CN111279507A - Organic electroluminescent element - Google Patents
Organic electroluminescent element Download PDFInfo
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- CN111279507A CN111279507A CN201880070505.1A CN201880070505A CN111279507A CN 111279507 A CN111279507 A CN 111279507A CN 201880070505 A CN201880070505 A CN 201880070505A CN 111279507 A CN111279507 A CN 111279507A
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- H10K50/00—Organic light-emitting devices
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- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/166—Electron transporting layers comprising a multilayered structure
Abstract
The invention provides an organic electroluminescent element, which comprises an anode, a light-emitting layer arranged on the anode, a1 st layer arranged on the light-emitting layer, a2 nd layer arranged on the 1 st layer, and a cathode arranged on the 2 nd layer, wherein the 1 st layer comprises an organic metal complex containing at least 1 selected from alkali metal elements, alkaline earth metal elements and rare earth metal elements, and the 2 nd layer comprises an electron-transporting organic compound and at least one metal selected from alkali metal and alkaline earth metal.
Description
Technical Field
The present invention relates to an organic electroluminescent element.
Background
An organic electroluminescent element (hereinafter, also referred to as an "organic EL element") includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode. In the organic EL element, holes and electrons injected from the anode and the cathode are recombined in the light-emitting layer, and light is emitted.
In an organic EL element, in order to reduce an electron injection barrier from a cathode to a light-emitting layer and realize low-voltage driving, a layer of an organometallic complex compound may be provided between the cathode and the light-emitting layer (patent document 1).
Documents of the prior art
Patent document
Patent document 1: japanese laid-open patent publication No. 11-233262
Disclosure of Invention
Problems to be solved by the invention
However, it is desired to further reduce the driving voltage for the organic EL element.
The present invention has been made in view of such circumstances, and an object thereof is to provide an organic EL element which can be driven at a lower voltage.
Means for solving the problems
An organic EL element of the present invention is an organic EL element having an anode, a cathode, and a light-emitting layer provided between the anode and the cathode, and comprises a1 st layer provided between the cathode and the light-emitting layer, and a2 nd layer provided between the 1 st layer and the cathode, wherein the 1 st layer contains an organic metal complex compound containing at least 1 selected from an alkali metal element, an alkaline earth metal element, and a rare earth metal element, and the 2 nd layer contains an electron-transporting organic compound, and a metal of at least one of the alkali metal and the alkaline earth metal. According to such an organic EL element, the driving can be performed at a lower voltage.
The above-mentioned 1 st layer may be in contact with the light-emitting layer. In addition, the 2 nd layer may be in contact with the 1 st layer. In addition, the cathode may be in contact with the 2 nd layer. By bringing the 1 st layer, the 2 nd layer, and the cathode into contact with each other, the organic EL element can be driven at a lower voltage.
The organometallic complex compound preferably contains at least one selected from the group consisting of 8-hydroxyquinoline sodium, 8-hydroxyquinoline lithium, 2- (2 ', 2' -bipyridin-6 '-yl) phenolate lithium, and 2- (2', 2 '-bipyridin-6' -yl) phenolate sodium.
The layer 1 preferably contains an organometallic complex compound in a proportion of 50 to 100 vol%.
The electron-transporting organic compound preferably contains a compound having a fluorene skeleton.
The 2 nd layer preferably contains at least 1 of Ca and Ba.
Effects of the invention
According to the present invention, an organic EL element which can be driven at a lower voltage can be provided.
Drawings
Fig. 1 is a diagram schematically showing a configuration of an organic EL element according to an embodiment.
Detailed Description
Hereinafter, embodiments of the present invention will be described with reference to the drawings. The same reference numerals are used for the same elements. Duplicate descriptions are omitted. The dimensional ratios in the drawings do not necessarily correspond to the dimensional ratios illustrated.
As schematically shown in fig. 1, in the organic electroluminescent element (organic EL element) 1 of the present embodiment, an anode E1, a hole injection layer 11, a hole transport layer 12, a light-emitting layer 13, a1 st layer 14b, a2 nd layer 14a, and a cathode E2 are provided in this order on a substrate P. Hereinafter, the 1 st layer 14b and the 2 nd layer 14a may be collectively referred to as the multilayer electron transport layer 14. The organic EL element 1 can be suitably used for a curved or planar lighting device, a planar light source used as a light source of a scanner, and a display device. The organic EL element 1 may be a bottom emission type in which light emitted from the light-emitting layer 13 passes through the substrate P and is emitted, or a top emission type in which light emitted from the light-emitting layer 13 is emitted from the side opposite to the substrate P (i.e., from the cathode E2 side).
< substrate >
The substrate P may be a substrate that does not chemically change in the process of manufacturing the organic EL element 1, and may be a rigid substrate such as a glass substrate or a silicon substrate, or a flexible substrate such as a plastic substrate or a polymer film. By using a flexible substrate, the organic EL element as a whole can become flexible. Electrodes for driving the organic EL element 1 or a driving circuit may be formed in advance on the substrate P. In the case where the organic EL element 1 is of the bottom emission type, the substrate P may be made of a plastic material that substantially transmits visible light (for example, light having a wavelength of 360nm to 830 nm) emitted from the light-emitting layer 13.
< Anode >
At least one of the anode E1 and the cathode E2 is transparent. A thin film having low resistance may be suitably used as the anode E1. When the organic EL element 1 is of a bottom emission type, the anode E1 disposed on the substrate P side is preferably transparent and has high transmittance for light in the visible light range. As the material of the anode E1, a metal oxide film having conductivity, a metal thin film, or the like can be used.
Among them, a thin film containing ITO, IZO, and tin oxide can be suitably used as the anode E1 from the viewpoint of high transmittance and ease of patterning. When light is extracted from the cathode E2 side, the anode E1 is preferably formed of a material that reflects light from the light-emitting layer 13 toward the cathode E2 side. As such a material, a metal oxide, or a metal sulfide having a work function of 3.0eV or more is preferable. For example, a thin metal film having a thickness of a degree of reflecting light can be used.
In the case where the organic EL element 1 is of a top emission type, since light from the light-emitting layer 13 is reflected by the anode E1 and is guided out from the cathode E2 side, a material having a high visible light reflectance is preferable as a material of the anode E1. Specific examples of the material of the anode E1 include aluminum and silver.
In the case where the organic EL element 1 is of the bottom emission type, since light from the light-emitting layer 13 is reflected by the cathode E2 and is guided out from the anode E1 side, a material having high visible light transmittance is preferable as the material of the anode E1. Specific examples of the material of the anode E1 include a thin film made of Indium Oxide, Zinc Oxide, tin Oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), or the like, gold, platinum, silver, copper, aluminum, or an alloy containing at least 1 of these metals.
Examples of the method for forming the anode E1 include a vacuum deposition method, a sputtering method, an ion plating method, a plating method, and the like. As the anode E1, a transparent conductive film of an organic material such as polyaniline or a derivative thereof, polythiophene or a derivative thereof, or the like can be used.
The thickness of the anode E1 may be appropriately determined in consideration of light transmittance, electrical conductivity, and the like. The thickness of the anode E1 is, for example, 10nm to 10 μm, preferably 20nm to 1 μm, and more preferably 50nm to 500 nm.
< hole injection layer >
The hole injection layer 11 is a functional layer having a function of improving the efficiency of hole injection from the anode E1. Examples of the hole injection material constituting the hole injection layer 11 include oxides such as vanadium oxide, molybdenum oxide, ruthenium oxide, and aluminum oxide, polyaniline compounds, starburst amine compounds, phthalocyanine compounds, amorphous carbon, polyaniline, and polythiophene derivatives such as polyethylene dioxythiophene (PEDOT).
The hole injection layer 11 can be formed by, for example, a coating method using a coating liquid containing the hole injection material described above. The solvent of the coating liquid may be any solvent as long as it dissolves the hole injecting material, and examples thereof include chloroform, water, chlorine-based solvents such as methylene chloride and dichloroethane, ether-based solvents such as tetrahydrofuran, aromatic hydrocarbon-based solvents such as toluene and xylene, ketone-based solvents such as acetone and methyl ethyl ketone, and ester-based solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate.
Examples of the coating method include a spin coating method, a casting method, a microgravure coating method, a gravure coating method, a bar coating method, a roll coating method, a wire bar coating method, a dip coating method, a spray coating method, a screen printing method, a flexographic printing method, an offset printing method, and an inkjet printing method. The hole injection layer 11 can be formed by applying the coating liquid described above on the substrate P on which the anode E1 is formed, using 1 of these coating methods.
The hole injection layer 11 may be formed by a vacuum deposition method or the like. When the hole injection layer 11 contains a metal oxide, the hole injection layer 11 may be formed by a sputtering method, an ion plating method, or the like.
The optimum value of the thickness of the hole injection layer 11 differs depending on the material used. The thickness of the hole injection layer 11 can be determined as appropriate in consideration of the required characteristics, the ease of film formation, and the like. The thickness of the hole injection layer 11 is, for example, 1nm to 1 μm, preferably 2nm to 500nm, and more preferably 5nm to 200 nm.
< hole transport layer >
The hole transport layer 12 is a functional layer having a function of improving hole injection into the light-emitting layer 13 from a layer (the hole injection layer 11 in fig. 1) in contact with the interface on the anode E1 side of the hole transport layer 12 or the hole transport layer 12 closer to the anode E1.
Examples of the hole transporting material constituting the hole transporting layer 12 include polyvinylcarbazole or a derivative thereof, polysilane or a derivative thereof, a polysiloxane derivative having an aromatic amine in a side chain or a main chain, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, polyaniline or a derivative thereof, polythiophene or a derivative thereof, polyarylamine or a derivative thereof, polypyrrole or a derivative thereof, poly (p-phenylene vinylene) or a derivative thereof, poly (2, 5-thienylene vinylene) or a derivative thereof, and the like. Further, a hole transport layer material disclosed in Japanese patent laid-open No. 2012-144722 may be mentioned.
The hole transport layer 12 can be formed by, for example, a coating method using a coating liquid containing the aforementioned hole transport material. The solvent used for forming a film from the solution may be any solvent as long as it dissolves the hole-transporting material, and examples thereof include chlorine-based solvents such as chloroform, dichloromethane, and dichloroethane, ether-based solvents such as tetrahydrofuran, aromatic hydrocarbon-based solvents such as toluene and xylene, ketone-based solvents such as acetone and methyl ethyl ketone, and ester-based solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate.
As a film formation method using a solution, the same coating method as that described as a method for forming a hole injection layer can be used.
The optimum value of the film thickness of the hole transport layer 12 differs depending on the material used. The film thickness of the hole transport layer 12 is appropriately set so that the driving voltage and the light emission efficiency are appropriate values. The hole transport layer 12 needs to have a thickness at least not to generate pinholes. If the hole transport layer 12 is too thick, the driving voltage of the element increases, which is not preferable. Therefore, the film thickness of the hole transport layer 12 is, for example, 1nm to 1 μm, preferably 2nm to 500nm, and more preferably 5nm to 200 nm.
< light emitting layer >
The light-emitting layer 13 usually contains an organic substance that mainly emits fluorescence and/or phosphorescence, or the organic substance and a dopant material that assists it. The dopant material is added to the light-emitting layer 13, for example, to improve the light-emitting efficiency or to change the light-emitting wavelength. The organic material is preferably a polymer compound from the viewpoint of solubility. The light-emitting layer 13 preferably contains polystyrene equivalent number average molecular weight of 1.0 × 103～108The polymer compound of (1). Examples of the organic material mainly emitting fluorescence and/or phosphorescence include the following pigment-based material, metal complex-based material, and polymer-based material.
Examples of the pigment-based material include cyclopentamine derivatives, tetraphenylbutadiene derivatives, triphenylamine derivatives, oxadiazole derivatives, pyrazoloquinoline derivatives, distyrylbenzene derivatives, distyrylarylene derivatives, pyrrole derivatives, thiophene ring compounds, pyridine ring compounds, perinone derivatives, perylene derivatives, oligothiophene derivatives, oxadiazole dimers, pyrazoline dimers, quinacridone derivatives, and coumarin derivatives.
Examples of the metal complex-based material include metal complexes having a rare earth metal such as Tb, Eu, or Dy as a central metal, or a metal complex having a structure of oxadiazole, thiadiazole, phenylpyridine, phenylbenzimidazole, quinoline, or the like as a ligand such as Al, Zn, Be, Pt, or Ir. Examples of the metal complex include metal complexes that emit light from a triplet excited state, such as iridium complexes and platinum complexes, aluminum hydroxyquinoline complexes, beryllium benzohydroxyquinoline complexes, zinc benzoxazolyl complexes, zinc benzothiazolyl complexes, zinc azomethylzinc complexes, zinc porphyrin complexes, and europium phenanthroline complexes.
Examples of the polymer-based material include polyparaphenylene vinylene derivatives, polythiophene derivatives, polyparaphenylene derivatives, polysilane derivatives, polyacetylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives, and materials obtained by polymerizing the above pigment-based material or metal complex material.
Among the above light-emitting materials, examples of a material emitting blue light include a distyrylarylene derivative, an oxadiazole derivative, a polymer thereof, a polyvinylcarbazole derivative, a polyparaphenylene derivative, a polyfluorene derivative, and the like. Among them, polyvinyl carbazole derivatives, polyparaphenylene derivatives, polyfluorene derivatives, and the like are preferable as the polymer material. As a material emitting blue light, a material disclosed in japanese patent laid-open No. 2012-144722 can be cited.
The green-emitting material includes quinacridone derivatives, coumarin derivatives, polymers thereof, polyparaphenylene vinylene derivatives, polyfluorene derivatives, and the like. Among them, a poly (p-phenylene vinylene) derivative, a polyfluorene derivative, and the like are preferable as the polymer material. As the material emitting green light, materials disclosed in japanese patent laid-open No. 2012-036388 can be mentioned.
Examples of the red-emitting material include coumarin derivatives, thiophene ring compounds, polymers thereof, polyparaphenylene vinylene derivatives, polythiophene derivatives, and polyfluorene derivatives. Among them, polyparaphenylene vinylene derivatives, polythiophene derivatives, polyfluorene derivatives, and the like are preferable as the polymer material. As the material emitting red light, a material disclosed in japanese patent application laid-open publication No. 2011-105701 can be cited.
Examples of the dopant material include perylene derivatives, coumarin derivatives, rubrene derivatives, quinacridone derivatives, squarylium salt derivatives, porphyrin derivatives, styryl pigments, tetracene derivatives, pyrazolone derivatives, decacycloalkene, phenoxazinone, and the like.
As a method for forming the light-emitting layer 13, a coating method such as a spin coating method, a casting method, a micro gravure coating method, a bar coating method, a roll coating method, a wire bar coating method, a dip coating method, a die coating method, a capillary coating method, a spray coating method, a nozzle coating method, a gravure printing method, a screen printing method, a flexographic printing method, an offset printing method, a reverse printing method, and an ink jet printing method can be used. From the viewpoint of ease of pattern formation and multi-color separation, a gravure printing method, a screen printing method, a flexographic printing method, an offset printing method, a reverse printing method, and an ink jet printing method are preferable. In the case of a low-molecular-weight compound exhibiting sublimability, a vacuum vapor deposition method can be used. The light-emitting layer 13 may be formed only in a desired place by a method such as transfer by laser or friction, thermal transfer, or the like. Among them, from the viewpoint of ease of the production process, it is preferable to form the light-emitting layer 13 by an application method using a solution containing a light-emitting material. As the solvent of the solution containing the light-emitting material, for example, the solvents mentioned above as the solvents of the coating liquid for forming the hole injection layer 11 can be used.
The thickness of the light-emitting layer 13 is preferably about 2nm to 200 nm.
< layer 1 >)
The 1 st layer 14b is provided between the light-emitting layer 13 and a cathode E2 described later. The 1 st layer 14b may be in direct contact with the light emitting layer 13. The 1 st layer 14b contains an organometallic complex compound.
The organometallic complex compound contains at least one element selected from the group consisting of alkali metal elements, alkaline earth metal elements, and rare earth metal elements. The organometallic complex compound may contain an alkali metal element or an alkaline earth metal element in an ionic state. Examples of the alkali metal ion include Li+、Na+、K+、Rb+And Cs+Among them, Li is preferable+、Na+Or Cs+More preferably Li+Or Na+. As alkaline earth metal ionsExamples thereof include Be2+、Mg2+、Ca2+、Sr2+And Ba2+Among them, Mg is preferable2+、Ca2+Or Ba2+More preferably Ca2+Or Ba2+。
The organometallic complex compound may contain a rare earth metal element in an ionic state. Examples of the rare earth metal ion include Y3+、La3+、Ce4+、Eu3+、Gd3+、Tb3+、Yb3+. Preferred among them is Eu3+Or Yb3+More preferably Yb3 +。
Examples of the ligand contained in the organometallic complex compound include hydroxyquinoline, benzohydroxyquinoline, hydroxyacridine (acridiniolato), hydroxyphenylphenanthridine (phenanthridinoloto), hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryl oxadiazole, hydroxydiaryl thiadiazole, hydroxyphenylbenzimidazole, hydroxybenzotriazole, hydroxyfluoroborane (hydroxyfluoroborane), bipyridine, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, a ligand having a 2- (2-pyridyl) phenol skeleton, β -diketones, azomethines, and derivatives thereof, and specific examples of the ligand contained in the organometallic complex compound include ligands represented by the following formulae (1) to (18).
[ solution 1]
[ solution 2]
[ solution 3]
[ solution 4]
[ solution 5]
In each of the ligands represented by the formulae (1) to (18), at least 1 hydrogen atom bonded to a carbon atom contained in the five-membered ring or the six-membered ring may be substituted with an alkyl group having 1 to 12 carbon atoms. The alkyl group having 1 to 12 carbon atoms is preferably a methyl group, an ethyl group, a propyl group, or a tert-butyl group.
In the formulae (1) to (18), the organometallic complex compound preferably contains a ligand represented by the formula (1) (8-hydroxyquinoline), the formula (2) (5-hydroxyquinoxaline), the formula (4) (8-hydroxyquinazoline), the formula (6) (benzo-8-hydroxyquinoline), the formula (7) (benzo-5-hydroxyquinoxaline), the formula (9) (benzo-8-hydroxyquinazoline), and the formula (18) (2- (2 ', 2 "-bipyridin-6' -yl) phenol group), and more preferably contains a ligand represented by the formula (1), the formula (2), or the formula (4).
Specific examples of the organometallic complex compound include lithium 8-quinolinolato (Liq), sodium 8-quinolinolato (Naq), potassium 8-quinolinolato, rubidium 8-quinolinolato, cesium 8-quinolinolato, lithium benzo-8-quinolinolato, sodium benzo-8-quinolinolato, potassium benzo-8-quinolinolato, rubidium benzo-8-quinolinolato, cesium benzo-8-quinolinolato, lithium 2-methyl-8-quinolinolato, sodium 2-methyl-8-quinolinolato, potassium 2-methyl-8-quinolinolato, rubidium 2-methyl-8-quinolinolato, cesium 2- (2 ', 2' -bipyridin-6 '-yl) phenolate Lithium (LiBPP), and sodium 2- (2', 2 '-bipyridin-6' -yl) phenolate (NaBPP).
Of the above, as the organometallic complex compound, at least 1 selected from 8-quinolinolato lithium, 8-quinolinolato sodium, 2- (2 ', 2 "-bipyridin-6' -yl) phenolato Lithium (LiBPP), and 2- (2 ', 2" -bipyridin-6' -yl) phenolato sodium (NaBPP) is preferably contained, and 8-quinolinolato sodium is more preferred.
The 1 st layer 14b may contain an electron-transporting organic compound. As the electron-transporting organic compound, a known organic compound generally used for an electron-transporting layer having a function of transporting electrons can be used. Examples of the compound include compounds having a condensed aryl ring such as naphthalene and anthracene, derivatives thereof, compounds having a fluorene skeleton, styrene-based aromatic ring derivatives represented by 4, 4-bis (diphenylvinyl) biphenyl, perylene derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone, naphthoquinone, diphenoquinone, anthraquinone dimethane, tetracyanoanthraquinone dimethane and other quinone derivatives, phosphorus oxide derivatives, carbazole derivatives, indole derivatives, tris (8-hydroxyquinoline) aluminum (III) and other hydroxyquinoline complexes, and hydroxyphenyl oxazole complexes such as hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes and flavonol metal complexes, and compounds having a heteroaryl ring containing an electron-accepting nitrogen.
Specific examples of the electron-transporting organic compound include PPT (2, 8-bis (diphenylphosphoryl) benzo [ B, d ] thiophene) represented by the following formula (I), TPBi (1, 3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene) represented by the following formula (II), TmPyPB (1, 3, 5-tris (3-pyridyl-3-phenyl) benzene) represented by the following formula (III), and B3PyPB (1, 3-bis (3, 5-bipyridin-3-ylphenyl) benzene) represented by the following formula (IV).
[ solution 6]
[ solution 7]
[ solution 8]
[ solution 9]
The electron accepting nitrogen is a nitrogen atom having a multiple bond with an adjacent atom. Since the nitrogen atom has a high electronegativity, the multiple bond also has an electron accepting property. Thus, heteroaryl rings with electron accepting nitrogen have high electrophilicity. Examples of the compound having a heteroaryl ring structure containing an electron-accepting nitrogen include benzimidazole derivatives, benzothiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, triazole derivatives, pyridine derivatives, pyrazine derivatives, phenanthroline derivatives, quinoxaline derivatives, quinoline derivatives, benzoquinoline derivatives, bipyridine derivatives, terpyridine and other oligomeric pyridine derivatives, quinoxaline derivatives, naphthyridine derivatives, phenanthroline derivatives and the like, which are preferable compounds.
As the electron-transporting organic compound, a compound having a fluorene skeleton is preferable. Examples of the compound having a fluorene skeleton include 1 to 8 polymers of 9, 9-spirobifluorene. The compound having a fluorene skeleton may be a compound in which at least one of hydrogen directly bonded to a fluorene ring is substituted by a carbazolyl group, a phosphinoxide group, a trimethylsilyl group, a triphenylsilyl group, a thienyl group, a triazinyl group, a bipyridyl group, a pyridyl group, or the like. More specifically, 2 ": 7 ", 2" "-tris-9, 9' -spirobis [ 9H-fluorene ] (TSBF).
From the viewpoint of further reducing the driving voltage of the organic EL element, the 1 st layer 14b preferably contains the organometallic complex compound in a proportion of 50 to 100 vol%, more preferably 80 to 100 vol%, relative to 100 vol% of the total amount of the materials contained in the 1 st layer 14 b.
As a method for forming the 1 st layer 14b, for example, a method of vacuum vapor-depositing an organic metal complex compound is given. In the case where the 1 st layer 14b contains an electron-transporting organic compound, the electron-transporting organic compound and the organometallic complex compound may be co-deposited by a vacuum deposition method. In the case of co-depositing an electron-transporting organic compound and an organometallic complex compound by a vacuum deposition method, the ratio of the organometallic complex compound contained in the 1 st layer 14b can be adjusted by changing the deposition rate of the electron-transporting organic compound and the deposition rate of the organometallic complex compound.
The thickness of the 1 st layer is not particularly limited, and may be, for example, 0.1 to 10 nm.
< layer 2 >
The 2 nd layer 14a is a layer provided between the 1 st layer 14b and the cathode E2, and includes an electron-transporting organic compound (hereinafter also referred to as the 1 st material) and at least one of an alkali metal and an alkaline earth metal (hereinafter also referred to as the 2 nd material). That is, the 2 nd layer 14a is a layer containing a mixture of the 1 st material and the 2 nd material. The 2 nd layer 14a may be in direct contact with the 1 st layer 14 b.
As the 1 st material contained in the 2 nd layer 14a, a known organic compound generally used in an electron transport layer can be used. More specifically, the organic compound is exemplified as the electron-transporting organic compound contained in the 1 st layer 14 b. Among them, a compound having a fluorene skeleton is preferable.
Examples of the alkali metal in the 2 nd material contained in the 2 nd layer 14a include Li, Na, K, Rb, and Cs, and Li, Na, K, and Cs are preferable. The alkaline earth metal contained in the 2 nd layer 14a includes Be, Mg, Ca, Sr, and Ba, and among them, Ca and Ba are preferable. The 2 nd material contained in the 2 nd layer 14a is preferably an alkaline earth metal.
From the viewpoint of further reducing the driving voltage of the organic EL element or the visible light transmittance, the 2 nd layer 14a preferably contains the 1 st material in an amount of 70 to 99 vol% and the 2 nd material in an amount of 1 to 30 vol% based on 100 vol% of the total amount of the materials contained in the 2 nd layer 14a, and more preferably contains the 1 st material in an amount of 90 to 99 vol% and the 2 nd material in an amount of 1 to 10 vol%.
According to the organic EL element of the present embodiment having the 1 st layer 14b and the 2 nd layer 14a, the driving voltage can be reduced. The reason for this is not necessarily determined, but the present inventors consider it as follows. First, in the case where the 2 nd layer is not present, that is, in the case where the 1 st layer is directly in contact with a cathode such as Al or a reductive metal layer such as Ba, the alkali metal element or the like contained in the organometallic complex compound of the 1 st layer can accept electrons from the cathode or the metal layer depending on the oxidation state thereof and transfer the electrons to the light-emitting layer. Thereby, holes and electrons are combined in the light-emitting layer, and the light-emitting layer emits light. However, when the organometallic complex compound is reduced by the cathode or the metal layer, a complex of the ligand of the organometallic complex compound and the metal contained in the cathode or the metal layer is formed as a by-product at the interface between the 1 st layer and the cathode or the metal layer or in the cathode or the metal layer. It is considered that the by-product acts as a resistance component, and thus the driving voltage of the organic EL element tends to be increased. Here, in the organic EL element of the present embodiment, since the 2 nd layer contains both the 2 nd material and the 1 st material having an electron-transporting property, the reduction of the organometallic complex compound by the 2 nd material is performed via the 1 st material. Therefore, it is considered that the generation of the by-products is suppressed and the driving voltage of the organic EL element can be reduced. It is also considered that the 1 st material also has a function of lowering an electron injection barrier from the cathode to the 1 st layer.
Examples of a method for forming the 2 nd layer include a method of co-evaporating the 1 st material and the 2 nd material by a vacuum evaporation method. The deposition rates of the 1 st material and the 2 nd material are not particularly limited, but the deposition rate of the 1 st material is preferably set to
The deposition rate of the No. 2 material is
In the case of co-depositing the 1 st material and the 2 nd material by a vacuum deposition method, the ratio of the 1 st material and the 2 nd material contained in the 2 nd layer 14a can be adjusted by changing the deposition rate of the 1 st material and the deposition rate of the 2 nd material.
The 2 nd layer preferably has a thickness of 0.1nm to 200 nm.
< cathode >
The material of the cathode E2 is preferably a material having a small work function, easy electron injection into the 2 nd layer 14a, and high electrical conductivity. The cathode E2 may be in contact with the 2 nd layer 14 a.
The thickness of the cathode E2 can be appropriately set in consideration of the electrical conductivity and durability. The thickness of the cathode E2 is, for example, 10nm to 10 μm, preferably 20nm to 1 μm, and more preferably 50nm to 500 nm.
When the organic EL element 1 is of a top emission type, a material having high visible light transmittance is preferable as the material of the cathode E2 in order to extract light from the light-emitting layer 13 from the cathode E2 side. As a material of the cathode E2, for example, a thin film containing Indium Oxide, Zinc Oxide, Tin Oxide, Indium Tin Oxide (ITO) or Indium Zinc Oxide (IZO), gold, platinum, silver, copper, aluminum, an alkali metal, an alkaline earth metal, or an alloy containing at least 1 of these metals can be used.
In the case where the organic EL element 1 is of the bottom emission type, since light from the light-emitting layer 13 is reflected by the cathode E2 and is guided out from the anode E1 side, a material having a high visible light reflectance is preferable as the material of the cathode E2. Specific examples of the material of the cathode E2 include a thin film containing Indium Oxide, Zinc Oxide, tin Oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), or the like, gold, platinum, silver, copper, aluminum, an alkali metal, an alkaline earth metal, or an alloy containing at least 1 of these metals.
Examples of the method for forming the cathode E2 include a vacuum deposition method, a sputtering method, and a lamination method in which a metal thin film is thermocompression bonded.
While various embodiments of the present invention have been described above, the present invention is not limited to the exemplary embodiments, and is intended to include all modifications within the meaning and range equivalent to the claimed range, given by the claimed range.
For example, the structure of the organic EL element is not limited to the structure illustrated in fig. 1.
The organic EL device may have the 1 st layer 14b and the 2 nd layer 14a between the light-emitting layer 13 and the cathode E2. An example of a layer configuration that the organic EL element can take is given. In the following a) to c), the layer including the 1 st layer and the 2 nd layer is also referred to as a multilayer electron transport layer.
a) Anode/hole injection layer/light-emitting layer/multi-layer type electron transport layer/cathode
b) Anode/hole injection layer/hole transport layer/light-emitting layer/multilayer type electron transport layer/cathode
c) Anode/light-emitting layer/multilayer type electron transport layer/cathode
The symbol "/" indicates that the layers on both sides of the symbol "/" are joined.
The "multilayer electron transport layer" in a) to c) is specifically any of the following laminated structures (i) to (vi).
(i) 1 st laminated structure: layer 1/layer 2
(ii) 2 nd laminated structure: layer 1/layer 2/electron injection layer
(iii) The 3 rd laminated structure: layer 1/layer 2/electron transport layer/electron injection layer
(iv) The 4 th laminated structure: layer 1/layer 2/electron transport layer
(v) 5 th laminated structure: layer 1/electron injection layer/layer 2/electron transport layer
(vi) 6 th laminated structure: layer 1/Electron transport layer/layer 2/Electron transport layer
In the above-mentioned (ii), (iii) and (v), the electron injection layer is a functional layer having a function of improving the electron injection efficiency from the cathode E2 to the 2 nd layer 14a or the electron injection efficiency from the 2 nd layer 14a to the 1 st layer 14 b. The optimum value of the thickness of the electron injection layer varies depending on the material used, but the thickness of the electron injection layer may be appropriately set in consideration of electrical characteristics, ease of film formation, and the like. The thickness of the electron injection layer is, for example, 0.1nm to 1 μm.
As the material of the electron injection layer, a known electron injection material can be used. Examples of the material of the electron injection layer include alkali metals, alkaline earth metals, alloys containing 1 or more of alkali metals and alkaline earth metals, oxides, halides, carbonates, fluorides of alkali metals and alkaline earth metals, and mixtures thereof. In addition, a layer obtained by mixing a conventionally known electron-transporting organic material with an alkali metal organometallic complex can be used as the electron injection layer.
In the above-mentioned (iii), (iv) and (vi), the electron transport layer is a layer having a function of transporting electrons from the cathode E2 to the 2 nd layer 14a or the electron injection layer, or transporting electrons from the 2 nd layer 14a to the 1 st layer 14 b. The electron-transporting material constituting the electron-transporting layer is not particularly limited as long as it is a material that is generally used as an electron-transporting material, and examples thereof include the electron-transporting organic compounds contained in the 1 st layer 14b and the 2 nd layer 14a described above. The thickness of the electron transport layer may be, for example, 0.1nm to 1 μm. In the above (v) and (vi), each electron transport layer may be replaced with an electron injection layer or an electron transport layer/electron injection layer.
When at least one of the layers constituting the multilayer electron transport layer is a layer having a function of blocking the transport of holes, such a layer having a function of blocking the transport of holes may be referred to as a hole blocking layer.
In the case where the hole blocking layer has a function of blocking the transport of holes, for example, an organic EL element in which only a hole current flows can be manufactured, and the effect of blocking can be confirmed by a decrease in the current value.
In addition, in the case where the hole injection layer and/or the hole transport layer in a) and b) has a function of blocking the transport of electrons, these layers may be referred to as electron blocking layers. In the case where the electron blocking layer has a function of blocking the transport of electrons, for example, an organic EL element through which only electron current flows may be fabricated, and the effect of blocking the transport of electrons may be confirmed by using the measured decrease in current value. An electron blocking layer may be provided between the anode and the light-emitting layer in addition to the hole injection layer and/or the hole transport layer.
The organic EL element may have a single-layer light-emitting layer or 2 or more light-emitting layers. In any of the layer configurations a) to c), if a laminate disposed between an anode and a cathode is referred to as "structural unit a", the layer configuration shown in d) below can be given as a configuration of an organic EL element having 2 light-emitting layers. The layer structures in which 2 layers (structural units a) are present may be the same or different from each other.
d) Anode/(structural unit A)/charge generation layer/(structural unit A)/cathode
The charge generation layer is a layer that generates holes and electrons when an electric field is applied. Examples of the charge generation layer include a thin film containing vanadium Oxide, Indium Tin Oxide (ITO), molybdenum Oxide, or the like.
If "(structural unit a)/charge generation layer" is "structural unit B", the layer structure shown in e) below can be given as the structure of the organic EL element having 3 or more light-emitting layers 13.
e) Anode/(structural unit B) x/(structural unit A)/cathode
The symbol "x" represents an integer of 2 or more, and the symbol "(structural unit B) x" represents a laminate in which x stages (structural unit B) are laminated. The layer structure in which a plurality of layers (structural units B) exist may be the same or different.
Instead of providing a charge generation layer, a plurality of light-emitting layers may be directly stacked to form an organic EL element.
In the description so far, an example in which the anode is disposed on the substrate side has been described, but the cathode may be disposed on the substrate side. In this case, for example, when the organic EL elements a) to c) are fabricated on a substrate, the layers may be stacked on the substrate in order from the right side of the cathode (the components a) to c)).
The organic electroluminescent element of this embodiment mode can be used for an organic EL display.
Examples
The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to the following examples.
[ example 1]
As example 1, an organic EL device was produced in which an anode, a hole injection layer, a hole transport layer, a light-emitting layer, a1 st layer, a2 nd layer, and a cathode were sequentially stacked on a substrate as shown in fig. 1. Hereinafter, the organic EL device of example 1 is referred to as an organic EL device a 1. In example 1, the organic EL element a1 was sealed with glass. Hereinafter, a method for manufacturing the organic EL device will be described in detail.
< substrate and anode >
A glass substrate was prepared as a substrate of the organic EL element. On a glass substrate, an ITO thin film is formed in a given pattern as an anode. An ITO thin film is formed by a sputtering method. The thickness of the ITO film was 45 nm. A glass substrate having an ITO film formed on the surface thereof was ultrasonically cleaned in this order with an organic solvent, an alkaline detergent and ultrapure water, and then boiled in the organic solvent for 10 minutes and dried. Then, the surface on which the ITO thin film was formed was subjected to ultraviolet ozone treatment for about 15 minutes using an ultraviolet ozone (UV-O3) apparatus.
< hole injection layer >
A hole injection material obtained by combining an organic material having a charge transport property and an electron accepting material was applied onto an ITO thin film by a spin coating method to form a coating film having a thickness of 35 nm.A hole injection material used in example 1 is hereinafter referred to as a hole injection material α 1. in the air, a glass substrate provided with the coating film was dried on a hot plate to form a hole injection layer.A drying step using a hot plate was carried out by first drying at 80 ℃ for 4 minutes and then at 230 ℃ for 15 minutes.
< hole transport layer >
The hole transport layer-forming composition used in example 1 was applied to a hole injection layer by a spin coating method to obtain a coating film having a film thickness of 20nm, and the glass substrate provided with the coating film was heated at 200 ℃ for 30 minutes under a nitrogen atmosphere (inert atmosphere) with a hot plate to evaporate the solvent, and then was naturally cooled to room temperature to obtain a hole transport layer.
< light emitting layer >
The light-emitting layer-forming composition was prepared by mixing a light-emitting conjugated polymer material with xylene to obtain a light-emitting layer-forming composition having a light-emitting conjugated polymer material concentration of 1.3%, in example 1, a blue light-emitting conjugated polymer material was used as the light-emitting conjugated polymer material, hereinafter, the blue light-emitting conjugated polymer material used in example 1 was referred to as "blue light-emitting conjugated polymer material α 3", the obtained light-emitting layer-forming composition was applied onto the hole-transporting layer by a spin coating method to obtain a coating film having a film thickness of 60nm, and the glass substrate provided with the coating film was heated at 180 ℃ for 10 minutes by a hot plate under a nitrogen atmosphere (inactive atmosphere) to evaporate the solvent and then naturally cooled to room temperature to obtain a light-emitting layer.
< layer 1 >)
The glass substrate on which the light emitting layer was formed was moved to a deposition chamber, and the 1 st layer was formed on the light emitting layer. Specifically, the degree of vacuum of the exhaust gas into the deposition chamber was 1.0 × 10－5Pa or less, 8-hydroxyquinoline sodium (Naq) represented by the following formula was deposited on the light-emitting layer by vacuum deposition to a film thickness of 2nm to form a1 st layer of Naq. The evaporation speed is
[ solution 10]
< layer 2 >
After the 1 st layer is formed, a2 nd layer is formed on the 1 st layer in the evaporation chamber. Specifically, TSBF represented by the following formula as a1 st material and barium as a2 nd material were co-evaporated on the 1 st layer by a vacuum evaporation method to form a2 nd layer having a thickness of 10 nm. TSBF has a vapor deposition rate of
The deposition rate of barium is
At this time, in the 2 nd layer, TSBF was contained at a rate of 90 vol%, and barium was contained at a rate of 10 vol%.
[ solution 11]
< cathode >
After the 2 nd layer is formed, a cathode is formed in a vapor deposition chamber dedicated to metal. Specifically, aluminum was deposited on the 2 nd layer by vacuum deposition to form a cathode having a film thickness of 100 nm. Thereby completing the organic EL element a 1.
< glass sealing >
After the cathode was formed, the organic EL element a1 was transported from the vapor deposition chamber to the sealing treatment chamber without being exposed to the atmosphere, and the sealing glass coated with the UV curable resin on its periphery was bonded to the glass substrate transported from the vapor deposition chamber in a nitrogen atmosphere (inert atmosphere) and irradiated with UV light, whereby the UV curable resin was cured, and the organic EL element a1 was sealed with glass.
The organic EL element a1 produced as described above was driven, and the driving voltage was measured. The driving voltage was set to 10mA/cm for the organic EL element A12Voltage at constant current drive. The driving voltage of the organic EL element a1 was 3.4V.
Comparative example 1
As comparative example 1, an organic EL element B1 described in the prior art (japanese patent No. 4514841) was produced. An organic EL element B1 was produced in the same manner as the organic EL element a1, except that the 2 nd layer was not formed. The produced organic EL element B1 was glass-sealed in the same manner as in example 1.
The organic EL element B1 of comparative example 1 was driven, and the driving voltage was measured under the same conditions as in example 1. The driving voltage of the organic EL element B1 was 7.9V.
Comparative example 2
As comparative example 2, an organic EL device C1 was produced. An organic EL element C1 was produced in the same manner as the organic EL element a1, except that a barium monolayer was formed instead of the 2 nd layer of the organic EL element a 1. By using exhaust gas to 1.0X 10－5Vacuum deposition method in a vacuum chamber under Pa (deposition rate:
) A barium metal was formed on the layer 1 to form a barium monolayer. The thickness of the barium monolayer was 1 nm. The organic EL element C1 thus produced was glass-sealed in the same manner as in example 1.
The organic EL device C1 of comparative example 2 was driven, and the driving voltage was measured under the same conditions as in example 1. The driving voltage of the organic EL element C1 was 6.6V.
Comparative example 3
As comparative example 3, an organic EL device D1 was produced. An organic EL element D1 was produced in the same manner as in the organic EL element a1, except that a barium monolayer, a TSBF monolayer, and a sodium fluoride layer were formed in this order on the 1 st layer instead of the 2 nd layer of the organic EL element a 1. By venting to 1.0X 10－5Vacuum deposition method in vacuum chamber under Pa, respectively
And
the deposition rate of (3) is such that a barium monolayer, a TSBF monolayer and a sodium fluoride layer are formed. The thicknesses of the barium monolayer, the TSBF monolayer and the sodium fluoride layer are 1nm, 10nm and 3nm respectively. The organic EL device D1 thus produced was glass-sealed in the same manner as in example 1.
The organic EL device D1 of comparative example 3 was driven, and the driving voltage was measured under the same conditions as in example 1. The driving voltage of the organic EL element D1 was 7.0V.
[ comparison of example 1 and comparative examples 1 to 3]
The measurement results of the driving voltage for the organic EL devices of example 1 and comparative examples 1 to 3 are shown in table 1.
[ Table 1]
[ example 2]
As example 2, an organic EL device a2 was produced. An organic EL element a2 was produced in the same manner as the organic EL element a1 of example 1, except that the layer 1 included TSBF. Note that Naq and TSBF were co-evaporated on the light-emitting layer by a vacuum evaporation method to form the 1 st layer of the organic EL element a 2. Naq has a vapor deposition rate of
TSBF has a vapor deposition rate of
At this time, Naq was contained in the layer 1 at a ratio of 50 vol%, and TSBF was contained at a ratio of 50 vol%. The thickness of the 1 st layer of the organic EL element A2 was 2 nm. The organic EL element a2 thus produced was glass-sealed in the same manner as in example 1.
The organic EL element a2 of example 2 was driven, and the driving voltage was measured under the same conditions as in example 1. The driving voltage of the organic EL element a2 was 3.8V.
[ example 3]
An organic EL device a3 was produced as example 3. Except that the vapor deposition rate of Naq in the formation of the 1 st layer was set to
TSBF has a vapor deposition rate of
Except for this, an organic EL device a3 was produced in the same manner as in example 2. The organic EL element a3 thus produced was glass-sealed in the same manner as in example 1. At this time, Naq was contained in the layer 1 at a ratio of 80 vol%, and TSBF was contained at a ratio of 20 vol%.
The organic EL element a3 of example 3 was driven, and the driving voltage was measured under the same conditions as in example 1. The driving voltage of the organic EL element a3 was 3.5V.
[ comparison of examples 1 to 3 and comparative example 1]
The results of measuring the driving voltages of examples 1 to 3 and comparative example 1 are shown in table 2.
[ Table 2]
[ example 4]
As example 4, an organic EL device a4 was produced. An organic EL element a4 was produced in the same manner as the organic EL element a1, except that calcium was used as the 2 nd material of the 2 nd layer instead of barium. The layer 2 of the organic EL element a4 was formed by co-evaporation of TSBF and calcium metal by a vacuum evaporation method. The film thickness of the 2 nd layer was 10 nm. At this time, the deposition rate of TSBF is
The deposition rate of calcium is
At this time, in the 2 nd layer, TSBF was contained at a rate of 90 vol%, and calcium was contained at a rate of 10 vol%. The organic EL element a4 thus produced was glass-sealed in the same manner as in example 1.
The organic EL element a4 of example 4 was driven, and the driving voltage was measured under the same conditions as in example 1. The driving voltage of the organic EL element a4 was 3.8V.
[ comparison of examples 1 and 4 and comparative example 1]
The measurement results of the driving voltage for the organic EL devices of examples 1 and 4 and comparative example 1 are shown in table 3.
[ Table 3]
[ example 5]
As example 5, an organic EL device a5 was produced. An organic EL element a5 was produced in the same manner as the organic EL element a1, except that 8-hydroxyquinoline lithium (Liq) was used as the 1 st layer instead of Naq. Note that Liq is deposited by a vacuum deposition method on the light-emitting layer to form the 1 st layer of the organic EL element a5 (deposition rate:
). The film thickness of the 1 st layer was 1 nm. The organic EL element a5 thus produced was glass-sealed in the same manner as in example 1.
The organic EL element a5 of example 5 was driven, and the driving voltage was measured under the same conditions as in example 1. The driving voltage of the organic EL element a5 was 4.1V.
Comparative example 4
As comparative example 4, an organic EL device F1 described in the prior art (japanese patent No. 4514841) was produced. An organic EL element F1 was produced in the same manner as the organic EL element a5, except that the 2 nd layer was not formed. The produced organic EL device F1 was glass-sealed in the same manner as in example 1.
The organic EL device F1 of comparative example 4 was driven, and the driving voltage was measured under the same conditions as in example 1. The driving voltage of the organic EL element F1 was 7.8V.
[ comparison between example 5 and comparative example 4]
The measurement results of the drive voltage for the organic EL devices of example 5 and comparative example 4 are shown in table 4.
[ Table 4]
Description of the symbols
1 organic EL element, 11 hole injection layer, 12 hole transport layer, 13 light emitting layer, 14a 2 nd layer, 14b 1 st layer, E1 anode, E2 cathode.
Claims (8)
1. An organic electroluminescent element comprising an anode, a cathode, and a light-emitting layer provided between the anode and the cathode,
the organic electroluminescent element includes:
a1 st layer disposed between the cathode and the light-emitting layer, and
a2 nd layer disposed between the 1 st layer and the cathode,
the 1 st layer contains an organometallic complex compound containing at least 1 selected from an alkali metal element, an alkaline earth metal element, and a rare earth metal element,
the 2 nd layer contains an electron-transporting organic compound and at least one metal selected from alkali metals and alkaline earth metals.
2. The organic electroluminescent element according to claim 1, wherein,
the 1 st layer is in contact with the light-emitting layer.
3. The organic electroluminescent element according to claim 1 or 2, wherein,
the 2 nd layer is in contact with the 1 st layer.
4. The organic electroluminescent element according to any one of claims 1 to 3, wherein,
the cathode is in contact with the 2 nd layer.
5. The organic electroluminescent element according to any one of claims 1 to 4, wherein,
the organometallic complex compound contains at least one selected from 8-hydroxyquinoline sodium, 8-hydroxyquinoline lithium, 2- (2 ', 2' -bipyridin-6 '-yl) phenolate lithium, and 2- (2', 2 '-bipyridin-6' -yl) phenolate sodium.
6. The organic electroluminescent element according to any one of claims 1 to 5, wherein,
the 1 st layer contains the organometallic complex compound in a proportion of 50 to 100% by volume.
7. The organic electroluminescent element according to any one of claims 1 to 6, wherein,
the electron-transporting organic compound includes a compound having a fluorene skeleton.
8. The organic electroluminescent element according to any one of claims 1 to 7, wherein,
at least one of the alkali metal and the alkaline earth metal is an alkaline earth metal.
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| JP2017213107A JP7021906B2 (en) | 2017-11-02 | 2017-11-02 | Organic electroluminescence element |
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| PCT/JP2018/040884 WO2019088262A1 (en) | 2017-11-02 | 2018-11-02 | Organic electroluminescent element |
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|---|---|---|---|---|
| US20050025993A1 (en) * | 2003-07-25 | 2005-02-03 | Thompson Mark E. | Materials and structures for enhancing the performance of organic light emitting devices |
| CN101919084A (en) * | 2007-12-19 | 2010-12-15 | 全球Oled科技有限责任公司 | Organic element for low voltage electroluminescent devices |
| CN102097419A (en) * | 2009-11-27 | 2011-06-15 | 精工爱普生株式会社 | Light-emitting device, display device, and electronic apparatus |
| CN106356461A (en) * | 2015-07-14 | 2017-01-25 | 住友化学株式会社 | Organic electroluminescence element |
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| JP4514841B2 (en) | 1998-02-17 | 2010-07-28 | 淳二 城戸 | Organic electroluminescent device |
| US8283853B2 (en) | 2010-03-31 | 2012-10-09 | General Electric Company | Light-emitting device and article |
| EP3069395A1 (en) | 2013-11-17 | 2016-09-21 | Solvay Sa | Multilayer structure with sbf matrix materials in adjacent layers |
| CN105473600B (en) | 2014-01-31 | 2019-03-15 | 出光兴产株式会社 | Compound, material for organic electroluminescent element, and electronic device |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050025993A1 (en) * | 2003-07-25 | 2005-02-03 | Thompson Mark E. | Materials and structures for enhancing the performance of organic light emitting devices |
| CN101919084A (en) * | 2007-12-19 | 2010-12-15 | 全球Oled科技有限责任公司 | Organic element for low voltage electroluminescent devices |
| CN102097419A (en) * | 2009-11-27 | 2011-06-15 | 精工爱普生株式会社 | Light-emitting device, display device, and electronic apparatus |
| CN106356461A (en) * | 2015-07-14 | 2017-01-25 | 住友化学株式会社 | Organic electroluminescence element |
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