WO2017221662A1 - 有機エレクトロルミネッセンス素子の製造方法及び有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子の製造方法及び有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2017221662A1 WO2017221662A1 PCT/JP2017/020429 JP2017020429W WO2017221662A1 WO 2017221662 A1 WO2017221662 A1 WO 2017221662A1 JP 2017020429 W JP2017020429 W JP 2017020429W WO 2017221662 A1 WO2017221662 A1 WO 2017221662A1
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- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
- H10K71/164—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition
Definitions
- the present invention relates to a method for producing an organic electroluminescence element and an organic electroluminescence element.
- the present invention is applicable to a flexible substrate, and relates to a method for manufacturing an organic electroluminescent element and an organic electroluminescent element capable of manufacturing an organic electroluminescent element with high luminous efficiency and long life at low cost.
- organic electroluminescence (hereinafter referred to as “organic EL”) element can be cited.
- An organic EL device has a structure in which a light emitting layer containing a compound that emits light is sandwiched between a cathode and an anode, and injects electrons and holes into the light emitting layer to recombine excitons. It is an element that emits light by utilizing light emission (fluorescence / phosphorescence) when the exciton is deactivated. Light emission is possible at a voltage of several V to several tens of V.
- the organic EL element has a feature that it is a surface light source.
- a lamination method using a curing agent has been proposed.
- an organic EL device having two light emitting layers made of a crosslinkable polymer is disclosed (for example, see Patent Document 2).
- an electron transport material having a functional group such as a fluoroalkyl group and a light-emitting material are coated to form a mixed layer, and the electron transport material is moved in the mixed layer to transport electrons.
- a technique has been proposed in which a material and a light-emitting material are separated to form a pseudo laminated structure to enable lamination of four or more layers (for example, see Patent Document 3).
- Patent Document 2 requires post-treatment at a high temperature for a long time after coating film formation, and further layers cannot be stacked on the layer without post-treatment. Further, there is a problem that not only energy and time are required for post-processing, but also the flexible substrate is distorted by the energy, yield decreases, and manufacturing cost cannot be reduced. Further, in the technique described in Patent Document 3, since mixing due to contact between the light emitting material and the electron transport material is unavoidable even after the material separation in the mixed layer, between the light emitting material and the electron transport material. Ligand exchange and complex formation occur, quenching occurs, and device performance deteriorates. Moreover, since molecular design is required over a plurality of types of materials, there is also a problem that it is difficult to design the entire layer.
- the present invention has been made in view of the above-mentioned problems and situations, and the solution is applicable to a flexible substrate, and it can produce an organic electroluminescence device with high luminous efficiency and long life at low cost. It is providing the manufacturing method of an organic electroluminescent element which can be performed, and an organic electroluminescent element.
- an organic EL device comprising a light-emitting layer, a block layer, and an electron transport layer between an anode and a cathode.
- the block layer is formed by using a coating solution containing a compound having a structure represented by the general formula (1) and a polar fluorinated solvent, so that it can be applied to a flexible substrate and has high luminous efficiency. It was also found that a long-life organic electroluminescence device can be produced at low cost. That is, the subject concerning this invention is solved by the following means.
- a method for producing an organic electroluminescent device comprising a light emitting layer, a block layer, and an electron transport layer between an anode and a cathode,
- the said block layer is formed using the coating liquid containing the compound which has a structure represented by following General formula (1), and a polar fluorinated solvent,
- the manufacturing method of the organic electroluminescent element characterized by the above-mentioned.
- X represents O, S or NR 9 .
- R 9 represents a hydrogen atom, a deuterium atom, an alkyl group, an alkenyl group, an alkynyl group, an arylalkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, or a non-aromatic heterocyclic ring.
- R 1 to R 8 are each a hydrogen atom, deuterium atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, acyl group, amino group, silyl group, phosphine oxide group, aromatic carbonization
- At least one of R 1 to R 9 represents a substituent represented by the following general formula (2).
- R 1 to R 9 may be the same as or different from each other, and may further have a substituent. ]
- L represents an alkylene group, an alkenylene group, an o-phenylene group, an m-phenylene group, a p-phenylene group, an amide group, or a divalent aromatic heterocyclic group, respectively. It may have a group.
- n represents an integer of 1 to 8. When n represents an integer of 2 or more, L of 2 or more may be the same as or different from each other.
- R represents an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a fluorinated alkyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, or a non-aromatic group.
- m represents an integer of 1 to 3.
- At least one of L and R represents an alkylene group or an alkyl group.
- L and R may be the same or different from each other, but they are not connected to each other to form a ring.
- Item 3 The method for producing an organic electroluminescent element according to Item 1 or 2, wherein the polar fluorinated solvent contains a fluorinated alcohol having 3 to 5 carbon atoms.
- Any one of the substituents represented by the general formula (2) is characterized in that at least one L is an alkylene group having 1 to 6 carbon atoms, The manufacturing method of the organic electroluminescent element of description.
- the light emitting layer contains a compound having a dibenzofuran ring, a dibenzothiophene ring or a carbazole ring, and having no alkyl group, alkenyl group, alkynyl group or arylalkyl group.
- An organic electroluminescence device comprising a light emitting layer, a block layer, and an electron transport layer between an anode and a cathode,
- the said block layer contains the compound and polar fluorinated solvent which have a structure represented by following General formula (1),
- the organic electroluminescent element characterized by the above-mentioned.
- X represents O, S or NR 9 .
- R 9 represents a hydrogen atom, a deuterium atom, an alkyl group, an alkenyl group, an alkynyl group, an arylalkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, or a non-aromatic heterocyclic ring.
- R 1 to R 8 are each a hydrogen atom, deuterium atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, acyl group, amino group, silyl group, phosphine oxide group, aromatic carbonization
- At least one of R 1 to R 9 represents a substituent represented by the following general formula (2).
- R 1 to R 9 may be the same as or different from each other, and may further have a substituent. ]
- L represents an alkylene group, an alkenylene group, an o-phenylene group, an m-phenylene group, a p-phenylene group, an amide group, or a divalent aromatic heterocyclic group, respectively. It may have a group.
- n represents an integer of 1 to 8. When n represents an integer of 2 or more, L of 2 or more may be the same as or different from each other.
- R represents an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a fluorinated alkyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, or a non-aromatic group.
- m represents an integer of 1 to 3.
- At least one of L and R represents an alkylene group or an alkyl group.
- L and R may be the same or different from each other, but they are not connected to each other to form a ring.
- Item 12 The organic electroluminescent element according to item 11, wherein the polar fluorinated solvent is contained in an amount of 1000 ppm by mass or less as a whole of each constituent layer.
- the manufacturing method and organic electroluminescent element of an organic electroluminescent element which can be applied also to a flexible substrate and can manufacture an organic electroluminescent element of high luminous efficiency and long life at low cost are provided. can do.
- the expression mechanism or action mechanism of the effect of the present invention is not clear, but is presumed as follows.
- the compound having the structure represented by the general formula (1) according to the present invention includes an alkylene group or an alkyl group and has a structure close to a general host material that can be contained in the light emitting layer.
- the compound having the structure represented by the general formula (1) includes an alkylene group or an alkyl group having a crystallographically large disorder, so that the solubility in a solid state is improved and the light emitting layer is not dissolved.
- the solubility in (polar fluorinated solvent) is improved.
- the polar fluorinated solvent used in the production method of the present invention is characterized by low intermolecular force and low surface free energy due to the low polarizability of C—F bond.
- the block layer has excellent water and oil repellency and non-adhesiveness, and when the block layer is formed using the coating liquid containing the polar fluorinated solvent, it is difficult to dissolve the underlying constituent material.
- the block layer is formed using a polar fluorinated solvent, it is possible to suppress deterioration in device performance due to aggregation of the block layer material when the coating film is dried, and penetration of the block layer material into the lower layer Can also be suppressed.
- surface tension acts on the surface of the coating film so as to minimize the surface free energy.
- a hydrophobic group having a low surface energy on the surface of the coating film and stabilizes the polar group and an aromatic ring having a relatively small hydrophobicity in an oriented state in the coating film.
- the block layer is formed using a coating liquid containing a compound having a structure represented by the general formula (1) as in the present invention, the surface free energy is increased as described above until the coating film is dried.
- a portion having a large number of polar groups and aromatic rings and a small amount of hydrophobic groups is oriented to the light emitting layer side, and a portion containing a large amount of hydrophobic groups is oriented to the coating film surface side.
- the electron transport layer can be wet-formed with a hydrophilic polar solvent on the block layer formed by drying the coating film. Therefore, according to the present invention, since the block layer is formed by the compound having the structure represented by the general formula (1) and the polar fluorinated solvent, it is mainly composed of a material that is easily dissolved in a solvent such as a low molecular compound. On the light emitting layer, the block layer can be laminated without dissolving the light emitting layer, and the electron transport layer can be laminated by a coating method without dissolving the block layer.
- the method for producing an organic EL device of the present invention is a method for producing an organic EL device comprising a light emitting layer, a block layer, and an electron transport layer between an anode and a cathode, wherein the block layer is represented by a general formula. It is formed using a coating solution containing a compound having a structure represented by (1) and a polar fluorinated solvent.
- the polar fluorinated solvent is preferably a solvent selected from fluorinated alcohols, fluorinated esters and fluorinated ethers.
- the polar fluorinated solvent preferably contains a fluorinated alcohol having 3 to 5 carbon atoms.
- At least one L is preferably an alkylene group having 1 to 6 carbon atoms.
- L is an alkylene group having 1 or more carbon atoms
- solubility in a polar fluorinated solvent is improved, and crystallization of a compound having a structure represented by the general formula (1) can be suppressed.
- L is an alkylene group having 6 or less carbon atoms
- the electron mobility is reduced due to the formation of a rough film due to the disorder of the compound having the structure represented by the general formula (1) more than necessary. Therefore, the effects of the present invention can be maximized.
- At least one R is preferably an alkyl group having 1 to 6 carbon atoms.
- R is an alkyl group having 1 or more carbon atoms
- the solubility in a polar fluorinated solvent is improved, and not only crystallization of the compound having the structure represented by the general formula (1) can be suppressed, but also to the light emitting layer. Can be prevented.
- R is an alkyl group having 6 or less carbon atoms
- the said electron carrying layer it is preferable to form the said electron carrying layer using the coating liquid containing an electron carrying material.
- the coating liquid containing the said electron transport material contains a polar fluorination solvent.
- the said light emitting layer is comprised with the compound whose solubility with respect to a polar fluorination solvent is lower than the compound which has a structure represented by the said General formula (1). It is preferable.
- the light emitting layer is preferably composed of a compound having a molecular weight of 3000 or less.
- the light emitting layer is composed of a low-molecular compound that is easily dissolved in a solvent, other functional layers can be stacked without dissolving the light emitting layer, so that an organic EL element with high luminous efficiency and long life can be obtained. It can be manufactured reliably.
- the said light emitting layer contains the compound which has a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring and does not have an alkyl group, an alkenyl group, an alkynyl group, or an arylalkyl group.
- the compound contained in the light emitting layer has a skeleton similar to that of the general formula (1), the electron transport property can be increased, and since a film having a high density can be formed by having no alkyl group or the like, a block Intrusion of the layer material into the light emitting layer can be suppressed, and the effects of the present invention can be exhibited to the maximum.
- the organic EL device of the present invention is an organic EL device comprising a light emitting layer, a block layer, and an electron transport layer between an anode and a cathode, and the block layer is represented by the following general formula (1).
- a polar fluorinated solvent is preferably contained in an amount of 1000 mass ppm or less as a whole of each constituent layer.
- ⁇ is used to mean that the numerical values described before and after it are included as a lower limit value and an upper limit value.
- FIG. 1 is a schematic cross-sectional view of an organic EL element 10 which is an example of an organic EL element manufactured by the manufacturing method of the present invention.
- the organic EL element 10 includes a substrate 11, an anode 12, a hole injection layer 13, a hole transport layer 14, a light emitting layer 15, a block layer 16, an electron transport layer 17, an electron injection layer 18, and a cathode 19 in this order. Yes.
- the element configuration of the organic EL element is not limited to the configuration example shown in FIG. 1.
- the following configurations can be given as typical element configurations.
- the light emitting layer is composed of a single layer or multiple layers. If necessary, a hole blocking layer (hole blocking layer), an electron injection layer (cathode buffer layer) or the like may be provided between the light emitting layer and the cathode, and between the light emitting layer and the anode. An electron blocking layer (electron barrier layer), a hole injection layer (anode buffer layer), and the like are provided. Each of these layers can be formed by a known material and method.
- the method for producing an organic EL device of the present invention is a method for producing an organic EL device comprising a light emitting layer, a block layer, and an electron transport layer between an anode and a cathode, wherein the block layer is represented by the general formula ( It is formed using a coating liquid containing a compound having a structure represented by 1) and a polar fluorinated solvent.
- the manufacturing method of the organic EL element of the present invention will be specifically described.
- the anode 12 is formed on the base material 11.
- the hole injection layer 13 and the hole transport layer 14 are formed in this order on the anode 12.
- the light emitting layer 15 is formed.
- the block layer 16 is formed on the light emitting layer 15 using a block layer forming coating solution containing a compound having a structure represented by the general formula (1) and a polar fluorinated solvent.
- the electron transport layer 17 is formed on the block layer 16.
- an electron injection layer 18 and a cathode 19 are formed on the electron transport layer 17.
- any methods such as a wet method, vapor deposition, and a sputtering, may be sufficient.
- the element after forming the cathode 19 is sealed.
- a sealing means used for sealing the element known members and methods can be used.
- the organic EL element 10 can be manufactured as described above.
- the light emitting layer is a layer that provides a field in which electrons and holes injected from an electrode or an adjacent layer are recombined to emit light via excitons.
- the light-emitting layer preferably contains a light-emitting dopant (a light-emitting dopant compound, a dopant compound, also simply referred to as a dopant) and a host compound (a matrix material, a light-emitting host compound, also simply referred to as a host).
- a material that is soluble in a polar solvent other than the polar fluorinated solvent and insoluble in the polar fluorinated solvent is preferably used. All the light emitting layer materials described below satisfy this condition. Many of the conventionally known light emitting layer materials are insoluble in polar fluorinated solvents.
- the solvent used for the light emitting layer is preferably a polar solvent other than the polar fluorinated solvent, and the polar solvent other than the polar fluorinated solvent does not contain a fluorine atom in the solvent molecule and has a relative dielectric constant of 3 or more and 25 ° C.
- alcohols that do not contain fluorine such as methanol, ethanol, methoxyethanol, ethoxyethanol, propanol, butanol, pentanol, cyclohexanol, ethylene glycol, phenol, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, etc.
- Fluorine-free esters acetonitrile, propionitrile, benzonitrile and other fluorine-free nitriles, acetone, butanone, cyclohexanone and other fluorine-free ketones, dimethyl ether, diethyl ether, methyl ethyl ether, dipropyl ether And ethers that do not contain fluorine, such as
- the light emitting layer material constituting the light emitting layer may be a compound having a molecular weight of 3000 or less. By using a compound having a molecular weight of 3000 or less, the solubility in a solvent is improved.
- a block layer described later is formed on the light-emitting layer, so that it is composed of a light-emitting layer material having a molecular weight of 3000 or less.
- Another organic layer can be stacked on the light emitting layer without dissolving the light emitting layer.
- the molecular weight of the light emitting dopant and the host compound used as the light emitting layer material is not particularly limited, but the light emitting layer according to the present invention has a dibenzofuran ring, a dibenzothiophene ring or a carbazole ring, and an alkyl group. It is preferable to contain a compound having no alkenyl group, alkynyl group or arylalkyl group.
- the formation method of the light emitting layer is not particularly limited, and can be formed by, for example, a conventionally known vacuum deposition method or wet method. Especially, it is preferable to form by a wet method from a viewpoint of reducing the manufacturing cost of an organic EL element.
- wet method examples include spin coating method, casting method, ink jet method, printing method, die coating method, blade coating method, roll coating method, spray coating method, curtain coating method, LB method (Langmuir-Blodgett method) and the like. Can be used. Among them, a method applicable to a roll-to-roll method such as a die coating method, a roll coating method, an ink jet method, or a spray coating method is preferable from the viewpoint of obtaining a homogeneous thin film easily and high productivity.
- liquid medium in which the light emitting layer material is dissolved or dispersed in the wet method examples include ketones such as methyl ethyl ketone and cyclohexanone, fatty acid esters such as ethyl acetate, halogenated hydrocarbons such as dichlorobenzene, toluene, xylene, and mesitylene.
- Aromatic hydrocarbons such as cyclohexylbenzene, aliphatic hydrocarbons such as cyclohexane, decalin, and dodecane, and organic solvents such as dimethylformamide (DMF) and dimethylsulfoxide (DMSO) can be used.
- a dispersion method such as ultrasonic wave, high shearing force dispersion or media dispersion.
- the vapor deposition conditions vary depending on the type of compound used, but generally a boat heating temperature of 50 to 450 ° C., a vacuum degree of 10 ⁇ 6 to 10 ⁇ 2 Pa, and vapor deposition. It is desirable to appropriately select the speed within a range of 0.01 to 50 nm / second, a substrate temperature of ⁇ 50 to 300 ° C., and a layer thickness of 0.1 nm to 5 ⁇ m, preferably 5 to 200 nm.
- Luminescent dopant As the luminescent dopant, a fluorescent luminescent dopant (also referred to as a fluorescent dopant or a fluorescent compound) or a phosphorescent dopant (also referred to as a phosphorescent dopant or a phosphorescent compound) is preferably used.
- concentration of the light-emitting dopant in the light-emitting layer can be arbitrarily determined based on the specific dopant used and the device requirements.
- the concentration of the light emitting dopant may be contained at a uniform concentration in the thickness direction of the light emitting layer, or may have an arbitrary concentration distribution.
- the light emitting layer may contain a plurality of kinds of light emitting dopants.
- a combination of dopants having different structures or a combination of a fluorescent luminescent dopant and a phosphorescent luminescent dopant may be used. Thereby, arbitrary luminescent colors can be obtained.
- one or a plurality of light-emitting layers contain a plurality of light-emitting dopants having different emission colors and emit white light as a whole of the organic EL element.
- the combination of light-emitting dopants that exhibit white include a combination of blue and orange, a combination of blue, green, and red.
- the phosphorescent dopant is a compound in which light emission from an excited triplet is observed. Specifically, the phosphorescent dopant is a compound that emits phosphorescence at room temperature (25 ° C.), and has a phosphorescence quantum yield of 0 at 25 ° C. .01 or more compounds. In the phosphorescent dopant used for a light emitting layer, a preferable phosphorescence quantum yield is 0.1 or more.
- the phosphorescent quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of the Fourth Edition Experimental Chemistry Course 7.
- the phosphorescence quantum yield in a solution can be measured using various solvents.
- the phosphorescent dopant used in the light emitting layer may be any phosphorescent quantum yield (0.01 or more) in any solvent.
- the phosphorescent dopant can be appropriately selected from known materials used for the light emitting layer of the organic EL element.
- a preferable phosphorescent dopant is an organometallic complex having Ir as a central metal. More preferably, a complex containing at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, or a metal-sulfur bond is preferable.
- the fluorescent light-emitting dopant is a compound that can emit light from an excited singlet, and is not particularly limited as long as light emission from the excited singlet is observed.
- Examples of the fluorescent light-emitting dopant include anthracene derivatives, pyrene derivatives, chrysene derivatives, fluoranthene derivatives, perylene derivatives, fluorene derivatives, arylacetylene derivatives, styrylarylene derivatives, styrylamine derivatives, arylamine derivatives, boron complexes, coumarin derivatives, Examples include pyran derivatives, cyanine derivatives, croconium derivatives, squalium derivatives, oxobenzanthracene derivatives, fluorescein derivatives, rhodamine derivatives, pyrylium derivatives, perylene derivatives, polythiophene derivatives, rare earth complex compounds, and the like.
- a light emitting dopant utilizing delayed fluorescence may be used as the fluorescent light emitting dopant.
- the luminescent dopant using delayed fluorescence include compounds described in, for example, International Publication No. 2011/156793, Japanese Patent Application Laid-Open No. 2011-213643, Japanese Patent Application Laid-Open No. 2010-93181, and the like.
- the host compound is a compound mainly responsible for charge injection and transport in the light emitting layer, and its own light emission is not substantially observed in the organic EL element.
- it is a compound having a phosphorescence quantum yield of phosphorescence emission of less than 0.1 at room temperature (25 ° C.), more preferably a compound having a phosphorescence quantum yield of less than 0.01.
- the mass ratio in the layer is 20% or more among the compounds contained in a light emitting layer.
- the excited state energy of a host compound is higher than the excited state energy of the light emission dopant contained in the same layer.
- a host compound may be used independently or may be used in combination of multiple types. By using a plurality of types of host compounds, it is possible to adjust the movement of electric charges, and it is possible to increase the efficiency of the organic EL element.
- the compound conventionally used with an organic EL element can be used.
- a low molecular compound, a high molecular compound having a repeating unit, or a compound having a reactive group such as a vinyl group or an epoxy group may be used.
- Tg glass transition temperature
- the glass transition point (Tg) is a value determined by a method based on JIS-K-7121 using DSC (Differential Scanning Colorimetry).
- the host compound is preferably a compound whose solubility in a polar fluorinated solvent is lower than that of the compound having the structure represented by the general formula (1) from the viewpoint of manifesting the effect of the present invention.
- the solubility means the limit number of solute grams dissolved per liter of solvent at 25 ° C. and 1 atm.
- the block layer represents a layer inserted between the light-emitting layer and the electron transport layer, and transports electrons injected from the electron transport layer to the light-emitting layer side and is transported from the light-emitting layer side. It is a layer having a function of confining excitons generated by recombination of holes and electrons and holes on the light emitting layer in the light emitting layer. Therefore, the block layer functions as a so-called hole blocking layer.
- the block layer can be formed by applying a block layer forming coating solution containing a compound having a structure represented by the general formula (1) and a polar fluorinated solvent.
- a block layer forming coating solution containing a compound having a structure represented by the general formula (1) and a polar fluorinated solvent.
- coating the coating liquid for block layer formation and forming a block layer it can suppress that a solvent melt
- by forming the block layer mixing of the light emitting layer and the electron transport layer is suppressed when forming the upper electron transport layer regardless of the vapor deposition method / coating method. Mixing and reaction of the light-emitting layer material and the electron transport layer material due to the energy of can be suppressed. For this reason, the performance fall of an organic EL element can be suppressed.
- a block layer contains the compound and polar fluorinated solvent which have a structure represented by General formula (1).
- Whether or not a polar fluorinated solvent is contained in the block layer can be determined as follows. That is, the distribution of the polar fluorinated solvent contained in the block layer of the organic EL element is analyzed by TOF-SIMS (time-of-flight secondary ion mass spectrometry), and the fluorine distribution in the layer thickness direction is measured (measurement). In this case, the ions are emitted from the substrate side, and care is taken so that the direction in which the component is implanted during ion collision does not coincide with the direction of solvent penetration during lamination. Thereby, when a fluorine atom is detected, it can be judged that the polar fluorinated solvent is contained in the block layer.
- TOF-SIMS time-of-flight secondary ion mass spectrometry
- Examples of the coating method for forming the block layer according to the present invention include spray coating, electrospray coating, ink jet, mist CVD, gravure coating, bar coating, roll coating, dip coating, screen printing, flexographic printing, and offset printing. Can be mentioned. Further, these coating methods include a case where the solvent is dried before the coating liquid for forming the block layer lands on the lower layer.
- the formation of the block layer by a coating method may be performed under any condition in the air or in an inert gas atmosphere.
- the block layer may be formed in a plurality of layers.
- the layer thickness of the block layer is preferably in the range of 1 to 100 nm, and more preferably in the range of 5 to 50 nm.
- the total layer thickness is preferably within the above range.
- the total thickness of the block layer is 1 nm or more, not only can the charge and exciton blocking functions be exhibited effectively, but also the effect that the penetration of the coating liquid for forming the upper layer (electron transport layer) can be more reliably suppressed can be obtained. It is done.
- the total layer thickness of the block layer is 100 nm or less, the effect of molecular orientation by the compound having the structure represented by the general formula (1) and the polar fluorinated solvent is easily obtained, and the upper layer (electron transport layer) material In addition to being able to more reliably suppress the penetration of the light, sufficient charge transportability can be ensured, and absorption and scattering of the emitted light can be suppressed to obtain high luminous efficiency as the entire organic EL element.
- the block layer may contain a material other than the compound having the structure represented by the general formula (1) within a range not impairing the effects of the present invention.
- the content of the other material in the block layer is preferably 20% by mass or less with respect to the entire formed block layer, for example, although it depends on the type of material. If it is within this range, it is considered that the effects of the present invention can be prevented from being impaired.
- the block layer can be formed using a coating solution containing a compound having a structure represented by the following general formula (1).
- X represents O, S or NR 9 .
- R 9 represents a hydrogen atom, a deuterium atom, an alkyl group, an alkenyl group, an alkynyl group, an arylalkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, or a non-aromatic heterocyclic ring.
- R 1 to R 8 are each a hydrogen atom, deuterium atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, acyl group, amino group, silyl group, phosphine oxide group, aromatic carbonization
- At least one of R 1 to R 9 represents a substituent represented by the following general formula (2).
- R 1 to R 9 may be the same as or different from each other, and may further have a substituent. ]
- L represents an alkylene group, an alkenylene group, an o-phenylene group, an m-phenylene group, a p-phenylene group, an amide group, or a divalent aromatic heterocyclic group, respectively. It may have a group.
- n represents an integer of 1 to 8. When n represents an integer of 2 or more, L of 2 or more may be the same as or different from each other.
- R represents an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a fluorinated alkyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, or a non-aromatic group.
- m represents an integer of 1 to 3.
- At least one of L and R represents an alkylene group or an alkyl group.
- L and R may be the same or different from each other, but they are not connected to each other to form a ring.
- examples of the alkyl group represented by R 1 to R 9 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a (t) butyl group, a pentyl group, a hexyl group, and an octyl group.
- Examples of the alkenyl group represented by R 1 to R 9 include those having one or more double bonds in the alkyl group, and more specifically, vinyl group, allyl group, 1- Examples include propenyl group, isopropenyl group, 2-butenyl group, 1,3-butadienyl group, 2-pentenyl group, 2-hexenyl group and the like.
- Examples of the alkynyl group represented by R 1 to R 9 include ethynyl group, acetylenyl group, 1-propynyl group, 2-propynyl group (propargyl group), 1-butynyl group, 2-butynyl group, 3- Butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 1-hexynyl group, 2-hexynyl group, 3-hexynyl group, 1-heptynyl group, 2-heptynyl group, 5-heptynyl group, 1- Examples include octynyl group, 3-octynyl group, and 5-octynyl group.
- examples of the aromatic hydrocarbon ring group (also referred to as an aryl group) represented by R 1 to R 9 include a phenyl group, a p-chlorophenyl group, a mesityl group, a tolyl group, and a xylyl group.
- a phenyl group a p-chlorophenyl group
- mesityl group a tolyl group
- a xylyl group examples of the aromatic hydrocarbon ring group represented by R 1 to R 9 include a phenyl group, a p-chlorophenyl group, a mesityl group, a tolyl group, and a xylyl group.
- Examples of the aromatic heterocyclic group represented by R 1 to R 9 include a pyridyl group, pyrimidinyl group, furyl group, pyrrolyl group, imidazolyl group, benzoimidazolyl group, pyrazolyl group, pyrazinyl group, triazolyl group (for example, 1,2,4-triazol-1-yl group, 1,2,3-triazol-1-yl group, etc.), oxazolyl group, benzoxazolyl group, thiazolyl group, isoxazolyl group, isothiazolyl group, furazanyl group, thienyl Group, quinolyl group, benzofuryl group, dibenzofuryl group, benzothienyl group, dibenzothienyl group, indolyl group, carbazolyl group, carbolinyl group, diazacarbazolyl group (one of the carbon atoms constituting the carboline ring of the carbolinyl group
- examples of the non-aromatic hydrocarbon ring group represented by R 1 to R 9 include a cycloalkyl group (eg, cyclopentyl group, cyclohexyl group, etc.), a cycloalkoxy group (eg, cyclopentyl).
- a cycloalkyl group eg, cyclopentyl group, cyclohexyl group, etc.
- a cycloalkoxy group eg, cyclopentyl
- Examples of the non-aromatic hydrocarbon ring group represented by R 1 to R 9 include an epoxy ring, an aziridine ring, a thiirane ring, an oxetane ring, an azetidine ring, a thietane ring, a tetrahydrofuran ring, a dioxolane ring, a pyrrolidine ring, Pyrazolidine ring, imidazolidine ring, oxazolidine ring, tetrahydrothiophene ring, sulfolane ring, thiazolidine ring, ⁇ -caprolactone ring, ⁇ -caprolactam ring, piperidine ring, hexahydropyridazine ring, hexahydropyrimidine ring, piperazine ring, morpholine ring, tetrahydro Pyran ring, 1,3-dioxane ring, 1,4-d
- examples of the alkoxy group represented by R 1 to R 8 include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, 2- Ethylhexyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy Groups and the like.
- Examples of the acyl group represented by R 1 to R 8 include an acetyl group, an ethylcarbonyl group, a propylcarbonyl group, a pentylcarbonyl group, a cyclohexylcarbonyl group, an octylcarbonyl group, a 2-ethylhexylcarbonyl group, and a dodecylcarbonyl group. , Phenylcarbonyl group, naphthylcarbonyl group, pyridylcarbonyl group and the like.
- Examples of the amino group represented by R 1 to R 8 include an amino group, an ethylamino group, a dimethylamino group, a butylamino group, a cyclopentylamino group, a 2-ethylhexylamino group, a dodecylamino group, an anilino group, Examples thereof include a naphthylamino group and a 2-pyridylamino group.
- Examples of the silyl group represented by R 1 to R 8 include a trimethylsilyl group, a triisopropylsilyl group, a triphenylsilyl group, and a phenyldiethylsilyl group.
- Examples of the phosphine oxide group represented by R 1 to R 8 include diphenylphosphine oxide group, ditolylphosphine oxide group, dimethylphosphine oxide group, dinaphthylphosphine oxide group, 9,10-dihydro-9-oxa And -10-phosphaphenanthrene-10-oxide group.
- examples of the arylalkyl group represented by R 9 include benzyl group, phenethyl group, diphenylmethyl group, 1,1-diphenylethyl group, 1,2-diphenylethyl group, and tolyl group. And an ethylphenyl group.
- examples of the substituent that the groups represented by R 1 to R 9 may further include an alkyl group (for example, a methyl group, an ethyl group, and a propyl group).
- an alkyl group for example, a methyl group, an ethyl group, and a propyl group.
- cycloalkyl group for example, cyclopentyl group, cyclohexyl group etc.
- Alkenyl groups for example, vinyl groups, allyl groups, etc.
- alkynyl groups for example, propargyl groups, etc.
- aromatic hydrocarbon groups also called aryl groups, for example, phenyl groups, p-
- examples of the alkylene group represented by L include a methylene group, an ethylene group, a trimethylene group, a propylene group, a butylene group, a butane-1,2-diyl group, and a hexylene group.
- examples of the alkenylene group represented by L include vinylene group, propenylene group, butenylene group, pentenylene group, 1-methylvinylene group, 1-methylpropenylene group, 2-methylpropenylene group, 1-methylpentene.
- Examples include a tenylene group, a 3-methylpentenylene group, a 1-ethylvinylene group, a 1-ethylpropenylene group, a 1-ethylbutenylene group, and a 3-ethylbutenylene group.
- Examples of the amide group represented by L include a methylcarbonylamino group, an ethylcarbonylamino group, a dimethylcarbonylamino group, a propylcarbonylamino group, a pentylcarbonylamino group, a cyclohexylcarbonylamino group, and a 2-ethylhexylcarbonylamino group.
- Examples of the divalent aromatic heterocyclic group represented by L are derived from those exemplified as the aromatic heterocyclic groups represented by R 1 to R 9 in the general formula (1). A divalent group is mentioned.
- examples of the alkyl group having 1 to 20 carbon atoms represented by R include those exemplified as the alkyl group represented by R 1 to R 9 in the general formula (1). Of these, groups having 1 to 20 carbon atoms can be mentioned.
- examples of the fluorinated alkyl group having 1 to 20 carbon atoms represented by R include a group in which a hydrogen atom of the alkyl group having 1 to 20 carbon atoms is substituted with a fluorine atom.
- examples of the alkoxy group having 1 to 20 carbon atoms represented by R include those represented by the general formula (1) as the alkoxy groups represented by R 1 to R 8 having 1 to 2 carbon atoms. There are 20 groups.
- Examples of the aromatic hydrocarbon ring group, aromatic heterocyclic group or non-aromatic hydrocarbon ring group represented by R include aromatic hydrocarbons represented by R 1 to R 9 in the general formula (1). The same thing as a cyclic group, an aromatic heterocyclic group, or a non-aromatic hydrocarbon cyclic group is mentioned.
- the compound having a structure represented by the general formula (1) among the substituents represented by the general formula (2), those in which at least one L is an alkylene group having 1 to 6 carbon atoms are preferable.
- at least one R is preferably an alkyl group having 1 to 6 carbon atoms.
- a polar fluorinated solvent is used for forming the block layer. Moreover, it is preferable that a polar fluorinated solvent is used also for formation of an electron carrying layer.
- the polar fluorinated solvent refers to a solvent containing a fluorine atom in a solvent molecule and having a relative dielectric constant of 3 or more and a solubility in water at 25 ° C. of 5 g / L or more.
- the boiling point of the polar fluorinated solvent is preferably within the range of 50 to 200 ° C.
- the temperature By setting the temperature to 50 ° C. or higher, the occurrence of unevenness due to the heat of evaporation during drying of the coating film can be more reliably suppressed.
- the temperature By setting the temperature to 200 ° C. or lower, the solvent can be quickly dried, and the solvent content in the formed layer is reduced, so that crystal growth in the layer can be more reliably suppressed, and the solvent escape route is rough. Therefore, the density is improved and the current efficiency can be increased. More preferably, it is in the range of 70 to 150 ° C.
- the water content of the polar fluorinated solvent is preferably as low as possible since it becomes a luminescence quencher even if it is a very small amount, and is preferably 100 ppm or less, and more preferably 20 ppm or less.
- the content of impurities other than moisture in the polar fluorinated solvent is similarly good even if it is a very small amount, because it becomes a quencher for light emission or causes deterioration of film quality after bubbles or drying.
- it is 20 ppm or less.
- impurities other than moisture include oxygen, inert gases such as nitrogen, argon and carbon dioxide, catalysts used during preparation and purification, inorganic compounds or metals brought in from adsorbents and instruments, and the like.
- polar fluorinated solvent for example, fluorinated alcohol, fluorinated acrylate, fluorinated methacrylate, fluorinated ester, fluorinated ether or fluorinated hydroxyalkylbenzene, and fluorinated amine are preferable, and fluorinated alcohol, fluorinated ester or fluorinated Ether is more preferable, and fluorinated alcohol is more preferable from the viewpoints of solubility and drying properties.
- the number of carbon atoms of the fluorinated alcohol is preferably 3 to 5 from the viewpoints of boiling point and material solubility.
- fluorine substitution position examples include the position of hydrogen in the case of alcohol, and the fluorination rate may be any degree that does not impair the solubility of the layer material, and is fluorinated to the extent that the lower layer material is not eluted. It is desirable.
- fluorinated alcohol examples include 1H, 1H-pentafluoropropanol, 6- (perfluoroethyl) hexanol, 1H, 1H-heptafluorobutanol, 2- (perfluorobutyl) ethanol (FBEO), 3- (perfluoro Butyl) propanol, 6- (perfluorobutyl) hexanol, 2-perfluoropropoxy-2,3,3,3-tetrafluoropropanol, 2- (perfluorohexyl) ethanol, 3- (perfluorohexyl) propanol, 6 -(Perfluorohexyl) hexanol, 1H, 1H- (perfluorohexyl) hexanol, 6- (perfluoro-1-methylethyl) hexanol, 1H, 1H, 3H-tetrafluoropropanol (TFPO), 1H, 1H,
- TFPO fluorinated ether
- fluorinated ether examples include hexafluorodimethyl ether, perfluorodimethoxymethane, perfluorooxetane, perfluoro-1,3-dioxolane, 1,1,2,2-tetrafluoroethyl-2,2,3,3-tetra
- fluoropropyl ether examples include fluoropropyl ether.
- fluorinated ester examples include methyl perfluorobutyrate, ethyl perfluorobutyrate, methyl perfluoropropionate, methyl difluoroacetate, ethyl difluoroacetate, methyl-2-trifluoromethyl-3,3,3- Examples thereof include trifluoropropionate.
- the content of the compound having the structure represented by the general formula (1) of the present invention is 0.05 to 10% by mass, and the content of the polar fluorinated solvent is 90 to 99.95%. % Is preferred.
- the polar fluorinated solvent may be a mixed solvent of two or more polar fluorinated solvents or a mixture of a polar fluorinated solvent and a solvent other than the polar fluorinated solvent as long as it does not dissolve the light emitting layer material.
- a solvent may be used.
- a mixed solvent of fluorinated alcohol and alcohol can be used.
- the content of the polar fluorinated solvent is preferably 50% by mass or more.
- the polar fluorinated solvent is preferably contained in an amount of 1000 mass ppm or less as a whole of each constituent layer.
- the organic EL element material is reoriented by energy such as heat generated at the time of driving without deteriorating the charge transfer between the organic EL element materials, and the crystal grain boundary charges are not re-oriented. Transportability is not reduced by the trap.
- the content of the polar fluorinated solvent as a whole of each constituent layer can be measured as follows. First, the sample which formed each layer from a positive hole injection layer to an electron carrying layer on a 30 mm square glass substrate similarly to the organic EL element of a measuring object is produced. Two samples of about 1 cm mouth are cut out from the flat film portion of this sample.
- the sample whose area was determined was measured with a temperature-programmed thermal desorption analyzer manufactured by Denshi Kagaku Co., and the desorbed gas component was quantified from the mass fragment spectrum corresponding to the polar fluorinated solvent used for forming the layer.
- the mass ratio of the polar fluorinated solvent per volume of the organic layer laminate is determined. As described above, the content of the polar fluorinated solvent can be determined.
- Base material there is no limitation in particular in the material of the base material used for an organic EL element, Preferably, glass, quartz, a resin film etc. can be mentioned, for example. Particularly preferred is a resin film capable of giving flexibility to the organic EL element.
- polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polyethylene, polypropylene, cellophane, cellulose diacetate, cellulose triacetate (TAC), cellulose acetate butyrate, cellulose acetate propionate ( CAP), cellulose esters such as cellulose acetate phthalate, cellulose nitrate or derivatives thereof, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide , Polyethersulfone (PES), polyphenylene sulfide, polysulfones Cycloolefins such as polyetherimide, polyetherketoneimide, polyamide, fluororesin, nylon, polymethylmethacrylate, acrylic or polyarylates, Arton (trade name, manufactured by JSR) or Appel (trade name, manufactured by J
- a gas barrier film may be formed on the surface of the resin film using an inorganic or organic coating or a hybrid coating of both.
- the gas barrier membrane has a water vapor permeability (25 ⁇ 0.5 ° C., humidity (90 ⁇ 2)% RH) measured by a method according to JIS K 7129-1992 of 0.01 g / (m 2 ⁇ 24 h) or less. It is preferable that it is a gas barrier film.
- the oxygen permeability measured by a method according to JIS K 7126-1987 is 1 ⁇ 10 ⁇ 3 mL / (m 2 ⁇ 24 h ⁇ atm) or less, and the water vapor permeability is 1 ⁇ 10 ⁇ 5 g / A high gas barrier film of (m 2 ⁇ 24 h) or less is preferable.
- the material for forming the gas barrier film may be any material that has a function of suppressing intrusion of moisture, oxygen, and the like.
- silicon oxide, silicon dioxide, silicon nitride, or the like can be used.
- the method for forming the gas barrier film is not particularly limited.
- the vacuum deposition method, sputtering method, reactive sputtering method, molecular beam epitaxy method, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma weight A combination method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used.
- an atmospheric pressure plasma polymerization method as described in JP-A-2004-68143 is preferable.
- the electron transport layer is made of a material having a function of transporting electrons, and in a broad sense, the electron injection layer is also included in the electron transport layer.
- the electron transport layer can be provided as a single layer or a plurality of layers.
- the coating solution preferably contains a polar fluorinated solvent. The solubility in a polar fluorinated solvent is preferably decreased in the order of the electron transport layer material, the block layer material, and the light emitting layer material.
- the electron transport material used for an electron transport layer (in the case of a plurality of layers, an electron transport layer adjacent to the cathode side), the electron transport material only needs to have a function of transmitting electrons injected from the cathode to the light emitting layer.
- the material any one of conventionally known compounds can be selected and used. Examples thereof include metal complexes such as fluorene derivatives, carbazole derivatives, azacarbazole derivatives, oxadiazole derivatives, triazole derivatives, silole derivatives, pyridine derivatives, pyrimidine derivatives, 8-quinolinol derivatives, and the like.
- metal-free or metal phthalocyanine or those in which the terminal thereof is substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transport material.
- a carbazole derivative, an azacarbazole derivative, a pyridine derivative, and the like are preferable in the present invention, and an azacarbazole derivative is more preferable.
- the electron transport layer can be formed by thinning the electron transport material by a known method such as a spin coating method, a casting method, a printing method including an ink jet method, an LB method, and the like, preferably It can be formed by a wet process using a coating solution containing an electron transport material and a fluorinated alcohol solvent.
- the layer thickness of the electron transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 to 200 nm.
- the electron transport layer may have a single layer structure composed of one or more of the above materials.
- an electron transport layer having a high n property doped with an impurity as a guest material can also be used.
- Examples thereof include JP-A-4-297076, JP-A-10-270172, JP-A-2000-196140, 2001-102175, J.A. Appl. Phys. 95, 5773 (2004), and the like.
- the electron transport layer in the present invention preferably contains an organic alkali metal salt.
- organic alkali metal salt there are no particular restrictions on the type of organic substance, but formate, acetate, propionic acid, butyrate, valerate, caproate, enanthate, caprylate, oxalate, malonate, succinate Benzoate, phthalate, isophthalate, terephthalate, salicylate, pyruvate, lactate, malate, adipate, mesylate, tosylate, benzenesulfonate , Preferably formate, acetate, propionate, butyrate, valerate, caprate, enanthate, caprylate, oxalate, malonate, succinate, benzoate, more preferably Is preferably an alkali metal salt of an aliphatic carboxylic acid such as formate, acetate, propionate or butyrate, and the aliphatic carboxylic acid preferably has 4
- the type of alkali metal of the alkali metal salt of the organic substance is not particularly limited, and examples thereof include Na, K, Cs, and Li, preferably K, Cs, and more preferably Cs.
- the alkali metal salt of the organic substance include a combination of the organic substance and the alkali metal, preferably, formic acid Li, formic acid K, formic acid Na, formic acid Cs, acetic acid Li, acetic acid K, Na acetate, acetic acid Cs, propionic acid Li, Propionic acid Na, propionic acid K, propionic acid Cs, oxalic acid Li, oxalic acid Na, oxalic acid K, oxalic acid Cs, malonic acid Li, malonic acid Na, malonic acid K, malonic acid Cs, succinic acid Li, succinic acid Na, succinic acid K, succinic acid Cs, benzoic acid Li, benzoic acid Na, benzoic acid K, benzoic acid Cs
- the hole transport layer is composed of a hole transport material having a function of transporting holes, and in a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer. Moreover, a positive hole transport layer can be provided in single layer or multiple layers.
- the hole transport material has any one of hole injection or transport and electron barrier properties, and may be either organic or inorganic.
- triazole derivatives oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives
- Examples include stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers, and thiophene oligomers.
- hole transport material those described above can be used, but porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds can be used, and in particular, aromatic tertiary amine compounds can be used. preferable.
- aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl, N, N′-diphenyl-N, N′— Bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine (abbreviation: TPD), 2,2-bis (4-di-p-tolylaminophenyl) propane, 1,1 -Bis (4-di-p-tolylaminophenyl) cyclohexane, N, N, N ', N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis (4-di-p -Tolylaminophenyl) -4-phenylcyclohexane, bis (4-dimethylamino-2-methylphenyl) phenylmethane, bis (4-di-p
- polymer materials in which these materials are introduced into polymer chains or these materials are used as polymer main chains can also be used.
- inorganic compounds such as p-type-Si and p-type-SiC can also be used as the hole injection material and the hole transport material.
- JP-A-11-251067 J. Org. Huang et. al. Applied Physics Letters, 80 (2002), p.
- a so-called p-type hole transport material as described in 139 can also be used. In the present invention, these materials are preferably used from the viewpoint of obtaining a light-emitting element with higher efficiency.
- the hole transport material may be formed by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, and an LB method (Langmuir Brodget, LangmuirmBlodgett method). Thus, it can be formed by thinning.
- the layer thickness of the hole transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 to 200 nm.
- This hole transport layer may have a single layer structure composed of one or more of the above materials.
- the p property can be increased by doping impurities into the material of the hole transport layer.
- Examples thereof include JP-A-4-297076, JP-A-2000-196140, 2001-102175 and J.P. Appl. Phys. 95, 5773 (2004), and the like.
- An injection layer (a hole injection layer and an electron injection layer) is a layer provided between an electrode and a light-emitting layer in order to reduce drive voltage or improve light emission luminance. The details are described in Volume 2, Chapter 2, “Electrode Materials” (pages 123-166) of “November 30, 1998, NTS Co., Ltd.”. There is.
- the injection layer can be provided as necessary. If it is a hole injection layer, it may exist between the anode and the light emitting layer or the hole transport layer, and if it is an electron injection layer, it may exist between the cathode and the light emitting layer or the electron transport layer.
- JP-A-9-45479 JP-A-9-260062, JP-A-8-288069 and the like.
- Specific examples include a phthalocyanine layer represented by copper phthalocyanine, Examples thereof include an oxide layer typified by vanadium oxide, an amorphous carbon layer, and a polymer layer using a conductive polymer such as polyaniline (emeraldine) or polythiophene.
- the electron injection layer Details of the electron injection layer are described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Specifically, a metal layer represented by strontium, aluminum, or the like. And an alkali metal halide layer typified by potassium fluoride, an alkaline earth metal compound layer typified by magnesium fluoride, and an oxide layer typified by molybdenum oxide.
- the electron injection layer is a very thin film, and the layer thickness is preferably in the range of 1 nm to 10 ⁇ m although it depends on the constituent materials.
- the electron blocking layer has a function of a hole transport layer in a broad sense.
- the electron blocking layer is made of a material that has the ability to transport holes and has a very small ability to transport electrons. By blocking holes while transporting holes, the probability of recombination of electrons and holes is improved. Can be made.
- the structure of a positive hole transport layer can be used as an electron blocking layer as needed.
- the layer thickness of the hole blocking layer applied to the present invention is preferably in the range of 3 to 100 nm, more preferably in the range of 5 to 30 nm.
- an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used.
- an electrode substance include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , ZnO, and IZO.
- conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , ZnO, and IZO.
- an amorphous material such as IDIXO (In 2 O 3 —ZnO) that can form a transparent conductive film may be used.
- these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method.
- pattern accuracy is not so high (about 100 ⁇ m or more)
- a pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material.
- wet film forming methods such as a printing system and a coating system, can also be used.
- the transmittance be greater than 10%
- the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
- the film thickness depends on the material, it is usually selected within the range of 10 to 1000 nm, preferably within the range of 10 to 200 nm.
- cathode a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used.
- electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.
- a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this for example, a magnesium / silver mixture, Magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al 2 O 3 ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred.
- the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
- the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably in the range of 50 to 200 nm.
- the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably in the range of 50 to 200 nm.
- a transparent or semi-transparent cathode can be produced by producing the conductive transparent material mentioned in the description of the anode on the cathode after producing the metal with a thickness of 1 to 20 nm on the cathode.
- an element in which both the anode and the cathode are transmissive can be manufactured.
- Examples of the sealing means used for sealing the organic EL element of the present invention include a method of bonding a sealing member, an electrode, and a support substrate with an adhesive.
- the sealing member may be disposed so as to cover the display area of the organic EL element, and may be a concave plate shape or a flat plate shape. Moreover, transparency and electrical insulation are not particularly limited.
- Specific examples include a glass plate, a polymer plate / film, and a metal plate / film.
- the glass plate include soda-lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
- the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone.
- the metal plate include those made of one or more metals or alloys selected from the group consisting of stainless steel, iron, copper, aluminum, magnesium, nickel, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum.
- a polymer film and a metal film can be preferably used because the organic EL element can be thinned.
- the polymer film preferably has an oxygen permeability of 10 ⁇ 3 g / (m 2 ⁇ 24 h) or less and a water vapor permeability of 10 ⁇ 3 g / (m 2 ⁇ 24 h) or less. Further, it is more preferable that both the water vapor permeability and the oxygen permeability are 10 ⁇ 5 g / (m 2 ⁇ 24 h) or less.
- the adhesive include photocuring and thermosetting adhesives having reactive vinyl groups of acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylate. be able to.
- fever and chemical curing types such as an epoxy type, can be mentioned.
- hot-melt type polyamide, polyester, and polyolefin can be mentioned.
- a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.
- a desiccant may be dispersed in the adhesive.
- coating of the adhesive agent to a sealing part may use commercially available dispenser, and may print like screen printing.
- the electrode and the organic layer on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and form an inorganic or organic layer in contact with the support substrate to form a sealing film.
- a material for forming the film any material may be used as long as it has a function of suppressing intrusion of elements that cause deterioration of elements such as moisture and oxygen.
- silicon oxide, silicon dioxide, silicon nitride, or the like may be used. it can.
- vacuum deposition sputtering, reactive sputtering, molecular beam epitaxy, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma
- a polymerization method a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used.
- an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil is injected in the gas phase and the liquid phase.
- a vacuum can also be used.
- a hygroscopic compound can also be enclosed inside.
- hygroscopic compound examples include metal oxides (for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide) and sulfates (for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate).
- metal oxides for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide
- sulfates for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate.
- metal halides eg, calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide, etc.
- perchloric acids eg, barium perchlorate
- Magnesium perchlorate, etc. anhydrous salts are preferably used in sulfates, metal halides and perchloric acids.
- a protective film or a protective plate may be provided outside the sealing film or sealing film on the side facing the support substrate with the organic layer interposed therebetween.
- the mechanical strength is not necessarily high, and thus it is preferable to provide such a protective film and a protective plate.
- the same glass plate, polymer plate / film, metal plate / film, etc. used for the sealing can be used, but the polymer film is light and thin. Is preferably used.
- the organic EL element of the embodiment described above is a surface light emitter, it can be used as various light emission sources.
- lighting devices such as home lighting and interior lighting, backlights for clocks and liquid crystals, lighting for billboard advertisements, light sources for traffic lights, light sources for optical storage media, light sources for electrophotographic copying machines, light sources for optical communication processors, Examples include, but are not limited to, a light source of an optical sensor, and can be effectively used as a backlight of a liquid crystal display device combined with a color filter and a light source for illumination.
- Example 1 Production of Organic EL Element 101 >> As shown below, the anode / hole injection layer / hole transport layer / light emitting layer / blocking layer / electron transport layer / electron injection layer / cathode are laminated and sealed on the base material to form a bottom emission type organic material. An EL element 101 was produced.
- an atmospheric pressure plasma discharge treatment apparatus having a configuration described in Japanese Patent Application Laid-Open No. 2004-68143 is used on the entire surface of the polyethylene naphthalate film (manufactured by Teijin DuPont, hereinafter abbreviated as PEN) on the anode forming side.
- PEN polyethylene naphthalate film
- an inorganic gas barrier layer made of SiO x was formed to a thickness of 500 nm.
- a flexible base material having a gas barrier property with an oxygen permeability of 0.001 mL / (m 2 ⁇ 24 h) or less and a water vapor permeability of 0.001 g / (m 2 ⁇ 24 h) or less was produced.
- ITO indium tin oxide
- the base material on which the hole injection layer was formed was transferred to a nitrogen atmosphere using nitrogen gas (grade G1), and a coating liquid for forming a hole transport layer having the following composition was used to form a 5 m / After being applied for min and dried naturally, it was held at 130 ° C. for 30 minutes to form a hole transport layer having a layer thickness of 30 nm.
- nitrogen gas grade G1
- the base material on which the hole transport layer was formed was applied at 5 m / min by a die coating method using a light emitting layer forming coating solution having the following composition, naturally dried, and then held at 120 ° C. for 30 minutes.
- a light emitting layer having a layer thickness of 50 nm was formed.
- the base material on which the light-emitting layer was formed was applied at 5 m / min by a die coating method using a coating solution for forming a block layer having the following composition, naturally dried, and then kept at 80 ° C. for 30 minutes to obtain a layer thickness. A 10 nm block layer was formed.
- the base material on which the block layer was formed was applied at 5 m / min by a die coating method using a coating liquid for forming an electron transport layer having the following composition, naturally dried, and then held at 80 ° C. for 30 minutes, An electron transport layer having a thickness of 30 nm was formed.
- the sealing base material was adhere
- An agent layer was provided, and a laminate of a polyethylene terephthalate (PET) film having a thickness of 12 ⁇ m was prepared.
- PET polyethylene terephthalate
- thermosetting adhesive as a sealing adhesive was uniformly applied at a thickness of 20 ⁇ m along the adhesive surface (shiny surface) of the aluminum foil of the sealing substrate using a dispenser. This was dried under a vacuum of 100 Pa or less for 12 hours. Further, the sealing substrate is moved to a nitrogen atmosphere having a dew point temperature of ⁇ 80 ° C. or less and an oxygen concentration of 0.8 ppm, and is dried for 12 hours or more so that the moisture content of the sealing adhesive is 100 ppm or less. It was adjusted.
- thermosetting adhesive an epoxy adhesive mixed with the following (A) to (C) was used.
- DGEBA Bisphenol A diglycidyl ether
- DIY Dicyandiamide
- C Epoxy adduct curing accelerator
- the sealing substrate was closely attached to the laminate, and was tightly sealed using a pressure-bonding roll under pressure-bonding conditions of a pressure-rolling roll temperature of 100 ° C., a pressure of 0.5 MPa, and an apparatus speed of 0.3 m / min. .
- a pressure-bonding roll temperature of 100 ° C.
- a pressure of 0.5 MPa a pressure of 0.5 MPa
- an apparatus speed 0.3 m / min.
- Luminous efficiency measurement Luminous efficiency is measured at room temperature (25 ° C) at a constant current density of 2.5 mA / cm 2 and a spectral radiance meter CS-2000 (manufactured by Konica Minolta). Was used to measure the light emission luminance of each element, and the light emission efficiency (external extraction efficiency) at the current value was determined. It represents with the relative value which sets the luminous efficiency of the organic EL element 145 (comparative example) to 100.
- the luminescence lifetime is measured by driving the organic EL element continuously under conditions of room temperature 25 ° C and humidity 55% RH, and measuring the luminance using the above-mentioned spectral radiance meter CS-2000. The time (half life) during which the brightness was reduced by half was determined as a measure of life.
- the driving condition was set to a current value of 10,000 cd / m 2 at the start of continuous driving. And it represented with the relative value which sets the light emission lifetime of the organic EL element 145 (comparative example) to 100.
- the entire layer from the hole injection layer to the electron transport layer was removed by immersion in toluene, and the membrane area was determined from the weight ratio before and after the removal.
- the mass ratio of the polar fluorinated solvent per volume of was determined.
- the case where a dominant peak is not detected in the mass fragment spectrum corresponding to each polar fluorinated solvent is indicated as “nd” (not detected).
- the organic EL device according to the present invention is superior in luminous efficiency and luminous lifetime as compared with the organic EL device of the comparative example.
- each component layer is mainly formed using the apply
- Example 2 Production of Organic EL Element 201 >> An organic EL element 201 was produced in the same manner as in the production of the organic EL element 101 of Example 1 except that the material contained in the block layer forming coating solution was changed to HS-12.
- the substrate on which the light emitting layer was formed was attached to a vacuum deposition apparatus without being exposed to the atmosphere. Also, a molybdenum resistance heating boat with HS-12 is attached to a vacuum deposition apparatus, and the vacuum chamber is depressurized to 4 ⁇ 10 ⁇ 5 Pa. Vapor deposition was performed on the light emitting layer at 1 nm / second to form a block layer having a layer thickness of 10 nm.
- the organic EL device according to the present invention is superior in luminous efficiency and luminous lifetime as compared with the organic EL device of the comparative example.
- the organic EL element 202 of the comparative example has a block layer formed by a vapor deposition method, so that the hydrophobic block of HS-12 does not orient on the surface of the layer (the surface on the electron transport layer side). This is probably because the electron transport layer material penetrated into the light emitting layer during the formation of the electron transport layer. Therefore, according to the method for producing an organic EL element of the present invention, it can be said that it is possible to produce an organic EL element having a higher light emission efficiency and a longer life than when a block layer is formed by vapor deposition.
- the substrate on which the block layer was formed was attached to a vacuum deposition apparatus without being exposed to the atmosphere.
- a molybdenum resistance heating boat containing Compound A was attached to a vacuum deposition apparatus, and after the vacuum chamber was depressurized to 4 ⁇ 10 ⁇ 5 Pa, the boat was energized and heated to heat Compound A to 0.1 nm / The film was deposited on the light emitting layer in seconds to form an electron transport layer having a layer thickness of 30 nm.
- the organic EL device according to the present invention is superior in luminous efficiency and luminous lifetime as compared with the organic EL device of the comparative example. Therefore, according to the method for producing an organic EL device of the present invention, although not as much as when an electron transport layer is formed by a coating method, even when an electron transport layer is formed by a vapor deposition method, high luminous efficiency and long It can be said that a long-life organic EL element can be manufactured.
- the substrate on which the hole transport layer was formed was attached to a vacuum deposition apparatus without being exposed to the atmosphere. Further, a molybdenum resistance heating boat containing the host compound S-5 and a phosphorescent dopant D-76 were each attached to a vacuum deposition apparatus. After reducing the vacuum chamber to 4 ⁇ 10 ⁇ 5 Pa, the boat was energized and heated to co-evaporate the host compound S-5 at 0.01 nm / sec and D-76 at 0.09 nm / sec. A 50 nm light emitting layer was formed.
- the organic EL device according to the present invention is superior in luminous efficiency and luminous lifetime as compared with the organic EL device of the comparative example. Therefore, according to the method for producing an organic EL element of the present invention, it can be said that an organic EL element having a high luminous efficiency and a long lifetime can be produced even when a light emitting layer is formed by vapor deposition.
- the present invention can be applied to a flexible substrate, and a method for producing an organic electroluminescence element and an organic electroluminescence capable of producing an organic electroluminescence element with high luminous efficiency and long life at low cost. Suitable for providing an element.
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Abstract
Description
しかしながら、有機EL素子の発光層や電子輸送層等を構成する機能材料の多くは、化学的に類似した構造骨格からなる物質が多く、塗布積層溶媒への溶解性も近いために積層時に混合してしまうことがある。そのため、溶媒と溶質(機能材料)の溶解度差により積層を試みた場合は、発光層の電子輸送層と反対側に積層される正孔輸送層や正孔注入層を含めて4層程度の積層が限界であった。
また、例えば、フルオロアルキル基等の機能性基を有する電子輸送性材料と、発光材料とを塗布成膜して混合層を形成し、当該混合層内で電子輸送材料を移動させることで電子輸送材料と発光材料とを分離し、疑似的な積層構造を形成して、4層以上の積層を可能とする技術が提案されている(例えば、特許文献3参照。)。
また、上記特許文献3に記載の技術にあっては、混合層内の材料分離後も発光材料と電子輸送材料との接触による混合が避けられないため、発光材料と電子輸送材料との間での配位子交換や錯体形成が起きてクエンチングが発生し、素子性能が低下する。また、複数種の材料に亘って分子設計が必要となるため、層全体の設計が難しいという問題もある。
すなわち、本発明に係る課題は、以下の手段により解決される。
前記ブロック層を、下記一般式(1)で表される構造を有する化合物及び極性フッ化溶媒を含有する塗布液を用いて形成することを特徴とする有機エレクトロルミネッセンス素子の製造方法。
前記ブロック層は、下記一般式(1)で表される構造を有する化合物及び極性フッ化溶媒を含有することを特徴とする有機エレクトロルミネッセンス素子。
本発明の効果の発現機構ないし作用機構については、明確にはなっていないが、以下のように推察している。
本発明に係る一般式(1)で表される構造を有する化合物は、アルキレン基又はアルキル基を含み、発光層に含有され得る一般的なホスト材料に近い構造を持つことを特徴としている。当該一般式(1)で表される構造を有する化合物は、結晶学的にディスオーダーが大きいアルキレン基又はアルキル基を含むことで、固体状態での溶解性が向上し、発光層を溶かさない溶媒(極性フッ化溶媒)への溶解性が向上している。更に、立体障害の効果により発光材料への反応性が低減されていることで、発光層に影響が少ないブロック機能を有する層が形成可能となる。
一方で、本発明の製造方法で用いられる極性フッ化溶媒は、C-F結合の分極率の低さから分子間力が弱く、表面自由エネルギーが小さいという特徴を持つ。これにより、優れた撥水撥油性や非粘着性を有し、当該極性フッ化溶媒を含有する塗布液を用いてブロック層を形成する際に、その下層の構成材料を溶解させにくい。また、極性フッ化溶媒を用いてブロック層を形成する場合、塗布膜を乾燥させる際にブロック層材料が凝集することによる素子性能の低下を抑制することができ、ブロック層材料の下層への浸透も抑制することができる。
また、一般に、塗布法により形成された塗布膜(ウェット膜)が乾燥するまでの間、当該塗布膜の表面では、表面自由エネルギーを最小化するように表面張力が働くため、塗布膜中の分子は表面エネルギーの低い疎水基を塗布膜表面に出し、極性基や比較的疎水性の小さい芳香環を塗布膜内部に配向させた状態で安定化する。本発明のように、一般式(1)で表される構造を有する化合物を含有する塗布液を用いてブロック層を形成すると、その塗布膜が乾燥するまでの間、上記のとおり表面自由エネルギーを最小とするために、極性基及び芳香環を多く有し疎水基が少ない部位が発光層側へ、疎水基を多く含む部位が塗布膜表面側に配向する。その結果、塗布膜が乾燥して形成されたブロック層の上に電子輸送層を親水性極性溶媒で湿式成膜することが可能となる。
したがって、本発明によれば、一般式(1)で表される構造を有する化合物及び極性フッ化溶媒によりブロック層を形成するため、主に低分子化合物等の溶媒に溶解しやすい材料で構成される発光層上に、当該発光層を溶解させることなくブロック層を積層でき、かつブロック層を溶解させることなく電子輸送層を塗布法で積層することができる。
本発明においては、前記極性フッ化溶媒が、フッ化アルコール、フッ化エステル及びフッ化エーテルから選ばれる溶媒であることが好ましい。これらの溶媒を用いることで、下層の溶解抑制と、一般式(1)で表される構造を有する化合物の溶解及び配向性の制御とをより確実に両立させることができ、本発明の効果を好適に得ることができる。
また、本発明においては、前記極性フッ化溶媒が、炭素原子数3~5のフッ化アルコールを含有することが好ましい。これにより、塗布膜乾燥までの間に塗布膜がレベリングし揮発ムラを抑制できる一方で、膜外に溶媒分子が素早く排出されるため溶質分子の結晶化や層内の溶媒含有による性能の低下を低減できるため本発明の効果を最大限に発揮することができる。
また、本発明においては、前記一般式(2)で表される置換基のうち、少なくとも一つのLが炭素原子数1~6のアルキレン基であることが好ましい。Lが炭素原子数1以上のアルキレン基であると、極性フッ化溶媒への溶解度が向上し、一般式(1)で表される構造を有する化合物の結晶化を抑制できる。一方で、Lが炭素原子数6以下のアルキレン基であると、一般式(1)で表される構造を有する化合物が必要以上にディスオーダーすることによる粗膜形成に起因する電子移動度の低下を抑制できるため、本発明の効果を最大限に発揮することができる。
また、本発明においては、前記一般式(2)で表される置換基のうち、少なくとも一つのRが炭素原子数1~6のアルキル基であることが好ましい。Rが炭素原子数1以上のアルキル基であると、極性フッ化溶媒への溶解度が向上し、一般式(1)で表される構造を有する化合物の結晶化を抑制できるだけでなく、発光層への浸透を抑制することができる。一方で、Rが炭素原子数6以下のアルキル基であると、必要以上に一般式(1)で表される構造を有する化合物の分子間距離が離れることによる電子移動度の低下を抑制できるため、本発明の効果を最大限に発揮することができる。
また、本発明においては、前記電子輸送層を、電子輸送材料を含有する塗布液を用いて形成することが好ましい。これにより、電子輸送層を湿式製膜した場合でも下層溶解を抑制でき、発光層への電子輸送層成分の混入を低減できるため、本発明の効果を最大限に発揮することができる。
また、本発明においては、前記電子輸送材料を含有する塗布液が、極性フッ化溶媒を含有することが好ましい。これにより、ブロック層に対して当該塗布液が塗れにくくなり、電子輸送材料及びブロック層材料の下層浸透を抑制できるだけでなく、ブロック層と電子輸送層との界面の適度な混合が得られるため、電子輸送性の低下を抑制でき、本発明の効果を最大限に発揮することができる。
また、本発明においては、本発明の効果発現の観点から、前記発光層が、極性フッ化溶媒に対する溶解度が前記一般式(1)で表される構造を有する化合物より低い化合物で構成されていることが好ましい。
また、本発明においては、前記発光層が、分子量3000以下の化合物で構成されていることが好ましい。このように、発光層が溶媒に溶解しやすい低分子化合物で構成されていても、当該発光層を溶解させることなく他の機能層を積層できるため、高発光効率及び高寿命の有機EL素子を確実に製造することができる。
また、本発明においては、前記発光層が、ジベンゾフラン環、ジベンゾチオフェン環又はカルバゾール環を有し、かつアルキル基、アルケニル基、アルキニル基又はアリールアルキル基を有しない化合物を含有することが好ましい。発光層に含有される化合物が、一般式(1)と類似する骨格を有することで電子輸送性を高めることができ、アルキル基等を有しないことで密度の高い膜を形成可能なため、ブロック層材料の発光層への侵入を抑制でき、本発明の効果を最大限に発揮することができる。
本発明においては、極性フッ化溶媒が、各構成層全体として1000質量ppm以下含有されていることが好ましい。これにより、有機EL素子材料間の電荷授受を損なうことなく、駆動時に発生する熱等のエネルギーにより有機EL素子材料が再配向して結晶粒とならず、結晶粒界の電荷トラップにより輸送性が低下することもない。
本発明の有機EL素子の製造方法により製造される有機EL素子の構成について、図1を参照して説明する。図1は、本発明の製造方法により製造される有機EL素子の一例である有機EL素子10の概略断面図である。
(1)発光層/ブロック層/電子輸送層
(2)正孔輸送層/発光層/ブロック層/電子輸送層
(3)正孔輸送層/発光層/ブロック層/電子輸送層/電子注入層
(4)正孔注入層/正孔輸送層/発光層/ブロック層/電子輸送層
(5)正孔注入層/正孔輸送層/発光層/ブロック層/電子輸送層/電子注入層
(6)正孔注入層/正孔輸送層/電子阻止層/発光層/ブロック層/電子輸送層/電子注入層
上記の中で(5)及び(6)の構成が好ましく用いられるが、これに限定されるものではない。
本発明の有機EL素子の製造方法は、陽極と陰極との間に、発光層と、ブロック層と、電子輸送層とを備える有機EL素子の製造方法であって、ブロック層を、一般式(1)で表される構造を有する化合物及び極性フッ化溶媒を含有する塗布液を用いて形成することを特徴とする。
まず、基材11上に、陽極12を形成する。次に、陽極12上に、正孔注入層13及び正孔輸送層14をこの順に形成する。次に、発光層15を形成する。次に、発光層15上に、一般式(1)で表される構造を有する化合物及び極性フッ化溶媒を含有するブロック層形成用塗布液を用いてブロック層16を形成する。次に、ブロック層16上に、電子輸送層17を形成する。次に、電子輸送層17上に、電子注入層18及び陰極19を形成する。
なお、有機EL素子10を構成するブロック層以外の各層の形成方法としては、上記したとおり、湿式法、蒸着及びスパッタ等いずれの方法であっても良い。
以上のようにして有機EL素子10を製造することができる。
発光層は、電極又は隣接層から注入される電子と正孔とが再結合し、励起子を経由して発光する場を提供する層である。発光層は、発光ドーパント(発光性ドーパント化合物、ドーパント化合物、単にドーパントともいう。)と、ホスト化合物(マトリックス材料、発光ホスト化合物、単にホストともいう。)とを含有することが好ましい。
また、発光層材料を液媒体中に分散させる場合には、例えば、超音波、高剪断力分散やメディア分散等の分散方法により分散させることができる。
発光ドーパントとしては、蛍光発光性ドーパント(蛍光ドーパント、蛍光性化合物ともいう。)又はリン光発光性ドーパント(リン光ドーパント、リン光性化合物ともいう。)が好ましく用いられる。発光層中の発光ドーパントの濃度については、使用される特定のドーパント及びデバイスの必要条件に基づいて、任意に決定することができる。発光ドーパントの濃度は、発光層の層厚方向に対し、均一な濃度で含有されていても良いし、任意の濃度分布を有していても良い。
リン光発光性ドーパントは、励起三重項からの発光が観測される化合物であり、具体的には、室温(25℃)にてリン光発光する化合物であり、25℃においてリン光量子収率が0.01以上の化合物である。発光層に用いられるリン光発光性ドーパントにおいて、好ましいリン光量子収率は0.1以上である。
蛍光発光性ドーパントは、励起一重項からの発光が可能な化合物であり、励起一重項からの発光が観測される限り特に限定されない。
遅延蛍光を利用した発光ドーパントの具体例としては、例えば、国際公開第2011/156793号、特開2011-213643号公報、特開2010-93181号公報等に記載の化合物が挙げられる。
ホスト化合物は、発光層において主に電荷の注入及び輸送を担う化合物であり、有機EL素子においてそれ自体の発光は実質的に観測されない。
好ましくは室温(25℃)においてリン光発光のリン光量子収率が、0.1未満の化合物であり、更に好ましくは、リン光量子収率が0.01未満の化合物である。また、発光層に含有される化合物の内で、その層中での質量比が20%以上であることが好ましい。
ホスト化合物は、単独で用いても良く、又は複数種併用して用いても良い。ホスト化合物を複数種用いることで、電荷の移動を調整することが可能であり、有機EL素子の高効率化が可能となる。
ここで、ガラス転移点(Tg)とは、DSC(Differential Scanning Colorimetry:示差走査熱量法)を用いて、JIS-K-7121に準拠した方法により求められる値である。
本発明において、ブロック層とは、発光層と電子輸送層との間に挿入される層を表し、電子輸送層から注入される電子を発光層側へ輸送し、発光層側から輸送される正孔及び、発光層上で電子と正孔が再結合することにより生じる励起子を発光層内に閉じ込める機能を有する層である。したがって、ブロック層はいわゆる正孔阻止層として機能する。
ブロック層に極性フッ化溶媒が含有されているか否かについては、次のようにして判断することができる。すなわち、有機EL素子のブロック層中に含有される極性フッ化溶媒の分布を、TOF-SIMS(飛行時間型二次イオン質量分析)により分析し、層厚方向でのフッ素分布を測定する(測定は基板側からイオンを出射する形で進め、イオン衝突時の構成物の打ち込み方向と積層時の溶媒浸透方向が一致しないよう配慮する。)。これによりフッ素原子が検出された場合には、ブロック層に極性フッ化溶媒が含有されていると判断することができる。
ブロック層は、下記一般式(1)で表される構造を有する化合物を含有する塗布液を用いて形成することができる。
また、R1~R9で表されるアルケニル基としては、例えば、上記アルキル基に1個以上の二重結合を有するものが挙げられ、より具体的には、ビニル基、アリル基、1-プロペニル基、イソプロペニル基、2-ブテニル基、1,3-ブタジエニル基、2-ペンテニル基、2-ヘキセニル基等が挙げられる。
また、R1~R9で表されるアルキニル基としては、例えば、エチニル基、アセチレニル基、1-プロピニル基、2-プロピニル基(プロパルギル基)、1-ブチニル基、2-ブチニル基、3-ブチニル基、1-ペンチニル基、2-ペンチニル基、3-ペンチニル基、1-ヘキシニル基、2-ヘキシニル基、3-ヘキシニル基、1-ヘプチニル基、2-ヘプチニル基、5-ヘプチニル基、1-オクチニル基、3-オクチニル基、5-オクチニル基等が挙げられる。
また、R1~R9で表される芳香族複素環基としては、例えば、ピリジル基、ピリミジニル基、フリル基、ピロリル基、イミダゾリル基、ベンゾイミダゾリル基、ピラゾリル基、ピラジニル基、トリアゾリル基(例えば、1,2,4-トリアゾール-1-イル基、1,2,3-トリアゾール-1-イル基等)、オキサゾリル基、ベンゾオキサゾリル基、チアゾリル基、イソオキサゾリル基、イソチアゾリル基、フラザニル基、チエニル基、キノリル基、ベンゾフリル基、ジベンゾフリル基、ベンゾチエニル基、ジベンゾチエニル基、インドリル基、カルバゾリル基、カルボリニル基、ジアザカルバゾリル基(前記カルボリニル基のカルボリン環を構成する炭素原子の一つが窒素原子で置き換わったものを示す。)、キノキサリニル基、ピリダジニル基、トリアジニル基、キナゾリニル基、フタラジニル基等が挙げられる。
また、R1~R9で表される非芳香族炭化水素環基としては、例えば、エポキシ環、アジリジン環、チイラン環、オキセタン環、アゼチジン環、チエタン環、テトラヒドロフラン環、ジオキソラン環、ピロリジン環、ピラゾリジン環、イミダゾリジン環、オキサゾリジン環、テトラヒドロチオフェン環、スルホラン環、チアゾリジン環、ε-カプロラクトン環、ε-カプロラクタム環、ピペリジン環、ヘキサヒドロピリダジン環、ヘキサヒドロピリミジン環、ピペラジン環、モルホリン環、テトラヒドロピラン環、1,3-ジオキサン環、1,4-ジオキサン環、トリオキサン環、テトラヒドロチオピラン環、チオモルホリン環、チオモルホリン-1,1-ジオキシド環、ピラノース環、ジアザビシクロ[2,2,2]-オクタン環、フェノキサジン環、フェノチアジン環、オキサントレン環、チオキサンテン環、フェノキサチイン環等から導出される一価の基等が挙げられる。
また、R1~R8で表されるアシル基としては、例えば、アセチル基、エチルカルボニル基、プロピルカルボニル基、ペンチルカルボニル基、シクロヘキシルカルボニル基、オクチルカルボニル基、2-エチルヘキシルカルボニル基、ドデシルカルボニル基、フェニルカルボニル基、ナフチルカルボニル基、ピリジルカルボニル基等が挙げられる。
また、R1~R8で表されるアミノ基としては、例えば、アミノ基、エチルアミノ基、ジメチルアミノ基、ブチルアミノ基、シクロペンチルアミノ基、2-エチルヘキシルアミノ基、ドデシルアミノ基、アニリノ基、ナフチルアミノ基、2-ピリジルアミノ基等が挙げられる。
また、R1~R8で表されるシリル基としては、例えば、トリメチルシリル基、トリイソプロピルシリル基、トリフェニルシリル基、フェニルジエチルシリル基等が挙げられる。
また、R1~R8で表されるホスフィンオキシド基としては、例えば、ジフェニルホスフィンオキシド基、ジトリルホスフィンオキシド基、ジメチルホスフィンオキシド基、ジナフチルホスフィンオキシド基、9,10-ジヒドロ-9-オキサ-10-ホスファフェナントレン-10-オキサイド基等を挙げることができる。
また、Lで表されるアルケニレン基としては、例えば、ビニレン基、プロペニレン基、ブテニレン基、ペンテニレン基、1-メチルビニレン基、1-メチルプロペニレン基、2-メチルプロペニレン基、1-メチルペンテニレン基、3-メチルペンテニレン基、1-エチルビニレン基、1-エチルプロペニレン基、1-エチルブテニレン基、3-エチルブテニレン基等が挙げられる。
また、Lで表されるアミド基としては、例えば、メチルカルボニルアミノ基、エチルカルボニルアミノ基、ジメチルカルボニルアミノ基、プロピルカルボニルアミノ基、ペンチルカルボニルアミノ基、シクロヘキシルカルボニルアミノ基、2-エチルヘキシルカルボニルアミノ基、オクチルカルボニルアミノ基、ドデシルカルボニルアミノ基、フェニルカルボニルアミノ基、ナフチルカルボニルアミノ基等が挙げられる。
また、Lで表される二価の芳香族複素環基としては、例えば、上記一般式(1)においてR1~R9で表される芳香族複素環基として挙げられたものから導出される二価の基が挙げられる。
Rで表される炭素原子数1~20のフッ化アルキル基としては、例えば、上記炭素原子数1~20のアルキル基の水素原子がフッ素原子に置換した基が挙げられる。
Rで表される炭素原子数1~20のアルコキシ基としては、例えば、上記一般式(1)においてR1~R8で表されるアルコキシ基として挙げられたもののうち、炭素原子数が1~20の基が挙げられる。
Rで表される芳香族炭化水素環基、芳香族複素環基又は非芳香族炭化水素環基としては、例えば、上記一般式(1)においてR1~R9で表される芳香族炭化水素環基、芳香族複素環基又は非芳香族炭化水素環基と同様のものが挙げられる。
本発明の有機EL素子の製造方法において、ブロック層の形成には極性フッ化溶媒が用いられる。また、電子輸送層の形成にも極性フッ化溶媒が用いられることが好ましい。
ここで、極性フッ化溶媒とは、溶媒分子中にフッ素原子を含み、比誘電率が3以上かつ25℃における水への溶解度が5g/L以上である溶媒をいう。
また、極性フッ化溶媒中の水分以外の不純物含有量も同様に、極微量であっても発光のクエンチャーとなったり、気泡や乾燥後の膜質低下要因となるため少ない程良く、100ppm以下が好ましく、20ppm以下であることが更に好ましい。水分以外の不純物としては、酸素や、窒素、アルゴン及び二酸化炭素等の不活性ガス、調製及び精製時に使用される触媒、吸着材及び器具等から持ち込まれる無機化合物又は金属等が挙げられる。
また、フッ化アルコールの炭素原子数は、沸点及び材料の可溶性の観点から、炭素原子数3~5であることが好ましい。
また、フッ化エーテルとしては、例えば、ヘキサフルオロジメチルエーテル、ペルフルオロジメトキシメタン、ペルフルオロオキセタン、ペルフルオロ-1,3-ジオキソラン、1,1,2,2-テトラフルオロエチル-2,2,3,3-テトラフルオロプロピルエーテル等が挙げられる。
また、フッ化エステルとしては、例えば、メチルパーフルオロブチレート、エチルパーフルオロブチレート、メチルパーフルオロプロピオネート、メチルジフルオロアセテート、エチルジフルオロアセテート、メチル-2-トリフルオロメチルー3,3,3-トリフルオロプロピオネート等が挙げられる。
また、極性フッ化溶媒としては、発光層材料を溶解させないものであれば、2種以上の極性フッ化溶媒の混合溶媒でも良いし、極性フッ化溶媒と極性フッ化溶媒以外の溶媒との混合溶媒でも良い。例えば、フッ化アルコールとアルコールとの混合溶媒等を用いることができる。混合溶媒を用いる場合、極性フッ化溶媒の含有量は50質量%以上であることが好ましい。
まず、30mm角のガラス基板上に、測定対象の有機EL素子と同様にして、正孔注入層から電子輸送層までの各層を形成したサンプルを作製する。このサンプルの平坦膜部から1cm口程度のサンプルを2つ切り出す。その一方は、トルエンを浸したクリーンワイパーで正孔注入層から電子輸送層までの全層を一部剥ぎ取って段差をつけ、サンユー電子社製SC-701 MkII ECOでAg薄膜をスパッタ後、Veeco社製WYKOを用いて段差を計測し、膜厚を決定する。更に、切り出したもう一方のサンプルは、正孔注入層から電子輸送層までの全層をトルエン浸漬により除去し、除去前後の重量比から膜面積を求める。上記面積が決定されたサンプルを電子科学社製の昇温熱脱離分析装置により測定し、層の形成に使用した極性フッ化溶媒に対応するマスフラグメントスペクトルから、脱離ガス成分を定量し、各有機層積層体の体積当たりの極性フッ化溶媒の質量比を求める。以上のようにして、極性フッ化溶媒の含有量を求めることができる。
有機EL素子に用いられる基材の材料には特に限定はなく、好ましくは、例えば、ガラス、石英又は樹脂フィルム等を挙げることができる。特に好ましくは、有機EL素子にフレキシブル性を与えることが可能な樹脂フィルムである。
電子輸送層とは電子を輸送する機能を有する材料からなり、広い意味で電子注入層も電子輸送層に含まれる。電子輸送層は単層又は複数層設けることができる。
また、電子輸送層は、以下に説明する電子輸送材料を含有する塗布液を用いて形成することが好ましい。また、当該塗布液は極性フッ化溶媒を含有することが好ましい。極性フッ化溶媒に対する溶解度は、電子輸送層の材料、ブロック層の材料、発光層の材料の順に低くなることが好ましい。
これらの中でもカルバゾール誘導体、アザカルバゾール誘導体、ピリジン誘導体等が本発明では好ましく、アザカルバゾール誘導体であることがより好ましい。
これらドープ材の含有量は、添加する電子輸送層に対し、好ましくは1.5~35質量%であり、より好ましくは3~25質量%であり、最も好ましくは5~15質量%である。
正孔輸送層は、正孔を輸送する機能を有する正孔輸送材料から構成されており、広い意味で正孔注入層、電子阻止層も正孔輸送層に含まれる。また、正孔輸送層は、単層又は複数層設けることができる。
注入層(正孔注入層及び電子注入層)とは、駆動電圧低下や発光輝度向上のために、電極と発光層の間に設けられる層のことで、「有機EL素子とその工業化最前線(1998年11月30日エヌ・ティー・エス社発行)」の第2編第2章「電極材料」(123~166頁)にその詳細が記載されており、正孔注入層と電子注入層とがある。
電子阻止層とは、広い意味では、正孔輸送層の機能を有する。電子阻止層は、正孔を輸送する機能を有しつつ、電子を輸送する能力が著しく小さい材料からなり、正孔を輸送しつつ電子を阻止することで電子と正孔の再結合確率を向上させることができる。また、正孔輸送層の構成を必要に応じて電子阻止層として用いることができる。本発明に適用する正孔阻止層の層厚としては、好ましくは3~100nmの範囲であり、更に好ましくは5~30nmの範囲である。
有機EL素子における陽極としては、仕事関数の大きい(4eV以上)金属、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。このような電極物質の具体例としてはAu等の金属、CuI、インジウムチンオキシド(ITO)、SnO2、ZnO、IZO等の導電性透明材料が挙げられる。また、IDIXO(In2O3-ZnO)等非晶質で透明導電膜を作製可能な材料を用いても良い。陽極はこれらの電極物質を蒸着やスパッタリング等の方法により、薄膜を形成させ、フォトリソグラフィー法で所望の形状のパターンを形成しても良く、パターン精度をあまり必要としない場合は(100μm以上程度)、上記電極物質の蒸着やスパッタリング時に所望の形状のマスクを介してパターンを形成しても良い。また、有機導電性化合物のように塗布可能な物質を用いる場合には、印刷方式、コーティング方式など湿式製膜法を用いることもできる。この陽極より発光を取り出す場合には、透過率を10%より大きくすることが望ましく、また陽極としてのシート抵抗は数百Ω/□以下が好ましい。更に、膜厚は材料にもよるが、通常10~1000nmの範囲内、好ましくは10~200nmの範囲内で選ばれる。
一方、陰極としては、仕事関数の小さい(4eV以下)金属(電子注入性金属と称する。)、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが用いられる。このような電極物質の具体例としては、ナトリウム、ナトリウム-カリウム合金、マグネシウム、リチウム、マグネシウム/銅混合物、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、インジウム、リチウム/アルミニウム混合物、希土類金属等が挙げられる。これらの中で、電子注入性及び酸化等に対する耐久性の点から、電子注入性金属とこれより仕事関数の値が大きく安定な金属である第二金属との混合物、例えば、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、リチウム/アルミニウム混合物、アルミニウム等が好適である。陰極はこれらの電極物質を蒸着やスパッタリング等の方法により薄膜を形成させることにより、作製することができる。また、陰極としてのシート抵抗は数百Ω/□以下が好ましく、膜厚は通常10nm~5μmの範囲内、好ましくは50~200nmの範囲内で選ばれる。なお、発光した光を透過させるため、有機EL素子の陽極又は陰極のいずれか一方が、透明又は半透明であれば発光輝度が向上し好都合である。
本発明の有機EL素子の封止に用いられる封止手段としては、例えば、封止部材と、電極、支持基板とを接着剤で接着する方法を挙げることができる。
有機層を挟み支持基板と対向する側の封止膜又は封止用フィルムの外側に、素子の機械的強度を高めるために、保護膜又は保護板を設けても良い。特に、封止が封止膜により行われている場合には、その機械的強度は必ずしも高くないため、このような保護膜、保護板を設けることが好ましい。これに使用することができる材料としては、上記封止に用いたのと同様なガラス板、ポリマー板・フィルム、金属板・フィルム等を用いることができるが、軽量かつ薄膜化ということからポリマーフィルムを用いることが好ましい。
上述した実施形態の有機EL素子は、面発光体であるため各種の発光光源として用いることができる。例えば、家庭用照明や車内照明などの照明装置、時計や液晶用のバックライト、看板広告用照明、信号機の光源、光記憶媒体の光源、電子写真複写機の光源、光通信処理機の光源、光センサーの光源等が挙げられるが、これに限定するものではなく、特にカラーフィルターと組み合わせた液晶表示装置のバックライト、照明用光源としての用途に有効に用いることができる。
《有機EL素子101の作製》
以下のように、基材上に、陽極/正孔注入層/正孔輸送層/発光層/ブロック層/電子輸送層/電子注入層/陰極を積層して封止し、ボトムエミッション型の有機EL素子101を作製した。
まず、ポリエチレンナフタレートフィルム(帝人デュポン社製、以下、PENと略記する。)の陽極を形成する側の全面に、特開2004-68143号公報に記載の構成の大気圧プラズマ放電処理装置を用いて、SiOxからなる無機物のガスバリアー層を層厚500nmとなるように形成した。これにより、酸素透過度0.001mL/(m2・24h)以下、水蒸気透過度0.001g/(m2・24h)以下のガスバリアー性を有する可撓性の基材を作製した。
上記基材上に厚さ120nmのITO(インジウム・スズ酸化物)をスパッタ法により製膜し、フォトリソグラフィー法によりパターニングを行い、陽極を形成した。なお、パターンは発光領域の面積が5cm×5cmになるようなパターンとした。
陽極を形成した基材をイソプロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。そして、陽極を形成した基材上に、特許第4509787号公報の実施例16と同様に調製したポリ(3,4-エチレンジオキシチオフェン)/ポリスチレンスルホネート(PEDOT/PSS)の分散液をイソプロピルアルコールで希釈した2質量%溶液をダイコート法にて塗布、自然乾燥し、層厚40nmの正孔注入層を形成した。
次に、正孔注入層を形成した基材を、窒素ガス(グレードG1)を用いた窒素雰囲気下に移し、下記組成の正孔輸送層形成用塗布液を用いて、ダイコート法にて5m/minで塗布、自然乾燥した後に、130℃で30分間保持し、層厚30nmの正孔輸送層を形成した。
正孔輸送材料(下記化合物(60))(重量平均分子量Mw=80000)
10質量部
クロロベンゼン 3000質量部
次に、正孔輸送層を形成した基材を、下記組成の発光層形成用塗布液を用い、ダイコート法にて5m/minで塗布し、自然乾燥した後に、120℃で30分間保持し、層厚50nmの発光層を形成した。
ホスト化合物S-5 9質量部
リン光発光ドーパントD-76 1質量部
酢酸イソプロピル 2000質量部
次に、発光層を形成した基材を、下記組成のブロック層形成用塗布液を用い、ダイコート法にて5m/minで塗布し、自然乾燥した後に、80℃で30分間保持し、層厚10nmのブロック層を形成した。
HS-1 2質量部
IPA 1500質量部
OFAO 500質量部
次に、ブロック層を形成した基材を、下記組成の電子輸送層形成用塗布液を用い、ダイコート法にて5m/minで塗布し、自然乾燥した後に、80℃で30分間保持し、層厚30nmの電子輸送層を形成した。
下記化合物A 6質量部
TFPO 2000質量部
続いて、基板を大気に曝露することなく真空蒸着装置へ取り付けた。また、モリブデン製抵抗加熱ボートにフッ化ナトリウム及びフッ化カリウムを入れたものを真空蒸着装置に取り付け、真空槽を4×10-5Paまで減圧した。その後、ボートに通電して加熱し、フッ化ナトリウムを0.02nm/秒で前記電子輸送層上に蒸着し、膜厚1nmの薄膜を形成した。同様に、フッ化カリウムを0.02nm/秒でフッ化ナトリウム薄膜上に蒸着し、層厚1.5nmの電子注入層を形成した。
引き続き、アルミニウムを蒸着して厚さ100nmの陰極を形成した。
以上の工程により形成した積層体に対し、市販のロールラミネート装置を用いて封止基材を接着した。
封止基材として、可撓性を有する厚さ30μmのアルミニウム箔(東洋アルミニウム(株)製)に、ドライラミネーション用の2液反応型のウレタン系接着剤を用いて層厚1.5μmの接着剤層を設け、厚さ12μmのポリエチレンテレフタレート(PET)フィルムをラミネートしたものを作製した。
(A)ビスフェノールAジグリシジルエーテル(DGEBA)
(B)ジシアンジアミド(DICY)
(C)エポキシアダクト系硬化促進剤
以上のようにして、上述の図1に示す構成の有機EL素子と同様の形態の有機EL素子101を作製した。
上記有機EL素子101の作製において、ブロック層形成用塗布液に含有される材料及び溶媒、並びに電子輸送層形成用塗布液に含有される溶媒を表2及び表3に記載のとおりに変更した以外は同様にして、有機EL素子102~145を作製した。なお、ブロック層形成用塗布液に複数種の溶媒が含有される場合には、総含有量が2000質量部となるように調整した。
上記のように作製した有機EL素子101~145について、以下の評価を行った。その評価結果を表2及び表3に示す。
発光効率の測定は、室温(25℃)で、2.5mA/cm2の定電流密度条件下による点灯を行い、分光放射輝度計CS-2000(コニカミノルタ社製)を用いて、各素子の発光輝度を測定し、当該電流値における発光効率(外部取り出し効率)を求めた。有機EL素子145(比較例)の発光効率を100とする相対値で表した。
発光寿命の測定は、有機EL素子を室温25℃、湿度55%RHの条件下で連続駆動させ、上記分光放射輝度計CS-2000を用いて輝度を測定し、測定した輝度が半減する時間(半減寿命)を寿命の尺度として求めた。駆動条件は、連続駆動開始時に10000cd/m2となる電流値とした。そして、有機EL素子145(比較例)の発光寿命を100とする相対値で表した。
30mm角のガラス基板上に、上記有機EL素子101~145と同様にして、正孔注入層から電子輸送層までの各層を形成したサンプルを作製した。このサンプルの平坦膜部から1cm口程度のサンプルを2つ切り出した。その一方は、トルエンを浸したクリーンワイパーで正孔注入層から電子輸送層までの全層を一部剥ぎ取って段差をつけ、サンユー電子社製SC-701 MkII ECOでAg薄膜をスパッタ後、Veeco社製WYKOを用いて段差を計測し、膜厚を決定した。更に、切り出したもう一方のサンプルは、正孔注入層から電子輸送層までの全層をトルエン浸漬により除去し、除去前後の重量比から膜面積を求めた。上記面積が決定されたサンプルを電子科学社製の昇温熱脱離分析装置により測定し、使用した極性フッ化溶媒に対応するマスフラグメントスペクトルから、脱離ガス成分を定量し、各有機層積層体の体積当たりの極性フッ化溶媒の質量比を求めた。なお、各極性フッ化溶媒に対応するマスフラグメントスペクトルに優位なピークが検出されなかった場合を「n.d.」(not detected)と示す。
各有機EL素子のブロック層中に含まれる極性フッ化溶媒の分布を、TOF-SIMS(飛行時間型二次イオン質量分析)により分析し、層厚方向でのフッ素分布を測定した(測定は基板側からイオンを出射する形で進め、イオン衝突時の構成物の打ち込み方向と積層時の溶媒浸透方向が一致しないよう配慮した。)。これによりフッ素原子が検出された場合に、ブロック層に極性フッ化溶媒が含有されていると判断した。
したがって、本発明の有機EL素子の製造方法によれば、可撓性基板にも適用可能であって、高発光効率及び長寿命の有機EL素子を低コストで製造可能であるといえる。
《有機EL素子201の作製》
上記実施例1の有機EL素子101の作製において、ブロック層形成用塗布液に含有される材料をHS-12に変更した以外は同様にして、有機EL素子201を作製した。
上記実施例1の有機EL素子101の作製において、ブロック層の形成方法を以下のように変更した以外は同様にして、有機EL素子202を作製した。
発光層を形成した基板を大気に曝露することなく真空蒸着装置へ取り付けた。また、モリブデン製抵抗加熱ボートにHS-12を入れたものを真空蒸着装置に取り付け、真空槽を4×10-5Paまで減圧した後、ボートに通電して加熱してHS-12を0.1nm/秒で発光層上に蒸着し、層厚10nmのブロック層を形成した。
上記のようにして作製した有機EL素子201、202に対し、上記実施例1と同様に、発光効率及び発光寿命について評価を行った。評価結果を表4に示す。なお、表4における発光効率及び発光寿命の測定結果は、有機EL素子202(比較例)の測定値を100とする相対値で表した。
したがって、本発明の有機EL素子の製造方法によれば、蒸着法によりブロック層を形成した場合よりも、高発光効率及び長寿命の有機EL素子を製造可能であるといえる。
《有機EL素子301の作製》
上記実施例1の有機EL素子101の作製において、ブロック層形成用塗布液に含有される材料をHS-2に変更した以外は同様にして、有機EL素子301を作製した。
上記実施例1の有機EL素子101の作製において、ブロック層形成用塗布液に含有される材料を表5に記載のとおりに変更するとともに、電子輸送層の形成方法を以下のように変更した以外は同様にして、有機EL素子302、303を作製した。
ブロック層を形成した基板を大気に曝露することなく真空蒸着装置へ取り付けた。また、モリブデン製抵抗加熱ボートに化合物Aを入れたものを真空蒸着装置に取り付け、真空槽を4×10-5Paまで減圧した後、ボートに通電して加熱して化合物Aを0.1nm/秒で発光層上に蒸着し、層厚30nmの電子輸送層を形成した。
上記のようにして作製した有機EL素子301~303に対し、上記実施例1と同様に、発光効率及び発光寿命について評価を行った。評価結果を表5に示す。なお、表5における発光効率及び発光寿命の測定結果は、有機EL素子303(比較例)の測定値を100とする相対値で表した。
《有機EL素子401、402の作製》
上記実施例1の有機EL素子101の作製において、ブロック層形成用塗布液に含有される材料を表6に記載のとおりに変更するとともに、発光層の形成方法を以下のように変更した以外は同様にして、有機EL素子401、402を作製した。
正孔輸送層を形成した基板を大気に曝露することなく真空蒸着装置へ取り付けた。また、モリブデン製抵抗加熱ボートにホスト化合物S-5を入れたもの及びリン光発光ドーパントD-76を入れたものをそれぞれ真空蒸着装置に取り付けた。真空槽を4×10-5Paまで減圧した後、ボートに通電して加熱してホスト化合物S-5を0.01nm/秒、D-76を0.09nm/秒で共蒸着し、層厚50nmの発光層を形成した。
上記のようにして作製した有機EL素子401、402に対し、上記実施例1と同様に、発光効率及び発光寿命について評価を行った。評価結果を表6に示す。なお、表6における発光効率及び発光寿命の測定結果は、有機EL素子402(比較例)の測定値を100とする相対値で表した。
11 基材
12 陽極
13 正孔注入層
14 正孔輸送層
15 発光層
16 ブロック層
17 電子輸送層
18 電子注入層
19 陰極
Claims (12)
- 陽極と陰極との間に、発光層と、ブロック層と、電子輸送層とを備える有機エレクトロルミネッセンス素子の製造方法であって、
前記ブロック層を、下記一般式(1)で表される構造を有する化合物及び極性フッ化溶媒を含有する塗布液を用いて形成することを特徴とする有機エレクトロルミネッセンス素子の製造方法。
- 前記極性フッ化溶媒が、フッ化アルコール、フッ化エステル及びフッ化エーテルから選ばれる溶媒であることを特徴とする請求項1に記載の有機エレクトロルミネッセンス素子の製造方法。
- 前記極性フッ化溶媒が、炭素原子数3~5のフッ化アルコールを含有することを特徴とする請求項1又は請求項2に記載の有機エレクトロルミネッセンス素子の製造方法。
- 前記一般式(2)で表される置換基のうち、少なくとも一つのLが炭素原子数1~6のアルキレン基であることを特徴とする請求項1から請求項3まで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の製造方法。
- 前記一般式(2)で表される置換基のうち、少なくとも一つのRが炭素原子数1~6のアルキル基であることを特徴とする請求項1から請求項4まで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の製造方法。
- 前記電子輸送層を、電子輸送材料を含有する塗布液を用いて形成することを特徴とする請求項1から請求項5まで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の製造方法。
- 前記電子輸送材料を含有する塗布液が、極性フッ化溶媒を含有することを特徴とする請求項6に記載の有機エレクトロルミネッセンス素子の製造方法。
- 前記発光層が、極性フッ化溶媒に対する溶解度が前記一般式(1)で表される構造を有する化合物より低い化合物で構成されていることを特徴とする請求項1から請求項7まで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の製造方法。
- 前記発光層が、分子量3000以下の化合物で構成されていることを特徴とする請求項1から請求項8まで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の製造方法。
- 前記発光層が、ジベンゾフラン環、ジベンゾチオフェン環又はカルバゾール環を有し、かつアルキル基、アルケニル基、アルキニル基又はアリールアルキル基を有しない化合物を含有することを特徴とする請求項1から請求項9まで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の製造方法。
- 陽極と陰極との間に、発光層と、ブロック層と、電子輸送層とを備える有機エレクトロルミネッセンス素子であって、
前記ブロック層は、下記一般式(1)で表される構造を有する化合物及び極性フッ化溶媒を含有することを特徴とする有機エレクトロルミネッセンス素子。
- 極性フッ化溶媒が、各構成層全体として1000質量ppm以下含有されていることを特徴とする請求項11に記載の有機エレクトロルミネッセンス素子。
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CN111788707A (zh) * | 2018-02-23 | 2020-10-16 | 柯尼卡美能达株式会社 | 电子器件用组合物、电子器件用墨及电子器件的制造方法 |
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JPWO2019194209A1 (ja) * | 2018-04-06 | 2021-04-30 | コニカミノルタ株式会社 | インク組成物、有機エレクトロルミネッセンス素子の製造方法及び有機エレクトロルミネッセンス素子 |
JP7259847B2 (ja) | 2018-04-06 | 2023-04-18 | コニカミノルタ株式会社 | インク組成物及び有機エレクトロルミネッセンス素子の製造方法 |
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