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WO2006062001A1 - Materiau pour element electroluminescent organique et element electroluminescent organique - Google Patents

Materiau pour element electroluminescent organique et element electroluminescent organique Download PDF

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WO2006062001A1
WO2006062001A1 PCT/JP2005/021775 JP2005021775W WO2006062001A1 WO 2006062001 A1 WO2006062001 A1 WO 2006062001A1 JP 2005021775 W JP2005021775 W JP 2005021775W WO 2006062001 A1 WO2006062001 A1 WO 2006062001A1
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Hiroaki Tanaka
Yasumasa Taba
Yasumasa Suda
Shinichiro Maki
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Artience Co Ltd
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Toyo Ink Mfg Co Ltd
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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    • 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
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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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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom

Definitions

  • the present invention relates to an organic electoluminescence device (hereinafter also referred to as “organic EL device”) used for a planar light source and display. More specifically, the present invention relates to a red light emitting organic EL element that exhibits high color purity and luminance at a low driving voltage, and a material for the organic EL element.
  • An organic EL device that emits light when an electron injected with an anode and a hole injected with an anode is recombined in an organic phosphor sandwiched between these two electrodes is a solid-state display.
  • the use as an element is considered promising, and research and development has been actively conducted in recent years.
  • organic EL elements especially organic EL elements that emit red light have been studied using various materials because of their usefulness.
  • An effective method is to obtain a light emission from a dopant by mixing a small amount of dopant in a host material by a method such as co-evaporation to form a light emitting layer.
  • a method such as co-evaporation to form a light emitting layer.
  • CH Chen et al., Macromol. Symp., 125, 34-36 and 49-58 contains tris (8-hydroxyquinolinato) aluminum.
  • Organic EL devices that emit light from orange to red using 4H-pyran derivatives such as DCM, DCJ, DCJT, and DCJTB as dopants have been reported.
  • the organic EL element using a 4H-pyran derivative as a dopant has an insufficient emission color and has a high emission voltage with a high driving voltage. There was a problem that it was low.
  • an organic EL device using a compound having a 1,4-diketopyro (3, 4-c) pyrrole structure as a dopant has high color purity, and although the device can be produced, the cohesiveness of molecules is high. Control of doping concentration, which is easy to cause concentration quenching due to its high value, is an important issue. Therefore, there has been a demand for a material for an organic EL device that can obtain red light emission exhibiting high light emission luminance and long life without causing problems such as concentration quenching.
  • the present invention relates to a material for an organic electroluminescent element including a diketopyrophyllium compound having the general formula (1) below.
  • R 1 and R 2 each independently represents a substituted or unsubstituted alkylene group, and R 3 and R 4 each independently represent a substituted or unsubstituted aliphatic heterocyclic group or a general formula ( 2) represents a substituent represented by 2)
  • X represents an oxygen atom or a sulfur atom
  • R 15 represents a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted group. Or represents an unsubstituted monovalent aromatic heterocyclic group.
  • R 16 and R 17 are each independently a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted group. Or an unsubstituted monovalent aromatic heterocyclic group.
  • Another aspect of the present invention relates to an organic electoluminescence device material comprising the organic electroluminescence device material according to the present invention and an amine compound represented by the general formula (6).
  • R 42 and R 43 are each independently a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted group. It is a monovalent aromatic heterocyclic group. Ar 1 and R 42 , Ar 1 and R 43 , and R 42 and R 43 may be bonded to each other to form a ring. )
  • Another aspect of the present invention is an organic electoluminescence comprising a pair of electrodes each composed of an anode and a cathode, and a light emitting layer formed between the electrodes or a plurality of organic compound thin film layers including the light emitting layer. It is an element, Comprising: At least one layer formed between electrodes relates to the organic electoluminescence element containing the organic electroluminescent luminescence element material which concerns on the said invention.
  • Still another aspect of the present invention provides an organic electronic outer opening including a pair of electrodes each including an anode and a cathode, and a light emitting layer formed between the electrodes or a plurality of organic compound thin film layers including the light emitting layer. It is a luminescence element, Comprising: This light emitting layer is related with the organic electoluminescence element containing the organic electroluminescent element material which concerns on the said invention.
  • the organic EL device material containing the diketopyrrole-pillar compound of the present invention is particularly excellent in red light emission and hardly causes concentration quenching because of the specific structure of the diketopyrrole-pillar compound. It is characterized by being able to achieve both high light emission brightness and long life.
  • Organic EL devices made using this material can be used favorably as flat panel displays and flat light emitters.
  • Light sources such as copiers and printers, light sources such as liquid crystal displays and instruments, display boards, and signs It can be applied to lights and the like.
  • R 1 and R 2 represent a substituted or unsubstituted alkylene group.
  • R 3 and R 4 represent a substituted or unsubstituted aliphatic heterocyclic group or a substituent represented by the general formula (2) (described later).
  • R 5 to R W represent a hydrogen atom or a substituent, but at least one of R 5 to R 14 is an amino group represented by the general formula (3) (described later).
  • a monovalent aliphatic hydrocarbon group a monovalent aromatic hydrocarbon group, a monovalent aliphatic heterocyclic group, a monovalent aromatic heterocyclic group, a halogen atom, an alkoxyl group , Aryloxy groups, alkylthio groups, arylthio groups, acyl groups, alkoxy carbo yl groups, aryloxy carboxylic groups, alkyl sulfonyl groups, aryl sulfonyl groups, trialkyl silyl groups, cyano groups, An amino group etc. are mentioned.
  • the alkylene group includes methylene, ethylene, propylene, butylene, sec -butylene, tert-butylene, pentylene, hexylene, heptylene, octylene, etc. Of the alkylene group.
  • the aliphatic heterocyclic group includes 1,3 dioxoral group, 1,3 dioxal group, 1,4 dioxal group, 2-tetrahydrofuryl group, 2 morpholino group, 4 morpholino group, Examples thereof include monovalent aliphatic heterocyclic groups having 3 to 18 carbon atoms such as a peridino group.
  • the monovalent aliphatic hydrocarbon group is preferably a monovalent aliphatic hydrocarbon group having 1 to 18 carbon atoms.
  • Examples of such a group include an alkyl group, an alkyl group, an alkyl group, and a cycloalkyl group.
  • alkyl group examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec butyl group, a tert butyl group, a pentyl group, an isopentyl group, a hexyl group, a heptyl group, and an octyl group.
  • Alkyl groups having 1 to 18 carbon atoms such as decyl group, dodecyl group, pentadecyl group and octadecyl group.
  • the alkenyl group includes a butyl group, a 1-probe group, a 2-probele group, an iso- propyl group, a 1-butur group, a 2-butur group, a 3-butur group, a 1-octatur group, and a 1-decenyl group. And alkenyl groups having 2 to 18 carbon atoms such as 1-octadecenyl group.
  • alkyl group examples include an ether group, a 1-propyl group, a 2-propyl group, a 1-butynyl group, a 2-butyl group, a 3-propyl group, a 1-octyl group, 1
  • alkyl group having 2 to 18 carbon atoms such as a decyl group and a 1-octadecyl group.
  • Cycloalkyl groups include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclooctadecyl group, 2-boryl group, 2 isobornyl group, 1-adamantyl group And a cycloalkyl group having 3 to 18 carbon atoms such as a group.
  • Preferred examples of the monovalent aromatic hydrocarbon group include monovalent monocyclic, condensed rings, and ring-aggregated aromatic hydrocarbon groups having 6 to 30 carbon atoms.
  • Examples of the monovalent monocyclic aromatic hydrocarbon group include a phenyl group, o-tolyl group, m- tolyl group, p-tolyl group, 2,4-xylyl group, p-tyl group, mesityl group and the like having 6 to 6 carbon atoms. 30 monovalent monocyclic aromatic hydrocarbon groups.
  • the monovalent condensed ring aromatic hydrocarbon group includes 1 naphthyl group, 2 naphthyl group, 1-annsolinole group, 2 anthrinole group, 5 anthrinole group, 1-phenanthrinole group, 9 phenanthryl group, 1-acenaphthyl group Group, 2-azaryl group, 1-pyrylene group, 2-triphenyl group, 1-pyrrel group, 2 pyrel group, 1 perylene group, 2 perylene group, 3 perylene group
  • a monovalent condensed ring hydrocarbon group having 10 to 30 carbon atoms such as 2-trephenyl-enyl group, 2-indulyl group, 1-naphthnaphthyl group, 2-naphthyl group, 2 pentacenyl group, etc. Can be mentioned.
  • Monovalent ring-assembled aromatic hydrocarbon groups include: o Biphenyl-, m-biphenyl-, p-biphenyl-, terphenyl-, 7- (2 naphthyl) 2 naphthyl, etc. Examples thereof include 12-30 monovalent ring-assembled hydrocarbon groups.
  • the monovalent aromatic heterocyclic group includes 2 furyl group, 3 furyl group, 2 chael group, 3-chael group, N-pyrrolyl group, 2-benzzofuryl group, 2-benzoche group
  • Examples thereof include monovalent aromatic heterocyclic groups having 3 to 30 carbon atoms such as -l group, 2-pyridyl group, 3 pyridyl group, 4 pyridyl group, 2 quinolyl group, and 5 isoquinolyl group.
  • halogen atom examples include a fluorine atom, a chlorine atom, and a bromine atom.
  • alkoxyl group examples include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a tert-butoxy group, an octyloxy group, a tert-octyloxy group, a 2-boroxyloxy group, a 2 isobornyloxy group, and a 1-adamanman Examples thereof include an alkoxyl group having 1 to 18 carbon atoms such as a thioloxy group.
  • aryloxy group examples include an aryloxy group having 6 to 30 carbon atoms such as a phenoxy group, a 4 tert butyl phenoxy group, a 1 naphthyloxy group, a 2 naphthyloxy group, and a 9 anthryloxy group.
  • alkylthio group examples include alkylthio groups having 1 to 18 carbon atoms such as a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, and an octylthio group.
  • arylthio group examples include arylthio groups having 6 to 30 carbon atoms, such as a phenylthio group, a 2-methylphenolthio group, and a 4tert-butylphenylthio group.
  • acyl group examples include carbon numbers such as acetyl group, propiol group, bivaloyl group, cyclohexyl carboxyl group, benzoyl group, toluoyl group, ether group and cinnamoyl group.
  • Examples include 2 to 18 acyl groups.
  • alkoxycarbo yl group examples include C2-C18 alkoxy carbo ol groups such as a methoxy carbo ol group, an ethoxy carbo ol group, a benzyloxy carbo ol group and the like.
  • aryl carboxylic group examples include a phenoxy carbo yl group and a naphthyl oxy group. Examples thereof include arylcarbonyl groups having 7 to 30 carbon atoms, such as a diol group.
  • alkylsulfol group examples include C1-C18 alkylsulfol groups such as a mesyl group, an ethylsulfol group, and a propylsulfol group.
  • arylsulfol groups include arylaryl groups having 6 to 30 carbon atoms such as benzenesulfol groups and p-toluenesulfol groups.
  • trialkylsilyl group examples include trialkylsilyl groups having 6 to 18 carbon atoms such as a trimethylsilyl group, a triethylsilyl group, a dimethylethylsilyl group, a triisopropylpropylsilyl group, and a tributylsilyl group.
  • amino group examples include amino groups having 6 to 30 carbon atoms such as a jetylamino group, a dibutylamino group, a diphenylamino group, a ditolylamino group, and an ethylphenylamino group.
  • substituents may be further substituted with other substituents, or these substituents may be bonded to each other to form a ring.
  • R 15 represents an oxygen atom or a sulfur atom
  • R 15 represents a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, or Represents a substituted or unsubstituted monovalent aromatic heterocyclic group.
  • the monovalent aliphatic hydrocarbon group, the monovalent aromatic hydrocarbon group, and the monovalent aromatic heterocyclic group are the monovalent aliphatic hydrocarbon group in the general formula (1), the monovalent These are synonymous with the aromatic hydrocarbon group and monovalent aromatic heterocyclic group.
  • R 16 and R 17 are each independently a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted group. Represents a monovalent aromatic heterocyclic group.
  • the monovalent aliphatic hydrocarbon group, the monovalent aromatic hydrocarbon group, and the monovalent aromatic heterocyclic group are the monovalent aliphatic hydrocarbon group in the general formula (1), the monovalent These are synonymous with the aromatic hydrocarbon group and monovalent aromatic heterocyclic group.
  • the diketopyrrolopyrrole compound represented by the general formula (1) is preferably a diketopyrrolopyrrole compound represented by the following general formula (4).
  • Ri to R 12 are the same as Ri to R 12 in the general formula (1).
  • R 18 to R 21 are each independently a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted group. Represents a monovalent aromatic heterocyclic group.
  • the monovalent aliphatic hydrocarbon group, the monovalent aromatic hydrocarbon group, and the monovalent aromatic heterocyclic group are the monovalent aliphatic hydrocarbon group in the general formula (1), the monovalent These are synonymous with the aromatic hydrocarbon group and monovalent aromatic heterocyclic group.
  • the diketopyropyrotic compound represented by the general formula (4) is represented by the following general formula (5): It is preferable that it is a diketopyro-pillar compound.
  • Ri to R 12 are the same as Ri to R 12 in the general formula (1).
  • R 2 2 to R 41 each independently represent a hydrogen atom or a substituent.
  • the substituent is synonymous with the substituent in the general formula (1) described above, and is a monovalent aliphatic hydrocarbon group, a monovalent aromatic hydrocarbon group, or a monovalent aliphatic heterocyclic group.
  • the number of carbon atoms in Ri ⁇ R 41 substituents described above [0044] are 1 to 18 preferably tool 12 are more preferred. This is because if the carbon number of these substituents is too large, there is a concern that the vapor deposition property may deteriorate when an element is formed by vapor deposition.
  • the power described above for diketopyrrolopyrrole compounds are 2000 or less, preferably 1500 or less, and more preferably 1000 or less. This is because if the molecular weight is too large, there is a concern that the vapor deposition property may deteriorate when an element is formed by vapor deposition.
  • Table 1 below shows typical examples of the diketopyrophyllopyrotic compound represented by the general formula (1).
  • the present invention is not limited to these.
  • the material for an organic EL device includes a diketopyropyrotic compound represented by the above general formula (1), and further includes a known hole injection material, hole transport material, and light emitting material. It may contain a material, an electron injection material, etc. (described later).
  • another organic EL device material includes the above-mentioned organic EL device material, that is, at least a diketopyro-pillar compound represented by the general formula (1), And an amine compound represented by the following general formula (6).
  • Ar 1 represents a substituted or unsubstituted perylenyl group
  • R 42 and R 43 each independently represents a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent group.
  • Ar 1 and R 42 , Ar 1 and R 43 , and R 42 and R 43 may be bonded to each other to form a ring.
  • this organic EL device material may be a known hole injection material, hole transport material, light emitting material, electron injection material, etc. (described later). May be included.
  • Ar 1 in the general formula (6) represents a substituted or unsubstituted perylenyl group, and examples of the unsubstituted perylyl group include a 1 perylenyl group, a 2 perylenyl group, and a 3 perylenyl group. These perylenyl groups may be further substituted with other substituents. Of these, unsubstituted 3-perylenyl groups are preferred, with substituted or unsubstituted 3-perylenyl groups being particularly preferred.
  • Ar 1 includes a monovalent aliphatic hydrocarbon group, a monovalent aromatic hydrocarbon group, a monovalent aliphatic heterocyclic group, a monovalent aromatic heterocyclic group, a halogen Atom, alkoxyl group, aryloxy group, alkylthio group, arylothio group, acyl group, alkoxy carbo yl group, aroxy carboxy group, alkyl sulphonyl group, aryl sulphonyl group, trialkyl silyl group, cyano group Etc.
  • R 42 and R 43 are substituted or unsubstituted monovalent aromatic hydrocarbon groups, or Or a monovalent organic residue selected from unsubstituted monovalent aromatic heterocyclic groups.
  • the substituent for R 43 has the same meaning as the substituent described for the substituent for Ar 1 .
  • the monovalent aliphatic hydrocarbon group a monovalent aliphatic hydrocarbon group having 1 to 18 carbon atoms is preferable.
  • Examples of such a monovalent aliphatic hydrocarbon group include an alkyl group, an alkenyl group, An alkynyl group and a cycloalkyl group are mentioned.
  • alkyl group examples include the same groups as those in the general formula (1).
  • Examples of the monovalent aromatic hydrocarbon group include monovalent monocyclic, condensed ring, and ring-aggregated aromatic hydrocarbon groups having 6 to 30 carbon atoms.
  • the monovalent monocyclic aromatic hydrocarbon group having 6 to 30 carbon atoms, the monovalent condensed ring aromatic hydrocarbon group, and the monovalent ring assembly aromatic hydrocarbon group are represented by the following formula (1). These are the same.
  • Examples of the monovalent aliphatic heterocyclic group include 3-isochromanyl group, 7-chromal group, and 3-tamari group.
  • monovalent aliphatic heterocyclic groups having 3 to 18 carbon atoms such as -l group, piperidino group, morpholino group and 2-morpholino group.
  • substituents may be further substituted with other substituents, or these substituents may be bonded to each other to form a ring.
  • the number of carbons in the R 42 and R 43 substituents described above is preferably 1-18, more preferably 1-12 forces S. This is because if the number of carbon atoms of these substituents is too large, there is a concern that the vapor deposition property may deteriorate when an element is formed by vapor deposition.
  • the force described above for the amine compound represented by the general formula (6) The molecular weight of these amine compounds is 2000 or less force S, preferably 1500 or less, more preferably 1000 or less. . This is because, when the molecular weight is large, there is a concern that the vapor deposition property may deteriorate when an element is formed by vapor deposition.
  • Table 2 below shows typical examples of amine compounds represented by the general formula (6), but the present invention is not limited to these. In the table, t Bu represents a tert butyl group, Ph represents a phenyl group, and Tol represents a p tolyl group.
  • This organic EL element is formed by forming a light emitting layer or a plurality of organic compound thin films (thin film layers) including a light emitting layer between a pair of electrodes consisting of an anode and a cathode, and at least one of the thin film layers.
  • organic compound thin films thin film layers
  • it contains the above-mentioned materials for organic EL elements.
  • the layer containing the organic EL element material is preferably a light emitting layer.
  • the organic EL element is composed of an element in which one or more organic layers are formed between an anode and a cathode.
  • a single-layer organic EL element refers to an element in which only a light emitting layer is formed between an anode and a cathode.
  • a multilayer organic EL device facilitates injection of holes and electrons into the light emitting layer in addition to the light emitting layer, and facilitates recombination of holes and electrons in the light emitting layer. For the purpose of this, it refers to a stack of a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, and the like.
  • Typical device configurations of multilayer organic EL devices are: (1) anode Z hole injection layer Z light emitting layer Z cathode; (2) anode Z hole injection layer Z hole transport layer Z light emitting layer Z cathode; 3) Anode Z hole injection layer Z emission layer Z electron injection layer Z cathode; (4) Anode Z hole injection layer Z hole transport layer Z emission layer Z electron injection layer Z cathode; (5) Anode Z hole Injection layer Z emission layer Z hole blocking layer Z electron injection layer Z cathode; (6) Anode Z hole injection layer Z hole transport layer Z emission layer Z hole blocking layer Z electron injection layer Z cathode; A multilayer structure such as anode Z light-emitting layer Z hole blocking layer Z electron injection layer Z cathode; (8) anode Z light-emitting layer Z electron injection layer Z cathode;
  • Each thin film layer such as the hole injection layer, the light emitting layer, and the electron injection layer may be formed of two or more layers.
  • hole injection layer a hole injection material that exhibits an excellent hole injection effect with respect to the light-emitting layer and can form a layer having excellent adhesion to the anode interface and thin film formability is used.
  • hole transporting layer a hole transporting material that exhibits an excellent hole transporting effect with respect to the light emitting layer and that can form a layer having excellent adhesion with an adjacent thin film layer and a thin film forming property is used.
  • hole injection materials or hole transport materials include phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxadiazole derivatives, triazole derivatives, imidazole derivatives, imidazolone derivatives, imidazolethione derivatives, pyrazoline derivatives, pyrazolones.
  • Derivatives tetrahydroimidazole derivatives, oxazole Derivatives, oxaziazole derivatives, hydrazone derivatives, acyl hydrazone derivatives, stilbene derivatives, aromatic tertiary amine derivatives, polybulur rubazole derivatives, polysilan derivatives, etc.
  • it is a material that can inject holes and transport holes, it is not limited to these materials.
  • hole injection materials or hole transport materials that can be used particularly preferably include aromatic tertiary amine derivatives and phthalocyanine derivatives.
  • aromatic tertiary amine derivatives include: , N, N'—Diphenyl— N, N ′-(3-Methylphenol) 1 1, 1 Biferro- 4, 4, 1 Diamine, N, N, ⁇ ', ⁇ '-(4-Methyl (Rufer) — 1, 1, Fir — 4, 4, — Diamine, ⁇ , ⁇ , ⁇ ', ⁇ '-(4-Methylphenyl) 1, 1, —Bipherol 4, 4, —Diamine , ⁇ , ⁇ , —Difel-Lo ⁇ , ⁇ , —Dinaphthyl— 1, 1, Bi-Fell 4, 4, —Diamine, ⁇ , ⁇ , (Methylphenol) ⁇ , ⁇ , One (4— ⁇ — (Butylphenol) ⁇ , ⁇ , One (4
  • phthalocyanine (p c ) derivative examples include H2Pc CuPc CoPc NiPc ZnP c PdPc FePc MnPc ClAlPc ClGaPc ClInPc ClSnPc C12SiPc (HO) AlPc (HO) GaPc VOPc TiOPc MoOPc GaPc— O-GaPc It can be used suitably for a hole injection material.
  • an electron injection material that exhibits an excellent electron injection effect with respect to the light emitting layer and can form a layer having excellent adhesion to the cathode interface and thin film formability is used.
  • electron injection materials include metal complex compounds, nitrogen-containing five-membered ring derivatives, fluorenone derivatives, anthraquinodimethane derivatives, diphenoquinone derivatives, thiopyran dioxide derivatives, perylene tetracarboxylic acid derivatives, fluorenylidene methane derivatives, Anthrone derivatives, silole derivatives, calcium acetyl cetate, sodium acetate and the like.
  • inorganic Z doped with phosphorus such as cesium Organic Composites (Proceedings of the Society of Polymer Science, No. 50, No. 4, page 660, published in 2001) and the 50th Applied Physics-related Joint Lecture Proceedings, No. 3, page 1402, 2003
  • electron injection materials include BCP, TPP, and T5MPyTZ described in the publication.
  • the material is not particularly limited as long as it is a material that can form a thin film necessary for device fabrication, inject electrons from the cathode, and can transport electrons.
  • electron injection materials particularly effective electron injection materials include metal complex compounds and nitrogen-containing five-membered ring derivatives.
  • Preferred metal complex compounds include tris (8-hydroxyquinolinato) aluminum (Alq3), tris (2-methyl 8-hydroxyquinolinato) aluminum, tris (5-phenol mono 8-hydroxyquinolinate).
  • the nitrogen-containing five-membered ring derivative includes an oxazole derivative, a thiazole derivative, an oxadiazole derivative, a thiadiazole derivative, and a triazole derivative.
  • 2,5 bis (1 phenol) -1,3,4-oxazole, 2,5 bis (1—phenol) -1,3,4 thiazole, 2,5 bis (1-phenol) 1) 1, 3, 4—Oxadiazole, 2— (4, —tert-Butylphenol) 5— (4 ”—Biphenyl) 1,3,4—Oxadiazole, 2,5 Bis (1 Naphthyl) -1,3,4 oxadiazole, 1,4 bis [2— (5—phenoloxazolyl)] benzene, 1,4 bis [2— (5-phenol oxaziazolyl) 4 tert butyl Benzene], 2— (4 ′ tert butylphenol) — 5— (4,1 biphenyl) 1
  • a hole blocking material is used for the hole blocking layer, which can prevent holes that have passed through the light emitting layer from reaching the electron injection layer and can form a layer having excellent thin film formability.
  • hole blocking materials include aluminum complex compounds such as bis (8-hydroxyquinolinate) (4 phenolphenolate) aluminum, bis (2-methyl-8 hydroxyquinolinato) (4 phenol Enolate) gallium complex compounds such as gallium, and nitrogen-containing condensed aromatic compounds such as 2,9 dimethyl-4,7 diphenyl-1,10 phenanthrene (BCP).
  • aluminum complex compounds such as bis (8-hydroxyquinolinate) (4 phenolphenolate) aluminum, bis (2-methyl-8 hydroxyquinolinato) (4 phenol Enolate) gallium complex compounds such as gallium, and nitrogen-containing condensed aromatic compounds such as 2,9 dimethyl-4,7 diphenyl-1,10 phenanthrene (BCP).
  • the organic EL device material when used for the light emitting layer, it may contain other host material or dopant.
  • the dopant concentration is in the range of 0.001 to 30% by weight with respect to the host material. More preferably, it is contained in the range of 0.1 to 5% by weight.
  • the light emitting layer in addition to the above organic EL element material, if necessary, not only other light emitting materials and doping materials, but also the above-described hole injection materials and electron injection materials. These may be contained alone or in combination of two or more.
  • Materials used for the anode include metals such as carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, and alloys thereof; zinc oxide, tin oxide, Examples thereof include conductive metal oxides such as indium oxide and indium oxide indium (ITO); and conductive polymers such as polythiophene, polypyrrole, and polyarine.
  • ITO glass and NESA glass which preferably have a resistance value as low as possible, are preferably used.
  • the material used for the cathode is not particularly limited as long as it can efficiently inject electrons into the organic EL device.
  • the alloy magnesium Z silver, magnesium Z indium, lithium Z aluminum, and the like, which are typical examples, alloys containing low work function metals such as lithium, sodium, potassium, calcium, and magnesium are preferable. It is also possible to use an inorganic salt such as lithium fluoride in place of the low work function metal.
  • these cathodes can be produced by known methods such as resistance heating, electron beam irradiation, sputtering, ion plating, and coating.
  • the anode and the cathode described above may be formed with a layer structure of two or more layers as necessary.
  • the thickness of each electrode is not particularly limited, but it is 0. Olnn! From the viewpoints of conductivity, light transmission, and film formability. It is preferably about 10 m.
  • the substrate material on the surface from which the light is extracted is sufficiently transparent.
  • the light transmittance is preferably 50% or more, more preferably 90% or more.
  • These substrates are not particularly limited as long as they have mechanical and thermal strength and are light transmissive.
  • polyethylene, polyether sulfone can be used.
  • Transparent polymers such as polypropylene and polypropylene are recommended.
  • each layer of the organic EL element dry deposition methods such as vacuum deposition, electron beam irradiation, sputtering, plasma and ion plating, or wet deposition methods such as spin coating, dating, and flow coating are used. Any method of law can be applied.
  • the film thickness of each layer is not particularly limited, but if the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. Holes or the like are generated, and it becomes difficult to obtain sufficient light emission luminance even when an electric field is applied.
  • the thickness of each layer is suitably in the range of lnm to 1 ⁇ m, and the range of lOnm force and 0.2 m is more preferable, and the range of lnm force and 0.2 ⁇ m ⁇ is more preferable.
  • a protective layer may be provided on the surface of the element, or the whole element may be covered or sealed with grease or the like.
  • a photocurable resin that is cured by light is preferably used as a material for covering or sealing the entire element.
  • this organic EL element can obtain red light emission exhibiting high color purity and luminance at a low driving voltage. Therefore, this organic EL element can be used as a flat panel display such as a wall-mounted television or a flat light emitter, and further to a light source such as a copying machine or a printer, a light source such as a liquid crystal display or instrument, a display board, or a sign lamp Can be considered.
  • a light source such as a copying machine or a printer, a light source such as a liquid crystal display or instrument, a display board, or a sign lamp Can be considered.
  • NPD NPD-deposited on the cleaned glass plate with an ITO electrode to obtain a 20 nm-thick hole transport layer.
  • the compound 2 shown in Table 1 was vacuum-deposited as a diketopyro-pyropyrotic compound to obtain a light-emitting layer having a thickness of 40 nm.
  • tris (8-hydroxyquinolinate) aluminum (Alq3) was vapor-deposited to obtain an electron injection layer having a thickness of 30 nm.
  • 0.2 nm of LiF was vapor-deposited, and A1 was vapor-deposited to form an electrode with a thickness of 150 nm, thereby obtaining an organic EL device. It was.
  • An organic EL device was produced in the same manner as in Example 1 except that the following Comparative Compound A and Comparative Compound B were used instead of Compound 2.
  • Table 3 shows the maximum light emission luminance of the devices obtained in these Examples and Comparative Examples, and the half life when driven at a constant current at an initial light emission luminance of 500 cd / m 2 .
  • NPD was vacuum-deposited on the cleaned glass plate with an ITO electrode to obtain a 20 nm-thick hole transport layer.
  • the compound 2 of Table 1 as a diketopyro-pillar compound and the compound 43 of Table 2 as an amine compound were co-deposited at a composition ratio of 5:95 (weight ratio), and the film thickness was 40 nm. A light emitting layer was obtained.
  • tris (8-hydroxyquinolinate) aluminum (Alq3) was vapor-deposited to obtain an electron injection layer having a thickness of 30 nm. Furthermore, after depositing 0.2 nm of LiF on it, Al was evaporated to form an electrode having a thickness of 150 nm, and an organic EL device was obtained.
  • An organic EL device was produced in the same manner as in Example 1 except that tris (8-hydroxyquinolinate) aluminum (Alq3) was used instead of compound 43.
  • Table 4 shows the maximum light emission luminance of the devices obtained in these examples and comparative examples, and the half-life when driven at a constant current with an initial light emission luminance of 500 cd / m 2 .

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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
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  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne un matériau pour éléments électroluminescents organiques contenant un composé dicéto pyrrolopyrrole représenté par la formule générale suivante (1). Formule générale (1) (Dans la formule, R1 à R2 représentent chacun indépendamment un alkylène (non) substitué; R3 et R4 représentent chacun indépendamment un groupe hétérocyclique aliphatique (non) substitué ou un substituant représenté par la formule générale (2); et R5 à R14 représentent chacun indépendamment l'hydrogène ou un substituant, sous réserve qu'au moins un des radicaux R5 à R14 soit un aminé représenté par la formule générale (3).) Formule générale (2) (Dans la formule, X représente l'oxygène ou le soufre; et R15 représente un groupe hydrocarbure aliphatique monovalent (non) substitué, un groupe hydrocarbure aromatique monovalent (non) substitué, ou un groupe hétérocyclique aromatique monovalent (non) substitué.) Formule générale (3) (Dans la formule, R16 et R17 représentent chacun indépendamment l'hydrogène, un groupe hydrocarbure aliphatique monovalent (non) substitué, un groupe hydrocarbure aromatique monovalent (non) substitué ou un groupe hétérocyclique aromatique monovalent (non) substitué.)
PCT/JP2005/021775 2004-12-10 2005-11-28 Materiau pour element electroluminescent organique et element electroluminescent organique Ceased WO2006062001A1 (fr)

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CN113045435B (zh) * 2021-03-15 2022-05-31 江苏信息职业技术学院 一种具有a-d-a结构的含苝化合物及其制备方法与应用

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WO2003048268A1 (fr) * 2001-12-03 2003-06-12 Toyo Ink Mfg. Co., Ltd. Composition pour element electroluminescent organique et element electroluminescent organique utilisant cette composition

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WO2003048268A1 (fr) * 2001-12-03 2003-06-12 Toyo Ink Mfg. Co., Ltd. Composition pour element electroluminescent organique et element electroluminescent organique utilisant cette composition

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008111553A1 (fr) * 2007-03-09 2008-09-18 Idemitsu Kosan Co., Ltd. Dispositif électroluminescent organique et dispositif d'affichage

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