WO2017043502A1 - 有機エレクトロニクス材料及びその利用 - Google Patents
有機エレクトロニクス材料及びその利用 Download PDFInfo
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- WO2017043502A1 WO2017043502A1 PCT/JP2016/076245 JP2016076245W WO2017043502A1 WO 2017043502 A1 WO2017043502 A1 WO 2017043502A1 JP 2016076245 W JP2016076245 W JP 2016076245W WO 2017043502 A1 WO2017043502 A1 WO 2017043502A1
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- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
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Definitions
- Embodiments of the present invention relate to an organic electronics material, an ink composition, an organic layer, an organic electronics element, an organic electroluminescence element (also referred to as “organic EL element”), a display element, a lighting device, and a display device.
- organic EL element organic electroluminescence element
- Organic EL elements are attracting attention as large-area solid-state light source applications, for example, as an alternative to incandescent lamps and gas-filled lamps. It is also attracting attention as the most powerful self-luminous display that can replace the liquid crystal display (LCD) in the flat panel display (FPD) field, and its commercialization is progressing.
- LCD liquid crystal display
- FPD flat panel display
- Organic EL elements are roughly classified into two types, low molecular organic EL elements using low molecular compounds and high molecular organic EL elements using high molecular compounds, depending on the organic materials used.
- the manufacturing method of the organic EL element includes a dry process in which film formation is mainly performed in a vacuum system and a wet process in which film formation is performed by plate printing such as letterpress printing and intaglio printing, and plateless printing such as inkjet. It is roughly divided into two. Since simple film formation is possible, the wet process is expected as an indispensable method for future large-screen organic EL displays (see Patent Document 1).
- an organic layer having excellent solvent resistance can be formed by using a polymer having a large molecular weight or a polymer having a branched structure.
- the solubility of the polymer itself in a solvent decreases, and there is a concern that it will be difficult to obtain an ink composition for use in a wet process.
- the area ratio occupied by components having a molecular weight of less than 20,000 is 40% or less, and the area ratio occupied by components having a molecular weight of 500 or less is 1% or less.
- the present invention relates to an organic electronic material containing a charge transporting polymer.
- Another embodiment of the present invention is a charge transporting polymer from which a component having a molecular weight of less than 20,000 is removed, and an area ratio occupied by the component having a molecular weight of less than 20,000 in a molecular weight distribution chart measured by GPC
- the present invention relates to an organic electronic material containing a charge transporting polymer whose A is 40% or less.
- Another embodiment of the present invention is a method for producing an organic electronic material containing a charge transporting polymer in which an area ratio occupied by components having a molecular weight of less than 20,000 is 40% or less in a molecular weight distribution chart measured by GPC.
- the present invention relates to a method for producing an organic electronic material, including a step of removing a component having a molecular weight of less than 20,000 from a charge transporting polymer.
- Another embodiment of the present invention relates to an ink composition comprising the organic electronic material or the organic electronic material produced by the production method and a solvent. Another embodiment of the present invention relates to an organic layer formed using the organic electronics material or the ink composition.
- Another embodiment of the present invention relates to an organic electronic device comprising at least one organic layer.
- Other embodiment of this invention is related with an organic electroluminescent element provided with at least one said organic layer.
- Another embodiment of this invention is related with the display element provided with the said organic electroluminescent element.
- Other embodiment of this invention is related with the illuminating device provided with the said organic electroluminescent element.
- another embodiment of the present invention relates to a display device comprising the illumination device and a liquid crystal element as display means.
- the organic electronic material and ink composition according to the embodiment of the present invention can form an organic layer suitable for a wet process and having excellent solvent resistance. Moreover, the organic layer which is embodiment of this invention is suitable for the improvement of the luminous efficiency and the light emission lifetime of an organic electronics element. Furthermore, the organic electronics element, the organic EL element, the display element, the lighting device, and the display device according to the embodiment of the present invention are excellent in luminous efficiency characteristics and luminous lifetime characteristics.
- the organic electronic material of this embodiment has an area ratio of 40% or less occupied by a component having a molecular weight of less than 20,000 (hereinafter also referred to as “low molecular weight component”). And a charge transporting polymer (hereinafter, also referred to as “charge transporting polymer 1”) having an area ratio occupied by components having a molecular weight of 500 or less of 1% or less.
- the organic electronic material of another embodiment is a charge transporting polymer from which a component having a molecular weight of less than 20,000 is removed, and an area occupied by the component having a molecular weight of less than 20,000 in a molecular weight distribution chart measured by GPC It is characterized by containing a charge transporting polymer having a ratio of 40% or less (hereinafter also referred to as “charge transporting polymer 2”).
- the organic electronic materials of these embodiments may contain only one kind or two or more kinds of the charge transporting polymer having a low ratio of the low molecular weight component.
- charge transporting polymer or “polymer”
- it means both the charge transporting polymer 1 and the charge transporting polymer 2 without distinction.
- the ratio of the low molecular weight component of 20,000 or less in the polymer is low, and the GPC area ratio is suppressed to 40% or less, so that the polymer itself can be dissolved without increasing the molecular weight of the entire polymer.
- the organic layer having excellent solvent resistance can be formed by improving the curability while maintaining the properties. Therefore, the organic electronic material of the present embodiment is suitable for application to an ink composition for a wet process. Although it is inferred, the low molecular weight component is more easily dissolved than the high molecular weight component, so it is thought that the remaining film ratio (solvent resistance) of the organic layer obtained when a large amount of the low molecular weight component remains is deteriorated. It is done.
- crosslinking group a polymer having a polymerizable functional group (crosslinking group) at the terminal (described later)
- the crosslinking reaction rate is also low. It is considered that reducing the ratio of such low molecular weight components can improve the curability of the resulting organic layer and increase the solvent resistance.
- the organic EL device using this organic layer improves the light emission characteristics and is driven. It has been found that effects such as reduction in voltage, improvement in luminous efficiency, and improvement in luminous lifetime can be obtained. Moreover, the physical property of the polymer as the charge transport material can be controlled by reducing the ratio of the low molecular weight component in the polymer.
- the elution time of a polymer having a molecular weight of 20,000 can be determined using a calibration curve calculated from the elution time of a polystyrene standard sample having a known molecular weight.
- the low molecular weight component specified as described above is preferably 40% or less, and more preferably 30% or less from the viewpoint of obtaining higher curability and more uniform material properties. 20% or less is particularly preferable.
- the charge transporting polymer 1 has a characteristic configuration in which an area ratio occupied by components having a molecular weight of 500 or less is 1% or less.
- an unreacted monomer and an oligomer in which extension of a polymer chain is inhibited by some defect of the monomer itself for example, only about 1 to 4 monomer units are polymerized.
- these unreacted monomers and oligomers can be collectively referred to as “defects”, and “the area ratio occupied by components having a molecular weight of 500 or less is 1% or less” means that these defects are almost present. Means no.
- the method for obtaining the component ratio of the component having a molecular weight of 500 or less is the same as the method for obtaining the component ratio of the low molecular weight component.
- the charge transporting polymer 1 can be conveniently obtained by simply removing a low molecular weight component from a polymer produced by ordinary synthesis, but it is not necessarily required to be removed in the production process.
- a polymer having a low molecular weight component and a small number of defects may be produced by controlling the monomer ratio, reaction solution concentration, monomer addition timing, and the like.
- the removal method is not particularly limited, and any known method can be used. For example, it can be removed by washing the polymer with a solvent in which only low molecular weight components dissolve, reprecipitation, fractionation by preparative GPC, or fractionation using a dialysis membrane. By these general removal methods, the above-mentioned defect in the low molecular weight component is also removed.
- the low molecular weight component can be removed preferably by fractionation by preparative GPC, more preferably by reprecipitation, particularly preferably by washing with a solvent in which only the low molecular weight component is dissolved.
- the charge transporting polymer 2 is obtained by removing a low molecular weight component having a molecular weight of less than 20,000.
- “removal” means to reduce the amount of low molecular weight components having a molecular weight of less than 20,000. Therefore, not only the removal of reducing the low molecular weight component from the polymer having the amount of the low molecular weight component larger than 40% in the GPC chart area ratio until the ratio becomes 40% or less in the area ratio, but also the range in which the area ratio is 40% or less.
- the concept also includes removal to further reduce the low molecular weight component.
- One preferred embodiment is a charge transporting polymer in which components having a molecular weight of less than 20,000 are removed to a ratio of 40% or less (from more than 40%) in the area ratio of the molecular weight distribution chart measured by GPC. .
- FIG. 2 is a diagram conceptually showing “removal of low molecular weight components of a polymer” using a GPC molecular weight distribution chart, and schematically showing a GPC measurement chart before and after the removal of low molecular weight components. ing. In the measurement chart (solid line) before removing the low molecular weight component, detection is also observed on the low molecular weight side where the elution time is long. On the other hand, in the measurement chart (one-dot chain line) after removing the low molecular weight component, the low molecular weight component with a long elution time disappears, while the distribution of the high molecular weight component is before and after the removal of the low molecular weight component. No change is seen in.
- the dispersity (mass average molecular weight / number average molecular weight; Mw / Mn) of the charge transporting polymer is preferably as wide as possible in order to lower the crystallinity of the polymer and ensure solubility in a solvent. Is more preferably 2.3 or more, and most preferably 2.5 or more.
- the degree of dispersion is preferably 20 or less, and more preferably 15 or less, 10 or less, and 7 or less in this order.
- the number average molecular weight of the charge transporting polymer can be appropriately adjusted in consideration of solubility in a solvent, film formability, and the like.
- the number average molecular weight is preferably 500 or more, preferably 1,000 or more, more preferably 2,000 or more, still more preferably 3,000 or more, from the viewpoint of excellent film formation stability and charge transport properties. The above is most preferable.
- the number average molecular weight is preferably 1,000,000 or less, more preferably 800,000 or less, and 600,000 or less. Is more preferable, and 100,000 or less and 50,000 or less are more preferable in this order.
- the weight average molecular weight of the charge transporting polymer can be appropriately adjusted in consideration of solubility in a solvent, film formability, and the like.
- the weight average molecular weight is preferably 1,000 or more, more preferably 5,000 or more, and still more preferably 10,000 or more, from the viewpoint of excellent charge transportability.
- the weight average molecular weight is preferably 1,000,000 or less, more preferably 700,000 or less, and more preferably 400,000 from the viewpoint of maintaining good solubility in a solvent and facilitating preparation of an ink composition. The following is more preferable, and 300,000 or less is most preferable.
- the number average molecular weight and the weight average molecular weight can be measured by GPC using a standard polystyrene calibration curve.
- the measurement conditions for GPC are the same as those described for the low molecular weight component.
- the dispersity, the number average molecular weight, and the weight average molecular weight are all preferable ranges for the charge transporting polymer 2 after the low molecular weight component is removed in the charge transporting polymer 2.
- the weight average molecular weight does not change significantly because there is no change in the molecular weight distribution on the high molecular weight side, although there is a slight increase due to the removal.
- the number average molecular weight more clearly shows an increase in value due to removal.
- the number average molecular weight before removal of the low molecular weight component is less than 10,000, and the number average molecular weight after removal is 10,000 or more.
- the degree of polymerization of the charge transporting polymer is preferably 5 or more and 10,000 or less, and more preferably 10 or more and 3000 or less.
- n is too small, the film-forming stability is lowered, and when it is too large, the solubility tends to be lowered.
- the charge transporting polymer is a polymer having an ability to transport charges, and as described above, the structure is not particularly limited as long as the ratio of the low molecular weight component is reduced.
- the structure of the polymer in the preferred embodiment will be specifically described.
- the charge transporting polymer may be linear or have a branched structure.
- the charge transporting polymer preferably includes at least a divalent structural unit L having charge transporting properties and a monovalent structural unit T constituting a terminal portion, and a trivalent or higher structural unit B constituting a branched portion. Further, it may be included.
- the charge transporting polymer may contain only one type of each structural unit, or may contain a plurality of types. In the charge transporting polymer, each structural unit is bonded to each other at a binding site of “monovalent” to “trivalent or more”.
- Examples of the partial structure contained in the charge transporting polymer include the following.
- the charge transporting polymer is not limited to those having the following partial structures.
- L represents the structural unit L
- B represents the structural unit B
- T represents the structural unit T.
- * in the formula represents a binding site with another structural unit.
- a plurality of L may be the same structural unit or different structural units. The same applies to B and T.
- the structural unit L is a divalent structural unit having charge transportability.
- the structural unit L is not particularly limited as long as it contains an atomic group having the ability to transport charges.
- the structural unit L is a substituted or unsubstituted aromatic amine structure, carbazole structure, thiophene structure, fluorene structure, benzene structure, biphenyl structure, terphenyl 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, benzo Thiophene structure, benzoxazole structure, benzoo
- the structural unit L includes a substituted or unsubstituted aromatic amine structure, carbazole structure, thiophene structure, fluorene structure, benzene structure, pyrrole structure, and these from the viewpoint of obtaining excellent hole transport properties.
- it is selected from a structure containing one or more of these, and is selected from a substituted or unsubstituted aromatic amine structure, carbazole structure, and a structure containing one or more of these Is more preferable.
- the structural unit L is a substituted or unsubstituted fluorene structure, benzene structure, phenanthrene structure, pyridine structure, quinoline structure, and one or two of these. It is preferably selected from structures containing more than one species.
- structural unit L includes the following.
- the structural unit L is not limited to the following.
- Each R independently represents a hydrogen atom or a substituent.
- each R independently represents —R 1 , —OR 2 , —SR 3 , —OCOR 4 , —COOR 5 , —SiR 6 R 7 R 8 , a halogen atom, and a polymerizable functional group described later. Selected from the group consisting of containing groups.
- R 1 to R 8 each independently represents a hydrogen atom; 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.
- 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 ring.
- the alkyl group may be further substituted with an aryl group or heteroaryl group having 2 to 20 carbon atoms, and the aryl group or heteroaryl group may be further linear, cyclic or branched having 1 to 22 carbon atoms. It may be substituted with an alkyl group.
- R is preferably a hydrogen atom, an alkyl group, an aryl group, or an alkyl-substituted aryl group.
- Ar represents an arylene group or heteroarylene group having 2 to 30 carbon atoms.
- 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 heterocycle.
- Ar is preferably an arylene group, more preferably a phenylene group.
- the structural unit T is a monovalent structural unit constituting the terminal portion 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, aromatic heterocyclic structure, and a structure including one or more of these.
- the structural unit T is preferably a substituted or unsubstituted aromatic hydrocarbon structure from the viewpoint of imparting durability without deteriorating charge transportability, and is preferably a substituted or unsubstituted benzene structure. A structure is more preferable.
- the structural unit T when the charge transporting polymer has a polymerizable functional group at the terminal portion, the structural unit T has a polymerizable structure (for example, a polymerizable functional group such as a pyrrol-yl group). ).
- the structural unit T may have the same structure as the structural unit L or may have a different structure.
- structural unit T includes the following.
- the structural unit T is not limited to the following.
- R is the same as R in the structural unit L.
- the charge transporting polymer has a polymerizable functional group to be described later at the terminal portion, preferably at least one of R is a group containing a polymerizable functional group.
- the structural unit B is a trivalent or higher-valent structural unit that constitutes a branched portion when the charge transporting polymer has a branched structure.
- the structural unit B is preferably hexavalent or less, more preferably trivalent or tetravalent, from the viewpoint of improving the durability of the organic electronic element.
- the structural unit B is preferably a unit having charge transportability.
- the structural unit B is a substituted or unsubstituted aromatic amine structure, carbazole structure, condensed polycyclic aromatic hydrocarbon structure, and one or two of these from the viewpoint of improving the durability of the organic electronic device. Selected from structures containing more than one species.
- the structural unit B may have the same structure as the structural unit L or may have a different structure, may have the same structure as the structural unit T, or may have a different structure. You may have.
- 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 arenetriyl group or a heteroarenetriyl group having 2 to 30 carbon atoms.
- the arenetriyl group is an atomic group obtained by removing three hydrogen atoms from an aromatic hydrocarbon.
- the heteroarene triyl group is an atomic group obtained by removing three hydrogen atoms from an aromatic heterocyclic ring.
- Ar each independently represents a divalent linking group, for example, each independently represents an arylene group or heteroarylene group having 2 to 30 carbon atoms.
- Ar is preferably an arylene group, more preferably a phenylene group.
- Y represents a divalent linking group.
- one R atom in the structural unit L (excluding a group containing a polymerizable functional group) has one more hydrogen atom from a group having one or more hydrogen atoms.
- divalent groups excluding. Z represents any of a carbon atom, a silicon atom, or a phosphorus atom.
- the benzene ring and Ar may have a substituent, and examples of the substituent include R in the structural unit L.
- the charge transporting polymer preferably has at least one polymerizable functional group (also referred to as “polymerizable substituent”) from the viewpoint of curing by a polymerization reaction and changing the solubility in a solvent.
- the “polymerizable functional group” refers to a functional group that can form a bond with each other by applying heat and / or light.
- Examples of the polymerizable functional group include a group having a carbon-carbon multiple bond (for example, vinyl group, allyl group, butenyl group, ethynyl group, acryloyl group, acryloyloxy group, acryloylamino group, methacryloyl group, methacryloyloxy group, methacryloylamino group).
- groups, vinyloxy groups, vinylamino groups, etc.) groups having a small ring (eg, cyclic alkyl groups such as cyclopropyl groups, cyclobutyl groups; cyclic ether groups such as epoxy groups (oxiranyl groups), oxetane groups (oxetanyl groups), etc.
- Diketene group Diketene group; episulfide group; lactone group; lactam group, etc.), heterocyclic group (for example, furan-yl group, pyrrol-yl group, thiophen-yl group, silole-yl group) and the like.
- a vinyl group, an acryloyl group, a methacryloyl group, an epoxy group, and an oxetane group are particularly preferable, and from the viewpoint of reactivity and characteristics of the organic electronics element, a vinyl group, an oxetane group, or an epoxy group is more preferable. An oxetane group is preferred and the most preferred.
- the main skeleton of the charge transporting polymer and the polymerizable functional group are, for example, linear alkylene chains having 1 to 8 carbon atoms. It is preferable that it is connected.
- a hydrophilic chain such as an ethylene glycol chain or a diethylene glycol chain from the viewpoint of improving the affinity with a hydrophilic electrode such as ITO. preferable.
- the charge transporting polymer is polymerized with the end of the alkylene chain and / or the hydrophilic chain, that is, with these chains.
- An ether bond or an ester bond may be present at the connecting portion with the functional group and / or the connecting portion between these chains and the skeleton of the charge transporting polymer.
- group containing a polymerizable functional group means a polymerizable functional group itself or a group obtained by combining a polymerizable functional group with an alkylene chain or the like.
- a group containing a polymerizable functional group for example, a group exemplified in International Publication No. WO2010 / 140553 can be suitably used.
- the polymerizable functional group may be introduced into the terminal part (that is, the structural unit T) of the charge transporting polymer, or may be introduced into a part other than the terminal part (that is, the structural unit L or B). And may be introduced into both of the portions other than the terminal. From the viewpoint of curability, it is preferably introduced at least at the end portion, and from the viewpoint of achieving both curability and charge transportability, it is preferably introduced only at the end portion.
- the polymerizable functional group may be introduced into the main chain of the charge transporting polymer or into the side chain, and both the main chain and the side chain may be introduced. May be introduced.
- 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.
- the number of polymerizable functional groups is preferably 1,000 or less, more preferably 500 or less, from the viewpoint of maintaining charge transportability.
- the number of polymerizable functional groups per molecule of the charge transporting polymer is the amount of the polymerizable functional group used to synthesize the charge transporting polymer (for example, the amount of the monomer having a polymerizable functional group), each structure
- the average value can be obtained by using the monomer charge corresponding to the unit and the weight average molecular weight of the charge transporting polymer.
- the number of polymerizable functional groups is the ratio between the integral value of the signal derived from the polymerizable functional group and the integral value of the entire spectrum in the 1 H NMR (nuclear magnetic resonance) spectrum of the charge transporting polymer, the charge transporting polymer
- the weight average molecular weight can be used to calculate the average value. Since it is simple, when the preparation amount is clear, a value obtained by using the preparation amount is preferably adopted.
- the proportion of the structural unit L contained in the charge transporting polymer is preferably 10 mol% or more, more preferably 20 mol% or more, and more preferably 30 mol% or more based on the total structural unit from the viewpoint of obtaining sufficient charge transportability. Is more preferable. Further, 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 in consideration of the structural unit T and the structural unit B introduced as necessary.
- the proportion of the structural unit T contained in the charge transporting polymer is based on the total structural unit from the viewpoint of improving the characteristics of the organic electronics element or suppressing the increase in the viscosity and satisfactorily synthesizing the charge transporting polymer. 5 mol% or more is preferable, 10 mol% or more is more preferable, and 15 mol% or more is still more preferable.
- 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 sufficient charge transport properties.
- the proportion of the structural unit B is preferably 1 mol% or more, more preferably 5 mol% or more, based on the total structural units, from the viewpoint of improving the durability of the organic electronics element. 10 mol% or more is more preferable.
- the proportion of the structural unit B is preferably 50 mol% or less, preferably 40 mol% or less, from the viewpoint of suppressing the increase in viscosity and satisfactorily synthesizing the charge transporting polymer or obtaining sufficient charge transportability. Is more preferable, and 30 mol% or less is still more preferable.
- the proportion of the polymerizable functional group is preferably 0.1 mol% or more based on the total structural unit from the viewpoint of efficiently curing the charge transporting polymer, 1 mol% or more is more preferable, and 3 mol% or more is still more 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 polymerizable functional groups” here refers to the ratio of structural units having a polymerizable functional group.
- the proportion of the structural unit can be determined by using the charged amount of the monomer corresponding to each structural unit used for synthesizing the charge transporting polymer. Moreover, the ratio of the structural unit can be calculated as an average value using an integrated value of the spectrum derived from each structural unit in the 1 H NMR spectrum of the charge transporting polymer. Since it is simple, when the preparation amount is clear, a value obtained by using the preparation amount is preferably adopted.
- the charge transporting polymer is mainly composed of a structural unit having an aromatic amine structure and / or a structural unit having a carbazole structure from the viewpoint of having a high hole injection property, a hole transporting property, and the like.
- a compound having a unit (main skeleton) is preferred.
- the charge transporting polymer is preferably a compound having at least two polymerizable substituents from the viewpoint of easily multilayering. From the viewpoint of having excellent curability, the polymerizable substituent is preferably a group having a cyclic ether structure, a group having a carbon-carbon multiple bond, or the like.
- the charge transporting polymer of this embodiment is preferably a polymer or copolymer of a monomer containing a structural unit having a hole transporting property.
- a monomer mixture containing one or more monomers including the structural unit L and one or more monomers including the structural unit T, and optionally including a monomer including the structural unit B, is used to convert these monomers.
- the copolymer can be preferably produced by copolymerization.
- the type of copolymerization may be an alternating, random, block or graft copolymer, or a copolymer having an intermediate structure thereof, for example, a random copolymer having a block property. .
- the charge transporting polymer can be produced by various synthetic methods and is not particularly limited.
- known coupling reactions 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 together.
- 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 and the like with a phosphine ligand can also be used.
- the description of International Publication No. WO2010 / 140553 can be referred to.
- the charge transporting polymer 2 can be obtained by removing a predetermined low molecular weight component by an arbitrary method, and the charge transporting polymer 1 having a low low molecular weight component can be easily removed by removing the low molecular weight component. Can get to.
- the organic electronic material may contain any additive, for example, may further contain a dopant.
- the dopant can be added to the organic electronic material to exhibit a doping effect and improve the charge transport property.
- Doping includes p-type doping and n-type doping.
- p-type doping a substance serving as an electron acceptor is used as a dopant
- n-type doping a substance serving as an electron donor is used as a dopant. It is preferable to perform p-type doping for improving hole transportability and n-type doping for improving electron transportability.
- the dopant used in the organic electronic material may be a dopant that exhibits any effect of p-type doping or n-type doping. Further, one kind of dopant may be added alone, or plural kinds of dopants may be mixed and added.
- the dopant used for p-type doping is an electron-accepting compound, and examples thereof include Lewis acids, proton acids, transition metal compounds, ionic compounds, halogen compounds, and ⁇ -conjugated compounds.
- Lewis acid FeCl 3 , PF 5 , AsF 5 , SbF 5 , BF 5 , BCl 3 , BBr 3 and the like;
- protonic acid HF, HCl, HBr, HNO 5 , H 2 SO 4 , HClO 4 and other inorganic acids, 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; transition metal compounds include FeCl 3
- the electron-accepting compounds described in JP 2000-36390 A, JP 2005-75948 A, JP 2003-213002 A, and the like can also be used.
- the dopant used for n-type doping is an electron donating compound, for example, alkali metals such as Li and Cs; alkaline earth metals such as Mg and Ca; alkali metals such as LiF and Cs 2 CO 3 and / or Examples include alkaline earth metal salts; metal complexes; electron-donating organic compounds.
- alkali metals such as Li and Cs
- alkaline earth metals such as Mg and Ca
- alkali metals such as LiF and Cs 2 CO 3 and / or Examples include alkaline earth metal salts; metal complexes; electron-donating organic compounds.
- the charge transporting polymer has a polymerizable functional group
- a compound that can act as a polymerization initiator for the polymerizable functional group as a dopant in order to facilitate the change in solubility of the organic layer.
- the organic electronic material may further contain a charge transporting low molecular weight 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 transporting property. 80 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 an additive such as a dopant, the content of the charge transporting polymer may be, for example, 95% by mass or less, 90% by mass or less, and the like.
- the content is preferably 0.01% by mass or more, and 0.1% by mass or more with respect to the total mass of the organic electronic material from the viewpoint of improving the charge transport property of the organic electronic material. More preferred is 0.5% by mass or more. Moreover, from a viewpoint of maintaining favorable film formability, 50 mass% or less is preferable with respect to the total mass of the organic electronic material, 30 mass% or less is more preferable, and 20 mass% or less is still more preferable.
- an organic electronic material containing a charge transporting polymer having an area ratio occupied by a component having a molecular weight of less than 20,000 is 40% or less in a molecular weight distribution chart measured by GPC.
- the preferred structure, number average molecular weight, weight average molecular weight, and dispersity of the charge transporting polymer to be produced are also as described above.
- a method for producing an organic electronic material containing a charge transporting polymer comprises the steps of providing a charge transporting polymer, and removing a component having a molecular weight of less than 20,000 from the charge transporting polymer.
- a step of obtaining a charge transporting polymer having an area ratio occupied by components having a molecular weight of less than 20,000 in a molecular weight distribution chart measured by GPC is 40% or less.
- the charge transporting polymer synthesized by general polymerization or copolymerization contains a low molecular weight component in an amount of more than 40% in terms of a GPC chart area ratio, it is removed. Including reducing to 40% or less.
- An ink composition according to an embodiment of the present invention includes the organic electronics material of the above-described embodiment (including the organic electronics material obtained by the method for producing the organic electronics material of the above-described embodiment; the same applies to the following description). And a solvent capable of dissolving or dispersing the material.
- the organic layer can be easily formed by a simple method such as a coating method.
- solvent water, an organic solvent, or a mixed solvent thereof can be used.
- Organic solvents 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; ethylene glycol 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, 2,4-dimethylanisole, 2,4
- Amide solvents dimethyl sulfoxide, tetrahydrofuran, acetone, chloroform, methylene chloride and the like can be mentioned.
- the ink 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 the ink composition, it is preferable to use a substance having both a function as a dopant and a function as a polymerization initiator. As such a substance, the said ionic compound is mentioned, for example.
- the ink composition may further contain an additive as an optional component.
- additives include polymerization inhibitors, stabilizers, thickeners, gelling agents, flame retardants, antioxidants, antioxidants, oxidizing agents, reducing agents, surface modifiers, emulsifiers, antifoaming agents, Examples thereof include a dispersant and a surfactant.
- the content of the solvent in the ink 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 0.5% by mass or more. More preferred is an amount of
- 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 which is an embodiment of the present invention is a layer formed using the organic electronic material or ink composition of the above embodiment.
- the organic layer can be satisfactorily and easily formed by a coating method.
- the coating method include spin coating method; casting method; dipping method; letterpress printing, intaglio printing, offset printing, planographic printing, letterpress inversion offset printing, screen printing, gravure printing and other plate printing methods; ink jet method, etc.
- a known method such as a plateless printing method may be used.
- the organic layer (coating layer) obtained after the coating may be dried using a hot plate or an oven to remove the solvent.
- the solubility of the organic layer can be changed by proceeding the polymerization reaction of the charge transporting polymer by light irradiation, heat treatment or the like.
- the solubility of the organic layer can be changed by proceeding the polymerization reaction of the charge transporting polymer by light irradiation, heat treatment or the like.
- By laminating organic layers with different solubility it is possible to easily increase the number of organic electronics elements.
- the description of International Publication No. WO2010 / 140553 can be referred to.
- the thickness of the organic layer after drying or curing is preferably 0.1 nm or more, more preferably 1 nm or more, and further preferably 3 nm or more.
- 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 electrical resistance.
- the organic electronic device which is an embodiment of the present invention has at least one organic layer of the above-described embodiment.
- the organic electronics element include an organic EL element, an organic photoelectric conversion element, and an organic transistor.
- the organic electronic element preferably has a structure in which an organic layer is disposed between at least a pair of electrodes.
- the organic EL element which is an embodiment of the present invention has at least one organic layer of the above-described embodiment.
- the organic EL element usually includes a light emitting layer, an anode, a cathode, and a substrate, and other functional layers such as a hole injection layer, an electron injection layer, a hole transport layer, and an electron transport layer are provided as necessary. I have. Each layer may be formed by a vapor deposition method or a coating method.
- the organic EL element preferably has the organic layer as a light emitting layer or other functional layer, more preferably as a functional layer, and still more preferably as at least one of a hole injection layer and a hole transport layer.
- FIG. 1 is a schematic cross-sectional view showing an embodiment of an organic EL element.
- the organic EL element of FIG. 1 is an element having a multilayer structure, and includes a substrate 8, an anode 2, a hole injection layer 3 and 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. Hereinafter, each layer will be described.
- Light emitting layer As a material used for the light emitting layer, a light emitting material such as a low molecular compound, a polymer, or a dendrimer can be used. A polymer is preferable because it has high solubility in a solvent and is suitable for a coating method. Examples of the light emitting material include a fluorescent material, a phosphorescent material, a thermally activated delayed fluorescent material (TADF), and the like.
- TADF thermally activated delayed fluorescent material
- Fluorescent materials such as perylene, coumarin, rubrene, quinacdrine, stilbene, dyes for dye lasers, aluminum complexes, and derivatives thereof; polyfluorene, polyphenylene, polyphenylene vinylene, polyvinylcarbazole, fluorene-benzothiadiazole copolymer , Fluorene-triphenylamine copolymers, polymers thereof such as 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) that emits blue light (iridium (III) bis [(4,6-difluorophenyl) -pyridinate-N, C 2 ] picolinate), and Ir (ppy) 3 that 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), CDBP (4,4′- Bis (carbazol-9-yl) -2,2′-dimethylbiphenyl), derivatives thereof, and the like.
- the polymer include the organic electronic materials, polyvinyl carbazole, polyphenylene, polyfluorene, derivatives thereof, and the like of the embodiment. It is done.
- thermally activated delayed fluorescent materials include Adv.AMater., 21, 4802-4906 (2009); Appl. Phys. Lett., 98, 083302 (2011); Chem. Comm., 48, 9580 (2012) ; Appl. Phys. Lett., 101, 093306 (2012); J. Am. Chem. Soc., 134, 14706 (2012); Chem. Comm., 48, 11392 (2012); Nature, 492, 234 (2012) ); Adv. Mater., 25, 3319 (2013); J. Phys. Chem. A, 117, 5607 (2013); Phys. Chem. Chem. Phys., 15, 15850 (2013); Chem. Comm., 49, 10385) (2013); Chem. Lett., 43, 319 (2014) and the like.
- the organic layer formed using the organic electronic material is preferably used as at least one of a hole injection layer and a hole transport layer, and more preferably at least as a hole transport layer. As described above, these layers can be easily formed by using an ink composition containing an organic electronic material.
- a known material can be used for the hole injection layer.
- a known material can be used for the hole transport layer.
- Examples of materials that can be used for the hole injection layer and the hole transport layer include aromatic amine compounds (for example, N, N′-di (naphthalen-1-yl) -N, N′-diphenyl-benzidine ( aromatic diamines such as ⁇ -NPD), phthalocyanine compounds, thiophene compounds (eg, thiophene-based conductive polymers (eg, poly (3,4-ethylenedioxythiophene): poly (4-styrenesulfonate)) (PEDOT: PSS) and the like.
- aromatic amine compounds for example, N, N′-di (naphthalen-1-yl) -N, N′-diphenyl-benzidine ( aromatic diamines such as ⁇ -NPD), phthalocyanine compounds, thiophene compounds (eg, thiophene-based conductive polymers (eg, poly (3,4-ethylenedioxythiophene): poly (4-styrenesulfonate
- Electrode transport layer examples include phenanthroline derivatives, bipyridine derivatives, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, condensed ring tetracarboxylic anhydrides such as naphthalene and perylene, and carbodiimides. Fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, thiadiazole derivatives, benzimidazole derivatives, quinoxaline derivatives, aluminum complexes, and the like. Moreover, the organic electronic material of the said embodiment 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.
- examples of other materials include oxides (for example, ITO: indium oxide / tin oxide) and conductive polymers (for example, polythiophene-polystyrene sulfonic acid mixture (PEDOT: PSS)).
- substrate glass, plastic or the like can be used.
- the substrate is preferably transparent and is preferably a flexible substrate having flexibility. Quartz glass, light transmissive resin film, and the like are preferably used.
- the resin film examples include films made of polyethylene terephthalate, polyethylene naphthalate, polyethersulfone, polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate, cellulose triacetate, cellulose acetate propionate, and the like. Can be mentioned.
- an inorganic substance such as silicon oxide or silicon nitride may be coated on the resin film in order to suppress permeation of water vapor, oxygen and the like.
- the organic EL element may be sealed in order to reduce the influence of outside air and extend the life.
- a material used for sealing glass, epoxy resin, acrylic resin, polyethylene terephthalate, polyethylene naphthalate and other plastic films, or inorganic materials such as silicon oxide and silicon nitride can be used. Absent.
- the sealing method 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, interior lighting, a clock, or a liquid crystal backlight.
- a method of simultaneously emitting a plurality of emission colors using a plurality of light emitting materials and mixing the colors can be used.
- a combination of a 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 of blue and yellow, yellow green and orange, etc. Is mentioned.
- the emission color can be controlled by adjusting the type and amount of the light emitting material.
- the display element which is embodiment of this invention is equipped with the organic EL element of the said embodiment.
- 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 according to the embodiment of the present invention.
- the display apparatus which is embodiment of this invention is equipped with the illuminating device and the liquid crystal element as a display means.
- the display device can be a display device using a known liquid crystal element as a display unit, that is, a liquid crystal display device using the illumination device according to the embodiment of the present invention as a backlight.
- % means “mass%”.
- the monomers constituting the structural unit L, the structural unit B, and the structural unit T are referred to as “L monomer”, “B monomer”, and “T monomer”, respectively.
- T1 monomer and T2 monomer may be used.
- the scavenger was filtered off with a polytetrafluoroethylene filter (Dismic 25JP020AN) having a pore diameter of 0.2 ⁇ m, and mixed with methanol to reprecipitate.
- the polymer was collected by filtration and vacuum-dried in a desiccator to obtain a charge transporting polymer 1-1 from which low molecular weight components were not removed.
- the weight average molecular weight, number average molecular weight, and ratio of low molecular weight components (GPC chart area ratio) of the obtained polymer were determined by GPC.
- the measurement conditions for GPC are as described above.
- Table 7 shows the obtained values.
- FIG. 3 shows the GPC measurement chart of the charge transporting polymer 1-1 and the charge transporting polymer 2-1 in an overlapping manner.
- the charge transporting polymer 2-1 is obtained by removing the low molecular weight component, the amount of the component having a molecular weight of less than 20,000 is reduced as compared with the charge transporting polymer 1-1 not removed. It is shown that.
- UV-VIS spectrum was measured under the following conditions.
- An organic layer was formed in the same manner as in Comparative Example 1-1 except that one of the charge transporting polymers shown in Table 8 below was used instead of the charge transporting polymer 1-1, and the remaining film ratio was determined. It was measured. The results are shown in Table 8.
- the charge transporting polymer 3-1 (4.5 mg), the ionic compound 1 (0.13 mg), and toluene (1.2 mL) were mixed to prepare an ink composition for forming a hole transporting layer.
- This ink composition was spin-coated on the hole injection layer obtained above at a rotation speed of 3000 min ⁇ 1 and then cured by heating on a hot plate at 120 ° C. for 10 minutes to obtain a hole transport layer (40 nm). Formed.
- the glass substrate obtained above was transferred into a vacuum vapor deposition machine, and CBP: Ir (ppy) 3 (94: 6, 30 nm), BAlq (10 nm), Alq 3 (30 nm), LiF (on the hole transport layer) 0.8 nm) and Al (100 nm) were deposited in this order to form a film, and a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode were laminated.
- the laminated glass substrate is transferred to a dry nitrogen environment without opening to the atmosphere.
- This is a sealing glass obtained by applying 0.4 mm counterbore to 0.7 mm non-alkali glass, and photocuring.
- a polymer type organic EL device having a multilayer structure was produced by sealing using an adhesive epoxy resin.
- Example 4-1 An organic EL device was produced in the same manner as in Comparative Example 4-1, except that the hole transport layer was formed using the charge transport polymer 4-1 instead of the charge transport polymer 3-1.
- Examples 4-2 to 4-7 An organic EL device was produced in the same manner as in Comparative Example 4-1, except that the hole transport layer was formed using any of the polymers shown in Table 10 instead of the charge transport polymer 3-1.
- the glass substrate obtained above is transferred into a vacuum deposition machine, and ⁇ NPD (20 nm), CBP: Ir (ppy) 3 (94: 6, 30 nm), BAlq (10 nm), Alq 3 (30 nm), LiF (0.8 nm), and Al (100 nm) are vapor-deposited in this order to form a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and A cathode was laminated.
- the laminated glass substrate is transferred to a dry nitrogen environment without opening to the atmosphere.
- This is a sealing glass obtained by applying 0.4 mm counterbore to 0.7 mm non-alkali glass, and photocuring.
- a polymer type organic EL device having a multilayer structure was produced by sealing using an adhesive epoxy resin.
- Example 5-1 An organic EL device was produced in the same manner as in Comparative Example 5-1, except that the hole injection layer was formed using the charge transporting polymer 4-1 instead of the charge transporting polymer 3-1.
- Examples 5-2 to 5-7 An organic EL device was produced in the same manner as in Comparative Example 5-1, except that a hole injection layer was formed using any one of the polymers shown in Table 12 instead of the charge transporting polymer 3-1.
- the organic EL device of the example had a lower driving voltage, superior luminous efficiency, and a longer luminous lifetime than those of the comparative example. That is, by using a charge transporting polymer with a low content of low molecular weight components, a special effect of improving luminous efficiency and luminous lifetime was obtained.
Abstract
Description
電荷輸送性ポリマーから分子量20,000未満の成分を除去する工程を含む、有機エレクトロニクス材料の製造方法に関する。
本発明の他の実施形態は、前記有機エレクトロニクス材料、又は前記インク組成物を用いて形成された、有機層に関する。
本発明の他の実施形態は、前記有機層を少なくとも一つ備える、有機エレクトロルミネセンス素子に関する。
本発明の他の実施形態は、前記有機エレクトロルミネセンス素子を備えた、照明装置に関する。
さらに、本発明の他の実施形態は、前記照明装置と、表示手段として液晶素子とを備えた、表示装置に関する。
本実施形態の有機エレクトロニクス材料は、GPCにより測定される分子量分布チャートにおいて、分子量20,000未満の成分(以下、これを「低分子量成分」とも記す。)の占める面積比が40%以下であり、かつ、分子量500以下の成分の占める面積比が1%以下である電荷輸送性ポリマー(以下、これを「電荷輸送性ポリマー1」とも記す。)を含有することを特徴とする。
なお、本明細書において、単に「電荷輸送性ポリマー」(又は「ポリマー」)と記す場合は、上記電荷輸送性ポリマー1と電荷輸送性ポリマー2の双方を、特に区別無く意味している。
推論ではあるが、低分子量成分は高分子量成分に比べ、それ自身が溶解しやすいので、低分子量成分が多く残存することにより得られる有機層の残膜率(耐溶剤性)を悪化させると考えられる。加えて、末端に重合性官能基(架橋基)を持つポリマー(後述)とした場合には、低分子量成分においては末端の架橋基の量が少なく、よって架橋反応率も低いと考えられるので、こうした低分子量成分の比率を減じることで、得られる有機層の硬化性を向上させ、耐溶剤性を高めることができると考察する。
また、ポリマー中の低分子量成分の比率が下がることで、電荷輸送材料としてのポリマーの物性を制御することができる。
(低分子量成分)
はじめに、GPC(ゲルパーミエーションクロマトグラフィ)を用いて規定される、電荷輸送性ポリマーの低分子量成分の成分比率の求め方について説明する。
「GPCにより測定される分子量分布チャートにおいて、分子量20,000未満の成分(すなわち低分子量成分)の占める面積比が40%以下である」とは、溶出時間と検出強度によって表されるGPCチャート(溶出パターン)において、該チャートの全面積に対する、後述するポリスチレン換算分子量で20,000未満の成分の占める面積比が、40%以下であることを意味する。すなわち、溶出時間が長い低分子量側の面積比が、全チャート面積の40%以下である。なお、全チャート面積は、溶媒及び不純物ピークを除いたピーク全体の面積である。
装置:高速液体クロマトグラフ Prominence(株)島津製作所
送液ポンプ(LC-20AD)
脱気ユニット(DGU-20A)
オートサンプラ(SIL-20AHT)
カラムオーブン(CTO-20A)
PDA検出器(SPD-M20A)
示差屈折率検出器(RID-20A)
カラム:Gelpack(登録商標)
GL-A160S(製造番号:686-1J27)
GL-A150S(製造番号:685-1J27)日立化成(株)
溶離液:テトラヒドロフラン(THF)(HPLC用、安定剤含有)和光純薬工業(株)
流速:1mL/min
カラム温度:40℃
検出波長:254nm
分子量標準物質:PStQuick A/B/C 東ソー(株)
一般に、通常のポリマー合成では、得られたポリマーに未反応モノマー、及び、モノマー自身の何らかの欠陥によってポリマ鎖の伸張が阻害されたオリゴマー(例えば、モノマーユニットが1~4個程度しか重合していないもの)が、いかに高分子量のポリマーであっても、数パーセント以上程度は不可避的に含まれていることが多い。これらの未反応モノマー及びオリゴマーを、まとめて「欠陥体」とも呼ぶことができ、「分子量500以下の成分の占める面積比が1%以下である」とは、これらの欠陥体がほとんど存在していないことを意味する。この場合の、分子量500以下の成分の成分比率の求め方も、上記の低分子量成分の成分比率の求め方と同様である。
除去の方法については、特に限定されず、任意の公知の方法を用いることができる。例えば、低分子量成分のみが溶解する溶媒によるポリマーの洗浄、再沈殿、分取GPCによる分画、もしくは、透析膜を用いた分画などにより除去することができる。これらの一般の除去方法により、低分子量成分中の上記欠陥体も、併せて除去される。操作性の観点から、好ましくは分取GPCによる分画、より好ましくは再沈殿、特に好ましくは低分子量成分のみが溶解する溶媒による洗浄により、低分子量成分の除去を行うことができる。
好ましい一実施形態は、分子量20,000未満の成分が、GPCにより測定される分子量分布チャートの面積比で(40%超から)40%以下の割合になるまで除去された電荷輸送性ポリマーである。
電荷輸送性ポリマーの分散度(質量平均分子量/数平均分子量;Mw/Mn)は、ポリマの結晶性を下げ、溶媒への溶解性を担保するため、広いほうが好ましく、2.0以上であることが好ましく、2.3以上であることがより好ましく、最も好ましくは2.5以上である。一方、有機エレクトロニクス素子の特性のバラツキを抑え、又は、ポリマーを簡便に合成する観点からは、分散度は20以下が好ましく、15以下、10以下、7以下であることが、この順にさらに好ましい。
電荷輸送性ポリマーの数平均分子量は、溶剤への溶解性、成膜性等を考慮して適宜、調整できる。数平均分子量は、成膜安定性及び電荷輸送性に優れるという観点から、500以上が好ましく、1,000以上が好ましく、2,000以上がより好ましく、3,000以上が一層好ましく、10,000以上が最も好ましい。また、溶媒への良好な溶解性を保ち、インク組成物の調製を容易にするという観点から、数平均分子量は1,000,000以下が好ましく、800,000以下がより好ましく、600,000以下が更に好ましく、100,000以下、50,000以下がこの順でより一層好ましい。
電荷輸送性ポリマーの重量平均分子量は、溶剤への溶解性、成膜性等を考慮して適宜、調整できる。重量平均分子量は、電荷輸送性に優れるという観点から、1,000以上が好ましく、5,000以上がより好ましく、10,000以上が更に好ましい。また、重量平均分子量は、溶媒への良好な溶解性を保ち、インク組成物の調製を容易にするという観点から、1,000,000以下が好ましく、700,000以下がより好ましく、400,000以下が更に好ましく、300,000以下が最も好ましい。
低分子量成分の除去の前後において、重量平均分子量では、除去による多少の増加はあっても、高分子量側の分子量分布の変更はないため大きな変化は見られない。これに対し、数平均分子量では、除去による値の増加がより明確に示される。好ましい一実施形態において、低分子量成分除去前の数平均分子量は10,000未満であり、除去後の数平均分子量は10,000以上である。
電荷輸送性ポリマーの重合度は、5以上10,000以下が好ましく、10以上3000以下がより好ましい。nが小さすぎると製膜安定性が低下し、大きすぎると溶解度が低下する傾向がある。
電荷輸送性ポリマーは、電荷を輸送する能力を有するポリマーであり、上述のとおり、低分子量成分の比率が低減されたものであれば、その構造について特に限定されることはない。
以下に、好ましい実施形態におけるポリマーの構造を具体的に説明する。
構造単位Lは、電荷輸送性を有する2価の構造単位である。構造単位Lは、電荷を輸送する能力を有する原子団を含んでいればよく、特に限定されない。例えば、構造単位Lは、置換又は非置換の、芳香族アミン構造、カルバゾール構造、チオフェン構造、フルオレン構造、ベンゼン構造、ビフェニル構造、ターフェニル構造、ナフタレン構造、アントラセン構造、テトラセン構造、フェナントレン構造、ジヒドロフェナントレン構造、ピリジン構造、ピラジン構造、キノリン構造、イソキノリン構造、キノキサリン構造、アクリジン構造、ジアザフェナントレン構造、フラン構造、ピロール構造、オキサゾール構造、オキサジアゾール構造、チアゾール構造、チアジアゾール構造、トリアゾール構造、ベンゾチオフェン構造、ベンゾオキサゾール構造、ベンゾオキサジアゾール構造、ベンゾチアゾール構造、ベンゾチアジアゾール構造、ベンゾトリアゾール構造、及び、これらの1種又は2種以上を含む構造から選択される。芳香族アミン構造は、好ましくはトリアリールアミン構造であり、より好ましくはトリフェニルアミン構造である。
構造単位Tは、電荷輸送性ポリマーの末端部を構成する1価の構造単位である。構造単位Tは、特に限定されず、例えば、置換又は非置換の、芳香族炭化水素構造、芳香族複素環構造、及び、これらの1種又は2種以上を含む構造から選択される。一実施形態において、構造単位Tは、電荷の輸送性を低下させずに耐久性を付与するという観点から、置換又は非置換の芳香族炭化水素構造であることが好ましく、置換又は非置換のベンゼン構造であることがより好ましい。また、他の実施形態において、後述するように、電荷輸送性ポリマーが末端部に重合性官能基を有する場合、構造単位Tは重合可能な構造(例えば、ピロール-イル基等の重合性官能基)であってもよい。構造単位Tは、構造単位Lと同じ構造を有していても、又は、異なる構造を有していてもよい。
構造単位Bは、電荷輸送性ポリマーが分岐構造を有する場合に、分岐部を構成する3価以上の構造単位である。構造単位Bは、有機エレクトロニクス素子の耐久性向上の観点から、好ましくは6価以下であり、より好ましくは3価又は4価である。構造単位Bは、電荷輸送性を有する単位であることが好ましい。例えば、構造単位Bは、有機エレクトロニクス素子の耐久性向上の観点から、置換又は非置換の、芳香族アミン構造、カルバゾール構造、縮合多環式芳香族炭化水素構造、及び、これらの1種又は2種以上を含有する構造から選択される。構造単位Bは、構造単位Lと同じ構造を有していても、又は、異なる構造を有していてもよく、また、構造単位Tと同じ構造を有していても、又は、異なる構造を有していてもよい。
一実施形態において電荷輸送性ポリマーは、重合反応により硬化させ、溶剤への溶解度を変化させる観点から、重合性官能基(「重合可能な置換基」とも記す。)を少なくとも1つ有することが好ましい。「重合性官能基」とは、熱及び/又は光を加えることにより、互いに結合を形成し得る官能基をいう。
電荷輸送性ポリマーに含まれる構造単位Lの割合は、十分な電荷輸送性を得る観点から、全構造単位を基準として、10モル%以上が好ましく、20モル%以上がより好ましく、30モル%以上が更に好ましい。また、構造単位Lの割合は、構造単位T及び必要に応じて導入される構造単位Bを考慮すると、95モル%以下が好ましく、90モル%以下がより好ましく、85モル%以下が更に好ましい。
本実施形態の電荷輸送性ポリマーは、正孔輸送性を有する構造単位を含むモノマーの重合体又は共重合体であることが好ましい。好ましくは、上記構造単位Lを含む一種以上のモノマーと、上記構造単位Tを含む一種以上のモノマーとを含み、任意に上記構造単位Bを含むモノマーを含むモノマー混合物を用いて、これらのモノマーを共重合させることにより、好ましく製造することができる。共重合の形式は、交互、ランダム、ブロック又はグラフト共重合体であってもよいし、それらの中間的な構造を有する共重合体、例えばブロック性を帯びたランダム共重合体であってもよい。
有機エレクトロニクス材料は、任意の添加剤を含むことができ、例えばドーパントを更に含有してよい、ドーパントは、有機エレクトロニクス材料に添加することでドーピング効果を発現させ、電荷の輸送性を向上させ得るものであればよく、特に制限はない。ドーピングには、p型ドーピングとn型ドーピングがあり、p型ドーピングではドーパントとして電子受容体として働く物質が用いられ、n型ドーピングではドーパントとして電子供与体として働く物質が用いられる。正孔輸送性の向上にはp型ドーピング、電子輸送性の向上にはn型ドーピングを行うことが好ましい。有機エレクトロニクス材料に用いられるドーパントは、p型ドーピング又はn型ドーピングのいずれの効果を発現させるドーパントであってもよい。また、1種のドーパントを単独で添加しても、複数種のドーパントを混合して添加してもよい。
有機エレクトロニクス材料は、電荷輸送性低分子化合物、他のポリマー等を更に含有してもよい。
有機エレクトロニクス材料中の電荷輸送性ポリマーの含有量は、良好な電荷輸送性を得る観点から、有機エレクトロニクス材料の全質量に対して50質量%以上であることが好ましく、70質量%以上がより好ましく、80質量%以上が更に好ましい。電荷輸送性ポリマーの含有量の上限は特に限定されず、100質量%とすることも可能である。ドーパント等の添加剤を含むことを考慮し、電荷輸送性ポリマーの含有量を、例えば95質量%以下、90質量%以下、等としてもよい。
本実施形態の有機エレクトロニクス材料の製造方法は、GPCにより測定される分子量分布チャートにおいて、分子量20,000未満の成分の占める面積比が40%以下である電荷輸送性ポリマーを含有する有機エレクトロニクス材料の製造方法であり、電荷輸送性ポリマーから分子量20,000未満の成分を除去する工程を含むことを特徴とする。
「除去」については、電荷輸送性ポリマーにおいて説明したとおりである。また、製造される電荷輸送性ポリマーの好ましい構造、数平均分子量、重量平均分子量、及び分散度も、上述のとおりである。
本発明の実施形態であるインク組成物は、前記実施形態の有機エレクトロニクス材料(前記実施形態の有機エレクトロニクス材料の製造方法により得られた有機エレクトロニクス材料を含む。以下の記載においても同じ。)と、該材料を溶解又は分散し得る溶媒とを含有する。インク組成物を用いることによって、塗布法といった簡便な方法によって有機層を容易に形成できる。
溶媒としては、水、有機溶媒、又はこれらの混合溶媒を使用できる。有機溶媒としては、メタノール、エタノール、イソプロピルアルコール等のアルコール;ペンタン、ヘキサン、オクタン等のアルカン;シクロヘキサン等の環状アルカン;ベンゼン、トルエン、キシレン、メシチレン、テトラリン、ジフェニルメタン等の芳香族炭化水素;エチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、プロピレングリコール-1-モノメチルエーテルアセタート等の脂肪族エーテル;1,2-ジメトキシベンゼン、1,3-ジメトキシベンゼン、アニソール、フェネトール、2-メトキシトルエン、3-メトキシトルエン、4-メトキシトルエン、2,3-ジメチルアニソール、2,4-ジメチルアニソール等の芳香族エーテル;酢酸エチル、酢酸n-ブチル、乳酸エチル、乳酸n-ブチル等の脂肪族エステル;酢酸フェニル、プロピオン酸フェニル、安息香酸メチル、安息香酸エチル、安息香酸プロピル、安息香酸n-ブチル等の芳香族エステル;N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド等のアミド系溶媒;ジメチルスルホキシド、テトラヒドロフラン、アセトン、クロロホルム、塩化メチレンなどが挙げられる。好ましくは、芳香族炭化水素、脂肪族エステル、芳香族エステル、脂肪族エーテル、芳香族エーテル等である。
電荷輸送性ポリマーが重合性官能基を有する場合、インク組成物は、好ましくは、重合開始剤を含有する。重合開始剤として、公知のラジカル重合開始剤、カチオン重合開始剤、アニオン重合開始剤等を使用できる。インク組成物を簡便に調製できる観点から、ドーパントとしての機能と重合開始剤としての機能とを兼ねる物質を用いることが好ましい。そのような物質として、例えば、前記イオン化合物が挙げられる。
インク組成物は、更に、任意成分として添加剤を含有してもよい。添加剤としては、例えば、重合禁止剤、安定剤、増粘剤、ゲル化剤、難燃剤、酸化防止剤、還元防止剤、酸化剤、還元剤、表面改質剤、乳化剤、消泡剤、分散剤、界面活性剤等が挙げられる。
インク組成物における溶媒の含有量は、種々の塗布方法へ適用することを考慮して定めることができる。例えば、溶媒の含有量は、溶媒に対し電荷輸送性ポリマーの割合が、0.1質量%以上となる量が好ましく、0.2質量%以上となる量がより好ましく、0.5質量%以上となる量が更に好ましい。また、溶媒の含有量は、溶媒に対し電荷輸送性ポリマーの割合が、20質量%以下となる量が好ましく、15質量%以下となる量がより好ましく、10質量%以下となる量が更に好ましい。
本発明の実施形態である有機層は、前記実施形態の有機エレクトロニクス材料、又はインク組成物を用いて形成された層である。インク組成物を用いることによって、塗布法により有機層を良好かつ簡便に形成できる。塗布方法としては、例えば、スピンコーティング法;キャスト法;浸漬法;凸版印刷、凹版印刷、オフセット印刷、平版印刷、凸版反転オフセット印刷、スクリーン印刷、グラビア印刷等の有版印刷法;インクジェット法等の無版印刷法などの公知の方法が挙げられる。塗布法によって有機層を形成する場合、塗布後に得られた有機層(塗布層)を、ホットプレート又はオーブンを用いて乾燥させ、溶媒を除去してもよい。
本発明の実施形態である有機エレクトロニクス素子は、少なくとも一つ以上の前記実施形態の有機層を有する。有機エレクトロニクス素子として、例えば、有機EL素子、有機光電変換素子、有機トランジスタ等が挙げられる。有機エレクトロニクス素子は、好ましくは、少なくとも一対の電極の間に有機層が配置された構造を有する。
本発明の実施形態である有機EL素子は、少なくとも一つ以上の前記実施形態の有機層を有する。有機EL素子は、通常、発光層、陽極、陰極、及び基板を備えており、必要に応じて、正孔注入層、電子注入層、正孔輸送層、電子輸送層等の他の機能層を備えている。各層は、蒸着法により形成してもよく、塗布法により形成してもよい。有機EL素子は、好ましくは、前記有機層を発光層又は他の機能層として有し、より好ましくは機能層として有し、更に好ましくは正孔注入層及び正孔輸送層の少なくとも一方として有する。
発光層に用いる材料として、低分子化合物、ポリマー、デンドリマー等の発光材料を使用できる。ポリマーは、溶媒への溶解性が高く、塗布法に適しているため好ましい。発光材料としては、蛍光材料、燐光材料、熱活性化遅延蛍光材料(TADF)等が挙げられる。
上記の有機エレクトロニクス材料を用いて形成された有機層を、正孔注入層及び正孔輸送層の少なくとも一方として使用することが好ましく、少なくとも正孔輸送層として使用することが一層好ましい。上述のとおり、有機エレクトロニクス材料を含むインク組成物を用いることにより、これらの層を容易に形成することができる。
有機EL素子が、上記の有機エレクトロニクス材料を用いて形成された有機層を正孔輸送層として有し、さらに正孔注入層を有する場合、正孔注入層には公知の材料を使用できる。また、有機EL素子が、上記の有機エレクトロニクス材料を用いて形成された有機層を正孔注入層として有し、更に正孔輸送層を有する場合、正孔輸送層には公知の材料を使用できる。
正孔注入層及び正孔輸送層に用いることができる材料として、例えば、芳香族アミン系化合物(例えば、N,N’-ジ(ナフタレン-1-イル)-N,N’-ジフェニル-ベンジジン(α-NPD)などの芳香族ジアミン)、フタロシアニン系化合物、チオフェン系化合物(例えば、チオフェン系導電性ポリマー(たとえば、ポリ(3,4-エチレンジオキシチオフェン):ポリ(4-スチレンスルホン酸塩)(PEDOT:PSS)等)等が挙げられる。
電子輸送層及び電子注入層に用いる材料としては、例えば、フェナントロリン誘導体、ビピリジン誘導体、ニトロ置換フルオレン誘導体、ジフェニルキノン誘導体、チオピランジオキシド誘導体、ナフタレン、ペリレンなどの縮合環テトラカルボン酸無水物、カルボジイミド、フルオレニリデンメタン誘導体、アントラキノジメタン及びアントロン誘導体、オキサジアゾール誘導体、チアジアゾール誘導体、ベンゾイミダゾール誘導体、キノキサリン誘導体、アルミニウム錯体等が挙げられる。また、前記実施形態の有機エレクトロニクス材料も使用できる。
陰極材料としては、例えば、Li、Ca、Mg、Al、In、Cs、Ba、Mg/Ag、LiF、CsF等の金属又は金属合金が用いられる。
陽極材料としては、例えば、金属(例えば、Au)又は導電性を有する他の材料が用いられる。他の材料として、例えば、酸化物(例えば、ITO:酸化インジウム/酸化錫)、導電性高分子(例えば、ポリチオフェン-ポリスチレンスルホン酸混合物(PEDOT:PSS))が挙げられる。
基板として、ガラス、プラスチック等を使用できる。基板は、透明であることが好ましく、また、フレキシブル性を有するフレキシブル基板であることが好ましい。石英ガラス、光透過性樹脂フィルム等が好ましく用いられる。
有機EL素子は、外気の影響を低減させて長寿命化させるため、封止されていてもよい。封止に用いる材料としては、ガラス、エポキシ樹脂、アクリル樹脂、ポリエチレンテレフタレート、ポリエチレンナフタレート等のプラスチックフィルム、又は酸化珪素、窒化ケイ素等の無機物を用いることができるが、これらに限定されることはない。
封止の方法も、特に限定されず、公知の方法で行うことができる。
有機EL素子の発光色は特に限定されるものではない。白色の有機EL素子は、家庭用照明、車内照明、時計又は液晶のバックライト等の各種照明器具に用いることができるため好ましい。
本発明の実施形態である表示素子は、前記実施形態の有機EL素子を備えている。例えば、赤、緑及び青(RGB)の各画素に対応する素子として、有機EL素子を用いることで、カラーの表示素子が得られる。画像の形成方法には、マトリックス状に配置した電極でパネルに配列された個々の有機EL素子を直接駆動する単純マトリックス型と、各素子に薄膜トランジスタを配置して駆動するアクティブマトリックス型とがある。
窒素雰囲気下のグローブボックス中で、室温下、サンプル管にトリス(ジベンジリデンアセトン)ジパラジウム(73.2mg、80μmol)を秤取り、アニソール(15ml)を加え、30分間攪拌した。同様に、サンプル管にトリス(t-ブチル)ホスフィン(129.6mg、640μmol)を秤取り、アニソール(5mL)を加え、5分間攪拌した。これらの溶液を混合し、室温で30分間攪拌して、触媒の溶液を得た。なお、触媒の調製において、すべての溶媒は、30分以上窒素バブルにより脱気した後に使用した。
三口丸底フラスコに、Lモノマーとして下記モノマー2(4.0mmol)、Bモノマーとしてモノマー3(5.0mmol)、第1のTモノマー(T1モノマー)としてモノマー1(0.1mmol)、第2のTモノマー(T2モノマー)としてモノマー4(1.9mmol)、及びアニソール(20mL)を加え、さらに、上記調製したPd触媒溶液(7.5mL)を加えた。30分撹拌した後、10%テトラエチルアンモニウム水酸化物水溶液(20mL)を追加した。この混合物を2時間、加熱・還流した。なお、ここまでの全ての操作は、窒素気流下で行った。また、すべての溶媒は、30分以上窒素バブルにより脱気した後に使用した。
上記電荷輸送性ポリマー1-1と同様に、電荷輸送性ポリマー1-2、電荷輸送性ポリマー1-3、電荷輸送性ポリマー1-4、及び電荷輸送性ポリマー1-5を合成した。それぞれの合成に用いたモノマーの化学式を以下に示し、その組み合わせをまとめて表1に以下に示す。なお、表1には、上記電荷輸送性ポリマー1-1、及び後述する電荷輸送性ポリマー1-6と1-7のモノマーについても併せて記載する。
Tモノマーとして、上記モノマー1を単独で2.0mmol用いた以外は、上記電荷輸送性ポリマー1-1と同様にして、低分子量成分を除去していない電荷輸送性ポリマー1-6を得た。
Bモノマーとして、モノマー3に代えてモノマー5を用いた以外は、上記電荷輸送性ポリマー1-6と同様にして、低分子量成分を除去していない電荷輸送性ポリマー1-7を得た。
三口丸底フラスコに、上記電荷輸送性ポリマー1-1と同様に、Lモノマーとして上記モノマー2(4.0mmol)、Bモノマーとして上記モノマー3(5.0mmol)、第1のTモノマー(T1モノマー)として上記モノマー1(0.1mmol)、及び第2のTモノマー(T2モノマー)として上記モノマー4(1.9mmol)を加え、さらに、アニソール(20mL)と上記調製したPd触媒溶液(7.5mL)を加えた。30分撹拌した後、10%テトラエチルアンモニウム水酸化物水溶液(20mL)を追加した。この混合物を2時間、加熱・還流した。なお、ここまでの全ての操作は、窒素気流下で行った。また、すべての溶媒は、30分以上窒素バブルにより脱気した後に使用した。
以降は、上記電荷輸送性ポリマー1-1と同様にスカベンジャを用いた操作とメタノールからの再沈殿を行って、低分子量成分を除去した電荷輸送性ポリマー2-1を得た。
上記電荷輸送性ポリマー2-1と同様に、電荷輸送性ポリマー2-2、電荷輸送性ポリマー2-3、電荷輸送性ポリマー2-4、及び電荷輸送性ポリマー2-5を合成した。それぞれの合成に用いたモノマーの組み合わせを表2に示す。なお、表2には、上記電荷輸送性ポリマー2-1、及び後述する電荷輸送性ポリマー2-6と2-7のモノマーについても併せて記載する。
Tモノマーとして、上記モノマー1を単独で2.0mmol用いた以外は、上記電荷輸送性ポリマー2-1と同様にして、低分子量成分を除去した電荷輸送性ポリマー2-6を得た。
Bモノマーとして、モノマー3に代えてモノマー5を用いた以外は、上記電荷輸送性ポリマー2-6と同様にして、低分子量成分を除去した電荷輸送性ポリマー2-7を得た。
三口丸底フラスコに、Lモノマーとして上記モノマー2(4.0mmol)、Bモノマーとして上記モノマー3(5.0mmol)、第1のTモノマー(T1モノマー)として上記モノマー1(0.1mmol)、第2のTモノマー(T2モノマー)として上記モノマー4(1.9mmol)、及びアニソール(8mL)を加え、さらに、別途調製した上記Pd触媒の溶液(7.5mL)を加えた。30分撹拌した後、10%テトラエチルアンモニウム水酸化物水溶液(20mL)を追加した。この混合物を2時間、加熱・還流した。なお、ここまでの全ての操作は、窒素気流下で行った。また、すべての溶媒は、30分以上窒素バブルにより脱気した後に使用した。以降は上記電荷輸送性ポリマー1-1と同様に精製処理を行い、低分子量成分を除去していない電荷輸送性ポリマー3-1を得た。
上記電荷輸送性ポリマー3-1と同様に、電荷輸送性ポリマー3-2、電荷輸送性ポリマー3-3、電荷輸送性ポリマー3-4、及び電荷輸送性ポリマー3-5を合成した。それぞれの合成に用いたモノマーの組み合わせを表3に示す。なお、表3には、上記電荷輸送性ポリマー3-1、及び後述する電荷輸送性ポリマー3-6と3-7のモノマーについても併せて記載する。
Tモノマーとして、上記モノマー1を単独で2.0mmol用いた以外は、上記電荷輸送性ポリマー3-1と同様にして、低分子量成分を除去していない電荷輸送性ポリマー3-6を得た。
Bモノマーとして、モノマー3に代えてモノマー5を用いた以外は、上記電荷輸送性ポリマー3-6と同様にして、低分子量成分を除去していない電荷輸送性ポリマー3-7を得た。
三口丸底フラスコに、Lモノマーとして上記モノマー2(4.0mmol)、Bモノマーとして上記モノマー3(5.0mmol)、第1のTモノマー(T1モノマー)として上記モノマー1(0.1mmol)、第2のTモノマー(T2モノマー)として上記モノマー4(1.9mmol)、及びアニソール(8mL)を加え、さらに、別途調製した上記Pd触媒の溶液(7.5mL)を加えた。30分撹拌した後、10%テトラエチルアンモニウム水酸化物水溶液(20mL)を追加した。この混合物を2時間、加熱・還流した。なお、ここまでの全ての操作は、窒素気流下で行った。また、すべての溶媒は、30分以上窒素バブルにより脱気した後に使用した。以降は上記電荷輸送性ポリマー2-1と同様に低分子量成分の除去と精製処理を行い、低分子量成分を除去した電荷輸送性ポリマー4-1を得た。
上記電荷輸送性ポリマー4-1と同様に、電荷輸送性ポリマー4-2、電荷輸送性ポリマー4-3、電荷輸送性ポリマー4-4、及び電荷輸送性ポリマー4-5を合成した。それぞれの合成に用いたモノマーの組み合わせを表4に示す。なお、表4には、上記電荷輸送性ポリマー4-1、及び後述する電荷輸送性ポリマー4-6と4-7のモノマーについても併せて記載する。
Tモノマーとして、上記モノマー1を単独で2.0mmol用いた以外は、上記電荷輸送性ポリマー3-1と同様にして、低分子量成分を除去した電荷輸送性ポリマー4-6を得た。
Bモノマーとして、モノマー3に代えてモノマー5を用いた以外は、上記電荷輸送性ポリマー4-6と同様にして、低分子量成分を除去した電荷輸送性ポリマー4-7を得た。
三口丸底フラスコに、Lモノマーとして上記モノマー2(4.0mmol)、Bモノマーとして上記モノマー3(5.0mmol)、第1のTモノマー(T1モノマー)として上記モノマー1(0.1mmol)、第2のTモノマー(T2モノマー)として上記モノマー4(1.9mmol)、及びアニソール(4mL)を加え、さらに、別途調製した上記Pd触媒の溶液(7.5mL)を加えた。30分撹拌した後、10%テトラエチルアンモニウム水酸化物水溶液(20mL)を追加した。この混合物を2時間、加熱・還流した。なお、ここまでの全ての操作は、窒素気流下で行った。また、すべての溶媒は、30分以上窒素バブルにより脱気した後に使用した。以降は上記電荷輸送性ポリマー1-1と同様に精製処理を行い、低分子量成分を除去していない電荷輸送性ポリマー5-1を得た。
上記電荷輸送性ポリマー5-1と同様に、電荷輸送性ポリマー5-2、電荷輸送性ポリマー5-3、電荷輸送性ポリマー5-4、及び電荷輸送性ポリマー5-5を合成した。それぞれの合成に用いたモノマーの組み合わせを表5に示す。なお、表5には、上記電荷輸送性ポリマー5-1、及び後述する電荷輸送性ポリマー5-6と5-7のモノマーについても併せて記載する。
Tモノマーとして、上記モノマー1を単独で2.0mmol用いた以外は、上記電荷輸送性ポリマー5-1と同様にして、低分子量成分を除去していない電荷輸送性ポリマー5-6を得た。
Bモノマーとして、モノマー3に代えてモノマー5を用いた以外は、上記電荷輸送性ポリマー5-6と同様にして、低分子量成分を除去していない電荷輸送性ポリマー5-7を得た。
三口丸底フラスコに、Lモノマーとして上記モノマー2(4.0mmol)、Bモノマーとして上記モノマー3(5.0mmol)、第1のTモノマー(T1モノマー)として上記モノマー1(0.1mmol)、第2のTモノマー(T2モノマー)として上記モノマー4(1.9mmol)、及びアニソール(4mL)を加え、さらに、別途調製した上記Pd触媒の溶液(7.5mL)を加えた。30分撹拌した後、10%テトラエチルアンモニウム水酸化物水溶液(20mL)を追加した。この混合物を2時間、加熱・還流した。なお、ここまでの全ての操作は、窒素気流下で行った。また、すべての溶媒は、30分以上窒素バブルにより脱気した後に使用した。以降は上記電荷輸送性ポリマー2-1と同様に低分子量成分の除去と精製処理を行い、低分子量成分を除去した電荷輸送性ポリマー6-1を得た。
上記電荷輸送性ポリマー6-1と同様に、電荷輸送性ポリマー6-2、電荷輸送性ポリマー6-3、電荷輸送性ポリマー6-4、及び電荷輸送性ポリマー6-5を合成した。それぞれの合成に用いたモノマーの組み合わせを表6に示す。なお、表6には、上記電荷輸送性ポリマー6-1、及び後述する電荷輸送性ポリマー6-6と6-7のモノマーについても併せて記載する。
Tモノマーとして、上記モノマー1を単独で2.0mmol用いた以外は、上記電荷輸送性ポリマー6-1と同様にして、低分子量成分を除去した電荷輸送性ポリマー6-6を得た。
Bモノマーとして、モノマー3に代えてモノマー5を用いた以外は、上記電荷輸送性ポリマー6-6と同様にして、低分子量成分を除去した電荷輸送性ポリマー6-7を得た。
[比較例1-1]
電荷輸送性ポリマー1-1(10mg)を1100μLのトルエンに溶解させた溶液と、下記化学式で表されるイオン化合物1(1mg)を50μLのトルエンに溶解させた溶液を混合した塗布溶液を、3000rpmで石英板上にスピンコートした。ついで、ホットプレート上、180℃で10分間加熱して重合反応を行った。加熱後にトルエン溶媒に石英板を10秒間浸漬し、洗浄を行った。
洗浄前:λmax=383nm 、 Abs=0.229
洗浄後:λmax=383nm 、 Abs=0.180
残膜率(%)=洗浄後Abs/洗浄前Abs×100
=(0.180/0.229)×100=78.6
装置:U-3900H形分光光度計(日立ハイテクノロジーズ)
スリット:2nm
スキャンスピード:600nm/min
開始波長:500nm
終了波長:250nm
リファレンス:石英基板
電荷輸送性ポリマー1-1に代えて、下記表8に示すいずれかの電荷輸送性ポリマーを用いた以外は、上記比較例1-1と同様にして有機層を形成し、その残膜率を測定した。結果を表8に示す。
[比較例4-1]
ITOを1.6mm幅にパターンニングしたガラス基板上に、PEDOT:PSS分散液(シュタルク・ヴィテック社製、AI4083 LVW142)を、回転速度1500min-1でスピン塗布し、ホットプレート上で空気中、200℃/10分加熱乾燥して、正孔注入層(40nm)を形成した。以後の実験は乾燥窒素環境下で行った。
電荷輸送性ポリマー3-1に代えて、表9に示すいずれかのポリマーを用いて正孔輸送層を形成した以外は、比較例4-1と同様にして有機EL素子を作製した。
電荷輸送性ポリマー3-1の代わりに電荷輸送性ポリマー4-1を用いて正孔輸送層を形成した以外は、比較例4-1と同様にして有機EL素子を作製した。
電荷輸送性ポリマー3-1に代えて、表10に示すいずれかのポリマーを用いて正孔輸送層を形成した以外は、比較例4-1と同様にして有機EL素子を作製した。
電荷輸送性ポリマー3-1(4.5mg)、上記イオン化合物1(0.13mg)、及びトルエン(500μL)を混合し、正孔注入層形成用のインク組成物を調製した。以後の実験は乾燥窒素環境下で行った。
ITOを1.6mm幅にパターンニングしたガラス基板上に、前記インク組成物を回転速度3000min-1でスピンコートし、ホットプレート上で120℃、10分間加熱して硬化させ、正孔注入層(40nm)を形成した。
電荷輸送性ポリマー3-1に代えて、表11に示すいずれかのポリマーを用いて正孔注入層を形成した以外は、比較例5-1と同様にして有機EL素子を作製した。
電荷輸送性ポリマー3-1の代わりに電荷輸送性ポリマー4-1を用いて正孔注入層を形成した以外は、比較例5-1と同様にして有機EL素子を作製した。
電荷輸送性ポリマー3-1に代えて、表12に示すいずれかのポリマーを用いて正孔注入層を形成した以外は、比較例5-1と同様にして有機EL素子を作製した。
既に述べられたもの以外に、本発明の新規かつ有利な特徴から外れることなく、上記の実施形態に様々な修正や変更を加えてもよいことに注意すべきである。したがって、そのような全ての修正や変更は、添付の請求の範囲に含まれることが意図されている。
2 陽極
3 正孔注入層
4 陰極
5 電子注入層
6 正孔輸送層
7 電子輸送層
8 基板
Claims (14)
- GPCにより測定される分子量分布チャートにおいて、分子量20,000未満の成分の占める面積比が40%以下であり、かつ、分子量500以下の成分の占める面積比が1%以下である電荷輸送性ポリマーを含有する、有機エレクトロニクス材料。
- 分子量20,000未満の成分が除去された電荷輸送性ポリマーであって、GPCにより測定される分子量分布チャートにおいて、前記分子量20,000未満の成分の占める面積比が40%以下である電荷輸送性ポリマーを含有する、有機エレクトロニクス材料。
- 前記電荷輸送性ポリマーの分散度(質量平均分子量/数平均分子量)が2.0以上である、請求項1又は2記載の有機エレクトロニクス材料。
- GPCにより測定される分子量分布チャートにおいて、分子量20,000未満の成分の占める面積比が40%以下である電荷輸送性ポリマーを含有する有機エレクトロニクス材料の製造方法であって、
電荷輸送性ポリマーから分子量20,000未満の成分を除去する工程を含む、有機エレクトロニクス材料の製造方法。 - 分子量20,000未満の成分を除去した後の前記電荷輸送性ポリマーの分散度(質量平均分子量/数平均分子量)が2.0以上である、請求項4記載の有機エレクトロニクス材料の製造方法。
- 請求項1~3のいずれか1項記載の有機エレクトロニクス材料、又は、請求項4又は5記載の製造方法により製造された有機エレクトロニクス材料と、溶媒とを含む、インク組成物。
- 請求項1~3のいずれか1項記載の有機エレクトロニクス材料、請求項4又は5記載の製造方法により製造された有機エレクトロニクス材料、又は請求項6記載のインク組成物を用いて形成された、有機層。
- 請求項7記載の有機層を少なくとも一つ備える、有機エレクトロニクス素子。
- 請求項7記載の有機層を少なくとも一つ備える、有機エレクトロルミネセンス素子。
- フレキシブル基板を更に備える、請求項9記載の有機エレクトロルミネセンス素子。
- 樹脂フィルム基板を更に備える、請求項9記載の有機エレクトロルミネセンス素子。
- 請求項9~11のいずれか1項記載の有機エレクトロルミネセンス素子を備えた、表示素子。
- 請求項9~11のいずれか1項記載の有機エレクトロルミネセンス素子を備えた、照明装置。
- 請求項13記載の照明装置と、表示手段として液晶素子とを備えた、表示装置。
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Also Published As
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US20190305225A1 (en) | 2019-10-03 |
KR102224393B1 (ko) | 2021-03-08 |
JP6782418B2 (ja) | 2020-11-11 |
EP3348620A4 (en) | 2019-05-01 |
EP3348620A1 (en) | 2018-07-18 |
KR102494404B1 (ko) | 2023-01-31 |
CN108026378A (zh) | 2018-05-11 |
JPWO2017043502A1 (ja) | 2018-07-05 |
CN108026378B (zh) | 2022-04-15 |
US10868252B2 (en) | 2020-12-15 |
TW201718774A (zh) | 2017-06-01 |
KR20180041158A (ko) | 2018-04-23 |
TWI808929B (zh) | 2023-07-21 |
KR20210025720A (ko) | 2021-03-09 |
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