WO2013157367A1 - Nouveau dérivé de triphénylène, et élément électroluminescent organique dans lequel ledit dérivé est utilisé - Google Patents

Nouveau dérivé de triphénylène, et élément électroluminescent organique dans lequel ledit dérivé est utilisé Download PDF

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WO2013157367A1
WO2013157367A1 PCT/JP2013/058998 JP2013058998W WO2013157367A1 WO 2013157367 A1 WO2013157367 A1 WO 2013157367A1 JP 2013058998 W JP2013058998 W JP 2013058998W WO 2013157367 A1 WO2013157367 A1 WO 2013157367A1
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organic
triphenylene
compound
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紀昌 横山
寛史 大熊
長岡　誠
大三 神田
秀一 林
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保土谷化学工業株式会社
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Definitions

  • the present invention relates to a novel compound (triphenylene derivative) suitable for an organic electroluminescence element which is a self-luminous element suitable for various display devices, and an organic electroluminescence element comprising an organic layer containing the compound.
  • organic electroluminescence elements (hereinafter sometimes referred to as organic EL elements) are self-luminous elements, they are brighter and more visible than liquid crystal elements, and can be clearly displayed. I came.
  • organic electroluminescence elements using organic materials practical by developing a laminated structure element that shares various roles with each material. They consist of a stack of a phosphor capable of transporting electrons and an aromatic amine compound capable of transporting holes, and both charges are injected into the phosphor layer. By emitting light, high luminance of 1000 cd / m 2 or more can be obtained at a voltage of 10 V or less.
  • an element having a structure in which various roles are further subdivided and an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially provided on a substrate is known.
  • Such an element achieves high efficiency and durability.
  • the light emitting layer can also be prepared by doping a charge transporting compound generally called a host material with a phosphor or a phosphorescent light emitter.
  • a charge transporting compound generally called a host material with a phosphor or a phosphorescent light emitter.
  • an organic EL element charges injected from both electrodes recombine in the light emitting layer to emit light, but it is important to efficiently transfer both holes and electrons to the light emitting layer. For example, the probability of recombination of holes and electrons is improved by increasing the hole injection property and blocking the electron injected from the cathode, and further excitons generated in the light emitting layer. By confining, high luminous efficiency can be obtained. Therefore, the role of the hole transport material is important, and there is a demand for a hole transport material that has high hole injectability, high hole mobility, high electron blocking properties, and high durability against electrons. ing.
  • the heat resistance and amorphous nature of the material are important for the lifetime of the element.
  • thermal decomposition occurs even at a low temperature due to heat generated when the element is driven, and the material is deteriorated.
  • the thin film is crystallized even in a short time, and the element is deteriorated. For this reason, the material used is required to have high heat resistance and good amorphous properties.
  • NPD N, N′-diphenyl-N, N′-di ( ⁇ -naphthyl) benzidine
  • Tg glass transition point
  • Patent Document 1 and Patent Document 2 various aromatic amine derivatives
  • the aromatic amine derivatives described in Patent Document 1 and Patent Document 2 there are those having an excellent mobility of hole mobility of 10 ⁇ 3 cm 2 / Vs or more, but the electron blocking property. Insufficient amount of electrons pass through the light-emitting layer, and improvement in luminous efficiency cannot be expected.For higher efficiency, electron blocking is higher, thin film is more stable and heat resistant High-quality materials were demanded.
  • Patent Documents 3 and 4 propose arylamine compounds A and B having a substituted triphenylene structure represented by the following formula.
  • JP-A-8-48656 Japanese Patent No. 3194657 WO2010 / 002850 publication WO2011 / 081423
  • the present inventors have a high hole injection / transport capability of the aromatic tertiary amine structure, and the triphenylene ring structure has good heat resistance and thin film stability. Focusing on this, various compounds having a triphenylene ring structure were designed and chemically synthesized, and various organic electroluminescence devices were prototyped using the compounds. As a result, the present invention has been completed.
  • a triphenylene derivative represented by the following general formula (1) is provided.
  • p and q each represents 0 or an integer of 1 to 4;
  • s represents 0 or an integer of 1 to 3
  • Ar 1 and Ar 2 each represent an aromatic hydrocarbon group or an aromatic heterocyclic group, and Ar 1 and Ar 2 are a single bond, a methylene group which may have a substituent, an oxygen atom Alternatively, they may be bonded to each other via a sulfur atom to form a ring
  • R 1 , R 2 and R 3 are each a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms,
  • An alkenyl group having 2 to 6 carbon atoms It represents an alkyloxy group having 1 to 6 carbon atoms, a cycloalkyloxy group having 5 to 10 carbon
  • the organic electroluminescence device having a pair of electrodes and at least one organic layer sandwiched therebetween, At least one layer of the organic layer contains the triphenylene derivative, and an organic electroluminescence device is provided.
  • the organic EL device of the present invention has, for example, a hole transport layer, an electron blocking layer, a hole injection layer, or a light emitting layer as the organic layer containing the triphenylene derivative.
  • the triphenylene derivative of the present invention represented by the general formula (1) described above is a novel compound, and has a structure in which an aromatic tertiary amino group (disubstituted aromatic amino group) is introduced into the triphenylene ring. In relation to such a structure, it has the following characteristics.
  • the triphenylene derivative of the present invention is useful as a hole transporting material used in an organic EL device and has a stable thin film state. Therefore, the triphenylene derivative is particularly used as an organic layer provided in the organic EL device.
  • the following characteristics can be imparted to the element.
  • an organic EL device in which a hole injection layer and / or a hole transport layer are formed using the triphenylene derivative of the present invention has a high hole injection / transfer rate, a high electron blocking property, and a high resistance to electrons. Since the stability is high, excitons generated in the light emitting layer can be confined, and further, the probability of recombination of holes and electrons is improved, and high luminous efficiency is exhibited. Further, the driving voltage is lowered, and the durability can be improved.
  • the organic EL device having the electron blocking layer formed using the triphenylene derivative of the present invention has a high emission efficiency due to an excellent electron blocking ability and an excellent hole transport property, and a driving voltage is high. Low, current resistance is improved, and maximum light emission brightness is improved.
  • the triphenylene derivative of the present invention has excellent hole transport properties and a wide band gap as compared with conventional materials, it can be used as a host material for a light-emitting layer.
  • a fluorescent luminescent material or phosphorescent luminescent material called a dopant By supporting a fluorescent luminescent material or phosphorescent luminescent material called a dopant and using it as a luminescent layer, the driving voltage of the organic EL element can be lowered and the luminous efficiency can be improved.
  • the triphenylene derivative of the present invention is extremely useful as a constituent material of the hole injection layer, the hole transport layer, the electron blocking layer, or the light emitting layer of the organic EL element, and improves the light emission efficiency and power efficiency of the organic EL element. It is possible to improve, lower the practical driving voltage, and increase the durability.
  • the triphenylene derivative of the present invention is represented by the following general formula (1), and has a structure in which an aromatic tertiary amino group (—NAr 1 Ar 2 ) is bonded to the triphenylene ring.
  • p and q indicating the number of substituents R 1 and R 2 bonded to the triphenylene ring are each 0 or an integer of 1 to 4. Further, s indicating the number of substituents R 3 bonded to the triphenylene ring represents 0 or an integer of 1 to 3.
  • Ar 1 and Ar 2 bonded to the nitrogen atom of the aromatic tertiary amino group bonded to the triphenylene ring are each an aromatic hydrocarbon group or an aromatic heterocyclic ring.
  • Such an aromatic hydrocarbon group and aromatic heterocyclic group may have a monocyclic structure or may have a condensed polycyclic structure.
  • aromatic groups include phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthryl group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group.
  • aromatic heterocyclic groups oxygen-containing aromatic heterocyclic groups such as furanyl group, benzofuranyl group, benzoxazolyl group, dibenzofuranyl group; thienyl group, benzothienyl group, benzothiazolyl group, dibenzothienyl group
  • a sulfur-containing aromatic heterocyclic group such as N-phenylcarbazolyl group and N-phenyl-9,10-dihydroacridinyl group are preferable, and a sulfur-containing aromatic heterocyclic group is most preferable.
  • the aromatic group (aromatic hydrocarbon group and aromatic heterocyclic group) exemplified above is preferably an aromatic hydrocarbon group, an N-phenylcarbazolyl group, or a dibenzofuranyl group, and an aromatic group A hydrocarbon group is particularly preferred.
  • the above aromatic group may have a substituent.
  • substituents include: deuterium atom; cyano group; nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom and iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n- Linear or branched alkyl groups having 1 to 6 carbon atoms such as butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group; methoxy group, ethoxy group A linear or branched alkyloxy group having 1 to 6 carbon atoms such as propyloxy group; alkenyl group such as allyl group; aralkyl group such as benzyl group, naphthylmethyl group and phenethyl group; phenoxy group and tolyl
  • the substituent of the aromatic group is preferably a linear or branched alkyl group having 1 to 6 carbon atoms, particularly preferably a methyl group or a tert-butyl group.
  • Ar 1 and Ar 2 are a single bond, a methylene group which may have a substituent (for example, a substituted methylene group such as an unsubstituted methylene group or a dimethylmethylene group), an oxygen atom or a sulfur atom. And may be bonded to each other to form a ring together with the nitrogen atom of the amino group.
  • a substituent for example, a substituted methylene group such as an unsubstituted methylene group or a dimethylmethylene group
  • an oxygen atom or a sulfur atom may be bonded to each other to form a ring together with the nitrogen atom of the amino group.
  • Examples of such a ring include a carbazole ring, an acridine ring, a phenothiazine ring, a phenoxazine ring (see compounds 64-70 described later), and an acridine ring (see compounds 65-67 described later) is particularly preferable. These rings may also
  • R 1 , R 2 and R 3 bonded to the triphenylene ring are each a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a C 1-6 carbon atom.
  • Alkyl group, cycloalkyl group having 5 to 10 carbon atoms, alkenyl group having 2 to 6 carbon atoms, alkyloxy group having 1 to 6 carbon atoms, cycloalkyloxy group having 5 to 10 carbon atoms, aromatic carbonization Represents a hydrogen group, an aromatic heterocyclic group or an aryloxy group.
  • the alkyl group having 1 to 6 carbon atoms may be linear or branched, and specific examples thereof include a methyl group, an ethyl group, and n-propyl.
  • a cycloalkyl group having 5 to 10 carbon atoms an alkenyl group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, and a cycloalkyloxy group having 5 to 10 carbon atoms in R 1 to R 3
  • the groups may be either linear or branched, and specific examples include the following. Examples of cycloalkyl groups; Cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group and the like. Examples of alkenyl groups; Vinyl group, allyl group, etc.
  • alkyloxy groups Methyloxy group, ethyloxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, tert-butyloxy group, n- Pentyloxy group, n-hexyloxy group and the like.
  • cycloalkyloxy groups A cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, a cyclooctyloxy group, a 1-adamantyloxy group and a 2-adamantyloxy group.
  • alkyl group, cycloalkyl group, alkenyl group, alkyloxy group and cycloalkyloxy group may also have a substituent, and examples of such a substituent include the aromatic groups in Ar 1 and Ar 2 described above.
  • the thing similar to the substituent which a hydrocarbon group and an aromatic heterocyclic group may have can be mentioned.
  • aromatic hydrocarbon group and aromatic heterocyclic group in R 1 to R 3 are the same groups as those exemplified for Ar 1 and Ar 2 described above, and the same may be included in the substituent. is there.
  • aryloxy group in R 1 to R 3 phenyloxy group, tolyloxy group, biphenylyloxy group, terphenylyloxy group, naphthyloxy group, anthryloxy group, phenanthryloxy group, fluorenyloxy group Indenyloxy group, pyrenyloxy group, perylenyloxy group and the like can be mentioned.
  • these aryloxy groups may also have a substituent, and as such a substituent, the aromatic hydrocarbon group and the aromatic heterocyclic group in Ar 1 and Ar 2 may have a substituent. The same thing as a group can be mentioned.
  • the following general formula (1a) In the formula, p, q, s, Ar 1 , Ar 2 and R 1 to R 3 have the meanings described in the general formula (1).
  • a triphenylene derivative in which an aromatic tertiary amino group (—NAr 1 Ar 2 ) is bonded to the 2-position ( ⁇ -position) of the triphenylene ring is preferable.
  • triphenylene derivative is a novel compound and is synthesized, for example, as follows.
  • triphenylene corresponding to the triphenylene ring possessed by the triphenylene derivative of the general formula (1) is used, and the 2-position ( ⁇ -position) of this triphenylene is brominated with N-bromosuccinimide or the like.
  • a cross-coupling reaction such as a Buchwald reaction (see, for example, Org. Synth., 10, 423 (2002)) with an amine compound (HNAr 1 Ar 2 ) corresponding to an amino group
  • the compound is represented by the general formula (1a).
  • the triphenylene derivative can be synthesized.
  • triphenylene derivatives having different bonding positions of aromatic tertiary amino groups can be synthesized.
  • introduction of further substituents into the triphenylene derivative can synthesize various brominated compounds, for example, by brominating a compound having a triphenylene ring structure with N-bromosuccinimide or the like.
  • the above-described triphenylene derivative of the present invention has a glass transition point (Tg) and a melting point higher than those of conventionally known hole transport materials, can form a thin film excellent in heat resistance, and is stable in an amorphous state. Since it is maintained, the thin film state can be stably maintained.
  • the electron blocking ability is high. For example, when the work function is measured by forming a deposited film having a thickness of 100 nm using the triphenylene derivative of the present invention, an extremely high value is shown. Therefore, the triphenylene derivative of the present invention is extremely useful as a material for forming an organic layer of an organic EL element.
  • the organic EL element provided with the organic layer formed using the triphenylene derivative of the present invention described above has a layer structure shown in FIG. 7, for example. That is, a transparent anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer on a glass substrate 1 (a transparent substrate such as a transparent resin substrate may be used). 7 and a cathode 8 are provided.
  • the organic EL element to which the triphenylene derivative of the present invention is applied is not limited to the above layer structure, and an electron blocking layer, a light emitting layer 5 and a hole transport layer 4 are disposed between the hole transport layer 4 and the light emitting layer 5.
  • a hole blocking layer or the like can be provided between the electron transport layer 6 and a simple layer structure in which the electron injection layer 7 and the hole injection layer 3 are omitted can be obtained.
  • some layers can be omitted.
  • a simple layer structure in which the anode 2, the hole transport layer 3, the light emitting layer 4, the electron transport layer 6, and the cathode 8 are provided on the substrate 1 can be used.
  • the triphenylene derivative of the present invention has an organic layer (for example, a hole injection layer 3, a hole transport layer 4, an electron blocking layer not shown, or a light emitting layer 4) provided between the anode 2 and the cathode 8 described above. ) Is preferably used as a forming material.
  • the transparent anode 2 may be formed of a known electrode material, and an electrode material having a large work function such as ITO or gold is formed on the substrate 1 (transparent substrate such as a glass substrate). It is formed by vapor deposition.
  • the hole injection layer 3 provided on the transparent anode 2 can be formed using the above-described triphenylene derivative of the present invention, or can be formed using a conventionally known material, for example, the following materials.
  • Application-type polymer materials such as poly (3,4-ethylenedioxythiophene) (PEDOT), poly (styrene sulfonate) (PSS), etc .; Acceptor heterocyclic compounds such as hexacyanoazatriphenylene;
  • Formation of a layer (thin film) using the above materials can be performed by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method. Similarly, various layers described below can be formed by vapor deposition, spin coating, ink jetting, or the like.
  • the hole transport layer 4 provided on the hole injection layer 3 can also be formed using the above-described triphenylene derivative of the present invention, or can be formed using a conventionally known hole transport material. You can also. Typical examples of such conventionally known hole transport materials are as follows.
  • Benzidine derivatives such as N, N′-diphenyl-N, N′-di (m-tolyl) benzidine (hereinafter abbreviated as TPD); N, N′-diphenyl-N, N′-di ( ⁇ -naphthyl) benzidine (hereinafter abbreviated as NPD); N, N, N ′, N′-tetrabiphenylylbenzidine; Amine derivatives such as 1,1-bis [4- (di-4-tolylamino) phenyl] cyclohexane (hereinafter abbreviated as TAPC); Various triphenylamine trimers and tetramers; A carbazole derivative; The above coating type polymer material that is also used for a hole injection layer;
  • Such a compound of the hole transport material may be formed alone, but may be formed by mixing two or more kinds, or by using one or more of the above compounds.
  • a multilayer film in which a plurality of layers are formed and in which such layers are stacked can be used as a hole transport layer.
  • hole injection layer 3 and the hole transport layer 4 can also be used.
  • a hole injection / transport layer is made of poly (3,4-ethylenedioxythiophene (hereinafter referred to as PEDOT). It can be formed by coating with a polymer material such as (abbreviated).
  • the hole transport layer 4 (the same applies to the hole injection layer 3), it is possible to use a material which is usually used for the layer and further P-doped with trisbromophenylamine hexachloroantimony or the like.
  • the hole transport layer 4 (or the hole injection layer 3) can be formed using a polymer compound having a basic skeleton of TPD.
  • an electron blocking layer (not shown) (which can be provided between the light emitting layer 5 and the hole transport layer 3) can be formed using the triphenylene derivative of the present invention having an electron blocking action, It can also be formed using a known electron blocking compound such as a carbazole derivative or a compound having a triphenylsilyl group and a triarylamine structure. Specific examples of the compound having a carbazole derivative and a triarylamine structure are as follows.
  • TCTA 9,9-bis [4- (carbazol-9-yl) phenyl] Fluorene
  • mCP 1,3-bis (carbazol-9-yl) benzene
  • Ad-Cz 2,2-bis (4-carbazol-9-ylphenyl) adamantane
  • the electron blocking layer is formed using one or more of the triphenylene compound of the present invention and the above-described known hole transport materials alone or in combination of two or more of these hole transport materials.
  • a plurality of layers can be used to form a multilayer film in which such layers are stacked as an electron blocking layer.
  • metal complexes of quinolinol derivatives such as Alq 3
  • various metal complexes such as zinc, beryllium, and aluminum
  • anthracene derivatives bisstyrylbenzene derivatives
  • pyrene derivatives oxazole derivatives
  • polypara It can be formed using a light emitting material such as a phenylene vinylene derivative.
  • the light emitting layer 5 can also be comprised with a host material and a dopant material.
  • a host material in this case, in addition to the above light emitting material, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, or the like can be used, and further, the above-described triphenylene derivative of the present invention can also be used.
  • the dopant material quinacridone, coumarin, rubrene, perylene and derivatives thereof, benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives, and the like can be used.
  • Such a light-emitting layer 5 can also have a single-layer configuration using one or more of the light-emitting materials, or a multilayer structure in which a plurality of layers are stacked.
  • the light emitting layer 5 can also be formed using a phosphorescent light emitting material as the light emitting material.
  • a phosphorescent material a phosphorescent material of a metal complex such as iridium or platinum can be used.
  • green phosphorescent emitters such as Ir (ppy) 3
  • blue phosphorescent emitters such as FIrpic and FIr6
  • red phosphorescent emitters such as Btp 2 Ir (acac)
  • the material is used by doping into a hole injecting / transporting host material or an electron transporting host material.
  • the triphenylene derivative of the present invention carbazole derivatives such as 4,4′-di (N-carbazolyl) biphenyl (hereinafter abbreviated as CBP), TCTA, and mCP are used. be able to.
  • CBP 4,4′-di (N-carbazolyl) biphenyl
  • TCTA 4,4′-di (N-carbazolyl) biphenyl
  • mCP mCP
  • an electron transporting host material p-bis (triphenylsilyl) benzene (hereinafter abbreviated as UGH2), 2,2 ′, 2 ′′-(1,3,5-phenylene) -tris ( 1-phenyl-1H-benzimidazole) (hereinafter abbreviated as TPBI) and the like can be used.
  • the host material with a phosphorescent light emitting material by co-evaporation in the range of 1 to 30 weight percent with respect to the entire light emitting layer in order to avoid concentration quenching.
  • a hole blocking layer (not shown in FIG. 7) that can be provided between the light emitting layer 5 and the electron transport layer 6 can be formed using a compound having a known hole blocking action.
  • known compounds having such a hole blocking action include phenanthroline derivatives such as bathocuproin (hereinafter abbreviated as BCP), aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylpheno
  • BCP bathocuproin
  • BAlq metal complexes of quinolinol derivatives
  • triazole derivatives, triazine derivatives, oxadiazole derivatives, and the like can be given.
  • These materials can also be used for forming the electron transport layer 6 described below, and the hole blocking layer and the electron transport layer 6 can be used in combination.
  • Such a hole blocking layer can also have a single layer or multilayer structure, and each layer is formed using one or more of the compounds having the hole blocking action described above.
  • the electron transport layer 6 is an electron transport compound known per se, for example, metal complexes of quinolinol derivatives such as Alq 3 and BAlq, as well as various metal complexes such as zinc, beryllium, and aluminum, triazole derivatives, and triazine derivatives. Oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silole derivatives, and the like.
  • the electron transport layer 6 can also have a single layer or multilayer structure, and each layer is formed using one or more of the electron transport compounds described above.
  • the electron injection layer 7 is also known per se, for example, an alkali metal salt such as lithium fluoride or cesium fluoride, an alkaline earth metal salt such as magnesium fluoride, or a metal oxide such as aluminum oxide. Can be formed.
  • an alkali metal salt such as lithium fluoride or cesium fluoride
  • an alkaline earth metal salt such as magnesium fluoride
  • a metal oxide such as aluminum oxide.
  • an electrode material having a low work function such as aluminum, or an alloy having a lower work function such as a magnesium silver alloy, a magnesium indium alloy, or an aluminum magnesium alloy is used as the electrode material.
  • the organic EL device in which at least one of the organic layers (for example, the hole injection layer 3, the hole transport layer 4, the electron blocking layer or the light emitting layer 5) is formed using the triphenylene derivative of the present invention has a luminous efficiency and power. It has high efficiency, low practical driving voltage, low light emission starting voltage, and extremely excellent durability.
  • the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 24.0 g of a brown crude product.
  • the obtained crude product was dissolved in 300 ml of toluene and subjected to adsorption purification using 10.0 g of silica gel. After concentration under reduced pressure, crystallization using a mixed solvent of toluene / n-hexane, crystallization using a mixed solvent of toluene / methanol, and reflux washing using methanol were performed, whereby bis (9,9- 12.0 g (yield 60%) of a light yellow powder of dimethyl-9H-fluoren-2-yl)-(triphenylene-2-yl) amine (Compound 14) was obtained.
  • Tetrakis (triphenylphosphine) palladium 1.06g
  • the mixture was heated and stirred for 5.5 hours under reflux.
  • the mixture was allowed to cool to room temperature, 200 ml of toluene and 100 ml of water were added, and the organic layer was collected by a liquid separation operation.
  • the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a crude product.
  • Example 7 (Measurement of glass transition point)
  • the glass transition point was determined by a high-sensitivity differential scanning calorimeter (manufactured by Bruker AXS, DSC3100S). The results were as follows. Glass transition point Compound of Example 1 129 ° C Compound of Example 2 146 ° C Compound of Example 3 126 ° C. Compound of Example 4 140 ° C This shows that the triphenylene derivative of the present invention has a glass transition point of 100 ° C. or higher and exhibits a stable thin film state.
  • Example 9 (Characteristic evaluation of organic EL elements) An organic EL device having the structure shown in FIG. 7 was prepared which was provided with a hole transport layer formed using the triphenylene derivative (compound 4) obtained in Example 1.
  • the glass substrate 1 on which ITO having a thickness of 150 nm was formed was washed with an organic solvent, and then the surface was washed by oxygen plasma treatment. Thereafter, the glass substrate 1 with ITO electrode is mounted in a vacuum vapor deposition machine, the pressure inside the vapor deposition machine is reduced to 0.001 Pa or less, and in this state, a film thickness is formed so as to cover the transparent anode 2 using the compound 100 having the following structural formula. Formed a 20 nm hole injection layer 3.
  • the triphenylene derivative (compound 4) obtained in Example 1 was deposited to form a hole transport layer 4 having a thickness of 40 nm.
  • the light emitting layer 5 having a thickness of 30 nm was formed.
  • Alq 3 was used to form an electron transport layer 6 having a thickness of 30 nm on the light emitting layer 5. Further, lithium fluoride was used to form an electron injection layer 7 having a thickness of 0.5 nm on the electron transport layer 6. Finally, aluminum was vapor-deposited to a thickness of 150 nm to form the cathode 8 to obtain an organic EL device having the structure shown in FIG.
  • Table 1 summarizes the measurement results of the light emission characteristics of the organic EL elements produced as described above when a DC voltage was applied in the atmosphere at room temperature.
  • the driving voltage when a current with a current density of 10 mA / cm 2 was applied was the compound of Example 1 (Compound 4) compared to 5.17 V of the organic EL device using Compound 103.
  • the organic EL element used has a low voltage of 5.06 V, and the power efficiency is 5.49 lm / W of the organic EL element using Compound 103, and the compound (Compound 4) of Example 1 of the present invention is used.
  • the organic EL element used was greatly improved to 6.52 lm / W.
  • the organic EL device using the triphenylene derivative of the present invention is improved in luminous efficiency and power efficiency as compared with the organic EL device using the compound 103 which is a known material, It was found that a decrease in practical driving voltage can be achieved.
  • the triphenylene derivative of the present invention is excellent as a compound for an organic EL device because it has a high hole transport capability, is excellent in amorphous properties, and is stable in a thin film state.
  • high luminous efficiency and power efficiency can be obtained, practical driving voltage can be lowered, and durability can be improved. For example, it has become possible to develop home appliances and lighting.

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Abstract

Un dérivé de triphénylène selon la présente invention est représenté par la formule générale (1) (avec Ar1 et Ar2 représentant de manière indépendante un groupement aromatique). Le composé possède une structure telle qu'une amine tertiaire aromatique est introduite dans un cycle triphénylène. Ainsi, le composé a les propriétés de (A) à (E) mentionnées ci-dessous qui sont associées avec la structure, et est utile en tant que substance de transport de trous destinée à être utilisée dans un élément électroluminescent organique : (A) la propriété d'injection de trous est bonne ; (B) la mobilité des trous est élevée ; (C) la capacité d'arrêt d'électrons est excellente ; (D) l'état est stable lorsqu'il est formé en une couche mince ; et (E) la résistance thermique est excellente.
PCT/JP2013/058998 2012-04-18 2013-03-27 Nouveau dérivé de triphénylène, et élément électroluminescent organique dans lequel ledit dérivé est utilisé WO2013157367A1 (fr)

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