[go: up one dir, main page]

WO2014204464A1 - Phosphorescent organic light emitting devices having a hole-transporting host in the emissive region - Google Patents

Phosphorescent organic light emitting devices having a hole-transporting host in the emissive region Download PDF

Info

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
Authority
WO
WIPO (PCT)
Prior art keywords
compound
group
substituted
host
light emitting
Prior art date
Application number
PCT/US2013/046802
Other languages
French (fr)
Inventor
Hitoshi Yamamoto
Vadim Adamovich
Michael S. Weaver
Norimasa Yokoyama
Kouki Kase
Daizo KANDA
Hiroshi Ohkuma
Makoto Nagaoka
Original Assignee
Universal Display Corporation
Hodogaya Chemical Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Universal Display Corporation, Hodogaya Chemical Co., Ltd. filed Critical Universal Display Corporation
Priority to PCT/US2013/046802 priority Critical patent/WO2014204464A1/en
Priority to JP2016521385A priority patent/JP6286033B2/en
Priority to TW103120364A priority patent/TWI640599B/en
Publication of WO2014204464A1 publication Critical patent/WO2014204464A1/en

Links

Classifications

    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
    • 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.

Landscapes

  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Indole Compounds (AREA)

Abstract

An improved OLED includes an emissive layer disposed between a cathode and an anode where the emissive layer includes a multi-component host material and a phosphorescent emitter material. The host material includes at least a first host compound and a second host compound, where the first host compound is hole-transporting host compound having the general formula wherein R1, R2, R3, R4, R5, and R6 may be the same or different fluorine atom, chlorine atom, a deuterium atom, a cyano group, a trifluoromethyl group, a nitro group, linear or branched alkyl group (C1-C6), cyclo-alkyl group (C5-C10), linear or branched alkoxy group (C1-C6), cyclo-alkoxy group (C5~C10), substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted fused polycyclic aromatic group, r1, r4, r5 = 0, 1, 2, 3, or 4, r2, r3, r6; = 0, 1, 2 or 3, n = 0 or 1, and Ar1, Ar2, and Ar3 may be the same or different, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted fused polycyclic aromatic group, deuterium substituted aromatic hydrocarbon group, deuterium substituted aromatic heterocyclic group, or deuterium substituted fused polycyclic aromatic group.

Description

PHOSPHORESCENT ORGANIC LIGHT EMITTING DEVICES HAVING A HOLE-TRANSPORTING HOST IN THE EMISSIVE REGION
FIELD
[0001] 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.
BACKGROUND
[0002] 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.
[0003] OLEDs make use of thin organic films that emit light when a voltage is applied across the device. Generally, 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. When a voltage is applied across a device, the cathode effectively reduces the adjacent organic layers (i.e., injects electrons), and 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.
[0004] Despite the recent discoveries such as the use of efficient heavy metal phosphors and the resulting advancements in OLED technology, there remains a continued need for longer device stability and higher efficiency. An improved OLED device that exhibit improved lifetimes and efficiencies is disclosed herein along with the associated materials that may be used to construct such OLED.
[0005] As used herein, the term "organic" includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic opto-electronic devices. As used herein, "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
circumstances, e.g. oligomers. For example, using a long chain alkyl group as a substituent does not remove a molecule from the "small molecule" class. 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.
[0006] As used herein, "top" means furthest away from the substrate, while "bottom" means closest to the substrate. Where a 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. For example, a cathode may be described as "disposed over" an anode, even though there are various organic layers in between.
[0007] As used herein, "solution processible" means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium, either in solution or suspension form.
[0008] 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.
[0009] As used herein, and as would be generally understood by one skilled in the art, 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. Since ionization potentials (IP) are measured as a negative energy relative to a vacuum level, a higher HOMO energy level corresponds to an IP having a smaller absolute value (an IP that is less negative). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (an EA that is less negative). On a conventional energy level diagram, with the vacuum level at the top, 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.
[0010] As used herein, and as would be generally understood by one skilled in the art, 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.
SUMMARY
[0011] The present disclosure provides OLEDs having a multi-component emissive layer. In one aspect, 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
Figure imgf000004_0001
(HI) wherein 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; Arls A¾ and A¾ may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group, where A and Ar2, or Ar2 and Ar3 may bind to each other via a single bond or via substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring; Ri to R9 may be the same or different, and represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano, nitro, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or substituted or unsubstituted aryloxy, which may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring; and Rio and Rn may be the same or different, and represent linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or substituted or unsubstituted aryloxy, which may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring.
[0012] In another aspect, 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.
[0013] The inventors have discovered that the OLED incorporating the teachings of the present disclosure exhibits an unexpectedly improved color saturation in the emission spectrum.
BRIEF DESCRIPTION OF THE DRAWING
[0014] The figures are not necessarily drawn to scale.
[0015] FIG. 1 is a schematic illustration of an OLED architecture. [0016] 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.
[0017] 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.
[0018] 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.
[0019] 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.
[0020] FIG. 6 is a schematic illustration of an inverted OLED.
DETAILED DESCRIPTION
[0021] In the present disclosure, 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; and ETL refers to an electron transport layer. The terms electroluminescent and emissive are used interchangeably.
[0022] 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
Figure imgf000006_0001
(HI) wherein 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; Arls Ar2, and Ar3 may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group, where A and Ar2, or Ar2 and Ar3 may bind to each other via a single bond or via substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring; Ri to R9 may be the same or different, and represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano, nitro, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or substituted or unsubstituted aryloxy, which may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring; and Rio and Rn may be the same or different, and represent linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or substituted or unsubstituted aryloxy, which may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring.
[0023] The resulting OLED exhibits improved color saturation in the emission spectrum. According to an aspect of the present disclosure, the host material can also include a third host compound. The second and third host compounds are described below.
[0024] 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.
7,279,704 at columns 6-10, the disclosure of which is incorporated herein by reference in its entirety.
[0025] Structures and materials not specifically described may also be used, such as 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. By way of further example, 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. For example, 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.
[0026] Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For the organic layers, 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. 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. For the other layers, 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.
[0027] 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. 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).
[0028] The materials and structures described herein may have applications in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures. More generally, organic devices, such as organic transistors, may employ the materials and structures.
[0029] 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: [0030] Any suitable phosphorescent dopant may be used in the emissive layer. Some examples are provided in Table 5 below. In one embodiment, 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.
[0031] According to an embodiment, 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.
[0032] 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 Hole-transporting Host Compound:
[0033] The first host compound is represented by the following general formula HI :
Figure imgf000010_0001
HI
wherein 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; Arls Ar2, and Ar3 may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group, where A and Ar2, or Ar2 and Ar3 may bind to each other via a single bond or via substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring; Ri to R9 may be the same or different, and represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano, nitro, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or substituted or unsubstituted aryloxy, which may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring; and Rio and Rn may be the same or different, and represent linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or substituted or unsubstituted aryloxy, which may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring.
[0034] Examples of specific compounds having the structure of formula HI are shown below. The first host compound can be selected from the group consisting of the compounds shown below, wherein D represents deuterium:
Figure imgf000011_0001
Compound Hl-1 Compound HI -2
Figure imgf000012_0001
Compound H 1 -3 Compound H 1 -4
Figure imgf000012_0002
Compound H 1 -5 Compound H 1 -6
Figure imgf000012_0003
Com ound HI -7 Compound HI -8
Figure imgf000012_0004
Compound H 1 -9 Compound H 1 - 10
Figure imgf000013_0001
Compound HI- 11 Compound HI- 12
Figure imgf000013_0002
Compound HI- 13 Compound HI -14
Figure imgf000013_0003
Compound HI -15 Compound HI -16
Figure imgf000013_0004
Compound HI- 17 Compound HI- 18
Figure imgf000014_0001
Compound HI- 19 Compound HI -20
Figure imgf000014_0002
Compound H 1 -21 Compound H 1 -22
Figure imgf000014_0003
Compound H 1 -23 Compound H 1 -24
Figure imgf000014_0004
Compound H 1 -25 Compound H 1 -26
Figure imgf000015_0001
Compound HI -27 Compound HI -28
Figure imgf000015_0002
Compound HI -29 Compound HI -30
Figure imgf000015_0003
Compound HI -31 Compound HI -32
Figure imgf000016_0001
Compound HI -33 Compound HI -34
Figure imgf000016_0002
Compound HI -35 Compound HI -36
Figure imgf000016_0003
Compound HI -37 Compound HI -38
Figure imgf000016_0004
Compound HI -39 Compound HI -40
Figure imgf000017_0001
Compound HI -41 Compound HI -42
Figure imgf000017_0002
Compound HI -43 Compound HI -44
Figure imgf000017_0003
Compound HI -45 Compound HI -46
Figure imgf000018_0001
Compound HI -47 Compound HI -48
Figure imgf000018_0002
Compound HI -49
H
Figure imgf000018_0003
Compound HI -50 3
H,
Figure imgf000019_0001
Compound HI -51
Figure imgf000019_0002
Compound HI -52 Compound HI -53
Figure imgf000019_0003
Compound Hl-54 Compound Hl-55
Figure imgf000020_0001
Compound HI -56 Compound HI -57
Figure imgf000020_0002
Compound HI -58 Compound HI -59
3
Figure imgf000021_0001
Compound HI -60 Compound HI -61
Figure imgf000021_0002
Compound HI -62 Compound HI -63
Figure imgf000021_0003
Compound H 1 -64 Compound H 1 -65
Figure imgf000022_0001
Compound HI -66 Compound HI -67
Figure imgf000022_0002
Compound HI -68 Compound HI -69
Figure imgf000022_0003
Compound HI -70 Compound HI -71
Figure imgf000022_0004
Compound HI -72 Compound HI -73
Figure imgf000023_0001
Compound HI -74 Compound HI -75
Figure imgf000023_0002
Compound HI -76 Compound HI -77
Compound HI -78 Compound HI -79
Figure imgf000023_0004
Compound HI -80 Compound HI -81
Figure imgf000024_0001
Compound HI -82 Compound HI -83
Figure imgf000024_0002
Compound Hl-84 Compound HI -85
Figure imgf000024_0003
Compound HI -86 Compound HI -87
Figure imgf000024_0004
Compound HI -88 Compound Hl-89
Figure imgf000025_0001
Compound HI -90 Compound HI -91
Figure imgf000025_0002
Compound HI -92 Compound HI -93
Figure imgf000025_0003
Compound HI -94 Compound HI -95
Figure imgf000026_0001
Compound HI -96 Compound HI -97
Figure imgf000026_0002
Compound HI -98 Compound HI -99
Figure imgf000026_0003
Compound HI -100 Compound HI -101
Figure imgf000027_0001
Compound H 1 - 102 Compound HI -103
Figure imgf000027_0002
Compound HI -104 Compound HI -105
Figure imgf000027_0003
Compound HI -106 Compound HI -107
Figure imgf000028_0001
Compound Hl-1 10 Compound Hl-1 11
Figure imgf000028_0002
Compound Hl-1 12 Compound Hl-1 13
Figure imgf000029_0001
Compound Hl-114 Compound Hl-115
Figure imgf000029_0002
Compound Hl-116
Figure imgf000029_0003
Compound Hl-117 Compound Hl-118
Figure imgf000030_0001
Compound HI -1 19 Compound HI -120
[0035] Preferably, 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. Because the first host compound is a hole-transporting type, 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.
[0036] Synthesis of examples of the first host compound HI :
[0037] Example 1 - Synthesis of Compound Hl-1
Synthesis of 12, 12-dimethyl-10-phenyl-7-(9-phenyl-9H-carbazol-3-yl)- 10,12- dihydroindenor2, 1 -blcarbazole: N-(9,9-dimethyl-9H-fluorene-2-yl)-2-bromo-aniline (18.5 g), potassium acetate (6.98 g), and DMF (95 ml) were added to a nitrogen-substituted reaction vessel and aerated with nitrogen gas for 1 hour. The mixture was heated after adding tetrakis(triphenylphosphine)palladium (1.18 g) and stirred at 100 °C for 1 1 hours. After the mixture was cooled to a room temperature, the reaction liquid was added to water (300 ml) and extraction was performed with toluene (300 ml). An organic layer obtained was washed with water (200 ml) twice, 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/n-hexane) to obtain a pale yellow powder of 12, 12-dimethyl-10, 12-dihydroindeno[2, l-b]carbazole (7.9 g; yield 55.2%).
[0038] The resulting 12, 12-dimethyl-10,12-dihydroindeno[2, l-b]carbazole (7.8 g), iodobenzene (3.7 ml), sodium bisulfite (0.43 g), a copper powder (0.17 g), 3,5-di(tert- butyl)salicylic acid (0.69 g), potassium carbonate (5.71 g), and dodeeylbenzene (10 ml) were added to a nitrogen-substituted reaction vessel, heated, and stirred at 170 °C for 10 hours. The mixture was cooled to 100 °C, extracted by adding toluene (100 ml), concentrated under reduced pressure, and crystallized using n-hexane (30 ml) to obtain a pale yellow powder of 12,12-dimethyl-10-phenyl-10,12-dihydroindeno[2,l-b]carbazole (8.73 g; yield 88.3%).
[0039] The resulting 12, 12-dimethyl-10-phenyl-10,12-dihydroindeno[2, l-b]carbazole (7.5 g) and DMF (53 ml) were added to a reaction vessel. N-bromosuccinimide (3.72 g) was added under ice-cooled conditions, and the mixture was stirred for 9 hours and then left for one night. Water (260 ml) was added, and the mixture was subjected to filtration to obtain a brownish white powder of 7-bromo-12, 12-dimethyl-10-phenyl-10, 12-dihydroindeno[2, l- b]carbazole (8.67 g; yield 94.6%).
[0040] The resulting 7-bromo-12,12-dimethyl-10-phenyl-10, 12-dihydroindeno[2, l- b]carbazole (2.0 g), 9-phenyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-9H-carbazole (1.68 g), a toluene/ethanol (4/1, v/v) mixed solvent (15 ml), and a 2M potassium carbonate aqueous solution (3.4 ml) were added to a nitrogen-substituted reaction vessel and aerated with nitrogen gas for 30 min under ultrasonic irradiation. 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
concentrated under reduced pressure to obtain a crude product. 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%).
[0041] The structure of the resulting white powder was identified by NMR. ^- MR (THF-ds) detected 32 hydrogen signals, as follows. 5(ppm) = 8.66(1H), 8.64(1H), 8.59(1H), 8.23-8.29(lH), 7.88-7.90(lH), 7.83-7.85(lH), 7.78-7.80(lH), 7.66-7.71(8H), 7.42-7.53(7H), 7.37-7.40(lH), 7.31-7.33(1H), 7.26-7.29(lH), 7.21-7.24(1H), 1.51(6H).
[0042] Example 2 - Synthesis of Compound H 1 - 1 18
Synthesis of 10-('biphenyl-4-vn-12.12-dimethyl-7-('9-phenyl-9H-carbazol-3-vn-10.12- dihydroindeno|"2. l-b]carbazole: 12, 12-dimethyl- 10, 12-dihydroindeno[2, 1 -b]carbazole synthesized in Example 1 (35.5 g), 4-bromobiphenyl (35.0 g), sodium bisulfite (6.0 g), a copper powder (2.4 g), 3,5-di(tert-butyl)salicylic acid (9.4 g), potassium carbonate (31.2 g), and dodecylbenzene (52 ml) were added to a nitrogen-substituted reaction vessel, heated, and stirred at 190 °C for 26 hours. After cooled to 120 °C, the mixture was stirred after adding toluene (35 ml), and a crude product was collected by filtration. After adding toluene (1.6 L) to the crude product, the crude product was heated and extracted at 1 10 °C. After cooled to a room temperature, the crude product was concentrated under reduced pressure. The product was crystallized with methanol (120 ml) to obtain a white powder of 10-(biphenyl-4-yl)- 12,12-dimethyl-10, 12-dihydroindeno[2, l-b]carbazole (48.5 g; yield 88.1%)
[0043] The resulting 10-(biphenyl-4-yl)-12, 12-dimethyl-10, 12-dihydroindeno[2, l- b]carbazole (42.5 g) and DMF (2.5 L) were added to a reaction vessel, and the mixture was heated up to 70 °C and dissolved. After cooled to a room temperature, N-bromo-succinimide (17.4 g) was added, and the mixture was stirred for 7 hours. Water (2.5 L) was added, and filtration was performed to obtain a white powder of 10-(biphenyl-4-yl)-7-bromo-12, 12- dimethyl-10,12-dihydroindeno[2, l-b]carbazole (34.9 g; yield 69.5%).
[0044] The resulting 10-(biphenyl-4-yl)-7-bromo-12,12-dimethyl-10, 12- dihydroindeno[2, l-b]carbazole (16.5 g), 9-phenyl-3 -(4,4,5, 5-tetramethyl- 1,3, 2-dioxaborolan- 2-yl)-9H- carbazole (14.2 g), a toluene/ethanol (4/1, v/v) mixed solvent (250 ml), and a 2M potassium carbonate aqueous solution (48 ml) were added to a nitrogen-substituted reaction vessel and aerated with nitrogen gas for 30 min under ultrasonic irradiation. The mixture was heated after adding tetrakis(triphenylphosphine)palladium (1.9 g), and stirred at 73 °C for 5 hours. After the mixture was cooled to a room temperature, a precipitated crude product was collected by filtration. 1,2 Dichlorobenzene (450 ml) was added to the crude product, and the crude product was dissolved while being heated, and after removing insoluble matter by filtration, a filtrate was concentrated under reduced pressure. Purification by crystallization using 1 ,2-dichlorobenzene (150 ml) and n-hexane (300 ml) was performed to obtain a white powder of 10-(biphenyl-4-yl)- 12, 12-dimethyl-7-(9-phenyl-9H-carbazol-3 -yl)- 10,12- dihydroindeno[2, l-b]carbazole (9.8 g; yield 45.2%).
[0045] The structure of the resulting white powder was identified by NMR. ^- MR (THF-ds) detected 36 hydrogen signals, as follows. 5(ppm) = 8.69(1H), 8.64(1H), 8.59(1H), 8.28(1H), 7.99(2H), 7.89(1H), 7.85-7.78(6H), 7.66(4H), 7.56-7.49(6H), 7.44-7.37(4H), 7.32(1H), 7.27(1H), 7.23(1H), 1.52(6H). [0046] Example 3 - Synthesis of HI- 1 19
Synthesis of 12, 12-dimethyl-10-('9,9-dimethyl-9H-fluorene-2-yl -7-('9-phenyl-9H-carbazol-3- yl)- 10, 12-dihydroindenor2, 1 -blcarbazole: 12, 12-Dimethyl- 10, 12-dihydroindeno [2, 1- b]carbazole synthesized in Example 1 (5.5 g), 2-bromo-9,9-dimethyl-9H-fluorene (6.4 g), sodium bisulfite (0.3 g), a copper powder (0.1 g), 3,5-di(tert-butyl)salicylic acid (0.5 g), potassium carbonate (4.0 g), and dodecylbenzene (5 ml) were added to a nitrogen-substituted reaction vessel, heated, and stirred at 180 C for 29 hours. The mixture was cooled to 100 C, and insoluble matter was removed by filtration after adding toluene (80 ml), and a filtrate was concentrated. Crystallization using n-hexane (20 ml) was performed to obtain an ocher powder of 12, 12-dimethyl-10-(9,9-dimethyl-9H-fluorene-2-yl)-10, 12- dihydroindeno[2, l-b]carbazole (7.4 g; yield 80.0%).
[0047] The resulting 12, 12-dimethyl-10-(9,9-dimethyl-9H-fluorene-2-yl)-10, 12- dihydroindeno[2, l-b]carbazole (7.0 g) and DMF (140 ml) were added to a reaction vessel. The mixture was heated up to 100 °C, dissolved, and cooled. N-bromo-succinimide (2.6 g) was added under ice-cooled conditions, and the mixture was stirred for 1 hour at a room temperature. Water (500 ml) was added, and the mixture was subjected to filtration to obtain a pale red powder of 7-bromo-12, 12-dimethyl-10-(9,9-dimethyl-9H-fluorene-2-yl)-10, 12- dihydroindeno[2, l-b]carbazole (5.7 g; yield 70.3%).
[0048] The resulting 7-bromo-12, 12-dimethyl-10-(9,9-dimethyl-9H-fluorene-2-yl)-10, 12- dihydroindeno[2, l-b]carbazole (4.0 g), 9-phenyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)-9H-carbazole (3.2 g), a toluene/ethanol (4/1, v/v) mixed solvent (50 ml), and a 2M potassium carbonate aqueous solution (10 ml) were added to a nitrogen-substituted reaction vessel and aerated with nitrogen gas for 30 min under ultrasonic irradiation. 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%).
[0049] The structure of the resulting white powder was identified by NMR. ^- MR (THF-ds) detected 40 hydrogen signals, as follows. 5(ppm) = 8.67(1H), 8.65(1H), 8.60(1H), 8.28(1H), 8.08(1H), 7.90-7.82(5H), 7.69-7.66(5H), 7.58-7.49(5H), 7.43(2H), 7.39(2H), 7.36(1H), 7.33(1H), 7.28(1H), 7.23(1H), 1.61(6H), 1.51(6H).
Second and Third Host Compounds:
[0050] 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:
Figure imgf000034_0001
wherein X1 to X8 is selected from C or N; and wherein Z1 and Z2 is S or O. Preferably, the second host compound and the third host compound are different compounds.
[0051] According to an aspect of the present disclosure, any substituent in the second and third host compounds is preferably an unfused substituent independently selected from the group consisting of CnH2n+i, OCnH2n+i, OArb N(CnH2n+i)2, N(Ari)(Ar2), CH=CH-CnH2n+i, C=CHCnH2n+i, Ari, Ari-Ar2, CnH2n-Ari, or no substitution, wherein n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and wherein Ari and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.
[0052] According to another embodiment, 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.
[0053] Similar to the characterization of benzo-fused thiophenes, benzo-fused furans are also typically hole transporting materials having relatively high triplet energy. Examples of 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.
[0054] The compounds for the second host compound may be substituted with groups that are not necessarily triphenylenes, benzo-fused thiophenes, and benzo-fused furans.
Preferably, 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). Examples of such groups that may be used as substituents of the compound may include any unfused substituent independently selected from the group consisting of CnH2n+i, OC„H2„+i, OAri, N(CnH2n+i)2, N(Ari)(Ar2), CH=CH-CnH2n+1, C=CHCnH2n+i, Ari, Ari-Ar2, CnH2n-Ari, or no substitution, wherein n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and wherein Ari and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof. 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.
[0055] The 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).
[0056] Materials provided herein may also offer improved film formation in the device as fabricated by both vapor deposition and solution processing methods. In particular, 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.
[0057] According to another embodiment, the second and/or third host compounds are triphenylene-containing benzo-fused thiophenes or benzo-fused furans. Examples of 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):
Figure imgf000036_0001
(H-IV) (H-V) (H-VI)
In the formula (H-IV), X is S or O; Ri, R2 and R3 are unfused substituents that are independently selected from the group consisting of CnH2n+i, OCnH2n+i, OAri, N(CnH2n+i)2, N(Ari)(Ar2), CH=CH-CnH2n+i, C=CHCnH2n+i, Arb Ar Ar2, CnH2n-Ari, and hydrogen; n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; Ari and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof; p is 1, 2, 3, or 4; and at least one of Ri, R2 and R3 includes a triphenylene group.
[0058] In the formula (H-V), X is S or O; Ri, and R2 are unfused substituents that are independently selected from the group consisting of CnH2n+i, OCnH2n+i, OAri, N(CnH2n+i)2, N(Ari)(Ar2), CH=CH-CnH2n+i, C=CHCnH2n+i, Arh Ari-Ar2, CnH2n-Ari, and hydrogen; n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; Ari and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof; o is 1, 2, 3, or 4, and p is 1 or 2; and at least one of Rls and R2 includes a triphenylene group.
[0059] In the formula (H-VI), X is S or O; Ri, and R2 are unfused substituents that are independently selected from the group consisting of CnH2n+i, OCnH2n+i, OAri, N(CnH2n+i)2, N(Ari)(Ar2), CH=CH-CnH2n+i, C=CHCnH2n+i, Arb Ar Ar2, CnH2n-Ari, and hydrogen; n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; Ari and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof; o and p is 1, 2, 3, or 4; and at least one of Ri, and R2 includes a triphenylene group.
[0060] Examples of compounds having the structure of the formula (H-IV) include:
Figure imgf000037_0001
Compound 11 G Compound 11 where X is S or O. Preferably, X is S. Ri to Rn are independently selected from the group consisting of CnH2n+i, OCnH2n+i, OAn, N(CnH2n+i)2, N(An)(Ar2), CH=CH-CnH2n+i, C=CHCnH2n+i, Ari, Ari-Ar2, CnH2n-Ari, or no substitution. Each of Ri to Rn may represent mono, di, tri, or tetra substitutions., n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Ari and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof. At least one of Ri, R2, and R3 includes a triphenylene group. [0061] Examples of compounds having the structure of the formula (H-V) include:
Figure imgf000038_0001
where X is S or O. Preferably, X is S. Ri to Rn are independently selected from the group consisting of CnH2n+1, OCnH2n+i, OAn, N(CnH2n+1)2, N(An)(Ar2), CH=CH-CnH2n+1, C=CHCnH2n+i, Ari, Ari-Ar2, CnH2n-Ari, or no substitution. Each of Ri to Rn may represent mono, di, tri, or tetra substitutions, and n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Ari and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof. At least one of Ri, R2, and R3 includes a triphenylene group.
[0062] Examples of compounds having the structure of the formula (H-VI) include:
Figure imgf000039_0001
Figure imgf000040_0001
Figure imgf000041_0001
40
Figure imgf000042_0001
41
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
44
Figure imgf000046_0001
Com ound 41 G Compound 41
Figure imgf000046_0002
Compound 42G Compound 42
Figure imgf000046_0003
Compound 43
Figure imgf000047_0001
Figure imgf000047_0002
where X is S or O. In a preferred embodiment, X is S. Ri to Rn are independently selected from the group consisting of CnH2n+i, OCnH2„+i, OArb N(CnH2n+i)2, N(Ari)(Ar2), CH=CH- CnH2n+i, C=CHCnH2n+i, Ari, Ari-Ar2, CnH2n-Ari, or no substitution. Each of Ri to Rn may represent mono, di, tri, or tetra substitutions, n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Ari and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof. At least one of Ri, R2, and R3 includes a triphenylene group.
[0063] 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.
[0064] 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. Depending on the phosphorescent dopant that is used, in some cases, 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. In some cases, 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. In particular, 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.
[0065] The synthesis information for the examples of the second host compounds described above can be found in PCT publication Nos. WO 2009/021 126 published on 12 February 2009, the contents of which are incorporated herein by reference, and WO 2010/083359 published on 22 July 2010, the contents of which are incorporated herein by reference.
[0066] 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.
[0067] 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.
According to one embodiment, 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.
Exciton/Electron Blocking Layer:
[0068] According to another aspect, 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. The EBL blocks at least one or both of excitons or electrons.
[0069] 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.
Hole Transport Layer:
[0070] 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
Figure imgf000050_0001
wherein 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;
(HTL-II) is
Figure imgf000050_0002
wherein 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
unsubstituted phenyl group, or a phenyl group having a lower alkyl group or a lower alkoxy group as a substituent(s); R24 represents a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group or a chlorine atom; and
Ai represents a group represented by any one of the following structural formulae (al) to (il);
Figure imgf000051_0001
in which R25 represents a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group or a chlorine atom;
(HTL-III) is
Figure imgf000051_0002
wherein R31, R32 and R33 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); R34 represents a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group or a chlorine atom; and
A2 represents a group represented by any one of the following formulae (j l) to (nl);
Figure imgf000052_0001
wherein 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
unsubstituted phenyl group or a phenyl group having a deuterium atom, a lower alkyl group or a lower alkoxy group as a substituent(s); R43 represents a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group or a chlorine atom; and
A3 represents a group represented by anyone of the following structural formulae (a2) to (i2);
Figure imgf000052_0002
Figure imgf000053_0001
in which R44 represents a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group or a chlorine atom;
(HTL-V) is
Figure imgf000053_0002
wherein 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
unsubstituted phenyl group or a phenyl group having a deuterium atom, a lower alkyl group or a lower alkoxy group as a substituent(s); R53 represents a hydrogen atom, a deuterium atom, a lower alkyl group, a lower alkoxy group or a chlorine atom; and
A4 represents a group represented by anyone of the following structural formulae (j2) to (n2);
Figure imgf000054_0001
(HTL-VI) is
Figure imgf000054_0002
where ¾ι to ¾9, 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; r6i to which may be the same or different, represent 0, 1 or 2.
[0071] The terms "lower alkyl group" and "lower alkoxy group" as used herein mean "C1-4 alkyl group" and "C1-4 alkoxy group," respectively.
[0072] The synthesis information for the compounds of the formulae (HTL-I) to (HTL-VI) and the specific examples of the compounds of formulae (HTL-I) to (HTL-VI) are provided in United States patent No. 5,707,747 to Tomiyama et al, the contents of which are incorporated herein by reference. Examples of compounds having the structure of formula (HTL-I) to (HTL-VI)
Compound- la,
Compound-2a,
Compound-3a,
Compound-4a,
Figure imgf000055_0001
Compound-5a,
I- 10a,
Figure imgf000056_0001
Figure imgf000057_0001
Compound- 12a.
Substrate:
[0074] 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. In particular, 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.
Electrodes:
[0075] 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. Typically 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. 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.
[0076] When light is emitted from the light emitting layer, 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 Ω/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 μιη, and preferably from about 10 nm to about 200 nm.
[0077] 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. For transparent or top-emitting devices, a TOLED cathode such as disclosed in U.S. Patent No. 6,548,956 is preferred.
[0078] 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.
Inverted PLED:
[0079] 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.
[0080] The simple layered structures of 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.
[0081] Although many of the examples provided herein described various layers as comprising a single material, it is understood that combinations of materials, or more generally a mixture, may be used. Also, the layers may have various sub-layers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 400, 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. In one embodiment, 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. EXAMPLES
[0082] The invention will be described in further detail with reference to the following example devices and comparative example devices. However, the invention is not limited by the following examples. The chemical structures of the particular organic compounds Hl-1, Hl-118, Hl-119, H, El, Gl, NPD and Alq3 used in making the example devices are shown below.
Figure imgf000059_0001
Figure imgf000060_0001
Alq3
[0083] 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 Alq3. 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, and the third host compound was El as an electron-transporting host. As shown in the experimental device data summary of Table 3, 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.
Table 1. Energy levels of the EML components
Figure imgf000060_0002
The functions of the organic compounds used in the exemplary devices according to the present disclosure are provided in Table 2 below.
Table 2. Functions of the organic compounds Compound Hl-1 Hl-1 Hl-118 Hl-118 Hl-119 Hl-119
Layer exciton/electron Emissive exciton/electron Emissive exciton/electron Emissive location blocking layer Layer blocking layer Layer blocking layer Layer
Hole- Hole- Hole-
Exciton and/or Exciton and/or Exciton and/or
Function transporting transporting transporting
Electron blocker Electron blocker Electron blocker
host host host
Table 2 (cont'd).
Figure imgf000061_0001
[0084] 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. For example, in the Example Device #1, 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.
[0085] 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. 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.
[0086] In the 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.
[0087] Compound HI as a host and an EBL - Example Devices #4 through #8:
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.%).
[0088] The measured CIE 1931 coordinates, mm and FWHM (Full Width at Half
Maximum) of the emission spectrum from the example devices are shown in Table 3. The example devices #1 through #8 with compounds Hl-l, Hl-1 19 or Hl-118 as a component in the EML exhibited better color saturation compared to the comparative reference device CE. As shown in Table 3, 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
Figure imgf000063_0001
[0089] 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.
[0090] All organic layers were deposited under high-vacuum conditions (lxlO 7 Torr). The PHOLED was transferred directly from vacuum into an inert environment glove-box, where it was encapsulated using a UV-curable epoxy, and a glass lid with a moisture getter.
[0091] Unless otherwise specified, any of the layers of the various embodiments of the invention described herein may be deposited by any suitable method. For the organic layers, 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. 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. For the other layers, 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. 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 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.
[0092] 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.
0093] Table 5. Examples of phosphorescent dopants.
Figure imgf000064_0001
Figure imgf000065_0001
Figure imgf000066_0001
and its derivatives
Figure imgf000067_0001
Figure imgf000068_0001
Figure imgf000069_0001
Figure imgf000070_0001
Figure imgf000071_0001
Figure imgf000072_0001
Figure imgf000073_0001

Claims

WHAT IS CLAIMED IS:
1. An organic light emitting device comprising an anode, a cathode and a plurality of organic layers provided between them, the plurality of organic layers comprising:
an emissive layer comprising a host material and a phosphorescent emitter material, the host material comprising:
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,
Figure imgf000074_0001
wherein 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;
Ar1; Ar2, and Ar3 may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group, where A and A¾ or A¾ and A¾ may bind to each other via a single bond or via substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring;
Ri to R9 may be the same or different, and represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano, nitro, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or substituted or unsubstituted aryloxy, which may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring; and
Rio and Rn may be the same or different, and represent linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or substituted or unsubstituted aryloxy, which may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring.
2. The organic light emitting device of claim 1, wherein the first host compound constitutes no more than 25 wt.% of the emissive layer.
3. The organic light emitting device of claim 1, wherein the first host compound constitutes 10 - 20 wt.% of the emissive layer.
4. The organic light emitting device of claim 1, wherein the first host compound is selected from the group consisting of:
Figure imgf000075_0001
Compound Hl-1 Compound HI -2
Figure imgf000075_0002
Compound HI -3 Compound HI -4
Figure imgf000076_0001
Compound HI -5 Compound HI -6
Figure imgf000076_0002
Com ound HI -7 Compound HI -8
Figure imgf000076_0003
Compound HI -9 Compound HI -10
Figure imgf000076_0004
Compound Hl-11 Compound Hl-12
Figure imgf000077_0001
Compound HI- 13 Compound HI -14
Figure imgf000077_0002
Compound HI -15 Compound HI -16
Figure imgf000077_0003
Compound HI- 17 Compound HI- 18
Figure imgf000078_0001
Compound HI- 19 Compound HI -20
Figure imgf000078_0002
Compound H 1 -21 Compound H 1 -22
Figure imgf000078_0003
Compound H 1 -23 Compound H 1 -24
Figure imgf000078_0004
Compound H 1 -25 Compound H 1 -26
Figure imgf000079_0001
Compound HI -27 Compound HI -28
Figure imgf000079_0002
Compound HI -29 Compound HI -30
Figure imgf000079_0003
Compound HI -31 Compound HI -32
Figure imgf000080_0001
Compound HI -33 Compound HI -34
Figure imgf000080_0002
Compound HI -35 Compound HI -36
Figure imgf000080_0003
Compound HI -37 Compound HI -38
Figure imgf000080_0004
Compound HI -39 Compound HI -40
Figure imgf000081_0001
Compound HI -41 Compound HI -42
Figure imgf000081_0002
Compound HI -43 Compound HI -44
Figure imgf000081_0003
Compound HI -45 Compound HI -46
Figure imgf000082_0001
Compound HI -47 Compound HI -48
Figure imgf000082_0002
Compound HI -49
H
Figure imgf000082_0003
Compound HI -50 3
H,
Figure imgf000083_0001
Compound HI -51
Figure imgf000083_0002
Compound HI -52 Compound HI -53
Figure imgf000083_0003
Compound Hl-54 Compound Hl-55
Figure imgf000084_0001
Compound HI -56 Compound HI -57
Figure imgf000084_0002
Compound HI -58 Compound HI -59
3
Figure imgf000085_0001
Compound HI -60 Compound HI -61
Figure imgf000085_0002
Compound HI -62 Compound HI -63
Figure imgf000085_0003
Compound H 1 -64 Compound H 1 -65
Figure imgf000086_0001
Compound HI -66 Compound HI -67
Figure imgf000086_0002
Compound HI -68 Compound HI -69
Figure imgf000086_0003
Compound HI -70 Compound HI -71
Figure imgf000086_0004
Compound HI -72 Compound HI -73
Figure imgf000087_0001
Compound HI -74 Compound HI -75
Figure imgf000087_0002
Compound HI -76 Compound HI -77
Figure imgf000087_0003
Compound HI -78 Compound HI -79
Figure imgf000087_0004
Compound HI -80 Compound HI -81
Figure imgf000088_0001
Compound HI -82 Compound HI -83
Figure imgf000088_0002
Compound Hl-84 Compound HI -85
Figure imgf000088_0003
Compound HI -86 Compound HI -87
Figure imgf000088_0004
Compound HI -88 Compound Hl-89
Figure imgf000089_0001
Compound HI -90 Compound HI -91
Figure imgf000089_0002
Compound HI -92 Compound HI -93
Figure imgf000089_0003
Compound HI -94 Compound HI -95
Figure imgf000090_0001
Compound HI -96 Compound HI -97
Figure imgf000090_0002
Compound HI -98 Compound HI -99
Figure imgf000090_0003
Compound HI -100 Compound HI -101
Figure imgf000091_0001
Compound H 1 - 102 Compound HI -103
Figure imgf000091_0002
Compound HI -104 Compound HI -105
Figure imgf000091_0003
Compound HI -106 Compound HI -107
Figure imgf000092_0001
Compound Hl-1 10 Compound Hl-1 11
Figure imgf000092_0002
Compound Hl-1 12 Compound Hl-1 13
Figure imgf000093_0001
Compound Hl-1 14
Figure imgf000093_0002
Compound Hl-1 15
Figure imgf000093_0003
Compound Hl-1 16
Figure imgf000094_0001
Compound Hl-1 17 Compound Hl-118
Figure imgf000094_0002
Compound H 1 - 1 19 , and Compound H 1 - 120 .
5. The organic light emitting device of claim 1, wherein the second host compound contains at least one of the following groups:
Figure imgf000094_0003
wherein X1 to X8 is selected from C or N; and
wherein Z1 and Z2 is S or O.
6. The organic light emitting device according to claim 5, wherein any substituent in the second host compound is an unfused substituent independently selected from the group consisting of CnH2n+1, OCnH2n+i, OAn, N(CnH2n+1)2, N(An)(Ar2), CH=CH-CnH2n+1,
C=CHCnH2n+i, Ari, Ari-Ar2, CnH2n-Ari, or no substitution, wherein n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and wherein Ari and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.
7. The organic light emitting device according to claim 1, wherein the second host compound is represented by the structure of formula (H-IV):
Figure imgf000095_0001
wherein X is S or O;
wherein Ri, R2, and R3 are unfused substituents independently selected from the group consisting CnH2n+i, OCnH2n+i, OArb N(CnH2n+i)2, N(Ari)(Ar2), CH=CH-CnH2n+i, C=CHCnH2n+i, Ari, Ari-Ar2, CnH2n-Ari, and hydrogen;
wherein n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;
wherein Ari and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof;
wherein p is 1, 2, 3, or 4; and
wherein at least one of Ri, R2 and R3 includes a triphenylene group.
8. The organic light emitting device according to claim 7, wherein X is S.
9. The organic light emitting device according to claim 7, wherein X is O.
10. The organic light emitting device according to claim 1, wherein the second host compound is represented by the structure of formula (H-V):
Figure imgf000096_0001
wherein X is S or O;
wherein Ri and R2 are unfused substituents independently selected from the group consisting CnH2n+1, OCnH2n+1, OAn, N(CnH2n+1)2, N(An)(Ar2), CH=CH-CnH2n+1,
C=CHCnH2n+i, Ari, Ari-Ar2, CnH2n-Ari, and hydrogen, and
wherein n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;
wherein Ari and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof;
wherein 0 is 1, 2, 3 or 4, and p is 1 or 2; and
wherein at least one of Ri and R2 includes a triphenylene group.
11. The organic light emitting device according to claim 10, wherein X is S.
12. The organic light emitting device according to claim 10, wherein X is O.
13. The organic light emitting device according to claim 6, wherein the second host compound is represented by the structure of formula (H-VI):
Figure imgf000096_0002
(H-VI)
wherein X is S or O; and
wherein Ri and R2 are independently selected from the group consisting CnH2n+i, OCnH2n+i, OAn, N(CnH2n+i)2, N(An)(Ar2), CH=CH-CnH2n+i, C=CHCnH2n+i, An, An-Ar2, CnH2n-Ari, and hydrogen; and
wherein n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;
wherein Ari and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof;
wherein 0 and p is 1, 2, 3, or 4; and
wherein at least one of Ri and R2 includes a triphenylene group.
14. The organic light emitting device according to claim 13, wherein X is S.
15. The organic light emitting device according to claim 13, wherein X is O.
16. The organic light emitting device according to claim 13, wherein the second host compound has the formula H:
Figure imgf000097_0001
(H) .
17. The organic light emitting device according to claim 1, further comprising a third host compound in the emissive layer, wherein the third host compound is
Figure imgf000097_0002
18. The organic light emitting device according to claim 1, wherein 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.
19. The organic light emitting device according to claim 18, wherein the phosphorescent organometallic platinum compound has an aromatic ligand.
20. The organic light emitting device according to claim 18, wherein the phosphorescent organometallic iridium compound has an aromatic ligand.
21. The organic light emitting device according to claim 18, wherein the phosphorescent organometallic osmium compound has an aromatic ligand.
22. An organic light emitting device comprising an anode, a cathode and a plurality of organic layers provided between them, the plurality of organic layers comprising: an emissive layer comprising a host material and a phosphorescent emitter material, wherein the host material comprising:
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,
Figure imgf000098_0001
wherein 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;
Ar1; Ar2, and Ar3 may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group, where A and A¾ or A¾ and A¾ may bind to each other via a single bond or via substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring;
Ri to R9 may be the same or different, and represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano, nitro, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or substituted or unsubstituted aryloxy, which may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring; and
Rio and Rn may be the same or different, and represent linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or substituted or unsubstituted aryloxy, which may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring ; and
an exciton/electron blocking layer disposed between the emissive layer and the anode, wherein the exciton/electron blocking layer comprises a blocking compound having the indeno-carbazole ring structure represented by the general formula HI, the exciton/electron blocking layer blocks at least one of excitons or electrons, and wherein the first host compound and the blocking compound can be the same or different.
23. The organic light emitting device according to claim 22, wherein the first host compound and the blocking compound are independently selected from the group consisting of:
Figure imgf000099_0001
Compound Hl-1 Compound HI -2
Figure imgf000099_0002
Compound HI -3 Compound HI -4
Figure imgf000100_0001
Compound HI -5 Compound HI -6
Figure imgf000100_0002
Compound HI -7 Compound HI -8
Figure imgf000100_0003
Compound HI -9 Compound HI -10
Figure imgf000100_0004
Compound HI- 11 Compound HI- 12
Figure imgf000101_0001
Compound HI- 13 Compound HI -14
Figure imgf000101_0002
Compound HI -15 Compound HI -16
Figure imgf000101_0003
Compound HI- 17 Compound HI- 18
Figure imgf000101_0004
Compound HI- 19 Compound HI -20
Figure imgf000102_0001
Compound HI -21 Compound HI -22
Figure imgf000102_0002
Compound HI -23 Compound HI -24
Figure imgf000102_0003
Compound HI -25 Compound HI -26 B3C CHS
Figure imgf000102_0004
Compound HI -27 Compound HI -28
Figure imgf000103_0001
Compound HI -29 Compound HI -30
Figure imgf000103_0002
Compound HI -31 Compound HI -32
Figure imgf000103_0003
Compound HI -33 Compound Hl-34
Figure imgf000103_0004
Compound HI -35 Compound HI -36
Figure imgf000104_0001
Compound HI -37 Compound HI -38
Figure imgf000104_0002
Compound HI -39 Compound HI -40
Figure imgf000104_0003
Compound H 1 -41 Compound H 1 -42
Figure imgf000104_0004
Compound H 1 -43 Compound H 1 -44
Figure imgf000105_0001
Compound HI -45 Compound HI -46
Figure imgf000105_0002
Compound HI -47 Compound HI -48
Figure imgf000105_0003
Compound HI -49 Compound HI -50
Figure imgf000105_0004
Compound HI -51 Compound HI -52
Figure imgf000106_0001
Compound HI -53 Compound HI -54
Figure imgf000106_0002
Compound HI -55 Compound HI -56
Figure imgf000106_0003
Compound HI -57 Compound HI -58
Figure imgf000107_0001
Compound HI -59 Compound HI -60
Figure imgf000107_0002
Compound HI -61 Compound HI -62
Figure imgf000107_0003
Compound HI -63 Compound HI -64
Figure imgf000107_0004
Compound H 1 -65 Compound H 1 -66
Figure imgf000108_0001
Compound H 1 -67 Compound H 1 -68
Figure imgf000108_0002
Compound HI -69
Figure imgf000108_0003
Compound HI -70 Compound HI -71
Figure imgf000108_0004
Compound HI -72 Compound HI -73
Figure imgf000109_0001
Compound HI -74 Compound HI -75
Figure imgf000109_0002
Compound HI -76 Compound HI -77
Figure imgf000109_0003
Compound HI -78 Compound HI -79
Figure imgf000109_0004
Compound HI -80 Compound HI -81
Figure imgf000110_0001
Compound HI -82 Compound HI -83
Figure imgf000110_0002
Compound Hl-84 Compound HI -85
Figure imgf000110_0003
Compound HI -86 Compound HI -87
Figure imgf000110_0004
Compound HI -88 Compound Hl-89
Figure imgf000111_0001
Compound HI -90 Compound HI -91
Figure imgf000111_0002
Compound HI -92 Compound HI -93
Figure imgf000111_0003
Compound HI -94 Compound HI -95
Figure imgf000112_0001
Compound HI -96 Compound HI -97
Figure imgf000112_0002
Compound HI -98 Compound HI -99
Figure imgf000112_0003
Compound HI -100 Compound HI -101
Figure imgf000113_0001
Compound H 1 - 102 Compound HI -103
Figure imgf000113_0002
Compound HI -104 Compound HI -105
Figure imgf000113_0003
Compound HI -106 Compound HI -107
Figure imgf000114_0001
Compound HI -110 Compound HI -111
Figure imgf000114_0002
Compound Hl-112 Compound Hl-113
Figure imgf000115_0001
Compound Hl-114 Compound Hl-115 ¾
Figure imgf000115_0002
Compound Hl-116 Compound Hl-117
Figure imgf000115_0003
Compound Hl-118 Compound H 1 - 119 , and
Figure imgf000116_0001
Compound HI -120
24. The organic light emitting device according to claim 22, further comprising a third host compound in the emissive layer, wherein the third host compound is
Figure imgf000116_0002
25. The organic light emitting device according to claim 22, wherein the exciton/electron blocking layer blocks both excitons and electrons.
26. The organic light emitting device according to claim 22, wherein 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.
27. The organic light emitting device according to claim 26, wherein the phosphorescent organometallic platinum compound has an aromatic ligand.
28. The organic light emitting device according to claim 26, wherein the phosphorescent organometallic iridium compound has an aromatic ligand.
29. The organic light emitting device according to claim 26, wherein the phosphorescent organometallic osmium compound has an aromatic ligand.
30. An organic light emitting device comprising an anode, a cathode and a plurality of organic layers provided between them, the plurality of organic layers comprising:
an emissive layer comprising a host material and a phosphorescent emitter material, the host material comprising:
a first host compound and a second host compound, wherein the first host compound is selected from a group consisting of
Figure imgf000117_0001
Hl-118 wherein the second host compound is represented by the formula H
Figure imgf000117_0002
(H) ; and
the phosphorescent emitter material is a compound represented by the formula Gl
Figure imgf000118_0001
31. The organic light emitting device of claim 30, wherein the first host compound constitutes no more than 25 wt.% of the emissive layer.
32. The organic light emitting device of claim 31, wherein the first host compound is 10- 20 wt.% of the emissive layer.
PCT/US2013/046802 2013-06-20 2013-06-20 Phosphorescent organic light emitting devices having a hole-transporting host in the emissive region WO2014204464A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
PCT/US2013/046802 WO2014204464A1 (en) 2013-06-20 2013-06-20 Phosphorescent organic light emitting devices having a hole-transporting host in the emissive region
JP2016521385A JP6286033B2 (en) 2013-06-20 2013-06-20 Phosphorescent organic light-emitting device having a hole-transporting host in the light-emitting region
TW103120364A TWI640599B (en) 2013-06-20 2014-06-12 Phosphorescent organic light-emitting device having a hole transmission body in an emission region

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2013/046802 WO2014204464A1 (en) 2013-06-20 2013-06-20 Phosphorescent organic light emitting devices having a hole-transporting host in the emissive region

Publications (1)

Publication Number Publication Date
WO2014204464A1 true WO2014204464A1 (en) 2014-12-24

Family

ID=52105033

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2013/046802 WO2014204464A1 (en) 2013-06-20 2013-06-20 Phosphorescent organic light emitting devices having a hole-transporting host in the emissive region

Country Status (3)

Country Link
JP (1) JP6286033B2 (en)
TW (1) TWI640599B (en)
WO (1) WO2014204464A1 (en)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016076629A1 (en) * 2014-11-11 2016-05-19 Rohm And Haas Electronic Materials Korea Ltd. A plurality of host materials and an organic electroluminescence device comprising the same
WO2016116521A1 (en) * 2015-01-20 2016-07-28 Cynora Gmbh Organic molecules, in particular for use in optoelectronic components
WO2016122150A3 (en) * 2015-01-29 2016-10-06 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using same, and electronic device thereof
KR20160142909A (en) * 2015-06-03 2016-12-14 (주)위델소재 Dibenzothiophene derivative compound and organic electroluminescent device using the same
WO2017041874A1 (en) * 2015-09-08 2017-03-16 Merck Patent Gmbh Materials for organic electroluminescent devices
KR20170031860A (en) * 2015-09-11 2017-03-22 삼성디스플레이 주식회사 Organic light emitting device
KR20170093061A (en) * 2016-02-03 2017-08-14 에스에프씨 주식회사 Organic light-emitting compounds and Organic light-emitting device comprising the same
CN107108578A (en) * 2015-01-30 2017-08-29 默克专利有限公司 The material of electronic device
CN107207434A (en) * 2015-01-20 2017-09-26 西诺拉股份有限公司 Organic molecule, particularly for the organic molecule in photoelectric device
WO2017199622A1 (en) * 2016-05-19 2017-11-23 コニカミノルタ株式会社 Organic electroluminescence element, display device, and lighting device
WO2018070835A1 (en) * 2016-10-14 2018-04-19 주식회사 두산 Organic compound and organic electroluminescent element using same
CN108586441A (en) * 2018-05-03 2018-09-28 上海天马有机发光显示技术有限公司 A kind of compound, a kind of organic light-emitting display device
US10186668B2 (en) 2017-03-04 2019-01-22 Feng-wen Yen Organic electroluminescent material and use thereof
CN109844978A (en) * 2016-10-19 2019-06-04 保土谷化学工业株式会社 Indeno carbazole compound and organic electroluminescent device
CN110317206A (en) * 2018-03-29 2019-10-11 江苏三月光电科技有限公司 It is a kind of using triaryl amine as the compound of core and its application
US10580997B2 (en) 2016-06-02 2020-03-03 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
CN111063818A (en) * 2019-12-26 2020-04-24 武汉华星光电半导体显示技术有限公司 Display panel and preparation method thereof
US11130747B2 (en) 2014-11-11 2021-09-28 Rohm And Haas Electronic Materials Korea Ltd Plurality of host materials and an organic electroluminescence device comprising the same
US11476426B2 (en) 2016-02-03 2022-10-18 Sfc Co., Ltd. Organic light emitting compounds and organic light emitting devices including the same
US11691957B2 (en) 2019-12-27 2023-07-04 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105658626A (en) * 2013-10-25 2016-06-08 E.I.内穆尔杜邦公司 Blue luminescent compounds
JPWO2018061421A1 (en) * 2016-09-28 2018-09-27 住友化学株式会社 Composition and light emitting device
KR102654237B1 (en) * 2017-09-25 2024-04-03 머티어리얼사이언스 주식회사 An organic compound and an organic light emitting device comprising the same
KR102668688B1 (en) * 2018-07-23 2024-05-24 삼성디스플레이 주식회사 Organic light-emitting device
KR102595739B1 (en) * 2018-08-09 2023-10-30 덕산네오룩스 주식회사 Organic electronic element comprising mixture mixed with different compounds as host material and an electronic device thereof
KR102595744B1 (en) * 2018-08-09 2023-10-30 덕산네오룩스 주식회사 Organic electronic element comprising mixture mixed with different compounds as host material and an electronic device thereof
CN111129330A (en) * 2019-12-26 2020-05-08 武汉华星光电半导体显示技术有限公司 Display panel and preparation method thereof
CN119053586A (en) * 2022-03-31 2024-11-29 出光兴产株式会社 Compound, material for organic electroluminescent element, and electronic device

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009021126A2 (en) * 2007-08-08 2009-02-12 Universal Display Corporation Benzo-fused thiophene or benzo-fused furan compounds comprising a triphenylene group
US20090108737A1 (en) * 2006-12-08 2009-04-30 Raymond Kwong Light-emitting organometallic complexes
WO2010083359A2 (en) * 2009-01-16 2010-07-22 Universal Display Corporation New materials with aza-dibenzothiophene or aza-dibenzofuran core for pholed
KR20120123353A (en) * 2009-12-21 2012-11-08 이 아이 듀폰 디 네모아 앤드 캄파니 Electroactive composition and electronic device made with the composition
US20130126856A1 (en) * 2010-07-30 2013-05-23 Hodogaya Chemical Co., Ltd. Compound having indenocarbazole ring structure, and organic electroluminescent device

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010027583A1 (en) * 2008-09-03 2010-03-11 Universal Display Corporation Phosphorescent materials
DE102009023155A1 (en) * 2009-05-29 2010-12-02 Merck Patent Gmbh Materials for organic electroluminescent devices
EP2758372B1 (en) * 2011-09-21 2017-05-17 Merck Patent GmbH Carbazole derivatives for organic electroluminescent devices

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090108737A1 (en) * 2006-12-08 2009-04-30 Raymond Kwong Light-emitting organometallic complexes
WO2009021126A2 (en) * 2007-08-08 2009-02-12 Universal Display Corporation Benzo-fused thiophene or benzo-fused furan compounds comprising a triphenylene group
WO2010083359A2 (en) * 2009-01-16 2010-07-22 Universal Display Corporation New materials with aza-dibenzothiophene or aza-dibenzofuran core for pholed
KR20120123353A (en) * 2009-12-21 2012-11-08 이 아이 듀폰 디 네모아 앤드 캄파니 Electroactive composition and electronic device made with the composition
US20130126856A1 (en) * 2010-07-30 2013-05-23 Hodogaya Chemical Co., Ltd. Compound having indenocarbazole ring structure, and organic electroluminescent device

Cited By (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016076629A1 (en) * 2014-11-11 2016-05-19 Rohm And Haas Electronic Materials Korea Ltd. A plurality of host materials and an organic electroluminescence device comprising the same
US11130747B2 (en) 2014-11-11 2021-09-28 Rohm And Haas Electronic Materials Korea Ltd Plurality of host materials and an organic electroluminescence device comprising the same
WO2016116521A1 (en) * 2015-01-20 2016-07-28 Cynora Gmbh Organic molecules, in particular for use in optoelectronic components
CN107207434A (en) * 2015-01-20 2017-09-26 西诺拉股份有限公司 Organic molecule, particularly for the organic molecule in photoelectric device
WO2016122150A3 (en) * 2015-01-29 2016-10-06 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using same, and electronic device thereof
US20180006237A1 (en) * 2015-01-30 2018-01-04 Merck Patent Gmbh Materials for electronic devices
KR102626977B1 (en) * 2015-01-30 2024-01-19 메르크 파텐트 게엠베하 Materials for electronic devices
CN107108578A (en) * 2015-01-30 2017-08-29 默克专利有限公司 The material of electronic device
KR20170110641A (en) * 2015-01-30 2017-10-11 메르크 파텐트 게엠베하 Materials for electronic devices
JP2018507194A (en) * 2015-01-30 2018-03-15 メルク パテント ゲーエムベーハー Materials for electronic devices
KR20160142909A (en) * 2015-06-03 2016-12-14 (주)위델소재 Dibenzothiophene derivative compound and organic electroluminescent device using the same
KR101694496B1 (en) 2015-06-03 2017-01-11 (주)위델소재 Dibenzothiophene derivative compound and organic electroluminescent device using the same
CN107922398B (en) * 2015-09-08 2022-01-28 默克专利有限公司 Material for organic electroluminescent device
WO2017041874A1 (en) * 2015-09-08 2017-03-16 Merck Patent Gmbh Materials for organic electroluminescent devices
CN107922398A (en) * 2015-09-08 2018-04-17 默克专利有限公司 Material for organic electroluminescence device
US11581491B2 (en) 2015-09-08 2023-02-14 Merck Patent Gmbh Materials for organic electroluminescent devices
KR20180044423A (en) * 2015-09-08 2018-05-02 메르크 파텐트 게엠베하 Material for organic electroluminescence device
JP2018528216A (en) * 2015-09-08 2018-09-27 メルク パテント ゲーエムベーハー Materials for organic electroluminescent devices
KR102610950B1 (en) * 2015-09-08 2023-12-06 메르크 파텐트 게엠베하 Materials for organic electroluminescent devices
KR20170031860A (en) * 2015-09-11 2017-03-22 삼성디스플레이 주식회사 Organic light emitting device
KR102490887B1 (en) * 2015-09-11 2023-01-25 삼성디스플레이 주식회사 Organic light emitting device
KR20170093061A (en) * 2016-02-03 2017-08-14 에스에프씨 주식회사 Organic light-emitting compounds and Organic light-emitting device comprising the same
KR102338428B1 (en) * 2016-02-03 2021-12-14 에스에프씨 주식회사 Organic light-emitting compounds and Organic light-emitting device comprising the same
US11476426B2 (en) 2016-02-03 2022-10-18 Sfc Co., Ltd. Organic light emitting compounds and organic light emitting devices including the same
JPWO2017199622A1 (en) * 2016-05-19 2019-03-14 コニカミノルタ株式会社 Organic electroluminescence element, display device and lighting device
WO2017199622A1 (en) * 2016-05-19 2017-11-23 コニカミノルタ株式会社 Organic electroluminescence element, display device, and lighting device
US10580997B2 (en) 2016-06-02 2020-03-03 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
KR102673121B1 (en) * 2016-10-14 2024-06-07 솔루스첨단소재 주식회사 Organic compound and organic electroluminescent device using the same
KR20180041361A (en) * 2016-10-14 2018-04-24 주식회사 두산 Organic compound and organic electroluminescent device using the same
WO2018070835A1 (en) * 2016-10-14 2018-04-19 주식회사 두산 Organic compound and organic electroluminescent element using same
CN109844978A (en) * 2016-10-19 2019-06-04 保土谷化学工业株式会社 Indeno carbazole compound and organic electroluminescent device
US11925114B2 (en) 2016-10-19 2024-03-05 Hodogaya Chemical Co., Ltd. Indenocarbazole compound and organic electroluminescence device
EP3514845A4 (en) * 2016-10-19 2020-05-06 Hodogaya Chemical Co., Ltd. INDENOCARBAZOLIC COMPOUND AND ORGANIC ELECTROLUMINESCENT ELEMENT
US10186668B2 (en) 2017-03-04 2019-01-22 Feng-wen Yen Organic electroluminescent material and use thereof
CN110317206A (en) * 2018-03-29 2019-10-11 江苏三月光电科技有限公司 It is a kind of using triaryl amine as the compound of core and its application
US11345689B2 (en) 2018-05-03 2022-05-31 Shanghai Tianma AM-OLED Co., Ltd. Compound and organic light emitting display device
CN108586441B (en) * 2018-05-03 2020-12-29 上海天马有机发光显示技术有限公司 A compound, an organic light-emitting display device
CN108586441A (en) * 2018-05-03 2018-09-28 上海天马有机发光显示技术有限公司 A kind of compound, a kind of organic light-emitting display device
US11864442B2 (en) 2019-12-26 2024-01-02 Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. Display panel and manufacturing method thereof
CN111063818A (en) * 2019-12-26 2020-04-24 武汉华星光电半导体显示技术有限公司 Display panel and preparation method thereof
US11691957B2 (en) 2019-12-27 2023-07-04 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same

Also Published As

Publication number Publication date
JP6286033B2 (en) 2018-02-28
TW201500518A (en) 2015-01-01
JP2016524333A (en) 2016-08-12
TWI640599B (en) 2018-11-11

Similar Documents

Publication Publication Date Title
JP6286033B2 (en) Phosphorescent organic light-emitting device having a hole-transporting host in the light-emitting region
US9705099B2 (en) Phosphorescent organic light emitting devices having a hole transporting cohost material in the emissive region
US9705092B2 (en) Phosphorescent organic light emitting devices combined with hole transport material having high operating stability
KR102776293B1 (en) Novel compound and organic electroluminescent device comprising same
JP6076949B2 (en) New materials with aza-dibenzothiophene or aza-dibenzofuran nuclei for PHOLED
CN104768940B (en) organic electroluminescent element
CN103959503B (en) Material for organic electroluminescence element and organic electroluminescence element
EP2541635B1 (en) Organic electroluminescent element
KR20240149861A (en) Novel compound and organic electroluminescent device comprising same
KR102559622B1 (en) Novel compound and organic electroluminescent device comprising same
KR101682844B1 (en) Nitrogen-containing heterocyclic derivative, organic electroluminescence element material using same, and organic electroluminescence element and electronic device using same
CN105408310B (en) Carbazole derivative, material for organic electroluminescent element using same, and organic electroluminescent element and electronic device using same
WO2014024880A1 (en) Organic electroluminescent element and electronic apparatus
CN103313980A (en) Biscarbazole derivative and organic electroluminescent element using same
KR102671576B1 (en) Novel compound and organic electroluminescent device comprising same
WO2023093094A1 (en) Organic electroluminescent device and display apparatus
JP5669539B2 (en) Quinolino [3,2,1-kl] phenoxazine compound and organic light emitting device using the same
CN104918915A (en) Compound, material for organic electroluminescent element, and electronic device
CN105593216B (en) Compound, material for organic electroluminescent element using same, organic electroluminescent element and electronic device using same
KR20230121083A (en) Organic electroluminescent device and manufacturing method thereof
CN109928974B (en) Organic compound and application thereof in organic electroluminescent device
KR20200095709A (en) Organic Light Emitting Material and Organic Light Emitting Diode Having The Same
KR20230129396A (en) Organic electroluminescent device and method of manufacturing the same
CN115594597A (en) Organic compound and organic electroluminescent device comprising same
CN112300052A (en) A compound and its application, organic electroluminescent device comprising the same

Legal Events

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

Ref document number: 13887132

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2016521385

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 13887132

Country of ref document: EP

Kind code of ref document: A1