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WO2010016405A1 - Nouveau dérivé d'amine aromatique et élément électroluminescent organique l'utilisant - Google Patents

Nouveau dérivé d'amine aromatique et élément électroluminescent organique l'utilisant Download PDF

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WO2010016405A1
WO2010016405A1 PCT/JP2009/063350 JP2009063350W WO2010016405A1 WO 2010016405 A1 WO2010016405 A1 WO 2010016405A1 JP 2009063350 W JP2009063350 W JP 2009063350W WO 2010016405 A1 WO2010016405 A1 WO 2010016405A1
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amine derivative
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文雄 奥田
哲也 井上
正和 舟橋
光則 伊藤
由美子 水木
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Idemitsu Kosan Co Ltd
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    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
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    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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    • 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
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • 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
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    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
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    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3

Definitions

  • the present invention relates to an aromatic amine derivative and an organic electroluminescence device using the aromatic amine derivative, and more particularly to an organic electroluminescence device having a long lifetime and high emission efficiency, which can produce green or blue light emission, and an aromatic amine derivative that realizes the organic electroluminescence device.
  • an organic EL element (organic electroluminescence element) using light emission of an organic compound.
  • the organic EL element has a plurality of organic thin films stacked between an anode and a cathode.
  • a voltage is applied between the anode and the cathode, holes and electrons are injected into the organic thin film from the anode and the cathode, respectively.
  • Excited molecules are generated in the light emitting layer in the organic thin film by the injected holes and electrons. Then, energy when returning from the excited state to the ground state is emitted as light.
  • Patent Documents 1 and 2 disclose various combinations of an anthracene host and an aryldiamine dopant, and express performances that can withstand practical use. Further, Patent Document 3 discloses a combination of a diaminopyrene dopant having a specific structure and an anthracene host, but there is no description regarding element lifetime and the like. Recently, there is an increasing demand for higher performance element performance, and a higher performance light emitting material is desired.
  • the present invention has been made to solve the above-described problems, and in particular, an organic EL device having a long lifetime and high emission efficiency, which can obtain green or blue light emission, a novel aromatic amine derivative and an organic EL device that realizes the same.
  • the object is to provide a material-containing solution.
  • the present inventors have a long lifetime by using an aromatic amine derivative having a specific structure.
  • the inventors have found that the object of obtaining green or blue light emission with high luminous efficiency can be achieved.
  • the present invention has been completed based on such findings.
  • An aromatic amine derivative represented by the following formula (1) is an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • a1 is an integer of 0 to 11.
  • R 1 and R 2 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group; May be the same or different.
  • b1 and c1 are each an integer of 0 to 10.
  • a 1 to A 4 are phenyl groups when X is pyrene and the 1-position and 6-position thereof are substituted with amino groups and no substituents are present at other parts of the pyrene ring except for. Except when X is pyrene and the 1- and 6-positions thereof are substituted with amino groups, the pyrene ring has sec-butyl groups at the 3rd and 8th positions.
  • n1 is an integer of 2 to 12 in the formula (2).
  • n1 is an integer of 3 to 12 in the formula (2). 4).
  • X is naphthalene, phenanthrene, anthracene, diphenylanthracene, bisanthracene, chrysene, hydrochrysene, pyrene, diphenylpyrene, fluorene, spirofluorene, benzofluorene, dibenzofluorene, fluoranthene, benzothiophene, dibenzothiophene, 2.
  • the aromatic amine derivative according to 1 above selected from the group consisting of benzofuran, dibenzofuran, and the following formula (6 ′).
  • Ar 5 and Ar 6 each represent a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group. ] 5).
  • X is pyrene. 6).
  • R 1 and R 2 are each a substituted or unsubstituted aryl group, and b1 and c1 are each an integer of 1 to 10. 7).
  • the aromatic amine derivative according to 1 above, wherein the compound of the formula (1) is a compound of the following formula (3).
  • a 1 is represented by the following formula (7)
  • a 2 is represented by the following formula (8)
  • X is represented by the following formula (9)
  • a1 is 0, and b1 is 2.
  • Ar 7 to Ar 9 are each a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group
  • a 21 to A 23 are each a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group
  • at least one of A 21 to A 23 is represented by the formula (2)
  • n1 is an integer of 1 to 12
  • p, q, and r are integers of 0 or 1
  • the aromatic amine derivative according to 1 above, wherein the compound of the formula (1) is a compound of the following formula (10).
  • [In Formula (10), A 1 to A 4 are the same as in Formula (1). ] 16.
  • [In Formula (11), A 1 to A 4 are the same as in Formula (1), and R 5 to R 8 are the same as R 1 and R 2 in Formula (1). ] 18.
  • a light emitting material comprising the aromatic amine derivative according to any one of 1 to 17 above. 19. 19.
  • An anode and a cathode Having one or more organic thin film layers sandwiched between the anode and the cathode, 18.
  • An organic electroluminescence device wherein at least one of the organic thin film layers contains the aromatic amine derivative according to any one of 1 to 17 above. 21. 21. The organic electroluminescence device as described in 20 above, wherein the layer containing the aromatic amine derivative further contains a host material. 22. 21.
  • the host material wherein the host material is at least one selected from the group consisting of an anthracene compound, a bisanthracene compound, a pyrene compound, a fluorene compound, a triarylamine compound, a fluoranthene compound, and a compound represented by the following formula (2f).
  • the organic electroluminescent element of description Ar represents a trivalent group derived from an aromatic ring or a heteroaromatic ring, Ar 18 , Ar 19 and Ar 20 are each a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and at least one of the substituents of the aryl group of Ar 18 , Ar 19 and Ar 20 is a ring.
  • the organic electroluminescence device according to any one of 20 to 22, wherein the layer containing the aromatic amine derivative further contains at least one of a phosphorescent dopant and a fluorescent dopant. 24. 24. The organic electroluminescence device as described in 23 above, wherein the phosphorescent dopant is a metal complex. 25. 20. An organic electroluminescent material-containing solution containing the light-emitting material according to 18 or 19 above. 26. 26. An organic electroluminescence device produced using the organic electroluminescence material-containing solution described in 25 above.
  • the organic EL device using the aromatic amine derivative of the present invention has a high luminous efficiency and is not easily deteriorated even when used for a long time, and has a long life.
  • the aromatic amine derivative of the present invention is a compound represented by the following formula (1).
  • X is an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • a1 is an integer of 0 to 11, preferably an integer of 0 to 3.
  • Each of R 1 and R 2 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group; May be the same or different.
  • b1 and c1 are each an integer of 0 to 10, preferably an integer of 0 to 4.
  • a 1 to A 4 are each a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, and at least one of A 1 to A 4 is represented by the following formula (2 ).
  • the hydrogen atom bonded to the aromatic amine derivative of the present invention may be a deuterium atom.
  • n1 is an integer of 1 to 12.
  • Examples of the aromatic hydrocarbon ring or aromatic heterocycle of X include the following.
  • X is naphthalene, phenanthrene, anthracene, diphenylanthracene, bisanthracene, chrysene, hydrochrysene, pyrene, diphenylpyrene, fluorene, spirofluorene, benzofluorene, dibenzofluorene, fluoranthene, benzothiophene, dibenzothiophene, benzofuran, dibenzofuran and the following formula It is preferably selected from the group consisting of (6 ′).
  • Ar 5 and Ar 6 each represent a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group.
  • X is selected from pyrene, anthracene, chrysene, fluorene or the above formula (6 ').
  • R 1 and R 2 are each preferably a substituted or unsubstituted aryl group, and b1 and c1 are each preferably an integer of 1 to 10.
  • X is represented by the following formula (3), a1 is 1, b1 is 1, c1 is 1, and R 1 and R 2 are in the 3rd and 8th positions, respectively.
  • Aromatic amine derivatives that bind are preferred.
  • a 1 to A 4 , R 1 and R 2 are the same as those in the formula (1).
  • X is preferably represented by the following formula (6 ′).
  • Ar 5 and Ar 6 are each a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group.
  • X is the above formula (6 ′), a1 is 1, b1 is 0, and c1 is 0, an aromatic amine derivative represented by the following formula (6) Is preferred.
  • a 1 to A 4 , R 1 and R 2 are the same as those in the formula (1).
  • Ar 5 and Ar 6 are as described above.
  • Ar 7 to Ar 9 are each a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group.
  • a 21 to A 23 are each a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, and at least one of A 21 to A 23 is represented by the formula (2) (In the formula (2), n1 is an integer of 1 to 12).
  • p, q, and r are integers of 0 or 1, and p + q + r ⁇ 1.
  • the aromatic amine derivative has the following structure.
  • Ar 7 to Ar 9 , A 21 to A 23 , p, q and r are the same as in the above formulas (7) to (9).
  • X when X is fluorene, it is preferably represented by the following formula (11). More preferably, a1 in formula (1) is 1, b1 is 2, and both R 1 are bonded to the 5-position, and c1 is 2 and both R 2 are bonded to the 11-position. It is an aromatic amine derivative.
  • a 1 to A 4 are the same as the above formula (1).
  • R 5 to R 8 are the same as R 1 and R 2 in the formula (1).
  • Examples of the unsubstituted alkyl group for R 1 and R 2 include an alkyl group having 1 to 50 carbon atoms, specifically, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, Examples thereof include s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group and n-octyl group.
  • substituted alkyl groups for R 1 and R 2 include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxyethyl, 1,3-dihydroxy Isopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloro Ethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl
  • Examples of the aromatic hydrocarbon group of R 1 and R 2 include phenyl group, indenyl group, fluorenyl group, naphthyl group, anthryl group, phenanthryl group, naphthacenyl group, acenaphthylenyl group, biphenyl group, chrysenyl group, pyrenyl group, triphenyl group, Examples include a phenyl group, a fluoranthenyl group, and a perylenyl group, and a naphthyl group, a phenanthryl group, a chrysenyl group, a pyrenyl group, a triphenyl group, a fluorenyl group, and a terphenyl group.
  • the aromatic hydrocarbon group for R 1 and R 2 preferably has 6 to 60 ring carbon atoms, and more preferably 6 to 30 ring carbon atoms.
  • Examples of the aromatic heterocyclic group for R 1 and R 2 include a pyrrolyl group, a pyridinyl group, a pyrazinyl group, an indolyl group, a furyl group, a dibenzofuranyl group, a dibenzothienyl group, a quinolyl group, and a carbazolyl group.
  • the aromatic heterocyclic group for R 1 and R 2 preferably has 5 to 18 ring carbon atoms.
  • the aromatic hydrocarbon group and aromatic heterocyclic group of R 1 and R 2 may be substituted.
  • substituents include an alkyl group having 1 to 6 carbon atoms and an aromatic hydrocarbon having 6 to 60 carbon atoms. And aromatic heterocyclic groups having 2 to 60 carbon atoms.
  • Examples of the group that becomes the aromatic hydrocarbon group and aromatic heterocyclic group of A 1 to A 4 include the following.
  • At least one of A 1 to A 4 needs to have a substituent represented by the following formula (2).
  • n1 represents the number of substitutions of the group represented by the formula (2) for any one of A 1 to A 4 and is an integer of 1 to 12, preferably 2 to 12, more preferably 3 An integer of ⁇ 12.
  • n1 can be increased. Specifically, n1 can be 2 or more, or 3 or more.
  • substituents other than the substituent represented by the above formula (2) when A 1 to A 4 are a substituted aromatic hydrocarbon group or a substituted aromatic heterocyclic group
  • 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, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.
  • an alkenyl group preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 8 carbon atoms).
  • 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 having 6 to 30 carbon atoms, particularly preferably having 6 to 20 carbon atoms, Phenyl, fluorenyl, naphthyl, anthryl, phenanthryl, chrysenyl, pyrenyl, triphenylenyl, fluoranthenyl, etc.
  • a 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 such as amino, methylamino, dimethylamino, diethylamino, diphenylamino, dibenzylamino, etc.
  • Alkoxy groups preferably having 1 to 20 carbon atoms, more preferably having carbon atoms
  • 1 to 12 carbon atoms particularly preferably 1 to 8 carbon atoms
  • methoxy, eth And aryloxy groups preferably having 6 to 20 carbon atoms, more preferably 6 to 16 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyloxy, 2-naphthyloxy.
  • An acyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, and particularly preferably 1 to 12 carbon atoms, and examples thereof include acetyl, benzoyl, formyl, pivaloyl, and the like. ), An alkoxycarbonyl group (preferably having 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, etc.), aryloxy A carbonyl group (preferably having 7 to 20 carbon atoms, more preferably 7 to 16 carbon atoms, particularly preferably 7 to 10 carbon atoms). For example, phenyloxycarbonyl and the like can be mentioned.
  • An acyloxy group (preferably having 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy, benzoyloxy, etc.), an acylamino group (preferably 2-20 carbon atoms, more preferably 2-16 carbon atoms, particularly preferably 2-10 carbon atoms, and examples thereof include acetylamino, benzoylamino, and the like, and alkoxycarbonylamino groups (preferably having 2-2 carbon atoms).
  • aryloxycarbonylamino group preferably 7 to 20 carbon atoms, more preferably 7 to 16 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonylamino
  • a substituted or unsubstituted sulfonylamino group preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonyl.
  • a substituted or unsubstituted sulfamoyl group (preferably having a carbon number of 0 to 20, more preferably a carbon number of 0 to 16, particularly preferably a carbon number of 0 to 12, such as sulfamoyl, methylsulfayl).
  • Moyl, 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 carbon atoms).
  • An alkylthio group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio, ethylthio, etc.), an arylthio group ( Preferably, it has 6 to 20 carbon atoms, more preferably 6 to 16 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, etc.), a substituted or unsubstituted sulfonyl group (preferably 1 carbon atom) To 20, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl, tosyl, etc.), substituted or unsubstituted sulfinyl groups (preferably having 1 to 20 carbon atoms, More preferably, it has
  • a substituted or unsubstituted ureido group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include ureido, methylureido, phenylureido and the like.
  • Substituted or unsubstituted phosphoramide 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, etc.
  • hydroxy group preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphate amide, phenyl phosphate Amide, etc.
  • 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, A hydrazino group, an imino group, a heterocyclic group (preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, For example, those containing a nitrogen
  • a silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyl and triphenylsilyl). .
  • These substituents may be further substituted. Moreover, when there are two or more substituents, they may be the same or different. If possible, the above substituents 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, and triphenylsilyl.
  • the aromatic amine derivative of the present invention can be obtained, for example, by the synthetic route shown below. Each step can be performed by a method known to those skilled in the art.
  • the present invention also provides a polymer compound having the structure of the aromatic amine derivative represented by the formula (1) as at least a part of the repeating unit.
  • the polymer compound of the present invention is synthesized using any of the methods usually used in polymer synthesis (polycondensation reaction, coupling reaction, radical reaction, living polymerization, etc.).
  • the structure or the like is not particularly limited, but the molecular weight is preferably equal to or higher than the degree of polymerization having a glass transition point.
  • the ratio of the aromatic amine derivative is not particularly limited as long as the characteristics are exhibited, but usually the ratio is in the range of 50 to 99.99% by weight in order to exhibit the characteristics as the host material. Is preferred.
  • the aromatic amine derivative or polymer compound of the present invention can be used as a light emitting material for an organic EL device. Preferably it is used as a dopant material.
  • the organic EL device of the present invention has an anode and a cathode, and one or more organic thin film layers including a light emitting layer sandwiched between the anode and the cathode, and at least one of the organic thin film layers of the present invention.
  • the light-emitting layer preferably contains at least one aromatic amine derivative or polymer compound, and the light-emitting layer contains an aromatic amine derivative or polymer compound.
  • the aromatic amine derivative partial structure is preferably contained in an amount of 0.001 to 50% by weight, more preferably 0.005 to 10% by weight, and 0.01 to 5% by weight. Most preferred.
  • the layer containing the aromatic amine derivative or polymer compound 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 is preferably at least one selected from the group consisting of arylamine compounds, styrylamine compounds and fluoranthene compounds.
  • a metal complex is preferable. Specific examples thereof will be described in the description of the light emitting layer described later.
  • FIG. 1 shows the configuration of the organic EL element of (8) above.
  • the organic EL element includes an anode 10 and a cathode 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 a plurality of organic thin film layers. At least one of these organic thin film layers 30, 32, 34, and 36 contains the above aromatic amine derivative or polymer compound.
  • 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 has a work function of 4.5 eV or more by injecting holes into the hole injection layer, the hole transport layer, or the light emitting layer.
  • anode materials include indium tin oxide (ITO), a mixture of indium oxide and zinc oxide (IZO), a mixture of ITO and cerium oxide (ITCO), a mixture of IZO and cerium oxide (IZCO), and indium oxide and oxide. Examples thereof include a mixture of cerium (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 larger 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 the aggregation structure and the 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 other than the light-emitting material of the present invention that can be used in the light-emitting layer include anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone, naphthaloperinone, and diphenylbutadiene.
  • Tetraphenylbutadiene 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 compound, quinacridone, rubrene and these Derivatives and fluorescent dyes, and the like, but not limited thereto.
  • the aromatic amine derivative or polymer compound of the present invention is used as a light emitting material for an organic EL device, the light emitting layer contains at least one aromatic amine derivative or polymer compound represented by the following formulas (2a) to (2f). It is preferable to include at least one selected from the compounds represented.
  • Ar 11 and Ar 12 are each a group derived from a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms.
  • the aromatic ring may be substituted with one or more substituents.
  • the aromatic ring has a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms.
  • substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms substituted or unsubstituted aralkyl group (aryl portion having 6 to 50 carbon atoms, alkyl portion having 1 to 5 carbon atoms), substituted or unsubstituted carbon number 6 to 50 aryloxy groups, substituted or unsubstituted arylthio groups having 6 to 50 carbon atoms, substituted or unsubstituted alkoxycarbonyl groups (the alkoxy moiety has 1 to 50 carbon atoms), substituted or unsubstituted silyl groups, carboxyls group, a halogen atom, a cyano group, a nitro group and a hydroxyl group, is selected from the groups described below as specific examples of R 11 ⁇ R 18 That.
  • the substituents When the aromatic ring is substituted with two or more substituents, the substituents may be the same or different, and adjacent substituents are bonded to each other to form a saturated or unsaturated cyclic structure. It may be formed.
  • Ar 11 and Ar 12 is preferably different. Further, at least one of Ar 11 and Ar 12 is preferably a substituent having a substituted or unsubstituted condensed ring group having 10 to 30 carbon atoms, and having a substituted or unsubstituted naphthyl group. Is more preferable.
  • R 11 to R 18 are each a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 50 carbon atoms, a substituted or unsubstituted carbon atom having 1 to 50 alkyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl groups (the aryl moiety has 6 to 50 carbon atoms)
  • the alkyl moiety has 1 to 50 carbon atoms), a substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 50 carbon atoms, a substituted or unsubstituted alkoxycarbonyl group (alkyl The mo
  • the anthracene derivative represented by the formula (2a) is preferably a compound having a structure represented by the following formula (2a ′).
  • Ar 11, Ar 12 and R 11 to R 18 are as defined in the formula (2a).
  • the substituents Ar 11 and Ar 12 at the 9th and 10th positions of the anthracene structure are asymmetric with respect to the XY axis.
  • anthracene derivative represented by the formula (2a) used in the organic EL device of the present invention include those in the molecule described in JP-A-2004-356033 [0043] to [0063].
  • Examples include various anthracene derivatives known in the art, such as those having two anthracene skeletons and compounds having one anthracene skeleton shown in pages 27 to 28 of WO 2005/061656.
  • Ar 13 and Ar 14 are each a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms
  • L 1 and L 2 are each a substituted or unsubstituted phenylene group
  • m is an integer of 0 to 2
  • n is an integer of 1 to 4
  • s is an integer from 0 to 2
  • t is an integer from 0 to 4.
  • L 1 or Ar 13 is bonded to any one of positions 1 to 5 of pyrene
  • L 2 or Ar 14 is bonded to any of positions 6 to 10 of pyrene.
  • Ar 15 to Ar 17 are each selected from a group having an anthracene structure, a group having a phenanthrene structure, and a group having a pyrene structure, and R 19 to R 21 are each a hydrogen atom or Represents a substituent.
  • Ar 15 to Ar 17 in the formula (2c) are preferably selected from a substituted or unsubstituted anthrylphenyl group, anthryl group, phenanthrenyl group, perylenyl group and pyrenyl group, and more preferably an alkyl-substituted or unsubstituted anthryl. It is selected from a phenyl group, a phenanthryl group and a pyrenyl group, and particularly preferably selected from a pyrenyl group and a phenanthryl group.
  • R 19 to R 21 in the formula (2c) include a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an acyl group, an alkoxycarbonyl group, Aryloxycarbonyl group, acyloxy group, acylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, arylthio group, heteroarylthio group, sulfonyl group, sulfinyl group, ureido group, phosphoric acid amide Group, hydroxy group, mercapto group, halogen atom, cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydra
  • 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 aromatic heterocyclic group, substituted amino Represents a group, a cyano group or a halogen atom.
  • R 051 together to bind to a different fluorene group, R 052 each other or different may be the same, R 051 and R 052 bonding to the same fluorene group may be different even in the same.
  • R 053 and R 054 represent 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 aromatic heterocyclic group, and different fluorene groups R 053 and R 054 bonded to each other may be the same or different, and R 053 and R 054 bonded to the same fluorene group may be the same or different.
  • Ar 011 and Ar 012 are fluorenes of a substituted or unsubstituted condensed polycyclic aromatic hydrocarbon group having a total of 3 or more benzene rings or a substituted or unsubstituted carbon having a total of 3 or more benzene rings and heterocyclic rings.
  • n 1 represents an integer of 1 to 10.
  • Fluoranthene compounds represented by the following formulas (2e-1) to (2e-5).
  • R 401 to R 414 each independently represents a hydrogen atom, a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms, a substituted or unsubstituted group.
  • n 4 is 1 to 4
  • X 1 to X 16 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted straight chain, branched or A cyclic alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted straight chain, branched or cyclic alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted straight chain, branched or cyclic carbon atom number 1 30 to 30 alkylthio groups, substituted or unsubstituted linear, branched or cyclic alkenyl groups having 2 to 30 carbon atoms, substituted or unsubstituted linear, branched or cyclic alkenyloxy groups having 2 to 30 carbon atoms Substituted or unsubstituted linear, branched or cyclic alkenylthio group having 2 to 30 carbon atoms, substituted or unsubstituted linear, branched or
  • Ar 18 to Ar 20 each represents an aryl group having 6 to 50 ring carbon atoms, and the aryl group may be substituted with one or more substituents.
  • Ar 18 to Ar 20 and at least one of the substituents of these aryl groups have a condensed ring aryl structure having 10 to 20 ring carbon atoms or a condensed ring heteroaryl structure having 6 to 20 ring carbon atoms.
  • Ar represents a trivalent group derived from an aromatic ring or a heteroaromatic ring.
  • 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. Moreover, you may laminate
  • 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 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, and the like.
  • An appropriate complex may be selected depending on the device performance and the host compound to be used.
  • the content of the phosphorescent dopant in the light emitting layer is not particularly limited and may be appropriately selected depending on the intended purpose. For example, it is 0.1 to 70% by weight, and preferably 1 to 30% by weight. If the content of the phosphorescent compound is less than 0.1% by weight, light emission is weak and the effect of the content may not be sufficiently exhibited. If the content exceeds 70% by weight, a phenomenon called concentration quenching becomes prominent and the element Performance may be reduced.
  • 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 in accordance with 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 corresponding p-valent group of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a stilbenyl group, or a distyrylaryl group, and Ar 102 and Ar 103 each have 6 to 6 carbon atoms.
  • 20 aromatic hydrocarbon groups, Ar 101 , Ar 102 and Ar 103 may be substituted. Any one of Ar 101 to Ar 103 is substituted with a styryl group. More preferably, at least one of Ar 102 or Ar 103 is substituted with a styryl group.
  • p is an integer of 1 to 4, 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 each substituted or unsubstituted ring forming carbon atoms having 5 to 40 carbon atoms.
  • q is an integer of 1 to 4, preferably an integer of 1 to 2.
  • 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 it may be difficult to adjust the chromaticity. If the thickness 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 / When an electric field of cm is applied, it is preferably 10 ⁇ 4 cm 2 / V ⁇ second or more.
  • the material of 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 of organic EL devices. An arbitrary thing can be selected and used from the well-known things used for the transport layer.
  • an aromatic amine derivative represented by the following formula can be used.
  • 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 formation An aromatic heterocyclic group having 5 to 50 atoms.
  • a to f 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 aromatic heterocyclic group having 5 to 50 ring atoms.
  • L is a linking group, a single bond, a divalent substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a divalent substituted or unsubstituted aromatic group having 5 to 50 ring atoms.
  • Group heterocyclic group. 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.
  • 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
  • each of R 201 to R 206 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic 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, and are preferably electron-withdrawing groups such as a cyano group, a nitro group, a sulfonyl group, a carbonyl group, a trifluoromethyl group, and a halogen, respectively.
  • 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 help to inject electrons into the light emitting layer and transport electrons 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.
  • the Ar 304, Ar 307, Ar 308 represents respectively substituted or unsubstituted arylene group.
  • the electron transfer compound examples include the following.
  • Me represents a methyl group
  • t-Bu represents a tbutyl group.
  • a 311 to A 313 each represent a nitrogen atom or a carbon atom.
  • Ar 311 is a substituted or unsubstituted ring aryl group having 6 to 60, or a substituted or unsubstituted heteroaryl group having ring atoms 3 to 60, Ar 311 'is a substituted or unsubstituted An arylene group having 6 to 60 ring carbon atoms or a substituted or unsubstituted heteroarylene 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; An aryl group, a substituted or unsubstituted heteroaryl group having 3 to 60 ring atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 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 are each 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, An unsubstituted fluorenylene group.
  • R 4 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, a substituted or unsubstituted carbon.
  • the R 4 groups adjacent to each other may be bonded to each other to form a carbocyclic aliphatic ring or a carbocyclic aromatic ring.
  • HAr 30 is a nitrogen-containing heterocyclic group having 3 to 40 carbon atoms which may have a substituent
  • L 314 is a carbon having a single bond or a substituent.
  • Ar 321 has a substituent.
  • a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms, and Ar 322 may have an aryl group or substituent having 6 to 60 carbon atoms which may have a substituent. Or a heteroaryl group having 3 to 60 atoms.
  • X 301 and Y 301 each represent 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 structure forming a ring substituted or unsubstituted heterocyclic or X 301 and Y 301 are bonded to a saturated or unsaturated, R 301 ⁇ R 304 are independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group , Aryloxy group, perfluoroalkyl group, perfluoroalkoxy group, amino group, alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, azo group, alkylcarbonyloxy group, arylcarbonyloxy group, alkoxycarbonyl Oxy group, aryloxycarbon
  • 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 Represents an aryloxy 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 2 represents an integer of 1 to 3
  • R 321 to R 328 , X 302 , Y 302 , Z 322 and Z 321 may be the same or different.
  • n 2 is 1, X 302 , Y 302 and R 322 are methyl groups, R 328 is a hydrogen atom or
  • Gallium complex represented by formula (J) In formula (J), 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.
  • R 5 is a hydrogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted Or an unsubstituted aryl group, a substituted or unsubstituted aromatic heterocyclic group.
  • R 5 is a hydrogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted Or an unsubstituted aryl group, a substituted or unsubstituted aromatic heterocyclic group.
  • Q 304 Q 303 and Q 304 are the same as Q 301 and Q 302.
  • rings 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 two or more alkali metals is also preferable.
  • a combination containing Cs, such as 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 for light emission of the cathode is preferably larger than 10%.
  • the sheet resistance as a 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 evaporation 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 evaporation 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 aromatic amine derivative or polymer compound of the present invention can be obtained by vacuum evaporation, molecular beam deposition (MBE method), or a solution obtained by dissolving the aromatic amine derivative or polymer compound of the present invention in a solvent.
  • the film can be formed by a known method such as a dipping method, a spin coating method, a casting method, a bar coating 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 a dispersion liquid prepared 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 aromatic amine derivative or polymer compound 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.
  • aromatic solvents such as toluene, xylene, and mesitylene
  • halogen-based solvents such as chlorobenzene
  • ether-based solvents such as diphenyl ether
  • Specific examples of what is often a poor solvent include alcoholic solvents such as methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, etc.
  • examples thereof include branched alcohols, benzyl alcohol derivatives, and hydroxyalkylbenzene derivatives.
  • alkylbenzene derivative 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 aromatic amine derivative or polymer compound, the thickness of the organic thin film layer, and the like.
  • the organic EL element of the present invention may be one in which at least one organic thin film layer is produced using the above-described organic EL material-containing solution of the present invention.
  • Toluene was removed from the resulting heterogeneous solution, methanol was added, and the insoluble material was filtered off. Further, washing with water and methanol was performed. This insoluble matter was dissolved in 100 mL of hot toluene, and the fraction solution passed through a silica column (toluene) was concentrated to about 150 mL. 200 mL of ether was added to this to recrystallize the target product, and further washed with 200 mL of hot ethanol to obtain 2.8 g (yield 57%) of the target product.
  • Toluene was removed from the resulting heterogeneous solution, methanol was added, and the insoluble material was filtered off. Further, washing with water and methanol was performed. This insoluble matter was dissolved in 700 mL of hot toluene, and the fraction solution passed through a silica column (toluene) was concentrated to about 150 mL. Ether was added and recrystallized to obtain 4.2 g (yield 73%) of the desired product.
  • Toluene was removed from the resulting heterogeneous solution, methanol was added, and the insoluble material was filtered off. Further, washing with water and methanol was performed. This insoluble matter was dissolved in 500 mL of hot toluene, and the fraction solution passed through a silica column (toluene) was concentrated to about 50 mL. Ether was added and recrystallized to obtain 3.3 g (yield 65%) of the target product.
  • Example 1 Production of Organic EL Element A transparent electrode made of indium tin oxide having a thickness of 120 nm was provided on a glass substrate having a size of 25 mm ⁇ 75 mm ⁇ 1.1 mm. This transparent electrode serves as an anode. Subsequently, the glass substrate was cleaned by irradiating ultraviolet rays and ozone, and then the substrate was placed in a vacuum deposition apparatus.
  • N ′, N ′′ -bis [4- (diphenylamino) phenyl] -N ′, N ′′ -diphenylbiphenyl-4,4′-diamine was deposited to a thickness of 60 nm
  • N, N, N ′, N′-tetrakis (4-biphenyl) -4,4′-benzidine was deposited to a thickness of 20 nm as a hole transport layer.
  • an anthracene derivative (H-1) as a host material and an amine derivative (D-1) as a doping material were co-evaporated at a mass ratio of 40: 2 to form a light-emitting layer having a thickness of 40 nm.
  • tris (8-hydroxyquinolinato) aluminum was deposited to a thickness of 20 nm as an electron injection layer.
  • lithium fluoride was deposited to a thickness of 1 nm, and then aluminum was deposited to a thickness of 150 nm to produce an organic EL device.
  • the aluminum / lithium fluoride serves as a cathode.
  • Examples 2 to 15 and Comparative Examples 1 and 2 An organic EL device was prepared in the same manner as in Example 1 except that the dopant material and the host material were changed to the compounds shown in Table 1 below, and the device performance was evaluated. The results are shown in Table 1 below.
  • the host materials described in Table 1 represent the following.
  • the dopant used by the comparative example in Table 1 represents the following.
  • compound (B-2) 23.4 mmol (6.57 g), 1,6-dibromo-3,8-di (2′-naphthyl) pyrene (BrPyr) instead of compound ( A-12) Synthesis was performed in the same manner as Compound (D-1) except that 5.2 mmol (2.43 g) was used, and 2.85 g (yield 63.0%) of Compound (D-12) was obtained. .
  • Examples 16 to 18 and Comparative Example 3 An organic EL device was prepared in the same manner as in Example 1 except that the dopant material and the host material were changed to the compounds shown in Table 2, and the device performance was evaluated. The results are shown in Table 2.
  • the dopant used by the comparative example in Table 2 represents the following.
  • Examples 19 and 20 and Comparative Examples 4 and 5 An organic EL device was prepared in the same manner as in Example 1 except that the dopant material and the host material were changed to the compounds shown in Table 3 and the initial luminance in the half-life measurement was changed to 2000 cd / m 2 , and the device performance was evaluated. It was. The results are shown in Table 3.
  • the dopant used by the comparative example in Table 3 represents the following.
  • the organic EL device having a light emitting layer using the aromatic amine derivative of the present invention as a dopant has high luminous efficiency and long half-life.
  • the aromatic amine derivative of the present invention is useful as a light emitting material for an organic EL device.
  • ADVANTAGE OF THE INVENTION According to this invention, the outstanding organic electroluminescent element from which green or blue light emission with a long lifetime and high luminous efficiency can be obtained can be provided.
  • An aromatic amine derivative represented by the following formula (1) is an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • a1 is an integer of 0 to 11.
  • R 1 and R 2 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group; May be the same or different.
  • b1 and c1 are each an integer of 0 to 10.
  • a 1 to A 4 are phenyl groups when X is pyrene and the 1-position and 6-position thereof are substituted with amino groups and no substituents are present at other parts of the pyrene ring except for. ] 2.
  • X is naphthalene, phenanthrene, anthracene, diphenylanthracene, bisanthracene, chrysene, hydrochrysene, pyrene, diphenylpyrene, styryl, fluorene, spirofluorene, benzofluorene, dibenzofluorene, fluoranthene, benzothiophene, dibenzo 2.
  • the aromatic amine derivative according to 1 above which is a group selected from the group consisting of thiophene, benzofuran, and dibenzofuran. 3. 3. A polymer compound having a structure derived from the aromatic amine derivative according to 1 or 2 as at least a part of a repeating unit. 4). 3. A light emitting material comprising the aromatic amine derivative according to 1 or 2 or the polymer compound according to 3 above. 5). 5. The light emitting material as described in 4 above, wherein the aromatic amine derivative or polymer compound is a dopant material. 6). An anode and a cathode; Having one or more organic thin film layers sandwiched between the anode and the cathode, 3.
  • An organic electroluminescence device in which at least one of the organic thin film layers contains the aromatic amine derivative described in 1 or 2 above or the polymer compound described in 3 above. 7). 7. The organic electroluminescence device according to 6 above, wherein the layer containing the aromatic amine derivative or polymer compound further contains a host material. 8). The above 7 wherein the host material is at least one selected from the group consisting of anthracene compounds, bisanthracene compounds, pyrene compounds, fluorene compounds, triarylamine compounds, fluoranthene compounds, and compounds represented by the following formula (2f).
  • the organic electroluminescent element of description is at least one selected from the group consisting of anthracene compounds, bisanthracene compounds, pyrene compounds, fluorene compounds, triarylamine compounds, fluoranthene compounds, and compounds represented by the following formula (2f).
  • Ar represents a trivalent group derived from an aromatic ring or a heteroaromatic ring
  • Ar 18 , Ar 19 and Ar 20 are each a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms
  • at least one of the substituents of the aryl group of Ar 18 , Ar 19 and Ar 20 is a ring. It has a condensed ring aryl structure having 10 to 20 carbon atoms or a condensed heteroaryl structure having 6 to 20 ring carbon atoms.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention porte sur un dérivé d'amine aromatique représenté par la formule (1) [dans laquelle X représente un noyau hydrocarboné aromatique ou un noyau hétérocyclique aromatique ; a1 représente un nombre de 0 à 11 ; R1 et R2 représentent indépendamment un groupe alkyle substitué ou non substitué ayant 1 à 20 atomes de carbone, un groupe hydrocarboné aromatique substitué ou non substitué, ou un groupe hétérocyclique aromatique substitué ou non substitué ; b1 et c1 représentent indépendamment un entier de 0 à 10 ; et A1 à A4 représentent indépendamment un groupe hydrocarboné aromatique substitué ou non substitué, ou un groupe hétérocyclique aromatique substitué ou non substitué, à la condition qu'au moins l'un de A1 à A4 ait un substituant représenté par la formule (2) (dans laquelle n1 représente un nombre de 1 à 12)].
PCT/JP2009/063350 2008-08-07 2009-07-27 Nouveau dérivé d'amine aromatique et élément électroluminescent organique l'utilisant Ceased WO2010016405A1 (fr)

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JP2011225546A (ja) * 2010-03-29 2011-11-10 Jnc Corp ベンゾフルオレン化合物、該化合物を用いた発光層用材料および有機電界発光素子
WO2012018120A1 (fr) * 2010-08-05 2012-02-09 出光興産株式会社 Dérivé de monoamine et élément électroluminescent organique l'utilisant
WO2012048780A1 (fr) * 2010-10-15 2012-04-19 Merck Patent Gmbh Composés pour dispositifs électroniques
JP2014177442A (ja) * 2013-03-15 2014-09-25 Idemitsu Kosan Co Ltd ジアミノアントラセン誘導体及び有機エレクトロルミネッセンス素子
WO2015041352A1 (fr) * 2013-09-20 2015-03-26 出光興産株式会社 Composé aminé et élément électroluminescent organique
US9331285B2 (en) 2009-12-16 2016-05-03 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent element using same
US9590182B2 (en) 2011-11-25 2017-03-07 Jnc Corporation Benzofluorene compound, material for luminescent layer using said compound and organic electroluminescent device
US9902687B2 (en) 2014-09-19 2018-02-27 Idemitsu Kosan Co., Ltd. Compound
WO2019012373A1 (fr) * 2017-07-14 2019-01-17 株式会社半導体エネルギー研究所 Composé organique, élément électroluminescent, dispositif électroluminescent, dispositif électronique et dispositif d'éclairage
US10263191B2 (en) 2009-04-24 2019-04-16 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element comprising the same
CN111211247A (zh) * 2015-05-27 2020-05-29 三星显示有限公司 有机发光器件

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US10686137B2 (en) 2009-04-24 2020-06-16 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element comprising the same
US10263191B2 (en) 2009-04-24 2019-04-16 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element comprising the same
US9923146B2 (en) 2009-12-16 2018-03-20 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent element using same
US9331285B2 (en) 2009-12-16 2016-05-03 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent element using same
JP2011219461A (ja) * 2010-03-23 2011-11-04 Jnc Corp ベンゾフルオレン化合物、該化合物を用いた発光層用材料および有機電界発光素子
JP2011225546A (ja) * 2010-03-29 2011-11-10 Jnc Corp ベンゾフルオレン化合物、該化合物を用いた発光層用材料および有機電界発光素子
WO2012018120A1 (fr) * 2010-08-05 2012-02-09 出光興産株式会社 Dérivé de monoamine et élément électroluminescent organique l'utilisant
CN102712570A (zh) * 2010-08-05 2012-10-03 出光兴产株式会社 单胺衍生物以及使用其的有机电致发光元件
WO2012048780A1 (fr) * 2010-10-15 2012-04-19 Merck Patent Gmbh Composés pour dispositifs électroniques
US9590182B2 (en) 2011-11-25 2017-03-07 Jnc Corporation Benzofluorene compound, material for luminescent layer using said compound and organic electroluminescent device
JP2014177442A (ja) * 2013-03-15 2014-09-25 Idemitsu Kosan Co Ltd ジアミノアントラセン誘導体及び有機エレクトロルミネッセンス素子
US9991455B2 (en) 2013-09-20 2018-06-05 Idemitsu Kosan Co., Ltd. Amine compound and organic electroluminescent element
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US9902687B2 (en) 2014-09-19 2018-02-27 Idemitsu Kosan Co., Ltd. Compound
US10435350B2 (en) 2014-09-19 2019-10-08 Idemitsu Kosan Co., Ltd. Organic electroluminecence device
CN111211247A (zh) * 2015-05-27 2020-05-29 三星显示有限公司 有机发光器件
CN111211247B (zh) * 2015-05-27 2023-04-18 三星显示有限公司 有机发光器件
WO2019012373A1 (fr) * 2017-07-14 2019-01-17 株式会社半導体エネルギー研究所 Composé organique, élément électroluminescent, dispositif électroluminescent, dispositif électronique et dispositif d'éclairage
JPWO2019012373A1 (ja) * 2017-07-14 2020-07-30 株式会社半導体エネルギー研究所 有機化合物、発光素子、発光装置、電子機器、および照明装置
JP7225097B2 (ja) 2017-07-14 2023-02-20 株式会社半導体エネルギー研究所 有機化合物、発光素子、発光装置、電子機器、および照明装置

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