WO2012056919A1 - SPIRO[CYCLOPENTA[def]TRIPHENYLENE-4,9'-FLUORENE] COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE HAVING THE SAME - Google Patents
SPIRO[CYCLOPENTA[def]TRIPHENYLENE-4,9'-FLUORENE] COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE HAVING THE SAME Download PDFInfo
- Publication number
- WO2012056919A1 WO2012056919A1 PCT/JP2011/073772 JP2011073772W WO2012056919A1 WO 2012056919 A1 WO2012056919 A1 WO 2012056919A1 JP 2011073772 W JP2011073772 W JP 2011073772W WO 2012056919 A1 WO2012056919 A1 WO 2012056919A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- groups
- compound
- triphenylene
- emitting device
- organic light
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/72—Spiro hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting 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
- H10K85/60—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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/94—Spiro compounds containing "free" spiro atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting 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
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—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
Definitions
- the present invention relates to
- An organic light-emitting device includes an anode, a cathode, and an organic compound layer disposed between the electrodes.
- holes and electrons that are injected to the organic compound layer from the anode and the cathode, respectively, are recombined to generate excitons, and light is emitted when the excitons return to the ground state.
- the organic light- emitting device has remarkably progressed recently, and it is possible to provide light-emitting devices that are driven with low voltages, emit various emission wavelengths, and are rapidly responsive, thin, and lightweight.
- a phosphorescent device is an organic light- emitting device that includes a phosphorescent material in the organic compound layer and emits light due to the triplet excitons, and there is a demand for further improvement in luminous efficiency of the phosphorescent device .
- PTL 1 describes Compound H01
- PTL 2 describes Compound H02
- PTL 3 describes Compound H03. These compounds are shown below. Note that the terms HOI to H03 are names given in this description .
- the compounds disclosed in PTLs 1 and 2 have 9,9'- spirobi [ fluorene] as the basic skeletons, and, therefore, the difference between the triplet energy (Tl energy) level and the singlet energy (SI energy) level is large. Accordingly, the driving voltages of phosphorescent devices produced using these compounds as raw materials are high. Meanwhile, the compound disclosed in PTL 3 includes a triphenylene group having high planarity and thereby shows high crystallinity, resulting in low film-forming property.
- the present invention provides a
- the present invention further provides an organic light-emitting device that includes the compound and has a high luminous
- the present invention provides
- Rj to R 8 are independently selected from the group consisting of hydrogen atoms, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthryl groups, triphenylene groups, fluorenyl groups, dibenzothiophene groups, carbonyl groups, amino groups, and spiro [cyclopenta [def ] triphenylene-4 , 9 ' -fluorene] groups .
- the phenyl groups, the biphenyl groups, the terphenyl groups, the naphthyl groups, the phenanthryl groups, the triphenylene groups, the fluorenyl groups, the dibenzothiophene groups, the carbonyl groups, the amino groups, and the spiro [cyclopenta [def ] triphenylene-4 , 9 ' - fluorene] groups may optionally have substituents selected from alkyl groups, phenyl groups, carbonyl groups having phenyl groups, substituted amino groups, and
- new compounds having small differences between the triplet and singlet energy levels and high glass transition temperatures can be provided.
- organic light-emitting devices having high luminous efficiencies and low driving voltages can be provided by using the compounds.
- Fig. 1 is a schematic diagram illustrating
- Fig. 2 is a schematic cross-sectional view illustrating organic light-emitting devices and switching devices
- spiro [cyclopenta [def] triphenylene-4 , 9 ' -fluorene] compounds may be also referred to as compounds according to the present invention.
- the present invention relates to
- Ri to Re are independently selected from the group consisting of hydrogen atoms, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, phenanthryl groups, triphenylene groups, fluorenyl groups, dibenzothiophene groups, carbonyl groups, amino groups, and spiro [cyclopenta [def] triphenylene- , 9 ' -fluorene] groups .
- the above-mentioned substituents may further have substituents .
- the optional substituents include alkyl groups such as a methyl group, an ethyl group, and a butyl group; hydrocarbon aromatic ring groups such as a phenyl group, a naphthyl group, a phenanthryl group, and a 9, 9-dimethylfluorenyl group; heteroaromatic ring groups such as a thienyl group, a pyrrolyl group, a pyridyl group, and a dibenzothiophene group; substituted amino groups such as a dimethylamino group, a diethylamino group, a dibenzylamino group, a diphenylamino group, a ditolylamino group, and a dianisolylamino group; carbonyl groups having phenyl groups; alkoxy groups such as a methoxy group and an ethoxy group
- an alkyl group having 1 to 4 carbon atoms having 1 to 4 carbon atoms, a substituted amino group, a dibenzothiophene group, a
- the basic skeleton of compounds according to the present invention has a small difference between the singlet energy (SI energy) level and the triplet energy (Tl energy) level and a high glass transition temperature.
- SI energy singlet energy
- Tl energy triplet energy
- the basic skeleton is that shown as skeleton of the invention in the following Table 1.
- Table 1 shows SI energy, Tl energy, differences between the SI and Tl energy levels, and glass transition temperatures of the basic skeleton of compounds according to the present invention, triphenylene, 9, 9 ' -spirobi [fluorene] , and fluorene.
- the materials used for organic light- emitting devices can be compounds having small SI energy levels. This is because the driving voltage is low when the SI energy of the material is low.
- phosphorescent devices emit light using the Tl energy.
- the Tl energy level necessary for phosphorescence depends on the emission color.
- the SI energy is required to be lowered while a necessary Tl energy level being maintained, i.e., a small difference between the SI and Tl energy levels is required.
- the basic skeleton of compounds according to the present invention and triphenylene have high Tl energy levels and small differences between the SI and Tl energy levels and can be therefore used as materials of
- the basic skeleton of compounds according to the present invention has a glass transition temperature of
- high film-forming property means that an amorphous state can be maintained without causing crystallization even at high temperature.
- An example of measured value for the film-forming property is a glass transition temperature.
- a compound having a high glass transition temperature has a high film-forming
- a low film-forming property may have high
- triphenylene has high planarity and is thereby high in crystallinity and that the glass transition temperature cannot be detected.
- the basic skeleton of compounds according to the present invention has a spiro structure that exhibits high steric hindrance against triphenylene, which suppresses planarity to show low crystallinity. That is, the film- forming property is high.
- the molecular weight can be increased without changing the SI and Tl energy levels.
- a larger molecular weight can reduce crystallinity.
- the basic skeleton of compounds according to the present invention can simultaneously solve both a problem of high crystallinity of triphenylene and a problem of large difference between the Si and Tl energy levels of 9,9'- spirobi [fluorene] .
- One characteristic of the basic skeleton of compounds according to the present invention is a high triplet energy level.
- the triplet energy is obtained at 431 nm, which is a level higher than the blue region (440 to 480 nm) .
- Tl energy levels of substituents that bind to Ri to R 8 in General Formula [1] are paid attention to.
- Table 2 shows Tl energy levels (wavelength equivalents) of aryl groups and condensed polycyclic groups. These substituents have Tl energy levels higher than the blue region (440 to 480 nm) and can be applied to a region from blue to red (440 to 620 nm) in a combination thereof .
- a substituent can be located at a position to which ⁇ - conjugated system is hardly connected, that is, at least either the position 1 or 2 in Fig. 1.
- a high film-forming property can be achieved, without reducing the SI and Tl energy levels, by introducing a substituent into the substitution position 1 or 2.
- a substituent having ⁇ -conjugation such as an aryl group, can be located at a position to which ⁇ -conjugated system is connected, that is, the position 3 or 4 of the fluorene group or the position 5 or 6 of the triphenylene group in Fig. 1.
- the Tl energy level can be high.
- a single molecule can have two
- the substituent in order to keep the Tl energy level high, the substituent can be introduced into the
- positions 1 and 2 may have substituents.
- substitution positions 5 to 8 can add steric hindrance of the substituent itself to the triphenylene group, in
- the compounds according to the present invention can have reduced crystallinity compared to triphenylene and thereby have high film-forming properties.
- the compounds according to the present invention can be used as the host materials of the electron- transporting layers, the hole-transporting layers, or the light-emitting layers of phosphorescent devices in a broad emission color range.
- the compounds can be used as the host materials of light-emitting layers.
- the host material of a light-emitting layer is a compound of which weight ratio is the highest in the compounds constituting the light-emitting layer.
- the guest material is a compound of which weight ratio is less than that of the host material in the
- the assist material is a compound of which weight ratio is less than that of the host material in the compounds constituting the light- emitting layer and assists the light emission of the guest material .
- the compound according to the present invention that is used as the host material of the electron- transporting layer, the hole-transporting layer, or the light-emitting layer of an organic light-emitting device can have appropriate SI and Tl energy levels in light of
- the compound according to the present invention can change HOMO-LU O levels by appropriately selecting the substituent.
- deep HOMO-LUMO levels can be obtained by introducing a carbonyl group.
- the compounds according to the present invention have high film-forming properties and high Tl energy levels.
- Example Compound A03 has a substituent showing a large steric hindrance, and thereby the basic skeleton can have further reduced crystallinity.
- the ⁇ - conjugated system is disconnected by the spiro bond, the characteristics of triphenylene, the high Tl energy level and the small difference between the SI and Tl energy levels, can be maintained. That is, the substituent can provide a new function while maintaining the characteristics of the triphenylene group.
- Compounds have substituents on the triphenylene side and are thereby provided with steric hindrance of the substituent itself, in addition to the steric hindrance of the spiro structure .
- the crystallinity can be reduced compared to unsubstituted triphenylene.
- the ⁇ -conjugated system is disconnected by the spiro bond, and thereby the substituent can provide a new function while maintaining the characteristics of the triphenylene group.
- a temperature of the basic skeleton of compounds according to the present invention is high, 120 °C, a compound having two basic skeletons also has a high glass transition temperature. That is, a material having a high film-forming property can be provided.
- R 8 is any of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, a fluorenyl group, a dibenzothiophene group, a carbonyl group, an amino group, or a spiro [cyclopenta [def] triphenylene-4 , 9 ' -fluorene] group.
- R & can be a biphenyl group.
- substituents may have substituents selected from alkyl groups having 1 to 4 carbon atoms, substituted amino groups, dibenzothiophene groups, carbonyl groups having phenyl groups, and spiro [cyclopenta [def] triphenylene- 4 , 9 ' -fluorene] groups.
- the compound according to the present invention is synthesized as in the above-mentioned synthesis example by forming a spiro bond between a bromobiphenyl derivative and a bromofluorenone derivative, then binding a
- Ri to R 8 are independently selected from the group consisting of hydrogen atoms, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups,
- phenanthryl groups triphenylene groups, fluorenyl groups, dibenzothiophene groups, carbonyl groups, and amino groups.
- a desired compound of the present invention can be synthesized by appropriately selecting a bromobiphenyl derivative, a bromofluorenone derivative, and an
- the organic compound used in the organic light-emitting device can have a molecular weight of 1000 or less so that sublimation purification can be
- the organic light-emitting device includes at least an anode and a cathode, as an example of a pair of electrodes facing each other, and an organic compound layer disposed between thereof.
- the organic compound layer includes a light-emitting material
- the layer serves as a light-emitting layer.
- the organic light-emitting device according to this embodiment includes a spiro [cyclopenta [def] triphenylene-4 , 9 1 -fluorene] compound represented by General Formula [1] in the organic compound layer .
- the organic compound layer of the organic light- emitting device according to the embodiment may be a
- the multilayer is a layer
- a hole-injecting layer including those appropriately selected from, for example, a hole-injecting layer, a hole-transporting layer, a light- emitting layer, a hole-blocking layer, an electron- transporting layer, an electron-in ecting layer, and an exciton-blocking layer.
- a plurality of layers selected from the above-mentioned layers may be used in combination.
- the structure of the organic light-emitting device according to the embodiment is not limited to the above- mentioned ones, and various layer structures can be employed.
- a structure having an insulating layer at the interface between an organic compound layer and an electrode, a structure having an adhesion layer or an interference layer, or a structure having an electron-transporting layer or a hole-transporting layer constituted of two layers having different ionization potentials can be employed.
- the configuration of the device may be a top emission type, which extracts light from the electrode on the substrate side, or a bottom emission type, which
- the compound according to the present invention can be used in any layer structure as the organic compound layer of an organic light-emitting device and, in particular, can be used as the host material of a light-emitting layer.
- the concentration of the host material of a light- emitting layer can be 50 wt% or more and 99.9 wt% or less, preferably 80 wt% or more and 99.9 wt% or less, based on the total weight of the light-emitting layer.
- the concentration of the guest material can be 0.01 wt% or more and 10 wt% or less in order to avoid concentration quenching.
- the guest material may be uniformly contained in the entire layer of a host material or may be contained with concentration gradient or may be contained in a specific region of a host material layer so that the host material layer has a region not containing the guest material.
- the phosphorescent material used as the guest may be uniformly contained in the entire layer of a host material or may be contained with concentration gradient or may be contained in a specific region of a host material layer so that the host material layer has a region not containing the guest material.
- the material is a metal complex such as an iridium complex, a platinum complex, a rhenium complex, a copper complex, a europium complex, or a ruthenium complex.
- the iridium complex which has a strong phosphorescent property, can be used.
- the light-emitting layer may include a plurality of phosphorescent materials in order to assist transmission of excitons or carriers.
- known low-molecular-weight and high- molecular-weight compounds can be optionally used. More specifically, for example, a hole-injecting compound, a hole-transporting compound, a host material, a light- emitting compound, an electron-injecting compound, or an electron-transporting compound can be used together with the compound of the present invention.
- the hole-injection/transporting material can be a material having a high hole mobility to facilitate the injection of holes from an anode and to transport the
- low-molecular-weight and high-molecular-weight compounds having the hole-injection/transporting ability include triarylamine derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly (vinylcarbazole) , poly (thiophene) , and other electrically conductive polymers.
- Examples of the light-emitting material mainly relating to the emission function include, in addition to the above-mentioned phosphorescent guest materials and
- condensation compounds e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, and rubrene derivatives
- quinacridone derivatives e.g., quinacridone derivatives, coumarin derivatives, stilbene derivatives, organic aluminum complexes such as tris(8- quinolinolato) aluminum, organic beryllium complexes, and polymer derivatives such as poly ( fluorene ) derivatives and poly (phenylene) derivatives.
- the electron injection/transporting material can be appropriately selected from those that facilitate the
- the material having the electron injection/transporting ability include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine
- anode material a material having a large work function can be used. Examples of such materials
- metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten; alloys of these metals; metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide; and electrically conductive polymers such as
- the anode may have either a monolayer or multilayer structure.
- the cathode material a material having a small work function can be used.
- examples of such materials include alkali metals such as lithium; alkaline earth metals such as calcium; simple metals such as aluminum, titanium, manganese, silver, lead, and chromium; alloys of these simple metals such as magnesium-silver, aluminum- lithium, and aluminum-magnesium; and metal oxides such as indium tin oxide (ITO).
- ITO indium tin oxide
- the cathode may have either a monolayer or multilayer structure.
- compound according to the present invention and a layer of another organic compound are thin films generally formed by vacuum deposition, ionic vapor deposition, sputtering, plasma CVD, or a known method of applying the compound dissolved in a suitable solvent (e.g., spin coating, dipping, casting, LB method, ink jet method). Particularly, in the layer formed by vacuum deposition or application of a suitable solvent (e.g., spin coating, dipping, casting, LB method, ink jet method). Particularly, in the layer formed by vacuum deposition or application of a suitable solvent (e.g., spin coating, dipping, casting, LB method, ink jet method).
- a suitable solvent e.g., spin coating, dipping, casting, LB method, ink jet method
- the solution for example, crystallization hardly occurs to achieve high long-term stability.
- the solution may additionally contain a suitable binder resin.
- binder resin examples include, but not limited to, polyvinylcarbazole resins, polycarbonate resins, polyester resins, ABS resins, acrylic resins, polyimide resins, phenol resins, epoxy resins, silicone resins, and urea resins. These binder resins may be singly used as a homopolymer or a copolymer or as a mixture of two or more of polymers. Furthermore, an additive such as a known
- plasticizer, antioxidant, or ultraviolet absorber may be optionally used.
- the organic light-emitting device according to the present invention can be applied not only to a display or a lighting system, but also to an exposing light source of an electrographic image-forming apparatus or a backlight of a liquid crystal display.
- the display includes the organic light-emitting device according to the embodiment in a display section.
- This display section includes a plurality of pixels.
- the pixel includes an organic light-emitting device according to the embodiment and a TFT device as an example of the
- the display can be used as an image- displaying apparatus of, for example, a personal computer.
- the display may be an image input apparatus that further includes an input section for inputting image information from, for example, an area CCD, a linear CCD, or memory card and outputs the input image to the display section.
- the display section of an image pickup apparatus or an ink-jet printer may have both an image output function for displaying image information input from the outside and an input function for inputting information processed into an image as an operation panel.
- the display may be used in a display section of a multi-functional printer.
- Fig. 2 is a schematic cross-sectional view of a display, illustrating organic light-emitting devices
- TFT devices as an example of the switching devices connected to the organic light- emitting devices.
- This figure shows two pairs of the organic light-emitting device and the TFT device. The details of the structure will be described below.
- This display includes a substrate 1 such as a glass substrate and a moisture-proof film 2 disposed on the substrate 1 for protecting the TFT devices or the organic composition layer.
- Reference numeral 3 denotes a metal gate electrode
- reference numeral 4 denotes a gate insulating film 4
- reference numeral 5 denotes a semiconductor layer .
- the TFT device 8 includes a semiconductor layer 5, a drain electrode 6, and a source electrode 7.
- the insulating film 9 is disposed on the TFT device 8.
- the anode 11 of the organic light-emitting device and the source electrode 7 are connected via a contact hole 10.
- the display is not limited this configuration as long as either the anode or the cathode is connected to either the source electrode or the drain electrode of the TFT device.
- the organic compound layer 12 of a multilayer is shown as one layer. Furthermore, a first protective layer 14 and a second protective layer 15 are disposed on the cathode 13 in order to inhibit deterioration of the organic light-emitting device.
- the switching device of the display according to the embodiment is not particularly limited and may be a monocrystal silicon substrate, an MIM device, or an a-Si type device.
- a Grignard reagent was prepared by putting 1.5 g (61.8 mmol) of magnesium in a reaction vessel, replacing the atmosphere inside the reaction vessel with argon, and then dropping 11.7 g (50.2 mmol) of 2-bromobiphenyl dissolved in 55 mL of dehydrated diethyl ether into the reaction vessel with stirring.
- reaction solution was cooled to 0°C and was subjected to extraction with a saturated ammonium chloride aqueous solution and ethyl acetate, and the organic layer was collected. After drying with sodium sulfate, the solvent was distilled off to obtain an intermediate of Compound 01.
- tripotassium phosphate 400 mg (0.472 mmol), bisdibenzylideneacetone palladium: 27.0 mg (0.0471 mmol) , and
- ALDI-TOF MS matrix-assisted laser desorption/ionization time-of-flight mass spectrometry
- dichloromethane 60 mL were put in a reaction vessel. This reaction solution was cooled to 0°C, followed by dropping of 3.40 mL (3.40 mmol) of a dichloromethane solution of boron tribromide (1 mol/L) .
- GS-MS chromatography-mass spectrometer
- reaction solution was stirred at 100°C for 12 hr under a nitrogen atmosphere. It was confirmed by thin layer chromatography that the raw materials disappeared, and instead, a new compound was produced. The reaction solution was cooled to room
- tripotassium phosphate 411 mg (1.94 mmol), and
- tetrakistriphenylphosphine palladium 55.9 mg (0.0484 mmol) were put in a reaction vessel. This reaction solution was stirred at 90 °C for 12 hr under a nitrogen atmosphere. It was confirmed by thin layer chromatography that the raw materials disappeared, and instead, a new compound was produced. The reaction solution was cooled to room
- reaction solution wa stirred at 110 °C for 12 hr under a nitrogen atmosphere. was confirmed by thin layer chromatography that the raw materials disappeared, and instead, a new compound was produced.
- Example Compound B22 was measured for triplet energy by the following method. The phosphorescence
- the triplet energy level determined from the peak wavelength on the shortest wavelength side in the resulting phosphorescence spectrum was 2.66 eV (467 nm) .
- Example Compound B22 was measured for singlet energy by the following method.
- the absorption spectrum of a diluted solution of the compound in dichloromethane was measured using an ultraviolet and visible spectrophotometer (manufactured by JASCO Corp., V-560).
- the singlet energy level determined from the absorption edge of the resulting absorption spectrum was 3.42 eV (363 nm) .
- Compound B22 was further measured using a differential scanning calorimeter (manufactured by NETZSCH GmbH,
- Example Compound D01 was subjected to the same measurements as in Example Compound of Example 5 to give a single energy level of 3.42 eV (363 nm) , a triplet energy level of 2.64 eV (470 nm) , a difference between the singlet and triplet energy levels of 0.78 eV, and a glass transition temperature of 256°C.
- Comparative Compound 01 Comparative Compound 01 was subjected to the same measurements as in Example Compound of Example 5 to give a glass transition temperature of 108°C.
- Example Compound DOl The difference between the singlet and triplet energy levels was 0.78 eV in Example Compound DOl and was 0.76 eV in Example Compound B22. These values are similar to the value, 0.64 eV, of the basic skeleton of the present invention .
- Example Compound DOl having two basic skeletons of compounds according to the present invention was 256°C.
- glass transition temperature was increased with an increase in number of the basic skeletons of
- Comparative Compound 01 which was different from Example Compound B22 in that the basic skeleton was triphenylene, was 108°C.
- an organic light-emitting device having a configuration of anode/hole-transporting
- a film of ITO was formed on a glass substrate by sputtering as an anode having a thickness of 120 nm, and the resulting product was used as a transparent electrically conductive support substrate (ITO substrate) .
- ITO substrate transparent electrically conductive support substrate
- an organic compound layers and electrode layers shown below were successively formed by resistance heating vacuum vapor deposition in a vacuum chamber of 10 ⁇ 5 Pa. On this occasion, the area of electrodes facing each other was adjusted to be 3 mm 2 .
- the layers were: hole-transporting layer (40 nm) : HTL-1,
- Example Compound B22 70 wt%), HBL-1 (20 wt%), and Ir-1 (10 wt%),
- hole-blocking layer (10 nm) HBL-1,
- metal electrode layer 1 (0.5 nm) : LiF
- metal electrode layer 2 (100 nm) : Al .
- a light-emitting device was produced in the same manner as the method of Example 7 using the following materials :
- hole-transporting layer (40 nm) HTL-1
- hole-blocking layer (10 nm) HBL-1,
- metal electrode layer 1 (0.5 nm) : LiF
- metal electrode layer 2 (100 nm) : Al .
- a voltage of 5.2 V was applied to the resulting device to observe green light emission with a luminous efficiency of 58 cd/A and a luminance of 4000 cd/m 2 .
- a light-emitting device was produced in the same manner as the method of Example 7 using the following materials :
- hole-transporting layer (40 nm) HTL-1
- hole-blocking layer (10 nm) Example Compound A09, electron-transporting layer (30 nm) : ETL-1,
- metal electrode layer 1 (0.5 nm) : LiF
- metal electrode layer 2 (100 nm) : Al .
- a voltage of 5.8 V was applied to the resulting device to observe green light emission with a luminous efficiency of 70 cd/A and a luminance of 4000 cd/m 2 .
- a light-emitting device was produced in the same manner as the method of Example 7 using the following materials :
- hole-transporting layer (40 nm) Example Compound A10, light-emitting layer (30 nm) : HOST-1 (70 wt%), HBL-1 (20 wt%) , and Ir-1 (10 wt%) ,
- hole-blocking layer (10 nm) HBL-1,
- metal electrode layer 1 (0.5 nm) : LiF
- metal electrode layer 2 (100 nm) : Al .
- a voltage of 5.7 V was applied to the resulting device to observe green light emission with a luminous efficiency of 68 cd/A and a luminance of 4000 cd/m 2 .
- a light-emitting device was produced in the same manner as the method of Example 7 using the following materials :
- hole-transporting layer (40 nm) HTL-1
- HOST-1 70 wt%)
- HBL-1 20 wt%)
- Ir-1 10 wt%)
- hole-blocking layer (10 nm) HBL-1,
- metal electrode layer 1 (0.5 nm) : LiF
- metal electrode layer 2 (100 nm) : Al .
- a voltage of 6.0 V was applied to the resulting device to observe green light emission with a luminous efficiency of 57 cd/A and a luminance of 4000 cd/m 2 .
- a light-emitting device was produced in the same manner as the method of Example 7 using the following materials :
- hole-transporting layer (40 nm) HTL-1
- HOST-2 70 wt%)
- HBL-1 20 wt%)
- Ir-1 10 wt%)
- hole-blocking layer (10 nm) HBL-1,
- metal electrode layer 1 (0.5 nm) : LiF
- metal electrode layer 2 (100 nm) : Al .
- the light- emitting layer host is the component having the largest weight ratio in the light-emitting layer.
- the compounds of the present invention are materials having small differences between the singlet and triplet energy levels and showing high glass transition temperatures.
- Organic light-emitting devices including the compounds can have low driving voltages and high luminous efficiencies.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Manufacturing & Machinery (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/881,359 US9991450B2 (en) | 2010-10-27 | 2011-10-11 | Spiro[cyclopenta[def]triphenylene-4,9′-fluorene] compound and organic light-emitting device having the same |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010241203 | 2010-10-27 | ||
| JP2010-241203 | 2010-10-27 | ||
| JP2011159077A JP5901167B2 (ja) | 2010-10-27 | 2011-07-20 | スピロ[シクロペンタ[def]トリフェニレン−4,9’−フルオレン]化合物及びそれを有する有機発光素子 |
| JP2011-159077 | 2011-07-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2012056919A1 true WO2012056919A1 (en) | 2012-05-03 |
Family
ID=45993636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2011/073772 Ceased WO2012056919A1 (en) | 2010-10-27 | 2011-10-11 | SPIRO[CYCLOPENTA[def]TRIPHENYLENE-4,9'-FLUORENE] COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE HAVING THE SAME |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US9991450B2 (enExample) |
| JP (1) | JP5901167B2 (enExample) |
| WO (1) | WO2012056919A1 (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105503518A (zh) * | 2014-10-14 | 2016-04-20 | 上海华显新材料科技有限公司 | 高纯度2-溴三亚苯的制备方法 |
| KR20170095602A (ko) * | 2016-02-15 | 2017-08-23 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
| CN107141191A (zh) * | 2017-06-27 | 2017-09-08 | 维思普新材料(苏州)有限公司 | 螺双芴衍生物及其在有机电致发光领域中的应用 |
| US9831437B2 (en) * | 2013-08-20 | 2017-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN107698605A (zh) * | 2017-10-30 | 2018-02-16 | 宁波博润新材料科技有限公司 | 含4,4’‑二(甲氧基苯基)氨基的噻吩螺环类化合物及其衍生物和应用 |
| KR20190098438A (ko) * | 2018-02-14 | 2019-08-22 | 주식회사 엘지화학 | 아민 유도체 및 이를 포함하는 유기 발광 소자 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102098740B1 (ko) * | 2012-07-11 | 2020-04-09 | 삼성디스플레이 주식회사 | 전자 주입 능력 및/또는 전자 수송 능력을 가지는 신규한 화합물 및 이를 포함한 유기 발광 소자 |
| KR102643057B1 (ko) * | 2016-10-26 | 2024-03-04 | 솔루스첨단소재 주식회사 | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 |
| JP7002925B2 (ja) * | 2017-11-13 | 2022-01-20 | 東ソー株式会社 | ジナフトテトラフェニレン化合物を含む有機エレクトロルミネッセンス素子 |
| CN112534600B (zh) * | 2018-09-28 | 2024-03-05 | 株式会社Lg化学 | 有机电致发光器件 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007332139A (ja) * | 2006-06-15 | 2007-12-27 | Samsung Sdi Co Ltd | シクロペンタフェナントレン系化合物及びそれを利用した有機電界発光素子 |
| US20090092853A1 (en) * | 2007-10-08 | 2009-04-09 | Sang-Hoon Park | Cyclopentaphenanthrene-based compound and organic light emitting device employing the same |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5026894A (en) | 1990-03-12 | 1991-06-25 | University Of South Carolina | Compound for use in the synthesis of semiconducting polymers with perpendicularly arranged cores and method of synthesizing said compound |
| EP0676461B1 (de) * | 1994-04-07 | 2002-08-14 | Covion Organic Semiconductors GmbH | Spiroverbindungen und ihre Verwendung als Elektrolumineszenzmaterialien |
| WO2000027946A1 (en) * | 1998-11-11 | 2000-05-18 | Kabushiki Kaisha Toyota Chuo Kenkyusho | Organic electroluminescent element |
| JP3141023B2 (ja) | 1999-12-10 | 2001-03-05 | キヤノン株式会社 | 電界発光素子 |
| US6939624B2 (en) * | 2000-08-11 | 2005-09-06 | Universal Display Corporation | Organometallic compounds and emission-shifting organic electrophosphorescence |
| JP4554047B2 (ja) * | 2000-08-29 | 2010-09-29 | 株式会社半導体エネルギー研究所 | 発光装置 |
| TWI314947B (en) * | 2002-04-24 | 2009-09-21 | Eastman Kodak Compan | Organic light emitting diode devices with improved operational stability |
| KR100718104B1 (ko) * | 2004-01-15 | 2007-05-14 | 삼성에스디아이 주식회사 | 스피로사이클로펜타페난트렌플루오렌계 화합물 및 이를이용한 유기 전계 발광 소자 |
| US20060088728A1 (en) * | 2004-10-22 | 2006-04-27 | Raymond Kwong | Arylcarbazoles as hosts in PHOLEDs |
| JP2006150707A (ja) * | 2004-11-29 | 2006-06-15 | Seiko Epson Corp | 透明基板、電気光学装置、画像形成装置及び電気光学装置の製造方法 |
| KR101209289B1 (ko) * | 2005-04-07 | 2012-12-10 | 삼성디스플레이 주식회사 | 표시 패널과, 이를 구비한 표시 장치 및 구동 방법 |
| EP1888708B1 (en) * | 2005-05-31 | 2012-11-21 | Universal Display Corporation | Triphenylene hosts in phosphorescent light emitting diodes |
| US8779655B2 (en) * | 2007-07-07 | 2014-07-15 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
| JP5825846B2 (ja) * | 2010-09-13 | 2015-12-02 | キヤノン株式会社 | 新規縮合多環化合物およびそれを有する有機発光素子 |
-
2011
- 2011-07-20 JP JP2011159077A patent/JP5901167B2/ja active Active
- 2011-10-11 WO PCT/JP2011/073772 patent/WO2012056919A1/en not_active Ceased
- 2011-10-11 US US13/881,359 patent/US9991450B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007332139A (ja) * | 2006-06-15 | 2007-12-27 | Samsung Sdi Co Ltd | シクロペンタフェナントレン系化合物及びそれを利用した有機電界発光素子 |
| US20090092853A1 (en) * | 2007-10-08 | 2009-04-09 | Sang-Hoon Park | Cyclopentaphenanthrene-based compound and organic light emitting device employing the same |
Non-Patent Citations (1)
| Title |
|---|
| POLYMER, vol. 49, no. 26, 2008, pages 5643 - 5649 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9831437B2 (en) * | 2013-08-20 | 2017-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN105503518A (zh) * | 2014-10-14 | 2016-04-20 | 上海华显新材料科技有限公司 | 高纯度2-溴三亚苯的制备方法 |
| KR20170095602A (ko) * | 2016-02-15 | 2017-08-23 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
| KR102620119B1 (ko) | 2016-02-15 | 2024-01-03 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
| CN107141191A (zh) * | 2017-06-27 | 2017-09-08 | 维思普新材料(苏州)有限公司 | 螺双芴衍生物及其在有机电致发光领域中的应用 |
| CN107141191B (zh) * | 2017-06-27 | 2021-03-19 | 维思普新材料(苏州)有限公司 | 螺双芴衍生物及其在有机电致发光领域中的应用 |
| CN107698605A (zh) * | 2017-10-30 | 2018-02-16 | 宁波博润新材料科技有限公司 | 含4,4’‑二(甲氧基苯基)氨基的噻吩螺环类化合物及其衍生物和应用 |
| KR20190098438A (ko) * | 2018-02-14 | 2019-08-22 | 주식회사 엘지화학 | 아민 유도체 및 이를 포함하는 유기 발광 소자 |
| KR102230994B1 (ko) | 2018-02-14 | 2021-03-22 | 주식회사 엘지화학 | 아민 유도체 및 이를 포함하는 유기 발광 소자 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20130214267A1 (en) | 2013-08-22 |
| US9991450B2 (en) | 2018-06-05 |
| JP2012106979A (ja) | 2012-06-07 |
| JP5901167B2 (ja) | 2016-04-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5618753B2 (ja) | 有機発光素子 | |
| US9991450B2 (en) | Spiro[cyclopenta[def]triphenylene-4,9′-fluorene] compound and organic light-emitting device having the same | |
| KR101463705B1 (ko) | 크산톤 화합물, 이를 포함하는 유기 발광 디바이스, 디스플레이 장치, 화상 입력 장치 및 조명 장치 | |
| KR101489613B1 (ko) | 인돌로페녹사진 화합물 및 이를 사용한 유기 발광 디바이스 | |
| KR101041867B1 (ko) | 바이나프틸 화합물 및 이것을 사용한 유기발광소자 | |
| US20110198582A1 (en) | Organic light-emitting device | |
| JP5574860B2 (ja) | ジベンゾスベロン骨格を有する有機発光素子用材料 | |
| WO2013058137A1 (en) | Novel organic compound and organic light-emitting device | |
| US20120235888A1 (en) | NEW BENZO[c]PHENANTHRENE COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE CONTAINING SAME | |
| KR20130024915A (ko) | 신규 m-터페닐 화합물 및 이를 포함하는 유기 발광 소자 | |
| US20130299811A1 (en) | Dibenzothiophene dioxide compound and organic light-emitting device using the same | |
| US8729541B2 (en) | Phenanthrene compound and organic light emitting device using the same | |
| WO2011102102A1 (en) | Novel organic compound and organic light-emitting device | |
| WO2013077142A1 (en) | Novel organic compound and organic light-emitting device including the same | |
| JP2012092047A (ja) | ピラゾロインドール化合物及びこれを用いた有機発光素子 | |
| JP5656438B2 (ja) | 新規ベンゾ[b]クリセン化合物及びこれを有する有機発光素子 | |
| JP2010132651A (ja) | ジベンゾ[c,g]フルオレン化合物及びこれを使用した有機発光素子 |
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: 11836056 Country of ref document: EP Kind code of ref document: A1 |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 13881359 Country of ref document: US |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 11836056 Country of ref document: EP Kind code of ref document: A1 |