WO2009154207A1 - Dérivé d’anthracène et élément électroluminescent organique l’utilisant - Google Patents

Dérivé d’anthracène et élément électroluminescent organique l’utilisant Download PDF

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WO2009154207A1
WO2009154207A1 PCT/JP2009/060963 JP2009060963W WO2009154207A1 WO 2009154207 A1 WO2009154207 A1 WO 2009154207A1 JP 2009060963 W JP2009060963 W JP 2009060963W WO 2009154207 A1 WO2009154207 A1 WO 2009154207A1
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group
substituted
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ring
carbon atoms
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光則 伊藤
昌宏 河村
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出光興産株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
    • C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
    • C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/27—Polycyclic condensed hydrocarbons containing three rings
    • C07C15/28—Anthracenes
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    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24—Anthracenes; Hydrogenated anthracenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a novel anthracene compound useful as a light-emitting material of an organic electroluminescence device and an organic electroluminescence device using the same.
  • An organic electroluminescence (EL) element is a self-luminous element utilizing the principle that a light-emitting material emits light by recombination energy of holes injected from an anode and electrons injected from a cathode when an electric field is applied.
  • Organic EL devices have made remarkable progress, and organic EL devices have features such as low-voltage driving, high brightness, diversity of emission wavelengths, high-speed response, and the ability to produce thin and light-emitting devices. Application to applications is expected.
  • Luminescent materials used in organic EL elements have been actively studied since they have a great influence on the color of light emitted from the elements and the emission lifetime.
  • the light-emitting material one that emits light by a single substance or one that emits light by adding a small amount of dopant to a host material is known.
  • fluorescent materials it has been studied to use phosphorescent compounds as light emitting materials and to use triplet state energy for light emission. With such various light emitting materials, light emission in a visible region from blue to red is obtained.
  • Patent Documents 1 to 3 disclose anthracene compounds tetra-substituted with a phenyl group or a biphenyl group.
  • Patent Document 4 discloses an anthracene compound tetrasubstituted with a substituent containing a fluorenyl group.
  • Patent Documents 5 to 8 disclose anthracene compounds having substituents at the 2, 6, 9, and 10 positions of the anthracene skeleton.
  • An object of the present invention is to provide a novel luminescent material and an organic EL element using the luminescent material.
  • anthracene derivative represented by the following formula (1) except for an anthracene derivative represented by the following formula (1 ′)).
  • Ar 11 to Ar 14 are each a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group.
  • Ar 21 to Ar 24 are each a hydrogen atom, substituted or unsubstituted, An alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heterocyclic group.
  • Ar 11 to Ar 14 are all benzene rings, Ar 21 to Ar 24 are not all hydrogen atoms. When at least one of Ar 11 to Ar 14 is a 9,9′-dimethylfluorenyl group or a 9,9′-diphenylfluorenyl group, the remaining Ar 11 to Ar 14 are all unsubstituted phenyl groups. None become. ) 2.
  • An anthracene derivative represented by the following formula (1 ′). In the formula, Ar 11 to Ar 14 and Ar 21 to Ar 24 are the same groups as in claim 1. However, in the formula (1 ′), Ar 11 to Ar 14 are each a benzene ring or a naphthalene ring.
  • Ar 33 represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring forming atom number.
  • the anthracene derivative according to 4 wherein Ar 33 is a hydrogen atom, and Ar 31 is an unsubstituted condensed aromatic ring group having 10 to 30 carbon atoms. 6). 6.
  • Ar 31 and Ar 32 are each a substituted or unsubstituted phenylene group,
  • Ar 33 to Ar 36 are substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 ring carbon atoms, or substituted or unsubstituted ring formation 5.
  • Ar 35 to Ar 38 are each a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • Indicates. Ra and Rb each represents a hydrogen atom or a substituent, and p and q each represents an integer of 1 to 4.
  • each of Ar 41 to Ar 46 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • Ar 43 to Ar 46 are substituted or unsubstituted condensed aromatic ring groups having 10 to 30 ring carbon atoms, or substituted or unsubstituted ring forming atoms having 10 to 30 ring atoms.
  • a light emitting material comprising the anthracene derivative according to any one of 1 to 10 above. 12 12.
  • the light emitting material according to 11, wherein the anthracene derivative is a host material. 13.
  • An organic electroluminescence device in which one or more organic thin film layers are sandwiched between an anode and a cathode, wherein at least one of the organic thin film layers contains the anthracene derivative according to any one of 1 to 10 element.
  • 14 The organic electroluminescence device according to 13, wherein the layer containing the anthracene derivative further contains at least one of a phosphorescent dopant and a fluorescent dopant.
  • the fluorescent dopant is at least one of an arylamine compound, a styrylamine compound, and a fluoranthene compound. 16.
  • An organic electroluminescent material-containing solution containing the light-emitting material according to 11 or 12 above. 18. 18.
  • 18. An organic electroluminescent device produced using the organic electroluminescent material-containing solution described in 17 above.
  • the organic EL element obtained using a novel anthracene derivative, a luminescent material which consists of this, an organic EL material containing solution containing a luminescent material, and an organic EL material containing solution can be provided.
  • the organic EL device using the anthracene derivative of the present invention has an excellent lifetime.
  • the anthracene derivative of the present invention is a compound represented by the following formula (1) (except when it is an anthracene derivative represented by the following formula (1 ′)).
  • the anthracene derivative of the present invention is a compound represented by the following formula (1 ′).
  • Formula (1 ′) when Ar 11 to Ar 14 are each a benzene ring or a naphthalene ring, all of Ar 21 to Ar 24 do not become hydrogen atoms.
  • Ar 11 to Ar 14 are each a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group.
  • Ar 21 to Ar 24 are each a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heterocyclic group.
  • Ar 21 to Ar 24 are assumed to be hydrogen atoms, and each group of Ar 11 to Ar 14 includes other than hydrogen atoms and hydrogen atoms. When these groups are bonded, groups other than the hydrogen atom are referred to as Ar 21 to Ar 24 .
  • Ar 21 to Ar 24 are hydrogen atoms, a substituted or unsubstituted phenyl group, indenyl group, fluorenyl group, naphthyl group, anthryl group, phenanthryl group, naphthacenyl group Group, acenaphthylenyl group, biphenyl group, chrysenyl group, pyrenyl group, triphenyl group, fluoranthenyl group, perylenyl group, fluorenyl group, and terphenyl group.
  • the aromatic hydrocarbon group of Ar 11 to Ar 14 preferably has 6 to 60 ring-forming carbon atoms, and more preferably 6 to 30 carbon atoms.
  • Ar 21 to Ar 24 are not hydrogen atoms
  • examples of Ar 11 to Ar 14 include divalent groups obtained by removing one hydrogen atom from the above groups.
  • heterocyclic group of Ar 11 to Ar 14 examples include, when Ar 21 to Ar 24 are hydrogen atoms, a substituted or unsubstituted pyrrolyl group, pyridinyl group, pyrazinyl group, indolyl group, furyl group, dibenzofuranyl group , Dibenzothienyl group, quinolyl group, carbazolyl group and the like.
  • the heterocyclic group of Ar 11 to Ar 14 preferably has 5 to 18 ring carbon atoms.
  • An example of Ar 11 to Ar 14 when Ar 21 to Ar 24 is not a hydrogen atom is a divalent group obtained by removing one hydrogen atom from the above group.
  • the aromatic hydrocarbon group and heterocyclic group of Ar 11 to Ar 14 may be substituted.
  • substituents include an alkyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 60 carbon atoms, Examples thereof include a heterocyclic group having 2 to 60 carbon atoms.
  • substituents include an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, and n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl groups (preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably carbon numbers).
  • alkyl group preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, and n-octyl, n-decyl, n-hexadecyl, cyclopropyl,
  • alkynyl group preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably carbon number
  • alkynyl group preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably carbon number
  • an aryl group preferably having 6 to 60 carbon atoms, more preferably 6 to 30 carbon atoms, particularly preferably 6 to 20 carbon atoms, such as phenyl, fluorenyl, naphthyl, anthryl, phenanthryl, chrysenyl, pyrenyl, triphenylenyl, fluoranthenyl, etc.
  • substituted or unsubstituted amino Group preferably having 0 to 20 carbon atoms, more preferably 0 to 12 carbon atoms, particularly preferably 0 to 6 carbon atoms, and examples thereof include amino, methylamino, dimethylamino, diethylamino, di
  • An alkoxy group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, such as methoxy, ethoxy, butoxy, etc.), an aryloxy group ( Preferably 6 to 20 carbon atoms, more preferably 6 to 16 carbon atoms, particularly preferred Has 6 to 12 carbon atoms, for example, phenyloxy, 2-naphthyloxy, etc.), an acyl group (preferably 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 carbon atom).
  • acetyl acetyl, benzoyl, formyl, pivaloyl, etc.
  • an alkoxycarbonyl group preferably having 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably 2 to 12 carbon atoms.
  • methoxycarbonyl, ethoxycarbonyl, etc. aryloxycarbonyl groups (preferably having 7 to 20 carbon atoms, more preferably 7 to 16 carbon atoms, particularly preferably 7 to 10 carbon atoms, such as phenyl Oxycarbonyl, etc.), acyloxy groups (preferably having 2 to 20 carbon atoms, more preferably having carbon atoms) It has 2 to 16, particularly preferably 2 to 10 carbon atoms, and examples thereof include acetoxy and benzoyloxy.
  • An acylamino group (preferably having 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetylamino, benzoylamino, etc.), an alkoxycarbonylamino group (Preferably having 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably 2 to 12 carbon atoms such as methoxycarbonylamino), aryloxycarbonylamino group (preferably having carbon number) 7 to 20, more preferably 7 to 16 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonylamino), substituted or unsubstituted sulfonylamino groups (preferably having 1 carbon atom) To 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms.
  • substituted or unsubstituted sulfamoyl groups (preferably having 0 to 20 carbon atoms, more preferably 0 to 16 carbon atoms, and particularly preferably 0 to 12 carbon atoms.
  • sulfamoyl Methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl etc.
  • substituted or unsubstituted carbamoyl groups preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms such as carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl, etc.
  • an alkylthio group preferably 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably carbon atoms).
  • An arylthio group (preferably having 6 to 20 carbon atoms, more preferably 6 to 16 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio), substituted or unsubstituted sulfonyl A group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl, tosyl, etc.), a substituted or unsubstituted sulfinyl group (preferably Has 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl, benzenesulfinyl, etc.), a substituted or unsubstituted ureido group (preferably It has 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, and
  • Substituted or unsubstituted phosphate amide groups (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphate amide, phenyl phosphate amide) Hydroxy group, mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino Group, imino group, heterocyclic group (preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom.
  • halogen atom eg fluorine atom, chlorine atom, bromine atom, iodine atom
  • cyano group e
  • Is for example, imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzoimidazolyl Benzothiazolyl, carbazolyl, etc.), silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyl, triphenylsilyl, etc. And the like. These substituents may be further substituted. Moreover, when there are two or more substituents, they may be the same or different. If possible, they may be linked to each other to form a ring.
  • substituents include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, trimethylsilyl, triphenylsilyl.
  • Preferred examples of Ar 11 to Ar 14 are shown below.
  • Ar 21 to Ar 24 are each a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted heterocyclic group.
  • the alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 8 carbon atoms.
  • Ar 21 ⁇ Ar 24 examples of the aromatic hydrocarbon group or heterocyclic group, similar to Ar 11 ⁇ Ar 14 described above groups (example when Ar 21 ⁇ Ar 24 is a hydrogen atom) and the like.
  • the alkyl group, aromatic hydrocarbon group and heterocyclic group of Ar 21 to Ar 24 may be substituted, and examples of the substituent include the same groups as Ar 11 to Ar 14 described above. Preferred examples of Ar 21 to Ar 24 are shown below.
  • Ar 11 to Ar 14 are all benzene rings
  • Ar 21 to Ar 24 are not all hydrogen atoms. That is, the following compounds are not anthracene derivatives of the present invention.
  • Ar 11 to Ar 14 When at least one of Ar 11 to Ar 14 is a 9,9′-dimethylfluorenyl group or a 9,9′-diphenylfluorenyl group, the remaining Ar 11 to Ar 14 are all unsubstituted phenyl groups. None become.
  • anthracene derivatives represented by the following formulas (2) to (6) are preferred.
  • Ar 11 to Ar 14 and Ar 21 to Ar 24 are the same groups as in the above formula (1), and specific examples thereof are also the same.
  • an anthracene derivative represented by the following formula (7) is also preferable.
  • each of Ar 31 , Ar 32 , Ar 34 , Ar 35, and Ar 36 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring forming atom number.
  • Ar 33 represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • Ar 31 to Ar 34 are a substituted or unsubstituted condensed aromatic ring group having 10 to 30 ring carbon atoms, or a heterocyclic group having 9 to 30 substituted or unsubstituted ring atoms.
  • a ring group is shown.
  • Ar 33 is preferably a hydrogen atom
  • Ar 31 is preferably an unsubstituted condensed aromatic ring group having 10 to 30 carbon atoms.
  • Ar 31 is preferably a metaphenylene group.
  • Ar 31 and Ar 32 are each a substituted or unsubstituted phenylene group
  • Ar 33 to Ar 36 are substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 ring carbon atoms, or substituted or unsubstituted A heterocyclic group having 5 to 30 ring-forming atoms is preferable.
  • An anthracene derivative represented by the following formula (8) is also preferable.
  • Ar 35 to Ar 38 each represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • Ra and Rb each represents a hydrogen atom or a substituent
  • p and q each represents an integer of 1 to 4.
  • Ar 37 and Ar 38 are each preferably a substituted or unsubstituted condensed ring group having 10 to 30 ring carbon atoms.
  • An anthracene derivative represented by the following formula (9) is also preferable.
  • each of Ar 41 to Ar 46 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • Ar 43 to Ar 46 are a substituted or unsubstituted condensed aromatic ring group having 10 to 30 ring carbon atoms, or a heterocyclic ring having 10 to 30 substituted or unsubstituted ring atoms. Indicates a group.
  • each group of formulas (7) to (9) represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring atom number of 5 to 30.
  • Specific examples of the heterocyclic group are the same as the examples of Ar 11 and the like in formula (1) described above.
  • Examples of the substituent represented by Ra and Rb in the formula (8) are the same as the substituents that the groups Ar 11 to Ar 14 in the formula (1) can have.
  • the anthracene derivative of the present invention can be synthesized by an ordinary method, for example, a method of synthesizing from a dihalogenated anthraquinone or a Suzuki coupling method. Examples of synthesis are given in the examples.
  • the anthracene derivative of the present invention can be used as a light emitting material for an organic EL device. Preferably it is used as a host material.
  • a polymerized one can also be used. When the polymer is made, it is synthesized by a method usually used in polymer synthesis (polycondensation reaction, coupling reaction, radical reaction, living polymerization, etc.). Although there is no restriction
  • one or more organic thin film layers are sandwiched between the anode and the cathode, and at least one of the organic thin film layers contains the above-described anthracene derivative of the present invention.
  • the layer containing the anthracene derivative of the present invention can further contain at least one of a phosphorescent dopant and a fluorescent dopant.
  • a dopant By including such a dopant, it can function as a phosphorescent light emitting layer, a fluorescent light emitting layer, and a hybrid light emitting layer having both phosphorescence and fluorescence.
  • the fluorescent dopant at least one of an arylamine compound, a styrylamine compound, and a fluoranthene compound is preferable.
  • the phosphorescent dopant a metal complex is preferable. For these specific examples, the description of the light emitting layer described later may be referred to.
  • the anthracene derivative of the present invention may be used in any of the organic layers described above, but is preferably contained in the light emitting band, and particularly preferably contained in the light emitting layer.
  • the content is preferably 30 to 100 wt%.
  • Fig. 1 shows the configuration (8).
  • the organic EL element includes a cathode 10 and an anode 20 and a hole injection layer 30, a hole transport layer 32, a light emitting layer 34, and an electron injection layer 36 sandwiched therebetween.
  • the hole injection layer 30, the hole transport layer 32, the light emitting layer 34, and the electron injection layer 36 correspond to organic thin film layers, respectively.
  • At least one of the layers 30, 32, 34, and 36 contains the anthracene derivative.
  • the organic EL element is usually produced on a substrate, and the substrate supports the organic EL element. It is preferable to use a smooth substrate. When light is extracted through this substrate, it is desirable that the substrate is translucent and that the transmittance of light in the visible region with a wavelength of 400 to 700 nm is 50% or more.
  • substrate a glass plate, a synthetic resin board, etc. are used suitably, for example.
  • the glass plate include soda-lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
  • the synthetic resin plate include plates made of polycarbonate resin, acrylic resin, polyethylene terephthalate resin, polyether sulfide resin, polysulfone resin, and the like.
  • the anode It is effective for the anode to inject holes into the hole injection layer, the hole transport layer, or the light emitting layer and to have a work function of 4.5 eV or more.
  • the anode material include indium tin oxide (ITO), a mixture of indium oxide and zinc oxide, a mixture of ITO and cerium oxide (ITCO), a mixture of indium oxide and zinc oxide and cerium oxide (IZCO), an oxidation Examples thereof include a mixture of indium and cerium oxide (ICO), a mixture of zinc oxide and aluminum oxide (AZO), tin oxide (NESA), gold, silver, platinum, and copper.
  • the anode can be formed from these electrode materials by vapor deposition or sputtering.
  • the transmittance of the anode for light emission is greater than 10%.
  • the sheet resistance of the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness of the anode depends on the material, it is usually 10 nm to 1 ⁇ m, preferably 10 to 200 nm.
  • the light emitting layer has the following functions.
  • injection function function capable of injecting holes from the anode or hole injection layer when an electric field is applied, and electron injection from the cathode or electron injection layer
  • transport function injected charge (electrons (Iii) light emission function; function to recombine electrons and holes and connect them to light emission
  • the light emitting layer is particularly preferably a molecular deposited film.
  • the molecular deposited film is a film formed by depositing a material compound in a gas phase state or a film formed by solidifying a material compound in a solution state or a liquid phase state.
  • this molecular deposited film is an LB.
  • the thin film (molecular accumulation film) formed by the method can be classified by the difference in aggregated structure and higher order structure, and the functional difference resulting therefrom.
  • the light emitting layer can also be formed by dissolving a binder such as a resin and a material compound in a solvent to form a solution, and then thinning the solution by a spin coating method or the like.
  • Examples of the light emitting material (host material or dopant material) that can be used for the light emitting layer include anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone, naphthaloperinone, diphenylbutadiene, Tetraphenylbutadiene, coumarin, oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene, quinoline metal complex, aminoquinoline metal complex, benzoquinoline metal complex, imine, diphenylethylene, vinylanthracene, diaminocarbazole, pyran Thiopyran, polymethine, merocyanine, imidazole chelating oxinoid compounds, quinac
  • Ar 001 is a substituted or unsubstituted condensed aromatic hydrocarbon group having 10 to 50 ring carbon atoms.
  • Ar 002 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms.
  • X 001 to X 003 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and a substituted group.
  • a gen atom, a cyano group, a nitro group, and a hydroxy group, a, b and c are each an integer of 0 to 4.
  • n is an integer of 1 to 3. When n is 2 or more, [] May be the same or different.)
  • R 001 to R 010 are each independently a hydrogen atom, a substituted or unsubstituted aromatic ring group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted group Or an unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, A substituted or unsubstituted aryloxy group having 5 to 50 ring atoms, a substituted or unsubstituted arylthio group having 5 to 50 ring atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, substituted or An unsubstituted silyl
  • Ar 005 and Ar 006 are each a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms.
  • L 001 and L 002 are a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted dibenzosilolylene group, respectively.
  • m is an integer from 0 to 2
  • n is an integer from 1 to 4
  • s is an integer from 0 to 2
  • t is an integer from 0 to 4.
  • L 001 or Ar 005 binds to any of the 1-5 positions of pyrene
  • L 002 or Ar 006 binds to any of the 6-10 positions of pyrene.
  • n + t is an even number
  • Ar 005 , Ar 006 , L 001 , and L 002 satisfy the following (1) or (2).
  • a 001 and A 002 are each independently a substituted or unsubstituted condensed aromatic ring group having 10 to 20 ring carbon atoms.
  • Ar 007 and Ar 008 are each independently a hydrogen atom or a substituted or unsubstituted aromatic ring group having 6 to 50 ring carbon atoms.
  • R 011 to R 020 are each independently a hydrogen atom, a substituted or unsubstituted aromatic ring group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted group Or an unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, A substituted or unsubstituted aryloxy group having 5 to 50 ring atoms, a substituted or unsubstituted arylthio group having 5 to 50 ring atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, substituted or An unsubstituted silyl
  • Ar 007 , Ar 008 , R 019 and R 020 may each be plural, and adjacent ones may form a saturated or unsaturated cyclic structure.
  • a group that is symmetrical with respect to the XY axis shown on the anthracene is not bonded to the 9th and 10th positions of the central anthracene.
  • R 021 to R 030 are each independently a hydrogen atom, alkyl group, cycloalkyl group, optionally substituted aryl group, alkoxyl group, aryloxy group, alkylamino group, alkenyl group, arylamino group, or substituted.
  • a and b each represent an integer of 1 to 5, and when they are 2 or more, R 021s or R 022s may be the same or different from each other In addition, R 021 or R 022 may be bonded to each other to form a ring, or R 023 and R 024 , R 025 and R 026 , R 027 and R 028 , R 029 and R 030 are L 003 may be a single bond, —O—, —S—, —N (R) — (R is an alkyl group or an optionally substituted aryl group). Represents an alkylene group or an arylene group.)
  • R 031 to R 040 each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an alkoxyl group, an aryloxy group, an alkylamino group, an arylamino group, or an optionally substituted multicyclic group
  • C, d, e and f each represent an integer of 1 to 5, and when they are 2 or more, R 031s , R 032s , R 036s or R 037s may be the same.
  • R 031 may be different from each other, R 032 may be bonded to each other, R 033 may be bonded to each other, or R 037 may be bonded to each other to form a ring, and R 033 and R 034 , R 039 and R 040 are based on each other.
  • bonded to ring the optionally formed .L 004 is a single bond, -O -, - S -, - N (R) - (R is an aryl group which may be alkyl or substituted), Al Shows the alkylene group or an arylene group.)
  • a 005 to A 008 are each independently a substituted or unsubstituted biphenylyl group or a substituted or unsubstituted naphthyl group.
  • a 011 to A 013 are each independently a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
  • a 014 to A 016 are each independently a hydrogen atom, An unsubstituted aryl group having 6 to 50 ring carbon atoms, each of R 041 to R 043 independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a carbon atom; An alkoxyl group having 1 to 6 carbon atoms, an aryloxy group having 5 to 18 carbon atoms, an aralkyloxy group having 7 to 18 carbon atoms, an arylamino group having 5 to 16 carbon atoms, a nitro group, a cyano group, and 1 to 6 carbon atoms.
  • a fluorene compound represented by the following formula (ix) is represented by the following formula (ix).
  • R 051 and R 052 are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or a substituted amino group.
  • R 053 and R 054 may be a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic ring.
  • R 053 and R 054 which represent a group and are bonded to different fluorene groups may be the same or different, R 053 and R 054 bonded to the same fluorene group may be the same or different, and Ar 011 and Ar 012 are substituted or unsubstituted condensed polycyclic aromatics having a total of three or more benzene rings.
  • the light emitting layer may contain a phosphorescent dopant and / or a fluorescent dopant in addition to the light emitting material of the present invention, if desired.
  • a light emitting layer containing these dopants may be stacked on the light emitting layer containing the anthracene derivative of the present invention.
  • a phosphorescent dopant is a compound that can emit light from triplet excitons. Although it is not particularly limited as long as it emits light from triplet excitons, it is preferably a metal complex containing at least one metal selected from the group consisting of Ir, Ru, Pd, Pt, Os and Re, and is preferably a porphyrin metal complex or ortho Metalated metal complexes are preferred.
  • the phosphorescent compounds may be used alone or in combination of two or more.
  • the porphyrin metal complex is preferably a porphyrin platinum complex.
  • ligands that form orthometalated metal complexes.
  • Preferred ligands include compounds having a phenylpyridine skeleton, bipyridyl skeleton or phenanthroline skeleton, or 2-phenylpyridine derivatives, 7,8. -Benzoquinoline derivatives, 2- (2-thienyl) pyridine derivatives, 2- (1-naphthyl) pyridine derivatives, 2-phenylquinoline derivatives and the like.
  • These ligands may have a substituent as needed.
  • a fluorinated compound or a compound having a trifluoromethyl group introduced is preferable as a blue dopant.
  • you may have ligands other than the said ligands, such as an acetylacetonate and picric acid, as an auxiliary ligand.
  • metal complexes include tris (2-phenylpyridine) iridium, tris (2-phenylpyridine) ruthenium, tris (2-phenylpyridine) palladium, bis (2-phenylpyridine) platinum, tris (2- Phenylpyridine) osmium, tris (2-phenylpyridine) rhenium, octaethylplatinum porphyrin, octaphenylplatinum porphyrin, octaethylpalladium porphyrin, octaphenylpalladium porphyrin, etc.
  • An appropriate complex is selected depending on the device performance and the host compound to be used.
  • content in the light emitting layer of a phosphorescent dopant there is no restriction
  • Fluorescent dopants are required from amine compounds, aromatic compounds, chelate complexes such as tris (8-quinolinolato) aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives, etc. It is preferable to select a compound according to the emission color, and a styrylamine compound, a styryldiamine compound, an arylamine compound, and an aryldiamine compound are more preferable. Moreover, the condensed polycyclic aromatic compound which is not an amine compound is also preferable. These fluorescent dopants may be used alone or in combination.
  • styrylamine compound and styryldiamine compound those represented by the following formula (A) are preferable.
  • Ar 101 is a p-valent group, and a corresponding p-valent group of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a stilbenyl group, or a distyrylaryl group
  • Ar 102 and Ar 103 are Each of them is an aromatic hydrocarbon group having 6 to 20 carbon atoms
  • Ar 101 , Ar 102 and Ar 103 may be substituted, and any one of Ar 101 to Ar 103 is substituted with a styryl group.
  • At least one of Ar 102 or Ar 103 is substituted with a styryl group, and p is an integer of 1 to 4, and preferably an integer of 1 to 2.
  • examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a naphthyl group, an anthranyl group, a phenanthryl group, and a terphenyl group.
  • arylamine compound and the aryldiamine compound those represented by the following formula (B) are preferable.
  • Ar 111 is a q-valent substituted or unsubstituted aromatic hydrocarbon group having 5 to 40 ring carbon atoms
  • Ar 112 and Ar 113 are substituted or unsubstituted ring forming carbon atoms having 5 to 40 carbon atoms, respectively.
  • Q is an integer of 1 to 4, preferably an integer of 1 to 2.
  • aryl group having 5 to 40 ring carbon atoms for example, phenyl group, naphthyl group, anthranyl group, phenanthryl group, pyrenyl group, coronyl group, biphenyl group, terphenyl group, pyrrolyl group, furyl group, Thienyl group, benzothienyl group, oxadiazolyl group, diphenylanthranyl group, indolyl group, carbazolyl group, pyridyl group, benzoquinolyl group, fluoranthenyl group, acenaphthofluoranthenyl group, stilbene group, perylenyl group, chrysenyl group, picenyl group, A triphenylenyl group, a rubicenyl group, a benzoanthracenyl group, a phenylanthranyl
  • Preferred substituents for substitution on the aryl group are alkyl groups having 1 to 6 carbon atoms (ethyl group, methyl group, i-propyl group, n-propyl group, s-butyl group, t-butyl group, pentyl group).
  • hexyl group, cyclopentyl group, cyclohexyl group, etc. alkoxy group having 1 to 6 carbon atoms (ethoxy group, methoxy group, i-propoxy group, n-propoxy group, s-butoxy group, t-butoxy group, pentoxy group) Hexyloxy group, cyclopentoxy group, cyclohexyloxy group, etc.), an aryl group having 5 to 40 ring carbon atoms, an amino group substituted with an aryl group having 5 to 40 ring carbon atoms, and 5 to 5 carbon atoms forming a ring Examples include an ester group having a 40 aryl group, an ester group having an alkyl group having 1 to 6 carbon atoms, a cyano group, a nitro group, and a halogen atom.
  • the light emitting layer may contain a hole transport material, an electron transport material, and a polymer binder as necessary.
  • the thickness of the light emitting layer is preferably 5 to 50 nm, more preferably 7 to 50 nm, and most preferably 10 to 50 nm. If the thickness is less than 5 nm, it is difficult to form a light emitting layer and the adjustment of chromaticity may be difficult, and if it exceeds 50 nm, the driving voltage may increase.
  • the hole injection layer and the hole transport layer help to inject holes into the light emitting layer and transport to the light emitting region, and have a high hole mobility and a small ionization energy of usually 5.5 eV or less.
  • a material for such a hole injection layer and a hole transport layer a material that transports holes to the light emitting layer with lower electric field strength is preferable, and the hole mobility is, for example, 10 4 to 10 6 V / cm. When applying the electric field of 10 ⁇ 4 cm 2 / V ⁇ sec or more, it is preferable.
  • the material for the hole injection layer and the hole transport layer is not particularly limited, and is conventionally used as a charge transport material for holes in optical transmission materials, and the hole injection layer and holes for organic EL devices. An arbitrary thing can be selected and used from the well-known things used for the transport layer.
  • Ar 211 to Ar 213 , Ar 221 to Ar 223 and Ar 203 to Ar 208 are each a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring atom number of 5 to 5 50 heterocyclic groups.
  • a to c and p to r are integers of 0 to 3, respectively.
  • Ar 203 and Ar 204 , Ar 205 and Ar 206 , Ar 207 and Ar 208 may be connected to each other to form a saturated or unsaturated ring.
  • Ar 231 to Ar 234 are each a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • L is a linking group, which is a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • x is an integer of 0 to 5.
  • Ar 232 and Ar 233 may combine with each other to form a saturated or unsaturated ring. Specific examples of the substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms and the substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms are the same as those described above. can give.
  • the material for the hole injection layer and the hole transport layer include, for example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives. And amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (particularly thiophene oligomers).
  • the above materials can be used for the hole injection layer and the hole transport layer, but porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds, particularly aromatic tertiary amine compounds should be used. Is preferred.
  • NPD 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl
  • MTDATA triphenylamine
  • R 201 to R 206 each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted heterocyclic group.
  • R 201 and R 202 , R 203 and R 204 , R 205 and R 206 , R 201 and R 206 , R 202 and R 203 , or R 204 and R 205 may form a condensed ring.
  • R 211 to R 216 are substituents, each preferably an electron-withdrawing group such as a cyano group, a nitro group, a sulfonyl group, a carbonyl group, a trifluoromethyl group, or a halogen.
  • inorganic compounds such as p-type Si and p-type SiC can also be used as materials for the hole injection layer and the hole transport layer.
  • the hole injection layer and the hole transport layer can be formed by thinning the above-described compound by a known method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method.
  • the thickness of the hole injection layer and the hole transport layer is not particularly limited, but is usually 5 nm to 5 ⁇ m.
  • the hole injection layer and the hole transport layer may be composed of one or more layers made of the above-mentioned materials, or a plurality of hole injection layers and hole transport layers made of different compounds are laminated. There may be.
  • the organic semiconductor layer is a layer that assists hole injection or electron injection into the light emitting layer, and preferably has a conductivity of 10 ⁇ 10 S / cm or more.
  • a conductive oligomer such as a thiophene-containing oligomer or an arylamine oligomer, a conductive dendrimer such as an arylamine dendrimer, or the like can be used.
  • the electron injection layer and the electron transport layer are layers that assist injection of electrons into the light emitting layer and transport them to the light emitting region, and have a high electron mobility.
  • the adhesion improving layer is a kind of an electron injecting layer made of a material that particularly adheres well to the cathode.
  • the electron transport layer is appropriately selected with a film thickness of 5 nm to 5 ⁇ m. In particular, when the film thickness is large, the electron mobility is 10 ⁇ 5 cm when an electric field of 10 4 to 10 6 V / cm is applied in order to avoid an increase in voltage. It is preferable that it is 2 / Vs or more.
  • 8-hydroxyquinoline or a metal complex of its derivative or an oxadiazole derivative is preferable.
  • metal complexes of 8-hydroxyquinoline or its derivatives include metal chelate oxinoid compounds containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline), such as tris (8-quinolinolato) aluminum. it can.
  • Examples of the oxadiazole derivative include an electron transfer compound represented by the following formula.
  • Ar 301 , Ar 302 , Ar 303 , Ar 305 , Ar 306 , and Ar 309 each represent a substituted or unsubstituted aryl group.
  • Ar 304 , Ar 307 , and Ar 308 are each substituted or unsubstituted. Represents an arylene group.
  • the electron transfer compound is preferably a thin film-forming compound.
  • the electron transfer compound examples include the following. (Me represents a methyl group, and tBu represents a tbutyl group.)
  • materials represented by the following formulas (E) to (J) can also be used as materials used for the electron injection layer and the electron transport layer.
  • a 311 to A 313 each represent a nitrogen atom or a carbon atom.
  • Ar 311 is a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 60 ring atoms
  • Ar 311 ′ is a substituted or unsubstituted aryl group having 3 to 60 ring atoms.
  • Ar 312 is a hydrogen atom, a substituted or unsubstituted ring carbon atom having 6 to 60 carbon atoms;
  • any one of Ar 311 and Ar 312 is a substituted or unsubstituted condensed ring group having 10 to 60 ring carbon atoms, or a substituted or unsubstituted monoheterofused ring group having 3 to 60 ring atoms.
  • L 311 , L 312 and L 313 each represent a single bond, a substituted or unsubstituted arylene group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 60 ring atoms, or a substituted group. Or it is an unsubstituted fluorenylene group.
  • R and R 311 are each a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 ring atoms, and a substituted or unsubstituted carbon number.
  • adjacent R groups may be bonded to each other to form a carbocyclic aliphatic ring or a carbocyclic aromatic ring. The nitrogen-containing heterocyclic derivative represented by this.
  • HAr-L 314 -Ar 321 -Ar 322 (G) (In the formula, HAr is a nitrogen-containing heterocyclic ring having 3 to 40 carbon atoms which may have a substituent, and L 314 has a carbon number of 6 to 60 optionally having a single bond or a substituent.
  • X 301 and Y 301 are each a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, an alkenyloxy group, an alkynyloxy group, a hydroxy group, a substituted or unsubstituted aryl group, a substituted group Or an unsubstituted heterocycle or a structure in which X and Y are combined to form a saturated or unsaturated ring
  • R 301 to R 304 are each a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryloxy group Perfluoroalkyl group, perfluoroalkoxy group, amino group, alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, alkylcarbonyloxy group, arylcarbonyloxy group, alkoxycarbonyloxy group, aryl Oxycarbonyloxy group,
  • R 321 to R 328 and Z 322 are each a hydrogen atom, a saturated or unsaturated hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, a substituted amino group, a substituted boryl group, an alkoxy group or an aryl group.
  • X 302 , Y 302 and Z 321 each represents a saturated or unsaturated hydrocarbon group, aromatic hydrocarbon group, heterocyclic group, substituted amino group, alkoxy group or aryloxy group; 321 and Z 322 may be bonded to each other to form a condensed ring.
  • N represents an integer of 1 to 3, and when n or (3-n) is 2 or more, R 321 to R 328 , X 302 , Y 302 , Z 322 and Z 321 may be the same or different, provided that n is 1, X 302 , Y 302 and R 322 are methyl groups and R 328 is a hydrogen atom or a substituted boryl group. And a compound in which n is 3 and Z 321 is a methyl group).
  • Q 301 and Q 302 each represent a ligand represented by the following formula (K), and L 315 represents a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group , Substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, —OR (where R is a hydrogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryl Group, a substituted or unsubstituted heterocyclic group) or a ligand represented by —O—Ga—Q 303 (Q 304 ) (Q 303 and Q 304 are the same as Q 301 and Q 302 ). . ] The gallium complex represented by this.
  • ring A 301 and A 302 are each a 6-membered aryl ring structure condensed with each other, which may have a substituent. ]
  • This metal complex has strong properties as an n-type semiconductor and has a large electron injection capability. Furthermore, since the generation energy at the time of complex formation is also low, the bondability between the metal and the ligand of the formed metal complex is strengthened, and the fluorescence quantum efficiency as a light emitting material is large.
  • a reducing dopant is contained in a region for transporting electrons or an interface region between the cathode and the organic layer.
  • the reducing dopant is defined as a substance capable of reducing the electron transporting compound. Accordingly, various materials can be used as long as they have a certain reducibility, such as alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metals.
  • preferable reducing dopants include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV) and Cs (work function: 1. 95 eV), at least one alkali metal selected from the group consisting of Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), and Ba (work function: 2.52 eV) At least one alkaline earth metal selected from the group consisting of: A work function of 2.9 eV or less is particularly preferable.
  • a more preferable reducing dopant is at least one alkali metal selected from the group consisting of K, Rb and Cs, more preferably Rb or Cs, and most preferably Cs.
  • alkali metals have particularly high reducing ability, and the addition of a relatively small amount to the electron injection region can improve the light emission luminance and extend the life of the organic EL element.
  • a reducing dopant having a work function of 2.9 eV or less a combination of these two or more alkali metals is also preferable.
  • a combination containing Cs, for example, Cs and Na, Cs and K, Cs and Rb, A combination of Cs, Na and K is preferred.
  • An electron injection layer composed of an insulator or a semiconductor may be further provided between the cathode and the organic layer. With such a layer, current leakage can be effectively prevented, and the electron injection property can be improved. If the electron injection layer is an insulating thin film, a more uniform thin film is formed, so that pixel defects such as dark spots can be reduced.
  • the insulator it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides. It is preferable that the electron injection layer is composed of these alkali metal chalcogenides and the like, since the electron injection property can be further improved.
  • preferable alkali metal chalcogenides include, for example, Li 2 O, K 2 O, Na 2 S, Na 2 Se, and Na 2 O
  • preferable alkaline earth metal chalcogenides include, for example, CaO, BaO. , SrO, BeO, BaS, and CaSe.
  • preferable alkali metal halides include, for example, LiF, NaF, KF, CsF, LiCl, KCl, and NaCl.
  • preferable alkaline earth metal halides include fluorides such as CaF 2 , BaF 2 , SrF 2 , MgF 2 and BeF 2 , and halides other than fluorides.
  • the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film.
  • a material having a work function (for example, 4 eV or less) metal, an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, cesium, magnesium / silver alloy, aluminum / aluminum oxide, Al / Li 2 O, Al / LiO, Al / LiF, aluminum Examples include lithium alloys, indium, and rare earth metals.
  • the cathode can be produced from these electrode materials by vapor deposition or sputtering.
  • the transmittance of the cathode for light emission is preferably greater than 10%.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually 10 nm to 1 ⁇ m, preferably 50 to 200 nm.
  • an insulating thin film layer may be inserted between the pair of electrodes.
  • the material used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, Examples include germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. A mixture or laminate of these may be used.
  • the above-described materials and methods may be used to sequentially form the necessary layers from the anode and finally form the cathode.
  • an organic EL element can also be produced in the reverse order from the cathode to the anode.
  • an example of manufacturing an organic EL element having a structure in which an anode / a hole injection layer / a light emitting layer / an electron injection layer / a cathode are sequentially provided on a translucent substrate will be described.
  • a thin film made of an anode material is formed on a translucent substrate by vapor deposition or sputtering to form an anode.
  • a hole injection layer is provided on the anode.
  • the hole injection layer can be formed by a method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method.
  • the deposition conditions vary depending on the compound used (material of the hole injection layer), the structure of the target hole injection layer, etc., but generally the deposition source temperature is 50 to 450. It is preferable to appropriately select at a temperature of 10 ° C., a degree of vacuum of 10 ⁇ 7 to 10 ⁇ 3 Torr, a deposition rate of 0.01 to 50 nm / second, and a substrate temperature of ⁇ 50 to 300 ° C.
  • a light emitting layer is provided on the hole injection layer.
  • the light emitting layer can also be formed by thinning the light emitting material by a method such as vacuum deposition, sputtering, spin coating, or casting, but it is easy to obtain a uniform film and pinholes are not easily generated. From the point of view, it is preferable to form by vacuum deposition.
  • the vapor deposition conditions vary depending on the compound used, but can generally be selected from the same condition range as the formation of the hole injection layer.
  • an electron injection layer is provided on the light emitting layer.
  • a vacuum evaporation method like the hole injection layer and the light emitting layer, it is preferable to form by a vacuum evaporation method because it is necessary to obtain a homogeneous film.
  • Deposition conditions can be selected from the same condition range as the hole injection layer and the light emitting layer.
  • a cathode can be laminated
  • the cathode can be formed by vapor deposition or sputtering. In order to protect the underlying organic material layer from damage during film formation, vacuum deposition is preferred.
  • the above organic EL device is preferably produced from the anode to the cathode consistently by a single vacuum.
  • the method for forming each layer of the organic EL element is not particularly limited.
  • the organic thin film layer containing the anthracene derivative of the present invention can be prepared by vacuum deposition, molecular beam deposition (MBE method), dipping method of a solution obtained by dissolving the anthracene derivative of the present invention in a solvent, spin coating method, casting method, bar coating. It can be formed by a known method using a coating method such as a method or a roll coating method.
  • the solvent used is a good solvent for the organic EL material according to its purpose. It is possible to prepare and use a uniform solution, or to use a poor solvent or to prepare a dispersion using a mixed solvent of a good solvent and a poor solvent.
  • the organic EL material-containing solution of the present invention contains the above-described anthracene derivative of the present invention.
  • the solvent to be used is not particularly limited as long as it is generally available, and may be selected depending on the viscosity and solubility in accordance with process compatibility.
  • those that are often good solvents include aromatic solvents, halogen solvents, ether solvents, and those that are often poor solvents include alcohol solvents, ketone solvents, paraffin solvents. Examples thereof include a solvent or an alkylbenzene derivative having 4 or more carbon atoms.
  • solvents that are often good solvents include aromatic solvents such as toluene, xylene, mesitylene, halogen solvents such as chlorobenzene, and ether solvents such as diphenyl ether.
  • Alcohol-based linear or branched alcohols having 1 to 20 carbon atoms such as methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, etc., benzyl alcohol derivatives, hydroxyalkylbenzene derivatives, alkylbenzenes Examples of the derivatives include linear or branched butylbenzene, dodecylbenzene, tetralin, cyclohexylbenzene and the like.
  • the amount of the solvent used can be appropriately adjusted in consideration of the amount and type of the anthracene derivative, the thickness of the organic thin film layer, and the like.
  • the organic EL element of the present invention may be prepared by producing at least one organic thin film layer using the above-described organic EL material-containing solution of the present invention.
  • the evaluation of the organic EL element is as follows. (1) Initial performance: Emission luminance value and CIE1931 chromaticity coordinates at 10 mA / cm 2 were measured and evaluated with a luminance meter (Spectral luminance radiometer CS-1000 manufactured by Minolta). (2) life: 1000 cd / m 2 or constant current driving at an initial luminance of 5000 cd / m 2, the half-life of luminance, and was evaluated by the change in chromaticity.
  • the following compound A-2 having a thickness of 20 nm was formed as a hole transport layer on the A-1 film. Further, on this A-2 film, the compound H-1 of the present invention and the diamine derivative D-1 were formed in a film thickness ratio of 40: 2 at a film thickness ratio of 40: 2 to obtain a blue light emitting layer. H-1 functions as a host and D-1 functions as a dopant.
  • the following compound Alq was deposited as an electron transport layer with a thickness of 20 nm by vapor deposition. Thereafter, LiF was formed to a thickness of 1 nm. On the LiF film, metal Al was deposited to a thickness of 150 nm to form a metal cathode, thereby forming an organic EL device.
  • Example 2 to 4 A device was fabricated and evaluated in the same manner as in Example 1 except that D-1 was changed to the following dopant material shown in Table 1 in Example 1. The results are shown in Table 1.
  • Examples 6 to 28 A device was prepared and evaluated in the same manner as in Example 1 except that H-1 and / or D-1 was changed to the compounds shown in Table 1 in Example 1. The results are shown in Table 1 or 2. The synthesis of the anthracene compound was sequentially carried out in the same manner as in Example 1 or 5 with reference to reaction formulas 1 to 3.
  • Examples 27 to 38, Comparative Examples 3 and 4 A device was prepared and evaluated in the same manner as in Example 1 except that H-1 and / or D-1 was changed to the following compounds shown in Table 2 in Example 1. The results are shown in Table 3.
  • Compound H-12 was synthesized in the same manner using 3- (2-naphthyl) phenylboronic acid synthesized by a known method instead of 3- (1-naphthyl) phenylboronic acid.
  • Example 56-106 An organic EL device was produced using the anthracene derivative synthesized in Examples 39-55. Specifically, in Example 1, instead of H-1, the anthracene derivative synthesized in Examples 39-55 was replaced with the compounds shown in Table 4-6 instead of D-1, and instead of A-2 The following A-3 was used for the hole transport layer. Further, the following ET-1 was used in place of Alq. The other elements were fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 4.
  • the anthracene derivative of the present invention can be used as a light emitting material for an organic EL device.
  • the organic EL device of the present invention can be suitably used for light sources such as flat light emitters and display backlights, display units such as mobile phones, PDAs, car navigation systems, and vehicle instrument panels, and lighting.
  • light sources such as flat light emitters and display backlights
  • display units such as mobile phones, PDAs, car navigation systems, and vehicle instrument panels, and lighting.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Furan Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L’invention concerne un dérivé d’anthracène représenté par la formule (1) (à l’exception d’un dérivé d’anthracène représenté par la formule (1')). (Dans les formules, Ar11 à Ar14 représentent chacun un groupe hydrocarbure aromatique substitué ou non substitué ou un groupe hétérocyclique aromatique substitué ou non substitué; et Ar21 à Ar24 représentent chacun un atome d’hydrogène, un groupe alkyle substitué ou non substitué, un groupe hydrocarbure aromatique substitué ou non substitué ou un groupe hétérocyclique aromatique substitué ou non substitué. Incidemment, lorsque tous les Ar11 à Ar14 sont des cycles benzène, tous les Ar21 à Ar24 ne sont pas des atomes d’hydrogène; et, lorsqu’au moins l’un parmi Ar11 à Ar14 est un groupe 9,9'-diméthylfluorényle ou un groupe 9,9'-diphénylfluorényle, tous les autres ne sont pas des groupes phényles non substitués).
PCT/JP2009/060963 2008-06-17 2009-06-16 Dérivé d’anthracène et élément électroluminescent organique l’utilisant WO2009154207A1 (fr)

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JP2019134049A (ja) * 2018-01-31 2019-08-08 ソニー株式会社 光電変換素子および撮像装置
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JP2013207139A (ja) * 2012-03-29 2013-10-07 Kaneka Corp 発光材料および有機ｅｌ素子
CN103896715A (zh) * 2012-12-27 2014-07-02 乐金显示有限公司 蓝色荧光化合物和使用其的有机发光二极管装置
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WO2016117848A1 (fr) * 2015-01-20 2016-07-28 에스에프씨 주식회사 Composé pour dispositif électroluminescent organique et dispositif électroluminescent organique comprenant celui-ci
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WO2019035412A1 (fr) 2017-08-14 2019-02-21 出光興産株式会社 Élément électroluminescent organique et dispositif électronique
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US10109804B1 (en) 2017-08-14 2018-10-23 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and electronic device
KR20200040225A (ko) 2017-08-14 2020-04-17 이데미쓰 고산 가부시키가이샤 유기 일렉트로루미네센스 소자 및 전자 기기
US10103338B1 (en) 2017-08-14 2018-10-16 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and electronic device
US11665962B2 (en) 2017-08-14 2023-05-30 Idemitsu Kosan Co., Ltd. Organic electroluminescence element and electronic device
JP2019134049A (ja) * 2018-01-31 2019-08-08 ソニー株式会社 光電変換素子および撮像装置
WO2019150988A1 (fr) * 2018-01-31 2019-08-08 ソニー株式会社 Transducteur photoélectrique et dispositif de prise de vue
JP7117110B2 (ja) 2018-01-31 2022-08-12 ソニーグループ株式会社 光電変換素子および撮像装置
WO2020039708A1 (fr) 2018-08-23 2020-02-27 国立大学法人九州大学 Élément électroluminescent organique

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