Composition, organic electroluminescent element, method for producing same, display device, and lighting device

Abstract

The present invention addresses the problem of providing a composition that improves the luminous efficacy of an organic electroluminescent element. The present invention pertains to: a composition that contains an arylamine compound represented by a specific formula and an electron-accepting compound represented by a specific formula; and an organic electroluminescent element having, upon a substrate, an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer contains a cross-linking reaction product of an arylamine compound represented by a specific formula and an electron-accepting compound represented by a specific formula.

Description

Composition, organic electroluminescent device and method for producing the same, display device, and lighting device

[0001] The present invention relates to a composition, an organic electroluminescent element and a method for producing the same, a display device, and a lighting device.

[0002] In recent years, organic electroluminescent devices using organic thin films have been developed instead of those using inorganic materials as thin-film electroluminescent devices. Organic electroluminescent devices (OLEDs) usually have a charge injection layer, a charge transport layer, an organic light-emitting layer, an electron transport layer, etc. between an anode and a cathode, and materials suitable for each of these layers are being developed, and development is progressing for each of the emitted colors, red, green, and blue.

[0003] Methods for forming organic layers of organic electroluminescent devices include vacuum deposition and wet film-forming methods (coating methods). Vacuum deposition methods are advantageous in that they facilitate lamination, improving charge injection from the anode and / or cathode and facilitating exciton confinement in the light-emitting layer. On the other hand, wet film-forming methods have the advantages of not requiring a vacuum process, facilitating large-area fabrication, and easily forming layers containing multiple materials with various functions by using a coating solution containing a mixture of multiple materials with various functions. For this reason, in recent years, research and development of organic electroluminescent devices using film-forming methods by coating methods has been actively conducted.

[0004] Patent Document 1 describes an organic electroluminescent device having a polymer containing a crosslinking group and an electron-accepting compound containing a crosslinking group as charge injection materials. Patent Document 2 describes an organic electroluminescent device having a composition containing a fluorene aryldiamine compound containing a crosslinking group and an electron-accepting compound. Patent Document 3 describes an organic electroluminescent device having a composition containing a carbazole arylamine compound containing a crosslinking group and an electron-accepting compound. Patent Document 4 discloses an organic electroluminescent device containing a compound having one or more polymerizable substituents and two or more carbazole groups in the molecule.

[0005] International Publication No. 2019 / 059331 International Publication No. 2019 / 231257 US Patent Application Publication No. 2021 / 0151685 Japanese Patent Application Laid-Open No. 2008-244471

[0006] Generally, when an organic electron donor such as an arylamine and an organic electron acceptor are mixed in an appropriate ratio, and the N atoms of the arylamine partially form an ionic complex with the organic electron acceptor, the formation of this ionic complex reduces the barrier to hole injection from the anode. Therefore, materials that form stable ionic complexes have attracted attention. The materials and techniques disclosed in Patent Documents 1 to 3 form ionic complexes from an organic electron donor such as an arylamine polymer, a low-molecular-weight arylamine compound, or a carbazole arylamine compound with an organic electron acceptor, but the reduction in the driving voltage of the organic electroluminescent device is insufficient. Patent Document 4 also discloses a biscarbazole compound containing an oxetane crosslinking group. However, the organic electron acceptor without a crosslinking group is used as a photopolymerization initiator, which insufficiently prevents the organic electron acceptor from diffusing into the light-emitting layer, failing to improve the luminous efficiency and driving life.

[0007] The present invention has been made in view of the above-mentioned conventional circumstances, and an object of the present invention is to provide a composition that improves the luminous efficiency of an organic electroluminescent device.

[0008]

[0009] As a result of extensive investigations, the present inventors have found that the above-mentioned problems can be solved by using a hole injection layer and / or a hole transport layer containing a crosslinking reaction product of an arylamine compound having a crosslinking group and an electron-accepting compound having a crosslinking group, and have thereby completed the present invention.

[0010] As a result of extensive investigations, the present inventors have found that the above-mentioned problems can be solved by using a hole injection layer and / or a hole transport layer containing a crosslinking reaction product of an arylamine compound having a crosslinking group and a polymer having a crosslinking group, the polymer having a twisted main chain whose planarity is disrupted by introducing a substituent into an aromatic ring in the main chain, and have thereby completed the present invention.

[0009] That is, the gist of the present invention is as follows: [1] A composition containing an arylamine compound represented by any one of the following formulas (3-1) to (3-4), and an electron-accepting compound represented by the following formula (81):

[0010]

[0011] (In formulas (3-1) to (3-4), Ar２ , Ar ３ are each independently any one of formulas (4-1) to (4-3), and a plurality of R ２ are each independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, a2 is each independently 0 or 1, and a ２ are each independently a hydrogen atom or a bridging group.

[0012]

[0013] (In formulas (4-1) to (4-3), * represents a bonding position, and multiple R １ are each independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, a plurality of a1's are each independently 0 or 1, and a plurality of A's are each independently 0 or 1. １ are each independently a hydrogen atom or a bridging group. １ At least one of the groups consisting of

[0014]

[0015] (In formula (81), five R ８１ , the five Rs ８２ , the five Rs ８３ , the five Rs ８４ are independent of each other, and R ８１ ~R ８４ are each independently a hydrogen atom, a deuterium atom, a halogen atom, an aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 50 carbon atoms which may have a substituent, a fluorine-substituted alkyl group having 1 to 12 carbon atoms, or a bridging group. １ , Ph ２ , Ph ３ , Ph ４ is a symbol indicating each benzene ring. ＋ represents a counter cation. However, formula (81) has at least two bridging groups.

[0016] [2] The composition according to [1], further comprising a polymer having an arylamine structure represented by the following formula (50) as a repeating unit and having a crosslinking group:

[0017]

[0018] (In formula (50), Ar ５１ represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a group in which a plurality of groups selected from aromatic hydrocarbon groups and aromatic heterocyclic groups are linked together; ５２ represents a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group, or a divalent group in which a plurality of at least one group selected from the group consisting of the divalent aromatic hydrocarbon group and the divalent aromatic heterocyclic group is linked together directly or via a linking group. ５１ and Ar ５２ may form a ring via a single bond or a linking group. ５１ , Ar ５２ may have a substituent.)

[0019] [3] The composition according to [2], wherein the arylamine compound represented by any one of formulas (3-1) to (3-4), the electron-accepting compound represented by formula (81), and the polymer having an arylamine structure represented by formula (50) as a repeating unit each independently have a crosslinking group selected from formulas (X1) to (X17) in the following crosslinking group group T. <Crosslinking Group Group T>

[0020]

[0021] (In formulas (X1) to (X17), Q represents a direct bond or a linking group. * represents a bonding position. R in formulas (X3), (X4), (X5) and (X9) １１０ represents a hydrogen atom or an alkyl group which may have a substituent. In formulas (X1) to (X3), the benzene ring and the naphthalene ring may have a substituent. In addition, the substituents may be bonded to each other to form a ring. In formulas (X1) and (X2), the cyclobutene ring may have a substituent.

[0022] [4] The composition according to [3], wherein the crosslinking group is any one of the formulas (X1) to (X3).

[0023] [5] The composition according to any one of [2] to [4], wherein the repeating unit represented by the formula (50) is a repeating unit represented by the following formula (54):

[0024]

[0025] (In formula (54), Ar ５１ represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a group in which a plurality of groups selected from aromatic hydrocarbon groups and aromatic heterocyclic groups are linked together; X represents —C(R ２０７ ) (R ２０８ ) -, -N(R ２０９ ) - or -C(R ２１１ ) (R ２１２ )-C(R ２１３ ) (R ２１４ )- and R ２０１ , R ２０２ , R ２２１ and R ２２２ each independently represents an alkyl group which may have a substituent, and R ２０７ ~R ２０９ and R ２１１ ~R ２１４ are each independently a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent; a and b are each independently an integer of 0 to 4; c is an integer of 0 to 3; d is an integer of 0 to 4; and i and j are each independently an integer of 0 to 3.

[0026] [6] Ar ２ , Ar ３ , Ar ５１ , Ar ５２ , R １ , R ２ , R ２０１ , R ２０２ , R ２２１ , R ２２２ , R ２０７ ~R ２０９ , R ２１１ ~R ２１４wherein none of the organic layers has a substituent. [7] The composition according to any one of [1] to [6], further containing a solvent. [8] A method for manufacturing an organic electroluminescent device having an anode and a cathode on a substrate, and an organic layer between the anode and the cathode, the method comprising forming the organic layer by a wet film formation method using the composition according to [7]. [9] A method for manufacturing an organic electroluminescent device according to [8], wherein the organic layer is an organic layer between the anode and the light-emitting layer.

[0027]

[10] An organic electroluminescent device having an anode and a cathode on a substrate, and an organic layer between the anode and the cathode, wherein the organic layer contains a crosslinked reaction product of an arylamine compound represented by any one of the following formulas (3-1) to (3-4) and an electron-accepting compound represented by the following formula (81):

[0028]

[0029] (In formulas (3-1) to (3-4), Ar ２ , Ar ３ are each independently any one of formulas (4-1) to (4-3), and a plurality of R ２ are each independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, a2 is each independently 0 or 1, and a ２ are each independently a hydrogen atom or a bridging group.

[0030]

[0031] (In formulas (4-1) to (4-3), * represents a bonding position, and multiple R １ are each independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, a plurality of a1's are each independently 0 or 1, and a plurality of A's are each independently 0 or 1. １ are each independently a hydrogen atom or a bridging group. １ At least one of the groups consisting of

[0032]

[0033] (In formula (81), five R ８１ , the five Rs ８２ , the five Rs ８３ , the five Rs ８４ are independent of each other, and R ８１ ~R ８４ are each independently a hydrogen atom, a deuterium atom, a halogen atom, an aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 50 carbon atoms which may have a substituent, a fluorine-substituted alkyl group having 1 to 12 carbon atoms, or a bridging group. １ , Ph ２ , Ph ３ , Ph ４ is a symbol indicating each benzene ring. ＋ represents a counter cation. However, formula (81) has at least two bridging groups.

[0034]

[11] An organic electroluminescent device having an anode and a cathode on a substrate, and an organic layer between the anode and the cathode, wherein the organic layer contains a crosslinking reaction product between an arylamine compound represented by any one of the following formulas (3-1) to (3-4) and a polymer having an arylamine structure represented by the following formula (50) as a repeating unit and having a crosslinking group:

[0035]

[0036] (In formulas (3-1) to (3-4), Ar ２ , Ar ３ are each independently any one of formulas (4-1) to (4-3), and a plurality of R ２ are each independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, a2 is each independently 0 or 1, and a ２ are each independently a hydrogen atom or a bridging group.

[0037]

[0038] (In formulas (4-1) to (4-3), * represents a bonding position, and multiple R １are each independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, a plurality of a1's are each independently 0 or 1, and a plurality of A's are each independently 0 or 1. １ are each independently a hydrogen atom or a bridging group. １ At least one of the groups consisting of

[0039]

[0040] (In formula (50), Ar ５１ represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a group in which a plurality of groups selected from aromatic hydrocarbon groups and aromatic heterocyclic groups are linked together; ５２ represents a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group, or a divalent group in which a plurality of at least one group selected from the group consisting of the divalent aromatic hydrocarbon group and the divalent aromatic heterocyclic group is linked together directly or via a linking group. ５１ and Ar ５２ may form a ring via a single bond or a linking group. ５１ , Ar ５２ may have a substituent.)

[0041]

[12] Ar ２ , Ar ３ , Ar ５１ , Ar ５２ , R １ , R ２

[13] An organic electroluminescent element according to

[11] , wherein none of the elements has a substituent.

[13] An organic electroluminescent element produced by the method for producing an organic electroluminescent element according to [8] or [9].

[14] A display device comprising the organic electroluminescent element according to any one of

[10] to

[13] .

[15] A lighting device comprising the organic electroluminescent element according to any one of

[10] to

[13] .

[0042] According to the present invention, there is provided a composition that improves the luminous efficiency of an organic electroluminescent device.

[0043] FIG. 1 is a cross-sectional view showing a structural example of an organic electroluminescent device according to the present invention.

[0044] Hereinafter, embodiments of a composition, an organic electroluminescent element and a method for producing the same, a display device, and a lighting device according to one embodiment of the present invention will be described in detail. The following description is of a first embodiment, which is one example (typical example) of an embodiment of the present invention, but the present invention is not limited to these contents as long as it does not deviate from the gist of the present invention. In the present invention, "optionally having a substituent" means that the compound may have one or more substituents.

[0045] [Definitions] In the following detailed description of the structures of the arylamine compound, electron-accepting compound, and polymer (charge-transporting polymer compound) according to the present invention, the common partial structures are assumed to be the following structures unless otherwise specified.

[0046] <Aromatic Hydrocarbon Group> The aromatic hydrocarbon group refers to a monovalent, divalent, or trivalent or higher aromatic hydrocarbon ring structure, depending on the bonding state in the structure of the compound to be described later. In the aromatic hydrocarbon ring structure, the number of carbon atoms is generally not limited, but is preferably 6 to 60 carbon atoms, with the upper limit of the carbon number being more preferably 48 or less carbon atoms, and more preferably 30 or less carbon atoms. Specific examples include 6-membered monocyclic or 2- to 5-condensed ring groups such as benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring, acenaphthene ring, fluoranthene ring, and fluorene ring, as well as structures in which multiple groups selected from these are linked together. When multiple aromatic hydrocarbon rings are linked together, typically, structures in which 2 to 10 rings are linked together are exemplified, with structures in which 2 to 5 rings are linked together being preferred. When multiple aromatic hydrocarbon rings are linked together, the linked rings may be the same structure or different structures. Preferred aromatic hydrocarbon ring structures are a benzene ring, a biphenyl ring, i.e., a structure in which two benzene rings are linked together, a terphenyl ring, i.e., a structure in which three benzene rings are linked together, a quaterphenylene ring, i.e., a structure in which four benzene rings are linked together, a naphthalene ring, and a fluorene ring.

[0047] <Aromatic heterocyclic group> The aromatic heterocyclic group refers to a monovalent, divalent, or trivalent or higher aromatic heterocyclic structure depending on the bonding state in the structure of the compound to be described later. In the aromatic heterocyclic structure, the number of carbon atoms is not usually limited, but is preferably 3 to 60, and the upper limit of the carbon number is more preferably 48 or less, and more preferably 30 or less. Specific examples thereof include divalent groups of a 5- to 6-membered monocyclic or 2- to 4-fused ring such as a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, an oxadiazole ring, an indole ring, a carbazole ring, a pyrroloimidazole ring, a pyrrolopyrazole ring, a pyrrolopyrrole ring, a thienopyrrole ring, a thienothiophene ring, a furopyrrole ring, a furofuran ring, a thienofuran ring, a benzisoxazole ring, a benzisothiazole ring, a benzimidazole ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinoxaline ring, a phenanthridine ring, a benzimidazole ring, a perimidine ring, a quinazoline ring, a quinazolinone ring, or an azulene ring, or groups in which a plurality of these are linked together. When a plurality of aromatic heterocycles are linked, they may be the same structure or different structures. When a plurality of aromatic heterocycles are linked, typically, a structure in which 2 to 10 rings are linked is mentioned, and a structure in which 2 to 5 rings are linked is preferred. Preferred aromatic heterocycle structures are a thiophene ring, a benzothiophene ring, a pyrimidine ring, a triazine ring, a carbazole ring, a dibenzofuran ring, and a dibenzothiophene ring.

[0048] <Substituents> In the following description of the structures of the polymer compound and the low molecular weight compound of the present invention, unless otherwise specified, the substituent is any group, but is preferably a group or a crosslinking group selected from the following substituent group Z. Furthermore, in the description of the structures of the polymer compound and the low molecular weight compound of the present invention, when it is stated that the substituent that may be possessed is selected from the substituent group Z, or that the substituent that may be possessed is preferably selected from the substituent group Z, the preferred substituents are also as described in the following substituent group Z. Furthermore, when Ar ２ , Ar ３ , R１ , R ２ , R ８１ ~R ８５ , R １１０ , Ar ５１ ~Ar ５６ , Ar ｄ１８ , Ar ６３ ~Ar ６５ , Ar ７１ ~Ar ７３ , R ２０１ , R ２０２ , R ２０７ ~R ２０９ , R ２１１ ~R ２１４ , R ２２１ , R ２２２ , R ３０４ , R ３０５ , R ５１７ ~R ５１９ In the description of the structure of (1), when it is stated that the substituent that may be possessed is selected from a crosslinking group, or that the substituent that may be possessed is preferably selected from a crosslinking group, the preferred crosslinking group is also as described in the crosslinking group below. When the composition of the present invention described later contains a polymer having an arylamine structure represented by formula (54) described later as a repeating unit, Ar ２ , Ar ３ , Ar ５１ , Ar ５２ , R １ , R ２ , R ２０１ , R ２０２ , R ２２１ , R ２２２ , R ２０７ ~R ２０９ , R ２１１ ~R ２１４ In the organic electroluminescent device of the present invention described later, when the organic layer contains a crosslinking reaction product of an arylamine compound represented by any one of formulas (3-1) to (3-4) described later and a polymer having an arylamine structure represented by formula (50) described later as a repeating unit and having a crosslinking group, Ar ２ , Ar ３ , Ar ５１ , Ar ５２ , R １ , R ２ It is preferred that none of the groups have a substituent.

[0049] <Substituent Group Z> Substituent Group Z is a group consisting of alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, aryloxy groups, heteroaryloxy groups, alkoxycarbonyl groups, dialkylamino groups, diarylamino groups, arylalkylamino groups, acyl groups, halogen atoms, haloalkyl groups, alkylthio groups, arylthio groups, silyl groups, siloxy groups, cyano groups, aromatic hydrocarbon groups, and aromatic heterocyclic groups. These substituents may have any of a linear, branched, and cyclic structure.

[0050] More specific examples of the substituent group Z include the following structures: A linear, branched, or cyclic alkyl group having 1 or more carbon atoms, preferably 4 or more and 24 or less, preferably 12 or less, further preferably 8 or less, and more preferably 6 or less. Specific examples include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a tert-butyl group, an n-hexyl group, a cyclohexyl group, and a dodecyl group. A linear, branched, or cyclic alkenyl group having usually 2 or more carbon atoms and usually 24 or less, preferably 12 or less, specific examples include a vinyl group. A linear or branched alkynyl group having usually 2 or more carbon atoms and usually 24 or less, preferably 12 or less, specific examples include an ethynyl group. An alkoxy group having 1 or more carbon atoms and 24 or less, preferably 12 or less, specific examples include a methoxy group and an ethoxy group. An aryloxy group or heteroaryloxy group having 4 or more carbon atoms, preferably 5 or more, and 36 or less, preferably 24 or less. Specific examples include a phenoxy group, a naphthoxy group, a pyridyloxy group, etc. An alkoxycarbonyl group having 2 or more carbon atoms, 24 or less, preferably 12 or less. Specific examples include a methoxycarbonyl group, an ethoxycarbonyl group, etc. A dialkylamino group having 2 or more carbon atoms, 24 or less, preferably 12 or less. Specific examples include a dimethylamino group, a diethylamino group, etc. A diarylamino group having 10 or more carbon atoms, preferably 12 or more, and 36 or less, preferably 24 or less. Specific examples include a diphenylamino group, a ditolylamino group, an N-carbazolyl group, etc. An arylalkylamino group having 7 or more carbon atoms, 36 or less, preferably 24 or less. Specific examples include a phenylmethylamino group. An acyl group having 2 or more carbon atoms, 24 or less, preferably 12 or less. Specific examples include an acetyl group and a benzoyl group. a halogen atom such as a fluorine atom or a chlorine atom, preferably a fluorine atom; a haloalkyl group having 1 to 12, preferably 6, carbon atoms, specifically a trifluoromethyl group;An alkylthio group having 1 or more carbon atoms and usually 24 or less, preferably 12 or less. Specific examples include a methylthio group and an ethylthio group. An arylthio group having 4 or more carbon atoms, preferably 5 or more, and 36 or less, preferably 24 or less. Specific examples include a phenylthio group, a naphthylthio group, a pyridylthio group, etc. A silyl group having 2 or more carbon atoms, preferably 3 or more, and usually 36 or less, preferably 24 or less. Specific examples include a trimethylsilyl group and a triphenylsilyl group. A siloxy group having 2 or more carbon atoms, preferably 3 or more, and usually 36 or less, preferably 24 or less. Specific examples include a trimethylsiloxy group and a triphenylsiloxy group. A cyano group. An aromatic hydrocarbon group having 6 or more carbon atoms, 36 or less, preferably 24 or less. Specific examples include a phenyl group, a naphthyl group, a group in which multiple phenyl groups are linked, etc. An aromatic heterocyclic group having 3 or more carbon atoms, preferably 4 or more, and 36 or less, preferably 24 or less. Specific examples include a thienyl group and a pyridyl group.

[0051] The substituents may have any of a linear, branched, or cyclic structure. When the substituents are adjacent to each other, the adjacent substituents may be bonded to each other to form a ring. The preferred ring size is a 4-membered ring, a 5-membered ring, or a 6-membered ring, and specific examples thereof include a cyclobutane ring, a cyclopentane ring, and a cyclohexane ring.

[0052] Among the above-mentioned substituent group Z, preferred are alkyl groups, alkoxy groups, aromatic hydrocarbon groups, and aromatic heterocyclic groups, more preferred are alkyl groups and aromatic hydrocarbon groups, and most preferred is having no substituent.

[0053] Furthermore, each substituent in the above-mentioned substituent group Z may further have a substituent. Examples of such substituents include the same as those in the above-mentioned substituent group Z or a crosslinking group. Preferably, the substituent does not have any further substituent, or is an alkyl group having 8 or less carbon atoms, an alkoxy group having 8 or less carbon atoms, or a phenyl group, more preferably an alkyl group having 6 or less carbon atoms, an alkoxy group having 6 or less carbon atoms, or a phenyl group. From the viewpoint of charge transportability, it is more preferable that the substituent does not have any further substituent. When the substituent that each substituent in the above-mentioned substituent group Z may further have is a crosslinking group, the crosslinking group is preferably a crosslinking group selected from the above-mentioned crosslinking group group T. The substituent that preferably further has a crosslinking group is an alkyl group or an aromatic hydrocarbon group.

[0054] <Crosslinking group> A crosslinking group refers to a group that reacts with another crosslinking group located in the vicinity thereof upon exposure to heat and / or active energy rays to form a new chemical bond. In this case, the reactive group may be the same as or different from the crosslinking group.

[0055] The crosslinking group is not limited to, but includes a group containing an alkenyl group, a group containing a conjugated diene structure, a group containing an alkynyl group, a group containing an oxirane structure, a group containing an oxetane structure, a group containing an aziridine structure, an azide group, a group containing a maleic anhydride structure, a group containing an alkenyl group bonded to an aromatic ring, a cyclobutene ring fused to an aromatic ring, etc. Specific preferred crosslinking groups are preferably represented by any of the following formulae (X1) to (X17) in the following crosslinking group group T:

[0056] <Bridging group group T>

[0057]

[0058] (In formulas (X1) to (X17), Q represents a direct bond or a linking group. * represents a bonding position. R in formulas (X3), (X4), (X5) and (X9) １１０ represents a hydrogen atom or an alkyl group which may have a substituent. In formulas (X1) to (X3), the benzene ring and the naphthalene ring may have a substituent. In addition, the substituents may be bonded to each other to form a ring. In formulas (X1) and (X2), the cyclobutene ring may have a substituent.

[0059] (Q) When Q is a linking group, the linking group is not particularly limited, but is preferably an alkylene group, a divalent oxygen atom, or a divalent aromatic hydrocarbon group which may have a substituent. The alkylene group is typically an alkylene group having 1 to 12 carbon atoms, preferably 1 to 8 carbon atoms, and more preferably 1 to 6 carbon atoms. The divalent aromatic hydrocarbon group typically has 6 or more carbon atoms and typically has 36 or less, preferably 30 or less, and more preferably 24 or less carbon atoms. The aromatic hydrocarbon ring structure is preferably a benzene ring, and the optional substituent can be selected from the substituent group Z described above.

[0060] R １１０ The alkyl group represented by the formula (I) has a linear, branched or cyclic structure and has 1 or more carbon atoms, preferably 24 or less, more preferably 12 or less, and even more preferably 8 or less.

[0061] The benzene ring and naphthalene ring of formulas (X1) to (X3), and R of formulas (X3), (X4), (X5), and (X9) １１０Preferred substituents that may be present in the formula (X1) are alkyl groups, aromatic hydrocarbon groups, alkyloxy groups, and aralkyl groups. The alkyl group as a substituent has a linear, branched, or cyclic structure and preferably has 24 or less carbon atoms, more preferably 12 or less, even more preferably 8 or less, and preferably 1 or more. The aromatic hydrocarbon group as a substituent has preferably 24 or less carbon atoms, more preferably 18 or less, even more preferably 12 or less, and preferably 6 or more. The aromatic hydrocarbon group may further have the above-mentioned alkyl group as a substituent. The alkyloxy group as a substituent has preferably 24 or less carbon atoms, more preferably 12 or less, even more preferably 8 or less, and preferably 1 or more. The aralkyl group as a substituent has preferably 30 or less carbon atoms, more preferably 24 or less, even more preferably 14 or less, and preferably 7 or more. The alkylene group contained in the aralkyl group preferably has a linear or branched structure. The aryl group contained in the aralkyl group may further have the above-mentioned alkyl group as a substituent. The substituent that the cyclobutene ring of formula (X1) or (X2) may preferably have is an alkyl group. The alkyl group as the substituent has a linear, branched or cyclic structure and preferably has 24 or less carbon atoms, more preferably 12 or less carbon atoms, even more preferably 8 or less carbon atoms, and preferably 1 or more carbon atoms.

[0062] As the crosslinking group, a crosslinking group represented by either formula (X1) or formula (X2) is preferred because the crosslinking reaction proceeds only with heat, the polarity is small, and the effect on charge transport is small.

[0063] In the crosslinking group represented by formula (X1), the cyclobutene ring is opened by heat, and the ring-opened groups bond together to form a crosslinked structure, as shown in the following formula: Note that in the following, the linking group Q in formulas (X1) to (X3) is omitted.

[0064]

[0065] In the crosslinking group represented by formula (X2), the cyclobutene ring is opened by heat, and the ring-opened groups bond to each other to form a crosslinked structure, as shown in the following formula.

[0066]

[0067] In the crosslinking group represented by either formula (X1) or formula (X2), the cyclobutene ring is opened by heat, and if a double bond is present nearby, the ring-opened group reacts with the double bond to form a crosslinked structure. Below is an example in which a crosslinked structure is formed by a group obtained by ring-opening the crosslinking group represented by formula (X1) and a crosslinking group represented by formula (X3) having a double bond moiety.

[0068]

[0069] Examples of the double bond-containing group capable of reacting with the crosslinking group represented by either formula (X1) or formula (X2) include the crosslinking group represented by formula (X3), as well as the crosslinking group represented by any of formulas (X4), (X5), (X11), (X14), (X15), (X16), and (X17). When these double bond-containing groups are used as crosslinking groups in the electron-accepting compound, it is preferable to incorporate the crosslinking group represented by either formula (X1) or formula (X2) into other components forming the hole injection layer and / or hole transport layer, such as a hole transport compound, because this increases the possibility of forming a crosslinked structure.

[0070] As the crosslinking group, a radically polymerizable crosslinking group represented by any one of formulas (X3), (X4) and (X5) is preferred because it has low polarity and is unlikely to interfere with charge transport.

[0071] As the crosslinking group, a crosslinking group represented by formula (X6) is preferred in terms of enhancing electron-accepting property. When a crosslinking group represented by formula (X6) is used, the following crosslinking reaction proceeds.

[0072]

[0073] The crosslinking group represented by either formula (X7) or (X8) is preferred because of its high reactivity. When the crosslinking group represented by formula (X7) or the crosslinking group represented by formula (X8) is used, the following crosslinking reaction proceeds.

[0074]

[0075] As the crosslinking group, a cationic polymerizable crosslinking group represented by any one of formulas (X9), (X10) and (X11) is preferred in terms of high reactivity.

[0076] <Charge Transport Material> The charge transport material according to the present invention is a material capable of transporting holes and / or electrons. The arylamine compound having a crosslinking group and the charge transporting polymer compound according to the present invention, which will be described later, are both charge transport materials. Furthermore, the charge transport material according to the present invention is preferably hole transportable, and is preferably a material that is oxidized by an electron accepting compound to form a cation radical. In the present invention, the charge transporting polymer compound is preferably a hole transporting polymer compound, and a polymer containing an arylamine structure as a repeating unit is preferred. In this case, the charge is usually a hole, transporting a charge means transporting holes, the charge transport film is a hole transport film, and the charge injection layer is a hole injection layer.

[0077] [Composition of the Present Invention] The composition of the present invention comprises an arylamine compound represented by any one of the following formulae (3-1) to (3-4) (hereinafter sometimes referred to as the "arylamine compound of the present invention"), and an electron-accepting compound represented by the following formula (81) (hereinafter sometimes referred to as the "electron-accepting compound of the present invention"). Another composition of the present invention is a composition that, in addition to the composition of the present invention, further comprises a polymer having an arylamine structure represented by the following formula (50) as a repeating unit and having a crosslinking group. Yet another composition of the present invention is a composition that comprises an arylamine compound represented by any one of the following formulae (3-1) to (3-4) and a polymer having an arylamine structure represented by the following formula (50) as a repeating unit and having a crosslinking group. Here, the polymer represented by the following formula (50) is a polymer that contains, as a repeating unit, an arylamine structure having a twisted structure that inhibits conjugation. It is preferable that the composition of the present invention comprises a polymer represented by the following formula (50) from the viewpoint of extending the life.

[0078]

[0079] (In formulas (3-1) to (3-4), Ar ２ , Ar ３ are each independently any one of formulas (4-1) to (4-3), and a plurality of R ２are each independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, a2 is each independently 0 or 1, and a ２ are each independently a hydrogen atom or a bridging group.

[0080]

[0081] (In formulas (4-1) to (4-3), * represents a bonding position, and multiple R １ are each independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, a plurality of a1's are each independently 0 or 1, and a plurality of A's are each independently 0 or 1. １ are each independently a hydrogen atom or a bridging group. １ At least one of the groups consisting of

[0082]

[0083] (In formula (81), five R ８１ , the five Rs ８２ , the five Rs ８３ , the five Rs ８４ are independent of each other, and R ８１ ~R ８４ are each independently a hydrogen atom, a deuterium atom, a halogen atom, an aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 50 carbon atoms which may have a substituent, a fluorine-substituted alkyl group having 1 to 12 carbon atoms, or a bridging group. １ , Ph ２ , Ph ３ , Ph ４ is a symbol indicating each benzene ring. ＋ is a counter cation, and preferably has a structure represented by the following formula (83): However, formula (81) has at least two bridging groups.

[0084]

[0085] (In formula (83), Ar ８１ , Ar ８２ are each independently an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent.

[0086]

[0087] (In formula (50), Ar ５１ represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a group in which a plurality of groups selected from aromatic hydrocarbon groups and aromatic heterocyclic groups are linked together; ５２ represents a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group, or a divalent group in which a plurality of at least one group selected from the group consisting of the divalent aromatic hydrocarbon group and the divalent aromatic heterocyclic group is linked together directly or via a linking group. ５１ and Ar ５２ may form a ring via a single bond or a linking group. ５１ , Ar ５２ may have a substituent, but preferably has no substituent.)

[0088] In the composition of the present invention, it is preferable from the viewpoint of reactivity that the arylamine compound represented by any one of formulas (3-1) to (3-4), the electron-accepting compound represented by formula (81), and the polymer having an arylamine structure represented by formula (50) as a repeating unit each independently have a crosslinking group selected from formulas (X1) to (X17) in the group of crosslinking groups T, and it is more preferable from the viewpoint of charge transportability that the crosslinking group is any one of formulas (X1) to (X3).

[0089] <Arylamine Compound Having a Crosslinking Group> The arylamine compound according to the present invention is a compound represented by any one of (3-1) to (3-4), and is contained as a charge transport material in the composition for organic electroluminescent elements of the present invention.

[0090]

[0091] (In formulas (3-1) to (3-4), Ar ２ , Ar ３ are each independently any one of formulas (4-1) to (4-3), and a plurality of R ２ are each independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, a2 is each independently 0 or 1, and a ２are each independently a hydrogen atom or a bridging group.

[0092]

[0093] (In formulas (4-1) to (4-3), * represents a bonding position, and multiple R １ are each independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, a plurality of a1's are each independently 0 or 1, and a plurality of A's are each independently 0 or 1. １ are each independently a hydrogen atom or a bridging group. １ At least one of the groups consisting of

[0094] (R １ , R ２ ) R １ and R ２ are each independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms, which may have a substituent. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 50, more preferably 6 to 30, and even more preferably 6 to 18. Specific examples of the aromatic hydrocarbon group include monovalent groups of aromatic hydrocarbon structures having a carbon number of typically 6 or more and typically 30 or less, preferably 18 or less, and more preferably 14 or less, such as a benzene ring, naphthalene ring, anthracene ring, tetraphenylene ring, phenanthrene ring, chrysene ring, pyrene ring, benzanthracene ring, or perylene ring, or monovalent groups of a structure in which multiple structures selected from these structures are bonded in a chain or branched manner. When multiple aromatic hydrocarbon rings are bonded, typically, a structure in which 2 to 8 rings are bonded is mentioned, and a structure in which 2 to 5 rings are bonded is preferred. When multiple aromatic hydrocarbon rings are bonded, the same structure may be bonded, or different structures may be bonded.

[0095] R １ , R ２are preferably each independently a phenyl group, a divalent group in which a plurality of benzene rings are bonded in a chain or branched manner, a divalent group in which one or more benzene rings and at least one naphthalene ring are bonded in a chain or branched manner, a divalent group in which one or more benzene rings and at least one phenanthrene ring are bonded in a chain or branched manner, or a divalent group in which one or more benzene rings and at least one tetraphenylene ring are bonded in a chain or branched manner, and more preferably a divalent group in which a plurality of benzene rings are bonded in a chain or branched manner, and in any case, the order of bonding does not matter.

[0096] As described above, the number of benzene rings, naphthalene rings, phenanthrene rings, and tetraphenylene rings that are bonded together is usually 2 to 8, and preferably 2 to 5. Among these, preferred are a divalent structure in which 1 to 4 benzene rings are bonded together, a divalent structure in which 1 to 4 benzene rings and a naphthalene ring are bonded together, a divalent structure in which 1 to 4 benzene rings and a phenanthrene ring are bonded together, and a divalent structure in which 1 to 4 benzene rings and a tetraphenylene ring are bonded together.

[0097] These aromatic hydrocarbon groups may have a substituent. The substituents that the aromatic hydrocarbon groups may have are as described above. When the substituent is selected from the substituent group Z, the preferred substituents are the preferred substituents of the substituent group Z.

[0098] R １ , R ２ From the viewpoint of the solubility and durability of the compound, it is preferable that the compound has at least one partial structure selected from the following formulas (72-1) to (72-6).

[0099]

[0100] In each of the above formulas (72-1) to (72-6), * represents a bond to an adjacent structure or a hydrogen atom, and at least one of the two * represents a bonding position to an adjacent structure. In the following description, * has the same definition unless otherwise specified.

[0101] More preferably, R １ , R ２has at least one partial structure selected from formulas (72-1) to (72-4). １ , R ２ has at least one partial structure selected from formulas (72-1) to (72-3). Particularly preferably, R １ , R ２ has at least one partial structure selected from formulas (72-1) to (72-2).

[0102] Formula (72-2) is preferably the following formula (72-2-2).

[0103]

[0104] Formula (72-2) is more preferably formula (72-2-3) below.

[0105]

[0106] In addition, from the viewpoint of the solubility and durability of the compound, R １ , R ２ The partial structure preferably has includes a partial structure represented by formula (72-1) and a partial structure represented by formula (72-2).

[0107] (Substituent) R １ , R ２ However, the substituent that may be possessed is preferably a substituent selected from the aforementioned group of substituents Z or a crosslinking group selected from the aforementioned group of crosslinking groups T. A structure having no substituent is more preferred.

[0108] (a1, a2) a1 and a2 each independently represent 0 or 1.

[0109] (A １ , A ２ ) A １ , A ２ are each independently a hydrogen atom or a bridging group. １ , A ２ is a crosslinking group, it is preferably a crosslinking group selected from the group T of crosslinking groups. The number of crosslinking groups contained in the compounds represented by formulas (3-1) to (3-4) is preferably 1 or more and 5 or less, more preferably 2 or more and 4 or less.

[0110] (Specific Examples of Arylamine Compounds) Preferred specific examples of arylamine compounds are shown below, but the present invention is not limited to these.

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122] <Reasons why the compounds represented by formulas (3-1) to (3-4) are effective> The compounds represented by formulas (3-1) to (3-4) have an arylamine structure at the meta or ortho position of a phenyl or biphenyl group, and therefore have a larger band gap and a higher excited triplet energy level than compounds having an arylamine structure at the para position of a phenyl or biphenyl group. Furthermore, the compounds represented by formulas (3-1) to (3-4) have two or more arylamine structures, and therefore have excellent charge transport ability, particularly hole transport ability. Furthermore, the compounds represented by formulas (3-1) to (3-4) have an arylamine structure at the meta or ortho position of a phenyl or biphenyl group, and therefore can suppress intermolecular interactions and have higher solubility than compounds having an arylamine structure at the para position of a phenyl or biphenyl group, and can suppress crystal precipitation when made into a coating solution. In addition, since the compound of the present invention can suppress intermolecular interactions and has high solubility, it has good compatibility with the electron-accepting compound of the present invention, and an ionic compound between the counter anion of the electron-accepting ionic compound and the cation radical of the arylamine compound of the present invention is easily formed. For the above reasons, it is believed that an organic electroluminescent device exhibiting high luminous efficiency can be obtained by using the arylamine compound of the present invention and a composition of the arylamine compound and an electron-accepting compound of the present invention.

[0123] [Electron Accepting Compound] In order to improve hole injection from the anode to the hole injection layer or hole transport layer, or to improve charge transport within the hole injection layer or hole transport layer, the charge transport material contained in the hole injection layer or hole transport layer preferably contains a cation radical moiety. To convert the charge transport material into a cation radical, an electron accepting compound is used when forming the hole injection layer or hole transport layer. As the backbone of the electron accepting compound, an ionic compound consisting of a tetraarylborate ion, which is an anion with an ionic valence of 1 described below, and a counter cation is preferred because of its high stability.

[0124] (Conversion of Charge Transport Material into Cation Radicals) The conversion of a charge transport material into a cation radical is carried out as follows: When a compound having an amine structure is used as the charge transport material, and a tetraarylborate salt having diaryliodonium as a counter cation is used as the electron accepting compound, the counter cation can change from diaryliodonium to an ammonium cation as shown in the following formula during the formation of the hole injection layer or hole transport layer.

[0125]

[0126] (e.g., Ar, Ar １’ ~Ar ４’ are each independently an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or a monovalent group in which a plurality of structures selected from an aromatic hydrocarbon ring group which may have a substituent and an aromatic heterocyclic group which may have a substituent are linked together.

[0127] The ammonium cation produced by the above reaction has a half-occupied molecular orbital (SOMO) capable of accepting electrons, and therefore the tetraarylborate salt serving as the counter cation for the ammonium ion is an electron-accepting compound.

[0128] In the present invention, the compound comprising the cation of the charge transport material and the anion, tetraarylborate ion, is referred to as a charge transporting ionic compound, as will be described in detail later.

[0129] As described later, the hole injection layer and / or hole transport layer of the organic electroluminescent element of the present invention is preferably obtained by wet film formation of the composition for forming a charge transport film of the present invention, and the composition for forming a charge transport film of the present invention is preferably a composition obtained by a process of dissolving or dispersing an electron-accepting compound having a tetraarylborate ion structure described later and a charge transport material described later in an organic solvent. The charge transport layer of the organic electroluminescent element of the present invention preferably contains a charge transporting ionic compound having the tetraarylborate ion structure described later in the present invention as an anion and the cation of the charge transport material of the present invention as a counter cation.

[0130] (Crosslinking Reaction Product) When the charge transport material according to the present invention has a crosslinking group, the crosslinking reaction product with an electron accepting compound having a crosslinking group includes the following crosslinking reaction products: A compound in which electron accepting compounds are crosslinked with each other. A compound in which an electron accepting compound is crosslinked with a charge transport material. A compound in which an electron accepting compound is crosslinked with the tetraarylborate ion of the present invention. A compound in which tetraarylborate ions of the present invention are crosslinked with each other. A compound in which a tetraarylborate ion of the present invention is crosslinked with a charge transport material.

[0131] Here, the term "tetraarylborate ion in the present invention" includes a case where it exists as an electron-accepting compound, which is an ionic compound comprising a tetraarylborate ion and a counter cation, as described below, and a case where it exists as a charge-transporting ionic compound comprising a tetraarylborate ion and a cation of a charge-transporting material, as described below.

[0132] The two crosslinking groups that undergo a crosslinking reaction may be the same or different, as long as they are capable of crosslinking.

[0133] [Electron-Accepting Compound] The electron-accepting compound, which is an ionic compound comprising a tetraarylborate ion and a counter cation, is an electron-accepting ionic compound comprising a counter anion, which is a non-coordinating anion, represented by the following formula (81), and a counter cation. The following formula (81) has a tetraarylborate ion represented by the below-described formula (82) as an anion. The electron-accepting compound according to the present invention may be referred to as an electron-accepting ionic compound.

[0134]

[0135] (In formula (81), five R ８１ , the five Rs ８２ , the five Rs ８３ , the five Rs ８４ are independent of each other, and R ８１ ~R ８４are each independently a hydrogen atom, a deuterium atom, a halogen atom (I atom, Br atom, Cl atom, F atom), an aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 50 carbon atoms which may have a substituent, a fluorine-substituted alkyl group having 1 to 12 carbon atoms, or a bridging group. １ , Ph ２ , Ph ３ , Ph ４ is a symbol indicating each benzene ring. ＋ represents a counter cation.)

[0136] The electron-accepting compound represented by formula (81) preferably has a crosslinking group, and more preferably has two or more crosslinking groups. The crosslinking group is preferably present in the anion moiety of the electron-accepting compound represented by formula (81), i.e., in formula (82) described below, which is a tetraarylborate ion.

[0137] [Tetraarylborate ion] As the mother skeleton of the above-mentioned electron-accepting compound, an ionic compound consisting of a tetraarylborate ion, which is an anion having an ionic valence of one, in which four optionally substituted aromatic hydrocarbon rings or optionally substituted aromatic heterocycles are substituted on a boron atom, and a counter cation, is preferred because it has high stability.

[0138] The tetraarylborate ion is an anion of the formula (81) shown above, represented by the following formula (82).

[0139]

[0140] (In formula (82), R ８１ ~R ８４ are R in formula (81), respectively. ８１ ~R ８４ It is the same as １ ~Ph ４ are the Ph of formula (81), respectively. １ ~Ph ４ is the same as the symbol for four benzene rings.)

[0141] R ８１ ~R ８４The number of carbon atoms in the aromatic hydrocarbon group used is preferably 6 to 50. The aromatic hydrocarbon ring structure is preferably a monocyclic ring or 2 to 6 condensed rings, or a structure in which 2 to 8 of these are linked together. Specific examples of the aromatic hydrocarbon group include a monovalent group of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring, a triphenylene ring, an acenaphthene ring, a fluoranthene ring, a fluorene ring, a biphenyl structure, a terphenyl structure, or a quaterphenyl structure, and a monovalent group in which 2 to 8 of these are linked together.

[0142] R ８１ ~R ８４ The number of carbon atoms in the aromatic heterocyclic group used is preferably 3 to 50. The aromatic heterocyclic structure is preferably a single ring or 2 to 6 condensed rings, or a structure in which 2 to 8 of these are linked together. Specific examples of the aromatic heterocyclic group include a monovalent group of a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, an oxadiazole ring, an indole ring, a carbazole ring, a pyrroloimidazole ring, a pyrrolopyrazole ring, a pyrrolopyrrole ring, a thienopyrrole ring, a thienothiophene ring, a furopyrrole ring, a furofuran ring, a thienofuran ring, a benzisoxazole ring, a benzisothiazole ring, a benzimidazole ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinoxaline ring, a phenanthridine ring, a perimidine ring, a quinazoline ring, a quinazolinone ring, or an azulene ring, and a monovalent group of 2 to 8 of these linked together. Furthermore, the aromatic heterocyclic group referred to here may contain at least one of these independent structures, and may also contain an aromatic hydrocarbon ring structure as a connecting structure. When an aromatic hydrocarbon ring structure is contained, it may be a structure in which 2 to 8 of the aromatic heterocyclic rings and aromatic hydrocarbon rings are connected together. Here, the aromatic hydrocarbon ring may be any of the above-mentioned R ８１ ~R ８４ A single structure of the aromatic hydrocarbon ring used in the above can be used.

[0143] Among these, monovalent groups such as a monovalent group of a benzene ring, a naphthalene ring, a fluorene ring, a pyridine ring, or a carbazole ring, or a biphenyl group formed by linking 2 to 5 of these groups, are more preferred because of their excellent stability and heat resistance. Particularly preferred are monovalent groups of a benzene ring or groups formed by linking 2 to 5 benzene rings, and specific examples thereof include a phenyl group, a biphenyl group, and a terphenyl group.

[0144] The number of aromatic hydrocarbon groups and aromatic heterocyclic groups contained in a monovalent group in which a plurality of structures selected from aromatic hydrocarbon groups which may have a substituent and aromatic heterocyclic groups which may have a substituent are linked together is 2 or more and preferably 8 or less, more preferably 4 or less, and even more preferably 3 or less. However, when the aromatic hydrocarbon group is a biphenyl group, a terphenyl group, or a quaterphenyl group, it is considered to have a structure in which 2, 3, or 4 phenyl groups are linked together, respectively.

[0145] R ８１ ~R ８４ The substituent that may be possessed by is preferably a group selected from the above-mentioned group Z of substituents or a bridging group.

[0146] R ８１ ~R ８４ is preferably a fluorine atom or a fluorine-substituted alkyl group, since this increases the stability of the anion and improves the effect of stabilizing the cation. The compound preferably contains two or more fluorine atoms or fluorine-substituted alkyl groups, more preferably three or more fluorine atoms or fluorine-substituted alkyl groups, and most preferably four fluorine atoms or fluorine-substituted alkyl groups.

[0147] R ８１ ~R ８４The fluorine-substituted alkyl group used in is preferably a linear or branched alkyl group having 1 to 12 carbon atoms substituted with a fluorine atom, more preferably a perfluoroalkyl group, still more preferably a linear or branched perfluoroalkyl group having 1 to 5 carbon atoms, particularly preferably a linear or branched perfluoroalkyl group having 1 to 3 carbon atoms, and most preferably a perfluoromethyl group. The reason for this is that the charge injection layer containing the crosslinking reaction product of the electron-accepting compound having a crosslinking group and the coating film laminated thereon will be stable. The fluorine-substituted alkyl group is preferably bonded to the para-position of the boron atom.

[0148] The tetraarylborate ion is preferred because it further increases the stability of the anion and further improves the effect of stabilizing the cation. １ - (R ８１ ) ５ , *-Ph ２ - (R ８２ ) ５ , *-Ph ３ - (R ８３ ) ５ , *-Ph ４ - (R ８４ ) ５ , (* represents a bond to boron B in formula (82)), it is preferable that at least one of them is a group represented by the following formula (84) having four fluorine atoms, it is more preferable that at least two of them are the same group represented by formula (84) in terms of improving the stability of the anion, and it is most preferable that at least three of them are the same group represented by formula (84) in terms of further improving the stability of the anion.

[0149]

[0150] (In formula (84), * represents a bond with boron B in formula (82), and F ４ represents that four fluorine atoms are substituted, and R ８５ represents an aromatic hydrocarbon group which may have a substituent, or a crosslinking group.

[0151] R ８５The number of carbon atoms of the aromatic hydrocarbon group that can be used is preferably 3 to 40. The aromatic hydrocarbon ring structure is preferably a monocyclic ring or 2 to 6 fused rings, or a structure in which 2 to 5 of these are linked together. Specific examples include a single monovalent group of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring, a triphenylene ring, an acenaphthene ring, a fluoranthene ring, a fluorene ring, a biphenyl structure, a terphenyl structure, or a quaterphenyl structure, and a monovalent group in which 2 to 6 of these are linked together. The crosslinking group that the aromatic hydrocarbon group may have is a crosslinking group selected from the group T of crosslinking groups.

[0152] R ８５ The crosslinking group that can be used is preferably a crosslinking group selected from the crosslinking group group T. The aromatic hydrocarbon group and the substituent that the aromatic hydrocarbon group may have but is not a crosslinking group are preferably groups selected from the substituent group Z, and among them, aromatic hydrocarbon groups are preferred from the viewpoint of stability, and alkyl groups are preferred from the viewpoint of solubility.

[0153] <Ionic Compound Containing Tetraarylborate Ion> The tetraarylborate ion is used as an electron-accepting ionic compound containing a tetraarylborate ion.

[0154] (Counter Cation) The counter cation is preferably an iodonium cation, a sulfonium cation, a carbocation, an oxonium cation, an ammonium cation, a phosphonium cation, a cycloheptyltrienyl cation, or a ferrocenium cation having a transition metal, more preferably an iodonium cation, a sulfonium cation, a carbocation, or an ammonium cation, and particularly preferably an iodonium cation.

[0155] The iodonium cation is preferably a structure represented by the following formula (4), and the same also applies to more preferred structures.

[0156] Specific preferred iodonium cations include diphenyliodonium cation, bis(4-tert-butylphenyl)iodonium cation, 4-tert-butoxyphenylphenyliodonium cation, 4-methoxyphenylphenyliodonium cation, and 4-isopropylphenyl-4-methylphenyliodonium cation.

[0157] Specific preferred examples of the sulfonium cation include triphenylsulfonium cation, 4-hydroxyphenyldiphenylsulfonium cation, 4-cyclohexylphenyldiphenylsulfonium cation, 4-methanesulfonylphenyldiphenylsulfonium cation, (4-tert-butoxyphenyl)diphenylsulfonium cation, bis(4-tert-butoxyphenyl)phenylsulfonium cation, and 4-cyclohexylsulfonylphenyldiphenylsulfonium cation.

[0158] Specific examples of the carbocation include trisubstituted carbocations such as triphenyl carbocation, tri(methylphenyl) carbocation, and tri(dimethylphenyl) carbocation.

[0159] Specific examples of the ammonium cation include trialkylammonium cations such as trimethylammonium cation, triethylammonium cation, tripropylammonium cation, tributylammonium cation, and tri(n-butyl)ammonium cation; N,N-dialkylanilinium cations such as N,N-diethylanilinium cation and N,N-2,4,6-pentamethylanilinium cation; and dialkylammonium cations such as di(isopropyl)ammonium cation and dicyclohexylammonium cation.

[0160] Specific examples of the phosphonium cation include tetraarylphosphonium cations such as tetraphenylphosphonium cation, tetrakis(methylphenyl)phosphonium cation, and tetrakis(dimethylphenyl)phosphonium cation; and tetraalkylphosphonium cations such as tetrabutylphosphonium cation and tetrapropylphosphonium cation.

[0161] Among these, in terms of film stability of the compound, iodonium cation, carbocation and sulfonium cation are preferred, with iodonium cation being more preferred.

[0162] (X ＋ : iodonium cation) X which is a counter cation in the formula (81) ＋ is preferably an iodonium cation having the structure of the following formula (83):

[0163]

[0164] In formula (83), Ar ８１ , Ar ８２ are each independently an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent. The aromatic hydrocarbon group is preferably an aromatic hydrocarbon group having 6 to 18 carbon atoms, more preferably an aromatic hydrocarbon group having 6 to 12 carbon atoms, and most preferably a phenyl group. The substituent which may be possessed is a group selected from the aforementioned substituent group Z, of which an alkyl group is most preferred. Preferred examples of the aromatic hydrocarbon group include a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a naphthyl group, a phenanthrenyl group, a triphenylene group, and a naphthylphenyl group, with a phenyl group being most preferred from the viewpoint of the stability of the compound.

[0165] (Molecular Weight) The molecular weight of the electron-accepting compound of the present invention is usually 900 or more, preferably 1000 or more, more preferably 1200 or more, and usually 10000 or less, preferably 5000 or less, more preferably 3000 or less. If the molecular weight is too small, the delocalization of positive and negative charges will be insufficient, which may result in a decrease in electron-accepting ability, whereas if the molecular weight is too large, charge transport may be hindered.

[0166] Specific Examples Specific examples of the electron-accepting compound of the present invention represented by formula (81) are listed below, but the present invention is not limited to these.

[0167]

[0168]

[0169]

[0170] [Charge Transporting Polymer Compound] The composition of the present invention preferably contains a hole transporting polymer compound as the charge transporting polymer compound. The hole transporting polymer compound is usually used to form a hole injection layer or a hole transport layer, and is contained in the composition for forming a charge transport film described later. In this case, the composition of the present invention can be used to form a hole injection layer or a hole transport layer.

[0171] [Polymer Having an Arylamine Structure as a Repeating Unit] The hole transport polymer compound is preferably a polymer having an arylamine structure as a repeating unit, as shown below, and having a crosslinking group. The repeating unit of the arylamine structure of the polymer having an arylamine structure as a repeating unit is represented by the following formula (50):

[0172]

[0173] (In formula (50), Ar ５１ represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a group in which a plurality of groups selected from aromatic hydrocarbon groups and aromatic heterocyclic groups are linked together; ５２ represents a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group, or a divalent group in which a plurality of at least one group selected from the group consisting of the divalent aromatic hydrocarbon group and the divalent aromatic heterocyclic group is linked together directly or via a linking group. ５１ and Ar ５２ may form a ring via a single bond or a linking group. ５１ , Ar ５２ may have a substituent.)

[0174] Ar ５１ , Ar ５２The substituent which may be possessed by is preferably a substituent or a bridging group selected from the above-mentioned group Z of substituents.

[0175] Ar ５１ , Ar ５２ When has a crosslinking group, the crosslinking group is preferably a crosslinking group selected from the group T of crosslinking groups.

[0176] (Terminal Group) In this specification, the term "terminal group" refers to the structure of the terminal portion of a polymer formed by an endcapping agent used at the end of polymerization of the polymer. In the composition of the present invention, the terminal group of the polymer containing the repeating unit represented by formula (50) is preferably a hydrocarbon group. From the viewpoint of charge transportability, the hydrocarbon group is preferably a hydrocarbon group having 1 to 60 carbon atoms, more preferably a hydrocarbon group having 1 to 40 carbon atoms, and even more preferably a hydrocarbon group having 1 to 30 carbon atoms.

[0177] Examples of the hydrocarbon group include: a linear, branched, or cyclic alkyl group having usually 1 or more, preferably 4 or more, and usually 24 or less, preferably 12 or less carbon atoms, such as a methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group, or dodecyl group; a linear, branched, or cyclic alkenyl group having usually 2 or more and 24 or less, preferably 12 or less carbon atoms, such as a vinyl group; a linear or branched alkynyl group having usually 2 or more and 24 or less, preferably 12 or less carbon atoms, such as an ethynyl group; an aromatic hydrocarbon group having usually 6 or more and 36 or less, preferably 24 or less carbon atoms, such as a phenyl group or a naphthyl group; and a crosslinking group that is a hydrocarbon group selected from the group T of crosslinking groups, preferably a crosslinking group represented by any of the formulae (X1) to (X4).

[0178] These hydrocarbon groups may further have a substituent, and the optional substituent is preferably an alkyl group or an aromatic hydrocarbon group. When there are multiple optional substituents, they may be bonded to each other to form a ring. When these hydrocarbon groups are groups other than crosslinking groups, the substituents may further have a crosslinking group selected from the group T of crosslinking groups.

[0179] From the viewpoint of charge transport properties and durability, the terminal group is preferably an alkyl group, an aromatic hydrocarbon group, or a crosslinking group which is a hydrocarbon group selected from the group T of crosslinking groups, more preferably an aromatic hydrocarbon group. When the terminal group is not a crosslinking group, it is also preferable that the terminal group further has a crosslinking group selected from the group T of crosslinking groups.

[0180] (Ar ５２ ) Ar ５２ represents a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group, or a divalent group in which at least one group selected from the group consisting of the divalent aromatic hydrocarbon group and the divalent aromatic heterocyclic group is linked directly or via a linking group, and the aromatic hydrocarbon group and the aromatic heterocyclic group may have a substituent. The optional substituent is preferably a substituent or a bridging group selected from the substituent group Z. ５２ When has a crosslinking group, the crosslinking group is preferably a crosslinking group selected from the group T of crosslinking groups.

[0181] (Twisted Structure) The repeating unit represented by the formula (50) may have a partial structure represented by the following formula (63) as Ar ５２ It is preferable that the main chain has a twisted structure and inhibits conjugation.

[0182]

[0183] (In formula (63), R ６０１ represents an alkyl group which may have a substituent, and Ar ６２１ represents a divalent aromatic hydrocarbon group which may have a substituent, or a divalent aromatic heterocyclic group which may have a substituent; the ring Ar represents an aromatic hydrocarbon structure which may have a substituent, or a divalent aromatic heterocyclic structure which may have a substituent; and -* represents a bond to an adjacent atom.) In addition, Ar in the repeating unit of the arylamine structure represented by the formula (50) ５２ In this case, it does not matter whether it is on the left or right side of the formula (63). That is, the following formula (63') also has the same meaning as the formula (63).

[0184]

[0185] (Ar ５１) Ar ５１ represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a group in which a plurality of groups selected from aromatic hydrocarbon groups and aromatic heterocyclic groups are linked together, and the aromatic hydrocarbon group and the aromatic heterocyclic group may have a substituent. The optional substituent is preferably a substituent or a crosslinking group selected from the aforementioned group of substituents Z, and when a crosslinking group is present, the crosslinking group is preferably a crosslinking group selected from the aforementioned group of crosslinking groups T.

[0186] (Ar having a bridging group) ５１ Preferred structures of Ar ５１ When Ar has a bridging group, ５１ Ar preferably has a structure in which a crosslinking group selected from the group T of crosslinking groups is attached to the terminal of a monovalent group in which 2 to 5 benzene rings, each of which may have a substituent, are linked. ５１ More preferably, the structure has a crosslinking group selected from the group T of crosslinking groups at the end of a monovalent group in which 2 to 5 unsubstituted benzene rings are linked together.

[0187] <Preferred Ar ５１ > Ar ５１ is preferably an aromatic hydrocarbon group from the viewpoints of excellent charge transport properties and excellent durability, and among these, a benzene ring (phenyl group), a group in which 2 to 5 benzene rings are linked, or a monovalent group of a fluorene ring (fluorenyl group) is more preferred, a fluorenyl group is even more preferred, and a 2-fluorenyl group is particularly preferred. These may have a substituent. As the substituent, a group selected from the substituent group Z or a crosslinking group is preferred. When a crosslinking group is present, the crosslinking group is preferably a crosslinking group selected from the crosslinking group group T.

[0188] Ar ５１ The substituent that the aromatic hydrocarbon group and aromatic heterocyclic group may have is not particularly limited as long as it does not significantly impair the properties of the present polymer. The substituent is preferably a group selected from the substituent group Z described below, more preferably an alkyl group, an alkoxy group, an aromatic hydrocarbon group, or an aromatic heterocyclic group, and still more preferably an alkyl group.

[0189] Ar ５１From the viewpoint of solubility in a solvent, a fluorenyl group substituted with an alkyl group having 1 to 24 carbon atoms is preferred, and a 2-fluorenyl group substituted with an alkyl group having 4 to 12 carbon atoms is particularly preferred. Furthermore, a 9-alkyl-2-fluorenyl group in which the 9-position of the 2-fluorenyl group is substituted with an alkyl group is preferred, and a 9,9'-dialkyl-2-fluorenyl group substituted with two alkyl groups is particularly preferred.

[0190] The fluorenyl group substituted with an alkyl group at at least one of the 9- and 9'-positions tends to improve the solubility in solvents and the durability of the fluorene ring. Furthermore, the fluorenyl group substituted with an alkyl group at both the 9- and 9'-positions tends to further improve the solubility in solvents and the durability of the fluorene ring.

[0191] Also, Ar ５１ is also preferably a spirobifluorenyl group from the viewpoint of solubility in a solvent.

[0192] In addition, the polymer containing the repeating unit represented by the formula (50) may be a polymer containing the repeating unit represented by the formula (50) ５１ preferably contains a repeating unit which is a group represented by the following formula (51), a group represented by the following formula (52), or a group represented by the following formula (53).

[0193] <Group represented by formula (51)>

[0194]

[0195] (In formula (51), * represents a bond to a nitrogen atom of the main chain of formula (50), Ar ５３ , Ar ５４ each independently represents a divalent aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or a divalent group in which a plurality of aromatic hydrocarbon groups which may have a substituent or aromatic heterocyclic groups which may have a substituent are linked together directly or via a linking group, ５５represents an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or a monovalent group in which a plurality of aromatic hydrocarbon groups or aromatic heterocyclic groups which may have a substituent are linked together directly or via a linking group, ５６ represents a hydrogen atom or a substituent.

[0196] Here, each aromatic hydrocarbon group and each aromatic heterocyclic group may have a substituent. The optional substituent is preferably a group selected from the above-mentioned substituent group Z or a crosslinking group. When a crosslinking group is present, the crosslinking group is preferably a group selected from the above-mentioned crosslinking group group T.

[0197] (Ar ５３ ) Ar ５３ is preferably a group in which 1 to 6 divalent aromatic hydrocarbon groups are linked together, more preferably a group in which 2 to 4 divalent aromatic hydrocarbon groups are linked together, and among these, a group in which 1 to 4 phenylene rings are linked together is more preferred, and a biphenylene group in which 2 phenylene rings are linked together is particularly preferred.

[0198] These groups may have a substituent. The substituent that may be had is preferably a group selected from the above-mentioned group Z of substituents or a crosslinking group. When a crosslinking group is had, the crosslinking group is preferably a group selected from the above-mentioned group T of crosslinking groups. Preferably, Ar ５３ has no substituents or bridging groups.

[0199] Furthermore, when a plurality of these divalent aromatic hydrocarbon groups or divalent aromatic heterocyclic groups are linked, the group is preferably one in which the plurality of linked divalent aromatic hydrocarbon groups are bonded so as not to conjugate. Specifically, it preferably contains a 1,3-phenylene group or a group having a substituent and forming a twisted structure due to the steric effect of the substituent, and more preferably a 1,3-phenylene group having no substituent or crosslinking group or a group in which a plurality of 1,3-phenylene groups having no substituent or crosslinking group are linked.

[0200] (Ar ５４ ) Ar ５４In terms of excellent charge transport properties and durability, the divalent aromatic hydrocarbon group is preferably a group in which one or more divalent aromatic hydrocarbon groups, which may be the same or different, are linked together, and the divalent aromatic hydrocarbon group may have a substituent. When multiple groups are linked together, the number of linked groups is preferably 2 to 10, more preferably 6 or less, and particularly preferably 3 or less from the viewpoint of film stability. Preferred aromatic hydrocarbon ring structures are benzene rings, naphthalene rings, anthracene rings, and fluorene rings, and more preferably benzene rings and fluorene rings. Preferred groups in which multiple groups are linked together are groups in which 1 to 4 phenylene rings are linked together, or groups in which a phenylene ring and a fluorene ring are linked together. In terms of broadening the LUMO, a biphenylene group in which two phenylene rings are linked together is particularly preferred.

[0201] These groups may have a substituent. The substituent that may be had is preferably a group selected from the above-mentioned group Z of substituents or a crosslinking group. When a crosslinking group is had, the crosslinking group is preferably a group selected from the above-mentioned group T of crosslinking groups. More preferred substituents are a phenyl group, a naphthyl group, and a fluorenyl group. It is also preferable that the group has no substituent.

[0202] (Ar ５５ ) Ar ５５ is an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or a monovalent group in which a plurality of aromatic hydrocarbon groups or aromatic heterocyclic groups which may have a substituent are linked directly or via a linking group. Preferably, it is a monovalent aromatic hydrocarbon group or a group in which a plurality of monovalent aromatic hydrocarbon groups are linked.

[0203] These groups may have a substituent. The optional substituent is preferably a group selected from the above-mentioned group Z of substituents or a crosslinking group. When a crosslinking group is present, the crosslinking group is preferably a group selected from the above-mentioned group T of crosslinking groups.

[0204] When a plurality of these groups are linked together, it is preferably a divalent group in which 2 to 10 groups are linked together, and more preferably a monovalent group in which 2 to 5 groups are linked together. ５１ The same aromatic hydrocarbon groups and aromatic heterocyclic groups as those mentioned above can be used.

[0205] Ar ５５ It is preferable that the compound has a structure represented by any one of the following schemes 2A, 2B, and 2C.

[0206]

[0207]

[0208]

[0209] In the above Schemes 2A to 2C, "-*" represents Ar ５４ When there are multiple "-*", one of them is Ar ５４ These structures may have a substituent. The substituent that these structures may have is preferably a group selected from the group of substituents Z or a crosslinking group. When a crosslinking group is present, the crosslinking group is preferably a group selected from the group of crosslinking groups T.

[0210] (R ３１ and R ３２ ) R in Scheme 2A and 2B ３１ and R ３２ are each independently a linear, branched, or cyclic alkyl group which may have a substituent. The number of carbon atoms in the alkyl group is not particularly limited, but in order to maintain the solubility of the polymer, the number of carbon atoms is preferably 1 to 6, more preferably 3 or less, and further preferably a methyl group or an ethyl group.

[0211] R ３１ and R ３２ may be the same or different, but it is preferred that all R ３１ and R ３２ are preferably the same group.

[0212] (Ar ｄ１８ ) Ar in Scheme 2B ｄ１８ are each independently an aromatic hydrocarbon group or an aromatic heterocyclic group. ｄ１８is preferably an aromatic hydrocarbon group from the viewpoint of stability, and more preferably a phenyl group. These groups may further have a substituent or a crosslinking group. The substituent that may be had is preferably a group selected from the above-mentioned group Z of substituents or a crosslinking group. When a crosslinking group is present, the crosslinking group is preferably a group selected from the above-mentioned group T of crosslinking groups.

[0213] From the viewpoint of distributing the LUMO of the molecule, Ar ５５ As the structure, a structure selected from the above a-1 to a-4, b-1 to b-9, c-1 to c-4, d-1 to d-18, and e-1 to e-4 is preferred. Furthermore, from the viewpoint of promoting the broadening of the LUMO of the molecule by having an electron-withdrawing group, a structure selected from a-1 to a-4, b-1 to b-9, d-1 to d-12, d-17, d-18, and e-1 to e-4 is preferred. Furthermore, from the viewpoint of the effect of confining excitons formed in the light-emitting layer, which have a high triplet level, a structure selected from a-1 to a-4, d-1 to d-12, d-17, d-18, and e-1 to e-4 is preferred. From the viewpoints of easy synthesis and excellent stability, d-1, d-10, d-17, d-18 and e-1 are more preferable, and the benzene ring structure of d-1, the fluorene ring structure of d-6 or the carbazole structure of d-17 are particularly preferable.

[0214] Ar ５５ In the case of a fluorene structure represented by d-6, a 2-fluorenyl group is preferred. Furthermore, the 9- and 9'-positions may have substituents, and the substituents that may be had are preferably a group selected from the aforementioned group of substituents Z or a crosslinking group. In the case of a crosslinking group, the crosslinking group is preferably a group selected from the aforementioned group of crosslinking groups T. Among these, an alkyl group is preferred as the substituent.

[0215] (Ar ５６ ) Ar ５６ represents a hydrogen atom or a substituent. ５６ When Ar is a substituent, it is not particularly limited, but is preferably an aromatic hydrocarbon group, an aromatic heterocyclic group, or a bridging group, and in the case of an aromatic hydrocarbon group or an aromatic heterocyclic group, it may further have a substituent selected from the substituent group Z or a bridging group. ５６ When is a crosslinking group, it is preferably a crosslinking group selected from the group T of crosslinking groups.

[0216] Ar ５６ is a substituent, in formula (51), Ar ５６ From the viewpoint of improving durability, it is preferable that Ar is bonded to the 3-position of the carbazole structure to which Ar is bonded. ５６ is preferably a hydrogen atom from the viewpoint of ease of synthesis and charge transport properties. ５６ From the viewpoint of improving durability and charge transport properties, is preferably an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent, and more preferably an aromatic hydrocarbon group which may have a substituent.

[0217] Ar ５６ is preferably a hydrogen atom from the viewpoint of ease of synthesis and charge transport properties.

[0218] (Specific Examples of Groups Represented by Formula (51)) Specific examples of groups represented by formula (51) are listed below, but the groups represented by formula (51) are not limited to these.

[0219]

[0220] <Group represented by formula (52)>

[0221]

[0222] (In formula (52), Ar ６１ and Ar ６２ are each independently a divalent aromatic hydrocarbon group which may have a substituent, a divalent aromatic heterocyclic group which may have a substituent, or a divalent group in which a plurality of aromatic hydrocarbon groups which may have a substituent or aromatic heterocyclic groups which may have a substituent are linked together directly or via a linking group, and Ar ６３ ~Ar ６５ are each independently a hydrogen atom or a substituent. * represents the bonding position to the nitrogen atom of the main chain in formula (50).

[0223] Substituents which each aromatic hydrocarbon group may have, substituents which each aromatic heterocyclic group may have, and Ar when it is a substituent ６３ ~Ar ６５is preferably a group or a bridging group selected from the above-mentioned substituent group Z. The bridging group which each aromatic hydrocarbon group may have, the bridging group which each aromatic heterocyclic group may have, and Ar when it is a bridging group are ６３ ~Ar ６５ is preferably a group selected from the group T of crosslinking groups.

[0224] (Ar ６３ ~Ar ６５ ) Ar ６３ ~Ar ６５ are each independently the Ar ５６ Ar ６３ ~Ar ６５ is preferably a hydrogen atom.

[0225] (Ar ６２ ) Ar ６２ is a divalent aromatic hydrocarbon group which may have a substituent, a divalent aromatic heterocyclic group which may have a substituent, or a divalent group in which a plurality of aromatic hydrocarbon groups which may have a substituent or aromatic heterocyclic groups which may have a substituent are linked directly or via a linking group. Preferably, it is a divalent aromatic hydrocarbon group which may have a substituent or a group in which a plurality of divalent aromatic hydrocarbon groups which may have a substituent are linked. Here, the substituents which the aromatic hydrocarbon group may have and the substituents which the aromatic heterocyclic group may have are preferably the same groups as those in the substituent group Z or crosslinking groups. As a crosslinking group in which a crosslinking group is preferred, a group selected from the crosslinking group group T is preferred.

[0226] Ar ６２ The specific structure of Ar ５４ is the same as:

[0227] Ar ６２Specific preferred groups are divalent groups of a benzene ring, a naphthalene ring, an anthracene ring, or a fluorene ring, or a group in which multiple such groups are linked together, more preferably a divalent group of a benzene ring or a group in which multiple such groups are linked together, particularly preferably a 1,4-phenylene group in which benzene rings are linked together at the 1- and 4-positions, a 2,7-fluorenylene group in which fluorene rings are linked together at the 2- and 7-positions, or a group in which multiple such groups are linked together, and most preferably a group containing "1,4-phenylene group-2,7-fluorenylene group-1,4-phenylene group-".

[0228] Ar ６２ In these preferred structures, the phenylene group does not have a substituent or a bridging group other than at the linking position, which is advantageous in that the steric effect of the substituents on Ar ６２ This is preferred because it does not cause twisting. Furthermore, it is preferred that the fluorenylene group has substituents at the 9,9' positions from the viewpoint of improving solubility and durability of the fluorene structure. The substituent is preferably a substituent or a crosslinking group selected from the above-mentioned substituent group Z, and among these, an alkyl group is more preferred. These substituents may be further substituted with a crosslinking group. The crosslinking group is preferably a crosslinking group selected from the above-mentioned crosslinking group group T. Preferably, it is a substituent selected from the substituent group Z.

[0229] (Ar ６１ ) Ar ６１ is the Ar ５３ The groups are the same as those shown above, and the preferred structures are also the same.

[0230] (Specific Examples of Groups Represented by Formula (52)) Specific examples of groups represented by formula (52) are listed below, but the groups represented by formula (52) are not limited to these.

[0231]

[0232] <Group represented by formula (53)>

[0233]

[0234] (In formula (53), * represents a bond to the nitrogen atom of the main chain of formula (50), Ar ７１ represents a divalent aromatic hydrocarbon group, ７２ and Ar ７３each independently represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a monovalent group in which two or more groups selected from aromatic hydrocarbon groups and aromatic heterocyclic groups are linked together directly or via a linking group, and these groups may have a substituent; ring HA is an aromatic heterocycle containing a nitrogen atom; X ２ , Y ２ each independently represents a carbon atom or a nitrogen atom; X ２ and Y ２ When at least one of is a carbon atom, the carbon atom may have a substituent.)

[0235] The optional substituent is preferably a group or a crosslinking group selected from the group Z of substituents. When a crosslinking group is present, the crosslinking group is preferably a group selected from the group T of crosslinking groups.

[0236] <Ar ７１ > Ar ７１ is the Ar ５３ is a group similar to

[0237] Ar ７１ As the alkyl group, a group in which 2 to 6 benzene rings which may have a substituent are linked is particularly preferred, and a quaterphenylene group in which 4 benzene rings which may have a substituent are linked is most preferred.

[0238] Also, Ar ７１ preferably contains at least one benzene ring linked at the 1,3-position, which is a non-conjugated moiety, and more preferably contains two or more.

[0239] Ar ７１ In the case where a plurality of divalent aromatic hydrocarbon groups which may have a substituent are linked together, it is preferred that all of them are linked together by direct bonding from the viewpoint of charge transport properties or durability.

[0240] For this reason, Ar ７１Preferred structures linking the nitrogen atom in the main chain of the polymer and the ring HA in formula (53) are as shown in Scheme 2-1 and Scheme 2-2 below. "-*" represents the bonding site with the nitrogen atom in the main chain of the polymer or the ring HA in formula (53). Either of the two "-*"s may be bonded to the nitrogen atom in the main chain of the polymer or to the ring HA.

[0241]

[0242] Ar ７１ As the substituent that Ar may have, any one of the substituents in the above-mentioned group Z or a combination thereof can be used. ７１ The preferred range of the substituents that may be possessed by Ar is the same as that of the above-mentioned Ar ５３ is the same as the substituent that may be possessed when it is an aromatic hydrocarbon group.

[0243] <X ２ and Y ２ > X ２ and Y ２ each independently represents a C (carbon) atom or an N (nitrogen) atom. ２ and Y ２ When at least one of the groups is a carbon atom, it may have a substituent.

[0244] From the viewpoint of making it easier to localize LUMO around the ring HA, X ２ and Y ２ are preferably all N atoms.

[0245] X ２ and Y ２ When at least one of X is a C atom, the substituent that may be present may be any one of the substituents in the above-mentioned group Z or a combination thereof. ２ and Y ２ More preferably, has no substituent.

[0246] <Ar ７２ and Ar ７３ > Ar ７２ and Ar ７３are each independently an aromatic hydrocarbon group, an aromatic heterocyclic group, or a monovalent group in which two or more groups selected from aromatic hydrocarbon groups and aromatic heterocyclic groups are linked together directly or via a linking group. These groups may have a substituent, and the optional substituent is preferably a group selected from the aforementioned group Z of substituents or a crosslinking group. When a crosslinking group is present, the crosslinking group is preferably a group selected from the aforementioned group T of crosslinking groups.

[0247] From the viewpoint of distributing the LUMO of the molecule, Ar ７２ and Ar ７３ are preferably each independently a structure selected from a-1 to a-4, b-1 to b-9, c-1 to c-4, d-1 to d-16, and e-1 to e-4 shown in Schemes 2A to 2C. Furthermore, from the viewpoint of promoting the broadening of the LUMO of the molecule by having an electron-withdrawing group, a structure selected from a-1 to a-4, b-1 to b-9, c-1 to c-4, d-1 to d-12, and e-1 to e-4 is preferred. Furthermore, from the viewpoint of the effect of confining excitons formed in the light-emitting layer with a high triplet level, a structure selected from a-1 to a-4, d-1 to d-12, and e-1 to e-4 is preferred. In order to prevent molecular aggregation, a structure selected from d-1 to d-12 and e-1 to e-4 is more preferred. From the viewpoint of easy synthesis and excellent stability, Ar ７２ = Ar ７３ = d-1 or d-10 is preferred, and the benzene ring structure of d-1 is particularly preferred. These structures may also have a substituent.

[0248] (Specific Examples of Groups Represented by Formula (53)) Specific examples of groups represented by formula (53) are listed below, but the groups represented by formula (53) are not limited to these.

[0249]

[0250] (Preferred repeating unit represented by formula (50)) The repeating unit represented by formula (50) is preferably a repeating unit selected from the group consisting of a repeating unit represented by formula (54), a repeating unit represented by formula (55), a repeating unit represented by formula (56), a repeating unit represented by formula (57), and a repeating unit represented by formula (60). It is more preferable that the repeating unit represented by formula (50) is a repeating unit represented by formula (54).

[0251] <Repeating unit represented by formula (54)>

[0252]

[0253] (In formula (54), Ar ５１ represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a group in which a plurality of groups selected from aromatic hydrocarbon groups and aromatic heterocyclic groups are linked together; X represents —C(R ２０７ ) (R ２０８ ) -, -N(R ２０９ ) - or -C(R ２１１ ) (R ２１２ )-C(R ２１３ ) (R ２１４ )- and R ２０１ , R ２０２ , R ２２１ and R ２２２ each independently represents an alkyl group which may have a substituent, and R ２０７ ~R ２０９ and R ２１１ ~R ２１４ are each independently a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent; a and b are each independently an integer of 0 to 4; c is an integer of 0 to 3; d is an integer of 0 to 4; and i and j are each independently an integer of 0 to 3.

[0254] (R ２０１ , R ２０２ , R ２２１ , R ２２２ R in the repeating unit represented by the above formula (54) ２０１ , R ２０２ , R２２１ and R ２２２ R are each independently an alkyl group which may have a substituent. ２０１ , R ２０２ , R ２２１ and R ２２２ It is preferred that the group has no substituent.

[0255] The alkyl group is a linear, branched, or cyclic alkyl group. The number of carbon atoms in the alkyl group is not particularly limited, but in order to maintain the solubility of the polymer, it is preferably 1 or more, and is preferably 8 or less, more preferably 6 or less, and even more preferably 3 or less. The alkyl group is more preferably a methyl group or an ethyl group.

[0256] R ２０１ If there are multiple R ２０１ may be the same or different, R ２０２ If there are multiple R ２０２ may be the same or different. Since the charge can be uniformly distributed around the nitrogen atom and synthesis is easy, all of the R ２０１ and R ２０２ are preferably the same groups.

[0257] R ２２１ If there are multiple R ２２１ may be the same or different, R ２２２ If there are multiple R ２２２ may be the same or different. For ease of synthesis, all R ２２１ and R ２２２ are preferably the same groups.

[0258] (R ２０７ ~R ２０９ and R ２１１ ~R ２１４ ) R ２０７ ~R ２０９ and R ２１１ ~R ２１４ R are each independently a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. ２０７ ~R ２０９and R ２１１ ~R ２１４ It is preferred that the group has no substituent.

[0259] The alkyl group is not particularly limited, but since this tends to improve the solubility of the polymer, the number of carbon atoms is preferably 1 or more and is preferably 24 or less, more preferably 8 or less, and even more preferably 6 or less. The alkyl group may have a linear, branched, or cyclic structure.

[0260] Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a tert-butyl group, an n-hexyl group, an n-octyl group, a cyclohexyl group, and a dodecyl group.

[0261] The aralkyl group is not particularly limited, but preferably has 5 or more carbon atoms, and preferably 60 or less, more preferably 40 or less, since this tends to improve the solubility of the polymer.

[0262] Specific examples of the aralkyl group include a 1,1-dimethyl-1-phenylmethyl group, a 1,1-di(n-butyl)-1-phenylmethyl group, a 1,1-di(n-hexyl)-1-phenylmethyl group, a 1,1-di(n-octyl)-1-phenylmethyl group, a phenylmethyl group, a phenylethyl group, a 3-phenyl-1-propyl group, a 4-phenyl-1-n-butyl group, a 1-methyl-1-phenylethyl group, a 5-phenyl-1-n-propyl group, a 6-phenyl-1-n-hexyl group, a 6-naphthyl-1-n-hexyl group, a 7-phenyl-1-n-heptyl group, an 8-phenyl-1-n-octyl group, and a 4-phenylcyclohexyl group.

[0263] The aromatic hydrocarbon group is not particularly limited, but preferably has 6 or more carbon atoms, and preferably 60 or less, more preferably 30 or less, since this tends to improve the solubility of the polymer.

[0264] Specific examples of the aromatic hydrocarbon group include monovalent groups of 6-membered monocyclic rings or 2 to 5 condensed rings such as a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring, a triphenylene ring, an acenaphthene ring, a fluoranthene ring, and a fluorene ring, or groups in which a plurality of these rings are linked together.

[0265] From the viewpoint of improving charge transportability and durability, R ２０７ and R ２０８ is preferably a methyl group or an aromatic hydrocarbon group, and R ２０７ and R ２０８ is more preferably a methyl group, and R ２０９ is more preferably a phenyl group.

[0266] R ２０１ , R ２０２ , R ２２１ , R ２２２ an alkyl group of R ２０７ ~R ２０９ and R ２１１ ~R ２１４ The alkyl group, aralkyl group and aromatic hydrocarbon group may have a substituent. ２０７ ~R ２０９ and R ２１１ ~R ２１４ Examples of the crosslinking group include those groups listed as preferred groups of the alkyl group, aralkyl group and aromatic hydrocarbon group in the above formula (1) or crosslinking groups. Examples of the crosslinking group include crosslinking groups selected from the group T of crosslinking groups.

[0267] R ２０１ , R ２０２ , R ２２１ , R ２２２ an alkyl group of R ２０７ ~R ２０９ and R ２１１ ~R ２１４ From the viewpoint of reducing the voltage, it is most preferable that the alkyl group, aralkyl group and aromatic hydrocarbon group have no substituent.

[0268] When a crosslinking group is bonded to the main chain structure of the repeating unit represented by formula (54), the crosslinking group is an alkyl group, an aralkyl group, or an aromatic hydrocarbon group, and R ２０７ ~R２０９ , R ２１１ ~R ２１３ , or R ２１４ It is preferred that the hydroxyl group is bonded to the hydroxyl group.

[0269] (a, b, c, and d) In the repeating unit represented by the above formula (54), a and b are each independently an integer of 0 to 4. It is preferable that a+b is 1 or greater, and it is further preferable that a and b are each 2 or less, and it is more preferable that both a and b are 1. Here, when b is 1 or greater, d is also 1 or greater. Furthermore, when c is 2 or greater, multiple a's may be the same or different, and when d is 2 or greater, multiple b's may be the same or different.

[0270] When a+b is 1 or more, the aromatic rings of the main chain are twisted due to steric hindrance, the solubility of the polymer in a solvent is excellent, and the coating film formed by a wet film-forming method and heat-treated tends to be excellent insolubility in a solvent. Therefore, when a+b is 1 or more, when another organic layer (e.g., a light-emitting layer) is formed on this coating film by a wet film-forming method, the elution of the polymer into the composition for forming the other organic layer containing an organic solvent is suppressed.

[0271] In the repeating unit represented by the above formula (54), c is an integer of 0 to 3, and d is an integer of 0 to 4. It is preferable that c and d are each 2 or less, more preferably c and d are equal, and particularly preferably that both c and d are 1 or both c and d are 2.

[0272] In the repeating unit represented by the above formula (54), when both c and d are 1 or both c and d are 2 and both a and b are 2 or 1, R ２０１ and R ２０２ are most preferably bonded at positions symmetrical to each other.

[0273] Here, R ２０１ and R ２０２ and are bonded at positions symmetrical to each other means that R ２０１ and R ２０２In this case, a 180-degree rotation around the main chain is considered to be the same structure.

[0274] R ２２１ and R ２２２ When present, each of R is preferably independently located at the 1st, 3rd, 6th, or 8th position relative to the carbon atom of the benzene ring to which X is bonded. ２２１ and / or R ２２２ The existence of R ２２１ and / or R ２２２ is bonded to a fused ring and the adjacent benzene ring on the main chain are twisted due to steric hindrance, and the polymer has excellent solubility in solvents, and a coating film formed by a wet film-forming method and heat-treated tends to have excellent insolubility in solvents, which is preferable.

[0275] (i, j) In the repeating unit represented by the above formula (54), i and j are each independently an integer of 0 to 3. i and j are each independently preferably an integer of 0 to 2, more preferably 0 or 1. i and j are preferably the same integer. i and j are preferably 1 or 2 in order to twist the main chain of the polymer, and R ２２１ and / or R ２２２ is preferably bonded to the 1st and / or 3rd positions of the benzene ring. From the viewpoint of ease of synthesis, it is preferable that i and j are 0. The bonding position of the benzene ring is the carbon atom adjacent to the carbon atom to which X is bonded, and R ２２１ or R ２２２ The carbon atom to which the bond can be made is the first position, and the carbon atom that is bonded to the adjacent structure as the main chain is the second position.

[0276] (X) In the above formula (54), X is —C(R ２０７ ) (R ２０８ )- or -N(R ２０９ )-, and —C(R ２０７ ) (R ２０８ )- is more preferred.

[0277] (Preferred Repeating Unit) The repeating unit represented by the above formula (54) is particularly preferably a repeating unit represented by any one of the following formulae (54-1) to (54-8).

[0278]

[0279]

[0280] In the above formula, R ２０１ and R ２０２ are identical, and R ２０１ and R ２０２ are bonded at symmetric positions to each other.

[0281] <Preferred Examples of the Main Chain of the Repeating Unit Represented by Formula (54)> The main chain structure excluding the nitrogen atom in the above formula (54) is not particularly limited, but for example, the following structures are preferred.

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290] <Repeating unit represented by formula (55)>

[0291]

[0292] (In formula (55), Ar ５１ is Ar in the formula (54). ５１ is the same as R ３０３ and R ３０６ are each independently an alkyl group which may have a substituent, and R ３０４ and R ３０５are each independently an alkyl group which may have a substituent, an alkoxy group which may have a substituent, or an aralkyl group which may have a substituent, l is 0 or 1, m is 1 or 2, n is 0 or 1, p is 0 or 1, and q is 0 or 1.

[0293] (R ３０３ , R ３０６ R in the repeating unit represented by the above formula (55) ３０３ and R ３０６ are each independently an alkyl group which may have a substituent.

[0294] The alkyl group is R ２０１ and R ２０２ The substituents that may be possessed and preferred structures are the same as those of R ２０１ and R ２０２ The same can be mentioned.

[0295] R ３０３ If there are multiple R ３０３ may be the same or different, R ３０６ If there are multiple R ３０６ may be the same or different.

[0296] (R ３０４ , R ３０５ R in the repeating unit represented by the above formula (55) ３０４ and R ３０５ R are each independently an alkyl group which may have a substituent, an alkoxy group which may have a substituent, or an aralkyl group which may have a substituent. An alkyl group which may have a substituent is preferred. ３０４ and R ３０４ are preferably the same.

[0297] The alkyl group is a linear, branched, or cyclic alkyl group. The number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 or more, and is preferably 24 or less, more preferably 8 or less, and even more preferably 6 or less, since this tends to improve the solubility of the polymer.

[0298] Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a tert-butyl group, an n-hexyl group, an n-octyl group, a cyclohexyl group, and a dodecyl group.

[0299] The alkoxy group is not particularly limited, and may be an alkoxy group (—OR １０ ) R １０ The alkyl group represented by the formula (I) may have any of a linear, branched, or cyclic structure, and since this tends to improve the solubility of the polymer, the number of carbon atoms is preferably 1 or more, and is preferably 24 or less, and more preferably 12 or less.

[0300] Specific examples of the alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, a hexyloxy group, a 1-methylpentyloxy group, and a cyclohexyloxy group.

[0301] The aralkyl group is not particularly limited, but preferably has 5 or more carbon atoms, and preferably 60 or less, more preferably 40 or less, since this tends to improve the solubility of the polymer.

[0302] Specific examples of the aralkyl group include a 1,1-dimethyl-1-phenylmethyl group, a 1,1-di(n-butyl)-1-phenylmethyl group, a 1,1-di(n-hexyl)-1-phenylmethyl group, a 1,1-di(n-octyl)-1-phenylmethyl group, a phenylmethyl group, a phenylethyl group, a 3-phenyl-1-propyl group, a 4-phenyl-1-n-butyl group, a 1-methyl-1-phenylethyl group, a 5-phenyl-1-n-propyl group, a 6-phenyl-1-n-hexyl group, a 6-naphthyl-1-n-hexyl group, a 7-phenyl-1-n-heptyl group, an 8-phenyl-1-n-octyl group, and a 4-phenylcyclohexyl group.

[0303] R ３０４ , R ３０５ The substituents that the alkyl group, alkoxy group, and aralkyl group may have are the same as those of the R ２０７ ~R ２０９ and R ２１１ ~R ２１４Examples of the crosslinking group include those groups listed as preferred groups of the alkyl group, aralkyl group and aromatic hydrocarbon group in the above formula (1) or crosslinking groups. Examples of the crosslinking group include crosslinking groups selected from the group T of crosslinking groups.

[0304] R ３０４ , R ３０５ From the viewpoint of reducing voltage, it is most preferable that the alkyl group, alkoxy group and aralkyl group have no substituent.

[0305] When a crosslinking group is bonded to the main chain structure of the repeating unit represented by formula (55), the crosslinking group is R ３０４ and R ３０５ It is preferred that the hydroxyl group is bonded to the hydroxyl group.

[0306] (l, m and n) l represents 0 or 1, and n represents 0 or 1.

[0307] l and n are each independent, and l+n is preferably 1 or more, more preferably 1 or 2, and even more preferably 2. When l+n is within the above range, the solubility of the polymer tends to be increased, and precipitation from the composition of the present invention containing the polymer also tends to be suppressed.

[0308] m represents 1 or 2, and is preferably 1 because the organic electroluminescent device produced using the composition of the present invention can be driven at a low voltage and tends to have improved hole injection ability, transport ability, and durability.

[0309] (p and q) p represents 0 or 1, and q represents 0 or 1. When l = n = 1, p and q cannot be 0 at the same time. When p and q are not 0 at the same time, the solubility of the polymer is increased, and precipitation from the composition of the present invention containing the polymer tends to be suppressed. Furthermore, for the same reasons as in a and b above, when p + q is 1 or more, the aromatic rings of the main chain are twisted due to steric hindrance, and the polymer has excellent solubility in solvents, and a coating film formed by a wet film-forming method and heat-treated tends to have excellent insolubility in solvents. Therefore, when p + q is 1 or more, when another organic layer (e.g., a light-emitting layer) is formed on this coating film by a wet film-forming method, elution of the polymer into the composition for forming the other organic layer containing an organic solvent is suppressed.

[0310] <Specific Examples of Main Chain of Repeating Unit Represented by Formula (55)> The main chain structure excluding the nitrogen atom in formula (55) is not particularly limited, but examples thereof include the following structures.

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318] <Repeating unit represented by formula (56)>

[0319]

[0320] (In formula (56), Ar ５１ is Ar in the formula (54). ５１ and Ar ４１ is a divalent aromatic hydrocarbon group which may have a substituent, a divalent aromatic heterocyclic group which may have a substituent, or a divalent group in which a plurality of at least one group selected from the group consisting of the divalent aromatic hydrocarbon group and the divalent aromatic heterocyclic group is linked together directly or via a linking group, and R ４４１ and R ４４２ are each independently an alkyl group which may have a substituent, t is 1 or 2, u is 0 or 1, and r and s are each independently an integer of 0 to 4.

[0321] (R ４４１ , R ４４２ R in the repeating unit represented by the above formula (56) ４４１ , R ４４２ are each independently an alkyl group which may have a substituent.

[0322] The alkyl group is a linear, branched, or cyclic alkyl group. The number of carbon atoms in the alkyl group is not particularly limited, but in order to maintain the solubility of the polymer, the number of carbon atoms is preferably 1 or more, and is preferably 10 or less, more preferably 8 or less, and even more preferably 6 or less. The alkyl group is more preferably a methyl group or a hexyl group.

[0323] R ４４１ and R ４４２ When there are a plurality of R ４４１ and R ４４２ may be the same or different.

[0324] (r, s, t, and u) In the repeating unit represented by formula (56), r and s each independently represent an integer of 0 to 4. When t is 2, the multiple r's may be the same or different. It is preferable that r+s is 1 or greater, and it is further preferable that r and s are each 2 or less. When r+s is 1 or greater, it is believed that the driving life of the organic electroluminescent device will be further extended for the same reasons as for a and b in formula (54).

[0325] In the repeating unit represented by the above formula (56), t is 1 or 2, and u is 0 or 1. t is preferably 1, and u is preferably 1.

[0326] (Ar ４１ ) Ar ４１ is a divalent aromatic hydrocarbon group which may have a substituent, a divalent aromatic heterocyclic group which may have a substituent, or a divalent group in which a plurality of at least one group selected from the group consisting of the divalent aromatic hydrocarbon group and the divalent aromatic heterocyclic group is linked together directly or via a linking group.

[0327] Ar ４１ The aromatic hydrocarbon group in the formula (50) is preferably Ar ５２ The aromatic hydrocarbon group and the substituents which the aromatic hydrocarbon group may have are preferably groups selected from the substituent group Z, and the substituents which the aromatic hydrocarbon group may further have are preferably the same as those in the substituent group Z.

[0328] <Repeating unit represented by formula (57)>

[0329]

[0330] (In formula (57), Ar ５１ is Ar in the formula (54). ５１ is the same as R ５１７ ~R ５１９ each independently represents an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an aralkyl group which may have a substituent, an aromatic hydrocarbon group which may have a substituent, or an aromatic heterocyclic group which may have a substituent; f, g, and h each independently represent an integer of 0 to 4; and e represents an integer of 0 to 3, with the proviso that when g is 1 or greater, e is 1 or greater.

[0331] (R ５１７ ~R ５１９ ) R ５１７ ~R ５１９ The aromatic hydrocarbon group and aromatic heterocyclic group in each of the Ar ５１ The substituents which these groups may have are preferably the substituent group Z or crosslinking groups, and the crosslinking groups are preferably crosslinking groups selected from the crosslinking group T.

[0332] R ５１７ ~R ５１９ The alkyl group and aralkyl group in ２０７ The same groups as those listed in the above are preferred, and the substituents that may further be contained are the same as those listed in the above R ２０７ Groups similar to the following are preferred.

[0333] R ５１７ ~R ５１９ The alkoxy group in the formula (I) is preferably an alkoxy group exemplified in the above-mentioned group Z of substituents, and the substituent that may further be possessed is preferably an alkoxy group exemplified in the above-mentioned group Z of substituents.

[0334] (f, g, h) f, g, and h each independently represent an integer of 0 to 4. When e is 2 or greater, multiple g's may be the same or different. It is preferable that f + g + h is 1 or greater. It is preferable that f + h is 1 or greater, more preferably that f + h is 1 or greater and f, g, and h are 2 or less, even more preferably that f + h is 1 or greater and f and h are 1 or less, and most preferably that both f and h are 1.

[0335] When f and h are both 1, R ５１７ and R ５１９ are preferably bonded at positions symmetrical to each other. ５１７ and R ５１９ are preferably the same as

[0336] More preferably, g is 2. When g is 2, two R ５１８ are most preferably bonded to each other at the para position, and when g is 2, two R ５１８ are most preferably the same.

[0337] Here, R ５１７ and R ５１９ are bonded at positions symmetrical to each other, the bond positions are as follows: However, for the purposes of notation, structures rotated 180 degrees around the main chain axis are considered to have the same structure.

[0338]

[0339] When the polymer of this embodiment contains repeating units represented by formula (54) and repeating units represented by formula (57), the ratio of repeating units represented by formula (54) to repeating units represented by formula (57), i.e., (number of moles of repeating units represented by formula (57)) / (number of moles of repeating units represented by formula (54)), is preferably 0.1 or more, more preferably 0.3 or more, even more preferably 0.5 or more, even more preferably 0.9 or more, and particularly preferably 1.0 or more. Furthermore, this ratio is preferably 2.0 or less, more preferably 1.5 or less, and even more preferably 1.2 or less.

[0340] The repeating unit represented by the formula (57) is preferably a repeating unit represented by the following formula (58).

[0341]

[0342] In the case of the repeating unit represented by the formula (58), it is preferable that g=0 or 2. When g=2, the bonding positions are the 2-position and the 5-position. When g=0, that is, R ５１８ When there is no steric hindrance due to g=2 and the bonding positions are 2 and 5, that is, when there is no steric hindrance due to two R ５１８ When the bonded benzene ring is diagonal to the ５１７ and R ５１９ and can be bonded at positions symmetrical to each other.

[0343] Furthermore, the repeating unit represented by the formula (58) is more preferably a repeating unit represented by the following formula (59) in which e=3.

[0344]

[0345] In the case of the repeating unit represented by the formula (59), it is preferable that g=0 or 2. When g=2, the bonding positions are the 2-position and the 5-position. When g=0, that is, R ５１８ When there is no steric hindrance due to g = 2 and the bonding positions are 2 and 5, that is, when there is no steric hindrance due to two R ５１８ When the bonded benzene ring is diagonal to the ５１７ and R ５１９ and can be bonded at positions symmetrical to each other.

[0346] <Specific Examples of Main Chain of Repeating Unit Represented by Formula (57)> The main chain structure of the repeating unit represented by formula (57) is not particularly limited, but examples thereof include the following structures.

[0347]

[0348] The repeating units represented by the above formulas (50) to (59) preferably do not have a crosslinking group. When a crosslinking group is not present, polymer chain distortion is less likely to occur upon heat drying or baking (heat baking) after wet film formation, which is preferable. This is because a volume change may occur when the crosslinking group reacts, resulting in polymer chain distortion. Furthermore, polymer chain distortion may occur even when no volume change occurs.

[0349] <Repeating unit represented by formula (60)>

[0350] (In formula (60), Ar ５１ is Ar in the formula (50). ５１ and n ６０ represents an integer of 1 to 5.)

[0351] (n ６０ ) n ６０ represents an integer of 1 to 5, preferably an integer of 1 to 4, and more preferably an integer of 1 to 3.

[0352] (Twisted Structure That Inhibits Conjugation) When the functional material used in the composition of the present invention is a polymer having a repeating unit represented by formula (50), the repeating unit represented by formula (50) is more preferably a repeating unit represented by formula (54), a repeating unit represented by formula (55), a repeating unit represented by formula (56), or a repeating unit represented by formula (57), and particularly preferably a repeating unit represented by formula (54). Furthermore, the partial structure represented by formula (63) is preferably a partial structure represented by the following formula (61) or the following formula (61'): Therefore, the repeating unit represented by formula (50) is more preferably a repeating unit represented by formula (54) containing a partial structure represented by formula (61) or formula (61′) below as a main chain structure, a repeating unit represented by formula (55) containing a partial structure represented by formula (61) or formula (61′) below as a main chain structure, a repeating unit represented by formula (56) containing a partial structure represented by formula (61) or formula (61′) below as a main chain structure, or a repeating unit represented by formula (57) containing a partial structure represented by formula (61) or formula (61′) below as a main chain structure, and particularly preferably a repeating unit represented by formula (54) containing a partial structure represented by formula (61) or formula (61′) below as a main chain structure:

[0353]

[0354] (In formula (61) and formula (61′), R ６０１ is R in formula (54) ２０１ or R ２０２ , R in formula (55) ３０３ , R ３０４ , R ３０５ , or R ４０６ , R in formula (56) ４４１ or R ４４２ , R in formula (57) ５１７ , R ５１８ or R ５１９and -* represents a bond to the adjacent atom. When formula (61) is a partial structure of formula (54) or a partial structure of formula (56), Ring B may be a part of a fused ring. When formula (61') is a partial structure of formula (54) or a partial structure of formula (56), Ring B may be a part of a fused ring. The partial structures represented by formula (61) and formula (61') are represented by R ６０１ In addition, when Ring A and Ring B are a partial structure of formula (54), R ２０１ or R ２０２ , when it is a partial structure of formula (55), R ３０３ , R ３０４ , R ３０５ , or R ３０６ , when it is a partial structure of formula (56), R ４４１ or R ４４２ , when it is a partial structure of formula (57), R ５１７ , R ５１８ or R ５１９ It may have.)

[0355] (Formula (62)) Particularly preferred as the repeating unit represented by formula (50) is a polymer containing a repeating unit represented by the following formula (62), which is a repeating unit represented by formula (54) containing a partial structure represented by formula (61) or formula (61') as a main chain structure.

[0356]

[0357] (In formula (62), Ar ５１ , X, R ２０１ , R ２０２ , R ２２１ , R ２２２ , a, b, c, and d are Ar in the formula (54). ５１ , X, R ２０１ , R ２０２ , R ２２１ , R ２２２ , a, b, c, d are the same, and a １ , a ２ , b １ , b ２ , i １ , i ２ , j １ , j ２are each independently 0 or 1, provided that either of the following conditions (1) or (2) is satisfied: １ , a ２ and at least one of a is 1 or more; １ , b ２ and at least one of b is 1 or more, c is 1 or more, d is 1 or more, and when c is 1, a １ or a ２ At least one of d is 1, and when d is 1, b １ or b ２ At least one of the is 1. (2) i １ , i ２ , j １ and j ２ At least one of the is 1. Ring A1 is R ２０１ Ring A2 refers to a divalent benzene ring which may have R ２０１ wherein, when c=1, it refers to a monocyclic divalent benzene ring; Ring A3 refers to a divalent fused ring in which a biphenyl structure is further bonded via X; Ring A4 refers to R ２０２ wherein R represents a divalent group having d-1 benzene rings linked together, and when d=1, the divalent group represents a monocyclic benzene ring; ２０２ It refers to a divalent benzene ring which may have

[0358] Here, a in formula (54) being 1 or more means that a １ , a ２ and a are 1 or more, and b being 1 or more in formula (54) means that b １ , b ２ and at least one of b is 1 or more.)

[0359] As shown below, the formula (62) contains the formula (61) or the formula (61′) as a partial structure. １ , a ２ and at least one of a is 1 or more, １ or a ２When at least one of the above is 1, when c is 2 or more, Ring A1 and Ring A2, when c is 1, Ring A1 and Ring A3, when a is 1, Ring A2 and Ring A1, or Ring A2 and Ring A3, contain the formula (61) or the formula (61') as a partial structure. １ , b ２ It can be seen that when at least one of and b is 1 or more, the formula (61) or the formula (61') is included as a partial structure. １ , i ２ , j １ and j ２ If at least one of i is 1, １ and i ２ If one or both of these are 1, then R of Ring A3 ２２１ The ring to which is bonded and the benzene ring of Ring A2 form a partial structure represented by formula (61'), and j １ and j ２ If one or both of these are 1, then R of Ring A3 ２２２ It can be seen that the ring to which is bonded and the benzene ring of Ring A4 form the partial structure of formula (61). That is, it can be seen that Ring A3 and Ring A2, or Ring A3 and Ring A4, have a twisted structure. Therefore, formula (62) has a twisted structure that inhibits conjugation because the aromatic ring of the main chain has a twisted structure, and is therefore preferable.

[0360] [Molecular Weight of Polymer] The molecular weight of the polymer contained in the composition of the present invention will be described below.

[0361] The weight-average molecular weight (Mw) of the polymer having the above-mentioned arylamine structure as a repeating unit is usually 1,000,000 or less, preferably 500,000 or less, more preferably 100,000 or less, even more preferably 70,000 or less, and particularly preferably 50,000 or less, and is usually 5,000 or more, preferably 10,000 or more, even more preferably 12,000 or more, and particularly preferably 15,000 or more.

[0362] When the weight-average molecular weight of the polymer having the above-mentioned arylamine structure as a repeating unit is below the upper limit, the polymer tends to be soluble in solvents and have excellent film-forming properties.Furthermore, when the weight-average molecular weight of the polymer is above the lower limit, the polymer's glass transition temperature, melting point, and vaporization temperature are prevented from decreasing, and heat resistance may be improved.In addition, the coating film after crosslinking reaction may have sufficient insolubility in organic solvents.

[0363] The number average molecular weight (Mn) of the polymer having the above-mentioned arylamine structure as a repeating unit is usually 750,000 or less, preferably 250,000 or less, more preferably 100,000 or less, and particularly preferably 50,000 or less, and is usually 2,000 or more, preferably 4,000 or more, more preferably 6,000 or more, and even more preferably 8,000 or more.

[0364] Furthermore, the dispersity (Mw / Mn) of the polymer having the above-mentioned arylamine structure as a repeating unit is preferably 3.5 or less, more preferably 2.5 or less, and particularly preferably 2.0 or less. Since the smaller the dispersity value, the better, the lower limit is ideally 1. When the dispersity of the polymer is the above-mentioned upper limit or less, purification is easy, and the solubility in solvents and charge transport ability are good.

[0365] The weight-average molecular weight and number-average molecular weight of a polymer are usually determined by SEC (size exclusion chromatography) measurement. In SEC measurement, the elution time of a higher molecular weight component is shorter and the elution time of a lower molecular weight component is longer. The weight-average molecular weight and number-average molecular weight are calculated by converting the elution time of the sample into molecular weight using a calibration curve calculated from the elution time of polystyrene (standard sample) with known molecular weight.

[0366] (Content of repeating unit represented by formula (50)) In the polymer, the content of the repeating unit represented by formula (50) is not particularly limited, but the repeating unit represented by formula (50) is usually contained in an amount of 10 mol % or more, preferably 30 mol % or more, more preferably 40 mol % or more, and even more preferably 50 mol % or more, based on 100 mol % of all repeating units in the polymer.

[0367] The polymer may be composed solely of repeating units represented by formula (50), but for the purpose of balancing various performances when made into an organic electroluminescent device, the polymer may contain repeating units other than the repeating units represented by formula (50). In this case, the content of the repeating units represented by formula (50) in the polymer is usually 99 mol % or less, preferably 95 mol % or less.

[0368] <Repeating Unit Represented by Formula (50-2)> The polymer of the present invention containing an arylamine structure as a repeating unit may further contain a structure represented by the following formula (50-2) in the main chain.

[0369]

[0370] (In the formula, R ８１ , R ８３ R each independently represents a hydrogen atom, an alkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group. ８１ , R ８３ When there are a plurality of p, they may be the same or different. ８０ represents an integer of 1 to 5.)

[0371] R ８１ , R ８３ When is an alkyl group, the alkyl group may be a linear, branched, or cyclic alkyl group. The number of carbon atoms in the alkyl group is not particularly limited, but in order to maintain the solubility of the polymer, it is preferably 1 or more, and is preferably 8 or less, more preferably 6 or less, and even more preferably 3 or less. The alkyl group is more preferably a methyl group or an ethyl group.

[0372] R ８１ , R ８３When is an aromatic hydrocarbon group or an aromatic heterocyclic group, the structures described above in the "Definition" section are preferred.

[0373] R ８１ , R ８３ may have a substituent. The substituent is preferably a substituent or a crosslinking group selected from the above-mentioned group Z of substituents. In the case of a crosslinking group, it is preferably a crosslinking group selected from the above-mentioned group T of crosslinking groups.

[0374] From the viewpoint of durability and charge transport property of the polymer, ８０ is preferably 3 or less, more preferably 2 or less, and most preferably 1.

[0375] By including the structure represented by formula (50-2), conjugation of the main chain of the polymer is broken, and the S1 energy level and the T1 energy level of the polymer are increased. When a composition including this polymer is used in a hole transport layer of an organic electroluminescent device, it is considered that excitons in the light-emitting layer are less likely to be deactivated, and the light-emitting efficiency is increased, which is preferable.

[0376] (Preferred Repeating Unit Structure of Polymer) Here, in the repeating unit represented by each formula, a specific structure is referred to as a "repeat unit structure." A specific structure is a structure obtained by substituting specific structures or numerical values ​​for all symbols in the general formula. That is, a polymer having an arylamine structure as a repeating unit may contain only one repeating unit structure among the repeating unit structure represented by formula (54), the repeating unit structure represented by formula (55), the repeating unit structure represented by formula (56), the repeating unit structure represented by formula (57), and the repeating unit structure represented by formula (60), or may contain two or more repeating unit structures. When two or more repeating unit structures are contained, these two or more repeating units may be repeating unit structures represented by the same general formula or may be repeating unit structures represented by different general formulas. From the viewpoint of charge transport properties and durability, it is more preferable that the polymer having an arylamine structure as a repeating unit is a polymer that contains one or two specific repeating unit structures represented by each of these formulas and does not contain any other repeating unit structures.

[0377] [Specific Examples] Specific examples of the polymers are shown below, but the polymers are not limited to these. The numbers in the chemical formulas represent the molar ratios of repeating units. These polymers may be random copolymers, alternating copolymers, block copolymers, graft copolymers, or the like, and the order of the monomers is not limited.

[0378]

[0379]

[0380] <Method for producing polymer> The method for producing the polymer contained in the composition of the present invention is not particularly limited and is optional. For example, a polymerization method by Suzuki reaction, a polymerization method by Grignard reaction, a polymerization method by Yamamoto reaction, a polymerization method by Ullmann reaction, a polymerization method by Buchwald-Hartwig reaction, etc. can be mentioned. In addition, it can be produced by a production method similar to the production method of the polymer described in WO 2019 / 177175, WO 2020 / 171190, and WO 2021 / 125011.

[0381] In the case of the polymerization method by the Ullmann reaction and the polymerization method by the Buchwald-Hartwig reaction, for example, a polymer containing a repeating unit represented by the formula (54) is synthesized by reacting an aryl dihalide represented by the following formula (2a) (Z represents a halogen atom such as I, Br, Cl, or F) with a primary amino aryl represented by the following formula (2b):

[0382]

[0383] (In the above reaction formula, Ar ５１ , R ２０１ , R ２０２ , X, and a to d are defined as in the formula (54).

[0384] In the case of the polymerization method using the Ullmann reaction and the polymerization method using the Buchwald-Hartwig reaction, for example, a polymer containing a repeating unit represented by formula (55) is synthesized by reacting an aryl dihalide represented by formula (3a) (Z represents a halogen atom such as I, Br, Cl, or F) with a primary amino aryl represented by formula (3b).

[0385]

[0386] (In the above reaction formula, Ar ５１ , R ３０３ ~R ３０６ , n, m, l, p, and q are defined as in the formula (55).

[0387] In the above polymerization method, the reaction for forming the N-aryl bond is usually carried out in the presence of a base such as potassium carbonate, sodium tert-butoxide, triethylamine, etc. Alternatively, it can be carried out in the presence of a transition metal catalyst such as a copper or palladium complex.

[0388] <Content of Arylamine Compound of the Present Invention> From the viewpoint of reducing the injection barrier in the charge transport layer, the content of the arylamine compound of the present invention is preferably 10% by weight or more, more preferably 25% by weight or more, and even more preferably 30% by weight or more, in terms of the composition ratio of the solid components of the composition. On the other hand, from the viewpoint of maintaining the charge transport property in the charge transport layer, the content of the arylamine compound of the present invention in the composition of the present invention is preferably 99% by weight or less, more preferably 90% by weight or less, and even more preferably 80% by weight or less, in terms of the composition ratio of the solid components of the composition.

[0389] <Composition Ratio and Content of Arylamine Compound and Electron-Accepting Compound in the Composition> In the composition of the present invention, the content of the arylamine compound of the present invention relative to the total amount of the arylamine compound of the present invention and the electron-accepting compound of the present invention is preferably 99% by weight or less, more preferably 97% by weight or less, and even more preferably 95% by weight or less. It is also preferably 50% by weight or more, more preferably 70% by weight or more, and even more preferably 80% by weight or more. When the content is within these ranges, a film formed using the composition of the present invention is sufficiently crosslinked and insolubilized, making it possible to directly form a film by wet coating onto the film formed using the composition of the present invention. Furthermore, when a film formed using the composition of the present invention is used as a charge injection film, it is believed that the injection barrier in the charge transport layer is reduced, resulting in excellent charge transport properties and improved stability during charge transport, thereby improving the durability of a device including a film formed using the composition of the present invention.

[0390] <Content of Charge Transport Polymer Compound> In order to improve the charge transport property of the film formed by the arylamine compound of the present invention and the electron acceptor compound of the present invention, it is preferable to use these compounds in combination with a charge transport polymer compound. In this case, the content of the charge transport polymer compound in the composition of the present invention is preferably 10% by weight or more, more preferably 20% by weight or more, in terms of the composition ratio of the solid components of the composition of the present invention, from the viewpoint of charge transport property. On the other hand, from the viewpoint of reducing the charge injection barrier between the charge injection layer and the charge transport layer adjacent to the charge injection layer, it is preferably 95% by weight or less, more preferably 90% by weight or less, and even more preferably 85% by weight or less.

[0391] [Composition] The composition of the present invention may further contain a solvent, a polymerization initiator, an additive, and the like.

[0392] <Solvent> The composition of the present invention preferably further contains a solvent. In particular, when a charge transport film is formed by a wet film formation method using the composition of the present invention, it is preferable to use a solvent to dissolve the arylamine compound of the present invention, the electron accepting compound of the present invention, and the charge transport polymer compound.

[0393] The solvent contained in the composition of the present invention is not particularly limited as long as it is capable of dissolving both the arylamine compound of the present invention, the electron-accepting compound of the present invention, and the charge-transporting polymer compound. Here, the solvent capable of dissolving the arylamine compound of the present invention and the electron-accepting compound of the present invention is a solvent that dissolves the arylamine compound of the present invention at a concentration of preferably 0.005% by weight or more, more preferably 0.5% by weight or more, and even more preferably 1% by weight or more. It is also a solvent that dissolves the electron-accepting compound at a concentration of preferably 0.001% by weight or more, more preferably 0.1% by weight or more, and even more preferably 0.2% by weight or more. It is also a solvent that dissolves the charge-transporting polymer compound at a concentration of preferably 0.005% by weight or more, more preferably 0.5% by weight or more, and even more preferably 1% by weight or more.

[0394] Preferred solvents include, for example, aromatic hydrocarbon solvents, ether solvents, and ester solvents. Specific examples of aromatic hydrocarbon solvents include toluene, xylene, mesitylene, tetralin, and cyclohexylbenzene. Examples of ether solvents include aliphatic ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and propylene glycol-1-monomethyl ether acetate (PGMEA); and aromatic ethers such as 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole, phenetole, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3-dimethylanisole, and 2,4-dimethylanisole. Examples of ester solvents include aliphatic esters such as ethyl acetate, n-butyl acetate, ethyl lactate, and n-butyl lactate; and aromatic esters such as phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, propyl benzoate, and n-butyl benzoate. These may be used alone or in any combination of two or more in any ratio.

[0395] Examples of solvents that can be used other than the above-mentioned ether-based solvents and ester-based solvents include amide-based solvents such as N,N-dimethylformamide and N,N-dimethylacetamide, and dimethyl sulfoxide. Any one of these may be used alone, or two or more may be used in any combination and ratio. Furthermore, one or more of these solvents may be used in combination with one or more of the above-mentioned ether-based solvents and ester-based solvents. In particular, aromatic hydrocarbon-based solvents such as benzene, toluene, and xylene have a low ability to dissolve electron-accepting compounds and free carriers (cation radicals), so it is preferable to use them in combination with ether-based solvents and ester-based solvents.

[0396] When a solvent is used, the concentration of the solvent relative to the composition of the present invention is preferably 10% by weight or more, more preferably 30% by weight or more, and even more preferably 50% by weight or more. The concentration of the solvent relative to the composition is preferably 99.999% by weight or less, more preferably 99.99% by weight or less, and even more preferably 99.9% by weight or less. When two or more solvents are used in combination, the total amount of these solvents should satisfy this range.

[0397] When the composition of the present invention is used in an organic electroluminescent device, the organic electroluminescent device is formed by laminating layers composed of a large number of organic compounds, and therefore each layer is required to be a uniform layer. When forming a layer by a wet film-forming method, if moisture is present in the solution (composition) for forming a thin film, the moisture will be mixed into the coating film and the uniformity of the film will be impaired, so it is preferable that the moisture content in the solution is as low as possible. In addition, since organic electroluminescent devices generally use many materials that are significantly deteriorated by moisture, such as the cathode, the presence of moisture is also undesirable from the viewpoint of deterioration of the device.

[0398] Specifically, the water content of the composition of the present invention is preferably 1 wt % or less, more preferably 0.1 wt % or less, and even more preferably 0.05 wt % or less. Methods for reducing the water content in the composition include, for example, nitrogen gas blanketing, use of a desiccant, pre-dehydrating the solvent, and use of a solvent with low water solubility. Among these, from the viewpoint of preventing the phenomenon in which the solution coating film absorbs moisture from the atmosphere and turns white during the coating process, it is preferable to use a solvent with low water solubility. When used in applications involving film formation by a wet film formation method, the composition of the present invention preferably contains a solvent with low water solubility, specifically, a solvent with a water solubility of 1 wt % or less, preferably 0.1 wt % or less at 25°C, at a concentration of preferably 10 wt % or more, more preferably 30 wt % or more, and particularly 50 wt % or more, relative to the total composition.

[0399] <Composition for Charge Transport Film> When the electron-accepting compound having a crosslinking group is the electron-accepting ionic compound described above, it is preferably used as a composition containing the electron-accepting ionic compound and an arylamine compound having a crosslinking group represented by any one of the formulas (3-1) to (3-4) described above (hereinafter referred to as "composition for charge transport film (A)"), or as a composition containing a charge-transporting ionic compound consisting of a cation radical of an arylamine compound having a crosslinking group described below and a counter anion that is a part of the electron-accepting ionic compound (hereinafter referred to as "composition for charge transport film (B)"). For convenience, the compositions for charge transport films are described separately as compositions for charge transport film (A) and composition for charge transport film (B). However, the composition for charge transport film also includes compositions containing the electron-accepting ionic compound described above, an arylamine compound having a crosslinking group described below, and a charge-transporting ionic compound consisting of a cation radical of an arylamine compound having a crosslinking group described below and a counter anion that is a part of the electron-accepting ionic compound described above.

[0400] The compositions (A) and (B) for a charge transport film are compositions (compositions for a charge transport material) that can be widely used for charge transport material applications. However, since they are usually formed into a film and used as a hole injection layer and / or a hole transport layer, i.e., as a "charge transport film" that transports holes, which are electric charges, they are specifically referred to as "compositions for a charge transport film" in this specification.

[0401] <Composition (A) for Charge Transport Film> The composition (A) for charge transport film contains the arylamine compound having a crosslinking group, the electron-accepting compound having a crosslinking group, and a solvent. The arylamine compound having a crosslinking group may be contained alone or in combination with two or more different compounds. The composition (A) may further contain the hole-transporting polymer compound.

[0402] <Method for preparing composition (A) for charge transport film> The composition (A) for charge transport film is prepared by mixing at least the electron-accepting compound of the present invention and the arylamine compound of the present invention. In this case, the composition (A) for charge transport film preferably contains a solvent, and the electron-accepting compound of the present invention and the arylamine compound of the present invention are dissolved in the solvent and mixed.

[0403] The content of the electron-accepting compound of the present invention in the composition (A) for charge transport films is usually 0.1% by weight or more, preferably 1% by weight or more, and usually 100% by weight or less, preferably 40% by weight or less, based on the arylamine compound of the present invention. A content of the electron-accepting compound equal to or greater than the lower limit is preferred because sufficient free carriers (cation radicals of the arylamine compound of the present invention) can be generated, while a content of the electron-accepting compound equal to or less than the upper limit is preferred because sufficient charge transport ability can be ensured. When two or more electron-accepting compounds are used in combination, the total content of these compounds should be within the above range. The same applies to the charge-transporting compound.

[0404] <Composition (B) for Charge Transport Film> As described above, composition (B) for charge transport film is a composition containing a charge transporting ionic compound consisting of the cation radical of the arylamine compound of the present invention and the counter anion of the electron-accepting ionic compound. The cation radical of the arylamine compound of the present invention, which is the cation of the charge transporting ionic compound, is a chemical species obtained by removing one electron from the electrically neutral compound represented by the arylamine compound of the present invention. The cation radical of the arylamine compound of the present invention is an aromatic arylamine compound having a structure represented by the following formulas (300-1) to (300-4).

[0405]

[0406] In the above formulas (300-1) to (300-4), Ar ２ , Ar ３ , R ２ , A ２ , a ２ respectively represent Ar in the formulas (3-1) to (3-4). ２ , Ar ３ , R ２ , A ２ , a ２ is the same as:

[0407] As the compounds of formulas (300-1) to (300-4), aromatic arylamine compounds having structures represented by the following formulas (310-1) to (310-4), respectively, are particularly preferred, in terms of having an appropriate oxidation-reduction potential and being able to obtain stable charge-transporting ionic compounds.

[0408]

[0409] In the above formulas (310-1) to (310-4), Ar ２ , Ar ３ , R ２ , A ２ , a ２ respectively represent Ar in the formulas (3-1) to (3-4). ２ , Ar ３ , R ２ , A ２ , a ２ The same as Ar ４ is Ar in the formulas (300-1) to (300-4). ２ is a structure that can be bonded to an arylamine structure via a phenylene group; ２ is a residue obtained by removing the phenylene group from

[0410] <Charge-Transporting Ionic Compound> The charge-transporting ionic compound is a compound in which a cation radical of the arylamine compound of the present invention is ionically bonded to a counter anion, which is part of an electron-accepting ionic compound. The charge-transporting ionic compound can be obtained by mixing an electron-accepting ionic compound with the arylamine compound of the present invention, and is easily soluble in various solvents. Specifically, it can be obtained by the method described below in <Method for Preparing Composition (B) for Charge-Transport Film>. The molecular weight of the charge-transporting ionic compound is usually 1,000 or more, preferably 1,100 or more, more preferably 1,200 or more, and usually 9,000 or less, preferably 5,000 or less, more preferably 4,000 or less, except when the cation radical is a polymer compound.

[0411] <Method for preparing composition (B) for charge transport film> The charge transporting ionic compound (B) is preferably prepared by dissolving an electron-accepting ionic compound and the arylamine compound of the present invention in a solvent and mixing them. In this solution, the arylamine compound of the present invention is oxidized by the electron-accepting ionic compound to form a cation radical, thereby generating a charge transporting ionic compound, which is an ionic compound of the counter anion of the electron-accepting ionic compound and the cation radical of the arylamine compound of the present invention.

[0412] In this case, by mixing the arylamine compound of the present invention with the electron-accepting ionic compound in a solution, the probability that the electron-accepting ionic compound will be present in the vicinity of the nitrogen atom of the arylamine, which is a site that is easily oxidized in the arylamine compound of the present invention, increases, and the amine structure of the arylamine compound of the present invention is oxidized by the electron-accepting ionic compound to form a cation radical, which makes it easier to generate an ionic compound of the counter anion of the electron-accepting ionic compound and the cation radical of the arylamine compound of the present invention. In this case, it is preferable to heat the solution from the viewpoint of accelerating the reaction.

[0413] The composition may also be prepared by heating a mixture of an electron-accepting ionic compound and the arylamine compound of the present invention. This mixture is preferably a film formed by coating and drying a solution in which a mixture of an electron-accepting ionic compound and the arylamine compound of the present invention is dissolved in a solvent. Heating the mixture causes the electron-accepting ionic compound and the arylamine compound of the present invention to diffuse into each other in the mixture, increasing the probability that the electron-accepting compound will be present near the nitrogen atom of the amine structure, which is a site susceptible to oxidation in the arylamine compound of the present invention. This increases the likelihood of the electron-accepting compound being present near the nitrogen atom of the amine structure, which is a site susceptible to oxidation in the arylamine compound of the present invention, thereby facilitating the formation of an ionic compound between the counter anion of the electron-accepting ionic compound and the cation radical of the arylamine compound of the present invention. The heating temperature is preferably such that the crosslinking groups in the composition do not undergo crosslinking reaction. However, even at a temperature at which the crosslinking groups undergo crosslinking reaction, the crosslinking reaction also occurs while diffusing, and therefore the electron-accepting ionic compound is formed without any problems.

[0414] The composition (B) for a charge transport film may contain one or more of the above-mentioned charge transporting ionic compounds. It is preferable to contain one or two charge transporting ionic compounds, and it is more preferable to contain one charge transporting ionic compound alone. This is because the ionization potential of the charge transporting ionic compound varies little and the hole transport property is excellent. A composition containing one or two charge transporting ionic compounds alone is a composition prepared using only two or three electron-accepting ionic compounds and the arylamine compounds of the present invention in total, i.e., a composition prepared using at least one electron-accepting ionic compound and at least one arylamine compound of the present invention.

[0415] The composition (B) for a charge transport film preferably contains a charge transporting compound in addition to the charge transporting ionic compound. The charge transporting compound is particularly preferably a polymer containing the arylamine structure as a repeating unit, which is the hole transporting polymer compound and has a repeating unit represented by formula (50). When preparing the composition (B) for a charge transport film, the content of the arylamine compound of the present invention as a charge amount is preferably 10% by weight or more, more preferably 20% by weight or more, and even more preferably 30% by weight or more, based on the charge transporting ionic compound, and is preferably 10,000% by weight or less, and even more preferably 1,000% by weight or less.

[0416] The charge transport film formed from the composition (B) for a charge transport film exhibits high hole injection and transport capabilities due to the transfer of positive charges from the charge transporting ionic compound to a nearby neutral charge transporting compound. Therefore, the mass ratio of the charge transporting ionic compound to the neutral arylamine compound of the present invention is preferably about 1:100 to 100:1, and more preferably about 1:20 to 20:1.

[0417] <Relationship between Compositions (A) and (B) for Charge Transport Film> The charge transport film formed using Composition (A) for Charge Transport Film has excellent heat resistance and high hole injection and transport capabilities. The reasons for these excellent properties are explained below. Composition (A) for Charge Transport Film contains the above-mentioned electron-accepting compound and charge-transporting compound. The cation in the electron-accepting ionic compound has a hypervalent central atom and its positive charge is widely delocalized, resulting in high electron-accepting properties. This causes electron transfer from the charge-transporting compound to the cation of the electron-accepting ionic compound, resulting in the generation of a charge-transporting ionic compound consisting of a cation radical of the charge-transporting compound and a counter anion. This cation radical of the charge-transporting compound acts as a charge carrier, thereby increasing the electrical conductivity of the charge-transporting film. That is, when Composition (A) for Charge Transport Film is prepared, it is believed that a charge-transporting ionic compound consisting at least in part of a cation radical of the charge-transporting compound and a counter anion of the electron-accepting ionic compound is generated. For example, when electrons are transferred from a charge transporting compound represented by the following formula (7) to an electron accepting compound represented by formula (6), a charge transporting ionic compound represented by formula (9) is generated, which is composed of a cation radical of the charge transporting compound and a counter anion.

[0418]

[0419] [Preparation of Composition] The composition of the present invention can be prepared by mixing a functional material containing the arylamine compound of the present invention, the electron-accepting compound of the present invention, and preferably further the above-mentioned electron-accepting compound, with a solvent, and heating for a certain period of time to dissolve or disperse the mixture. To uniformly dissolve or disperse the functional material in the solvent, the heating temperature is preferably 80°C or higher, more preferably 90°C or higher, and even more preferably 100°C or higher, for example, 100 to 115°C. The heating time is preferably 30 minutes or longer, more preferably 45 minutes or longer, and even more preferably 60 minutes or longer, for example, 60 to 180 minutes.

[0420] The heated composition is filtered using a membrane filter, a depth filter, etc. to remove coarse particles before use. Considering that the composition is applied by being ejected from the nozzle of an inkjet head, the pore size of the filter is preferably 0.5 μm or less, more preferably 0.2 μm or less, and even more preferably 0.1 μm or less.

[0421] [Film formation method using composition] When forming a film using the composition of the present invention, the composition of the present invention is preferably a solution containing a solvent, and the composition of the present invention is preferably wet-formed into a film. The wet film formation method refers to a method in which a composition containing a solvent is applied to a substrate and the solvent is dried and removed to form a film. The application method is not particularly limited, and examples thereof include spin coating, dip coating, die coating, bar coating, blade coating, roll coating, spray coating, capillary coating, inkjet printing, screen printing, gravure printing, and flexographic printing.

[0422] The method for drying and removing the solvent usually involves heating. Examples of heating means used in the heating step include a clean oven, a hot plate, and infrared heating. For infrared heating, a halogen heater, a ceramic-coated halogen heater, a ceramic heater, or the like can be used. Infrared heating directly applies thermal energy to the substrate or film, allowing for drying in a shorter time than heating using an oven or hot plate. This makes it possible to minimize the effects of gases (moisture and oxygen) in the heating atmosphere and minute dust particles, improving productivity and making this method preferable.

[0423] The heating temperature is usually 80°C or higher, preferably 100°C or higher, and more preferably 150°C or higher. The heating temperature is usually 300°C or lower, preferably 280°C or lower, and more preferably 260°C or lower. The heating time is usually 10 seconds or longer, preferably 60 seconds or longer, and more preferably 90 seconds or longer, and usually 120 minutes or shorter, preferably 60 minutes or shorter, and more preferably 30 minutes or shorter. It is also preferable to perform vacuum drying before heat drying. The film thickness of the organic layer formed from the composition of the present invention by a wet film formation method is usually 5 nm or higher, preferably 10 nm or higher, and more preferably 20 nm or higher. The film thickness is usually 1000 nm or lower, preferably 500 nm or lower, and more preferably 300 nm or lower.

[0424] [Organic Electroluminescent Device] The organic electroluminescent device of the present invention is an organic electroluminescent device having an anode and a cathode on a substrate, and an organic layer between the anode and the cathode, and the organic layer can be formed using the composition of the present invention. The organic electroluminescent device of the present invention may also be manufactured by the manufacturing method of an organic electroluminescent device described below. A film using the composition of the present invention and a film formed using the composition of the present invention can be suitably used as a charge transport layer. This charge transport layer is particularly preferably used as a charge transport film of the organic electroluminescent device.

[0425] In one embodiment, the organic electroluminescent device of the present invention is an organic electroluminescent device having an anode and a cathode on a substrate, and an organic layer between the anode and the cathode, wherein the organic layer contains a crosslinked reaction product of an arylamine compound represented by any one of the above formulas (3-1) to (3-4) and an electron-accepting compound represented by the above formula (81).

[0426] In another embodiment, the organic electroluminescent device of the present invention has an anode and a cathode on a substrate, and an organic layer between the anode and the cathode, wherein the organic layer contains a crosslinked reaction product between an arylamine compound represented by any one of the above formulas (3-1) to (3-4) and a polymer having an arylamine structure represented by the above formula (50) as a repeating unit and having a crosslinking group.

[0427] As an example of the structure of the organic electroluminescent element of the present invention, a schematic diagram (cross section) of an example of the structure of an organic electroluminescent element 8 is shown in Fig. 1. In Fig. 1, 1 represents a substrate, 2 represents an anode, 3 represents a hole injection layer, 4 represents a hole transport layer, 5 represents a light-emitting layer, 6 represents an electron transport layer, and 7 represents a cathode.

[0428] [Substrate] The substrate 1 serves as a support for the organic electroluminescent element, and is typically made of a quartz or glass plate, a metal plate or metal foil, a plastic film or sheet, or the like. Of these, a glass plate or a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, or polysulfone is preferred. The substrate is preferably made of a material with high gas barrier properties, as this makes it less likely for the organic electroluminescent element to deteriorate due to the outside air. Therefore, particularly when a material with low gas barrier properties, such as a synthetic resin substrate, is used, it is preferable to provide a dense silicon oxide film or the like on at least one side of the substrate to improve the gas barrier properties.

[0429] [Anode] The anode 2 has the function of injecting holes into the layer on the light-emitting layer 5 side.

[0430] The anode 2 is usually made of a metal such as aluminum, gold, silver, nickel, palladium, or platinum; a metal oxide such as indium and / or tin oxide; a metal halide such as copper iodide; or a conductive polymer such as carbon black, poly(3-methylthiophene), polypyrrole, or polyaniline.

[0431] The anode 2 is usually formed by a dry method such as sputtering or vacuum deposition. When the anode is formed using metal fine particles such as silver, fine particles such as copper iodide, carbon black, conductive metal oxide fine particles, or conductive polymer fine powder, the anode can be formed by dispersing the material in an appropriate binder resin solution and applying it to the substrate. In the case of a conductive polymer, a thin film can be formed directly on the substrate by electrolytic polymerization, or the conductive polymer can be applied to the substrate to form the anode (Appl. Phys. Lett., Vol. 60, p. 2711, 1992).

[0432] The anode 2 usually has a single layer structure, but may have a laminated structure as appropriate. When the anode 2 has a laminated structure, a different conductive material may be laminated on the first layer of the anode.

[0433] The thickness of the anode 2 may be determined depending on the required transparency, material, etc. When particularly high transparency is required, a thickness that provides a visible light transmittance of 60% or more is preferred, and a thickness that provides a visible light transmittance of 80% or more is more preferred. The thickness of the anode 2 is usually 5 nm or more, preferably 10 nm or more, and usually 1000 nm or less, preferably 500 nm or less. On the other hand, when transparency is not required, the thickness of the anode 2 may be arbitrarily determined depending on the required strength, etc. In this case, the anode 2 may have the same thickness as the substrate.

[0434] When another layer is formed on the surface of the anode 2, it is preferable to perform a treatment with ultraviolet light / ozone, oxygen plasma, argon plasma, or the like before the film formation to remove impurities on the anode 2 and adjust the ionization potential thereof to improve the hole injection property.

[0435] [Hole Injection Layer] A layer that transports holes from the anode 2 side to the light-emitting layer 5 side is usually called a hole injection transport layer or a hole transport layer. When there are two or more layers that transport holes from the anode 2 side to the light-emitting layer 5 side, the layer closer to the anode side may be called the hole injection layer 3. The hole injection layer 3 is preferably formed in order to enhance the function of transporting holes from the anode 2 to the light-emitting layer 5 side. When the hole injection layer 3 is formed, the hole injection layer 3 is usually formed on the anode 2.

[0436] The hole injection layer 3 formed using the composition of the present invention contains a crosslinked reaction product of the arylamine compound of the present invention and the electron accepting compound of the present invention.

[0437] The method for forming the hole injection layer 3 is not particularly limited, and examples thereof include a vacuum deposition method, a wet film formation method, etc. When forming a layer by a wet film formation method, the composition of the present invention is prepared, applied to the anode 2 by a wet film formation method such as a spin coating method or a dip coating method, and dried to form the hole injection layer 3.

[0438] It is particularly preferred to use a composition containing the arylamine compound of the present invention and the electron-accepting compound of the present invention, or to use a film formed using a composition containing the arylamine compound of the present invention and the electron-accepting compound of the present invention. The thickness of the hole injection layer 3 thus formed is usually 5 nm or more, preferably 10 nm or more, and usually 1,000 nm or less, preferably 500 nm or less.

[0439] The hole injection layer may be formed by vacuum deposition or wet film formation. From the viewpoint of excellent film-forming properties, wet film formation is preferred. Examples of solvents include ether-based solvents, ester-based solvents, aromatic hydrocarbon-based solvents, and amide-based solvents.

[0440] Examples of ether-based solvents include aliphatic ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and propylene glycol-1-monomethyl ether acetate (PGMEA); and aromatic ethers such as 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole, phenetole, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3-dimethylanisole, and 2,4-dimethylanisole.

[0441] Examples of the ester solvent include aromatic esters such as phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, propyl benzoate, and n-butyl benzoate.

[0442] Examples of aromatic hydrocarbon solvents include toluene, xylene, cyclohexylbenzene, 3-isopropylbiphenyl, 1,2,3,4-tetramethylbenzene, 1,4-diisopropylbenzene, cyclohexylbenzene, and methylnaphthalene.

[0443] Examples of the amide solvent include N,N-dimethylformamide and N,N-dimethylacetamide.

[0444] In addition to these, dimethyl sulfoxide and the like can also be used.

[0445] The formation of the hole injection layer 3 by a wet film formation method is usually carried out by preparing a composition for forming a hole injection layer, applying the composition to a layer corresponding to the lower layer of the hole injection layer 3 (usually the anode 2), and drying the composition.

[0446] After the hole injection layer 3 is formed, the coated film is usually dried by heating, drying under reduced pressure, or the like.

[0447] [Hole Transport Layer] The hole transport layer 4 is a layer that transports holes from the anode 2 side to the light-emitting layer 5 side. The hole transport layer 4 is not an essential layer in the organic electroluminescent device of the present invention, but it is preferable to form this layer in order to enhance the function of transporting holes from the anode 2 to the light-emitting layer 5. When the hole transport layer 4 is formed, it is usually formed between the anode 2 and the light-emitting layer 5. Furthermore, when the above-mentioned hole injection layer 3 is present, it is formed between the hole injection layer 3 and the light-emitting layer 5.

[0448] The thickness of the hole transport layer 4 is usually 5 nm or more, preferably 10 nm or more, and on the other hand, usually 300 nm or less, preferably 100 nm or less.

[0449] The material forming the hole transport layer 4 is preferably a material that has high hole transport properties and can efficiently transport injected holes. To this end, it is preferable that the material has a low ionization potential, high transparency to visible light, high hole mobility, excellent stability, and is unlikely to generate impurities that become traps during production or use. Furthermore, since the hole transport layer 4 is often in contact with the light-emitting layer 5, it is preferable that the hole transport layer 4 does not quench the light emission from the light-emitting layer 5 or form exciplexes with the light-emitting layer 5, thereby reducing efficiency.

[0450] The material for such hole transport layer 4 may be any material that has conventionally been used as a constituent material for hole transport layers, and examples thereof include those exemplified as the hole transport compounds used in the hole injection layer 3. Other examples include arylamine derivatives, fluorene derivatives, spiro derivatives, carbazole derivatives, pyridine derivatives, pyrazine derivatives, pyrimidine derivatives, triazine derivatives, quinoline derivatives, phenanthroline derivatives, phthalocyanine derivatives, porphyrin derivatives, silole derivatives, oligothiophene derivatives, condensed polycyclic aromatic derivatives, and metal complexes.

[0451] Other examples include polyvinylcarbazole derivatives, polyarylamine derivatives, polyvinyltriphenylamine derivatives, polyfluorene derivatives, polyarylene derivatives, polyarylene ether sulfone derivatives containing tetraphenylbenzidine, polyarylene vinylene derivatives, polysiloxane derivatives, polythiophene derivatives, and poly(p-phenylene vinylene) derivatives. These may be any of alternating copolymers, random polymers, block polymers, and graft copolymers. Furthermore, they may be polymers having a branched main chain with three or more terminals, or so-called dendrimers.

[0452] Among them, polyarylamine derivatives and polyarylene derivatives are preferred. As the polyarylamine derivative, a polymer containing a repeating unit represented by the following formula (I) is preferred. In particular, a polymer consisting of a repeating unit represented by the following formula (I) is preferred, and in this case, in each repeating unit, Ar ａ ' or Ar ｂ ' may be different.

[0453]

[0454] (In formula (I), Ar ａ ' and Ar ｂ Each of the 's independently represents an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent.

[0455] Examples of polyarylene derivatives include polymers having, as repeating units, arylene groups such as aromatic hydrocarbon groups which may have a substituent or aromatic heterocyclic groups which may have a substituent.

[0456] The polyarylene derivative is preferably a polymer having repeating units represented by the following formula (II-1) and / or the following formula (II-2).

[0457]

[0458] (In formula (II-1), R ａ , R ｂ , R ｃ and R ｄ each independently represents an alkyl group, an alkoxy group, a phenylalkyl group, a phenylalkoxy group, a phenyl group, a phenoxy group, an alkylphenyl group, an alkoxyphenyl group, an alkylcarbonyl group, an alkoxycarbonyl group, or a carboxy group. x11 and x12 each independently represent an integer of 0 to 3. When x11 or x12 is 2 or more, multiple R ａ or R ｂ may be the same or different, and adjacent R ａ or R ｂ may bond together to form a ring.)

[0459]

[0460] (In formula (II-2), R ｅ and R ｆ are each independently R in formula (II-1). ａ , R ｂ , R ｃ or R ｄ x13 and x14 each independently represent an integer of 0 to 3. When x13 or x14 is 2 or more, multiple R ｅ and R ｆ may be the same or different, and adjacent R ｅ or R ｆ may combine with each other to form a ring. L represents an atom or a group of atoms constituting a 5-membered or 6-membered ring.

[0461] Specific examples of L include an oxygen atom, an optionally substituted boron atom, an optionally substituted nitrogen atom, an optionally substituted silicon atom, an optionally substituted phosphorus atom, an optionally substituted sulfur atom, an optionally substituted carbon atom, or a group formed by bonding these together.

[0462] Furthermore, the polyarylene derivative preferably has a repeating unit represented by the following formula (III-3) in addition to the repeating unit represented by the above formula (II-1) and / or the above formula (II-2).

[0463]

[0464] (In formula (III-3), Ar ｃ ~Ar ｉ each independently represents an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent; x15 and x16 each independently represent 0 or 1.

[0465] Specific examples of the above formulas (III-1) to (III-3) and specific examples of polyarylene derivatives include those described in JP-A-2008-98619.

[0466] When the hole transport layer 4 is formed by a wet film-forming method, a composition for forming the hole transport layer is prepared in the same manner as in the formation of the hole injection layer 3, and then the composition is wet-formed and then dried by heating.

[0467] The hole transport layer-forming composition contains the hole transport compound and a solvent. The solvent used is the same as that used in the hole injection layer-forming composition. The film formation conditions, heat drying conditions, etc. are also the same as those for forming the hole injection layer 3.

[0468] When the hole transport layer is formed by vacuum deposition, the film formation conditions are the same as those for forming the hole injection layer 3 described above.

[0469] The hole transport layer 4 may contain, in addition to the hole transport compound, various light-emitting materials, electron transport compounds, binder resins, coating property improvers, and the like.

[0470] The hole transport layer 4 may also be a layer formed by crosslinking a crosslinkable compound. The crosslinkable compound is a compound having a crosslinkable group, and forms a network polymer compound by crosslinking.

[0471] Examples of the crosslinkable group include groups derived from cyclic ethers such as oxetane and epoxy; groups derived from unsaturated double bonds such as vinyl, trifluorovinyl, styryl, acrylic, methacryloyl, and cinnamoyl; and groups derived from benzocyclobutene.

[0472] The crosslinkable compound may be any of a monomer, an oligomer, and a polymer. The crosslinkable compound may be one kind or two or more kinds in any combination and ratio.

[0473] As the crosslinkable compound, it is preferable to use a hole transport compound having a crosslinkable group. Examples of the hole transport compound include those exemplified above, and examples of the crosslinkable compound include those in which a crosslinkable group is bonded to the main chain or side chain of these hole transport compounds. In particular, it is preferable that the crosslinkable group is bonded to the main chain via a linking group such as an alkylene group. Furthermore, in particular, the hole transport compound is preferably a polymer containing a repeating unit having a crosslinkable group, and it is preferably a polymer having a repeating unit in which a crosslinkable group is bonded directly or via a linking group to the above formula (I) or formulas (II-1) to (III-3).

[0474] To form the hole transport layer 4 by crosslinking the crosslinkable compound, a composition for forming the hole transport layer is usually prepared by dissolving or dispersing the crosslinkable compound in a solvent, and the composition is formed into a film by wet film formation to be crosslinked.

[0475] The thickness of the hole transport layer 4 thus formed is usually 5 nm or more, preferably 10 nm or more, and usually 300 nm or less, preferably 150 nm or less.

[0476] [Light-emitting layer] The light-emitting layer 5 is a layer that is excited by the recombination of holes injected from the anode 2 and electrons injected from the cathode 7 when an electric field is applied between the pair of electrodes, and thus emits light. The light-emitting layer 5 is a layer formed between the anode 2 and the cathode 7. When a hole-injection layer is present on the anode, the light-emitting layer is formed between the hole-injection layer and the cathode, and when a hole-transport layer is present on the anode, the light-emitting layer is formed between the hole-transport layer and the cathode. As described above, the organic electroluminescent element of the present invention preferably contains a light-emitting layer-forming material that is suitable for the light-emitting layer.

[0477] The thickness of the light-emitting layer 5 is arbitrary as long as it does not significantly impair the effects of the present invention, but a thicker layer is preferable in terms of preventing defects from occurring in the film, and a thinner layer is preferable in terms of facilitating a low driving voltage. For this reason, the thickness is preferably 3 nm or more, more preferably 5 nm or more, and usually 200 nm or less, more preferably 100 nm or less.

[0478] The light-emitting layer 5 contains at least a material having light-emitting properties (light-emitting material), and preferably contains one or more host materials.

[0479] [Suitable Materials for Forming the Light-Emitting Layer] The light-emitting layer of the present invention contains a light-emitting material and a charge-transporting material. The light-emitting material may be a phosphorescent material or a fluorescent material. Preferably, the red and green light-emitting materials are phosphorescent materials, and the blue light-emitting material is a fluorescent material.

[0480] <Phosphorescent Material> A phosphorescent material is a material that emits light from an excited triplet state. Representative examples include metal complex compounds containing Ir, Pt, Eu, etc., and the material structure preferably includes a metal complex.

[0481] Among metal complexes, examples of phosphorescent organometallic complexes that emit light via a triplet state include Werner complexes or organometallic complex compounds containing, as a central metal, a metal selected from Groups 7 to 11 of the long periodic table (hereinafter, unless otherwise specified, "periodic table" refers to the long periodic table). Examples of such phosphorescent materials include the phosphorescent materials described in WO 2014 / 024889, WO 2015 / 087961, WO 2016 / 194784, and JP 2014-074000 A. Preferably, the compound represented by formula (201) or formula (205) below is preferred, and more preferably, the compound represented by formula (201) below.

[0482]

[0483] In formula (201), ring A1 represents an aromatic hydrocarbon ring structure which may have a substituent or an aromatic heterocyclic structure which may have a substituent. Ring A2 represents an aromatic heterocyclic structure which may have a substituent. R １０１ , R １０２ are each independently a structure represented by formula (202), and "*" represents the bonding position with ring A1 or ring A2. １０１ , R １０２ may be the same or different, and R １０１ , R １０２ When there are a plurality of each of the groups, they may be the same or different.

[0484] Ar ２０１ , Ar ２０３ each independently represents an aromatic hydrocarbon ring structure which may have a substituent, or an aromatic heterocyclic ring structure which may have a substituent. ２０２ represents an aromatic hydrocarbon ring structure which may have a substituent, an aromatic heterocyclic structure which may have a substituent, or an aliphatic hydrocarbon structure which may have a substituent. The substituents bonded to ring A1, the substituents bonded to ring A2, or the substituents bonded to ring A1 and the substituents bonded to ring A2 may be bonded to each other to form a ring.

[0485] B ２０１ -L２００ -B ２０２ represents an anionic bidentate ligand. ２０１ and B ２０２ each independently represents a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms may be atoms constituting a ring. ２００ is a single bond, or B ２０１ and B ２０２ represents an atomic group that together with B constitutes a bidentate ligand. ２０１ -L ２００ -B ２０２ When there are multiple groups, they may be the same or different.

[0486] In the formulas (201) and (202), i1 and i2 each independently represent an integer of 0 to 12, and i3 represents Ar. ２０２ i4 represents an integer of 0 or more, the upper limit of which is the number of substitutions that can be made for Ar ２０１ represents an integer of 0 or greater, the upper limit of which is the number of groups that can be substituted on ring A1 and ring A2; k1 and k2 each independently represent an integer of 0 or greater, the upper limit of which is the number of groups that can be substituted on ring A1 and ring A2; and z represents an integer of 1 to 3.

[0487] (Substituents) Unless otherwise specified, the substituents are preferably groups selected from the following substituent group S.

[0488] <Substituent Group S> - Alkyl groups, preferably alkyl groups having 1 to 20 carbon atoms, more preferably alkyl groups having 1 to 12 carbon atoms, even more preferably alkyl groups having 1 to 8 carbon atoms, and particularly preferably alkyl groups having 1 to 6 carbon atoms. - Alkoxy groups, preferably alkoxy groups having 1 to 20 carbon atoms, more preferably alkoxy groups having 1 to 12 carbon atoms, and even more preferably alkoxy groups having 1 to 6 carbon atoms. - Aryloxy groups, preferably aryloxy groups having 6 to 20 carbon atoms, more preferably aryloxy groups having 6 to 14 carbon atoms, even more preferably aryloxy groups having 6 to 12 carbon atoms, and particularly preferably aryloxy groups having 6 carbon atoms. - Heteroaryloxy groups, preferably heteroaryloxy groups having 3 to 20 carbon atoms, and more preferably heteroaryloxy groups having 3 to 12 carbon atoms. - Alkylamino groups, preferably alkylamino groups having 1 to 20 carbon atoms, and more preferably alkylamino groups having 1 to 12 carbon atoms. - Arylamino groups, preferably arylamino groups having 6 to 36 carbon atoms, and more preferably arylamino groups having 6 to 24 carbon atoms. An aralkyl group, preferably an aralkyl group having 7 to 40 carbon atoms, more preferably an aralkyl group having 7 to 18 carbon atoms, and even more preferably an aralkyl group having 7 to 12 carbon atoms. A heteroaralkyl group, preferably a heteroaralkyl group having 7 to 40 carbon atoms, and even more preferably a heteroaralkyl group having 7 to 18 carbon atoms. An alkenyl group, preferably an alkenyl group having 2 to 20 carbon atoms, more preferably an alkenyl group having 2 to 12 carbon atoms, even more preferably an alkenyl group having 2 to 8 carbon atoms, and particularly preferably an alkenyl group having 2 to 6 carbon atoms. An alkynyl group, preferably an alkynyl group having 2 to 20 carbon atoms, and more preferably an alkynyl group having 2 to 12 carbon atoms. An aryl group, preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 24 carbon atoms, even more preferably an aryl group having 6 to 18 carbon atoms, and particularly preferably an aryl group having 6 to 14 carbon atoms. Heteroaryl groups, preferably heteroaryl groups having 3 to 30 carbon atoms, more preferably heteroaryl groups having 3 to 24 carbon atoms, even more preferably heteroaryl groups having 3 to 18 carbon atoms, and particularly preferably heteroaryl groups having 3 to 14 carbon atoms.- An alkylsilyl group, preferably an alkylsilyl group having an alkyl group with 1 to 20 carbon atoms, more preferably an alkylsilyl group having an alkyl group with 1 to 12 carbon atoms. - An arylsilyl group, preferably an arylsilyl group having an aryl group with 6 to 20 carbon atoms, more preferably an arylsilyl group having an aryl group with 6 to 14 carbon atoms. - An alkylcarbonyl group, preferably an alkylcarbonyl group having 2 to 20 carbon atoms. - An arylcarbonyl group, preferably an arylcarbonyl group having 7 to 20 carbon atoms.

[0489] In the above groups, one or more hydrogen atoms may be replaced with a fluorine atom, or one or more hydrogen atoms may be replaced with a deuterium atom. Unless otherwise specified, aryl is an aromatic hydrocarbon ring, and heteroaryl is an aromatic heterocyclic ring. - A hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, or -SF ５ .

[0490] Of the above substituent group S, preferred are alkyl groups, alkoxy groups, aryloxy groups, arylamino groups, aralkyl groups, alkenyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, arylsilyl groups, and groups in which one or more hydrogen atoms of these groups have been replaced with fluorine atoms, fluorine atoms, cyano groups, and -SF ５ and more preferably an alkyl group, an arylamino group, an aralkyl group, an alkenyl group, an aryl group, a heteroaryl group, a group in which one or more hydrogen atoms of these groups have been replaced with fluorine atoms, a fluorine atom, a cyano group, or —SF ５ and more preferably an alkyl group, an alkoxy group, an aryloxy group, an arylamino group, an aralkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkylsilyl group, or an arylsilyl group, particularly preferably an alkyl group, an arylamino group, an aralkyl group, an alkenyl group, an aryl group, or a heteroaryl group, and most preferably an alkyl group, an arylamino group, an aralkyl group, an aryl group, or a heteroaryl group.

[0491] These substituents in the substituent group S may further have, as a substituent, a substituent selected from the substituent group S. The preferred groups, more preferred groups, further more preferred groups, particularly preferred groups, and most preferred groups of the substituents that may be had are the same as the preferred groups in the substituent group S.

[0492] (Ring A1) Ring A1 represents an aromatic hydrocarbon ring structure which may have a substituent or an aromatic heterocyclic structure which may have a substituent.

[0493] The aromatic hydrocarbon ring is preferably an aromatic hydrocarbon ring having a carbon number of 6 to 30. Specifically, a benzene ring, a naphthalene ring, an anthracene ring, a triphenylyl ring, an acenaphthene ring, a fluoranthene ring, and a fluorene ring are preferred.

[0494] The aromatic heterocycle is preferably an aromatic heterocycle having 3 to 30 carbon atoms and containing a nitrogen atom, oxygen atom, or sulfur atom as a heteroatom. A furan ring, a benzofuran ring, a thiophene ring, or a benzothiophene ring is more preferred. Ring A1 is more preferably a benzene ring, a naphthalene ring, or a fluorene ring, particularly preferably a benzene ring or a fluorene ring, and most preferably a benzene ring.

[0495] (Ring A2) Ring A2 represents an aromatic heterocyclic structure which may have a substituent. The aromatic heterocyclic ring is preferably an aromatic heterocyclic ring having 3 to 30 carbon atoms and containing a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom. Specific examples include a pyridine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, an imidazole ring, an oxazole ring, a thiazole ring, a benzothiazole ring, a benzoxazole ring, a benzimidazole ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring, a naphthyridine ring, and a phenanthridine ring. Preferred are a pyridine ring, a pyrazine ring, a pyrimidine ring, an imidazole ring, a benzothiazole ring, a benzoxazole ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, and a quinazoline ring. More preferred are a pyridine ring, an imidazole ring, a benzothiazole ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, and a quinazoline ring. Most preferred are a pyridine ring, an imidazole ring, a benzothiazole ring, a quinoline ring, a quinoxaline ring, and a quinazoline ring.

[0496] (Combination of Ring A1 and Ring A2) Preferred combinations of Ring A1 and Ring A2, when expressed as (Ring A1-Ring A2), include (benzene ring-pyridine ring), (benzene ring-quinoline ring), (benzene ring-quinoxaline ring), (benzene ring-quinazoline ring), (benzene ring-benzothiazole ring), (benzene ring-imidazole ring), (benzene ring-pyrrole ring), (benzene ring-diazole ring), and (benzene ring-thiophene ring).

[0497] (Substituents of Ring A1 and Ring A2) The substituents that Ring A1 and Ring A2 may have can be selected arbitrarily, but are preferably one or more types of substituents selected from the above-mentioned group S of substituents.

[0498] (Ar ２０１ , Ar ２０２ , Ar ２０３ ) Ar ２０１ , Ar ２０３ each independently represents an aromatic hydrocarbon ring structure which may have a substituent, or an aromatic heterocyclic ring structure which may have a substituent. ２０２represents an aromatic hydrocarbon ring structure which may have a substituent, an aromatic heterocyclic structure which may have a substituent, or an aliphatic hydrocarbon structure which may have a substituent.

[0499] Ar ２０１ , Ar ２０２ , Ar ２０３ is an aromatic hydrocarbon ring structure which may have a substituent, the aromatic hydrocarbon ring structure is preferably an aromatic hydrocarbon ring having 6 to 30 carbon atoms. Specifically, a benzene ring, a naphthalene ring, an anthracene ring, a triphenylyl ring, an acenaphthene ring, a fluoranthene ring, or a fluorene ring is preferred, a benzene ring, a naphthalene ring, or a fluorene ring is more preferred, and a benzene ring is most preferred.

[0500] Ar ２０１ , Ar ２０２ is a benzene ring which may have a substituent, at least one benzene ring is preferably bonded to an adjacent structure at an ortho position or a meta position, and more preferably at least one benzene ring is bonded to an adjacent structure at a meta position.

[0501] Ar ２０１ , Ar ２０２ , Ar ２０３ When either of the above is a fluorene ring which may have a substituent, the 9- and 9'-positions of the fluorene ring preferably have a substituent or are bonded to an adjacent structure.

[0502] Ar ２０１ , Ar ２０２ , Ar ２０３is an aromatic heterocyclic structure optionally having a substituent, the aromatic heterocyclic structure is preferably an aromatic heterocyclic ring having 3 to 30 carbon atoms and containing a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom, and specific examples thereof include a pyridine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, an imidazole ring, an oxazole ring, a thiazole ring, a benzothiazole ring, a benzoxazole ring, a benzimidazole ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring, a naphthyridine ring, a phenanthridine ring, a carbazole ring, a dibenzofuran ring, and a dibenzothiophene ring, and preferably a pyridine ring, a pyrimidine ring, a triazine ring, a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring.

[0503] Ar ２０１ , Ar ２０２ , Ar ２０３ When either of the above is a carbazole ring which may have a substituent, the N-position of the carbazole ring preferably has a substituent or is bonded to an adjacent structure.

[0504] Ar ２０２ When is an aliphatic hydrocarbon structure which may have a substituent, it is an aliphatic hydrocarbon structure having a linear, branched, or cyclic structure, and preferably has 1 or more and 24 or less carbon atoms, more preferably has 1 or more and 12 or less carbon atoms, and still more preferably has 1 or more and 8 or less carbon atoms.

[0505] (i1, i2, i3, i4, k1, k2) i1 and i2 each independently represent an integer of 0 to 12, preferably 1 to 12, more preferably 1 to 8, and even more preferably 1 to 6. Within this range, improved solubility and improved charge transport properties are expected. i3 preferably represents an integer of 0 to 5, more preferably 0 to 2, and even more preferably 0 or 1. i4 preferably represents an integer of 0 to 2, and even more preferably 0 or 1. k1 and k2 each independently represent an integer of 0 to 3, more preferably 1 to 3, more preferably 1 or 2, and particularly preferably 1.

[0506] (Ar ２０１ , Ar ２０２ , Ar２０３ Preferred substituents for Ar ２０１ , Ar ２０２ , Ar ２０３ The substituents that Ar may have can be arbitrarily selected, but are preferably one or more substituents selected from the above-mentioned substituent group S. Preferred groups are also the same as those in the above-mentioned substituent group S, but are more preferably unsubstituted (hydrogen atom), alkyl groups, or aryl groups, particularly preferably unsubstituted (hydrogen atom) or alkyl groups, and most preferably unsubstituted (hydrogen atom) or tertiary butyl groups, and the tertiary butyl groups are the same as those in Ar ２０３ If there is Ar ２０３ To, Ar ２０３ If there is no Ar ２０２ To, Ar ２０２ and Ar ２０３ If there is no Ar ２０１ It is preferred that the substituent is

[0507] (Preferred embodiment of the compound represented by formula (201)) The compound represented by formula (201) is preferably a compound that satisfies any one or more of the following (I) to (IV):

[0508] (I) Phenylene-linked structure The structure represented by formula (202) is preferably a structure having a group linked to benzene rings, i.e., a benzene ring structure, i1 being 1 to 6, with at least one of the benzene rings being bonded to an adjacent structure at the ortho or meta position. Such a structure is expected to improve solubility and charge transport properties.

[0509] (II) (phenylene)-aralkyl(alkyl) A structure having an aromatic hydrocarbon group or aromatic heterocyclic group to which an alkyl group or an aralkyl group is bonded in the ring A1 or ring A2, that is, Ar ２０１ is an aromatic hydrocarbon structure or an aromatic heterocyclic structure, i1 is 1 to 6, Ar ２０２ is an aliphatic hydrocarbon structure, i2 is 1 to 12, preferably 3 to 8, Ar ２０３ is a benzene ring structure, i3 is 0 or 1, preferably Ar ２０１is the aromatic hydrocarbon structure, more preferably a structure in which 1 to 5 benzene rings are linked together, and even more preferably a structure in which there is one benzene ring. Such a structure is expected to improve solubility and charge transport properties.

[0510] (III) Dendron A structure in which a dendron is bonded to ring A1 or ring A2, for example, Ar ２０１ , Ar ２０２ is a benzene ring structure, Ar ２０３ is a biphenyl or terphenyl structure, i1 and i2 are 1 to 6, i3 is 2, and j is 2. Such a structure is expected to improve solubility and charge transport properties.

[0511] (IV) B ２０１ -L ２００ -B ２０２ B ２０１ -L ２００ -B ２０２ The structure represented by the formula (203) is preferably a structure represented by the formula (204) below.

[0512]

[0513] In formula (203), R ２１１ , R ２１２ , R ２１３ each independently represents a substituent. In formula (204), ring B3 represents an aromatic heterocyclic structure containing a nitrogen atom, which may have a substituent. Ring B3 is preferably a pyridine ring.

[0514] (Preferred Phosphorescent Material) The phosphorescent material represented by the formula (201) is not particularly limited, but preferred examples include the following.

[0515]

[0516]

[0517] Also preferred is a phosphorescent material represented by the following formula (205):

[0518]

[0519] [In formula (205), M２ represents a metal, and T represents a carbon atom or a nitrogen atom. ９２ ~R ９５ each independently represents a substituent, provided that when T is a nitrogen atom, R ９４ and R ９５ There is none.]

[0520] In formula (205), M ２ Specific examples of the metal include metals selected from Groups 7 to 11 of the periodic table. Among these, preferred are ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, and gold, and particularly preferred are divalent metals such as platinum and palladium.

[0521] Also, in formula (205), R ９２ and R ９３ each independently represents a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an alkenyl group, a cyano group, an amino group, an acyl group, an alkoxycarbonyl group, a carboxyl group, an alkoxy group, an alkylamino group, an aralkylamino group, a haloalkyl group, a hydroxyl group, an aryloxy group, an aromatic hydrocarbon group, or an aromatic heterocyclic group.

[0522] Furthermore, when T is a carbon atom, R ９４ and R ９５ are each independently R ９２ and R ９３ In addition, when T is a nitrogen atom, R ９４ or R ９５ does not exist. ９２ ~R ９５ may further have a substituent. The substituent may be the same as those described above. ９２ ~R ９５ Any two or more of the groups may be linked to each other to form a ring.

[0523] (Molecular Weight) The molecular weight of the phosphorescent material is preferably 5000 or less, more preferably 4000 or less, and particularly preferably 3000 or less. The molecular weight of the phosphorescent material is preferably 800 or more, more preferably 1000 or more, and even more preferably 1200 or more. It is believed that by having the molecular weight within this range, the phosphorescent material does not aggregate and can be uniformly mixed with the charge transport material, thereby enabling the production of an emitting layer with high luminous efficiency.

[0524] The molecular weight of the phosphorescent material is preferably large in terms of high Tg, melting point, decomposition temperature, etc., and excellent heat resistance of the phosphorescent material and the formed light-emitting layer, and in terms of preventing deterioration of film quality due to gas generation, recrystallization, molecular migration, etc., and increase in impurity concentration due to thermal decomposition of the material, etc. On the other hand, the molecular weight of the phosphorescent material is preferably small in terms of facilitating purification of the organic compound.

[0525] <Charge Transport Material> The charge transport material used in the light-emitting layer is a material having a skeleton with excellent charge transport properties, and is preferably selected from electron transport materials, hole transport materials, and bipolar materials capable of transporting both electrons and holes.

[0526] Specific examples of skeletons having excellent charge transport properties include an aromatic structure, an aromatic amine structure, an arylamine structure, a dibenzofuran structure, a naphthalene structure, a phenanthrene structure, a phthalocyanine structure, a porphyrin structure, a thiophene structure, a benzylphenyl structure, a fluorene structure, a quinacridone structure, a triphenylene structure, a carbazole structure, a pyrene structure, an anthracene structure, a phenanthroline structure, a quinoline structure, a pyridine structure, a pyrimidine structure, a triazine structure, an oxadiazole structure, and an imidazole structure.

[0527] As the electron transporting material, from the viewpoint of a material having excellent electron transporting properties and a relatively stable structure, a compound having a pyridine structure, a pyrimidine structure, or a triazine structure is more preferable, and a compound having a pyrimidine structure or a triazine structure is even more preferable.

[0528] The hole transport material is a compound having a structure with excellent hole transport properties. Among the central skeletons with excellent charge transport properties, a carbazole structure, a dibenzofuran structure, an arylamine structure, a naphthalene structure, a phenanthrene structure, or a pyrene structure is preferred as a structure with excellent hole transport properties, and a carbazole structure, a dibenzofuran structure, or an arylamine structure is more preferred.

[0529] The charge transport material used in the light-emitting layer preferably has a fused ring structure of three or more rings, and more preferably is a compound having two or more fused ring structures of three or more rings or a compound having at least one fused ring of five or more rings. These compounds increase the rigidity of the molecules, making it easier to achieve the effect of suppressing the degree of molecular motion in response to heat. Furthermore, in terms of charge transport properties and material durability, it is preferable that the fused rings of three or more rings and the fused rings of five or more rings have an aromatic hydrocarbon ring or an aromatic heterocyclic ring.

[0530] Specific examples of the fused ring structure having three or more rings include an anthracene structure, a phenanthrene structure, a pyrene structure, a chrysene structure, a naphthacene structure, a triphenylene structure, a fluorene structure, a benzofluorene structure, an indenofluorene structure, an indolofluorene structure, a carbazole structure, an indenocarbazole structure, an indolocarbazole structure, a dibenzofuran structure, a dibenzothiophene structure, etc. From the viewpoint of charge transportability and solubility, at least one selected from the group consisting of a phenanthrene structure, a fluorene structure, an indenofluorene structure, a carbazole structure, an indenocarbazole structure, an indolocarbazole structure, a dibenzofuran structure, and a dibenzothiophene structure is preferred, and from the viewpoint of durability against charges, a carbazole structure or an indolocarbazole structure is more preferred.

[0531] In the present invention, from the viewpoint of durability of the organic electroluminescent device against charges, it is preferable that at least one of the charge transport materials in the light-emitting layer is a material having a pyrimidine skeleton or a triazine skeleton.

[0532] The charge transport material of the light-emitting layer is preferably a polymer material from the viewpoint of excellent flexibility. A light-emitting layer formed using a material with excellent flexibility is preferable as the light-emitting layer of an organic electroluminescent device formed on a flexible substrate. When the charge transport material contained in the light-emitting layer is a polymer material, the molecular weight is preferably 5,000 to 1,000,000, more preferably 10,000 to 500,000, and even more preferably 10,000 to 100,000.

[0533] Furthermore, the charge transport material of the light-emitting layer is preferably a low-molecular-weight material from the viewpoints of ease of synthesis and purification, ease of designing electron transport performance and hole transport performance, and ease of adjusting viscosity when dissolved in a solvent. When the charge transport material contained in the light-emitting layer is a low-molecular-weight material, the molecular weight is preferably 5,000 or less, more preferably 4,000 or less, particularly preferably 3,000 or less, and most preferably 2,000 or less, and is preferably 300 or more, more preferably 350 or more, and even more preferably 400 or more.

[0534] <Fluorescent Material> The fluorescent material is not particularly limited, but a compound represented by the following formula (211) is preferred.

[0535]

[0536] In the above formula (211), Ar ２４１ represents an aromatic hydrocarbon condensed ring structure which may have a substituent, Ar ２４２ , Ar ２４３ each independently represents an alkyl group, an aromatic hydrocarbon group, an aromatic hetero group, or a group formed by combining these groups, which may have a substituent; and n41 is an integer of 1 to 4.

[0537] Ar ２４１ represents an aromatic hydrocarbon condensed ring structure preferably having 10 to 30 carbon atoms, and specific ring structures include naphthalene, acenaphthene, fluorene, anthracene, phenanthrene, fluoranthene, pyrene, tetracene, chrysene, and perylene. ２４１is more preferably an aromatic hydrocarbon condensed ring structure having 12 to 20 carbon atoms, and specific examples of the ring structure include acenaphthene, fluorene, anthracene, phenanthrene, fluoranthene, pyrene, tetracene, chrysene, and perylene. ２４１ is more preferably an aromatic hydrocarbon condensed ring structure having 16 to 18 carbon atoms, and specific examples of the ring structure include fluoranthene, pyrene, and chrysene.

[0538] n41 is 1 to 4, preferably 1 to 3, more preferably 1 or 2, and most preferably 2.

[0539] Ar ２４２ , Ar ２４３ The alkyl group of Ar is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms. ２４２ , Ar ２４３ The aromatic hydrocarbon group of Ar is preferably an aromatic hydrocarbon group having 6 to 30 carbon atoms, more preferably an aromatic hydrocarbon group having 6 to 24 carbon atoms, and most preferably a phenyl group or a naphthyl group. ２４２ , Ar ２４３ The aromatic hetero group is preferably an aromatic hetero group having 3 to 30 carbon atoms, more preferably an aromatic hydrocarbon group having 5 to 24 carbon atoms, specifically preferably a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, more preferably a dibenzofuranyl group.

[0540] Ar ２４１ , Ar ２４２ , Ar ２４３ The substituent that may be possessed by is preferably a group selected from the substituent group S, more preferably a hydrocarbon group included in the substituent group S, and even more preferably a hydrocarbon group among the groups preferred as the substituent group S.

[0541] The charge transport material used together with the fluorescent light-emitting material is not particularly limited, but is preferably one represented by the following formula (212).

[0542]

[0543] In the above formula (212), R ２５１ , R２５２ are each independently a structure represented by formula (213), and R ２５３ represents a substituent, and R ２５３ When there are a plurality of n43, they may be the same or different, and n43 is an integer of 0 to 8.

[0544]

[0545] In the above formula (213), * represents a bond to the anthracene ring of formula (212), and Ar ２５４ , Ar ２５５ each independently represents an aromatic hydrocarbon structure which may have a substituent, or a heteroaromatic ring structure which may have a substituent; Ar ２５４ , Ar ２５５ When there are a plurality of each, they may be the same or different; n44 is an integer of 1 to 5; and n45 is an integer of 0 to 5.

[0546] Ar ２５４ is preferably an aromatic hydrocarbon structure which is a monocyclic or fused ring having 6 to 30 carbon atoms and which may have a substituent, and more preferably an aromatic hydrocarbon structure which is a monocyclic or fused ring having 6 to 12 carbon atoms and which may have a substituent.

[0547] Ar ２５５ is preferably an aromatic hydrocarbon structure which is a monocyclic or fused ring having 6 to 30 carbon atoms, which may have a substituent, or an aromatic heterocyclic structure which is a fused ring having 6 to 30 carbon atoms, which may have a substituent. ２５５ is more preferably an aromatic hydrocarbon structure which is a monocyclic or fused ring having 6 to 12 carbon atoms, which may have a substituent, or an aromatic heterocyclic structure which is a fused ring having 12 carbon atoms, which may have a substituent.

[0548] n44 is preferably an integer of 1 to 3, more preferably 1 or 2. n45 is preferably an integer of 0 to 3, more preferably 0 to 2.

[0549] The substituent R ２５３ , Ar ２５４ and Ar ２５５The substituent that may be possessed by is preferably a group selected from the above-mentioned substituent group S. More preferably, it is a hydrocarbon group included in the substituent group S, and even more preferably, it is a hydrocarbon group among the groups preferred as the substituent group S.

[0550] The molecular weight of the fluorescent material and the charge transport material is preferably 5,000 or less, more preferably 4,000 or less, particularly preferably 3,000 or less, and most preferably 2,000 or less, and is preferably 300 or more, more preferably 350 or more, and even more preferably 400 or more.

[0551] [Hole Blocking Layer] A hole blocking layer may be provided between the light emitting layer 5 and the electron injection layer described below. The hole blocking layer is a layer laminated on the light emitting layer 5 so as to be in contact with the interface of the light emitting layer 5 on the cathode 7 side.

[0552] This hole-blocking layer has the role of preventing holes migrating from the anode 2 from reaching the cathode 7 and the role of efficiently transporting electrons injected from the cathode 7 toward the light-emitting layer 5. The properties required for the material constituting the hole-blocking layer are high electron mobility and low hole mobility, a large energy gap (difference between HOMO and LUMO), and a high excited triplet level (T １ ) is high.

[0553] Examples of materials for the hole-blocking layer that satisfy these conditions include mixed ligand complexes such as bis(2-methyl-8-quinolinolato)(phenolato)aluminum and bis(2-methyl-8-quinolinolato)(triphenylsilanolato)aluminum; metal complexes such as bis(2-methyl-8-quinolinolato)aluminum-μ-oxo-bis-(2-methyl-8-quinolinolato)aluminum binuclear metal complex; styryl compounds such as distyrylbiphenyl derivatives (Japanese Patent Laid-Open No. 11-242996); triazole derivatives such as 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (Japanese Patent Laid-Open No. 7-41759); and phenanthroline derivatives such as bathocuproine (Japanese Patent Laid-Open No. 10-79297). Furthermore, compounds having at least one pyridine ring substituted at the 2-, 4-, and 6-positions, as described in WO 2005 / 022962, are also preferred as materials for the hole-blocking layer.

[0554] There is no limitation on the method for forming the hole blocking layer, and it can be formed by a wet film forming method, a vapor deposition method, or other methods.

[0555] The thickness of the hole blocking layer is arbitrary as long as it does not significantly impair the effects of the present invention, but is usually 0.3 nm or more, preferably 0.5 nm or more, and usually 100 nm or less, preferably 50 nm or less.

[0556] [Electron Transport Layer] The electron transport layer 6 is provided between the light emitting layer 5 and the cathode 7 for the purpose of further improving the current efficiency of the device.

[0557] The electron transport layer 6 is formed from a compound capable of efficiently transporting electrons injected from the cathode 7 between electrodes to which an electric field is applied, toward the light-emitting layer 5. The electron transporting compound used in the electron transport layer 6 is required to have a high efficiency of electron injection from the cathode 7, a high electron mobility, and the ability to efficiently transport the injected electrons.

[0558] Specific examples of the electron transporting compound used in the electron transport layer include metal complexes such as aluminum complexes of 8-hydroxyquinoline (Japanese Patent Laid-Open No. 59-194393), metal complexes of 10-hydroxybenzo[h]quinoline, oxadiazole derivatives, distyrylbiphenyl derivatives, silole derivatives, 3-hydroxyflavone metal complexes, 5-hydroxyflavone metal complexes, benzoxazole metal complexes, benzothiazole metal complexes, trisbenzimidazolylbenzene (U.S. Pat. No. 5,645,948), quinoxaline compounds (Japanese Patent Laid-Open No. 6-207169), phenanthroline derivatives (Japanese Patent Laid-Open No. 5-331459), 2-tert-butyl-9,10-N,N'-dicyanoanthraquinone diimine, n-type hydrogenated amorphous silicon carbide, n-type zinc sulfide, and n-type zinc selenide.

[0559] The thickness of the electron transport layer 6 is usually 1 nm or more, preferably 5 nm or more, and usually 300 nm or less, preferably 100 nm or less.

[0560] The electron transport layer 6 is formed by laminating it on the hole blocking layer by a wet film-forming method or a vacuum deposition method as described above. Usually, a vacuum deposition method is used. In the present invention, as described above, the electron transport layer can be formed by a wet film-forming method on the light-emitting layer containing a suitable light-emitting layer-forming material.

[0561] [Electron Injection Layer] The electron injection layer may be provided to efficiently inject electrons injected from the cathode 7 into the electron transport layer 6 or the light-emitting layer 5 .

[0562] To efficiently inject electrons, the material forming the electron injection layer is preferably a metal with a low work function. Examples include alkali metals such as sodium and cesium, and alkaline earth metals such as barium and calcium. The thickness of the electron injection layer is preferably 0.1 nm or more and 5 nm or less.

[0563] Furthermore, it is also preferable to dope an organic electron transporting material, typified by a nitrogen-containing heterocyclic compound such as bathophenanthroline or a metal complex such as an aluminum complex of 8-hydroxyquinoline, with an alkali metal such as sodium, potassium, cesium, lithium, or rubidium (as described in JP-A Nos. 10-270171, 2002-100478, and 2002-100482, for example), because this improves both the electron injection and transport properties and enables excellent film quality to be achieved.

[0564] The thickness of the electron injection layer is usually 5 nm or more, preferably 10 nm or more, and usually 200 nm or less, preferably 100 nm or less.

[0565] The electron injection layer is formed by laminating it on the light-emitting layer 5 or the hole blocking layer or electron transport layer 6 thereon by a wet film-forming method or a vacuum deposition method. Details of the wet film-forming method are the same as those of the light-emitting layer described above.

[0566] In some cases, the hole blocking layer, electron transporting layer, and electron injecting layer are formed into one layer by co-doping the electron transporting material with a lithium complex.

[0567] [Cathode] The cathode 7 plays a role of injecting electrons into the layer (electron injection layer or luminescent layer, etc.) on the luminescent layer 5 side.

[0568] The cathode 7 can be made of any of the materials used for the anode 2, but for efficient electron injection, it is preferable to use a metal with a low work function, such as tin, magnesium, indium, calcium, aluminum, silver, or an alloy thereof. Specific examples include low-work-function alloy electrodes such as a magnesium-silver alloy, a magnesium-indium alloy, or an aluminum-lithium alloy.

[0569] In terms of the stability of the organic electroluminescent device, it is preferable to protect the cathode made of a metal having a low work function by laminating a metal layer having a high work function and stability against the atmosphere on the cathode. Examples of the metal to be laminated include aluminum, silver, copper, nickel, chromium, gold, and platinum.

[0570] The thickness of the cathode is usually the same as that of the anode.

[0571] [Other Layers] The organic electroluminescent device of the present invention may further include other layers as long as the effects of the present invention are not significantly impaired. That is, the organic electroluminescent device of the present invention may include any of the above-described other layers between the anode and the cathode.

[0572] [Other Device Configurations] The organic electroluminescent device of the present invention may have a structure opposite to that described above, i.e., for example, a cathode, an electron injection layer, an electron transport layer, a hole blocking layer, a light-emitting layer, a hole transport layer, a hole injection layer, and an anode stacked in this order on a substrate.

[0573] When the organic electroluminescent element of the present invention is applied to an organic electroluminescent device, it may be used as a single organic electroluminescent element, or may be used in a configuration in which a plurality of organic electroluminescent elements are arranged in an array, or may be used in a configuration in which anodes and cathodes are arranged in an XY matrix.

[0574] [Method for manufacturing organic electroluminescent element] The method for manufacturing an organic electroluminescent element of the present invention is a method for manufacturing an organic electroluminescent element having an anode and a cathode on a substrate and an organic layer between the anode and the cathode, and can include a step of forming the organic layer by a wet film formation method using the composition of the present invention containing a solvent.

[0575] In the method for producing an organic electroluminescent device of the present invention, the organic layer is preferably an organic layer located between the anode and the light-emitting layer.

[0576] [Display Device] The display device (organic electroluminescent device display device) of the present invention comprises the organic electroluminescent device of the present invention. The type and structure of the display device of the present invention are not particularly limited, and it can be assembled using the organic electroluminescent device of the present invention according to a conventional method.

[0577] For example, the organic EL display device of the present invention can be formed by the method described in "Organic EL Display" (Ohmsha, published on August 20, 2004, by Shizuo Tokito, Chinaya Adachi, and Hideyuki Murata).

[0578] [Lighting Device] The lighting device (organic electroluminescent element lighting device) of the present invention includes the organic electroluminescent element of the present invention. The type and structure of the lighting device of the present invention are not particularly limited, and it can be assembled using the organic electroluminescent element of the present invention according to a conventional method.

[0579] The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to the following examples, and the present invention can be practiced with any modifications without departing from the gist of the present invention.

[0580] In this specification, Ac means an acetyl group, Ph means a phenyl group, dba means dibenzylideneacetone, and Amphos means [4-(N,N-dimethylamino)phenyl]di-tert-butylphosphine. ｔ Bu means a tertiary butyl group, and dppf means 1,1'-bis(diphenylphosphino)ferrocene.

[0581] <Synthesis of Compound 1> (Synthesis of Intermediate 1-2)

[0582]

[0583] 4-Bromoaniline (14.5 g, 84.29 mmol), intermediate 1-1 (8.3 g, 19.22 mmol), potassium phosphate (2 M aqueous solution, 104 mL), toluene (210 mL), and ethanol (104 mL) were charged into a flask, and the system was thoroughly purged with nitrogen and heated to 60°C. Bis(triphenylphosphine)palladium(II) dichloride (0.25 g, 0.36 mmol) was added, and the mixture was stirred at 63°C for 5 hours. Water was added to the reaction solution, and extraction was carried out with toluene. The organic layer was dried over anhydrous magnesium sulfate. The crude product was purified by column chromatography to obtain intermediate 1-2 (2.9 g, yield 72%).

[0584] (Synthesis of Intermediate 1-3)

[0585]

[0586] Intermediate 1-2 (2.9 g, 13.86 mmol), 2-bromo-9,9'-spirobifluorene (5.21 g, 13.18 mmol), sodium tert-butoxide (3.6 g, 35.59 mmol), and toluene (60 mL) were charged, and the system was thoroughly purged with nitrogen and heated to 60°C (Solution A1-1). 1,1'-bis(diphenylphosphino)ferrocene (dppf) (0.73 g, 1.32 mmol) was added to a 10 mL toluene solution of tris(dibenzylideneacetone)dipalladium chloroform complex (0.34 g, 0.33 mmol), and the mixture was heated to 60°C (Solution B1-1). Solution B1-1 was added to Solution A1-1 in a nitrogen stream, and the mixture was heated under reflux for 2.5 hours. After cooling to room temperature, toluene (200 mL) and water (100 mL) were added to the reaction solution, and the mixture was stirred and then separated. The aqueous layer was extracted with toluene (100 mL x 2). The organic layers were combined, dried over magnesium sulfate, and concentrated. The mixture was further purified by silica gel column chromatography to obtain intermediate 1-3 (3.6 g, yield 52%) as a pale yellow oil.

[0587] (Synthesis of Compound 1)

[0588]

[0589] Intermediate 1-3 (3.6 g, 6.87 mmol), 1,3-dibromobenzene (0.77 g, 3.27 mmol), sodium tert-butoxide (1.9 g, 19.62 mmol), and toluene (55 mL) were charged, and the system was thoroughly purged with nitrogen and heated to 60°C (Solution A1-2). [4-(N,N-dimethylamino)phenyl]di-tert-butylphosphine (Amphos) (0.28 g, 1.06 mmol) was added to a 10 mL toluene solution of tris(dibenzylideneacetone)dipalladium chloroform complex (0.136 g, 0.131 mmol), and the mixture was heated to 60°C (Solution B1-2). Solution B1-2 was added to Solution A1-2 in a nitrogen stream, and the mixture was heated under reflux for 3 hours. After cooling to room temperature, toluene (200 mL) and water (100 mL) were added to the reaction mixture, followed by stirring. The mixture was separated, the aqueous layer was extracted with toluene (100 mL x 2), the organic layers were combined, dried over magnesium sulfate, and concentrated. The mixture was further purified by silica gel column chromatography to obtain Compound 1 (1.9 g, yield 52%) as a colorless solid.

[0590] <Synthesis of Compound 2> (Synthesis of Intermediate 2-1)

[0591]

[0592] 3-Bromoaniline (5.90 g, 34.30 mmol), intermediate 1-1 (7.39 g, 17.11 mmol), potassium phosphate (2 M aqueous solution, 42 mL), toluene (176 mL), and ethanol (88 mL) were charged into a flask, and the system was thoroughly purged with nitrogen and heated to 60°C. Tetrakis(triphenylphosphine)palladium(0) (0.7946 g, 0.69 mmol) was added, and the mixture was stirred at 100°C for 3 hours. Water was added to the reaction solution, and extraction was carried out with toluene. The organic layer was dried over anhydrous sodium sulfate. The crude product was purified by column chromatography to obtain intermediate 2-1 (6.8 g, yield 95%).

[0593] (Synthesis of Intermediate 2-2)

[0594]

[0595] Intermediate 2-1 (2.97 g, 14.19 mmol), 2-bromo-9,9'-spirobifluorene (5.18 g, 13.10 mmol), sodium tert-butoxide (3.57 g, 37.15 mmol), and toluene (47 mL) were charged, and the system was thoroughly purged with nitrogen and heated to 60°C (Solution A2-1). 1,1'-bis(diphenylphosphino)ferrocene (0.3880 g, 0.6998 mmol) was added to a 10 mL toluene solution of tris(dibenzylideneacetone)dipalladium chloroform complex (0.1855 g, 0.1792 mmol), and the mixture was heated to 60°C (Solution B2-1). Solution B2-1 was added to Solution A2-1 in a nitrogen stream, and the mixture was heated under reflux for 2 hours. After cooling to room temperature, methylene chloride was added to the reaction mixture, followed by stirring, suction filtration, and concentration. Further purification by silica gel column chromatography gave intermediate 2-2 (4.99 g, yield 73%) as a pale yellow oil.

[0596] (Synthesis of Compound 2)

[0597]

[0598] Intermediate 2-2 (4.9930 g, 9.5344 mmol), 1,3-dibromobenzene (1.06 g, 4.4932 mmol), sodium tert-butoxide (2.2529 g, 23.4433 mmol), and toluene (90 mL) were charged, and the system was thoroughly purged with nitrogen and heated to 60°C (Solution A2-2). [4-(N,N-dimethylamino)phenyl]di-tert-butylphosphine (Amphos) (0.1874 g, 0.7061 mmol) was added to a 10 mL toluene solution of tris(dibenzylideneacetone)dipalladium chloroform complex (0.0836 g, 0.0913 mmol), and the mixture was heated to 60°C (Solution B2-2). Solution B2-2 was added to Solution A2-2 in a nitrogen stream, and the mixture was heated under reflux for 3 hours. After cooling to room temperature, methylene chloride (100 mL) was added to the reaction mixture, followed by stirring, suction filtration, and concentration. The mixture was further purified by silica gel column chromatography to give Compound 2 (1.95 g, yield 39%) as a colorless solid.

[0599] <Synthesis of Compound 3> (Synthesis of Intermediate 3-3)

[0600]

[0601] To the intermediate 3-1 (0.50 g, 0.77 mmol) and the intermediate 3-2 (1.23 g, 3.83 mmol), nitrogen-bubbled toluene (20 mL), ethanol (10 mL), and an aqueous solution of tripotassium phosphate (2.0 mol / L, 10 mL) were added in this order, and the mixture was heated to 50°C. ３ ) ４ (44 mg, 0.038 mmol) was added and the mixture was stirred at 90°C for 6 hours. After cooling to room temperature, saturated aqueous sodium chloride solution was added and extraction was carried out using toluene. The organic layer was washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate, and the solvent was then distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain intermediate 3-3 (yield 0.62 g, 73%).

[0602] (Synthesis of Compound 3)

[0603]

[0604] Toluene (20 mL) containing nitrogen was added to intermediate 3-3 (0.62 g, 0.56 mmol), bromobenzene (0.18 g, 1.12 mmol), and sodium tert-butoxide (0.15 g, 1.51 mmol) (Solution A3-1). ２ (dba) ３ To a solution of 2-(2-methyl-2-propanol) (51 mg, 0.056 mmol) in toluene (5 ml), Amphos (0.12 g, 0.45 mmol) was added and heated to 50°C (Solution B3-1). Solution B3-1 was added to Solution A3-1 in a nitrogen stream, and the mixture was heated to reflux for 7.5 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain Compound 3 (yield 0.21 g, 32%).

[0605] <Synthesis of Compound 4> (Synthesis of Intermediate 4-3)

[0606]

[0607] To the intermediate 4-1 (6.68 g, 24.5 mmol), the intermediate 4-2 (6.00 g, 24.5 mmol), and sodium tert-butoxide (6.35 g, 66.0 mmol), toluene (90 mL) with nitrogen bubbling was added (Solution A4-1). ２ (dba) ３ CHCl ３ To a solution of 4-hydroxybenzoic acid (0.63 g, 0.61 mmol) in toluene (30 ml), dppf (1.36 g, 2.45 mmol) was added and stirred at room temperature for 15 minutes (Solution B4-1). Solution B4-1 was added to Solution A4-1 in a nitrogen stream, and the mixture was heated to reflux for 6 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain Intermediate 4-3 (yield 8.62 g, 81%).

[0608] (Synthesis of Compound 4)

[0609]

[0610] To the intermediate 4-3 (2.83 g, 6.46 mmol), 3,3'-dibromobiphenyl (0.96 g, 3.08 mmol), and sodium tert-butoxide (1.60 g, 16.6 mmol), toluene (50 mL) was added with nitrogen bubbling (Solution A4-2). ２ (dba) ３ Amphos (0.65 g, 2.46 mmol) was added to a solution of methyl 2-(2-methyl-2-propanol) (0.28 g, 0.31 mmol) in toluene (15 ml), and the mixture was heated to 50°C (Solution B4-2). Solution B4-2 was added to Solution A4-2 in a nitrogen stream, and the mixture was heated to reflux for 6 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain Compound 4 (yield 0.70 g, 22%).

[0611] <Synthesis of Compound 5> (Synthesis of Compound 5)

[0612]

[0613] To the intermediate 4-3 (4.38 g, 10.0 mmol), 1,3,5-tribromobenzene (1.00 g, 3.18 mmol), and sodium tert-butoxide (2.47 g, 25.7 mmol), toluene (50 mL) was added with nitrogen bubbling (Solution A5-1). ２ (dba) ３ Amphos (0.67 g, 2.54 mmol) was added to a solution of methyl 2-(2-methyl-2-propanol) (0.29 g, 0.32 mmol) in toluene (20 ml), and the mixture was heated to 50°C (Solution B5-1). Solution B5-1 was added to Solution A5-1 in a nitrogen stream, and the mixture was heated to reflux for 6 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain Compound 5 (yield 0.50 g, 11%).

[0614] <Synthesis of Comparative Compound 1> (Synthesis of Intermediate C1-2)

[0615]

[0616] To the intermediate C1-1 (2.88 g, 13.6 mmol), 2-bromo-9,9'-spirobi[9H-fluorene] (5.13 g, 12.9 mmol), and sodium tert-butoxide (3.35 g, 34.8 mmol), nitrogen-bubbled toluene (30 mL) was added (Solution C1-1). ２ (dba) ３ CHCl ３ Dppf (0.72 g, 1.29 mmol) was added to a solution of dppf (0.33 g, 0.32 mmol) in toluene (15 ml), and the mixture was stirred at room temperature for 10 minutes (Solution D1-1). Solution D1-1 was added to Solution C1-1 in a nitrogen stream, and the mixture was heated to reflux for 4 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain intermediate C1-2 (yield 5.99 g, 88%).

[0617] (Synthesis of Comparative Compound 1)

[0618]

[0619] To the intermediate C1-2 (3.37 g, 6.41 mmol), 1-bromo-3-iodobenzene (0.86 g, 3.05 mmol), and sodium tert-butoxide (1.58 g, 16.5 mmol), toluene (50 mL) with nitrogen bubbling was added (Solution C1-2). ２ (dba) ３ To a solution of (0.28 g, 0.31 mmol) in toluene (15 ml), Amphos (0.66 g, 2.48 mmol) was added and heated to 50°C (Solution C1-2). Solution D1-2 was added to Solution C1-2 in a nitrogen stream, and the mixture was heated to reflux for 2 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain Comparative Compound 1 (yield 1.2 g, 35%).

[0620] <Synthesis of Comparative Compound 2> (Synthesis of Intermediate C2-2)

[0621]

[0622] To the intermediate C2-1 (0.76 g, 1.17 mmol) and phenylboronic acid (0.86 g, 7.02 mmol), nitrogen-bubbled toluene (20 mL), ethanol (10 mL), and an aqueous solution of tripotassium phosphate (2.0 mol / L, 10 mL) were added in this order, and the mixture was heated to 50°C. ３ ) ４ (81 mg, 0.070 mmol) was added and the mixture was stirred at 90°C for 6 hours. After cooling to room temperature, saturated aqueous sodium chloride solution was added and extraction was carried out using toluene. The organic layer was washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate, and the solvent was then distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain intermediate C2-2 (yield 0.68 g, 91%).

[0623] (Synthesis of Comparative Compound 2)

[0624]

[0625] To the intermediate C2-2 (0.62 g, 0.96 mmol), 4-bromobiphenyl (0.34 g, 1.45 mmol), and sodium tert-butoxide (0.25 g, 2.59 mmol), toluene (20 mL) was added with nitrogen bubbling (Solution C2-1). ２ (dba) ３ Amphos (20.4 mg, 0.076 mmol) was added to a solution of 2-(4-methyl-2-propanol)-2-propanol (8.8 mg, 0.0096 mmol) in toluene (10 ml), and the mixture was heated to 50°C (Solution D2-1). Solution D2-1 was added to Solution C2-1 in a nitrogen stream, and the mixture was heated to reflux for 3.5 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain comparative compound 2 (yield 0.63 g, 83%).

[0626] <Synthesis of Comparative Compound 3> (Synthesis of Intermediate C3-2)

[0627]

[0628] To the intermediate C3-1 (5.08 g, 12.7 mmol) and 4-vinylphenylboronic acid (1.87 g, 12.7 mmol), nitrogen-bubbled toluene (40 mL), ethanol (20 mL), and an aqueous solution of tripotassium phosphate (2.0 mol / L, 20 mL) were added in this order, and the mixture was heated to 50°C. ３ ) ４ (0.146 g, 0.127 mmol) was added and the mixture was stirred at 90°C for 4 hours. After cooling to room temperature, saturated aqueous sodium chloride solution was added and extraction was carried out using toluene. The organic layer was washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate, and the solvent was then distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain intermediate C3-2 (yield 0.88 g, 16%).

[0629] (Synthesis of Comparative Compound 3)

[0630]

[0631] To the intermediate C3-2 (0.79 g, 1.87 mmol), N,N'-diphenylbenzidine (0.29 g, 0.848 mmol), and sodium tert-butoxide (0.44 g, 4.58 mmol), toluene (30 mL) was added with nitrogen bubbling (Solution C3-1). ２ (dba) ３ Amphos (0.18 g, 0.68 mmol) was added to a solution of (77.7 mg, 0.085 mmol) in toluene (10 ml), and the mixture was heated to 50°C (Solution D3-1). Solution D3-1 was added to Solution C3-1 in a nitrogen stream, and the mixture was heated to reflux for 4 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain comparative compound 3 (yield 0.58 g, 67%).

[0632]

[0633]

[0634] <Evaluation of Solvent Resistance> The formation of a film for evaluating solvent resistance using the obtained compound and the evaluation of the solvent resistance of the obtained film were carried out as follows. First, a solution was prepared by dissolving Compound A in a concentration of 2.0 mass % and Compound B in a concentration of 0.4 mass % in ethyl benzoate. This solution was dropped onto an ITO substrate in the atmosphere to perform spin coating, and then dried on a hot plate at 100°C for 1 minute. Next, ultraviolet light was irradiated using a spot light source LC8 manufactured by Hamamatsu Photonics. The ultraviolet light irradiation was at 46 mW / cm ２ The substrate was dried on a hot plate at 230° C. to form a film for evaluating solvent resistance with a thickness of 30 nm.

[0635] Next, the substrate with the solvent resistance evaluation film formed thereon was placed on a spin coater, and 150 μL of the test solvent was dropped onto the substrate. After dropping, the substrate was allowed to stand for 90 seconds to conduct the solvent resistance test. Phenylcyclohexane was used as the test solvent. The substrate was then rotated at 1500 rpm for 30 seconds, then at 4000 rpm for 30 seconds to spin out the dropped solvent. The substrate was then dried on a hot plate at 145°C for 15 minutes. The solvent resistance was estimated from the change in film thickness before and after the solvent resistance test.

[0636] The solvent resistance of the compound after film formation was evaluated based on the following criteria: ◯◯: No decrease in film thickness was observed. ◯: 80% or more of the film was confirmed to remain. ×: The film dissolved and disappeared.

[0637] The combinations of Compound A and Compound B, and the time (baking time) for drying on a hot plate at 230°C after UV irradiation are summarized in Table 1. Table 1 also summarizes the films produced and the results of their solvent resistance tests.

[0638]

[0639]

[0640]

[0641]

[0642] <Fabrication of Organic Electroluminescent Devices> [Example 1] An organic electroluminescent device was fabricated by the following method. A 50 nm thick indium tin oxide (ITO) transparent conductive film (manufactured by Geomatec Co., Ltd., sputter-deposited film) was deposited on a glass substrate and patterned into 2 mm wide stripes using standard photolithography techniques and hydrochloric acid etching to form an anode. The substrate with the ITO pattern thus formed was cleaned in this order: ultrasonic cleaning with a surfactant aqueous solution, rinsing with ultrapure water, ultrasonic cleaning with ultrapure water, and rinsing with ultrapure water, then dried with compressed air, and finally cleaned with ultraviolet ozone.

[0643] A composition for forming a hole injection layer was prepared by dissolving 2.0 wt % of compound 3 having a structure included in formula (3-4) and 0.4 wt % of electron-accepting compound (A-1) having a structure included in formula (81) in ethyl benzoate. This composition was spin-coated onto the substrate in the atmosphere and dried on a hot plate at 100°C for 1 minute. Next, ultraviolet light was irradiated using a spot light source LC8 manufactured by Hamamatsu Photonics. The ultraviolet light irradiation was at 46 mW / cm. ２ The substrate was dried on a hot plate in the atmosphere at 230° C. for 30 minutes to form a uniform thin film with a thickness of 30 nm, which was used as a hole injection layer.

[0644] Next, a charge-transporting polymer compound having the following structural formula (HT-1) was dissolved in cyclohexylbenzene to prepare a 3.0 wt % solution. This solution was spin-coated onto the substrate on which the hole-injection layer had been formed in a nitrogen glove box, and dried on a hot plate in the nitrogen glove box at 230°C for 30 minutes to form a uniform thin film with a thickness of 50 nm, which served as a hole-transporting layer.

[0645]

[0646] Subsequently, as materials for the light-emitting layer, a composition for forming a light-emitting layer was prepared by dissolving in cyclohexylbenzene 1.25% by weight of compound (H-1), 1.25% by weight of compound (H-2), 2.5% by weight of compound (H-3), and 1.5% by weight of compound (D-1) having the following structure.

[0647]

[0648]

[0649] This solution was spin-coated in a nitrogen glove box onto the substrate on which the hole transport layer had been formed, and dried on a hot plate in the nitrogen glove box at 120°C for 20 minutes to form a uniform thin film with a thickness of 70 nm, which served as the light-emitting layer. The substrate on which the light-emitting layer had been formed was placed in a vacuum deposition apparatus, and the inside of the apparatus was heated to 2 × 10 －４ The pressure was then evacuated to a pressure of 0.1 Pa or less.

[0650] Next, the following structural formula (ET-1) and 8-hydroxyquinolinolatolithium were co-deposited on the light-emitting layer in a thickness ratio of 2:3 by vacuum deposition to form an electron transport layer with a thickness of 30 nm.

[0651]

[0652] Next, a 2 mm wide striped shadow mask was attached to the substrate as a mask for cathode deposition so as to be perpendicular to the ITO stripes of the anode, and aluminum was heated in a molybdenum boat to form an aluminum layer with a thickness of 80 nm, thereby forming a cathode. In this way, an organic electroluminescent device having a light-emitting area of ​​2 mm × 2 mm was obtained.

[0653] Example 2 An organic electroluminescent device was produced in the same manner as in Example 1, except that a composition for forming a hole injection layer of the present invention was prepared by dissolving 2.0 wt % of compound 3 included in formula (3-4) and 0.4 wt % of an electron-accepting compound (A-2) having a structure included in formula (81) in ethyl benzoate, and using this composition to form a hole injection layer.

[0654] Example 3 An organic electroluminescent device was produced in the same manner as in Example 1, except that a composition for forming a hole injection layer of the present invention was prepared by dissolving 2.0 wt % of compound 2 included in formula (3-1) and 0.4 wt % of electron-accepting compound (A-1) included in formula (81) in ethyl benzoate, and the hole injection layer was formed using this composition.

[0655] Comparative Example 1 A comparative composition for forming a hole injection layer was prepared by dissolving 2.0 wt % of Comparative Compound 3 and 0.4 wt % of the electron-accepting compound (A-1) represented by Formula (81) in ethyl benzoate, and an organic electroluminescent device was produced in the same manner as in Example 1, except that the hole injection layer was formed using this composition.

[0656] [Evaluation of Devices] The organic electroluminescent devices obtained in Examples 1 to 3 and Comparative Example 1 were evaluated for luminance at 1,000 cd / m ２ The current efficiency (cd / A) was measured when the composition of Comparative Example 1 was set to 1. The results are shown in Table 2. The results in Table 2 demonstrate that the organic electroluminescent device using the composition of the present invention has improved luminous efficiency.

[0657]

[0658] Example 4 A composition for forming a hole injection layer of the present invention was prepared by dissolving 1.0 wt % of compound 1 having a structure represented by formula (3-1), 1.0 wt % of a hole transporting polymer compound having a repeating structure represented by formula (P-1) below, and 0.4 wt % of an electron accepting compound (A-1) represented by formula (81) in ethyl benzoate.

[0659]

[0660] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that this composition was spin-coated onto the substrate in the atmosphere and dried on a hot plate in the atmosphere at 230°C for 30 minutes to form a uniform thin film with a thickness of 30 nm, which was used as a hole injection layer.

[0661] Example 5 An organic electroluminescent device was produced in the same manner as in Example 4, except that a composition for forming a hole injection layer of the present invention was prepared by dissolving 1.0 wt % of compound 2 included in formula (3-1), 1.0 wt % of (P-1), and 0.4 wt % of the electron-accepting compound (A-1) included in formula (81) in ethyl benzoate, and the hole injection layer was formed using this composition.

[0662] Comparative Example 2 A comparative composition for forming a hole injection layer was prepared by dissolving 1.0 wt % of compound 2 included in formula (3-1), 1.0 wt % of polymer compound (P-1), and 0.4 wt % of electron-accepting compound (CA-1) in ethyl benzoate, and an organic electroluminescent device was produced in the same manner as in Example 4, except that the hole injection layer was formed using this composition.

[0663] [Evaluation of Devices] The organic electroluminescent devices obtained in Examples 4 and 5 and Comparative Example 2 were subjected to a luminance test at 1,000 cd / m ２ The current efficiency (cd / A) was measured when the composition of Comparative Example 2 was set to 1. The results are shown in Table 3. The results in Table 3 demonstrate that the organic electroluminescent device using the composition of the present invention has improved luminous efficiency.

[0664]

[0665] In the organic electroluminescent devices obtained in Examples 3 and 5, the current was 15 mA / cm ２ When a current was continuously applied to the element at a current density of 1000 kJ / s, the time (LT95) until the luminance decreased to 95% of the initial luminance was measured. The results of these measurements are shown in Table 4. In Table 4, the values ​​for Example 5 are relative values, with the value for Example 3 being taken as 1. The results in Table 4 demonstrate that the luminous efficiency and operating life of an organic electroluminescent device in which a polymer was added to the composition of the present invention were improved.

[0666]

[0667] Example 6 An organic electroluminescent device was fabricated as follows. A 50 nm thick indium tin oxide (ITO) transparent conductive film (manufactured by Geomatec Co., Ltd., sputter-deposited) was deposited on a glass substrate and patterned into 2 mm wide stripes using standard photolithography and hydrochloric acid etching to form an anode. The substrate with the ITO pattern thus formed was cleaned in this order: ultrasonic cleaning with a surfactant aqueous solution, rinsing with ultrapure water, ultrasonic cleaning with ultrapure water, and rinsing with ultrapure water, then dried with compressed air, and finally cleaned with ultraviolet ozone.

[0668] A composition for forming a hole injection layer was prepared by dissolving 2.0 wt % of compound 4 having a structure included in formula (3-3) and 0.4 wt % of electron-accepting compound (A-1) included in formula (81) in ethyl benzoate. This composition was spin-coated onto the substrate in the atmosphere and dried on a hot plate at 100°C for 1 minute. Next, ultraviolet light was irradiated using a spot light source LC8 manufactured by Hamamatsu Photonics. The ultraviolet light irradiation was at 46 mW / cm. ２ The substrate was dried on a hot plate in the atmosphere at 230° C. for 30 minutes to form a uniform thin film with a thickness of 30 nm, which was used as a hole injection layer.

[0669] Next, a charge-transporting polymer compound having the following structural formula (HT-1) was dissolved in cyclohexylbenzene to prepare a 3.0 wt % solution. This solution was spin-coated in a nitrogen glove box onto the substrate on which the hole-injection layer had been formed, and dried on a hot plate in the nitrogen glove box at 230°C for 30 minutes to form a uniform thin film with a thickness of 40 nm, which served as a hole-transporting layer.

[0670]

[0671] Subsequently, as a material for the light-emitting layer, a compound (H-4) having the following structure was dissolved in cyclohexylbenzene at a concentration of 4.0 wt % and (D-2) was dissolved in cyclohexylbenzene at a concentration of 0.4 wt %, to prepare a composition for forming the light-emitting layer.

[0672]

[0673] This solution was spin-coated in a nitrogen glove box onto the substrate on which the hole transport layer had been formed, and dried on a hot plate in the nitrogen glove box at 120°C for 20 minutes to form a uniform thin film with a thickness of 40 nm, which served as the light-emitting layer. After forming the light-emitting layer, an organic electroluminescent device was fabricated in the same manner as in Example 1.

[0674] Example 7 An organic electroluminescent device was produced in the same manner as in Example 6, except that a composition for forming a hole injection layer of the present invention was prepared by dissolving 2.0 wt % of compound 5 included in formula (3-2) and 0.4 wt % of electron-accepting compound (A-2) included in formula (81) in ethyl benzoate, and the hole injection layer was formed using this composition.

[0675] Comparative Example 3 A comparative composition for forming a hole injection layer was prepared by dissolving 2.0 wt % of compound 4 included in formula (3-3) and 0.4 wt % of electron-accepting compound (CA-1) in ethyl benzoate, and an organic electroluminescent device was produced in the same manner as in Example 6, except that the hole injection layer was formed using this composition.

[0676] Comparative Example 4 A comparative composition for forming a hole injection layer was prepared by dissolving Comparative Compound 3 at a concentration of 2.0 wt % and electron-accepting compound (CA-1) at a concentration of 0.4 wt % in ethyl benzoate, and an organic electroluminescent device was produced in the same manner as in Example 6, except that the hole injection layer was formed using this composition.

[0677] Example 8 A composition for forming a hole injection layer of the present invention was prepared by dissolving 1.0 wt % of compound 4 included in formula (3-3), 1.0 wt % of a hole transporting polymer compound having a repeating structure of formula (P-2) below, and 0.4 wt % of electron accepting compound (A-1) included in formula (81) in ethyl benzoate.

[0678]

[0679] An organic electroluminescent device was fabricated in the same manner as in Example 6, except that this composition was spin-coated onto the substrate in the atmosphere and dried on a hot plate in the atmosphere at 230°C for 30 minutes to form a uniform thin film with a thickness of 30 nm, which was used as a hole injection layer.

[0680] Example 9 An organic electroluminescent device was produced in the same manner as in Example 8, except that a composition for forming a hole injection layer of the present invention was prepared by dissolving 1.0 wt % of compound 5 included in formula (3-2), 1.0 wt % of polymer compound (P-2), and 0.4 wt % of electron-accepting compound (A-1) included in formula (81) in ethyl benzoate, and the hole injection layer was formed using this composition.

[0681] Comparative Example 5 A comparative composition for forming a hole injection layer was prepared by dissolving 1.0 wt % of Comparative Compound 3, 1.0 wt % of Polymer Compound (P-2), and 0.4 wt % of the electron-accepting compound (A-1) represented by Formula (81) in ethyl benzoate, and an organic electroluminescent device was produced in the same manner as in Example 8, except that the hole injection layer was formed using this composition.

[0682] [Evaluation of Devices] The organic electroluminescent devices obtained in Examples 6 to 9 and Comparative Examples 3 to 5 were evaluated at 1,000 cd / m ２ The current efficiency (cd / A) was measured when the composition of Comparative Example 4 was used as 1. The results are shown in Table 5. It was found from the results in Table 5 that the organic electroluminescent device using the composition of the present invention had improved luminous efficiency.

[0683]

[0684] Although the present invention has been described in detail with reference to specific embodiments, it will be apparent to those skilled in the art that various modifications can be made without departing from the spirit and scope of the invention.

[0685] Although various embodiments have been described above with reference to the drawings, it goes without saying that the present invention is not limited to such examples. It is clear that a person skilled in the art can conceive of various modifications or alterations within the scope of the claims, and it is understood that these also naturally fall within the technical scope of the present invention. Furthermore, the components of the above-described embodiments may be combined in any manner without departing from the spirit of the invention.

[0686] This application is based on a Japanese patent application (Patent Application No. 2022-054580) filed on March 29, 2022, the contents of which are incorporated herein by reference.

[0687] The composition of the present invention can be used to improve the luminous efficiency of organic electroluminescent devices.

[0688] REFERENCE SIGNS LIST 1 substrate 2 anode 3 hole injection layer 4 hole transport layer 5 light emitting layer 6 electron transport layer 7 cathode 8 organic electroluminescent device

Claims

1. A composition comprising an arylamine compound represented by any one of the following formulas (3-1) to (3-4) and an electron accepting compound represented by the following formula (81): 【Chemistry 1】 (In formulas (3-1) to (3-4), Ar ２ , Ar ３ each independently represents any one of formulas (4-1) to (4-3), Multiple R ２ each independently represents a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, Each of the multiple a2's independently represents 0 or 1; Multiple A's ２ are each independently a hydrogen atom or a bridging group. 【Chemistry 2】 (In formulas (4-1) to (4-3), * indicates the bond position. Multiple R １ each independently represents a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, Each of the multiple a1's is independently 0 or 1; Multiple A's １ are each independently a hydrogen atom or a bridging group. However, all A １ At least one of the groups consisting of the above-mentioned bridging group. 【Chemistry 3】 (In formula (81), five R ８１ , 5 R's ８２ , 5 R's ８３ , 5 R's ８４ are independent of each other, and R ８１ ~R ８４ each independently represents a hydrogen atom, a deuterium atom, a halogen atom, an aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 50 carbon atoms which may have a substituent, a fluorine-substituted alkyl group having 1 to 12 carbon atoms, or a bridging group. Ph １ , Ph ２ , Ph ３ , Ph ４ are symbols that refer to each benzene ring. X ＋ represents a counter cation. However, formula (81) has at least two bridging groups.

2. The composition according to claim 1, further comprising a polymer having an arylamine structure represented by the following formula (50) as a repeating unit and having a crosslinking group: 【Chemistry 4】 (In formula (50), Ar ５１ represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a group in which a plurality of groups selected from aromatic hydrocarbon groups and aromatic heterocyclic groups are linked together; Ar ５２ represents a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group, or a divalent group in which a plurality of at least one group selected from the group consisting of the divalent aromatic hydrocarbon group and the divalent aromatic heterocyclic group are linked together directly or via a linking group. Ar ５１ and Ar ５２ may form a ring via a single bond or a linking group. Ar ５１ , Ar ５２ may have a substituent.)

3. The composition according to claim 2, wherein the arylamine compound represented by any one of formulas (3-1) to (3-4), the electron accepting compound represented by formula (81), and the polymer having the arylamine structure represented by formula (50) as a repeating unit each independently have a crosslinking group selected from formulas (X1) to (X17) in the following crosslinking group group T: <Bridging group group T> 【Chemistry 5】 In formulas (X1) to (X17), Q represents a direct bond or a linking group. * indicates the bond position. R in formula (X3), formula (X4), formula (X5) and formula (X9) １１０ represents a hydrogen atom or an alkyl group which may have a substituent. In the formulae (X1) to (X3), the benzene ring and the naphthalene ring may have a substituent. In addition, the substituents may be bonded to each other to form a ring. In formula (X1) and formula (X2), the cyclobutene ring may have a substituent.

4. The composition according to claim 3, wherein the crosslinking group is any one of the formulas (X1) to (X3).

5. The composition according to claim 2, wherein the repeating unit represented by the formula (50) is a repeating unit represented by the following formula (54): 【Chemistry 6】 (In formula (54), Ar ５１ represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a group in which a plurality of groups selected from aromatic hydrocarbon groups and aromatic heterocyclic groups are linked together; X is -C(R ２０７ ) (R ２０８ ) -, -N(R ２０９ )-or-C(R ２１１ ) (R ２１２ )-C(R ２１３ ) (R ２１４ ) - and R ２０１ , R ２０２ , R ２２１ and R ２２２ each independently represents an alkyl group which may have a substituent, R ２０７ ~R ２０９ and R ２１１ ~R ２１４ each independently represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aralkyl group, or an optionally substituted aromatic hydrocarbon group, a and b each independently represent an integer from 0 to 4; c is an integer from 0 to 3; d is an integer from 0 to 4; i and j each independently represent an integer from 0 to 3.

6. Ar ２ , Ar ３ , Ar ５１ , Ar ５２ , R １ , R ２ , R ２０１ , R ２０２ , R ２２１ , R ２２２ , R ２０７ ~R ２０９ , R ２１１ ~R ２１４ The composition according to claim 5 , wherein none of the groups has a substituent.

7. The composition according to any one of claims 1 to 6, further comprising a solvent.

8. 8. A method for manufacturing an organic electroluminescence device having an anode and a cathode on a substrate, and an organic layer between the anode and the cathode, the method comprising the step of forming the organic layer by a wet film formation method using the composition according to claim 7.

9. The method for producing an organic electroluminescent device according to claim 8 , wherein the organic layer is an organic layer between the anode and the light-emitting layer.

10. The organic electroluminescence device has an anode and a cathode on a substrate, and an organic layer between the anode and the cathode, wherein the organic layer contains a crosslinked reaction product of an arylamine compound represented by any one of the following formulas (3-1) to (3-4) and an electron-accepting compound represented by the following formula (81): 【Chemistry 7】 (In formulas (3-1) to (3-4), Ar ２ , Ar ３ each independently represents any one of formulas (4-1) to (4-3), Multiple R ２ each independently represents a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, Each of the multiple a2's independently represents 0 or 1; Multiple A's ２ are each independently a hydrogen atom or a bridging group. 【Chemistry 8】 (In formulas (4-1) to (4-3), * indicates the bond position. Multiple R １ each independently represents a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, Each of the multiple a1's is independently 0 or 1; Multiple A's １ are each independently a hydrogen atom or a bridging group. However, all A １ At least one of the groups consisting of the above-mentioned bridging group. 【Chemistry 9】 (In formula (81), five R ８１ , 5 R's ８２ , 5 R's ８３ , 5 R's ８４ are independent of each other, and R ８１ ~R ８４ each independently represents a hydrogen atom, a deuterium atom, a halogen atom, an aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 50 carbon atoms which may have a substituent, a fluorine-substituted alkyl group having 1 to 12 carbon atoms, or a bridging group. Ph １ , Ph ２ , Ph ３ , Ph ４ are symbols that refer to each benzene ring. X ＋ represents a counter cation. However, formula (81) has at least two bridging groups.

11. The organic electroluminescence device has an anode and a cathode on a substrate, and an organic layer between the anode and the cathode, wherein the organic layer contains a crosslinking reaction product between an arylamine compound represented by any one of formulas (3-1) to (3-4) below and a polymer having an arylamine structure represented by formula (50) below as a repeating unit and having a crosslinking group. 【Chemistry 10】 (In formulas (3-1) to (3-4), Ar ２ , Ar ３ each independently represents any one of formulas (4-1) to (4-3), Multiple R ２ each independently represents a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, Each of the multiple a2's independently represents 0 or 1; Multiple A's ２ are each independently a hydrogen atom or a bridging group. 【Chemistry 11】 (In formulas (4-1) to (4-3), * indicates the bond position. Multiple R １ each independently represents a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, Each of the multiple a1's is independently 0 or 1; Multiple A's １ are each independently a hydrogen atom or a bridging group. However, all A １ At least one of the groups consisting of the above-mentioned bridging group. 【Chemistry 12】 (In formula (50), Ar ５１ represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a group in which a plurality of groups selected from aromatic hydrocarbon groups and aromatic heterocyclic groups are linked together; Ar ５２ represents a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group, or a divalent group in which a plurality of at least one group selected from the group consisting of the divalent aromatic hydrocarbon group and the divalent aromatic heterocyclic group are linked together directly or via a linking group. Ar ５１ and Ar ５２ may form a ring via a single bond or a linking group. Ar ５１ , Ar ５２ may have a substituent.)

12. Ar ２ , Ar ３ , Ar ５１ , Ar ５２ , R １ , R ２ The organic electroluminescent device according to claim 11 , wherein none of the groups has a substituent.

13. An organic electroluminescent device manufactured by the manufacturing method of an organic electroluminescent device described in claim 8.

14. A display device comprising an organic electroluminescent element according to claim 10.

15. A lighting device comprising an organic electroluminescent element according to any one of claims 10 to 12.

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