WO2018101491A2 - Élément électroluminescent organique et dispositif électronique - Google Patents

Élément électroluminescent organique et dispositif électronique Download PDF

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WO2018101491A2
WO2018101491A2 PCT/JP2018/010875 JP2018010875W WO2018101491A2 WO 2018101491 A2 WO2018101491 A2 WO 2018101491A2 JP 2018010875 W JP2018010875 W JP 2018010875W WO 2018101491 A2 WO2018101491 A2 WO 2018101491A2
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general formula
layer
group
organic
light emitting
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PCT/JP2018/010875
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Japanese (ja)
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WO2018101491A3 (fr
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裕基 中野
知浩 長尾
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出光興産株式会社
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • the present invention relates to an organic electroluminescence element and an electronic device.
  • an organic electroluminescence element hereinafter sometimes referred to as an organic EL element
  • holes from the anode and electrons from the cathode are injected into the light emitting layer. Then, in the light emitting layer, the injected holes and electrons are recombined to form excitons.
  • the organic EL element includes a light emitting layer between an anode and a cathode. Moreover, it may have a laminated structure including organic layers such as a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer. As an organic EL element having a laminated structure of a plurality of organic layers, for example, there are organic EL elements described in Patent Document 1 and Patent Document 2.
  • the following organic electroluminescence device is provided.
  • the organic layer includes a light-emitting layer, and a hole transport region disposed between the anode and the light-emitting layer,
  • the light emitting layer contains a compound represented by the following general formula (1):
  • the hole transport region includes a compound represented by the following general formula (2).
  • Ar 1 represents a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms.
  • Ar 2 represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms
  • R 1 to R 9 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, —NR 10 R 11 , Or a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms
  • R 10 and R 11 each independently represents a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms.
  • R 2 and R 3 may combine to form a ring structure of the following general formula (3-1) or general formula (3-2). ]
  • R 1 and R 4 to R 9 are respectively synonymous with the groups in the general formula (2), Ph represents a phenyl group.
  • an electronic apparatus including the organic electroluminescence element is provided.
  • an organic electroluminescence element having light emission characteristics at a practical level
  • an electronic apparatus including the organic electroluminescence element
  • the organic electroluminescence device is The anode, A cathode, An organic layer disposed between the anode and the cathode, The organic layer includes a light-emitting layer, and a hole transport region disposed between the anode and the light-emitting layer,
  • the light emitting layer contains a compound represented by the following general formula (1):
  • the hole transport region includes a compound represented by the following general formula (2).
  • Ar 1 represents a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms.
  • Ar 2 represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms
  • R 1 to R 9 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, —NR 10 R 11 , Or a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms
  • R 10 and R 11 each independently represents a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms.
  • R 2 and R 3 may combine to form a ring structure of the following general formula (3-1) or general formula (3-2). ]
  • Examples of the aryl group having 6 to 20 ring carbon atoms in Ar 1 , Ar 2 , and R 1 to R 11 include a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, and a fluoranthenyl group.
  • Ar 1 is preferably a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a 9,9′-dimethylolfluorenyl group, a 9,9′-diphenylfluorenyl group or a floranthenyl group.
  • Examples of the alkyl group having 1 to 10 carbon atoms in R 1 to R 9 include a methyl group, an ethyl group, a propyl group, a t-butyl group, and an n-butyl group.
  • Examples of the heterocyclic group having 3 to 20 ring atoms in R 1 to R 9 include a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.
  • the “substituent” in “substituted or unsubstituted” of each group of Ar 1 , Ar 2 , and R 1 to R 11 is an alkyl group having 1 to 10 carbon atoms or an aryl having 6 to 20 ring carbon atoms Groups.
  • Examples of the alkyl group having 1 to 10 carbon atoms as the “substituent” of each group of Ar 1 , Ar 2 , and R 1 to R 11 include, for example, a methyl group, an ethyl group, a propyl group, a t-butyl group, or n -A butyl group etc. are mentioned.
  • Examples of the 6 to 20 aryl group as the “substituent” of each group of Ar 1 , Ar 2 , and R 1 to R 11 include a phenyl group, a biphenyl group, and a naphthyl group.
  • the compound represented by the general formula (1) can be synthesized, for example, by the following production route.
  • the compound represented by the general formula (2) can be synthesized, for example, by the following production route.
  • the hydrogen atom includes light hydrogen (protium) and deuterium which are isotopes having different numbers of neutrons.
  • FIG. 1 shows an outline of an example of the layer configuration of the organic EL element.
  • the organic EL element 1 in FIG. 1 includes a substrate 2, an anode 3, a cathode 4, and a light emitting unit (organic layer) 10 disposed between the anode 3 and the cathode 4.
  • the light emitting unit (organic layer) 10 includes at least one light emitting layer 5 and a hole transport region (hole injection layer, hole transport layer, etc.) 6 disposed between the anode 3 and the light emitting layer 5.
  • An electron transport region (electron injection layer, electron transport layer, etc.) 7 may be formed between the light emitting layer 5 and the cathode 4.
  • an electron blocking layer (not shown) may be provided on the light emitting layer 5 on the anode 3 side, and a hole blocking layer (not shown) may be provided on the light emitting layer 5 on the cathode 4 side.
  • the organic EL device includes a compound represented by the general formula (1) in the light emitting layer 5, and the hole transport region (hole injection layer, hole transport layer, etc.) 6 has the general formula.
  • the compound represented by (2) is included.
  • the organic EL device according to the present invention is not limited to the layer configuration of the organic EL device 1 illustrated in FIG. 1.
  • the hole transport region 6 may have a stacked configuration of two or more layers.
  • the electron transport region 7 may also have a laminated structure of two or more layers.
  • the organic EL device may be, for example, a fluorescent or phosphorescent monochromatic light emitting device or a fluorescent / phosphorescent white light emitting device. Further, it may be a simple type having a single light emitting unit or a tandem type having two or more light emitting units.
  • the “light emitting unit” described in this specification includes an organic layer, and at least one of the organic layers is a light emitting layer, and emits light by recombination of injected holes and electrons. Say the smallest unit.
  • the “light emitting layer” described in the present specification is an organic layer having a light emitting function.
  • the light emitting layer is, for example, a phosphorescent light emitting layer, a fluorescent light emitting layer or the like, and may be one layer or two or more layers.
  • the light emitting unit may be a laminated type having two or more phosphorescent light emitting layers or fluorescent light emitting layers. In this case, for example, a space for preventing excitons generated in the phosphorescent light emitting layer from diffusing into the fluorescent light emitting layer. You may have a layer between each light emitting layer.
  • the layer structure of the organic EL element according to one embodiment of the present invention is not limited to these.
  • the organic EL element has a hole injection layer and a hole transport layer
  • a hole injection layer is provided between the hole transport layer and the anode.
  • an organic EL element has an electron injection layer and an electron carrying layer
  • the electron injection layer is provided between the electron carrying layer and the cathode.
  • Each of the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer may be composed of one layer, or may be composed of two or more layers.
  • the substrate 2 is used as a support for the organic EL element.
  • glass, quartz, plastic, or the like can be used as the substrate.
  • a flexible substrate may be used.
  • the flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate made of polycarbonate or polyvinyl chloride.
  • anode As the anode 3, it is preferable to use, for example, a metal, an alloy, a conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more).
  • anode materials include indium tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and oxide containing zinc oxide. Indium, graphene, and the like can be given.
  • anode 3 gold, silver, platinum, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, nitrides of these metals (for example, titanium nitride), and the like can be given.
  • the method for forming the anode 3 include sputtering, vacuum deposition, coating, ink jet, and spin coating.
  • the hole injection layer formed in contact with the anode 3 is a layer containing a substance having a high hole injection property and has a function of injecting holes from the anode into the organic layer.
  • substances having a high hole injection property include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, and silver oxide. Materials, tungsten oxides, manganese oxides, aromatic amine compounds, electron-withdrawing (acceptor) compounds, polymer compounds, and the like.
  • the hole transport layer included in the hole transport region 6 is a layer containing a substance having a high hole transport property, and has a function of transporting holes from the anode 3 to the organic layer 10.
  • the substance having a high hole transporting property is preferably a substance having a hole mobility of 10 ⁇ 6 cm 2 / (V ⁇ s) or more.
  • the organic EL element which concerns on 1 aspect of this invention contains the compound represented by General formula (2) in the positive hole transport area
  • the hole transport region 6 and the hole transport layer constituting the hole transport region 6 may be a single layer or two or more layers may be laminated. In this case, it is preferable to dispose a layer containing a substance having a larger energy gap among substances having a high hole transporting property on the side close to the light emitting layer.
  • the organic EL element is represented by the general formula (2) in at least one layer constituting the hole transport region 6. Are included.
  • the light emitting layer 5 is a layer containing a substance (dopant material) having a high light emitting property.
  • a substance (dopant material) having a high light emitting property various materials can be used.
  • a fluorescent compound (fluorescent dopant), a phosphorescent compound (phosphorescent dopant), or the like can be used.
  • a fluorescent compound is a compound that can emit light from a singlet excited state, and a light-emitting layer containing the compound is called a fluorescent light-emitting layer.
  • a phosphorescent compound is a compound that can emit light from a triplet excited state, and a light-emitting layer containing the compound is called a phosphorescent light-emitting layer.
  • the light emitting layer 5 usually contains a dopant material and a host material for efficiently emitting light.
  • the dopant material may be referred to as a guest material, an emitter, or a light-emitting material depending on the literature.
  • the host material may be referred to as a matrix material depending on the literature.
  • One light emitting layer may contain two or more dopant materials and two or more host materials. Further, the light emitting layer may be two or more.
  • the organic EL device according to one embodiment of the present invention includes the compound represented by the general formula (1) in the light emitting layer 5.
  • the compound represented by the general formula (1) functions as a host material.
  • the host material combined with the fluorescent dopant is referred to as “fluorescent host”, and the host material combined with the phosphorescent dopant is referred to as “phosphorescent host”.
  • the fluorescent host and the phosphorescent host are not classified only by the molecular structure.
  • the phosphorescent host is a material for forming a phosphorescent light emitting layer containing a phosphorescent dopant, but does not mean that it cannot be used as a material for forming a fluorescent light emitting layer. The same applies to the fluorescent host.
  • the content of the dopant material in the light emitting layer 5 is not particularly limited, but is preferably 0.1 to 99% by mass, for example, from the viewpoint of sufficient light emission and concentration quenching, and 0.1 to 70%. More preferably, it is more preferably 0.1 to 30% by mass.
  • fluorescent dopant examples include condensed polycyclic aromatic derivatives, styrylamine derivatives, condensed ring amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, carbazole derivatives, and the like. Among these, condensed ring amine derivatives, boron-containing compounds, and carbazole derivatives are preferable.
  • the condensed ring amine derivative examples include diaminopyrene derivatives, diaminochrysene derivatives, diaminoanthracene derivatives, diaminofluorene derivatives, diaminofluorene derivatives in which one or more benzofuro skeletons are condensed.
  • the boron-containing compound include a pyromethene derivative and a triphenylborane derivative.
  • fluorescent dopants include the compounds shown below.
  • the compound represented by the general formula (1) functions as a host material in the light-emitting layer.
  • a host material in a light emitting layer in addition to the compound represented by General formula (1), you may contain another host material.
  • the fluorescent host that can be used in combination is preferably a compound having a singlet level higher than that of the fluorescent dopant, and examples thereof include a heterocyclic compound and a condensed aromatic compound.
  • the condensed aromatic compound for example, anthracene derivatives, pyrene derivatives, chrysene derivatives, naphthacene derivatives and the like are preferable.
  • the electron transport region 7 and the electron transport layer constituting the electron transport region 7 are layers containing a substance having a high electron transport property.
  • the substance having a high electron transporting property is preferably a substance having an electron mobility of 10 ⁇ 6 cm 2 / Vs or more.
  • the metal complex examples include an aluminum complex, a beryllium complex, and a zinc complex.
  • tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq3) bis (10-hydroxybenzo [h] quinolinato) beryllium (Abbreviation: BeBq2)
  • bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) abbreviation: BAlq
  • aromatic heterocyclic compound examples include imidazole derivatives such as benzimidazole derivatives, imidazopyridine derivatives, and benzimidazophenanthridine derivatives; azine derivatives such as pyrimidine derivatives and triazine derivatives; quinoline derivatives, isoquinoline derivatives, phenanthroline derivatives, and the like.
  • imidazole derivatives such as benzimidazole derivatives, imidazopyridine derivatives, and benzimidazophenanthridine derivatives
  • azine derivatives such as pyrimidine derivatives and triazine derivatives
  • quinoline derivatives isoquinoline derivatives, phenanthroline derivatives, and the like.
  • examples thereof include compounds containing a nitrogen six-membered ring structure (including those having a phosphine oxide substituent in the heterocyclic ring).
  • aromatic heterocyclic compound used for the electron transport layer include the following compounds.
  • aromatic hydrocarbon compound examples include anthracene derivatives and fluoranthene derivatives.
  • the electron transport layer examples include metals such as alkali metals, magnesium, alkaline earth metals, alloys containing two or more of these metals; alkali metal compounds such as 8-quinolinolato lithium (abbreviation: Liq), A metal compound such as an alkaline earth metal compound may be contained.
  • a metal such as an alkali metal, magnesium, an alkaline earth metal, or an alloy containing two or more of these metals is contained in the electron transport layer, the content is not particularly limited, but 0 It is preferably 1 to 50% by mass, more preferably 0.1 to 20% by mass, and still more preferably 1 to 10% by mass.
  • the content is preferably 1 to 99% by mass, more preferably 10 to 90% by mass. It is. Note that the layer on the light emitting layer side in the case where the electron transport layer is two or more layers can be formed of only these metal compounds.
  • the electron injection layer is a layer containing a substance having a high electron injection property and has a function of efficiently injecting electrons from the cathode to the light emitting layer.
  • the substance having a high electron injecting property include alkali metals, magnesium, alkaline earth metals, and compounds thereof. Specifically, lithium, cesium, calcium, lithium fluoride, cesium fluoride, calcium fluoride, lithium oxide, and the like can be given.
  • an alkali metal, magnesium, alkaline earth metal, or a compound containing these compounds, for example, an Alq containing magnesium, or the like can also be used in a substance having an electron transporting property.
  • a composite material including an organic compound and a donor compound can be used. Since an organic compound receives electrons from a donor compound, such a composite material is excellent in electron injecting property and electron transporting property.
  • a substance having excellent transportability of received electrons is preferable.
  • a metal complex or an aromatic heterocyclic compound which is the above-described substance having high electron transportability can be used.
  • the donor compound may be any substance that can donate electrons to an organic compound, and examples thereof include alkali metals, magnesium, alkaline earth metals, and rare earth metals. Specifically, lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like can be given.
  • Alkali metal oxides and alkaline earth metal oxides are preferable, and specific examples include lithium oxide, calcium oxide, and barium oxide.
  • a Lewis base such as magnesium oxide can also be used.
  • an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.
  • the cathode is preferably a metal, an alloy, a conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less).
  • the material of the cathode include alkali metals such as lithium and cesium; magnesium; alkaline earth metals such as calcium and strontium; alloys containing these metals (for example, magnesium-silver, aluminum-lithium); europium, ytterbium, and the like Rare earth metals; alloys containing rare earth metals.
  • the cathode is usually formed by vacuum deposition or sputtering. Moreover, when using a silver paste etc., the apply
  • the cathode is formed using various conductive materials such as aluminum, silver, ITO, graphene, silicon or indium oxide-tin oxide containing silicon oxide regardless of the work function. Can be formed. These conductive materials can be formed by a sputtering method, an inkjet method, a spin coating method, or the like.
  • the method for forming each layer of the organic EL element is not particularly limited unless otherwise specified.
  • a forming method a known method such as a dry film forming method or a wet film forming method can be used.
  • Specific examples of the dry film forming method include a vacuum deposition method, a sputtering method, a plasma method, and an ion plating method.
  • Specific examples of the wet film forming method include various coating methods such as a spin coating method, a dipping method, a flow coating method, and an ink jet method.
  • the thickness of each layer of the organic EL element is not particularly limited unless otherwise specified. If the film thickness is too small, defects such as pinholes are likely to occur, and sufficient light emission luminance cannot be obtained. On the other hand, if the film thickness is too large, a high driving voltage is required, and the efficiency is lowered. From such a viewpoint, the film thickness is usually preferably from 0.1 nm to 10 ⁇ m, preferably from 5 nm to 10 ⁇ m, and more preferably from 10 nm to 0.2 ⁇ m.
  • An electronic device includes the above-described organic EL element according to one embodiment of the present invention.
  • Specific examples of the electronic device include display components such as an organic EL panel module; display devices such as a television, a mobile phone, a smartphone, and a personal computer; lighting, a light emitting device for a vehicle lamp, and the like.
  • Example 1 A 25 mm ⁇ 75 mm ⁇ 1.1 mm thick glass substrate with an ITO transparent electrode line (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes.
  • the film thickness of the ITO transparent electrode was 130 nm.
  • the glass substrate with the transparent electrode line after washing is attached to the substrate holder of the vacuum deposition apparatus, and the compound HT1 and the compound HI are co-deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed. Then, a co-evaporated film layer (H-1 layer) having a thickness of 10 nm was formed.
  • the concentration of compound HI in the H-1 layer was 3% by weight.
  • the compound HT1 was vapor-deposited on the co-evaporated film layer to form an HT1 layer (H-2 layer) having a thickness of 80 nm.
  • the compound HT2 was vapor-deposited to form a HT2 layer (H-3 layer) having a thickness of 10 nm.
  • the compound GH1 as a host material and the compound GD1 as a light emitting dopant material (fluorescent dopant) were co-evaporated to form a light emitting layer having a thickness of 25 nm.
  • the concentration of the compound GD1 in the light emitting layer was 4% by mass.
  • the compound ET1 and the compound Liq were co-evaporated to form a 20 nm thick layer (E-1 layer).
  • the concentration of Compound Liq in this layer was 30% by weight.
  • a compound Liq was deposited on this layer at a film formation rate of 0.1 angstrom / min to form a Liq layer (E-2) having a thickness of 1 nm.
  • Metal Al was vapor-deposited on this layer, and a metal cathode was formed with a film thickness of 80 nm.
  • the organic EL element of Example 1 has the following layer structure.
  • ITO (130 nm) / HT1 + HI (5 nm) / HT1 (80 nm) / HT2 (10 nm) / GH1: GD (25 nm) / ET1: Liq (20 nm) / Liq (1 nm) / Al (80 nm)
  • voltage was applied to the obtained organic EL device, it showed light emission characteristics at a practical level.
  • Example 2 to 12 An organic EL device was produced in the same manner as in Example 1 except that each compound shown in Table 1 was used as a material for the hole transport region, the light emitting layer, and the electron transport region. When voltage was applied to the organic EL elements obtained in Examples 2 to 12, all showed light emission characteristics at a practical level.

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

Abstract

Un élément électroluminescent organique (1) est pourvu d'une anode (3), d'une cathode (4) et d'une couche organique (10) placée entre l'anode (3) et la cathode (4), laquelle couche organique (10) comprend une couche émissive (5) et une région de transport de trous (6) placée entre l'anode (3) et la couche émissive (5), la couche émissive (5) comprenant un composé représenté par la formule générale (1), et la région de transport de trous (6) comprenant un composé représenté par la formule générale (2).
PCT/JP2018/010875 2018-03-19 2018-03-19 Élément électroluminescent organique et dispositif électronique WO2018101491A2 (fr)

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Publication number Priority date Publication date Assignee Title
WO2021241738A1 (fr) * 2020-05-29 2021-12-02 出光興産株式会社 Mélange, élément électroluminescent organique, procédé de fabrication d'élément électroluminescent organique et appareil électronique
WO2022230843A1 (fr) * 2021-04-26 2022-11-03 出光興産株式会社 Élément électroluminescent organique, appareil d'affichage électroluminescent organique et dispositif électronique

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KR101604168B1 (ko) * 2012-02-27 2016-03-16 주식회사 엘지화학 유기 발광 소자
KR101566578B1 (ko) * 2012-02-27 2015-11-05 주식회사 엘지화학 유기 발광 소자
KR101596547B1 (ko) * 2012-02-27 2016-02-23 주식회사 엘지화학 유기 발광 소자
EP3161885B1 (fr) * 2014-06-30 2021-05-19 Basf Se Procédé de fabrication de matériaux de cathode pour batteries au lithium-ion
KR102493763B1 (ko) * 2014-12-05 2023-01-30 호도가야 가가쿠 고교 가부시키가이샤 유기 일렉트로루미네선스 소자
US10497876B2 (en) * 2014-12-24 2019-12-03 Hodogaya Chemical Co., Ltd. Organic electroluminescent device

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021241738A1 (fr) * 2020-05-29 2021-12-02 出光興産株式会社 Mélange, élément électroluminescent organique, procédé de fabrication d'élément électroluminescent organique et appareil électronique
WO2022230843A1 (fr) * 2021-04-26 2022-11-03 出光興産株式会社 Élément électroluminescent organique, appareil d'affichage électroluminescent organique et dispositif électronique

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