WO2006087945A1 - 成膜用組成物及び有機電界発光素子 - Google Patents
成膜用組成物及び有機電界発光素子 Download PDFInfo
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- WO2006087945A1 WO2006087945A1 PCT/JP2006/302118 JP2006302118W WO2006087945A1 WO 2006087945 A1 WO2006087945 A1 WO 2006087945A1 JP 2006302118 W JP2006302118 W JP 2006302118W WO 2006087945 A1 WO2006087945 A1 WO 2006087945A1
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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
- H10K71/12—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
- 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
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/50—Sympathetic, colour changing or similar inks
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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
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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
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
- H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
Definitions
- the present invention relates to a film forming composition used for film formation of a hole injection 'transport layer of an organic electroluminescent device, and an organic material in which a hole injection' transport layer is formed from the film forming composition.
- the present invention relates to an electroluminescent element.
- Patent Documents 1 to 3 below describe forming a hole injection layer of an organic electroluminescent element by a wet film forming method.
- Reference 1 shows that an aromatic diamine-containing polyether, which is a hole transport material, and tris (4 bromophenol) ammonium hexachloroantimonate (TBP AH), which is an electron-accepting compound, are mixed with dichloromethane.
- TBP AH tris (4 bromophenol) ammonium hexachloroantimonate
- Reference 2 discloses a method of forming a hole injection layer by spin coating using a 1,2-dichloroethane solution containing an aromatic diamine-containing polyether.
- Reference 3 describes a mixture of 4,4, -bis [(N- (m-tolyl) -N phenolamino] biphenyl and the electron-accepting compound pentasalt-antimony 1, 2 — Disclose a method for forming a hole transport layer by spin coating using a dichloroethane solution.
- Patent Documents 4 and 5 describe compositions for forming a hole injection 'transport layer by an ink jet method.
- Reference 4 discloses a coating liquid in which copper phthalocyanine or a conductive polymer such as polyethylene dioxythiophene (PEDT) and polystyrene sulfonic acid (PSS) are dispersed in a mixed solvent composed of water, lower alcohol, and the like. .
- PEDT polyethylene dioxythiophene
- PSS polystyrene sulfonic acid
- Document 5 discloses a coating solution in which PEDT and PSS are dispersed in a solvent composed of water, ethanol, and dipropylene glycol.
- Patent Document 1 Japanese Patent Laid-Open No. 11-283750
- Patent Document 2 JP 2000-36390 A Patent Document 3: Japanese Patent Laid-Open No. 2002-56985
- Patent Document 4 Japanese Unexamined Patent Publication No. 2000-106278
- Patent Document 5 Japanese Patent Application Laid-Open No. 2004-204114
- All of the hole injection and transport layer coating compositions applied to conventional wet film-forming methods contain water as a solvent.
- Organic electroluminescent elements are usually those whose characteristics are impaired by moisture. For this reason, when a composition containing water is used, it is necessary to remove water as much as possible after film formation. It is difficult to completely remove water from the hole injection / transport layer after film formation. Due to moisture remaining in the film, the characteristics of the conventional organic electroluminescent device are degraded. Due to variations in the amount of residual moisture in the film formation process, the characteristics of individual elements are not constant during the manufacture of organic electroluminescent elements.
- a hole injection layer of an organic electroluminescence device is used as a material for forming a hole transport layer.
- aromatic diamine-containing polyethers, etc. are often poorly soluble in solvents. Therefore, when forming thin layers of organic materials by a wet film formation method, prepare a solution with an appropriate concentration. Hard to do.
- the drying speed of the coating solution is very important in determining the efficiency of the manufacturing process. For example, if a solvent with a high vapor pressure is used, the solvent evaporates when the coating liquid is sprayed from the spray nozzle onto the coating surface, which makes it difficult to clog the nozzle and immediately form a highly uniform organic layer. Become.
- An object of the present invention is to provide a film-forming composition that does not contain water and is used when forming a hole injection layer or a hole transport layer of an organic electroluminescence device.
- the present invention also provides solubility in a hole injecting / transporting material, ejection stability from an injection nozzle, affinity for a formed coating film with an undercoat layer, and a suitable coating layer that can form a uniform coating layer. At least the drying speed It is an object to provide a film-forming composition in which any one, preferably all are improved.
- an object of the present invention is to provide an organic electroluminescent device in which a hole injecting / transporting layer is formed from the film forming composition.
- the film-forming composition of the present invention is a composition used for film formation of a hole injection / transport layer of an organic electroluminescence device, and comprises a hole injection / transport material and a Z or electron-accepting compound. And a film-forming composition containing the material and Z or a liquid in which the compound is dissolved, the liquid having an aromatic ring and Z or alicyclic ring and an oxygen atom in the molecule, and having a boiling point.
- a solvent having a vapor pressure at 25 ° C of not more than ltorr hereinafter referred to as “first solvent”
- first solvent A solvent having a vapor pressure at 25 ° C of not more than ltorr
- the organic electroluminescence device of the present invention is characterized in that the hole injection / transport layer is formed of this film-forming composition.
- FIG. 1 is a cross-sectional view illustrating an example of a configuration of an organic electroluminescent element having a thin layer formed using a film-forming composition to which the present embodiment is applied. is there.
- FIGS. 2a and 2b are schematic views for explaining a coating test method for evaluating the coating state in Examples 1 to 23.
- FIG. 2a is schematic views for explaining a coating test method for evaluating the coating state in Examples 1 to 23.
- FIG. 3 is a schematic diagram showing a spot width evaluated in an example.
- FIG. 4 is a graph showing the relationship between the solvent composition ratio and the spot width in Examples 21 to 23.
- FIG. 5 is a schematic diagram for explaining a coating test method for evaluating the coating state in Examples 24-28.
- FIG. 6 is a graph showing the relationship between the solvent composition ratio and the spot width in Examples 24-28. Detailed description of preferred embodiments and forms of the invention
- the solubility of the hole injecting / transporting material and the Z or electron accepting compound is improved, and a positive drying speed capable of stably forming a uniform coating film is obtained.
- a film-forming composition suitable for film formation of a hole injection 'transport layer is provided.
- a solvent comprising a compound having an aromatic ring and Z or alicyclic ring and an oxygen atom in the molecule is an aromatic Because of its high solubility in hole-injecting / transporting materials such as aromatic amine compounds and electron-accepting compounds such as aromatic boron compounds,
- the first solvent has a boiling point of 200 ° C or higher or a vapor pressure at 25 ° C of ltorr (133Pa) or lower, and is very difficult to evaporate. Therefore, when the first solvent is used for application by the ink jet method or the spray method, nozzle clogging of the injection head due to solvent evaporation is prevented. By suppressing the evaporation of the first solvent from the coating film, a uniform thickness film with no unevenness can be formed due to the self-leveling property of the coating film.
- the film-forming composition of the present invention is suitable for film formation of a hole injection / transport layer by an ink jet method and a spray method because of its leveling ability to dry.
- the resulting device has stable characteristics and improved hole transport capability.
- the present inventors In order to form a uniform film by the inkjet method, the present inventors have a solvent having a low boiling point or a high vapor pressure, and a solvent having a high boiling point or a low vapor pressure. It has been found that it is preferable to use a mixture of a solvent and an appropriate mixing ratio.
- the liquid includes a first solvent, a second solvent that has an aromatic ring and Z or an alicyclic ring and an oxygen atom in the molecule, and does not belong to the first solvent.
- the weight content of the solvent is W
- the weight content of the second solvent is W
- the weight ratio W / W of the second solvent to the first solvent is 1
- W ZW is particularly preferably 1 to 2.5.
- the liquid has an aromatic ester (weight content W) as the first solvent and a boiling point higher than that of the aromatic ester, or a vapor pressure at 25 ° C.
- Low including a low-evaporation solvent (weight content W) belonging to the first solvent, and having a weight ratio W / W power of ⁇ 20.
- W / W is particularly preferably 1 to 2.5. This a b
- a benzoic acid ester as the aromatic ester and an acetic acid ester having an aromatic ring as the low evaporation solvent.
- the liquid a liquid having only the power of the first solvent may be used, and this suppresses evaporation of the solvent from the composition during film formation.
- the hole injecting / transporting material may be an aromatic amine compound, and the electron accepting compound may be an aromatic boron compound and Z or a salt thereof. That ’s right.
- each layer is a uniform layer.
- moisture mixed into the composition for forming a layer may cause moisture to be mixed into the coating film and impair the uniformity of the film.
- the water content in the film composition is preferably as low as possible.
- the film-forming composition of the present invention has a moisture content of 1% by weight. As a result, it is preferable that the uniformity of the film is increased and deterioration of the organic electroluminescent device, particularly deterioration of the cathode is prevented.
- the film-forming composition of the present invention can be suitably used as a coating liquid for forming at least one of a hole injection layer and a hole transport layer.
- a film formed using the film-forming composition of the present invention is excellent in uniformity.
- This film may be a hole injection / transport layer formed in a specific region of the substrate surface where irregularities due to patterned electrodes and partition walls between pixels remain.
- the film-forming composition of the present invention is suitably used as a coating liquid for forming a hole injection layer and a Z or hole transport layer provided between an anode and a light emitting layer.
- the layer in contact with the anode is referred to as “hole injection layer”
- the “hole injection layer” and the other layers are collectively referred to as the “hole transport layer”.
- the layers provided between the anode and the light emitting layer may be collectively referred to as “hole injection / transport layer”.
- the film-forming composition of the present invention includes a hole injection / transport material and a Z or electron accepting compound that form at least one of a hole injection layer and a hole transport layer of an organic electroluminescence device, and these Hole injection 'transport material and liquid that dissolves Z or electron accepting compound , Containing.
- This liquid is a first solvent having an aromatic ring and Z or alicyclic ring and an oxygen atom in the molecule and having a boiling point of 200 ° C or higher or a vapor pressure at 25 ° C of ltorr or lower.
- the aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocyclic ring, but is preferably an aromatic hydrocarbon ring.
- the concentration of the first solvent in the film-forming composition is usually 3% by weight or more, preferably 10% by weight or more, more preferably 50% by weight or more, and further preferably 80% by weight or more. It is preferable that 50% by weight or more of the liquid contained in the composition is the first solvent.
- the liquid in the composition may be substantially only the first solvent.
- the upper limit of the boiling point or the lower limit of the vapor pressure of the first solvent is 200 ° C or higher, the vapor pressure at 25 ° C is ltorr or lower.
- the preferred range of boiling point and vapor pressure varies depending on the ratio of the first solvent in the total solvent and the type of other solvents used in combination, and cannot generally be said, but usually the boiling point of the first solvent is preferably 200 to
- the vapor pressure at 25 ° C is preferably about 0.001 to ltorr.
- Examples of the first solvent include aromatic esters such as methyl benzoate, ethyl benzoate, isopropyl benzoate, propyl benzoate, n-butyl benzoate, dimethyl phthalate, 2-phenoxychetyl acetate, and phenyl propionate. Can be mentioned.
- the liquid may contain a plurality of types of first solvents!
- the liquid may include a first solvent that is relatively less volatile and a first solvent that is relatively volatile.
- the liquid contains at least one first solvent and at least one second solvent that has an aromatic ring and Z or alicyclic ring and an oxygen atom in the molecule and does not belong to the first solvent. But you can.
- Aromatic esters that do not belong to the first solvent such as phenyl acetate and ethyl (pentafluoro oral benzoate);
- Aromatic ethers such as carsol and funnel
- Cycloaliphatic ketones such as cyclohexanone, methylcyclohexanone, cyclopentanone, cycloheptanone, cyclotanone;
- Cyclohexanol Methinorecyclohexanol, Cyclopentanol, Cycloheptano Alicyclic alcohols such as alcohol and cyclooctanol;
- the second solvent has a boiling point of less than 200 ° C and a vapor pressure at 25 ° C exceeding ltorr.
- the second solvent preferably has a boiling point of 150 ° C or higher and a vapor pressure at 25 ° C of 5 torr or lower.
- the second solvent may have a higher solubility than the first solvent, which preferably dissolves the hole injecting / transporting material and the electron accepting compound well.
- the liquid may contain at least one first solvent and at least one second solvent.
- the ratio W / W is 1 to 20, more preferably 1 to 19.
- the first solvent is more than this range
- This ratio W / W may be 3-19.
- W ZW is preferably 1 to 2.5.
- the liquid may contain a plurality of types of first solvents.
- a first solvent having a relatively high evaporation property and a first solvent having a relatively low evaporation property may be included.
- a low-evaporation first solvent with a vapor pressure of 0.1 ltorr or less may be mixed and used.
- ZW is preferably 1 to 20, particularly 1 to 19.
- W ZW is particularly preferably 1 to 2.5.
- a benzoic acid ester such as ethyl benzoate
- an acetic ester having an aromatic ring such as 2-phenoxychetyl acetate
- the first solvent having a relatively high evaporation property and the first solvent having a relatively low evaporation property have a difference in vapor pressure at a force of 25 ° C with a boiling point difference of 20 ° C or more, particularly 40 to 100 ° C. Is greater than 0.09 torr, especially 0.2 It is preferable to be-. 999 torr.
- the solubility of the highly-evaporable first solvent in the hole-injecting / transporting material and the electron-accepting compound may be higher than that of the low-evaporating first solvent.
- the liquid may contain three or more first solvents.
- the liquid may contain three or more kinds of first solvents having different evaporabilities. In this case, if the weight content of the first solvent with the highest evaporation is W and the weight content of the first solvent with the lowest evaporation is W, W /
- W is preferably 1-20, in particular 1-19, and may be 1-2.5.
- the liquid is still another solvent, for example, at least one aromatic hydrocarbon such as benzene, toluene and xylene; or at least one kind such as N, N-dimethylformamide, N, N-dimethylacetamide and the like. May contain one or more amides such as dimethyl sulfoxide.
- aromatic hydrocarbon such as benzene, toluene and xylene
- amides such as dimethyl sulfoxide.
- the liquid as described above contains 50% by weight or more of the first solvent, and the force of the first solvent may be substantially constituted.
- Examples of the hole injecting / transporting material include aromatic amine compounds, phthalocyanine derivatives, porphyrin derivatives, metal complexes of 8-hydroxyquinoline derivatives having a diarylamino group, oligothiophene derivatives, and the like. Furthermore, a polymer compound having a hole transporting site in the molecule can also be used. These hole injection and transport materials can be used alone or in combination of two or more.
- Examples of the polymer compound having a hole transporting site in the molecule include a polymer aromatic amine compound containing an aromatic tertiary amino group as a constituent unit in the main skeleton.
- Specific examples include a hole injection / transport material having a structure represented by the following general formula (I) as a repeating unit.
- a ⁇ Ar represents a divalent aromatic ring group that may have a substituent each independently, and R U to R 12 may each independently have a substituent.
- X represents a direct bond or the following linking group power.
- aromatic ring group includes both “group derived from an aromatic hydrocarbon ring” and “group derived from an aromatic heterocycle”.
- 8 to 8 !: 14 are preferably each independently a divalent benzene ring, naphthalene ring, anthracene ring, or biphenyl which may have a substituent.
- a group derived from -ru preferably a group derived from a benzene ring.
- the substituent include a halogen atom; a straight-chain or branched alkyl group having 1 to 6 carbon atoms such as a methyl group and an ethyl group; a alkenyl group such as a vinyl group; a methoxycarbol group, an ethoxycarbol group, etc.
- an alkyl group having 1 to 3 carbon atoms is preferable, and a methyl group is particularly preferable.
- R 11 and R 12 are each independently a phenyl group, naphthyl group, anthryl group, pyridyl group, triazyl group, birazyl group, quinoxalyl group, chael group, which may have a substituent, Or a phenyl group, preferably a phenyl group, a naphthyl group or a biphenyl group, more preferably a phenyl group.
- substituent include the same groups as those described above as the group that the aromatic ring group in Ar ⁇ Ar 14 may have.
- the compound having the structure represented by the general formula (I) as a repeating unit is, for example, the method of Kido et al. (Polymers for Advanced Tecnologies, 7 ⁇ , p. 31, 1996; JP-A-9-188). 756)).
- the hole injecting / transporting material which is a polymer compound having a hole transporting site in the molecule, is most preferably a homopolymer having a structure represented by the general formula (I). It may be a copolymer (copolymer) with any of the above monomers. In the case of a copolymer, it is preferable to contain 50 mol% or more, particularly 70 mol% or more of the structural unit represented by the general formula (I).
- the hole injecting / transporting material which is a polymer compound may contain a plurality of types of structures represented by the general formula (I) in one compound.
- a plurality of compounds containing a structure represented by the general formula (I) may be used in combination.
- Examples of the hole injecting / transporting material that also has high polymer compound power include conjugated polymers, such as polyfluorene, polypyrrole, polyarrin, polythiophene, polyparaffin. Phenylene vinylene is preferred.
- Examples of the aromatic amine compound as a hole-injecting / transporting material include compounds having a triarylamine structure, and a conventional hole-injecting / transporting layer-forming material in an organic electroluminescence device. It can also be used by appropriately selecting from the compounds that have been used as.
- conventionally known compounds can be used in addition to the compound having the structure represented by the general formula (I).
- Such conventionally known compounds include, for example, aromatic diamine compounds in which tertiary aromatic amine units such as 1,1-bis (4di-p-tolylaminophenol) cyclohexane are linked (Japanese Patent Laid-Open No. Sho 59). — No.
- One of these compounds may be used alone, or two or more thereof may be mixed and used as necessary.
- the content of the hole injecting / transporting material in the film-forming composition of the present invention is usually 0.05% by weight or more, preferably 1% by weight or more. However, it is usually 50% by weight or less, preferably 30% by weight or less.
- Examples of the electron-accepting compound contained in the film-forming composition to which this embodiment is applied include, for example, an aromatic boron compound or a salt thereof, a metal halide, a Lewis acid, an organic acid, an aromatic amine and a halogeni. Examples thereof include one or two or more compounds selected from a group consisting of a salt with a metal and a salt of an aromatic amine and a Lewis acid. These electron-accepting compounds are used in combination with a hole injecting / transporting material, and the conductivity of the hole injecting layer can be improved by oxidizing the hole injecting / transporting material.
- aromatic boron compound or a salt thereof Specific examples are shown below, but are not limited thereto.
- the electron-accepting compound one selected from the group force consisting of a metal halide, a Lewis acid, an organic acid, a salt of an aromatic amine and a metal halide, a salt of an aromatic amine and a Lewis acid, or Specific examples of the two or more compounds include the following compounds.
- the ratio W / W between the weight content W of the electron-accepting compound and the weight content W of the hole e injection 'transport material in the film-forming composition of the present invention is 0.001 or more, preferably Is 0. 01
- the film-forming composition of the present invention preferably has a low water content for the uniformity of the film formed by the ink-jet film-forming method as described above and the prevention of deterioration of the organic electroluminescence device.
- the amount of water contained in the film-forming composition is preferably 1% by weight or less, more preferably 0.1% by weight or less, and particularly preferably 0.05% by weight or less.
- the solvent used for the preparation of the film-forming composition, the hole injecting / transporting material, and Z or the electron-accepting compound so that the amount of water in the film-forming composition is not more than the above upper limit. It is preferable to use after purification or drying treatment to remove enough water if necessary!
- the film-forming composition of the present invention contains various additives such as a leveling agent and an antifoaming agent, as necessary, in addition to the solvent, the hole injecting / transporting material and / or the electron accepting compound. It may be included. Moreover, you may contain the binder resin mentioned later.
- FIGS. La to lc are cross-sectional views illustrating an example of an organic electroluminescence device having a thin layer formed using the film-forming composition of the present invention.
- An organic electroluminescent device 100a shown in FIG. La includes a substrate 101, an anode 102, a hole injection layer 103, a light emitting layer 105, and a cathode 107, which are sequentially stacked on the substrate 101.
- the substrate 101 is a support for the organic electroluminescent element 100a.
- the material forming the substrate 101 include a quartz plate, a glass plate, a metal plate, a metal foil, a plastic film, and a plastic sheet.
- a transparent plastic sheet such as a glass plate, polyester, polymetatalylate, polycarbonate, and polysulfone is preferable.
- plastic it is preferable to provide a dense silicon oxide film or the like on one or both surfaces of the substrate 101 so as to improve the gas normality.
- the anode 102 is provided on the substrate 101 and plays the role of hole injection into the hole injection layer 103.
- Materials for the anode 102 include metals such as aluminum, gold, silver, nickel, palladium and platinum; conductive metal oxides such as oxides of indium and Z or tin; And halogenated metals such as copper, carbon black, and conductive polymers such as poly (3-methylthiophene), polypyrrole, and polyarine.
- the anode 102 is usually formed by sputtering, vacuum deposition, etc. on the substrate 101; metal fine particles such as silver, fine particles such as copper iodide, carbon black, conductive metal oxide fine particles or conductive A method in which fine polymer powder or the like is dispersed in a suitable binder resin solution and applied onto the substrate 101; a method in which a conductive polymer thin film is directly formed on the substrate 101 by electrolytic polymerization; a conductive property on the substrate 101 Examples include a method of applying a polymer solution.
- the anode 102 usually has a visible light transmittance of 60% or more, particularly preferably 80% or more.
- the thickness of the anode 102 is usually lOOOnm or less, preferably 500 nm or less, and usually 5 nm or more, preferably 10 nm or more.
- the hole injection layer 103 provided on the anode 102 is preferably formed by a wet film-forming method, preferably using the film-forming composition of the present invention. Since organic electroluminescent elements are formed by laminating a large number of layers having organic compound power, it is very important that the film quality is uniform.
- a layer is formed by a wet film formation method, a known film formation method such as a coating method such as a spin coating method or a spray method, or a printing method such as an ink jet method or a screen method is adopted depending on the material and properties of the base.
- the inkjet method is optimal in that a uniform film can be formed in a desired region by high-definition patterning.
- the ink jet method is suitable when a layer made of an organic compound is provided in a specific region of the substrate surface where unevenness due to patterned electrodes and partition walls between pixels remains.
- the hole injection layer 103 is preferably formed using a hole-injecting / transporting material and an electron-accepting compound capable of oxidizing the hole-injecting / transporting material.
- the film thickness of the hole injection layer 103 formed in this way is usually 5 nm or more, preferably lOnm or more. However, it is usually 1, OOOnm or less, preferably 500 nm or less.
- the light-emitting layer 105 is provided on the hole injection layer 103 and efficiently recombines electrons injected from the cathode 107 and holes transported from the hole injection layer 103 between electrodes to which an electric field is applied. And a material that efficiently emits light by recombination.
- the light-emitting layer 105 can be made of a metal complex such as an aluminum complex of 8-hydroxyquinoline, a metal complex of 10-hydroxybenzo [h] quinoline, a bisstyrylbenzene derivative, a bisstyryl alcohol.
- Low molecular light-emitting materials such as mono-ene derivatives, metal complexes of (2-hydroxyphenol) benzothiazole, silole derivatives; poly (P-phenylene-ylene), poly [2-methoxy-5- (2-ethyl) And xyloxy) 1,4 phenylene vinylene], poly (3 alkylthiophene), and a polymer compound such as polyvinylcarbazole mixed with a light emitting material and an electron transfer material.
- a metal complex such as an aluminum complex of 8-hydroxyquinoline as a host material, a naphthacene derivative such as rubrene, a condensed polycyclic aromatic ring such as a quinacridone derivative or perylene, etc. 1 to:
- Doping with LO weight% can greatly improve the light emission characteristics of the device, particularly the driving stability.
- These materials are formed into a thin film on the hole injection layer 103 by a wet film forming method such as a vacuum deposition method or an ink jet film forming method.
- the film thickness of the light emitting layer 105 formed in this manner is usually 10 nm or more, preferably 30 nm or more. However, it is usually 200 nm or less, preferably lOOnm or less.
- the cathode 107 serves to inject electrons into the light emitting layer 105.
- the material used as the cathode 107 is preferably a metal having a low work function, for example, a suitable metal such as tin, magnesium, indium, calcium, aluminum, silver, or an alloy thereof. Specific examples include low work function alloy electrodes such as magnesium-silver alloy, magnesium-indium alloy, and aluminum-lithium alloy.
- the film thickness of the cathode 107 is usually the same as that of the anode 102.
- the cathode 107 made of a low work function metal it is effective to increase the stability of the device by further laminating a metal layer having a high work function and stable to the atmosphere.
- metals such as aluminum, silver, copper, nickel, chromium, gold and platinum are used.
- ultra-thin insulation such as LiF, MgF, LiO, etc. at the interface between the cathode 107 and the light emitting layer 105
- the efficiency of the device can be improved.
- FIG. Lb is a diagram for explaining a function-separated light emitting element.
- a hole transport layer 104 is provided between the hole injection layer 103 and the light emitting layer 105 in order to improve the light emitting characteristics of the device, and the other layers are formed.
- the structure is similar to that of the organic electroluminescent device 100a shown in FIG.
- the hole transport layer 104 As a material of the hole transport layer 104, the hole injection efficiency from the hole injection layer 103 is high. In addition, it is necessary to be a material that can efficiently transport injected holes. For this purpose, it is required that the ion potential is small, the hole mobility is large, and the stability is high, and impurities that become traps are hardly generated at the time of manufacture and use. In addition, since the layer is in direct contact with the light-emitting layer 105, it is preferable that a substance that quenches light emission is not included.
- Examples of the hole injection / transport material for forming the hole transport layer 104 include the same compounds as those exemplified as the hole injection / transport material in the film-forming composition of the present invention.
- polymer materials such as polyarylene ether sulfone containing polyvinylcarbazole, polyvinyltriphenylamine, and tetraphenylbenzidine can be used.
- the hole transport layer 104 is formed by laminating these hole injection and transport materials on the hole injection layer 103 by a wet film formation method such as an ink jet film formation method or a vacuum deposition method.
- the thickness of the hole transport layer 104 formed in this manner is usually lOnm or more, preferably 30 nm. However, it is usually 300 nm or less, preferably lOOnm or less.
- FIG. Lc is a diagram for explaining another embodiment of the function-separated light emitting device.
- the electron transport layer 106 is provided between the light emitting layer 105 and the cathode 107, and the other layers have the same structure as the organic electroluminescent device 100b shown in FIG. Have a success.
- the compound used for the electron transport layer 106 is required to be capable of easily injecting electrons from the cathode 107 and further having an electron transport capability.
- electron transporting materials include 8-hydroxyquinoline aluminum complexes, oxadiazole derivatives, or systems in which they are dispersed in a resin such as polymethyl methacrylate (PMMA), phenantorin derivatives, 2-t-butyl. —9,10-N, N, —Discyananthraquinone dimine, n-type hydrogenated amorphous silicon carbide, n-type zinc sulfide, n-type selenium zinc, and the like.
- PMMA polymethyl methacrylate
- phenantorin derivatives 2-t-butyl.
- the electron transport layer 106 is formed by laminating these electron transport materials on the light emitting layer 105 by a wet film forming method such as an ink jet film forming method or a vacuum deposition method.
- the thickness of the electron transport layer 106 formed in this way is usually 5 nm or more, preferably lOnm or more. However, it is usually 200 ⁇ m or less, preferably lOOnm or less.
- the organic electroluminescent element of the present invention is not limited to the illustrated one.
- Example a structure opposite to that shown in FIGS. La to lc, that is, a cathode 107, a light emitting layer 105, a hole injection layer 103, and an anode 102 can be stacked on the substrate 101 in this order. It is also possible to provide an organic electroluminescent element between two substrates, at least one of which is highly transparent. Further, the layer containing the hole injecting / transporting material and the electron accepting compound need not be the hole injecting layer 103 in contact with the anode 102, and is provided between the anode 102 and the light emitting layer 105. In particular, the hole injection layer 103 is preferable.
- an arbitrary layer may be provided between the layers shown in FIGS. La to lc.
- a wall-like structure made of an insulating material surrounding the pixel what is called a “bank”, a partition that divides the cathode, a nonlinear element that drives the pixel, and the like may be provided.
- the anode 102 is formed on the substrate 101 by sputtering, vacuum deposition or the like.
- at least one layer of a hole injection layer 103 and a hole transport layer 104 is formed by an ink jet film forming method using the composition of the present invention.
- a light emitting layer 105 is formed on the hole injection layer 103 and / or the hole transport layer 104 by a vacuum deposition method or an ink jet film formation method.
- the electron carrying layer 106 is formed as needed by a vacuum evaporation method or the inkjet film-forming method.
- a cathode 107 is formed on the light emitting layer 105 or the electron transport layer 106.
- the hole injection layer and the electron-accepting compound are usually in the place of a hole injection and transport material
- an additive such as a binder resin or coating property improving agent that does not become a hole trap is added if necessary, and dissolved to prepare a coating solution, that is, a film-forming composition.
- This composition is applied onto the anode 102 by an inkjet film formation method and dried to form at least one layer of a hole injection layer 103 and a hole transport layer 104.
- the content of the binder resin is usually preferably 50% by weight or less, more preferably 30% by weight or less, in terms of hole mobility, in terms of the content in these formed layers. Most preferably, it contains substantially no binder resin.
- the content of the binder resin is usually preferably 50% by weight or less, more preferably 30% by weight or less, in terms of hole mobility, in terms of the content in these formed layers. Most preferably, it contains substantially no binder resin.
- a heating process is performed, and then the film is obtained. The characteristics of the element can be improved by reducing the amount of residual solvent mixed in or the amount of moisture mixed in the inkjet film forming process.
- the substrate is heated by means such as a hot plate or an oven.
- a hot plate or an oven In order to sufficiently obtain the effect of the heat treatment, it is preferable to perform the treatment at 100 ° C or higher.
- the heating time is usually about 1 minute to 8 hours.
- the layer containing the hole-injecting / transporting material and the Z or electron-accepting compound formed by the ink-jet film forming method in this manner has a smooth surface, and is therefore caused by the surface roughness of the anode 102 such as ITO. It is possible to solve the problem of a short circuit during device fabrication.
- the exemplified compound (I3) was used as the hole injecting / transporting material, and the exemplified compound (D-30) was used as the electron-accepting compound.
- composition for film formation was prepared by mixing each component compound and the solvent in the formulation shown in Table 2.
- the prepared film forming composition is simply referred to as “ink”.
- an ink jet coating apparatus equipped with a piezo drive type ejection head was used to observe how the ink also ejected the nozzle force of the ejection head as follows.
- Nozzle force is continuously ejected for 5 minutes, and the ejection state after 5 minutes is observed.
- the nozzle is clogged and ink cannot be ejected, or the ink is ejected diagonally and normal ejection is possible.
- the number of missing defective nozzles was counted and evaluated as follows.
- NG (Not Good): Number of defective nozzles Z Ratio of all nozzles is 50% or more
- the anode 202 is formed by patterning into a predetermined shape using a photoetching method, Thereafter, a bank 203 was formed on the substrate 201 by forming a polyimide pattern.
- the size of the pixel portion 204 surrounded by the bank 203 is 135 ⁇ 85 / ⁇ m, and the pixel area is arranged in a matrix of 54 columns ⁇ 32 rows.
- the ink 205 was prepared for the pixel 204 divided by the nozzle 203 using the 206 nozzle force of the ejection head 207. Was spray coated.
- G A film that spreads over the entire area of the pixel is formed although there is some unevenness.
- -Jim width means the width of a region where the film thickness of the ink 205 at the edge portion of the bank 203 is not uniform as shown in FIG.
- FIG. 4 shows the relationship between the solvent composition ratio and the jimi width.
- a good film can be obtained with any of the inks of the ethyl benzoate of Examples 5 and 14, and the mixed solvent of ethyl benzoate and 2-funchetyl acetate of Examples 6 to 8, 14 to 18, and 20 to 23. It was. This is because the boiling point of ethyl benzoate and 2-phenoxychetyl acetate is as high as 200 ° C or higher, the vapor pressure at room temperature is less than ltorr, and the coating solution was difficult to dry. This is thought to be due to the fact that the spread and leveling were even better.
- Example 21 to 23 the spot width was 20 / zm or less, and a good coating state was obtained with all inks.
- composition for film formation (ink) was prepared by mixing each component compound and the solvent in the formulation shown in Table 4. [0111] Evaluation of spray condition
- the “normally sprayed” state means that the shape of the spray that also ejects the nozzle force becomes a clean conical shape. If the nozzle is clogged, the spray shape will be disturbed at the clogged part, and the spray shape will not normally be conical.
- the coating state was evaluated in the same manner as in Examples 1 to 23.
- the spot width was evaluated in the same manner as in Examples 21-23.
- FIG. 6 shows the relationship between the solvent composition ratio and the jimi width.
- Example 24 Ink 24 3.00 0.60 3 1 G VG 16.17
- Example 25 Ink 25 3.00 0.60 2.5 1 G VG 1 1.98
- Example 26 Ink 26 3.00 0.60 2 1 G VG 1 1.31
- Example 27 Ink 27 3.00 0.60 1.5 1 G VG 10.99
- Example 28 Ink 28 3.00 0.60 1 1 G VG 10.78
- the spot width was 20 / zm or less, and a good coating state was obtained with all inks.
- the ink according to the present invention is suitable not only for the inkjet method but also for spray coating.
- the ink according to the present invention has excellent characteristics such as "hard to dry” and “good leveling", such as coating methods other than the ink jet method and spray method, for example, various printing methods such as flexographic printing method, The same applies to a coating method in which ink is supplied from a slit-like nozzle such as blade coating or a spin coating method.
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Abstract
Description
Claims
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KR1020127018157A KR101415586B1 (ko) | 2005-02-15 | 2006-02-08 | 막형성용 조성물 및 유기 전계 발광 소자 |
JP2007503622A JP5194787B2 (ja) | 2005-02-15 | 2006-02-08 | 成膜用組成物及び有機電界発光素子 |
EP06713261.3A EP1850368B2 (en) | 2005-02-15 | 2006-02-08 | Film forming composition and organic electroluminescent device |
KR1020077018685A KR101237264B1 (ko) | 2005-02-15 | 2006-02-08 | 막형성용 조성물 및 유기 전계 발광 소자 |
US11/815,669 US8053973B2 (en) | 2005-02-15 | 2006-02-08 | Film forming composition and organic electroluminescent device |
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JP2005037902 | 2005-02-15 | ||
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US (1) | US8053973B2 (ja) |
EP (1) | EP1850368B2 (ja) |
JP (4) | JP5194787B2 (ja) |
KR (2) | KR101415586B1 (ja) |
CN (1) | CN100573965C (ja) |
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US10323181B2 (en) | 2015-01-26 | 2019-06-18 | Sumitomo Chemical Company, Limited | Composition containing phosphorescent compound and light emitting device using the same |
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JP2019523998A (ja) * | 2016-06-17 | 2019-08-29 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
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JP7082984B2 (ja) | 2017-02-20 | 2022-06-09 | ノヴァレッド ゲーエムベーハー | 電子半導体デバイスおよびその電子半導体デバイスの製造方法および化合物 |
US12022672B2 (en) | 2017-02-20 | 2024-06-25 | Novaled Gmbh | Electronic semiconducting device, method for preparing the electronic semiconducting device and compound |
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Also Published As
Publication number | Publication date |
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KR101415586B1 (ko) | 2014-08-06 |
KR101237264B1 (ko) | 2013-02-27 |
US8053973B2 (en) | 2011-11-08 |
JP2016054311A (ja) | 2016-04-14 |
TWI396703B (zh) | 2013-05-21 |
JP5194787B2 (ja) | 2013-05-08 |
JP2012084909A (ja) | 2012-04-26 |
JP5720559B2 (ja) | 2015-05-20 |
EP1850368A1 (en) | 2007-10-31 |
KR20120096075A (ko) | 2012-08-29 |
US20090033208A1 (en) | 2009-02-05 |
JP6172243B2 (ja) | 2017-08-02 |
JP2015092602A (ja) | 2015-05-14 |
EP1850368B2 (en) | 2021-04-21 |
EP1850368A4 (en) | 2012-04-04 |
CN101120459A (zh) | 2008-02-06 |
EP1850368B1 (en) | 2013-04-24 |
JP6044625B2 (ja) | 2016-12-14 |
JPWO2006087945A1 (ja) | 2008-07-03 |
TW200640993A (en) | 2006-12-01 |
KR20070103452A (ko) | 2007-10-23 |
CN100573965C (zh) | 2009-12-23 |
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