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WO2012014779A1 - Elément électroluminescent organique, et composé associé - Google Patents

Elément électroluminescent organique, et composé associé Download PDF

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WO2012014779A1
WO2012014779A1 PCT/JP2011/066579 JP2011066579W WO2012014779A1 WO 2012014779 A1 WO2012014779 A1 WO 2012014779A1 JP 2011066579 W JP2011066579 W JP 2011066579W WO 2012014779 A1 WO2012014779 A1 WO 2012014779A1
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渡辺　康介
外山　弥
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Fujifilm Corp
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    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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    • 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
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H05B33/00—Electroluminescent light sources
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    • 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
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    • H10K59/875—Arrangements for extracting light from the devices
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    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the present invention relates to an organic electroluminescent device and a compound used for the device.
  • Organic electroluminescent elements (hereinafter also referred to as “elements” and “organic EL elements”) are actively researched and developed because they can emit light with high luminance when driven at a low voltage.
  • An organic electroluminescent element has an organic layer between a pair of electrodes, and electrons injected from the cathode and holes injected from the anode recombine in the organic layer, and the generated exciton energy is used for light emission. To do.
  • Patent Document 1 discloses that a specific compound having a benzothiophene structure or a benzofuran structure is effective in order to provide an organic EL device having high luminous efficiency, no pixel defects, excellent heat resistance, and a long lifetime.
  • Patent Document 2 discloses an organic electroluminescence device using a compound in which two dibenzothiophenes are linked by a biphenyl group as a charge transport material.
  • Organic electroluminescence devices are required to have excellent luminous efficiency and durability, and can be driven at a low voltage, and in conventional devices, luminous efficiency decreases when stored at high temperatures. It becomes clear that there is a problem, and there is a demand for an element whose characteristics do not change even after high-temperature storage, particularly in in-vehicle applications. All the devices using the compounds reported so far have problems such as low luminous efficiency, large change in chromaticity and low durability when driven after storage at 100 ° C. for 72 hours. . Even in the conventional elements described in Patent Documents 1 and 2, it becomes clear that there is a problem that the luminous efficiency decreases when stored at a high temperature, the chromaticity changes greatly, and the durability deteriorates. Improvements were sought.
  • Patent Documents 1 and 2 do not specifically disclose a compound having a structure in which three or more dibenzothiophene structures or dibenzofuran structures are bonded via a linking group.
  • the inventors of the present invention use a compound in which three or more dibenzothiophene structures or dibenzofuran structures are bonded via a linking group, thereby suppressing a decrease in luminous efficiency after storage at high temperature of the device and improving durability.
  • the inventors have found that an organic electroluminescent device satisfying the standards is provided and have completed the invention.
  • Patent Documents 1 and 2 do not describe suppression of a decrease in light emission efficiency after high-temperature storage of the element.
  • an object of the present invention is to provide an organic electroluminescent device that satisfies a high level of high luminous efficiency and durability, suppression of driving voltage, and suppression of decrease in luminous efficiency after high-temperature storage.
  • Another object of the present invention is to provide a compound useful for an organic electroluminescence device as a host material, an electron transporting material, or the like, a composition containing the compound, and a film.
  • another object of the present invention is to provide a light emitting device, a display device, and a lighting device including the organic electroluminescent element of the present invention.
  • the present inventors by using a compound having a specific dibenzothiophene structure or dibenzofuran structure according to the present invention, it has high luminous efficiency, durability, low driving voltage, and reduced luminous efficiency after high-temperature storage. It has been found that an organic electroluminescence device satisfying the above-described suppression at a high level is provided.
  • the high luminous efficiency of the organic electroluminescent device of the present invention is derived from having sufficient triplet energy with respect to the luminescent material. High durability and high luminous efficiency after high temperature storage are improved in thermal stability. It is estimated that the suppression of the driving voltage is derived from the improvement of the charge transport property and / or the electron injection property.
  • An organic electroluminescent device comprising a substrate and a pair of electrodes comprising an anode and a cathode, and at least one organic layer including a light emitting layer between the electrodes, wherein at least one of the at least one organic layer
  • each X independently represents an oxygen atom or a sulfur atom
  • R 111 to R 130 each independently represents a hydrogen atom or a substituent
  • L 1 and L 2 each independently represent Represents a divalent linking group.
  • each X independently represents an oxygen atom or a sulfur atom
  • R 111 and R 130 each independently represent a hydrogen atom or a substituent.
  • R T3 ′, R T3 , R T4 , R T5 and R T6 each independently represent a hydrogen atom or a substituent.
  • R T3 , R T4 , R T5 and R T6 may be any two adjacent to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or hetero It is aryl, and the condensed 4- to 7-membered ring may further have a substituent.
  • Ring Q is a 5- or 6-membered aromatic heterocyclic ring or condensed aromatic heterocyclic ring containing one or more nitrogen atoms.
  • (XY) represents an auxiliary ligand.
  • m represents an integer of 1 to 3.
  • n represents an integer of 0-2.
  • m + n 3.
  • X each independently represents an oxygen atom or a sulfur atom
  • R 111 to R 130 each independently represents a hydrogen atom or a substituent
  • L 1 and L 2 each independently represent 2 Represents a valent linking group.
  • an organic electroluminescence device having high luminous efficiency and durability, low driving voltage, and satisfying suppression of lowering of luminous efficiency after high temperature storage at a high level.
  • a hydrogen atom includes an isotope (deuterium atom and the like), and an atom constituting a substituent further includes the isotope.
  • the substituent when referred to as “substituent”, the substituent may be substituted.
  • the term “alkyl group” in the present invention includes an alkyl group substituted with a fluorine atom (for example, trifluoromethyl group) and an alkyl group substituted with an aryl group (for example, triphenylmethyl group).
  • alkyl group having 1 to 6 carbon atoms it means that all groups including substituted ones have 1 to 6 carbon atoms.
  • the substituent group A is defined as follows.
  • An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl , 3-pentyny
  • An aryloxycarbonyl group (preferably having 7 to 30 carbon atoms) More preferably, it has 7-20 carbon atoms, particularly preferably 7-12 carbon atoms, and examples thereof include phenyloxycarbonyl. ), An acyloxy group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy and benzoyloxy), an alkylthio group (preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio and ethylthio, and arylthio groups (preferably having 6 to 30 carbon atoms, more preferably Has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, and the like, and a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, especially Preferably
  • a sulfinyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl, benzenesulfinyl, etc.), halogen atom (for example, fluorine atom) Chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, sulfino group, imino group, heterocyclic group (including aromatic heterocyclic group, preferably having 1 to 30 carbon atoms, More preferably, it has 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, Atom, selenium atom, tellurium atom, specifically pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyr
  • the organic electroluminescent element of the present invention is an organic electroluminescent element having a pair of electrodes comprising an anode and a cathode and at least one organic layer including a luminescent layer between the electrodes on a substrate, wherein the at least one layer At least one of the organic layers contains a compound represented by the general formula (1).
  • the compound represented by the general formula (1) is a compound having a structure in which dibenzothiophene or dibenzofuran is bonded via a linking group, and the ratio per molecule of the dibenzofuran or dibenzothiophene unit that is a charge transporting unit is increased.
  • the present invention also relates to a compound represented by the general formula (1).
  • the compound represented by the general formula (1) is useful as a charge transport material or a material for an organic electroluminescence device. [Compound represented by the general formula (1)]
  • X each independently represents an oxygen atom or a sulfur atom
  • R 111 to R 130 each independently represents a hydrogen atom or a substituent
  • L 1 and L 2 each independently represent 2 Represents a valent linking group.
  • the general formula (1) does not have a pyrene residue. This is because having a pyrene residue results in a decrease in T 1 energy and a significant decrease in luminous efficiency.
  • the pyrene residue refers to a group obtained by removing an arbitrary hydrogen atom from pyrene.
  • L 1 and L 2 do not form a pyrene ring, and the pyrene ring does not have a substituent.
  • R 111 to R 130 do not have a pyrene ring as a substituent.
  • R 111 to R 130 are not particularly limited, and examples thereof include the substituents exemplified as the substituent group A.
  • R 111 to R 130 are each independently preferably a hydrogen atom, an alkyl group, an aryl group, or a cyano group, more preferably a hydrogen atom, an aryl group, or a cyano group, and a hydrogen atom or an aryl group. More preferably it is.
  • the aryl group is preferable in that it contributes to improvement of heat resistance and charge injection property.
  • the alkyl group represented by R 111 to R 130 is a linear, branched or cyclic alkyl group, preferably an alkyl group having 1 to 18 carbon atoms, more preferably an alkyl group having 1 to 12 carbon atoms. And more preferably an alkyl group having 1 to 6 carbon atoms.
  • the alkyl group represented by R 111 to R 130 is particularly preferably a methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, t-butyl group, i-butyl group, n-pentyl.
  • the aryl group represented by R 111 to R 130 preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms.
  • phenyl, biphenyl group, terphenyl group, p -A methylphenyl group, a naphthyl group, an anthracenyl group, etc. are mentioned, A phenyl group, a biphenyl group, and a terphenyl group are preferable, and a phenyl group is more preferable.
  • R 111 to R 130 represent a substituent
  • any of R 111 , R 113 , R 116 , R 119 , R 122 , R 125 , R 128 , and R 130 represents a substituent from the viewpoint of durability.
  • R 111 and R 130 preferably represent a substituent
  • R 112 to R 129 preferably represent a hydrogen atom.
  • Examples of the divalent linking group represented by L 1 and L 2 include an arylene group, a heteroarylene group, a linking group in which an arylene group and a heteroarylene group are linked in a chain, and an arylene group from the viewpoint of charge transportability. Is preferred.
  • the divalent linking group represented by L 1 and L 2 may further have a substituent, and adjacent substituents may be linked to form a ring. Examples of the further substituent include an alkyl group, An aryl group or a heteroaryl group can be mentioned.
  • the alkyl group as a further substituent is synonymous with the alkyl group represented by R 111 to R 130 , and preferred ones are also the same.
  • the aryl group as a further substituent preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and is preferably a phenyl group, a biphenyl group, or a terphenyl group. , A phenanthryl group, more preferably a phenyl group.
  • the heteroaryl group as a further substituent preferably has 4 to 30 carbon atoms, more preferably 4 to 20 carbon atoms.
  • Group, an oxazolyl group, a thiazolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and the like, and a pyridyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group is preferable.
  • the arylene group represented by L 1 and L 2 is preferably a phenylene group, a naphthylene group, an anthracenylene group, a biphenylene group, a terphenylene group, a quarterphenylene group, or a kink phenylene group, more preferably a phenylene group, It is a biphenylene group or a terphenylene group, more preferably a phenylene group or a biphenylene group.
  • Examples of the heteroarylene group represented by L 1 and L 2 include a pyridine ring group, a pyrimidine ring group, and a triazine ring group, and a pyridine ring group, a pyrimidine ring group, and a triazine ring group are preferable.
  • Two or more of the substituents represented by R 111 to R 117 , two or more of the substituents represented by R 118 to R 123 , and two or more of the substituents represented by R 124 to R 130 are condensed with each other to give an aromatic A ring may be formed.
  • the ring formed include a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyrrole ring, a pyrazole ring, an imidazole ring, a furan ring, and a thiophene ring. From the viewpoint of sublimation, an aromatic ring may be used. It is preferable not to form them.
  • the substituent represented by R 111 to R 130 may further have a substituent, and examples of the further substituent include an alkyl group and an aryl group.
  • the alkyl group as a further substituent is synonymous with the alkyl group represented by R 111 to R 130 , and preferred ones are also the same.
  • the aryl group as a further substituent preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and is preferably a phenyl group.
  • L 1 and L 2 are preferably each independently a linking group represented by any of the following general formulas (1-1) to (1-3).
  • R 411 each independently represents a substituent.
  • N 411 each independently represents an integer of 0 to 4. * represents a connecting position.
  • n 411 independently represents an integer of 0 to 4, preferably 0 to 2, more preferably 0 or 1. This is because when n 411 is 2 or more, the dihedral angle with the group to be connected is increased, resulting in a decrease in durability.
  • X represents an oxygen atom or a sulfur atom each independently, and R111 and R130 each independently represent a hydrogen atom or a substituent.
  • X in the general formula (2), R 111, and R 130 is, X in the general formula (1), R 111, and has the same meaning as R 130, preferred ranges are also the same.
  • each X independently represents an oxygen atom or a sulfur atom
  • R 111 and R 130 each independently represent a hydrogen atom or a substituent.
  • X in the general formula (3), R 111, and R 130 is, X in the general formula (1), R 111, and has the same meaning as R 130, preferred ranges are also the same.
  • the compound represented by any one of the general formulas (1) to (3) is preferably a compound consisting of only a carbon atom, a hydrogen atom, an oxygen atom or a sulfur atom. This provides improved durability.
  • the molecular weight of the compound represented by any one of the general formulas (1) to (3) is usually 400 or more and 1500 or less, preferably 450 or more and 1200 or less, more preferably 500 or more and 1100 or less, and 600 More preferably, it is 1000 or less.
  • the molecular weight is 450 or more, it is advantageous for forming a high-quality amorphous thin film, and when the molecular weight is 1200 or less, the solubility and sublimation property are improved, which is advantageous for improving the purity of the compound.
  • the compound represented by any one of the general formulas (1) to (3) is used as a host material for a light emitting layer of an organic electroluminescent device or a charge transport material for a layer adjacent to the light emitting layer,
  • the energy gap the light emitting material is a phosphorescent light emitting material
  • the minimum excited triplet (T 1 ) energy in a thin film state is large, which prevents the light emission from being quenched and is advantageous for improving the efficiency.
  • the energy gap and T 1 energy are not too large.
  • the T 1 energy in the film state of the compound represented by any one of the general formulas (1) to (3) is preferably 2.39 eV (55 kcal / mol) or more and 3.51 eV (80 kcal / mol) or less. More preferably, it is 2.52 eV (58 kcal / mol) or more and 3.04 eV (70 kcal / mol) or less.
  • the T 1 energy is preferably in the above range.
  • the T 1 energy can be obtained from the short wavelength end of a phosphorescence emission spectrum of a thin film of material. For example, a material is deposited on a cleaned quartz glass substrate to a thickness of about 50 nm by vacuum deposition, and the phosphorescence emission spectrum of the thin film is measured at F-7000 Hitachi Spectrofluorimeter (Hitachi High Technologies) under liquid nitrogen temperature. Use to measure.
  • the T 1 energy can be obtained by converting the rising wavelength on the short wavelength side of the obtained emission spectrum into energy units.
  • the glass transition temperature (Tg) of the compound represented by the general formula (1) is 100 ° C. or higher and 400 ° C. or lower from the viewpoint of stably operating the organic electroluminescent device against heat generated during high temperature driving or driving the device.
  • the temperature is 120 ° C. or higher and 400 ° C. or lower, more preferably 140 ° C. or higher and 400 ° C. or lower.
  • the purity of the compound represented by any one of the general formulas (1) to (3) is low, impurities work as a charge transport trap or promote deterioration of the device.
  • the purity can be measured by, for example, high performance liquid chromatography (HPLC), and the area ratio of the compound represented by the general formula (1) when detected with a light absorption intensity of 254 nm is preferably 95.0% or more, and more It is preferably 97.0% or more, particularly preferably 99.0% or more, and most preferably 99.9% or more.
  • the compound represented by the general formula (1) can be synthesized, for example, by a method described in International Publication No. 2007/069569, International Publication No. 2009/073245, or the like.
  • the compound represented by General formula (1) is a novel compound, it is compoundable as follows, for example with said method.
  • the compound represented by any one of the general formulas (1) to (3) is not limited in its use, and may be contained in any layer in the organic layer.
  • the compound-introduced layer represented by the general formula (1) is contained in one or more of the light emitting layer, the layer between the light emitting layer and the cathode, the layer between the light emitting layer and the anode, or a plurality thereof.
  • the compound represented by any one of the general formulas (1) to (3) is added to the light emitting layer and the light emitting layer between the light emitting layer and the cathode in order to further suppress the decrease in light emission efficiency after high temperature driving. It is preferably contained in any one of an adjacent organic layer (a layer adjacent to the light emitting layer on the cathode side from the light emitting layer) and an electron injection layer adjacent to the cathode on the light emitting layer side from the cathode, More preferably, it is contained in any of the layers adjacent to the light emitting layer on the cathode side of the light emitting layer, and more preferably contained in the light emitting layer.
  • the compound represented by any one of the general formulas (1) to (3) may be contained in both the light emitting layer and the layer adjacent to the light emitting layer on the cathode side of the light emitting layer.
  • the compound represented by the general formula (1) to (3) has a concentration of 0.0. It is preferable to contain 1 to 99% by mass, more preferably 1 to 97% by mass, and still more preferably 10 to 96% by mass.
  • the compound represented by any one of the general formulas (1) to (3) is further contained in a layer other than the light emitting layer, it is contained in an amount of 70 to 100% by mass with respect to the total mass of the layer other than the light emitting layer. And more preferably 85 to 100% by mass.
  • the present invention also relates to a charge transport material represented by the general formula (1).
  • the charge transport material represented by the general formula (1) is preferably a charge transport material represented by the general formula (2) or (3).
  • the compound represented by the general formula (1) and the charge transport material of the present invention are preferably used for organic electronic elements such as electrophotography, organic transistors, organic photoelectric conversion elements (energy conversion applications, sensor applications, etc.), and organic electroluminescence elements. It can be used and is particularly preferably used for an organic electroluminescent device.
  • composition containing a compound represented by any one of the general formulas (1) to (3) also relates to a composition comprising a compound (charge transport material) represented by any one of the general formulas (1) to (3).
  • the content of the compound represented by any one of the general formulas (1) to (3) is preferably 30 to 99% by mass with respect to the total solid content in the composition, The content is more preferably 50 to 97% by mass, and further preferably 70 to 96% by mass.
  • Other components that may be contained in the composition of the present invention may be organic or inorganic, and as organic materials, materials described as host materials, fluorescent light emitting materials, phosphorescent light emitting materials, and hydrocarbon materials described later can be applied.
  • a host material, a phosphorescent material, and a hydrocarbon material are preferable.
  • the composition of the present invention can form an organic layer of an organic electroluminescence device by a dry film forming method such as a vapor deposition method or a sputtering method, or a wet film forming method such as a transfer method or a printing method.
  • the present invention also relates to a thin film containing a charge transport material represented by any one of the general formulas (1) to (3).
  • the film (thin film) of the present invention can be formed by using the composition of the present invention by a dry film forming method such as a vapor deposition method or a sputtering method, or a wet film forming method such as a transfer method or a printing method.
  • the thickness of the thin film may be any thickness depending on the application, but is preferably 0.1 nm to 1 mm, more preferably 0.5 nm to 1 ⁇ m, still more preferably 1 nm to 200 nm, and particularly preferably 1 nm to 100 nm. is there.
  • the organic electroluminescent element of the present invention is an organic electroluminescent device having a pair of electrodes comprising an anode and a cathode and at least one organic layer including a light emitting layer between the electrodes on the substrate, wherein the light emitting layer And at least one of the at least one organic layer contains a compound represented by any one of the general formulas (1) to (3) of the present invention.
  • at least one of the pair of electrodes, the anode and the cathode is preferably transparent or translucent.
  • Examples of the organic layer include a hole injection layer, a hole transport layer, a block layer (such as a hole block layer and an exciton block layer), and an electron transport layer in addition to the light emitting layer.
  • a plurality of these organic layers may be provided, and when a plurality of layers are provided, they may be formed of the same material, or may be formed of different materials for each layer.
  • FIG. 1 an example of a structure of the organic electroluminescent element which concerns on this invention is shown.
  • the organic electroluminescent element 10 of FIG. 1 has an organic layer including a light emitting layer 6 between a pair of electrodes (anode 3 and cathode 9) on a substrate 2.
  • As the organic layer a hole injection layer 4, a hole transport layer 5, a light emitting layer 6, a hole block layer 7 and an electron transport layer 8 are laminated in this order from the anode side 3.
  • Anode / hole transport layer / light emitting layer / electron transport layer / cathode Anode / hole transport layer / light emitting layer / block layer / electron transport layer / cathode, Anode / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode, Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / cathode, Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / cathode, Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode, Anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode, Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport
  • the element configuration, the substrate, the cathode, and the anode of the organic electroluminescence element are described in detail in, for example, Japanese Patent Application Laid-Open No. 2008-270736, and the matters described in the publication can be applied to the present invention.
  • the substrate used in the present invention is preferably a substrate that does not scatter or attenuate light emitted from the organic layer.
  • an organic material it is preferable that it is excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation, and workability.
  • the anode usually only needs to have a function as an electrode for supplying holes to the organic layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element, It can select suitably from well-known electrode materials.
  • the anode is usually provided as a transparent anode.
  • the cathode usually has a function as an electrode for injecting electrons into the organic layer, and there is no particular limitation on the shape, structure, size, etc., and it is known depending on the use and purpose of the light-emitting element.
  • the electrode material can be selected as appropriate.
  • Organic layer in the present invention will be described.
  • each organic layer is preferably formed by any of dry film forming methods such as vapor deposition and sputtering, and solution coating methods such as transfer, printing, spin coating, and bar coating. Can be formed.
  • the light emitting layer receives holes from the anode, hole injection layer or hole transport layer and receives electrons from the cathode, electron injection layer or electron transport layer when an electric field is applied, and provides a field for recombination of holes and electrons. And a layer having a function of emitting light.
  • the light emitting layer in the organic electroluminescent element of the present invention contains at least one phosphorescent material.
  • Luminescent material in addition to at least one phosphorescent light-emitting material contained in the light-emitting layer, a fluorescent light-emitting material or a phosphorescent light-emitting material different from the phosphorescent light-emitting material contained in the light-emitting layer can be used as the light-emitting material. Details of these fluorescent materials and phosphorescent materials are described in, for example, paragraph numbers [0100] to [0164] of JP-A-2008-270736 and paragraph numbers [0088] to [0090] of JP-A-2007-266458. The matters described in these publications can be applied to the present invention.
  • Examples of phosphorescent light-emitting materials that can be used in the present invention include US Pat. / 19373A2, JP-A No. 2001-247859, JP-A No. 2002-302671, JP-A No. 2002-117978, JP-A No. 2003-133074, JP-A No. 2002-1235076, JP-A No. 2003-123684, JP-A No. 2002-170684, EP No. 121157, JP-A No.
  • Examples of such a light emitting material include Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb complex, Gd.
  • Examples include phosphorescent metal complex compounds such as complexes, Dy complexes, and Ce complexes.
  • an Ir complex, a Pt complex, or a Re complex among which an Ir complex or a Pt complex containing at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, and a metal-sulfur bond. Or Re complexes are preferred. Furthermore, from the viewpoints of luminous efficiency, driving durability, chromaticity and the like, an Ir complex and a Pt complex are particularly preferable, and an Ir complex is most preferable.
  • These phosphorescent metal complex compounds are preferably contained in the light emitting layer together with the compound represented by any one of the general formulas (1) to (3).
  • an iridium complex represented by the following general formula (T-1) or a platinum complex represented by the following general formula (C-1) is used as the phosphorescent material contained in the light emitting layer in the present invention. It is preferable.
  • R T3 ′, R T3 , R T4 , R T5 and R T6 each independently represent a hydrogen atom or a substituent.
  • R T3 , R T4 , R T5 and R T6 may be any two adjacent to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or hetero It is aryl, and the condensed 4- to 7-membered ring may further have a substituent.
  • Ring Q is a 5- or 6-membered aromatic heterocyclic ring or condensed aromatic heterocyclic ring containing one or more nitrogen atoms.
  • (XY) represents an auxiliary ligand.
  • m represents an integer of 1 to 3.
  • n represents an integer of 0-2.
  • m + n 3.
  • R T3 ′, R T3 , R T4 , R T5 and R T6 examples include the above-mentioned substituent group A, preferably an alkyl group, an alkenyl group, an alkynyl group, —CN, Represents a perfluoroalkyl group, a trifluorovinyl group, —CO 2 R T , —C (O) R T , —N (R T ) 2 , —NO 2 , —OR T , a fluorine atom, an aryl group or a heteroaryl group Furthermore, you may have the following substituents T.
  • Each substituent T independently, a fluorine atom, -R ', - OR', - N (R ') 2, -SR', - C (O) R ', - C (O) OR', - C ( O) represents N (R ′) 2 , —CN, —NO 2 , —SO 2 , —SOR ′, —SO 2 R ′, or —SO 3 R ′, and each R ′ independently represents a hydrogen atom, alkyl Represents a group, a perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • an alkyl group, an alkoxy group, a fluorine atom, a cyano group, and a dialkylamino group are preferable, and a hydrogen atom is more preferable.
  • the alkyl group represented by R T3 ′, R T3 , R T4 , R T5 , R T6 may have a substituent, may be saturated or unsaturated, Examples of the preferable group include the substituent T described above.
  • the alkyl group represented by R T3 ′, R T3 , R T4 , R T5 and R T6 is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms. Group, for example, methyl group, ethyl group, i-propyl group, t-butyl group and the like.
  • the cycloalkyl group represented by R T3 ′, R T3 , R T4 , R T5 , R T6 may have a substituent, may be saturated or unsaturated, Examples of the group which may be mentioned include the substituent T described above.
  • the cycloalkyl group represented by R T3 ′, R T3 , R T4 , R T5 , and R T6 is preferably a cycloalkyl group having 4 to 7 ring members, and more preferably a cycloalkyl group having 5 to 6 total carbon atoms. Examples of the alkyl group include a cyclopentyl group and a cyclohexyl group.
  • the alkenyl group represented by R T3 ′, R T3 , R T4 , R T5 and R T6 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. Examples thereof include vinyl, allyl, 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl and the like.
  • the alkynyl group represented by R T3 ′, R T3 , R T4 , R T5 , R T6 is preferably a group having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. For example, ethynyl, propargyl, 1-propynyl, 3-pentynyl and the like.
  • the aryl group represented by R T3 ′, R T3 , R T4 , R T5 , and R T6 is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, such as a phenyl group, a tolyl group, and a naphthyl group. Groups and the like.
  • the heteroaryl group represented by R T3 ′, R T3 , R T4 , R T5 , and R T6 is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or 6-membered substituent.
  • an unsubstituted heteroaryl group for example, pyridyl group, pyrazinyl group, pyridazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, cinnolinyl group, phthalazinyl group, quinoxalinyl group, pyrrolyl group, indolyl group , Furyl group, benzofuryl group, thienyl group, benzothienyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, triazolyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, isothiazolyl group, benzisothiazolyl group , Thiadiazolyl group, a Examples include a soxazolyl group, a benzisoxazo
  • R T3 ′, R T3 , R T4 , R T5 and R T6 are preferably a hydrogen atom, alkyl group, cyano group, trifluoromethyl group, perfluoroalkyl group, dialkylamino group, fluorine atom, aryl group, heteroaryl group And more preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a fluorine atom or an aryl group, and still more preferably a hydrogen atom, an alkyl group or an aryl group.
  • R T3 , R T4 , R T5 and R T6 may be any two adjacent to each other to form a condensed 4- to 7-membered ring, and R T3 and R T4 are bonded to each other to form a condensed 4- to 7-membered It is preferable to form a ring.
  • the fused 4- to 7-membered ring is cycloalkyl, aryl or heteroaryl, and the fused 4- to 7-membered ring may further have a substituent, and preferably have a substituent T. .
  • cycloalkyl, aryl and heteroaryl formed are the same as the cycloalkyl group, aryl group and heteroaryl group defined by R T3 ′, R T3 , R T4 , R T5 and R T6 .
  • Examples of the aromatic heterocyclic ring represented by ring Q include a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyrazole ring, an imidazole ring, a triazole ring, an oxazole ring, an oxadiazole ring, a thiazole ring, and a thiadiazole ring.
  • a pyridine ring and a pyrazine ring are preferable, and a pyridine ring is more preferable.
  • Examples of the condensed aromatic heterocycle represented by ring Q include a quinoline ring, an isoquinoline ring, and a quinoxaline ring. Preferred are a quinoline ring and an isoquinoline ring, and more preferred is a quinoline ring.
  • M is preferably 1 to 3, and more preferably 2 or 3. That is, n is preferably 0 or 1. It is preferable that the kind of ligand in a complex is comprised from 1 or 2 types, More preferably, it is 1 type. When introducing a reactive group into the complex molecule, it is also preferred that the ligand consists of two types from the viewpoint of ease of synthesis.
  • the metal complex represented by the general formula (T-1) includes a ligand represented by the following general formula (T-1-A) in the general formula (T-1) or a tautomer thereof, and (X -Y) or a combination with a tautomer thereof, or all of the ligands of the metal complex are represented by the following general formula (T-1-A) Or a tautomer thereof.
  • R T3 ′, R T3 , R T4 , R T5 , R T6 and Q are the same as R T3 ′, R T3 , R T4 , (It is synonymous with R T5 , R T6 and Q. * represents the coordination position to iridium.)
  • a ligand used for forming a conventionally known metal complex
  • a ligand also referred to as a coordination compound
  • XY a ligand represented by (XY). You may do it.
  • ligands used in conventionally known metal complexes.
  • ligands eg, halogen ligands (preferably chlorine ligands), etc., published in 1987, published by Yersin, “Organometallic Chemistry-Fundamentals and Applications-”
  • Nitrogen heteroaryl ligands for example, bipyridyl, phenanthroline, etc.
  • diketone ligands for example, acetylacetone, etc.
  • the ligand represented by (XY) is preferably a diketone or a picolinic acid.
  • the derivative is most preferably acetylacetonate (acac) shown below from the viewpoint of obtaining stability of the complex and high luminous efficiency.
  • Rx, Ry and Rz each independently represents a hydrogen atom or a substituent.
  • substituent include a substituent selected from the substituent group A.
  • Rx and Rz are each independently an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, A fluorine atom and an optionally substituted phenyl group are most preferred, and a methyl group, an ethyl group, a trifluoromethyl group, a fluorine atom and a phenyl group are most preferred.
  • Ry is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an optionally substituted phenyl group. And most preferably a hydrogen atom or a methyl group. Since these ligands are considered not to be sites where electrons are transported in the device or where electrons are concentrated by excitation, Rx, Ry, and Rz may be any chemically stable substituent, and the effects of the present invention can be achieved. Also has no effect. Since complex synthesis is easy, (I-1), (I-4) and (I-5) are preferred, and (I-1) is most preferred.
  • Ligands having these ligands can be synthesized in the same manner as in known synthesis examples by using corresponding ligand precursors. For example, in the same manner as described in International Publication No. 2009-073245, page 46, it can be synthesized by the following method using commercially available difluoroacetylacetone.
  • a monoanionic ligand represented by the general formula (I-15) can also be used as the ligand.
  • R T7 to R T10 in general formula (I-15) have the same meanings as R T3 to R T6 in general formula (T-1), and the preferred ranges are also the same.
  • R T7 ′ to R T10 ′ have the same meaning as R T3 ′, and the preferred range is also the same as R T3 ′. * Represents a coordination position to iridium.
  • the compound represented by the general formula (T-1) is preferably a compound represented by the following general formula (T-2).
  • R T3 ′ to R T6 ′ and R T3 to R T6 are each independently a hydrogen atom, alkyl group, alkenyl group, alkynyl group, —CN, perfluoroalkyl group, trifluorovinyl.
  • R T3 , R T4 , R T5 and R T6 may be combined with each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring further has a substituent T. It may be.
  • a ring may be formed by linking with a linking group selected from —O—C (R T ) 2 —, —NR T —C (R T ) 2 —, and —N ⁇ CR T —.
  • R T each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group, or a heteroaryl group, and may further have a substituent T.
  • Each substituent T independently, a fluorine atom, -R ', - OR', - N (R ') 2, -SR', - C (O) R ', - C (O) OR', - C ( O) represents N (R ′) 2 , —CN, —NO 2 , —SO 2 , —SOR ′, —SO 2 R ′, or —SO 3 R ′, and each R ′ independently represents a hydrogen atom, alkyl Represents a group, a perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • (XY) represents a ligand.
  • m T represents an integer of 1 to 3
  • n T represents an integer of 0 to 2.
  • m T + n T is 3.
  • R T3 in the general formula (T-2) ', R T3 ⁇ R T6, (X-Y), the preferred range of m T and n T is, R T3 in the general formula (T-1)', R T3 ⁇ R This is the same as the preferred range of T6 , (XY), m and n.
  • R T4 ′ is preferably a hydrogen atom, an alkyl group, an aryl group, or a fluorine atom, and more preferably a hydrogen atom.
  • R T5 ′ and R T6 ′ represent a hydrogen atom or are preferably bonded to each other to form a condensed 4- to 7-membered cyclic group, and the condensed 4- to 7-membered cyclic group includes cycloalkyl, cyclohetero More preferred is alkyl, aryl, or heteroaryl, and even more preferred is aryl.
  • substituent T in R T4 ′ to R T6 ′ an alkyl group, an alkoxy group, a fluorine atom, a cyano group, an alkylamino group, and a diarylamino group are preferable, and an alkyl group is more preferable.
  • One of preferable forms of the compound represented by the general formula (T-2) is R T3 ′, R T4 ′, R T5 ′, R T6 ′, R T3 , R T4 in the general formula (T-2). , R T5 and R T6 , any two adjacent groups are not bonded to each other to form a condensed ring.
  • T-2 One preferred form of the compound represented by the general formula (T-2) is a case represented by the following general formula (T-3).
  • R T3 ' ⁇ R T6' in the general formula (T3) R T3 ⁇ R T6 is, R T3 in the general formula (T-2) ' ⁇ R T6', have the same meaning as R T3 ⁇ R T6, preferably The range is the same.
  • m T3 represents 2.
  • R T7 to R T10 have the same meanings as R T3 to R T6 , and preferred ranges are also the same.
  • R T7 ′ to R T10 ′ have the same meanings as R T3 ′ to R T6 ′, and preferred ranges are also the same.
  • T-2 Another preferred embodiment of the compound represented by the general formula (T-2) is a compound represented by the following general formula (T-4).
  • R T3 ′ to R T7 ′, R T3 to R T6 , (XY), m T and n T in the general formula (T-4) are R T3 ′ to R T6 ′ in the general formula (T-2).
  • R T3 to R T6 , (XY), m T, and n T are R T3 ′ to R T6 ′ in the general formula (T-2).
  • R T3 to R T6 , (XY), m T, and n T and the preferred range is also the same.
  • R T3 ′ to R T7 ′ and R T3 to R T6 it is particularly preferred that 0 to 2 are alkyl groups or phenyl groups and the rest are all hydrogen atoms, and R T3 ′ to R T6 ′ and R T3 to R More preferably, one or two of T6 are alkyl groups and the rest are all hydrogen atoms.
  • T-2 Another preferred embodiment of the compound represented by the general formula (T-2) is a compound represented by the following general formula (T-5).
  • R T3 ′ to R T7 ′, R T3 to R T6 , (XY), m T and n T in the general formula (T-5) are R T3 ′ to R T6 ′ in the general formula (T-2).
  • R T3 to R T6 , (XY), m T and n T have the same meanings, and preferred examples are also the same.
  • T-1 Another preferred embodiment of the compound represented by the general formula (T-1) is a case represented by the following general formula (T-6).
  • R 1a to R 1i are the same as those in R T3 to R T6 in general formula (T-1). Further, it is particularly preferable that 0 to 2 of R 1a to R 1i are alkyl groups or aryl groups and the rest are all hydrogen atoms.
  • the definitions and preferred ranges of (XY), m and n are the same as (XY), m and n in formula (T-1).
  • the compounds exemplified as the compound represented by the general formula (T-1) can be synthesized by the method described in JP2009-99783A or various methods described in US Pat. No. 7,279,232. After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.
  • the compound represented by the general formula (T-1) is contained in the light emitting layer, but its use is not limited and may be further contained in any layer in the organic layer.
  • a compound represented by the following general formula (T-7) or a compound having a carbene as a ligand can also be preferably used.
  • R T11 to R T17 have the same meanings as R T3 to R T6 in the general formula (T-2), and preferred ranges thereof are also the same.
  • (XY), n, and m have the same meanings as (XY), n T , and m T in formula (T-2), and the preferred ranges are also the same.
  • the light emitting material in the light emitting layer is generally contained in the light emitting layer in an amount of 0.1% by mass to 50% by mass with respect to the total mass of the compound forming the light emitting layer. From the viewpoint of durability and external quantum efficiency.
  • the content is preferably 1% by mass to 50% by mass, and more preferably 2% by mass to 40% by mass.
  • the thickness of the light emitting layer is not particularly limited, but is usually preferably 2 nm to 500 nm, and more preferably 3 nm to 200 nm, and more preferably 5 nm to 100 nm from the viewpoint of external quantum efficiency. More preferably.
  • the light emitting layer in the element of the present invention may have a mixed layer of a host material and a light emitting material.
  • the light emitting material may be a fluorescent light emitting material or a phosphorescent light emitting material, and the dopant may be one kind or two or more kinds.
  • the host material is preferably a charge transport material.
  • the host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed.
  • the light emitting layer may include a material that does not have charge transporting properties and does not emit light.
  • the light emitting layer may be a single layer or a multilayer of two or more layers. In addition, each light emitting layer may emit light with different emission colors.
  • the compound represented by the general formula (T-1) is included in the light emitting layer from the viewpoint of improving luminous efficiency and durability (particularly durability at high temperature driving). It is not limited and may be contained in any layer in addition to the light emitting layer in the organic layer.
  • a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, and a charge block layer can be used. It is preferable to be contained in one or a plurality.
  • composition containing a compound represented by the general formula (1) and a compound represented by the general formula (T-1) The present invention also relates to a composition containing the compound represented by the general formula (1) and the compound represented by the general formula (T-1).
  • the content of the compound represented by the general formula (1) in the composition of the present invention is preferably 50 to 99% by mass, and more preferably 70 to 95% by mass.
  • the content of the compound represented by formula (T-1) in the composition of the present invention is preferably 1 to 30% by mass, and more preferably 5 to 20% by mass.
  • Other components that may be contained in the composition of the present invention may be organic or inorganic, and as organic materials, materials described as host materials, fluorescent materials, and phosphorescent materials described later can be applied.
  • the composition of the present invention can form an organic layer of an organic electroluminescent element by a dry film forming method such as a vapor deposition method or a sputtering method, a transfer method, a printing method, or the like.
  • Q 1 , Q 2 , Q 3 and Q 4 each independently represent a ligand coordinated to Pt.
  • L 1 , L 2 and L 3 are each independently Represents a single bond or a divalent linking group.
  • Q 1 , Q 2 , Q 3 and Q 4 each independently represent a ligand coordinated to Pt.
  • the bond between Q 1 , Q 2 , Q 3 and Q 4 and Pt may be any of a covalent bond, an ionic bond, a coordinate bond, and the like.
  • a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a phosphorus atom are preferable, and in Q ⁇ 1 >, Q ⁇ 2 >, Q ⁇ 3 > and Q ⁇ 4 >
  • a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a phosphorus atom are preferable, and in Q ⁇ 1 >, Q ⁇ 2 >, Q ⁇ 3 > and Q ⁇ 4 >
  • at least one is preferably a carbon atom, more preferably two are carbon atoms, and particularly preferably two are carbon atoms and two are nitrogen atoms.
  • Q 1 , Q 2 , Q 3 and Q 4 bonded to Pt by a carbon atom may be an anionic ligand or a neutral ligand, and the anionic ligand is a vinyl ligand, Aromatic hydrocarbon ring ligand (eg benzene ligand, naphthalene ligand, anthracene ligand, phenanthrene ligand etc.), heterocyclic ligand (eg furan ligand, thiophene ligand, pyridine) Ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, thiazole ligand, oxazole ligand, pyrrole ligand, imidazole ligand, pyrazole ligand, triazole And a condensed ring containing them (for example, quinoline ligand, benzothiazole ligand, etc.).
  • Q 1 , Q 2 , Q 3 and Q 4 bonded to Pt with a nitrogen atom may be neutral ligands or anionic ligands, and as neutral ligands, nitrogen-containing aromatic hetero Ring ligand (pyridine ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, imidazole ligand, pyrazole ligand, triazole ligand, oxazole ligand, Examples include thiazole ligands and condensed rings containing them (for example, quinoline ligands, benzimidazole ligands), amine ligands, nitrile ligands, and imine ligands.
  • nitrogen-containing aromatic hetero Ring ligand pyridine ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, imidazole
  • anionic ligands include amino ligands, imino ligands, nitrogen-containing aromatic heterocyclic ligands (pyrrole ligands, imidazole ligands, triazole ligands, and condensed rings containing them) (For example, indole ligand, benzimidazole ligand, etc.)).
  • Q 1 , Q 2 , Q 3 and Q 4 bonded to Pt with an oxygen atom may be neutral ligands or anionic ligands, and neutral ligands are ether ligands, Examples include ketone ligands, ester ligands, amide ligands, oxygen-containing heterocyclic ligands (furan ligands, oxazole ligands and condensed rings containing them (benzoxazole ligands, etc.)). It is done.
  • the anionic ligand include an alkoxy ligand, an aryloxy ligand, a heteroaryloxy ligand, an acyloxy ligand, a silyloxy ligand, and the like.
  • Q 1 , Q 2 , Q 3 and Q 4 bonded to Pt with a sulfur atom may be neutral ligands or anionic ligands, and neutral ligands include thioether ligands, Examples include thioketone ligands, thioester ligands, thioamide ligands, sulfur-containing heterocyclic ligands (thiophene ligands, thiazole ligands and condensed rings containing them (such as benzothiazole ligands)). It is done.
  • the anionic ligand include an alkyl mercapto ligand, an aryl mercapto ligand, and a heteroaryl mercapto ligand.
  • Q 1 , Q 2 , Q 3 and Q 4 bonded to Pt with a phosphorus atom may be neutral ligands or anionic ligands, and neutral ligands include phosphine ligands, Examples include phosphate ester ligands, phosphite ester ligands, and phosphorus-containing heterocyclic ligands (phosphinin ligands, etc.).
  • Anionic ligands include phosphino ligands and phosphinyl ligands. And phosphoryl ligands.
  • the groups represented by Q 1 , Q 2 , Q 3, and Q 4 may have a substituent, and those listed as the substituent group A can be appropriately applied as the substituent. Moreover, substituents may be connected to each other (when Q 3 and Q 4 are connected, a Pt complex of a cyclic tetradentate ligand is formed).
  • the group represented by Q 1 , Q 2 , Q 3 and Q 4 is preferably an aromatic hydrocarbon ring ligand bonded to Pt with a carbon atom, and an aromatic heterocyclic ligand bonded to Pt with a carbon atom.
  • L 1 , L 2 and L 3 represent a single bond or a divalent linking group.
  • the divalent linking group represented by L 1 , L 2 and L 3 include alkylene groups (methylene, ethylene, propylene, etc.), arylene groups (phenylene, naphthalenediyl), heteroarylene groups (pyridinediyl, thiophenediyl, etc.) ), Imino group (—NR L —) (such as phenylimino group), oxy group (—O—), thio group (—S—), phosphinidene group (—PR L —) (such as phenylphosphinidene group), silylene (-SiR L R L '-) ( dimethylsilylene group, a diphenylsilylene group), or the like combinations thereof.
  • examples of R L and R L ′ include an alkyl group and an aryl group. These linking groups may further have a substituent. As the substituent, those exemplified as the substituent group A can be appropriately applied. From the viewpoint of the stability of the complex and the emission quantum yield, L 1 , L 2 and L 3 are preferably a single bond, an alkylene group, an arylene group, a heteroarylene group, an imino group, an oxy group, a thio group or a silylene group.
  • a single bond, an alkylene group, an arylene group or an imino group still more preferably a single bond, an alkylene group or an arylene group, still more preferably a single bond, a methylene group or a phenylene group, still more preferably.
  • Single bond, disubstituted methylene group more preferably single bond, dimethylmethylene group, diethylmethylene group, diisobutylmethylene group, dibenzylmethylene group, ethylmethylmethylene group, methylpropylmethylene group, isobutylmethylmethylene group, diphenyl Methylene group, methylphenylmethylene group, cyclohexanediyl group, A lopentanediyl group, a fluorenediyl group, and a fluoromethylmethylene group, particularly preferably a single bond, a dimethylmethylene group, a diphenylmethylene group, and a cyclohexanediyl group.
  • platinum complexes represented by the general formula (C-1) a platinum complex represented by the following general formula (C-2) is more preferable.
  • L 21 represents a single bond or a divalent linking group.
  • a 21 and A 22 each independently represent a carbon atom or a nitrogen atom.
  • Z 21, Z 22 each independently represents a nitrogen-containing aromatic heterocyclic ring.
  • Z 23 and Z 24 each independently represent a benzene ring or an aromatic heterocycle.
  • L 21 has the same meaning as L 1 in formula (C-1), and the preferred range is also the same.
  • a 21 and A 22 each independently represent a carbon atom or a nitrogen atom. Of A 21, A 22, Preferably, at least one is a carbon atom, it A 21, A 22 are both carbon atoms are preferred from the standpoint of emission quantum yield stability aspects and complexes of the complex .
  • Z 21 and Z 22 each independently represent a nitrogen-containing aromatic heterocycle.
  • the nitrogen-containing aromatic heterocycle represented by Z 21 and Z 22 include a pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole ring, Examples include thiadiazole rings.
  • the ring represented by Z 21 and Z 22 is preferably a pyridine ring, a pyrazine ring, an imidazole ring or a pyrazole ring, more preferably a pyridine ring.
  • the nitrogen-containing aromatic heterocycle represented by Z 21 and Z 22 may have a substituent, and the substituent group A is a substituent on a carbon atom, and the substituent on a nitrogen atom is The substituent group B can be applied.
  • the substituent on carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a halogen atom.
  • the substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of shortening the wavelength, an electron donating group, a fluorine atom, and an aromatic ring group are preferable.
  • an alkyl group, a dialkylamino group, an alkoxy group, A fluorine atom, an aryl group, an aromatic heterocyclic group and the like are selected.
  • an electron withdrawing group is preferable, and for example, a cyano group, a perfluoroalkyl group, and the like are selected.
  • the substituent on the nitrogen atom is preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex.
  • the substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like.
  • Z 23 and Z 24 each independently represent a benzene ring or an aromatic heterocycle.
  • the nitrogen-containing aromatic heterocycle represented by Z 23 and Z 24 include pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadi Examples include an azole ring, a thiadiazole ring, a thiophene ring, and a furan ring.
  • the ring represented by Z 23 and Z 24 is preferably a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring, or a thiophene ring, More preferred are a benzene ring, a pyridine ring and a pyrazole ring, and still more preferred are a benzene ring and a pyridine ring.
  • the benzene ring and nitrogen-containing aromatic heterocycle represented by Z 23 and Z 24 may have a substituent.
  • the substituent group A is substituted on the nitrogen atom.
  • the substituent group B can be applied as the group.
  • the substituent on carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a halogen atom.
  • the substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of increasing the wavelength, an electron donating group and an aromatic ring group are preferable, for example, an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, An aromatic heterocyclic group or the like is selected.
  • an electron withdrawing group is preferable, and for example, a fluorine atom, a cyano group, a perfluoroalkyl group, and the like are selected.
  • the substituent on the nitrogen atom is preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex.
  • the substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like.
  • platinum complexes represented by the general formula (C-2) one of more preferred embodiments is a platinum complex represented by the following general formula (C-3).
  • a 301 to A 313 each independently represent C—R or a nitrogen atom.
  • R represents a hydrogen atom or a substituent.
  • L 31 represents a single bond or a divalent linking group.
  • L 31 has the same meaning as L 21 in formula (C-2), and the preferred range is also the same.
  • a 301 to A 306 each independently represents C—R or a nitrogen atom.
  • R represents a hydrogen atom or a substituent.
  • substituent represented by R those exemplified as the substituent group A can be applied.
  • a 301 to A 306 are preferably C—R, and Rs may be connected to each other to form a ring.
  • R in A 302 and A 305 is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom, or a cyano group. More preferably a hydrogen atom, an amino group, an alkoxy group, an aryloxy group or a fluorine atom, particularly preferably a hydrogen atom or a fluorine atom, and preferably R as A 301 , A 303 , A 304 or A 306 is a hydrogen atom.
  • a 307 , A 308 , A 309 and A 310 each independently represent C—R or a nitrogen atom.
  • R represents a hydrogen atom or a substituent. As the substituent represented by R, those exemplified as the substituent group A can be applied.
  • R is preferably a hydrogen atom, alkyl group, perfluoroalkyl group, aryl group, aromatic heterocyclic group, dialkylamino group, diarylamino Group, alkyloxy group, cyano group, halogen atom, more preferably hydrogen atom, alkyl group, perfluoroalkyl group, aryl group, dialkylamino group, cyano group, fluorine atom, more preferably hydrogen atom, alkyl group. , A trifluoromethyl group and a fluorine atom. If possible, the substituents may be linked to form a condensed ring structure.
  • a 308 is preferably a nitrogen atom.
  • the 6-membered ring formed from two carbon atoms and A 307 , A 308 , A 309 and A 310 includes a pyridine ring, a pyrazine ring, a pyrimidine ring, and a pyridazine ring. And a triazine ring, more preferably a pyridine ring, a pyrazine ring, a pyrimidine ring and a pyridazine ring, and particularly preferably a pyridine ring.
  • the 6-membered ring is a pyridine ring, a pyrazine ring, a pyrimidine ring, or a pyridazine ring (particularly preferably a pyridine ring), a hydrogen atom present at a position where a metal-carbon bond is formed as compared with a benzene ring. Since the acidity is improved, a metal complex is more easily formed, which is advantageous.
  • a 311 , A 312 and A 313 each independently represent C—R or a nitrogen atom.
  • R represents a hydrogen atom or a substituent.
  • substituent represented by R those exemplified as the substituent group A can be applied.
  • R is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkyl An oxy group, a cyano group, and a halogen atom, more preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, a dialkylamino group, a cyano group, and a fluorine atom, and more preferably a hydrogen atom, an alkyl group, and trifluoro A methyl group and a fluorine atom.
  • substituents may be linked to form a condensed ring structure.
  • the 5-membered ring formed by A 311 , A 312 and A 313 and one nitrogen atom and one carbon atom include a pyrrole ring, a pyrazole ring, an imidazole ring, a furan ring, and a thiophene ring, and more preferable.
  • the 5-membered ring is a pyrrole ring, a pyrazole ring, or an imidazole ring (more preferably, a pyrrole ring or a pyrazole ring), it is advantageous because the stability of the metal complex is improved.
  • platinum complexes represented by the general formula (C-2) one of the more preferred embodiments is a platinum complex represented by the following general formula (C-4).
  • a 401 to A 414 each independently represents C—R or a nitrogen atom.
  • R represents a hydrogen atom or a substituent.
  • L 41 represents a single bond or a divalent linking group.
  • a 401 to A 414 each independently represents C—R or a nitrogen atom.
  • R represents a hydrogen atom or a substituent.
  • a 401 to A 406 and L 41 have the same meanings as A 301 to A 306 and L 31 in formula (C-3), and preferred ranges thereof are also the same.
  • the number of nitrogen atoms is preferably 0 to 2, and more preferably 0 to 1.
  • a 408 and A 412 are preferably nitrogen atoms, and both A 408 and A 412 are more preferably nitrogen atoms.
  • R in A 408 and A 412 is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom, A cyano group, more preferably a hydrogen atom, a perfluoroalkyl group, an alkyl group, an aryl group, a fluorine atom and a cyano group, and particularly preferably a hydrogen atom, a perfluoroalkyl group and a cyano group.
  • R represented by A 407 , A 409 , A 411 and A 413 is preferably a hydrogen atom, alkyl group, perfluoroalkyl group, aryl group, amino group, alkoxy group, aryloxy group, fluorine atom or cyano group, more preferably Is a hydrogen atom, a perfluoroalkyl group, a fluorine atom or a cyano group, particularly preferably a hydrogen atom or a fluorine atom.
  • R represented by A 410 and A 414 is preferably a hydrogen atom or a fluorine atom, and more preferably a hydrogen atom.
  • Rs may be connected to each other to form a ring.
  • platinum complexes represented by the general formula (C-1) another more preferable embodiment is a platinum complex represented by the following general formula (C-5).
  • L 51 represents a single bond or a divalent linking group.
  • a 51 each independently represent a carbon atom or a nitrogen atom.
  • Z 51 and Z 52 each independently represent a nitrogen-containing aromatic heterocycle.
  • Z 53 each independently represents a benzene ring or an aromatic heterocycle.
  • Y is an anionic acyclic ligand that binds to Pt.
  • L 51 has the same meaning as L 1 in formula (C-1), and the preferred range is also the same.
  • a 51 represents a carbon atom or a nitrogen atom. In view of the stability of the complex and the light emission quantum yield of the complex, A 51 is preferably a carbon atom.
  • Z 51 and Z 52 are synonymous with Z 21 and Z 22 in the general formula (C-2), respectively, and preferred ranges thereof are also the same.
  • Z 53 has the same meaning as Z 23 in the general formula (C-2), and the preferred ranges are also the same.
  • Y is an anionic acyclic ligand that binds to Pt.
  • An acyclic ligand is one in which atoms bonded to Pt do not form a ring in the form of a ligand.
  • a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom are preferable, a nitrogen atom and an oxygen atom are more preferable, and an oxygen atom is the most preferable.
  • a vinyl ligand is mentioned as Y couple
  • Examples of Y bonded to Pt with an oxygen atom include an alkoxy ligand, an aryloxy ligand, a heteroaryloxy ligand, an acyloxy ligand, a silyloxy ligand, a carboxyl ligand, a phosphate ligand, Examples thereof include sulfonic acid ligands.
  • Examples of Y bonded to Pt with a sulfur atom include alkyl mercapto ligands, aryl mercapto ligands, heteroaryl mercapto ligands, and thiocarboxylic acid ligands.
  • the ligand represented by Y may have a substituent, and those listed as the substituent group A can be appropriately applied as the substituent. Moreover, substituents may be connected to each other.
  • the ligand represented by Y is preferably a ligand bonded to Pt with an oxygen atom, more preferably an acyloxy ligand, an alkyloxy ligand, an aryloxy ligand, a heteroaryloxy ligand. , A silyloxy ligand, and more preferably an acyloxy ligand.
  • platinum complexes represented by the general formula (C-5) one of more preferred embodiments is a platinum complex represented by the following general formula (C-6).
  • a 601 to A 610 each independently represents C—R or a nitrogen atom.
  • R represents a hydrogen atom or a substituent.
  • L 61 represents a single bond or a divalent linking group.
  • Y is an anionic acyclic ligand that binds to Pt.
  • L 61 has the same meaning as L 51 in formula (C-5), and the preferred range is also the same.
  • a 601 to A 610 have the same meanings as A 301 to A 310 in formula (C-3), and preferred ranges are also the same.
  • Y has the same meaning as that in formula (C-5), and the preferred range is also the same.
  • platinum complex represented by the general formula (C-1) include paragraph numbers [0143] to [0152], [0157] to [0158], [0162] to [0162] to [0162] of [2005-310733].
  • 0168 compounds described in JP-A-2006-256999, paragraphs [0065] to [0083], compounds described in JP-A-2006-93542, paragraphs [0065]-[0090] , Compounds described in paragraph numbers [0063] to [0071] of JP-A No. 2007-73891, compounds described in paragraph numbers [0079] to [0083] of JP-A No. 2007-324309, and JP-A 2006-93542 Compounds described in paragraph Nos.
  • Examples of the platinum complex compound represented by the general formula (C-1) include Journal of Organic Chemistry 53,786, (1988), G.S. R. Newkome et al. ), Page 789, method described in left column 53 to right column 7, line 790, method described in left column 18 to 38, method 790, method described in right column 19 to 30 and The combination, Chemische Berichte 113, 2749 (1980), H.C. Lexy et al.), Page 2752, lines 26 to 35, and the like.
  • a ligand or a dissociated product thereof and a metal compound are mixed with a solvent (for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, an amide solvent, a sulfone solvent,
  • a solvent for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, an amide solvent, a sulfone solvent
  • a base inorganic and organic bases such as sodium methoxide, t-butoxypotassium, triethylamine, potassium carbonate, etc.
  • a base inorganic and organic bases such as sodium methoxide, t-butoxypotassium, triethylamine, potassium carbonate, etc.
  • the content of the compound represented by formula (C-1) in the light emitting layer of the present invention is preferably 1 to 30% by mass, more preferably 3 to 25% by mass in the light emitting layer. More preferably, it is 20 mass%.
  • the host material is a compound mainly responsible for charge injection and transport in the light emitting layer, and itself is a compound that does not substantially emit light.
  • “substantially does not emit light” means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less, more preferably 3% or less of the total amount of light emitted from the entire device. Preferably it says 1% or less.
  • the host material a compound represented by any one of the general formulas (1) to (3) of the present invention can be used.
  • Examples of other host materials that can be used in the present invention include the following compounds. Pyrrole, indole, carbazole, azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone , Stilbene, silazane, aromatic tertiary amine compounds, styrylamine compounds, porphyrin compounds, polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiophene oligomers, polythiophene and other conductive polymer oligomers Organic silane, carbon film, pyridine, pyrimidine, triazine, imidazole, pyr
  • the host material that can be used in combination may be a hole transporting host material or an electron transporting host material, but a hole transporting host material can be used.
  • the light emitting layer preferably contains a host material.
  • the host material is preferably a compound represented by the following general formula (4-1) or (4-2). In the present invention, it is more preferable that the light emitting layer contains at least one compound represented by the general formula (4-1) or (4-2).
  • the compound represented by the general formula (4-1) or (4-2) when the compound represented by the general formula (4-1) or (4-2) is contained in the light emitting layer, the compound represented by the general formula (4-1) or (4-2) is
  • the light emitting layer preferably contains 30 to 100% by mass, more preferably 40 to 100% by mass, and particularly preferably 50 to 100% by mass.
  • each layer when the compound represented by the general formula (4-1) or (4-2) is used in a plurality of organic layers, it is preferable that each layer contains the above-mentioned range.
  • the compound represented by the general formula (4-1) or (4-2) may contain only one kind in any organic layer, and a plurality of general formulas (4-1) or (4) The compound represented by -2) may be contained in combination at any ratio.
  • R ′ 8 is Each independently represents a substituent, and when d, e and f are 2 or more, R ′ 8 may be different or the same, and at least one of R ′ 8 is represented by the following general formula (5). Represents a carbazole group.
  • R ′ 9 each independently represents a substituent.
  • G represents an integer of 0 to 8.
  • R ′ 8 independently represents a substituent, specifically, a halogen atom, an alkoxy group, a cyano group, a nitro group, an alkyl group, an aryl group, a heterocyclic group, or a substituent represented by the general formula (5) It is.
  • R ′ 8 does not represent the general formula (5), it is preferably an alkyl group having 10 or less carbon atoms, a substituted or unsubstituted aryl group having 10 or less carbon atoms, and more preferably an alkyl group having 6 or less carbon atoms. It is.
  • R ′ 9 each independently represents a substituent, specifically a halogen atom, an alkoxy group, a cyano group, a nitro group, an alkyl group, an aryl group, or a heterocyclic group, preferably an alkyl group having 10 or less carbon atoms, A substituted or unsubstituted aryl group having 10 or less carbon atoms, more preferably an alkyl group having 6 or less carbon atoms.
  • g represents an integer of 0 to 8 and is preferably 0 to 4 from the viewpoint of not shielding too much the carbazole skeleton responsible for charge transport. From the viewpoint of ease of synthesis, when carbazole has a substituent, those having a substituent so as to be symmetric with respect to the nitrogen atom are preferable.
  • the sum of d and e is preferably 2 or more from the viewpoint of maintaining the charge transport ability.
  • R ′ 8 is preferably substituted with meta for the other benzene ring. The reason for this is that in ortho substitution, the steric hindrance between adjacent substituents is large, so that the bond is easily cleaved, and the durability is lowered.
  • the molecular shape approaches a rigid rod shape and is easily crystallized, so that element degradation is likely to occur under high temperature conditions.
  • a compound represented by the following structure is preferable.
  • f is preferably 2 or more from the viewpoint of maintaining the charge transport ability.
  • R ′ 8 is substituted with meta from the same viewpoint.
  • a compound represented by the following structure is preferable.
  • an isotope of hydrogen such as a deuterium atom
  • all hydrogen atoms in the compound may be replaced with hydrogen isotopes, or a mixture in which a part is a compound containing hydrogen isotopes may be used.
  • R ′ 9 in the general formula (5) is substituted with deuterium, and the following structures are particularly preferable.
  • the atoms constituting the substituents also include their isotopes.
  • the compounds represented by the general formulas (4-1) and (4-2) can be synthesized by combining various known synthesis methods.
  • carbazole compounds are synthesized by dehydroaromatization after the Athercorp rearrangement reaction of a condensate of an aryl hydrazine and a cyclohexane derivative (LF Tieze, by Th. Eicher, translated by Takano, Ogasawara, Precision organic synthesis, page 339 (published by Nankodo).
  • LF Tieze by Th. Eicher, translated by Takano, Ogasawara, Precision organic synthesis, page 339 (published by Nankodo).
  • LF Tieze by Th. Eicher, translated by Takano, Ogasawara, Precision organic synthesis, page 339 (published by Nankodo).
  • LF Tieze by Th. Eicher, translated by Takano, Ogasawara, Precision organic synthesis, page 339 (published by Nankodo).
  • the compounds represented by the general formulas (4-1) and (4-2) preferably form a thin layer by a vacuum deposition process, but a wet process such as solution coating is also preferably used. I can do it.
  • the molecular weight of the compound is preferably 2000 or less, more preferably 1200 or less, and particularly preferably 800 or less from the viewpoints of deposition suitability and solubility. Also, from the viewpoint of vapor deposition suitability, if the molecular weight is too small, the vapor pressure becomes small, the change from the gas phase to the solid phase does not occur, and it is difficult to form an organic layer. Particularly preferred.
  • the general formulas (4-1) and (4-2) are preferably the following structures or compounds in which one or more hydrogen atoms are substituted with deuterium atoms.
  • the triplet lowest excitation energy (T 1 energy) of the host material is preferably higher than the T 1 energy of the phosphorescent light emitting material in terms of color purity, light emission efficiency, and driving durability. It is preferable T 1 is greater 0.1eV higher than the T 1 of the phosphorescent material of the host material, more preferably at least 0.2eV higher, and further preferably more than 0.3eV large. T 1 of the host material is a large T 1 is obtained from the phosphorescent material to the host material for thereby quench T 1 is less than the light emission of the phosphorescent material.
  • the content of the host compound in the present invention is not particularly limited, but from the viewpoint of light emission efficiency and driving voltage, it is 15% by mass to 95% by mass with respect to the total compound mass forming the light emitting layer. Preferably there is.
  • the light emitting layer contains a plurality of types of host compounds including the compound represented by any one of the general formulas (1) to (3), the compound represented by any one of the general formulas (1) to (3) is It is preferable that it is 50 to 99 mass% in all the host compounds.
  • the pair of electrodes include an anode, and at least one organic layer is included between the light emitting layer and the anode, and at least one of the following general formulas ( It is preferable to contain a compound represented by M-1).
  • the compound represented by the general formula (M-1) is more preferably contained in an organic layer adjacent to the light emitting layer between the light emitting layer and the anode, but its use is not limited, and It may be further contained in any of these layers.
  • a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, a charge block It can be contained in any or a plurality of layers.
  • the organic layer adjacent to the light emitting layer between the light emitting layer and the anode and containing the compound represented by the general formula (M-1) is more preferably a hole transport layer.
  • Ar 1 and Ar 2 are each independently one or more selected from alkyl, aryl, heteroaryl, arylamino, alkylamino, morpholino, thiomorpholino, N, O, and S It represents a 5- or 6-membered heterocycloalkyl or cycloalkyl containing a hetero atom, and may further have a substituent Z.
  • Ar 1 and Ar 2 may be bonded to each other by a single bond, alkylene, or alkenylene (with or without a condensed ring) to form a condensed 5- to 9-membered ring.
  • Ar 3 represents p-valent alkyl, aryl, heteroaryl, or arylamino, and may further have a substituent Z.
  • the substituents Z are each independently a halogen atom, —R ′′, —OR ′′, —N (R ′′) 2 , —SR ′′, —C (O) R ′′, —C (O) OR ′′, —C ( O) represents N (R ′′) 2 , —CN, —NO 2 , —SO 2 , —SOR ′′, —SO 2 R ′′, or —SO 3 R ′′, and each R ′′ independently represents a hydrogen atom, alkyl Represents a group, a perhaloalkyl group, an alkenyl group, an alkynyl group, an aryl group or a heteroaryl group.
  • p is an integer of 1 to 4, and when p is 2 or more, Ar 1 and Ar 2 may be the same or different.
  • Another preferred embodiment of the compound represented by the general formula (M-1) is a case represented by the following general formula (M-2).
  • R M1 represents an alkyl group, an aryl group, or a heteroaryl group.
  • R M2 to R M23 each independently represent a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, an amino group, a silyl group, a cyano group, a nitro group, or a fluorine atom.
  • R M1 represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). Which may have the aforementioned substituent Z.
  • R M1 is preferably an aryl group or a heteroaryl group, and more preferably an aryl group. Preferred substituents when the aryl group of R M1 has a substituent include an alkyl group, a halogen atom, a cyano group, an aryl group, and an alkoxy group, and an alkyl group, a halogen atom, a cyano group, and an aryl group are more preferable.
  • the aryl group of R M1 is preferably a phenyl group that may have a substituent Z, and more preferably a phenyl group that may have an alkyl group or a cyano group.
  • R M2 to R M23 are each independently a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), a heteroaryl group (preferably having 4 to 12 carbon atoms), Alkoxy group (preferably having 1 to 8 carbon atoms), aryloxy group (preferably having 6 to 30 carbon atoms), amino group (preferably having 0 to 24 carbon atoms), silyl group (preferably having 0 to 18 carbon atoms), cyano Represents a group, a nitro group, or a fluorine atom, and these may have the aforementioned substituent Z.
  • R M2 , R M7 , R M8 , R M15 , R M16 and R M23 are preferably a hydrogen atom or an alkyl group or an aryl group which may have a substituent Z, more preferably a hydrogen atom.
  • R M4 , R M5 , R M11 , R M12 , R M19, and R M20 are preferably a hydrogen atom, an alkyl or aryl group optionally having substituent Z, or a fluorine atom, more preferably a hydrogen atom. Is an atom.
  • R M3 , R M6 , R M9 , R M14 , R M17 and R M22 are preferably a hydrogen atom, an alkyl or aryl group optionally having substituent Z, a fluorine atom, or a cyano group, and more A hydrogen atom or an alkyl group which may have a substituent Z is preferable, and a hydrogen atom is more preferable.
  • R M10 , R M13 , R M18 and R M21 are preferably a hydrogen atom, an alkyl group optionally having a substituent Z, an aryl group, a heteroaryl group or an amino group, a nitro group, a fluorine atom, or a cyano group More preferably a hydrogen atom, an alkyl or aryl group optionally having a substituent Z, a nitro group, a fluorine atom, or a cyano group, still more preferably a hydrogen atom or a substituent Z. It is an alkyl group that may be present.
  • the substituent is preferably a fluorine atom
  • the alkyl group which may have the substituent Z preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms. is there.
  • Another preferred embodiment of the compound represented by the general formula (M-1) is a case represented by the following general formula (M-3).
  • R S1 to R S5 are each independently an alkyl group, cycloalkyl group, alkenyl group, alkynyl group, —CN, perfluoroalkyl group, trifluorovinyl group, —CO 2 R, —C (O) represents R, —NR 2 , —NO 2 , —OR, a halogen atom, an aryl group or a heteroaryl group, and may further have a substituent Z.
  • Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, an aryl group or a heteroaryl group.
  • R S1 to R S5 When a plurality of R S1 to R S5 are present, they may be bonded to each other to form a ring, and may further have a substituent Z.
  • a represents an integer of 0 to 4, and when a plurality of R S1 are present, they may be the same or different and may be bonded to each other to form a ring.
  • b to e each independently represent an integer of 0 to 5, and when there are a plurality of R S2 to R S5 , they may be the same or different, and any two may combine to form a ring.
  • q is an integer of 1 to 5, and when q is 2 or more, a plurality of R S1 may be the same or different, and may be bonded to each other to form a ring.
  • the alkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z.
  • the alkyl group represented by R S1 to R S5 is preferably an alkyl group having 1 to 8 carbon atoms in total, more preferably an alkyl group having 1 to 6 carbon atoms in total, such as a methyl group or an ethyl group. , I-propyl group, cyclohexyl group, t-butyl group and the like.
  • the cycloalkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z.
  • the cycloalkyl group represented by R S1 to R S5 is preferably a cycloalkyl group having 4 to 7 ring members, more preferably a cycloalkyl group having 5 to 6 carbon atoms in total, such as a cyclopentyl group and cyclohexyl group. Groups and the like.
  • the alkenyl group represented by R S1 to R S5 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms.
  • vinyl, allyl, 1-propenyl Examples include 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl and the like.
  • the alkynyl group represented by R S1 to R S5 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms.
  • Examples of the perfluoroalkyl group represented by R S1 to R S5 include those in which all hydrogen atoms of the aforementioned alkyl group are replaced with fluorine atoms.
  • the aryl group represented by R S1 to R S5 is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, such as a phenyl group, a tolyl group, a biphenyl group, and a terphenyl group.
  • the heteroaryl group represented by R S1 to R S5 is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or 6-membered substituted or unsubstituted heteroaryl group,
  • R S1 to R S5 are preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluoro group, an aryl group, or a heteroaryl group, more preferably a hydrogen atom or an alkyl group.
  • Group, cyano group, trifluoromethyl group, fluoro group and aryl group more preferably a hydrogen atom, an alkyl group and an aryl group.
  • substituent Z an alkyl group, an alkoxy group, a fluoro group, a cyano group, and a dialkylamino group are preferable, and a hydrogen atom and an alkyl group are more preferable.
  • R S1 to R S5 may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl;
  • the 7-membered ring may further have a substituent Z.
  • the definition and preferred range of cycloalkyl, aryl, and heteroaryl formed are the same as the cycloalkyl group, aryl group, and heteroaryl group defined by R S1 to R S5 .
  • the compound represented by the general formula (M-1) is preferably contained in an amount of 50 to 100% by mass, The content is preferably 100% by mass, and particularly preferably 95 to 100% by mass.
  • each layer contains the above-mentioned range.
  • the compound represented by the general formula (M-1) may contain only one kind in any organic layer, and the compound represented by the plurality of general formulas (M-1) You may contain in combination.
  • the thickness of the hole transport layer containing the compound represented by the general formula (M-1) is preferably 1 nm to 500 nm, more preferably 3 nm to 200 nm, and more preferably 5 nm to 100 nm. Further preferred.
  • the hole transport layer is preferably provided in contact with the light emitting layer.
  • the hole transport layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
  • the lowest excited triplet (T 1 ) energy in the film state of the compound represented by the general formula (M-1) is preferably 2.52 eV (58 kcal / mol) or more and 3.47 eV (80 kcal / mol) or less. It is more preferably 2.60 eV (60 kcal / mol) or more and 3.25 eV (75 kcal / mol) or less, and further preferably 2.69 eV (62 kcal / mol) or more and 3.04 eV (70 kcal / mol) or less.
  • the hydrogen atom constituting the general formula (M-1) includes hydrogen isotopes (such as deuterium atoms). In this case, all hydrogen atoms in the compound may be replaced with hydrogen isotopes, or a mixture in which a part is a compound containing hydrogen isotopes may be used.
  • the compound represented by the general formula (M-1) can be synthesized by combining various known synthesis methods.
  • carbazole compounds are synthesized by dehydroaromatization after the Athercorp rearrangement reaction of a condensate of an aryl hydrazine and a cyclohexane derivative (LF Tieze, by Th. Eicher, translated by Takano, Ogasawara, Precision organic synthesis, page 339 (published by Nankodo).
  • LF Tieze by Th. Eicher, translated by Takano, Ogasawara, Precision organic synthesis, page 339 (published by Nankodo).
  • LF Tieze by Th. Eicher
  • Takano, Ogasawara, Precision organic synthesis page 339 (published by Nankodo).
  • Tetrahedron Letters 39: 617 (1998), 39: 2367 (1998) and 40: 6393 (1999) and the like Tetrahedron Letters 39: 617 (1998), 39: 2367 (1998) and 40
  • the compound represented by the general formula (M-1) of the present invention is preferably formed into a thin layer by a vacuum deposition process, but a wet process such as solution coating can also be suitably used.
  • the molecular weight of the compound is preferably 2000 or less, more preferably 1200 or less, and particularly preferably 800 or less from the viewpoints of deposition suitability and solubility. Also, from the viewpoint of vapor deposition suitability, if the molecular weight is too small, the vapor pressure becomes small, the change from the gas phase to the solid phase does not occur, and it is difficult to form an organic layer. Particularly preferred. *
  • the pair of electrodes preferably includes a cathode, and preferably includes at least one organic layer between the light emitting layer and the cathode, and the organic layer includes an aromatic hydrocarbon compound. It is preferable to do.
  • the aromatic hydrocarbon compound is more preferably contained in an organic layer adjacent to the light emitting layer between the light emitting layer and the cathode, but its use is not limited, and any of the organic layers may be further added. It may be contained.
  • any one or more of a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, and a charge block layer are used. It can contain.
  • the organic layer adjacent to the light emitting layer between the light emitting layer and the cathode and containing the aromatic hydrocarbon compound is preferably a charge blocking layer or an electron transporting layer, and more preferably an electron transporting layer.
  • the aromatic hydrocarbon compound preferably comprises only carbon atoms and hydrogen atoms from the viewpoint of ease of synthesis.
  • the aromatic hydrocarbon compound is contained in a layer other than the light emitting layer, it is preferably contained in an amount of 70 to 100% by mass, more preferably 85 to 100% by mass.
  • the aromatic hydrocarbon compound is contained in the light emitting layer, it is preferably contained in an amount of 0.1 to 99% by weight, more preferably 1 to 95% by weight, based on the total weight of the light emitting layer. It is more preferable to include the mass%.
  • the condensed polycyclic skeleton having 13 to 22 carbon atoms is preferably any one of fluorene, anthracene, phenanthrene, tetracene, chrysene, pentacene, pyrene, perylene, and triphenylene.
  • fluorene, triphenylene, phenanthrene Is more preferable, and triphenylene is more preferable from the viewpoint of stability of the compound and charge injection / transport properties, and a compound represented by the general formula (Tp-1) is particularly preferable.
  • the hydrocarbon compound represented by the general formula (Tp-1) preferably has a molecular weight in the range of 400 to 1200, more preferably 400 to 1000, and still more preferably 400 to 800. If the molecular weight is 400 or more, a high-quality amorphous thin film can be formed, and if the molecular weight is 1200 or less, it is preferable in terms of solubility in a solvent, sublimation, and appropriate deposition.
  • hydrocarbon compound represented by the general formula (Tp-1) is not limited, and it may be further contained not only in the organic layer adjacent to the light emitting layer but also in any layer within the organic layer.
  • R 12 to R 23 are each independently a hydrogen atom, an alkyl group or an alkyl group, a phenyl group optionally substituted with a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, Represents a fluorenyl group, a naphthyl group, or a triphenylenyl group, provided that R 12 to R 23 are not all hydrogen atoms.
  • Examples of the alkyl group represented by R 12 to R 23 are substituted or unsubstituted, for example, methyl group, ethyl group, isopropyl group, n-butyl group, tert-butyl group, n-octyl group, n-decyl group, and an n-hexadecyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, and the like, preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, and a cyclohexyl group, more preferably a methyl group, an ethyl group, or A tert-butyl group.
  • R 12 to R 23 are preferably an alkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group (these are further an alkyl group, a phenyl group, a fluorenyl group). More preferably a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, which may be substituted with a group, a naphthyl group, or a triphenylenyl group.
  • a benzene ring that may be substituted with a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group (which may be further substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group); It is particularly preferred.
  • the total number of aryl rings is preferably 2 to 8, and preferably 3 to 5. By setting it as this range, a high-quality amorphous thin film can be formed, and solubility in a solvent, sublimation, and deposition suitability are improved.
  • R 12 to R 23 each independently preferably has a total carbon number of 20 to 50, more preferably a total carbon number of 20 to 36. By setting it as this range, a high-quality amorphous thin film can be formed, and solubility in a solvent, sublimation, and deposition suitability are improved.
  • the hydrocarbon compound represented by the general formula (Tp-1) is preferably a hydrocarbon compound represented by the following general formula (Tp-2).
  • a plurality of Ar 1 are the same, and a phenyl group, a fluorenyl group, a naphthyl group, which may be substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, Or represents a triphenylenyl group.
  • An alkyl group and an alkyl group represented by Ar 1 , a phenyl group, a fluorenyl group, a naphthyl group, or a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group that may be substituted with a triphenylenyl group include R 12 to R 23 . It is synonymous with what was mentioned, and a preferable thing is also the same.
  • the hydrocarbon compound represented by the general formula (Tp-1) is preferably a hydrocarbon compound represented by the following general formula (Tp-3).
  • L represents an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a phenyl group, a fluorenyl group, a naphthyl group, a triphenylenyl group, which may be substituted with a triphenylenyl group, or a combination thereof.
  • n represents an integer of 1 to 6.
  • the alkyl group, phenyl group, fluorenyl group, naphthyl group, or triphenylenyl group that forms the n-valent linking group represented by L has the same meaning as that described for R 12 to R 23 .
  • L is preferably an alkyl group or an n-valent linking group formed by combining a benzene ring, a fluorene ring, or a combination thereof, which may be substituted with a benzene ring.
  • L is bonded to the triphenylene ring by *.
  • N is preferably 1 to 5, and more preferably 1 to 4.
  • the hydrocarbon compound represented by the general formula (Tp-1) is preferably a hydrocarbon compound represented by the following general formula (Tp-4).
  • Ar 2 in the case where a plurality of Ar 2 are present is the same, and Ar 2 represents a group formed by substitution with an alkyl group, phenyl group, naphthyl group, or triphenylenyl group, or a combination thereof.
  • Ar 2 represents a group formed by substitution with an alkyl group, phenyl group, naphthyl group, or triphenylenyl group, or a combination thereof.
  • And q each independently represent 0 or 1, but p and q are not simultaneously 0.
  • Ar 2 represents a hydrogen atom.
  • Ar 2 is preferably a group formed by combining an alkyl group having 1 to 4 carbon atoms, a phenyl group, a naphthyl group, or a triphenylenyl group, and more preferably a combination of a methyl group, a t-butyl group, a phenyl group, or a triphenylenyl group. It is a group consisting of Ar 2 is particularly preferably a benzene ring substituted with an alkyl group having 1 to 4 carbon atoms at the meta position, a phenyl group, a naphthyl group, a triphenylenyl group, or a combination thereof.
  • the hydrocarbon compound according to the present invention is used as a host material of a light emitting layer of an organic electroluminescent device or a charge transport material of a layer adjacent to the light emitting layer, the energy gap in a thin film state than the light emitting material (the light emitting material is a phosphorescent light emitting material)
  • the energy gap and T 1 energy are not too large.
  • the T 1 energy in the film state of the hydrocarbon compound represented by the general formula (Tp-1) is preferably 52 kcal / mol or more and 80 kcal / mol or less, and 55 kcal / mol or more and 68 kcal / mol or less. Is more preferable, and it is still more preferable that they are 58 kcal / mol or more and 63 kcal / mol or less. In particular, when a phosphorescent light emitting material is used as the light emitting material, the T 1 energy is preferably in the above range.
  • the T 1 energy can be obtained by a method similar to the method in the description of the general formula (1) described above.
  • the glass transition temperature (Tg) of the hydrocarbon compound according to the present invention is 80 ° C. or more and 400 ° C. or less from the viewpoint of stably operating the organic electroluminescence device against heat generated during high temperature driving or during device driving. Preferably, it is 100 degreeC or more and 400 degrees C or less, More preferably, it is 120 degreeC or more and 400 degrees C or less.
  • the compounds exemplified as the hydrocarbon compounds according to the present invention include those described in International Publication No. 05/013388, International Publication No. 06/130598, International Publication No. 09/021107, US2009 / 0009065, International Publication No. 09 / It can be synthesized by the methods described in the 008311 pamphlet and the international publication 04/018587 pamphlet. After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.
  • the light emitting device of the present invention preferably includes at least one organic layer between the light emitting layer and the cathode, and the organic layer contains at least one compound represented by the following general formula (O-1). Is preferable from the viewpoints of element efficiency and driving voltage.
  • the general formula (O-1) will be described below.
  • R O1 represents an alkyl group, an aryl group, or each independently .A O1 ⁇ A O4 representing the heteroaryl group, the C-R A or .R A representing the nitrogen atom Represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R A may be the same or different, and L O1 represents a divalent to hexavalent linking group comprising an aryl ring or a heteroaryl ring.
  • N O1 represents an integer of 2 to 6.
  • R O1 represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms).
  • Z ′ may be included.
  • R O1 is preferably an aryl group or a heteroaryl group, more preferably an aryl group.
  • an alkyl group, an aryl group or a cyano group can be mentioned, an alkyl group or an aryl group is more preferable, and an aryl group is still more preferable.
  • the aryl group of R O1 When the aryl group of R O1 has a plurality of substituents, the plurality of substituents may be bonded to each other to form a 5- or 6-membered ring.
  • the aryl group of R O1 is preferably a phenyl group which may have a substituent Z ′, more preferably a phenyl group which may be substituted with an alkyl group or an aryl group, and still more preferably unsubstituted.
  • a O1 to A O4 each independently represent C—R A or a nitrogen atom.
  • 0 to 2 are preferably nitrogen atoms, and 0 or 1 is more preferably a nitrogen atom.
  • all of A O1 ⁇ A O4 is C-R A, or A O1 be a nitrogen atom, is preferably A O2 ⁇ A O4 is C-R A, A O1 be a nitrogen atom, A O2 ⁇ More preferably, A O4 is C—R A , more preferably A O1 is a nitrogen atom, A O2 to A O4 are C—R A , and R A is all a hydrogen atom.
  • R A represents a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). It may have a substituent Z ′.
  • the plurality of RA may be the same or different.
  • R A is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
  • L O1 represents a divalent to hexavalent linking group composed of an aryl ring (preferably having 6 to 30 carbon atoms) or a heteroaryl ring (preferably having 4 to 12 carbon atoms).
  • L O1 is preferably an arylene group, heteroarylene group, aryltriyl group, or heteroaryltriyl group, more preferably a phenylene group, a biphenylene group, or a benzenetriyl group, still more preferably a biphenylene group, Or it is a benzenetriyl group.
  • L O1 may have the above-described substituent Z ′, and when it has a substituent, the substituent is preferably an alkyl group, an aryl group, or a cyano group. Specific examples of L O1 include the following.
  • n O1 represents an integer of 2 to 6, preferably an integer of 2 to 4, more preferably 2 or 3. n O1 is most preferably 3 from the viewpoint of device efficiency, and most preferably 2 from the viewpoint of device durability.
  • the compound represented by the general formula (O-1) is more preferably a compound represented by the following general formula (O-2).
  • R O1 represents an alkyl group, an aryl group, or a heteroaryl group.
  • R O2 to R O4 each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group.
  • a O1 to A O4 each independently represent C—R A or a nitrogen atom, R A represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R A may be the same or different. May be.
  • R O1 and A O1 ⁇ A O4 the general formula (O1) in the same meaning as R O1 and A O1 ⁇ A O4 of, also the same preferable ranges thereof.
  • R 02 to R 04 are each independently a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). Which may have the aforementioned substituent Z ′.
  • R 02 to R 04 are preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an aryl group, and most preferably a hydrogen atom.
  • the compound represented by the general formula (O-1) has a glass transition temperature (Tg) of 100 ° C. from the viewpoint of stable operation at high temperature storage, stable operation against high temperature driving, and heat generation during driving. It is preferably from ⁇ 300 ° C., more preferably from 120 ° C. to 300 ° C., further preferably from 120 ° C. to 300 ° C., and still more preferably from 140 ° C. to 300 ° C.
  • the compound represented by the general formula (O-1) can be synthesized by the method described in JP-A No. 2001-335776. After synthesis, purification by column chromatography, recrystallization, reprecipitation, etc., followed by purification by sublimation is preferred. Not only can organic impurities be separated by sublimation purification, but inorganic salts, residual solvents, moisture, and the like can be effectively removed.
  • the compound represented by the general formula (O-1) is contained in an organic layer between the light emitting layer and the cathode, but is contained in a layer on the cathode side adjacent to the light emitting layer. Is preferred.
  • the charge transport layer is a layer in which charge transfer occurs when a voltage is applied to the organic electroluminescent element.
  • Specific examples include a hole injection layer, a hole transport layer, an electron block layer, a light emitting layer, a hole block layer, an electron transport layer, and an electron injection layer.
  • a hole injection layer, a hole transport layer, an electron blocking layer, or a light emitting layer is preferable. If the charge transport layer formed by the coating method is a hole injection layer, a hole transport layer, an electron blocking layer, or a light emitting layer, it is possible to manufacture an organic electroluminescent element with low cost and high efficiency.
  • the charge transport layer is more preferably a hole injection layer, a hole transport layer, or an electron block layer.
  • the hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side.
  • the hole injection layer and the hole transport layer the matters described in paragraph numbers [0165] to [0167] of JP-A-2008-270736 can be applied to the present invention.
  • the hole injection layer preferably contains an electron accepting dopant.
  • an electron-accepting dopant may be any organic material or inorganic material as long as it can extract electrons from the doped material and generate radical cations.
  • TCNQ tetracyanoquinodimethane
  • F 4 -TCNQ tetrafluorotetracyanoquinodimethane
  • molybdenum oxide and the like.
  • the electron-accepting dopant in the hole injection layer is preferably contained in an amount of 0.01% by mass to 50% by mass, and preferably 0.1% by mass to 40% by mass with respect to the total mass of the compound forming the hole injection layer. %, More preferably 0.2% by mass to 30% by mass.
  • the electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side.
  • the electron injection material and the electron transport material used for these layers may be a low molecular compound or a high molecular compound.
  • As the electron transport material a compound represented by any one of the general formulas (1) to (3) of the present invention can be used.
  • Other materials include pyridine derivatives, quinoline derivatives, pyrimidine derivatives, pyrazine derivatives, phthalazine derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, Metal complexes of anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, naphthalene, perylene, and other aromatic ring tetracarboxylic anhydrides, phthalocyanine derivatives, 8-quinolinol derivatives And metal phthalocyanines, various metal complexes represented by metal complexes with benzoxazole and benzothiazole ligands, It is preferable that a layer
  • the thicknesses of the electron injection layer and the electron transport layer are each preferably 500 nm or less from the viewpoint of lowering the driving voltage.
  • the thickness of the electron transport layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.
  • the thickness of the electron injection layer is preferably from 0.1 nm to 200 nm, more preferably from 0.2 nm to 100 nm, and even more preferably from 0.5 nm to 50 nm.
  • the electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
  • the electron injection layer preferably contains an electron donating dopant.
  • an electron donating dopant may be any organic material or inorganic material as long as it can give electrons to the doped material and generate radical anions.
  • TTF tetrathiafulvalene
  • TTT dithiaimidazole compounds
  • TTT tetrathianaphthacene
  • bis- [1,3 diethyl-2-methyl-1,2-dihydrobenzimidazolyl] lithium, cesium and the like.
  • the electron donating dopant in the electron injection layer is preferably contained in an amount of 0.01% by mass to 50% by mass, and 0.1% by mass to 40% by mass with respect to the total mass of the compound forming the electron injection layer. More preferably, the content is 0.5 to 30% by mass.
  • the hole blocking layer is a layer having a function of preventing holes transported from the anode side to the light emitting layer from passing through to the cathode side.
  • a hole blocking layer can be provided as an organic layer adjacent to the light emitting layer on the cathode side.
  • organic compounds constituting the hole blocking layer include aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (Aluminum (III) bis (2-methyl-8-quinolinato) 4- aluminum complexes such as phenylphenolate (abbreviated as Balq)), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (2,9-dimethyl-4,7-diphenyl-1,10-) phenanthroline derivatives such as phenanthroline (abbreviated as BCP)) and the compounds of the present invention.
  • BCP phenanthroline
  • the hole blocking layer is not limited to the function of actually blocking holes, and the exciton of the light emitting layer may not diffuse into the electron transport layer, or may have a function of blocking energy transfer quenching. .
  • the compound of the present invention can also be preferably applied as a hole blocking layer (add this description to the dibenzothiophene-phenanthrene project).
  • the thickness of the hole blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.
  • the hole blocking layer may have a single layer structure made of one or more of the materials described above, or may have a multilayer structure made of a plurality of layers having the same composition or different compositions.
  • the electron blocking layer is a layer having a function of preventing electrons transported from the cathode side to the light emitting layer from passing through to the anode side.
  • an electron blocking layer can be provided as an organic layer adjacent to the light emitting layer on the anode side.
  • the thickness of the electron blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.
  • the electron blocking layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
  • the entire organic EL element may be protected by a protective layer.
  • the protective layer the matters described in JP-A-2008-270736, paragraphs [0169] to [0170] can be applied to the present invention.
  • the element of this invention may seal the whole element using a sealing container.
  • the sealing container the matters described in paragraph [0171] of JP-A-2008-270736 can be applied to the present invention.
  • the organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode.
  • a direct current which may include an alternating current component as necessary
  • the driving method of the organic electroluminescence device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-290080, JP-A-7-134558, JP-A-8-234585, and JP-A-8-2441047.
  • the driving methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6,023,308 can be applied.
  • the external quantum efficiency of the organic electroluminescent element of the present invention is preferably 7% or more, more preferably 10% or more, and further preferably 12% or more.
  • the value of the external quantum efficiency should be the maximum value of the external quantum efficiency when the device is driven at 20 ° C., or the value of the external quantum efficiency around 300 to 400 cd / m 2 when the device is driven at 20 ° C. Can do.
  • the internal quantum efficiency of the organic electroluminescence device of the present invention is preferably 30% or more, more preferably 50% or more, and further preferably 70% or more.
  • the internal quantum efficiency of the device is calculated by dividing the external quantum efficiency by the light extraction efficiency. In a normal organic EL element, the light extraction efficiency is about 20%.
  • the element of the present invention can be suitably used for a display element, a display, a backlight, electrophotography, an illumination light source, a recording light source, an exposure light source, a reading light source, a sign, a signboard, an interior, or optical communication.
  • a device driven in a region having a high light emission luminance such as a lighting device or a display device.
  • FIG. 2 is a cross-sectional view schematically showing an example of the light emitting device of the present invention.
  • the light-emitting device 20 of FIG. 2 is comprised by the board
  • FIG. 1 is a cross-sectional view schematically showing an example of the light emitting device of the present invention.
  • the light-emitting device 20 of FIG. 2 is comprised by the board
  • the organic electroluminescent device 10 is configured by sequentially laminating an anode (first electrode) 3, an organic layer 11, and a cathode (second electrode) 9 on a substrate 2.
  • a protective layer 12 is laminated on the cathode 9, and a sealing container 16 is provided on the protective layer 12 with an adhesive layer 14 interposed therebetween.
  • a part of each electrode 3 and 9, a partition, an insulating layer, etc. are abbreviate
  • the adhesive layer 14 a photocurable adhesive such as an epoxy resin or a thermosetting adhesive can be used, and for example, a thermosetting adhesive sheet can also be used.
  • the use of the light-emitting device of the present invention is not particularly limited, and for example, it can be a display device such as a television, a personal computer, a mobile phone, and electronic paper in addition to a lighting device.
  • FIG. 3 is a cross-sectional view schematically showing an example of the illumination device of the present invention.
  • the illumination device 40 of the present invention includes the organic EL element 10 and the light scattering member 30 described above. More specifically, the lighting device 40 is configured such that the substrate 2 of the organic EL element 10 and the light scattering member 30 are in contact with each other.
  • the light scattering member 30 is not particularly limited as long as it can scatter light.
  • the light scattering member 30 is a member in which fine particles 32 are dispersed on a transparent substrate 31.
  • the transparent substrate 31 for example, a glass substrate can be preferably cited.
  • transparent resin fine particles can be preferably exemplified.
  • the glass substrate and the transparent resin fine particles known ones can be used.
  • the incident light is scattered by the light scattering member 30, and the scattered light is emitted from the light emitting surface 30B. It is emitted as illumination light.
  • a 500 ml three-necked flask was purged with nitrogen, and 4 g of compound (a-4) and 100 ml of dehydrated THF were added and stirred. After dissolution, it was immersed in a dry ice-acetone bath, and 4.8 ml of n-BuLi was added dropwise at -78 ° C to -60 ° C. The temperature was raised to ⁇ 40 ° C. and the mixture was stirred for 1.5 hours, and then the temperature was raised to 0 ° C. and the mixture was stirred for 1 hour. The mixture was cooled again to ⁇ 40 ° C., 0.9 ml of trimethoxyborane was added dropwise, and the mixture was stirred for 1.5 hours.
  • the obtained compound (1-1) was identified by 1 H-NMR. The 1 H-NMR data is shown in FIG.
  • Synthesis Example 2 Synthesis of Compounds 1-2 to 1-5 Compounds 1-2 to 1-5 were synthesized according to the scheme shown below. Reaction conditions and purification operations are the same as in Synthesis Example 1.
  • the compound containing a dibenzofuran structure was synthesized in the same manner as the compound containing a dibenzothiophene structure.
  • Example 1 A glass substrate having a thickness of 0.5 mm and a 2.5 cm square ITO film (manufactured by Geomat Co., Ltd., surface resistance 10 ⁇ / ⁇ ) is placed in a cleaning container, subjected to ultrasonic cleaning in 2-propanol, and then subjected to UV-ozone treatment for 30 minutes. Went. The following organic layers were sequentially deposited on the transparent anode (ITO film) by vacuum deposition.
  • ITO film transparent anode
  • First layer Compound A: film thickness 10 nm
  • Second layer NPD: film thickness 25 nm
  • Third layer Compound (1-1) and GD-1 (mass ratio 90:10): film thickness 30 nm
  • Fourth layer Compound (1-1): Film thickness 10 nm
  • Fifth layer Alq: film thickness 45 nm
  • 0.1 nm of lithium fluoride and 100 nm of metallic aluminum were vapor-deposited in this order to form a cathode.
  • This laminated body is put in a glove box substituted with nitrogen gas without being exposed to the atmosphere, and sealed with a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.). The device 1 was obtained.
  • Examples 2 to 7, Comparative Examples 1 to 3 As in the case of the element 1, the compound (1-1) of the third layer and the fourth layer is changed from the compound (1-2) to the compound (1-5), the compound (1-7), the compound (1-11) and the comparison. By substituting compound (1) to comparative compound (3), devices 2 to 7 and comparative devices 1 to 3 were obtained. Table 1 shows the results of evaluating these elements by the following methods in terms of efficiency, durability, efficiency change after high-temperature storage, and driving voltage.
  • Table 1 shows the case where it is 800 hours or longer as ⁇ , the case where it is 500 hours or longer and shorter than 800 hours, ⁇ , the case where it is 100 hours or longer and shorter than 500 hours, ⁇ , and the case where it is shorter than 100 hours as x.
  • the light-emitting element of the present invention is designed to increase the light emission efficiency in such a case. Therefore, it can be used advantageously.
  • the element of the present invention is excellent in luminous efficiency and durability even when used in a high temperature environment such as in-vehicle use, and is suitable for a light emitting device, a display device, and a lighting device.
  • the organic electroluminescent element can be used for a display element, a display, a backlight, electrophotography, an illumination light source, a recording light source, an exposure light source, a reading light source, a sign, a signboard, an interior, or optical communication.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Manufacturing & Machinery (AREA)
  • Electroluminescent Light Sources (AREA)
  • Furan Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Devices For Indicating Variable Information By Combining Individual Elements (AREA)

Abstract

La présente invention concerne un élément électroluminescent organique, présentant à un degré élevé les attributs suivants : fort rendement lumineux, durabilité, faible tension d'excitation, et inhibition de la baisse du rendement lumineux après un stockage sous haute température. L'invention concerne également un composé servant dans ledit élément électroluminescent organique. L'élément électroluminescent organique décrit comporte, sur un substrat, une paire d'électrodes composée d'une électrode positive et d'une électrode négative, et, entre lesdites électrodes, une ou plusieurs couches organiques incluant une couche émettrice de lumière. Ladite couche émettrice de lumière contient au moins une sorte de matériau phosphorescent, et au moins une couche parmi ladite ou lesdites couches organiques contient un composé spécifique présentant une structure de dibenzothiophène ou de dibenzofurane. L'invention concerne également ledit composé.
PCT/JP2011/066579 2010-07-30 2011-07-21 Elément électroluminescent organique, et composé associé Ceased WO2012014779A1 (fr)

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KR102571401B1 (ko) * 2018-06-01 2023-08-31 엘지디스플레이 주식회사 유기 화합물과 이를 포함하는 유기발광다이오드 및 유기발광 표시장치
US11697645B2 (en) 2018-12-28 2023-07-11 Samsung Electronics Co., Ltd. Heterocyclic compound, composition including heterocyclic compound, and organic light-emitting device including heterocyclic compound
KR102739126B1 (ko) 2020-06-10 2024-12-05 삼성전자주식회사 조성물 및 이를 포함한 유기 발광 소자

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