WO2014181878A1 - Composé arylamine et son utilisation - Google Patents

Composé arylamine et son utilisation Download PDF

Info

Publication number
WO2014181878A1
WO2014181878A1 PCT/JP2014/062521 JP2014062521W WO2014181878A1 WO 2014181878 A1 WO2014181878 A1 WO 2014181878A1 JP 2014062521 W JP2014062521 W JP 2014062521W WO 2014181878 A1 WO2014181878 A1 WO 2014181878A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
groups
mmol
valent
Prior art date
Application number
PCT/JP2014/062521
Other languages
English (en)
Japanese (ja)
Inventor
松本　直樹
宏和 新屋
Original Assignee
東ソー株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 東ソー株式会社 filed Critical 東ソー株式会社
Publication of WO2014181878A1 publication Critical patent/WO2014181878A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems

Definitions

  • the present invention relates to a novel arylamine compound and an organic EL device having high emission efficiency and excellent durability using the same.
  • An organic EL element is a surface-emitting element in which an organic thin film is held between a pair of electrodes, and has features such as a thin and light weight, a high viewing angle, and a high-speed response, and is expected to be applied to various display elements. .
  • An organic EL element is an element that utilizes light emitted when holes injected from an anode and electrons injected from a cathode are recombined in a light emitting layer, and has a structure of a hole transport layer, a light emitting layer
  • a multi-layer laminate type in which an electron transport layer and the like are laminated is the mainstream.
  • the charge transport layer such as the hole transport layer and the electron transport layer does not emit light by itself, but facilitates the injection of charges into the light emitting layer, and the charge injected into the light emitting layer or the light emitting layer. It plays the role of confining the energy of the generated excitons. Therefore, the charge transport layer is very important for lowering the driving voltage and improving the light emission efficiency of the organic EL element.
  • an arylamine compound having an appropriate ionization potential and hole transport ability is used as the hole transport material.
  • an amine compound 4,4′-bis [N- (1-naphthyl) -N-phenylamino is used.
  • Biphenyl hereinafter abbreviated as NPD
  • NPD has a problem in device lifetime because the glass transition temperature is not sufficiently high. Further, the driving voltage and luminous efficiency of the device using NPD for the hole transport layer are not sufficient to satisfy the market requirements.
  • An object of the present invention is to provide an arylamine compound that is superior in device lifetime and luminous efficiency as compared with conventionally known arylamine compounds, and an organic EL device using the arylamine compound.
  • the present inventors have found that the benzo [b] phenanthreno [9,10-d] thiophene ring or the benzo [b] phenanthreno [9,10-d] furan ring has the following general formula.
  • the arylamine compound represented by (1) was found to be superior in device lifetime and light emission efficiency of the organic EL device as compared with conventional amine compounds, and the present invention was completed.
  • n represents an integer of 0 to 2.
  • M represents an (n + 1) -valent aromatic hydrocarbon group having 6 to 20 carbon atoms, or an (n + 1) -valent heteroaromatic group having 3 to 18 carbon atoms [these groups include a methyl group, an ethyl group, and a carbon number 3-18 linear, branched or cyclic alkyl group, methoxy group, ethoxy group, 3-18 linear, branched or cyclic alkoxy group, 1 to 3 halogenated alkyl group, carbon A halogenated alkoxy group having 1 to 3 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, It may have one or more substituents selected from the group consisting of a triarylsilyl group having 18 to 40 carbon atoms,
  • Ar 1 represents a substituent represented by the following general formula (2) or (3).
  • Ar 2 to Ar 4 are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms or a heteroaromatic group having 3 to 18 carbon atoms [these groups are a methyl group, an ethyl group, a carbon number 3 to 18 linear, branched, or cyclic alkyl groups, methoxy groups, ethoxy groups, linear, branched, or cyclic alkoxy groups having 3 to 18 carbon atoms, halogenated alkyl groups having 1 to 3 carbon atoms, 1 carbon atom Halogenated alkoxy group having 3 to 3, aryl group having 6 to 20 carbon atoms, aryloxy group having 6 to 18 carbon atoms, heteroaryl group having 3 to 18 carbon atoms, trialkylsilyl group having 3 to 18 carbon atoms, carbon number It may have one or more substituents selected from the group consisting of 18 to 40 triarylsilyl groups, cyano groups, hal
  • X represents an oxygen atom or a sulfur atom.
  • L is a single bond, a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a divalent heteroaromatic group having 3 to 18 carbon atoms. [These groups include a methyl group, an ethyl group, and 3 to 18 carbon atoms.
  • R 1 to R 3 each independently represents an aromatic hydrocarbon group having 6 to 20 carbon atoms or a heteroaromatic group having 3 to 18 carbon atoms [these groups are a methyl group, an ethyl group, 18 linear, branched, or cyclic alkyl groups, methoxy groups, ethoxy groups, linear, branched, or cyclic alkoxy groups having 3 to 18 carbon atoms, halogenated alkyl groups having 1 to 3 carbon atoms, 1 carbon atom Halogenated alkoxy group having 3 to 3, aryl group having 6 to 20 carbon atoms, aryloxy group having 6 to 18 carbon atoms, heteroaryl group having 3 to 18 carbon atoms, trialkylsilyl group having 3 to 18 carbon atoms, carbon number It may have one or more substituents selected from the group consisting of 18 to 40 triarylsilyl groups, cyano groups, halogen atoms, and deuterium atoms.
  • the present invention resides in an arylamine compound represented by the above general formula (1) and its use, particularly an organic EL device using the arylamine compound. Moreover, this invention contains the halogen compound which is an intermediate body for synthesize
  • the organic EL device using the arylamine compound of the present invention exhibits a remarkable effect that it has a high luminous efficiency (current efficiency), a low driving voltage, and an excellent device lifetime as compared with conventional materials.
  • the characteristics of the organic EL device of the present invention are as follows.
  • the arylamine compound of the present invention represented by the formula (1) the substituent represented by the formula (2) or the general formula (3) is bonded via —L—. This is thought to be due to the strong influence of the position and number of amino groups to be bound. That is, the triarylamine structure of the arylamine compound of the present invention represented by the formula (1) has a remarkable effect as a hole transport material as compared with a conventionally known triarylamine structure.
  • n represents an integer of 0-2.
  • n is preferably 0 or 1 from the viewpoint of excellent hole transport properties.
  • M is an (n + 1) -valent aromatic hydrocarbon group having 6 to 20 carbon atoms or an (n + 1) -valent heteroaromatic group having 3 to 18 carbon atoms.
  • These groups include a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms.
  • halogenated alkyl group having 1 to 3 carbon atoms halogenated alkoxy group having 1 to 3 carbon atoms
  • aryl group having 6 to 12 carbon atoms aryloxy group having 6 to 18 carbon atoms
  • heterogeneous group having 3 to 18 carbon atoms It has at least one substituent selected from the group consisting of an aryl group, a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom.
  • the (n + 1) -valent aromatic hydrocarbon group having 6 to 20 carbon atoms represents a substituent consisting only of a hydrogen atom and a carbon atom constituting an aromatic ring.
  • the (n + 1) -valent heteroaromatic group having 3 to 18 carbon atoms represents a hydrogen atom and a substituent composed of only carbon atoms and heteroatoms constituting an aromatic ring.
  • the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms in M is not particularly limited, and examples thereof include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, and a benzofluorenyl group. , Dibenzofluorenyl group, phenanthryl group, fluoranthenyl group, anthryl group, chrysenyl group, pyrenyl group, triphenylene group, perylenyl group and the like.
  • the monovalent heteroaromatic group having 3 to 18 carbon atoms in M is not particularly limited, and examples thereof include heterocycles having 3 to 18 carbon atoms containing at least one oxygen atom, nitrogen atom, or sulfur atom.
  • Aromatic groups can be mentioned.
  • the divalent aromatic hydrocarbon group having 6 to 20 carbon atoms in M is not particularly limited, but includes phenylene group, biphenylene group, terphenylene group, naphthylene group, phenylnaphthalene-diyl group, binaphthylene group, fluorene.
  • -Diyl group benzofluorene-diyl group, dibenzofluorene-diyl group, phenanthrene-diyl group, fluoranthene-diyl group, anthracene-diyl group, chrysene-diyl group, pyrene-diyl group, triphenylene-diyl group, perylene-diyl group Etc.
  • the divalent heteroaromatic group having 3 to 18 carbon atoms in M is not particularly limited.
  • the divalent heteroaromatic group having 3 to 18 carbon atoms contains at least one oxygen atom, nitrogen atom, or sulfur atom.
  • Valent heteroaromatic groups are not particularly limited.
  • the trivalent aromatic hydrocarbon group having 6 to 20 carbon atoms in M is not particularly limited, but benzene-triyl group, biphenyl-triyl group, terphenyl-triyl group, naphthalene-triyl group, binaphthalene- Triyl group, fluorene-triyl group, benzofluorene-triyl group, dibenzofluorene-triyl group, phenanthrene-triyl group, fluoranthene-triyl group, anthracene-triyl group, chrysene-triyl group, pyrene-triyl group, triphenylene-triyl group, And perylene-triyl group.
  • the trivalent heteroaromatic group having 3 to 18 carbon atoms in M is not particularly limited.
  • the trivalent heteroaromatic group having 3 to 18 carbon atoms contains at least one oxygen atom, nitrogen atom, or sulfur atom.
  • Valent heteroaromatic groups are not particularly limited.
  • the definition of the substituent that may be possessed by the (n + 1) -valent aromatic hydrocarbon group having 6 to 20 carbon atoms and the (n + 1) -valent heteroaromatic group having 3 to 18 carbon atoms in M is shown below. .
  • the linear, branched or cyclic alkyl group having 3 to 18 carbon atoms is not particularly limited, and examples thereof include a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, and a pentyl group. Hexyl group, heptyl group, octyl group, stearyl group, cyclopropyl group, cyclohexyl group and the like.
  • the linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms is not particularly limited, and examples thereof include a propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, and a tert-butoxy group. , A pentyloxy group, a hexyloxy group, a stearyloxy group, and the like.
  • the halogenated alkyl group having 1 to 3 carbon atoms is not particularly limited, and examples thereof include a trifluoromethyl group, a trichloromethyl group, and a 2-fluoroethyl group.
  • the halogenated alkoxy group having 1 to 3 carbon atoms is not particularly limited, and examples thereof include a trifluoromethoxy group, a trichloromethoxy group, and a 2-fluoroethoxy group.
  • the aryl group having 6 to 12 carbon atoms is not particularly limited, and examples thereof include a phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-methoxyphenyl group, 3- Methoxyphenyl group, 4-methoxyphenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, 3,4-dimethylphenyl group, 2,6-dimethylphenyl group, biphenyl group, naphthyl group, Examples thereof include 1-methylnaphthyl group, 2-methylnaphthyl group, 1-methoxynaphthyl group, 2-methoxynaphthyl group and the like.
  • aryl group having 6 to 12 carbon atoms is an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent (eg, a methyl group, a methoxy group, a phenyl group, etc.). be able to.
  • the aryloxy group having 6 to 18 carbon atoms is not particularly limited, and examples thereof include phenoxy group, 2-methylphenoxy group, 3-methylphenoxy group, 4-methylphenoxy group, 2-methoxyphenoxy group, 3 -Methoxyphenoxy group, 4-methoxyphenoxy group, 2-cyanophenoxy group, 3-cyanophenoxy group, 4-cyanophenoxy group, 3,4-dimethylphenoxy group, 2,6-dimethylphenoxy group, biphenyloxy group, naphthyl An oxy group etc. are mentioned.
  • aryloxy group having 6 to 18 carbon atoms may have a substituent (for example, a methyl group, a methoxy group, a phenyl group, etc.), and an aromatic hydrocarbon oxy group having 6 to 18 carbon atoms in total. It can be said that.
  • the heteroaryl group having 3 to 18 carbon atoms is not particularly limited, and examples thereof include pyrrolyl group, 1-methylpyrrolyl group, 1-phenylpyrrolyl group, thienyl group, 2-methylthienyl group, and 2-cyanothienyl group.
  • the heteroaryl group having 3 to 18 carbon atoms is a heteroaromatic group having 3 to 18 carbon atoms which may have a substituent (for example, a methyl group, a methoxy group, a phenyl group, etc.). , And can be.
  • the trialkylsilyl group having 3 to 18 carbon atoms is not particularly limited, and examples thereof include a trimethylsilyl group, a triethylsilyl group, and a tributylsilyl group.
  • the triarylsilyl group having 18 to 40 carbon atoms is not particularly limited, and examples thereof include triphenylsilyl group, tri (2-methylphenyl) silyl group, tri (3-methylphenyl) silyl group, tri ( 4-methylphenyl) silyl group, tri (4-biphenylyl) silyl group and the like.
  • Examples of the halogen atom include fluorine, chlorine, bromine, or iodine.
  • monovalent M examples include phenyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4 -N-propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec-butylphenyl group, 4-tert-butylphenyl group, 4 -N-pentylphenyl group, 4-isopentylphenyl group, 4-neopentylphenyl group, 4-n-hexylphenyl group, 4-n-octylphenyl group, 4-n-decylphenyl group, 4-n-dodecyl Phenyl group, 4-cyclopentylphenyl group, 4-cyclohexylphenyl group,
  • phenyl group for monovalent M, from the point of excellent hole transport properties, phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthryl group, triphenylene group, fluorenyl group, benzofluorenyl group, dibenzothienyl group, dibenzofuran Nyl group, or carbazolyl group (these groups are a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a straight chain having 3 to 18 carbon atoms, Branched or cyclic alkoxy group, halogenated alkyl group having 1 to 3 carbon atoms, aryl group having 6 to 12 carbon atoms, aryloxy group having 6 to 18 carbon atoms, heteroaryl group having 3 to 18 carbon atoms, carbon number Selected from the group consisting of a trialkylsilyl
  • the substituents may be 1 or more.) It is preferably.
  • phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthryl group, triphenylene group, fluorenyl group, dibenzothienyl group, dibenzofuranyl group, or carbazolyl group (these groups are methyl group, ethyl group, C3-C18 linear, branched, or cyclic alkyl group, methoxy group, ethoxy group, C3-C18 linear, branched, or cyclic alkoxy group, C1-C3 halogenated alkyl group
  • An aryl group having 6 to 12 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, and a triarylsilyl group having 18 to 40 carbon atoms More preferably one or more
  • a phenyl group (which may have a methyl group, a cyano group, or a fluoro group), a naphthylphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, 9-dimethylfluorenyl group, dibenzothienyl group, dibenzofuranyl group, 9-phenylcarbazolyl group, carbazolylphenyl group, 9-phenylcarbazolylphenyl group, dibenzothienylphenyl group, or dibenzofuranylphenyl It is preferably a group.
  • phenyl group 4-methylphenyl group, 3-methylphenyl group, 4-cyanophenyl group, 3-cyanophenyl group, 4-fluorophenyl group, 3-fluorophenyl group, 4- (4- Dibenzothienyl) phenyl group, 4- (4-dibenzofuranyl) phenyl group, 4- (9-carbazolyl) phenyl group, 4- (9-phenylcarbazol-3-yl) phenyl group, 4-biphenyl group, 3- Biphenyl group, p-terphenyl group, m-terphenyl group, 1-naphthyl group, 2-naphthyl group, 4- (1-naphthyl) phenyl group, 3- (1-naphthyl) phenyl group, 9,9-dimethyl A -2-fluorenyl group, a 9-phenylcarbazol-3-yl group, a 2-dibenzo
  • divalent M examples include 1,4-phenylene group, 2-methyl-1,4-phenylene group, 2-ethyl-1,4-phenylene group, 2-n-propyl-1,4-phenylene.
  • phenylene group For divalent M, phenylene group, biphenylene group, terphenylene group, naphthylene group, anthracene-diyl group, or fluorene-diyl group (these groups are methyl, ethyl, Groups, linear, branched or cyclic alkyl groups having 3 to 18 carbon atoms, methoxy groups, ethoxy groups, linear, branched or cyclic alkoxy groups having 3 to 18 carbon atoms, halogenated groups having 1 to 3 carbon atoms An alkyl group, a halogenated alkoxy group having 1 to 3 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, and a triaryl having 3 to 18 carbon atoms.
  • It may have one or more substituents selected from the group consisting of alkylsilyl groups, triarylsilyl groups having 18 to 40 carbon atoms, cyano groups, halogen atoms, and deuterium atoms. .) It is preferred that.
  • 1,4-phenylene group, 1,3-phenylene group, 4,4′-biphenylene group, 3,3′-biphenylene group, 3,4′-biphenylene group, 4,4 ′′- p-terphenylene group, 4,4 ′′ -m-terphenylene group, 2,6-naphthylene group, or fluorene-2,7-diyl group (these groups are a methyl group, an ethyl group, 18 linear, branched, or cyclic alkyl groups, methoxy groups, ethoxy groups, linear, branched, or cyclic alkoxy groups having 3 to 18 carbon atoms, halogenated alkyl groups having 1 to 3 carbon atoms, 1 carbon atom Halogenated alkoxy group having 3 to 3, aryl group having 6 to 12 carbon atoms, aryloxy group having 6 to 18 carbon atoms, heteroaryl group having 3 to 18 carbon atoms, trialkylsilyl group
  • trivalent M examples include benzene-1,3,5-triyl group, 2-methylbenzene-1,3,5-triyl group, and 2,4-dimethylbenzene-1,3,5-triyl group.
  • Trivalent M is a benzene-triyl group (this group is a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, methoxy group) because it has excellent hole transport properties.
  • one or more substituents selected from the group consisting of deuterium atoms may be present.
  • a benzene-1,3,5-triyl group is preferred.
  • (n + 1) -valent phenyl group (n + 1) -valent biphenyl group, (n + 1) -valent terphenyl group, (n + 1) -valent naphthyl group, (n + 1) -valent phenanthryl group, (n + 1) Valent fluorenyl group, (n + 1) valent triphenylene group, (n + 1) valent dibenzothienyl group, (n + 1) valent dibenzofuranyl group, or (n + 1) valent carbazolyl group (these groups are methyl, cyano It may have one or more substituents selected from the group consisting of a group, a fluoro group, a phenyl group, a dibenzothienyl group, a dibenzofuranyl group, a carbazolyl group, and a naphthyl group.
  • an (n + 1) -valent phenyl group (which may have a methyl group, a cyano group, or a fluoro group), an (n + 1) -valent naphthylphenyl group, an (n + 1) -valent biphenyl group, (N + 1) -valent terphenyl group, (n + 1) -valent naphthyl group, (n + 1) -valent phenanthryl group, (n + 1) -valent 9,9-dimethylfluorenyl group, (n + 1) -valent dibenzothienyl group, n + 1) -valent dibenzofuranyl group, (n + 1) -valent 9-phenylcarbazolyl group, (n + 1) -valent carbazolylphenyl group, (n + 1) -valent 9-phenylcarbazolylphenyl group, (n + 1) It is more preferably a divalent dibenzothienylphenyl group or a (n + 1) -valent
  • Ar 1 represents a substituent represented by the following general formula (2) or (3).
  • Ar 2 to Ar 4 are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms or a heteroaromatic group having 3 to 18 carbon atoms.
  • Groups (these groups are a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic group having 3 to 18 carbon atoms).
  • the aromatic hydrocarbon group having 6 to 20 carbon atoms in Ar 2 to Ar 4 is not particularly limited, but is the same as the aromatic hydrocarbon group having 6 to 20 carbon atoms shown for the monovalent M described above. Groups.
  • the heteroaromatic group having 3 to 18 carbon atoms in Ar 2 to Ar 4 is not particularly limited, but the same group as the heteroaromatic group having 3 to 18 carbon atoms shown in the monovalent M may be used. Can be mentioned.
  • the following substituents that the aromatic hydrocarbon group having 6 to 20 carbon atoms and the heteroaromatic group having 3 to 18 carbon atoms in Ar 2 to Ar 4 may have are the substituents shown in the above M, The same substituents can be exemplified.
  • the aryl group having 6 to 20 carbon atoms is not particularly limited, and examples thereof include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, 3,4-dimethylphenyl group, 2,6-dimethylphenyl group, biphenyl group, naphthyl Group, 1-methylnaphthyl group, 2-methylnaphthyl group, 1-methoxynaphthyl group, 2-methoxynaphthyl group, 9,9-dimethylfluorenyl group and the like.
  • Ar 2 to Ar 4 are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a triphenylene group, a benzofluorenyl group, because they are excellent in hole transport properties.
  • Dibenzothienyl group, dibenzofuranyl group, carbazolyl group (these groups are methyl group, ethyl group, linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, methoxy group, ethoxy group, 3 to 3 carbon atoms) 18 linear, branched, or cyclic alkoxy groups, halogenated alkyl groups having 1 to 3 carbon atoms, aryl groups having 6 to 20 carbon atoms, aryloxy groups having 6 to 18 carbon atoms, heterocycles having 3 to 18 carbon atoms An aryl group, a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom.
  • a substituent selected from the group may have one or more.),
  • a phenyl group (which may have a methyl group, a cyano group, or a fluoro group), a naphthylphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, 9-dimethylfluorenyl group, dibenzothienyl group, dibenzofuranyl group, 9-phenylcarbazolyl group, carbazolylphenyl group, 9-phenylcarbazolylphenyl group, dibenzothienylphenyl group, or dibenzofuranylphenyl It is more preferable that it is a group and the substituent represented by the said General formula (2) or (3).
  • phenyl group 4-methylphenyl group, 3-methylphenyl group, 4-cyanophenyl group, 3-cyanophenyl group, 4-fluorophenyl group, 3-fluorophenyl group, 4- (4-dibenzo group) Thienyl) phenyl group, 4- (4-dibenzofuranyl) phenyl group, 4- (9-carbazolyl) phenyl group, 4- (9-phenylcarbazol-3-yl) phenyl group, 4-biphenyl group, 3-biphenyl Group, p-terphenyl group, m-terphenyl group, 1-naphthyl group, 2-naphthyl group, 4- (1-naphthyl) phenyl group, 3- (1-naphthyl) phenyl group, 9,9-dimethyl- 2-fluorenyl group, 9-phenylcarbazol-3-yl group, 2-dibenzothieny
  • the compound represented by the general formula (1) of the present invention is characterized in that at least one substituent represented by the general formula (2) or (3) is present.
  • the operability of the compound (ease of operation such as synthesis, purification, film formation, etc.) 1 to 3 is preferable, and 1 or 2 is more preferable.
  • the substituent represented by the general formula (2) or (3) may be a substituent represented by any of the following general formulas (4) to (7) in consideration of the planarity of the molecule. preferable.
  • X, L, and R 1 to R 3 are the same as defined in the general formula (2) or (3).
  • X represents an oxygen atom or a sulfur atom.
  • L is a single bond, a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a divalent heteroaromatic group having 3 to 18 carbon atoms.
  • Groups (these groups are a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic group having 3 to 18 carbon atoms).
  • the divalent aromatic hydrocarbon group having 6 to 20 carbon atoms in L is not particularly limited, but the same group as the aromatic hydrocarbon group having 6 to 20 carbon atoms shown in the above divalent M may be used. Can be mentioned.
  • the divalent heteroaromatic group having 3 to 18 carbon atoms in L is not particularly limited, and examples thereof include the same groups as the heteroaromatic group having 3 to 18 carbon atoms shown in the above divalent M. .
  • L is a single bond or a phenylene group (methyl group, ethyl group, straight chain having 3 to 18 carbon atoms) from the viewpoint of excellent hole transport properties.
  • the general formulas (2) to (7) are preferably the following general formulas (2 ′) to (7 ′) from the viewpoint of excellent hole transport properties.
  • R 1 to R 3 are each independently an aromatic group having 6 to 20 carbon atoms.
  • a hydrocarbon group or a heteroaromatic group having 3 to 18 carbon atoms (these groups include a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, Straight, branched or cyclic alkoxy group having 3 to 18 carbon atoms, halogenated alkyl group having 1 to 3 carbon atoms, halogenated alkoxy group having 1 to 3 carbon atoms, aryl group having 6 to 20 carbon atoms, carbon number 6-18 aryloxy groups, C3-C18 heteroaryl groups, C3-C18 trialkylsilyl groups, C18-C40 triarylsilyl groups, cyano groups, halogen atoms, and deuter
  • halogenated alkyl group having 1 to 3 carbon atoms aryloxy group having 6 to 18 carbon atoms, trialkylsilyl group having 3 to 18 carbon atoms, triarylsilyl group having 18 to 40 carbon atoms, cyano group, halogen atom Represents a deuterium atom or a hydrogen atom.
  • the aromatic hydrocarbon group having 6 to 20 carbon atoms in R 1 to R 3 is not particularly limited, but is the same as the aromatic hydrocarbon group having 6 to 20 carbon atoms shown for the monovalent M described above.
  • the heteroaromatic group having 3 to 18 carbon atoms in R 1 to R 3 is not particularly limited, but the same group as the heteroaromatic group having 3 to 18 carbon atoms shown in the monovalent M may be used. Can be mentioned.
  • Halogenated alkoxy groups, C6-C20 aryl groups, C6-C18 aryloxy groups, C3-C18 heteroaryl groups, C3-C18 trialkylsilyl groups, C18-C18 Forty triarylsilyl groups and halogen atoms can be exemplified as the substituent.
  • R 1 to R 3 are each a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group from the viewpoint of excellent hole transport properties.
  • These groups include a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms.
  • halogenated alkyl group having 1 to 3 carbon atoms halogenated alkoxy group having 1 to 3 carbon atoms
  • aryl group having 6 to 20 carbon atoms aryloxy group having 6 to 18 carbon atoms
  • heterogeneous group having 3 to 18 carbon atoms It has at least one substituent selected from the group consisting of an aryl group, a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom.
  • a phenyl group, a methyl group, a methoxy group, a cyano group, a deuterium atom, or a hydrogen atom is more preferable. Further, among these, a methyl group or a hydrogen atom is particularly preferable.
  • the arylamine compound represented by the general formula (1) can be synthesized by a known method (Tetrahedron Letters, 1998, 39, 2367).
  • the halogen compound represented by the general formula (11) can be used as a raw material and synthesized by amination using a copper catalyst or a palladium catalyst in the presence of a base. .
  • Ar 1 to Ar 4 , M and n are as defined above, and Y represents iodine, bromine, chlorine or fluorine.
  • Examples of the palladium catalyst that can be used in the above reaction include palladium chloride (II), palladium bromide (II), palladium acetate (II), palladium acetylacetonate (II), dichlorobis (benzonitrile) palladium (II), Dichlorobis (acetonitrile) palladium (II), dichlorobis (triphenylphosphine) palladium (II), dichlorotetraamminepalladium (II), dichloro (cycloocta-1,5-diene) palladium (II), palladium trifluoroacetate (II), etc.
  • Divalent palladium compound tris (dibenzylideneacetone) dipalladium (0), tris (dibenzylideneacetone) dipalladium chloroform complex (0), tetrakis (triphenylphosphine) palladium (0) 0-valent palladium compound and the like.
  • fixed palladium catalysts such as a fiber-supported palladium catalyst and palladium carbon are also exemplified.
  • monodentate aryl phosphines such as triphenylphosphine and tri (o-tolyl) phosphine
  • monodentate alkyl phosphines such as tri (cyclohexyl) phosphine, tri (isopropyl) phosphine and tri (tert-butyl) phosphine, and 1,2-bis.
  • bidentate phosphines such as (diphenylphosphino) ethane, 1,2-bis (diphenylphosphino) propane, 1,2-bis (diphenylphosphino) butane, 1,2-bis (diphenylphosphino) ferrocene. You may make it react.
  • Examples of the base used in the above reaction include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, potassium phosphate, sodium phosphate, sodium-methoxide, sodium-ethoxide, potassium-methoxide, potassium-ethoxide, Examples include alkali metal alkoxides such as lithium-tert-butoxide, sodium-tert-butoxide, potassium-tert-butoxide, triethylamine, tributylamine, and pyridine.
  • reaction solvent can be used. Any reaction solvent may be used as long as it does not adversely affect the reaction, aromatic organic solvents such as benzene, toluene and xylene, ether organic solvents such as diethyl ether, tetrahydrofuran and dioxane, acetonitrile, dimethylformamide, Examples thereof include dimethyl sulfoxide and hexamethylphosphotriamide, and aromatic organic solvents such as benzene, toluene and xylene are preferred.
  • aromatic organic solvents such as benzene, toluene and xylene
  • ether organic solvents such as diethyl ether, tetrahydrofuran and dioxane
  • acetonitrile dimethylformamide
  • dimethylformamide examples thereof include dimethyl sulfoxide and hexamethylphosphotriamide
  • aromatic organic solvents such as benzene, toluene and xylene are preferred.
  • halogen compound represented by the general formula (11) a halogen compound represented by the following general formula (12) or (13) (halogenated benzo [b] phenanthreno [9,10-d] thiophene) Or halogenated benzo [b] phenanthreno [9,10-d] furan).
  • halogenated benzo [b] phenanthreno [9,10-d] thiophene and halogenated benzo [b] phenanthreno [9,10-d] furan can be obtained by a known method (Angewandte Chemie International Edition, 2012). 51, page 12293).
  • R 1 to R 3 are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms and a heteroaromatic group having 3 to 18 carbon atoms in that they are suitable for the synthesis of the arylamine compound of the present invention.
  • These groups include a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms.
  • halogenated alkyl groups having 1 to 3 carbon atoms halogenated alkoxy groups having 1 to 3 carbon atoms
  • aryl groups having 6 to 20 carbon atoms aryloxy groups having 6 to 18 carbon atoms
  • heterogeneous groups having 3 to 18 carbon atoms It has at least one substituent selected from the group consisting of an aryl group, a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a fluorine atom, and a deuterium atom. May be.
  • a phenyl group a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group (these groups are a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms).
  • a phenyl group, a naphthyl group, or a biphenyl group (these groups are a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a carbon number)
  • It may have one or more substituents selected from the group consisting of 3 to 18 linear, branched, or cyclic alkoxy groups, cyano groups, and deuterium atoms
  • a phenyl group, a methyl group, a methoxy group, a cyano group, a deuterium atom, or a hydrogen atom is more preferable.
  • a methyl group or a hydrogen atom is particularly preferable.
  • the preferred range for X and L is the same as described above.
  • the arylamine compound represented by the general formula (1) of the present invention can be used as a light emitting layer, a hole transport layer or a hole injection layer of an organic EL device.
  • the arylamine compound represented by the general formula (1) is excellent in hole transport ability, when used as a hole transport layer and / or a hole injection layer, a low driving voltage of the organic EL device is used. , High luminous efficiency, and improved durability can be realized.
  • the arylamine compound represented by the general formula (1) When the arylamine compound represented by the general formula (1) is used as a hole injection layer and / or a hole transport layer of an organic EL device, a known fluorescence or phosphorescence conventionally used is used for the light emitting layer.
  • a luminescent material can be used.
  • the light emitting layer may be formed of only one kind of light emitting material, or one or more kinds of light emitting materials may be doped in the host material.
  • the hole injection layer and / or hole transport layer comprising the arylamine compound represented by the general formula (1)
  • two or more kinds of materials may be contained or laminated as necessary.
  • oxides such as molybdenum oxide, 7,7,8,8-tetracyanoquinodimethane, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane, hexacyano
  • a known electron accepting material such as hexaazatriphenylene may be contained or laminated.
  • the arylamine compound represented by the general formula (1) of the present invention can also be used as a light emitting layer of an organic EL device.
  • the arylamine compound represented by the general formula (1) is used as the light emitting layer of the organic EL device, the arylamine compound is used alone, used by doping a known light emitting host material, or known light emission. It can be used by doping with a dopant.
  • a method for forming a hole injection layer, a hole transport layer, or a light emitting layer containing the arylamine compound represented by the general formula (1) for example, known methods such as vacuum deposition, spin coating, and casting The method can be applied.
  • the basic structure of the organic EL device that can obtain the effects of the present invention includes a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode.
  • the anode and cathode of the organic EL element are connected to a power source via an electrical conductor.
  • the organic EL element operates by applying a potential between the anode and the cathode. Holes are injected into the organic EL element from the anode, and electrons are injected into the organic EL element at the cathode.
  • the organic EL element is typically placed on a substrate, and the anode or cathode can be in contact with the substrate.
  • the electrode in contact with the substrate is called the lower electrode for convenience.
  • the lower electrode is an anode, but the organic EL device of the present invention is not limited to such a form.
  • the substrate may be light transmissive or opaque depending on the intended emission direction.
  • the light transmission property can be confirmed by electroluminescence emission through the substrate.
  • transparent glass or plastic is used as the substrate in such a case.
  • the substrate may be a composite structure including multiple material layers. When the electroluminescent emission is confirmed through the anode, the anode is formed by passing or substantially passing through the emission.
  • the general transparent anode (anode) material used in the present invention is not particularly limited, and examples thereof include indium-tin oxide (ITO), indium-zinc oxide (IZO), and tin oxide.
  • ITO indium-tin oxide
  • IZO indium-zinc oxide
  • tin oxide Other metal oxides such as aluminum or indium doped tin oxide, magnesium-indium oxide, or nickel-tungsten oxide can also be used.
  • metal nitrides such as gallium nitride, metal selenides such as zinc selenide, or metal sulfides such as zinc sulfide can be used as the anode.
  • the anode can be modified with plasma deposited fluorocarbon. If electroluminescence emission is confirmed only through the cathode, the transmission properties of the anode are not critical and any conductive material that is transparent, opaque or reflective can be used. Examples of conductors for this application include gold, iridium, molybdenum, palladium, platinum, and the like.
  • a plurality of hole transporting layers such as a hole injection layer and a hole transport layer can be provided between the anode and the light emitting layer.
  • the hole injection layer and the hole transport layer have a function of transmitting holes injected from the anode to the light emitting layer. By interposing these layers between the anode and the light emitting layer, the hole injection layer and the hole transport layer are often used in a lower electric field. Holes can be injected into the light emitting layer.
  • the hole transport layer and / or hole injection layer contains the arylamine compound represented by the general formula (1).
  • any one of known hole transport materials and / or hole injection materials is selected together with the arylamine compound represented by the general formula (1). Can be used in combination.
  • hole injection materials and hole transport materials include, for example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, Examples thereof include oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers, particularly thiophene oligomers.
  • hole injecting material and the hole transporting material those described above can be used, but porphyrin compounds, aromatic tertiary amine compounds, styrylamine compounds and the like can also be used, and in particular, aromatic tertiary amine compounds. Is preferably used.
  • aromatic tertiary amine compound and styrylamine compound include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl, N, N′-diphenyl-N, N ′.
  • Examples of the host material for the light emitting layer include compounds having a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, or an anthranyl group.
  • DPVBi 4,4′-bis (2,2-diphenylvinyl) -1,1′-biphenyl
  • BCzVBi 4,4′-bis (9-ethyl-3-carbazovinylene) 1,1′-biphenyl
  • TBADN (2-tert-butyl-9,10-di (2-naphthyl) anthracene
  • ADN (9,10-di (2-naphthyl) anthracene
  • CBP 4,4′-bis (carbazole-9) -Yl) biphenyl
  • CDBP 4,4′-bis (carbazol-9-yl) -2,2′-dimethylbiphenyl
  • the host material in the light emitting layer may be an electron transport material as defined below, a hole transport material as defined above, another material that supports hole / electron recombination (support), or a combination of
  • fluorescent dopants include anthracene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compound, thiopyran compound, polymethine compound, pyrylium or thiapyrylium compound, fluorene derivative, perifanthene derivative, indenoperylene derivative, Examples thereof include bis (azinyl) amine boron compounds, bis (azinyl) methane compounds, and carbostyryl compounds.
  • an organometallic complex of a transition metal such as iridium, platinum, palladium, or osmium can be given.
  • dopants include Alq 3 (tris (8-hydroxyquinoline) aluminum)), DPAVBi (4,4′-bis [4- (di-para-tolylamino) styryl] biphenyl), perylene, Ir (PPy) 3 ( Examples include tris (2-phenylpyridine) iridium (III), FlrPic (bis (3,5-difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium (III)), and the like.
  • Examples of the electron transporting material include alkali metal complexes, alkaline earth metal complexes, and earth metal complexes.
  • Examples of the alkali metal complex, alkaline earth metal complex, or earth metal complex include 8-hydroxyquinolinate lithium (Liq), bis (8-hydroxyquinolinato) zinc, and bis (8-hydroxyquinolinate).
  • a hole blocking layer may be provided between the light emitting layer and the electron transport layer for the purpose of improving carrier balance.
  • Preferred compounds for the hole blocking layer include BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), BAlq (bis (2 -Methyl-8-quinolinolato) -4- (phenylphenolate) aluminum), or bis (10-hydroxybenzo [h] quinolinato) beryllium).
  • an electron injection layer may be provided for the purpose of improving electron injection properties and improving device characteristics (for example, light emission efficiency, constant voltage driving, or high durability).
  • Preferred compounds for the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, anthrone, etc. Is mentioned.
  • metal complexes alkali metal oxides, alkaline earth oxides, rare earth oxides, alkali metal halides, alkaline earth halides, rare earth halides, SiO 2 , AlO, SiN, SiON, AlON, Various oxides such as GeO, LiO, LiON, TiO, TiON, TaO, TaON, TaN, and C, inorganic compounds such as nitride, and oxynitride can also be used.
  • the cathode used in the present invention can be formed from any conductive material.
  • Desirable cathode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) mixture, indium , Lithium / aluminum mixtures, rare earth metals and the like.
  • Synthesis Example 2 (Synthesis of 3-phenylbenzothiophene-2-boronic acid [compound (16)]) Under a nitrogen stream, 20.0 g (95.2 mmol) of 3-phenylbenzothiophene obtained in Synthesis Example 1 was charged into a 500 mL eggplant-shaped flask and dissolved in 120 mL of dehydrated tetrahydrofuran. After cooling the reaction solution to ⁇ 78 ° C., 60.9 mL (99.9 mmol as n-butyllithium) of n-butyllithium in hexane (1.64 mol / L) was added dropwise. After completion of the dropwise addition, the reaction solution was stirred at ⁇ 78 ° C. for 30 minutes.
  • Synthesis Example 4 (Synthesis of [Compound (18)]) Under a nitrogen stream, 7.2 g (17.2 mmol) of the compound (17) obtained in Synthesis Example 3 was charged into a 500 mL three-necked flask and dissolved in 350 mL of dichloromethane. Thereafter, 4.8 g (34.5 mmol) of boron trifluoride-diethyl ether complex was added, and the mixture was stirred at room temperature for 30 minutes. After adding 50 g of a saturated aqueous sodium hydrogen carbonate solution, liquid separation was performed, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was washed with methanol to isolate 4.0 g (12.5 mmol) of a white fluffy solid of compound (18) (yield 72 %).
  • Synthesis Example 7 (Synthesis of [Compound (21)]) Under a nitrogen stream, 8.3 g (19.9 mmol) of the compound (20) obtained in Synthesis Example 6 was charged into a 500 mL three-necked flask and dissolved in 350 mL of dichloromethane. Thereafter, 5.6 g (39.7 mmol) of boron trifluoride-diethyl ether complex was added, and the mixture was stirred at room temperature for 1 hour. 100 g of methanol was added to the reaction solution, the deposited precipitate was collected by filtration, and further washed with methanol to isolate 4.5 g (14.1 mmol) of a white flocculent solid of compound (21) (yield 71%) ).
  • Synthesis Example 10 Synthesis of [Compound (24)]
  • 5.5 g (13.7 mmol) of the compound (23) obtained in Synthesis Example 9 was charged into a 500 mL three-necked flask and dissolved in 300 mL of dichloromethane. Thereafter, 3.9 g (27.4 mmol) of boron trifluoride-diethyl ether complex was added, and the mixture was stirred at room temperature for 30 minutes. After adding 40 g of saturated aqueous sodium hydrogen carbonate solution, the solution was separated.
  • Synthesis Example 13 Synthesis of [Compound (27)]
  • 24.5 g (47.5 mmol) of the compound (26) obtained in Synthesis Example 12 was charged into a 2000 mL three-necked flask and dissolved in 1000 mL of dichloromethane. Thereafter, 8.5 g (47.5 mmol) of N-bromosuccinimide was added, and the mixture was stirred at room temperature for 15 hours. After mixing 500 g of pure water, liquid separation was performed, and the obtained organic layer was washed with a saturated aqueous solution of sodium chloride, further dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane) to isolate 27.9 g (47.1 mmol) of a pale yellow powder of compound (27) (yield 99%).
  • Synthesis Example 14 (Synthesis of [Compound (28)]) Under a nitrogen stream, 7.0 g (11.9 mmol) of the compound (27) obtained in Synthesis Example 13 in a 200 mL three-necked flask, 3.4 g (15.4 mmol) of 1-pyrrolidinylazobenzene-2-boronic acid, tetrakis 0.41 g (0.36 mmol) of (triphenylphosphine) palladium, 50 mL of tetrahydrofuran, and 19 g of a 20 wt% aqueous sodium carbonate solution (35.6 mmol as sodium carbonate) were added, and the mixture was heated to reflux for 15 hours.
  • Synthesis Example 15 (Synthesis of [Compound (29)]) Under a nitrogen stream, 4.4 g (7.5 mmol) of the compound (27) obtained in Synthesis Example 13 in a 200 mL three-neck flask, 1.4 g (8.3 mmol) of 5-methyl-2-chlorophenylboronic acid, tetrakis (tri Phenylphosphine) palladium (0.26 g, 0.23 mmol), tetrahydrofuran (50 mL), and 20 wt% aqueous sodium carbonate solution (12 g) (22.5 mmol as sodium carbonate) were added, and the mixture was heated to reflux for 15 hours.
  • Synthesis Example 16 (Synthesis of [Compound (30)]) Under a nitrogen stream, 6.6 g (26.0 mmol) of the compound (19) obtained in Synthesis Example 5 in a 200 mL three-necked flask, 5.8 g (20.0 mmol) of 1-pyrrolidinylazo-2-bromo-5-chlorobenzene, tetrakis 0.69 g (0.60 mmol) of (triphenylphosphine) palladium, 35 mL of tetrahydrofuran, and 32 g of a 20 wt% aqueous sodium carbonate solution (60.0 mmol as sodium carbonate) were added and heated to reflux for 10 hours.
  • Synthesis Example 17 (Synthesis of [Compound (31)]) Under a nitrogen stream, 5.8 g (14.0 mmol) of the compound (30) obtained in Synthesis Example 16 was charged into a 500 mL three-necked flask and dissolved in 300 mL of dichloromethane. Thereafter, 4.0 g (28.0 mmol) of boron trifluoride-diethyl ether complex was added, and the mixture was stirred at room temperature for 1 hour. 100 g of methanol was added to the reaction solution, the deposited precipitate was collected by filtration, and further washed with methanol to isolate 3.2 g (9.9 mmol) of the brown powder of compound (31) (yield 71%).
  • Synthesis Example 18 (Synthesis of [Compound (32)]) Under a nitrogen stream, 7.0 g (27.6 mmol) of the compound (16) obtained in Synthesis Example 2 in a 200 mL three-necked flask, 6.6 g (23.0 mmol) of 1-pyrrolidinylazo-2-bromo-5-chlorobenzene, tetrakis (Triphenylphosphine) palladium 0.80 g (0.69 mmol), tetrahydrofuran 35 mL, and 20 wt% sodium carbonate aqueous solution 36 g (68.9 mmol as sodium carbonate) were added, and the mixture was heated to reflux for 10 hours.
  • Triphenylphosphine Triphenylphosphine
  • Synthesis Example 19 (Synthesis of [Compound (33)]) Under a nitrogen stream, 7.3 g (17.5 mmol) of the compound (32) obtained in Synthesis Example 18 was charged into a 500 mL three-necked flask and dissolved in 360 mL of dichloromethane. Thereafter, 5.0 g (35.0 mmol) of boron trifluoride-diethyl ether complex was added, and the mixture was stirred at room temperature for 1 hour. 150 g of methanol was added to the reaction solution, the deposited precipitate was collected by filtration, and further washed with methanol to isolate 3.9 g (12.3 mmol) of a brown powder of compound (33) (yield 70%).
  • Example 1 (Synthesis of Compound (E7)) In a 50 mL three-necked flask under a nitrogen stream, 2.0 g (6.2 mmol) of the compound (18), 2.0 g (6.2 mmol) of N, N-bisbiphenylamine, and 0.84 g (8. 8) of sodium-tert-butoxide. 7 mmol) and 20 mL of o-xylene were added, and 42 mg (0.18 mmol) of palladium acetate and 132 mg (0.65 mmol) of tri (tert-butyl) phosphine were added to the slurry reaction solution, followed by stirring at 140 ° C. for 4 hours did.
  • Example 2 Synthesis of Compound (E11)
  • 2.1 g (4.6 mmol) of N, N-bisphenylphenylamine, and 0.63 g of sodium tert-butoxide (6. 5 mmol) and 15 mL of o-xylene were added, and 31 mg (0.13 mmol) of palladium acetate and 99 mg (0.48 mmol) of tri (tert-butyl) phosphine were added to the slurry-like reaction solution, followed by stirring at 140 ° C. for 6 hours. did.
  • Example 3 (Synthesis of Compound (A7)) In a 50 mL three-necked flask under a nitrogen stream, 3.0 g (9.4 mmol) of Compound (21), 3.0 g (9.4 mmol) of N, N-bis (4-biphenyl) amine, sodium-tert-butoxide 2 g (13.2 mmol) and 20 mL o-xylene were added. To the resulting slurry mixture, 42 mg (0.18 mmol) of palladium acetate and 132 mg (0.65 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 6 hours.
  • Example 4 Synthesis of Compound (A26)
  • 1.0 g (3.1 mmol) of compound (21), 0.13 g (1.5 mmol) of aniline, 0.42 g (4.4 mmol) of sodium-tert-butoxide, and o- Xylene 5 mL was added.
  • 7 mg (0.03 mmol) of palladium acetate and 21 mg (0.10 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 3 hours. After cooling to room temperature, 5 mL of pure water was added and stirred.
  • the product precipitated in the organic layer was collected by filtration and washed with water and ethanol.
  • the obtained brown powder was recrystallized from o-xylene to isolate 0.83 g (1.2 mmol) of a light brown powder of compound (A26) (yield 84%).
  • the compound was identified by FDMS measurement (FDMS (m / z): 657).
  • Example 5 Synthesis of Compound (B7)
  • compound (24) In a 100 mL three-necked flask under a nitrogen stream, 2.7 g (9.0 mmol) of compound (24), 2.9 g (9.1 mmol) of N, N-bis (4-biphenyl) amine, sodium-tert-butoxide 2 g (12.6 mmol) and 30 mL of o-xylene were added.
  • 40 mg (0.18 mmol) of palladium acetate and 146 mg (0.72 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 6 hours.
  • Example 6 Synthesis of Compound (B27)
  • compound (24) In a 50 mL three-necked flask under a nitrogen stream, 0.8 g (2.6 mmol) of compound (24), 0.14 g (1.3 mmol) of p-toluidine, 0.34 g (3.6 mmol) of sodium-tert-butoxide, and 10 mL of o-xylene was added.
  • 11 mg (0.05 mmol) of palladium acetate and 35 mg (0.17 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 4 hours. After cooling to room temperature, 10 mL of pure water was added and stirred.
  • Example 7 Synthesis of Compound (E26)
  • 0.05 g (0.59 mmol) of aniline 0.16 g (1.7 mmol) of sodium-tert-butoxide, and o- Xylene 5 mL was added.
  • 2 mg (0.01 mmol) of palladium acetate and 8 mg (0.04 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 2 hours. After cooling to room temperature, 5 mL of pure water was added and stirred.
  • Example 8 Synthesis of Compound (F7) Under a nitrogen stream, 5.5 g (8.1 mmol) of compound (28) was charged into a 500 mL three-necked flask, and 250 mL of dichloromethane was added and dissolved. To the obtained solution, 2.3 g (16.1 mmol) of boron trifluoride-diethyl ether complex was added and stirred at room temperature for 30 minutes. After adding and mixing 20 g of saturated aqueous sodium hydrogen carbonate solution, liquid separation was performed, and the organic layer was washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure.
  • Example 9 Synthesis of Compound (A5)
  • a 50 mL three-necked flask under a nitrogen stream 1.1 g (3.5 mmol) of the compound (21), 1.0 g (3.5 mmol) of N-phenyl-N-2- (9,9-dimethylfluorenyl) amine , 0.47 g (4.9 mmol) of sodium-tert-butoxide and 10 mL of o-xylene were added.
  • 16 mg (0.07 mmol) of palladium acetate and 57 mg (0.28 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 2 hours.
  • Example 10 Synthesis of Compound (A17)
  • 0.86 g (2.7 mmol) of Compound (21) 0.74 g (2.7 mmol) of N-phenyl-N-2-dibenzothienylamine, sodium tert-butoxide 0. 36 g (3.8 mmol) and 10 mL o-xylene were added.
  • 11 mg (0.05 mmol) of palladium acetate and 40 mg (0.20 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 5 hours.
  • Example 11 Synthesis of Compound (A18) Under a nitrogen stream, 0.96 g (3.0 mmol) of Compound (21), 0.78 g (3.0 mmol) of N-phenyl-N-2-dibenzofuranylamine, sodium tert-butoxide 40 g (4.2 mmol) and 10 mL o-xylene were added. To the resulting slurry mixture, 14 mg (0.06 mmol) of palladium acetate and 49 mg (0.24 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 3 hours. After cooling to room temperature, 10 mL of pure water was added and stirred.
  • Example 12 Synthesis of Compound (A31)
  • 1.0 g (3.1 mmol) of compound (21), 0.18 g (1.5 mmol) of 4-cyanoaniline, 0.42 g (4.4 mmol) of sodium-tert-butoxide, And 10 mL of o-xylene was added.
  • 7 mg (0.03 mmol) of palladium acetate and 24 mg (0.12 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 5 hours. After cooling to room temperature, 10 mL of pure water was added and stirred.
  • the product precipitated in the organic layer was collected by filtration and washed with water and ethanol.
  • the obtained brown powder was recrystallized from o-xylene, and 0.82 g (2.5 mmol) of a light brown powder of compound (A31) was isolated (yield 80%).
  • the compound was identified by FDMS measurement (FDMS (m / z): 684).
  • Example 13 Synthesis of Compound (B2)
  • 0.91 g (3.0 mmol) of Compound (24) 0.89 g (3.0 mmol) of N- (1-naphthyl) -N-4-biphenylamine, sodium-tert- 0.40 g (4.2 mmol) of butoxide and 10 mL of o-xylene were added.
  • 14 mg (0.06 mmol) of palladium acetate and 49 mg (0.24 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 6 hours.
  • Example 14 Synthesis of Compound (B12)
  • 0.70 g (2.3 mmol) of Compound (24) 0.68 g (2.3 mmol) of N-phenyl-N-4- (1-naphthyl) phenylamine, sodium-tert -0.31 g (3.2 mmol) of butoxide and 8 mL of o-xylene were added.
  • 10 mg (0.05 mmol) of palladium acetate and 37 mg (0.18 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 6 hours.
  • Example 15 (Synthesis of Compound (B20)) In a 50 mL three-necked flask under a nitrogen stream, 0.82 g (2.7 mmol) of Compound (24), 0.95 g (2.7 mmol) of N-phenyl-N-4- (4-dibenzothienyl) phenylamine, sodium- 0.36 g (3.8 mmol) of tert-butoxide and 10 mL of o-xylene were added. To the resulting slurry mixture, 12 mg (0.05 mmol) of palladium acetate and 42 mg (0.21 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 8 hours.
  • Example 16 Synthesis of Compound (B21)
  • 0.82 g (2.7 mmol) of compound (24) 0.91 g (2.7 mmol) of N-phenyl-N-4- (4-dibenzofuranyl) phenylamine, sodium -Tert-butoxide 0.36 g (3.8 mmol) and o-xylene 10 mL were added.
  • 12 mg (0.05 mmol) of palladium acetate and 42 mg (0.21 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 6 hours.
  • Example 18 (Synthesis of Compound (B31)) In a 50 mL three-necked flask under a nitrogen stream, 0.36 g (1.2 mmol) of Compound (24), 0.06 g (0.59 mmol) of 4-fluoroaniline, 0.16 g (1.7 mmol) of sodium-tert-butoxide, And 5 mL of o-xylene was added. To the obtained slurry mixture, palladium acetate (2 mg, 0.01 mmol) and tri (tert-butyl) phosphine (8 mg, 0.04 mmol) were added, followed by stirring at 140 ° C. for 5 hours. After cooling to room temperature, 5 mL of pure water was added and stirred.
  • Example 21 (Synthesis of Compound (C7)) In a 50 mL three-necked flask under a nitrogen stream, 0.73 g (2.3 mmol) of Compound (31), 0.74 g (2.3 mmol) of N, N-bis (4-biphenyl) amine, sodium tert-butoxide 0. 31 g (3.2 mmol) and 8 mL o-xylene were added. To the obtained slurry mixture, 10 mg (0.05 mmol) of palladium acetate and 37 mg (0.18 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 6 hours.
  • Example 22 Synthesis of Compound (C25)
  • 0.64 g (2.0 mmol) of compound (31) 0.67 g (2.0 mmol) of N-phenyl-N-4- (9-carbazolyl) phenylamine, sodium-tert -0.27 g (2.8 mmol) of butoxide and 8 mL of o-xylene were added.
  • 9 mg (0.04 mmol) of palladium acetate and 32 mg (0.16 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 6 hours.
  • Example 23 (Synthesis of Compound (E19)) In a 100 mL three-necked flask under a nitrogen stream, 1.5 g (4.7 mmol) of compound (18), 1.6 g (4.7 mmol) of N-phenyl-N-3- (9-phenylcarbazolyl) amine, sodium -0.63 g (6.6 mmol) of tert-butoxide and 15 mL of o-xylene were added. To the resulting slurry mixture, 20 mg (0.09 mmol) of palladium acetate and 73 mg (0.36 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 6 hours.
  • Example 24 (Synthesis of Compound (E24)) In a 50 mL three-necked flask under a nitrogen stream, 0.80 g (2.5 mmol) of compound (18), 1.0 g (2.5 mmol) of N-phenyl-N-4- (9-phenylcarbazolyl) phenylamine, Sodium-tert-butoxide 0.34 g (3.5 mmol) and o-xylene 10 mL were added. To the resulting slurry mixture, 12 mg (0.05 mmol) of palladium acetate and 40 mg (0.20 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 8 hours.
  • Example 25 (Synthesis of Compound (E25)) In a 50 mL three-necked flask under a nitrogen stream, 0.83 g (2.6 mmol) of Compound (18), 0.87 g (2.6 mmol) of N-phenyl-N-4- (9-carbazolyl) phenylamine, sodium-tert -0.27 g (3.6 mmol) of butoxide and 10 mL of o-xylene were added. To the resulting slurry mixture, 12 mg (0.05 mmol) of palladium acetate and 42 mg (0.21 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 6 hours.
  • Example 26 Synthesis of Compound (E30)
  • 0.80 g (2.5 mmol) of compound (18) 0.80 g (2.5 mmol) of N-phenyl-2-triphenylenylamine, 0.34 g of sodium tert-butoxide ( 3.5 mmol)
  • 10 mL of o-xylene 10 mL
  • 12 mg (0.05 mmol) of palladium acetate and 40 mg (0.20 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 6 hours.
  • Example 27 Synthesis of Compound (F33) Under a nitrogen stream, 4.5 g (7.1 mmol) of compound (29), 4.5 g (21.3 mmol) of tripotassium phosphate, and 100 mL of N-methylpyrrolidone were added to a 300 mL three-necked flask. To the resulting slurry mixture, 80 mg (0.36 mmol) of palladium acetate and 202 mg (0.72 mmol) of tricyclohexylphosphine were added, followed by stirring at 130 ° C. for 8 hours. After cooling to room temperature, 100 mL of pure water was added and stirred.
  • the product precipitated in the organic layer was collected by filtration and washed with water and methanol.
  • the obtained gray powder was recrystallized with toluene, and 2.7 g (4.6 mmol) of the gray powder of compound (F33) was isolated (yield 65%).
  • the compound was identified by FDMS measurement (FDMS (m / z): 601).
  • Example 28 Synthesis of Compound (G4)
  • 0.96 g (3.0 mmol) of Compound (33) 0.78 g (3.0 mmol) of N- (p-tolyl) -N-4-biphenylamine, sodium-tert- 0.40 g (4.2 mmol) of butoxide and 10 mL of o-xylene were added.
  • 13 mg (0.06 mmol) of palladium acetate and 48 mg (0.24 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 8 hours.
  • Example 29 Synthesis of Compound (G7)
  • 0.80 g (2.5 mmol) of Compound (33) 0.80 g (2.5 mmol) of N, N-bis (4-biphenyl) amine, sodium tert-butoxide 34 g (3.5 mmol) and 10 mL of o-xylene were added.
  • 12 mg (0.05 mmol) of palladium acetate and 40 mg (0.20 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 8 hours.
  • Example 30 (Synthesis of Compound (N8)) In a 50 mL three-necked flask under a nitrogen stream, 0.41 g (1.3 mmol) of the compound (21), 0.63 g (1.3 mmol) of N, N′-diphenyl-N- (4-biphenyl) benzidine, sodium-tert -0.17 g (1.8 mmol) of butoxide and 5 mL of o-xylene were added. To the obtained slurry mixture, 6 mg (0.03 mmol) of palladium acetate and 21 mg (0.10 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 6 hours.
  • Example 31 Synthesis of Compound (P2)
  • 0.48 g (1.6 mmol) of Compound (24) 0.78 g of N-phenyl-N ′, N′-bis (4-biphenyl) -1,4-phenylenediamine ( 1.6 mmol), 0.22 g (2.2 mmol) of sodium-tert-butoxide, and 5 mL of o-xylene were added.
  • 7 mg (0.03 mmol) of palladium acetate and 26 mg (0.13 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C.
  • Example 32 (Synthesis of Compound (Q10)) In a 50 mL three-necked flask under nitrogen flow, 0.48 g (1.5 mmol) of compound (18), 0.85 g (1.5 mmol) of N-phenyl-N ′, N′-bis (4-biphenyl) benzidine, sodium -0.20 g (2.1 mmol) of tert-butoxide and 5 mL of o-xylene were added. To the obtained slurry mixture, 7 mg (0.03 mmol) of palladium acetate and 24 mg (0.12 mmol) of tri (tert-butyl) phosphine were added, followed by stirring at 140 ° C. for 8 hours.
  • Example 33 (Element Evaluation of Compound (E7)) A glass substrate on which an ITO (Indium Tin Oxide) transparent electrode (anode) having a thickness of 200 nm was laminated was subjected to ultrasonic cleaning with acetone and pure water and boiling cleaning with isopropyl alcohol. Further, ultraviolet ozone cleaning was carried out, and after evacuation with a vacuum pump until it was 1 ⁇ 10 ⁇ 4 Pa after installation in a vacuum deposition apparatus. First, copper phthalocyanine was deposited on the ITO transparent electrode at a deposition rate of 0.1 nm / second to form a 25 nm hole injection layer.
  • ITO Indium Tin Oxide
  • the compound (E7) was deposited at 45 nm at a deposition rate of 0.3 nm / second to form a hole transport layer.
  • DPAVBi 4,4′-bis (2- (4- (N, N-diphenylamino) phenyl) vinyl) biphenyl
  • 2-tert-butyl-9,10 as a host material -Di (2-naphthyl) anthracene (TBADN) was co-evaporated at a deposition rate of 0.25 nm / second so that the weight ratio was 3:97 to obtain a 40 nm light-emitting layer.
  • Examples 34 to 64 Compound (E7) is converted into Compound (E11), (A7), (A26), (B7), (B27), (E26), (F7), (A5), (A17), (A18), (A31), (B2), (B12), (B20), (B21), (B27), (B31), (B33), (C3), (C7), (C25), (E19), (E24), (E25 ), (E30), (F33), (G4), (G7), (N8), (P2), or (Q10) except that the organic EL device was fabricated in the same manner as in Example 33 did.
  • Table 1 summarizes the driving voltage and current efficiency when a current of 20 mA / cm 2 was applied to the device.
  • Comparative Example 1 An EL device was produced in the same manner as in Example 33 except that the compound (E7) was changed to 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPD). Table 1 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied to the obtained device.
  • Comparative Example 2 An organic EL device was produced in the same manner as in Example 33 except that the compound (E7) was changed to the comparative compound (1).
  • Table 1 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied to the obtained device. Comparative compound (1) was synthesized according to the following scheme.
  • Comparative Example 3 An organic EL device was produced in the same manner as in Example 33 except that the compound (E7) was changed to the comparative compound (2).
  • Table 1 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied to the obtained device. Comparative compound (2) was synthesized according to the following scheme.
  • the arylamine compound of the present invention can be used as a light-emitting material of an organic EL device, or a hole injection material or a hole transport material excellent in hole transport capability, and further, an organic thin film solar cell, an organic transistor, an image sensor, It can also be used as a material for organic devices.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Furan Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne : un nouveau composé arylamine ; et un élément EL organique qui est fabriqué à l'aide du composé arylamine et qui présente une efficacité lumineuse élevée et une excellente durabilité. L'invention concerne ainsi un composé arylamine représenté par la formule (1) ; un matériau d'élément EL organique contenant ledit composé arylamine ; et un élément EL organique. (n : entier situé dans la plage allant de 0 à 2, M : groupe hydrocarbure aromatique (n+1)-valent ayant de 6 à 20 atomes de carbone, ou analogue, Ar1 : substituant représenté par la formule (2) ou (3), Ar2 à Ar4 : groupe hydrocarbure aromatique ayant de 6 à 20 atomes de carbone, ou analogue) (X : atome d'oxygène ou atome de soufre, L : liaison simple, groupe hydrocarbure aromatique bivalent ayant de 6 à 20 atomes de carbone, ou analogue, R1 à R3 : groupe hydrocarbure aromatique ayant de 6 à 20 atomes de carbone, ou analogue)
PCT/JP2014/062521 2013-05-10 2014-05-09 Composé arylamine et son utilisation WO2014181878A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2013100594 2013-05-10
JP2013-100594 2013-05-10
JP2013-214189 2013-10-11
JP2013214189 2013-10-11

Publications (1)

Publication Number Publication Date
WO2014181878A1 true WO2014181878A1 (fr) 2014-11-13

Family

ID=51867350

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2014/062521 WO2014181878A1 (fr) 2013-05-10 2014-05-09 Composé arylamine et son utilisation

Country Status (3)

Country Link
JP (1) JP6274000B2 (fr)
TW (1) TW201446709A (fr)
WO (1) WO2014181878A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015194791A3 (fr) * 2014-06-18 2016-08-11 덕산네오룩스 주식회사 Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique associé
JP2019011286A (ja) * 2017-06-30 2019-01-24 公益財団法人相模中央化学研究所 ホスフィン化合物及びこれを配位子とするカップリング用触媒
WO2022080477A1 (fr) * 2020-10-15 2022-04-21 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2020090989A1 (ja) * 2018-10-31 2021-09-24 日産化学株式会社 フッ化芳香族第二級または第三級アミン化合物の製造方法
JP2020152655A (ja) * 2019-03-19 2020-09-24 東ソー株式会社 縮環基を有するベンゾヘテロフェナントレン化合物及びその用途

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012045710A1 (fr) * 2010-10-07 2012-04-12 Basf Se Phénanthro[9,10-b]furanes pour applications électroniques
US20130009137A1 (en) * 2011-07-05 2013-01-10 Plextronics, Inc. Vertically phase-separating semiconducting organic material layers
WO2013055132A2 (fr) * 2011-10-13 2013-04-18 덕산하이메탈(주) Composé pour dispositif électrique organique, dispositif électrique organique l'utilisant et dispositif électronique correspondant

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101516856B (zh) * 2006-09-14 2013-01-02 西巴控股有限公司 杂环桥联联苯及其在场致发光装置中的应用
WO2011037429A2 (fr) * 2009-09-28 2011-03-31 덕산하이메탈(주) Composés ayant des dérivés hétérocycliques à cycle aryle condensé de 5 chaînons, dispositif électronique organique utilisant les composés, et terminal comprenant le dispositif électronique organique

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012045710A1 (fr) * 2010-10-07 2012-04-12 Basf Se Phénanthro[9,10-b]furanes pour applications électroniques
US20130009137A1 (en) * 2011-07-05 2013-01-10 Plextronics, Inc. Vertically phase-separating semiconducting organic material layers
WO2013055132A2 (fr) * 2011-10-13 2013-04-18 덕산하이메탈(주) Composé pour dispositif électrique organique, dispositif électrique organique l'utilisant et dispositif électronique correspondant

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015194791A3 (fr) * 2014-06-18 2016-08-11 덕산네오룩스 주식회사 Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique associé
US20170125689A1 (en) * 2014-06-18 2017-05-04 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US10424741B2 (en) 2014-06-18 2019-09-24 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
JP2019011286A (ja) * 2017-06-30 2019-01-24 公益財団法人相模中央化学研究所 ホスフィン化合物及びこれを配位子とするカップリング用触媒
WO2022080477A1 (fr) * 2020-10-15 2022-04-21 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique

Also Published As

Publication number Publication date
JP2015096484A (ja) 2015-05-21
TW201446709A (zh) 2014-12-16
JP6274000B2 (ja) 2018-02-07

Similar Documents

Publication Publication Date Title
US11800785B2 (en) Material for organic device and organic electroluminescent device using the same
CN110382590B (zh) 含有取代三芳基胺骨架的高分子化合物
JP6281414B2 (ja) ４−カルバゾリルアミン化合物
WO2017086357A1 (fr) Élément électroluminescent organique
KR102556378B1 (ko) 축합고리 화합물
JP6274000B2 (ja) アリールアミン化合物及びその用途
WO2014024446A1 (fr) Composé ayant une structure de noyau triphénylène, et élément électroluminescent organique
WO2018155275A1 (fr) Composé de triarylamine à pont d'oxygène, précurseur de celui-ci et matériau électroluminescent
JP6398322B2 (ja) ベンゾチエノフルオレン化合物及びその用途
JP7363045B2 (ja) トリフェニレン化合物及びその用途
JP7135428B2 (ja) 縮合環化合物
CN111303113A (zh) 有机化合物、电子器件及电子装置
JP6083282B2 (ja) ４−アミノカルバゾール化合物及びその用途
TWI546295B (zh) 具有經取代之鄰聯三苯結構之化合物及有機電激發光元件
CN112204030B (zh) 化合物及包含其的有机发光器件
JP7143670B2 (ja) トリフェニレン化合物及びその用途
JP7310132B2 (ja) 縮合環化合物および有機エレクトロルミネッセンス素子用材料
JP7443668B2 (ja) 縮合環化合物、その製法、及びその製造中間体
JP7234532B2 (ja) ジベンゾ［ｇ，ｐ］クリセン化合物
CN113056463A (zh) 化合物及包含其的有机发光器件
WO2022211123A1 (fr) Matériau de suppression de courant transversal, composé de carbazole, couche d'injection de trous et élément électroluminescent organique
WO2023013615A1 (fr) Composé amine, couche d'injection de trous et élément électroluminescent organique
JP7176195B2 (ja) 酸素架橋型トリアリールアミン化合物及びその前駆体ならびに発光材料
WO2020111140A1 (fr) Composé cyclique fusionné, son procédé de production et matériau d'élément électroluminescent organique
WO2019131691A1 (fr) Composé à cycle condensé et matériau pour élément électroluminescent organique

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 14794736

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 14794736

Country of ref document: EP

Kind code of ref document: A1