WO2018101492A2 - Organic electroluminescent element and electronic device - Google Patents
Organic electroluminescent element and electronic device Download PDFInfo
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- 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 includes a phosphorescent light emitting material,
- the hole transport region is represented by the following general formula (1) and includes two kinds of compounds having different structures from each other.
- Organic electroluminescence device is represented by the following general formula (1) and includes two kinds of compounds having different structures from each other.
- Ar represents a hydrogen atom or an unsubstituted aryl group having 6 to 20 ring carbon atoms
- R is represented by any one of general formula (1-1), general formula (1-2), and general formula (1-3);
- Ar 1 and Ar 2 each independently represents an unsubstituted aryl group having 6 to 20 ring carbon atoms,
- Ar 3 represents a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms.
- 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 includes a phosphorescent light emitting material, The hole transport region includes two kinds of compounds represented by the following general formula (1) and having different structures.
- Ar represents a hydrogen atom or an unsubstituted aryl group having 6 to 20 ring carbon atoms
- R is represented by any one of general formula (1-1), general formula (1-2), and general formula (1-3);
- Ar 1 and Ar 2 each independently represents an unsubstituted aryl group having 6 to 20 ring carbon atoms,
- Ar 3 represents a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms.
- Examples of the aryl group having 6 to 20 ring carbon atoms in Ar, Ar 1 , Ar 2 and Ar 3 include a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group and a phenanthryl group.
- Ar, Ar 1 and Ar 2 are preferably each independently a phenyl group, a naphthyl group, a biphenyl group, or a terphenyl group.
- Examples of the “substituent” in the “substituted or unsubstituted” of Ar 3 include an alkyl group having 1 to 10 carbon atoms or an alkyl group having 6 to 20 ring carbon atoms.
- Examples of the alkyl group having 1 to 10 carbon atoms as the “substituent” of each of Ar 1 to Ar 5 and L 1 to L 3 include a methyl group, an ethyl group, a propyl group, a t-butyl group, and n-butyl. Groups and the like.
- Examples of the 6 to 20 alkyl group as the “substituent” of each of the groups Ar 1 to Ar 5 and L 1 to L 3 include a phenyl group, a biphenyl group, and a naphthyl group.
- 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.
- the organic EL device includes a phosphorescent light-emitting material in the light-emitting layer 5 and is represented by the general formula (1) in the hole transport region (hole injection layer, hole transport layer, or the like) 6. And two kinds of compounds having different structures from each other.
- FIG. 2 shows an outline of another example of the layer structure of the organic EL element.
- the hole transport layer in the hole transport region 6 and the electron transport in the electron transport region 7 of the light emitting unit 10 of the organic EL element 1 in FIG. Each layer has a two-layer structure.
- the hole transport region 6 has a first hole transport layer 6a on the anode 3 side and a second hole transport layer 6b on the cathode 4 side.
- the electron transport region 7 includes a first electron transport layer 7a on the anode side and a second hole transport layer 7b on the cathode side.
- the other reference numerals are the same as those in FIG.
- the first hole transport layer 6a on the anode 3 side is a compound represented by the general formula (1) (referred to as “first compound”).
- the second hole transport layer 6b on the cathode 4 and light emitting layer 5 side is represented by the general formula (1), and has a structure different from that of the first compound (referred to as “second compound”). It is preferable to include.
- the organic EL device according to the present invention is not limited to the layer configuration of the organic EL devices 1 and 11 illustrated in FIGS. 1 and 2.
- the hole transport region 6 is a stacked configuration of three or more layers.
- the electron transport region 7 may also have a laminated structure of three 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 layers 6 a and 6 b are layers containing a substance having a high hole transport property and have 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.
- an aromatic amine compound, a carbazole derivative, an anthracene derivative, a polymer compound Etc As long as the hole transporting property is higher than the electron transporting property, substances other than these may be used for the hole transporting layers 6a and 6b.
- the hole transport layers 6a and 6b and 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 device includes two types of compounds represented by the general formula (1) in the hole transport region (hole injection layer, hole transport layer, etc.) 6 and having different structures. including.
- the first hole transport layer 6a on the anode 3 side includes a compound represented by the general formula (1) (first compound)
- the second hole transport layer 6b on the cathode 4 and light emitting layer 5 side is preferably represented by the general formula (1) and contains a compound (second compound) having a structure different from that of the first compound.
- the light emitting layer 5 is a layer containing a substance (dopant material) having a high light emitting property.
- the organic EL element according to one embodiment of the present invention includes a phosphorescent light emitting material in the light emitting layer 5 as a dopant material.
- 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 (light emitting material) and a host material for efficiently emitting light.
- the dopant material may be referred to as a guest material or an emitter 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 content of the dopant material (light emitting 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, More preferably, it is 1 to 70% by mass, and further preferably 0.1 to 30% by mass.
- phosphorescent dopant phosphorescent light-emitting material
- phosphorescent dopants include phosphorescent heavy metal complexes and phosphorescent rare earth metal complexes.
- heavy metal complexes include iridium complexes, osmium complexes, platinum complexes, and the like.
- the heavy metal complex is preferably an orthometalated complex of a metal selected from iridium, osmium, and platinum.
- rare earth metal complexes include terbium complexes and europium complexes.
- phosphorescent host material As the phosphorescent host, a compound having a triplet level higher than that of the phosphorescent dopant is preferable, and examples thereof include metal complexes, heterocyclic compounds, and condensed aromatic compounds. Among these, for example, indole derivatives, carbazole derivatives, pyridine derivatives, pyrimidine derivatives, triazine derivatives, quinoline derivatives, isoquinoline derivatives, quinazoline derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, naphthalene derivatives, triphenylene derivatives, phenanthrene derivatives, fluoranthene derivatives, etc. preferable.
- the electron transport layers 7a and 7b and 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 glass substrate with an ITO transparent electrode line of 25 mm ⁇ 75 mm ⁇ thickness 1.1 mm (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, UV ozone cleaning was performed 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.
- a compound HT5 was vapor-deposited on the co-evaporated film layer to form a HT5 layer (H-2 layer) having a thickness of 100 nm.
- a compound HT9 was vapor-deposited to form a HT9 layer (H-3 layer) having a thickness of 15 nm.
- the compound PRH as a host material and the compound RD as a light emitting dopant material were co-evaporated to form a light emitting layer having a thickness of 30 nm.
- the concentration of Compound RD in the light emitting layer was 5% by mass.
- compound ET1 and compound Liq were co-evaporated to form a 30 nm thick layer (E-1 layer).
- the concentration of Compound Liq in this layer was 30% by weight. Further, a compound Liq was vapor-deposited on this layer at a film formation rate of 0.1 angstrom / min to form a Liq layer (E-2 layer) 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.
- Example 2 to 48 An organic EL device was produced in the same manner as in Example 1 except that the compounds shown in Tables 1 and 2 were used as materials 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 48, all showed light emission characteristics at a practical level.
Abstract
An organic electroluminescent element (1) provided with an anode (3), a cathode (4), and an organic layer (10) disposed between the anode (3) and the cathode (4), the organic layer (10) comprising an emissive layer (5) and a hole transport region (6) disposed between the anode (3) and the emissive layer (5), the emissive layer (5) comprising a phosphorescent light-emitting material, and the hole transport region (6) comprising at least two types compounds that are each represented by general formula (1) and have mutually different structures.
Description
本発明は、有機エレクトロルミネッセンス素子及び電子機器に関する。
The present invention relates to an organic electroluminescence element and an electronic device.
有機エレクトロルミネッセンス素子（以下、有機ＥＬ素子ということがある）に電圧を印加すると、陽極から正孔が、また陰極から電子が、それぞれ発光層に注入される。そして、発光層において、注入された正孔と電子とが再結合し、励起子が形成される。
When a voltage is applied to 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.
有機ＥＬ素子は、陽極と陰極の間に、発光層を含む。また、正孔注入層、正孔輸送層、電子注入層、電子輸送層等の有機層を含む積層構造を有する場合もある。複数の有機層の積層構造を有する有機ＥＬ素子としては、例えば、特許文献１や特許文献２に記載の有機ＥＬ素子がある。
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.
本発明の一態様によれば、以下の有機エレクトロルミネッセンス素子が提供される。
陽極と、
陰極と、
前記陽極と前記陰極の間に配された有機層と、を備え、
前記有機層は、発光層、及び、前記陽極と前記発光層との間に配された正孔輸送領域を含み、
前記発光層は、燐光性の発光材料を含み、
前記正孔輸送領域は、下記一般式（１）で表され、且つ、互いに構造が異なる２種類の化合物を含む、
有機エレクトロルミネッセンス素子。 According to one aspect of the present invention, the following organic electroluminescence device is provided.
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 includes a phosphorescent light emitting material,
The hole transport region is represented by the following general formula (1) and includes two kinds of compounds having different structures from each other.
Organic electroluminescence device.
陽極と、
陰極と、
前記陽極と前記陰極の間に配された有機層と、を備え、
前記有機層は、発光層、及び、前記陽極と前記発光層との間に配された正孔輸送領域を含み、
前記発光層は、燐光性の発光材料を含み、
前記正孔輸送領域は、下記一般式（１）で表され、且つ、互いに構造が異なる２種類の化合物を含む、
有機エレクトロルミネッセンス素子。 According to one aspect of the present invention, the following organic electroluminescence device is provided.
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 includes a phosphorescent light emitting material,
The hole transport region is represented by the following general formula (1) and includes two kinds of compounds having different structures from each other.
Organic electroluminescence device.
[一般式（１）中、
Ａｒは、水素原子、又は無置換の環形成炭素数６～２０のアリール基を表し、
Ｒは、一般式（１－１）、一般式（１－２）、一般式（１－３）のいずれかで表され、
Ａｒ１及びＡｒ２は、それぞれ独立に、無置換の環形成炭素数６～２０のアリール基を表し、
Ａｒ３は、置換もしくは無置換の環形成炭素数６～２０のアリール基を表す。] [In general formula (1),
Ar represents a hydrogen atom or an unsubstituted aryl group having 6 to 20 ring carbon atoms,
R is represented by any one of general formula (1-1), general formula (1-2), and general formula (1-3);
Ar 1 and Ar 2 each independently represents an unsubstituted aryl group having 6 to 20 ring carbon atoms,
Ar 3 represents a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms. ]
Ａｒは、水素原子、又は無置換の環形成炭素数６～２０のアリール基を表し、
Ｒは、一般式（１－１）、一般式（１－２）、一般式（１－３）のいずれかで表され、
Ａｒ１及びＡｒ２は、それぞれ独立に、無置換の環形成炭素数６～２０のアリール基を表し、
Ａｒ３は、置換もしくは無置換の環形成炭素数６～２０のアリール基を表す。] [In general formula (1),
Ar represents a hydrogen atom or an unsubstituted aryl group having 6 to 20 ring carbon atoms,
R is represented by any one of general formula (1-1), general formula (1-2), and general formula (1-3);
Ar 1 and Ar 2 each independently represents an unsubstituted aryl group having 6 to 20 ring carbon atoms,
Ar 3 represents a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms. ]
本発明の他の態様によれば、上記有機エレクトロルミネッセンス素子を備える電子機器が提供される。
According to another aspect of the present invention, an electronic apparatus including the organic electroluminescence element is provided.
本発明の一態様によれば、実用レベルの発光特性を有する有機エレクトロルミネッセンス素子、及びそれを備えた電子機器を提供することが可能となる。
According to one embodiment of the present invention, it is possible to provide an organic electroluminescence element having light emission characteristics at a practical level, and an electronic apparatus including the organic electroluminescence element.
本発明の一態様に係る有機エレクトロルミネッセンス素子は、
陽極と、
陰極と、
前記陽極と前記陰極の間に配された有機層と、を備え、
前記有機層は、発光層、及び、前記陽極と前記発光層との間に配された正孔輸送領域を含み、
前記発光層は、燐光性の発光材料を含み、
前記正孔輸送領域は、下記一般式（１）で表され、且つ、互いに構造が異なる２種類の化合物を含む。 The organic electroluminescence device according to one embodiment of the present invention 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 includes a phosphorescent light emitting material,
The hole transport region includes two kinds of compounds represented by the following general formula (1) and having different structures.
陽極と、
陰極と、
前記陽極と前記陰極の間に配された有機層と、を備え、
前記有機層は、発光層、及び、前記陽極と前記発光層との間に配された正孔輸送領域を含み、
前記発光層は、燐光性の発光材料を含み、
前記正孔輸送領域は、下記一般式（１）で表され、且つ、互いに構造が異なる２種類の化合物を含む。 The organic electroluminescence device according to one embodiment of the present invention 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 includes a phosphorescent light emitting material,
The hole transport region includes two kinds of compounds represented by the following general formula (1) and having different structures.
[一般式（１）中、
Ａｒは、水素原子、又は無置換の環形成炭素数６～２０のアリール基を表し、
Ｒは、一般式（１－１）、一般式（１－２）、一般式（１－３）のいずれかで表され、
Ａｒ１及びＡｒ２は、それぞれ独立に、無置換の環形成炭素数６～２０のアリール基を表し、
Ａｒ３は、置換もしくは無置換の環形成炭素数６～２０のアリール基を表す。] [In general formula (1),
Ar represents a hydrogen atom or an unsubstituted aryl group having 6 to 20 ring carbon atoms,
R is represented by any one of general formula (1-1), general formula (1-2), and general formula (1-3);
Ar 1 and Ar 2 each independently represents an unsubstituted aryl group having 6 to 20 ring carbon atoms,
Ar 3 represents a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms. ]
Ａｒは、水素原子、又は無置換の環形成炭素数６～２０のアリール基を表し、
Ｒは、一般式（１－１）、一般式（１－２）、一般式（１－３）のいずれかで表され、
Ａｒ１及びＡｒ２は、それぞれ独立に、無置換の環形成炭素数６～２０のアリール基を表し、
Ａｒ３は、置換もしくは無置換の環形成炭素数６～２０のアリール基を表す。] [In general formula (1),
Ar represents a hydrogen atom or an unsubstituted aryl group having 6 to 20 ring carbon atoms,
R is represented by any one of general formula (1-1), general formula (1-2), and general formula (1-3);
Ar 1 and Ar 2 each independently represents an unsubstituted aryl group having 6 to 20 ring carbon atoms,
Ar 3 represents a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms. ]
Ａｒ、Ａｒ１、Ａｒ２及びＡｒ３における環形成炭素数６～２０のアリール基としては、フェニル基、ナフチル基、ビフェニル基、ターフェニル基、フェナントリル基が挙げられる。
Ａｒ、Ａｒ１及びＡｒ２は、それぞれ独立に、フェニル基、ナフチル基、ビフェニル基、又はターフェニル基であることが好ましい。 Examples of the aryl group having 6 to 20 ring carbon atoms in Ar, Ar 1 , Ar 2 and Ar 3 include a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group and a phenanthryl group.
Ar, Ar 1 and Ar 2 are preferably each independently a phenyl group, a naphthyl group, a biphenyl group, or a terphenyl group.
Ａｒ、Ａｒ１及びＡｒ２は、それぞれ独立に、フェニル基、ナフチル基、ビフェニル基、又はターフェニル基であることが好ましい。 Examples of the aryl group having 6 to 20 ring carbon atoms in Ar, Ar 1 , Ar 2 and Ar 3 include a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group and a phenanthryl group.
Ar, Ar 1 and Ar 2 are preferably each independently a phenyl group, a naphthyl group, a biphenyl group, or a terphenyl group.
Ａｒ３の「置換もしくは無置換の」における「置換基」としては、炭素数１～１０のアルキル基、又は環形成炭素数６～２０のアルキル基が挙げられる。
Ａｒ１～Ａｒ５及びＬ１～Ｌ３各基の「置換基」としての炭素数１～１０のアルキル基としては、例えば、メチル基、エチル基、プロピル基、ｔ－ブチル基又はｎ－ブチル基等が挙げられる。
Ａｒ１～Ａｒ５及びＬ１～Ｌ３各基の「置換基」としての６～２０のアルキル基としては、例えば、フェニル基、ビフェニル基又はナフチル基が挙げられる。 Examples of the “substituent” in the “substituted or unsubstituted” of Ar 3 include an alkyl group having 1 to 10 carbon atoms or an alkyl group having 6 to 20 ring carbon atoms.
Examples of the alkyl group having 1 to 10 carbon atoms as the “substituent” of each of Ar 1 to Ar 5 and L 1 to L 3 include a methyl group, an ethyl group, a propyl group, a t-butyl group, and n-butyl. Groups and the like.
Examples of the 6 to 20 alkyl group as the “substituent” of each of the groups Ar 1 to Ar 5 and L 1 to L 3 include a phenyl group, a biphenyl group, and a naphthyl group.
Ａｒ１～Ａｒ５及びＬ１～Ｌ３各基の「置換基」としての炭素数１～１０のアルキル基としては、例えば、メチル基、エチル基、プロピル基、ｔ－ブチル基又はｎ－ブチル基等が挙げられる。
Ａｒ１～Ａｒ５及びＬ１～Ｌ３各基の「置換基」としての６～２０のアルキル基としては、例えば、フェニル基、ビフェニル基又はナフチル基が挙げられる。 Examples of the “substituent” in the “substituted or unsubstituted” of Ar 3 include an alkyl group having 1 to 10 carbon atoms or an alkyl group having 6 to 20 ring carbon atoms.
Examples of the alkyl group having 1 to 10 carbon atoms as the “substituent” of each of Ar 1 to Ar 5 and L 1 to L 3 include a methyl group, an ethyl group, a propyl group, a t-butyl group, and n-butyl. Groups and the like.
Examples of the 6 to 20 alkyl group as the “substituent” of each of the groups Ar 1 to Ar 5 and L 1 to L 3 include a phenyl group, a biphenyl group, and a naphthyl group.
一般式（１）で表される化合物の具体例としては、例えば、下記に示す化合物が挙げられる。
Specific examples of the compound represented by the general formula (1) include the compounds shown below.
本明細書において、水素原子とは、中性子数が異なる同位体である軽水素（protium）、重水素（deuterium）を包含する。
In this specification, the hydrogen atom includes light hydrogen (protium) and deuterium which are isotopes having different numbers of neutrons.
図１に、有機ＥＬ素子の層構成の一例の概略を示す。
図１の有機ＥＬ素子１は、基板２、陽極３、陰極４、及び該陽極３と陰極４との間に配置された発光ユニット（有機層）１０とを有する。発光ユニット（有機層）１０は、少なくとも１つの発光層５と、陽極３と発光層５との間に配置された正孔輸送領域（正孔注入層、正孔輸送層等）６を有する。
発光層５と陰極４との間に電子輸送領域（電子注入層、電子輸送層等）７を形成してもよい。また、発光層５の陽極３側に電子阻止層（図示せず）を、発光層５の陰極４側に正孔阻止層（図示せず）をそれぞれ設けてもよい。これにより、電子や正孔を発光層５に閉じ込めて、発光層５における励起子の生成効率をさらに高めることができる。
本発明の一態様に係る有機ＥＬ素子は、発光層５に燐光性の発光材料を含み、正孔輸送領域（正孔注入層、正孔輸送層等）６に、一般式（１）で表され、且つ、互いに構造が異なる２種類の化合物を含む。 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 asubstrate 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 thelight emitting layer 5 and the cathode 4. Further, 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. Thereby, electrons and holes can be confined in the light emitting layer 5 and the exciton generation efficiency in the light emitting layer 5 can be further increased.
The organic EL device according to one embodiment of the present invention includes a phosphorescent light-emitting material in the light-emittinglayer 5 and is represented by the general formula (1) in the hole transport region (hole injection layer, hole transport layer, or the like) 6. And two kinds of compounds having different structures from each other.
図１の有機ＥＬ素子１は、基板２、陽極３、陰極４、及び該陽極３と陰極４との間に配置された発光ユニット（有機層）１０とを有する。発光ユニット（有機層）１０は、少なくとも１つの発光層５と、陽極３と発光層５との間に配置された正孔輸送領域（正孔注入層、正孔輸送層等）６を有する。
発光層５と陰極４との間に電子輸送領域（電子注入層、電子輸送層等）７を形成してもよい。また、発光層５の陽極３側に電子阻止層（図示せず）を、発光層５の陰極４側に正孔阻止層（図示せず）をそれぞれ設けてもよい。これにより、電子や正孔を発光層５に閉じ込めて、発光層５における励起子の生成効率をさらに高めることができる。
本発明の一態様に係る有機ＥＬ素子は、発光層５に燐光性の発光材料を含み、正孔輸送領域（正孔注入層、正孔輸送層等）６に、一般式（１）で表され、且つ、互いに構造が異なる２種類の化合物を含む。 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
An electron transport region (electron injection layer, electron transport layer, etc.) 7 may be formed between the
The organic EL device according to one embodiment of the present invention includes a phosphorescent light-emitting material in the light-emitting
図２に、有機ＥＬ素子の層構成の他の一例の概略を示す。図２に示す有機ＥＬ素子１１では、発光ユニット（有機層）２０において、図１の有機ＥＬ素子１の発光ユニット１０の正孔輸送領域６の正孔輸送層、及び電子輸送領域７の電子輸送層を、それぞれ２層構造としている。正孔輸送領域６は、陽極３側の第１正孔輸送層６ａ、及び陰極４側の第２正孔輸送層６ｂを有している。電子輸送領域７は、陽極側の第１電子輸送層７ａ、及び陰極側の第２正孔輸送層７ｂを有している。なお、その他の符号については、図１と同じであるため、説明を省略する。
FIG. 2 shows an outline of another example of the layer structure of the organic EL element. In the organic EL element 11 shown in FIG. 2, in the light emitting unit (organic layer) 20, the hole transport layer in the hole transport region 6 and the electron transport in the electron transport region 7 of the light emitting unit 10 of the organic EL element 1 in FIG. Each layer has a two-layer structure. The hole transport region 6 has a first hole transport layer 6a on the anode 3 side and a second hole transport layer 6b on the cathode 4 side. The electron transport region 7 includes a first electron transport layer 7a on the anode side and a second hole transport layer 7b on the cathode side. The other reference numerals are the same as those in FIG.
本発明の一態様に係る有機ＥＬ素子において、正孔輸送領域６のうち、陽極３側の第１正孔輸送層６ａが一般式（１）で表される化合物（「第一化合物」と称する）を含み、陰極４及び発光層５側の第２正孔輸送層６ｂが一般式（１）で表され、且つ前記第一化合物とは構造の異なる化合物（「第二化合物」と称する）を含むことが好ましい。
本発明に係る有機ＥＬ素子は、図１及び図２に図示した有機ＥＬ素子１、１１の層構成に限定されるものではなく、例えば、正孔輸送領域６は３層以上の層の積層構成であってもよく、電子輸送領域７も３層以上の層の積層構成であってもよい。 In the organic EL device according to one embodiment of the present invention, in thehole transport region 6, the first hole transport layer 6a on the anode 3 side is a compound represented by the general formula (1) (referred to as “first compound”). ), The second hole transport layer 6b on the cathode 4 and light emitting layer 5 side is represented by the general formula (1), and has a structure different from that of the first compound (referred to as “second compound”). It is preferable to include.
The organic EL device according to the present invention is not limited to the layer configuration of theorganic EL devices 1 and 11 illustrated in FIGS. 1 and 2. For example, the hole transport region 6 is a stacked configuration of three or more layers. The electron transport region 7 may also have a laminated structure of three or more layers.
本発明に係る有機ＥＬ素子は、図１及び図２に図示した有機ＥＬ素子１、１１の層構成に限定されるものではなく、例えば、正孔輸送領域６は３層以上の層の積層構成であってもよく、電子輸送領域７も３層以上の層の積層構成であってもよい。 In the organic EL device according to one embodiment of the present invention, in the
The organic EL device according to the present invention is not limited to the layer configuration of the
本発明の一態様に係る有機ＥＬ素子は、例えば、蛍光又は燐光発光型の単色発光素子であってもよく、蛍光／燐光ハイブリッド型の白色発光素子であってもよい。また、単独の発光ユニットを有するシンプル型であってもよく、２以上の発光ユニットを有するタンデム型であってもよい。
なお、本明細書に記載の「発光ユニット」とは、有機層を含み、該有機層のうちの少なくとも１層が発光層であり、注入された正孔と電子が再結合することにより発光する最小単位を言う。
また、本明細書に記載の「発光層」とは、発光機能を有する有機層である。発光層は、例えば、燐光発光層、蛍光発光層等であり、また、１層でも２以上の層でもよい。
発光ユニットは、燐光発光層や蛍光発光層を２以上有する積層型であってもよく、この場合、例えば、燐光発光層で生成された励起子が蛍光発光層に拡散することを防ぐためのスペース層を各発光層の間に有していてもよい。 The organic EL device according to one embodiment of the present invention 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.
Note that 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.
Further, 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.
なお、本明細書に記載の「発光ユニット」とは、有機層を含み、該有機層のうちの少なくとも１層が発光層であり、注入された正孔と電子が再結合することにより発光する最小単位を言う。
また、本明細書に記載の「発光層」とは、発光機能を有する有機層である。発光層は、例えば、燐光発光層、蛍光発光層等であり、また、１層でも２以上の層でもよい。
発光ユニットは、燐光発光層や蛍光発光層を２以上有する積層型であってもよく、この場合、例えば、燐光発光層で生成された励起子が蛍光発光層に拡散することを防ぐためのスペース層を各発光層の間に有していてもよい。 The organic EL device according to one embodiment of the present invention 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.
Note that 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.
Further, 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.
ただし、本発明の一態様に係る有機ＥＬ素子の層構成は、これらに限定されるものではない。例えば、有機ＥＬ素子が、正孔注入層及び正孔輸送層を有する場合には、正孔輸送層と陽極との間に正孔注入層が設けられていることが好ましい。また、有機ＥＬ素子が、電子注入層及び電子輸送層を有する場合には、電子輸送層と陰極との間に電子注入層が設けられていることが好ましい。また、正孔注入層、正孔輸送層、電子輸送層、及び電子注入層のそれぞれは、１層で構成されていてもよく、２以上の層で構成されていてもよい。
However, the layer structure of the organic EL element according to one embodiment of the present invention is not limited to these. For example, when the organic EL element has a hole injection layer and a hole transport layer, it is preferable that a hole injection layer is provided between the hole transport layer and the anode. Moreover, when an organic EL element has an electron injection layer and an electron carrying layer, it is preferable that 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.
（基板）
基板２は、有機ＥＬ素子の支持体として用いられる。基板としては、例えば、ガラス、石英、プラスチックなどを用いることができる。また、可撓性基板を用いてもよい。可撓性基板とは、折り曲げることができる（フレキシブル）基板のことであり、例えば、ポリカーボネート、ポリ塩化ビニルからなるプラスチック基板等が挙げられる。 (substrate)
Thesubstrate 2 is used as a support for the organic EL element. For example, glass, quartz, plastic, or the like can be used as the substrate. Further, 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.
基板２は、有機ＥＬ素子の支持体として用いられる。基板としては、例えば、ガラス、石英、プラスチックなどを用いることができる。また、可撓性基板を用いてもよい。可撓性基板とは、折り曲げることができる（フレキシブル）基板のことであり、例えば、ポリカーボネート、ポリ塩化ビニルからなるプラスチック基板等が挙げられる。 (substrate)
The
（陽極）
陽極３としては、例えば、金属、合金、導電性化合物、及びこれらの混合物等であって、仕事関数の大きい（具体的には、４．０ｅＶ以上）ものを用いることが好ましい。陽極の材料の具体例としては、酸化インジウム－酸化スズ（ＩＴＯ：Ｉｎｄｉｕｍ Ｔｉｎ Ｏｘｉｄｅ）、ケイ素もしくは酸化ケイ素を含有する酸化インジウム－酸化スズ、酸化インジウム－酸化亜鉛、酸化タングステン、酸化亜鉛を含有する酸化インジウム、グラフェン等が挙げられる。また、金、銀、白金、ニッケル、タングステン、クロム、モリブデン、鉄、コバルト、銅、パラジウム、チタン、及びこれらの金属の窒化物（例えば、窒化チタン）等が挙げられる。
陽極３の形成方法としては、スパッタリング法、真空蒸着法、塗布法、インクジェット法、スピンコート法等が挙げられる。 (anode)
As theanode 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). Specific examples of 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. In addition, 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.
Examples of the method for forming theanode 3 include sputtering, vacuum deposition, coating, ink jet, and spin coating.
陽極３としては、例えば、金属、合金、導電性化合物、及びこれらの混合物等であって、仕事関数の大きい（具体的には、４．０ｅＶ以上）ものを用いることが好ましい。陽極の材料の具体例としては、酸化インジウム－酸化スズ（ＩＴＯ：Ｉｎｄｉｕｍ Ｔｉｎ Ｏｘｉｄｅ）、ケイ素もしくは酸化ケイ素を含有する酸化インジウム－酸化スズ、酸化インジウム－酸化亜鉛、酸化タングステン、酸化亜鉛を含有する酸化インジウム、グラフェン等が挙げられる。また、金、銀、白金、ニッケル、タングステン、クロム、モリブデン、鉄、コバルト、銅、パラジウム、チタン、及びこれらの金属の窒化物（例えば、窒化チタン）等が挙げられる。
陽極３の形成方法としては、スパッタリング法、真空蒸着法、塗布法、インクジェット法、スピンコート法等が挙げられる。 (anode)
As the
Examples of the method for forming the
（正孔注入層）
陽極３に接して形成される正孔注入層は、正孔注入性の高い物質を含む層であり、陽極から有機層に正孔を注入する機能を有する。正孔注入性の高い物質としては、例えば、モリブデン酸化物、チタン酸化物、バナジウム酸化物、レニウム酸化物、ルテニウム酸化物、クロム酸化物、ジルコニウム酸化物、ハフニウム酸化物、タンタル酸化物、銀酸化物、タングステン酸化物、マンガン酸化物、芳香族アミン化合物、電子吸引性（アクセプター性）の化合物、高分子化合物等が挙げられる。 (Hole injection layer)
The hole injection layer formed in contact with theanode 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. Examples of 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.
陽極３に接して形成される正孔注入層は、正孔注入性の高い物質を含む層であり、陽極から有機層に正孔を注入する機能を有する。正孔注入性の高い物質としては、例えば、モリブデン酸化物、チタン酸化物、バナジウム酸化物、レニウム酸化物、ルテニウム酸化物、クロム酸化物、ジルコニウム酸化物、ハフニウム酸化物、タンタル酸化物、銀酸化物、タングステン酸化物、マンガン酸化物、芳香族アミン化合物、電子吸引性（アクセプター性）の化合物、高分子化合物等が挙げられる。 (Hole injection layer)
The hole injection layer formed in contact with the
（正孔輸送層）
正孔輸送層６ａ、６ｂは、正孔輸送性の高い物質を含む層であり、陽極３から有機層１０に正孔を輸送する機能を有する。
正孔輸送性の高い物質としては、１０－６ｃｍ２／（Ｖ・ｓ）以上の正孔移動度を有する物質であることが好ましく、例えば、芳香族アミン化合物、カルバゾール誘導体、アントラセン誘導体、高分子化合物等が挙げられる。
電子輸送性よりも正孔輸送性の方が高い化合物であれば、正孔輸送層６ａ、６ｂに、これら以外の物質を用いてもよい。 (Hole transport layer)
The hole transport layers 6 a and 6 b are layers containing a substance having a high hole transport property and have 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 −6cm 2 / (V · s) or more. For example, an aromatic amine compound, a carbazole derivative, an anthracene derivative, a polymer compound Etc.
As long as the hole transporting property is higher than the electron transporting property, substances other than these may be used for the hole transporting layers 6a and 6b.
正孔輸送層６ａ、６ｂは、正孔輸送性の高い物質を含む層であり、陽極３から有機層１０に正孔を輸送する機能を有する。
正孔輸送性の高い物質としては、１０－６ｃｍ２／（Ｖ・ｓ）以上の正孔移動度を有する物質であることが好ましく、例えば、芳香族アミン化合物、カルバゾール誘導体、アントラセン誘導体、高分子化合物等が挙げられる。
電子輸送性よりも正孔輸送性の方が高い化合物であれば、正孔輸送層６ａ、６ｂに、これら以外の物質を用いてもよい。 (Hole transport layer)
The
The substance having a high hole transporting property is preferably a substance having a hole mobility of 10 −6
As long as the hole transporting property is higher than the electron transporting property, substances other than these may be used for the
正孔輸送層６ａ、６ｂ及び正孔輸送領域６は、単層でもよく、２層以上が積層されていてもよい。この場合、発光層に近い側に、正孔輸送性の高い物質のうち、エネルギーギャップのより大きい物質を含む層を配置することが好ましい。
The hole transport layers 6a and 6b and 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.
本発明の一態様に係る有機ＥＬ素子は、正孔輸送領域（正孔注入層、正孔輸送層等）６に、一般式（１）で表され、且つ、互いに構造が異なる２種類の化合物を含む。
本発明の一態様に係る有機ＥＬ素子において、正孔輸送領域６のうち、陽極３側の第１正孔輸送層６ａが一般式（１）で表される化合物（第一化合物）を含み、陰極４及び発光層５側の第２正孔輸送層６ｂが一般式（１）で表され、且つ前記第一化合物とは構造の異なる化合物（第二化合物）を含むことが好ましい。 The organic EL device according to one embodiment of the present invention includes two types of compounds represented by the general formula (1) in the hole transport region (hole injection layer, hole transport layer, etc.) 6 and having different structures. including.
In the organic EL device according to one aspect of the present invention, in thehole transport region 6, the first hole transport layer 6a on the anode 3 side includes a compound represented by the general formula (1) (first compound), The second hole transport layer 6b on the cathode 4 and light emitting layer 5 side is preferably represented by the general formula (1) and contains a compound (second compound) having a structure different from that of the first compound.
本発明の一態様に係る有機ＥＬ素子において、正孔輸送領域６のうち、陽極３側の第１正孔輸送層６ａが一般式（１）で表される化合物（第一化合物）を含み、陰極４及び発光層５側の第２正孔輸送層６ｂが一般式（１）で表され、且つ前記第一化合物とは構造の異なる化合物（第二化合物）を含むことが好ましい。 The organic EL device according to one embodiment of the present invention includes two types of compounds represented by the general formula (1) in the hole transport region (hole injection layer, hole transport layer, etc.) 6 and having different structures. including.
In the organic EL device according to one aspect of the present invention, in the
（発光層）
発光層５は、発光性の高い物質（ドーパント材料）を含む層である。本発明の一態様に係る有機ＥＬ素子は、ドーパント材料としては、燐光性の発光材料を発光層５に含む。
燐光発光性化合物とは、三重項励起状態から発光可能な化合物であり、これを含む発光層は、燐光発光層と呼ばれる。 (Light emitting layer)
Thelight emitting layer 5 is a layer containing a substance (dopant material) having a high light emitting property. The organic EL element according to one embodiment of the present invention includes a phosphorescent light emitting material in the light emitting layer 5 as a dopant material.
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.
発光層５は、発光性の高い物質（ドーパント材料）を含む層である。本発明の一態様に係る有機ＥＬ素子は、ドーパント材料としては、燐光性の発光材料を発光層５に含む。
燐光発光性化合物とは、三重項励起状態から発光可能な化合物であり、これを含む発光層は、燐光発光層と呼ばれる。 (Light emitting layer)
The
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.
発光層５は、通常、ドーパント材料（発光材料）、及びこれを効率よく発光させるためのホスト材料を含有する。なお、ドーパント材料（発光材料）は、文献によっては、ゲスト材料、又はエミッターと称する場合もある。また、ホスト材料は、文献によっては、マトリックス材料と称する場合もある。
１つの発光層に、２以上のドーパント材料、及び２以上のホスト材料を含んでもよい。また、発光層が２以上であってもよい。 Thelight emitting layer 5 usually contains a dopant material (light emitting material) and a host material for efficiently emitting light. Note that the dopant material (light-emitting material) may be referred to as a guest material or an emitter 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.
１つの発光層に、２以上のドーパント材料、及び２以上のホスト材料を含んでもよい。また、発光層が２以上であってもよい。 The
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.
発光層５におけるドーパント材料（発光材料）の含有量は、特に限定されるものではないが、十分な発光及び濃度消光の観点から、例えば、０．１～９９質量％であることが好ましく、０．１～７０質量％であることがより好ましく、０．１～３０質量％であることがさらに好ましい。
The content of the dopant material (light emitting 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, More preferably, it is 1 to 70% by mass, and further preferably 0.1 to 30% by mass.
（燐光ドーパント（燐光性の発光材料））
燐光ドーパントとしては、例えば、燐光発光性の重金属錯体、燐光発光性の希土類金属錯体が挙げられる。
重金属錯体としては、例えば、イリジウム錯体、オスミウム錯体、白金錯体等が挙げられる。重金属錯体は、イリジウム、オスミウム、及び白金から選択される金属のオルトメタル化錯体が好ましい。
希土類金属錯体としては、例えば、テルビウム錯体、ユーロピウム錯体等が挙げられる。 (Phosphorescent dopant (phosphorescent light-emitting material))
Examples of phosphorescent dopants include phosphorescent heavy metal complexes and phosphorescent rare earth metal complexes.
Examples of heavy metal complexes include iridium complexes, osmium complexes, platinum complexes, and the like. The heavy metal complex is preferably an orthometalated complex of a metal selected from iridium, osmium, and platinum.
Examples of rare earth metal complexes include terbium complexes and europium complexes.
燐光ドーパントとしては、例えば、燐光発光性の重金属錯体、燐光発光性の希土類金属錯体が挙げられる。
重金属錯体としては、例えば、イリジウム錯体、オスミウム錯体、白金錯体等が挙げられる。重金属錯体は、イリジウム、オスミウム、及び白金から選択される金属のオルトメタル化錯体が好ましい。
希土類金属錯体としては、例えば、テルビウム錯体、ユーロピウム錯体等が挙げられる。 (Phosphorescent dopant (phosphorescent light-emitting material))
Examples of phosphorescent dopants include phosphorescent heavy metal complexes and phosphorescent rare earth metal complexes.
Examples of heavy metal complexes include iridium complexes, osmium complexes, platinum complexes, and the like. The heavy metal complex is preferably an orthometalated complex of a metal selected from iridium, osmium, and platinum.
Examples of rare earth metal complexes include terbium complexes and europium complexes.
（燐光ホスト材料）
燐光ホストとしては、燐光ドーパントよりも高い三重項準位を有する化合物が好ましく、例えば、金属錯体、複素環化合物、縮合芳香族化合物等が挙げられる。これらの中でも、例えば、インドール誘導体、カルバゾール誘導体、ピリジン誘導体、ピリミジン誘導体、トリアジン誘導体、キノリン誘導体、イソキノリン誘導体、キナゾリン誘導体、ジベンゾフラン誘導体、ジベンゾチオフェン誘導体、ナフタレン誘導体、トリフェニレン誘導体、フェナントレン誘導体、フルオランテン誘導体等が好ましい。 (Phosphorescent host material)
As the phosphorescent host, a compound having a triplet level higher than that of the phosphorescent dopant is preferable, and examples thereof include metal complexes, heterocyclic compounds, and condensed aromatic compounds. Among these, for example, indole derivatives, carbazole derivatives, pyridine derivatives, pyrimidine derivatives, triazine derivatives, quinoline derivatives, isoquinoline derivatives, quinazoline derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, naphthalene derivatives, triphenylene derivatives, phenanthrene derivatives, fluoranthene derivatives, etc. preferable.
燐光ホストとしては、燐光ドーパントよりも高い三重項準位を有する化合物が好ましく、例えば、金属錯体、複素環化合物、縮合芳香族化合物等が挙げられる。これらの中でも、例えば、インドール誘導体、カルバゾール誘導体、ピリジン誘導体、ピリミジン誘導体、トリアジン誘導体、キノリン誘導体、イソキノリン誘導体、キナゾリン誘導体、ジベンゾフラン誘導体、ジベンゾチオフェン誘導体、ナフタレン誘導体、トリフェニレン誘導体、フェナントレン誘導体、フルオランテン誘導体等が好ましい。 (Phosphorescent host material)
As the phosphorescent host, a compound having a triplet level higher than that of the phosphorescent dopant is preferable, and examples thereof include metal complexes, heterocyclic compounds, and condensed aromatic compounds. Among these, for example, indole derivatives, carbazole derivatives, pyridine derivatives, pyrimidine derivatives, triazine derivatives, quinoline derivatives, isoquinoline derivatives, quinazoline derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, naphthalene derivatives, triphenylene derivatives, phenanthrene derivatives, fluoranthene derivatives, etc. preferable.
（電子輸送層）
電子輸送層７ａ、７ｂ及び電子輸送領域７は、電子輸送性の高い物質を含む層である。電子輸送性の高い物質としては、１０－６ｃｍ２／Ｖｓ以上の電子移動度を有する物質であることが好ましく、例えば、金属錯体、芳香族複素環化合物、芳香族炭化水素化合物、高分子化合物等が挙げられる。 (Electron transport layer)
Theelectron transport layers 7a and 7b and 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. For example, a metal complex, an aromatic heterocyclic compound, an aromatic hydrocarbon compound, a polymer compound Etc.
電子輸送層７ａ、７ｂ及び電子輸送領域７は、電子輸送性の高い物質を含む層である。電子輸送性の高い物質としては、１０－６ｃｍ２／Ｖｓ以上の電子移動度を有する物質であることが好ましく、例えば、金属錯体、芳香族複素環化合物、芳香族炭化水素化合物、高分子化合物等が挙げられる。 (Electron transport layer)
The
金属錯体としては、例えば、アルミニウム錯体、ベリリウム錯体、亜鉛錯体等が挙げられる。具体的には、トリス（８－キノリノラト）アルミニウム（III）（略称：Ａｌｑ）、トリス（４－メチル－８－キノリノラト）アルミニウム（略称：Ａｌｍｑ３）、ビス（１０－ヒドロキシベンゾ［ｈ］キノリナト）ベリリウム（略称：ＢｅＢｑ２）、ビス（２－メチル－８－キノリノラト）（４－フェニルフェノラト）アルミニウム（III）（略称：ＢＡｌｑ）、ビス（８－キノリノラト）亜鉛（II）（略称：Ｚｎｑ）、ビス［２－（２－ベンゾオキサゾリル）フェノラト］亜鉛（II）（略称：ＺｎＰＢＯ）、ビス［２－（２－ベンゾチアゾリル）フェノラト］亜鉛（II）（略称：ＺｎＢＴＺ）等が挙げられる。
Examples of the metal complex include an aluminum complex, a beryllium complex, and a zinc complex. Specifically, tris (8-quinolinolato) aluminum (III) (abbreviation: Alq), 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), bis (8-quinolinolato) zinc (II) (abbreviation: Znq), bis [2- (2-Benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ), and the like.
芳香族複素環化合物としては、例えば、ベンズイミダゾール誘導体、イミダゾピリジン誘導体、ベンズイミダゾフェナントリジン誘導体等のイミダゾール誘導体；ピリミジン誘導体、トリアジン誘導体等のアジン誘導体；キノリン誘導体、イソキノリン誘導体、フェナントロリン誘導体等の含窒素六員環構造を含む化合物（複素環にホスフィンオキサイド系の置換基を有するものも含む。）等が挙げられる。
Examples of the aromatic heterocyclic compound 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. Examples thereof include compounds containing a nitrogen six-membered ring structure (including those having a phosphine oxide substituent in the heterocyclic ring).
電子輸送層に用いられる芳香族複素環化合物の具体例としては、例えば、下記に示す化合物が挙げられる。
Specific examples of the aromatic heterocyclic compound used for the electron transport layer include the following compounds.
芳香族炭化水素化合物としては、例えば、アントラセン誘導体、フルオランテン誘導体等が挙げられる。
Examples of the aromatic hydrocarbon compound include anthracene derivatives and fluoranthene derivatives.
電子輸送層には、例えば、アルカリ金属、マグネシウム、アルカリ土類金属、これらのうちの２以上の金属を含む合金等の金属；８－キノリノラトリチウム（略称：Ｌｉｑ）等のアルカリ金属化合物、アルカリ土類金属化合物等の金属化合物が含まれていてもよい。
アルカリ金属、マグネシウム、アルカリ土類金属、又はこれらのうちの２以上の金属を含む合金等の金属が、電子輸送層に含まれる場合、その含有量は、特に限定されるものではないが、０．１～５０質量％であることが好ましく、より好ましくは０．１～２０質量％、さらに好ましくは１～１０質量％である。
アルカリ金属化合物、又はアルカリ土類金属化合物等の金属化合物の金属化合物が電子輸送層に含まれる場合、その含有量は、１～９９質量％であることが好ましく、より好ましくは１０～９０質量％である。なお、電子輸送層が２以上の層である場合の発光層側にある層は、これらの金属化合物のみで形成することもできる。 Examples of the electron transport layer 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.
When 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.
When a metal compound of a metal compound such as an alkali metal compound or an alkaline earth metal compound is contained in the electron transport layer, 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.
アルカリ金属、マグネシウム、アルカリ土類金属、又はこれらのうちの２以上の金属を含む合金等の金属が、電子輸送層に含まれる場合、その含有量は、特に限定されるものではないが、０．１～５０質量％であることが好ましく、より好ましくは０．１～２０質量％、さらに好ましくは１～１０質量％である。
アルカリ金属化合物、又はアルカリ土類金属化合物等の金属化合物の金属化合物が電子輸送層に含まれる場合、その含有量は、１～９９質量％であることが好ましく、より好ましくは１０～９０質量％である。なお、電子輸送層が２以上の層である場合の発光層側にある層は、これらの金属化合物のみで形成することもできる。 Examples of the electron transport layer 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.
When 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.
When a metal compound of a metal compound such as an alkali metal compound or an alkaline earth metal compound is contained in the electron transport layer, 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.
（電子注入層）
電子注入層は、電子注入性の高い物質を含む層であり、陰極から発光層へ効率よく電子注入する機能を有する。電子注入性の高い物質としては、例えば、アルカリ金属、マグネシウム、アルカリ土類金属、これらの化合物等が挙げられる。具体的には、リチウム、セシウム、カルシウム、フッ化リチウム、フッ化セシウム、フッ化カルシウム、リチウム酸化物等が挙げられる。その他、電子輸送性を有する物質に、アルカリ金属、マグネシウム、アルカリ土類金属、又はこれらの化合物を含有させたもの、例えば、Ａｌｑにマグネシウムを含有させたもの等を用いることもできる。 (Electron injection layer)
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. Examples of 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. In addition, 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.
電子注入層は、電子注入性の高い物質を含む層であり、陰極から発光層へ効率よく電子注入する機能を有する。電子注入性の高い物質としては、例えば、アルカリ金属、マグネシウム、アルカリ土類金属、これらの化合物等が挙げられる。具体的には、リチウム、セシウム、カルシウム、フッ化リチウム、フッ化セシウム、フッ化カルシウム、リチウム酸化物等が挙げられる。その他、電子輸送性を有する物質に、アルカリ金属、マグネシウム、アルカリ土類金属、又はこれらの化合物を含有させたもの、例えば、Ａｌｑにマグネシウムを含有させたもの等を用いることもできる。 (Electron injection layer)
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. Examples of 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. In addition, 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.
また、電子注入層には、有機化合物及びドナー性の化合物を含む複合材料を用いることもできる。有機化合物がドナー性の化合物から電子を受け取るため、このような複合材料は電子注入性及び電子輸送性に優れている。
有機化合物としては、受け取った電子の輸送性に優れた物質が好ましく、例えば、上述した電子輸送性の高い物質である金属錯体や芳香族複素環化合物等を用いることができる。
ドナー性の化合物としては、有機化合物に電子を供与することができる物質であればよく、例えば、アルカリ金属、マグネシウム、アルカリ土類金属、希土類金属等が挙げられる。具体的には、リチウム、セシウム、マグネシウム、カルシウム、エルビウム、イッテルビウム等が挙げられる。また、アルカリ金属酸化物やアルカリ土類金属酸化物が好ましく、具体的には、リチウム酸化物、カルシウム酸化物、バリウム酸化物等が挙げられる。また、酸化マグネシウムのようなルイス塩基を用いることもできる。また、テトラチアフルバレン（略称：ＴＴＦ）等の有機化合物を用いることもできる。 For the electron injection layer, 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.
As the organic compound, a substance having excellent transportability of received electrons is preferable. For example, 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. Alternatively, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.
有機化合物としては、受け取った電子の輸送性に優れた物質が好ましく、例えば、上述した電子輸送性の高い物質である金属錯体や芳香族複素環化合物等を用いることができる。
ドナー性の化合物としては、有機化合物に電子を供与することができる物質であればよく、例えば、アルカリ金属、マグネシウム、アルカリ土類金属、希土類金属等が挙げられる。具体的には、リチウム、セシウム、マグネシウム、カルシウム、エルビウム、イッテルビウム等が挙げられる。また、アルカリ金属酸化物やアルカリ土類金属酸化物が好ましく、具体的には、リチウム酸化物、カルシウム酸化物、バリウム酸化物等が挙げられる。また、酸化マグネシウムのようなルイス塩基を用いることもできる。また、テトラチアフルバレン（略称：ＴＴＦ）等の有機化合物を用いることもできる。 For the electron injection layer, 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.
As the organic compound, a substance having excellent transportability of received electrons is preferable. For example, 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. Alternatively, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.
（陰極）
陰極は、金属、合金、導電性化合物、及びこれらの混合物等であって、仕事関数の小さい（具体的には、３．８ｅＶ以下）ものを用いることが好ましい。陰極の材料としては、例えば、リチウム、セシウム等のアルカリ金属；マグネシウム；カルシウム、ストロンチウム等のアルカリ土類金属；これらの金属を含む合金（例えば、マグネシウム－銀、アルミニウム－リチウム）；ユーロピウム、イッテルビウム等の希土類金属；希土類金属を含む合金等が挙げられる。
陰極は、通常、真空蒸着法やスパッタリング法で形成される。また、銀ペースト等を用いる場合は、塗布法やインクジェット法等を用いることができる。 (cathode)
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). Examples of 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 | coating method, the inkjet method, etc. can be used.
陰極は、金属、合金、導電性化合物、及びこれらの混合物等であって、仕事関数の小さい（具体的には、３．８ｅＶ以下）ものを用いることが好ましい。陰極の材料としては、例えば、リチウム、セシウム等のアルカリ金属；マグネシウム；カルシウム、ストロンチウム等のアルカリ土類金属；これらの金属を含む合金（例えば、マグネシウム－銀、アルミニウム－リチウム）；ユーロピウム、イッテルビウム等の希土類金属；希土類金属を含む合金等が挙げられる。
陰極は、通常、真空蒸着法やスパッタリング法で形成される。また、銀ペースト等を用いる場合は、塗布法やインクジェット法等を用いることができる。 (cathode)
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). Examples of 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 | coating method, the inkjet method, etc. can be used.
また、電子注入層が設けられる場合、仕事関数の大小に関わらず、アルミニウム、銀、ＩＴＯ、グラフェン、ケイ素もしくは酸化ケイ素を含有する酸化インジウム－酸化スズ等、種々の導電性材料を用いて陰極を形成することができる。これらの導電性材料は、スパッタリング法やインクジェット法、スピンコート法等を用いて成膜することができる。
When the electron injection layer is provided, 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.
（層形成方法）
有機ＥＬ素子の各層の形成方法は、別途の記載がない限り、特に限定されるものではない。形成方法としては、乾式成膜法、湿式成膜法等の公知の方法を用いることができる。乾式成膜法の具体例としては、真空蒸着法、スパッタリング法、プラズマ法、イオンプレーティング法等が挙げられる。湿式成膜法の具体例としては、スピンコーティング法、ディッピング法、フローコーティング法、インクジェット法等の各種塗布法が挙げられる。 (Layer formation method)
The method for forming each layer of the organic EL element is not particularly limited unless otherwise specified. As 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.
有機ＥＬ素子の各層の形成方法は、別途の記載がない限り、特に限定されるものではない。形成方法としては、乾式成膜法、湿式成膜法等の公知の方法を用いることができる。乾式成膜法の具体例としては、真空蒸着法、スパッタリング法、プラズマ法、イオンプレーティング法等が挙げられる。湿式成膜法の具体例としては、スピンコーティング法、ディッピング法、フローコーティング法、インクジェット法等の各種塗布法が挙げられる。 (Layer formation method)
The method for forming each layer of the organic EL element is not particularly limited unless otherwise specified. As 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.
（膜厚）
有機ＥＬ素子の各層の膜厚は、別途の記載がない限り、特に限定されるものではない。膜厚が小さすぎると、ピンホール等の欠陥が生じやすく、十分な発光輝度が得られない。一方、膜厚が大きすぎると、高い駆動電圧が必要となり、効率が低下する。このような観点から、膜厚は、通常、０．１ｎｍ～１０μｍが好ましく、好ましくは５ｎｍ～１０μｍであり、さらに好ましくは１０ｎｍ～０．２μｍである。 (Film thickness)
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 μm, preferably from 5 nm to 10 μm, and more preferably from 10 nm to 0.2 μm.
有機ＥＬ素子の各層の膜厚は、別途の記載がない限り、特に限定されるものではない。膜厚が小さすぎると、ピンホール等の欠陥が生じやすく、十分な発光輝度が得られない。一方、膜厚が大きすぎると、高い駆動電圧が必要となり、効率が低下する。このような観点から、膜厚は、通常、０．１ｎｍ～１０μｍが好ましく、好ましくは５ｎｍ～１０μｍであり、さらに好ましくは１０ｎｍ～０．２μｍである。 (Film thickness)
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 μm, preferably from 5 nm to 10 μm, and more preferably from 10 nm to 0.2 μm.
［電子機器］
本発明の一態様に係る電子機器は、上述した本発明の一態様に係る有機ＥＬ素子を備えている。電子機器の具体例としては、有機ＥＬパネルモジュール等の表示部品；テレビ、携帯電話、スマートフォン、パーソナルコンピュータ等の表示装置；照明、車両用灯具の発光装置等が挙げられる。 [Electronics]
An electronic device according to one embodiment of the present invention 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.
本発明の一態様に係る電子機器は、上述した本発明の一態様に係る有機ＥＬ素子を備えている。電子機器の具体例としては、有機ＥＬパネルモジュール等の表示部品；テレビ、携帯電話、スマートフォン、パーソナルコンピュータ等の表示装置；照明、車両用灯具の発光装置等が挙げられる。 [Electronics]
An electronic device according to one embodiment of the present invention 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.
次に、実施例を挙げて本発明をさらに詳しく説明するが、本発明はこれらの実施例の記載内容に何ら制限されるものではない。
Next, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to the description of these examples.
実施例で用いた化合物を以下に示す。
The compounds used in the examples are shown below.
（実施例１）
２５ｍｍ×７５ｍｍ×厚さ１．１ｍｍのＩＴＯ透明電極ライン付きガラス基板（ジオマティック株式会社製）を、イソプロピルアルコール中で超音波洗浄を５分間行なった後、
ＵＶオゾン洗浄を３０分間行った。ＩＴＯ透明電極の膜厚は１３０ｎｍとした。
洗浄後の透明電極ライン付きガラス基板を真空蒸着装置の基板ホルダーに装着し、透明電極ラインが形成されている側の面上に透明電極を覆うようにして、化合物ＨＴ１と化合物ＨＩを共蒸着し、膜厚１０ｎｍの共蒸着膜層（Ｈ－１層）を成膜した。Ｈ－１層における化合物ＨＩの濃度は３重量％であった。
次いで、この共蒸着膜層上に化合物ＨＴ５を蒸着し、膜厚１００ｎｍのＨＴ５の層（Ｈ－２層）を成膜した。
続いて、化合物ＨＴ９を蒸着し、膜厚１５ｎｍのＨＴ９の層（Ｈ－３層）を成膜した。
さらに、ホスト材料として化合物ＰＲＨと、発光ドーパント材料としての化合物ＲＤとを共蒸着し、膜厚３０ｎｍの発光層を成膜した。発光層における化合物ＲＤの濃度は５質量％であった。
この発光層上に、化合物ＥＴ１と化合物Ｌｉｑとを共蒸着し、膜厚３０ｎｍの層（Ｅ－１層）を成膜した。この層における化合物Ｌｉｑの濃度は３０重量％であった。
さらに、この層の上に化合物Ｌｉｑを成膜速度０．１オングストローム／ｍｉｎで蒸着し、膜厚１ｎｍのＬｉｑ層（Ｅ－２層）を形成した。この層上に金属Ａｌを蒸着させ、金属陰極を膜厚８０ｎｍで形成した。
実施例１の有機ＥＬ素子は、次の層構成を有している。
ＩＴＯ（１３０ｎｍ）／ＨＴ１＋ＨＩ（１０ｎｍ）／ＨＴ５（１００ｎｍ）／ＨＴ９（１５ｎｍ）／ＰＲＨ：ＲＤ（３０ｎｍ）／ＥＴ１：Ｌｉｑ（３０ｎｍ）／Ｌｉｑ（１ｎｍ）／Ａｌ（８０ｎｍ）
得られた有機ＥＬ素子に電圧を印加したところ、実用レベルの発光特性を示した。 Example 1
A glass substrate with an ITO transparent electrode line of 25 mm × 75 mm × thickness 1.1 mm (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes,
UV ozone cleaning was performed 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.
Next, a compound HT5 was vapor-deposited on the co-evaporated film layer to form a HT5 layer (H-2 layer) having a thickness of 100 nm.
Subsequently, a compound HT9 was vapor-deposited to form a HT9 layer (H-3 layer) having a thickness of 15 nm.
Further, the compound PRH as a host material and the compound RD as a light emitting dopant material were co-evaporated to form a light emitting layer having a thickness of 30 nm. The concentration of Compound RD in the light emitting layer was 5% by mass.
On this light emitting layer, compound ET1 and compound Liq were co-evaporated to form a 30 nm thick layer (E-1 layer). The concentration of Compound Liq in this layer was 30% by weight.
Further, a compound Liq was vapor-deposited on this layer at a film formation rate of 0.1 angstrom / min to form a Liq layer (E-2 layer) 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 (10 nm) / HT5 (100 nm) / HT9 (15 nm) / PRH: RD (30 nm) / ET1: Liq (30 nm) / Liq (1 nm) / Al (80 nm)
When voltage was applied to the obtained organic EL device, it showed light emission characteristics at a practical level.
２５ｍｍ×７５ｍｍ×厚さ１．１ｍｍのＩＴＯ透明電極ライン付きガラス基板（ジオマティック株式会社製）を、イソプロピルアルコール中で超音波洗浄を５分間行なった後、
ＵＶオゾン洗浄を３０分間行った。ＩＴＯ透明電極の膜厚は１３０ｎｍとした。
洗浄後の透明電極ライン付きガラス基板を真空蒸着装置の基板ホルダーに装着し、透明電極ラインが形成されている側の面上に透明電極を覆うようにして、化合物ＨＴ１と化合物ＨＩを共蒸着し、膜厚１０ｎｍの共蒸着膜層（Ｈ－１層）を成膜した。Ｈ－１層における化合物ＨＩの濃度は３重量％であった。
次いで、この共蒸着膜層上に化合物ＨＴ５を蒸着し、膜厚１００ｎｍのＨＴ５の層（Ｈ－２層）を成膜した。
続いて、化合物ＨＴ９を蒸着し、膜厚１５ｎｍのＨＴ９の層（Ｈ－３層）を成膜した。
さらに、ホスト材料として化合物ＰＲＨと、発光ドーパント材料としての化合物ＲＤとを共蒸着し、膜厚３０ｎｍの発光層を成膜した。発光層における化合物ＲＤの濃度は５質量％であった。
この発光層上に、化合物ＥＴ１と化合物Ｌｉｑとを共蒸着し、膜厚３０ｎｍの層（Ｅ－１層）を成膜した。この層における化合物Ｌｉｑの濃度は３０重量％であった。
さらに、この層の上に化合物Ｌｉｑを成膜速度０．１オングストローム／ｍｉｎで蒸着し、膜厚１ｎｍのＬｉｑ層（Ｅ－２層）を形成した。この層上に金属Ａｌを蒸着させ、金属陰極を膜厚８０ｎｍで形成した。
実施例１の有機ＥＬ素子は、次の層構成を有している。
ＩＴＯ（１３０ｎｍ）／ＨＴ１＋ＨＩ（１０ｎｍ）／ＨＴ５（１００ｎｍ）／ＨＴ９（１５ｎｍ）／ＰＲＨ：ＲＤ（３０ｎｍ）／ＥＴ１：Ｌｉｑ（３０ｎｍ）／Ｌｉｑ（１ｎｍ）／Ａｌ（８０ｎｍ）
得られた有機ＥＬ素子に電圧を印加したところ、実用レベルの発光特性を示した。 Example 1
A glass substrate with an ITO transparent electrode line of 25 mm × 75 mm × thickness 1.1 mm (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes,
UV ozone cleaning was performed 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.
Next, a compound HT5 was vapor-deposited on the co-evaporated film layer to form a HT5 layer (H-2 layer) having a thickness of 100 nm.
Subsequently, a compound HT9 was vapor-deposited to form a HT9 layer (H-3 layer) having a thickness of 15 nm.
Further, the compound PRH as a host material and the compound RD as a light emitting dopant material were co-evaporated to form a light emitting layer having a thickness of 30 nm. The concentration of Compound RD in the light emitting layer was 5% by mass.
On this light emitting layer, compound ET1 and compound Liq were co-evaporated to form a 30 nm thick layer (E-1 layer). The concentration of Compound Liq in this layer was 30% by weight.
Further, a compound Liq was vapor-deposited on this layer at a film formation rate of 0.1 angstrom / min to form a Liq layer (E-2 layer) 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 (10 nm) / HT5 (100 nm) / HT9 (15 nm) / PRH: RD (30 nm) / ET1: Liq (30 nm) / Liq (1 nm) / Al (80 nm)
When voltage was applied to the obtained organic EL device, it showed light emission characteristics at a practical level.
（実施例２～４８）
正孔輸送領域、発光層、及び電子輸送領域の材料として、表１及び表２に示す各化合物を用いた以外、実施例１と同様に、有機ＥＬ素子を作製した。
得られた実施例２～４８有機ＥＬ素子に電圧を印加したところ、いずれも、実用レベルの発光特性を示した。 (Examples 2 to 48)
An organic EL device was produced in the same manner as in Example 1 except that the compounds shown in Tables 1 and 2 were used as materials 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 48, all showed light emission characteristics at a practical level.
正孔輸送領域、発光層、及び電子輸送領域の材料として、表１及び表２に示す各化合物を用いた以外、実施例１と同様に、有機ＥＬ素子を作製した。
得られた実施例２～４８有機ＥＬ素子に電圧を印加したところ、いずれも、実用レベルの発光特性を示した。 (Examples 2 to 48)
An organic EL device was produced in the same manner as in Example 1 except that the compounds shown in Tables 1 and 2 were used as materials 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 48, all showed light emission characteristics at a practical level.
１、１１・・有機ＥＬ素子、２・・基板、３・・陽極、４・・陰極、５・・発光層、６・・正孔輸送体域（正孔注入層、正孔輸送層等）、６ａ・・第１正孔輸送層、６ｂ・・第２正孔輸送層、７・・電子輸送体域（電子注入層、電子輸送層等）、７ａ・・第１電子輸送層、７ｂ・・第２電子輸送層、１０、２０・・発光ユニット（有機層）
1.11..Organic EL element 2..Substrate 3..Anode 4..Cathode 5..Light emitting layer 6..Hole transporter region (hole injection layer, hole transport layer, etc.) , 6a, first hole transport layer, 6b, second hole transport layer, 7. electron transport area (electron injection layer, electron transport layer, etc.), 7a, first electron transport layer, 7b,・ Second electron transport layer 10, 10, 20 ・ ・ Light emitting unit (organic layer)
Claims (6)
- 陽極と、
陰極と、
前記陽極と前記陰極の間に配された有機層と、を備え、
前記有機層は、発光層、及び、前記陽極と前記発光層との間に配された正孔輸送領域を含み、
前記発光層は、燐光性の発光材料を含み、
前記正孔輸送領域は、下記一般式（１）で表され、且つ、互いに構造が異なる２種類の化合物を含む、
有機エレクトロルミネッセンス素子。
[一般式（１）中、
Ａｒは、水素原子、又は無置換の環形成炭素数６～２０のアリール基を表し、
Ｒは、一般式（１－１）、一般式（１－２）、一般式（１－３）のいずれかで表され、
Ａｒ１及びＡｒ２は、それぞれ独立に、無置換の環形成炭素数６～２０のアリール基を表し、
Ａｒ３は、置換もしくは無置換の環形成炭素数６～２０のアリール基を表す。] 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 includes a phosphorescent light emitting material,
The hole transport region is represented by the following general formula (1) and includes two kinds of compounds having different structures from each other.
Organic electroluminescence device.
[In general formula (1),
Ar represents a hydrogen atom or an unsubstituted aryl group having 6 to 20 ring carbon atoms,
R is represented by any one of general formula (1-1), general formula (1-2), and general formula (1-3);
Ar 1 and Ar 2 each independently represents an unsubstituted aryl group having 6 to 20 ring carbon atoms,
Ar 3 represents a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms. ] - 前記正孔輸送領域は、少なくとも２つの層が前記陽極側から前記発光層側に向かって積層されて構成されている、
請求項１に記載の有機エレクトロルミネッセンス素子。 The hole transport region is configured by laminating at least two layers from the anode side toward the light emitting layer side.
The organic electroluminescent element according to claim 1. - Ａｒは、水素原子、フェニル基、ナフチル基、ビフェニル基、又はターフェニル基である、
請求項１又は２に記載の有機エレクトロルミネッセンス素子。 Ar is a hydrogen atom, a phenyl group, a naphthyl group, a biphenyl group, or a terphenyl group.
The organic electroluminescent element according to claim 1 or 2. - Ａｒ１及びＡｒ２は、それぞれ独立に、フェニル基、ナフチル基、ビフェニル基、又はターフェニル基である、
請求項１～３のいずれか一項に記載の有機エレクトロルミネッセンス素子。 Ar 1 and Ar 2 are each independently a phenyl group, a naphthyl group, a biphenyl group, or a terphenyl group.
The organic electroluminescence device according to any one of claims 1 to 3. - 前記有機層が、前記陰極と前記発光層との間に配された電子輸送領域を含む、請求項１～４のいずれか一項に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence device according to any one of claims 1 to 4, wherein the organic layer includes an electron transporting region disposed between the cathode and the light emitting layer.
- 請求項１～５のいずれか一項に記載の有機エレクトロルミネッセンス素子を備える電子機器。 An electronic device comprising the organic electroluminescence element according to any one of claims 1 to 5.
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| JP2020158528A (en) * | 2007-12-03 | 2020-10-01 | 株式会社半導体エネルギー研究所 | Compound, light-emitting element, light-emitting device, electronic apparatus, and lighting device |
| WO2021065774A1 (en) * | 2019-10-04 | 2021-04-08 | 出光興産株式会社 | Organic electroluminescent element and electronic device |
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| KR20120022861A (en) * | 2009-04-01 | 2012-03-12 | 이데미쓰 고산 가부시키가이샤 | Organic electroluminescent device |
| WO2013187894A1 (en) * | 2012-06-14 | 2013-12-19 | Universal Display Corporation | Biscarbazole derivative host materials and red emitter for oled emissive region |
| WO2014163228A1 (en) * | 2013-04-04 | 2014-10-09 | (주)피엔에이치테크 | Novel organic electroluminescent element compound and organic electroluminescent element comprising same |
| JP2015106658A (en) * | 2013-11-29 | 2015-06-08 | 出光興産株式会社 | Organic electroluminescent element and electronic device |
| JP2017005202A (en) * | 2015-06-15 | 2017-01-05 | 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． | Organic electroluminescent element |
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| WO2021065774A1 (en) * | 2019-10-04 | 2021-04-08 | 出光興産株式会社 | Organic electroluminescent element and electronic device |
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