WO2017104839A1 - Complexe d'iridium émettant de la lumière rouge et matériau électroluminescent et élément électroluminescent organique utilisant chacun ledit composé - Google Patents

Complexe d'iridium émettant de la lumière rouge et matériau électroluminescent et élément électroluminescent organique utilisant chacun ledit composé Download PDF

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WO2017104839A1
WO2017104839A1 PCT/JP2016/087675 JP2016087675W WO2017104839A1 WO 2017104839 A1 WO2017104839 A1 WO 2017104839A1 JP 2016087675 W JP2016087675 W JP 2016087675W WO 2017104839 A1 WO2017104839 A1 WO 2017104839A1
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group
compound
iridium complex
alkyl group
hydrogen atom
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今野　英雄
吉朗 杉田
伊藤　賢
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Furuya Metal Co Ltd
National Institute of Advanced Industrial Science and Technology AIST
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Furuya Metal Co Ltd
National Institute of Advanced Industrial Science and Technology AIST
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present disclosure relates to a novel red-emitting iridium complex useful as a light-emitting material for organic light-emitting devices (such as organic electroluminescent devices and organic electrochemiluminescent devices) and an organic light-emitting device using the compound.
  • organic light-emitting devices such as organic electroluminescence devices have been attracting attention as display or illumination technology, and research for practical application is being actively promoted.
  • improvement of luminous efficiency is an important research subject, and attention is currently focused on phosphorescent materials that utilize light emission from an excited triplet state as light emitting materials.
  • the generation ratio of singlet excitons and triplet excitons is 1: 3, and the generation probability of luminescent excitons is 25%. Further, since the light extraction efficiency is about 20%, the limit of the external extraction quantum efficiency is set to 5%. On the other hand, if the excited triplet state can also be used for this, the upper limit of the internal quantum efficiency is 100%, so that in principle, the luminous efficiency is four times that of the excited singlet. Against this background, phosphorescent materials have been actively developed so far.
  • an iridium complex having a dibenzo [f, h] quinoxaline ligand represented by Chemical Formula 2 has been reported as a red phosphorescent material used in an organic light-emitting device (see, for example, Non-Patent Document 1).
  • the luminescence of this iridium complex contains a lot of orange components, and it is difficult to obtain red with good color purity. Therefore, in order to reduce the orange component, there is a strong demand to shift the emission spectrum of an iridium complex having a dibenzo [f, h] quinoxaline ligand by a long wavelength.
  • Non-Patent Document 1 describes that this iridium complex (Chemical Formula 2) has an emission maximum wavelength at 608 nm in dichloromethane.
  • an iridium complex in which an aryl group is introduced into the dibenzo [f, h] quinoxaline ligand shown in Chemical Formula 3 in order to shift the emission of the iridium complex having a dibenzo [f, h] quinoxaline ligand by a long wavelength.
  • This document describes that this iridium complex (Chemical Formula 3) has an emission maximum wavelength at 640 nm in dichloromethane.
  • Patent Document 1 an iridium complex represented by Chemical Formula 4 in which an aryl group is introduced into a dibenzo [f, h] quinoxaline ligand is disclosed (for example, see Patent Document 2).
  • This document describes that this iridium complex (Chemical Formula 4) has an emission maximum wavelength at 614 nm in toluene.
  • the iridium complex having a dibenzo [f, h] quinoxaline ligand emits light in the orange-red region, but in the future, development of an iridium complex having strong light emission in the red region and excellent sublimation properties. Is strongly desired.
  • An object of the present disclosure is to provide a novel iridium complex that can be applied to an organic electroluminescence device, an organic electrochemiluminescence device, and the like and that exhibits excellent light emission characteristics in a red region and has excellent sublimation properties.
  • the present inventors have surprisingly found one ligand having a dibenzo [f, h] quinoxaline skeleton and two ligands having a 2-phenylpyridine skeleton. It has been found that the iridium complex having a specific structure having one has high efficiency in the red region. Specifically, the novel iridium complex represented by the general formula (1) introduces an aryl group into the specific position of the dibenzo [f, h] quinoxaline ligand as described in Patent Documents 1 and 2 above.
  • the iridium complex according to the present invention is represented by the following general formula (1).
  • N represents a nitrogen atom.
  • Ir represents iridium.
  • R 1 to R 9 each independently represents a hydrogen atom, an alkyl group, or a halogen atom.
  • R 10 to R 17. Each independently represents a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, a cyano group, or a halogen atom, wherein the alkyl group is an aryl group, an alkoxy group, or a heterocyclic group.
  • the aryl group may be substituted with an alkyl group (excluding trifluoromethyl group), an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, or a halogen atom. (Excluding a fluorine atom) may be substituted with an aralkyl group, and the alkoxy group may be an aryl group, an alkoxy group, or a hetero group.
  • the heterocyclic group may be substituted with an alkyl group, an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, or a halogen atom.
  • the aryloxy group may be substituted with an alkyl group, an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, or a halogen atom, and adjacent R 10 to R 17 are each bonded to form a ring structure. It may be formed.
  • R 1 to R 9 are preferably each independently a hydrogen atom or an alkyl group.
  • R 10 to R 17 are preferably each independently a hydrogen atom, an alkyl group, or an aryl group.
  • R 10 to R 17 is an alkyl group.
  • R 10 to R 17 is an aryl group.
  • the iridium complex according to the present invention is preferably represented by the following general formula (2).
  • N represents a nitrogen atom.
  • Ir represents iridium.
  • R 1 to R 9 each independently represents a hydrogen atom, an alkyl group, or a halogen atom.
  • R 18 to R 27. Each independently represents a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, a cyano group, or a halogen atom, wherein the alkyl group is an aryl group, an alkoxy group, or a heterocyclic group.
  • the aryl group may be substituted with an alkyl group (excluding trifluoromethyl group), an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, or a halogen atom. (Excluding a fluorine atom) may be substituted with an aralkyl group, and the alkoxy group may be an aryl group, an alkoxy group, or a hetero group.
  • the heterocyclic group may be substituted with an alkyl group, an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, or a halogen atom.
  • the aryloxy group may be substituted with an alkyl group, an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, or a halogen atom, and adjacent R 18 to R 27 are each bonded to form a ring structure. It may be formed.
  • each of R 18 to R 27 is preferably independently a hydrogen atom, an alkyl group, or an aryl group.
  • R 18 to R 27 is an alkyl group.
  • R 18 to R 27 is an aryl group.
  • the iridium complex according to the present invention is preferably represented by the following general formula (4).
  • N represents a nitrogen atom.
  • Ir represents iridium.
  • R 1 to R 9 each independently represents a hydrogen atom, an alkyl group, or a halogen atom.
  • R 38 to R 47. Each independently represents a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, a cyano group, or a halogen atom, wherein the alkyl group is an aryl group, an alkoxy group, or a heterocyclic group.
  • the aryl group may be substituted with an alkyl group (excluding trifluoromethyl group), an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, or a halogen atom. (Excluding a fluorine atom) may be substituted with an aralkyl group, and the alkoxy group may be an aryl group, an alkoxy group, or a hetero group.
  • the heterocyclic group may be substituted with an alkyl group, an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, or a halogen atom.
  • the aryloxy group may be substituted with an alkyl group, an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, or a halogen atom, and adjacent R 38 to R 47 are each bonded to form a ring structure. It may be formed.
  • R 38 to R 47 are preferably each independently a hydrogen atom, an alkyl group, or an aryl group.
  • R 38 to R 47 is an alkyl group.
  • R 38 to R 47 is an aryl group.
  • the luminescent material according to the present invention includes the iridium complex according to the present invention.
  • the organic light emitting device according to the present invention includes the light emitting material according to the present invention.
  • the present disclosure can be applied to an organic electroluminescence device, an organic electrochemiluminescence device, and the like, and can provide a novel iridium complex that is excellent in thermal stability and sublimation properties and exhibits red light emission with high efficiency.
  • the novel iridium complex of the present disclosure exhibits red light emission with good color purity at room temperature and is excellent in thermal stability and sublimation, and thus can be suitably used as a light emitting device material for various applications.
  • An organic light emitting device using the compound exhibits high luminance light emission in a red region, and thus is suitable for fields such as a display device, a display, a backlight, or an illumination light source.
  • 2 is an emission spectrum of the compound (Ir-10) of the present invention in THF under an argon atmosphere.
  • 2 is an emission spectrum of an organic electroluminescence device produced using the compound (Ir-10) of the present invention.
  • a hydrogen atom includes an isotope (such as a deuterium atom), and an atom constituting a substituent further includes the isotope.
  • the iridium complex according to the present invention is represented by the following general formula (1).
  • N represents a nitrogen atom.
  • Ir represents iridium.
  • R 1 to R 9 each independently represents a hydrogen atom, an alkyl group, or a halogen atom.
  • R 10 to R 17. Each independently represents a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, a cyano group, or a halogen atom, wherein the alkyl group is an aryl group, an alkoxy group, or a heterocyclic group.
  • the aryl group may be substituted with an alkyl group (excluding trifluoromethyl group), an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, or a halogen atom. (Excluding a fluorine atom) may be substituted with an aralkyl group, and the alkoxy group may be an aryl group, an alkoxy group, or a hetero group.
  • the heterocyclic group may be substituted with an alkyl group, an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, or a halogen atom.
  • the aryloxy group may be substituted with an alkyl group, an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, or a halogen atom, and adjacent R 10 to R 17 are each bonded to form a ring structure. It may be formed.
  • the iridium complex according to the present invention includes, for example, organic luminescence that exhibits good light emission in the red region by including these iridium complexes in a light emitting layer of an organic light emitting device or a plurality of organic compound layers including a light emitting layer by a vacuum deposition method. An element is obtained.
  • N represents a nitrogen atom.
  • Ir represents iridium
  • R 1 to R 9 each independently represents a hydrogen atom, an alkyl group, or a halogen atom, preferably a hydrogen atom or an alkyl group.
  • R 10 to R 17 each independently represents a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, a cyano group, or a halogen atom, ,
  • An alkyl group, an aryl group, a heterocyclic group, a cyano group, or a halogen atom a hydrogen atom, an alkyl group, an aryl group, or a halogen atom is more preferable, and a hydrogen atom, an alkyl group, or an aryl group is particularly preferable
  • a hydrogen atom or an alkyl group is more preferable.
  • the alkyl group is preferably an alkyl group having 1 to 30 carbon atoms, more preferably an alkyl group having 1 to 20 carbon atoms, particularly preferably an alkyl group having 1 to 10 carbon atoms, Most preferably, it is an alkyl group of 1 to 5.
  • the alkyl group may be a linear alkyl group or a branched alkyl group.
  • the alkyl group may be substituted with an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, or a halogen atom.
  • alkyl group examples include methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, and n-heptyl.
  • n-octyl group n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group Group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, cyclohexyl group, cyclooctyl group, or 3,5-tetramethylcyclohexyl group There is.
  • methyl group ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, neopentyl group, or 1-methylpentyl group.
  • a methyl group or a t-butyl group is more preferable, and a methyl group is particularly preferable.
  • the aryl group is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms, and particularly preferably an aryl group having 6 to 12 carbon atoms.
  • the aryl group may be substituted with an alkyl group (excluding a trifluoromethyl group), an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, or a halogen atom (excluding a fluorine atom). It will not be replaced.
  • the aryl group may be substituted with an unsubstituted alkyl group, aryl group, alkoxy group, heterocyclic group, aryloxy group, chlorine atom, bromine atom, or iodine atom.
  • An aryl group substituted with an alkyl group is particularly preferable because the sublimation property of the iridium complex is improved.
  • aryl group examples include a phenyl group, a biphenyl-2-yl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a p-terphenyl-4-yl group, and a p-terphenyl-3-yl group.
  • the alkoxy group is preferably an alkoxy group having 1 to 30 carbon atoms, more preferably an alkoxy group having 1 to 20 carbon atoms, particularly preferably an alkoxy group having 1 to 10 carbon atoms, Most preferably, it is an alkoxy group having a number of 1 to 5.
  • the alkoxy group may be substituted with an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, or a halogen atom.
  • alkoxy group examples include a methoxy group, an ethoxy group, a proxy group, an isoproxy group, an n-butoxy group, and a t-butoxy group, and a methoxy group is preferable.
  • the heterocyclic group is preferably a heterocyclic group having 1 to 30 carbon atoms, more preferably a heterocyclic group having 1 to 20 carbon atoms, and preferably a heterocyclic group having 1 to 10 carbon atoms. Particularly preferred is a heterocyclic group having 1 to 5 carbon atoms.
  • the heterocyclic group may be substituted with an alkyl group, an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, or a halogen atom.
  • heterocyclic group examples include 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 2-pyrimidyl group, 4-pyrimidyl group, 5-pyrimidyl group, 2-pyrazyl group, 3-pyridazinyl group, 4- Pyridazinyl, 5-pyridazinyl, quinolinyl, 1-pyrrolyl, 1-imidazolyl, 2-imidazolpyridinyl, 1-indolyl, 2-benzofuranyl, 7-isobenzofuranyl, 2-quinolyl Group, 1-isoquinolyl group, 1-phenanthridinyl group, 1-acridinyl group, 1-phenazinyl group, 2-thienyl group, 1-dibenzofuranyl group, 1,3,5-triazinyl group and the like.
  • the aryloxy group is preferably an aryloxy group having 6 to 30 carbon atoms, more preferably an aryloxy group having 6 to 20 carbon atoms, and an aryloxy group having 6 to 10 carbon atoms. Particularly preferred.
  • the aryloxy group may be substituted with an alkyl group, an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, or a halogen atom.
  • aryloxy group examples include a phenoxy group and a naphthyloxy group, and a phenoxy group is preferable.
  • the halogen atom is preferably a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.
  • a bromine atom or a fluorine atom is more preferred, and a bromine atom is particularly preferred.
  • R 1 to R 17 More desirable forms of R 1 to R 17 will be specifically described below.
  • R 1 and R 3 to R 9 are preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, particularly preferably a hydrogen atom or a methyl group, and most preferably a hydrogen atom.
  • R 2 is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, particularly preferably a hydrogen atom or a methyl group, and most preferably a methyl group.
  • R 10 and R 13 are preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, particularly preferably a hydrogen atom or a methyl group, and most preferably a hydrogen atom.
  • R 11 and R 12 are preferably a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and a hydrogen atom or a methyl group Is particularly preferred, and a hydrogen atom is most preferred.
  • R 14 is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and particularly preferably a hydrogen atom.
  • R 15 is preferably a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group, more preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms, a hydrogen atom, or An alkyl group having 1 to 10 carbon atoms is particularly preferable, and a hydrogen atom or a methyl group is particularly preferable.
  • R 16 is preferably a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms, a hydrogen atom or 1 carbon atom.
  • An alkyl group of ⁇ 10 is particularly preferred, and a hydrogen atom, a methyl group, or a t-butyl group is particularly preferred.
  • R 17 is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, particularly preferably a hydrogen atom or a methyl group, and most preferably a hydrogen atom.
  • R 10 to R 17 is an alkyl group.
  • At least one is preferably an aryl group.
  • Adjacent R 10 to R 17 may be bonded to each other to form a ring structure, and R 10 and R 11 , R 11 and R 12 , or R 12 and R 13 may be bonded to each other to form a ring structure. It is particularly preferable that R 10 and R 11 , or R 12 and R 13 are bonded to form a ring structure.
  • the ring structure represents a saturated ring or an unsaturated ring, and an unsaturated ring is preferable.
  • an unsaturated ring a carbocycle or a heterocycle is preferable, and a carbocycle is more preferable.
  • the saturated ring or unsaturated ring is preferably a 5-membered ring or 6-membered ring, particularly preferably a 6-membered ring, and most preferably a benzene ring.
  • the benzene ring is preferably substituted with an alkyl group (preferably having 1 to 5 carbon atoms).
  • R 10 and R 11 , R 11 and R 12 , or R 12 and R 13 are preferably bonded to each other to form a benzene ring, and R 10 and R 11 , or R 12 and More preferably, R 13 is bonded to form a benzene ring.
  • R 1 ⁇ R 9 in the general formula (1) have the same meanings as R 1 ⁇ R 9, and is the same desirable ranges.
  • R 18 to R 47 in the general formulas (2) to (4) each independently represent a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, a heterocyclic group, an aryloxy group, a cyano group, or a halogen atom.
  • a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, a cyano group, or a halogen atom is preferable, a hydrogen atom, an alkyl group, an aryl group, or a halogen atom is more preferable, and a hydrogen atom, an alkyl group, or An aryl group is particularly preferable, and a hydrogen atom or an alkyl group is more particularly preferable.
  • R 1 ⁇ R 17 in general formula (1) For the desired range as these substituents is the same as R 1 ⁇ R 17 in general formula (1).
  • Adjacent R 18 to R 47 may be bonded to each other to form a ring structure.
  • the ring structure represents a saturated ring or an unsaturated ring, and an unsaturated ring is preferable.
  • an unsaturated ring a carbocycle or a heterocycle is preferable, and a carbocycle is more preferable.
  • the saturated ring or unsaturated ring is preferably a 5-membered ring or 6-membered ring, particularly preferably a 6-membered ring, and most preferably a benzene ring.
  • the benzene ring is preferably substituted with an alkyl group (preferably having 1 to 5 carbon atoms).
  • R 18 to R 47 More desirable forms of R 18 to R 47 will be specifically described below.
  • R 18 , R 19 , R 21 , R 23 , R 28 to R 33 , R 38 to R 43 are preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, An atom or a methyl group is particularly preferred, and a hydrogen atom is most preferred.
  • R 20 and R 22 are preferably a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms, a hydrogen atom or An alkyl group having 1 to 10 carbon atoms is particularly preferable, a hydrogen atom or a methyl group is more particularly preferable, and a hydrogen atom is most preferable.
  • R 24 , R 34 and R 44 are preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and particularly preferably a hydrogen atom.
  • R 25 , R 27 , R 35 , R 37 , R 45 , R 47 are preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, a hydrogen atom, a methyl group, or The t-butyl group is particularly preferred.
  • R 26 , R 36 and R 46 are preferably a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 12 carbon atoms, and a hydrogen atom Or an alkyl group having 1 to 10 carbon atoms, particularly preferably a hydrogen atom, a methyl group, or a t-butyl group.
  • At least one of R 18 to R 27 is preferably an alkyl group, more preferably at least one of R 23 , R 25 , and R 27 is an alkyl group, and R 25 is particularly preferably an alkyl group.
  • R 23 , R 25 and R 27 is an alkyl group, red light emission with particularly good color purity can be obtained.
  • R 28 to R 37 is an alkyl group.
  • R 28 to R 37 is an aryl group.
  • R 38 to R 47 is an alkyl group.
  • R 38 to R 47 is an aryl group.
  • the iridium complex represented by the general formulas (2) to (4) is preferable in order to obtain red light emission with good color purity.
  • any of the forms ⁇ 1> to ⁇ 15> shown below is particularly desirable.
  • R 20 and iridium complex represented by the general formula R 23 is an alkyl group (2).
  • any of the forms ⁇ 16> to ⁇ 19> shown below is particularly desirable.
  • the emission quantum yield in a solution or in a thin film state at room temperature is preferably 0.1 or more, and is 0.2 or more. More preferably, it is particularly preferably 0.3 or more.
  • the measurement of the luminescence quantum yield in the solution is performed after passing argon gas or nitrogen gas through the solution in which the iridium complex is dissolved, or after freezing and degassing the solution in which the luminescent material is dissolved. Good to do.
  • a method for measuring the luminescence quantum yield either an absolute method or a relative method may be used. In the relative method, the luminescence quantum yield can be measured by comparing the emission spectrum with a standard substance (such as quinine sulfate).
  • the absolute method it is possible to measure the emission quantum yield in a solid state or in a solution by using a commercially available device (for example, an absolute PL quantum yield measuring device (C9920-02) manufactured by Hamamatsu Photonics Co., Ltd.). It is.
  • the luminescence quantum yield in the solution can be measured using various solvents (for example, tetrahydrofuran, 2-methyltetrahydrofuran, dichloromethane, chloroform, acetonitrile, toluene, 1,2-dichloroethane, benzene, DMF, DMSO, etc.)
  • the iridium complex according to the present invention only needs to achieve the above-mentioned emission quantum yield in any solvent.
  • the measurement of the luminescence quantum yield in a thin film state is performed by, for example, vacuum-depositing the iridium complex of the present invention on quartz glass, and a commercially available device (for example, Hamamatsu Photonics Co., Ltd., absolute PL quantum yield measurement device (C9920)). ) Can be used.
  • the luminescence quantum yield in a thin film can be measured by vapor-depositing the iridium complex of the present invention alone or co-deposited with various host materials. It is sufficient that the yield is achieved.
  • the iridium complex represented by the general formula (1) according to the present invention emits light mainly in the red region, but its wavelength region depends on the type or structure of the ligand.
  • the emission maximum wavelength of the emission spectrum in solution or in a thin film at room temperature is preferably in the range of 580 nm to 700 nm, and 600 nm It is more preferably in the range of ⁇ 680 nm, particularly preferably in the range of 610 nm to 650 nm, and particularly preferably in the range of 615 nm to 640 nm.
  • X is 0 in the CIE color coordinates of the emission spectrum in the solution, in the thin film, or in the organic light emitting device. 0.62 to 0.68, and Y is preferably 0.32 to 0.38. Furthermore, it is particularly preferable that X is 0.64 to 0.66 and Y is 0.34 to 0.36 because red is a good color purity.
  • Non-Patent Document 1 Japanese Patent Application Laid-Open No. 2008-179607
  • Patent Document 2 Japanese Patent Publication No. 2011-511821
  • the iridium complex represented by the general formula (1) according to the present invention can be synthesized, for example, by the method of the formula (A).
  • the iridium complex represented by the general formula (2) according to the present invention can be synthesized, for example, by the method of the formula (B).
  • the iridium complex represented by the general formula (3) according to the present invention can be synthesized, for example, by the method of the formula (C).
  • the iridium complex represented by the general formula (4) according to the present invention can be synthesized, for example, by the method of the formula (D).
  • the iridium complex represented by the general formula (1) according to the present invention can be used after being treated according to the post-treatment of a normal synthesis reaction, and if necessary, purified or not purified.
  • a post-treatment method for example, extraction, cooling, crystallization by adding water or an organic solvent, or an operation of distilling off the solvent from the reaction mixture can be performed alone or in combination.
  • a purification method recrystallization, distillation, sublimation, column chromatography or the like can be performed alone or in combination.
  • the iridium complex represented by the general formula (1) according to the present invention has geometric isomers (facial isomers, meridional isomers), and any geometric isomer may be used as long as the object of the present invention can be achieved. It may be a mixture of geometric isomers.
  • the iridium complex represented by the general formula (1) according to the present invention can emit red phosphorescence with high efficiency at room temperature
  • the light-emitting material or the light-emitting substance of the organic light-emitting element is used.
  • an organic light-emitting element preferably an organic electroluminescent element
  • an organic light-emitting element, a light-emitting device, or a lighting device with high luminous efficiency can be realized.
  • an organic light-emitting element, a light-emitting device, or a lighting device with low power consumption can be realized.
  • the organic electroluminescent element is an element in which a plurality of organic compounds are laminated between an anode and a cathode, and preferably contains an iridium complex represented by the general formula (1) as a light emitting material of the light emitting layer.
  • the light emitting layer is composed of a light emitting material and a host material.
  • Anode / light emitting layer / cathode (2) Anode / light emitting layer / electron transport layer / cathode (3) Anode / hole transport layer / light emitting layer / cathode (4) Anode / hole transport layer / light emitting layer / electron Transport layer / cathode (5) anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode (6) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode ( 7) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode ( 7) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode
  • a hole blocking layer (also referred to as a hole blocking layer) may be provided between the light emitting layer and the cathode.
  • an electron blocking layer (also referred to as an electron barrier layer) may be provided between the light emitting layer and the anode.
  • the light-emitting layer is a layer that recombines electrons and holes injected from the electrode and emits light via excitons. Even if the light-emitting portion is within the layer of the light-emitting layer, It may be an interface.
  • the film thickness of the light emitting layer is preferably in the range of 2 to 1000 nm, more preferably in the range of 2 to 200 nm, and still more preferably in the range of 3 to 150 nm.
  • the light emitting layer preferably contains a light emitting material and a host material.
  • the iridium complex represented by the general formula (1) according to the present invention may be contained singly or in plural kinds, and other luminescent materials may be contained.
  • the total content of the iridium complex represented by the general formula (1) according to the present invention is preferably 1 to 50% by mass ratio, and preferably 1 to 30%. More preferred is 5 to 20%.
  • light-emitting materials include anthracene derivatives, pyrene derivatives, chrysene derivatives, fluoranthene derivatives, perylene derivatives, fluorene derivatives, arylacetylene derivatives, styrylarylene derivatives, styrylamine derivatives, arylamine derivatives, boron complexes, squalium.
  • the host material is a compound mainly responsible for charge injection and transport in the light emitting layer. Moreover, it is preferable that the mass ratio in the layer is 20% or more among the compounds contained in a light emitting layer. More preferably, it is 50% or more, and particularly preferably 80% or more. Among the compounds contained in the light emitting layer, the upper limit of the content of the host material is preferably 99% or less, more preferably 95% or less, and particularly preferably 90% or less in terms of mass ratio. .
  • the excited state energy (T 1 level) of the host material is higher than the excited state energy (T 1 level) of the iridium complex represented by the general formula (1) according to the present invention contained in the same layer. Is preferred.
  • the host material may be used alone or in combination. By using a plurality of types of host compounds, charge transfer can be adjusted and the organic electroluminescence device can be made highly efficient.
  • the host material that can be used in the present invention is not particularly limited, and may be a low molecular compound or a high molecular compound having a repeating unit.
  • host materials include triarylamine derivatives, phenylene derivatives, condensed ring aromatic compounds (for example, naphthalene derivatives, phenanthrene derivatives, fluorene derivatives, pyrene derivatives, tetracene derivatives, coronene derivatives, chrysene derivatives, perylene derivatives, 9, 10-diphenylanthracene derivatives or rubrene), quinacridone derivatives, acridone derivatives, coumarin derivatives, pyran derivatives, nile red, pyrazine derivatives, benzimidazole derivatives, benzothiazole derivatives, benzoxazole derivatives, stilbene derivatives, organometallic complexes (for example, tris (8-quinolinolato) organic aluminum complexes such as aluminum, organic beryllium complexes, organic iridium complexes, or organic platinum complexes), or poly (fluoro Nirenbiniren) derivatives, poly (fluoro Ni
  • the electron transport layer is made of a material having a function of transporting electrons, and only needs to have a function of transmitting electrons injected from the cathode to the light emitting layer.
  • the thickness of the electron transport layer is not particularly limited, but is usually in the range of 2 to 5000 nm, more preferably in the range of 2 to 500 nm, and still more preferably in the range of 5 to 200 nm.
  • an electron transport material As a material used for the electron transport layer (hereinafter referred to as an electron transport material), any material that has either an electron injection property or a transport property or a hole barrier property may be used. Any one can be selected and used.
  • the electron transporting material include nitrogen-containing aromatic heterocyclic derivatives (carbazole derivatives, organoaluminum complexes such as tris (8-quinolinolato) aluminum, azacarbazole derivatives (one or more carbon atoms constituting the carbazole ring) Substituted with a nitrogen atom), pyridine derivatives, pyrimidine derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, oxazole derivatives, thiazole derivatives, oxadiazole derivatives, triazole derivatives, benzimidazole derivatives or benzoxazole derivatives, etc. ), Dibenzofuran derivatives, dibenzothiophene derivatives, or aromatic hydrocarbon ring derivatives (such as naphthalene derivatives, anthracene derivatives, or triphenylene).
  • aromatic heterocyclic derivatives such as tris (8-quinolinolato) aluminum, azac
  • the hole blocking layer is a layer having a function of an electron transport layer in a broad sense, and is preferably made of a material having a function of transporting electrons while having a small ability to transport holes, and transporting electrons while transporting holes. The probability of recombination of electrons and holes can be improved by blocking.
  • the hole blocking layer is preferably provided adjacent to the cathode side of the light emitting layer.
  • the film thickness of the hole blocking layer is preferably in the range of 3 to 100 nm, more preferably in the range of 5 to 30 nm.
  • the material used for the hole blocking layer is preferably used, and the host material is also preferably used as the material for the hole blocking layer.
  • An electron injection layer (also referred to as a “cathode buffer layer”) is a layer provided between a cathode and a light emitting layer in order to reduce driving voltage or improve light emission luminance.
  • the thickness of the electron injection layer is preferably in the range of 0.1 to 5 nm. More preferably, it is in the range of 0.1 to 1 nm.
  • materials that are preferably used for the electron injection layer include metals (strontium or aluminum), alkali metal compounds (lithium fluoride or sodium fluoride, etc.), alkaline earth metal compounds (magnesium fluoride or calcium fluoride). Etc.), metal oxides (such as aluminum oxide), or metal complexes (such as lithium 8-hydroxyquinolate (Liq)).
  • the above-described electron transport material can also be used.
  • examples of the electron injecting material include a phenanthroline derivative lithium complex (LiPB) and a phenoxypyridine lithium complex (LiPP).
  • the hole transport layer is made of a material having a function of transporting holes, and may have a function of transmitting holes injected from the anode to the light emitting layer. There may be a plurality of hole transport layers.
  • the thickness of the hole transport layer is not particularly limited, but is usually in the range of 2 to 5000 nm, more preferably in the range of 5 to 500 nm, and still more preferably in the range of 5 to 200 nm.
  • a material used for the hole transport layer may have any of a hole injection property or a transport property, or an electron barrier property. Any one can be selected and used.
  • hole transporting materials include porphyrin derivatives; phthalocyanine derivatives; oxazole derivatives; phenylenediamine derivatives; stilbene derivatives; triarylamine derivatives; carbazole derivatives; indolocarbazole derivatives; acene derivatives such as anthracene or naphthalene; Fluorene derivatives; fluorenone derivatives; polymer materials or oligomers in which polyvinyl carbazole or aromatic amine is introduced into the main chain or side chain; polysilanes; conductive polymers or oligomers (eg PEDOT: PSS, aniline copolymers, polyaniline, polythiophene, etc.) ) And the like.
  • PEDOT PSS, aniline copolymers, polyaniline, polythiophene, etc.
  • the electron blocking layer is a layer having a function of a hole transport layer in a broad sense, and is preferably made of a material having a function of transporting holes and a small ability to transport electrons, and transporting electrons while transporting holes. The probability of recombination of electrons and holes can be improved by blocking.
  • the thickness of the electron blocking layer is preferably in the range of 3 to 100 nm, more preferably in the range of 5 to 30 nm.
  • the above-described structure of the hole transport layer can be used as an electron blocking layer as necessary.
  • the hole injection layer (also referred to as “anode buffer layer”) is a layer provided between the anode and the light emitting layer in order to lower the driving voltage or improve the light emission luminance.
  • Examples of materials used for the hole injection layer include conductive materials such as phthalocyanine derivatives represented by copper phthalocyanine, hexaazatriphenylene derivatives, metal oxides represented by vanadium oxide, amorphous carbon, polyaniline (emeraldine), and polythiophene.
  • conductive materials such as phthalocyanine derivatives represented by copper phthalocyanine, hexaazatriphenylene derivatives, metal oxides represented by vanadium oxide, amorphous carbon, polyaniline (emeraldine), and polythiophene.
  • Preferred are high molecular weight polymers, cyclometalated complexes represented by tris (2-phenylpyridine) iridium complexes, and triarylamine derivatives.
  • the organic electroluminescent element of the present invention is preferably supported on a substrate.
  • a substrate There is no restriction
  • substrate For example, glass, such as alkali glass, alkali free glass, or quartz glass, or a transparent plastic currently used in the conventional organic electroluminescent element is mentioned.
  • anode examples include gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, tungsten, and the like, or alloys thereof; tin oxide, zinc oxide, indium oxide, and oxide. Metal oxides such as indium tin (ITO) or zinc indium oxide can be used. Further, conductive polymers such as polyaniline, polypyrrole, polythiophene or polyphenylene sulfide can also be used. These electrode materials may be used alone or in combination. Moreover, the anode may be composed of a single layer or a plurality of layers.
  • the material constituting the cathode include simple metals such as lithium, sodium, potassium, calcium, magnesium, aluminum, indium, ruthenium, titanium, manganese, yttrium, silver, lead, tin, or chromium. Further, these metals may be combined to form an alloy. For example, alloys such as lithium-indium, sodium-potassium, magnesium-silver, aluminum-lithium, aluminum-magnesium, or magnesium-indium can be used. In addition, metal oxides such as indium tin oxide (ITO) can be used. These electrode materials may be used alone or in combination.
  • the cathode may have a single layer structure or a multilayer structure.
  • the organic light-emitting device containing the iridium complex represented by the general formula (1) according to the present invention can be manufactured by a vacuum deposition method, a solution coating method, a transfer method using a laser, or the like, or a spray method.
  • a vacuum deposition method it is desirable to form the light emitting layer containing the iridium complex represented by the general formula (1) according to the present invention by a vacuum deposition method.
  • Hole transport layer by a vacuum deposition method in the case of forming the respective layers such as a light emitting layer or the electron transporting layer but vacuum deposition conditions are not particularly limited, 10 -4 ⁇ 10 -5 Pa approximately about 50 ⁇ 500 ° C. under a vacuum of Vapor deposition is preferably performed at a boat temperature of about ⁇ 50 to 300 ° C. and a substrate temperature of about 0.01 to 50 nm / second.
  • a boat temperature of about ⁇ 50 to 300 ° C.
  • a substrate temperature of about 0.01 to 50 nm / second.
  • Step 1 Microwave (2450 MHz, 1000 W) with 21.7 g of iridium trichloride nhydrate, 28.4 g of 1-phenylisoquinoline, 440 ml of DMF and 60 ml of pure water placed in a three-necked flask, fitted with a Dimroth condenser, and vented with argon gas was irradiated for 30 minutes. After the reaction solution was cooled to room temperature, the precipitate was collected by filtration and washed with pure water and methanol to obtain (Ir-62-A) in a yield of 95%.
  • Step 2 12.2 g of the compound (Ir-62-A) obtained in Step 1, 5.15 g of silver trifluoromethanesulfonate, 400 ml of methanol and 1250 ml of dichloromethane were placed in a three-necked flask and reacted at room temperature in an argon gas atmosphere for 24 hours. It was. The reaction solution was filtered through Celite, and the solvent was distilled off under reduced pressure to obtain (Ir-62-B) in a yield of 94%.
  • Step 3 1.99 g of the compound (Ir-62-B) obtained in Step 2, 2.46 g of 2-methyldibenzo [f, h] quinoxaline, and 100 ml of ethanol were added, and the mixture was heated at 100 ° C. for 48 hours under an argon atmosphere. I let you. After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure. The obtained solid was dissolved in dichloromethane and filtered through Celite. Methanol was added to the filtrate, and the precipitate was collected by filtration.
  • Step 1 1.40 g of iridium trichloride nhydrate, 2.17 g of 1- (p-tolyl) isoquinoline, 34 ml of 2-ethoxyethanol, and 11 ml of pure water were placed in a three-necked flask and heated at 120 ° C. for 20 hours in an argon atmosphere. It was. After the reaction solution was cooled to room temperature, the precipitate was collected by filtration and washed with methanol and pure water to obtain Compound (Ir-63-A) in a yield of 62%.
  • Step 2 500 mg of the compound (Ir-63-A) obtained in Step 1, 212.7 mg of silver trifluoromethanesulfonate, 1 ml of methanol and 48 ml of dichloromethane were placed in a three-necked flask and reacted at room temperature for 24 hours in an argon gas atmosphere. The reaction solution was filtered through celite, and the solvent was evaporated under reduced pressure to obtain compound (Ir-63-B) in a yield of 99%.
  • Step 3> The total amount of the compound (Ir-63-B) obtained in Step 2 and 459.3 mg of 2-methyldibenzo [f, h] quinoxaline and 24 ml of ethanol were added, and the mixture was heated and reacted at 90 ° C. for 87 hours in an argon atmosphere. . After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure. The obtained solid was dissolved in dichloromethane and filtered through Celite. Methanol was added to the filtrate, and the precipitate was collected by filtration. This was recrystallized from dichloromethane and methanol to obtain (Ir-63) in a yield of 22.3%. The 1 H-NMR data is shown below.
  • Step 1 1.40 g of iridium trichloride nhydrate, 2.73 g of 3-methyl-2-phenylquinoline, 34 ml of 2-ethoxyethanol and 11 ml of pure water are placed in a three-necked flask and heated at 120 ° C. for 20 hours in an argon atmosphere. It was. After the reaction solution was cooled to room temperature, the precipitate was collected by filtration and washed with methanol and pure water to obtain Compound (Ir-33-A) in a yield of 41%.
  • Step 2 995.3 mg of the compound (Ir-33-A) obtained in step 1, 423.4 mg of silver trifluoromethanesulfonate, 1 ml of methanol and 136 ml of dichloromethane were placed in a three-necked flask and reacted at room temperature for 24 hours under an argon gas atmosphere. . The reaction solution was filtered through celite, and the solvent was evaporated under reduced pressure to give compound (Ir-33-B) in 99% yield.
  • Step 3> The total amount of the compound (Ir-33-B) obtained in Step 2 and 914.1 mg of 2-methyldibenzo [f, h] quinoxaline and 51 ml of ethanol were added, and the mixture was reacted by heating at 90 ° C. for 72 hours in an argon atmosphere. . After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure. The obtained solid was dissolved in dichloromethane and filtered through Celite. Methanol was added to the filtrate, and the precipitate was collected by filtration. This was recrystallized from dichloromethane and methanol to obtain (Ir-33) in a yield of 42.0%. The 1 H-NMR data is shown below.
  • Step 1 1.41 g of iridium trichloride n-hydrate, 2.61 g of 2- (3- (t-butyl) phenyl) quinoline, 34 ml of 2-ethoxyethanol and 11 ml of pure water were placed in a three-necked flask at 120 ° C. under an argon atmosphere. The reaction was heated for 20 hours. After the reaction solution was cooled to room temperature, the precipitate was collected by filtration and washed with methanol and pure water to obtain Compound (Ir-38-A) in a yield of 55%.
  • Step 2 1.3 g of the compound (Ir-38-A) obtained in Step 1, 490.7 mg of silver trifluoromethanesulfonate, 1.2 ml of methanol and 202 ml of dichloromethane were placed in a three-necked flask and reacted at room temperature for 24 hours under an argon gas atmosphere. I let you. The reaction solution was filtered through celite, and the solvent was evaporated under reduced pressure to give compound (Ir-38-B) in a yield of 99%.
  • Step 3 The total amount of compound (Ir-38-B) obtained in Step 2, 1.06 g of 2-methyldibenzo [f, h] quinoxaline, and 55 ml of ethanol were added, and the mixture was heated and reacted at 90 ° C. for 72 hours under an argon atmosphere. . After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure. The obtained solid was dissolved in dichloromethane and filtered through Celite. Methanol was added to the filtrate, and the precipitate was collected by filtration. This was recrystallized twice using dichloromethane and methanol to obtain (Ir-38) in a yield of 23.1%. The 1 H-NMR data is shown below.
  • Step 1 1.40 g of iridium trichloride nhydrate, 2.17 g of 2- (3- (t-butyl) phenyl) -3-methylquinoline, 34 ml of 2-ethoxyethanol and 11 ml of pure water were placed in a three-necked flask under an argon atmosphere. The reaction was conducted at 120 ° C. for 20 hours. After the reaction solution was cooled to room temperature, the precipitate was collected by filtration and washed with methanol and pure water to obtain Compound (Ir-55-A) in a yield of 38%.
  • Step 2 1.256 g of the compound (Ir-55-A) obtained in Step 1, 415.6 mg of silver trifluoromethanesulfonate, 1.1 ml of methanol and 39 ml of dichloromethane were placed in a three-necked flask and reacted at room temperature for 24 hours under an argon gas atmosphere. I let you. The reaction solution was filtered through celite, and the solvent was evaporated under reduced pressure to give compound (Ir-55-B) in a yield of 99%.
  • Step 3 The total amount of the compound (Ir-55-B) obtained in Step 2, 650 mg of 2-methyldibenzo [f, h] quinoxaline, and 55 ml of ethanol were added, and the mixture was reacted by heating at 90 ° C. for 72 hours in an argon atmosphere. After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure. The obtained solid was dissolved in dichloromethane and filtered through Celite. Methanol was added to the filtrate, and the precipitate was collected by filtration. This was purified by silica gel column chromatography (eluent: dichloromethane and hexane) to obtain (Ir-55) in a yield of 31.6%.
  • Step 2 452.1 mg of the compound (Ir-58-A) obtained in Step 1, 147.3 mg of silver trifluoromethanesulfonate, 1 ml of methanol and 30 ml of dichloromethane were placed in a three-necked flask and reacted at room temperature for 24 hours in an argon gas atmosphere. . The reaction solution was filtered through celite, and the solvent was evaporated under reduced pressure to give compound (Ir-58-B) in a yield of 99%.
  • Step 3 The total amount of the compound (Ir-58-B) obtained in Step 2 was added to 279.9 mg of 2-methyldibenzo [f, h] quinoxaline, 6 ml of 2-ethoxyethanol, and 6 ml of DMF. The reaction was heated for an hour. After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure. The obtained solid was dissolved in dichloromethane and filtered through Celite. Methanol was added to the filtrate, and the precipitate was collected by filtration.
  • Step 1 1.40 g of iridium trichloride n-hydrate, 3.21 g of 2- (9,9-dimethyl-9H-fluoren-2-yl) quinoline, 34 ml of 2-ethoxyethanol and 11 ml of pure water were placed in a three-necked flask, and an argon atmosphere Then, the reaction was performed by heating at 120 ° C. for 20 hours. After the reaction solution was cooled to room temperature, the precipitate was collected by filtration and washed with methanol and pure water to obtain Compound (Ir-60-A) in a yield of 332 mg.
  • Step 2 624.4 mg of the compound (Ir-60-A) obtained in Step 1, 203.1 mg of silver trifluoromethanesulfonate, 0.5 ml of methanol and 18 ml of dichloromethane were placed in a three-necked flask and reacted at room temperature under an argon gas atmosphere for 24 hours. I let you. The reaction solution was filtered through celite, and the solvent was evaporated under reduced pressure to give compound (Ir-60-B) in a yield of 99%.
  • Step 3 The total amount of (Ir-60-B) obtained in Step 2 was added to 438.6 mg of 2-methyldibenzo [f, h] quinoxaline and 24 ml of ethanol, and the mixture was reacted by heating at 90 ° C. for 72 hours in an argon atmosphere. After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure. The obtained solid was dissolved in dichloromethane and filtered through Celite. Methanol was added to the filtrate, and the precipitate was collected by filtration. This was purified by silica gel column chromatography (eluent: dichloromethane and hexane) to obtain (Ir-60) in a yield of 9.7%.
  • Step 1> Put 0.857 g of iridium trichloride nhydrate, 1.13 g of 3-phenylisoquinoline, 40 ml of DMF and 10 ml of pure water into a three-necked flask, attach a Dimroth cooler, and ventilate argon gas, microwave (2450 MHz, 300 W) Were irradiated for 45 minutes. After the reaction solution was cooled to room temperature, the precipitate was collected by filtration and washed with pure water and methanol to obtain (Ir-77-A) in a yield of 88.8%.
  • Step 2 The total amount of the compound (Ir-77-A) obtained in Step 1, 0.578 g of silver trifluoromethanesulfonate, 40 ml of methanol and 60 ml of dichloromethane were placed in a three-necked flask and reacted at room temperature in an argon gas atmosphere for 24 hours. . The reaction solution was filtered through Celite, and the solvent was distilled off under reduced pressure to obtain (Ir-77-B) in a yield of 100%.
  • Step 3 The total amount of compound (Ir-77-B) obtained in Step 2 and 2.10 g of 2-methyldibenzo [f, h] quinoxaline, 18 ml of methanol and 42 ml of ethanol were added, and the mixture was heated at 95 ° C. for 48 hours under an argon atmosphere. Reacted. After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure. The obtained solid was dissolved in dichloromethane and filtered through Celite. Methanol was added to the filtrate, and the precipitate was collected by filtration.
  • Step 1 Place 2.00 g of iridium trichloride n-hydrate, 5.70 g of 3-biphenylisoquinoline, 66 ml of DMF and 10 ml of pure water in a three-necked flask, attach a Dimroth condenser, and ventilate argon gas, microwave (2450 MHz, 400 W) Was irradiated for 25 minutes.
  • the reaction solution was cooled to room temperature and pure water was added, and then the precipitate was collected by filtration and washed with pure water, methanol and acetone to obtain (Ir-95-A) in a yield of 91.5%.
  • Step 2 1.11 g of the compound (Ir-95-A) obtained in Step 1 and 0.370 g of silver trifluoromethanesulfonate, 55 ml of methanol and 55 ml of dichloromethane were placed in a three-necked flask and reacted at room temperature for 24 hours in an argon gas atmosphere. I let you. The reaction solution was filtered through Celite, and the solvent was distilled off under reduced pressure to obtain (Ir-95-B) in a yield of 89.7%.
  • Step 3 Add the total amount of compound (Ir-95-B) obtained in Step 2, 1.38 g of 2-methyldibenzo [f, h] quinoxaline, 15 ml of methanol, and 35 ml of ethanol, and heat at 95 ° C. for 48 hours under an argon atmosphere. Reacted. After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure. The obtained solid was dissolved in dichloromethane and filtered through Celite. Methanol was added to the filtrate, and the precipitate was collected by filtration.
  • Luminescence characteristics of the compound (Ir-62) of the present invention in THF After dissolving the compound (Ir-62) of the present invention in THF and venting with argon gas, an absolute PL quantum yield measuring apparatus (C9920 manufactured by Hamamatsu Photonics Co., Ltd.) ) was used to measure the emission spectrum at room temperature (excitation wavelength: 340 nm), and showed red emission (emission maximum wavelength: 619 nm).
  • the emission quantum yield was 0.59.
  • Luminescence characteristics of the compound of the present invention (Ir-63) in THF After dissolving the compound of the present invention (Ir-63) in THF and venting with argon gas, an absolute PL quantum yield measuring apparatus (C9920 manufactured by Hamamatsu Photonics Co., Ltd.) ) was used to measure the emission spectrum at room temperature (excitation wavelength: 340 nm), and showed red emission (emission maximum wavelength: 625 nm).
  • the emission quantum yield was 0.61.
  • Luminescence characteristics of the compound of the present invention (Ir-77) in chloroform After dissolving the compound of the present invention (Ir-77) in chloroform and venting with argon gas, an absolute PL quantum yield measuring apparatus (C9920 manufactured by Hamamatsu Photonics Co., Ltd.) ) was used to measure the emission spectrum (excitation wavelength: 340 nm) at room temperature, and showed red emission (emission maximum wavelength: 656 nm).
  • the emission quantum yield was 0.22.
  • Luminescence characteristics of the compound of the present invention (Ir-95) in chloroform After dissolving the compound of the present invention (Ir-95) in chloroform and venting with argon gas, an absolute PL quantum yield measuring apparatus (C9920 manufactured by Hamamatsu Photonics Co., Ltd.) ) was used to measure the emission spectrum at room temperature (excitation wavelength: 340 nm), and showed red emission (emission maximum wavelength: 625 nm).
  • the emission quantum yield was 0.47.
  • Luminescence characteristics of Comparative Compound (1) Regarding the luminescence characteristics of Comparative Compound (1) in solution, see Adv. Mater. 2003, Vol. 15, pp. 224-228 (Non-patent Document 1). That is, the emission maximum wavelength in dichloromethane is 608 nm, which shows orange-red emission.
  • an emission spectrum (excitation wavelength: 340 nm) at room temperature was measured using an absolute PL quantum yield measuring device (C9920) manufactured by Hamamatsu Photonics Co., Ltd. When measured, it showed weak deep red light emission (emission maximum wavelength: 687 nm). The emission quantum yield was 0.028.
  • an emission spectrum (excitation wavelength: 340 nm) at room temperature was obtained using an absolute PL quantum yield measuring device (C9920) manufactured by Hamamatsu Photonics Co., Ltd. When measured, it showed weak deep red light emission (emission maximum wavelength: 691 nm). The emission quantum yield was 0.017.
  • Example II-1 to Example II-8 it was revealed that all of the compounds of the present invention emitted red light in THF or chloroform at room temperature.
  • the emission spectrum of the compound of the present invention was shifted by a longer wavelength than that of the comparative compound (1), and it was revealed that pure red emission could be realized from the CIE chromaticity.
  • the luminescence of the comparative compounds (2) and (3) was a faint deep red, and it was revealed that the compound of the present invention showed superior red luminescence characteristics.
  • Example III-1 Sublimation purification of the compound (Ir-2) of the present invention 116 mg of the compound (Ir-2) of the present invention was placed in a sublimation purification apparatus (P-200, manufactured by ALS Technology Co., Ltd.), and the degree of vacuum was 1 ⁇ 10 ⁇ 4 Pa and the temperature was 300 to When sublimation purification was performed over 9 hours under the condition of 320 ° C., the yield of the sublimation product was 99.5%. There was no sublimation residue, and no decomposition by sublimation purification was observed. 0.5% was estimated to be a low-boiling component such as a residual solvent, and the material balance was 99.5%.
  • Example III-2 Sublimation purification of the compound (Ir-10) of the present invention 139 mg of the compound (Ir-10) of the present invention was put into a sublimation purification apparatus (P-200, manufactured by ALS Technology Co., Ltd.), and the degree of vacuum was 1 ⁇ 10 ⁇ 4 Pa and the temperature was from 315 to When sublimation purification was performed over 9 hours under the condition of 320 ° C., the yield of the sublimation product was 88%. Sublimation residue was as small as 12% of the input. No decomposition by sublimation purification was observed, and the material balance was 100%.
  • Example III-3 Sublimation purification of the compound (Ir-38) of the present invention 187 mg of the compound (Ir-38) of the present invention was put into a sublimation purification apparatus (P-200, manufactured by ALS Technology), and the degree of vacuum was 1 ⁇ 10 ⁇ 4 Pa, the temperature was 300 to When sublimation purification was performed over 9 hours under the condition of 320 ° C., the yield of the sublimation product was 85%. Sublimation residue was as small as 2% of the input. Decomposition by sublimation purification was not observed, and the material balance was 87%.
  • P-200 sublimation purification apparatus
  • Example III-4 Sublimation purification of the compound (Ir-77) of the present invention 159 mg of the compound (Ir-77) of the present invention was placed in a sublimation purification apparatus (P-200, manufactured by ALS Technology Co., Ltd.), with a vacuum degree of 1 ⁇ 10 ⁇ 4 Pa, a temperature of 300 to When sublimation purification was performed for 9 hours under the condition of 330 ° C., the yield of the sublimation product was 93%. Sublimation residue was as small as 4% of the input. Decomposition by sublimation purification was not observed, and the material balance was 97%.
  • a sublimation purification apparatus P-200, manufactured by ALS Technology Co., Ltd.
  • Example III-5 Sublimation purification of the compound (Ir-95) of the present invention 125 mg of the compound (Ir-95) of the present invention was placed in a sublimation purification apparatus (P-200, manufactured by ALS Technology Co., Ltd.), and the degree of vacuum was 1 ⁇ 10 ⁇ 4 Pa and the temperature was 340 to When sublimation purification was performed over 9 hours under the condition of 360 ° C., the yield of the sublimation product was 84%. Sublimation residue was as small as 9% of the input. No decomposition due to sublimation purification was observed, and the material balance was 93%.
  • P-200 sublimation purification apparatus
  • Example III Comparison of the results of sublimation purification in Example III and Comparative Example III revealed that the compound of the present invention can be purified by sublimation with a higher yield than Comparative Compound (1).
  • the thermal stability and sublimation properties of phosphorescent materials are dramatically improved by changing the acetylacetone ligand used in comparative compound (1) to a cyclometalated ligand with a strong iridium-carbon bond. It was revealed that the sublimation residue was greatly reduced.
  • Luminescence characteristics of the compound (Ir-10) of the present invention in a thin film The compound (Ir-10) of the present invention and 4,4′-N, N′-dicarbazole biphenyl (hereinafter referred to as CBP) were combined at a degree of vacuum of 1 ⁇ 10. -4 Pa, co-evaporated (30 nm) on a quartz substrate at 10:90 (mass concentration ratio), and emission spectrum at room temperature using an absolute PL quantum yield measuring device (C9920) manufactured by Hamamatsu Photonics Co., Ltd. When measured (excitation wavelength: 340 nm), it showed red light emission (emission maximum wavelength: 630 nm) with good color purity. The emission quantum yield was 0.61.
  • Example IV-2 Luminescent properties of the compound (Ir-62) of the present invention in a thin film
  • the compound (Ir-62) of the present invention and 4,4′-N, N′-dicarbazole biphenyl (hereinafter referred to as CBP) were combined at a degree of vacuum of 1 ⁇ 10. -4 Pa, co-evaporated (30 nm) on a quartz substrate at 10:90 (mass concentration ratio), and emission spectrum at room temperature using an absolute PL quantum yield measuring device (C9920) manufactured by Hamamatsu Photonics Co., Ltd. When measured (excitation wavelength: 340 nm), it showed red light emission (emission maximum wavelength: 619 nm) with good color purity. The emission quantum yield was 0.69.
  • Example IV-3 Luminescent properties of the compound (Ir-63) of the present invention in a thin film
  • the compound (Ir-63) of the present invention and 4,4′-N, N′-dicarbazole biphenyl (hereinafter referred to as CBP) were combined at a degree of vacuum of 1 ⁇ 10. -4 Pa, co-evaporated (30 nm) on a quartz substrate at 10:90 (mass concentration ratio), and emission spectrum at room temperature using an absolute PL quantum yield measuring device (C9920) manufactured by Hamamatsu Photonics Co., Ltd. When measured (excitation wavelength: 340 nm), it showed red light emission (emission maximum wavelength: 627 nm) with good color purity. The emission quantum yield was 0.74.
  • Luminescence characteristics of comparative compound (1) For luminescence characteristics of comparative compound (1), see Adv. Mater. 2003, Vol. 15, pp. 224-228 (Non-patent Document 1). That is, the maximum wavelength of light emission in the CBP thin film is 600 to 614 nm, indicating orange-red light emission.
  • Example IV-1 to Example IV-3 From Example IV-1 to Example IV-3, it was revealed that the compound of the present invention emits red light in a CBP thin film at room temperature. It has been clarified that the compound of the present invention has a longer emission wavelength than that of the comparative compound (1) and can realize red light emission with good color purity.
  • Example V-1 Evaluation of characteristics of organic electroluminescence device prepared using compound (Ir-10) of the present invention
  • an alkali-free film was formed by patterning indium tin oxide (ITO) into a comb shape having a film thickness of 100 nm and a line width of 2 mm.
  • a glass substrate manufactured by Atsugi Micro
  • the following organic layers are placed on the transparent conductive support substrate in a vacuum chamber of 1 ⁇ 10 ⁇ 4 Pa.
  • the film was sequentially formed by vacuum vapor deposition using resistance heating, and then the mask was changed, and electrode layers (electron injection layer and metal electrode layer) having a line width of 2 mm were sequentially formed to produce an organic electroluminescent device.
  • an operation of sealing in a glove box in a nitrogen atmosphere was performed so that the element was not exposed to the air.
  • a UV curable epoxy resin denatite R (manufactured by Nagase Chemitech) is applied to the periphery of a sealing glass (manufactured by Senyo Shoji Co., Ltd.) with a 1.5 mm dug in the center of a 3 mm thick glass plate and vapor deposited. After the element was covered and pressure-bonded, the element portion was covered with an aluminum plate and masked, and then irradiated with a UV irradiation apparatus with a shutter for 1 minute and then sealed for 1 minute by repeating the shielding cycle 5 times.
  • the obtained organic electroluminescence device is set in a sample holder of an integrating sphere unit A10094 for EL external quantum yield measurement manufactured by Hamamatsu Photonics, and a direct current constant voltage is applied to emit light by using a source meter 2400 manufactured by Keithley.
  • the luminance, emission wavelength, and CIE chromaticity coordinates were measured using a multichannel spectrometer PMA-12 manufactured by Hamamatsu Photonics.
  • luminescent properties of 4% when 1000 cd / m 2) was obtained.
  • the emission spectrum is shown in FIG.
  • Example V-2 Evaluation of characteristics of organic electroluminescence device produced using compound (Ir-62) of the present invention
  • the present invention in the light emitting layer was obtained by using (Ir-62) instead of (Ir-10) used in Example V-1.
  • An organic electroluminescent device was produced under the same conditions except that the mass concentration of the compound (Ir-62) was 20%, and the device characteristics were evaluated.
  • An emission characteristic of 5% when 1000 cd / m 2 ) was obtained.
  • Example V-3 Evaluation of characteristics of organic electroluminescence device produced using compound (Ir-63) of the present invention
  • the present invention in the light emitting layer was obtained by using (Ir-63) instead of (Ir-10) used in Example V-1.
  • An organic electroluminescent device was produced under the same conditions except that the mass concentration of the compound (Ir-63) was 20%, and the device characteristics were evaluated.
  • An emission characteristic of 3% (when 1000 cd / m 2 ) was obtained.
  • Example V-4 Evaluation of characteristics of organic electroluminescent device prepared using compound (Ir-95) of the present invention Under the same conditions except that (Ir-95) was used instead of (Ir-10) used in Example V-1.
  • An organic electroluminescent device was prepared and the device characteristics were evaluated.
  • a light emission characteristic of 0% when 1000 cd / m 2 ) was obtained.
  • the iridium complex represented by the general formula (1) according to the present invention is a novel compound that is particularly excellent in thermal stability and sublimation, and exhibits a high emission quantum yield in the red region.
  • an organic light emitting device having good light emitting characteristics can be produced.
  • an organic light-emitting device using the compound exhibits high luminance light emission, and thus is suitable for fields such as a display device, a display, a backlight, and an illumination light source.

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention a pour objet un nouveau complexe d'iridium qui peut être utilisé dans un élément électroluminescent organique, un élément électroluminescent électrochimique organique et similaire, qui présente des propriétés d'émission de lumière rouge ayant une meilleure pureté de couleur par comparaison avec les composés classiques et qui a d'excellentes propriétés de sublimation. Le complexe d'iridium selon la présente invention est caractérisé en ce qu'il est représenté par la formule générale (1). (Dans la formule générale (1), N représente un atome d'azote ; Ir représente un atome d'iridium ; R1 à R9 représentent chacun indépendamment un atome d'hydrogène, un groupe alkyle ou un atome d'halogène ; et R10 à R17 représentent chacun indépendamment un atome d'hydrogène, un groupe alkyle, un groupe aryle, un groupe alcoxy, un groupe hétérocyclique, un groupe aryloxy, un groupe cyano ou un atome d'halogène).
PCT/JP2016/087675 2015-12-18 2016-12-16 Complexe d'iridium émettant de la lumière rouge et matériau électroluminescent et élément électroluminescent organique utilisant chacun ledit composé Ceased WO2017104839A1 (fr)

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WO2019207409A1 (fr) * 2018-04-27 2019-10-31 株式会社半導体エネルギー研究所 Composé organique, dispositif électroluminescent, équipement électroluminescent, dispositif électronique et dispositif d'éclairage
CN114605474A (zh) * 2020-12-04 2022-06-10 广东阿格蕾雅光电材料有限公司 一种铱络合物及其应用
JP2023043496A (ja) * 2021-09-16 2023-03-29 キヤノン株式会社 有機化合物、有機発光素子、表示装置、光電変換装置、電子機器、照明装置、移動体、および、露光光源
WO2024169509A1 (fr) * 2023-02-14 2024-08-22 广东阿格蕾雅光电材料有限公司 Complexe d'iridium métallique et dispositif électroluminescent

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JP7238782B2 (ja) 2017-11-07 2023-03-14 三菱ケミカル株式会社 イリジウム錯体化合物、該化合物及び溶剤を含有する組成物、該化合物を含有する有機電界発光素子、表示装置及び照明装置
JPWO2019093369A1 (ja) * 2017-11-07 2021-01-14 三菱ケミカル株式会社 イリジウム錯体化合物、該化合物及び溶剤を含有する組成物、該化合物を含有する有機電界発光素子、表示装置及び照明装置
WO2019093369A1 (fr) * 2017-11-07 2019-05-16 三菱ケミカル株式会社 Composé complexe d'iridium, composition contenant ledit composé et solvant, élément électroluminescent organique contenant ledit composé, dispositif d'affichage et dispositif d'éclairage
JP2023036713A (ja) * 2017-11-07 2023-03-14 三菱ケミカル株式会社 イリジウム錯体化合物、該化合物及び溶剤を含有する組成物、該化合物を含有する有機電界発光素子、表示装置及び照明装置
JP7439891B2 (ja) 2017-11-07 2024-02-28 三菱ケミカル株式会社 イリジウム錯体化合物、該化合物及び溶剤を含有する組成物、該化合物を含有する有機電界発光素子、表示装置及び照明装置
WO2019207409A1 (fr) * 2018-04-27 2019-10-31 株式会社半導体エネルギー研究所 Composé organique, dispositif électroluminescent, équipement électroluminescent, dispositif électronique et dispositif d'éclairage
CN112041326A (zh) * 2018-04-27 2020-12-04 株式会社半导体能源研究所 有机化合物、发光器件、发光装置、电子设备、及照明装置
JPWO2019207409A1 (ja) * 2018-04-27 2021-06-17 株式会社半導体エネルギー研究所 有機化合物、発光デバイス、発光装置、電子機器、および照明装置
JP7287953B2 (ja) 2018-04-27 2023-06-06 株式会社半導体エネルギー研究所 有機金属錯体、発光デバイス、発光装置、電子機器、および照明装置
CN114605474A (zh) * 2020-12-04 2022-06-10 广东阿格蕾雅光电材料有限公司 一种铱络合物及其应用
JP2023043496A (ja) * 2021-09-16 2023-03-29 キヤノン株式会社 有機化合物、有機発光素子、表示装置、光電変換装置、電子機器、照明装置、移動体、および、露光光源
JP7749386B2 (ja) 2021-09-16 2025-10-06 キヤノン株式会社 有機化合物、有機発光素子、表示装置、光電変換装置、電子機器、照明装置、移動体、および、露光光源
WO2024169509A1 (fr) * 2023-02-14 2024-08-22 广东阿格蕾雅光电材料有限公司 Complexe d'iridium métallique et dispositif électroluminescent

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