US20110272676A1 - Benzimidazole compound organic photoelectric device including the same, and display element including the same - Google Patents

Benzimidazole compound organic photoelectric device including the same, and display element including the same Download PDF

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US20110272676A1
US20110272676A1 US13/086,640 US201113086640A US2011272676A1 US 20110272676 A1 US20110272676 A1 US 20110272676A1 US 201113086640 A US201113086640 A US 201113086640A US 2011272676 A1 US2011272676 A1 US 2011272676A1
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substituted
unsubstituted
benzimidazole compound
independently
layer
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Sung-Hyun Jung
Hyung-Sun Kim
Ho-Jae Lee
Seung-Gyoung Lee
Eun-Sun Yu
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, LEE, SEUNG-GYOUNG, JUNG, SUNG-HYUN, KIM, HYUNG-SUN, KIM, YOUNG-HOON, LEE, HO-JAE, YU, EUN-SUN
Publication of US20110272676A1 publication Critical patent/US20110272676A1/en
Priority to US13/892,604 priority Critical patent/US9530970B2/en
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    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
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    • 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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/08—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
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    • 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
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • C09K2211/1441—Heterocyclic
    • C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
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    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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    • 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

  • Embodiments relate to a benzimidazole compound, an organic photoelectric device including the same, and a display element including the same.
  • the organic photoelectric device has been highlighted for the next generation display device.
  • the organic photoelectric device may be used in a display element or device driven at a low voltage, and may have various advantages over a thin film transistor-liquid crystal display (TFT-LCD).
  • TFT-LCD thin film transistor-liquid crystal display
  • the organic photoelectric device may be used in a display element or device that may be thinner, may have a wide viewing angle, and may have rapid response speed.
  • a small or medium sized display element or device including an organic photoelectric device may also have an equivalent or better image quality compared to a TFT-LCD, and its manufacturing process may be very simple. Therefore, it is considered that it will be advantageous in terms of cost in the future.
  • An organic photoelectric device includes an organic light emitting material between a rear plate (including ITO transparent electrode patterns as an anode on a transparent glass substrate) and an upper plate (including a metal electrode as a cathode on a substrate). When a predetermined voltage is applied between the transparent electrode and the metal electrode, current flows through the organic light emitting material to emit light.
  • an organic photoelectric device is composed of an anode of a transparent electrode, an organic thin layer as a light emitting region, and a metal electrode (cathode) formed on a glass substrate, in that order.
  • the organic thin layer may include, e.g., an emission layer, a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), and/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.
  • the provided light emitting excitons produce light by transiting to the ground state.
  • the light emission layer material may be classified as a fluorescent material using singlet excitons and a phosphorescent material using triplet excitons according to the light emitting mechanism.
  • the electron spin is flipped, and then it is transited to the ground state so that it provides a characteristic of extending the lifetime (emission duration) to more than that of fluorescent emission.
  • 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.
  • the singlet and the triplet are produced in a ratio of 1:3, in which the triplet excitons are produced at three times the amount of the singlet excitons in the organic photoelectric device.
  • the percentage of the singlet exited state is 25% in the case of a fluorescent material, so it has limits in luminous efficiency.
  • a phosphorescent material 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 100%.
  • a phosphorescent light emitting material when used, it has advantages in a luminous efficiency of around four times that of the fluorescent light emitting material.
  • a light emitting colorant may be added to an emission layer (host) in order to increase the efficiency and stability in the emission state.
  • Embodiments are directed to a benzimidazole compound, an organic photoelectric device including the same, and a display element including the same.
  • the embodiments may be realized by providing a benzimidazole compound represented by the following Chemical Formula 1:
  • A is CR′′ or N wherein R′′ is hydrogen or a C1 to C10 alkyl
  • Ar 1 to Ar 2 are each independently one selected from the group of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C6 to C30 arylamine, a substituted or unsubstituted C2 to C30 heteroarylamine, a substituted or unsubstituted carbazole, and a substituted or unsubstituted fluorene
  • x and y are each independently an integer of 0 to 5, provided that 1 ⁇ x+y ⁇ 5, R is hydrogen or a C1 to C7 alkyl, n is an integer of 0 to 3,
  • R′ is one selected from the group of a substituted or unsubstituted C1 to C50 alkyl and a substituted or unsubstituted C6 to C50
  • R′ in the above Chemical Formula 1 may be a substituted or unsubstituted C6 to C50 aryl.
  • the benzimidazole compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 2:
  • A is CR′′ or N wherein R′′ is hydrogen or a C1 to C10 alkyl
  • Ar 1 to Ar 2 are each independently one selected from the group of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C6 to C30 arylamine, a substituted or unsubstituted C2 to C30 heteroarylamine, a substituted or unsubstituted carbazole, and a substituted or unsubstituted fluorene
  • x and y are each independently integers of 0 to 5, provided that 1 ⁇ x+y ⁇ 5, n is an integer of 0 to 3
  • R 1 ′ to R 5 ′ are each independently one selected from the group of hydrogen, a halogen, a cyano, a hydroxy, an amino, a nitro, a carboxyl, a substituted or unsubsti
  • Ar 1 to Ar 2 may each independently be one selected from the group of a substituted or unsubstituted C6 to C30 arylamine and a substituted or unsubstituted carbazole.
  • Ar 1 and Ar 2 may include a substituted or unsubstituted C6 to C30 arylamine, and another of Ar 1 and Ar 2 may include a substituted or unsubstituted carbazole.
  • Ar 1 to Ar 2 may each independently be represented by one of the following Chemical Formulae 3 to 33:
  • R 1 to R 76 are each independently one selected from the group of a halogen, a cyano, a hydroxy, an amino, a nitro, a carboxyl, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C20 alkenyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C1 to C20 alkoxy, a substituted or unsubstituted C6 to C20 aryloxy, a substituted or unsubstituted C3 to C40 silyloxy, a substituted or unsubstituted C1 to C20 acyl, a substituted or unsubstituted C2 to C20 alkoxycarbonyl, a substituted or unsubstituted
  • the benzimidazole compounds may be a charge transporting material or a host material in an organic photoelectric device.
  • the benzimidazole compound represented by Chemical Formula 1 may be represented by one of the following Chemical Formulae 34-40:
  • the embodiments may also be realized by providing an organic photoelectric device including an anode, a cathode, and at least one organic thin layer between the anode and cathode, the at least one organic thin layer including the benzimidazole compound of an embodiment.
  • the at least one organic thin layer may be an emission layer.
  • the at least one organic thin layer may include at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer.
  • EIL electron injection layer
  • ETL electron transport layer
  • the embodiments may also be realized by providing a display element including the organic photoelectric device of an embodiment.
  • FIG. 1 illustrates a schematic cross-sectional view showing a display element including an organic photoelectric device according to an embodiment.
  • FIG. 2 illustrates LC-MS data of a compound M-6 prepared in Example 4.
  • FIG. 3 illustrates a graph showing a photoluminescence (PL) wavelength of the compound M-6 prepared in Example 4.
  • FIG. 4 illustrates a graph showing current density versus voltage of organic photoelectric devices fabricated using a solution process according to Example 8 and Comparative Example 1.
  • FIG. 5 illustrates a graph showing current density versus voltage of organic photoelectric devices fabricated using a solution process according to Example 9 and Comparative Example 2.
  • FIG. 6 illustrates a graph showing luminance versus voltage of organic photoelectric devices fabricated using a solution process according to Example 8 and Comparative Example 1.
  • FIG. 7 illustrates a graph showing luminance versus voltage of organic photoelectric devices fabricated using a solution process according to Example 9 and Comparative Example 2.
  • FIG. 8 illustrates a graph showing luminous efficiency versus luminance of organic photoelectric devices fabricated using a solution process according to Example 8 and Comparative Example 1.
  • FIG. 9 illustrates a graph showing luminous efficiency versus luminance of organic photoelectric devices fabricated using a solution process according to Example 9 and Comparative Example 2.
  • substituted may refer to one substituted with a substituent selected from the group of a halogen, a cyano, a hydroxy, an amino, a nitro, a carboxyl, an azo, a ferro, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C20 alkenyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C1 to C20 alkoxy, a substituted or unsubstituted C6 to C20 aryloxy, a substituted or unsubstituted C3 to C40 silyloxy, a substituted or unsubstituted C1 to C20 acyl, a substituted or unsubstituted C2 to C
  • hetero may refer to one including 1 to 3 heteroatoms selected from the group of N, O, S, and P in one ring.
  • An embodiment provides a benzimidazole compound represented by the following Chemical Formula 1.
  • A may be C or N
  • Ar 1 to Ar 2 may each independently be selected from the group of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C6 to C30 arylamine, a substituted or unsubstituted C2 to C30 heteroarylamine, a substituted or unsubstituted carbazole, and a substituted or unsubstituted fluorene,
  • x and y may each independently be integers of 0 to 5, provided that 1 ⁇ x+y ⁇ 5,
  • R may be hydrogen or a lower, e.g., C1 to C7, alkyl,
  • n may be an integer of 0 to 3
  • R′ may include one selected from the group of a substituted or unsubstituted C1 to C50 alkyl and a substituted or unsubstituted C6 to C50 aryl, and
  • n may be 1 or 2.
  • R′ is preferably a substituted or unsubstituted C6 to C50 aryl.
  • the C6 to C50 aryl may include one selected from the group of a substituted or unsubstituted phenyl and a substituted or unsubstituted naphthyl.
  • the benzimidazole compound represented by Chemical Formula 1 is preferably represented by the following Chemical Formula 2.
  • A may be C or N
  • Ar 1 to Ar 2 may each independently be one selected from the group of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C6 to C30 arylamine, a substituted or unsubstituted C2 to C30 heteroarylamine, a substituted or unsubstituted carbazole, and a substituted or unsubstituted fluorene,
  • x and y may each independently be integers of 0 to 5, provided that 1 ⁇ x+y ⁇ 5,
  • n may be an integer of 0 to 3
  • R 1 ′ to R 5 ′ may each independently be one selected from the group of hydrogen, a halogen, a cyano, a hydroxy, an amino, a nitro, a carboxyl, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C20 alkenyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C1 to C20 alkoxy, a substituted or unsubstituted C6 to C20 aryloxy, a substituted or unsubstituted C3 to C40 silyloxy, a substituted or unsubstituted C1 to C20 acyl, a substituted or unsubstituted C2 to C20 alkoxycarbonyl, a substituted or unsubstituted C2 to C20
  • n may be 1 or 2.
  • Ar 1 to Ar 2 may each independently be one selected from the group of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C6 to C30 arylamine, a substituted or unsubstituted C2 to C30 heteroarylamine, a substituted or unsubstituted carbazole, and a substituted or unsubstituted fluorene.
  • the substituted or unsubstituted C6 to C30 aryl of Chemical Formulae 1 and 2 preferably includes one selected from the group of a substituted or unsubstituted phenyl, a substituted or unsubstituted tolyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted diphenylanthracenyl, a substituted or unsubstituted dinaphthylanthracenyl, a substituted or unsubstituted pentacenyl, a substituted or unsubstituted bromophenyl, a substituted or unsubstituted hydroxyphenyl, a substituted or unsubstituted stilbene, a substituted or unsubsti
  • the substituted or unsubstituted C2 to C30 heteroaryl of Chemical Formulae 1 and 2 preferably includes one selected from the group of a substituted or unsubstituted thienyl and a substituted or unsubstituted pyridyl.
  • Ar 1 to Ar 2 are each independently one selected from the group of a substituted or unsubstituted C6 to C30 arylamine and a substituted or unsubstituted carbazole, the compound may exhibit a desirable balance between electron and hole transporting characteristics.
  • Ar 1 to Ar 2 are preferably each independently represented by one of the following Chemical Formulae 3 to 33.
  • R 1 to R 76 may each independently be one selected from the group of a halogen, a cyano, a hydroxy, an amino, a nitro, a carboxyl, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C20 alkenyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C1 to C20 alkoxy, a substituted or unsubstituted C6 to C20 aryloxy, a substituted or unsubstituted C3 to C40 silyloxy, a substituted or unsubstituted C1 to C20 acyl, a substituted or unsubstituted C2 to C20 alkoxycarbonyl, a substituted or unsubstituted C2 to C20 acyloxy,
  • n 1 , n 2 , n 4 , n 6 , n 10 , n 21 , n 26 , n 27 , n 35 , n 39 , n 46 , n 47 , n 49 , n 53 , n 59 , n 61 , and n 62 may each independently be integers of 0 to 5,
  • n 3 , n 5 , n 7 , n 8 , n 11 , n 12 , n 16 , n 22 , n 23 , n 29 , n 30 , n 31 , n 33 , n 36 , n 37 , n 40 , n 41 to n 44 , n 48 , n 50 to n 52 , n 54 , n 55 , n 57 , n 60 , n 63 , n 65 , and n 67 to n 73 may each independently be integers of 0 to 4,
  • n 9 , n 13 , n 14 , n 18 , n 19 , n 20 , n 25 , n 28 , n 32 , n 34 , n 38 , n 45 , n 56 , n 58 , and n 66 may each independently be integers of 0 to 3, and
  • n 17 and n 24 may each independently be integers of 0 to 2.
  • the benzimidazole compound represented by Chemical Formula 1, above preferably includes a compound represented by one of the following Chemical Formulae 34 to 131.
  • the benzimidazole compound according to an embodiment may be applicable as a host material or a charge transporting material for an organic photoelectric device.
  • the benzimidazole compound may be also used as a nonlinear optical material, an electrode material, a chromic material, and/or as materials applicable to an optical switch, a sensor, a module, a waveguide, an organic transistor, a laser, an optical absorber, a dielectric material, and a membrane due to its optical and electrical properties.
  • a hole blocking layer When the benzimidazole compound is used in a hole blocking layer or an electron transport layer (ETL) of a light emitting diode, hole blocking properties thereof may be reduced due to the presence of a hole transport backbone. Therefore, when the compound is applied to a hole blocking layer, it is preferable that it does not include a hole transport backbone.
  • a hole transport backbone may include, e.g., carbazoles, arylamines, penoxazines, and the like.
  • the compound exhibit electron transport and hole transport properties including the hole transport backbone may improve life-span and reduce a driving voltage of a light emitting diode.
  • An organic photoelectric device may include an anode, a cathode, and at least one organic thin layer interposed between the anode and cathode, the at least one organic thin layer including the benzimidazole compound.
  • the organic photoelectric device may be implemented as a display element or device including, e.g., an organic light emitting diode, an organic solar cell, an organic transistor, an organic photo-conductor drum, an organic memory device, and the like.
  • the organic photoelectric device is preferably an organic light emitting diode.
  • the benzimidazole compound may be used in an emission layer of an organic thin layer.
  • the benzimidazole compound may also be applied to an organic thin layer selected from the group of an electron injection layer (EIL), an electron transport layer (ETL), a hole blocking layer, and combinations thereof.
  • EIL electron injection layer
  • ETL electron transport layer
  • hole blocking layer a hole blocking layer
  • the organic thin layer between the anode and cathode may include an emission layer.
  • the organic thin layer may further include, e.g., an inter-layer, a hole transport layer (HTL), and an electron transport layer (ETL).
  • the inter-layer may be a buffer layer, e.g., a hole injection layer (HIL), a hole blocking layer, an electron injection layer (EIL), or an electron blocking layer.
  • FIG. 1 illustrates a schematic cross-sectional view of an organic photoelectric device according to an embodiment.
  • FIG. 1 shows an organic photoelectric device including a substrate 11 , an anode 12 , a hole transport layer (HTL) 13 , an emission layer 14 , an electron transport layer (ETL) 15 , and a cathode 16 .
  • HTL hole transport layer
  • ETL electron transport layer
  • the organic photoelectric device may be fabricated using the benzimidazole compound of an embodiment as follows.
  • an anode 12 material may be coated on an upper side of the substrate 11 .
  • the substrate 11 may be a glass substrate or a transparent plastic substrate having excellent transparency, face smoothness, handling ease, and water repellency.
  • the anode 12 may include a transparent and highly conductive material, e.g., indium tin oxide (ITO), tin oxide (SnO 2 ), zinc oxide (ZnO), and the like.
  • ITO indium tin oxide
  • SnO 2 tin oxide
  • ZnO zinc oxide
  • the hole transport layer (HTL) 13 may be disposed on the anode 12 using, e.g., vacuum deposition, sputtering, or spin coating.
  • the emission layer 14 may be disposed on the hole transport layer (HTL) 13 using, e.g., vacuum deposition or a solution coating method such as spin coating, inkjet printing, and the like.
  • the electron transport layer (ETL) 15 may be disposed between the emission layer 14 and the cathode 16 .
  • the emission layer 14 , the hole transport layer (HTL) 13 , and the electron transport layer (ETL) 15 may have a predetermined thickness, but are not specifically limited.
  • the emission layer 14 may have a thickness of about 5 nm to about 1 ⁇ m, and preferably about 10 to about 500 nm.
  • the hole transport layer (HTL) 13 and electron transport layer (ETL) 15 may respectively have a thickness of about 10 to about 10,000 ⁇ .
  • the electron transport layer (ETL) 15 may be formed using, e.g., vacuum deposition, sputtering, or spin coating of generally-used electron transport layer (ETL) 15 materials.
  • the hole transport layer (HTL) 13 and the electron transport layer (ETL) 15 may efficiently transport a carrier to the emission layer 14 to facilitate light emitting recombination in the emission layer 14 .
  • the hole transport layer (HTL) 13 material may include, but is not limited to, poly(3,4-ethylenedioxy-thiophene) (PEDOT) doped with poly(styrenesulfonic acid) (PSS), and N,N′-bis(3-methylphenyl)-N,N-diphenyl-[1,1′-biphenyl]-4,4′-diamine (TPD).
  • PEDOT poly(3,4-ethylenedioxy-thiophene)
  • PSS poly(styrenesulfonic acid)
  • TPD N,N′-bis(3-methylphenyl)-N,N-diphenyl-[1,1′-biphenyl]-4,4′-diamine
  • the electron transport layer (ETL) 15 material may include, but is not limited to, aluminum trihydroxyquinoline (Alq 3 ), a 1,3,4-oxadiazole derivative such as 2-(4-biphenylyl-5-phenyl-1,3,4-oxadiazole (PBD), a quinoxaline derivative such as 1,3,4-tris[(3-phenyl-6-trifluoromethyl)quinoxalin-2-yl]benzene (TPQ), and a triazole derivative.
  • Alq 3 aluminum trihydroxyquinoline
  • PBD 2-(4-biphenylyl-5-phenyl-1,3,4-oxadiazole
  • TPQ 1,3,4-tris[(3-phenyl-6-trifluoromethyl)quinoxalin-2-yl]benzene
  • TPQ 1,3,4-tris[(3-phenyl-6-trifluoromethyl)quinoxalin-2-yl]benzene
  • the emission layer 14 may include the benzimidazole compound of an embodiment.
  • the benzimidazole compound of an embodiment may be mixed with a phosphorescent light-emitting organic compound.
  • the benzimidazole compound of an embodiment may be a host doped with the phosphorescent light-emitting organic compound.
  • the phosphorescent organic compound may be a phosphorescent light emitting organic metal complex that emits from its triplet state, and is preferably a metal complex of at least one group VIII metal ion according to the periodic table of Gregor Johann Mendel.
  • the group VIII metal ion may include one of, e.g., Fe, Co, Ni, Ru, Rh, Pd, Os, Ir, and Pt, and is preferably Ir or Pt.
  • Examples of the metal complex may be represented by the following Chemical Formulae 132 to 134, but are not limited thereto.
  • the organic layer including the organic compound is formed using a solution coating
  • another low molecular weight host material may be included along with the organic compound.
  • the low molecular weight host material may include compounds represented by the following Chemical Formulae 135 to 138, but are not limited thereto.
  • the benzimidazole compound may be used by mixing with polymers having conjugated double bonds, e.g., fluorene-based polymers, polyphenylenevinylene-based polymers, and/or polyparaphenylene-based polymers, and also by mixing with binder resins.
  • polymers having conjugated double bonds e.g., fluorene-based polymers, polyphenylenevinylene-based polymers, and/or polyparaphenylene-based polymers, and also by mixing with binder resins.
  • the binder resins may include, e.g., polyvinylcarbazole (PVK), polycarbonate, polyester, polyan arylate, polystyrene, acryl polymers, methacryl polymers, polybutyral, polyvinylacetal, diallylphthalate polymers, phenol resins, epoxy resins, silicone resins, polysulfone resins, and/or urea resins. These resins can be used singularly or in combinations thereof.
  • PVK polyvinylcarbazole
  • a hole blocking layer may be disposed using vacuum deposition to limit transport speed of holes into the emission layer 14 and thus to increase the recombination opportunity of electrons and holes.
  • a cathode 16 material may be coated on the electron transport layer (ETL).
  • ETL electron transport layer
  • the cathode material may include, e.g., lithium (Li), magnesium (Mg), calcium (Ca), aluminum (Al), Al:Li, Ba:Li, or Ca:Li having a small work function.
  • the reactant was cooled to room temperature and then extracted several times with methylene chloride and washed with water. The washed reactant was treated with anhydrous magnesium sulfate to remove moisture therefrom. The resulting reactant was filtered to remove the solvent. When the solvent was removed, the acquired solid was recrystallized with a mixed solvent of methylene chloride/hexane in a ratio of 1:6, preparing 1.2 g of a white compound M-2 (yield: 68.4%). This was sublimated and purified to prepare 0.79 g of a white crystal. This crystal had a maximum light emitting wavelength at 383 nm when it was fabricated into a thin film. It had an LC-MS theoretical value of C 55 H 36 N 4 [MH] + 753.2940 and a measurement value of 753.2978.
  • the reactant was cooled to room temperature and extracted several times with methylene chloride and washed with water. The washed reactant was treated with anhydrous magnesium sulfate to remove moisture. The remaining solid was filtered to remove the solvent. The resulting product was purified through a silica gel column with a methylene chloride solvent, providing 3.0 g of a white compound M-5 (yield: 56.8%).
  • the washed reactant was treated with anhydrous magnesium sulfate to remove moisture and then filtered to remove the solvent.
  • the resulting product was purified through a silica gel column with a methylene chloride solvent, providing 1.0 g of a white compound M-6 (yield: 82.6%).
  • a white compound M-6 yield: 82.6%
  • the resulting product was purified through a silica gel column with a methylene chloride solvent, providing 0.66 g of a white compound M-7 (yield: 45.5%). When it was fabricated into a thin film, it had a maximum light emitting wavelength at 404 nm. Its LC-MS theoretical value was C61H 39 N 5 [MH] + 842.3205, and the measurement value was 842.3331.
  • the washed reactant was treated with anhydrous magnesium sulfate to remove moisture and filtered to remove the solvent.
  • the resulting product was treated with a methylene chloride solvent through a silica gel column, providing 1.5 g of a white compound M-8 (yield: 44.9%). It had an LC-MS theoretical value of C 55 H 36 N 4 [MH] + 753.2940 and a measurement value of 753.2949.
  • the washed reactant was treated with anhydrous magnesium sulfate to remove moisture and filtered to remove the solvent.
  • the remaining solid was purified with a methylene chloride solvent through a silica gel column, providing 1.6 g of a white compound M-9 (yield: 47.9%). It had a theoretical value of LC-MS C 55 H 36 N 4 [MH] + 753.2940 and a measurement value of 753.2980.
  • the compounds (M-2 to M-4 and M-6 to M-9) of Examples 1 to 7 were measured regarding molecular weight to analyze the structure by using a liquid chromatography-mass analyzer (LC-MS, liquid chromatograph-mass spectrometry). LC-MS data of the compound M-6 prepared in Example 4 is shown in FIG. 2 .
  • LC-MS liquid chromatography-mass analyzer
  • FIG. 3 illustrates the PL wavelength result of the compound M-6 according to Example 4. Referring to FIG. 3 , when it was fabricated into a thin film, the compound M-6 had a maximum light emitting wavelength at 390 nm.
  • An ITO substrate was used as an anode.
  • the anode was spin-coated, forming a poly(3,4-ethylenedioxy-thiophene) (PEDOT) layer on a top thereof.
  • PEDOT poly(3,4-ethylenedioxy-thiophene)
  • a 400 ⁇ thick emission layer was spin-coated on the surface of the PEDOT by doping compound M-6 of Example 4 (as a host) with about 13 wt % of Ir(mppy) 3 as a dopant.
  • BAlq was vacuum-deposited to a thickness of 50 ⁇ to form a hole blocking layer.
  • Alq 3 was vacuum-deposited to a thickness of 200 ⁇ on top of the emission layer to form an electron transport layer (ETL).
  • ETL electron transport layer
  • a 10 ⁇ LiF layer and a 1,000 ⁇ Al layer were sequentially vacuum-deposited to fabricate a cathode of the resultant organic photoelectric device.
  • the organic photoelectric device included a 5-component organic thin layer, and in particular, it was ITO 1,500 ⁇ /PEDOT 600 ⁇ /EML (M-6:Ir(mppy) 3 ) 400 ⁇ /BAlq 50 ⁇ /Alq 3 200 ⁇ /LiF 10 ⁇ /Al 1,000 ⁇ .
  • a device included ITO 1,500 ⁇ /PEDOT 600 ⁇ /EML (TCTA:TPBI 1:1, Ir(mppy) 3 ) 400 ⁇ /BAlq 50 ⁇ /Alq 3 200 ⁇ /LiF 10 ⁇ /Al 1,000 ⁇ .
  • the emission layer was spin-coated to a thickness of 400 ⁇ by doping a mixture of 4,4′,4′′-tris(N-carbazolyl)triphenylamine (TCTA) and 2,2′,2′′-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (TPBI) prepared in a weight ratio of 1:1 as a host with about 13 wt % of Ir(mppy) 3 as a dopant.
  • TCTA 4,4′,4′′-tris(N-carbazolyl)triphenylamine
  • TPBI 2,2′,2′′-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole)
  • a device using a solution process was fabricated according to the same method as in Example 8, except for the differences described above.
  • An ITO substrate was used as an anode, and a device was fabricated by vacuum-depositing a series of layers thereon.
  • the device of Example 9 included a hole transport layer (HTL) formed by vacuum-depositing 4,4′-bis[N-[4-(N,N-di-m-tolylamino)phenyl]-N-phenylamino]biphenyl (DNTPD) and N-(1-naphthyl)-N-phenyl-amino]biphenyl (NPB) to respective thicknesses of 600 ⁇ and 200 ⁇ .
  • HTL hole transport layer
  • Example 9 also included an emission layer formed to a thickness of 300 ⁇ by vacuum-depositing compound M-4 of Example 3 as a host with about 7 wt % of Ir(ppy) 3 as a dopant.
  • a device including an emission layer was formed by vacuum-depositing 4,4′-N,N′-dicarbazole-bipheyl (CBP) as a host and 7 wt % of Ir(ppy) 3 as a dopant to a thickness of 300 ⁇ .
  • CBP 4,4′-N,N′-dicarbazole-bipheyl
  • the device using a deposition process device was fabricated according the same method as in Example 9 except for the differences described above.
  • Comparative Examples 1 and 2 were measured regarding current density and luminance change depending on voltage change and luminous efficiency change depending on luminance change. Specifically, they were measured as follows.
  • Each organic light emitting diode was measured regarding current value by using a current-voltage device (Keithley 2400) while its voltage was increased from 0. The current value was divided by area to calculate current density. The results are illustrated in FIGS. 4 and 5 .
  • the organic light emitting diodes were measured regarding luminance by using a luminance meter (Minolta Cs-1000A) while its voltage was increased from 0. The results are illustrated in FIGS. 6 and 7 .
  • the organic light emitting diodes were measured regarding luminous efficiency change depending on luminance change. The results are illustrated in FIGS. 8 and 9 .
  • Tables 1 and 2 comprehensively show all the results.
  • Table 1 shows performance evaluation results of the solution process devices according to Comparative Example 1 and Example 8.
  • a benzimidazole compound according to an embodiment decreased the driving voltage of an organic light emitting diode and improved luminance and efficiency when included as a host material.
  • Table 2 shows performance evaluation results of the deposition process devices according to Comparative Example 2 and Example 9.
  • a benzimidazole compound according to an embodiment decreased the driving voltage of an organic light emitting diode and improved luminance and efficiency when included as a host material.
  • Typical organic host materials may be exemplified by a material including naphthalene, anthracene, phenanthrene, tetracene, pyrene, benzopyrene, chrysene, pycene, carbazole, fluorene, biphenyl, terphenyl, triphenylene oxide, dihalobiphenyl, trans-stilbene, and 1,4-diphenylbutadiene.
  • 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.
  • the Alq 3 thin film functions as an electron transporting emission layer.
  • the host material may typically include 4,4-N,N-dicarbazole biphenyl (CBP) having a glass transition temperature of 110° C. or less and high symmetry, and thus may crystallize and cause a short circuit and a pixel defect according to results of thermal resistance tests of the devices.
  • CBP 4,4-N,N-dicarbazole biphenyl
  • the hole transporting property may be greater than the electron transporting property.
  • the excitons may be ineffectively formed in the emission layer. Therefore, the resultant device may exhibit deteriorated luminous efficiency.
  • the embodiments provide host materials, or charge transporting materials, e.g., electron transporting materials, hole blocking materials, and the like, that exhibit high thermal stability and triplet T1 energy.
  • the embodiments provide a benzimidazole compound exhibiting good charge transporting properties, good film stability, and high triplet T1 energy and thus may be applicable as host materials or charge transporting materials, e.g., electron transporting materials, hole blocking materials, and the like.
  • the benzimidazole compound of an embodiment may be applicable as host materials, electron transporting materials, or hole blocking materials, and thus may be used for an organic thin layer of an organic photoelectric device such as an organic emission layer, an electron transport layer (ETL), a hole blocking layer, and the like.
  • organic photoelectric device such as an organic emission layer, an electron transport layer (ETL), a hole blocking layer, and the like.
  • the embodiments provide benzimidazole compounds that have high solubility in an organic solvent and that are applicable as, e.g., a host material of an emission layer, an electron transporting material, or a hole blocking material, of an organic photoelectric device.
  • the benzimidazole compounds of an embodiment may emit fluorescence and phosphorescence at a red wavelength through a blue wavelength.

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US9530970B2 (en) 2016-12-27
EP2344611B1 (en) 2014-02-26
EP2344611A4 (en) 2012-04-04
KR101333697B1 (ko) 2013-11-27
TWI530493B (zh) 2016-04-21
JP2012505829A (ja) 2012-03-08
JP5694939B2 (ja) 2015-04-01
WO2010044607A1 (en) 2010-04-22
CN102159668A (zh) 2011-08-17
US20130256641A1 (en) 2013-10-03

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