Organic electronic materials and their applications

Abstract

An organic electronic material and its use, wherein the organic electronic material contains a charge transporting polymer, wherein the charge transporting polymer has a structure represented by the following formula (1) and has a structure branched in three or more directions (wherein Rf is independently a fluoroalkyl group, a and b are 0 or 1, and a and b are not 0 at the same time).

Description

Technical Field

[0001] The present disclosure relates to an organic electronic material containing a charge transporting polymer that is highly soluble in various solvents, and also to an ink composition, an organic film, an organic electronic element, and an organic electroluminescence element using the organic electronic material, a display element, a lighting device, and a display device using the element. Background Art

[0002] Organic electronic components are components that use organic matter to perform electrical operations. They are expected to have advantages such as energy saving, low price, and flexibility, and have attracted attention as a technology to replace existing inorganic semiconductors based on silicon. As an example of an organic electronic component, an organic electroluminescent element (hereinafter also referred to as an "organic EL element"), an organic photoelectric conversion element, an organic transistor, etc. can be cited.

[0003] Organic EL elements are attracting attention as large-area solid-state light sources that can be used as substitutes for incandescent lamps or gas-filled lamps. In addition, they are also attracting attention as the most powerful self-luminous display that can replace liquid crystal displays (LCDs) in the field of flat panel displays (FPDs), and are being promoted for commercialization.

[0004] The manufacturing methods of organic EL elements are roughly divided into two types: dry process, which mainly forms films in a vacuum system, and wet process, which can form films by plate printing such as relief printing and gravure printing, plateless printing such as inkjet printing, etc. Among them, the wet process is expected to be an indispensable method for future large-screen organic EL displays because it can achieve simple film formation.

[0005] Under such circumstances, the development of polymer compounds suitable for wet processes has been underway in recent years. For example, a method for forming a multilayer organic EL element by a wet process using a charge transporting polymer having a polymerizable functional group has been reported (for example, see Patent Document 1 and Non-Patent Document 1).

[0006] [Prior art literature]

[0007] [Patent Document]

[0008] Patent Document 1: Japanese Patent Application Publication No. 2006-279007

[0009] [Non-patent literature]

[0010] Non-patent document 1: Kengo Hirose, Daisuke Kumaki, Nobuaki Koike, Akira Kuriyama, Seiichiro Ikehata, Shizuo Tokito, 53rd Joint Lecture Meeting on Relations in Applied Physics, 26p-ZK-4 (2006) Summary of the invention

[0011] [Problems to be solved by the invention]

[0012] Organic EL elements manufactured by wet processes have the advantages of being easy to achieve low cost and large area. However, from the perspective of element characteristics such as driving voltage, luminous efficiency and luminous life, organic EL elements manufactured by wet processes may not be sufficient, and further improvement is desired.

[0013] In a wet process, an ink composition (also referred to as varnish) containing a charge transporting polymer and a solvent is typically used, and the charge transporting polymer is ideally excellent in charge transporting ability and highly soluble in various solvents. In particular, the solubility of the charge transporting polymer is important not only in terms of operability during film formation, but also in terms of the viewpoint of manufacturing a uniform film in order to improve the characteristics of the element. In addition, for example, in inkjet printing, in order to appropriately adjust the characteristics such as the viscosity of the ink composition, it is ideal to use various solvents.

[0014] However, conventional charge transport polymers have low solubility in solvents, and the solvents that can be used in the preparation of ink compositions are often limited, and their applicability to inkjet printing is not necessarily sufficient. Therefore, charge transport polymers that have high solubility in various solvents are required.

[0015] In view of the above circumstances, the present disclosure provides an organic electronic material including a charge transporting polymer having high solubility in various solvents. In addition, using the organic electronic material, the present disclosure provides an ink composition, an organic film, an organic electronic element, an organic EL element, a display element using the organic EL element, a lighting device, and a display device.

[0016] [Technical means to solve the problem]

[0017] The present inventors have conducted intensive studies and have found that the solubility of a charge transporting polymer is improved by introducing a fluoroalkyl group into a predetermined position of a benzene ring of a triphenylamine structure, thereby completing the present invention.

[0018] That is, the present invention relates to the embodiments described below. However, the present invention is not limited to the following embodiments, and includes various embodiments.

[0019] One embodiment relates to an organic electronic material including a charge-transporting polymer having a structure represented by the following formula (1) and having a structure branched in three or more directions.

[0020]

[0021] In the formula, Rf is independently a fluoroalkyl group, a and b are 0 or 1, and a and b are not 0 at the same time.

[0022] In the above embodiment, the charge transporting polymer preferably has a hole injecting property or a hole transporting property.

[0023] The charge transport polymer preferably further contains one or more structures selected from the group consisting of an aromatic amine structure, a pyrrole structure, a carbazole structure, a thiophene structure, a benzene structure, an aniline structure, a phenoxazine structure, and a fluorene structure other than the structure represented by the above formula (1).

[0024] The charge transport polymer preferably has at least one polymerizable functional group. The polymerizable functional group is preferably at least one selected from the group consisting of an oxetane group, an epoxy group, a vinyl group, an acryloyl group, and a methacryloyl group.

[0025] The organic electronic material preferably further contains a polymerization initiator. The polymerization initiator is preferably an ionic compound. The ionic compound is preferably an onium salt.

[0026] Another embodiment relates to an ink composition comprising: the organic electronic material of the above embodiment; and a solvent.

[0027] Still another embodiment relates to an organic thin film formed using the organic electronic material of the above embodiment or the ink composition of the above embodiment.

[0028] Another embodiment relates to an organic electroluminescent element having the organic thin film of the above embodiment. The organic electroluminescent element preferably further has a flexible substrate. The organic electroluminescent element preferably further has a resin film substrate.

[0029] Still another embodiment relates to a display element including the organic electroluminescent element of the above embodiment.

[0030] Still another embodiment relates to a lighting device including the organic electroluminescent element of the above embodiment.

[0031] Still another embodiment relates to a display device including: the lighting device of the above embodiment; and a liquid crystal element as a display member.

[0032] [Effects of the Invention]

[0033] According to the present invention, an organic electronic material containing a charge transporting polymer having high solubility in various solvents can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figure 1 It is a schematic cross-sectional view showing an example of an organic EL element which is one embodiment of the present disclosure.

[0035] [Explanation of Symbols]

[0036] 1: Luminous layer

[0037] 2: Anode

[0038] 3: Hole injection layer

[0039] 4: Cathode

[0040] 5: Electron injection layer

[0041] 6: Hole transport layer

[0042] 7: Electron transport layer

[0043] 8: Substrate DETAILED DESCRIPTION

[0044] Hereinafter, embodiments of the present invention will be described in detail, but the present invention is not limited to the following embodiments.

[0045] <Organic electronic materials>

[0046] In one embodiment, the organic electronic material contains a charge transporting polymer having a structure represented by the following formula (1) and having a structure branched in three or more directions.

[0047]

[0048] In the formula, Rf is independently a fluoroalkyl group, a and b are 0 or 1, and a and b are not 0 at the same time.

[0049] The "fluoroalkyl group" refers to a group having a structure in which at least one hydrogen atom in the alkyl group is substituted by a fluorine atom. The alkyl group may be a straight chain structure or a branched structure. The carbon number of the fluoroalkyl group is preferably 1 to 5, more preferably 1 to 3, and more preferably 1 or 2. In one embodiment, the fluoroalkyl group is preferably a perfluoroalkyl group. The carbon number of the perfluoroalkyl group is preferably 1 to 5, more preferably 1 to 3, and more preferably 1 or 2. In one embodiment, in the formula, Rf is preferably independently -CF3 or -C2F5.

[0050] As shown in the above formula (1), in the triphenylamine structure, by introducing a fluoroalkyl group such as -CF3 at the meta position of the benzene ring bonded to the nitrogen atom, it is easy to obtain high solubility in various solvents. The so-called "high solubility" means that the polymer dissolves in the solvent and presents a state in which the solution is not turbid and appears transparent, as specifically shown in the examples.

[0051] In one embodiment, in the above formula (1), a and b are more preferably 1 respectively. In one embodiment, in the triphenylamine structure, the hydrogen atoms in the benzene ring other than the benzene ring having the fluoroalkyl group may be substituted by a substituent. The substituent may be, for example, the same as the substituent R of the structural unit L2 described later. The organic electronic material may contain one or more of the charge transporting polymers. The charge transporting polymer is described in detail below.

[0052] (Charge Transporting Polymer)

[0053] The charge transporting polymer has a structure represented by the above formula (1) and has a branched structure branching in three or more directions. Therefore, the charge transporting polymer is characterized in that it contains at least a divalent structural unit L having charge transport properties, a trivalent or higher structural unit B constituting a branch portion, and a monovalent structural unit T constituting an end portion, wherein the divalent structural unit L contains at least a structural unit having a structure represented by the above formula (1). Regarding each structural unit, the charge transporting polymer may contain only one type, or may contain multiple types. In the charge transporting polymer, each structural unit is bonded to each other at a "monovalent" to "trivalent or higher" bonding site.

[0054] The charge transporting polymer has the ability to transport charge, and the transferred charge is preferably a hole. If the charge transporting polymer is a hole transporting compound, it can be used as a material for a hole injection layer or a hole transport layer of an organic EL element, for example. In addition, if it is an electron transporting compound, it can be used as a material for an electron transport layer or an electron injection layer. In addition, if it is a compound that transports both holes and electrons, it can be used in materials for light-emitting layers, etc. In one embodiment, the charge transporting polymer is preferably used as a material for a hole injection layer and / or a hole transport layer, and is more preferably used as a hole injection layer material.

[0055] In this specification, the term "charge transporting polymer" also includes low molecular weight "oligomers" having a low degree of polymerization. The structure of the charge transporting polymer including a plurality of structural units having charge transporting properties will be described in more detail below.

[0056] (Structure of Charge Transporting Polymer)

[0057] As examples of partial structures contained in charge transporting polymers, the following can be cited. Charge transporting polymers are not limited to polymers having the following partial structures. In the partial structure, "L" represents structural unit L, "T" represents structural unit T, and "B" represents structural unit B. "*" represents the bonding site with other structural units. In the following partial structures, multiple Ls may be structural units that are the same as each other or different from each other. The same is true for T and B.

[0058] Charge transport polymer with branched structure

[0059]

[0060] In one embodiment, the charge transporting polymer having a structure represented by the above formula (1) preferably further contains at least one structure selected from the group consisting of an aromatic amine structure (excluding the structure represented by the above formula (1)), a carbazole structure, a thiophene structure, a bithiophene structure, a benzene structure, a phenoxazine structure and a fluorene structure. These structures may preferably be included in the structural unit L, may be included in the structural unit B, or may be included in both the structural unit L and the structural unit B. By including any of the above structures in the charge transporting polymer, the charge transport property, in particular the hole transport property, may be improved. The structural unit of the charge transporting polymer is described in more detail below.

[0061] (Structural unit L)

[0062] The structural unit L is a divalent structural unit having charge transport properties, and at least includes a structural unit having a structure represented by the above formula (1) (hereinafter referred to as structural unit L1). In one embodiment, among the structural units represented by the above formula (1), the structural unit L1 preferably includes a structural unit L1-1 having a structure represented by the following formula (1-1).

[0063]

[0064] In the formula, Rf is independently a fluoroalkyl group. The fluoroalkyl group is as described above. In one embodiment, Rf is preferably independently -CF3 or -C2F5.

[0065] The charge transporting polymer having the structural unit L1 has excellent solubility in various solvents. Therefore, the workability during film formation, such as preparation of an organic thin film coating solution constituting an organic electronic element, can be improved. In addition, it is believed that by making it easy to produce a uniform film during film formation, the device characteristics can also be improved.

[0066] In addition to the structural unit L1, the structural unit L may also include a structural unit L2 different from the structural unit L1. The structural unit L2 is not particularly limited as long as it includes an atomic group having the ability to transport charge. For example, the structural unit L2 is selected from a substituted or unsubstituted aromatic amine structure (excluding the structure represented by the above formula (1)), a carbazole structure, a thiophene structure, a fluorene structure, a benzene structure, a biphenyl structure, a terphenyl structure, a naphthalene structure, an anthracene structure, a tetracene structure, a phenanthrene structure, a dihydrophenanthrene structure, a pyridine structure, a pyrazine structure, a quinoline structure, an isoquinoline structure, a quinoxaline structure, an acridine structure, a phenanthroline structure, a furan structure, a pyrrole structure, an oxazole structure, an oxadiazole structure, a thiazole structure, a thiadiazole structure, a triazole structure, a benzothiophene structure, a benzoxazole structure, a benzoxadiazole structure, a benzothiazole structure, a benzothiadiazole structure, a benzotriazole structure, and structures containing one or more of these.

[0067] The aromatic amine structure is a structure containing a nitrogen atom and an aromatic hydrocarbon group bonded to the nitrogen atom, and is preferably a structure selected from the group consisting of a diarylamine structure or a triarylamine structure, more preferably a triarylamine structure, and even more preferably a triphenylamine structure.

[0068] In one embodiment, from the perspective of obtaining excellent hole transport properties, the structural unit L2 is preferably selected from a substituted or unsubstituted aromatic amine structure, a carbazole structure, a thiophene structure, a fluorene structure, a benzene structure, a pyrrole structure, and one or more structures comprising these, more preferably selected from a substituted or unsubstituted aromatic amine structure, a carbazole structure, and one or more structures comprising these, and further preferably a substituted or unsubstituted aromatic amine structure. Here, the aromatic amine structure does not contain the structure represented by the above formula (1).

[0069] Specific examples of the structural unit L2 include the following. The structural unit L2 is not limited to the following.

[0070]

[0071]

[0072] R each independently represents a hydrogen atom or a substituent. Preferably, when R is a substituent, each independently selected from -R 1 、-OR 2 、-SR 3 、-OCOR 4 、-COOR 5 、-SiR 6 R 7 R 8 , a halogen atom, and a group containing a polymerizable functional group described below.1 ~R 8 Each independently represents a hydrogen atom (excluding -R 1 ); a linear, cyclic or branched alkyl group having 1 to 22 carbon atoms; or an aryl or heteroaryl group having 2 to 30 carbon atoms.

[0073] The aryl group is an atomic group obtained by removing a hydrogen atom from an aromatic hydrocarbon. The heteroaryl group is an atomic group obtained by removing a hydrogen atom from an aromatic heterocycle. The alkyl group may be further substituted by an aryl group or a heteroaryl group having 2 to 20 carbon atoms, and the aryl group or the heteroaryl group may be further substituted by a linear, cyclic or branched alkyl group having 1 to 22 carbon atoms.

[0074] R is preferably a hydrogen atom, an alkyl group, an aryl group, or an aryl group substituted with an alkyl group. Ar represents an arylene group or a 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, and more preferably a phenylene group.

[0075] Examples of aromatic hydrocarbons include monocyclic rings, condensed rings, or polycyclic rings in which two or more selected from monocyclic rings and condensed rings are bonded via a single bond. Examples of aromatic heterocyclic rings include monocyclic rings, condensed rings, or polycyclic rings in which two or more selected from monocyclic rings and condensed rings are bonded via a single bond.

[0076] In one embodiment, the structural unit L may only include the structural unit L1. In another embodiment, the structural unit L may be a combination of the structural unit L1 and the structural unit L2. From the perspective of improving the solubility of the charge transporting polymer, the proportion of the structural unit L1 is preferably 50 mol% or more, more preferably 75 mol% or more, and further preferably 85 mol% or more, based on all the structural units L. The proportion of the structural unit L1 may also be set to 100 mol%.

[0077] The desired properties can be easily improved by appropriately combining the structural unit L1 and the structural unit L2. For example, the structural unit L2 is preferably a structural unit including an aromatic amine structure represented by the following formula (2).

[0078]

[0079] In the formula, Ra is an alkyl group (-R 1 ), alkoxy (-OR 2 ) or a halogen atom, R is a substituent, and the details of each are as described above. c and d are each independently an integer of 0 to 4. In one embodiment, c and d are each preferably 0.

[0080] In one embodiment, the structural unit L may include the structural unit L1 and the structural unit L2-1 represented by the following formula (2-1). With such a combination of structural units, excellent solubility tends to be easily obtained.

[0081]

[0082] In the formula, -OR 2 is an alkoxyl group, and the details are as described above. In the embodiment, based on the total of the structural units L, the proportion of the structural unit L2-1 is preferably 75 mol% or less, more preferably 50 mol% or less, and further preferably 25 mol% or less. On the other hand, the proportion of the structural unit L1 is preferably 25 mol% or more, more preferably 50 mol% or more, and further preferably 75 mol% or more.

[0083] In one embodiment, the structural unit L may include the structural unit L1 and a structural unit L2-2 represented by the following formula (2-2).

[0084]

[0085] In the formula, X is a halogen atom. The halogen atom may be, for example, a chlorine atom or a fluorine atom. From the viewpoint of easily adjusting the highest occupied molecular orbital (HOMO) level, a fluorine atom is more preferred.

[0086] From the viewpoint of solubility and HOMO level of the charge transporting polymer, the proportion of the structural unit L2-2 is preferably 75 mol% or less, more preferably 50 mol% or less, and further preferably 25 mol% or less, based on the total of the structural unit L. On the other hand, the proportion of the structural unit L2-2 is preferably 25 mol% or more, more preferably 50 mol% or more, and further preferably 75 mol% or more.

[0087] (Structural unit B)

[0088] The structural unit B is a trivalent or higher structural unit having a structure constituting a branch portion of a charge transporting polymer. From the viewpoint of improving the durability of the organic electronic element, the structural unit B is preferably hexavalent or less, more preferably pentavalent or less, and further preferably trivalent or tetravalent. The structural unit B is preferably a unit having charge transport properties. For example, from the viewpoint of improving the durability of the organic electronic element, the structural unit B is selected from a substituted or unsubstituted aromatic amine structure, a carbazole structure, a condensed polycyclic aromatic hydrocarbon structure, and a structure containing one or more of these.

[0089] The following are mentioned as a specific example of structural unit B. The structural unit B is not limited to the following.

[0090]

[0091] W represents a trivalent linking group, for example, an aromatic triyl or heteroaromatic triyl having 2 to 30 carbon atoms. An aromatic triyl is an atomic group obtained by removing three hydrogen atoms from an aromatic hydrocarbon. A heteroaromatic triyl is an atomic group obtained by removing three hydrogen atoms from an aromatic heterocycle. Ar represents a divalent linking group independently of each other, for example, an arylene group or a heteroarylene group having 2 to 30 carbon atoms independently of each other. Ar is preferably an arylene group, more preferably a phenylene group. Y represents a divalent linking group, for example, a group having one or more hydrogen atoms in R (excluding a group containing a polymerizable functional group) in the structural unit L2 described above, and a divalent group obtained by removing one hydrogen atom. Z represents any one of a carbon atom, a silicon atom, or a phosphorus atom. In the structural unit, the benzene ring and Ar may have a substituent, and as an example of a substituent, the substituent R in the structural unit L2 can be listed.

[0092] In one embodiment, the structural unit B preferably has an aromatic amine structure, and more preferably includes a structural unit B1 having a structure represented by the following formula (3). As described above, the hydrogen atom in the benzene ring bonded to the nitrogen atom may be substituted with a substituent R.

[0093]

[0094] (Structural unit T)

[0095] 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, for example, selected from a substituted or unsubstituted aromatic hydrocarbon structure, an aromatic heterocyclic structure, and a structure containing one or more of these.

[0096] In one embodiment, from the viewpoint of improving hardenability, the charge transporting polymer preferably has a polymerizable functional group at the terminal portion. From this viewpoint, in one embodiment, the charge transporting polymer preferably contains a structural unit T1 having a polymerizable functional group as a terminal structure (structural unit T). In one embodiment, the structural unit T1 preferably has a structure represented by the following formula (4).

[0097] -Ar-QZ(4)

[0098] In the formula, Ar represents an arylene group or a heteroarylene group, Q represents a single bond or a linking group, and Z represents a substituted or unsubstituted polymerizable functional group.

[0099] In one embodiment, Q in the above formula is preferably a linking group. The linking group is not particularly limited, but preferably includes X and Y as represented by the following formula (4-1).

[0100] -Ar-XYZ(4-1)

[0101] In the formula, Ar represents an arylene group or a heteroarylene group, X represents a linking group described below, Y represents an aliphatic hydrocarbon group having 1 to 10 carbon atoms, and Z represents a substituted or unsubstituted polymerizable functional group.

[0102] In each formula, Ar represents an arylene group or heteroarylene group having 2 to 30 carbon atoms, and refers to a group having a structure obtained by removing two hydrogen atoms from an aromatic ring of an aromatic hydrocarbon or an aromatic heterocycle. Ar is preferably an arylene group or heteroarylene group having 2 to 30 carbon atoms. The aromatic ring may be a monocyclic structure such as benzene, or a condensed ring structure such as naphthalene in which the rings are condensed with each other.

[0103] Specific examples of compounds having an aromatic ring include aromatic hydrocarbons such as benzene, naphthalene, anthracene, tetracene, fluorene, and phenanthrene. Other specific examples include aromatic heterocycles such as pyridine, pyrazine, quinoline, isoquinoline, acridine, phenanthroline, furan, pyrrole, thiophene, carbazole, oxazole, oxadiazole, thiadiazole, triazole, benzoxazole, benzooxadiazole, benzothiadiazole, benzotriazole, and benzothiophene.

[0104] The aromatic ring may also be a structure formed by bonding two or more selected from independent monocyclic rings and condensed rings. As an example of an aromatic ring having such a structure, biphenyl, terphenyl and triphenylbenzene can be mentioned. The aromatic ring may be unsubstituted or have one or more substituents. The substituent may be, for example, a linear, cyclic or branched alkyl group having 1 to 22 carbon atoms.

[0105] In one embodiment, Ar is preferably a phenylene group or a naphthylene group, and more preferably a phenylene group.

[0106] In the above formula (4-1), X is any linking group selected from the group consisting of the following formulae (x1) to (x10).

[0107]

[0108] In the formula, R each independently represents a hydrogen atom, a linear, cyclic or branched alkyl group having 1 to 22 carbon atoms, or an aryl or heteroaryl group having 2 to 30 carbon atoms. In one embodiment, R is preferably a linear, cyclic or branched alkyl group having 1 to 22 carbon atoms. The carbon number is more preferably 2 to 16, further preferably 3 to 12, and particularly preferably 4 to 8. In another embodiment, R is preferably an aryl group having 6 to 30 carbon atoms, more preferably a phenyl group or a naphthyl group, and further preferably a phenyl group.

[0109] In a charge transporting polymer containing a structural unit represented by -Ar-CH2-O- at the end, the bonds in the molecule are easily cut by heating, and there is a tendency for insufficient heat resistance. In response to this, by forming a charge transporting polymer as follows, which contains a structural unit having a structure represented by the above formula (4-1), the heat resistance of the charge transporting polymer can be improved. With the improvement of heat resistance, the thermal degradation of the organic layer caused by the high temperature process during the manufacture of the element is improved, so it is easy to maintain the performance of the organic film.

[0110] From this viewpoint, in one embodiment, the charge transporting polymer preferably contains at least a divalent structural unit L1 represented by the above formula (1), a trivalent or higher structural unit B forming a branch, and a monovalent structural unit T1-1 represented by the above formula (4-1).

[0111] In one embodiment, the linking group X in the above formula (4-1) is preferably x1. That is, the charge transporting polymer more preferably has a structural unit T1-2 represented by the following formula (4-2).

[0112] -Ar-OYZ(4-2)

[0113] In the above formula (4-2), Y is a divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms. The aliphatic hydrocarbon group may have a linear, branched, cyclic, or a combination thereof structure. The aliphatic hydrocarbon group may be saturated or unsaturated.

[0114] In one embodiment, from the viewpoint of easy availability of monomers as raw materials, Y is preferably an aliphatic hydrocarbon group having a straight chain structure, and more preferably a saturated one. From these viewpoints, in the above formula (4-1), Y is preferably -(CH2) n That is, in one embodiment, the charge transporting polymer preferably has a structural unit T1-3 represented by the following formula (4-3).

[0115] -Ar-X-(CH2) n -Z(4-3)

[0116] In the formula, n is 1 to 10, preferably 1 to 8, and more preferably 1 to 6. From the viewpoint of heat resistance, n is more preferably 1 to 4, and most preferably 1 or 2.

[0117] As described above, the charge transporting polymer preferably contains a structural unit represented by at least one of the above formula (4-2) and formula (4-3) as the structural unit T1, and more preferably contains a structural unit T1-4 represented by the following formula (4-4).

[0118] -Ar-O-(CH2) n -Z(4-4)

[0119] In the above formulas, Z represents a polymerizable functional group. The so-called "polymerizable functional group" refers to a functional group that can form a bond by applying heat and / or light. The polymerizable functional group Z may be unsubstituted or may have a substituent. Specific examples of the polymerizable functional group Z include: a group having a carbon-carbon multiple bond (e.g., a vinyl group, an allyl group, a butenyl group, an ethynyl group, an acryloyl group, a methacryloyl group), a group having a small ring (e.g., a cyclic alkyl group such as a cyclopropyl group and a cyclobutyl group; a cyclic ether group such as an epoxy group (oxiranyl group), an oxetanyl group (oxetanyl group)); a diketene group; an epithio group; a lactone group; a lactam group, etc.), a heterocyclic group (e.g., a furan-group, a pyrrole-group, a thiophene-group, a silole-group), etc.

[0120] As the polymerizable functional group Z, vinyl, acryloyl, methacryloyl, epoxy, and oxetane are particularly preferred. From the viewpoint of reactivity and the characteristics of the organic electronic device, vinyl, oxetane, or epoxy are more preferred. These polymerizable functional groups may also have a substituent. The substituent is preferably a linear, cyclic or branched saturated alkyl group having 1 to 22 carbon atoms. The carbon number is more preferably 1 to 8, and further preferably 1 to 4. The substituent is most preferably a linear saturated alkyl group having 1 to 4 carbon atoms.

[0121] In one embodiment, from the viewpoint of storage stability, the polymerizable functional group Z is preferably an oxetane group represented by the following formula (z1): wherein R may be a hydrogen atom or a saturated alkyl group having 1 to 4 carbon atoms. R is particularly preferably a methyl group or an ethyl group.

[0122]

[0123] The charge transporting polymer containing the structural unit T1 contains at least one polymerizable functional group in its structure. The compound containing the polymerizable functional group can be hardened by polymerization reaction, and the solubility in the solvent can be changed by hardening. Therefore, the charge transporting polymer containing at least the structural unit T1 has excellent hardening property and is a material suitable for wet process.

[0124] The charge transporting polymer may contain a structural unit T2 having no polymerizable functional group as a terminal structure (structural unit T). Specific examples of the structural unit T2 include structural units having a structure represented by the following formula (5).

[0125]

[0126] In the formula, Rf is a fluoroalkyl group, a and b are 0 or 1, and a and b are not 0 at the same time. The fluoroalkyl group is as described in the structural unit L1. In one embodiment, preferably, in the formula, Rf is -CF3 or -C2F5, and a and b are 1 respectively.

[0127] A charge transporting polymer containing a structural unit having a structure represented by the above formula (5) at the terminal portion (hereinafter referred to as structural unit T2) tends to show high solubility. Therefore, when the charge transporting polymer also contains structural unit T2 having the above structure in addition to structural unit L1, high solubility is easily obtained.

[0128] In one embodiment, from the perspective of improving the hardenability of the charge transporting polymer, the proportion of the structural unit T1 having a polymerizable functional group is preferably 50 mol% or more, more preferably 75 mol% or more, and further preferably 85 mol% or more, based on all the structural units T. The proportion of the structural unit T1 may also be 100 mol%.

[0129] In one embodiment, from the viewpoint of improving the solubility of the charge transporting polymer, when the structural unit T2 is used in addition to the structural unit T1, the ratio of the structural unit T2 is preferably 75 mol% or less, more preferably 50 mol% or less, and further preferably 25 mol% or less, based on all the structural units T (T1 + T2). On the other hand, the ratio of the structural unit T1 is preferably 25 mol% or more, more preferably 50 mol% or more, and further preferably 75 mol% or more. By adjusting the ratio of the structural unit T1 and the structural unit T2 to within the range, the solubility can be further improved without reducing the hardenability of the charge transporting polymer.

[0130] (Polymerizable functional group)

[0131] In one embodiment, the charge transporting polymer preferably has at least one polymerizable functional group in the molecule. As described above, the polymerizable functional group, as the structural unit T1, can be introduced into the terminal portion of the charge transporting polymer, can be introduced into the portion other than the terminal portion (i.e., the structural unit L or the structural unit B), or can be introduced into both the terminal portion and the portion other than the terminal portion.

[0132] From the perspective of hardenability, it is preferably introduced at least to the terminal portion, and from the perspective of achieving both hardenability and charge transportability, it is preferably introduced only to the terminal portion. In addition, in the charge transport polymer having a branched structure, the polymerizable functional group may be introduced into the main chain of the charge transport polymer, may be introduced into the side chain, or may be introduced into both the main chain and the side chain.

[0133] From the viewpoint of contributing to the change of solubility, the polymerizable functional group is preferably contained in a large amount in the charge transporting polymer. On the other hand, from the viewpoint of not hindering the charge transporting property, it is preferably contained in a small amount in the charge transporting polymer. The content of the polymerizable functional group can be appropriately set in consideration of these.

[0134] For example, from the perspective of obtaining a sufficient change in solubility, the number of polymerizable functional groups per molecule of the charge transporting polymer is preferably two or more, more preferably three or more. In addition, from the perspective of ensuring charge transportability, the number of polymerizable functional groups is preferably 1,000 or less, more preferably 500 or less. Here, the number of polymerizable functional groups refers to, for example, the total of the polymerizable functional groups contained in the structural unit T1 and the polymerizable functional groups contained in other structural units.

[0135] The number of polymerizable functional groups per molecule of the charge transporting polymer can be calculated as an average value using the ratio of the amount of monomers having polymerizable functional groups added to the total amount of monomers corresponding to each structural unit used to synthesize the charge transporting polymer, the weight average molecular weight of the charge transporting polymer, etc.

[0136] In addition, the number of polymerizable functional groups can be adjusted by the 1 The ratio of the integral value of the signal derived from the polymerizable functional group in the H nuclear magnetic resonance (NMR) spectrum to the integral value of all spectra, the weight average molecular weight of the charge transporting polymer, etc. are calculated as average values. For simplicity, when the addition amount is clear, it is preferred to use the value calculated using the addition amount.

[0137] (Number average molecular weight)

[0138] The number average molecular weight of the charge transporting polymer can be appropriately adjusted in consideration of solubility in a solvent, film-forming properties, etc. From the viewpoint of excellent charge transport properties, the number average molecular weight is preferably 500 or more, more preferably 1,000 or more, and further preferably 2,000 or more. In addition, from the viewpoint of maintaining good solubility in a solvent and facilitating the preparation of an ink composition, the number average molecular weight is preferably 1,000,000 or less, more preferably 100,000 or less, and further preferably 50,000 or less.

[0139] (Weight average molecular weight)

[0140] The weight average molecular weight of the charge transporting polymer can be appropriately adjusted in consideration of solubility in the solvent, film-forming properties, etc. From the viewpoint of excellent charge transport properties, the weight average molecular weight is preferably 1,000 or more, more preferably 5,000 or more, and further preferably 10,000 or more. In addition, from the viewpoint of maintaining good solubility in the solvent and facilitating the preparation of the ink composition, the weight average molecular weight is preferably 1,000,000 or less, more preferably 700,000 or less, and further preferably 400,000 or less.

[0141] The number average molecular weight and the weight average molecular weight can be measured by gel permeation chromatography (GPC) using a calibration curve of standard polystyrene under the following conditions.

[0142] Liquid delivery pump: L-6050 Hitachi High-Technologies Co., Ltd.

[0143] UV-Vis detector: L-3000 Hitachi High-Technologies Co., Ltd.

[0144] Column: Gelpack (registered trademark) GL-A160S / GL-A150S Hitachi Chemical Co., Ltd.

[0145] Eluent: Tetrahydrofuran (THF) (for HPLC, without stabilizer) Wako Pure Chemical Industries, Ltd.

[0146] Flow rate: 1mL / min

[0147] Column temperature: room temperature

[0148] Molecular weight standard material: Standard polystyrene

[0149] (Ratio of structural units)

[0150] From the viewpoint of obtaining sufficient charge transportability, based on all structural units, the ratio of structural unit L contained in the charge transport polymer is preferably 10 mol% or more, more preferably 20 mol% or more, and more preferably 30 mol% or more. In addition, if structural unit T and structural unit B are considered, the ratio of structural unit L is preferably 95 mol% or less, more preferably 90 mol% or less, and more preferably 85 mol% or less. In one embodiment, when structural unit L only includes structural unit L1, the ratio refers to the ratio of structural unit L1. In another embodiment, when structural unit L is a combination of structural unit L1 and structural unit L2, the ratio refers to the total of structural unit L1 and structural unit L2.

[0151] From the viewpoint of improving the characteristics of organic electronic components or suppressing the increase in viscosity and performing the synthesis of charge transport polymers well, the ratio of the structural unit T contained in the charge transport polymer is preferably 5 mol% or more, more preferably 10 mol% or more, and more preferably 15 mol% or more, based on all structural units. In addition, from the viewpoint of obtaining sufficient charge transportability, the ratio of the structural unit T is preferably 60 mol% or less, more preferably 55 mol% or less, and more preferably 50 mol% or less. In one embodiment, when the structural unit T contains only the structural unit T1, the ratio refers to the ratio of the structural unit T1. In another embodiment, when the structural unit T is a combination of the structural unit T1 and the structural unit T2, the ratio refers to the total of the structural unit T1 and the structural unit T2.

[0152] From the viewpoint of improving the durability of organic electronic components, the proportion of structural unit B contained in the charge transporting polymer is preferably 1 mol% or more, more preferably 5 mol% or more, and more preferably 10 mol% or more, based on all structural units. In addition, from the viewpoint of suppressing the increase in viscosity, performing the synthesis of the charge transporting polymer well, or obtaining sufficient charge transportability, the proportion of structural unit B is preferably 50 mol% or less, more preferably 40 mol% or less, and more preferably 30 mol% or less.

[0153] With respect to the viewpoint of making the charge transport polymer harden efficiently, based on all structural units, the ratio of the polymerizable functional groups in the charge transport polymer is preferably 0.1 mol% or more, more preferably 1 mol% or more, and more preferably 3 mol% or more. In addition, with respect to the viewpoint of obtaining good charge transportability, the ratio of the polymerizable functional groups is preferably 70 mol% or less, more preferably 60 mol% or less, and more preferably 50 mol% or less. Furthermore, the so-called "ratio of polymerizable functional groups" herein refers to the ratio of structural units having polymerizable functional groups.

[0154] When considering the balance of charge transport properties, durability, productivity, etc., the ratio (molar ratio) of structural unit L, structural unit T and structural unit B is preferably L:T:B=100:10~200:10~100, more preferably 100:20~180:20~90, and even more preferably 100:40~160:30~80.

[0155] The ratio of the structural units can be determined by using the amount of monomers added to synthesize the charge transporting polymer corresponding to each structural unit. 1 The integrated value of the spectrum derived from each structural unit in the H NMR spectrum is calculated as an average value. For simplicity, when the amount of addition is clear, it is preferable to adopt the value obtained using the amount of addition.

[0156] When the charge transporting polymer is a hole transporting material, from the viewpoint of obtaining high hole injection and hole transport, the polymer is preferably a compound comprising a unit having an aromatic amine structure and / or a unit having a carbazole structure as the main structural unit. From the viewpoint of the above, the total number of units having an aromatic amine structure and / or units having a carbazole structure relative to the number of all structural units in the polymer (excluding the terminal structural units) is preferably 40% or more, more preferably 45% or more, and further preferably 50% or more. It is also possible to set the ratio of the total number of units having an aromatic amine structure and / or units having a carbazole structure to 100%. Furthermore, the ratio of the aromatic amine structure is also the value obtained by adding the ratio of the structural unit L1.

[0157] (Method for producing charge transporting polymer)

[0158] Charge transport polymers can be manufactured by various synthesis methods, and the manufacturing method is not particularly limited. For example, known coupling reactions such as Suzuki coupling, Negishi coupling, Sonogashira coupling, Stille coupling, and Buchwald-Hartwig coupling can be used. Suzuki coupling causes a cross-coupling reaction using a Pd catalyst between an aromatic boronic acid derivative and an aromatic halide. According to Suzuki coupling, charge transport polymers can be easily manufactured by bonding the desired aromatic rings to each other.

[0159] In the coupling reaction, as a catalyst, for example, a Pd(0) compound, a Pd(II) compound, a Ni compound, etc. are used. In addition, a catalyst type produced by mixing tris(dibenzylideneacetone)dipalladium(0), palladium(II) acetate, etc. as a precursor with a phosphine ligand can also be used. For the synthesis method of the charge transporting polymer, for example, reference can be made to the description of International Publication No. 2010 / 140553.

[0160] [Dopant]

[0161] The organic electronic material may further contain a dopant. The dopant is not particularly limited as long as it is a compound that exhibits a doping effect by being added to the organic electronic material and can improve the transportability of charges. There are p-type doping and n-type doping. In p-type doping, the dopant uses a substance that acts as an electron acceptor, and in n-type doping, the dopant uses a substance that acts as an electron donor. In order to improve the hole transportability, p-type doping is preferably performed, and in order to improve the electron transportability, n-type doping is preferably performed. The dopant used in the organic electronic material may be a dopant that exhibits any effect of p-type doping or n-type doping. In addition, a dopant may be added alone, or a plurality of dopants may be added in a mixed manner.

[0162] The dopant used for p-type doping is an electron-accepting compound, and examples thereof include Lewis acids, protonic acids, transition metal compounds, ionic compounds, halogen compounds, and π-conjugated compounds. Specifically, as Lewis acids, FeCl3, PF5, AsF5, SbF5, BF5, BCl3, BBr3, etc. can be listed; as protonic acids, inorganic acids such as HF, HCl, HBr, HNO3, H2SO4, HClO4, benzenesulfonic acid, p-toluenesulfonic acid, dodecylbenzenesulfonic acid, polyvinylsulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, trifluoroacetic acid, 1-butanesulfonic acid, vinylphenylsulfonic acid, camphorsulfonic acid, etc. can be listed; as transition metal compounds, FeOCl, TiCl4, ZrCl4, HfCl4, NbF5, AlCl3, NbCl5, TaCl5, MoF5 can be listed; as ionic compounds, tetrakis(pentafluorophenyl)borate ion, tris(trifluoromethanesulfonyl)methide ion, bis(trifluoromethanesulfonyl)imide ion, hexafluoroantimonate ion, AsF6 can be listed. - (hexafluoroarsenate ion), BF4 - (tetrafluoroborate ion), PF6 -As halogen compounds, Cl2, Br2, I2, ICl, ICl3, IBr, IF, etc. can be cited; as π conjugated compounds, TCNE (tetracyanoethylene) (tetracyanoethylene), TCNQ (tetracyanoquinodimethane) (tetracyanoquinodimethane), etc. can be cited. In addition, the electron accepting compounds recorded in Japanese Patent Laid-Open No. 2000-36390 Gazette, Japanese Patent Laid-Open No. 2005-75948 Gazette, Japanese Patent Laid-Open No. 2003-213002 Gazette, etc. can also be used. Lewis acids, ionic compounds, π conjugated compounds, etc. are preferred.

[0163] The dopant used in 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; salts of alkali metals and / or alkaline earth metals such as LiF and Cs2CO3; metal complexes; electron-donating organic compounds, etc.

[0164] In order to easily change the solubility of the organic layer, it is preferable to use a compound that can function as a polymerization initiator for the polymerizable functional group as a dopant. Examples of substances that have both the function of a dopant and the function of a polymerization initiator include the above-mentioned ionic compounds.

[0165] [Other optional ingredients]

[0166] The organic electronic material may further contain a charge-transporting low-molecular compound, other charge-transporting polymers, and the like.

[0167] [content]

[0168] From the viewpoint of obtaining good charge transport properties, the content of the charge transport polymer is preferably 50% by mass or more, more preferably 70% by mass or more, and even more preferably 80% by mass or more, relative to the total mass of the organic electronic material. It may also be 100% by mass.

[0169] In the case of containing a dopant, from the viewpoint of improving the charge transport property of the organic electronic material, the content of the dopant is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and further preferably 0.5% by mass or more, relative to the total mass of the organic electronic material. In addition, from the viewpoint of maintaining good film-forming properties, it is preferably 50% by mass or less, more preferably 30% by mass or less, and further preferably 20% by mass or less, relative to the total mass of the organic electronic material.

[0170] [Polymerization initiator]

[0171] In one embodiment, the organic electronic material may also contain a polymerization initiator. As the polymerization initiator, known free radical polymerization initiators, cationic polymerization initiators, anionic polymerization initiators, etc. can be used. From the viewpoint that the ink composition can be easily prepared, it is preferred to use a substance that has both the function of a dopant and the function of a polymerization initiator. As a polymerization initiator that also has the function of a dopant, for example, the ionic compound can be cited. As an example of an ionic compound, for example, a salt having the perfluoro anion can be cited, and as an example thereof, a salt (onium salt) of a perfluoro anion and an iodonium ion or an ammonium ion can be cited. As a specific example of such a compound, a compound having a structure represented by the following formula can be cited.

[0172]

[0173] <Ink composition>

[0174] One embodiment relates to an ink composition that further contains a solvent in the organic electronic material of the embodiment. The solvent can be any solvent that can dissolve or disperse the organic electronic material, such as the following examples. By using this ink composition, an organic layer can be easily formed by a simple method such as a coating method.

[0175] [Solvent]

[0176] As the solvent, water, an organic solvent, or a mixed solvent thereof can be used. Examples of the organic solvent include: alcohols such as methanol, ethanol, and isopropanol; alkanes such as pentane, hexane, and octane; cycloalkanes such as cyclohexane; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, tetralin, and diphenylmethane; aliphatic ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and propylene glycol-1-monomethyl ether acetate; 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole, phenethyl ether, 2-methoxytoluene, 3-methoxytoluene, 4- Aromatic ethers such as methoxytoluene, 2,3-dimethylanisole, and 2,4-dimethylanisole; aliphatic esters such as ethyl acetate, n-butyl acetate, ethyl lactate, and n-butyl lactate; aromatic esters such as phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, propyl benzoate, and n-butyl benzoate; amide solvents such as N,N-dimethylformamide and N,N-dimethylacetamide; dimethyl sulfoxide, tetrahydrofuran, acetone, chloroform, and dichloromethane. Preferred are aromatic hydrocarbons, aliphatic esters, aromatic esters, aliphatic ethers, and aromatic ethers.

[0177] Although the existing representative charge transport polymers are soluble in aromatic hydrocarbons such as benzene, their solubility in ester solvents such as aliphatic esters and aromatic esters is significantly low, or they are often insoluble. In contrast, the charge transport polymers disclosed in this specification also show excellent solubility in ester solvents. Therefore, in the preparation of the ink composition, various solvents can be used in combination, which can improve the applicability to coating methods such as inkjet printing.

[0178] [additive]

[0179] The ink composition may further contain additives as optional components. Examples of the additives include polymerization inhibitors, stabilizers, thickeners, gelling agents, flame retardants, antioxidants, reduction inhibitors, oxidants, reducing agents, surface modifiers, emulsifiers, defoamers, dispersants, surfactants, and the like.

[0180] [content]

[0181] The content of the solvent in the ink composition can be determined in consideration of the application in various coating methods. For example, the content of the solvent is preferably an amount in which the ratio of the charge transporting polymer to the solvent is 0.1% by mass or more, more preferably an amount in which the ratio of the charge transporting polymer to the solvent is 0.2% by mass or more, and further preferably an amount in which the ratio of the charge transporting polymer to the solvent is 20% by mass or less, more preferably an amount in which the ratio of the charge transporting polymer to the solvent is 15% by mass or less, and further preferably an amount in which the ratio of the charge transporting polymer to the solvent is 10% by mass or less.

[0182] <Organic thin film>

[0183] The organic thin film (organic layer) as an embodiment of the present disclosure can suppress thermal degradation and surface oxidation by drying the coating film after formation in a nitrogen environment, and has excellent performance. In addition, when an organic electronic material containing a charge transporting polymer having a polymerizable functional group is used as an organic layer forming material, an insoluble organic layer is obtained, so it is easy to realize multilayering by a wet process.

[0184] From the viewpoint of improving the efficiency of charge transfer, 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. In addition, from the viewpoint of reducing resistance, the thickness of the organic layer is preferably 300 nm or less, more preferably 200 nm or less, and further preferably 100 nm or less.

[0185] In one embodiment, a method for producing an organic thin film includes: forming a coating film of an organic electronic material including a charge transporting polymer; and heating the coating film to form the organic thin film.

[0186] The formation of the coating film is preferably carried out in an atmospheric environment or an inert gas environment using a coating solution containing an organic electronic material and a solvent. Examples of coating methods include spin coating, casting, dipping, plate printing such as relief printing, gravure printing, offset printing, lithography, relief reverse offset printing, screen printing, gravure printing, and other plateless printing methods such as inkjet printing.

[0187] The formation of the organic thin film is carried out by heating the coating film in an atmospheric environment or an inert gas environment. By heating the coating film, the solvent in the coating film evaporates to obtain a dry film. In the case where the charge transporting polymer has a polymerizable functional group, the polymerization reaction of the charge transporting polymer is carried out by heating and, if necessary, light irradiation to obtain an insoluble organic thin film.

[0188] Here, the term "inert gas" includes, for example, helium, argon, nitrogen, and mixed gases thereof. The term "inert gas atmosphere" means that the concentration of the inert gas in the atmosphere is 99.5% or more, preferably 99.9% or more, and more preferably 99.99% or more by volume.

[0189] The coating film can be heated using, for example, a hot plate or an oven. To perform heating in an inert gas atmosphere, a hot plate is used in an inert gas atmosphere, or the interior of an oven is set in an inert gas atmosphere.

[0190] From the viewpoint of efficiently removing the solvent, the heating is preferably carried out at a temperature above the boiling point of the solvent. In addition, when the charge transporting polymer has a polymerizable functional group, it is preferably a temperature at which the polymerization reaction is efficiently carried out. In one embodiment, the heating temperature of the coating film is preferably 140°C or more, more preferably 180°C or more, and further preferably 190°C or more. On the other hand, from the viewpoint of suppressing deterioration caused by heating, it is preferably 300°C or less, more preferably 280°C or less, and further preferably 250°C or less.

[0191] <Organic electronic components>

[0192] In one embodiment, the organic electronic element has at least the organic layer of the embodiment. Examples of the organic electronic element include organic EL elements, organic photoelectric conversion elements, organic transistors, etc. The organic electronic element preferably has a structure in which the organic layer is arranged between at least a pair of electrodes.

[0193] [Organic EL element]

[0194] The organic EL element of the embodiment has at least the organic layer of the embodiment. The organic EL element generally includes a light-emitting layer, an anode, a cathode and a substrate, and optionally includes other functional layers such as a hole injection layer, an electron injection layer, a hole transport layer, and an electron transport layer. Each layer can be formed by a vapor deposition method or by a coating method. The organic EL element preferably has an organic layer as a light-emitting layer or other functional layer, more preferably has an organic layer as a functional layer, and further preferably has an organic layer as at least one of a hole injection layer and a hole transport layer.

[0195] Figure 1 It is a schematic cross-sectional view showing one embodiment of an organic EL element. Figure 1 The organic EL element is a multilayered element, which sequentially comprises: a substrate 8, an anode 2, a hole injection layer 3 and a hole transport layer 6 including the organic layer of the embodiment, a light emitting layer 1, an electron transport layer 7, an electron injection layer 5, and a cathode 4. Each layer is described below.

[0196] Figure 1 For example, the hole injection layer 3 and the hole transport layer 6 are organic layers formed by coating using the organic electronic material. However, the organic EL element of the embodiment of the present invention is not limited to this structure, and other organic layers may be organic layers formed using the organic electronic material.

[0197] [Luminous layer]

[0198] As the material used in the light-emitting layer, light-emitting materials such as low molecular weight compounds, polymers, and dendrimers can be used. Polymers are highly soluble in solvents and are suitable for coating methods, so they are preferred. As light-emitting materials, fluorescent materials, phosphorescent materials, thermally activated delayed fluorescence materials (TADF), etc. can be listed.

[0199] Examples of fluorescent materials include low molecular weight compounds such as perylene, coumarin, rubrene, quinacridone, stilbene, dye laser pigments, aluminum complexes, and derivatives thereof; polymers such as polyfluorene, polyphenylene, polyphenylene vinylene, polyvinyl carbazole, fluorene-benzothiadiazole copolymers, fluorene-triphenylamine copolymers, and derivatives thereof; and mixtures thereof.

[0200] As the phosphorescent material, a metal complex containing a metal such as Ir or Pt can be used. Examples of the Ir complex include FIr(pic) (iridium(III)bis[(4,6-difluorophenyl)-pyridine-N,C 2] picolinic acid), green-emitting Ir(ppy)3(face-tri(2-phenylpyridine)iridium), red-emitting (btp)2Ir(acac)(bis[2-(2'-benzo[4,5-α]thienyl)pyridine-N,C 3 〕iridium (acetylacetonate)), Ir(piq)3 (tris(1-phenylisoquinoline)iridium), etc. Examples of Pt complexes include PtOEP (2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphine platinum) which emits red light.

[0201] In the case where the light-emitting layer includes a phosphorescent material, it is preferred that it also includes a host material in addition to the phosphorescent material. As the host material, a low molecular weight compound, a polymer, or a dendritic polymer can be used. As a low molecular weight compound, for example, CBP (4,4'-bis (9H-carbazole-9-yl) biphenyl), mCP (1,3-bis (9-carbazole) benzene), CDBP (4,4'-bis (carbazole-9-yl) -2,2'- dimethylbiphenyl), derivatives thereof, etc., as a polymer, the organic electronic material of the embodiment, polyvinyl carbazole, polyphenylene, polyfluorene, derivatives thereof, etc. can be listed.

[0202] Examples of thermally activated delayed fluorescent materials include: Advanced Materials (Adv. Mater.), 21, 4802-4906 (2009); Appl. Phys. Lett., 98, 083302 (2011); Chemical Communications (Chem. Comm.), 48, 9580 (2012); Appl. Phys. Lett., 101, 093306 (2012); Journal of the American Chemical Society (J. Am. Chem. Soc.), 134, 14706 (2012); Chemical Communications (Chem. Comm.), 4 Compounds described in Journal of Physical Chemistry A (J.Phys.Chem.A), 117, 5607 (2013); Journal of Physical Chemistry and Chemical Physics (Phys.Chem.Chem.Phys.), 15, 15850 (2013); Chemical Communications (Chem.Comm.), 49, 10385 (2013); Chemical Letters (Chem.Lett.), 43, 319 (2014), etc.

[0203] [Hole transport layer, hole injection layer]

[0204] Figure 1In the embodiment, the hole injection layer 3 and the hole transport layer 6 are organic layers formed using the organic electronic material, but the organic EL element of the embodiment is not limited to this structure, and other organic layers may be organic layers formed using the organic electronic material. It is preferably used as at least one of the hole transport layer and the hole injection layer formed using the organic electronic material, and it is further preferably used as at least the hole transport layer. For example, in the case where the organic EL element has an organic layer formed using the organic electronic material as a hole transport layer and also has a hole injection layer, a known material can be used in the hole injection layer. In addition, for example, in the case where the organic EL element has an organic layer formed using the organic electronic material as a hole injection layer and also has a hole transport layer, a known material can be used in the hole transport layer.

[0205] Examples of materials that can be used in the hole injection layer and the hole transport layer include aromatic amine compounds (e.g., aromatic diamines such as N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (α-NPD)), phthalocyanine compounds, and thiophene compounds (e.g., thiophene conductive polymers (e.g., poly(3,4-ethylenedioxythiophene): poly(sodium 4-Styrenesulfonate), PEDOT: PSS), etc.).

[0206] [Electron transport layer, electron injection layer]

[0207] Examples of materials used in the electron transport layer and the electron injection layer include phenanthroline derivatives, bipyridine derivatives, nitro-substituted fluorene derivatives, diphenylquinone derivatives, dioxythiopyran derivatives, fused rings such as naphthalene and perylene, tetracarboxylic anhydride, carbodiimide, fluorenylidene methane derivatives, anthraquinone dimethane and anthrone derivatives, oxadiazole derivatives, thiadiazole derivatives, benzimidazole derivatives (e.g., 2,2',2"-(1,3,5-phenyltriyl)tris(1-phenyl-1H-benzimidazole) (2 ,2',2'-(1,3,5-Benzenetriyl)tris[1-phenyl-1H-benzimidazole],TPBi)), quinoxaline derivatives, aluminum complexes (for example, bis(2-methyl-8-hydroxyquinoline)-4-(phenylphenoxy)aluminum (Bis(2-methyl-8-quino; -Biphenyl-4-olato)aluminum,BAlq)), etc. In addition, the organic electronic materials of the above-mentioned embodiments can also be used.

[0208] [cathode]

[0209] As the cathode material, for example, a metal or a metal alloy such as Li, Ca, Mg, Al, In, Cs, Ba, Mg / Ag, LiF, or CsF can be used.

[0210] [anode]

[0211] As the anode material, for example, metal (such as Au) or other conductive materials can be used. Examples of other materials include oxides (such as ITO: indium oxide / tin oxide) and conductive polymers (such as polythiophene-polystyrene sulfonic acid mixture (PEDOT: PSS)).

[0212] [Substrate]

[0213] As the substrate, glass, plastic, etc. can be used. The substrate is preferably transparent and preferably flexible. Quartz glass, a light-transmitting resin film, etc. can be preferably used.

[0214] Examples of the resin film include films containing 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.

[0215] When a resin film is used, in order to suppress the permeation of water vapor, oxygen, etc., the resin film may be coated with an inorganic substance such as silicon oxide or silicon nitride before use.

[0216] [Emitting color]

[0217] The color of light emitted by the organic EL element is not particularly limited. White organic EL elements are preferably used in various lighting devices such as home lighting, interior lighting for cars, clocks, and backlights for liquid crystals.

[0218] As a method for forming a white organic EL element, a method of mixing colors by using multiple luminescent materials to emit multiple luminescent colors simultaneously can be used. The combination of multiple luminescent colors is not particularly limited, and examples thereof include: a combination containing three maximum luminescent wavelengths of blue, green, and red; a combination containing two maximum luminescent wavelengths of blue and yellow, yellow-green and orange, etc. The luminescent color can be controlled by adjusting the type and amount of the luminescent material.

[0219] <Display element, lighting device, display device>

[0220] In one embodiment, the display element includes the organic EL element of the embodiment. For example, by using the organic EL element as an element corresponding to each pixel of red, green and blue (RGB), a color display element can be obtained. The image forming method includes: a simple matrix type, which directly drives each organic EL element arranged on a flat panel using electrodes arranged in a matrix; and an active matrix type, which configures a thin film transistor for each element to drive.

[0221] In one embodiment, the lighting device includes the organic EL element of the embodiment. In another embodiment, the display device includes the lighting device and a liquid crystal element as a display component. For example, the display device may be a display device using the lighting device of the embodiment as a backlight and a well-known liquid crystal element as a display component, that is, a liquid crystal display device.

[0222] [Example]

[0223] 1. Preparation of charge transport (hole transport) polymers

[0224] (Preparation of Pd Catalyst)

[0225] In a glove box under a nitrogen atmosphere, weigh tri(dibenzylideneacetone)dipalladium (73.2 mg, 80 μmol) into a sample tube at room temperature, add toluene (15 mL), and stir for 30 minutes. Similarly, weigh tri(tert-butyl)phosphine (129.6 mg, 640 μmol) into a sample tube, add toluene (5 mL), and stir for 5 minutes. Mix these solutions, stir at room temperature for 30 minutes, and use as a catalyst. All solvents were used after degassing for more than 30 minutes by bubbling with nitrogen.

[0226] The various monomers used in the preparation of the hole transporting polymers 1 to 13 described below are as follows.

[0227]

[0228]

[0229] (Preparation of Hole Transporting Polymer 1)

[0230] Monomer A1 (2.5 mmol), monomer A2 (2.5 mmol), monomer B1 (2.0 mmol), monomer C1 (2.0 mmol), monomer C2 (2.0 mmol), methyl tri-n-octylammonium chloride (Alfa Aesar "Aliquat 336") (0.03 g), potassium hydroxide (1.12 g), pure water (5.54 mL) and toluene (15 mL) were added to a three-necked round-bottom flask, and the previously prepared Pd catalyst toluene solution (1.0 mL) was added to mix, and the mixture was heated to reflux for 2 hours to react. All operations so far were performed under a nitrogen stream. In addition, all solvents were used after being degassed by nitrogen bubbling for more than 30 minutes.

[0231] After the reaction is completed, the organic layer is washed with water and injected into methanol-water (9:1). The generated precipitate is recovered by suction filtration and washed with methanol-water (9:1). The obtained precipitate is dissolved in toluene and reprecipitated from methanol. The obtained precipitate is recovered by suction filtration and dissolved in toluene, and a metal adsorbent ("Triphenylphosphine, polymer-bound on styrene-divinylbenzene copolymer" manufactured by Strem Chemicals, 200 mg relative to 100 mg of the precipitate) is added, and stirred at 80°C for 2 hours. After the stirring is completed, the metal adsorbent and insoluble matter are filtered off, and the filtrate is reprecipitated from methanol. The generated precipitate is recovered by suction filtration and washed with methanol. The obtained precipitate is vacuum dried to obtain a hole transport polymer 1.

[0232] The number average molecular weight of the obtained hole transporting polymer 1 was 21,700 and the weight average molecular weight was 49,400.

[0233] The number average molecular weight and the weight average molecular weight are measured by GPC (polystyrene conversion) using tetrahydrofuran (THF) as an eluent. The measurement conditions are as follows.

[0234] Liquid delivery pump: L-6050 Hitachi High-Technologies Co., Ltd.

[0235] UV-Vis detector: L-3000 Hitachi High-Technologies Co., Ltd.

[0236] Column: Gelpack (registered trademark) GL-A160S / GL-A150S Hitachi Chemical Co., Ltd.

[0237] Eluent: THF (for HPLC, without stabilizer) Wako Pure Chemical Industries, Ltd.

[0238] Flow rate: 1mL / min

[0239] Column temperature: room temperature

[0240] Molecular weight standard material: Standard polystyrene

[0241] (Preparation of Hole Transporting Polymer 2)

[0242] Monomer A1 (2.0 mmol), monomer A2 (3.0 mmol), monomer B1 (2.0 mmol), monomer C1 (2.0 mmol), monomer C2 (2.0 mmol), methyl tri-n-octylammonium chloride (Alfa Aesar "Aliquat 336") (0.03 g), potassium hydroxide (1.12 g), pure water (5.54 mL) and toluene (17 mL) were added to a three-necked round-bottom flask, and the previously prepared Pd catalyst toluene solution (1.0 mL) was added for mixing, and the mixture was reacted by heating the mixture under reflux for 2 hours. All operations so far were performed under a nitrogen gas stream. In addition, all solvents were used after being degassed for more than 30 minutes by nitrogen bubbling. Thereafter, the same operation as the preparation of hole transport polymer 1 was performed.

[0243] The obtained hole transporting polymer 2 had a number average molecular weight of 12,000 and a weight average molecular weight of 38,200.

[0244] (Preparation of Hole Transporting Polymer 3)

[0245] Monomer A1 (1.5 mmol), monomer A2 (3.5 mmol), monomer B1 (2.0 mmol), monomer C1 (2.0 mmol), monomer C2 (2.0 mmol), methyl tri-n-octylammonium chloride (Alfa Aesar "Aliquat 336") (0.03 g), potassium hydroxide (1.12 g), pure water (5.54 mL) and toluene (17 mL) were added to a three-necked round-bottom flask, and the previously prepared Pd catalyst toluene solution (1.0 mL) was added for mixing, and the resulting mixed solution was heated to reflux for 2 hours to react. All operations so far were performed under a nitrogen gas stream. In addition, all solvents were used after being degassed by nitrogen bubbling for more than 30 minutes. Thereafter, the same operations as those for the preparation of hole transport polymer 1 were performed.

[0246] The number average molecular weight of the obtained hole transporting polymer 3 was 10,800 and the weight average molecular weight was 40,000.

[0247] (Preparation of Hole Transporting Polymer 4)

[0248] Monomer A1 (2.5 mmol), monomer A2 (2.5 mmol), monomer B1 (2.0 mmol), monomer C1 (2.0 mmol), monomer C3 (2.0 mmol), methyl tri-n-octylammonium chloride (Alfa Aesar "Aliquat 336") (0.03 g), potassium hydroxide (1.12 g), pure water (5.54 mL) and toluene (17 mL) were added to a three-necked round-bottom flask, and the previously prepared Pd catalyst toluene solution (1.0 mL) was added for mixing, and the mixture was reacted by heating the mixture under reflux for 2 hours. All operations so far were performed under a nitrogen gas stream. In addition, all solvents were used after being degassed for more than 30 minutes by nitrogen bubbling. Thereafter, the same operation as the preparation of hole transport polymer 1 was performed.

[0249] The obtained hole transport polymer 4 had a number average molecular weight of 16,000 and a weight average molecular weight of 44,000.

[0250] (Preparation of Hole Transporting Polymer 5)

[0251] Monomer A1 (3.0 mmol), monomer A3 (2.0 mmol), monomer B1 (2.0 mmol), monomer C1 (2.0 mmol), monomer C3 (2.0 mmol), methyl tri-n-octylammonium chloride (Alfa Aesar "Aliquat 336") (0.03 g), potassium hydroxide (1.12 g), pure water (5.54 mL) and toluene (50 mL) were added to a three-necked round-bottom flask, and the previously prepared Pd catalyst toluene solution (1.0 mL) was added for mixing, and the mixture was reacted by heating the mixture under reflux for 2 hours. All operations so far were performed under a nitrogen gas stream. In addition, all solvents were used after being degassed for more than 30 minutes by nitrogen bubbling. Thereafter, the same operation as the preparation of hole transport polymer 1 was performed.

[0252] The number average molecular weight of the obtained hole transporting polymer 5 was 19,900 and the weight average molecular weight was 49,200.

[0253] (Preparation of Hole Transporting Polymer 6)

[0254] Monomer A1 (5.0 mmol), monomer B1 (2.0 mmol), monomer C1 (2.0 mmol), monomer C2 (2.0 mmol), methyl tri-n-octylammonium chloride (Alfa Aesar "Aliquat 336") (0.03 g), potassium hydroxide (1.12 g), pure water (5.54 mL) and toluene (17 mL) were added to a three-necked round-bottom flask, and the previously prepared Pd catalyst toluene solution (1.0 mL) was added for mixing, and the mixture was reacted by heating the mixture under reflux for 2 hours. All operations so far were performed under a nitrogen gas stream. In addition, all solvents were used after being degassed for more than 30 minutes by nitrogen bubbling. Thereafter, the same operation as the preparation of hole transport polymer 1 was performed.

[0255] The obtained hole transporting polymer 6 had a number average molecular weight of 14,300 and a weight average molecular weight of 60,000.

[0256] (Preparation of Hole Transporting Polymer 7)

[0257] Monomer A1 (5.0 mmol), monomer B1 (2.0 mmol), monomer C1 (2.0 mmol), monomer C3 (2.0 mmol), methyl tri-n-octylammonium chloride (Alfa Aesar "Aliquat 336") (0.03 g), potassium hydroxide (1.12 g), pure water (5.54 mL) and toluene (17 mL) were added to a three-necked round-bottom flask, and the previously prepared Pd catalyst toluene solution (1.0 mL) was added for mixing, and the mixture was heated to reflux for 2 hours to react. All operations so far were performed under a nitrogen gas stream. In addition, all solvents were used after being degassed for more than 30 minutes by nitrogen bubbling. Thereafter, the same operation as the preparation of hole transport polymer 1 was performed.

[0258] The number average molecular weight of the obtained hole transporting polymer 7 was 14,300 and the weight average molecular weight was 57,800.

[0259] (Preparation of Hole Transporting Polymer 8)

[0260] Monomer A1 (2.0 mmol), monomer A4 (3.0 mmol), monomer B1 (2.0 mmol), monomer C1 (2.0 mmol), monomer C2 (2.0 mmol), methyl tri-n-octylammonium chloride (Alfa Aesar "Aliquat 336") (0.03 g), potassium hydroxide (1.12 g), pure water (5.54 mL) and toluene (17 mL) were added to a three-necked round-bottom flask, and the previously prepared Pd catalyst toluene solution (1.0 mL) was added for mixing, and the mixture was reacted by heating the mixture under reflux for 2 hours. All operations so far were performed under a nitrogen gas stream. In addition, all solvents were used after being degassed for more than 30 minutes by nitrogen bubbling. Thereafter, the same operation as the preparation of hole transport polymer 1 was performed.

[0261] The number average molecular weight of the obtained hole transporting polymer 8 was 20,700 and the weight average molecular weight was 50,400.

[0262] (Preparation of Hole Transporting Polymer 9)

[0263] Monomer A1 (2.0 mmol), monomer A4 (3.0 mmol), monomer B1 (2.0 mmol), monomer C1 (2.0 mmol), monomer C3 (2.0 mmol), methyl tri-n-octylammonium chloride (Alfa Aesar "Aliquat 336") (0.03 g), potassium hydroxide (1.12 g), pure water (5.54 mL) and toluene (17 mL) were added to a three-necked round-bottom flask, and the previously prepared Pd catalyst toluene solution (1.0 mL) was added for mixing, and the mixture was reacted by heating the mixture under reflux for 2 hours. All operations so far were performed under a nitrogen gas stream. In addition, all solvents were used after being degassed for more than 30 minutes by nitrogen bubbling. Thereafter, the same operation as the preparation of hole transport polymer 1 was performed.

[0264] The obtained hole transporting polymer 9 had a number average molecular weight of 17,400 and a weight average molecular weight of 44,900.

[0265] (Preparation of Hole Transporting Polymer 10)

[0266] Monomer A2 (5.0 mmol), monomer B1 (2.0 mmol), monomer C1 (2.0 mmol), monomer C2 (2.0 mmol), methyl tri-n-octylammonium chloride (Alfa Aesar "Aliquat 336") (0.03 g), potassium hydroxide (1.12 g), pure water (5.54 mL) and toluene (50 mL) were added to a three-necked round-bottom flask, and the previously prepared Pd catalyst toluene solution (1.0 mL) was added for mixing, and the mixture was reacted by heating the mixture under reflux for 2 hours. All operations so far were performed under a nitrogen gas stream. In addition, all solvents were used after being degassed for more than 30 minutes by nitrogen bubbling. Thereafter, the same operation as the preparation of hole transport polymer 1 was performed.

[0267] The obtained hole transporting polymer 10 had a number average molecular weight of 15,700 and a weight average molecular weight of 45,100.

[0268] (Preparation of Hole Transporting Polymer 11)

[0269] Monomer A2 (5.0 mmol), monomer B1 (2.0 mmol), monomer C1 (2.0 mmol), monomer C3 (2.0 mmol), methyl tri-n-octylammonium chloride (Alfa Aesar "Aliquat 336") (0.03 g), potassium hydroxide (1.12 g), pure water (5.54 mL) and toluene (50 mL) were added to a three-necked round-bottom flask, and the previously prepared Pd catalyst toluene solution (1.0 mL) was added for mixing, and the mixture was reacted by heating the mixture under reflux for 2 hours. All operations so far were performed under a nitrogen gas stream. In addition, all solvents were used after being degassed for more than 30 minutes by nitrogen bubbling. Thereafter, the same operation as the preparation of hole transport polymer 1 was performed.

[0270] The obtained hole transporting polymer 11 had a number average molecular weight of 13,300 and a weight average molecular weight of 36,200.

[0271] (Preparation of Hole Transporting Polymer 12)

[0272] Monomer A4 (5.0 mmol), monomer B1 (2.0 mmol), monomer C1 (2.0 mmol), monomer C2 (2.0 mmol), methyl tri-n-octylammonium chloride (Alfa Aesar "Aliquat 336") (0.03 g), potassium hydroxide (1.12 g), pure water (5.54 mL) and toluene (50 mL) were added to a three-necked round-bottom flask, and the previously prepared Pd catalyst toluene solution (1.0 mL) was added for mixing, and the mixture was heated to reflux for 2 hours to react. All operations so far were performed under a nitrogen gas stream. In addition, all solvents were used after being degassed for more than 30 minutes by nitrogen bubbling. Thereafter, the same operation as the preparation of hole transport polymer 1 was performed.

[0273] The obtained hole transport polymer 12 had a number average molecular weight of 12,300 and a weight average molecular weight of 59,600.

[0274] (Preparation of Hole Transporting Polymer 13)

[0275] Monomer A4 (5.0 mmol), monomer B1 (2.0 mmol), monomer C1 (2.0 mmol), monomer C3 (2.0 mmol), methyl tri-n-octylammonium chloride (Alfa Aesar "Aliquat 336") (0.03 g), potassium hydroxide (1.12 g), pure water (5.54 mL) and toluene (50 mL) were added to a three-necked round-bottom flask, and the previously prepared Pd catalyst toluene solution (1.0 mL) was added for mixing, and the mixture was heated to reflux for 2 hours to react. All operations so far were performed under a nitrogen gas stream. In addition, all solvents were used after being degassed for more than 30 minutes by nitrogen bubbling. Thereafter, the same operation as the preparation of hole transport polymer 1 was performed.

[0276] The obtained hole transporting polymer 13 had a number average molecular weight of 15,100 and a weight average molecular weight of 56,500.

[0277] 2. Evaluation of Solubility of Charge Transporting Polymer

[0278] (Example 1 to Example 9 and Comparative Example 1 to Comparative Example 4)

[0279] The solubility of each of the hole transporting polymers prepared above in various solvents was evaluated by the following method. The results are shown in Table 1.

[0280] (Solubility Evaluation Method)

[0281] Weigh any amount of each hole transporting polymer prepared previously into a sample tube, adjust the amount of each solvent so that the polymer concentration reaches 3wt% and add it. Then, stir at 300rpm for 24 hours at room temperature (25°C) using a mixing rotor. Observe the stirred solution by visual judgment and judge the solubility according to the following criteria.

[0282] (Evaluation criteria for solubility)

[0283] G: Good solubility (the polymer is dissolved in the solvent. More specifically, no precipitate is observed, and the solution is not turbid but appears transparent.)

[0284] P: Poor solubility (the polymer is insoluble in the solvent. More specifically, a precipitate is observed or the solution is turbid.)

[0285] [Table 1]

[0286]

[0287] From the comparison between the examples and the comparative examples, it can be seen that when the charge transporting polymer has a structure represented by formula (1) having a fluoroalkyl group at a specific position of the benzene ring of the triphenylamine structure (the structure of monomer A1), high solubility can be obtained in various solvents. In addition, it can be seen that when the charge transporting polymer also has a fluoroalkyl group at the terminal, higher solubility can be obtained.

[0288] Furthermore, when an organic thin film was obtained by coating a solution containing the charge transporting polymer of each example, an organic hole-only device (HOD) having the organic thin film was manufactured and voltage was applied, current flowed in all cases, confirming that the devices had a hole transporting function.

[0289] The above results show that according to the present invention, a charge transporting polymer that can be preferably used as an organic electronic material and has high solubility in various solvents can be provided. Therefore, according to the present invention, an ink composition and an organic film that can improve device characteristics by using an organic electronic material containing the charge transporting polymer can be provided. Furthermore, an organic electronic device and an organic EL device having excellent device characteristics, as well as a display device, a lighting device, and a display device using the organic EL device can be provided.

Claims

1. An organic electronic material comprising a charge transporting polymer having a structure branched in three or more directions, The charge transporting polymer contains a trivalent or higher valent structural unit, a divalent structural unit including a structural unit L1 having a structure represented by the following formula (1), and a monovalent structural unit including a structural unit T1 having a structure represented by the following formula (4-4) and a structural unit T2 represented by the following formula (5), In the formula, Rf is independently a fluoroalkyl group, a and b are 0 or 1, and a and b are not 0 at the same time, -Ar-O-(CH2) n -Z (4-4) In the formula, Ar is an arylene group or a heteroarylene group, n is 1 to 4, and Z is a polymerizable functional group, wherein the polymerizable functional group is an oxetane group or an epoxy group. In the formula, Rf is independently a fluoroalkyl group, a and b are 0 or 1, and a and b are not 0 at the same time. 2 . The organic electronic material according to claim 1 , wherein the charge transporting polymer has a hole injecting property or a hole transporting property.

3. The organic electronic material according to claim 1, wherein the charge transporting polymer further comprises one or more structures selected from the group consisting of an aromatic amine structure, a pyrrole structure, a carbazole structure, a thiophene structure, a benzene structure, a phenoxazine structure and a fluorene structure other than the structure represented by the formula (1). The organic electronic material according to claim 3 , wherein the aromatic amine structure is an aniline structure. The organic electronic material according to claim 1 , further comprising a polymerization initiator. The organic electronic material according to claim 5 , wherein the polymerization initiator is an ionic compound. The organic electronic material according to claim 6 , wherein the ionic compound is an onium salt. 8 . An ink composition comprising: the organic electronic material according to claim 1 ; and a solvent. 9 . An organic thin film formed by using the organic electronic material according to claim 1 or the ink composition according to claim 8 . 10 . An organic electroluminescent element comprising the organic thin film according to claim 9 . The organic electroluminescent element according to claim 10 , further comprising a flexible substrate. 12 . The organic electroluminescent element according to claim 10 , further comprising a resin film substrate. 13 . A display element comprising the organic electroluminescent element according to claim 10 .

14. A lighting device comprising the organic electroluminescent element according to claim 10.

15. A display device, comprising: The lighting device according to claim 14; And a liquid crystal element as a display member.

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