure PCTKR2012008278-appb-I000087
    Figure PCTKR2012008278-appb-I000087
    Figure PCTKR2012008278-appb-I000088
    Figure PCTKR2012008278-appb-I000088
    Figure PCTKR2012008278-appb-I000089
    Figure PCTKR2012008278-appb-I000089
    Figure PCTKR2012008278-appb-I000090
    Figure PCTKR2012008278-appb-I000090
    Figure PCTKR2012008278-appb-I000091
    Figure PCTKR2012008278-appb-I000091
    Figure PCTKR2012008278-appb-I000092
    Figure PCTKR2012008278-appb-I000092
  5. 순차적으로 적층된 제 1 전극, 1층 이상의 유기물층 및 제 2전극을 포함하는 유기전기소자에 있어서,In an organic electric device comprising a first electrode, one or more organic material layers and a second electrode sequentially stacked,
    상기 유기물층은 제 1항의 화합물을 포함하는 것을 특징으로 하는 유기전기소자.The organic material layer is an organic electroluminescent device comprising the compound of claim 1.
  6. 제 5항에 있어서,The method of claim 5,
    용액공정(soluble process)에 의해 상기 화합물을 상기 유기물층으로 형성하는 것을 특징으로 하는 유기전기소자. An organic electric device, characterized in that to form the compound into the organic material layer by a solution process (soluble process).
  7. 제 5항에 있어서,The method of claim 5,
    상기 유기물층은 발광층 및/또는 정공수송층을 포함하며,The organic material layer includes a light emitting layer and / or a hole transport layer,
    상기 발광층 및 상기 정공수송층 중 적어도 일층은 상기 화합물로 형성된 것을 특징으로 하는 유기전기소자.At least one of the light emitting layer and the hole transport layer is formed of the compound.
  8. 제 5항의 유기전기소자를 포함하는 디스플레이장치; 및 A display device comprising the organic electroluminescent device of claim 5; And
    상기 디스플레이장치를 구동하는 제어부; 를 포함하는 전자장치.A controller for driving the display device; Electronic device comprising a.
  9. 제 8항의 유기전기소자는 유기전기발광소자(OLED), 유기태양전지, 유기감광체(OPC), 유기트랜지스터(유기 TFT), 단색 또는 백색 조명용 소자 중 하나인 것을 특징으로 하는 전자장치.The electronic device of claim 8, wherein the organic electronic device is one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a single color or white light emitting device.
PCT/KR2012/008278 2011-10-13 2012-10-11 Compound for organic electrical device, organic electrical device using same, and electronic device thereof WO2013055132A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR20110104787 2011-10-13
KR10-2011-0104787 2011-10-13

Publications (2)

Publication Number Publication Date
WO2013055132A2 true WO2013055132A2 (en) 2013-04-18
WO2013055132A3 WO2013055132A3 (en) 2013-07-04

Family

ID=48082664

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2012/008278 WO2013055132A2 (en) 2011-10-13 2012-10-11 Compound for organic electrical device, organic electrical device using same, and electronic device thereof

Country Status (2)

Country Link
KR (1) KR102079019B1 (en)
WO (1) WO2013055132A2 (en)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014034793A1 (en) * 2012-08-30 2014-03-06 出光興産株式会社 Aromatic amine derivative, and organic electroluminescent element using same
WO2014181878A1 (en) * 2013-05-10 2014-11-13 東ソー株式会社 Arylamine compound and use thereof
US20160099423A1 (en) * 2014-10-06 2016-04-07 Samsung Display Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
US20160322581A1 (en) * 2015-04-30 2016-11-03 Samsung Display Co., Ltd. Organic light-emitting device
KR20160129191A (en) * 2015-04-29 2016-11-09 삼성디스플레이 주식회사 Organic light emitting device comprising the same
WO2017022729A1 (en) * 2015-07-31 2017-02-09 出光興産株式会社 Compound, material for organic electroluminescent elements, organic electroluminescent element and electronic device
US20170186974A1 (en) * 2015-12-24 2017-06-29 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
WO2017209297A1 (en) * 2016-06-02 2017-12-07 国立大学法人名古屋大学 Triarylene compound and method for producing same
CN111499618A (en) * 2020-05-15 2020-08-07 上海天马有机发光显示技术有限公司 Compound and organic photoelectric device comprising same
JP2020152655A (en) * 2019-03-19 2020-09-24 東ソー株式会社 Benzoheterophenanthrene compound having condensed ring group and use thereof
US11038124B2 (en) 2018-10-03 2021-06-15 Luminescence Technology Corp. Organic compound and organic electroluminescence device using the same
CN113330096A (en) * 2018-10-03 2021-08-31 马克斯·普朗克索赔科学公司 Use of substituted or unsubstituted polycyclic aromatic hydrocarbon compounds for high resolution microscopy
CN113330096B (en) * 2018-10-03 2024-05-31 马克斯·普朗克索赔科学公司 Use of substituted or unsubstituted polycyclic aromatic compounds for high resolution microscopy

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6223558B2 (en) * 2013-06-14 2017-11-01 エルジー・ケム・リミテッド Organic solar cell and manufacturing method thereof
KR102212965B1 (en) * 2014-06-18 2021-02-05 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
KR20160030001A (en) * 2014-09-05 2016-03-16 삼성디스플레이 주식회사 Condensed-cyclic compound and organic light emitting device comprising the same
JP6844826B2 (en) * 2016-07-27 2021-03-17 エルジー・ケム・リミテッド Multiple ring compounds and organic light emitting devices containing them
KR102564917B1 (en) * 2020-12-21 2023-08-09 엘티소재주식회사 Heterocyclic compound, organic light emitting device comprising the same, and composition for organic layer of organic light emitting device

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011037429A2 (en) * 2009-09-28 2011-03-31 덕산하이메탈(주) Compounds having 5-membered aryl-ring-condensed heterocyclic derivatives, organic electronic device using the compounds, and terminal comprising the organic electronic device

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101219481B1 (en) * 2009-09-28 2013-01-15 덕산하이메탈(주) Compound Containing Heterocyclic 5-Membered Ring Derivative Condensed Aryl Ring And Organic Electronic Element Using The Same, Terminal Thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011037429A2 (en) * 2009-09-28 2011-03-31 덕산하이메탈(주) Compounds having 5-membered aryl-ring-condensed heterocyclic derivatives, organic electronic device using the compounds, and terminal comprising the organic electronic device

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
FRACHE. G. ET AL.: 'Post-source Decay of Alkylated and Functionalized Polycyclic Aromatic Compounds' RAPID COMMUNICATIONS IN MASS SPECTROMETRY vol. 21, 2007, ISSN 0951-4198 pages 2601 - 2607 *
KITAMURA, T ET AL.: 'Exclusive Cyclization at Sulfur in Photolysis of beta-[o-arylthio)phenyl] vinyl Bromides' CHEMISTRY LETTERS 1986, ISSN 0366-7022 pages 839 - 842 *
KITAMURA, T. ET AL.: 'Phenyl Migration to Thiophene Ring in Photolysis of 1-Phenylbenzo [b]thiophenium Salts' TETRAHEDRON LETTERS vol. 38, no. 29, 1997, ISSN 0040-4039 pages 5157 - 5160 *
LIANG, F. ET AL.: 'Determination of Polycyclic Aromatic Sulfur Heterocycles in Diesel Particulate Matter and Diesel Fuel by Gas Chromatography with Atomic Emission Detection' JOURNAL OF CHROMATOGRAPHY A vol. 1114, 2006, ISSN 0021-9673 pages 145 - 153 *
NAGAO, I. ET AL.: '9-Stannafluorenes: 1,4-Dimetal Equivalents for Aromatic Annulation by Double Cross-Coupling' ANGEWANDTE CHEMIE vol. 48, 2009, ISSN 1433-7851 pages 7573 - 7576 *

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014034793A1 (en) * 2012-08-30 2014-03-06 出光興産株式会社 Aromatic amine derivative, and organic electroluminescent element using same
US10985325B2 (en) 2012-08-30 2021-04-20 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element using same
WO2014181878A1 (en) * 2013-05-10 2014-11-13 東ソー株式会社 Arylamine compound and use thereof
JP2015096484A (en) * 2013-05-10 2015-05-21 東ソー株式会社 Arylamine compound and use thereof
US9856243B2 (en) 2014-10-06 2018-01-02 Samsung Display Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
US20160099423A1 (en) * 2014-10-06 2016-04-07 Samsung Display Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
EP3006436A1 (en) * 2014-10-06 2016-04-13 Samsung Display Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
CN105481829A (en) * 2014-10-06 2016-04-13 三星显示有限公司 Condensed cyclic compound and organic light-emitting device including the same
KR20160129191A (en) * 2015-04-29 2016-11-09 삼성디스플레이 주식회사 Organic light emitting device comprising the same
US20160329501A1 (en) * 2015-04-29 2016-11-10 Samsung Display Co., Ltd. Organic light emitting device
KR102370354B1 (en) 2015-04-29 2022-03-07 삼성디스플레이 주식회사 Organic light emitting device comprising the same
US9923147B2 (en) * 2015-04-29 2018-03-20 Samsung Display Co., Ltd. Organic light emitting device
US20160322581A1 (en) * 2015-04-30 2016-11-03 Samsung Display Co., Ltd. Organic light-emitting device
US9859503B2 (en) * 2015-04-30 2018-01-02 Samsung Display Co., Ltd. Organic light-emitting device
US11117857B2 (en) 2015-07-31 2021-09-14 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element and electronic device
WO2017022729A1 (en) * 2015-07-31 2017-02-09 出光興産株式会社 Compound, material for organic electroluminescent elements, organic electroluminescent element and electronic device
US11939279B2 (en) 2015-07-31 2024-03-26 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element and electronic device
US9960367B2 (en) * 2015-12-24 2018-05-01 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
US20170186974A1 (en) * 2015-12-24 2017-06-29 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
WO2017209297A1 (en) * 2016-06-02 2017-12-07 国立大学法人名古屋大学 Triarylene compound and method for producing same
US11038124B2 (en) 2018-10-03 2021-06-15 Luminescence Technology Corp. Organic compound and organic electroluminescence device using the same
CN113330096A (en) * 2018-10-03 2021-08-31 马克斯·普朗克索赔科学公司 Use of substituted or unsubstituted polycyclic aromatic hydrocarbon compounds for high resolution microscopy
CN113330096B (en) * 2018-10-03 2024-05-31 马克斯·普朗克索赔科学公司 Use of substituted or unsubstituted polycyclic aromatic compounds for high resolution microscopy
JP2020152655A (en) * 2019-03-19 2020-09-24 東ソー株式会社 Benzoheterophenanthrene compound having condensed ring group and use thereof
CN111499618A (en) * 2020-05-15 2020-08-07 上海天马有机发光显示技术有限公司 Compound and organic photoelectric device comprising same

Also Published As

Publication number Publication date
KR20130040133A (en) 2013-04-23
KR102079019B1 (en) 2020-02-20
WO2013055132A3 (en) 2013-07-04

Similar Documents

Publication Publication Date Title
WO2013055132A2 (en) Compound for organic electrical device, organic electrical device using same, and electronic device thereof
WO2019124902A1 (en) Organic electronic element using organic electronic element compound, and electronic device therefor
WO2011037429A2 (en) Compounds having 5-membered aryl-ring-condensed heterocyclic derivatives, organic electronic device using the compounds, and terminal comprising the organic electronic device
WO2014003336A1 (en) Compound, electro-organic device using same, and electronic device thereof
WO2014142472A1 (en) Compound for organic electrical element, organic electrical element using same, and electronic device thereof
WO2015083948A1 (en) Compound for organic electric element, organic electric element using same, and electronic device thereof
WO2017105078A1 (en) Compound for organic electrical element, organic electrical element using same, and electronic device thereof
WO2016056757A2 (en) Compound for organic electronic element, and organic electronic element and electronic apparatus using same
WO2021141356A1 (en) Compound for organic electronic element, organic electronic element using same, and electronic device thereof
WO2013009079A1 (en) Triphenylene-based compound and organic electroluminescent diode using same
WO2011149283A2 (en) Compound comprising a five-membered hetero ring, an organic electrical element using the same and a terminal thereof
WO2018056649A1 (en) Compound for organic electronic element, organic electronic element using same and electronic device therefor
WO2014142467A1 (en) Compound for organic electronic element, organic electronic element using compound, and electronic device comprising organic electronic element
WO2017052129A1 (en) Novel compound for organic electric device, organic electric device using same, and electronic device comprising same
WO2018056658A1 (en) Compound for organic electronic element, organic electronic element using same and electronic device therefor
WO2011108901A2 (en) Spiro-carbazole compound comprising a spiro skeleton, and an organic electronic element using the same and a terminal thereof
WO2011010842A2 (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
WO2011149284A2 (en) Hetero-atom-containing compound in which carbazole and fluorene are fused, an organic electrical element using the same and a terminal thereof
WO2019112214A1 (en) Compound for organic electric element, organic electric element using same, and electronic device thereof
WO2015030469A1 (en) Compound for organic electrical element, organic electrical element using same, and electronic device thereof
WO2019143031A1 (en) Compound for organic electric element, organic electric element using same, and electronic apparatus employing same
WO2019124903A1 (en) Compound for organic electronic device, organic electronic device using same, and electronic device therefor
WO2019093665A1 (en) Organic electronic device using compound for organic electronic device, and electronic apparatus thereof
WO2014137104A1 (en) Compound for organic electronic element, organic electronic element comprising compound, and electronic device using organic electronic element
WO2017022983A1 (en) Compound for organic electrical element, organic electrical element using compound, and electronic device therefor

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: 12840346

Country of ref document: EP

Kind code of ref document: A2

122 Ep: pct application non-entry in european phase

Ref document number: 12840346

Country of ref document: EP

Kind code of ref document: A2