WO2008127057A1 - Material for organic photoelectric device including electron transporting unit and hole transporting unit, and organic photoelectric device including the same - Google Patents

Material for organic photoelectric device including electron transporting unit and hole transporting unit, and organic photoelectric device including the same Download PDF

Info

Publication number
WO2008127057A1
WO2008127057A1 PCT/KR2008/002098 KR2008002098W WO2008127057A1 WO 2008127057 A1 WO2008127057 A1 WO 2008127057A1 KR 2008002098 W KR2008002098 W KR 2008002098W WO 2008127057 A1 WO2008127057 A1 WO 2008127057A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
unsubstituted
substituted
organic
photoelectric device
Prior art date
Application number
PCT/KR2008/002098
Other languages
French (fr)
Inventor
Eun-Sun Yu
Nam-Soo Kim
Young-Hoon Kim
Mi-Young Chae
Eui-Su Kang
Original Assignee
Cheil Industries Inc.
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 Cheil Industries Inc. filed Critical Cheil Industries Inc.
Priority to EP08741343.1A priority Critical patent/EP2134809B1/en
Priority to CN2008800107618A priority patent/CN101657517B/en
Priority to JP2010502951A priority patent/JP5364089B2/en
Publication of WO2008127057A1 publication Critical patent/WO2008127057A1/en
Priority to US12/588,365 priority patent/US8247805B2/en
Priority to US13/550,772 priority patent/US20120280221A1/en

Links

Classifications

    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • 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
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
    • 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
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the present invention relates to a material for an organic photoelectric device and an organic photoelectric device including the same. More particularly, the present invention relates to a material for an organic photoelectric device having thermal stability due to a glass transition temperature (Tg) of 120 ° C or more and a thermal decomposition temperature of 400° C or more, having bipolar characteristics due to good hole and electron transporting properties, and being capable of realizing high efficiency of an organic photoelectric device, and an organic photoelectric device including the same.
  • Tg glass transition temperature
  • a photoelectric device is, in a broad sense, a device for transforming photo energy to electrical energy, and conversely, for transforming electrical energy to photo energy.
  • the photoelectric device may be exemplified by an organic light emitting diode, a solar cell, a transistor, and so on.
  • the organic light emitting device employing organic light emitting diodes has recently drawn attention due to the increase in demand for flat panel displays.
  • the organic light emitting device transforms electrical energy into light by applying current to an organic light emitting material. It has a structure in which a functional organic material layer is interposed between an anode and a cathode.
  • the organic light emitting diode has similar electrical characteristics to those of light emitting diodes (LED) in which holes are injected from an anode and electrons are injected from a cathode, then the holes and electrons move to opposite electrodes and are recombined to form excitons having high energy.
  • the formed excitons generate lights having a certain wavelength while shifting to a ground state.
  • the organic light emitting diode is composed of an anode of a transparent electrode, an organic thin layer of a light emitting region, and a metal electrode (cathode) formed on a glass substrate, in that order.
  • the organic thin layer may includes an emission layer, a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection layer (EIL). It may further include an electron blocking layer or a hole blocking layer due to the emission characteristics of the emission layer.
  • the holes and electrons are injected from the anode and the cathode, respectively.
  • the injected holes and electrons are recombined on the emission layer though the hole transport layer (HTL) and the electron transport layer (ETL) to provide light emitting excitons.
  • HTL hole transport layer
  • ETL electron transport layer
  • the provided light emitting excitons emit light by transiting to the ground state.
  • the light emitting may be classified as a fluorescent material including singlet excitons and a phosphorescent material including triplet excitons.
  • the duration of fluorescent emission is extremely short at several nanoseconds, but the duration of phosphorescent emission is relatively long such as at several microseconds, so that it provides a characteristic of extending the lifetime (emission duration) to more than that of the fluorescent emission.
  • the singlet and the triplet are produced in a ratio of 1 :3, in which the triplet light emitting excitons are produced at three times the amount of the singlet light emitting excitons in the organic light emitting diode.
  • the percentage of the singlet exited state is 25% (the triplet is 75%) in the case of a fluorescent material, so it has limits in luminous efficiency
  • a phosphorescent material it can utilize 75% of the triplet exited state and 25% of the singlet exited state, so theoretically the internal quantum efficiency can reach up to 100%.
  • phosphorescent light emitting material it has advantages in an increase in luminous efficiency of around four times than that of the fluorescent light emitting material.
  • the organic host material can be exemplified by a material including naphthalene, anthracene, phenanthrene, tetracene, pyrene, benzopyrene, chrysene, pycene, carbazole, fluorene, biphenyl, terphenyl, triphenylene oxide, dihalobi phenyl, trans-stilbene, and 1 ,4- diphenylbutadiene.
  • the host material includes 4,4-N,N-dicarbazolebiphenyl (CBP) having a glass transition temperature of 110 ° C or less and a thermal decomposition temperature of 400 ° C or less, in which the thermal stability is low and the symmetry is excessively high. Thereby, it tends to crystallize and cause problems such as a short and a pixel defection according to results of thermal resistance tests of the devices.
  • CBP 4,4-N,N-dicarbazolebiphenyl
  • most host materials including CBP are materials in which the hole transporting property is greater than the electron transporting property.
  • the excitons are ineffectively formed in the emission layer. Therefore, the resultant device has deteriorated luminous efficiency.
  • a material for an organic photoelectric device having thermal stability due to a glass transition temperature (Tg) of 120° C or more and a thermal decomposition temperature of 400 ° C or more, having bipolar characteristics due to good hole and electron transporting properties, and being capable of realizing a high efficiency organic photoelectric device.
  • Tg glass transition temperature
  • 400 ° C or more thermal decomposition temperature
  • an organic photoelectric device having high luminous efficiency and a long life-span.
  • One embodiment of the present invention provides a material for an organic photoelectric device that includes the compound represented by the following Formula 1.
  • the material is a bipolar organic compound including both a hole transporting unit and an electron transporting unit.
  • the pyridine (C 6 H 5 N) is an electron transporting unit
  • the HTU and HTU 1 independently are as a hole transporting unit
  • the HTU and HTU 1 are the same or different.
  • Another embodiment of the present invention provides an organic photoelectric device that includes an anode, a cathode, and organic thin layers disposed between the anode and cathode.
  • the organic thin layer includes the above material for an organic photoelectric device.
  • the material for an organic photoelectric device can provide an organic photoelectric device having high luminous efficiency at a low driving voltage.
  • FIGS. 1 to 5 are cross-sectional views showing organic photoelectric devices including organic compounds according to various embodiments of the present invention.
  • the material for an organic photoelectric device includes a compound represented by the following Formula 1.
  • the material is a bipolar organic compound including both a hole transporting unit and an electron transporting unit.
  • the pyridine (C 6 H 5 N) is an electron transporting unit
  • the HTU and HTU 1 independently are a hole transporting unit
  • the HTU and HTU' are the same or different.
  • X and Y are independently selected from the group consisting of nitrogen (N), sulfur (S), and oxygen (O).
  • Ar 1 and Ar 2 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 alkylene, a substituted or unsubstituted C2 to C30 heteroaryl, and a substituted or unsubstituted C2 to C30 heteroarylene.
  • R 1 to R 4 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C2 to C30 heteroarylene, a substituted or unsubstituted C1 to C30 alkyl, and a substituted or unsubstituted C1 to C30 alkylene.
  • R 1 and R 2 form a cyclic ring or R 3 and R 4 form a cyclic ring.
  • R 2 When X is sulfur or oxygen, R 2 is a unshared electron pair, and when Y is sulfur or oxygen, R 4 is a unshared electron pair.
  • m and n are independently integers ranging from 0 to 3, m+n is more than or equal to 1 , and o and p are integers ranging from 0 to 2.
  • substituted refers to one substituted with at least a substituent selected from the group consisting of a halogen, a cyano, a hydroxy, an amino, a C1 to C30 alkyl, a C3 to C30 cycloalkyl, a C6 to C30 aryl, and a C2 to C30 heteroaryl.
  • hetero refers to one including 1 to 3 heteroatoms selected from the group consisting of nitrogen (N), oxygen (O), sulfur (S), phosphorus (P), and Si (silicon) instead of carbon.
  • the organic compound having the above Formula 2 may be represented by the following Formula 3.
  • Ar 3 and Ar 4 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 alkylene, a substituted or unsubstituted C2 to C30 heteroaryl, and a substituted or unsubstituted C2 to C30 heteroarylene.
  • R b to R 8 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C2 to C30 heteroarylene, a substituted or unsubstituted C1 to C30 alkyl, and a substituted or unsubstituted
  • R 5 and R 6 form a cyclic ring or R 7 and R 8 form a cyclic ring.
  • m and n are independently integers ranging from 0 to 3, and m+n is more than or equal to 1.
  • Ar 5 to Ar 10 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 alkylene, a substituted or unsubstituted C2 to C30 heteroaryl, and a substituted or unsubstituted C2 to C30 heteroarylene.
  • Ar 5 and Ar 6 form a cyclic ring
  • Ar 7 and Ar 8 form a cyclic ring
  • Ar 9 and Ar 10 form a cyclic ring.
  • q is an integer ranging from 0 to 2.
  • the organic compound having the above Formula 3 may be represented by the following Formula 5.
  • Ar 11 to Ar 15 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 alkylene, a substituted or unsubstituted C2 to C30 heteroaryl, and a substituted or unsubstituted C2 to C30 heteroarylene.
  • Ar 12 and Ar 13 form a cyclic ring
  • Air 14 and Ar 15 form a cyclic ring.
  • r is an integer ranging from 0 to 2.
  • At least one substituent selected from the group consisting of XR 1 R 2 , YR 3 R 4 , and a combination thereof may be selected from the following Formulae 6a to 6d.
  • Ar 16 and Ar 17 are independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl and a substituted or unsubstituted C2 to C30 heteroaryl.
  • R 9 to R 14 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C2 to C20 alkoxy, and SiR 15 Ri 6 Ru (where R- 15 to Rr / are independently selected from the group consisting of a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C3 to C30 cycloalkyl, a nitrile, a cyano, a nitro, a carbonyl, and an amide), si to S 6 are independently integers ranging from 0 to 4.
  • the organic compounds having the above Formulae 1 to 5 have thermal stability such as a glass transition temperature (Tg) of 120° C or more, and a thermal decomposition temperature (Td) of 400° C or more.
  • Tg glass transition temperature
  • Td thermal decomposition temperature
  • the organic compounds having the above Formula 2 may be selected from the group consisting of the following compounds (1) to (41), and combinations thereof, but are not limited thereto.
  • the organic compounds having the above Formula 5 may be selected from the group consisting of the following compounds (42) to (52), and combinations thereof, but are not limited thereto.
  • the exemplary organic compound may be used by itself, but it is generally used as a host material that is capable of binding with a dopant.
  • the dopant is a compound having a high emission property, by itself.
  • the dopant is a material that is doped to the host material to emit light, and generally includes a metal complex that emits light due to multiplet excitation into a triplet or higher state.
  • the dopant includes a phosphorescent dopant material.
  • the material should satisfy the requirement to have a high light emitting quantum efficiency, to be rarely agglomerated, and to be distributed uniformly in the host material.
  • the phosphorescent dopant is an organic metal compound including at least element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, and combinations thereof.
  • the blue phosphorescent dopant may include (4,6-F 2 PPy)2lrpic (reference: Appl. Phys. Lett., 79, 2082-2084, 2001).
  • FIGS. 1 to 5 are cross-sectional views showing organic photoelectric devices including the organic compounds according to various embodiments of the present invention.
  • An organic photoelectric device according to one embodiment of the present invention includes at least one layer of an organic thin layer interposed between an anode and a cathode.
  • the anode includes a transparent electrode such as ITO (indium tin oxide), and the cathode includes a metal electrode such as aluminum.
  • the organic photoelectric device 100 includes an organic thin layer 105 including only an emission layer 130.
  • a double-layered organic photoelectric device 200 includes an organic thin layer 105 including an emission layer 230 including an electron transport layer (ETL) (not shown), and a hole transport layer (HTL) 140.
  • the hole transport layer (HTL) 140 is a separate layer having an excellent binding property with a transparent electrode such as ITO or a excellent hole transporting property.
  • a three-layered organic photoelectric device 300 includes the organic thin layer 105 including an electron transport layer (ETL) 150, an emission layer 130, and a hole transport layer (HTL) 140.
  • the emission layer 130 is independently installed, and layers having an excellent electron transporting property or an excellent hole transporting property are separately stacked.
  • a four-layered organic photoelectric device 400 includes the organic thin layer 105 including an electron injection layer (EIL) 160, an emission layer 130, a hole transport layer (HTL) 140, and a hole injection layer (HIL) 170 for binding with the cathode of ITO, different from the structure of the three-layered organic photoelectric device 300 shown in FIG. 3.
  • EIL electron injection layer
  • HTL hole transport layer
  • HIL hole injection layer
  • a five layered organic photoelectric device 500 includes the organic thin layer 105 including an electron transport layer (ETL) 150, an emission layer 130, a hole transport layer (HTL) 140, and a hole injection layer (HIL) 170, and further includes an electron injection layer (EIL) 160 to achieve the low voltage.
  • ETL electron transport layer
  • HTL hole transport layer
  • HIL hole injection layer
  • EIL electron injection layer
  • the method may follow a dry coating method such as evaporation, sputtering, plasma plating, and ion plating, or a wet coating method such as spin coating, dipping, and flow coating.
  • a dry coating method such as evaporation, sputtering, plasma plating, and ion plating
  • a wet coating method such as spin coating, dipping, and flow coating.
  • At least one layer selected from the group consisting of the emission layer, electron transport layer (ETL), electron injection layer (EIL), hole transport layer (HTL), hole injection layer (HIL), hole blocking layer, and combination thereof includes a material for the organic photoelectric device.
  • the organic thin layer includes the phosphorescent light emitting compound such as a metal complex that emits light due to the multiple excitation into a triplet or higher state.
  • the phosphorescent light emitting compound such as a metal complex that emits light due to the multiple excitation into a triplet or higher state.
  • the reaction fluid was separated into two layers, and an organic layer thereof was cleaned with a sodium chloride saturated aqueous solution and dried with anhydrous sodium sulfate. Subsequently, the organic solvent was removed by distillation under reduced pressure, and the residue was recrystallized with toluene. The precipitated crystals were separated by filtration and cleaned with toluene to provide 5.5g (77.3%) of the compound (3).
  • the reaction fluid was cooled to room temperature, and separated into two layers. Then, the solvent of an organic layer thereof was removed under a reduced pressure to provide a fluid. The fluid was separated by column chromatography (hexane) to remove the solvent and to provide 15g of a gel intermediate (C) at a yield of 83%.
  • Step 2 Synthesis of Intermediate (D) 7g (24mmol) of the intermediate (C) was dissolved in 50ml of tetrahydrofuran, and added with 15ml (24mmol) of an n-butyl lithium hexane solution (1.6M) under an argon atmosphere at -7O 0 C. The obtained solution was agitated at -70 0 C for 30 minutes, and the reaction fluid was slowly added with 47.9ml (235mmol) of isopropyl tetramethyl dioxaborolane in a dropwise fashion. After the obtained solution was agitated at -7O 0 C for 1 hour, it was heated to room temperature and agitated for 6 hours. To the obtained reaction solution, 200ml of water was added and agitated for 20 minutes.
  • the reaction fluid was cooled to room temperature and recrystallized with methanol.
  • the precipitated crystals were separated by filtration, and the obtained residue was purified with silica gel column chromatography to provide 36.7g of the intermediate (E) at a yield of 62.4%.
  • 35.Og (72mmol) of the intermediate (E) was dissolved in 350 ml of tetrahydrofuran and added with 61.5ml (98mmol) of an n-butyl lithium hexane solution (1.6M) under an argon atmosphere at -7O 0 C.
  • the obtained solution was agitated at -7O 0 C to 4O 0 C for 1 hour.
  • the reaction flux was frozen to -7O 0 C and slowly added with 29.3ml (144mmol) of isopropyl tetramethyl dioxaborolane in a dropwise fashion.
  • the obtained solution was agitated at -7O 0 C for 1 hour, and heated to room temperature and agitated for 6 hours.
  • the obtained reaction solution was added with 200ml of water and agitated for 20 minutes.
  • triphenylphosphine palladium were suspended in 200ml of toluene, 200ml of tetrahydrofuran, and 50ml of purified water, then heated and agitated for 24 hours.
  • the compound 18 was synthesized according to the same method as in Example 3, except that an intermediate (H) was used instead of the intermediate (B). MS(ESI) m/z 729.25 (M+H) +
  • a compound (36) was prepared in accordance with the same procedure as in Example 3, except that an intermediate (I) was used instead of the intermediate (B). MS(ESI) m/z 779.26 (M+H) +
  • the reaction fluid was separated into two layers, and an organic layer thereof was cleaned with a sodium chloride saturated aqueous solution and dried with anhydrous sodium sulfate. Subsequently, the organic solvent was removed by distillation under reduced pressure, and the residue was recrystallized with toluene. The precipitated crystals were separated by filtration and cleaned with toluene to provide 5.5g of the intermediate (J).
  • CBP is a compound represented by the following Formula.
  • the organic compounds according to the above Examples of the present invention had a glass transition temperature (Tg) of 12O 0 C or more and a thermal decomposition temperature (Td) of 430 0 C or more according to the DSC and TGA measurement results, which shows that the organic compounds had much higher thermal stability than that of the comparative material, CBP.
  • Tg glass transition temperature
  • Td thermal decomposition temperature
  • (Al) was provided in a thickness of 1000A for a cathode.
  • the method of manufacturing an organic photoelectric device may be described in detail as follows: cutting an ITO glass substrate having a sheet resistance value of 15 ⁇ /cm 2 into a size of 50mm x 50mm x 0.7mm for a cathode; ultrasonic wave cleaning the same in acetone, isopropyl alcohol, and pure water for 15 minutes, respectively; and UV ozone cleaning for 30 minutes.
  • N,N l -di(1-naphthyl)-N,N'-diphenylbenzidine (NPD) was deposited on the upper surface of the substrate under the conditions of a vacuum degree of 650 x i0 'r Pa and a deposition speed of 0.1 to 0.3nm/s to provide a hole transport layer (HTL).
  • the host material and the phosphorescent dopant were simultaneously deposited to provide an emission layer having a thickness of 300A.
  • a phosphorescent dopant of lr(PPy) 3 was deposited at the same time, and the adding amount of the phosphorescent dopant was adjusted to 5 wt%.
  • AIq 3 were deposited on the upper surface of the emission layer under the same vacuum deposition conditions to provide a hole blocking layer and an electron transport layer (ETL).
  • ETL electron transport layer
  • LiF and Al were sequentially deposited to provide an organic photoelectric device having the following structure A.
  • Structure A NPD 700A/EML (5wt%, 300A)/BAIq 50A/Alq 3 200A/LiF 5A/AI
  • TCTA denotes 4,4',4"-tris(N-carbazolyl)triphenylamine (4,4',4"-tris(N- carbazolyl)triphenylamine).
  • Structure B NPD 700A/EML (5wt%, 300A)/Alq 3 250A/UF 5A/AI
  • Structure C NPD 600A/TCTA 100A/EML (5wt%, 300A)/Alq 3 25 ⁇ A/LiF 5A/AI
  • Each of obtained organic photoelectric devices was measured for a current value passing through the unit device using a current-voltage meter (Keithley 2400) while increasing the voltage from OV to 10V. The results are calculated by dividing the measured current value by the area. 2) Luminance according to a voltage change
  • Each of obtained organic photoelectric devices was measured for luminance by a luminance meter (Minolta Cs-IOOOA) while increasing the voltage from OV to 10V.
  • Luminous efficiency was calculated from the luminance, current density, and voltage.
  • Luminous efficiency of the organic photoelectric device having the structure A is shown in the following Table 2.
  • Luminance, driving voltages, and color coordinates are also shown in the following Table 2.
  • devices including hosts of the organic compounds according to the above Examples of the present invention had driving voltages of 5V or less (3.9-5. OV), which were around 2V less than that of comparative material at the same luminance of 100nit, and improved luminous efficiency that was significantly more than that of comparative material.
  • Table 3 shows the results of measuring characteristics of the organic photoelectric device having structure B.
  • devices including hosts of the organic compounds according to the above Examples of the present invention improved device characteristics in that the driving voltages (7.1 -8.6V) were decreased to around 2V less than that of the comparative material, and the luminous efficiency was significantly improved at the same luminance of 1000nit.
  • devices including host materials of the organic compounds according to the above Examples of the present invention showed device characteristics in which the driving voltages (6.3-6.5V) were decreased to maximumally 1.4V less than that of the comparative material, and the luminous efficiency was significantly improved at the same luminance of 1000nit.
  • devices including a host of the organic compound according to one embodiment of the present invention improved the lifetime of the device to 500% of that of the comparative material.
  • devices including a host of organic compound according to one embodiment of the present invention improved device characteristics such as driving voltage and luminous efficiency compared to those of comparative material of CBP at the same luminance of 1000nit.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Photovoltaic Devices (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The material for an organic photoelectric device is a phosphorescent material having thermal stability due to a glass transition temperature (Tg) of 120° C or more and a thermal decomposition temperature of 400° C or more. The material is capable of realizing a high efficiency organic photoelectric device The material for an organic photoelectric device includes a bipolar organic compound including both a hole transporting unit and an electron transporting unit. An organic photoelectric device including a material for the organic photoelectric device is also provided.

Description

TITLE OF THE INVENTION
MATERIAL FOR ORGANIC PHOTOELECTRIC DEVICE INCLUDING ELECTRON TRANSPORTING UNITAND HOLE TRANSPORTING UNIT, AND
ORGANIC PHOTOELECTRIC DEVICE INCLUDING THE SAME BACKGROUND OF THE INVENTION
(a) Field of the Invention
The present invention relates to a material for an organic photoelectric device and an organic photoelectric device including the same. More particularly, the present invention relates to a material for an organic photoelectric device having thermal stability due to a glass transition temperature (Tg) of 120° C or more and a thermal decomposition temperature of 400° C or more, having bipolar characteristics due to good hole and electron transporting properties, and being capable of realizing high efficiency of an organic photoelectric device, and an organic photoelectric device including the same.
(b) Description of the Related Art
A photoelectric device is, in a broad sense, a device for transforming photo energy to electrical energy, and conversely, for transforming electrical energy to photo energy. The photoelectric device may be exemplified by an organic light emitting diode, a solar cell, a transistor, and so on.
Particularly, among these photoelectric devices, the organic light emitting device employing organic light emitting diodes (OLED) has recently drawn attention due to the increase in demand for flat panel displays. The organic light emitting device transforms electrical energy into light by applying current to an organic light emitting material. It has a structure in which a functional organic material layer is interposed between an anode and a cathode. The organic light emitting diode has similar electrical characteristics to those of light emitting diodes (LED) in which holes are injected from an anode and electrons are injected from a cathode, then the holes and electrons move to opposite electrodes and are recombined to form excitons having high energy. The formed excitons generate lights having a certain wavelength while shifting to a ground state.
Generally, the organic light emitting diode is composed of an anode of a transparent electrode, an organic thin layer of a light emitting region, and a metal electrode (cathode) formed on a glass substrate, in that order. The organic thin layer may includes an emission layer, a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection layer (EIL). It may further include an electron blocking layer or a hole blocking layer due to the emission characteristics of the emission layer.
When the organic light emitting diode is applied with an electric field, the holes and electrons are injected from the anode and the cathode, respectively. The injected holes and electrons are recombined on the emission layer though the hole transport layer (HTL) and the electron transport layer (ETL) to provide light emitting excitons.
The provided light emitting excitons emit light by transiting to the ground state.
The light emitting may be classified as a fluorescent material including singlet excitons and a phosphorescent material including triplet excitons.
In other words, the duration of fluorescent emission is extremely short at several nanoseconds, but the duration of phosphorescent emission is relatively long such as at several microseconds, so that it provides a characteristic of extending the lifetime (emission duration) to more than that of the fluorescent emission.
In addition, evaluating quantum mechanically, when holes injected from the anode are recombined with electrons injected from the cathode to provide light emitting excitons, the singlet and the triplet are produced in a ratio of 1 :3, in which the triplet light emitting excitons are produced at three times the amount of the singlet light emitting excitons in the organic light emitting diode.
Accordingly, the percentage of the singlet exited state is 25% (the triplet is 75%) in the case of a fluorescent material, so it has limits in luminous efficiency On the other hand, in the case of a phosphorescent material, it can utilize 75% of the triplet exited state and 25% of the singlet exited state, so theoretically the internal quantum efficiency can reach up to 100%. When phosphorescent light emitting material is used, it has advantages in an increase in luminous efficiency of around four times than that of the fluorescent light emitting material.
In this structure, the efficiency and properties of the light emission diodes are dependent on the host material in the emission layer. According to studies regarding the emission layer (host), the organic host material can be exemplified by a material including naphthalene, anthracene, phenanthrene, tetracene, pyrene, benzopyrene, chrysene, pycene, carbazole, fluorene, biphenyl, terphenyl, triphenylene oxide, dihalobi phenyl, trans-stilbene, and 1 ,4- diphenylbutadiene.
Generally, the host material includes 4,4-N,N-dicarbazolebiphenyl (CBP) having a glass transition temperature of 110° C or less and a thermal decomposition temperature of 400° C or less, in which the thermal stability is low and the symmetry is excessively high. Thereby, it tends to crystallize and cause problems such as a short and a pixel defection according to results of thermal resistance tests of the devices.
In addition, most host materials including CBP are materials in which the hole transporting property is greater than the electron transporting property. In other words, as the injected hole transportation is faster than the injected electron transportation, the excitons are ineffectively formed in the emission layer. Therefore, the resultant device has deteriorated luminous efficiency.
Accordingly, in order to realize a highly efficient and long lifetime organic light emitting device, it is required to develop a phosphorescent host material having high electrical and thermal stability and that is capable of transporting both holes and electrons.
SUMMARY OF THE INVENTION
According to one embodiment of the present invention, provided is a material for an organic photoelectric device having thermal stability due to a glass transition temperature (Tg) of 120° C or more and a thermal decomposition temperature of 400° C or more, having bipolar characteristics due to good hole and electron transporting properties, and being capable of realizing a high efficiency organic photoelectric device. According to another embodiment of the present invention, provided is an organic photoelectric device having high luminous efficiency and a long life-span.
The embodiments of the present invention are not limited to the above technical purposes, and a person of ordinary skill in the art can understand other technical purposes. One embodiment of the present invention provides a material for an organic photoelectric device that includes the compound represented by the following Formula 1. The material is a bipolar organic compound including both a hole transporting unit and an electron transporting unit.
[Chemical Formula 1]
Figure imgf000007_0001
Wherein, in the above Formula 1 , the pyridine (C6H5N) is an electron transporting unit, the HTU and HTU1 independently are as a hole transporting unit, and the HTU and HTU1 are the same or different. Another embodiment of the present invention provides an organic photoelectric device that includes an anode, a cathode, and organic thin layers disposed between the anode and cathode. The organic thin layer includes the above material for an organic photoelectric device.
Hereinafter, other embodiments of the present invention will be described in detail. The material for an organic photoelectric device can provide an organic photoelectric device having high luminous efficiency at a low driving voltage. BRIEF DESCRIPTION OF THE DRAWINGS
FIGS. 1 to 5 are cross-sectional views showing organic photoelectric devices including organic compounds according to various embodiments of the present invention.
DETAILED DESCRIPTION OF THE EMBODIMENTS
Exemplary embodiments of the present invention will hereinafter be described in detail. However, these embodiments are only exemplary, and the present invention is not limited thereto. The material for an organic photoelectric device according to one embodiment of the present invention includes a compound represented by the following Formula 1. The material is a bipolar organic compound including both a hole transporting unit and an electron transporting unit.
[Chemical Formula 1]
Figure imgf000008_0001
In the above Formula 1 , the pyridine (C6H5N) is an electron transporting unit, the HTU and HTU1 independently are a hole transporting unit, and the HTU and HTU' are the same or different.
The organic compound of the above Formula 1 is exemplified by the organic compound of the following Formula 2. [Chemical Formula 2]
Figure imgf000009_0001
In the above Formula 2, X and Y are independently selected from the group consisting of nitrogen (N), sulfur (S), and oxygen (O).
Ar1 and Ar2 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 alkylene, a substituted or unsubstituted C2 to C30 heteroaryl, and a substituted or unsubstituted C2 to C30 heteroarylene. R1 to R4 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C2 to C30 heteroarylene, a substituted or unsubstituted C1 to C30 alkyl, and a substituted or unsubstituted C1 to C30 alkylene. Alternately, R1 and R2 form a cyclic ring or R3 and R4 form a cyclic ring. When X is sulfur or oxygen, R2 is a unshared electron pair, and when Y is sulfur or oxygen, R4 is a unshared electron pair. m and n are independently integers ranging from 0 to 3, m+n is more than or equal to 1 , and o and p are integers ranging from 0 to 2. In the present specification, when specific definition is not provided, the term "substituted" refers to one substituted with at least a substituent selected from the group consisting of a halogen, a cyano, a hydroxy, an amino, a C1 to C30 alkyl, a C3 to C30 cycloalkyl, a C6 to C30 aryl, and a C2 to C30 heteroaryl.
In the present specification, when specific definition is not provided, the term "hetero" refers to one including 1 to 3 heteroatoms selected from the group consisting of nitrogen (N), oxygen (O), sulfur (S), phosphorus (P), and Si (silicon) instead of carbon.
In the above Formula 2, when X and Y are nitrogen, and o and p are 1 , the organic compound having the above Formula 2 may be represented by the following Formula 3.
[Chemical Formula 3]
Figure imgf000010_0001
In the above Formula 3, Ar3 and Ar4 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 alkylene, a substituted or unsubstituted C2 to C30 heteroaryl, and a substituted or unsubstituted C2 to C30 heteroarylene.
Rb to R8 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C2 to C30 heteroarylene, a substituted or unsubstituted C1 to C30 alkyl, and a substituted or unsubstituted
C1 to C30 alkylene. Alternately, R5 and R6 form a cyclic ring or R7 and R8 form a cyclic ring. m and n are independently integers ranging from 0 to 3, and m+n is more than or equal to 1.
In the above Formula 3, when m+n is more than or equal to 2 and Ar3 and Ar4 are phenyl, the organic compound having the above Formula 3 may be represented by the following Formula 4. [Chemical Formula 4]
Figure imgf000011_0001
In the above Formula 4, Ar5 to Ar10 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 alkylene, a substituted or unsubstituted C2 to C30 heteroaryl, and a substituted or unsubstituted C2 to C30 heteroarylene. Alternately, Ar5 and Ar6 form a cyclic ring, Ar7 and Ar8 form a cyclic ring, or Ar9 and Ar10 form a cyclic ring. q is an integer ranging from 0 to 2.
In the above Formula 3, when m+n is more than or equal to 2, o is 1 , and p is 0, the organic compound having the above Formula 3 may be represented by the following Formula 5.
[Chemical Formula 5]
Figure imgf000012_0001
In the above Formula 5, Ar11 to Ar15 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 alkylene, a substituted or unsubstituted C2 to C30 heteroaryl, and a substituted or unsubstituted C2 to C30 heteroarylene. Alternately, Ar12 and Ar13 form a cyclic ring, or Air14 and Ar15 form a cyclic ring. r is an integer ranging from 0 to 2.
In the organic compound of the above Formula 2, at least one substituent selected from the group consisting of XR1R2, YR3R4, and a combination thereof may be selected from the following Formulae 6a to 6d. [Chemical Formula 6a]
Figure imgf000013_0001
[Chemical Formula 6b]
Figure imgf000013_0002
[Chemical Formula 6c]
Figure imgf000013_0003
[Chemical Formula 6d]
—
Figure imgf000013_0004
In the above Formulae 6a to 6d, Ar16 and Ar17 are independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl and a substituted or unsubstituted C2 to C30 heteroaryl.
R9 to R14 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C2 to C20 alkoxy, and SiR15Ri6Ru (where R-15 to Rr/ are independently selected from the group consisting of a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C3 to C30 cycloalkyl, a nitrile, a cyano, a nitro, a carbonyl, and an amide), si to S6 are independently integers ranging from 0 to 4.
The organic compounds having the above Formulae 1 to 5 have thermal stability such as a glass transition temperature (Tg) of 120° C or more, and a thermal decomposition temperature (Td) of 400° C or more.
The organic compounds having the above Formula 2 may be selected from the group consisting of the following compounds (1) to (41), and combinations thereof, but are not limited thereto.
Compound (1) Compound (2)
Figure imgf000014_0001
Compound (3) Compound (4)
Figure imgf000015_0001
Compound (5) Compound (6)
Figure imgf000015_0002
Compound (7) Compound (8)
Figure imgf000015_0003
Compound (9) Compound (10)
Figure imgf000015_0004
Compound (11) Compound (12)
Figure imgf000016_0001
Compound (13) Compound (14)
Figure imgf000016_0002
Compound (15) Compound (16)
Figure imgf000016_0003
Compound (17) Compound (18)
Figure imgf000016_0004
Compound (19) Compound (20)
Figure imgf000016_0005
Compound (21) Compound (22)
Figure imgf000017_0001
Compound (23) Compound (24)
Figure imgf000017_0002
Compound (25) Compound (26)
Figure imgf000017_0003
Compound (27) Compound (28)
Figure imgf000017_0004
Compound (29) Compound (30)
Figure imgf000018_0001
Compound (31)
Figure imgf000018_0002
Compound (32)
Figure imgf000018_0003
Compound (33) Compound (34)
Figure imgf000018_0004
Compound (35) Compound (36)
Figure imgf000019_0001
Compound (37) Compound (38)
Figure imgf000019_0002
Compound (39) Compound (40)
Figure imgf000019_0003
Compound (41)
Figure imgf000019_0004
The organic compounds having the above Formula 5 may be selected from the group consisting of the following compounds (42) to (52), and combinations thereof, but are not limited thereto.
Compound (42) Compound (43)
Figure imgf000020_0001
Compound (44) Compound (45)
Figure imgf000020_0002
Compound (46) Compound (47)
Figure imgf000020_0003
Figure imgf000020_0004
Compound (49)
Figure imgf000020_0005
Compound (50) Compound (51)
Figure imgf000021_0001
Compound (52)
Figure imgf000021_0002
The exemplary organic compound may be used by itself, but it is generally used as a host material that is capable of binding with a dopant.
The dopant is a compound having a high emission property, by itself.
However, it is usually added to a host in a minor amount, so it is also called a guest or dopant. In other words, the dopant is a material that is doped to the host material to emit light, and generally includes a metal complex that emits light due to multiplet excitation into a triplet or higher state.
When the organic compounds represented by the above Formulae 1 to
5 are used for a light emitting host material, all red (R), green (G), and blue (B) colors and white (W) fluorescent or phosphorescent dopant materials are available for a dopant. According to one embodiment, the dopant includes a phosphorescent dopant material. Generally, the material should satisfy the requirement to have a high light emitting quantum efficiency, to be rarely agglomerated, and to be distributed uniformly in the host material.
According to one embodiment, the phosphorescent dopant is an organic metal compound including at least element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, and combinations thereof.
Specifically, the red phosphorescent dopant may include PtOEP, lr(Piq)2(acac) (Piq=1-phenylisoquinoline, acac=pentane-2,4-dione), Ir(PJq)3, and RD 61 from UDC; the green phosphorescent dopant may include lr(PPy)3(PPy=2-phenylpyridine), lr(PPy)2(acac), and GD48 from UDC; and the blue phosphorescent dopant may include (4,6-F2PPy)2lrpic (reference: Appl. Phys. Lett., 79, 2082-2084, 2001).
FIGS. 1 to 5 are cross-sectional views showing organic photoelectric devices including the organic compounds according to various embodiments of the present invention. An organic photoelectric device according to one embodiment of the present invention includes at least one layer of an organic thin layer interposed between an anode and a cathode. The anode includes a transparent electrode such as ITO (indium tin oxide), and the cathode includes a metal electrode such as aluminum. Referring to FIG. 1 , the organic photoelectric device 100 includes an organic thin layer 105 including only an emission layer 130.
Referring to FIG. 2, a double-layered organic photoelectric device 200 includes an organic thin layer 105 including an emission layer 230 including an electron transport layer (ETL) (not shown), and a hole transport layer (HTL) 140. The hole transport layer (HTL) 140 is a separate layer having an excellent binding property with a transparent electrode such as ITO or a excellent hole transporting property. Referring to FIG. 3, a three-layered organic photoelectric device 300 includes the organic thin layer 105 including an electron transport layer (ETL) 150, an emission layer 130, and a hole transport layer (HTL) 140. The emission layer 130 is independently installed, and layers having an excellent electron transporting property or an excellent hole transporting property are separately stacked.
As shown in FIG. 4, a four-layered organic photoelectric device 400 includes the organic thin layer 105 including an electron injection layer (EIL) 160, an emission layer 130, a hole transport layer (HTL) 140, and a hole injection layer (HIL) 170 for binding with the cathode of ITO, different from the structure of the three-layered organic photoelectric device 300 shown in FIG. 3.
As shown in FIG. 5, a five layered organic photoelectric device 500 includes the organic thin layer 105 including an electron transport layer (ETL) 150, an emission layer 130, a hole transport layer (HTL) 140, and a hole injection layer (HIL) 170, and further includes an electron injection layer (EIL) 160 to achieve the low voltage.
In order to form the organic thin layer 105 having one through five layers, the method may follow a dry coating method such as evaporation, sputtering, plasma plating, and ion plating, or a wet coating method such as spin coating, dipping, and flow coating.
In one embodiment of the present invention, at least one layer selected from the group consisting of the emission layer, electron transport layer (ETL), electron injection layer (EIL), hole transport layer (HTL), hole injection layer (HIL), hole blocking layer, and combination thereof includes a material for the organic photoelectric device.
The organic thin layer includes the phosphorescent light emitting compound such as a metal complex that emits light due to the multiple excitation into a triplet or higher state. The following examples illustrate the present invention in more detail.
However, it is understood that the present invention is not limited by these examples.
1. Synthesis of material for an organic photoelectric device
(Example 1 : Synthesis of compound (3)) Compound (3) as a material for an organic photoelectric device was synthesized as shown in the following Reaction Scheme 1.
[Reaction Scheme 1]
Figure imgf000024_0001
Figure imgf000024_0002
Pd(PPh3)4, K2CO3, Toluene
Figure imgf000024_0003
Step 1 : Synthesis of Intermediate (A)
50.8g (304mmol) of carbazole, 71.6g (304mmol) of 1 ,4-dibromobenzene,
3.76g (38 mmol) of cuprous chloride, and 83.9g (607mmol) of potassium carbonate were suspended in 322ml of dimethylsulfoxide, and heated and refluxed under a nitrogen atmosphere for 8 hours. The reaction fluid was cooled to room temperature and recrystallized with methanol.
The precipitated crystals were separated by filtration and the obtained residue was purified by silica gel column chromatography, providing 59.9g of the intermediate (A) (yield 61.3%). Step 2: Synthesis of Intermediate (B)
37.8g (117mmol) of the intermediate (A) was dissolved in 378ml of tetrahydrofuran, then 100.5ml (161 mmol) of n-butyl lithium hexane solution (1.6M) was added thereto under an argon atmosphere at -7O0C. The obtained solution was agitated at -7O0C to 4O0C for 1 hour. The reaction fluid was frozen to -7O0C, and 47.9ml (235mmol) of isopropyl tetramethyl dioxaborolane was slowly added thereto in a dropwise fashion. The obtained solution was agitated at -7O0C for 1 hour and heated to room temperature, and then agitated for 6 hours. To the obtained reaction solution, 200ml of water was added and agitated for 20 minutes. The reaction solution was separated into two liquid layers, and an organic layer thereof was dried with anhydrous sodium sulfate. After the organic solvent was removed under a reduced pressure, the obtained residue was purified with silica gel column chromatography to provide 28.9g of the intermediate (B) (yield 66.7%).
Step 3: Synthesis of Compound (3)
10.3g (28mmol) of the intermediate (B), 3.Og (13mmol) of 3,5- dibromopyridine, and 0.73g (O.δmmol) of tetrakis-(triphenyl phosphine) palladium were suspended in 90 ml of tetrahydrofuran and 60ml of toluene, then added with a solution of 7.Og (51mmol) of potassium carbonate dissolved in
60ml of water. The obtained mixture was heated and refluxed for 9 hours.
The reaction fluid was separated into two layers, and an organic layer thereof was cleaned with a sodium chloride saturated aqueous solution and dried with anhydrous sodium sulfate. Subsequently, the organic solvent was removed by distillation under reduced pressure, and the residue was recrystallized with toluene. The precipitated crystals were separated by filtration and cleaned with toluene to provide 5.5g (77.3%) of the compound (3).
(EExample 2: Synthesis of Compound (13)) Compound (13) as a material for an organic photoelectric device was synthesized as shown in the following Reaction Scheme 2.
[Reaction Scheme 2]
Figure imgf000027_0001
Slep 1 : Synthesis of Intermediate (C)
15g (63mmol) of 1 ,4-dibromobenzene, 7.66g (44mmol) of 1- naphthaleneboron acid, 17.58g (127mmol) of potassium carbonate, and 1.83g (50mmol) of tetrakis-(triphenylphosphine) palladium were suspended in a mixed solvent including 200ml of tetrahydrofuran, 200ml of toluene, and 50 ml of purified water, and heated and refluxed under a nitrogen atmosphere for 24 hours.
The reaction fluid was cooled to room temperature, and separated into two layers. Then, the solvent of an organic layer thereof was removed under a reduced pressure to provide a fluid. The fluid was separated by column chromatography (hexane) to remove the solvent and to provide 15g of a gel intermediate (C) at a yield of 83%.
Step 2: Synthesis of Intermediate (D) 7g (24mmol) of the intermediate (C) was dissolved in 50ml of tetrahydrofuran, and added with 15ml (24mmol) of an n-butyl lithium hexane solution (1.6M) under an argon atmosphere at -7O0C. The obtained solution was agitated at -700C for 30 minutes, and the reaction fluid was slowly added with 47.9ml (235mmol) of isopropyl tetramethyl dioxaborolane in a dropwise fashion. After the obtained solution was agitated at -7O0C for 1 hour, it was heated to room temperature and agitated for 6 hours. To the obtained reaction solution, 200ml of water was added and agitated for 20 minutes.
After the reaction solution was separated into two liquid layers, an organic solvent thereof was removed under a reduced pressure. The obtained residue was purified with silica gel column chromatography to provide 6g of the intermediate (D) at a yield of 73%.
Step 3: Synthesis of Intermediate (E)
40.4g (241mmol) of carbazole, 38.Og (121mmol) of 1 ,3,5- tribromobenzene, 2.99g (30 mmol) of cuprous chloride, and 66.7g (483mmol) of potassium carbonate were suspended in 171ml of dimethylsulfoxide, and heated and refluxed under a nitrogen atmosphere for 8 hours.
The reaction fluid was cooled to room temperature and recrystallized with methanol. The precipitated crystals were separated by filtration, and the obtained residue was purified with silica gel column chromatography to provide 36.7g of the intermediate (E) at a yield of 62.4%.
Step 4: Synthesis of Intermediate (F)
35.Og (72mmol) of the intermediate (E) was dissolved in 350 ml of tetrahydrofuran and added with 61.5ml (98mmol) of an n-butyl lithium hexane solution (1.6M) under an argon atmosphere at -7O0C. The obtained solution was agitated at -7O0C to 4O0C for 1 hour. The reaction flux was frozen to -7O0C and slowly added with 29.3ml (144mmol) of isopropyl tetramethyl dioxaborolane in a dropwise fashion. The obtained solution was agitated at -7O0C for 1 hour, and heated to room temperature and agitated for 6 hours. The obtained reaction solution was added with 200ml of water and agitated for 20 minutes.
After the reaction solution was separated into two liquid layers, an organic layer thereof was dried with anhydrous sodium sulfate. After the organic solvent was removed under a reduced pressure, the obtained residue was purified with silica gel column chromatography to provide 25.1g (yield
65.4%) of the intermediate (F).
Step 5: Synthesis of Intermediate (G)
45.1g (84mmol) of the intermediate (F), 20.Og (84mmol) of 3,5- dibromopyridine, and 2.44g (2.1mmol) of tetrakis-(triphenyl phosphine) palladium were suspended in 600ml of tetrahydrofuran and 400 ml of toluene, and then the suspension was added with a solution in which 23.3 g (169mmol) of potassium carbonate was dissolved in 400ml of water. The obtained mixture was heated and refluxed for 9 hours. The reaction fluid was separated into two layers, and an organic layer thereof was cleaned with a sodium chloride saturated aqueous solution and dried with anhydrous sodium sulfate.
The organic solvent was removed by distillation under a reduced pressure, and the residue was recrystallized by toluene. The precipitated crystals were separated by filtration and cleansed with toluene to provide 30.7g (64.4%) of the intermediate (G).
Step 6: Synthesis of Compound (13)
4g (7mmol) of intermediate (G)1 2.81g (8.5mmol) of the intermediate (D), 1.96g (14mmol) of potassium carbonate, and 0.41g (0.3mmol) of tetrakis-
(triphenylphosphine) palladium were suspended in 200ml of toluene, 200ml of tetrahydrofuran, and 50ml of purified water, then heated and agitated for 24 hours.
After the reaction temperature was lowered to room temperature, the resultant was separated to two layers and a solvent of an organic layer thereof was removed under a reduced pressure. The obtained residue was purified by silica gel column chromatography to provide 4g (82%) of the compound (13).
(Example 3: Synthesis of Compound (21))
Compound (21) as a material for an organic photoelectric device was synthesized in accordance with a process as shown in the following Reaction Scheme 3.
[Reaction Scheme 3]
Figure imgf000030_0001
8.64g (23mmol) of the intermediate (B), 12.Og (21 mmol) of the intermediate (G), and 0.74g (O.δmmol) of tetrakis-(triphenylphosphine)palladium were suspended in 360ml of tetrahydrofuran and 240 ml of toluene, and it was added with a solution of 5.88g (43mmol) of sodium carbonate dissolved in 240ml of water. The obtained mixture was heated and refluxed for 9 hours.
After the reaction fluid was separated into two layers, an organic layer thereof was washed with a sodium chloride saturated aqueous solution and dried with anhydrous sodium sulfate. After the organic solvent was removed by distillation under a reduced pressure, the residue was recrystallized with toluene. The precipitated crystals were separated by filtration and washed with toluene to provide 9.8g (63.4%) of the compound (21). MS(ESI) m/z 727.24 (M+H)+
(Example 4: Synthesis of Compound (18))
Compound (18) as a material for an organic photoelectric device was synthesized as shown in the following Reaction Scheme 4.
[Reaction Scheme 4]
Figure imgf000031_0001
The compound 18 was synthesized according to the same method as in Example 3, except that an intermediate (H) was used instead of the intermediate (B). MS(ESI) m/z 729.25 (M+H)+
(Example 5: Synthesis of Compound (36)) The compound (36) as a material for an organic photoelectric device was synthesized as shown in the following Reaction Scheme 5. [Reaction Scheme 5]
Figure imgf000032_0001
A compound (36) was prepared in accordance with the same procedure as in Example 3, except that an intermediate (I) was used instead of the intermediate (B). MS(ESI) m/z 779.26 (M+H)+
(Example 6: Synthesis of Compound (22))
Compound (22) was synthesized in accordance with the following Reaction Scheme 6.
[Reaction Scheme 6]
Toluene
Figure imgf000033_0001
Figure imgf000033_0002
Figure imgf000033_0003
Step 1 : Synthesis of Intermediate (J)
10.3g of the intermediate (B) synthesized in Example 1 , 3.Og of 3,5- dibromopyridine, and 0.73g of tetrakis-(triphenylphosphine) palladium were suspended in 90 ml of tetrahydrofuran and 60ml of toluene, then added with a solution of 7.Og of potassium carbonate dissolved in 60ml of water. The obtained mixture was heated and refluxed for 9 hours.
The reaction fluid was separated into two layers, and an organic layer thereof was cleaned with a sodium chloride saturated aqueous solution and dried with anhydrous sodium sulfate. Subsequently, the organic solvent was removed by distillation under reduced pressure, and the residue was recrystallized with toluene. The precipitated crystals were separated by filtration and cleaned with toluene to provide 5.5g of the intermediate (J).
Step 2: Synthesis of Intermediate (K)
10.3g of the intermediate (F) synthesized in Example 2, 3.Og of 1 ,4- dibromobenzene, 17.58g of potassium carbonate, and 0.73g of tetrakis- (triphenylphosphine) palladium were suspended in 200ml of tetrahydrofuran,
20OmI of toluene, and 50 ml of purified water, and heated and refluxed under a nitrogen atmosphere for 24 hours.
15ml of an n-butyl lithium hexane solution (1.6M) was added and then the obtained solution was agitated at -7O0C for 30 minutes, and the reaction fluid was slowly added with 47.9ml (235mmol) of isopropyl tetramethyl dioxaborolane in a dropwise fashion. After the obtained solution was agitated at -7O0C for 1 hour, it was heated to room temperature and agitated for 6 hours.
To the obtained reaction solution, 200ml of water was added and agitated for 20 minutes. After the reaction solution was separated into two liquid layers, an organic solvent thereof was removed under a reduced pressure. The obtained residue was purified with silica gel column chromatography to provide 6g of the intermediate (K).
Slep 3: Synthesis of Compound (22)
10.3g of the intermediate (J) synthesized at Step 1 , 12.Og of the intermediate (K), and 0.74g of tetrakis-(triphenylphosphine) palladium were suspended in 90 ml of tetrahydrofuran and 60ml of toluene, then added with a solution of 5.88g of potassium carbonate dissolved in 240ml of water. The obtained mixture was heated and refluxed for 9 hours. The reaction fluid was separated into two layers, and an organic layer thereof was cleaned with a sodium chloride saturated aqueous solution and dried with anhydrous sodium sulfate. Subsequently, the organic solvent was removed by distillation under reduced pressure, and the residue was recrystallized with toluene. The precipitated crystals were separated by filtration and cleaned with toluene to provide 9.8g of the compound (22). MS(ESI) m/z 803.26 (M+H)+
2. Measurement of glass transition temperature and thermal decomposition temperature Organic compounds synthesized from Examples 1 to 3 and comparative material of CBP were measured for glass transition temperature (Tg) and thermal decomposition temperature Td through differential scanning calorimetry (DSC) and thermalgravimetry (TGA), and the results are shown in the following Table 1.
Table 1
Figure imgf000035_0002
In Table 1 , CBP is a compound represented by the following Formula.
Figure imgf000035_0001
Referring to Table 1 , the organic compounds according to the above Examples of the present invention had a glass transition temperature (Tg) of 12O0C or more and a thermal decomposition temperature (Td) of 4300C or more according to the DSC and TGA measurement results, which shows that the organic compounds had much higher thermal stability than that of the comparative material, CBP.
3. Fabrication of phosphorescent green-emitting organic photoelectric device, and evaluation thereof
Organic compounds prepared from Examples 1 to 6 and comparative material, CBP, were used as a host, and Ir(PPy)3 was used as a dopant to provide a phosphorescent green-emitting organic photoelectric device. The obtained device was analyzed for characteristics thereof. ITO was provided in a thickness of 1000A for an anode, and aluminum
(Al) was provided in a thickness of 1000A for a cathode.
The method of manufacturing an organic photoelectric device may be described in detail as follows: cutting an ITO glass substrate having a sheet resistance value of 15Ψ/cm2 into a size of 50mm x 50mm x 0.7mm for a cathode; ultrasonic wave cleaning the same in acetone, isopropyl alcohol, and pure water for 15 minutes, respectively; and UV ozone cleaning for 30 minutes. N,Nl-di(1-naphthyl)-N,N'-diphenylbenzidine (NPD) was deposited on the upper surface of the substrate under the conditions of a vacuum degree of 650 x i0'rPa and a deposition speed of 0.1 to 0.3nm/s to provide a hole transport layer (HTL). Subsequently, under the same vacuum deposition condition, the host material and the phosphorescent dopant were simultaneously deposited to provide an emission layer having a thickness of 300A. During this process, a phosphorescent dopant of lr(PPy)3 was deposited at the same time, and the adding amount of the phosphorescent dopant was adjusted to 5 wt%. Bis(2-methyl-8-quinolinolate)-4-(phenylphenolate)aluminum (BAIq) and
AIq3 were deposited on the upper surface of the emission layer under the same vacuum deposition conditions to provide a hole blocking layer and an electron transport layer (ETL). On the upper surface of the electron transport layer (ETL), LiF and Al were sequentially deposited to provide an organic photoelectric device having the following structure A.
Structure A: NPD 700A/EML (5wt%, 300A)/BAIq 50A/Alq3 200A/LiF 5A/AI
Organic photoelectric devices having the structures B and C were fabricated in accordance with the same process as in the above. TCTA denotes 4,4',4"-tris(N-carbazolyl)triphenylamine (4,4',4"-tris(N- carbazolyl)triphenylamine).
Structure B: NPD 700A/EML (5wt%, 300A)/Alq3 250A/UF 5A/AI
Structure C: NPD 600A/TCTA 100A/EML (5wt%, 300A)/Alq3 25θA/LiF 5A/AI
Current density, luminance, and luminous efficiency of each organic photoelectric device in accordance with voltage were measured. Specific measurements were performed as follows. 1) Current density according to voltage change
Each of obtained organic photoelectric devices was measured for a current value passing through the unit device using a current-voltage meter (Keithley 2400) while increasing the voltage from OV to 10V. The results are calculated by dividing the measured current value by the area. 2) Luminance according to a voltage change
Each of obtained organic photoelectric devices was measured for luminance by a luminance meter (Minolta Cs-IOOOA) while increasing the voltage from OV to 10V.
3) Luminous efficiency measurement Luminous efficiency was calculated from the luminance, current density, and voltage.
Luminous efficiency of the organic photoelectric device having the structure A is shown in the following Table 2. Luminance, driving voltages, and color coordinates are also shown in the following Table 2. Table 2
Figure imgf000039_0001
As shown in Table 2, devices including hosts of the organic compounds according to the above Examples of the present invention had driving voltages of 5V or less (3.9-5. OV), which were around 2V less than that of comparative material at the same luminance of 100nit, and improved luminous efficiency that was significantly more than that of comparative material.
The following Table 3 shows the results of measuring characteristics of the organic photoelectric device having structure B. Table 3
Figure imgf000040_0001
As shown in Table 3, devices including hosts of the organic compounds according to the above Examples of the present invention improved device characteristics in that the driving voltages (7.1 -8.6V) were decreased to around 2V less than that of the comparative material, and the luminous efficiency was significantly improved at the same luminance of 1000nit.
The following Table 4 shows the results for assessing characteristics of the organic photoelectric device having structure C.
Table 4
Figure imgf000041_0001
As shown in Table 4, devices including host materials of the organic compounds according to the above Examples of the present invention showed device characteristics in which the driving voltages (6.3-6.5V) were decreased to maximumally 1.4V less than that of the comparative material, and the luminous efficiency was significantly improved at the same luminance of 1000nit.
Furthermore, the flowing Table 4 shows results for assessing lifetime of the organic photoelectric device having structure C. Table 5
Figure imgf000042_0001
As shown in Table 5, devices including a host of the organic compound according to one embodiment of the present invention improved the lifetime of the device to 500% of that of the comparative material.
4. Fabrication of phosphorescent red-emitting organic photoelectric device, and evaluation thereof
Organic compounds obtained from Examples 1 to 6 and a comparative material of CBP were used for a host material and Ir(PJq)3 was used for a red dopant to provide a red phosphorescent organic photoelectric device having structure A, and the characteristics thereof were evaluated. The device was manufactured under the same conditions as in the green phosphorescent device. The obtained devices were measured for characteristics, and the results are shown in the following Table 6: Table 6
Figure imgf000043_0001
As shown in Table 6, devices including a host of organic compound according to one embodiment of the present invention improved device characteristics such as driving voltage and luminous efficiency compared to those of comparative material of CBP at the same luminance of 1000nit.
While this invention has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

WHAT IS CLAIMED IS:
1. A material for an organic photoelectric device comprising a compound represented by the following Formula 1 , being a bipolar organic compound including both a hole transporting unit and an electron transporting unit:
[Chemical Formula 1]
Figure imgf000044_0001
wherein, in the above Formula 1 , the pyridine (CΘHSN) is an electron transporting unit, the HTU and HTU1 independently function as a hole transporting unit, and the HTU and HTU1 are the same or different.
2. The material of claim 1 , wherein the organic compound of the Formula 1 is the organic compound of the following Formula 2: [Chemical Formula 2]
Figure imgf000044_0002
wherein, in the above Formula 2, X and Y are independently selected from the group consisting of nitrogen (N), sulfur (S), and oxygen (O),
Ar1 and Ar2 are independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 alkylene, a substituted or unsubstituted C2 to C30 heteroaryl, and a substituted or unsubstituted C2 to C30 heteroarylene, R1 to R4 are independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C2 to C30 heteroarylene, a substituted or unsubstituted C1 to C30 alkyl, and a substituted or unsubstituted C1 to C30 alkylene, or R1 and R2 form a cyclic ring or R3 and R4 form a cyclic ring, when X is sulfur or oxygen, R2 is a unshared electron pair, and when Y is sulfur or oxygen, R4 is a unshared electron pair, and m and n are independently integers ranging from 0 to 3, m+n is more than or equal to 1 , and o and p are integers ranging from 0 to 2.
3. The material for an organic photoelectric device of claim 1 , wherein the bipolar organic compound having the above Formula 1 is represented by the following Formula 3:
[Chemical Formula 3]
Figure imgf000045_0001
wherein, in the above Formula 3, Ar3 and Ar4 are independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 alkylene, a substituted or unsubstituted C2 to C30 heteroaryl, and a substituted or unsubstituted C2 to C30 heteroarylene,
R5 to R8 are independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C2 to C30 heteroarylene, a substituted or unsubstituted C1 to C30 alkyl, and a substituted or unsubstituted C1 to C30 alkylene, or R5 and R6 form a cyclic ring or R7 and R8 form a cyclic ring, and m and n are independently integers ranging from 0 to 3, and m+n is more than or equal to 1.
4. The material for an organic photoelectric device of claim 1 , wherein the organic compound of the Formula 1 is the organic compound of the following Formula 4:
[Chemical Formula 4]
Figure imgf000046_0001
wherein, in the above Formula 4, Ar5 to Ar10 are independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 alkylene, a substituted or unsubstituted C2 to C30 heteroaryl, and a substituted or unsubstituted C2 to C30 heteroarylene, or Ar5 and Ar6 form a cyclic ring, Ar7 and Ar8 form a cyclic ring, or Air9 and Ar10 form a cyclic ring, and q is an integer ranging from 0 to 2.
5. The material for an organic photoelectric device of claim 1 , wherein the organic compound of the Formula 1 is the organic compound of the following Formula 5:
[Chemical Formula 5]
Figure imgf000047_0001
wherein, in the above Formula 5, Ar11 to Ar15 are independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted
C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 alkylene, a substituted or unsubstituted C2 to C30 heteroaryl, and a substituted or unsubstituted C2 to
C30 heteroarylene, or Ar12 and Ar13 form a cyclic ring, or Ar14 and Ar15 form a cyclic ring, and r is an integer ranging from 0 to 2.
6. The material for an organic photoelectric device of claim 2, wherein of XR1R2 and YR3R4 in the organic compound of the Formula 2 is represented by the following Formula 6a: [Chemical Formula 6a]
Figure imgf000048_0001
wherein, in the above Formula 6a, Ar16 and Ar17 are independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl and a substituted or unsubstituted C2 to C30 heteroaryl.
7. The material for an organic photoelectric device of claim 2, wherein of XR1R2 and YR3R4 in the organic compound of the Formula 2 is represented by the following Formula 6b: [Chemical Formula 6b]
Figure imgf000048_0002
wherein, in the above Formula 6b, R9 and R10 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C2 to C20 alkoxy, and SiRi5Ri6Ri7 (where Ri5 to R-17 are independently selected from the group consisting of a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C3 to C30 cycloalkyl, a nitrile, a cyano, a nitro, a carbonyl, and an amide), and si and S2 are independently integers ranging from 0 to 4.
8. The material for an organic photoelectric device of claim 2, wherein of XR1R2 and YR3R4 in the organic compound of the Formula 2 is represented by the following Formula 6c: [Chemical Formula 6c]
Figure imgf000049_0001
wherein, in the above Formula 6c, R11 and R12 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C2 to C20 alkoxy, and SiRi5Ri6Ri7 (where R15 to Ru are independently selected from the group consisting of a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryi, a substituted or unsubstituted C3 to C30 cycloalkyl, a nitrile, a cyano, a nitro, a carbonyl, and an amide), and
S3 and S4 are independently integers ranging from 0 to 4.
9. The material for an organic photoelectric device of claim 2, wherein of XR1R2 and YR3R4 in the organic compound of the Formula 2 is represented by the following Formula 6d:
[Chemical Formula 6d]
-
Figure imgf000050_0001
wherein, in the above Formula 6d,
R13 and R14 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryi, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C2 to C20 alkoxy, and SiRisRiβRiz (where Ri5 to Ri7 are independently selected from the group consisting of a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryi, a substituted or unsubstituted C3 to C30 cycloalkyl, a nitrile, a cyano, a nitro, a carbonyl, and an amide), and
S5 and s6 are independently integers ranging from 0 to 4.
10. The material for an organic photoelectric device of claim 2, wherein the bipolar organic compound is selected from the group consisting of the following compounds (1) to (41), and combinations thereof:
Compound (1) Compound (2)
Figure imgf000051_0001
Compound (3) Compound (4)
Figure imgf000051_0002
Compound (5) Compound (6)
Figure imgf000051_0003
Compound (7) Compound (8)
Figure imgf000052_0001
Compound (9) Compound (10)
Figure imgf000052_0002
Compound (11) Compound (12)
Figure imgf000052_0003
Compound (13) Compound (14)
Figure imgf000052_0004
Compound (15) Compound (16)
Figure imgf000052_0005
Compound (17) Compound (18)
Figure imgf000053_0001
Compound (19) Compound (20)
Figure imgf000053_0002
Compound (21) Compound (22)
Compound (23) Compound (24)
Figure imgf000053_0004
Compound (25) Compound (26)
Figure imgf000053_0005
Compound (27) Compound (28)
Figure imgf000054_0001
Compound (29) Compound (30)
Figure imgf000054_0002
Compound (31)
Figure imgf000054_0003
Compound (32)
Figure imgf000054_0004
Compound (33) Compound (34)
Figure imgf000055_0001
Compound (35) Compound (36)
Figure imgf000055_0002
Compound (37) Compound (38)
Figure imgf000055_0003
Compound (39) Compound (40)
Figure imgf000055_0004
Compound (41)
Figure imgf000056_0001
11. The material for an organic photoelectric device of claim 5, wherein the bipolar organic compound is selected from the group consisting of the following compounds (42) to (52), and combinations thereof:
Compound (42) Compound (43)
Figure imgf000056_0002
Compound (44) Compound (45)
Figure imgf000056_0003
Compound (46) Compound (47)
Figure imgf000056_0004
Compound (48) Compound (49)
Figure imgf000057_0001
Compound (50) Compound (51)
Figure imgf000057_0002
Compound (52)
Figure imgf000057_0003
12. The material for an organic photoelectric device of claim 1 , wherein the dopant is a phosphorescent dopant selected from the group consisting of red, green, blue, and white phosphorescent dopants, and combinations thereof.
13. The material for an organic photoelectric device of claim 1 , wherein the dopant is a fluorescent dopant selected from the group consisting of red, green, blue, and white phosphorescent dopants, and combinations thereof.
14. An organic photoelectric device comprising an anode, a cathode, and an organic thin layer disposed between the anode and cathode, wherein the organic thin layer comprises the material according to one of claims 1 to 13.
15. The organic photoelectric device of claim 14, wherein the organic thin layer comprises: an emission layer; and at least one layer selected from the group consisting of a hole transport layer (HTL), a hole injection layer (HIL), an electron transport layer (ETL), an electron injection layer (EIL), and combinations thereof.
PCT/KR2008/002098 2007-04-13 2008-04-14 Material for organic photoelectric device including electron transporting unit and hole transporting unit, and organic photoelectric device including the same WO2008127057A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP08741343.1A EP2134809B1 (en) 2007-04-13 2008-04-14 Material for organic photoelectric device including electron transporting unit and hole transporting unit, and organic photoelectric device including the same
CN2008800107618A CN101657517B (en) 2007-04-13 2008-04-14 Material for organic photoelectric device including electron transporting unit and hole transporting unit, and organic photoelectric device including the same
JP2010502951A JP5364089B2 (en) 2007-04-13 2008-04-14 Material for organic photoelectric device including hole transport unit and electron transport unit, and organic photoelectric device including the same
US12/588,365 US8247805B2 (en) 2007-04-13 2009-10-13 Material for organic photoelectric device including electron transporting unit and hole transporting unit, and organic photoelectric device including the same
US13/550,772 US20120280221A1 (en) 2007-04-13 2012-07-17 Material for organic photoelectric device including electron transporting unit and hole transporting unit, and organic photoelectric device including the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR20070036407 2007-04-13
KR10-2007-0036407 2007-04-13

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/588,365 Continuation US8247805B2 (en) 2007-04-13 2009-10-13 Material for organic photoelectric device including electron transporting unit and hole transporting unit, and organic photoelectric device including the same

Publications (1)

Publication Number Publication Date
WO2008127057A1 true WO2008127057A1 (en) 2008-10-23

Family

ID=39864106

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2008/002098 WO2008127057A1 (en) 2007-04-13 2008-04-14 Material for organic photoelectric device including electron transporting unit and hole transporting unit, and organic photoelectric device including the same

Country Status (6)

Country Link
US (2) US8247805B2 (en)
EP (1) EP2134809B1 (en)
JP (1) JP5364089B2 (en)
KR (1) KR101030021B1 (en)
CN (1) CN101657517B (en)
WO (1) WO2008127057A1 (en)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009035524A (en) * 2007-08-03 2009-02-19 Chemiprokasei Kaisha Ltd New bicarbazole derivative, and host material and organic electroluminescent element each using the same
JP2009059767A (en) * 2007-08-30 2009-03-19 Konica Minolta Holdings Inc Organic electroluminescent element, illumination apparatus, and display device
WO2009096549A1 (en) * 2008-01-31 2009-08-06 Hodogaya Chemical Co., Ltd. Compound having substituted pyridyl group and pyridoindole ring structure linked through phenylene group, and organic electroluminescent device
WO2011004807A1 (en) * 2009-07-10 2011-01-13 コニカミノルタホールディングス株式会社 Organic photoelectric conversion element, solar cell using same, and optical sensor array
WO2011016202A1 (en) * 2009-08-05 2011-02-10 保土谷化学工業株式会社 Compound having substituted anthracene ring structure and pyridoindole ring structure and organic electroluminescence device
WO2011108707A1 (en) * 2010-03-05 2011-09-09 出光興産株式会社 Material for organic electroluminescent element, and organic electroluminescent element using same
WO2011145876A2 (en) * 2010-05-20 2011-11-24 주식회사 두산 Novel hybrid organic compound and organic electroluminescent device using same
JP2012530754A (en) * 2009-06-24 2012-12-06 ジョージア・テック・リサーチ・コーポレーション Bipolar small molecule host for phosphorescent guest emitters
US20120319052A1 (en) * 2010-03-02 2012-12-20 Merck Patent Gmbh Compounds for electronic devices
EP2711949A1 (en) * 2010-12-10 2014-03-26 Korea University Research and Business Foundation Compounds having hole conducting property, co-adsorbent body comprising same, and dye-sensitized solar cell comprising the co-adsorbent body
WO2014079527A1 (en) * 2012-11-23 2014-05-30 Merck Patent Gmbh Materials for electronic devices
US9543530B2 (en) 2010-05-03 2017-01-10 Cheil Industries, Inc. Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode
US9799834B2 (en) 2011-08-18 2017-10-24 Semiconductor Energy Laboratory Co., Ltd. Carbazole compound light-emitting element, light-emitting device, electronic device, and lighting device
WO2018189356A1 (en) * 2017-04-13 2018-10-18 Cynora Gmbh Organic molecules, in particular for use in optoelectronic devices
CN109651338A (en) * 2018-12-31 2019-04-19 瑞声科技（南京）有限公司 A kind of asymmetry carbazole pyridine compounds and its application
EP3575377A1 (en) * 2018-05-31 2019-12-04 Cynora Gmbh Organic molecules for optoelectronic devices
US11678568B2 (en) 2008-05-16 2023-06-13 Semiconductor Energy Laboratory Co., Ltd. Triarylamine derivative, light-emitting substance, light-emitting element, light-emitting device, and electronic device

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5364089B2 (en) * 2007-04-13 2013-12-11 チェイル インダストリーズ インコーポレイテッド Material for organic photoelectric device including hole transport unit and electron transport unit, and organic photoelectric device including the same
KR101311934B1 (en) * 2009-06-08 2013-09-26 제일모직주식회사 Composition　for organic photoelectric　device and organic photoelectric　device using the same
WO2012011642A1 (en) * 2010-07-23 2012-01-26 고려대학교 산학협력단 Quasi-solid polymer electrolyte for dye-sensitized solar cell, hole transport material contained in same, and dye-sensitized solar cell containing the electrolyte
WO2012077902A2 (en) 2010-12-08 2012-06-14 제일모직 주식회사 Compound for an organic optoelectronic device, organic light-emitting diode including the compound, and display device including the organic light-emitting diode
JP6355922B2 (en) * 2011-02-04 2018-07-11 ロレアル Composite pigment and preparation method thereof
US9859517B2 (en) 2012-09-07 2018-01-02 Nitto Denko Corporation White organic light-emitting diode
KR101297162B1 (en) * 2012-10-15 2013-08-21 제일모직주식회사 Composition　for organic photoelectric　device and organic photoelectric　device using the same
JP2014110313A (en) 2012-11-30 2014-06-12 Samsung Display Co Ltd Hole transporting material for organic electroluminescent element, and organic electroluminescent element employing the same
JP6764671B2 (en) * 2015-04-14 2020-10-07 株式会社半導体エネルギー研究所 Heterocyclic compounds, light emitting devices, light emitting devices, electronic devices, and lighting devices
US10043984B2 (en) * 2015-07-01 2018-08-07 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
JP2018104359A (en) * 2016-12-27 2018-07-05 株式会社半導体エネルギー研究所 Organic compound, light emitting element, light emitting device, electronic apparatus, and illumination device
CN109053690B (en) * 2018-08-03 2021-04-16 大连理工大学 Bipolar electroluminescent material containing carbazole group and application thereof
KR102605293B1 (en) * 2018-08-07 2023-11-22 엘지디스플레이 주식회사 Organic light emitting diode and organic light emitting device having the diode

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004311404A (en) 2003-03-26 2004-11-04 Konica Minolta Holdings Inc Organic electroluminescent element, illumination device and display device
EP1489155A1 (en) * 2002-03-22 2004-12-22 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent devices and organic electroluminescent devices made by using the same
WO2006067976A1 (en) * 2004-12-24 2006-06-29 Pioneer Corporation Organic compound, charge-transporting material, and organic electroluminescent element
JP2007067383A (en) * 2005-08-04 2007-03-15 Mitsubishi Chemicals Corp Charge transport material, organic electroluminescent element, and composition thereof

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3965800B2 (en) * 1997-12-01 2007-08-29 チッソ株式会社 Organic electroluminescent device using triarylamine derivative
JP2000113504A (en) * 1998-10-05 2000-04-21 Mitsui Chemicals Inc Optical recording medium
CN100366703C (en) * 2002-03-22 2008-02-06 出光兴产株式会社 Material for organic electroluminescent device and organic electroluminescent device using the same
KR20040089567A (en) * 2003-04-14 2004-10-21 가부시키가이샤 도요다 지도숏키 Organic electroluminescent element that suppresses generation of ultraviolet light and lighting system that has organic electroluminescent element
JP4379243B2 (en) * 2004-07-23 2009-12-09 コニカミノルタビジネステクノロジーズ株式会社 Image forming method, image forming apparatus, electrophotographic photosensitive member, and image forming unit
JP2006069964A (en) * 2004-09-02 2006-03-16 Koei Chem Co Ltd Bis(carbazol-9-yl)aryl compound
EP2437326A3 (en) * 2006-12-13 2013-11-13 Konica Minolta Holdings, Inc. Organic electroluminescent element, display device and lighting device
JP5364089B2 (en) * 2007-04-13 2013-12-11 チェイル インダストリーズ インコーポレイテッド Material for organic photoelectric device including hole transport unit and electron transport unit, and organic photoelectric device including the same
JP5325402B2 (en) * 2007-08-03 2013-10-23 ケミプロ化成株式会社 Novel bicarbazole derivative, host material and organic electroluminescence device using the same
KR100957620B1 (en) * 2007-11-01 2010-05-13 제일모직주식회사 Material for organic photoelectric device, and organic photoelectric device thereby

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1489155A1 (en) * 2002-03-22 2004-12-22 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent devices and organic electroluminescent devices made by using the same
JP2004311404A (en) 2003-03-26 2004-11-04 Konica Minolta Holdings Inc Organic electroluminescent element, illumination device and display device
WO2006067976A1 (en) * 2004-12-24 2006-06-29 Pioneer Corporation Organic compound, charge-transporting material, and organic electroluminescent element
JP2007067383A (en) * 2005-08-04 2007-03-15 Mitsubishi Chemicals Corp Charge transport material, organic electroluminescent element, and composition thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
APPL. PHYS. LETT., vol. 79, 2001, pages 2082 - 2084
See also references of EP2134809A4

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009035524A (en) * 2007-08-03 2009-02-19 Chemiprokasei Kaisha Ltd New bicarbazole derivative, and host material and organic electroluminescent element each using the same
JP2009059767A (en) * 2007-08-30 2009-03-19 Konica Minolta Holdings Inc Organic electroluminescent element, illumination apparatus, and display device
WO2009096549A1 (en) * 2008-01-31 2009-08-06 Hodogaya Chemical Co., Ltd. Compound having substituted pyridyl group and pyridoindole ring structure linked through phenylene group, and organic electroluminescent device
US8377573B2 (en) 2008-01-31 2013-02-19 Hodogaya Chemical Co., Ltd. Compound having substituted pyridyl group and pyridoindole ring structure linked through phenylene group, and organic electroluminescent device
EP2463288A1 (en) * 2008-01-31 2012-06-13 Hodogaya Chemical Co., Ltd. Compound having substituted pyridyl group and pyridoindole ring structure linked through phenylene group, and organic electroluminescent device
US11980087B2 (en) 2008-05-16 2024-05-07 Semiconductor Energy Laboratory Co., Ltd. Triarylamine derivative, light-emitting substance, light-emitting element, light-emitting device, and electronic device
US11678568B2 (en) 2008-05-16 2023-06-13 Semiconductor Energy Laboratory Co., Ltd. Triarylamine derivative, light-emitting substance, light-emitting element, light-emitting device, and electronic device
JP2012530754A (en) * 2009-06-24 2012-12-06 ジョージア・テック・リサーチ・コーポレーション Bipolar small molecule host for phosphorescent guest emitters
JPWO2011004807A1 (en) * 2009-07-10 2012-12-20 コニカミノルタホールディングス株式会社 Organic photoelectric conversion element, solar cell using the same, and optical sensor array
WO2011004807A1 (en) * 2009-07-10 2011-01-13 コニカミノルタホールディングス株式会社 Organic photoelectric conversion element, solar cell using same, and optical sensor array
JP5447521B2 (en) * 2009-07-10 2014-03-19 コニカミノルタ株式会社 Organic photoelectric conversion element, solar cell using the same, and optical sensor array
WO2011016202A1 (en) * 2009-08-05 2011-02-10 保土谷化学工業株式会社 Compound having substituted anthracene ring structure and pyridoindole ring structure and organic electroluminescence device
US9755152B2 (en) 2009-08-05 2017-09-05 Hodogaya Chemical Co., Ltd. Compound having substituted anthracene ring structure and pyridoindole ring structure, and organic electroluminescent device
CN102482274A (en) * 2009-08-05 2012-05-30 保土谷化学工业株式会社 Compound Having Substituted Anthracene Ring Structure And Pyridoindole Ring Structure And Organic Electroluminescence Device
US8927119B2 (en) 2009-08-05 2015-01-06 Hodogaya Chemical Co., Ltd. Compound having substituted anthracene ring structure and pyridoindole ring structure, and organic electroluminescent device
JP5636368B2 (en) * 2009-08-05 2014-12-03 保土谷化学工業株式会社 Compounds having substituted anthracene ring structure and pyridoindole ring structure and organic electroluminescence device
US10008673B2 (en) * 2010-03-02 2018-06-26 Merck Patent Gmbh Compounds for electronic devices
US20120319052A1 (en) * 2010-03-02 2012-12-20 Merck Patent Gmbh Compounds for electronic devices
US11264575B2 (en) 2010-03-02 2022-03-01 Merck Patent Gmbh Compounds for electronic devices
US8785003B2 (en) 2010-03-05 2014-07-22 Idemtisu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
WO2011108707A1 (en) * 2010-03-05 2011-09-09 出光興産株式会社 Material for organic electroluminescent element, and organic electroluminescent element using same
US9543530B2 (en) 2010-05-03 2017-01-10 Cheil Industries, Inc. Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode
WO2011145876A3 (en) * 2010-05-20 2012-04-19 주식회사 두산 Novel hybrid organic compound and organic electroluminescent device using same
KR101319734B1 (en) 2010-05-20 2013-10-17 주식회사 두산 Novel hybrid organic compounds and organic electroluminescence device comprising the same
WO2011145876A2 (en) * 2010-05-20 2011-11-24 주식회사 두산 Novel hybrid organic compound and organic electroluminescent device using same
EP2711949A1 (en) * 2010-12-10 2014-03-26 Korea University Research and Business Foundation Compounds having hole conducting property, co-adsorbent body comprising same, and dye-sensitized solar cell comprising the co-adsorbent body
US9799834B2 (en) 2011-08-18 2017-10-24 Semiconductor Energy Laboratory Co., Ltd. Carbazole compound light-emitting element, light-emitting device, electronic device, and lighting device
WO2014079527A1 (en) * 2012-11-23 2014-05-30 Merck Patent Gmbh Materials for electronic devices
US10020450B2 (en) 2012-11-23 2018-07-10 Merck Patent Gmbh Materials for electronic devices
WO2018189356A1 (en) * 2017-04-13 2018-10-18 Cynora Gmbh Organic molecules, in particular for use in optoelectronic devices
US11393984B2 (en) 2017-04-13 2022-07-19 Cynora Gmbh Organic molecules for use in organic optoelectronic devices
EP3575377A1 (en) * 2018-05-31 2019-12-04 Cynora Gmbh Organic molecules for optoelectronic devices
CN109651338A (en) * 2018-12-31 2019-04-19 瑞声科技（南京）有限公司 A kind of asymmetry carbazole pyridine compounds and its application

Also Published As

Publication number Publication date
CN101657517A (en) 2010-02-24
KR20080092890A (en) 2008-10-16
CN101657517B (en) 2013-03-27
US20100155706A1 (en) 2010-06-24
JP5364089B2 (en) 2013-12-11
EP2134809A1 (en) 2009-12-23
JP2010523648A (en) 2010-07-15
US20120280221A1 (en) 2012-11-08
EP2134809A4 (en) 2010-04-21
KR101030021B1 (en) 2011-04-20
US8247805B2 (en) 2012-08-21
EP2134809B1 (en) 2020-09-02

Similar Documents

Publication Publication Date Title
EP2134809B1 (en) Material for organic photoelectric device including electron transporting unit and hole transporting unit, and organic photoelectric device including the same
KR101650595B1 (en) Compound having substituted anthracene ring structure and pyridoindole ring structure and organic electroluminescence device
KR101348699B1 (en) Red color phosphorescent material and Organic electroluminescent device using the same
JP5774267B2 (en) Organic electroluminescent compound and light emitting diode using the same
EP2447335B1 (en) Compound for organic photoelectric device, organic light emitting diode including the same, and display including the organic light emitting diode
CN101784635B (en) Material for organic photoelectric device, and organic photoelectric device including the same
US10026901B2 (en) Organic electronic material and organic electroluminescent device
EP2447334B1 (en) Compound for an organic photoelectric element, and an organic photoelectric element comprising the same
KR101495547B1 (en) Novel compounds for electronic material and organic electronic device using the same
KR101247626B1 (en) Compounds for organic photoelectric device and organic photoelectric device containing the same
JP2016001749A (en) New organic electroluminescent compound and organic electroluminescent element including the same
US20120012830A1 (en) Material for organic photoelectric device, and organic photoelectric device thereby
KR101747976B1 (en) Compound having benzotriazole ring structure and organic electroluminescent element
JP2012508732A (en) Novel organometallic compound for electroluminescence and electroluminescent device using the same as luminescent material
US7652136B2 (en) Diarylaminofluorene-based organometallic phosphors and organic light-emitting devices made with such compounds
TWI483936B (en) Novel compound for organic photoelectric device and organic photoelectric device including the same
CN106518882A (en) Helical structural organic light emitting material and organic light emitting device thereof
KR102028503B1 (en) Phosphorescent material and organic light emitting diode device using the same
KR101984188B1 (en) Blue phosphorescent compound and Organic electroluminescent device using the same
US20030099861A1 (en) Efficient red organic electroluminescent devices
KR20100064587A (en) Green color phosphorescent material and organic electroluminescent device using the same
KR20140083413A (en) Red Phosphorescent Compounds and Organic Electroluminescent Device Using the Same
KR20060001405A (en) A 1-phenyl-7-azaindole based silicone compound and an organic electro luminescent device using the same

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200880010761.8

Country of ref document: CN

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

Ref document number: 08741343

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2010502951

Country of ref document: JP

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 2008741343

Country of ref document: EP

NENP Non-entry into the national phase

Ref country code: DE