WO2018084189A1 - Procédé de production de complexe d'iridium, complexe d'iridium et matériau électroluminescent comprenant ledit composé - Google Patents

Procédé de production de complexe d'iridium, complexe d'iridium et matériau électroluminescent comprenant ledit composé Download PDF

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WO2018084189A1
WO2018084189A1 PCT/JP2017/039582 JP2017039582W WO2018084189A1 WO 2018084189 A1 WO2018084189 A1 WO 2018084189A1 JP 2017039582 W JP2017039582 W JP 2017039582W WO 2018084189 A1 WO2018084189 A1 WO 2018084189A1
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group
ring
iridium complex
iridium
atom
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今野　英雄
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国立研究開発法人産業技術総合研究所
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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, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • 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

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  • the present invention relates to a method for producing an iridium complex suitably used as a light-emitting material such as an organic electroluminescent element and a light-emitting sensor, a novel iridium complex obtained by the production method, and a light-emitting material comprising the compound.
  • Luminescent materials used for organic electroluminescent elements can be broadly classified into fluorescent materials that utilize light emission from an excited singlet state and phosphorescent materials that utilize light emission from an excited triplet state.
  • the generation ratio of singlet excitons to triplet excitons is 1: 3, and the generation probability of luminescent excitons is 25%.
  • the limit of the external extraction quantum efficiency is set to 5%.
  • the excited triplet state can also be used, the upper limit of the internal quantum efficiency is 100%, so that in principle the light emission efficiency is four times that in the case of using only the excited singlet state. Therefore, phosphorescent materials have been actively studied as light emitting materials for organic electroluminescent elements.
  • cyclometalated iridium complexes are known as phosphorescent materials.
  • the triscyclometalated iridium complex having three cyclometalated aromatic heterocyclic ligands has high thermal stability and excellent durability because it has three strong iridium-carbon bonds. Phosphorescent material.
  • Patent Document 1 discloses an iridium complex in which all three cyclometalated aromatic heterocyclic ligands have the same structure (Chemical Formula 1).
  • Patent Document 2 discloses an iridium complex having a different structure of a cyclometalated aromatic heterocyclic ligand by one (Chemical Formula 2).
  • Non-Patent Document 1 discloses an iridium complex in which the structures of three cyclometalated aromatic heterocyclic ligands are all different (Chemical Formula 3).
  • Non-Patent Document 1 it is possible to produce a triscyclometalated iridium complex (Chemical Formula 3) having different aromatic heterocyclic ligand structures by a method comprising the following steps (A) to (E). It is disclosed.
  • Non-Patent Document 1 In the production method described in Non-Patent Document 1 described above, of the three types of iridium complexes (B-1) to (B-3) obtained in step (B), an aromatic heterocyclic ligand is used. It is necessary to isolate iridium complexes (B-1) having different structures. However, when the polarities of the three types of iridium complexes obtained in the step (B) are similar, it is extremely difficult to separate and purify the desired iridium complex. That is, the manufacturing method of the iridium complex described in Non-Patent Document 1 has an essential problem that can be applied only when the polarities of the three types of iridium complexes generated in the step (B) are greatly different. Furthermore, in the step (E), since the reaction is performed at a high temperature of 200 ° C., scrambling of the ligand is likely to occur, and it may be difficult to isolate a desired iridium complex.
  • An object of the present invention is to provide a method for efficiently producing a triscyclometalated iridium complex having different aromatic heterocyclic ligand structures, which is preferably used in an organic electroluminescent device, a luminescent sensor, and the like. It is an object of the present invention to provide a novel iridium complex obtained by the production method and a luminescent material using the compound.
  • a manufacturing method of A triscyclometalated iridium complex having two different aromatic heterocyclic ligands forming an iridium-nitrogen bond and an iridium-carbon bond is reacted with a halogenating agent to form a halogen to the triscyclometalated iridium complex.
  • ⁇ 3> The iridium complex according to 1 or 2 above, wherein the introduction of the halogen atom in the step (1) is performed by any one of two aromatic heterocyclic ligands having the same structure. Production method.
  • ⁇ 4> In the triscyclometalated iridium complex used in the step (1), one or two para positions counted from the carbon atom of the benzene ring bonded to iridium are an alkyl group, an aryl group, or a heterocyclic group. 4. The method for producing an iridium complex according to any one of 1 to 3, wherein the iridium complex is substituted with any one of the above.
  • the aromatic heterocyclic ligand is 2-phenylpyridine, 1-phenylisoquinoline, 2-phenylquinoline, 2-phenylimidazole, 5-phenyl-1,2,4-triazole, 3-phenyl- 1,2,4-triazole, 1-phenylpyrazole, 2-phenylpyrazine, 2-phenylpyrimidine, 4-phenylpyrimidine, 3-phenylpyridazine, benzo [h] quinoline, dibenzo [f, h] quinoxaline, 2,3 -Diphenylquinoxaline, imidazo [1,2-f] phenanthridine, and the ligand is at least one selected from the group consisting of an alkyl group, an aryl group, a heterocyclic group, an alkylsilyl group, or a halogen atom 5.
  • the iridium complex according to any one of 1 to 4 above, which may be substituted with one group Body manufacturing method.
  • Ir represents an iridium atom
  • N represents a nitrogen atom.
  • Ring A, ring B, and ring C each independently represent a 5-membered or 6-membered nitrogen-containing heterocycle.
  • R a to R c each represent a group or an atom bonded to an atom contained in the ring structure of ring A to ring C
  • R d to R f represent three carbons contained in the ring structure of each benzene ring.
  • Each of R a to R f and R 1 to R 3 bonded to an atom included in each ring structure independently represents a hydrogen atom, an alkyl group, or an aryl; Represents a group, a heterocyclic group, an alkylsilyl group, or a halogen atom, provided that at least one of R 1 to R 3 is a substituent represented by any one of formulas (2) to (7).
  • R 1 ⁇ R 2 ⁇ R 3 there, and a R 1 ⁇ R 2 ⁇ R 3 .
  • our R a ⁇ R f Fine R 1 groups each other adjacent the ⁇ R 3 may be bonded to form a condensed ring.)
  • N represents a nitrogen atom.
  • R 4 to R 27 each independently represents a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkylsilyl group, or a halogen atom. And an adjacent group of R 4 to R 27 may be bonded to each other to form a condensed ring.) ⁇ 7> The iridium complex as described in 6 above, which is represented by any one of the general formulas (8) to (15).
  • each of R a to R f bonded to an atom contained in each ring structure and R 2 to R 37 are each independently a hydrogen atom, an alkyl group, Represents an aryl group, a heterocyclic group, an alkylsilyl group, or a halogen atom, R a to R f and R 2 , adjacent groups of R 3 , and adjacent groups of R 4 to R 37 May be bonded to each other to form a condensed ring, provided that the phenyl group having R 4 to R 8 , R 2 , and R 3 are not the same group, and have R 4 to R 8 (The phenyl group, the phenyl group having R 28 to R 32 , and the phenyl group having R 33 to R 37 are not the same group.)
  • the ring A, ring B, and ring C are each independently a pyridine ring, a quinoline ring, an isoquinoline ring,
  • a luminescent material comprising the iridium complex according to any one of 6 to 12 above.
  • An organic light emitting device comprising the light emitting material as described in 13 above.
  • a new method for producing a triscyclometalated iridium complex which can be suitably used as a phosphorescent material such as an organic electroluminescent device and which has three different aromatic heterocyclic ligand structures.
  • the A novel iridium complex having excellent light emission characteristics can be provided using the production method.
  • novel iridium complex produced by the production method of the present invention is highly soluble in a solvent, excellent in processability, and exhibits strong light emission in the visible light region at room temperature. Can be suitably used.
  • a light-emitting element using the compound exhibits high-luminance light emission in the visible light region, and thus is suitable for use in fields such as a display element, a display, a backlight, or an illumination light source.
  • a hydrogen atom includes an isotope (such as a deuterium atom), and an atom constituting a substituent further includes the isotope.
  • Ir represents an iridium atom
  • N represents a nitrogen atom
  • Ring A, Ring B, and Ring C each independently represent a 5-membered or 6-membered nitrogen-containing heterocyclic ring, and preferably a 6-membered nitrogen-containing heterocyclic ring.
  • Ring A, ring B, and ring C may be the same or different, and are preferably the same.
  • the same means a nitrogen-containing heterocycle having the same skeleton, and does not consider substituents attached to the nitrogen-containing heterocycle.
  • Ring A, ring B and ring C are specifically pyridine ring, quinoline ring, isoquinoline ring, pyrimidine ring, pyrazine ring, pyridazine ring, quinoxaline ring, benzoquinoline ring, benzoquinoxaline ring, dibenzoquinoline ring, dibenzoquinoxaline Ring, phenanthridine ring, tetrazole ring, imidazole ring, or triazole ring are preferable, and pyridine ring, quinoline ring, isoquinoline ring, pyrimidine ring, pyrazine ring, pyridazine ring, quinoxaline ring, imidazole ring, or triazole ring are more preferable.
  • a pyridine ring, a quinoline ring, an isoquinoline ring, an imidazole ring or a triazole ring is particularly preferable, a pyridine ring or an isoquinoline ring is further particularly preferable, and a pyridine ring is most preferable.
  • Ring A, Ring B, and Ring C may be substituted with at least one group selected from the group consisting of an alkyl group, an aryl group, a heterocyclic group, an alkylsilyl group, or a halogen atom, and these substituents May be further substituted with the above substituents.
  • an alkyl group, an aryl group, or a heterocyclic group is preferable, an alkyl group or an aryl group is more preferable, and an alkyl group is especially preferable.
  • each of the ring A ⁇ ring C of R a ⁇ each represent a bond to group or atom to atom contained in the ring structure R c, each independently, a hydrogen atom, an alkyl group, an aryl Represents a group, a heterocyclic group, an alkylsilyl group, or a halogen atom.
  • R a to R c are preferably a hydrogen atom, an alkyl group, or an aryl group, and more preferably a hydrogen atom or an alkyl group.
  • substituents may be further substituted with at least one group selected from the group consisting of alkyl groups, aryl groups, heterocyclic groups, alkylsilyl groups, or halogen atoms.
  • each of R d to R f representing a group or atom bonded to three carbon atoms contained in the ring structure of each benzene ring is independently a hydrogen atom, an alkyl group Represents an aryl group, a heterocyclic group, an alkylsilyl group, or a halogen atom.
  • R d to R f are preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an alkyl group, and particularly preferably all hydrogen atoms.
  • These substituents may be further substituted with at least one group selected from the group consisting of alkyl groups, aryl groups, heterocyclic groups, alkylsilyl groups, or halogen atoms.
  • R 1 to R 3 each independently represents a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkylsilyl group, or a halogen atom. However, at least one of R 1 to R 3 is a substituent represented by any one of the general formulas (2) to (7). At least one of R 1 to R 3 is preferably the general formulas (2) to (4) or (7), more preferably the general formulas (2) to (4), The formula (2) is particularly preferable.
  • R 1 to R 3 are R 1 ⁇ R 2 ⁇ R 3 .
  • R 1 ⁇ R 2 ⁇ R 3 means that R 1 to R 3 are not the same group.
  • R 1 to R 3 are groups represented by the general formula (2), they are not the same group as long as any of R 4 to R 8 of the substituents is different.
  • R 1 to R 3 is preferably a hydrogen atom or a halogen atom, and more preferably a hydrogen atom.
  • R 3 is preferably a hydrogen atom.
  • adjacent groups of R a to R f and R 1 to R 3 may be bonded to each other to form a condensed ring.
  • R 4 to R 37 each independently represents a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkylsilyl group, or a halogen atom, preferably a hydrogen atom, an alkyl group, or an aryl group. These substituents may be further substituted with at least one group selected from the group consisting of alkyl groups, aryl groups, heterocyclic groups, alkylsilyl groups, or halogen atoms. Further, adjacent groups of R 4 to R 37 may be bonded to each other to form a condensed ring.
  • the alkyl group in the present specification does not include the carbon number of the substituent, and preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, 1 to 6 is more particularly preferable.
  • alkyl group in the present specification a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl are preferable.
  • the aryl group in the present specification does not include the carbon number of the substituent, and preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, 6 to 12 is more particularly preferable.
  • a phenyl group a biphenyl-2-yl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a p-terphenyl-4-yl group, or a p-terphenyl is preferable.
  • the heterocyclic group in the present specification does not include the carbon number of the substituent, preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, Numbers 1 to 6 are more particularly preferable.
  • heterocyclic group in the present specification preferably an imidazolyl group, a pyridyl group, a pyrimidyl group, a triazyl group, a pyrazyl group, a pyridazyl group, a quinolyl group, a furyl group, a thienyl group, a dibenzothienyl group, a piperidyl group, a morpholino group, A benzoxazolyl group, a benzimidazolyl group, a benzthiazolyl group, a carbazolyl group, or an azepinyl group, more preferably a pyridyl group, a pyrimidyl group, a triazyl group, a pyrazyl group, a pyridazyl group, or a dibenzothienyl group, Particularly preferred is a pyridyl group, pyrimidyl group, triazyl group
  • the alkylsilyl group in the present specification does not include the carbon number of the substituent, and preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, Numbers 1 to 6 are more particularly preferable.
  • the alkylsilyl group in the present specification is preferably a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, a dimethylphenyl group, a t-butyldimethylsilyl group, or a t-butyldiphenylsilyl group, and more preferably a trimethylsilyl group.
  • the halogen atom in the present specification is preferably a chlorine atom, a bromine atom or an iodine atom, more preferably a bromine atom or an iodine atom, and particularly preferably a bromine atom.
  • the method for producing an iridium complex according to the present invention is characterized by sequentially including steps (1) to (3) described in detail below.
  • a triscyclometalated iridium complex having two different aromatic heterocyclic ligands that form an iridium-nitrogen bond and an iridium-carbon bond is reacted with a halogenating agent to form a triscyclometal. It is characterized by introducing a halogen atom into an iridium iodide complex.
  • the triscyclometalated iridium complex having two different aromatic heterocyclic ligands in the step (1) is preferably represented by the general formula (16) or (17).
  • General formula (16) is a facial body
  • general formula (17) is a meridional body.
  • Y represents an aromatic heterocyclic ligand that forms an iridium-nitrogen bond and an iridium-carbon bond
  • Z forms an iridium-nitrogen bond and an iridium-carbon bond.
  • examples of the aromatic heterocyclic ligand include 2-phenylpyridine, 1-phenylisoquinoline, 2-phenylquinoline, 2-phenylimidazole, 5-phenyl-1,2,4-triazole, 3 -Phenyl-1,2,4-triazole, 1-phenylpyrazole, 2-phenylpyrazine, 2-phenylpyrimidine, 4-phenylpyrimidine, 3-phenylpyridazine, benzo [h] quinoline, dibenzo [f, h] quinoxaline, 2,3-diphenylquinoxaline or imidazo [1,2-f] phenanthridine is preferred, and 2-phenylpyridine, 1-phenylisoquinoline, 2-phenylquinoline, 2-phenylimidazole, 5-phenyl-1,2 , 4-triazole, 3-phenyl-1,2,4-triazole Or, imidazo [1,2-f] phenanthridine more preferably, 2-phenylpyridine,
  • aromatic heterocyclic ligands may be substituted with at least one group selected from the group consisting of an alkyl group, an aryl group, a heterocyclic group, an alkylsilyl group, or a halogen atom.
  • the group may be further substituted with the above substituents.
  • Introducing a halogen atom into the triscyclometalated iridium complex in the step (1) can be performed with reference to the methods described in WO2015 / 141603, WO2009 / 073245, JP2014-205643, and the like.
  • a reaction example is shown below.
  • the introduction of the halogen atom in the step (1) is performed at the benzene ring part of the aromatic heterocyclic ligand forming the iridium-carbon bond, and the position is para-positioned from the carbon atom bonded to iridium. It is preferable that
  • the introduction of the halogen atom in the step (1) is preferably performed with two aromatic heterocyclic ligands having the same structure (Y in the general formula (16) or (17)). More preferably, the reaction is carried out in any one of two aromatic heterocyclic ligands (Y in the general formula (16) or (17)).
  • the para-position (one or two, preferably one) counted from the carbon atom on the benzene ring bonded to iridium is an alkyl group, an aryl group, Alternatively, it is preferably substituted with a heterocyclic group, and more preferably substituted with an aryl group.
  • the aromatic heterocyclic ligand substituted with the above substituent is an aromatic heterocyclic ligand (of the general formula (16) or (17), which is different from one of the triscyclometalated iridium complexes). More preferably, Z).
  • the para position (one or two, preferably one) counted from the carbon atom on the benzene ring bonded to iridium is an alkyl group, aryl
  • the group is not substituted with a group or a heterocyclic group, as shown below, there are a plurality of types of aromatic heterocyclic ligands to be halogenated, so that various iridium complexes can be obtained.
  • the para-position one or two, preferably one counted from the carbon atom on the benzene ring bonded to iridium is an alkyl group, aryl Compared with the case where it is substituted with a group or a heterocyclic group, it takes more time to separate and purify the desired iridium complex in the step (2) or (3) described later.
  • an iodinating agent, a brominating agent or a chlorinating agent is preferable, an iodinating agent or a brominating agent is more preferable, and a brominating agent is particularly preferable.
  • N-iodosuccinimide N-iodosuccinimide
  • DIH 1,3-diiodo-5,5-dimethylhydantoin
  • N-bromosuccinimide N-bromosuccinimide
  • DBI dibromoisocyanuric acid
  • 1,3-dibromo-5,5-dimethylhydantoin 1,3-dibromo-5,5-dimethylhydantoin and the like are preferably used.
  • N-chlorosuccinimide N-chlorosuccinimide
  • sodium dichloroisocyanurate sodium dichloroisocyanurate
  • the step (1) is characterized by using a triscyclometalated iridium complex having two different aromatic heterocyclic ligands that form an iridium-nitrogen bond and an iridium-carbon bond.
  • a new geometric isomer is generated by the step (1), for example, as shown below.
  • a new geometric isomerism can be obtained by reacting a triscyclometalated iridium complex having two different aromatic heterocyclic ligands with a halogenating agent.
  • the body can be manufactured.
  • Step (2) is characterized in that the halogen atom of the triscyclometalated iridium complex produced in the step (1) is converted into a boronic ester.
  • step (2) when a triscyclometalated iridium complex into which a plurality of halogen atoms are introduced is used, an iridium complex into which a plurality of boronic acid esters are introduced may be generated. It is possible to separate and purify a triscyclometalated iridium complex into which one boronic acid ester has been introduced using silica gel column chromatography.
  • Step (3) is characterized in that the triscyclometalated iridium complex produced in Step (2) and an organic halogen compound are subjected to a cross-coupling reaction to form a carbon-carbon bond.
  • the method in which the triscyclometalated iridium complex and the halogen compound in the step (3) are cross-coupled is called a so-called Suzuki coupling reaction.
  • Suzuki coupling reaction WO2015 / 141603, WO2009 / 073246, JP2014 -139193 can be used.
  • the organic halogen compound includes a halogenated aryl compound, a halogenated alkyl compound, a halogenated heterocyclic compound, etc., and the halogen is preferably iodine, bromine, or chlorine, iodine, or Bromine is more preferred.
  • the iridium complex according to the present invention can be subjected to the post-treatment of a normal synthesis reaction, and then refined or used without further purification if necessary.
  • the post-treatment can be performed, for example, by a method such as extraction, cooling, crystallization by adding water or an organic solvent, or an operation of distilling off the solvent from the reaction mixture.
  • Purification can be performed by a single method or a combination of methods such as recrystallization, distillation, sublimation or column chromatography.
  • the iridium complex obtained by the production method of the present invention is preferably represented by the general formula (1).
  • the iridium complex represented by any one of the general formulas (8) to (15) is preferable, and the iridium complex represented by any one of the general formulas (8) to (10) and (13) to (15) Is more preferable, and an iridium complex represented by any one of the general formulas (9), (10), and (13) to (15) is particularly preferable.
  • those having an emission quantum yield in a solution at room temperature of 0.1 or more are preferable, and those having an emission quantum yield of 0.5 or more are more preferable. Preferably, it is 0.85 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.
  • the emission quantum yield can be measured by comparing the emission spectrum with a standard substance (such as quinine sulfate).
  • the absolute method the emission quantum yield in the solution can be measured by using a commercially available apparatus (for example, an absolute PL quantum yield measuring apparatus (C9920-02) manufactured by Hamamatsu Photonics Co., Ltd.).
  • the half width of the emission spectrum in a solution at room temperature is preferably 75.0 nm or less, and more preferably 72.5 nm or less. Those having a diameter of 70.0 nm or less are particularly preferable, and those having a diameter of 68.0 nm or less are particularly preferable. A narrow half-value width of the emission spectrum is particularly useful as a phosphorescent material for display applications.
  • the iridium complex represented by the general formula (1) according to the present invention is an octahedral 6-coordination complex, and there are a facial isomer and a meridional isomer as geometric isomers.
  • the iridium complex represented by the general formula (1) according to the present invention is preferably a facial body.
  • the iridium complex according to the present invention preferably contains 50% or more of the facial compound, more preferably contains 80% or more, particularly preferably contains 90% or more, and contains 99% or more. It is more particularly preferable.
  • the facial body or meridional body can be separated and purified using a technique such as column chromatography or recrystallization, and can be identified by NMR, mass spectrometry or X-ray crystal structure analysis. The content can be quantified by NMR or HPLC.
  • the iridium complex represented by the general formula (1) according to the present invention has three different aromatic heterocyclic ligands, it has further geometric isomers in addition to the facial and meridional isomers.
  • two types of geometric isomers are generated in step (1), and in step (2) and step (3), the two types of geometric isomers are probably isomerized to each other.
  • two geometric isomers are obtained.
  • the facial isomers of the present compound (K-40) shown below include geometric isomer 1 and geometric isomer 2. It was revealed that when the iridium complex represented by the general formula (1) according to the present invention was actually synthesized, it was obtained as a mixture of these geometric isomers (see Examples).
  • the iridium complex of the present invention has practically excellent characteristics such as good solubility in a solvent and suppression of crystallization due to such structural characteristics.
  • homoleptic tris-cyclometalated iridium complexes with three identical cyclometalated ligands are highly symmetric and have good crystallinity in the solid state. There was a problem of lowering.
  • the iridium complex of the present invention represented by the general formula (1) since the iridium complex of the present invention represented by the general formula (1) has low symmetry, the crystallinity in the solid state is low, the energy for linking the complexes decreases, and the sublimation property tends to be improved.
  • the method for producing an iridium complex according to the present invention enables simple and efficient production of triscyclometalated iridium complexes having different structures of all three aromatic heterocyclic ligands. It is. Further, the iridium complex produced by the method of the present invention is excellent in the visible light region by being contained in a light emitting layer of a light emitting element or a plurality of organic compound layers including a light emitting layer by a vacuum deposition method, a spin coating method, or the like. A light-emitting element that emits light is obtained.
  • the iridium complex of the present invention for a light-emitting element, a change in film quality (for example, crystallization of a material) is suppressed, and a light-emitting element having a stable and long life can be obtained.
  • Step 4 Synthesis of Compound E> 1.05 g of the compound (C) obtained in Step 3, 635 mg of bis (pinacolato) diboron, 1.1 g of potassium acetate, 50 ml of 1,4-dioxane, [1,1′-bis (diphenylphosphino) ferrocene] palladium ( II) 153 mg of dichloride dichloromethane adduct (Pd (dppf) 2 Cl 2 .CH 2 Cl 2 ) and 104 mg of 1,1′-bis (diphenylphosphino) ferrocene (dppf) were heated to reflux in an argon atmosphere for 17 hours.
  • reaction solution was cooled to room temperature, and the reaction solution was filtered through a celite layer to remove insoluble matters. The filtrate was concentrated under reduced pressure to obtain a solid. This was further separated and purified by silica gel chromatography (eluent: mixed solvent of dichloromethane and hexane) to obtain 510 mg of the desired compound (E) consisting of a mixture of geometric isomers. The yield was 84%.
  • 1 H-NMR data and ESI-MS data of the compound (E) are shown below.
  • Step 5 Synthesis of Compound (K-40)> Compound (E) 250 mg obtained in Step 4, SPhos (2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl) 24 mg, potassium phosphate 183 mg, 1-bromo-3,5-dimethylbenzene 160 mg, toluene 40 ml After argon gas was bubbled through the mixture of 4 ml of water for 30 minutes, 5.2 mg of tris (dibenzylideneacetone) dipalladium (0) was added, and the mixture was heated to reflux for 17 hours under an argon atmosphere. Thereafter, the reaction solution was cooled to room temperature, and the reaction solution was filtered through a celite layer to remove insoluble matters.
  • Example 2 (Synthesis of Compound (K-39) of the Present Invention) Compound (E) 150 mg, SPhos (2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl) 14 mg, potassium phosphate 110 mg, 1-bromo-4- (trifluoromethyl) benzene 116 mg, toluene 40 ml, water 4 ml After argon gas was bubbled through the mixture for 30 minutes, 3.1 mg of tris (dibenzylideneacetone) dipalladium (0) was added, and the mixture was heated to reflux for 17 hours under an argon atmosphere.
  • Example 3 (Synthesis of Compound (K-41) of the Present Invention) Compound (E) 300 mg, SPhos (2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl) 28 mg, potassium phosphate 220 mg, 5′-bromo-4,4 ′′ -diisopropyl-1,1-3 ′, 1 After argon gas was bubbled through a mixture of 406.2 mg of -terphenyl, 50 ml of toluene and 5 ml of water for 30 minutes, 6.2 mg of tris (dibenzylideneacetone) dipalladium (0) was added, and the mixture was added under argon atmosphere for 17 hours. Heated to reflux.
  • reaction solution was cooled to room temperature, and the reaction solution was filtered through a celite layer to remove insoluble matters.
  • Dichloromethane was added to the filtrate for extraction, and the organic layer was concentrated under reduced pressure.
  • the obtained solid was separated and purified by silica gel column chromatography (eluent: mixed solvent of dichloromethane and hexane) to obtain 180 mg of the present compound (K-41) comprising a mixture of geometric isomers.
  • the yield was 48.6%.
  • the 1 H-NMR data and ESI-MS data of the compound of the present invention (K-41) are shown below.
  • reaction solution was cooled to room temperature, and the reaction solution was filtered through a celite layer to remove insoluble matters.
  • Dichloromethane was added to the filtrate for extraction, and the organic layer was concentrated under reduced pressure.
  • the obtained solid was purified by silica gel column chromatography (eluent: mixed solvent of dichloromethane and hexane) to obtain 180 mg of the present compound (K-16) comprising a mixture of geometric isomers.
  • the yield was 50.0%.
  • the 1 H-NMR data and ESI-MS data of the compound of the present invention (K-16) are shown below.
  • Example 5 (Synthesis of Compound (K-34) of the Present Invention) Compound (E) 200 mg, SPhos (2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl) 19 mg, potassium phosphate 146 mg, 4-bromodibenzothiophene 182 mg, toluene 40 ml, water 4 ml to a mixture of 30 argon gas After venting for minutes, 4.1 mg of tris (dibenzylideneacetone) dipalladium (0) was added, and the mixture was heated to reflux for 17 hours under an argon atmosphere. Thereafter, the reaction solution was cooled to room temperature, and the reaction solution was filtered through a celite layer to remove insoluble matters.
  • Example 6 (Synthesis of Compound (K-10) of the Present Invention) Compound (E) 150 mg, SPhos (2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl) 14.1 mg, potassium phosphate 101 mg, 2-bromo-4,6-diphenylpyrimidine 161 mg, toluene 40 ml, water 4 ml After argon gas was bubbled through the mixture for 30 minutes, 3.1 mg of tris (dibenzylideneacetone) dipalladium (0) was added, and the mixture was heated to reflux for 17 hours under an argon atmosphere.
  • Step 1 Synthesis of Compound (K-42)> A mixture of 50 mg of compound (K-41) and 15 ml of dichloromethane was cooled to 0 ° C. To the reaction solution, 13.5 mg of N-bromosuccinimide was added under light shielding, and the mixture was stirred at 25 ° C. for 17 hours. After completion of the reaction, the reaction solution was distilled off under reduced pressure to obtain a solid. This solid was separated and purified by silica gel column chromatography (eluent: dichloromethane) to give the compound of the present invention (K-42) consisting of a mixture of geometric isomers.
  • reaction solution was cooled to room temperature, and the reaction solution was filtered through a celite layer to remove insoluble matters.
  • Dichloromethane was added to the filtrate for extraction, and the organic layer was concentrated under reduced pressure.
  • the obtained solid was separated and purified by silica gel column chromatography (eluent: mixed solvent of dichloromethane and hexane) to obtain 16 mg of the present compound (K-46) comprising a mixture of geometric isomers.
  • the yield was 24.4%.
  • the 1 H-NMR data and ESI-MS data of the compound (K-46) are shown below.
  • Example 8 (Synthesis of Compound (K-11) of the present invention)
  • Compound (E) 200 mg, SPhos (2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl) 19 mg, potassium phosphate 146 mg, 2-bromo-4,6-di-tert-butylpyrimidine 156 mg, toluene 50 ml, water Argon gas was bubbled through 5 ml of the mixture for 30 minutes, then 4.2 mg of tris (dibenzylideneacetone) dipalladium (0) was added, and the mixture was heated to reflux for 17 hours under an argon atmosphere.
  • Step 2 The total amount of the compound (G) obtained in Step 1 was 165 mg of bis (pinacolato) diboron, 286 mg of potassium acetate, 60 ml of 1,4-dioxane, [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) Dichlorochloride adduct (Pd (dppf) 2 Cl 2 .CH 2 Cl 2 ) (49 mg) and 1,1′-bis (diphenylphosphino) ferrocene (dppf) (27 mg) were heated to reflux for 17 hours under an argon atmosphere.
  • Step 2 Synthesis of Compound K>
  • the total amount of the compound (J) obtained in Step 1 was 565 mg of bis (pinacolato) diboron, 983 mg of potassium acetate, 150 ml of 1,4-dioxane, [1,1′-bis (diphenylphosphino) ferrocene] palladium (II)
  • Dichlorochloride adduct (Pd (dppf) 2 Cl 2 .CH 2 Cl 2 ) 136 mg and 1,1′-bis (diphenylphosphino) ferrocene (dppf) 93 mg were heated to reflux for 17 hours under an argon atmosphere.
  • triscyclometalated iridium complexes having different structures of the three aromatic heterocyclic ligands which were extremely difficult to synthesize by the conventional method, can be easily and widely produced by the production method of the present invention. It became possible to synthesize.
  • the production method of the present invention it is possible to greatly increase the variations of the triscyclometalated iridium complex that can be applied to organic electroluminescent elements and the like, and contribute to the development and practical application of phosphorescent materials.
  • Example 11 Luminescence of the compound (K-40) of the present invention in THF
  • the compound (K-40) of the present invention was dissolved in THF and aerated with argon gas, and then the emission spectrum (excitation wavelength) at room temperature was measured using an absolute PL quantum yield measuring device (C9920) manufactured by Hamamatsu Photonics Co., Ltd. : 350 nm), green light emission (emission maximum wavelength: 520.0 nm) was observed.
  • the emission quantum yield was 0.89.
  • the half width of the emission spectrum was 71.9 nm.
  • Example 12 emission of Compound (K-41) of the present invention in THF
  • the compound (K-41) of the present invention was dissolved in THF and aerated with argon gas, and then the emission spectrum (excitation wavelength) at room temperature was measured using an absolute PL quantum yield measuring device (C9920) manufactured by Hamamatsu Photonics Co., Ltd. : 350 nm), green light emission (emission maximum wavelength: 519.3 nm) was observed.
  • the emission quantum yield was 0.88.
  • the half width of the emission spectrum was 67.8 nm.
  • Example 13 Luminescence of the compound (K-16) of the present invention in THF
  • the compound (K-16) of the present invention was dissolved in THF and argon gas was passed through, and then the emission spectrum (excitation wavelength) at room temperature was measured using an absolute PL quantum yield measuring device (C9920) manufactured by Hamamatsu Photonics Co., Ltd. : 350 nm), green light emission (emission maximum wavelength: 518.5 nm) was exhibited.
  • the emission quantum yield was 0.89.
  • the half width of the emission spectrum was 69.3 nm.
  • Example 14 emission of compound of the present invention (K-34) in THF
  • the compound (K-34) of the present invention was dissolved in THF and aerated with argon gas, and then the emission spectrum (excitation wavelength) at room temperature was measured using an absolute PL quantum yield measuring device (C9920) manufactured by Hamamatsu Photonics Co., Ltd. : 350 nm), green light emission (emission maximum wavelength: 519.3 nm) was observed.
  • the emission quantum yield was 0.88.
  • the half width of the emission spectrum was 68.0 nm.
  • Example 15 (Emission of Compound (K-10) of the present invention in THF)
  • the compound (K-10) of the present invention was dissolved in THF and aerated with argon gas, and then the emission spectrum (excitation wavelength) at room temperature was measured using an absolute PL quantum yield measuring device (C9920) manufactured by Hamamatsu Photonics Co., Ltd. : 350 nm), green light emission (emission maximum wavelength: 515.6 nm) was exhibited.
  • the emission quantum yield was 0.87.
  • the half width of the emission spectrum was 66.8 nm.
  • Example 16 (luminescence of the present compound (K-46) in THF)
  • the compound (K-46) of the present invention was dissolved in THF and aerated with argon gas, and then the emission spectrum (excitation wavelength) at room temperature was measured using an absolute PL quantum yield measuring device (C9920) manufactured by Hamamatsu Photonics Co., Ltd. : 350 nm), green light emission (emission maximum wavelength: 520.8 nm) was observed.
  • the emission quantum yield was 0.88.
  • the half width of the emission spectrum was 70.7 nm.
  • Example 17 Solubility of the compound of the present invention
  • chloroform In order to confirm the solubility in toluene, 0.1 wt% solutions were prepared and visually confirmed, and it was found that they were completely dissolved.
  • Comparative Example 4 Solubility of Comparative Compound
  • a solvent chloroform, toluene
  • Comparative Example 5 Solubility of Comparative Compound
  • a 0.1 wt% solution was prepared and visually confirmed. occured.
  • the iridium complex represented by the general formula (1) of the present invention showed a higher emission quantum yield than Ir (ppy) 3 . Furthermore, it was revealed that the half width of the emission spectrum of the iridium complex represented by the general formula (1) of the present invention is narrower than Ir (ppy) 3 .
  • the iridium complex represented by the general formula (1) of the present invention is a novel compound synthesized for the first time by the production method of the present invention, and has a light emission spectrum having a sharper shape with higher luminous efficiency than Ir (ppy) 3. As shown, it is particularly useful as a phosphorescent material for display applications.
  • the iridium complex of the present invention in which the structures of the three aromatic heterocyclic ligands are all different, is an iridium complex in which all of the aromatic heterocyclic ligands have the same structure ( It can be seen that the solubility in the solvent is superior to Ir (ppy) 3 ) and the iridium complex (compound (B)) in which only one aromatic heterocyclic ligand structure is different.
  • the iridium complex of the present invention described in Example 17 was synthesized by introducing a substituent into the compound (B), and the structures of the three aromatic heterocyclic ligands were all different from each other. It was revealed that it showed high solubility in the solvent.

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  • Chemical & Material Sciences (AREA)
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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne : un nouveau procédé de production d'un complexe d'iridium triscyclométallé ayant trois ligands hétérocycliques aromatiques différents, qui est un complexe qui a été difficile à synthétiser jusqu'à présent ; et un nouveau complexe d'iridium qui est produit en utilisant le procédé de production, ledit composé a une solubilité élevée dans des solvants et une excellente aptitude au traitement, et peut émettre de la lumière à température ambiante avec une luminosité et une efficacité élevées. L'invention concerne également un procédé de production d'un complexe d'iridium triscyclométallé ayant trois ligands hétérocycliques aromatiques capables de former une liaison iridium-azote et une liaison iridium-carbone, les structures des ligands hétérocycliques aromatiques étant différentes les unes des autres, ledit procédé étant caractérisé en ce qu'il comprend, dans l'ordre suivant, les étapes consistant à : (1) faire réagir un complexe d'iridium triscyclométallé, qui a deux ligands hétérocycliques aromatiques différents respectivement capables de former une liaison iridium-azote et une liaison iridium-carbone, avec un agent d'halogénation pour introduire un atome d'halogène dans le complexe d'iridium triscyclométallé ; (2) convertir l'atome d'halogène dans le complexe d'iridium triscyclométallé produit à l'étape (1) en un ester d'acide boronique ; et (3) soumettre le complexe d'iridium triscyclométallé produit à l'étape (2) et un composé halogéné organique à une réaction de couplage croisé pour former une liaison carbone-carbone.
PCT/JP2017/039582 2016-11-02 2017-11-01 Procédé de production de complexe d'iridium, complexe d'iridium et matériau électroluminescent comprenant ledit composé WO2018084189A1 (fr)

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CN111961084A (zh) * 2019-05-20 2020-11-20 玉林师范学院 一种肺癌细胞抑制剂及其制备方法
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JP2018012686A (ja) * 2016-06-20 2018-01-25 ユニバーサル ディスプレイ コーポレイション 有機エレクトロルミネセンス材料及びデバイス
JP7319758B2 (ja) 2016-06-20 2023-08-02 ユニバーサル ディスプレイ コーポレイション 有機エレクトロルミネセンス材料及びデバイス
JP2018008936A (ja) * 2016-06-20 2018-01-18 ユニバーサル ディスプレイ コーポレイション 有機エレクトロルミネセンス材料及びデバイス
US11482683B2 (en) 2016-06-20 2022-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US11469383B2 (en) 2018-10-08 2022-10-11 Universal Display Corporation Organic electroluminescent materials and devices
US11581498B2 (en) 2019-05-09 2023-02-14 Beijing Summer Sprout Technology Co., Ltd. Organic luminescent material containing 6-silyl-substituted isoquinoline ligand
US11498937B2 (en) 2019-05-09 2022-11-15 Beijing Summer Sprout Technology Co., Ltd. Organic luminescent material including 3-deuterium-substituted isoquinoline ligand
US11653559B2 (en) 2019-05-09 2023-05-16 Beijing Summer Sprout Technology Co., Ltd. Metal complex containing a first ligand, a second ligand, and a third ligand
JP7274756B2 (ja) 2019-05-09 2023-05-17 北京夏禾科技有限公司 ３つの異なる配位子を含有する金属錯体
JP2020186235A (ja) * 2019-05-09 2020-11-19 北京夏禾科技有限公司 ３つの異なる配位子を含有する金属錯体
CN111961084B (zh) * 2019-05-20 2022-05-31 玉林师范学院 一种肺癌细胞抑制剂及其制备方法
CN111961084A (zh) * 2019-05-20 2020-11-20 玉林师范学院 一种肺癌细胞抑制剂及其制备方法
US11993617B2 (en) 2019-10-18 2024-05-28 Beijing Summer Sprout Technology Co., Ltd. Organic luminescent material having an ancillary ligand with a partially fluorine-substituted substituent
CN115010766A (zh) * 2022-07-21 2022-09-06 西安交通大学 基于刚性配位的交叠型红光铱（iii）配合物
CN115010766B (zh) * 2022-07-21 2024-01-09 西安交通大学 基于刚性配位的交叠型红光铱（iii）配合物

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