WO2020067300A1 - Matériau électronique organique et élément électronique organique - Google Patents

Matériau électronique organique et élément électronique organique Download PDF

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WO2020067300A1
WO2020067300A1 PCT/JP2019/037883 JP2019037883W WO2020067300A1 WO 2020067300 A1 WO2020067300 A1 WO 2020067300A1 JP 2019037883 W JP2019037883 W JP 2019037883W WO 2020067300 A1 WO2020067300 A1 WO 2020067300A1
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transporting polymer
organic
charge transporting
structural unit
organic electronic
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PCT/JP2019/037883
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English (en)
Japanese (ja)
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和幸 加茂
伊織 福島
広貴 佐久間
石塚　健一
智嗣 杉岡
涼 本名
児玉　俊輔
知美 内山
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日立化成株式会社
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Priority to JP2020549360A priority Critical patent/JPWO2020067300A1/ja
Priority to CN201980063265.7A priority patent/CN112771687A/zh
Publication of WO2020067300A1 publication Critical patent/WO2020067300A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • 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
    • 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
    • H10K59/50—OLEDs integrated with light modulating elements, e.g. with electrochromic elements, photochromic elements or liquid crystal elements

Definitions

  • Embodiments of the present invention relate to an organic electronic material, a liquid composition, an organic layer, an organic electronic device, an organic electroluminescent device, a display device, a lighting device, a display device, and a method of manufacturing an organic electronic device.
  • Organic electronic devices are devices that perform electrical operations using organic substances, and are expected to exhibit features such as energy saving, low cost, and flexibility, and are attracting attention as a technology that can replace conventional silicon-based inorganic semiconductors. Have been.
  • the organic electronic element include an organic electroluminescent element (organic EL element), an organic photoelectric conversion element, an organic transistor, and the like.
  • Organic EL devices are attracting attention, for example, as large-area solid-state light source applications that can replace incandescent lamps or gas-filled lamps. In addition, it is attracting attention as a leading self-luminous display replacing a liquid crystal display (LCD) in the field of a flat panel display (FPD), and its commercialization is progressing.
  • LCD liquid crystal display
  • FPD flat panel display
  • the organic EL elements are roughly classified into two types, a low-molecular type organic EL element and a polymer type organic EL element, according to the organic material used.
  • a polymer type organic EL device a polymer compound is used as an organic material
  • a low molecular weight organic EL device a low molecular compound is used.
  • a method of manufacturing an organic EL element includes a dry process in which film formation is mainly performed in a vacuum system, a wet process in which film formation is performed by plate printing such as letterpress printing, intaglio printing, and plateless printing such as inkjet printing. It is roughly divided into two. Since simple film formation is possible, a wet process is expected as an indispensable method for a large-screen organic EL display in the future.
  • a solution obtained by dissolving an organic material in a solvent is applied to form a coating layer, and then the organic layer is formed by drying the coating layer. Therefore, in order to form an organic layer having a sufficient thickness, it is preferable to use a high-concentration solution.
  • a solution containing a polymer compound the viscosity tends to increase as the concentration increases. If the viscosity of the solution is high, it may be difficult to form an organic layer depending on the application method.
  • an object of the present invention is to provide an organic electronic material and a liquid composition that can form an organic layer having a sufficient thickness by a wet process.
  • Another object of an embodiment of the present invention is to provide an organic layer which has a sufficient film thickness and can be easily formed by a wet process.
  • Still another object of the embodiments of the present invention is to provide an organic electronic element, an organic EL element, a display element, a lighting device, and a display device having excellent characteristics.
  • the present invention includes various embodiments. An example of the embodiment will be described below. The present invention is not limited to the following embodiments.
  • One embodiment is an organic electronic material containing a charge transporting polymer, wherein the charge transporting polymer has a branched structure, and the weight average molecular weight of the charge transporting polymer is 20,000 or more;
  • the viscosity of the solution at room temperature is less than 3.0 mPa ⁇ s.
  • the material is an organic electronic material containing a charge transporting polymer, wherein the charge transporting polymer has a branched structure, and the weight average molecular weight of the charge transporting polymer is 20,000 or more;
  • Another embodiment relates to a liquid composition containing the organic electronic material and a solvent.
  • Another embodiment relates to an organic layer formed using the organic electronic material or the liquid composition.
  • Another embodiment relates to an organic electronic device including the organic layer.
  • Another embodiment relates to an organic electroluminescence device including the organic layer.
  • Another embodiment relates to a display device including the organic electroluminescent element; a lighting device including the organic electroluminescent device; or a display device including the lighting device and a liquid crystal element as a display unit.
  • Still another embodiment relates to a method for manufacturing an organic electronic device, comprising forming an organic layer using the organic electronic material or the liquid composition.
  • an organic electronic material and a liquid composition capable of forming an organic layer having a sufficient thickness by a wet process. Further, according to the embodiment of the present invention, it is possible to provide an organic layer having a sufficient film thickness and which can be easily formed by a wet process. Furthermore, according to the embodiment of the present invention, it is possible to provide an organic electronic element, an organic EL element, a display element, a lighting device, and a display device having excellent characteristics.
  • FIG. 1 is a schematic sectional view showing an example of an organic EL device according to an embodiment of the present invention.
  • An organic electronic material according to an embodiment of the present invention has a branched structure, a weight average molecular weight of 20,000 or more, and contains a charge transporting polymer satisfying the following.
  • a solution containing the charge transporting polymer and toluene and having a charge transporting polymer concentration of 10% by mass is prepared, the viscosity of the solution at room temperature is less than 3.0 mPa ⁇ s.
  • the charge transporting polymer is a branched polymer and has a branched structure in the molecule.
  • the structural unit constituting the charge transporting polymer includes at least a trivalent or higher valent structural unit B and a monovalent structural unit T, and may further include a divalent structural unit.
  • the structural unit B is a structural unit forming a branch.
  • the structural unit T is a structural unit constituting the terminal of the molecular chain.
  • the structural unit L is preferably a structural unit having a charge transporting property.
  • the charge transporting polymer may include only one type of each structural unit, or may include a plurality of types. In the charge transporting polymer, each structural unit is bonded to each other at “one” to “three or more” bonding sites. Each structural unit will be described later.
  • the weight average molecular weight of the charge transporting polymer is 20,000 or more.
  • the weight average molecular weight is preferably 25,000 or more, more preferably 30,000 or more, and even more preferably 35,000 or more.
  • the weight average molecular weight of the charge transporting polymer is preferably 1,000,000 or less, more preferably 700,000 or less, and still more preferably 400,000 or less. When it is 1,000,000 or less, good solubility in a solvent is maintained, and a liquid composition can be easily prepared.
  • the weight average molecular weight of the charge transporting polymer is preferably 200,000 or less, more preferably 100,000 or less, and even more preferably 80,000 or less.
  • the viscosity of the solution tends to increase as the weight average molecular weight of the charge transporting polymer increases, and the viscosity of the solution tends to decrease as the weight average molecular weight of the charge transporting polymer decreases.
  • the number average molecular weight of the charge transporting polymer is preferably 10,000 or more, more preferably 12,000 or more, and even more preferably 15,000 or more. When the number average molecular weight is 10,000 or more, an organic layer having excellent film forming properties, heat resistance, and stability can be formed. On the other hand, the number average molecular weight of the charge transporting polymer is preferably 500,000 or less, more preferably 100,000 or less. When it is 500,000 or less, good solubility in a solvent is maintained, and a liquid composition can be easily prepared. In particular, the number average molecular weight of the charge transporting polymer is preferably 50,000 or less, more preferably 40,000 or less, and even more preferably 30,000 or less.
  • the weight average molecular weight and the number average molecular weight can be measured by gel permeation chromatography (GPC) using a standard polystyrene calibration curve.
  • the GPC measurement conditions may be, for example, the following conditions.
  • Equipment High-performance liquid chromatograph Prominence Shimadzu Corporation Liquid transfer pump (LC-20AD) Deaeration unit (DGU-20A) Autosampler (SIL-20AHT) Column oven (CTO-20A) PDA detector (SPD-M20A) Differential refractive index detector (RID-20A)
  • Eluent Tetrahydrofuran (THF) (for HPLC, containing stabilizer) Fujifilm Wako Pure Chemical Industries, Ltd.
  • Flow rate 1 mL / min
  • Molecular weight standard substance PStQuick A / B / C Tosoh Corporation
  • the charge transporting polymer is a polymer satisfying the following.
  • the viscosity of the solution at room temperature is less than 3.0 mPa ⁇ s.
  • the viscosity is measured at room temperature (25 ° C.).
  • a solution whose temperature is adjusted to 25 ° C. is used.
  • the concentration of the charge transporting polymer is a concentration based on the weight of the solution.
  • a measuring device utilizing a VROC technology Viscometer / Rheometer-on-a-Chip (VROC (R)) technology
  • VROC (R) Viscometer / Rheometer-on-a-Chip
  • microVISCO registered trademark
  • the measurement may be performed a plurality of times, and the average value of the measured values may be used as the viscosity value.
  • the solution for measurement can be prepared by the method described in Examples.
  • the viscosity of the solution can be measured by the method described in Examples.
  • the viscosity of the solution is less than 3.0 mPa ⁇ s, an organic layer having a sufficient film thickness can be easily formed using the charge transporting polymer.
  • the viscosity of the solution is preferably less than 3.0 mPa ⁇ s, more preferably 2.8 mPa ⁇ s or less, and even more preferably 2.7 mPa ⁇ s or less.
  • the lower limit of the viscosity is not particularly limited. As the viscosity is lower, an organic layer having a sufficient thickness tends to be easily formed.
  • the viscosity of the solution is, for example, preferably 1.0 mPa ⁇ s or more, more preferably 1.5 mPa ⁇ s or more, and 2.0 mPa ⁇ s in consideration of workability in forming an organic layer. More preferably, it is the above.
  • the viscosity of the solution can be adjusted by changing the ratio of the structural units in the charge transporting polymer, the molecular weight of the charge transporting polymer, and the like.
  • a charge transporting polymer having a viscosity of the toluene solution of less than 3.0 mPa ⁇ s is used, a high-concentration and low-viscosity liquid composition can be obtained.
  • a high-concentration and low-viscosity liquid composition By applying a high-concentration and low-viscosity liquid composition to, for example, an inkjet method, an organic layer having a sufficient film thickness can be easily formed.
  • the charge transporting polymer is preferably a hole transporting polymer having the ability to transport holes. More preferably, the charge transporting polymer has at least one structure selected from the group consisting of an aromatic amine structure, a carbazole structure, a thiophene structure, a fluorene structure, a benzene structure, a pyrrole structure, an aniline structure, and a phenoxazine structure. Including structural units. These structures can be substituted or unsubstituted. In addition, these structural units may be included as any of “monovalent” to “trivalent or more” structural units.
  • At least one of the structural unit B, the structural unit L, and the structural unit T is a substituted or unsubstituted, aromatic amine structure, carbazole structure, thiophene structure, fluorene structure, benzene structure, pyrrole structure, aniline structure, and It is preferable to include a structural unit including at least one structure selected from the group consisting of phenoxazine structures. At least one of the structural unit B, the structural unit L, and the structural unit T is selected from the group consisting of a substituted or unsubstituted aromatic amine structure, a carbazole structure, a thiophene structure, a fluorene structure, a benzene structure, and a pyrrole structure.
  • the aromatic amine structure is preferably a structure selected from the group consisting of a diarylamine structure and a triarylamine structure, more preferably a triarylamine structure, and even more preferably a triphenylamine structure.
  • the charge transporting polymer is a branched polymer. According to the branched charge transporting polymer, an organic layer having a sufficient film thickness can be efficiently formed.
  • the branched structure has at least one structural unit B and three or more structural units L bonded to the one structural unit B.
  • the branched structure has one structural unit B and three or more structural units L bonded to the one structural unit B, and further includes, for each of the three or more structural units L, It includes a multi-branched structure having at least another structural unit B bonded to the structural unit L and another two or more structural units L bonded to the another structural unit B.
  • Examples of the partial structure contained in the charge transporting polymer include the following.
  • the charge transporting polymer is not limited to a polymer having the following partial structure.
  • L represents a structural unit L
  • T represents a structural unit T
  • B represents a structural unit B.
  • * represents a binding site to another structure.
  • a plurality of Ls may be the same structural unit or different structural units. The same applies to T and B.
  • the structural unit L is preferably a divalent structural unit having a charge transporting property.
  • the structural unit L is not particularly limited as long as it contains an atomic group capable of transporting charges.
  • the structural unit L is a substituted or unsubstituted aromatic amine structure, carbazole structure, thiophene structure, fluorene structure, benzene structure, biphenylene structure, terphenylene structure, naphthalene structure, anthracene structure, tetracene structure, phenanthrene structure, dihydro Phenanthrene structure, pyridine structure, pyrazine structure, quinoline structure, isoquinoline structure, quinoxaline structure, acridine structure, diazaphenanthrene structure, furan structure, pyrrole structure, oxazole structure, oxadiazole structure, thiazole structure, thiadiazole structure, triazole structure, benzol A thiophene structure, a be
  • the structural unit L is a substituted or unsubstituted aromatic amine structure, carbazole structure, thiophene structure, fluorene structure, benzene structure, benzene structure, pyrrole structure, aniline structure, from the viewpoint of obtaining excellent hole transporting properties. It is preferably selected from a phenoxazine structure and a structure containing one or more of these, and is a substituted or unsubstituted aromatic amine structure, carbazole structure, thiophene structure, fluorene structure, benzene structure, pyrrole structure.
  • the structural unit L is a substituted or unsubstituted fluorene structure, a benzene structure, a phenanthrene structure, a pyridine structure, a quinoline structure, and one or two of these, from the viewpoint of obtaining excellent electron transportability.
  • it is selected from a structure containing more than one species.
  • the structural unit L includes the following.
  • the structural unit L is not limited to the following.
  • R represents a hydrogen atom or a substituent each independently.
  • the substituents are preferably each independently —R 1 , —OR 2 , —SR 3 , —OCOR 4 , —COOR 5 , —SiR 6 R 7 R 8 , a halogen atom, And a group comprising a group containing a polymerizable functional group described below.
  • R 1 represents a linear, cyclic or branched alkyl group having 1 to 22 carbon atoms; or an aryl group or heteroaryl group having 2 to 30 carbon atoms.
  • R 2 to R 8 each independently represent a hydrogen atom; a linear, cyclic or branched alkyl group having 1 to 22 carbon atoms; or an aryl group or a heteroaryl group having 2 to 30 carbon atoms.
  • Alkyl, aryl, and heteroaryl groups can be substituted or unsubstituted.
  • substituents when the alkyl group, the aryl group, and the heteroaryl group further have a substituent include -R 1 , -OR 2 , -SR 3 , -OCOR 4 , -COOR 5 , -SiR 6 R 7 R 8, a halogen atom, and, include groups containing described later polymerizable functional groups, preferably -R 1.
  • R is preferably a hydrogen atom, an alkyl group, an aryl group, an alkyl-substituted aryl group, a halogen atom, a halogen-substituted alkyl group, or the like.
  • Ar represents a divalent linking group each independently, for example, each independently represents an arylene group or a heteroarylene group.
  • Ar is preferably an arylene group having 2 to 30 carbon atoms or a heteroarylene group, more preferably an arylene group having 2 to 30 carbon atoms, and further preferably a phenylene group.
  • the aryl group is an atomic group obtained by removing one hydrogen atom from an aromatic hydrocarbon.
  • a heteroaryl group is an atomic group obtained by removing one hydrogen atom from an aromatic heterocyclic compound.
  • An arylene group is an atomic group obtained by removing two hydrogen atoms from an aromatic hydrocarbon.
  • a heteroarylene group is an atomic group obtained by removing two hydrogen atoms from an aromatic heterocyclic compound.
  • aromatic hydrocarbon a monocyclic ring, a condensed ring, or a polycyclic ring in which two or more selected from a monocyclic ring and a condensed ring are bonded via a direct bond
  • aromatic heterocyclic compound examples include a single ring, a condensed ring, or a polycyclic ring in which two or more selected from a single ring and a condensed ring are bonded via a direct bond.
  • the structural unit B is a trivalent or higher valent structural unit constituting a branched portion.
  • the structural unit B is preferably 6 or less, more preferably 5 or less, and still more preferably 4 or 3, from the viewpoint of improving the durability of the organic electronic element.
  • the structural unit B is preferably a unit having a charge transporting property.
  • the structural unit B is a substituted or unsubstituted aromatic amine structure, a carbazole structure, a condensed polycyclic aromatic hydrocarbon structure, and one or two of these, from the viewpoint of improving the durability of the organic electronic element. It is selected from structures containing more than one species.
  • the aromatic amine structure is preferably a structure selected from the group consisting of a diarylamine structure and a triarylamine structure, more preferably a triarylamine structure, and even more preferably a triphenylamine structure.
  • the structural unit B includes the following.
  • the structural unit B is not limited to the following.
  • W represents a trivalent linking group, for example, an areentriyl group having 2 to 30 carbon atoms or a heteroarenetriyl group.
  • Ar represents a divalent linking group each independently, for example, each independently represents an arylene group or a heteroarylene group.
  • Ar is preferably an arylene group having 2 to 30 carbon atoms or a heteroarylene group, more preferably an arylene group having 2 to 30 carbon atoms, and further preferably a phenylene group.
  • Y represents a direct bond or a divalent linking group, for example, a group having at least one hydrogen atom in R (excluding a group containing a polymerizable functional group) in the structural unit L, And a divalent group excluding one hydrogen atom.
  • Z represents any of a carbon atom, a silicon atom and a phosphorus atom.
  • the benzene ring and Ar may have a substituent, and examples of the substituent include R in the structural unit L.
  • Arenetriyl group is an atomic group obtained by removing three hydrogen atoms from an aromatic hydrocarbon.
  • the heteroarenetriyl group is an atomic group obtained by removing three hydrogen atoms from an aromatic heterocyclic compound.
  • the aromatic hydrocarbon and the aromatic heterocyclic compound are as described above.
  • the structural unit T is a monovalent structural unit constituting the terminal of the charge transporting polymer.
  • the structural unit T is not particularly limited, and is selected from, for example, a substituted or unsubstituted aromatic hydrocarbon structure, an aromatic heterocyclic structure, and a structure containing one or more of these.
  • the structural unit T may have the same structure as the structural unit L.
  • the structural unit T is preferably a substituted or unsubstituted aromatic hydrocarbon structure from the viewpoint of imparting durability without lowering the charge transportability, and is preferably a substituted or unsubstituted benzene. More preferably, it is a structure.
  • the structural unit T has a polymerizable structure (for example, a polymerizable functional group such as a pyrrol-yl group). ).
  • the structural unit T includes the following.
  • the structural unit T is not limited to the following.
  • R is independently the same as R in the structural unit L.
  • the structural unit T preferably includes a structural unit in which at least one of R in the above formula is a group containing a polymerizable functional group.
  • the structural unit T preferably includes a structural unit in which at least one of R in the above formula is an alkyl group or a fluoroalkyl group. Is preferred.
  • the alkyl group is preferably a straight-chain alkyl group, more preferably a straight-chain alkyl group having 20 or less carbon atoms, and still more preferably a straight-chain alkyl group having 6 to 12 carbon atoms.
  • the fluoroalkyl group is preferably a perfluoroalkyl group, more preferably a perfluoromethyl group or a perfluoroethyl group, and further preferably a perfluoromethyl group.
  • the charge transporting polymer preferably has at least one polymerizable functional group from the viewpoint of curing by a polymerization reaction and changing the solubility in a solvent.
  • “Polymerizable functional group” refers to a functional group capable of forming a bond with each other by applying heat, light, or the like.
  • a substituted or unsubstituted group having a carbon-carbon multiple bond for example, vinyl group, styryl group, allyl group, butenyl group, ethynyl group, acryloyl group, acryloyloxy group, acryloylamino group, A methacryloyl group, a methacryloyloxy group, a methacryloylamino group, a vinyloxy group, a vinylamino group, etc., a group having a small ring (for example, a cyclic alkyl group such as a cyclopropyl group, a benzocyclobutenyl group, a cyclobutyl group; an epoxy group ( Groups having a cyclic ether structure such as oxiranyl group), oxetane group (oxetanyl group); diketene group; episulfide group; lactone group; lactam group
  • the substituent is not particularly limited, and examples thereof include a linear, cyclic or branched alkyl group.
  • the carbon number of the alkyl group is preferably 1 to 22, more preferably 1 to 10, and still more preferably 1 to 4.
  • a substituted or unsubstituted group having a cyclic ether structure or a group having a carbon-carbon multiple bond is preferable, and a substituted or unsubstituted vinyl group, styryl group, acryloyl group, methacryloyl group, epoxy Groups or oxetane groups are more preferable, and a substituted or unsubstituted vinyl group or oxetane group is further preferable from the viewpoint of reactivity and characteristics of the organic electronic element.
  • the skeleton structure of the charge transporting polymer and the polymerizable functional group are preferably formed of an alkylene chain (for example, a straight chain having 1 to 8 carbon atoms). And an alkylene chain).
  • the solubility of the charge transporting polymer in a solvent tends to be improved by the alkylene chain.
  • the organic layer is bonded via a hydrophilic linking group such as an ethylene glycol chain or a diethylene glycol chain. You may.
  • one or more kinds selected from an ether bond, an ester bond, and the like are provided between the skeleton structure and the polymerizable functional group. May be included.
  • group containing a polymerizable functional group examples include “the polymerizable functional group” itself and "a group obtained by combining a polymerizable functional group with a linking group such as an alkylene chain or an ether bond”. included.
  • group containing a polymerizable functional group for example, a group exemplified in WO 2010/140553 can be suitably used.
  • the polymerizable functional group may be introduced into the terminal (ie, the structural unit T) of the charge transporting polymer or may be introduced into a portion other than the terminal (ie, the structural unit B or L). And a part other than the terminal part. From the viewpoint of curability, it is preferably introduced at least at the terminal portion, and from the viewpoint of achieving both curability and charge transportability, it is preferably introduced only at the terminal portion. Further, the polymerizable functional group may be introduced into the main chain of the charge transporting polymer, into the side chain, or into both the main chain and the side chain.
  • the polymerizable functional group is preferably contained in the charge transporting polymer in a large amount.
  • the amount contained in the charge transporting polymer is small.
  • the content of the polymerizable functional group can be appropriately set in consideration of these.
  • the number of polymerizable functional groups per molecule of the charge transporting polymer is preferably 2 or more, more preferably 3 or more, from the viewpoint of obtaining a sufficient change in solubility and facilitating multilayering.
  • the number of polymerizable functional groups is preferably 1,000 or less, more preferably 500 or less, and still more preferably 300 or less, from the viewpoint of maintaining charge transportability.
  • the number of polymerizable functional groups per molecule of the charge transporting polymer is calculated based on the charged amount of the polymerizable functional group used for synthesizing the charge transporting polymer (for example, the charged amount of the monomer having the polymerizable functional group), and each structure.
  • the average value can be determined using the charged amount of the monomer corresponding to the unit, the weight average molecular weight of the charge transporting polymer, and the like.
  • the number of polymerizable functional groups is determined by the ratio of the integrated value of the signal derived from the polymerizable functional group in the 1 H NMR (nuclear magnetic resonance) spectrum of the charge transporting polymer to the integrated value of the entire spectrum, the charge transporting polymer. Can be calculated as an average value using the weight average molecular weight and the like.
  • the proportion of the structural unit B contained in the charge transporting polymer is preferably 1 mol% or more based on all structural units. 5 mol% or more, more preferably 10 mol% or more. Further, the proportion of the structural unit B is preferably 17 mol% or less, more preferably 16 mol% or less, and preferably 15 mol% or less, from the viewpoint of suppressing the viscosity of the liquid composition to a low level and obtaining an organic layer having a sufficient film thickness. Is more preferred.
  • the proportion of the structural unit L is preferably 10 mol% or more, more preferably 20 mol% or more based on all structural units, from the viewpoint of obtaining sufficient charge transportability. , 30 mol% or more is more preferable. Further, in consideration of the structural unit T and the structural unit B, the ratio of the structural unit L is preferably 95 mol% or less, more preferably 90 mol% or less, and still more preferably 85 mol% or less.
  • the ratio of the structural units T contained in the charge transporting polymer is based on all structural units, from the viewpoint of improving the characteristics of the organic electronic element, or suppressing the rise in viscosity and favorably synthesizing the charge transporting polymer. 5 mol% or more, preferably 10 mol% or more, more preferably 15 mol% or more.
  • the proportion of the structural unit T is preferably 60 mol% or less, more preferably 55 mol% or less, and still more preferably 50 mol% or less, from the viewpoint of obtaining a sufficient charge transporting property.
  • the charge transporting polymer includes the structural unit L, the structural unit T, and the structural unit B
  • x is a ratio (mol%) of the structural unit B based on all the structural units contained in the charge transporting polymer. x is preferably at least 1 mol%, more preferably at least 5 mol%, even more preferably at least 10 mol%.
  • x is preferably 17 mol% or less, more preferably 16 mol% or less, and still more preferably 15 mol% or less.
  • the ratio of the polymerizable functional group is preferably 0.1 mol% or more based on all structural units from the viewpoint of efficiently curing the charge transporting polymer, 1 mol% or more is more preferable, and 3 mol% or more is further preferable.
  • the proportion of the polymerizable functional group is preferably 70 mol% or less, more preferably 60 mol% or less, and still more preferably 50 mol% or less, from the viewpoint of obtaining good charge transportability.
  • the “ratio of the polymerizable functional group” means the ratio of the structural unit having the polymerizable functional group.
  • the ratio of the structural units can be determined by using the charged amount of the monomer corresponding to each structural unit used for synthesizing the charge transporting polymer. Further, the ratio of the structural units can be calculated as an average value by using an integrated value of a spectrum derived from each structural unit in the 1 H NMR spectrum of the charge transporting polymer. For simplicity, when the charged amount is clear, preferably, a value obtained using the charged amount is used.
  • the charge transporting polymer can be produced by various synthetic methods and is not particularly limited.
  • a known coupling reaction such as Suzuki coupling, Negishi coupling, Sonogashira coupling, Stille coupling, Buchwald-Hartwig coupling and the like can be used.
  • Suzuki coupling causes a cross-coupling reaction using a Pd catalyst between an aromatic boronic acid derivative and an aromatic halide.
  • a charge transporting polymer can be easily produced by bonding desired aromatic rings.
  • a Pd (0) compound, a Pd (II) compound, a Ni compound, or the like is used as a catalyst.
  • a catalyst species generated by mixing tris (dibenzylideneacetone) dipalladium (0), palladium (II) acetate or the like with a phosphine ligand can also be used.
  • the description in WO 2010/140553 can be referred to.
  • the organic electronic material may include any additives, for example, may further include a dopant.
  • the dopant is not particularly limited as long as it is capable of exhibiting a doping effect and improving charge transportability by being added to the organic electronic material.
  • the dopant used for the organic electronic material may be a dopant that exhibits either the p-type doping or the n-type doping effect. Further, one kind of dopant may be added alone, or a plurality of kinds of dopants may be mixed and added.
  • the dopant used for the p-type doping is an electron-accepting compound, and examples thereof include a Lewis acid, a proton acid, a transition metal compound, an ionic compound, a halogen compound, and a ⁇ -conjugated compound.
  • the Lewis acid FeCl 3 , PF 5 , AsF 5 , SbF 5 , BF 5 , BCl 3 , BBr 3 or the like;
  • the protic acid HF, HCl, HBr, HNO 3 , H 2 SO 4 , Inorganic acids such as HClO 4 , benzenesulfonic acid, p-toluenesulfonic acid, dodecylbenzenesulfonic acid, polyvinylsulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, trifluoroacetic acid, 1-butanesulfonic acid, vinylphenylsulfonic acid , organic acids such as camphorsulfonic acid; the transition metal compound, FeOCl, TiCl 4, ZrCl 4 , HfCl 4, NbF 5, AlCl 3, NbCl 5, TaCl 5, MoF 5; as ionic compounds include tetraki
  • the dopant used for the n-type doping is an electron donating compound, for example, an alkali metal such as Li or Cs; an alkaline earth metal such as Mg or Ca; an alkali metal such as LiF or Cs 2 CO 3 and / or Alkaline earth metal salts; metal complexes; electron donating organic compounds, and the like.
  • an alkali metal such as Li or Cs
  • an alkaline earth metal such as Mg or Ca
  • an alkali metal such as LiF or Cs 2 CO 3 and / or Alkaline earth metal salts
  • metal complexes electron donating organic compounds, and the like.
  • the charge transporting polymer has a polymerizable functional group
  • the organic electronic material may further contain a charge transporting low molecular compound, another polymer, and the like.
  • the content of the charge transporting polymer in the organic electronic material is preferably 50% by mass or more, more preferably 70% by mass or more based on the total mass of the organic electronic material, from the viewpoint of obtaining good charge transportability. , 80% by mass or more is more preferable.
  • the upper limit of the content of the charge transporting polymer is not particularly limited, and may be 100% by mass. In consideration of including additives such as dopants, the content of the charge transporting polymer may be set to, for example, 95% by mass or less or 90% by mass or less.
  • the content is preferably 0.01% by mass or more, and more preferably 0.1% by mass or more based on the total mass of the organic electronic material, from the viewpoint of improving the charge transportability of the organic electronic material. More preferably, the content is more preferably 0.5% by mass or more.
  • the amount is preferably 50% by mass or less, more preferably 30% by mass or less, and still more preferably 20% by mass or less, based on the total mass of the organic electronic material.
  • a liquid composition according to an embodiment of the present invention contains the organic electronic material and a solvent.
  • An organic layer can be easily formed by a simple method such as a coating method using a liquid composition containing a solvent.
  • the liquid composition can be used as an ink composition.
  • solvent any solvent such as water, an organic solvent, or a mixed solvent thereof can be used.
  • organic solvent include alcohols such as methanol, ethanol, and isopropyl alcohol; alkanes such as pentane, hexane, and octane; cyclic alkanes such as cyclohexane; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, tetralin, and diphenylmethane; Aliphatic ethers such as dimethyl ether, ethylene glycol diethyl ether, propylene glycol-1-monomethyl ether acetate; 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole, phenetole, 2-methoxytoluene, 3-methoxytoluene; Aromatic ethers such as 4-methoxytoluene, 2,3-dimethylanisole and 2,4
  • the liquid composition preferably contains a polymerization initiator.
  • a polymerization initiator known radical polymerization initiators, cationic polymerization initiators, anionic polymerization initiators, and the like can be used. From the viewpoint of easily preparing a liquid composition, it is preferable to use a substance having both a function as a dopant and a function as a polymerization initiator. Such substances include, for example, the ionic compounds.
  • the liquid composition may further contain an additive as an optional component.
  • the additives include a polymerization inhibitor, a stabilizer, a thickener, a gelling agent, a flame retardant, an antioxidant, a reduction inhibitor, an oxidizing agent, a reducing agent, a surface modifier, an emulsifier, an antifoaming agent, Dispersants, surfactants and the like can be mentioned.
  • the content of the solvent in the liquid composition can be determined in consideration of application to various coating methods.
  • the content of the solvent is preferably such that the ratio of the charge transporting polymer to the solvent is 0.1% by mass or more, more preferably 0.2% by mass or more, and more preferably 0.5% by mass or more. Is more preferable.
  • the content of the solvent is preferably such that the ratio of the charge transporting polymer to the solvent is 20% by mass or less, more preferably 15% by mass or less, and even more preferably 10% by mass or less. .
  • the organic layer according to the embodiment of the present invention is a layer formed using the organic electronic material or the liquid composition.
  • the organic layer shows good charge transport properties.
  • an organic layer can be favorably and simply formed by a coating method.
  • the coating method include a spin coating method; a casting method; an immersion method; a letterpress printing method such as letterpress printing, intaglio printing, offset printing, planographic printing, letterpress reverse offset printing, screen printing, gravure printing, and the like; A known method such as a plateless printing method may be used.
  • the coating layer obtained after the coating may be dried by a heat treatment to remove the solvent.
  • the polymerization reaction of the charge transporting polymer can be advanced by light irradiation, heat treatment, or the like, and the solubility of the coating layer can be changed. Heat treatment is preferred for simplicity.
  • the heat treatment can be performed in an air atmosphere or an inert gas atmosphere.
  • the inert gas include helium gas, argon gas, nitrogen gas, and a mixed gas thereof.
  • the “inert gas atmosphere” is preferably an atmosphere in which the concentration of the inert gas is 99.5% or more by volume, more preferably 99.9% or more, and more preferably 99.99%. More preferably, the atmosphere is as described above.
  • the heat treatment can be performed using, for example, a heater such as a hot plate or an oven.
  • a heater such as a hot plate or an oven.
  • a hot plate is used in an inert gas atmosphere, or the inside of an oven is set to an inert gas atmosphere.
  • the heat treatment is preferably performed at a temperature equal to or higher than the boiling point of the solvent.
  • a temperature at which the polymerization reaction efficiently proceeds is preferable.
  • the temperature of the heat treatment is preferably 140 ° C. or higher, more preferably 180 ° C. or higher, even more preferably 190 ° C. or higher.
  • the temperature is preferably 300 ° C or lower, more preferably 280 ° C or lower, and further preferably 250 ° C or lower.
  • the thickness of the organic layer after drying or after curing is preferably 0.1 nm or more, more preferably 1 nm or more, and still more preferably 3 nm or more, from the viewpoint of improving charge transport efficiency.
  • the thickness of the organic layer is preferably 300 nm or less, more preferably 200 nm or less, and still more preferably 100 nm or less, from the viewpoint of reducing electric resistance.
  • An organic electronic device has at least one of the organic layers.
  • the organic electronic element include an organic EL element, an organic photoelectric conversion element, an organic transistor, and the like.
  • the organic electronic element preferably has a structure in which an organic layer is disposed between at least a pair of electrodes.
  • the organic electronic element can be manufactured by a manufacturing method including forming an organic layer using the organic electronic material or the liquid composition.
  • An organic EL device has at least one organic layer.
  • the organic EL device usually includes a light emitting layer, an anode, a cathode, and a substrate, and may further include, if necessary, other functional layers such as a hole injection layer, an electron injection layer, a hole transport layer, and an electron transport layer. Have. Each layer may be formed by an evaporation method or a coating method.
  • the organic EL device preferably has the organic layer as a light emitting layer or another functional layer, more preferably has the other functional layer, and still more preferably has at least one of a hole injection layer and a hole transport layer. Have.
  • FIG. 1 is a schematic cross-sectional view showing one embodiment of an organic EL device.
  • the organic EL device shown in FIG. 1 is a device having a multilayer structure, and includes a substrate 8, an anode 2, a hole injection layer 3, a hole transport layer 6, a light emitting layer 1, an electron transport layer 7, an electron injection layer 5, and a cathode 4. In this order.
  • a light emitting material such as a low molecular compound, a polymer, and a dendrimer can be used. Polymers are preferred because they have high solubility in solvents and are suitable for coating methods. Examples of the light emitting material include a fluorescent material, a phosphorescent material, and a thermally activated delayed fluorescent material (TADF).
  • TADF thermally activated delayed fluorescent material
  • fluorescent materials low molecular weight compounds such as perylene, coumarin, rubrene, quinacridone, stilbene, dyes for dye lasers, aluminum complexes and derivatives thereof; polyfluorene, polyphenylene, polyphenylenevinylene, polyvinylcarbazole, fluorene-benzothiadiazole copolymer, Polymers such as fluorene-triphenylamine copolymers and derivatives thereof; and mixtures thereof.
  • fluorescent materials low molecular weight compounds such as perylene, coumarin, rubrene, quinacridone, stilbene, dyes for dye lasers, aluminum complexes and derivatives thereof; polyfluorene, polyphenylene, polyphenylenevinylene, polyvinylcarbazole, fluorene-benzothiadiazole copolymer, Polymers such as fluorene-triphenylamine copolymers and derivatives thereof; and mixtures thereof.
  • a metal complex containing a metal such as Ir or Pt can be used as the phosphorescent material.
  • Ir complex include FIr (pic) which emits blue light (iridium (III) bis [(4,6-difluorophenyl) -pyridinate-N, C 2 ] picolinate) and Ir (ppy) 3 which emits green light.
  • the light emitting layer contains a phosphorescent material
  • a host material in addition to the phosphorescent material.
  • a host material a low molecular compound, a polymer, or a dendrimer can be used.
  • the low molecular weight compound include CBP (4,4′-bis (9H-carbazol-9-yl) biphenyl), mCP (1,3-bis (9-carbazolyl) benzene), and CDBP (4,4′-
  • the polymer include bis (carbazol-9-yl) -2,2′-dimethylbiphenyl) and derivatives thereof.
  • the polymer include the organic electronic materials, polyvinylcarbazole, polyphenylene, polyfluorene, and derivatives thereof.
  • thermally activated delayed fluorescent material examples include PIC-TRZ (2-biphenyl-4,6-bis (12-phenylindolo [2,3-a] carbazol-11-yl) -1,3,5-triazine). , Spiro-CN (2 ', 7'-bis (di-P-tolylamino) -9,9'-spirobifluorene-s, 7-dicarbonitrile), CC2TA (2,4-bis ⁇ 3- (9H-carbazol-9) -yl) -9H-carbazol-9-yl ⁇ -6-phenyl-1,3,5-triazine), CZ-PS (9,9 '-(4,4'-sulfonylbis (4,1-phenylene)) bis (3,6-di-tert-butyl-9H-carbazole)), 4CzPN (3,4,5,6-tetra (9H-carbazol-9-yl) phthalonitrile), HAP-3TPA
  • the organic layer is used as at least one of a hole injection layer and a hole transport layer.
  • these layers can be easily formed by using a liquid composition containing an organic electronic material and a solvent.
  • the organic EL device has the organic layer as a hole injection layer and further has a hole transport layer
  • a known material can be used for the hole transport layer.
  • a known material can be used for the hole injection layer. Both the hole injection layer and the hole transport layer may be the organic layers.
  • Suitable materials include, for example, aromatic amine compounds (eg, aromatic diamines such as N, N′-di (naphthalen-1-yl) -N, N′-diphenyl-benzidine ( ⁇ -NPD)), phthalocyanines And thiophene-based compounds (eg, poly (3,4-ethylenedioxythiophene): a thiophene-based conductive polymer such as poly (4-styrenesulfonate) (PEDOT: PSS)).
  • aromatic amine compounds eg, aromatic diamines such as N, N′-di (naphthalen-1-yl) -N, N′-diphenyl-benzidine ( ⁇ -NPD)
  • phthalocyanines And thiophene-based compounds eg, poly (3,4-ethylenedioxythiophene): a thiophene-based conductive polymer such as poly (4-styrenesulfonate) (PEDOT: PSS)
  • the hole transport layer is an organic layer whose solubility is changed by polymerization
  • the light emitting layer can be easily formed thereon by a wet process.
  • the polymerization initiator may be contained in the organic layer which is the hole transport layer, or may be contained in the organic layer below the hole transport layer.
  • Electrode transport layer, electron injection layer Materials used for the electron transporting layer and the electron injecting layer include, for example, phenanthroline derivatives, bipyridine derivatives, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, naphthalene, condensed ring tetracarboxylic anhydrides such as perylene, carbodiimide Fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, thiadiazole derivatives, benzimidazole derivatives, quinoxaline derivatives, aluminum complexes and the like.
  • the organic electronic materials can also be used.
  • cathode As the cathode material, for example, a metal or a metal alloy such as Li, Ca, Mg, Al, In, Cs, Ba, Mg / Ag, LiF, and CsF is used.
  • a metal or a metal alloy such as Li, Ca, Mg, Al, In, Cs, Ba, Mg / Ag, LiF, and CsF is used.
  • anode for example, a metal (for example, Au) or another material having conductivity is used.
  • Other materials include, for example, oxides (eg, ITO: indium oxide / tin oxide) and conductive polymers (eg, polythiophene-polystyrene sulfonic acid mixture (PEDOT: PSS)).
  • the substrate is preferably transparent and preferably has flexibility. Quartz glass, resin film and the like are preferably used.
  • a light-transmitting resin film is preferable.
  • the resin film for example, polyethylene terephthalate, polyethylene naphthalate, polyether sulfone, polyether imide, polyether ether ketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate, cellulose triacetate, cellulose acetate propionate and the like as a main component Film.
  • the resin film When a resin film is used, the resin film may be coated with an inorganic substance such as silicon oxide or silicon nitride in order to suppress the permeation of water vapor, oxygen, or the like.
  • an inorganic substance such as silicon oxide or silicon nitride
  • the organic EL element may be sealed in order to reduce the influence of the outside air and extend the life.
  • a material used for sealing glass, an epoxy resin, an acrylic resin, a plastic film such as polyethylene terephthalate or polyethylene naphthalate, or an inorganic substance such as silicon oxide or silicon nitride can be used, but is not limited thereto. There is no.
  • the method of sealing is not particularly limited, and can be performed by a known method.
  • the emission color of the organic EL element is not particularly limited.
  • the white organic EL element is preferable because it can be used for various lighting devices such as home lighting, car lighting, a clock, and a liquid crystal backlight.
  • a method for forming a white organic EL element a method in which a plurality of luminescent materials are simultaneously used to emit a plurality of luminescent colors to perform color mixing can be used.
  • the combination of the plurality of emission colors is not particularly limited, but a combination containing three emission maximum wavelengths of blue, green and red, a combination containing two emission maximum wavelengths such as blue and yellow, yellow green and orange, and the like. Is mentioned.
  • the emission color can be controlled by adjusting the type and amount of the emission material.
  • a display element includes the organic EL element.
  • a color display element can be obtained by using an organic EL element as an element corresponding to each pixel of red, green, and blue (RGB).
  • Image forming methods include a simple matrix type in which individual organic EL elements arranged in a panel are directly driven by electrodes arranged in a matrix, and an active matrix type in which a thin film transistor is arranged and driven in each element.
  • the lighting device according to the embodiment of the present invention includes the organic EL element.
  • the display device according to the embodiment of the present invention includes a lighting device and a liquid crystal element as display means.
  • the display device can be a display device using the lighting device as a backlight and a known liquid crystal element as a display means, that is, a liquid crystal display device.
  • An organic electronic material containing a charge transporting polymer The charge transporting polymer has a branched structure, The charge transporting polymer has a weight average molecular weight of 20,000 or more, When a solution containing the charge-transporting polymer and toluene and the concentration of the charge-transporting polymer is 10% by mass is prepared, the viscosity of the solution at room temperature is less than 3.0 mPa ⁇ s. material.
  • the charge transporting polymer has at least one structure selected from the group consisting of an aromatic amine structure, a carbazole structure, a thiophene structure, a fluorene structure, a benzene structure, a pyrrole structure, an aniline structure, and a phenoxazine structure.
  • a liquid composition comprising the organic electronic material according to any one of (1) to (6) and a solvent.
  • An organic electroluminescence device including the organic layer according to (8) as a hole injection layer or a hole transport layer.
  • a display device including the organic electroluminescence device according to (10) or (11).
  • a lighting device including the organic electroluminescent element according to (10) or (11).
  • a display device including the lighting device according to (13) and a liquid crystal element as display means.
  • Charge transporting polymers 1 to 8 were prepared using the following monomers.
  • the metal adsorbent and insolubles were removed by filtration, and then reprecipitation from methanol was performed.
  • the resulting precipitate was collected by suction filtration and washed with methanol.
  • the resulting precipitate was dried under vacuum to obtain a charge transporting polymer 1.
  • the number average molecular weight of the charge transporting polymer 1 was 7,600, and the weight average molecular weight was 36,000.
  • the number average molecular weight and the weight average molecular weight were measured by GPC (polystyrene conversion) using tetrahydrofuran (THF) as an eluent.
  • GPC polystyrene conversion
  • THF tetrahydrofuran
  • a toluene solution was prepared using the charge transporting polymers 1 to 8, and the viscosity of the toluene solution was measured.
  • a high-concentration and low-viscosity ink composition can be produced.
  • an organic layer having a large thickness can be easily obtained.
  • the charge transporting polymers 1 to 4 had a short dissolution time. It can be seen that the organic electronic material containing the charge transporting polymer that satisfies the viscosity of the 10% by mass toluene solution less than 3.0 mPa ⁇ s shows high solubility.
  • Organic EL element 1 (Organic EL element 1) The charge transporting polymer 1 (10.0 mg) was dissolved in toluene (2,200 ⁇ L) to obtain a polymer solution. Further, the following onium salt (0.1 mg) was dissolved in toluene (100 ⁇ L) to obtain an onium salt solution. The obtained polymer solution and the onium salt solution were mixed to prepare an ink composition containing the charge transporting polymer 1. The ink composition was spin-coated at 3,000 min -1 on a glass substrate on which ITO was patterned to a width of 1.6 mm under air, and then heated on a hot plate at 200 ° C. for 30 minutes to form a hole injection layer ( 20 nm).
  • the glass substrate was transferred into a vacuum evaporation machine, and NPD (40 nm), CBP: Ir (ppy) 3 (94: 6, 30 nm), BAlq (10 nm), and Alq 3 (30 nm) were placed on the hole injection layer. , LiF (0.8 nm), and Al (100 nm) in this order by a vapor deposition method, and a sealing treatment was performed to produce an organic EL device.
  • Organic EL devices 2 to 8 were produced in the same manner as in the organic EL device 1 except that the charge transporting polymer 1 was changed to the charge transporting polymers 2 to 8.
  • the organic EL devices prepared using the charge transporting polymers 1 to 8 exhibited the same driving voltage, luminous efficiency, and luminous life.
  • an organic electronic material containing a charge transporting polymer in which the viscosity of a 10% by mass toluene solution satisfying less than 3.0 mPa ⁇ s an organic layer having a sufficient film thickness can be formed. Can be formed without affecting the characteristics of

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Abstract

Un mode de réalisation de la présente invention concerne un matériau électronique organique qui contient un polymère de transport de charge, et qui est conçu de telle sorte que : le polymère de transport de charge a une structure ramifiée ; le polymère de transport de charge a un poids moléculaire moyen en poids de 20 000 ou plus ; et si une solution qui contient le polymère de transport de charge et le toluène et a une concentration du polymère de transport de charge de 10 % en masse est préparée, la viscosité de la solution à température ambiante est inférieure à 3,0 mPa·s.
PCT/JP2019/037883 2018-09-28 2019-09-26 Matériau électronique organique et élément électronique organique WO2020067300A1 (fr)

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Publication number Priority date Publication date Assignee Title
JP2014127585A (ja) * 2012-12-26 2014-07-07 Hitachi Chemical Co Ltd 有機エレクトロニクス素子及びその製造方法
JP2017218426A (ja) * 2016-06-08 2017-12-14 日立化成株式会社 イオン性化合物、有機エレクトロニクス材料、有機エレクトロニクス素子、及び有機エレクトロルミネセンス素子

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EP3401973B1 (fr) * 2016-01-08 2020-09-02 Hitachi Chemical Company, Ltd. Matière électronique organique, élément électronique organique et élément électroluminescent organique

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014127585A (ja) * 2012-12-26 2014-07-07 Hitachi Chemical Co Ltd 有機エレクトロニクス素子及びその製造方法
JP2017218426A (ja) * 2016-06-08 2017-12-14 日立化成株式会社 イオン性化合物、有機エレクトロニクス材料、有機エレクトロニクス素子、及び有機エレクトロルミネセンス素子

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