WO2012133165A1 - Élément électroluminescent et son procédé de fabrication - Google Patents

Élément électroluminescent et son procédé de fabrication Download PDF

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WO2012133165A1
WO2012133165A1 PCT/JP2012/057480 JP2012057480W WO2012133165A1 WO 2012133165 A1 WO2012133165 A1 WO 2012133165A1 JP 2012057480 W JP2012057480 W JP 2012057480W WO 2012133165 A1 WO2012133165 A1 WO 2012133165A1
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group
formula
light emitting
represented
layer
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PCT/JP2012/057480
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Japanese (ja)
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飯島　孝幸
東村　秀之
田中　正信
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住友化学株式会社
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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
    • H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/805—Electrodes
    • H10K59/8052—Cathodes
    • 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]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene

Definitions

  • the present invention is a light emitting device having an anode, a light emitting layer, an electron injection layer and a cathode, wherein the electron injection layer contains an organic compound having an anionic ionic group, and the cathode has an aspect ratio of 1. Contains less than 5 conductive materials.
  • the stacked structure 60 is configured by stacking a plurality of organic layers, and at least one of the plurality of organic layers is the light emitting layer 50.
  • the laminated structure 60 includes an electron injection layer 44 as at least one organic layer of the plurality of organic layers.
  • the electron injection layer 44 is disposed between the cathode 34 and the light emitting layer 50.
  • the hole injection layer is a layer adjacent to the anode and has a function of receiving holes from the anode, and further, a function of transporting holes as needed, and a function of supplying holes to the light emitting layer.
  • the hole transport layer is a layer mainly having a function of transporting holes, and further, if necessary, a function of receiving holes from the anode, a function of supplying holes to the light emitting layer, and injected from the cathode.
  • the electron transport layer and the hole transport layer may be collectively referred to as a charge transport layer.
  • the electron injection layer and the hole injection layer may be collectively referred to as a charge injection layer.
  • Carbon black is preferable as the carbon material.
  • the longest diameter of the nanostructure is preferably 1000 nm or less, more preferably 800 nm or less, still more preferably 500 nm or less, particularly preferably 300 nm or less, and particularly preferably 100 nm because the dispersibility of the nanostructure becomes good. In the following, it is particularly preferably 50 nm or less.
  • the number average ferret diameter (Feret diameter) of the conductive material is preferably 1000 nm or less, more preferably 800 nm or less, still more preferably 500 nm or less, particularly preferably 300 nm or less, particularly preferably 100 nm or less, and even more preferably. 50 nm or less.
  • a cathode is formed by a coating method by coating a coating solution containing a conductive material having an aspect ratio of less than 1.5, a spin coating method, a casting method, a micro gravure coating method, a gravure coating method, Adopting bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method, offset printing method, inkjet printing method, capillary coating method, nozzle coating method, etc.
  • a film can be formed.
  • the cathode 34 has a single-layer structure composed of only one layer or a laminated structure composed of two or more layers.
  • a laminated structure consisting of two or more layers for example, two or more layers are sequentially laminated by a coating method, or two or more layers formed separately by a casting method or the like are laminated by a lamination method.
  • the cathode 34 is produced.
  • the cathode 34 may contain an ionic compound in addition to the conductive material having an aspect ratio of less than 1.5.
  • the ionic compound here includes a cation and an anion.
  • the ionic compound may contain water of hydration and a neutral ligand.
  • the neutral ligand is a nonionic compound having a lone electron pair capable of coordination bonding, and means a compound that does not change the oxidation number of the ionic compound when bonded to the ionic compound. Examples of compounds that can be neutral ligands include pyridine, 2,2'-bipyridyl, phenanthroline, terpyridine, triphenylphosphine, carbon monoxide, and crown ether.
  • Examples of cations include metal cations, organic cations, and ammonium cations.
  • a metal cation is preferable since the stability of the cation is excellent.
  • metal cations examples include alkali metal cations, alkaline earth metal cations, typical metal cations, and transition metal cations.
  • the metal cation is preferably an alkali metal cation or an alkaline earth metal cation.
  • alkali metal cations include Li + , Na + , K + , Rb + , Cs + , Fr + .
  • Li + , Na + , K + , Rb + and Cs + are preferable, and Cs + is more preferable.
  • alkaline earth metal cation examples include Mg 2+ , Ca 2+ , Sr 2+ and Ba 2+ .
  • organic cation examples include an onium cation having a nitrogen-containing aromatic ring such as an imidazolium cation and a pyridinium cation, an ammonium cation, and a phosphonium cation.
  • anion examples include F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , OH ⁇ , CN ⁇ , NO 3 ⁇ , NO 2 ⁇ , ClO ⁇ , ClO 2 ⁇ , ClO 3 ⁇ , ClO 4 ⁇ , and CrO 4 2.
  • Examples of the optionally substituted hydrocarbyl group represented by R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 include a methyl group, an ethyl group, and a propyl group. , Isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, nonyl group, dodecyl group, pentadecyl group, octadecyl group, docosyl group, etc.
  • alkyl group having 1 to 50 carbon atoms
  • An alkyl group a cyclic saturated hydrocarbyl group having 3 to 50 carbon atoms such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclononyl group, a cyclododecyl group, a norbornyl group, an adamantyl group; an ethenyl group, a propenyl group Carbon such as 3-butenyl group, 2-butenyl group, 2-pentenyl group, 2-hexenyl group, 2-nonenyl group, 2-dodecenyl group, etc.
  • An alkenyl group having 2 to 50 atoms phenyl group, 1-naphthyl group, 2-naphthyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, 4-propyl Carbon atoms such as phenyl group, 4-isopropylphenyl group, 4-butylphenyl group, 4-tert-butylphenyl group, 4-hexylphenyl group, 4-cyclohexylphenyl group, 4-adamantylphenyl group, 4-phenylphenyl group Aryl group having 6 to 50 number; phenylmethyl group, 1-phenyleneethyl group, 2-phenylethyl group, 1-phenyl-1-propyl group, 1-phenyl-2-propyl group, 2-phenyl-2-propyl group Group, 3-phenyl-1-propyl group, 4-phenyl-1-butyl group, 5-phenyl
  • the hydrocarbyl group which may have a substituent is preferably an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 carbon atoms, an alkyl group having 1 to 12 carbon atoms, carbon An aryl group having 6 to 18 atoms is more preferable, an alkyl group having 1 to 6 carbon atoms, and an aryl group having 6 to 12 carbon atoms are more preferable.
  • Examples of the substituent that the hydrocarbyl group may have include an alkoxy group, an aryloxy group, an amino group, a substituted amino group, a silyl group, a substituted silyl group, a halogen atom, an imine residue, an amide group, an acid imide group, and a monovalent group.
  • the hydrocarbyl group may have, an amino group, a monovalent heterocyclic group, a mercapto group, a hydroxyl group, and a carboxyl group are preferable, and an amino group, a pyridyl group, a mercapto group, a hydroxyl group, and a carboxyl group are more preferable.
  • the plurality of substituents may be the same or different.
  • the alkoxy group which is a substituent that the hydrocarbyl group may have may be linear, branched or cyclic.
  • the number of carbon atoms of the alkoxy group is usually 1-20, and preferably 1-10.
  • Examples of the alkoxy group that the hydrocarbyl group may have include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group.
  • the hydrogen atom in the alkoxy group that the hydrocarbyl group may have may be substituted with a fluorine atom.
  • Examples of the alkoxy group substituted with a fluorine atom include a trifluoromethoxy group, a pentafluoroethoxy group, a perfluorobutoxy group, a perfluorohexyloxy group, a perfluorooctyloxy group, a methoxymethyloxy group, and 2-methoxy.
  • An ethyloxy group is mentioned.
  • the number of carbon atoms of the aryloxy group that is a substituent that the hydrocarbyl group may have is usually 6 to 60, and preferably 6 to 48.
  • Examples of the aryloxy group that the hydrocarbyl group may have include a phenoxy group and a C 1 to C 12 alkoxyphenoxy group (where C represents a carbon atom. The number attached represents the number of carbon atoms. “C 1 ”To C 12 ” represents that the number of carbon atoms is 1 to 12. The same shall apply hereinafter.), A C 1 to C 12 alkylphenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, and A pentafluorophenyloxy group is mentioned.
  • Examples of the C 1 -C 12 alkoxyphenoxy group include a methoxyphenoxy group, an ethoxyphenoxy group, a propyloxyphenoxy group, an isopropyloxyphenoxy group, a butoxyphenoxy group, an isobutoxyphenoxy group, a sec-butoxyphenoxy group, a tert-butoxyphenoxy group.
  • Examples of the C 1 -C 12 alkylphenoxy group include a methylphenoxy group, an ethylphenoxy group, a dimethylphenoxy group, a propylphenoxy group, a 1,3,5-trimethylphenoxy group, a methylethylphenoxy group, an isopropylphenoxy group, and a butylphenoxy group.
  • the substituted silyl group which is a substituent that the hydrocarbyl group may have, is selected from the group consisting of, for example, one or more hydrogen atoms in the silyl group consisting of an alkyl group, an aryl group, an arylalkyl group, and a monovalent heterocyclic group And silyl groups substituted with one or more of the above-described groups.
  • the number of carbon atoms of the substituted silyl group is usually 1 to 60, and preferably 2 to 48.
  • the imine residue which is a substituent which the hydrocarbyl group may have is one hydrogen atom in this structure from an imine compound having a structure represented by the formula: H—N ⁇ C ⁇ or a formula: —N ⁇ CH—. It means the residue without.
  • the imine compound include compounds in which a hydrogen atom bonded to a nitrogen atom in aldimine, ketimine, and aldimine is substituted with an alkyl group, aryl group, arylalkyl group, arylalkenyl group, arylalkynyl group, or the like.
  • the number of carbon atoms in the imine residue is usually 2-20, and preferably 2-18.
  • the acid imide group which is a substituent that the hydrocarbyl group may have is a residue obtained by removing a hydrogen atom bonded to the nitrogen atom from the acid imide.
  • the acid imide group usually has 4 to 20 carbon atoms, and preferably 4 to 18 carbon atoms. The following groups are mentioned as an example of an acid imide group.
  • a and b are each independently preferably an integer of 1 to 3, more preferably 1 or 2.
  • a and b are combinations in which there is no bias in the charge of the ionic compound represented by the formula (hh-1) as a whole.
  • m ′ represents an integer of 1 or more.
  • the definition, specific examples, and preferred examples of the metal cation represented by M m ′ + are as described above.
  • n ′ represents an integer of 1 or more.
  • the definition, specific examples, and preferred examples of the anion represented by X ′ n- are as described above.
  • Examples of the anode material constituting the anode 32 include conductive metal oxides, metals, carbon materials, and conductive polymer materials.
  • As anode materials constituting the anode 32 indium oxide, zinc oxide, tin oxide, and metal oxides such as ITO, AZO, IZO, NESA, etc., which are composites thereof, metals such as gold, platinum, silver, copper, etc.
  • Conductive polymers such as carbon materials such as carbon nanotubes, graphite, polyaniline, polythiophene (for example, poly (3,4-ethylenedioxythiophene) / polystyrenesulfonic acid), polypyrrole, and polymers containing these. Examples include polymer materials.
  • the anode has a single-layer structure consisting of only one layer or a laminated structure of two or more layers.
  • Examples of the method for forming the anode 32 include a vacuum deposition method, a sputtering method, a laminating method in which a metal thin film is thermocompression bonded, and a coating method, and a coating method is preferable.
  • a layer made of a conductive polymer material, or a layer made of a metal oxide, a metal fluoride, or an organic insulating material may be provided between the anode 32 and the electron injection layer 44.
  • the electron injection layer 44 contains an organic compound having an anionic ionic group.
  • the (n 2 +2) -valent aromatic group represented by Ar 2 is the remaining atomic group obtained by removing (n 2 +2) hydrogen atoms from the aromatic compound, and is substituted
  • the group which may have a group is meant.
  • organic compounds represented by formula (15), formula (17), formula (21), formula (24), formula (30), formula (59) to formula (61) are represented by formula (1) to Organic compounds represented by formula (3), formula (8), formula (10), and formula (59) are more preferred, and are represented by formula (1), formula (2), formula (8), and formula (59). Organic compounds Particularly preferred.
  • a hydrogen atom in the hydrocarbylcarbonyl group, amino group, or hydrocarbyl group that may have a substituent may be substituted with a substituent.
  • a hydrogen atom in the hydrocarbyl group that may have a substituent is substituted with a substituent.
  • R ′ represents a hydrocarbylene group which may have a substituent.
  • R ′ ′′ represents a trivalent hydrocarbon group which may have a substituent.
  • m represents an integer of 1 or more.
  • q represents an integer of 0 or more.
  • the hydrocarbylthio group which is a substituent that the organic compound may have, is a thio group in which one hydrogen atom constituting the group is substituted with the hydrocarbyl group.
  • the hydrocarbylthiocarbonyl group which is a substituent that the organic compound may have, is a thiocarbonyl group in which one hydrogen atom constituting the group is substituted with the hydrocarbyl group.
  • the hydrocarbyl dithio group which is a substituent which the organic compound may have is a dithio group in which one hydrogen atom constituting the group is substituted with the hydrocarbyl group.
  • hydrocarbyl carbamoyl group and dihydrocarbyl carbamoyl group which are substituents that the organic compound may have are carbamoyl groups in which one or two hydrogen atoms constituting the group are substituted with the hydrocarbyl group.
  • boric acid ester residue that is a substituent that the organic compound may have include groups selected from the following formulae.
  • the hydrocarbyl sulfo group that is a substituent that the organic compound may have is a sulfo group in which one hydrogen atom constituting the group is substituted with the hydrocarbyl group.
  • the hydrocarbylsulfonyl group, which is a substituent that the organic compound may have, is a sulfonyl group in which the hydrocarbyl group is bonded to one of the two bonds that the group has.
  • the hydrocarbylsulfino group which is a substituent that the organic compound may have is a sulfino group in which one hydrogen atom constituting the group is substituted with the hydrocarbyl group.
  • examples of the hydrocarbylene group represented by R ′ include methylene group, ethylene group, 1,2-propylene group, 1,3-propylene group, 1,2 -Number of carbon atoms such as butylene, 1,3-butylene, 1,4-butylene, 1,5-pentylene, 1,6-hexylene, 1,9-nonylene, 1,12-dodecylene, etc.
  • a carbon number of 2 to 50 such as a saturated hydrocarbylene group, an ethenylene group, a propenylene group, a 3-butenylene group, a 2-pentenylene group, a 2-hexenylene group, a 2-nonenylene group, a 2-dodecenylene group, Unsaturated hydrocarbylene group, cyclopropylene group, cyclobutylene group, cyclopentylene group, cyclohexylene group, cyclononylene group, cyclododecylene group, norbornylene group, adamantylene group, etc.
  • C3-C50 cyclic saturated hydrocarlene group ethenylene group, propenylene group, 3-butenylene group, 2-butenylene group, 2-pentenylene group, 2-hexenylene group, 2-nonenylene group, 2-dodecenylene group, etc.
  • Alkenylene group having 2 to 50 carbon atoms 1,3-phenylene group, 1,4-phenylene, 1,4-naphthylene group, 1,5-naphthylene group, 2,6-naphthylene group, biphenyl-4,4 Examples include arylene groups having 6 to 50 carbon atoms such as a '-diyl group.
  • the hydrocarbylene group represented by R ′ may have a substituent.
  • this substituent the same substituent as the substituent which the said hydrocarbyl group may have is mentioned.
  • the plurality of substituents may be the same or different.
  • An organic compound having an anionic ionic group preferably has a polar group in addition to the anionic ionic group, since the electron injecting property is improved.
  • Examples include acid, lactic acid, succinic acid, monochloroacetic acid, dichloroacetic acid, trichloroacetic acid, trifluoroacetic acid, nitroacetic acid, and triphenylacetic acid.
  • an organic sulfonic acid having a sulfo group such as aliphatic, aromatic, cycloaliphatic, such as benzenesulfonic acid, p-toluenesulfonic acid, xylenesulfonic acid, naphthalenesulfonic acid, decylbenzenesulfonic acid, Dodecylbenzenesulfonic acid, pentadecylbenzenesulfonic acid, methanesulfonic acid, ethanesulfonic acid, 1-propanesulfonic acid, 1-butanesulfonic acid, 1-hexanesulfonic acid, 1-heptanesulfonic acid, 1-octa
  • the charge separation layer 70 may contain one of each of an electron donating compound and an electron accepting compound, or may contain two or more kinds in combination.
  • the electron-donating compound and the electron-accepting compound are relatively determined from the energy levels of these compounds.
  • a step of forming an anode by coating in other words, one embodiment of a method for manufacturing a photoelectric conversion element is a step of coating and forming each of an anode and a cathode
  • a step of forming all other remaining layers by coating and forming in other words, a step of forming and forming each of all the layers by coating including.
  • ⁇ Analysis method> The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the conjugated compound are determined by gel permeation chromatography (GPC) (manufactured by Tosoh Corporation, trade name: HLC-8220GPC). It calculated
  • the sample to be measured was dissolved in tetrahydrofuran so as to have a concentration of about 0.5% by weight, and 50 ⁇ L was injected into GPC. Furthermore, tetrahydrofuran was used as the mobile phase of GPC and allowed to flow at a flow rate of 0.5 mL / min.
  • the detection wavelength was set at 254 nm.
  • 4-tert-butylphenylboronic acid (0.01 g) was added to the reaction solution, and the mixture was refluxed for 6 hours.
  • sodium diethyldithiacarbamate aqueous solution (10 mL, concentration: 0.05 g / mL) was added thereto, and the mixture was stirred for 2 hours.
  • the reaction solution was dropped into 300 mL of methanol and stirred for 1 hour, and then the deposited precipitate was filtered, dried under reduced pressure for 2 hours, and dissolved in 20 mL of tetrahydrofuran.
  • conjugated compound P-3 a conjugated compound
  • phenylboronic acid (0.06 g, 0.5 mmol) was added thereto, and the resulting mixture was stirred for 10 hours. After allowing to cool, the aqueous layer was removed from the reaction solution, an aqueous sodium diethyldithiocarbamate solution was added and stirred, the aqueous layer was removed, and the organic layer was washed successively with water and a 3 wt% aqueous acetic acid solution. When the organic layer was poured into methanol, a precipitate was formed. The precipitate collected by filtration was dissolved again in toluene and passed through a silica gel column and an alumina column.
  • the precipitate collected by filtration was dissolved in toluene and passed through a silica gel column and an alumina column.
  • a precipitate was formed.
  • the precipitate was vacuum-dried at 50 ° C. to obtain a polymer compound (hereinafter referred to as “light-emitting material B”) (12.5 g).
  • the light-emitting material B had a polystyrene-equivalent weight average molecular weight of 3.1 ⁇ 10 5 and a molecular weight distribution index (Mw / Mn) of 2.9.
  • the light emitting material B (11.3 mg) and 1 mL of xylene were mixed to prepare a light emitting layer composition containing 1.3% by weight of the light emitting material B.
  • the composition for the light emitting layer was applied by spin coating on the glass substrate F on which the hole transport layer was formed, to form a coating film having a thickness of 99 nm.
  • the substrate on which this coating film was formed was heated at 130 ° C. for 15 minutes in a nitrogen atmosphere to evaporate the solvent, and then naturally cooled to room temperature to obtain a glass substrate G on which a light emitting layer was formed.
  • This composition for electron injection layer was applied on the glass substrate G on which the light emitting layer was formed by spin coating to form a coating film having a thickness of 10 nm.
  • the substrate on which the coating film was formed was heated at 130 ° C. for 10 minutes in a nitrogen atmosphere to evaporate the solvent, and then naturally cooled to room temperature to obtain a glass substrate H on which an electron injection layer was formed. .
  • Example 2 (Production of light-emitting element k-3)
  • poly (3,4-ethylenedioxythiophene) / polystyrenesulfonic acid manufactured by HC Starck, PEDOT: PSS solution, trade name: CLEVIOS (registered trademark) PVP
  • CLEVIOS registered trademark
  • PVP hole injection material solution
  • a composition for cathode which is a dispersion of silver nanoparticles having a number average ferret diameter of 7 nm, using AQ-1200 which is a polythiophene sulfonic acid hole injection material obtained from Plextronics instead of AI 4083) (NPS-JL, manufactured by Harima Kasei Co., Ltd., silver particle aspect ratio: 1.0)
  • a cathode composition (25.0 wt% MDot-) which is a dispersion of silver nanoparticles having a number average ferret diameter of 80 nm SLP, manufactured by Mitsuboshi Belting, silver particle aspect ratio

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Abstract

La présente invention concerne un élément électroluminescent ayant une luminosité supérieure. L'élément électroluminescent présente une électrode positive, une couche électroluminescente, une couche d'implantation d'électrons, et une électrode négative. La couche d'implantation d'électrons contient un composé organique présentant un groupe anionique ionique, et l'électrode négative contient un matériau conducteur doté d'un rapport d'aspect inférieur à 1,5.
PCT/JP2012/057480 2011-03-28 2012-03-23 Élément électroluminescent et son procédé de fabrication WO2012133165A1 (fr)

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JP6167549B2 (ja) * 2013-02-18 2017-07-26 住友化学株式会社 電極形成用の組成物
JPWO2020130025A1 (ja) * 2018-12-18 2021-10-28 コニカミノルタ株式会社 電子デバイス及び電子デバイスの製造方法
WO2020130021A1 (fr) * 2018-12-18 2020-06-25 コニカミノルタ株式会社 Dispositif électronique et procédé de fabrication de dispositif électronique

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