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WO2014204464A1 - Dispositifs électroluminescents organiques phosphorescents ayant un hôte transportant des trous dans la région émissive - Google Patents

Dispositifs électroluminescents organiques phosphorescents ayant un hôte transportant des trous dans la région émissive Download PDF

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Publication number
WO2014204464A1
WO2014204464A1 PCT/US2013/046802 US2013046802W WO2014204464A1 WO 2014204464 A1 WO2014204464 A1 WO 2014204464A1 US 2013046802 W US2013046802 W US 2013046802W WO 2014204464 A1 WO2014204464 A1 WO 2014204464A1
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Prior art keywords
compound
group
substituted
host
light emitting
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Inventor
Hitoshi Yamamoto
Vadim Adamovich
Michael S. Weaver
Norimasa Yokoyama
Kouki Kase
Daizo KANDA
Hiroshi Ohkuma
Makoto Nagaoka
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Hodogaya Chemical Co Ltd
Universal Display Corp
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Hodogaya Chemical Co Ltd
Universal Display Corp
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Priority to JP2016521385A priority Critical patent/JP6286033B2/ja
Priority to PCT/US2013/046802 priority patent/WO2014204464A1/fr
Priority to TW103120364A priority patent/TWI640599B/zh
Publication of WO2014204464A1 publication Critical patent/WO2014204464A1/fr
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    • 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
    • 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
    • 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
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/90—Multiple hosts in the emissive layer
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/10—Transparent electrodes, e.g. using graphene
    • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking 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
    • H10K85/321—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
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Definitions

  • the present invention relates to an organic electroluminescent (EL) device such as an organic light emitting device (hereinafter abbreviated as an OLED) and materials capable of being used in such an OLED.
  • EL organic electroluminescent
  • OLED organic light emitting device
  • OLEDs which comprise an organic thin film layer which includes a light emitting layer located between an anode and a cathode are known in the art. In such devices, emission of light may be obtained from exciton energy, produced by recombination of a hole injected into a light emitting layer with an electron.
  • OLEDs make use of thin organic films that emit light when a voltage is applied across the device.
  • OLEDs are comprised of several organic layers in which at least one of the layers can be made to electro-luminesce by applying a voltage across the device.
  • the cathode effectively reduces the adjacent organic layers (i.e., injects electrons)
  • the anode effectively oxidizes the adjacent organic layers (i.e., injects holes).
  • Holes and electrons migrate across the device toward their respective oppositely charged electrodes. When a hole and an electron localize on the same molecule, recombination is said to occur, and an exciton is formed.
  • An exciton is a localized electron-hole pair having an excited energy state. Light is emitted (i.e., electroluminescence) when the exciton relaxes via a photo-emissive mechanism in luminescent compounds. In some cases, the exciton may be localized on an excimer or an exciplex.
  • organic includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic opto-electronic devices.
  • small molecule refers to any organic material that is not a polymer, i.e., organic material having molecules with a defined molecular weight, and “small molecules” may actually be quite large. Small molecules may include repeat units in some
  • Small molecules may also be incorporated into polymers, for example as a pendent group on a polymer backbone or as a part of the backbone. Small molecules may also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety.
  • the core moiety of a dendrimer may be a fluorescent or phosphorescent small molecule emitter.
  • a dendrimer may be a "small molecule,” and it is believed that all dendrimers currently used in the field of OLEDs are small molecules.
  • top means furthest away from the substrate, while “bottom” means closest to the substrate.
  • first layer is described as “disposed over” a second layer, the first layer is disposed further away from substrate. There may be other layers between the first and second layer, unless it is specified that the first layer is "in contact with” the second layer.
  • a cathode may be described as “disposed over” an anode, even though there are various organic layers in between.
  • solution processible means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium, either in solution or suspension form.
  • a ligand may be referred to as "photoactive” when it is believed that the ligand directly contributes to the photoactive properties of an emissive material.
  • a ligand may be referred to as "ancillary” when it is believed that the ligand does not contribute to the photoactive properties of an emissive material, although an ancillary ligand may alter the properties of a photoactive ligand.
  • a first "Highest Occupied Molecular Orbital” (HOMO) or “Lowest Unoccupied Molecular Orbital” (LUMO) energy level is "greater than” or "higher than” a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level.
  • IP ionization potentials
  • a higher HOMO energy level corresponds to an IP having a smaller absolute value (an IP that is less negative).
  • a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (an EA that is less negative).
  • the LUMO energy level of a material is higher than the HOMO energy level of the same material.
  • a "higher” HOMO or LUMO energy level appears closer to the top of such a diagram than a "lower” HOMO or LUMO energy level.
  • a first work function is "greater than” or “higher than” a second work function if the first work function has a higher absolute value. Because work functions are generally measured as negative numbers relative to vacuum level, this means that a "higher” work function is more negative. On a conventional energy level diagram, with the vacuum level at the top, a “higher” work function is illustrated as further away from the vacuum level in the downward direction. Thus, the definitions of HOMO and LUMO energy levels follow a different convention than work functions.
  • an OLED of the present disclosure comprises an anode electrode, a cathode electrode, and an organic electroluminescent layer disposed between the anode electrode and the cathode electrode.
  • the organic electroluminescent layer comprising a host material and a phosphorescent emitter dopant material.
  • the host material comprises at least a first host compound, and a second host compound, wherein the first host compound has an indeno- carbazole ring structure represented by the following general formula HI
  • A represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, or a divalent group of substituted or unsubstituted fused polycyclic aromatics
  • the OLED described above further comprises an exciton/electron blocking layer disposed between the electroluminescent layer and the anode, wherein the exciton/electron blocking layer blocks at least one of excitons or electrons and comprises a material that is the compound represented by the general formula HI.
  • the inventors have discovered that the OLED incorporating the teachings of the present disclosure exhibits an unexpectedly improved color saturation in the emission spectrum.
  • FIG. 1 is a schematic illustration of an OLED architecture.
  • FIG. 2 is a schematic illustration of an OLED architecture according to an embodiment of the present disclosure in which the hole transporting compound of the present disclosure is used as a hole-transporting host in a four-component emissive layer.
  • FIG. 3 is a schematic illustration of an OLED architecture according to another embodiment, in which the hole-transporting compound is used as a hole-transporting host in a four-component emissive layer and as an exciton/electron blocking layer.
  • FIG. 4 is an energy level diagram for the device of FIG. 2 in which the hole- transporting compound is used as a hole transporting host in the four-component emissive layer.
  • FIG. 5 is an energy level diagram for the device of FIG. 3 in which the hole- transporting compound is used as a hole transporting host in the four-component emissive layer and as an exciton/electron blocking layer.
  • FIG. 6 is a schematic illustration of an inverted OLED.
  • HIL refers to a hole injection layer
  • HTL refers to a hole transport layer
  • EBL refers to an exciton/electron blocking layer that may be capable of blocking excitons or electrons or both
  • EML refers to an emissive layer
  • HBL refers to a hole blocking layer
  • ETL refers to an electron transport layer.
  • electroluminescent and emissive are used interchangeably.
  • the present disclosure describes an OLED comprising an organic
  • electroluminescent layer comprising a phosphorescent emitter dopant dispersed in a host material wherein the host material comprises a first host compound, and a second host compound.
  • the first host compound is a hole-transporting host compound represented by the general formula HI
  • A represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, or a divalent group of substituted or unsubstituted fused polycyclic aromatics
  • the host material can also include a third host compound.
  • the second and third host compounds are described below.
  • FIG. 1 shows an OLED 100.
  • the OLED 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, and electron blocking layer 130, an emissive layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, and a cathode 160.
  • the cathode 160 can be a compound cathode having more than one conductive layers, such as a first conductive layer 162 and a second conductive layer 164 as shown.
  • the OLED 100 may be fabricated by depositing the layers described, in order. The properties and functions of these various layers, as well as example materials, are described in more detail in U.S. patent No.
  • OLEDs comprised of polymeric materials (PLEDs) such as disclosed in U.S. patent No. 5,247, 190 to Friend et al, which is incorporated by reference in its entirety.
  • PLEDs polymeric materials
  • OLEDs having a single organic layer may be used.
  • OLEDs may be stacked, for example as described in U.S. patent No. 5,707,745 to Forrest et al, which is incorporated by reference in its entirety.
  • the OLED structure may deviate from the simple layered structure illustrated in this disclosure.
  • the substrate may include an angled reflective surface to improve outcoupling, such as a mesa structure as described in U.S. patent No. 6,091, 195 to Forrest et al, and/or a pit structure as described in U.S. patent No. 5,834,893 to Bulovic et al, which are incorporated by reference in their entireties.
  • any of the layers of the various embodiments may be deposited by any suitable method.
  • preferred methods include thermal evaporation, ink-jet, such as described in U.S. patent No. 6,013,982 and No. 6,087,196, which are incorporated by reference in their entireties, organic vapor phase deposition (OVPD), such as described in U.S. patent No. 6,337,102 to Forrest et al, which is incorporated by reference in its entirety, and deposition by organic vapor jet printing (OVJP), such as described in U.S. patent No. 7,431 ,968, which is incorporated by reference in its entirety.
  • OVPD organic vapor phase deposition
  • OJP organic vapor jet printing
  • Other suitable deposition methods include spin coating and other solution based processes.
  • Solution based processes are preferably carried out in nitrogen or an inert atmosphere.
  • preferred methods include thermal evaporation.
  • Preferred patterning methods include deposition through a mask, cold welding such as described in U.S. patent No. 6,294,398 and No. 6,468,819, which are incorporated by reference in their entireties, and patterning associated with some of the deposition methods such as ink-jet and OVJD. Other methods may also be used.
  • the materials to be deposited may be modified to make them compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing.
  • Substituents having 20 carbons or more may be used, and 3-20 carbons is a preferred range. Materials with asymmetric structures may be better suited for solution processing than those having symmetric structures, because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.
  • Devices fabricated in accordance with embodiments of the invention may be incorporated into a wide variety of consumer products, including flat panel displays, computer monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads up displays, fully transparent displays, flexible displays, laser printers, telephones, cell phones, personal digital assistants (PDAs ), laptop computers, digital cameras, camcorders, viewfinders, micro-displays, vehicles, a large area wall, theater or stadium screen, or a sign.
  • PDAs personal digital assistants
  • Various control mechanisms may be used to control devices fabricated in accordance with the present invention, including passive matrix and active matrix. Many of the devices are intended for use in a temperature range comfortable to humans, such as 18 °C to 30 °C, and more preferably at room temperature (20-25 °C).
  • the materials and structures described herein may have applications in devices other than OLEDs.
  • other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures.
  • organic devices such as organic transistors, may employ the materials and structures.
  • the terms halo, halogen, alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, heterocyclic group, aryl, aromatic group, and heteroaryl are known to the art, and are defined in U.S. patent No. 7,279,704 at columns 31-32, the disclosure of which is incorporated herein by reference in its entirety.
  • the host material of the emissive layer in an organic light-emitting device provides a solid medium for the transport and recombination of charge carriers injected from the anode and the cathode. Compounds used for the host material can be categorized according to their charge transport properties. Some host compounds are predominantly electron-transporting and some others are predominantly hole-transporting. Although host compounds may be characterized as transporting predominantly one type of charge, the compound may also transport charges of both types.
  • Emitter dopant Any suitable phosphorescent dopant may be used in the emissive layer. Some examples are provided in Table 5 below.
  • the phosphorescent dopant is a phosphorescent emitter material comprising a phosphorescent organometallic compound that emits phosphorescent radiation from a triplet molecular excited state when a voltage is applied across the material. The selection of the host materials will vary depending on the selection of the phosphorescent emitter dopant. In some embodiments, the
  • electroluminescent layer contains additional dopants.
  • the phosphorescent emitter material is an
  • organometallic compound selected from the group consisting of phosphorescent
  • organometallic platinum compounds organometallic iridium compounds and organometallic osmium compounds.
  • the phosphorescent organometallic compound can include a carbon- metal bond.
  • the organometallic platinum compounds, iridium compounds and osmium compounds can each include an aromatic ligand.
  • the phosphorescent organometallic compounds can comprise heteroleptic complexes with extended conjugation on the heterocyclic ring. Examples of such
  • heteroleptic iridium compounds are described in PCT publication No. WO 2010/028151, published on March 1 1, 2010, the disclosure of which is incorporated herein by reference in its entirety.
  • the first host compound is represented by the following general formula HI :
  • A represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, or a divalent group of substituted or unsubstituted fused polycyclic aromatics
  • the first host compound can be selected from the group consisting of the compounds shown below, wherein D represents deuterium:
  • the HOMO level of the first host compound is relatively close to the HOMO level of the emitter dopant, which allows offloading of the hole transporting function from the emitter dopant material. This enhances the lifetime of the emitter dopant material in the OLED.
  • the HOMO level of the first host compound is higher (less electronegative) than the HOMO energy levels of the other host compounds. The right energy level alignment allow separate charges and excitons in the device emissive layer, minimize triplet-polaron annihilation and non-radiative quenchers formation. This improves the OLED's color saturation in the emission spectrum.
  • the mixture was heated after adding tetrakis(triphenylphosphine)palladium (0.26 g), and stirred at 73 °C for 5 hours. After the mixture was cooled to a room temperature, toluene (30 ml) and water (20 ml) were added to perform liquid separation in order to collect an organic layer. The organic layer was washed with saturated brine, dehydrated with anhydrous magnesium sulfate, and
  • the crude product was purified by column chromatography (carrier: silica gel; eluent: toluene/n-hexane) to obtain a white powder of 12,12-dimethyl-10-phenyl-7-(9-phenyl-9H-carbazol-3-yl)-10, 12- dihydroindeno[2, l-b]carbazole (1.5 g; yield 54.7%).
  • the mixture was heated after adding tetrakis(triphenylphosphine)palladium (0.4 g), and stirred at 71°C for 7 hours. After the mixture was cooled to a room temperature, water (20 ml) was added to perform liquid separation in order to collect an organic layer. The organic layer was dehydrated with anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a crude product.
  • the crude product was purified by column chromatography (carrier: silica gel; eluent: toluene/cyclohexane) to obtain a white powder of 12, 12-dimethyl-10-(9,9- dimethyl-9H-fluorene-2-yl)-7-(9-phenyl-9H-carbazole-3-yl)-10, 12-dihydroindeno[2, l- b]carbazole (3.4 g; yield 65.7%).
  • carrier silica gel
  • eluent toluene/cyclohexane
  • Each of the second and third host compounds is a wide band gap host compound that is more electron-transporting compared to the compound HI and can contain at least one of the following groups in the molecule:
  • X 1 to X 8 is selected from C or N; and wherein Z 1 and Z 2 is S or O.
  • the second host compound and the third host compound are different compounds.
  • the second host compound can be a compound comprising a triphenylene containing benzo-fused thiophene.
  • Triphenylene is a polyaromatic hydrocarbon with high triplet energy, yet high [pi]- conjugation and a relatively small energy difference between the first singlet and first triplet levels. This would indicate that triphenylene has relatively easily accessible HOMO and LUMO levels compared to other aromatic compounds with similar triplet energy (e.g., biphenyl).
  • the advantage of using triphenylene and its derivatives as hosts is that it can accommodate red, green and even blue phosphorescent dopants to give high efficiency without energy quenching.
  • Triphenylene hosts may be used to provide high efficiency and stability phosphorescent OLEDs (PHOLEDs). See Kwong and Alleyene, Triphenylene Hosts in Phosphorescent Light Emitting Diodes, 2006, 60 pp, US 2006/0280965 Al. Benzo-fused thiophenes may be used as hole transporting organic conductors. In addition, the triplet energies of benzothiophenes, namely dibenzo[/?, ⁇ i]thiophene (referred to herein as "dibenzothiophene"), benzo[Z?]thiophene and benzo[c]thiophene are relatively high.
  • a combination of benzo-fused thiophenes and triphenylene as hosts in PHOLEDs may be beneficial. More specifically, benzo-fused thiophenes are typically more hole transporting than electron transporting, and triphenylene is more electron transporting than hole transporting. Therefore combining these two moieties in one molecule may offer improved charge balance which may improve device performance in terms of lifetime, efficiency and low voltage. Different chemical linkage of the two moieties can be used to tune the properties of the resulting compound to make it the most appropriate for a particular phosphorescent emitter, device architecture, and/or fabrication process. For example, m-phenylene linkage is expected to result in higher triplet energy and higher solubility whereas -phenylene linkage is expected to result in lower triplet energy and lower solubility.
  • benzo-fused furans are also typically hole transporting materials having relatively high triplet energy.
  • benzo-fused furans include benzofuran and dibenzofuran. Therefore, a material containing both triphenylene and benzofuran may be advantageously used as emitter host or hole blocking material in PHOLED. A compound containing both of these two groups may offer improved electron stabilization which may improve device stability and efficiency with low voltage.
  • the properties of the triphenylene containing benzofuran compounds may be tuned as necessary by using different chemical linkages to link the triphenylene and the benzofuran.
  • the compounds for the second host compound may be substituted with groups that are not necessarily triphenylenes, benzo-fused thiophenes, and benzo-fused furans.
  • any group that is used as a substituent of the compound has a triplet energy high enough to maintain the benefit of having triphenylene benzo-fused thipohenes or benzo-fused furans (i.e. the triplet energy of the substituent maintains the high triplet energy of benzo- fused thiophenes, benzo-fused furans and triphenylenes).
  • the compounds for the host material described herein have a high enough triplet energy to be suitable for use in a device having phosphorescent blue emissive materials.
  • substituents of the compounds described herein are unfused such that the substituents are not fused to the triphenylene, benzo-fused furan or benzo-fused thiophene moieties of the compound.
  • the substituents may optionally be inter-fused (i.e. fused to each other).
  • Materials provided herein may also offer improved film formation in the device as fabricated by both vapor deposition and solution processing methods.
  • materials offering improved fabrication have a central pyridine ring to which the benzo-fused thiophenylene and triphenylene, or benzofuran and triphenylene, are attached.
  • the improved film formation is believed to be a result of the combination of polar and non-polar rings in the compound.
  • the second and/or third host compounds are triphenylene-containing benzo-fused thiophenes or benzo-fused furans.
  • triphenylene-containing benzo-fused thiophenes or benzo-fused furans include compounds having the structure of the following formulae (H-IV), (H-V), and (H-VI):
  • X is S or O;
  • X is S or O;
  • X is S or O;
  • Examples of compounds having the structure of the formula (H-IV) include:
  • Each of Ri to R n may represent mono, di, tri, or tetra substitutions., n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
  • Ari and Ar 2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof. At least one of Ri, R 2 , and R3 includes a triphenylene group. [0061] Examples of compounds having the structure of the formula (H-V) include:
  • Each of Ri to R n may represent mono, di, tri, or tetra substitutions, and n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
  • Ari and Ar 2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof. At least one of Ri, R 2 , and R3 includes a triphenylene group.
  • Examples of compounds having the structure of the formula (H-VI) include:
  • Each of Ri to R n may represent mono, di, tri, or tetra substitutions, n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
  • Ari and Ar 2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof. At least one of Ri, R 2 , and R3 includes a triphenylene group.
  • All of the host compound materials disclosed herein are compounds that have triplet energies greater than the triplet energy of the phosphorescent dopant. This energy configuration allows confinement of the triplet excited states on the dopant.
  • the use of the additional host materials in the emissive layer may reduce the interaction of the excitons with the charge carriers, thereby reducing exciton quenching, which may improve device efficiency and/or lifetime.
  • the wide band gap host compounds for the second host compound in the emissive layer have a HOMO-LUMO band gap of at least 2.0 eV.
  • the wide band gap host compound has a HOMO-LUMO band gap of at least 2.5 eV, and in some cases, at least 3.0 eV.
  • the HOMO- LUMO band gap of the wide band gap host compound is equal to or greater than that of the hole-transporting first host compound.
  • the wide band gap host compound does not readily transport charges of either type in the emissive layer.
  • the wide band gap host compound has a lower hole mobility than the hole-transporting first host compound.
  • the host compounds are preferably capable of mixing well with the other components of the emissive layer and capable of promoting the formation of an amorphous film.
  • the compounds for the emissive layer may be deposited using any suitable deposition technique, including vapor-phase deposition techniques such as vacuum thermal evaporation.
  • the different compounds in the emissive layer may be deposited separately or in combination. For example, each compound may be deposited at individually controlled rates, or alternatively, two or more of the host compounds may be pre-mixed and then be evaporated together.
  • the components of the multi-component emissive layer discussed herein can be used in the following quantities defined as wt. % of the total emissive layer materials.
  • the phosphorescent dopant can be provided in 0.5-20 %, more preferably in 1-10 %, most preferably 3-7%.
  • the first host compound preferably constitutes no more than 25 % and more preferably about 10-20 %.
  • the second host compound preferably constitutes about 50-90% and more preferably about 60-80%.
  • the third host compound preferably constitutes about 10-50% and more preferably about 20-40%.
  • the relative amounts of the emitter dopant and the host materials in the emissive layer will vary depending upon the particular application.
  • the OLED of the present disclosure can further comprise an exciton/electron blocking layer (EBL), formed of the material that is the compound represented by the general formula HI described above, disposed between the emissive layer and the anode.
  • EBL exciton/electron blocking layer
  • the material for the EBL can be selected from the group consisting of the following examples of compounds having the general formula HI : Compound Hl-1 ; Compound HI -2; Compound Hl-3; Compound Hl-4; Compound Hl-5; Compound Hl-6; Compound Hl-7; Compound Hl-8; Compound Hl-9; Compound Hl-10; Compound Hl-11; Compound Hl- 12; Compound Hl-13; Compound Hl-14; Compound Hl-15; Compound Hl-16; Compound HI -17 through Compound HI- 120 described herein.
  • the OLED according to another aspect of the present disclosure further comprises at least one hole transport layer disposed between the emissive layer and the anode.
  • the at least one hole transport layer is a material comprising at least one of the compounds having a formula selected from the following formulae (HTL-I) to (HTL-VI) listed below: (HTL-I) is
  • Rn and R12 may be the same or different and are independently selected from the group consisting of a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group, a phenyl group, a phenyl group having a lower alkyl group or deuterium substituent, and a phenyl group having a deuterium atom or a lower alkoxy group substituent with the proviso at least one of Rn and R12 is a deuterium atom, a normal butyl group, an isobutyl group, a secondary butyl group, a tertiary butyl group, a phenyl group, a phenyl group having a lower alkyl group substituent, or a phenyl group having a lower alkoxy group substituent; and Rn represents a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group or a chlorine atom;
  • R21, R22 and R23 may be the same or different and each independently represents a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group, an
  • R24 represents a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group or a chlorine atom;
  • Ai represents a group represented by any one of the following structural formulae (al) to (il);
  • R 2 5 represents a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group or a chlorine atom;
  • R 3 1, R 3 2 and R 33 may be the same or different and each independently represents a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group, an unsubstituted phenyl group, or a phenyl group having a deuterium atom, a lower alkyl group or a lower alkoxy group as a substituent(s);
  • R 3 4 represents a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group or a chlorine atom;
  • a 2 represents a group represented by any one of the following formulae (j l) to (nl);
  • R41 and R42 may be the same or different and each independently represents a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group, an
  • R43 represents a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group or a chlorine atom;
  • A3 represents a group represented by anyone of the following structural formulae (a2) to (i2);
  • R44 represents a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group or a chlorine atom;
  • R51 and R52 may be the same or different and each independently represent a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group, an
  • R53 represents a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group or a chlorine atom;
  • a 4 represents a group represented by anyone of the following structural formulae (j2) to (n2);
  • 3 ⁇ 4 ⁇ to 3 ⁇ 49 which may be the same or different, independently represent a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group, an unsubstituted aromatic hydrocarbon group, a phenyl group having a deuterium atom, a lower alkyl group or a lower alkoxy group; r 6 i to which may be the same or different, represent 0, 1 or 2.
  • lower alkyl group and lower alkoxy group as used herein mean “C1-4 alkyl group” and “C1-4 alkoxy group,” respectively.
  • the OLED of the present invention may be prepared on a substrate for supporting the OLED.
  • the substrate is preferably a flat substrate in which light in the visible region of about 400 to about 700 nm has a transmittance of at least about 50 %.
  • the substrate may include a glass plate, a polymer plate and the like.
  • the glass plate may include soda lime glass, barium » strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz and the like.
  • the polymer plate may include polycarbonate, acryl, polyethylene terephthalate, polyether sulfide, polysulfone and the like.
  • the anode 3 in the OLED 100 of the present invention assumes the role of injecting holes into the hole injecting layer, the hole transporting layer or the light emitting layer.
  • the anode has a work function of 4.5 eV or more.
  • Specific examples of a material suitable for use as the anode include indium tin oxide alloy (ITO), tin oxide (NESA), indium zinc oxide, gold, silver, platinum, copper and the like.
  • ITO indium tin oxide alloy
  • NESA tin oxide
  • the anode can be prepared by forming a thin film from electrode substances, such as those discussed above, by a method such as a vapor deposition method, a sputtering method and the like.
  • the transmittance of light in the visible light region in the anode is preferably larger than 10 %.
  • the sheet resistance of the anode is preferably several hundred ⁇ /square or less.
  • the film thickness of the anode is selected, depending on the material, and is typically in the range of from about 10 nm to about 1 ⁇ , and preferably from about 10 nm to about 200 nm.
  • the cathode 11 comprises preferably a material having a small work function for the purpose of injecting an electron into the electron injecting layer, the electron transporting layer or the light emitting layer.
  • Materials suitable for use as the cathode include, but are not limited to indium, aluminum, magnesium, magnesium-indium alloys, magnesium-aluminum alloys, aluminum-lithium alloys, aluminum-scandium-lithium alloys, magnesium-silver alloys and the like.
  • a TOLED cathode such as disclosed in U.S. Patent No. 6,548,956 is preferred.
  • the cathode can be prepared, as is the case with the anode, by forming a thin film by a method such as a vapor deposition method, a sputtering method and the like. Further, an embodiment in which light emission is taken out from a cathode side can be employed as well.
  • FIG. 6 shows an inverted OLED 400 according to another embodiment of the present disclosure.
  • the device includes a substrate 410, a cathode 415, an emissive layer 420, a hole transport layer 425, and an anode 430.
  • OLED 400 may be fabricated by depositing the layers described, in order. Because the most common OLED configuration has a cathode disposed over the anode, and device 400 has cathode 415 disposed under anode 430, device 400 may be referred to as an inverted OLED.
  • OLED 400 also illustrates an example of an OLED in which some of the layers illustrated in the OLED 100 of FIG. 1 are omitted from the device architecture.
  • OLEDs 100, 200, 300 and 400 are provided by way of non-limiting examples and it is understood that embodiments of the invention may be used in connection with a wide variety of other structures.
  • the specific materials and structures described are exemplary in nature, and other materials and structures may be used.
  • Functional OLEDs may be achieved by combining the various layers described in different ways, or certain layers may be omitted entirely, based on the design, performance, and cost factors. Other layers not specifically described herein may also be included.
  • hole transport layer 425 transports holes and injects holes into emissive layer 420, and may be described as a hole transport layer or a hole injection layer.
  • an OLED may be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described.
  • Compound HI as a host - Example Devices #1, #2 and #3 Experimental green PHOLEDs having a four-component emissive layer and having the architecture shown in FIG. 2 was constructed.
  • the example devices #1, #2 and #3 had an ITO anode (800 A) and a LiF/Al cathode. Disposed between the two electrodes were: 100 A thick hole injection layer (HIL) made of the compound LG-101 (from LG Chemical), a 500 A thick electron blocking layer (EBL) made of NPD, a 300 A thick four-component emissive layer (EML), a 100 A thick hole blocking layer (HBL) made of the compound El, and a 400 A thick electron transport layer (ETL) made of Alq 3 .
  • HIL thick hole injection layer
  • EBL 500 A thick electron blocking layer
  • EML 300 A thick four-component emissive layer
  • HBL 100 A thick hole blocking layer
  • HBL 400 A thick electron transport layer
  • the four-component EML in these experimental devices were formed with three host compounds.
  • the first host compound was the hole-transporting type host compound having the general formula HI
  • the second host compound was compound H as a wide band-gap matrix host
  • the third host compound was El as an electron-transporting host.
  • the particular hole-transporting host compounds in devices #1, #2 and #3 were H1-1, H1-1 19, and Hl-118, respectively.
  • the compound Gl was the green emitter dopant.
  • the HOMO- LUMO energy levels of these compounds are provided in Table 1 below.
  • the amount of each of the components of the emissive layer used are provided in Table 3 below. The amounts are provided in wt.% of the emissive layer.
  • the concentrations of the first host compound Hl-1, the second host compound H, the third host compound El, and the emitter dopant Gl were 15 wt.%, 60 wt.%, 20 wt.%, and 5 wt.%, respectively.
  • FIG. 4 The energy level diagram for the four-component EML of a device of FIG. 2 that incorporates the hole-transporting type compound HI as one of the hosts in the EML according to an embodiment is shown in FIG. 4.
  • FIG. 5 The energy level diagram for the four- component EML portion of the Example Device #4 is shown in FIG. 5.
  • the HOMO level of compound Hl-1 is 5.59 eV, which is higher (or less electronegative) than the HOMO levels of the other host compounds H and El which are 5.96 and 5.73, respectively.
  • the host compounds H and El are thus more electron-transporting than the hole-transporting type compounds Hl-1, Hl-118 and Hl-119.
  • the HOMO levels of compounds Hl-1, Hl-1 18, and Hl-1 19 are relatively close to HOMO level of the emitter dopant Gl (5.1 eV), and as discussed above, this allows the hole-transporting host compounds such as Hl-1, Hl-1 18, and Hl-119 to offload the hole transporting function from the emitter dopant which extends the life of the emitter dopant material.
  • Example Devices #1 through #8 with high 15 wt.% of compounds Hl-1, Hl- 118, and Hl-1 19 and low 5 wt.% of Gl in the EML, the majority of holes are believed to be transported by the hole-transporting host compounds Hl-1, Hl-1 18, and Hl-1 19 which enhances separation of the charge carriers and excitons and minimizes concentration quenching and polaron-exciton interaction.
  • the triplet energy of compound Hl-1 (2.80 eV) is higher than the triplet energy of Gl (2.4 eV) and does not cause the emission quenching.
  • Example devices #4, #5, #6, #7 and #8 had the architecture 300 shown in FIG. 3.
  • the EML of example devices #4, #5, #6, #7 and #8 had a four-component composition consisting of the hole-transporting compound having the general formula HI (15 wt.%) as the first host compound, the compound H (60 wt.%) as the second host compound, and the compound El (20 wt.%) as the third host compound, and the emitter dopant compound Gl (5 wt.%).
  • two groups of example devices were evaluated: (1) a first group using the hole-transporting type compound of the present disclosure as one of the host compounds in the emissive layer with NPD as EBL (example devices #1, #2 and #4); and (2) a second group using the compound of the present disclosure as one of the host compounds in the emissive layer and also as the EBL (example devices #5, #6, #8, #9, and #14).
  • the indeno- carbazole derivative compounds represented by the general formula HI were used as a host with the matrix host, H, the electron-transporting host, El, and provided the hole-transporting host function.
  • the comparative example device CE had only two host compounds, the matrix host H and the electron-transporting host El, and NPD as the EBL.
  • the superior color saturation was achieved with all of the example devices.
  • the example devices exhibited narrower FWHM than the comparative example device. The inventors believe that this may be an evidence of an increased microcavity effect induced by the addition of the hole- transporting host to the EML. This would suggest that in addition to the compound Hi 's transport functions, its refractive index may improve the reflectance characteristics in the EML, leading to spectral narrowing and enhanced intensity of emission. These beneficial effects were unexpected because such effects are generally not predictable based on the chemical structures of the compounds. Table 3. Example Devices Experimental Data
  • the HOMO, LUMO levels and the triplet energy levels are provided in Table 1 above.
  • the very shallow LUMO level of compounds HI- 1, HI- 1 18, and HI -1 19 (2.10, 2.20, and 2.33 eV, respectively) blocks electrons from leaking into HTL and high triplet energy of the compounds Hl-1, Hl-118, and Hl-119 (2.80, 2.79, and 2.77 eV, respectively) blocks excitons from leaking into HTL.
  • the excitons and electrons in the device with compounds, such as Hl-1, Hl-118, or Hl-119, as the exciton/electron blocking layer are better confined within the emissive layer. Thus, it combines both charge-exciton separation in the emissive layer and electron and exciton blocking in the exciton/electron blocking layer.
  • any of the layers of the various embodiments of the invention described herein may be deposited by any suitable method.
  • preferred methods include thermal evaporation, ink-jet, such as described in U.S. Pat. Nos. 6,013,982 and 6,087, 196, which are incorporated by reference in their entireties, organic vapor phase deposition (OVPD), such as described in U.S. Pat. No. 6,337, 102 to Forrest et al, which is incorporated by reference in its entirety, and deposition by organic vapor jet printing (OVJP), such as described in U.S. patent application Ser. No. 10/233,470, which is incorporated by reference in its entirety.
  • OVPD organic vapor phase deposition
  • OJP organic vapor jet printing
  • deposition methods include spin coating and other solution based processes. Solution based processes are preferably carried out in nitrogen or an inert atmosphere.
  • preferred methods include thermal evaporation.
  • Preferred patterning methods include deposition through a mask, cold welding such as described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entireties, and patterning associated with some of the deposition methods such as ink-jet and OVJD. Other methods may also be used. The materials to be deposited may be modified to make them compatible with a particular deposition method.
  • substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing.
  • Substituents having 20 carbons or more may be used, and 3-20 carbons is a preferred range.
  • Materials with asymmetric structures may have better solution processibility than those having symmetric structures, because asymmetric materials may have a lower tendency to recrystallize.
  • Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.
  • the structures illustrated herein are an example only and the OLED according to the disclosed invention is not limited to the particular structure and can include more layers or fewer layers or different combinations of the layers.

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Abstract

La présente invention concerne un dispositif OLED amélioré comprenant une couche émissive disposée entre une cathode et une anode, la couche émissive comprenant un matériau hôte multi-composant et un matériau émetteur phosphorescent. Le matériau hôte comprend au moins un premier composé hôte et un second composé hôte, le premier composé hôte étant un hôte transportant des trous représenté par la formule générale dans laquelle R1, R2, R3, R4, R5, et R6 peuvent être de façon identique ou différente un atome de fluor, un atome de chlore, un atome de deutérium, un groupe cyano, un groupe trifluorométhyle, un groupe nitro, un groupe alkyle linéaire ou ramifié (C1-C6), un groupe cyclo-alkyle (C5-C10), un groupe alcoxy linéaire ou ramifié (C1-C6), un groupe cyclo-alcoxy (C5-C10), un groupe hydrocarbure aromatique substitué ou non substitué, un groupe hétérocyclique aromatique substitué ou non substitué, un groupe aromatique polycyclique condensé substitué ou non substitué, r1, r4, r5 = 0, 1, 2, 3, ou 4, r2, r3, r6; = 0, 1, 2 or 3, n = 0 ou 1, et Ar1, Ar2, et Ar3 peuvent être de façon identique ou différente un groupe hydrocarbure aromatique substitué ou non substitué, un groupe hétérocyclique aromatique substitué ou non substitué, un groupe aromatique polycyclique condensé substitué ou non substitué, un groupe hydrocarbure aromatique à substitution deutérium, un groupe hétérocyclique aromatique à substitution deutérium ou un groupe aromatique polycyclique condensé à substitution deutérium.
PCT/US2013/046802 2013-06-20 2013-06-20 Dispositifs électroluminescents organiques phosphorescents ayant un hôte transportant des trous dans la région émissive Ceased WO2014204464A1 (fr)

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