WO2012005364A1 - Elément électroluminescent organique - Google Patents

Elément électroluminescent organique Download PDF

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WO2012005364A1
WO2012005364A1 PCT/JP2011/065719 JP2011065719W WO2012005364A1 WO 2012005364 A1 WO2012005364 A1 WO 2012005364A1 JP 2011065719 W JP2011065719 W JP 2011065719W WO 2012005364 A1 WO2012005364 A1 WO 2012005364A1
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group
substituent
general formula
aryl
ring
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PCT/JP2011/065719
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Japanese (ja)
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誠之 林
伊勢　俊大
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富士フイルム株式会社
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Priority to KR1020187004303A priority Critical patent/KR20180018861A/ko
Priority to KR1020137003055A priority patent/KR101995080B1/ko
Publication of WO2012005364A1 publication Critical patent/WO2012005364A1/fr

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    • 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
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • 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
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission

Definitions

  • the present invention relates to an organic electroluminescent device.
  • Organic electroluminescent elements (hereinafter also referred to as “elements” and “organic EL elements”) are actively researched and developed because they can emit light with high luminance when driven at a low voltage.
  • An organic electroluminescent element has an organic layer between a pair of electrodes, and electrons injected from the cathode and holes injected from the anode recombine in the organic layer, and the generated exciton energy is used for light emission. To do.
  • Patent Document 1 describes an organic electroluminescent element using an iridium complex as a phosphorescent material and a compound containing a carbazole structure as a host material in a light emitting layer.
  • Patent Document 2 describes an organic electroluminescence device in which an electron transport layer made of a specific compound containing an anthracene structure and a benzimidazole structure is provided between a light emitting layer containing a fluorescent material and a cathode.
  • Patent Document 3 an iridium complex is used as a phosphorescent material in the light emitting layer, a compound containing a carbazole structure is used as a host material, and an anthracene structure and a benzimidazole structure are included between the light emitting layer and the cathode.
  • An organic electroluminescent device provided with an electron transport layer made of a specific compound is described.
  • Patent Documents 4 and 5 also describe an organic electroluminescent device having a compound containing an anthracene structure and a benzimidazole structure.
  • an object of the present invention is a compound that is excellent in terms of light emission efficiency, drive voltage, and durability, has little decrease in efficiency during high luminance drive, and has an electron transport property between the light emitting layer and the cathode It is an object to provide an organic electroluminescence device in which the luminescence chromaticity of the device is less dependent on the film thickness of the layer containing the.
  • the above-mentioned problem is caused by containing a specific compound containing a carbazole structure in the light emitting layer, and including a specific compound containing an anthracene structure and a benzimidazole structure in the cathode side layer from the light emitting layer.
  • a specific compound containing a carbazole structure in the light emitting layer and including a specific compound containing an anthracene structure and a benzimidazole structure in the cathode side layer from the light emitting layer.
  • An organic electroluminescent device having a pair of electrodes consisting of an anode and a cathode on a substrate, a light emitting layer between the electrodes, and at least one organic layer between the light emitting layer and the cathode,
  • the light emitting layer contains at least one compound represented by the following general formula (1)
  • An organic electroluminescence device comprising at least one compound represented by the following general formula (E-1) in at least one organic layer between the light emitting layer and the cathode.
  • R 1 represents an alkyl group, an aryl group, or a silyl group, and may further have a substituent Z, provided that R 1 represents a carbazolyl group or a perfluoroalkyl group. If no .R 1 there are a plurality, the plurality of R 1 each may be the same or different. the plurality of R 1 may form an aryl ring which may have a substituent Z bonded to each other May be.
  • R 2 to R 5 each independently represents an alkyl group, an aryl group, a silyl group, a cyano group, or a fluorine atom, and may further have a substituent Z.
  • the substituent Z represents an alkyl group, an alkenyl group, an aryl group, an aromatic heterocyclic group, an alkoxy group, a phenoxy group, a fluorine atom, a silyl group, an amino group, a cyano group, or a group formed by combining these, and a plurality of substituents Z may combine with each other to form an aryl ring.
  • n1 represents an integer of 0 to 5.
  • n2 to n5 each independently represents an integer of 0 to 4.
  • R E1 and R E2 each independently represent a hydrogen atom, an aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group. However, R E1 and R E2 are not simultaneously hydrogen atoms.
  • Ar represents a substituted or unsubstituted arylene group or a substituted or unsubstituted divalent aromatic heterocyclic group.
  • R E3 represents a hydrogen atom, an aliphatic hydrocarbon, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group.
  • R E4 represents a hydrogen atom, an aliphatic hydrocarbon, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group.
  • R 6 and R 7 each independently represents an alkyl group which may have a substituent Z, an aryl group which may have an alkyl group, a cyano group or a fluorine atom.
  • R 6 and R 7 may be the same as or different from each other, and the plurality of R 6 and the plurality of R 7 are bonded to each other.
  • An aryl ring which may have a substituent Z may be formed.
  • n6 and n7 each independently represents an integer of 0 to 5.
  • R 8 to R 11 are each independently a hydrogen atom, an alkyl group optionally having substituent Z, an aryl group optionally having alkyl group, or a silyl group optionally having substituent Z Represents a cyano group or a fluorine atom.
  • the substituent Z represents an alkyl group, an alkenyl group, an aryl group, an aromatic heterocyclic group, an alkoxy group, a phenoxy group, a fluorine atom, a silyl group, an amino group, a cyano group, or a group formed by combining these, and a plurality of substituents Z may combine with each other to form an aryl ring.
  • R E1 and R E2 are each independently a hydrogen atom, an aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted group. However, R E1 and R E2 are not simultaneously hydrogen atoms.
  • R E3 represents a hydrogen atom, an aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group.
  • R T3 ′, R T3 , R T4 , R T5 and R T6 are each independently a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, Represents a fluorovinyl group, —CO 2 R T , —C (O) R T , —N (R T ) 2 , —NO 2 , —OR T , a halogen atom, an aryl group or a heteroaryl group; You may have.
  • E represents a carbon atom or a nitrogen atom.
  • Q is a 5-membered or 6-membered aromatic heterocyclic ring or condensed aromatic heterocyclic ring containing one or more nitrogen atoms.
  • the line connecting E and N is represented by a single line, but the bond type is not limited, and each may be a single bond or a double bond.
  • R T3 , R T4 , R T5 and R T6 may be any two adjacent to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or hetero It is aryl, and the condensed 4- to 7-membered ring may further have a substituent T.
  • Each substituent T independently, a fluorine atom, -R ', - OR', - N (R ') 2, -SR', - C (O) R ', - C (O) OR', - C ( O) represents N (R ′) 2 , —CN, —NO 2 , —SO 2 , —SOR ′, —SO 2 R ′, or —SO 3 R ′, and each R ′ independently represents a hydrogen atom, alkyl Represents a group, a perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • (XY) represents a ligand.
  • m represents an integer of 1 to 3
  • n represents an integer of 0 to 2.
  • m + n is 3.
  • Organic electroluminescent element Any one of [1] to [11] above, wherein at least one of the light emitting layer and the other organic layer existing between the anode and the cathode is formed by a solution coating process.
  • Organic electroluminescent element [13] A light emitting device using the organic electroluminescent element according to any one of [1] to [12].
  • a display device using the organic electroluminescent element according to any one of [1] to [12].
  • An organic electroluminescent device having a pair of electrodes consisting of an anode and a cathode on a substrate, a light emitting layer between the electrodes, and at least one organic layer between the light emitting layer and the cathode,
  • the light emitting layer contains at least one compound represented by the following general formula (1)
  • the light emitting layer contains a phosphorescent light emitting material represented by the following general formula (T-1)
  • An organic electroluminescence device comprising at least one compound represented by the following general formula (E-1) in at least one organic layer between the light emitting layer and the cathode.
  • R 1 represents an alkyl group or an aryl group, and may further have a substituent Z. However, R 1 does not represent a carbazolyl group or a perfluoroalkyl group. If 1 there are a plurality, the plurality of R 1 each may be the same or different. the plurality of R 1 may be formed an aryl ring which may have a substituent Z bonded to each other Good.
  • R 2 to R 5 each independently represents an alkyl group, an aryl group, a silyl group, a cyano group, or a fluorine atom, and may further have a substituent Z.
  • the substituent Z represents an alkyl group, an aryl group, or a fluorine atom.
  • n1 represents an integer of 1 to 4.
  • n2 to n5 each independently represents an integer of 0 to 4. )
  • R E1 and R E2 each independently represent an unsubstituted aryl group or an unsubstituted pyridyl group.
  • Ar represents an unsubstituted arylene group or an unsubstituted divalent pyridyl group.
  • R E3 represents a hydrogen atom or an unsubstituted aryl group.
  • R E4 represents an unsubstituted aryl group or an unsubstituted pyridyl group.
  • R T3 ′, R T3 , R T4 , R T5 and R T6 are each independently a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, Represents a fluorovinyl group, —CO 2 R T , —C (O) R T , —N (R T ) 2 , —NO 2 , —OR T , a halogen atom, an aryl group or a heteroaryl group; You may have.
  • E represents a carbon atom or a nitrogen atom.
  • Q is a 5-membered or 6-membered aromatic heterocyclic ring or condensed aromatic heterocyclic ring containing one or more nitrogen atoms.
  • the line connecting E and N is represented by a single line, but the bond type is not limited, and each may be a single bond or a double bond.
  • R T3 , R T4 , R T5 and R T6 may be any two adjacent to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or hetero It is aryl, and the condensed 4- to 7-membered ring may further have a substituent T.
  • Each substituent T independently, a fluorine atom, -R ', - OR', - N (R ') 2, -SR', - C (O) R ', - C (O) OR', - C ( O) represents N (R ′) 2 , —CN, —NO 2 , —SO 2 , —SOR ′, —SO 2 R ′, or —SO 3 R ′, and each R ′ independently represents a hydrogen atom, alkyl Represents a group, a perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • each R 6 and R 7 independently represent an alkyl group, if .R 6 and R 7 representing an aryl group, or a fluorine atom is present in plural, a plurality of R 6 and a plurality of R 7 may be the same or different, and the plurality of R 6 and the plurality of R 7 may be bonded to each other to form an aryl ring which may have a substituent Z.
  • n6 and n7 each independently represents an integer of 0 to 2.
  • R 8 to R 11 are each independently a hydrogen atom, an alkyl group optionally having substituent Z, an aryl group optionally having alkyl group, or a silyl group optionally having substituent Z Represents a cyano group or a fluorine atom.
  • the substituent Z represents an alkyl group, an aryl group, or a fluorine atom.
  • R E1 and R E2 each independently represents an unsubstituted aryl group or an unsubstituted pyridyl group.
  • R E3 represents a hydrogen atom or an unsubstituted aryl group.
  • Organic electroluminescent element Any one of [16] to [24] above, wherein at least one of the light emitting layer and the other organic layer existing between the anode and the cathode is formed by a solution coating process.
  • Organic electroluminescent element [26] A light emitting device using the organic electroluminescent element according to any one of [16] to [25]. [27] [16] A display device using the organic electroluminescent element as described in any one of [16] to [25]. [28] An illumination device using the organic electroluminescent element according to any one of [16] to [25].
  • a film of a layer including a compound having an electron transporting property between a light emitting layer and a cathode which is excellent in terms of luminous efficiency, driving voltage, and durability, has a small decrease in efficiency when driven at high luminance. It is possible to provide an organic electroluminescence device in which the emission chromaticity of the device is less dependent on the thickness.
  • the hydrogen atom also includes isotopes (deuterium atoms, etc.), and the atoms constituting the substituents also include the isotopes. .
  • the substituent group A, the substituent group B, and the substituent Z are defined as follows.
  • An alkyl group preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, neopentyl, etc.), alkenyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms) For example, vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms),
  • it 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. a heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms).
  • pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc. an acyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, For example, acetyl, benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms).
  • aryloxycarbonyl group ( The number of carbon atoms is preferably 7 to 30, more preferably 7 to 20, and particularly preferably 7 to 12, and examples thereof include phenyloxycarbonyl. ), An acyloxy group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy, benzoyloxy, etc.), an acylamino group (preferably 2-30 carbon atoms, more preferably 2-20 carbon atoms, particularly preferably 2-10 carbon atoms, and examples thereof include acetylamino, benzoylamino and the like, and alkoxycarbonylamino groups (preferably having 2-2 carbon atoms).
  • an aryloxycarbonylamino group preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, for example phenyloxycarbonyl And sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino).
  • an aryloxycarbonylamino group preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, for example phenyloxycarbonyl And sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino).
  • a sulfamoyl group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenyl Sulfamoyl, etc.), carbamoyl groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as carbamoyl, methylcarbamoyl, diethylcarbamoyl, Phenylcarbamoyl etc.), alkylthio group ( Preferably, it has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio, ethylthio, etc.), an arylthio group (preferably 6 to 30 carbon atoms).
  • Rufinyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include methanesulfinyl and benzenesulfinyl. ), A ureido group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as ureido, methylureido, phenylureido, etc.), phosphoric acid An amide group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenyl phosphoric acid amide), a hydroxy group , Mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carb
  • Is for example, a nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, silicon atom, selenium atom, tellurium atom, specifically pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, And isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, silolyl group and the like.
  • a silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyl and triphenylsilyl).
  • a aryloxy group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyloxy, triphenylsilyloxy, etc.), phosphoryl group (for example, A diphenylphosphoryl group, a dimethylphosphoryl group, etc.).
  • These substituents may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.
  • alkyl group preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.
  • alkenyl groups preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.
  • alkynyl group preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as propargyl , 3-pentynyl, etc.
  • aryl groups preferably having 6 to 30 carbon atoms, preferably 1
  • the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group B described above.
  • the substituent substituted by the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group B described above.
  • Substituent Z Represents an alkyl group, an alkenyl group, an aryl group, an aromatic heterocyclic group, an alkoxy group, a phenoxy group, a fluorine atom, a silyl group, an amino group, a cyano group or a combination thereof, and a plurality of substituents Z are bonded to each other Thus, an aryl ring may be formed.
  • substituent Z an alkyl group, an aryl group, a fluorine atom, or a cyano group is preferable, and an alkyl group, an aryl group, or a fluorine atom is more preferable.
  • the alkyl group represented by the substituent Z is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms.
  • a methyl group, an ethyl group, an isobutyl group, or a t-butyl group is preferable, and a methyl group is more preferable.
  • the alkenyl group represented by the substituent Z is preferably an alkenyl group having 2 to 8 carbon atoms, more preferably an alkenyl group having 2 to 6 carbon atoms, such as a vinyl group, an n-propenyl group, an isopropenyl group, Examples thereof include an isobutenyl group, an n-butenyl group, and the like, and a vinyl group, an n-propenyl group, an isobutenyl group, or an n-butenyl group is preferable, and a vinyl group is more preferable.
  • the aryl group represented by the substituent Z is preferably an aryl group having 6 to 18 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms.
  • a phenyl group, a biphenyl group, a naphthyl group, a tolyl group, a xylyl group and the like can be mentioned.
  • a phenyl group and a biphenyl group are preferable, and a phenyl group is more preferable.
  • the aromatic heterocyclic group represented by the substituent Z is preferably an aromatic heterocyclic group having 4 to 12 carbon atoms, and examples thereof include a pyridyl group, a furyl group, and a thienyl group, and a pyridyl group or a furyl group is preferable.
  • a pyridyl group is more preferable.
  • the alkoxy group represented by the substituent Z is preferably an alkoxy group having 1 to 8 carbon atoms, more preferably an alkoxy group having 1 to 4 carbon atoms, such as a methoxy group, an ethoxy group, an n-propoxy group, A propoxy group, an isobutoxy group, a t-butoxy group, an n-butoxy group, a cyclopropyloxy group, and the like can be given.
  • a methoxy group, an ethoxy group, an isobutoxy group, or a t-butoxy group is preferable, and a methoxy group is more preferable.
  • Examples of the silyl group and amino group represented by the substituent Z include those similar to the silyl group and amino group in the substituent group A described above.
  • Examples of the aryl ring formed by bonding a plurality of substituents Z to each other include a benzene ring and a naphthalene ring, and a benzene ring is preferable.
  • the organic electroluminescent device of the present invention comprises a substrate having a pair of electrodes consisting of an anode and a cathode, a light emitting layer between the electrodes, and an organic layer having at least one organic layer between the light emitting layer and the cathode.
  • An electroluminescent device comprising: Containing at least one compound represented by the general formula (1) in the light emitting layer; At least one compound represented by formula (E-1) is contained in at least one organic layer between the light emitting layer and the cathode.
  • R 1 represents an alkyl group, an aryl group, or a silyl group, and may further have a substituent Z, provided that R 1 represents a carbazolyl group or a perfluoroalkyl group. If no .R 1 there are a plurality, the plurality of R 1 each may be the same or different. the plurality of R 1 may form an aryl ring which may have a substituent Z bonded to each other May be.
  • R 2 to R 5 each independently represents an alkyl group, an aryl group, a silyl group, a cyano group, or a fluorine atom, and may further have a substituent Z.
  • the substituent Z represents an alkyl group, an alkenyl group, an aryl group, an aromatic heterocyclic group, an alkoxy group, a phenoxy group, a fluorine atom, a silyl group, an amino group, a cyano group, or a group formed by combining these, and a plurality of substituents Z may combine with each other to form an aryl ring.
  • n1 represents an integer of 0 to 5.
  • n2 to n5 each independently represents an integer of 0 to 4.
  • the alkyl group represented by R 1 may have a substituent.
  • substituents include the aforementioned substituent Z, and the substituent Z is preferably a fluorine atom.
  • the alkyl group represented by R 1 does not become a perfluoroalkyl group.
  • the alkyl group represented by R 1 is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and still more preferably an alkyl group having 1 to 4 carbon atoms. .
  • the aryl group represented by R 1 may be condensed or may have a substituent.
  • substituent Z examples include the above-described substituent Z.
  • the substituent Z is preferably an alkyl group, an aryl group, a fluorine atom or a cyano group which may be substituted with a fluorine atom. Groups are more preferred.
  • the aryl group represented by R 1 is preferably an aryl group having 6 to 30 carbon atoms, and more preferably an aryl group having 6 to 18 carbon atoms.
  • the aryl group having 6 to 18 carbon atoms is preferably an alkyl group optionally having a fluorine atom having 1 to 6 carbon atoms, a fluorine atom or a cyano group, and optionally having 6 to 18 carbon atoms. And more preferably an aryl group having 6 to 18 carbon atoms which may have an alkyl group having 1 to 4 carbon atoms.
  • the silyl group represented by R 1 may have a substituent.
  • substituent Z examples include the above-described substituent Z, and the substituent Z is preferably an alkyl group or a phenyl group, and more preferably a phenyl group.
  • the silyl group represented by R 1 is preferably a silyl group having 0 to 18 carbon atoms, and more preferably a silyl group having 3 to 18 carbon atoms.
  • the silyl group having 3 to 18 carbon atoms is preferably a silyl group having 3 to 18 carbon atoms substituted with an alkyl group having 1 to 6 carbon atoms or a phenyl group, and all three hydrogen atoms of the silyl group are carbon atoms. It is more preferably substituted with any one of an alkyl group of 1 to 6 and a phenyl group, and further preferably substituted with a phenyl group.
  • trimethylsilyl group triethylsilyl group, t-butyldimethylsilyl group, diethylisopropylsilyl group, dimethylphenylsilyl group, diphenylmethylsilyl group, triphenylsilyl group, and the like.
  • Group or triphenylsilyl group is preferable, and triphenylsilyl group is more preferable.
  • R 1 there are a plurality the plurality of R 1 may each be the same or different. Moreover, several R ⁇ 1 > may couple
  • substituent Z an alkyl group or an aryl group is preferable, and an alkyl group is more preferable.
  • Aryl ring plurality of R 1 is formed by bonding with, including the carbon atom to which R 1 of said plurality of substitution, preferably an aryl ring having 6 to 30 carbon atoms, more preferably having 6 to 14 carbon atoms An aryl ring.
  • the ring to be formed is preferably any one of a benzene ring, a naphthalene ring and a phenanthrene ring, more preferably a benzene ring or a phenanthrene ring, and further preferably a benzene ring.
  • a plurality of rings formed by a plurality of R 1 may exist, for example, a plurality of R 1 are bonded to each other to form two benzene rings, together with a benzene ring substituted by the plurality of R 1 A phenanthrene ring may be formed.
  • R 1 is preferably an alkyl group, an aryl group optionally having an alkyl group, and a silyl group substituted with an alkyl group or a phenyl group, from the viewpoint of charge transport ability and charge stability. More preferably an aryl group having 6 to 18 carbon atoms which may have an alkyl group having 1 to 6 carbon atoms, and still more preferably an alkyl group having an alkyl group having 1 to 4 carbon atoms. 6 to 18 aryl groups.
  • R 1 is preferably a methyl group, a t-butyl group, a neopentyl group, an unsubstituted phenyl group, a cyano group, a phenyl group substituted by a fluorine atom or a trifluoromethyl group, a biphenyl group, a terphenyl group.
  • An unsubstituted phenyl group, a biphenyl group, a naphthyl group, or a terphenyl group is more preferable, and an unsubstituted phenyl group, an unsubstituted biphenyl group, or an unsubstituted naphthyl group is more preferable.
  • N1 is preferably an integer of 0 to 4, more preferably an integer of 0 to 3, and still more preferably an integer of 0 to 2.
  • Specific examples and preferred examples of the aryl group and silyl group represented by R 2 to R 5 are the same as the specific examples and preferred examples of the aryl group and silyl group represented by R 1 .
  • Examples of the alkyl group represented by R 2 to R 5 include perfluoroalkyl groups such as a trifluoromethyl group in addition to the examples of the alkyl group represented by R 1 . Of these, a methyl group, a trifluoromethyl group, an isopropyl group, a t-butyl group, or a neopentyl group is preferable, a methyl group or a t-butyl group is more preferable, and a t-butyl group is still more preferable.
  • R 2 to R 5 are each independently preferably any of a silyl group substituted with an alkyl group, an aryl group, an alkyl group or a phenyl group, a cyano group, and a fluorine atom, from the viewpoint of charge transportability and charge stability.
  • R 2 to R 5 are preferably each independently methyl group, isopropyl group, t-butyl group, neopentyl group, trifluoromethyl group, phenyl group, dimethylphenyl group, trimethylsilyl group, triphenylsilyl group, fluorine Any of an atom and a cyano group, more preferably a t-butyl group, a phenyl group, a trimethylsilyl group, a triphenylsilyl group, and a cyano group, still more preferably a t-butyl group, a phenyl group, It is either a triphenylsilyl group or a cyano group.
  • N2 to n5 are each independently preferably an integer of 0 to 2, and more preferably 0 or 1.
  • the 3-position and the 6-position of the carbazole skeleton are reaction active positions. From the viewpoint of ease of synthesis and improvement in chemical stability, the substituent may be introduced at this position. preferable.
  • the compound represented by the general formula (1) is represented by the following general formula (2).
  • R 6 and R 7 each independently represents an alkyl group which may have a substituent Z, an aryl group which may have an alkyl group, a cyano group or a fluorine atom.
  • R 6 and R 7 may be the same as or different from each other, and the plurality of R 6 and the plurality of R 7 are bonded to each other.
  • An aryl ring which may have a substituent Z may be formed.
  • n6 and n7 each independently represents an integer of 0 to 5.
  • R 8 to R 11 are each independently a hydrogen atom, an alkyl group optionally having substituent Z, an aryl group optionally having alkyl group, or a silyl group optionally having substituent Z Represents a cyano group or a fluorine atom.
  • the substituent Z represents an alkyl group, an alkenyl group, an aryl group, an aromatic heterocyclic group, an alkoxy group, a phenoxy group, a fluorine atom, a silyl group, an amino group, a cyano group, or a group formed by combining these, and a plurality of substituents Z may combine with each other to form an aryl ring.
  • the alkyl group represented by R 6 and R 7 may have a substituent.
  • examples of the substituent include the aforementioned substituent Z, and the substituent Z is preferably a fluorine atom.
  • the alkyl group represented by R 6 and R 7 is preferably an alkyl group having 1 to 6 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms. Specific examples and preferred examples of the alkyl group represented by R 6 and R 7 are the same as the specific examples and preferred examples of the alkyl group represented by R 2 to R 5 in the general formula (1).
  • the alkyl group in the aryl group which may have an alkyl group represented by R 6 and R 7 is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms. It is. Specific examples and preferred examples of the alkyl group are the same as the specific examples and preferred examples of the alkyl group represented by R 2 to R 5 in the general formula (1).
  • the aryl group in the aryl group which may have an alkyl group represented by R 6 and R 7 is preferably an aryl group having 6 to 18 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. It is.
  • a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthranyl group, a phenanthryl group, a chrysenyl group, etc. among which a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group are preferable, a phenyl group, A biphenyl group or a terphenyl group is more preferable.
  • the aryl group that may have an alkyl group represented by R 6 and R 7 is preferably an unsubstituted aryl group.
  • Examples of the aryl group represented by R 6 and R 7 which may have an alkyl group include a phenyl group, a dimethylphenyl group, a t-butylphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, and a methyl group.
  • a naphthyl group, a t-butyl naphthyl group, an anthranyl group, a phenanthryl group, a chrysenyl group, and the like can be given.
  • a phenyl group, a t-butylphenyl group, or a biphenyl group is preferable, and a phenyl group is more preferable.
  • the plurality of R 6 and the plurality of R 7 may be the same as or different from each other.
  • a plurality of R 6 and a plurality of R 7 may be bonded to each other to form an aryl ring which may have the aforementioned substituent Z.
  • the substituent Z an alkyl group or an aryl group is preferable, and an alkyl group is more preferable.
  • the aryl ring formed by bonding a plurality of R 6 and a plurality of R 7 to each other includes a carbon atom substituted by each of the plurality of R 6 and the plurality of R 7 , and preferably has 6 to 30 carbon atoms.
  • an aryl ring having 6 to 14 carbon atoms More preferred is an aryl ring having 6 to 14 carbon atoms, and still more preferred is an aryl ring having 6 to 14 carbon atoms which may have an alkyl group having 1 to 4 carbon atoms.
  • the ring to be formed is preferably any of a benzene ring, a naphthalene ring and a phenanthrene ring, which may have an alkyl group having 1 to 4 carbon atoms, and has an alkyl group having 1 to 4 carbon atoms.
  • An benzene ring which may be substituted is more preferable, and examples thereof include a benzene ring and a benzene ring substituted with a t-butyl group.
  • a plurality of rings formed by a plurality of R 6 or a plurality of R 7 may exist, for example, a plurality of R 6 or a plurality of R 7 are bonded to each other to form two benzene rings, A phenanthrene ring may be formed together with a plurality of R 6 or the benzene ring substituted by the plurality of R 7 .
  • R 6 and R 7 are preferably an alkyl group having 1 to 6 carbon atoms and an alkyl group having 1 to 6 carbon atoms, preferably 6 to 18 carbon atoms, from the viewpoint of charge transport ability and charge stability. Any of aryl groups, cyano groups and fluorine atoms, more preferably an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 12 carbon atoms which may have an alkyl group having 1 to 4 carbon atoms. , Either a cyano group or a fluorine atom. From the viewpoint of charge transportability and charge stability, it is also preferable that R 6 and R 7 each independently represent an alkyl group or an aryl group that may have an alkyl group.
  • R 6 and R 7 are preferably each independently, preferably a methyl group, a trifluoromethyl group, a t-butyl group, an unsubstituted phenyl group, a phenyl group substituted by a t-butyl group, a biphenyl group, a cyano group.
  • N6 and n7 are each independently preferably an integer of 0 to 4, more preferably an integer of 0 to 2, and even more preferably 0 or 1.
  • the alkyl group represented by R 8 to R 11 may have a substituent.
  • examples of the substituent include the aforementioned substituent Z, and the substituent Z is preferably a fluorine atom.
  • the alkyl group represented by R 8 to R 11 is preferably an alkyl group having 1 to 6 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms. Specific examples and preferred examples of the alkyl group represented by R 8 to R 11 are the same as the specific examples and preferred examples of the alkyl group represented by R 2 to R 5 in the general formula (1).
  • the aryl group optionally having an alkyl group represented by R 8 to R 11 is preferably an aryl group having 6 to 18 carbon atoms which may have an alkyl group having 1 to 6 carbon atoms. And more preferably an aryl group having 6 to 12 carbon atoms which may have an alkyl group having 1 to 4 carbon atoms.
  • Specific examples and preferred examples of the aryl group optionally having an alkyl group represented by R 8 to R 11 may have an alkyl group represented by the aforementioned R 6 and R 7. This is the same as the specific examples and preferred examples of the aryl group.
  • the silyl group represented by R 8 to R 11 may have a substituent.
  • substituent Z examples include the above-described substituent Z, and the substituent Z is preferably an alkyl group or a phenyl group, and more preferably a phenyl group.
  • the silyl group represented by R 8 to R 11 is preferably a silyl group having 3 to 18 carbon atoms. Specific examples and preferred examples of the silyl group having 3 to 18 carbon atoms represented by R 8 to R 11 are The same as the specific examples and preferred examples of the silyl group having 3 to 18 carbon atoms in the silyl group represented by R 1 in the general formula (1).
  • R 8 to R 11 are each independently preferably substituted with a hydrogen atom, an alkyl group, an aryl group optionally having an alkyl group, an alkyl group or a phenyl group from the viewpoint of charge transportability and charge stability.
  • a silyl group, a cyano group, or a fluorine atom more preferably a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms.
  • R 8 to R 11 are preferably each independently a hydrogen atom, methyl group, isopropyl group, t-butyl group, neopentyl group, trifluoromethyl group, phenyl group, dimethylphenyl group, trimethylsilyl group, triphenylsilyl group.
  • Group, a fluorine atom, and a cyano group more preferably a hydrogen atom, a t-butyl group, a phenyl group, a trimethylsilyl group, a triphenylsilyl group, and a cyano group, and more preferably a hydrogen atom.
  • the compound represented by the general formula (1) or (2) is most preferably composed of only a carbon atom, a hydrogen atom and a nitrogen atom.
  • the glass transition temperature (Tg) of the compound represented by the general formula (1) or (2) is preferably 80 ° C. or higher and 400 ° C. or lower, more preferably 100 ° C. or higher and 400 ° C. or lower, and 120 ° C. or higher. More preferably, it is 400 degrees C or less.
  • an isotope such as a deuterium atom
  • all hydrogen atoms in the compound may be replaced with isotopes, or a mixture in which a part is a compound containing an isotope may be used.
  • this invention is not limited to these.
  • the compounds exemplified as the compounds represented by the general formula (1) or (2) can be synthesized with reference to International Publication No. 2004/074399 pamphlet and the like.
  • compound (A-1) can be synthesized by the method described in WO 2004/074399, paragraph 52, line 22 to paragraph 54, line 15.
  • the compound represented by the general formula (1) or (2) is contained in the light emitting layer, but its use is not limited, and it is further contained in any layer in the organic layer. Also good.
  • a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, a charge block layer Either can be mentioned.
  • the compound represented by the general formula (1) or (2) is preferably included in an amount of 50 to 99.9% by mass, more preferably 50 to 99% by mass, with respect to the total mass of the light emitting layer. It is more preferable to include 98% by mass.
  • the compound represented by the general formula (1) or (2) is further contained in a layer other than the light emitting layer, it is preferably contained in an amount of 70 to 100% by mass, and 85 to 100% by mass with respect to the total mass of the layer. % Is more preferable.
  • R E1 and R E2 each independently represent a hydrogen atom, an aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group. However, R E1 and R E2 are not simultaneously hydrogen atoms.
  • Ar represents a substituted or unsubstituted arylene group or a substituted or unsubstituted divalent aromatic heterocyclic group.
  • R E3 represents a hydrogen atom, an aliphatic hydrocarbon, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group.
  • R E4 represents a hydrogen atom, an aliphatic hydrocarbon, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group.
  • the compound represented by the general formula (E-1) is contained in at least one organic layer between the cathode and the light emitting layer, but may be further contained in other layers. .
  • the efficiency reduction during high luminance driving is suppressed.
  • the light emitting layer contains the compound represented by the general formula (1)
  • at least one organic layer between the light emitting layer and the cathode contains the compound represented by the general formula (E-1).
  • the electron affinity between the compound represented by the general formula (E-1) and the compound represented by the general formula (1) is in an optimum range, and the electron transport property of the electron transport layer from a low voltage is improved, This is presumably because a large amount of electrons can be transported to the light emitting layer.
  • the dependency of the emission chromaticity on the electron transport layer thickness was suppressed in the device of the present invention.
  • the light emitting layer contains the compound represented by the general formula (1), and the organic layer between the light emitting layer and the cathode has the general formula (E-1).
  • E-1 the organic layer between the light emitting layer and the cathode has the general formula (E-1).
  • R E1 and R E2 each independently represent a hydrogen atom, an aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group.
  • the aliphatic hydrocarbon group is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms, and an alkyl group (preferably having 1 to 10 carbon atoms).
  • alkenyl group preferably having 2 to 10 carbon atoms, such as vinyl, allyl, 2-butenyl, 3-pentenyl, etc.
  • alkynyl group preferably having 2 to 10 carbon atoms such as propargyl, 3 -Pentynyl, etc.
  • alkyl groups are more preferred, methyl groups, ethyl groups, isopropyl , Particularly preferably a t- butyl group, or cyclohexyl group.
  • the aryl group is preferably an aryl having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms. It is a group.
  • the aryl group include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a pyrenyl group, a triphenylenyl group, and the like.
  • Group or terphenyl group is preferable, phenyl group, naphthyl group, biphenyl group, or anthryl group is more preferable, and naphthyl group is most preferable.
  • the reason why the naphthyl group is preferable is considered to be that an appropriate interaction between molecules can be generated, whereby a reduction in driving voltage and a stable film quality can be obtained.
  • examples of the substituent include a substituent selected from the substituent group A, preferably an alkyl group (preferably an alkyl group having 1 to 8 carbon atoms, more Preferred is an alkyl group having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an isobutyl group, a t-butyl group, an n-butyl group, and a cyclopropyl group.
  • an alkyl group preferably an alkyl group having 1 to 8 carbon atoms, more Preferred is an alkyl group having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an isobutyl group, a t-butyl group, an n-butyl group, and a cyclopropyl group.
  • an ethyl group an isobutyl group, or a t-butyl group
  • an aryl group preferably an aryl group having 6 to 18 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms
  • a phenyl group or a biphenyl group is preferred.
  • a halogen atom preferably a fluorine atom
  • Group an alkoxy group, or an aromatic heterocyclic group (preferably an aromatic heterocyclic group having 4 to 12 carbon atoms, such as a pyridyl group, a furyl group, and a thienyl group, and a pyridyl group is more preferable). It is.
  • the aromatic heterocyclic group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably carbon atoms. It is an aromatic heterocyclic group of 2 to 12.
  • the aromatic heterocyclic group include an azole group, a diazole group, a triazole group, an oxazole group, a thiazole group, a pyridyl group, a furyl group, and a thienyl group, and an azole group, a diazole group, and a pyridyl group are preferable.
  • a pyridyl group is more preferred.
  • R E1 and R E2 are preferably a substituted or unsubstituted aryl group, and more preferably an unsubstituted aryl group from the viewpoint of obtaining an appropriate interaction between molecules. Specific examples and preferred ranges when R E1 and R E2 are aryl groups are as described above.
  • R E1 and R E2 may be the same or different from each other, but are preferably the same from the viewpoint of synthesis. However, R E1 and R E2 are not simultaneously hydrogen atoms.
  • Ar represents a substituted or unsubstituted arylene group or a substituted or unsubstituted divalent aromatic heterocyclic group.
  • the arylene group is preferably an arylene group having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms.
  • the arylene group include a phenylene group, a naphthylene group, a biphenylene group, an anthrylene group, a terphenylene group, a fluorenylene group, a phenanthrylene group, a pyrenylene group, a triphenylenylene group, and the like.
  • an anthrylene group is preferred, a phenylene group or a naphthylene group is more preferred, and a phenylene group is most preferred.
  • the arylene group has a substituent, examples of the substituent are the same as those of the substituent that may be present in the case where R E1 and R E2 are an aryl group.
  • the divalent aromatic heterocyclic group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably Is a divalent aromatic heterocyclic group having 2 to 12 carbon atoms.
  • the divalent aromatic heterocyclic group include a divalent azole group, a divalent diazole group, a divalent triazole group, a divalent oxazole group, a divalent thiazole group, a divalent pyridyl group, A bivalent furyl group, a bivalent thienyl group, etc.
  • a bivalent azole group, a bivalent diazole group, and a bivalent pyridyl group are preferable, and a bivalent pyridyl group (pyridylene group) is more preferable.
  • examples of the substituent are the same as those of the substituent that R E1 and R E2 may have in the case of an aryl group, and specific examples and preferred ranges thereof. is there.
  • Ar preferably represents a substituted or unsubstituted arylene group, more preferably an unsubstituted arylene group. Specific examples and preferred ranges when Ar is an arylene group are as described above.
  • R E3 represents a hydrogen atom, an aliphatic hydrocarbon, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group.
  • R E3 represents an aliphatic hydrocarbon group
  • the aliphatic hydrocarbon group preferably has 1 to 20 carbon atoms and is preferably an alkyl group (preferably having 1 to 10 carbon atoms, such as a methyl group, ethyl group, isopropyl Group, t-butyl group, n-octyl group, n-decyl group, n-hexadecyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, neopentyl group, etc.), alkenyl group (preferably having a carbon number of 2 to 10 such as vinyl, allyl, 2-butenyl, 3-pentenyl, and the like, or an alkynyl group (preferably having 2 to 10 carbon atoms, such as propargyl, 3-pentynyl, etc.).
  • alkyl group preferably having 1 to 10 carbon atoms, such as a methyl group, e
  • it is an alkyl group, more preferably a methyl group, an ethyl group, an isopropyl group, a t-butyl group, or a cyclohexyl group. Particularly preferred is a xyl group.
  • the aryl group is preferably an aryl group having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms.
  • the aryl group include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a pyrenyl group, and a triphenylenyl group, and a phenyl group, a naphthyl group, a biphenyl group, or the like.
  • anthryl group is preferable, and a phenyl group is more preferable.
  • the aryl group has a substituent
  • examples of the substituent include a substituent selected from the substituent group A, preferably an alkyl group (preferably an alkyl group having 1 to 8 carbon atoms, more Preferred is an alkyl group having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an isobutyl group, a t-butyl group, an n-butyl group, and a cyclopropyl group.
  • an ethyl group an isobutyl group, or a t-butyl group
  • an aryl group preferably an aryl group having 6 to 18 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms
  • a phenyl group or a biphenyl group is preferred.
  • a halogen atom preferably a fluorine atom
  • Group, alkoxy group, or aromatic heterocyclic group preferably an aromatic heterocyclic group having 2 to 12 carbon atoms, such as azole group, diazole group, triazole group, oxazole group, thiazole group, pyridyl group, furyl group
  • a thienyl group, an azole group, a diazole group, and a pyridyl group are preferable, and a benzoimidazolyl group is particularly preferable.
  • substituents may further have a substituent if possible, and examples of the further substituent include a substituent selected from the substituent group A, preferably an alkyl group, an aryl group. , Or an aromatic heterocyclic group, and specific examples and preferred ranges thereof are the same as the specific examples and preferred ranges of the substituent when R E3 represents a substituted aryl group.
  • R E3 represents an aryl group having a substituent
  • the substituents may be bonded to each other to form a ring, and examples of the ring include an aliphatic hydrocarbon ring, an aromatic ring, and an aromatic heterocycle.
  • An aromatic ring is preferable, and a benzene ring, a fluorene ring, an anthracene ring, a naphthyl ring, or a ring having a combination thereof, and the like, a fluorene ring, an anthracene ring, or a ring having a combination thereof are included. Is preferred.
  • the aromatic heterocyclic group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 2 carbon atoms. 12 aromatic heterocyclic groups.
  • the aromatic heterocyclic group include an azole group, a diazole group, a triazole group, an oxazole group, a thiazole group, a pyridyl group, a furyl group, and a thienyl group, and an azole group, a diazole group, and a pyridyl group are preferable.
  • Particularly preferred is a benzimidazolyl group.
  • examples of the substituent include a substituent selected from the substituent group A, preferably an alkyl group (preferably an alkyl group having 1 to 8 carbon atoms). More preferably an alkyl group having 1 to 6 carbon atoms, such as methyl group, ethyl group, n-propyl group, isopropyl group, isobutyl group, t-butyl group, n-butyl group, cyclopropyl group and the like.
  • an alkyl group preferably an alkyl group having 1 to 8 carbon atoms. More preferably an alkyl group having 1 to 6 carbon atoms, such as methyl group, ethyl group, n-propyl group, isopropyl group, isobutyl group, t-butyl group, n-butyl group, cyclopropyl group and the like.
  • an aryl group preferably an aryl group having 6 to 18 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms.
  • a phenyl group or a biphenyl group is preferable, and a phenyl group is more preferable.
  • a halogen A child preferably a fluorine atom
  • a cyano group preferably an alkoxy group
  • an aromatic heterocyclic group preferably an aromatic heterocyclic group having 2 to 12 carbon atoms, such as a pyridyl group, a furyl group, and a thienyl group.
  • a pyridyl group is more preferable.
  • an aryl group is particularly preferable.
  • R E3 is preferably a hydrogen atom or a substituted or unsubstituted aryl group, and more preferably a hydrogen atom from the viewpoint of obtaining an appropriate interaction between molecules.
  • R E4 represents a hydrogen atom, an aliphatic hydrocarbon, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group.
  • R E4 represents an aliphatic hydrocarbon group
  • the aliphatic hydrocarbon group preferably has 1 to 12 carbon atoms and is preferably an alkyl group (preferably having 1 to 10 carbon atoms, such as a methyl group, an ethyl group, isopropyl Group, t-butyl group, n-octyl group, n-decyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, neopentyl group, etc.), alkenyl group (preferably having 2 to 10 carbon atoms, for example, Vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), or alkynyl groups (preferably having 2 to 10 carbon atoms, such as propargyl, 3-pentynyl, etc.) are more preferred. More preferably, it is a methyl group, an ethyl group, an isopropyl group, a t-buty
  • the aryl group is preferably an aryl group having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms.
  • the aryl group include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a pyrenyl group, a triphenylenyl group, and the like.
  • a phenyl group, a naphthyl group, a biphenyl group, or An anthryl group is preferable, a phenyl group or a naphthyl group is more preferable, and a phenyl group is still more preferable.
  • the aryl group has a substituent, examples of the substituent are the same as those of the substituent that may be present when R E1 and R E2 are an aryl group.
  • the aromatic heterocyclic group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 2 carbon atoms. 12 aromatic heterocyclic groups.
  • the aromatic heterocyclic group include an azole group, a diazole group, a triazole group, an oxazole group, a thiazole group, a pyridyl group, a furyl group, and a thienyl group, and an azole group, a diazole group, and a pyridyl group are preferable.
  • a pyridyl group is more preferred.
  • R E4 is preferably a substituted or unsubstituted aryl group, and more preferably an unsubstituted aryl group, from the viewpoint of obtaining an appropriate interaction between molecules. Specific examples and preferred ranges in the case where R E4 is an aryl group are as described above.
  • the compound represented by the general formula (E-1) is preferably represented by the following general formula (E-2) or the following general formula (E-3).
  • R E1 and R E2 are each independently a hydrogen atom, an aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted group. However, R E1 and R E2 are not simultaneously hydrogen atoms.
  • R E3 represents a hydrogen atom, an aliphatic hydrocarbon, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group.
  • R E1 , R E2 , and R E3 are respectively synonymous with R E1 , R E2 , and R E3 in general formula (E-1), and are preferable.
  • the range is the same.
  • (e-1) to (e-10) are more preferred, (e-1) to (e-4), and (e-6) to (e-10) are more preferred, Particularly preferred are e-3), (e-4) and (e-8).
  • the compound represented by the general formula (E-1) can be synthesized by the method described in Japanese Patent No. 4308663. After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.
  • the compound represented by the general formula (E-1) is contained in at least one organic layer between the light emitting layer and the cathode, but its application is not limited. It may be further contained in any 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, a charge block It can be contained in any or a plurality of layers.
  • the organic layer between the light emitting layer containing the compound represented by the general formula (E-1) and the cathode is more preferably a charge blocking layer or an electron transporting layer, and further preferably an electron transporting layer. .
  • the organic electroluminescence device of the present invention has a pair of electrodes consisting of an anode and a cathode on a substrate, a light emitting layer between the electrodes, and an organic electroluminescence having at least one organic layer between the light emitting layer and the cathode.
  • An element comprising at least one compound represented by the general formula (1) in the light emitting layer and represented by the general formula (E-1) in at least one organic layer between the light emitting layer and the cathode. Containing at least one compound.
  • the light emitting layer is an organic layer, and further includes at least one organic layer between the light emitting layer and the cathode, but may further have an organic layer.
  • 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
  • the substrate used in the present invention is preferably a substrate that does not scatter or attenuate light emitted from the organic layer.
  • a substrate that does not scatter or attenuate light emitted from the organic layer In the case of an organic material, it is preferable that it is excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation, and workability.
  • the anode usually only needs to have a function as an electrode for supplying holes to the organic layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element, It can select suitably from well-known electrode materials.
  • the anode is usually provided as a transparent anode.
  • the cathode usually has a function as an electrode for injecting electrons into the organic layer, and there is no particular limitation on the shape, structure, size, etc., and it is known depending on the use and purpose of the light-emitting element.
  • the electrode material can be selected as appropriate.
  • Organic layer in the present invention will be described.
  • each organic layer is preferably formed by any one of a dry coating method such as a vapor deposition method and a sputtering method, a solution coating process such as a transfer method, a printing method, a spin coating method, and a bar coating method. Can be formed.
  • a dry coating method such as a vapor deposition method and a sputtering method
  • a solution coating process such as a transfer method, a printing method, a spin coating method, and a bar coating method.
  • a solution coating process such as a transfer method, a printing method, a spin coating method, and a bar coating method. It is preferable.
  • the light-emitting layer receives holes from the anode, the hole injection layer, or the hole transport layer when an electric field is applied, receives electrons from the cathode, the electron injection layer, or the electron transport layer, and recombines holes and electrons. It is a layer which has the function to provide and to emit light.
  • the substrate, anode, cathode, organic layer, and light emitting layer are described in detail in, for example, Japanese Patent Application Laid-Open No. 2008-270736 and Japanese Patent Application Laid-Open No. 2007-266458, and the matters described in these documents can be applied to the present invention.
  • the light emitting layer may include a material that does not have charge transporting properties and does not emit light.
  • Luminescent material As the light emitting material in the present invention, any of phosphorescent light emitting materials, fluorescent light emitting materials and the like can be used.
  • the light emitting layer in the present invention can contain two or more kinds of light emitting materials in order to improve the color purity and broaden the light emission wavelength region. At least one of the light emitting materials is preferably a phosphorescent light emitting material.
  • the light emitting material of the present invention further satisfies the relationship of 1.2 eV> ⁇ Ip> 0.2 eV and / or 1.2 eV> ⁇ Ea> 0.2 eV with the host material. It is preferable from the viewpoint.
  • ⁇ Ip means the difference in Ip value between the host material and the light emitting material
  • ⁇ Ea means the difference in Ea value between the host material and the light emitting material.
  • At least one of the light emitting materials is preferably a platinum complex material or an iridium complex material, and more preferably an iridium complex material.
  • the fluorescent light-emitting material and the phosphorescent light-emitting material are described in detail in paragraph numbers [0100] to [0164] of JP-A-2008-270736 and paragraph numbers [0088] to [0090] of JP-A-2007-266458, for example. The matters described in these publications can be applied to the present invention.
  • a phosphorescent material is preferable.
  • phosphorescent light-emitting materials that can be used in the present invention include US Pat. / 19373A2, JP-A No. 2001-247859, JP-A No. 2002-302671, JP-A No. 2002-117978, JP-A No. 2003-133074, JP-A No. 2002-1235076, JP-A No. 2003-123984, JP-A No. 2002-170684, EP No. 121157, JP-A No.
  • Examples of the light-emitting dopant include Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, and Tb complex. Gd complex, Dy complex, and Ce complex are mentioned.
  • an Ir complex, a Pt complex, or a Re complex among which an Ir complex or a Pt complex containing at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, and a metal-sulfur bond. Or Re complexes are preferred. Furthermore, from the viewpoints of luminous efficiency, driving durability, chromaticity and the like, an Ir complex and a Pt complex are particularly preferable, and an Ir complex is most preferable.
  • the platinum complex is preferably a platinum complex represented by the following general formula (C-1).
  • Q 1 , Q 2 , Q 3 and Q 4 each independently represent a ligand coordinated to Pt.
  • L 1 , L 2 and L 3 are each independently a single bond or a divalent linking group. Represents.
  • Q 1 , Q 2 , Q 3 and Q 4 each independently represent a ligand coordinated to Pt.
  • the bond between Q 1 , Q 2 , Q 3 and Q 4 and Pt may be any of a covalent bond, an ionic bond, a coordinate bond, and the like.
  • a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a phosphorus atom are preferable, and in Q ⁇ 1 >, Q ⁇ 2 >, Q ⁇ 3 > and Q ⁇ 4 >
  • a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a phosphorus atom are preferable, and in Q ⁇ 1 >, Q ⁇ 2 >, Q ⁇ 3 > and Q ⁇ 4 >
  • at least one is preferably a carbon atom, more preferably two are carbon atoms, particularly preferably two are carbon atoms and two are nitrogen atoms.
  • Q 1 , Q 2 , Q 3 and Q 4 bonded to Pt by a carbon atom may be an anionic ligand or a neutral ligand, and the anionic ligand is a vinyl ligand, Aromatic hydrocarbon ring ligand (eg benzene ligand, naphthalene ligand, anthracene ligand, phenanthrene ligand etc.), heterocyclic ligand (eg furan ligand, thiophene ligand, pyridine) Ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, thiazole ligand, oxazole ligand, pyrrole ligand, imidazole ligand, pyrazole ligand, triazole And a condensed ring containing them (for example, quinoline ligand, benzothiazole ligand, etc.).
  • a carbene ligand is mentioned as a neutral ligand.
  • Q 1 , Q 2 , Q 3 and Q 4 bonded to Pt with a nitrogen atom may be neutral ligands or anionic ligands, and as neutral ligands, nitrogen-containing aromatic hetero Ring ligand (pyridine ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, imidazole ligand, pyrazole ligand, triazole ligand, oxazole ligand, Examples include thiazole ligands and condensed rings containing them (for example, quinoline ligands, benzimidazole ligands), amine ligands, nitrile ligands, and imine ligands.
  • anionic ligands include amino ligands, imino ligands, nitrogen-containing aromatic heterocyclic ligands (pyrrole ligands, imidazole ligands, triazole ligands, and condensed rings containing them) (For example, indole ligand, benzimidazole ligand, etc.)).
  • Q 1 , Q 2 , Q 3 and Q 4 bonded to Pt with an oxygen atom may be neutral ligands or anionic ligands, and neutral ligands are ether ligands, Examples include ketone ligands, ester ligands, amide ligands, oxygen-containing heterocyclic ligands (furan ligands, oxazole ligands and condensed rings containing them (benzoxazole ligands, etc.)). It is done.
  • the anionic ligand include an alkoxy ligand, an aryloxy ligand, a heteroaryloxy ligand, an acyloxy ligand, a silyloxy ligand, and the like.
  • Q 1 , Q 2 , Q 3 and Q 4 bonded to Pt with a sulfur atom may be neutral ligands or anionic ligands, and neutral ligands include thioether ligands, Examples include thioketone ligands, thioester ligands, thioamide ligands, sulfur-containing heterocyclic ligands (thiophene ligands, thiazole ligands and condensed rings containing them (such as benzothiazole ligands)). It is done.
  • the anionic ligand include an alkyl mercapto ligand, an aryl mercapto ligand, and a heteroaryl mercapto ligand.
  • Q 1 , Q 2 , Q 3 and Q 4 bonded to Pt with a phosphorus atom may be neutral ligands or anionic ligands, and neutral ligands include phosphine ligands, Examples include phosphate ester ligands, phosphite ester ligands, and phosphorus-containing heterocyclic ligands (phosphinin ligands, etc.).
  • Anionic ligands include phosphino ligands and phosphinyl ligands.
  • phosphoryl ligands The groups represented by Q 1 , Q 2 , Q 3, and Q 4 may have a substituent, and those listed as the substituent group A can be appropriately applied as the substituent.
  • substituents may be connected to each other (when Q 3 and Q 4 are connected, a Pt complex of a cyclic tetradentate ligand is formed).
  • the group represented by Q 1 , Q 2 , Q 3 and Q 4 is preferably an aromatic hydrocarbon ring ligand bonded to Pt with a carbon atom, and an aromatic heterocyclic ligand bonded to Pt with a carbon atom.
  • L 1 , L 2 and L 3 represent a single bond or a divalent linking group.
  • the divalent linking group represented by L 1 , L 2 and L 3 include alkylene groups (methylene, ethylene, propylene, etc.), arylene groups (phenylene, naphthalenediyl), heteroarylene groups (pyridinediyl, thiophenediyl, etc.) ), Imino group (—NR—) (such as phenylimino group), oxy group (—O—), thio group (—S—), phosphinidene group (—PR—) (such as phenylphosphinidene group), silylene group (—SiRR′—) (dimethylsilylene group, diphenylsilylene group, etc.), or a combination thereof.
  • alkylene groups methylene, ethylene, propylene, etc.
  • arylene groups phenylene, naphthalenediyl
  • heteroarylene groups pyridined
  • R and R ′ each independently include an alkyl group, an aryl group, and the like. These linking groups may further have a substituent.
  • L 1 , L 2 and L 3 are preferably a single bond, an alkylene group, an arylene group, a heteroarylene group, an imino group, an oxy group, a thio group or a silylene group. More preferably a single bond, an alkylene group, an arylene group or an imino group, still more preferably a single bond, an alkylene group or an arylene group, still more preferably a single bond, a methylene group or a phenylene group, still more preferably.
  • Single bond, disubstituted methylene group more preferably single bond, dimethylmethylene group, diethylmethylene group, diisobutylmethylene group, dibenzylmethylene group, ethylmethylmethylene group, methylpropylmethylene group, isobutylmethylmethylene group, diphenyl Methylene group, methylphenylmethylene group, cyclohexanediyl group, A lopentanediyl group, a fluorenediyl group, and a fluoromethylmethylene group.
  • L 1 is particularly preferably a dimethylmethylene group, a diphenylmethylene group, or a cyclohexanediyl group, and most preferably a dimethylmethylene group.
  • L 2 and L 3 are most preferably a single bond.
  • platinum complexes represented by the general formula (C-1) a platinum complex represented by the following general formula (C-2) is more preferable.
  • L 21 represents a single bond or a divalent linking group.
  • a 21 and A 22 each independently represents a carbon atom or a nitrogen atom.
  • Z 21 and Z 22 each independently represent a nitrogen-containing aromatic heterocyclic ring.
  • Z 23 and Z 24 each independently represents a benzene ring or an aromatic heterocycle.
  • L 21 has the same meaning as L 1 in formula (C-1), and the preferred range is also the same.
  • a 21 and A 22 each independently represent a carbon atom or a nitrogen atom. Of A 21, A 22, Preferably, at least one is a carbon atom, it A 21, A 22 are both carbon atoms are preferred from the standpoint of emission quantum yield stability aspects and complexes of the complex .
  • Z 21 and Z 22 each independently represent a nitrogen-containing aromatic heterocycle.
  • the nitrogen-containing aromatic heterocycle represented by Z 21 and Z 22 include a pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole ring, Examples include thiadiazole rings.
  • the ring represented by Z 21 and Z 22 is preferably a pyridine ring, a pyrazine ring, an imidazole ring or a pyrazole ring, more preferably a pyridine ring.
  • the nitrogen-containing aromatic heterocycle represented by Z 21 and Z 22 may have a substituent, and the substituent group A is a substituent on a carbon atom, and the substituent on a nitrogen atom is The substituent group B can be applied.
  • the substituent on the carbon atom is preferably an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom.
  • the substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of shortening the wavelength, an electron donating group, a fluorine atom, and an aromatic ring group are preferable.
  • an alkyl group, a dialkylamino group, an alkoxy group, A fluorine atom, an aryl group, an aromatic heterocyclic group and the like are selected.
  • an electron withdrawing group is preferable, and for example, a cyano group, a perfluoroalkyl group, and the like are selected.
  • the substituent on the nitrogen atom is preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex.
  • the substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like.
  • Z 23 and Z 24 each independently represent a benzene ring or an aromatic heterocycle.
  • the nitrogen-containing aromatic heterocycle represented by Z 23 and Z 24 include pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadi Examples include an azole ring, a thiadiazole ring, a thiophene ring, and a furan ring.
  • the ring represented by Z 23 and Z 24 is preferably a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring, or a thiophene ring, More preferred are a benzene ring, a pyridine ring and a pyrazole ring, and still more preferred are a benzene ring and a pyridine ring.
  • the benzene ring and nitrogen-containing aromatic heterocycle represented by Z 23 and Z 24 may have a substituent.
  • the substituent group A is substituted on the nitrogen atom.
  • the substituent group B can be applied as the group.
  • Preferred substituents on carbon are alkyl groups, perfluoroalkyl groups, aryl groups, aromatic heterocyclic groups, dialkylamino groups, diarylamino groups, alkoxy groups, cyano groups, and fluorine atoms.
  • the substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of increasing the wavelength, an electron donating group and an aromatic ring group are preferable, for example, an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, An aromatic heterocyclic group or the like is selected.
  • an electron withdrawing group is preferable, and for example, a fluorine atom, a cyano group, a perfluoroalkyl group, and the like are selected.
  • the substituent on the nitrogen atom is preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex.
  • the substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like.
  • platinum complexes represented by the general formula (C-2) one of the more preferred embodiments is a platinum complex represented by the following general formula (C-4).
  • a 401 to A 414 each independently represents C—R or a nitrogen atom.
  • R represents a hydrogen atom or a substituent.
  • L 41 represents a single bond or a divalent linking group.
  • a 401 to A 414 each independently represents C—R or a nitrogen atom.
  • R represents a hydrogen atom or a substituent.
  • substituent represented by R those exemplified as the substituent group A can be applied.
  • a 401 to A 406 are preferably C—R, and Rs may be connected to each other to form a ring.
  • R in A 402 and A 405 is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom, or a cyano group.
  • R in A 401 , A 403 , A 404 and A 406 is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom or a cyano group, more preferably a hydrogen atom or an amino group.
  • L 41 has the same meaning as L 1 in formula (C-1), and the preferred range is also the same.
  • the number of N is preferably 0 to 2, and more preferably 0 to 1.
  • a 408 or A 412 is preferably a nitrogen atom, and both A 408 and A 412 are more preferably nitrogen atoms.
  • R in A 408 and A 412 is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom, A cyano group, more preferably a hydrogen atom, a perfluoroalkyl group, an alkyl group, an aryl group, a fluorine atom or a cyano group, and particularly preferably a hydrogen atom, a phenyl group, a perfluoroalkyl group or a cyano group.
  • R in A 407 , A 409 , A 411 and A 413 is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom or a cyano group, more preferably Of these, a hydrogen atom, a perfluoroalkyl group, a fluorine atom, and a cyano group are preferable, and a hydrogen atom, a phenyl group, and a fluorine atom are particularly preferable.
  • R in A 410 and A 414 is preferably a hydrogen atom or a fluorine atom, and more preferably a hydrogen atom.
  • platinum complexes represented by the general formula (C-2) one of the more preferred embodiments is a platinum complex represented by the following general formula (C-5).
  • a 501 to A 512 each independently represents C—R or a nitrogen atom, R represents a hydrogen atom or a substituent, and L 51 represents a single bond or a divalent linkage. Represents a group.
  • a 501 to A 506 and L 51 have the same meanings as A 401 to A 406 and L 41 in formula (C-4), and preferred ranges are also the same.
  • R represents a hydrogen atom or a substituent.
  • substituent represented by R those exemplified as the substituent group A can be applied.
  • R is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, an aromatic heterocyclic group, Dialkylamino group, diarylamino group, alkyloxy group, cyano group, fluorine atom, more preferably hydrogen atom, alkyl group, perfluoroalkyl group, aryl group, dialkylamino group, cyano group, fluorine atom, more preferably , Hydrogen atom, alkyl group, trifluoromethyl group, fluorine atom.
  • substituents may be linked to form a condensed ring structure.
  • At least one of A 507 , A 508 and A 509 and A 510 , A 511 and A 512 is preferably a nitrogen atom, and particularly preferably A 510 or A 507 is a nitrogen atom.
  • platinum complexes represented by the general formula (C-1) another more preferable embodiment is a platinum complex represented by the following general formula (C-6).
  • L 61 represents a single bond or a divalent linking group.
  • a 61 independently represents a carbon atom or a nitrogen atom.
  • Z 61 and Z 62 each independently represent a nitrogen-containing aromatic heterocyclic ring.
  • Z 63 independently represents a benzene ring or an aromatic heterocycle, and Y is an anionic acyclic ligand bonded to Pt.
  • L 61 has the same meaning as L 1 in formula (C-1), and the preferred range is also the same.
  • a 61 represents a carbon atom or a nitrogen atom. In view of the stability of the complex and the light emission quantum yield of the complex, A 61 is preferably a carbon atom.
  • Z 61 and Z 62 are synonymous with Z 21 and Z 22 in the general formula (C-2), respectively, and preferred ranges thereof are also the same.
  • Z 63 has the same meaning as Z 23 in formula (C-2), and the preferred range is also the same.
  • Y is an anionic acyclic ligand that binds to Pt.
  • An acyclic ligand is one in which atoms bonded to Pt do not form a ring in the form of a ligand.
  • a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom are preferable, a nitrogen atom and an oxygen atom are more preferable, and an oxygen atom is the most preferable.
  • a vinyl ligand is mentioned as Y couple
  • Examples of Y bonded to Pt with an oxygen atom include an alkoxy ligand, an aryloxy ligand, a heteroaryloxy ligand, an acyloxy ligand, a silyloxy ligand, a carboxyl ligand, a phosphate ligand, Examples thereof include sulfonic acid ligands.
  • Examples of Y bonded to Pt with a sulfur atom include alkyl mercapto ligands, aryl mercapto ligands, heteroaryl mercapto ligands, and thiocarboxylic acid ligands.
  • the ligand represented by Y may have a substituent, and those listed as the substituent group A can be appropriately applied as the substituent. Moreover, substituents may be connected to each other.
  • the ligand represented by Y is preferably a ligand bonded to Pt with an oxygen atom, more preferably an acyloxy ligand, an alkyloxy ligand, an aryloxy ligand, a heteroaryloxy ligand. , A silyloxy ligand, and more preferably an acyloxy ligand.
  • platinum complexes represented by the general formula (C-6) one of more preferred embodiments is a platinum complex represented by the following general formula (C-7).
  • a 701 to A 710 each independently represents C—R or a nitrogen atom, R represents a hydrogen atom or a substituent, L 71 represents a single bond or a divalent linking group, Y represents An anionic acyclic ligand that binds to Pt.
  • L 71 has the same meaning as L 61 in formula (C-6), and the preferred range is also the same.
  • a 701 to A 710 have the same meanings as A 401 to A 410 in formula (C-4), and preferred ranges are also the same.
  • Y has the same meaning as Y in formula (C-6), and the preferred range is also the same.
  • platinum complex represented by the general formula (C-1) include [0143] to [0152], [0157] to [0158], and [0162] to [0168] of JP-A-2005-310733.
  • Examples of the platinum complex compound represented by the general formula (C-1) include Journal of Organic Chemistry 53,786, (1988), G.S. R. Newkome et al. ), Page 789, method described in left column 53 to right column 7, line 790, method described in left column 18 to 38, method 790, method described in right column 19 to 30 and The combination, Chemische Berichte 113, 2749 (1980), H.C. Lexy et al.), Page 2752, lines 26 to 35, and the like.
  • a ligand or a dissociated product thereof and a metal compound are mixed with a solvent (for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, an amide solvent, a sulfone solvent,
  • a solvent for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, an amide solvent, a sulfone solvent
  • a base inorganic and organic bases such as sodium methoxide, t-butoxypotassium, triethylamine, potassium carbonate, etc.
  • a base inorganic and organic bases such as sodium methoxide, t-butoxypotassium, triethylamine, potassium carbonate, etc.
  • the content of the compound represented by formula (C-1) in the light emitting layer of the present invention is preferably 1 to 30% by mass, more preferably 3 to 25% by mass in the light emitting layer. More preferably, it is 20 mass%.
  • the iridium complex is preferably an iridium complex represented by the following general formula (T-1). [Compound represented by formula (T-1)] The compound represented by formula (T-1) will be described.
  • R T3 ′, R T3 , R T4 , R T5 and R T6 are each independently a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, Represents a fluorovinyl group, —CO 2 R T , —C (O) R T , —N (R T ) 2 , —NO 2 , —OR T , a halogen atom, an aryl group or a heteroaryl group; You may have.
  • E represents a carbon atom or a nitrogen atom.
  • Q is a 5-membered or 6-membered aromatic heterocyclic ring or condensed aromatic heterocyclic ring containing one or more nitrogen atoms.
  • the line connecting E and N is represented by a single line, but the bond type is not limited, and each may be a single bond or a double bond.
  • R T3 , R T4 , R T5 and R T6 may be any two adjacent to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or hetero It is aryl, and the condensed 4- to 7-membered ring may further have a substituent T.
  • the condensed 4- to 7-membered ring may be further condensed, and the further condensed ring may have a substituent T.
  • Each substituent T independently, a fluorine atom, -R ', - OR', - N (R ') 2, -SR', - C (O) R ', - C (O) OR', - C ( O) represents N (R ′) 2 , —CN, —NO 2 , —SO 2 , —SOR ′, —SO 2 R ′, or —SO 3 R ′, and each R ′ independently represents a hydrogen atom, alkyl Represents a group, a perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • (XY) represents a ligand.
  • m represents an integer of 1 to 3
  • n represents an integer of 0 to 2.
  • m + n is 3.
  • the alkyl group may have a substituent, and examples of the group that may be substituted include the substituent T described above.
  • the alkyl group represented by R T3 ′, R T3 , R T4 , R T5 and R T6 is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms. Groups such as a methyl group, an ethyl group, an i-propyl group, a cyclohexyl group, and a t-butyl group.
  • the cycloalkyl group may have a substituent, and examples of the group that may be substituted include the above-described substituent T.
  • the cycloalkyl group represented by R T3 ′, R T3 , R T4 , R T5 , and R T6 is preferably a cycloalkyl group having 4 to 7 ring members, and more preferably a cycloalkyl group having 5 to 6 total carbon atoms.
  • Examples of the alkyl group include a cyclopentyl group and a cyclohexyl group.
  • the alkenyl group represented by R T3 ′, R T3 , R T4 , R T5 and R T6 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms.
  • alkynyl group represented by R T3 ′, R T3 , R T4 , R T5 , R T6 is preferably a group having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms.
  • R T3 ′, R T3 , R T4 , R T5 , R T6 is preferably a group having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms.
  • ethynyl, propargyl, 1-propynyl, 3-pentynyl and the like are examples thereof.
  • Examples of the heteroalkyl group represented by R T3 ′, R T3 , R T4 , R T5 , and R T6 include groups in which at least one carbon of the alkyl group is replaced with O, NR T , or S.
  • Examples of the halogen atom represented by R T3 ′, R T3 , R T4 , R T5 , and R T6 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferable.
  • the aryl group represented by R T3 ′, R T3 , R T4 , R T5 and R T6 is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, more preferably 6 to 6 carbon atoms. 20 aryl groups.
  • the aryl group include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a pyrenyl group, a triphenylenyl group, and a tolyl group.
  • Group, biphenyl group, anthryl group or terphenyl group is preferable, and phenyl group, fluorenyl group and naphthyl group are more preferable.
  • the heteroaryl group represented by R T3 ′, R T3 , R T4 , R T5 , and R T6 is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or 6-membered substituent.
  • an unsubstituted heteroaryl group for example, pyridyl group, pyrazinyl group, pyridazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, cinnolinyl group, phthalazinyl group, quinoxalinyl group, pyrrolyl group, indolyl group , Furyl group, benzofuryl group, thienyl group, benzothienyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, triazolyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, isothiazolyl group, benzisothiazolyl group , Thiadiazolyl group, a Examples include a soxazolyl group, a benzisoxazo
  • R T3 ′, R T3 , R T4 , R T5 and R T6 are preferably a hydrogen atom, alkyl group, cyano group, trifluoromethyl group, perfluoroalkyl group, dialkylamino group, fluorine atom, aryl group, heteroaryl group And more preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a fluorine atom or an aryl group, and still more preferably a hydrogen atom, an alkyl group or an aryl group.
  • substituent T an alkyl group, an alkoxy group, a fluorine atom, a cyano group, and a dialkylamino group are preferable, and a hydrogen atom is more preferable.
  • R T3 , R T4 , R T5 and R T6 may be any two adjacent to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or hetero It is aryl, and the condensed 4- to 7-membered ring may further have a substituent T.
  • the definition and preferred range of the cycloalkyl, aryl and heteroaryl formed are the same as the cycloalkyl group, aryl group and heteroaryl group defined by R T3 ′, R T3 , R T4 , R T5 and R T6 .
  • Examples of the aromatic heterocycle represented by ring Q include a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyrazole ring, a pyrrole ring, an imidazole ring, a triazole ring, an oxazole ring, an oxadiazole ring, a thiazole ring, a thiadiazole ring, and the like.
  • a pyridine ring, a pyrazine ring and a pyrazole ring are preferable, and a pyridine ring and a pyrazole ring are more preferable.
  • Examples of the condensed aromatic heterocycle represented by ring Q include a quinoline ring, an isoquinoline ring, and a quinoxaline ring. Preferred are a quinoline ring and an isoquinoline ring, and more preferred is a quinoline ring.
  • M is preferably 1 to 3, and more preferably 2 or 3. That is, n is preferably 0 or 1. It is preferable that the kind of ligand in a complex is comprised from 1 or 2 types, More preferably, it is 1 type. When introducing a reactive group into the complex molecule, it is also preferred that the ligand consists of two types from the viewpoint of ease of synthesis.
  • the metal complex represented by the general formula (T-1) includes a ligand represented by the following general formula (T-1-A) in the general formula (T-1) or a tautomer thereof, and (X -Y) or a combination with a tautomer thereof, or all of the ligands of the metal complex are represented by the following general formula (T-1-A) Or a tautomer thereof.
  • R T3 ′, R T3 , R T4 , R T5 , R T6 , E and Q are the same as R T3 ′, R T3 , R in the general formula (T-1).
  • T4 , R T5 , R T6 , E and Q represents the coordination position to iridium.
  • a ligand used for forming a conventionally known metal complex
  • a ligand also referred to as a coordination compound
  • XY a ligand represented by (XY). You may do it.
  • ligands used in conventionally known metal complexes.
  • ligands eg, halogen ligands (preferably chlorine ligands), etc., published in 1987, published by Yersin, “Organometallic Chemistry-Fundamentals and Applications-”
  • Nitrogen heteroaryl ligands for example, bipyridyl, phenanthroline, etc.
  • diketone ligands for example, acetylacetone, etc.
  • the ligand represented by (XY) is preferably a diketone or a picolinic acid.
  • the derivative is most preferably acetylacetonate (acac) shown below from the viewpoint of obtaining stability of the complex and high luminous efficiency.
  • Rx, Ry and Rz each independently represents a hydrogen atom or a substituent.
  • substituents include a substituent selected from the substituent group A.
  • Rx and Rz are each independently an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, A fluorine atom and an optionally substituted phenyl group are most preferred, and a methyl group, an ethyl group, a trifluoromethyl group, a fluorine atom and a phenyl group are most preferred.
  • Ry is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, a fluorine atom, or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an optionally substituted phenyl group. And most preferably a hydrogen atom or a methyl group. Since these ligands are not considered to be sites where electrons are transported in the device or where electrons are concentrated by excitation, Rx, Ry, and Rz may be any chemically stable substituent, and the effects of the present invention can be achieved. Also has no effect. (I-1), (I-4) and (I-5) are preferred because complex synthesis is easy, and (I-1) is most preferred.
  • Ligands having these ligands can be synthesized in the same manner as in known synthesis examples by using corresponding ligand precursors. For example, in the same manner as described in International Publication No. 2009-073245, page 46, it can be synthesized by the following method using commercially available difluoroacetylacetone.
  • a monoanionic ligand represented by the general formula (I-15) can also be used as the ligand.
  • R T7 to R T10 in general formula (I-15) have the same meanings as R T3 to R T6 in general formula (T-1), and the preferred ranges are also the same.
  • R T7 ′ to R T10 ′ have the same meaning as R T3 ′, and the preferred range is also the same as R T3 ′. * Represents a coordination position to iridium.
  • the compound represented by the general formula (T-1) is preferably a compound represented by the following general formula (T-2).
  • R T3 ′ to R T6 ′ and R T3 to R T6 are each independently a hydrogen atom, alkyl group, alkenyl group, alkynyl group, —CN, perfluoroalkyl group, trifluorovinyl.
  • R T3 , R T4 , R T5 and R T6 may be any two adjacent to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring further has a substituent Z It may be.
  • a ring may be formed by linking with a linking group selected from —O—C (R T ) 2 —, —NR T —C (R T ) 2 —, and —N ⁇ CR T —.
  • R T each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group, or a heteroaryl group, and may further have a substituent T.
  • Each substituent T independently, a fluorine atom, -R ', - OR', - N (R ') 2, -SR', - C (O) R ', - C (O) OR', - C ( O) represents N (R ′) 2 , —CN, —NO 2 , —SO 2 , —SOR ′, —SO 2 R ′, or —SO 3 R ′, and each R ′ independently represents a hydrogen atom, alkyl Represents a group, a perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • (XY) represents a ligand.
  • m represents an integer of 1 to 3
  • n represents an integer of 0 to 2.
  • m + n is 3.
  • R T4 ′ is preferably a hydrogen atom, an alkyl group, an aryl group, or a fluorine atom, and more preferably a hydrogen atom.
  • R T5 ′ and R T6 ′ represent a hydrogen atom or are preferably bonded to each other to form a condensed 4- to 7-membered cyclic group, and the condensed 4- to 7-membered cyclic group includes cycloalkyl, cyclohetero More preferred is alkyl, aryl, or heteroaryl, and even more preferred is aryl.
  • substituent T in R T4 ′ to R T6 ′ an alkyl group, an alkoxy group, a fluorine atom, a cyano group, an alkylamino group, and a diarylamino group are preferable, and an alkyl group is more preferable.
  • One of preferable forms of the compound represented by the general formula (T-2) is R T3 ′, R T4 ′, R T5 ′, R T6 ′, R T3 , R T4 in the general formula (T-2). , R T5 and R T6 , any two adjacent groups are not bonded to each other to form a condensed ring.
  • T-2 One preferred form of the compound represented by the general formula (T-2) is a case represented by the following general formula (T-3).
  • R T3 ' ⁇ R T6' in the general formula (T3) R T3 ⁇ R T6 is, R T3 in the general formula (T-2) ' ⁇ R T6', have the same meaning as R T3 ⁇ R T6, preferably The range is the same.
  • R T7 to R T10 have the same meanings as R T3 to R T6 , and preferred ranges are also the same.
  • R T7 ′ to R T10 ′ have the same meanings as R T3 ′ to R T6 ′, and preferred ranges are also the same.
  • T-2 Another preferred embodiment of the compound represented by the general formula (T-2) is a compound represented by the following general formula (T-4).
  • R T3 ′ to R T6 ′, R T3 to R T6 , (XY), m and n in the general formula (T-4) are R T3 ′ to R T6 ′ and R in the general formula (T-2). It is synonymous with T3 to R T6 , (XY), m and n, and the preferred range is also the same.
  • R T3 ′ to R T6 ′ and R T3 to R T6 it is particularly preferred that 0 to 2 are alkyl groups or phenyl groups and the rest are all hydrogen atoms, and R T3 ′ to R T6 ′ and R T3 to R More preferably, one or two of T6 are alkyl groups and the rest are all hydrogen atoms.
  • T-2 Another preferred embodiment of the compound represented by the general formula (T-2) is a compound represented by the following general formula (T-5).
  • R T3 ′ to R T7 ′, R T3 to R T6 , (XY), m and n in the general formula (T-5) are R T3 ′ to R T6 ′ and R in the general formula (T-2).
  • T3 to R T6 have the same meanings as (XY), m and n, and the preferred ones are also the same.
  • T-1 Another preferred embodiment of the compound represented by the general formula (T-1) is a case represented by the following general formula (T-6).
  • R 1a to R 1i are the same as those in R T3 to R T6 in general formula (T-1). Further, it is particularly preferable that 0 to 2 of R 1a to R 1i are alkyl groups or aryl groups and the rest are all hydrogen atoms.
  • the definitions and preferred ranges of (XY), m, and n are the same as (XY), m, and n in formula (T-1).
  • T-1 Another preferred embodiment of the compound represented by the general formula (T-1) is a case represented by the following general formula (TC-1).
  • R T3 ′ to R T5 ′ and R T3 to R T6 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, or trifluorovinyl.
  • R T3 , R T4 , R T5 and R T6 may be combined with each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring further has a substituent T. It may be. R T3 ', R T4', and R T5 'are two arbitrary adjacent but may form a fused 4-7 membered ring bonded to each other, the condensed 4-7 membered ring may further have a substituent group T You may do it.
  • R T each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group, or a heteroaryl group, and may further have a substituent T.
  • Each substituent T independently, a fluorine atom, -R ', - OR', - N (R ') 2, -SR', - C (O) R ', - C (O) OR', - C ( O) represents N (R ′) 2 , —CN, —NO 2 , —SO 2 , —SOR ′, —SO 2 R ′, or —SO 3 R ′, and each R ′ independently represents a hydrogen atom, alkyl Represents a group, a perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • (XY) represents a ligand.
  • m represents an integer of 1 to 3
  • n represents an integer of 0 to 2.
  • m + n is 3.
  • R T3 ′, R T3 to R T6 , (XY), m and n in the general formula (TC-1) are preferably in the ranges R T3 ′, R T3 to R T6 in the general formula (T-1), This is the same as the preferred range of (XY), m and n.
  • R T4 ′ is preferably a hydrogen atom, an alkyl group, or an aryl group, and more preferably a hydrogen atom or an aryl group.
  • the aryl group is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and more preferably an aryl group having 6 to 20 carbon atoms.
  • aryl group examples include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a pyrenyl group, a triphenylenyl group, and a tolyl group.
  • Group, biphenyl group, triphenylenyl group, anthryl group or terphenyl group is preferable, and phenyl group, biphenyl group, naphthyl group and triphenylenyl group are more preferable.
  • R T5 ′ is preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an alkyl group.
  • the alkyl group preferably has 1 to 10 carbon atoms.
  • methyl group, ethyl group, isopropyl group, t-butyl group, n-octyl group, n-decyl group, n-hexadecyl group, cyclopropyl group, cyclopentyl Group, cyclohexyl group, neopentyl group and the like preferably methyl group, ethyl group, isopropyl group and t-butyl group, more preferably methyl group.
  • One of the preferable forms of the general formula (TC-1) is a case where any two adjacent R T4 , R T5 and R T6 are bonded to each other to form a condensed ring.
  • the ring is more preferably cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl.
  • R T4 and R T5 are preferably bonded to each other to form a heteroaryl ring.
  • m is preferably 3, and n is preferably 0.
  • the general formula (TC-1) is preferably the following general formula (TC-2).
  • R T3 ′ to R T5 ′, R T3 , R T6 , and R TC1 to R TC4 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cyano group, Represents a perfluoroalkyl group, a trifluorovinyl group, —CO 2 R T , —C (O) R T , —N (R T ) 2 , —NO 2 , —OR T , a halogen atom, an aryl group, or a heteroaryl group. Further, it may have a substituent T.
  • R T3 ', R T4', and R T5 ' are two arbitrary adjacent but may form a fused 4-7 membered ring bonded to each other, the condensed 4-7 membered ring may further have a substituent group T You may do it.
  • a ring may be formed by linking with a linking group selected from —O—C (R T ) 2 —, —NR T —C (R T ) 2 —, and —N ⁇ CR T —.
  • R T each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group, or a heteroaryl group, and may further have a substituent T.
  • Each substituent T independently, a fluorine atom, -R ', - OR', - N (R ') 2, -SR', - C (O) R ', - C (O) OR', - C ( O) represents N (R ′) 2 , —CN, —NO 2 , —SO 2 , —SOR ′, —SO 2 R ′, or —SO 3 R ′, and each R ′ independently represents a hydrogen atom, alkyl Represents a group, a perfluoroalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
  • W represents a carbon atom, an oxygen atom, or a sulfur atom to which a hydrogen atom or a substituent T is bonded.
  • (XY) represents a ligand.
  • m represents an integer of 1 to 3
  • n represents an integer of 0 to 2.
  • m + n is 3.
  • R T3 ′ to R T5 ′, R T3 and R T6 , (XY), m, and n preferably have R T3 ′ to R T5 in the general formula (TC-1).
  • R T3 and R T6 , (XY), m and n are the same as the preferred ranges.
  • the preferred range of R TC1 to R TC4 is the same as the preferred range of R T3 , preferably a hydrogen atom, an alkyl group, or an aryl group, and more preferably a hydrogen atom.
  • W is preferably a carbon atom having a substituent T
  • the substituent T is preferably an alkyl group
  • the alkyl group is preferably a methyl group, an ethyl group, an isopropyl group, or a t-butyl group. More preferably, it is a methyl group.
  • the general formula (TC-1) is also described in Japanese Patent Application Laid-Open No. 2008-147353.
  • the compounds exemplified as the compound represented by the general formula (T-1) can be synthesized by the method described in JP2009-99783A or various methods described in US Pat. No. 7,279,232. After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.
  • the compound represented by the general formula (T-1) is contained in the light emitting layer, but its use is not limited and may be further contained in any layer in the organic layer.
  • a compound represented by the following general formula (T-7) or a compound having a carbene as a ligand can also be preferably used.
  • R T11 to R T17 have the same meanings as R T3 to R T6 in the general formula (T-2), and preferred ranges thereof are also the same.
  • (XY), n, and m have the same meanings as (XY), n, and m in formula (T-2), and the preferred ranges are also the same.
  • the light emitting material in the light emitting layer is generally contained in the light emitting layer in an amount of 0.1% by mass to 50% by mass with respect to the total mass of the compound forming the light emitting layer. From the viewpoint of durability and external quantum efficiency.
  • the content is preferably 1% by mass to 50% by mass, and more preferably 2% by mass to 40% by mass.
  • the thickness of the light emitting layer is not particularly limited, but is usually preferably 2 nm to 500 nm, and more preferably 3 nm to 200 nm, and more preferably 5 nm to 100 nm from the viewpoint of external quantum efficiency. More preferably.
  • the light emitting layer in the element of the present invention may have a mixed layer of a host material and a light emitting material.
  • the light emitting material may be a fluorescent light emitting material or a phosphorescent light emitting material, and the dopant may be one kind or two or more kinds.
  • the host material is preferably a charge transport material.
  • the host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed.
  • the light emitting layer may include a material that does not have charge transporting properties and does not emit light.
  • the light emitting layer may be a single layer or a multilayer of two or more layers. In addition, each light emitting layer may emit light with different emission colors.
  • the host material used in the present invention is preferably a compound represented by the general formula (1).
  • the host material used in the present invention, in addition to the compound represented by the general formula (1), the following compounds may be contained.
  • the host material include an electron transport material and a hole transport material, and a charge transport material is preferable.
  • the host material may be one type or two or more types, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed.
  • pyrrole indole, carbazole (eg, CBP (4,4′-di (9-carbazolyl) biphenyl), 3,3′-di (9-carbazolyl) biphenyl)), azaindole, azacarbazole, triazole, oxazole, Oxadiazole, pyrazole, imidazole, thiophene, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound , Porphyrin compounds, polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiophene oligomers, conductive polymer oligomers such as polythiophene,
  • the host material triplet lowest excitation energy (T 1 energy) is preferably higher than the T 1 energy of the phosphorescent light emitting material in terms of color purity, light emission efficiency, and driving durability.
  • the content of the host compound in the present invention is not particularly limited, but from the viewpoint of light emission efficiency and driving voltage, it is 15% by mass to 95% by mass with respect to the total compound mass forming the light emitting layer. Preferably there is.
  • the charge transport layer is a layer in which charge transfer occurs when a voltage is applied to the organic electroluminescent element.
  • Specific examples include a hole injection layer, a hole transport layer, an electron block layer, a light emitting layer, a hole block layer, an electron transport layer, and an electron injection layer.
  • a hole injection layer, a hole transport layer, an electron blocking layer, or a light emitting layer is preferable. If the charge transport layer formed by the coating method is a hole injection layer, a hole transport layer, an electron blocking layer, or a light emitting layer, it is possible to manufacture an organic electroluminescent element with low cost and high efficiency.
  • the charge transport layer is more preferably a hole injection layer, a hole transport layer, or an electron block layer.
  • the hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side.
  • the hole injection layer and the hole transport layer are described in detail, for example, in JP-A-2008-270736 and JP-A-2007-266458, and the matters described in these publications can be applied to the present invention.
  • the thickness of the hole transport layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.
  • the thickness of the hole injection layer is preferably from 0.1 nm to 200 nm, more preferably from 0.5 nm to 100 nm, and even more preferably from 1 nm to 100 nm.
  • the following compounds can also be preferably used as the hole injection material.
  • the hole injection layer preferably contains an electron accepting dopant.
  • an electron-accepting dopant may be any organic material or inorganic material as long as it can extract electrons from the doped material and generate radical cations.
  • TCNQ tetracyanoquinodimethane
  • F 4 -TCNQ tetrafluorotetracyanoquinodimethane
  • molybdenum oxide and the like.
  • the electron-accepting dopant in the hole injection layer is preferably contained in an amount of 0.1% by mass to 50% by mass, and preferably 0.1% by mass to 40% by mass with respect to the total mass of the compound forming the hole injection layer. % Content is more preferable, and 0.5% by mass to 30% by mass is more preferable.
  • the electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side.
  • the electron injection material and the electron transport material used for these layers may be a low molecular compound or a high molecular compound.
  • the electron injection layer and the electron transport layer are described in detail, for example, in JP-A-2008-270736 and JP-A-2007-266458, and the matters described in these publications can be applied to the present invention.
  • the thickness of the electron transport layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.
  • the thickness of the electron injection layer is preferably from 0.1 nm to 200 nm, more preferably from 0.2 nm to 100 nm, and even more preferably from 0.5 nm to 50 nm.
  • the electron transport layer preferably contains a compound represented by the general formula (E-1).
  • the electron injection layer preferably contains an electron donating dopant.
  • the electron donating dopant may be any organic material or inorganic material as long as it can give electrons to the doped material and generate radical anions. For example, tetrathiafulvalene (TTF) , Tetrathianaphthacene (TTT), lithium, cesium and the like.
  • the electron donating dopant in the electron injection layer is preferably contained in an amount of 0.1% by mass to 50% by mass, and preferably 0.1% by mass to 40% by mass with respect to the total mass of the compound forming the electron injection layer. More preferably, the content is 0.5 to 30% by mass.
  • the device of the present invention has a small charge trap in the light emitting layer adjacent layer / light emitting layer interface on the cathode side and a small charge trap in the light emitting layer or the light emitting layer adjacent layer on the cathode side.
  • the driving voltage can be reduced without deteriorating efficiency, durability, various changes during high-intensity driving, etc. it can.
  • 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.
  • Examples of the organic compound constituting the hole blocking layer include the compound represented by the general formula (1) in the present invention, aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate ( Aluminum complexes such as Aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (abbreviated as BAlq)), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline ( And phenanthroline derivatives such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP)), triphenylene derivatives, and carbazole derivatives.
  • the triphenylene derivatives are described in, for example, International Publication No. 05/013388, International Publication No. 06/130598, and International Publication No. 09/021107.
  • the triphenylene derivative is preferably a compound represented by the following general formula (Tp-1).
  • R 12 to R 23 are each independently a hydrogen atom, an alkyl group or an alkyl group, a phenyl group optionally substituted with a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, Represents a fluorenyl group, a naphthyl group, or a triphenylenyl group, provided that R 12 to R 23 are not all hydrogen atoms.
  • Examples of the alkyl group represented by R 12 to R 23 include methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, n-octyl group, n-decyl group, n-hexadecyl group, and cyclopropyl.
  • R 12 to R 23 are preferably an alkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group (these are further an alkyl group, a phenyl group, a fluorenyl group). More preferably a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, which may be substituted with a group, a naphthyl group, or a triphenylenyl group.
  • 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.
  • a material contained in the protective layer any material may be used as long as it has a function of preventing materials that promote device deterioration such as moisture and oxygen from entering the device.
  • 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.
  • a sealing container the matters described in paragraph [0171] of JP-A-2008-270736 can be applied to the present invention.
  • a moisture absorbent or an inert liquid may be sealed in a space between the sealing container and the light emitting element.
  • a moisture absorber For example, barium oxide, sodium oxide, potassium oxide, calcium oxide, sodium sulfate, calcium sulfate, magnesium sulfate, phosphorus pentoxide, calcium chloride, magnesium chloride, copper chloride Cesium fluoride, niobium fluoride, calcium bromide, vanadium bromide, molecular sieve, zeolite, magnesium oxide and the like.
  • the inert liquid is not particularly limited, and examples thereof include paraffins, liquid paraffins, fluorine-based solvents such as perfluoroalkane, perfluoroamine, and perfluoroether, chlorine-based solvents, and silicone oils.
  • the organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode.
  • a direct current which may include an alternating current component as necessary
  • the driving method of the organic electroluminescence device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-290080, JP-A-7-134558, JP-A-8-234585, and JP-A-8-2441047.
  • the driving methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6,023,308 can be applied.
  • the external quantum efficiency of the organic electroluminescent element of the present invention is preferably 5% or more, more preferably 7% or more.
  • the value of the external quantum efficiency should be the maximum value of the external quantum efficiency when the device is driven at 20 ° C., or the value of the external quantum efficiency near 100 to 300 cd / m 2 when the device is driven at 20 ° C. Can do.
  • the internal quantum efficiency of the organic electroluminescence device of the present invention is preferably 30% or more, more preferably 50% or more, and further preferably 70% or more.
  • the internal quantum efficiency of the device is calculated by dividing the external quantum efficiency by the light extraction efficiency. In a normal organic EL element, the light extraction efficiency is about 20%.
  • the organic electroluminescent element of the present invention preferably has a maximum emission wavelength (maximum intensity wavelength of emission spectrum) of 350 nm to 700 nm, more preferably 350 nm to 600 nm, still more preferably 400 nm to 520 nm, particularly preferably. It is 400 nm or more and 465 nm or less.
  • 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 of FIG. 2 is comprised by the board
  • FIG. 1 is a cross-sectional view schematically showing an example of the light emitting device of the present invention.
  • the light-emitting device 20 of FIG. 2 is comprised by the board
  • the organic electroluminescent device 10 is configured by sequentially laminating an anode (first electrode) 3, an organic layer 11, and a cathode (second electrode) 9 on a substrate 2.
  • a protective layer 12 is laminated on the cathode 9, and a sealing container 16 is provided on the protective layer 12 with an adhesive layer 14 interposed therebetween.
  • a part of each electrode 3 and 9, a partition, an insulating layer, etc. are abbreviate
  • the adhesive layer 14 a photocurable adhesive such as an epoxy resin or a thermosetting adhesive can be used, and for example, a thermosetting adhesive sheet can also be used.
  • the use of the light-emitting device of the present invention is not particularly limited, and for example, it can be a display device such as a television, a personal computer, a mobile phone, and electronic paper in addition to a lighting device.
  • FIG. 3 is a cross-sectional view schematically showing an example of a lighting device according to an embodiment of the present invention.
  • the illumination device 40 according to the embodiment of the present invention includes the organic EL element 10 and the light scattering member 30 described above. More specifically, the lighting device 40 is configured such that the substrate 2 of the organic EL element 10 and the light scattering member 30 are in contact with each other.
  • the light scattering member 30 is not particularly limited as long as it can scatter light.
  • the light scattering member 30 is a member in which fine particles 32 are dispersed on a transparent substrate 31.
  • 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. In such an illuminating device 40, when light emitted from the organic electroluminescent element 10 enters the light incident surface 30A of the light scattering member 30, 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 compound represented by the general formula (1) used in the examples was synthesized with reference to International Publication No. 2004/074399 pamphlet and the like.
  • compound (1) can be synthesized by the method described in International Publication No. 2004/074399, page 52, line 22 to page 54, line 15.
  • the compound represented by the general formula (E-1) was synthesized with reference to Japanese Patent No. 4308663.
  • the organic materials used in this example were all purified by sublimation and analyzed by high performance liquid chromatography (Tosoh TSKgel ODS-100Z). Purity of 99.9 was obtained unless the absorption intensity area ratio was 254 nm. % Or more was used.
  • Example 1 ⁇ Production of organic electroluminescence device> A glass substrate (ITO film thickness is 100 nm) having an indium tin oxide (ITO) film with a thickness of 0.7 mm and a 2.5 cm square is placed in a cleaning container, subjected to ultrasonic cleaning in 2-propanol, and then UV-ozone for 30 minutes. Processed. The following layers were deposited on this glass substrate by a vacuum deposition method using a vacuum deposition apparatus (Small-ELVESS, manufactured by Tokki Co., Ltd.).
  • a vacuum deposition apparatus Small-ELVESS, manufactured by Tokki Co., Ltd.
  • a vapor deposition rate is 0.2 nm / sec unless there is particular notice.
  • the deposition rate was measured using a quartz resonator.
  • the pressure is 1 ⁇ 10 ⁇ 4 Pa or less.
  • the thickness of each layer below was measured using a quartz resonator.
  • HIL-1 purity 97%) was formed as a hole injection layer by vacuum deposition so as to have a thickness of 10 nm.
  • N, N′-dinaphthyl-N, N′-diphenyl- [1,1′-biphenyl] -4,4′-diamine is formed as a hole transport layer on the hole injection layer. It was formed by vacuum deposition so as to be 30 nm.
  • a film was formed by vacuum deposition.
  • a hole blocking layer was formed on the light emitting layer by vacuum deposition of HBL-A to a thickness of 10 nm.
  • e-4 was deposited as an electron transport layer on the hole blocking layer by vacuum deposition so as to have a thickness of 30 nm.
  • LiF was deposited as an electron injection layer on the electron transport layer by vacuum deposition so that the thickness was 1 nm.
  • a patterned mask (a mask having a light emitting area of 2 mm ⁇ 2 mm) was set as a cathode, and metal aluminum was vacuum deposited to a thickness of 100 nm to form a film.
  • the laminate produced as described above was placed in a glove box substituted with argon gas, and sealed with a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.).
  • the organic electroluminescent element of Example 1 was produced.
  • a device manufactured as described above was also manufactured.
  • Example 1 The organic electroluminescence device of Example 1 produced was evaluated for light emission efficiency, drive voltage, durability, and chromaticity as follows. Roll-off (decrease in efficiency during high-intensity drive) and electron transport layer thickness of about 10 nm The amount of change in chromaticity x was calculated.
  • Luminance 1,000 cd / m while maintaining the current density at second organic electroluminescent device of the continuous light emission is allowed time until the luminance 500 cd / m 2 to (h) was calculated as the durability.
  • the durability of Comparative Example 3 is set to 100
  • the durability of Comparative Example 11 is set to 100
  • the durability of Comparative Example 17 is set to 100
  • the durability of Comparative Example 24 was taken as 100, and is shown as a relative value.
  • a DC constant voltage was applied to the organic electroluminescence device of Example 1 to emit light using a source measure unit type 2400 manufactured by Toyo Technica.
  • the obtained emission spectrum was measured with an emission spectrum measurement system (ELS1500) manufactured by Shimadzu Corporation, and an x value was calculated from the obtained spectrum using a CIE color system.
  • the x value is a value at a current density of 10 mA / cm 2 .
  • Examples 2 to 31, and 33, and Comparative Examples 1 to 27 and 29 An element was prepared and evaluated in the same manner as in Example 1 except that the element configuration, the thickness of each layer, the compound used in each layer, and the content thereof were changed as shown in Tables 1 to 4 below.
  • the guest content of the light emitting layer is mass% with respect to the total mass of the light emitting layer.
  • Example 32 and Comparative Example 28 On the surface of the glass substrate having the washed indium tin oxide (ITO) film, an aqueous solution of poly (3,4-ethylenedioxythiophene) -poly (styrenesulfonic acid (PEDOT / PSS) (manufactured by Bayer) at 3000 to 4000 rpm.
  • the device of Example 32 was prepared and evaluated in the same manner as Example 22 except that the hole injection layer was formed by spin coating at a rotational speed of approximately, removing the film other than the light emitting region and then baking at 200 ° C.
  • a device of Comparative Example 28 was fabricated and evaluated in the same manner as in Example 32 except that the host material of the light emitting layer was changed to mCP.
  • Comparative Example 30 The device of Comparative Example 30 was prepared and evaluated in the same manner as in Example 1 except that the device configuration, the thickness of each layer, the compound used in each layer, and the content thereof were changed as shown in Table 5 below. The results are shown in Table 5 below.
  • the element of Comparative Example 30 is significantly inferior to the element of Example 1 in suppressing reduction in efficiency (roll-off) during high-intensity driving and in suppressing the dependence of chromaticity on the electron transport layer thickness. I understand.
  • a film of a layer including a compound having an electron transporting property between a light emitting layer and a cathode which is excellent in terms of luminous efficiency, driving voltage, and durability, has a small decrease in efficiency when driven at high luminance. It is possible to provide an organic electroluminescence device in which the emission chromaticity of the device is less dependent on the thickness.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un élément électroluminescent organique présentant d'excellentes efficacité lumineuse, tension de commande et durabilité, subissant rarement de détérioration d'efficacité pendant une commande de luminance élevée, dont la chromaticité luminescente dépend de l'épaisseur d'une couche disposée entre une couche d'émission de lumière et une cathode, et contenant un composé doté de propriétés de transport d'électrons. L'invention concerne en particulier un élément électroluminescent organique comprenant, sur un substrat, une paire d'électrodes composée d'une anode et d'une cathode et une couche d'émission de lumière disposée entre les électrodes, et comprenant également au moins une couche organique disposée entre la couche d'émission de lumière et la cathode, la couche d'émission de lumière contenant, par exemple, un composé (A-1), ladite couche organique au moins disposée entre la couche d'émission de lumière et la cathode contenant, par exemple, un composé (e-1).
PCT/JP2011/065719 2010-07-09 2011-07-08 Elément électroluminescent organique WO2012005364A1 (fr)

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JP2017208521A (ja) * 2016-05-18 2017-11-24 ▲いく▼▲雷▼光電科技股▲分▼有限公司 有機エレクトロルミネセントデバイス用化合物およびその化合物を用いた有機エレクトロルミネセントデバイス
CN111009616A (zh) * 2018-10-04 2020-04-14 三星显示有限公司 有机发光器件和包括该有机发光器件的显示装置
CN111048677A (zh) * 2015-12-22 2020-04-21 三星显示有限公司 有机发光装置
CN111233844A (zh) * 2018-11-29 2020-06-05 江苏三月光电科技有限公司 一种以咔唑为核心的有机化合物及其制备方法和其应用
US11617290B2 (en) 2015-12-22 2023-03-28 Samsung Display Co., Ltd. Organic light-emitting device
US11696496B2 (en) 2015-12-22 2023-07-04 Samsung Display Co., Ltd. Organic light-emitting device
US11937500B2 (en) 2015-12-22 2024-03-19 Samsung Display Co., Ltd. Organic light-emitting device

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KR101431645B1 (ko) * 2012-06-26 2014-08-20 롬엔드하스전자재료코리아유한회사 발광층 및 이를 포함하는 유기 전계 발광 소자
CN103730581B (zh) * 2012-10-15 2016-05-18 乐金显示有限公司 有机发光装置和使用其的有机发光显示装置
JP6433852B2 (ja) * 2015-05-28 2018-12-05 株式会社東芝 化合物、有機光電変換素子、及び固体撮像素子
CN105968041B (zh) * 2016-07-22 2019-03-22 吉林奥来德光电材料股份有限公司 联苯基双咔唑类化合物及其制备方法和由该化合物制成的有机发光器件
JP7456125B2 (ja) 2019-11-11 2024-03-27 東洋紡株式会社 パーフルオロアルキル基を有する含窒素複素環化合物及びその利用

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WO2008015949A1 (fr) * 2006-08-04 2008-02-07 Idemitsu Kosan Co., Ltd. Composant organique électroluminescent
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CN111048677A (zh) * 2015-12-22 2020-04-21 三星显示有限公司 有机发光装置
CN111048677B (zh) * 2015-12-22 2022-09-23 三星显示有限公司 有机发光装置
US11617290B2 (en) 2015-12-22 2023-03-28 Samsung Display Co., Ltd. Organic light-emitting device
US11696496B2 (en) 2015-12-22 2023-07-04 Samsung Display Co., Ltd. Organic light-emitting device
US11937500B2 (en) 2015-12-22 2024-03-19 Samsung Display Co., Ltd. Organic light-emitting device
JP2017208521A (ja) * 2016-05-18 2017-11-24 ▲いく▼▲雷▼光電科技股▲分▼有限公司 有機エレクトロルミネセントデバイス用化合物およびその化合物を用いた有機エレクトロルミネセントデバイス
CN111009616A (zh) * 2018-10-04 2020-04-14 三星显示有限公司 有机发光器件和包括该有机发光器件的显示装置
CN111233844A (zh) * 2018-11-29 2020-06-05 江苏三月光电科技有限公司 一种以咔唑为核心的有机化合物及其制备方法和其应用

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