US20120211736A1 - Compound for organic photoelectric device and organic photoelectric device including the same - Google Patents

Compound for organic photoelectric device and organic photoelectric device including the same Download PDF

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US20120211736A1
US20120211736A1 US13/463,211 US201213463211A US2012211736A1 US 20120211736 A1 US20120211736 A1 US 20120211736A1 US 201213463211 A US201213463211 A US 201213463211A US 2012211736 A1 US2012211736 A1 US 2012211736A1
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photoelectric device
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Hyung-Sun Kim
Eun-Sun Yu
Soo-Hyun Min
Ho-Jae Lee
Eui-Su Kang
Mi-Young Chae
Young-Hoon Kim
Ja-Hyun Kim
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Cheil Industries Inc
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Cheil Industries Inc
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Assigned to CHEIL INDUSTRIES, INC. reassignment CHEIL INDUSTRIES, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHAE, MI-YOUNG, KANG, EUI-SU, KIM (DECEASED), YOUNG-HOON, KIM (LEGAL REPRESENTATIVE), JA-HYUN, KIM, HYUNG-SUN, LEE, HO-JAE, MIN, SOO-HYUN, YU, EUN-SUN
Priority to US13/555,558 priority Critical patent/US8828561B2/en
Publication of US20120211736A1 publication Critical patent/US20120211736A1/en
Priority to US14/262,135 priority patent/US9478755B2/en
Priority to US14/518,912 priority patent/US9450193B2/en
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Definitions

  • Embodiments relate to a compound for organic photoelectric device and an organic photoelectric device including the same.
  • a photoelectric device is, in a broad sense, a device for transforming photo-energy to electrical energy, or conversely, for transforming electrical energy to photo-energy.
  • An organic photoelectric device may be classified as follows in accordance with its driving principles.
  • a first organic photoelectric device is an electron device driven as follows: excitons are generated in an organic material layer by photons from an external light source, the excitons are separated into electrons and holes, and the electrons and holes are transferred to different electrodes as a current source (voltage source).
  • a second organic photoelectric device is an electron device driven as follows: a voltage or a current is applied to at least two electrodes to inject holes and/or electrons into an organic material semiconductor positioned at an interface of the electrodes, and the device is driven by the injected electrons and holes.
  • the organic photoelectric device includes an organic light emitting diode (OLED), an organic solar cell, an organic photo-conductor drum, an organic transistor, an organic memory device, etc.
  • the organic photoelectric device may use a hole injecting or transporting material, an electron injecting or transporting material, or a light emitting material.
  • organic light emitting diode has recently drawn attention due to an increase in demand for flat panel displays.
  • organic light emission refers to transformation of electrical energy to photo-energy.
  • the organic light emitting diode transforms electrical energy into light by applying a voltage or current to an organic light emitting material.
  • the organic light emitting diode may have a functional organic material layer interposed between an anode and a cathode.
  • the organic material layer may be formed as a multi-layer including different materials, e.g., a hole injection layer (HIL), a hole transport layer (HTL), an emission layer, an electron transport layer (ETL), and an electron injection layer (EIL), in order to improve efficiency and stability of the organic light emitting diode.
  • HIL hole injection layer
  • HTL hole transport layer
  • ETL electron transport layer
  • EIL electron injection layer
  • an organic light emitting diode when a voltage is applied between an anode and a cathode, holes from the anode and electrons from the cathode are injected to an organic material layer.
  • the generated excitons generate light having certain wavelengths while shifting to a ground state.
  • An organic light emitting diode may include a low molecular aromatic diamine and aluminum complex as an emission layer-forming material.
  • the organic layer may have a structure in which a thin film (hole transport layer (HTL)) of a diamine derivative and a thin film of tris(8-hydroxy-quinolate)aluminum (Alq 3 ) are laminated.
  • HTL hole transport layer
  • a phosphorescent light emitting material may be used for a light emitting material of an organic light emitting diode in addition to a fluorescent light emitting material.
  • the phosphorescent material may emit light by transitioning electrons from a ground state to an excited state, non-radiative transitioning of a singlet exciton to a triplet exciton through intersystem crossing, and transitioning the triplet exciton to a ground state to emit light.
  • an organic material layer may include a light emitting material and a charge transport material, e.g., a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc.
  • a charge transport material e.g., a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc.
  • the light emitting material may be classified as blue, green, and red light emitting materials according to emitted colors, and yellow and orange light emitting materials to emit colors approaching natural colors.
  • Embodiments are directed to a compound for an organic photoelectric device, the compound being represented by the following Chemical Formula (“CF”) 1:
  • Ar1 and Ar2 may each be independently selected from the group of a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C2 to C30 heteroaryl group,
  • Ar3 and Ar4 may each be independently selected from the group of hydrogen, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group, and
  • R1 to R4 may each be independently selected from the group of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group.
  • the compound represented by CF 1 may be represented by the following CF 3:
  • Ar1 and Ar2 may each be independently selected from the group of a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C2 to C30 heteroaryl group,
  • Ar3 and Ar4 may each be independently selected from the group of hydrogen, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group, and
  • R1 to R4 may each be independently selected from the group of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group.
  • the compound represented by CF 3 may be represented by the following CF 5:
  • Ar2 and Ar5 may each be independently selected from the group of a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C2 to C30 heteroaryl group,
  • Ar3, Ar4 and Ar6 may each be independently selected from the group of hydrogen, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group, and
  • R1 to R6 may each be independently selected from the group of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group.
  • Ar5 may be a C6 to C12 aryl group, and Ar2 may be a C10 to C20 fused polycyclic group.
  • Ar5 may be a C6 to C12 aryl group
  • Ar2 may be selected from the group of a C6 to C30 substituted or unsubstituted an arylamine group, C6 to C30 substituted or unsubstituted aminoaryl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, and a substituted or unsubstituted triazine group.
  • the compound represented by CF 1 may be represented by the following CF 2:
  • Ar1 and Art may each be independently selected from the group of a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C2 to C30 heteroaryl group,
  • Ar3 and Ar4 may each be independently selected from the group of hydrogen, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group, and
  • R1 to R4 may each be independently selected from the group of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group.
  • the compound represented by CF 2 may be represented by the following CF 4:
  • Ar2 and Ar5 may each be independently selected from the group of a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C2 to C30 heteroaryl group,
  • Ar3, Ar4 and Ar6 may each be independently selected from the group of hydrogen, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group, and
  • R1 to R6 may each be independently selected from the group of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group.
  • Ar5 may be a C6 to C12 aryl group, and Ar2 may be a C10 to C20 fused polycyclic group.
  • Ar5 may be a C6 to C12 aryl group
  • Ar2 may be selected from the group of a C6 to C30 substituted or unsubstituted an arylamine group, C6 to C30 substituted or unsubstituted aminoaryl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, and a substituted or unsubstituted triazine group.
  • the compound represented by CF 1 may be represented by one or more of the following CF 6 to 37:
  • the compound represented by CF 1 may be represented by one or more of the following CF 38 and 42 to 72.
  • the compound represented by CF 1 may be represented by one or more of the following CF 73 to 83.
  • the compound represented by CF 1 may be represented by one or more of the following CF N-3 to N-54, A-2 to A-26, B-3 to B-22, and C-1 to C-18:
  • Embodiments are also directed to an organic photoelectric device, including an anode, a cathode, and at least one organic thin layer, the at least one organic thin layer being disposed between the anode and cathode, and including a compound according to an embodiment.
  • the organic thin layer may be selected from the group of an emission layer, a hole transport layer (HTL), a hole injection layer (HIL), an electron transport layer (ETL), an electron injection layer (EIL), a hole blocking layer, and a combination thereof.
  • HTL hole transport layer
  • HIL hole injection layer
  • ETL electron transport layer
  • EIL electron injection layer
  • the compound may be included in an electron transport layer (ETL) or an electron injection layer (EIL).
  • ETL electron transport layer
  • EIL electron injection layer
  • the compound may be included in an emission layer.
  • the compound may be used as a phosphorescent or fluorescent host material in an emission layer.
  • the compound may be used as a fluorescent blue dopant material in an emission layer.
  • Embodiments are also directed to a display device including an organic photoelectric device according to an embodiment.
  • FIGS. 1 to 5 illustrate cross-sectional views showing organic light emitting diodes including compounds according to various embodiments.
  • organic photoelectric device 110 cathode 120: anode 105: organic thin layer 130: emission layer 140: hole transport layer (HTL) 150: electron transport layer (ETL) 160: electron injection layer (EIL) 170: hole injection layer (HIL) 230: emission layer + electron transport layer (ETL)
  • hetero refers to one including 1 to 3 of N, O, S, or P, and remaining carbons in one ring.
  • the term “combination thereof” refers to at least two substituents bound to each other by a linker, or at least two substituents condensed to each other.
  • alkyl refers to an aliphatic hydrocarbon group.
  • the alkyl may be a saturated alkyl group that does not include any alkene or alkyne.
  • the alkyl may be branched, linear, or cyclic.
  • alkene refers to a group in which at least two carbon atoms are bound in at least one carbon-carbon double bond
  • alkyne refers to a group in which at least two carbon atoms are bound in at least one carbon-carbon triple bond
  • the alkyl group may have 1 to 20 carbon atoms.
  • the alkyl group may be a medium-sized alkyl having 1 to 10 carbon atoms.
  • the alkyl group may be a lower alkyl having 1 to 6 carbon atoms.
  • a C1-C4 alkyl may have 1 to 4 carbon atoms and may be selected from the group of methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, and t-butyl.
  • Examples of an alkyl group may be selected from the group of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, ethenyl, propenyl, butenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or the like, which may be individually and independently substituted.
  • aryl refers to an aryl group including a carbocyclic aryl (e.g., phenyl) having at least one ring having a covalent pi electron system.
  • carbocyclic aryl e.g., phenyl
  • the term also refers to monocyclic or fused polycyclic (i.e., rings sharing adjacent pairs of carbon atoms) groups.
  • this term also refers to a spiro compound having a contact point of one carbon.
  • substituted refers to one substituted with at least one selected from the group of a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C10 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group such as a trifluoromethyl group, and the like, a C12 to C30 carbazole group, a C6 to C30 arylamine group, a C6 to C30 substituted or unsubstituted aminoaryl group, or a cyano group.
  • a compound according to an embodiment for an organic photoelectric device is represented by the following Chemical Formula (“CF”) 1.
  • Ar1 and Ar2 may each be independently selected from the group of a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C2 to C30 heteroaryl group.
  • Ar3 and Ar4 may each be independently selected from the group of hydrogen, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group.
  • a ⁇ -conjugation length of Art to Ar4 may be adjusted to enlarge a triplet energy bandgap, and thereby the compound may be usefully applied to the emission layer of an organic photoelectric device as a phosphorescent host.
  • R1 to R4 may each be independently selected from the group of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group.
  • improved thermal stability and/or oxidation resistance may be provided, and the life-span characteristic of an organic photoelectric device may be improved.
  • two carbazole groups may be bound to each other at the 3 position or 4 position of each carbazole group, as shown in the following CF 2 or 3.
  • the two carbazole groups are bound to each other at the 3 position.
  • the compound may be synthesized easily and may provide improved oxidation stability by substituting hydrogen at the 3 position of the carbazole group.
  • the two carbazole groups are bound to each other at the 4 position.
  • the two carbazole groups may not occupy the same plane, and thus crystallization may be suppressed and solubility may be improved.
  • the ⁇ -conjugation length may become very short, and thus triplet bandgap may become high.
  • the Ar1 to Ar4 and R1 to R4 are the same as described above.
  • Ar1 may be another carbazole. Examples thereof are represented by the following CF 4 and 5.
  • Ar2 and Ar5 may each be independently selected from the group of a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C2 to C30 heteroaryl group
  • Ar3, Ar4 and Ar6 may each be independently selected from the group of hydrogen, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group.
  • a triplet energy bandgap may be enlarged due to adjustment of ⁇ -conjugation length of Ar2 to Ar6, and thereby the compound may be applied to an emission layer of an organic photoelectric device as a phosphorescent host. Also, due to an increase of carbazole, hole injection and transport properties may be improved.
  • R1 to R6 may each be independently selected from the group of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group.
  • improved thermal stability and/or oxidation resistance may be provided, and the life-span characteristic of an organic photoelectric device may be improved.
  • Ar5 may be a C6 to C12 aryl group
  • Ar2 may be a C10 to C20 fused polycyclic group.
  • the substituent is a fused polycyclic group, thermal stability, electron transporting, and injection properties may increase.
  • Ar5 may be a C6 to C12 aryl group
  • Ar2 may be selected from the group of a C6 to C30 substituted or unsubstituted arylamine group, a C6 to C30 substituted or unsubstituted aminoaryl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, and a substituted or unsubstituted triazine group.
  • substituents are an arylamine group, aminoaryl group, or carbazole group that increases hole transport properties, hole injection and transport properties of the compound may be improved.
  • substituents are a pyrimidine group or a triazine group that increase electron transport properties, electron injection and transporting properties of the compound may be improved.
  • Numbers of the substituents may control electron transporting properties of the compound.
  • the compound may have a bulky structure due to adjustment of the substituents, and thereby crystallinity may be decreased.
  • the decreased crystallinity of the compound may lengthen the life-span of a device.
  • the compound for an organic photoelectric device may be represented by, e.g., the following CF 6 to 38 and 42 to 83.
  • the compound for an organic photoelectric device may be represented by, e.g., the following CF N-3 to N-54.
  • the compound for an organic photoelectric device may be represented by, e.g., the following CF A-2 to A-26.
  • the compound for an organic photoelectric device may be represented by, e.g., the following CF B-3 to B-22.
  • the compound for an organic photoelectric device may be represented by, e.g., the following CF C-1 to C-18.
  • the compound for an organic photoelectric device may have a glass transition temperature of higher than or equal to 110° C., and/or a thermal decomposition temperature of higher than or equal to 400° C., so as to improve thermal stability. Thereby, it may be possible to produce an organic photoelectric device having a high efficiency.
  • the compound according to an embodiment may have an appropriate HOMO energy level, and hole injection may be realized smoothly, and holes and electrons may be transported well.
  • the compound according to an embodiment for an organic photoelectric device may play a role for emitting light or injecting and/or transporting electrons, and it may act as a light emitting host together with a suitable dopant.
  • the compound may be applied as, e.g., a phosphorescent or fluorescent host material, a blue light emitting dopant material, or an electron transport material.
  • the compound for an organic photoelectric device according to an embodiment is used for an organic thin layer. Thus, it may improve the life-span characteristic, efficiency characteristics, electrochemical stability, and thermal stability of an organic photoelectric device, and may decrease the driving voltage.
  • an organic photoelectric device may be provided that includes the compound for an organic photoelectric device.
  • the organic photoelectric device may include an organic light emitting diode, an organic solar cell, an organic transistor, an organic photosensitive drum, an organic memory device, or the like.
  • the compound for an organic photoelectric device according to an embodiment may be included in an electrode or an electrode buffer layer in the organic solar cell to improve the quantum efficiency, or it may be used as an electrode material for a gate, a source-drain electrode, or the like in the organic transistor.
  • the organic photoelectric device includes an anode, a cathode, and at least one organic thin layer interposed between the anode and the cathode.
  • the at least one organic thin layer may provide an organic photoelectric device including the compound for an organic photoelectric device according to an embodiment.
  • the organic thin layer that may include the compound for an organic photoelectric device may include a layer selected from the group of an emission layer, a hole transport layer (HTL), a hole injection layer (HIL), an electron transport layer (ETL), an electron injection layer (EIL), a hole blocking film, and a combination thereof.
  • the electron transport layer (ETL) or the electron injection layer (EIL) may include the compound for an organic photoelectric device according to an embodiment.
  • the compound for an organic photoelectric device when the compound for an organic photoelectric device is included in the emission layer, the compound for an organic photoelectric device may be included as a phosphorescent or fluorescent host, and particularly, as a fluorescent blue dopant material.
  • FIGS. 1 to 5 illustrate cross-sectional views showing an organic photoelectric device including the compound for an organic photoelectric device according to an embodiment.
  • organic photoelectric devices 100, 200, 300, 400, and 500 may include at least one organic thin layer 105 interposed between an anode 120 and a cathode 110.
  • the anode 120 may include an anode material laving a large work function to help hole injection into an organic thin layer.
  • the anode material may include: a metal such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); a combined metal and oxide such as ZnO:Al or SnO 2 :Sb; or a conductive polymer such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, polyaniline, etc. It is preferable to include a transparent electrode including indium tin oxide (ITO) as an anode.
  • ITO indium tin oxide
  • the cathode 110 may include a cathode material having a small work function to help electron injection into an organic thin layer.
  • the cathode material may include: a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; or a multi-layered material such as LiF/Al, Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al, BaF 2 /Ca, etc. It is preferable to include a metal electrode including aluminum as a cathode.
  • 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), and a hole transport layer (HTL) 140.
  • the emission layer 230 also functions as an electron transport layer (ETL), and the hole transport layer (HTL) 140 layer has an excellent binding property with a transparent electrode such as ITO or an excellent hole transporting property.
  • a three-layered organic photoelectric device 300 includes an 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 an 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.
  • EIL electron injection layer
  • HTL hole transport layer
  • HIL hole injection layer
  • a five layered organic photoelectric device 500 includes an 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 a low voltage.
  • ETL electron transport layer
  • HTL hole transport layer
  • HIL hole injection layer
  • EIL electron injection layer
  • the organic thin layer 105 including at least one selected from the group of an electron transport layer (ETL) 150, an electron injection layer (EIL) 160, an emission layer 130 and 230, a hole transport layer (HTL) 140, a hole injection layer (HIL) 170, and combinations thereof includes a compound for an organic photoelectric device according to an embodiment.
  • the material for the organic photoelectric device may be used for an electron transport layer (ETL) 150 including the electron transport layer (ETL) 150 or electron injection layer (EIL) 160.
  • ETL electron transport layer
  • the material for the organic photoelectric device may be included as a phosphorescent or fluorescent host or a fluorescent blue dopant.
  • the organic photoelectric device may be fabricated by, e.g.: forming an anode on a substrate, forming an organic thin layer in accordance with 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, and providing a cathode thereon.
  • 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
  • Another embodiment provides a display device including the organic photoelectric device according to an embodiment.
  • the compound represented by CF 12 was synthesized as in Reaction Scheme 1.
  • the compound represented by CF 12 was element-analyzed. The result is provided as follows.
  • the compound represented by CF 26 was synthesized as in Reaction Scheme 2.
  • the compound represented by CF 26 was element-analyzed. The result is provided as follows.
  • the compound represented by CF 10 was synthesized as in Reaction Scheme 3.
  • the compound represented by CF 10 was element-analyzed. The result is provided as follows.
  • the compound represented by CF N-4 was synthesized as in Reaction Scheme 4.
  • the compound represented by CF N-4 was element-analyzed. The result is provided as follows.
  • the compound represented by CF N-5 was synthesized as in Reaction Scheme 5.
  • the compound represented by CF N-5 was element-analyzed. The result is provided as follows.
  • the compound represented by CF N-14 was synthesized as in Reaction Scheme 6.
  • the compound represented by CF N-14 was element-analyzed. The result is provided as follows.
  • the compound represented by CF A-2 was synthesized as in Reaction Scheme 7.
  • the compound represented by CF A-10 was synthesized as in Reaction Scheme 8.
  • the mixture was heated at 110° C. and agitated for 12 hours under a nitrogen flow.
  • the compound represented by CF A-12 was synthesized as in Reaction Scheme 9.
  • the mixture was agitated for 12 hours under a nitrogen flow at 150° C.
  • the mixture was heated at 110° C. and agitated for 12 hours under a nitrogen flow.
  • the compound represented by CF B-5 was synthesized as in Reaction Scheme 10.
  • the mixture was heated at 110° C. and agitated for 12 hours under a nitrogen flow.
  • the compound represented by CF B-8 was synthesized as in Reaction Scheme 11.
  • the mixture was heated at 110° C. and agitated for 12 hours under a nitrogen flow.
  • the compound represented by CF B-21 was synthesized as in Reaction Scheme 12.
  • the mixture was heated at 110° C. and agitated for 12 hours under a nitrogen flow.
  • the compound represented by CF N-3 was synthesized as in Reaction Scheme 13.
  • the mixture was heated at 110° C. and agitated for 12 hours under a nitrogen flow.
  • the compound represented by CF N-54 was synthesized as in Reaction Scheme 14.
  • the mixture was heated at 110° C. and agitated for 12 hours under a nitrogen flow.
  • the compound represented by CF C-13 was synthesized as in Reaction Scheme 15.
  • the mixture was heated at 110° C. and agitated for 12 hours under a nitrogen flow.
  • An organic photoelectric device was fabricated by using a host of the compound represented by CF 11 obtained from Example 1, and a dopant of Ir(PPy) 3 .
  • the anode was ITO having a thickness of 1000 ⁇
  • the cathode was aluminum (Al) having a thickness of moo A.
  • the organic photoelectric device was fabricated by cutting an ITO glass substrate having a sheet resistance of 15 ⁇ /cm 2 to a size of 50 mm ⁇ 50 mm ⁇ 0.7 mm, ultrasonic wave cleaning the same in acetone, isopropyl alcohol, and pure water for 15 minutes for each, and UV ozone cleaning the same for 30 minutes to provide an anode.
  • N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB) (70 nm) and 4,4′,4′′-tri(N-carbazolyl)triphenylamine (TCTA) (10 nm) were deposited on the upper surface of the substrate under the conditions of a vacuum degree of 650 ⁇ 10 ⁇ 7 Pa and a deposition speed of 0.1 to 0.3 nm/s to provide a hole transport layer (HTL) having a thickness of 900 ⁇ .
  • HTL hole transport layer
  • a 300 ⁇ -thick emission layer was prepared by using the compound synthesized in Example 1 under the same vacuum deposition conditions, and a phosphorescence dopant of Ir(PPy) 3 was simultaneously deposited.
  • a deposition rate of phosphorescent dopant was adjusted so that the phosphorescent dopant was present in an amount of 7 wt % based on 100 wt % of emission layer.
  • Bis(8-hydroxy-2-methylquinolato)-aluminumbiphenoxide (BAlq) was deposited on the emission layer under the same vacuum deposition conditions to form a hole blocking layer having a thickness of 50 ⁇ .
  • Alq 3 was deposited under the same vacuum deposition conditions to provide an electron transport layer (ETL) having a thickness of 200 ⁇ .
  • ETL electron transport layer
  • LiF and Al were sequentially deposited on the upper surface of the electron transport layer (ETL) to fabricate an organic photoelectric device.
  • ETL electron transport layer
  • the organic photoelectric device had a structure of ITO/NPB (70 nm)/TCTA (10 nm)/EML (compound of Example 1 (93 wt %)+Ir(PPy) 3 (7 wt %), 30 nm)/BAlq (5 nm)/Alq 3 (20 nm)/LiF (1 nm)/Al (100 nm).
  • An organic photoelectric device was fabricated in accordance with the same procedure as in Example 4, except that the compound synthesized in Example 2 was used as a host of the emission layer.
  • An organic photoelectric device was fabricated in accordance with the same procedure as in Example 4, except that the compound synthesized in Example 3 was used as a host of the emission layer.
  • An organic photoelectric device was fabricated in accordance with the same procedure as in Example 4, except that the compound synthesized in Example N-1 was used as a host of the emission layer.
  • An organic photoelectric device was fabricated in accordance with the same procedure as in Example 4, except that the compound synthesized in Example N-2 was used as a host of the emission layer.
  • An organic photoelectric device was fabricated in accordance with the same procedure as in Example 4, except that the compound synthesized in Example N-4 was used as a host of the emission layer.
  • An organic photoelectric device was fabricated in accordance with the same procedure as in Example 4, except that the compound synthesized in Example N-6 was used as a host of the emission layer.
  • An organic photoelectric device was fabricated in accordance with the same procedure as in Example 4, except that the compound synthesized in Example N-7 was used as a host of the emission layer.
  • An organic photoelectric device was fabricated in accordance with the same procedure as in Example 4, except that the compound synthesized in Example N-10 was used as a host of the emission layer.
  • An organic photoelectric device was fabricated in accordance with the same procedure as in Example 4, except that the compound synthesized in Example N-11 was used as a host of the emission layer.
  • An organic photoelectric device was fabricated in accordance with the same procedure as in Example 4, except that the compound synthesized in Example N-12 was used as a host of the emission layer.
  • An organic photoelectric device was fabricated in accordance with the same procedure as in Example 4, except that 4,4-N,N-dicarbazolebiphenyl (CBP) was used as a host of the emission layer instead of the compound synthesized in Example 1.
  • CBP 4,4-N,N-dicarbazolebiphenyl
  • Comparative Example 1 was measured for luminance change, current density change depending upon voltage, and luminous efficiency.
  • the specific measurement methods were as follows and the results are shown in the following Table 1.
  • the obtained organic photoelectric device was measured for current value flowing in the unit device while increasing the voltage from 0 V to 10 V using a current-voltage meter (Keithley 2400), and the measured current value was divided by area to provide the result.
  • the obtained organic photoelectric device was measured for luminance using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V.
  • the current efficiency (cd/A) and electric power efficiency (lm/W) at the same luminance (1000 cd/m 2 ) were calculated by using luminance and current density from (1) and (2), and voltage
  • Examples 4 to 6 showed better driving voltage and efficiency compared to the reference material, CBP. These results showed that the compounds prepared in Examples 1 to 3 were applied as a material for an organic photoelectric device.
  • a maximum light emitting wavelength may be shifted to a long wavelength or color purity may decrease because of interactions between molecules, or device efficiency may decrease because of a light emitting quenching effect. Therefore, a host/dopant system may be used as a light emitting material in order to improve color purity and increase luminous efficiency and stability through energy transfer.
  • a material constituting an organic material layer for example a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and a light emitting material such as a host and/or a dopant, should be stable and have good efficiency. Such a material may also be useful other organic photoelectric devices.
  • a compound according to an embodiment may have excellent electrochemical and thermal stability, and may provide an organic photoelectric device having an excellent life span and high luminous efficiency at a low driving voltage.
  • a compound according to an embodiment may act as an electron injection and/or transport material, and may also act as a light emitting host along with an appropriate dopant.
  • a compound for an organic photoelectric device may have a structure in which two carbazole groups are bound to a core and a substituent is selectively bound to the core.
  • the compound for an organic photoelectric device may be a compound having various energy bandgaps by including the core and by introducing various substituents to the core, and thus may provide a compound satisfying conditions required for the emission layer as well as the electron injection layer (EIL) and transport layer.
  • EIL electron injection layer
  • an organic photoelectric device includes a compound having the appropriate energy level depending upon the substituents, and electron transporting properties may be controlled to provide excellent efficiency and driving voltage. Further, electrochemical and thermal stability may be improved to enhance the life-span characteristic while driving the organic photoelectric device.

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CN105670610B (zh) 2019-03-19
US20150069368A1 (en) 2015-03-12
CN102597158A (zh) 2012-07-18
EP2497811A2 (fr) 2012-09-12
JP2013510141A (ja) 2013-03-21
EP2497811A4 (fr) 2013-09-11
EP3460024B1 (fr) 2021-04-28
KR20110048840A (ko) 2011-05-12
WO2011055934A3 (fr) 2011-11-03
EP3460024A1 (fr) 2019-03-27
WO2011055934A2 (fr) 2011-05-12
EP2497811B1 (fr) 2018-12-19
US9450193B2 (en) 2016-09-20
CN105670610A (zh) 2016-06-15
KR101506999B1 (ko) 2015-03-31
WO2011055934A9 (fr) 2012-10-26

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