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WO2011024977A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

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Publication number
WO2011024977A1
WO2011024977A1 PCT/JP2010/064649 JP2010064649W WO2011024977A1 WO 2011024977 A1 WO2011024977 A1 WO 2011024977A1 JP 2010064649 W JP2010064649 W JP 2010064649W WO 2011024977 A1 WO2011024977 A1 WO 2011024977A1
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carbon atoms
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organic
light emitting
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桂樹 外崎
玲 武田
康介 渡辺
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Fujifilm Corp
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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
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to an organic electroluminescent element (hereinafter also referred to as “organic EL element”, “light emitting element” or “element”) that can emit light by converting electric energy into light, and in particular, emission characteristics and durability.
  • organic EL element organic electroluminescent element
  • the present invention relates to an organic electroluminescent device having excellent resistance.
  • organic light-emitting elements using organic light-emitting materials
  • organic EL elements can obtain high-luminance light emission at a low voltage and attract attention as promising display elements. ing.
  • phosphorescent materials include iridium complexes and platinum complexes (see, for example, Patent Documents 1 and 2).
  • Patent Literature iridium complex phosphorescent material having a hexafluoroacetylacetonate ligand has a significantly lower emission intensity than that having an acetylacetonato ligand.
  • red phosphorescent material an iridium complex having a quinoline ring or an isoquinoline ring as a partial structure of the ligand is disclosed, but further improvement is required regarding the color as red and the thermal behavior of the material. Yes.
  • An object of the present invention is to provide a red phosphorescent light emitting material that emits light with a good color and can be easily sublimated and deposited. Another object of the present invention is to provide an organic electroluminescent device having excellent light emission characteristics by using the phosphorescent material. Another object of the present invention is to provide a composition and a light emitting layer useful for an organic electroluminescent device. Another object of the present invention is to provide a light emitting device and a lighting device including an organic electroluminescent element.
  • A represents an aromatic heterocyclic ring containing a nitrogen atom
  • B represents an aromatic ring or an aromatic heterocyclic ring.
  • A represents a quinoline ring or an isoquinoline ring.
  • a and B represents a naphthalene ring
  • a and B may each have a substituent and may be further condensed
  • R 1 and R 3 each independently represents an alkyl group, an aryl group, or hetero Represents an aryl group
  • R 2 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, or a halogen atom, and at least one of at least one of R 1 , R 2 , and R 3 Containing fluorine atoms.
  • a light-emitting material for an organic electroluminescence device which is the organometallic complex according to any one of [8].
  • An organic electroluminescent element having a pair of electrodes and at least one organic layer including a light emitting layer between the electrodes on a substrate, wherein one of the organic layers is for organic EL according to [9] An organic electroluminescent device comprising a luminescent material.
  • the present invention improves the color by shortening the emission wavelength by introducing a fluorine atom into the acetylacetonate ligand of the red phosphorescent iridium (III) complex having the maximum emission wavelength on the longer wavelength side than 610 nm.
  • improvement in sublimation purification suitability and vapor deposition suitability by lowering the sublimation temperature was realized.
  • the organometallic complex of the present invention is represented by the following general formula (1).
  • the organometallic complex can be used for a phosphorescent material having a red emission color.
  • the use of the phosphorescent material is not particularly limited, and for example, it is preferably used for an organic EL (electroluminescence) element.
  • the use of the organic electroluminescent element of the present invention is not particularly limited.
  • a display device such as a television, a personal computer, a mobile phone, and electronic paper can be used.
  • A represents an aromatic heterocyclic ring containing a nitrogen atom
  • B represents an aromatic ring or an aromatic heterocyclic ring.
  • A represents a quinoline ring or an isoquinoline ring.
  • a and B represents a naphthalene ring
  • a and B may each have a substituent and may be further condensed
  • R 1 and R 3 each independently represents an alkyl group, an aryl group, or hetero Represents an aryl group
  • R 2 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, or a halogen atom, and at least one of at least one of R 1 , R 2 , and R 3 Containing fluorine atoms.
  • the aromatic heterocyclic ring containing a nitrogen atom represented by A is preferably a quinoline ring, a 1-isoquinoline ring or a 3-isoquinoline ring, and particularly preferably a quinoline ring. This is to realize red light emission with good color.
  • the aromatic ring represented by B is preferably a naphthalene ring. For at least one set of A and B, A represents a quinoline ring or an isoquinoline ring, and B represents a naphthalene ring.
  • a and B examples include a quinoline ring and a naphthalene ring, a 1-isoquinoline ring and a naphthalene ring, a 3-isoquinoline ring and a naphthalene ring, and a quinoline ring and a naphthalene ring are preferable.
  • a and B may each have a substituent and may further be condensed. In the general formula (1), it is preferable that two As are the same and two Bs are the same.
  • the alkyl group represented by R 1 , R 2 , and R 3 preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms.
  • the “carbon number” of a substituent such as an alkyl group includes the case where a substituent such as an alkyl group may be substituted by another substituent, and also includes the carbon number of the other substituent. Used in meaning.
  • the aryl group represented by R 1 , R 2 , and R 3 preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms.
  • the heteroaryl group represented by R 1 , R 2 , and R 3 preferably has 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms.
  • hetero atom examples include a nitrogen atom, an oxygen atom, and a sulfur atom.
  • Specific examples include imidazolyl, pyrazolyl, pyridyl, pyrazyl, pyrimidyl, triazinyl, quinolyl, isoquinolinyl, pyrrolyl, indolyl, furyl, thienyl, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl, azepinyl and the like.
  • Examples of the halogen atom represented by R 1 , R 2 , and R 3 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • At least one of R 1 , R 2 , and R 3 contains at least one fluorine atom.
  • the number of fluorine atoms contained in R 1 , R 2 , and R 3 is preferably 1 to 6, and more preferably 3 to 6. This is because if the number of fluorine atoms is within the above range, the sublimation purification yield is improved and the color is improved. More preferably, R 1 is a trifluoromethyl group and R 3 is a methyl group. This is to achieve both the sublimation purification yield and the improvement in color.
  • R 2 is preferably a hydrogen atom.
  • the organometallic complex represented by the general formula (1) is preferably an organometallic complex represented by the general formula (1-1).
  • a ′ represents a 2-quinolyl ring, a 1-isoquinolyl ring or a 3-isoquinolyl ring.
  • B ′ is represented by any one of the following general formulas (2) to (4).
  • R 4 and R 5 each independently represent a substituent on A ′ and B ′.
  • R 1 and R 3 each independently represents an alkyl group, an aryl group, or a heteroaryl group.
  • R 2 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, or a halogen atom.
  • At least one of R 1 , R 2 , and R 3 is a substituent containing one or more fluorine atoms.
  • n and m each independently represents an integer of 0 to 6.
  • a ′ represents a 2-quinolyl ring, a 1-isoquinolyl ring or a 3-isoquinolyl ring, preferably a 1-isoquinolyl ring or a 2-quinolyl ring, and more preferably a 2-quinolyl ring.
  • B represents a naphthyl skeleton represented by any one of the general formulas (2) to (4).
  • the skeleton is more preferably the general formula (2) or the general formula (3), and the most preferable case is the general formula (3).
  • * is a bonding position to B ′.
  • n and n each independently represents an integer of 0 to 6.
  • M is preferably from 0 to 3, more preferably from 0 to 2, even more preferably from 0 to 1, and most preferably 0.
  • N is preferably from 0 to 3, more preferably from 0 to 2, even more preferably from 0 to 1, and most preferably 0.
  • R 4 when m is 2 or more, R 4 may be the same or different; when n is 2 or more, R 5 may be the same or different; when m is 1 or more and n is 1 or more, R 4 and R 5 may be the same or different.
  • R 4 When m is 2 or more, R 4 may be bonded to each other and condensed, or when n is 2 or more, R 5 may be bonded to each other and condensed.
  • R 4 Examples of the substituent represented by R 5 is not particularly limited, for example, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an amino group, an alkoxy group, an aryloxy group, a heterocyclic group, a hetero Ring oxy group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylthio group, hydroxy group, amino group, halogen atom, acyl group, acyloxy group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino Group, sulfamoyl group, carbamoyl group, alkylthio group, arylthio group, heteroarylthio group, sulfonyl group, sulfinyl group, ureido group, phosphoric acid amide group, mercapto group,
  • the alkyl group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms.
  • the “carbon number” of a substituent such as an alkyl group includes the case where a substituent such as an alkyl group may be substituted by another substituent, and also includes the carbon number of the other substituent. Used in meaning
  • the alkenyl group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms.
  • the alkynyl group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. Examples thereof include ethynyl, propargyl, 1-propynyl, and 3-pentynyl. It is done.
  • the aryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms.
  • the heteroaryl group preferably has 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom, specifically, for example, imidazolyl and pyrazolyl. , Pyridyl, pyrazyl, pyrimidyl, triazinyl, quinolyl, isoquinolinyl, pyrrolyl, indolyl, furyl, thienyl, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl, azepinyl and the like.
  • the amino group preferably has 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 10 carbon atoms.
  • amino, methylamino, dimethylamino, diethylamino, dibenzylamino examples include diphenylamino and ditolylamino.
  • the alkoxy group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms. Examples thereof include methoxy, ethoxy, butoxy, 2-ethylhexyloxy and the like. It is done.
  • the aryloxy group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms.
  • phenyloxy, 1-naphthyloxy, 2-naphthyloxy, etc. Is mentioned.
  • the heterocyclic group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms.
  • the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom.
  • Specific examples include imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, azepinyl group and the like.
  • the heterocyclic oxy group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy and the like. .
  • the acyl group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms, and examples thereof include acetyl, benzoyl, formyl, and pivaloyl.
  • the alkoxycarbonyl group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonyl and ethoxycarbonyl.
  • the aryloxycarbonyl group preferably has 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, and particularly preferably 7 to 12 carbon atoms, and examples thereof include phenyloxycarbonyl.
  • the acyloxy group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, and examples thereof include acetoxy and benzoyloxy.
  • the acylamino group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, and examples thereof include acetylamino and benzoylamino.
  • the alkoxycarbonylamino group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms, and examples thereof include methoxycarbonylamino.
  • the aryloxycarbonylamino group preferably has 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, and particularly preferably 7 to 12 carbon atoms, and examples thereof include phenyloxycarbonylamino.
  • the sulfonylamino group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms. Examples thereof include methanesulfonylamino and benzenesulfonylamino.
  • the sulfamoyl group preferably has 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 12 carbon atoms.
  • sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl groups are preferred. Famoyl etc. are mentioned.
  • the carbamoyl group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms. Examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl, and phenylcarbamoyl. .
  • the alkylthio group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, and examples thereof include methylthio and ethylthio.
  • the arylthio group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms, and examples thereof include phenylthio.
  • the heterocyclic thio group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms.
  • pyridylthio, 2-benzimidazolylthio, 2-benz Examples include oxazolylthio and 2-benzthiazolylthio.
  • the sulfonyl group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, and examples thereof include mesyl and tosyl.
  • the sulfinyl group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, and examples thereof include methanesulfinyl and benzenesulfinyl.
  • the ureido group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, and examples thereof include ureido, methylureido, and phenylureido.
  • the phosphoric acid amide group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms. Examples thereof include diethyl phosphoric acid amide and phenyl phosphoric acid amide. It is done.
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • the silyl group preferably has 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, and particularly preferably 3 to 24 carbon atoms.
  • the silyloxy group preferably has 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, and particularly preferably 3 to 24 carbon atoms.
  • R 4 and R 5 are preferably an alkyl group, an aryl group, an alkenyl group, an alkoxy group, an acyl group, an amino group, a cyano group, a silyl group, or a halogen atom, and more preferably an alkyl group, an aryl group, an alkoxy group, An amino group and a halogen atom are particularly preferable, and an alkyl group, an aryl group, an alkoxy group, and a halogen atom are particularly preferable, and an alkyl group and an aryl group are most preferable.
  • a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, and a tert-butyl group are preferable, a methyl group and an ethyl group are more preferable, and a methyl group Is particularly preferred.
  • the aryl group of R 4 and R 5 is preferably a phenyl group, an o-methylphenyl group, an m-methylphenyl group, a p-methylphenyl group, a naphthyl group, an anthranyl group, or an imidazolyl group.
  • a methylphenyl group, m-methylphenyl group, and p-methylphenyl group are more preferable, and a phenyl group is particularly preferable.
  • alkenyl group for R 4 and R 5 a vinyl group, an allyl group, a 1-propenyl group, a 1-isopropenyl group, a 1-butenyl group, a 2-butenyl group, and a 3-pentenyl group are preferable, and a vinyl group, An allyl group and a 1-propenyl group are more preferable, and a vinyl group and an allyl group are particularly preferable.
  • R 5 a methoxy group, an ethoxy group, a butoxy group are preferable, a methoxy group, more preferably an ethoxy group, a methoxy group is particularly preferred.
  • the acyl group of R 4 and R 5 is preferably an acetyl group, a benzoyl group, a formyl group, or a pivaloyl group, more preferably an acetyl group or a benzoyl group, and particularly preferably an acetyl group.
  • the amino group of R 4 and R 5 is preferably a dimethylamino group, a diethylamino group, or a diisopropylamino group, more preferably a dimethylamino group or a diethylamino group, and particularly preferably a dimethylamino group.
  • the amino group of R 4 and R 5 is preferably a methylamino group, a dimethylamino group, a diethylamino group or a diisopropylamino group, more preferably a dimethylamino group or a diethylamino group, and particularly preferably a dimethylamino group.
  • the silyl group of R 4 and R 5 is preferably a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, or a triphenylsilyl group, more preferably a trimethylsilyl group, a triethylsilyl group, or a triphenylsilyl group, and particularly preferably a trimethylsilyl group. preferable.
  • R 4 iodine atom as the halogen atom of R 5, a bromine atom, a chlorine atom, preferably a fluorine atom, a chlorine atom, more preferably a fluorine atom, a fluorine atom is particularly preferred.
  • R 1 containing a fluorine atom, R 2 examples of the substituent of R 3 is not particularly limited, for example, fluorine atom, fluoroalkyl group, fluoroalkenyl group, fluoroalkyl group, include fluoroaryl group.
  • the fluoroalkyl group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms.
  • fluoromethyl, difluoromethyl, trifluoromethyl 1- Fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 1,2-difluoroethyl, 2,2-difluoroethyl, 1,1,2-trifluoroethyl, 1,2,2-trifluoroethyl, 2 , 2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, 1,2,2,2-tetrafluoroethyl, 1,1,2,2,2-pentafluoroethyl, 1-fluoro -1-propyl, 2-fluoro-1-propyl, 3-fluoro-1-propyl, 1,1-difluoro-1-propyl, 1,2-difluoro
  • the fluoroalkenyl group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms.
  • the fluoroallyl group refers to a substituent in which one fluorine atom is bonded to any carbon of the allyl group.
  • a partial structure of the following general formula (5) is a 1-fluoroallyl group
  • a partial structure of the general formula (6) is a 2-fluoroallyl group
  • a partial structure of the general formula (7) is a 3-fluoroallyl group
  • fluorine Those in which two atoms are introduced are called difluoroallyl groups, and those in which three atoms are introduced are called trifluoroallyl groups.
  • the fluorovinyl group refers to a substituent in which one fluorine atom is bonded to any carbon of the vinyl group.
  • a partial structure of the following general formula (8) is a 1-fluoroallyl group
  • a partial structure of the general formula (9) is a 2-fluoroallyl group
  • two fluorine atoms introduced are difluorovinyl groups, The introduced one is called a trifluorovinyl group.
  • the fluoroalkynyl group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, and particularly preferably 3 to 10 carbon atoms.
  • 3 to 30 carbon atoms more preferably 3 to 20 carbon atoms, and particularly preferably 3 to 10 carbon atoms.
  • the fluoroaryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 10 carbon atoms.
  • the substituent for R 1 , R 2 and R 3 containing a fluorine atom is preferably a fluorine atom, a fluoroalkyl group, a fluoroalkenyl group, a fluoroalkynyl group or a fluoroaryl group, more preferably a fluorine atom or a fluoroalkyl group.
  • a fluoroalkenyl group and a fluoroaryl group more preferably a fluorine atom, a fluoroalkyl group and a fluoroaryl group.
  • the fluoroalkyl group for R 1 , R 2 , and R 3 is preferably a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, 1,2-difluoroethyl group, 2,2-difluoroethyl group, 1,1,2-trifluoroethyl group, 1,2,2-trifluoroethyl group, 2,2,2-trifluoroethyl group More preferably, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 1,1,2-trifluoroethyl group, a 1,2,2-trifluoroethyl group, or a 2,2,2-trifluoroethyl group And particularly preferred are a fluoromethyl group, a difluoromethyl group, and a triflu
  • fluoroalkenyl group for R 1 , R 2 and R 3 , 1-fluorovinyl, 2-fluorovinyl, 1,2-difluorovinyl, 2,2-difluorovinyl, 1,2,2-trifluorovinyl, 1 -Fluoroallyl, 2-fluoroallyl, 3-fluoroallyl, 1,1-difluoroallyl, 1,2-difluoroallyl, 1,3-difluoroallyl, 2,3-difluoroallyl, 3,3-difluoroallyl, , 1,2-trifluoroallyl, 1,1,3-trifluoroallyl, 1,2,3-trifluoroallyl, 1,3,3-trifluoroallyl, 1-fluoro-1-propenyl, 2-fluoro -1-propenyl, 3-fluoro-1-propenyl, 1,2-difluoro-1-propenyl, 1,3-difluoro-1-propenyl
  • the fluoroalkynyl group for R 1 , R 2 and R 3 is preferably 1-fluoropropargyl, 3-fluoropropargyl, 1,1-difluoropropargyl, 1,3-difluoropropargyl, 1,1,3-trifluoropropargyl More preferred are 1-fluoropropargyl and 3-fluoropropargyl, and particularly preferred is 3-fluoropropargyl.
  • the fluoroaryl group for R 1 , R 2 and R 3 is preferably 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl.
  • R 1 containing no fluorine atom, R 2 is not particularly limited as substituents of R 3, for example, a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an amino group, an alkoxy group, an aryl Oxy group, heterocyclic group, heterocyclic oxy group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylthio group, hydroxy group, amino group, halogen atom, acyl group, acyloxy group, acylamino group, alkoxycarbonylamino group, Aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, arylthio group, heteroarylthio group, sulfonyl group, sulfinyl group, ureido group, phosphoric
  • R 1 , R 2 and R 3 not containing a fluorine atom are preferably a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an aryloxy group, an alkoxy group, a hydroxy group, an amino group, a heterocyclic group,
  • a silyl group more preferably a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an aryloxy group, an alkoxy group, or a silyl group, still more preferably a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, An alkoxy group and a silyl group are preferable, and a hydrogen atom, an alkyl group, and an aryl group are particularly preferable.
  • a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, and a tert-butyl group are preferable, and a methyl group, an ethyl group, and a tert-butyl group are preferable.
  • a butyl group is more preferable, and a methyl group is particularly preferable.
  • the alkenyl groups of R 1 , R 2 and R 3 are preferably vinyl, allyl, 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, and 3-pentenyl.
  • a vinyl group, an allyl group, and a 1-propenyl group are more preferable, and an allyl group is particularly preferable.
  • R ⁇ 1 >, R ⁇ 2 >, R ⁇ 3 >, a propargyl group and a butynyl group are preferable, and a propargyl group is more preferable.
  • the aryl group of R 1 , R 2 and R 3 is preferably a phenyl group, o-methylphenyl group, m-methylphenyl group, p-methylphenyl group, naphthyl group, anthranyl group or imidazolyl group.
  • O-methylphenyl group, m-methylphenyl group, and p-methylphenyl group are more preferable, and phenyl group is particularly preferable.
  • the aryloxy group for R 1 , R 2 and R 3 is preferably a phenyloxy group, 1-naphthyloxy group or 2-naphthyloxy group, more preferably a phenyloxy group.
  • a methoxy group, an ethoxy group, a butoxy group, a propoxy group, and a 2-ethylhexyloxy group are preferable, a methoxy group and an ethoxy group are more preferable, and a methoxy group is particularly preferable preferable.
  • the amino group of R 1 , R 2 , and R 3 is preferably an amino group, a methylamino group, a dimethylamino group, a diethylamino group, a dibenzylamino group, a diphenylamino group, or a ditolylamino group, and an amino group or a methylamino group
  • a dimethylamino group is more preferable, and a dimethylamino group is particularly preferable.
  • heterocyclic groups of R 1 , R 2 and R 3 include imidazolyl group, pyridyl group, quinolyl group, furyl group, thienyl group, piperidyl group, morpholino group, benzoxazolyl group, benzimidazolyl group, and benzthiazolyl group.
  • Carbazolyl group is preferable, imidazolyl group, pyridyl group, furyl group, benzoxazolyl group, benzimidazolyl group, benzthiazolyl group, carbazolyl group is more preferable, imidazolyl group, pyridyl group, furyl group, carbazolyl group is more preferable, imidazolyl group A group, pyridyl group and furyl group are particularly preferred.
  • the silyl group of R 1 , R 2 and R 3 is preferably a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, a tert-butyldimethylsilyl group, a tert-butyldiphenylsilyl group or a triphenylsilyl group.
  • Group, triethylsilyl group and triphenylsilyl group are more preferable, trimethylsilyl group and triethylsilyl group are further preferable, and trimethylsilyl group is particularly preferable.
  • R 1 is a substituent containing a fluorine atom
  • the number of fluorine atoms on R 1 is 1 to 10, preferably 1 to 6, and more preferably 1 to 3.
  • R 2 is a substituent containing a fluorine atom
  • the number of fluorine atoms on R 2 is 1 to 10, preferably 1 to 6, and more preferably 1 to 3.
  • R 3 is a substituent containing a fluorine atom
  • the number of fluorine atoms on R 3 is 1 to 10, preferably 1 to 6, and more preferably 1 to 3.
  • At least one substituent includes at least one fluorine atom.
  • the number of all fluorine atoms contained in the substituents R 1 , R 2 and R 3 is 1 to 30, preferably 1 to 10, more preferably 1 to 6, still more preferably 1 to 5, and 1 to 3 is particularly preferred, and 1 to 2 is most preferred.
  • R 1 , R 2 , and R 3 are not particularly limited, and examples thereof include combinations shown in (10-1) to (10-44) in Tables 1 and 2 below.
  • R 1 , R 2 and R 3 are preferably combinations shown in (10-1) to (10-38) in Tables 1 and 2, and more preferably (10-1) to (10-26). More preferred are combinations shown in (10-1) to (10-11).
  • the compound of the present invention can be synthesized by various methods. For example, a ligand having ring A and ring B and a halogen ion coordinated to iridium is used as a raw material, and an acetylacetone derivative having at least one fluorine atom is allowed to act on the compound in the presence of a base. It can be obtained by carrying out an exchange reaction.
  • ether solvents, alcohol solvents and halogen solvents are preferable, tetrahydrofuran, 2-ethoxyethanol, 2-methoxyethanol, 2-propanol, ethanol, dichloromethane, chloroform.
  • the reaction temperature during the synthesis is preferably 0 ° C. to 150 ° C., more preferably 25 ° C. to 140 ° C., further preferably 50 ° C. to 120 ° C., and particularly preferably 60 ° C. to 100 ° C.
  • a solvent having a boiling point of less than 50 ° C. the range from 25 ° C. to the boiling point of the solvent is preferred, and in the case of a boiling point of less than 60 ° C., the range from 25 ° C. to the boiling point of the solvent is more preferred.
  • the reaction time for the synthesis is preferably 20 minutes to 24 hours, more preferably 30 minutes to 12 hours, still more preferably 40 minutes to 6 hours, and 1 hour to 4 hours. Some cases are particularly preferred.
  • the base used in the synthesis may be either an organic base or an inorganic base, preferably a metal alkoxide or carbonate, more preferably sodium methoxide, sodium carbonate, or potassium carbonate, and even more preferably sodium carbonate.
  • the partial structure consisting of A and B in the general formula (1) is defined as a partial structure L1, and an example of the partial structure L1 is shown below.
  • the structure of the acetylacetonato ligand moiety having a fluorine atom in the general formula (1) is defined as a partial structure L2, and an example of the partial structure L2 is shown below.
  • the organometallic complex of the present invention can be used as a light emitting material for an organic electroluminescent element.
  • the organometallic complex of the present invention is used as a light-emitting material for an organic electroluminescent device, it is preferable because an organic electroluminescent device having better suitability and color can be produced.
  • the present invention also relates to a light emitting layer containing the light emitting material for an organic electroluminescent element of the present invention.
  • the light emitting layer of this invention can be used for an organic electroluminescent element.
  • the light emitting layer of the present invention preferably further contains at least one of a host material and a hydrocarbon compound.
  • an organic electroluminescence device having more excellent production suitability and color can be obtained.
  • the content of the organic electroluminescent element material in the light emitting layer of the present invention is preferably 1 to 30% by mass, more preferably 3 to 20% by mass in the light emitting layer.
  • the present invention also relates to a composition containing a compound represented by the light emitting material for an organic electroluminescent element of the present invention.
  • the content of the organic electroluminescent element material in the composition of the present invention is preferably 1 to 40% by mass, and more preferably 5 to 20% by mass.
  • Other components that may be contained in the composition of the present invention may be organic or inorganic, and as organic materials, materials described as host materials, fluorescent materials, phosphorescent materials, and hydrocarbon compounds described later can be applied.
  • the host material and the hydrocarbon compound are preferable, and the host material and the compound represented by the general formula (VI) are more preferable.
  • the content of the host material in the composition of the present invention is preferably 50 to 95% by mass, and more preferably 70 to 90% by mass.
  • the composition of the present invention can form an organic layer of an organic electroluminescence device by a dry film forming method such as a vapor deposition method or a sputtering method, a transfer method, a printing method, or the like.
  • An organic electroluminescent element of the present invention is an organic electroluminescent element having a pair of electrodes and at least one organic layer including a light emitting layer between the electrodes on a substrate, and is formed on any one of the organic layers.
  • the compound represented by General formula (1) is contained. It is preferable to further have a layer containing the compound represented by the general formula (1) between the light emitting layer and the cathode.
  • the light-emitting layer and the layer containing the compound represented by the general formula (1) are organic layers, and may further have a plurality of organic layers.
  • at least one of the anode and the cathode is preferably transparent or translucent.
  • FIG. 1 shows an example of the configuration of an organic electroluminescent device according to the present invention.
  • a light emitting layer 6 is sandwiched between an anode 3 and a cathode 9 on a support substrate 2.
  • a hole injection layer 4, a hole transport layer 5, a light emitting layer 6, a hole block layer 7, and an electron transport layer 8 are laminated in this order between the anode 3 and the cathode 9.
  • Anode / hole transport layer / light emitting layer / electron transport layer / cathode Anode / hole transport layer / light emitting layer / block layer / electron transport layer / cathode, Anode / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode, Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / cathode, Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / cathode, Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode.
  • the element configuration, the substrate, the cathode, and the anode of the organic electroluminescence element are described in detail in, for example, Japanese Patent Application Laid-Open No. 2008-270736, and the matters described in the publication can be applied to the present invention.
  • the substrate used in the present invention is preferably a substrate that does not scatter or attenuate light emitted from the organic layer.
  • an organic material it is preferable that it is excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation, and workability.
  • the anode usually only needs to have a function as an electrode for supplying holes to the organic layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element, It can select suitably from well-known electrode materials.
  • the anode is usually provided as a transparent anode.
  • the cathode usually has a function as an electrode for injecting electrons into the organic layer, and there is no particular limitation on the shape, structure, size, etc., and it is known depending on the use and purpose of the light emitting device.
  • the electrode material can be selected as appropriate.
  • Organic layer in the present invention will be described.
  • each organic layer can be suitably formed by any of a dry film forming method such as a vapor deposition method and a sputtering method, a transfer method, and a printing method.
  • the light emitting material in the present invention is preferably a compound represented by the general formula (1).
  • the light emitting material in the light emitting layer is generally contained in the light emitting layer in an amount of 0.1% by mass to 50% by mass with respect to the total mass of the compound forming the light emitting layer. From the viewpoint of durability and external quantum efficiency.
  • the content is preferably 1% by mass to 50% by mass, and more preferably 2% by mass to 40% by mass.
  • the thickness of the light emitting layer is not particularly limited, but is usually preferably 2 nm to 500 nm, and more preferably 3 nm to 200 nm, and more preferably 5 nm to 100 nm from the viewpoint of external quantum efficiency. More preferably.
  • the light emitting layer in the element of the present invention may be composed of only a light emitting material, or may be a mixed layer of a host material and a light emitting material.
  • the light emitting material may be a fluorescent light emitting material or a phosphorescent light emitting material, and the dopant may be one kind or two or more kinds.
  • the host material is preferably a charge transport material.
  • the host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed.
  • the light emitting layer may include a material that does not have charge transporting properties and does not emit light.
  • the light emitting layer in the element of the present invention a material using a host material and a compound represented by the general formula (1) as the light emitting material is preferable. Further, the light emitting layer may be a single layer or a multilayer of two or more layers. When there are a plurality of light emitting layers, the compound represented by the general formula (1) may be contained in two or more light emitting layers. In addition, each light emitting layer may emit light with different emission colors.
  • the host material used in the present invention may contain the following compounds.
  • the triplet lowest excitation energy (T 1 energy) of the host material is higher than the T 1 energy of the phosphorescent light emitting material.
  • the content of the host compound in the present invention is not particularly limited, but from the viewpoint of light emission efficiency and driving voltage, it is 15% by mass or more and 99% by mass or less with respect to the total compound mass forming the light emitting layer. Preferably there is.
  • fluorescent material examples include, for example, benzoxazole derivatives, benzimidazole derivatives, benzothiazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives.
  • Condensed aromatic compounds perinone derivatives, oxadiazole derivatives, oxazine derivatives, aldazine derivatives, pyralidine derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiadiazolopyridine derivatives, cyclopentadiene derivatives, styryl Complexes of amine derivatives, diketopyrrolopyrrole derivatives, aromatic dimethylidin compounds, 8-quinolinol derivatives and pyromethene derivatives
  • complexes represented, polythiophene, polyphenylene, polyphenylene vinylene polymer compounds include compounds such as organic silane derivatives.
  • phosphorescent material examples include, in addition to the compound represented by the general formula (1), for example, US6303238B1, US6097147, WO00 / 57676, WO00 / 70655, WO01 / 08230, WO01 / 39234A2, WO01 / 41512A1, WO02 / 02714A2, WO02 / 15645A1, WO02 / 44189A1, WO05 / 19373A2, JP2001-247859, JP2002-302671, JP2002-117978, JP2003-133074, JP2002-235076, JP2003-200376 123982, JP2002-170684, EP121257, JP2002-226495, JP2002-234894, JP2001-247859, JP2001-29 470, JP 2002-173675, JP 2002-203678, JP 2002-203679, JP 2004-357771, JP 2006-256999,
  • luminescent dopants include Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex. Eu complex, Tb complex, Gd complex, Dy complex, and Ce complex.
  • an Ir complex, a Pt complex, or a Re complex among which an Ir complex or a Pt complex containing at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, and a metal-sulfur bond. Or Re complexes are preferred.
  • an Ir complex, a Pt complex, or a Re complex containing a tridentate or higher polydentate ligand is particularly preferable.
  • the content of the phosphorescent material is preferably in the range of 0.1% by mass to 50% by mass and preferably in the range of 0.2% by mass to 50% by mass with respect to the total mass of the light emitting layer in the light emitting layer. More preferably, the range of 0.3% by mass or more and 40% by mass or less is further preferable, and the range of 20% by mass or more and 30% by mass or less is most preferable.
  • the content of the phosphorescent material (the compound represented by the general formula (1) and / or the phosphorescent material used in combination) that can be used in the present invention is 0.1% by mass or more based on the total mass of the light emitting layer.
  • a range of 50% by mass or less is preferable, a range of 1% by mass or more and 40% by mass or less is more preferable, and a range of 5% by mass or more and 30% by mass or less is most preferable.
  • the chromaticity of light emission of the organic electroluminescent element is less dependent on the addition concentration of the phosphorescent light emitting material.
  • the organic electroluminescent element of the present invention most preferably contains 5 to 30% by mass of at least one of the above-described luminescent materials (compound represented by the general formula (1)) with respect to the total mass of the luminescent layer.
  • the organic electroluminescent element preferably further contains a hydrocarbon compound, and more preferably contains a hydrocarbon compound in the light emitting layer.
  • the hydrocarbon compound is preferably a compound represented by the following general formula (VI).
  • the compound represented by the general formula (VI) used in the organic electroluminescence device is excellent in chemical stability, has little alteration such as decomposition of the material during device driving, and is caused by a decomposition product of the material. It is possible to prevent a decrease in the efficiency of the organic electroluminescence device and a decrease in the device life.
  • the compound represented by the general formula (VI) will be described.
  • R 4 , R 6 , R 8 , R 10 , and X 4 to X 15 each independently represent a hydrogen atom, an alkyl group, or an aryl group.
  • the alkyl group represented by R 4 , R 6 , R 8 , R 10 , X 4 to X 15 in the general formula (VI) may be substituted with an adamantane structure or an aryl structure, and has 1 to 70 carbon atoms. Preferably 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, still more preferably 1 to 10 carbon atoms, particularly preferably 1 to 6 carbon atoms, and linear alkyl having 2 to 6 carbon atoms. The group is most preferred.
  • Examples of the alkyl group represented by R 4 , R 6 , R 8 , R 10 , X 4 to X 15 in the general formula (VI) include, for example, an nC 50 H 101 group and an nC 30 H 61 group. , 3- (3,5,7-triphenyladamantan-1-yl) propyl group (31 carbon atoms), trityl group (19 carbon atoms), 3- (adamantan-1-yl) propyl group (13 carbon atoms) 9-decalyl group (10 carbon atoms), benzyl group (7 carbon atoms), cyclohexyl group (6 carbon atoms), n-hexyl group (6 carbon atoms), n-pentyl group (5 carbon atoms), n-butyl A group (4 carbon atoms), an n-propyl group (3 carbon atoms), a cyclopropyl group (3 carbon atoms), an ethyl group (2 carbon atoms), a methyl
  • the aryl group represented by R 4 , R 6 , R 8 , R 10 , X 4 to X 15 in the general formula (VI) may be substituted with an adamantane structure or an alkyl structure, and has 6 to 30 carbon atoms. Preferably 6 to 20 carbon atoms, more preferably 6 to 15 carbon atoms, particularly preferably 6 to 10 carbon atoms, and most preferably 6 carbon atoms.
  • Examples of the aryl group represented by R 4 , R 6 , R 8 , R 10 , X 4 to X 15 in the general formula (VI) include, for example, a 1-pyrenyl group (16 carbon atoms), a 9-anthracenyl group ( 14) carbon, 1-naphthyl group (10 carbon atoms), 2-naphthyl group (10 carbon atoms), pt-butylphenyl group (10 carbon atoms), 2-m-xylyl group (8 carbon atoms), 5-m-xylyl group (8 carbon atoms), o-tolyl group (7 carbon atoms), m-tolyl group (7 carbon atoms), p-tolyl group (7 carbon atoms), phenyl group (6 carbon atoms), etc. Is mentioned.
  • R 4 , R 6 , R 8 and R 10 in the general formula (VI) may be a hydrogen atom, an alkyl group or an aryl group, but the above-mentioned high glass transition temperature is preferable. From the viewpoint, at least one is preferably an aryl group, more preferably at least two are aryl groups, and particularly preferably 3 to 4 are aryl groups.
  • X 4 to X 15 in the general formula (VI) may be a hydrogen atom, an alkyl group, or an aryl group, but are preferably a hydrogen atom or an aryl group, Particularly preferred is an atom.
  • the molecular weight of the compound represented by the general formula (VI) in the present invention is 2000 or less from the viewpoint of vapor deposition suitability and solubility since an organic electroluminescent device is prepared using a vacuum vapor deposition process or a solution coating process. Is preferable, 1200 or less is more preferable, and 1000 or less is particularly preferable. Further, from the viewpoint of vapor deposition suitability, if the molecular weight is too small, the vapor pressure becomes small, the change from the gas phase to the solid phase does not occur, and it is difficult to form an organic layer. Is more preferable, and 400 or more is particularly preferable.
  • the compound represented by the general formula (VI) is preferably solid at room temperature (25 ° C), more preferably solid at room temperature (25 ° C) to 40 ° C, and from room temperature (25 ° C). Particularly preferred is a solid in the range of 60 ° C.
  • a solid phase can be formed at room temperature by combining with other materials.
  • the use of the compound represented by the general formula (VI) is not limited, and the compound may be contained in any layer in the organic layer.
  • a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, and a charge block layer described later are used.
  • it is contained in any one or more of, and more preferably contained in any one or more of the light emitting layer, hole injection layer, hole transport layer, electron transport layer, and electron injection layer, and light emission. It is particularly preferable that it is contained in any one or more of the layer, the hole injection layer, and the hole transport layer, and most preferably included in the light emitting layer.
  • the content of the compound represented by the general formula (VI) needs to be limited to an amount that does not suppress the charge transport property.
  • the compound represented by the general formula (VI) is preferably contained in an amount of 0.1 to 70% by mass, more preferably 0.1 to 30% by mass, and 0.1 to 25% by mass. Is particularly preferred.
  • the compound represented by the general formula (VI) may contain only one kind in any organic layer, and contains a combination of a plurality of compounds represented by the general formula (VI) in any ratio. You may do it.
  • hydrocarbon compounds are listed below, but are not limited to the following.
  • the compound represented by the general formula (VI) can be synthesized by appropriately combining adamantane or a halogenated adamantane with an alkyl halide or an alkylmagnesium halide (Grignard reagent).
  • a halogenated adamantane and an alkyl halide can be coupled using indium (Reference 1).
  • alkyl halides can be converted to alkyl copper reagents and coupled with aromatic Grignard reagents (Reference 2).
  • Alkyl halides can also be coupled using an appropriate aryl boric acid and a palladium catalyst (Reference 3).
  • Reference 1 Tetrahedron Lett. 39, 1998, 9557-9558.
  • Reference 2 Tetrahedron Lett. 39, 1998, 2095-2096.
  • Reference 3 J.M. Am. Chem. Soc. 124, 2002, 13662-13663.
  • the adamantane skeleton having an aryl group can be synthesized by appropriately combining adamantane or a halogenated adamantane with the corresponding arene or aryl halide.
  • the thickness of the light emitting layer is not particularly limited, but is usually preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and further preferably 10 nm to 100 nm.
  • -Hole injection layer, hole transport layer- The hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side.
  • -Electron injection layer, electron transport layer- The electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side.
  • the hole injection layer, the hole transport layer, the electron injection layer, and the electron transport layer the matters described in paragraph numbers [0165] to [0167] of JP-A-2008-270736 can be applied to the present invention. .
  • the hole blocking layer is a layer having a function of preventing holes transported from the anode side to the light emitting layer from passing through to the cathode side.
  • a hole blocking layer can be provided as an organic layer adjacent to the light emitting layer on the cathode side.
  • organic compounds constituting the hole blocking layer include aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (Aluminum (III) bis (2-methyl-8-quinolinato) 4- aluminum complexes such as phenylphenolate (abbreviated as BAlq), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (2,9-Dimethyl-4,7-diphenyl-1,10-) phenanthroline derivatives such as phenanthroline (abbreviated as BCP)) and the like.
  • BAlq phenylphenolate
  • BAlq phenylphenolate
  • BCP phenanthroline
  • the thickness of the hole blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.
  • the hole blocking layer may have a single layer structure made of one or more of the materials described above, or may have a multilayer structure made of a plurality of layers having the same composition or different compositions.
  • the electron blocking layer is a layer having a function of preventing electrons transported from the cathode side to the light emitting layer from passing through to the anode side.
  • an electron blocking layer can be provided as an organic layer adjacent to the light emitting layer on the anode side.
  • the thickness of the electron blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.
  • the electron blocking layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
  • the entire organic EL element may be protected by a protective layer.
  • the protective layer the matters described in JP-A-2008-270736, paragraphs [0169] to [0170] can be applied to the present invention.
  • the element of this invention may seal the whole element using a sealing container.
  • the sealing container the matters described in paragraph [0171] of JP-A-2008-270736 can be applied to the present invention.
  • the present invention also relates to a film forming method for forming a film by sublimation by simultaneously heating a compound used in the same organic layer as the compound represented by the general formula (1).
  • the compound represented by the general formula (1) and the compound used in the same organic layer are preferably mixed, and the composition of the present invention may be used.
  • the content ratio of the compound used in the same organic layer as the compound represented by the general formula (1) is 1% to 45% of the compound used in the same organic layer with respect to the compound represented by the general formula (1). Preferably, it is 1% to 25%.
  • the heating temperature is preferably 200 ° C. to 400 ° C., more preferably 250 ° C. to 320 ° C.
  • the heating time is preferably 0.1 hours to 350 hours, more preferably 0.1 hours to 150 hours. According to the film forming method of the present invention, there is an advantage that a light emitting layer film having high efficiency, high durability, and little color change at high temperature driving can be easily formed.
  • the organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode.
  • a direct current which may include an alternating current component as necessary
  • the driving method of the organic electroluminescence device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-290080, JP-A-7-134558, JP-A-8-234585, and JP-A-8-2441047.
  • the driving methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6,023,308 can be applied.
  • the light emitting element of the present invention can improve the light extraction efficiency by various known devices. For example, by processing the substrate surface shape (for example, forming a fine concavo-convex pattern), controlling the refractive index of the substrate / ITO layer / organic layer, controlling the film thickness of the substrate / ITO layer / organic layer, etc. It is possible to improve light extraction efficiency and external quantum efficiency.
  • the external quantum efficiency of the light emitting device of the present invention is preferably 20% or more and 30% or less.
  • the value of the external quantum efficiency should be the maximum value of the external quantum efficiency when the device is driven at 20 ° C., or the value of the external quantum efficiency near 100 to 300 cd / m 2 when the device is driven at 20 ° C. Can do.
  • the light-emitting element of the present invention may be a so-called top emission type in which light emission is extracted from the anode side.
  • the organic EL element in the present invention may have a resonator structure.
  • a multilayer film mirror made of a plurality of laminated films having different refractive indexes, a transparent or translucent electrode, a light emitting layer, and a metal electrode are superimposed on a transparent substrate.
  • the light generated in the light emitting layer resonates repeatedly with the multilayer mirror and the metal electrode as a reflection plate.
  • a transparent or translucent electrode and a metal electrode each function as a reflecting plate on a transparent substrate, and light generated in the light emitting layer repeats reflection and resonates between them.
  • the optical path length determined from the effective refractive index of the two reflectors and the refractive index and thickness of each layer between the reflectors is adjusted to an optimum value to obtain the desired resonant wavelength. Is done.
  • the calculation formula in the case of the first embodiment is described in JP-A-9-180883.
  • the calculation formula in the case of the second embodiment is described in Japanese Patent Application Laid-Open No. 2004-127795.
  • the light-emitting element of the present invention can be suitably used for light-emitting devices, pixels, display elements, displays, backlights, electrophotography, illumination light sources, recording light sources, exposure light sources, reading light sources, signs, signboards, interiors, optical communications, and the like. .
  • it is preferably used for a device driven in a region having a high light emission luminance such as a lighting device and a display device.
  • FIG. 2 is a cross-sectional view schematically showing an example of the light emitting device of the present invention.
  • the light emitting device 20 in FIG. 2 includes a transparent substrate (support substrate) 2, an organic electroluminescent element 10, a sealing container 16, and the like.
  • the organic electroluminescent device 10 is configured by sequentially laminating an anode (first electrode) 3, an organic layer 11, and a cathode (second electrode) 9 on a substrate 2.
  • a protective layer 12 is laminated on the cathode 9, and a sealing container 16 is provided on the protective layer 12 with an adhesive layer 14 interposed therebetween.
  • a part of each electrode 3 and 9, a partition, an insulating layer, etc. are abbreviate
  • the adhesive layer 14 a photocurable adhesive such as an epoxy resin or a thermosetting adhesive can be used, and for example, a thermosetting adhesive sheet can also be used.
  • the use of the light-emitting device of the present invention is not particularly limited, and for example, it can be a display device such as a television, a personal computer, a mobile phone, and electronic paper in addition to a lighting device.
  • the illumination device 40 includes the organic electroluminescent element 10 and the light scattering member 30 described above. More specifically, the lighting device 40 is configured such that the substrate 2 of the organic electroluminescent element 10 and the light scattering member 30 are in contact with each other.
  • the light scattering member 30 is not particularly limited as long as it can scatter light.
  • the light scattering member 30 is a member in which fine particles 32 are dispersed on a transparent substrate 31.
  • the transparent substrate 31 for example, a glass substrate can be preferably cited.
  • the fine particles 32 transparent resin fine particles can be preferably exemplified.
  • the glass substrate and the transparent resin fine particles known ones can be used.
  • the incident light is scattered by the light scattering member 30, and the scattered light is scattered by the light emitting surface 30B. Is emitted as illumination light.
  • the crystals were transferred to a 200 ml eggplant flask, and 100 ml of 2-propanol was added thereto, boiled and dried to obtain 0.88 g of red crystals. 0.65 g of this crystal was taken and subjected to short column purification with methylene chloride, and hexane was added to the resulting red solution. The resulting precipitated product was filtered off and dried to obtain 0.46 g of red-brown crystalline metal complex B.
  • the metal complexes A to D of the present invention were used as light emitting materials.
  • the structures of the light emitting materials A to D are shown below.
  • the light emitting materials B to D of the present invention sublimate at a lower temperature and can be performed at a lower deposition temperature than the comparative light emitting material A.
  • the light-emitting materials B to D of the present invention can be purified by sublimation at a higher yield than the comparative light-emitting material A, that is, have good sublimation purification suitability.
  • the light-emitting materials C and D of the present invention have a maximum of an emission wavelength close to 610 nm, which is preferable for the relative luminous efficiency of red than the comparative light-emitting material A. It has also been shown that the number of fluorine atoms contained in the acetylacetonato ligand is preferably 3 rather than 6 from the viewpoint of quantum yield.
  • First layer Compound B: Film thickness 120 nm
  • Second layer Compound C: film thickness 10 nm
  • Third layer Compound D and luminescent material (mass ratio 85:15): film thickness 30 nm
  • Fourth layer Compound D: Film thickness 40 nm
  • 1.0 nm of lithium fluoride and 100 nm of metallic aluminum were vapor-deposited in this order to form a cathode.
  • the obtained laminate is put into a glove box substituted with argon gas without being exposed to the atmosphere, and a stainless steel sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.) are used. Then, an organic EL element was produced.
  • the vapor deposition rate in the examples of the present invention is 0.2 nm / second unless otherwise specified.
  • the deposition rate was measured using a crystal resonator film formation controller CRTM-9000 manufactured by ULVAC.
  • the film thickness described above is also calculated from a calibration curve created based on the numerical value of CRTM-9000 and the film thickness measured with the Dektak stylus type film thickness meter.
  • the structures of compounds B, C, and D are shown below.
  • the organic electroluminescent element using the organometallic complex of the present invention can be used for a light emitting device, a display device, and a lighting device.
  • the light-emitting element of the present invention can be advantageously used because it is designed to emit red light with excellent color.
  • the present invention improves the color by shortening the emission wavelength by introducing a fluorine atom into the acetylacetonate ligand of the red phosphorescent iridium (III) complex having the maximum emission wavelength on the longer wavelength side than 610 nm.
  • improvement in sublimation purification suitability and vapor deposition suitability by lowering the sublimation temperature was realized.
  • Cathode 10 Organic electroluminescent device (organic EL device) DESCRIPTION OF SYMBOLS 11 ... Organic layer 12 ... Protective layer 14 ... Adhesive layer 16 ... Sealing container 20 ... Light emitting device 30 ... Light scattering member 30A ... Light incident surface 30B ... Light Outgoing surface 32 ... fine particle 40 ... illumination device

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention porte sur une matière phosphorescente rouge qui émet de la lumière avec une excellente couleur et présente une sublimation aisée et une évaporation aisée. De façon spécifique, l'invention porte sur un complexe de métal organique qui est caractérisé comme étant représenté par la formule générale (1). (A représente un hétérocycle aromatique comprenant des atomes d'azote, et B représente un noyau aromatique ou un hétérocycle aromatique. En ce qui concerne au moins une paire de A et B, A représente un noyau quinoléine ou un noyau isoquinoléine, et B représente un naphtalène. A et B peuvent chacun être dotés d'un substituant, et peuvent également être un noyau fusionné. R1 et R3 représentent chacun indépendamment un groupe alkyle, un groupe aryle ou un groupe hétéroaryle. R2 représente un atome d'hydrogène, un groupe alkyle, un groupe aryle, un groupe hétéroaryle ou un atome d'halogène. De plus, au moins l'un parmi R1, R2 et R3 comprend au moins un ou plusieurs atomes de fluor).
PCT/JP2010/064649 2009-08-31 2010-08-27 Élément électroluminescent organique Ceased WO2011024977A1 (fr)

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US20190077818A1 (en) * 2017-09-08 2019-03-14 Chuanjun Xia Organic luminescent materials containing fluorine ancillary ligands
JP2021031490A (ja) * 2019-08-16 2021-03-01 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
US11127906B2 (en) 2016-10-03 2021-09-21 Universal Display Corporation Organic electroluminescent materials and devices
US11183642B2 (en) 2016-10-03 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11189804B2 (en) 2016-10-03 2021-11-30 Universal Display Corporation Organic electroluminescent materials and devices
US11196010B2 (en) 2016-10-03 2021-12-07 Universal Display Corporation Organic electroluminescent materials and devices

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JP5337896B2 (ja) * 2012-05-31 2013-11-06 株式会社日立製作所 有機発光層形成用材料，有機発光層形成用材料を用いた有機発光層形成用塗布液，有機発光層形成用塗布液を用いた有機発光素子および有機発光素子を用いた光源装置
JP5703350B2 (ja) * 2013-07-31 2015-04-15 株式会社日立製作所 有機発光層材料，有機発光層材料を用いた有機発光層形成用塗布液，有機発光層形成用塗布液を用いた有機発光素子および有機発光素子を用いた光源装置
KR102486941B1 (ko) 2018-02-02 2023-01-11 삼성디스플레이 주식회사 유기 전계 발광 소자, 이를 포함하는 유기 전계 발광 표시 장치, 및 유기 전계 발광 소자용 유기금속 화합물
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US11127906B2 (en) 2016-10-03 2021-09-21 Universal Display Corporation Organic electroluminescent materials and devices
US11183642B2 (en) 2016-10-03 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11189804B2 (en) 2016-10-03 2021-11-30 Universal Display Corporation Organic electroluminescent materials and devices
US11196010B2 (en) 2016-10-03 2021-12-07 Universal Display Corporation Organic electroluminescent materials and devices
US20190077818A1 (en) * 2017-09-08 2019-03-14 Chuanjun Xia Organic luminescent materials containing fluorine ancillary ligands
JP2021031490A (ja) * 2019-08-16 2021-03-01 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

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