Organic electroluminescent element, display, lighting device

Abstract

To provide an organic electroluminescent element with excellent luminous efficiency.SOLUTION: In an organic electroluminescent element having an anode, a cathode, a first organic layer and a second organic layer, the first organic layer is provided between the anode and the cathode, the second organic layer is formed adjacent to the anode side of the first organic layer, the first organic layer contains compounds represented by specific formula (240) or formula (241), and the second organic layer contains polymers having a triarylamine structure and lacking crosslinking groups.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to an organic electroluminescent device, a display device, and a lighting device. [Background technology]

[0002] Various electronic devices using organic EL elements, such as organic EL lighting and organic EL displays, have been put to practical use. Organic electroluminescent elements consume little power due to the low applied voltage and are capable of emitting light in all three primary colors, so they are beginning to be applied not only to large display monitors but also to small and medium-sized displays such as those used in mobile phones and smartphones.

[0003] Organic electroluminescent devices are manufactured by stacking multiple layers, such as a light-emitting layer, a charge injection layer, and a charge transport layer. Currently, most organic electroluminescent devices are manufactured by depositing organic materials under vacuum, but the vacuum deposition method requires a complicated deposition process and is poor in productivity. Furthermore, it is extremely difficult to enlarge the panels of organic electroluminescent devices manufactured by the vacuum deposition method for lighting or displays.

[0004] In recent years, wet film formation (coating) has been researched as an efficient process for manufacturing organic electroluminescent elements that can be used in large displays and lighting. The wet film formation method has the advantage of being able to easily form stable layers compared to vacuum deposition methods, and is therefore expected to be applied to the mass production of displays and lighting devices and to large devices.

[0005] Patent Document 1 discloses an organic electroluminescent device in which an emitting layer containing a compound having a biscarbazole skeleton as shown below is formed by a vacuum deposition method, and attempts are made to improve the driving voltage and efficiency.

[0006] [ka]

[0007] Patent Document 2 discloses an organic electroluminescent device in which an emitting layer containing a compound having a biscarbazole skeleton as shown below is formed by a wet film-forming method, and attempts are made to provide a composition for forming an emitting layer for an organic electroluminescent device that has excellent solubility in organic solvents.

[0008] [ka] [Prior art documents] [Patent documents]

[0009] [Patent Document 1] Japan Special Publication No. 2019-525463 [Patent Document 2] Japanese Patent Application Publication No. 2020-105152 Summary of the Invention [Problem to be solved by the invention]

[0010] However, the above-mentioned prior art cannot be said to be sufficient in terms of the performance of the organic electroluminescent element for display applications, and there has been a demand for further improvement in the luminous efficiency and driving life of organic electroluminescent elements formed by a wet film-forming method.

[0011] The present invention has been made in view of the above-mentioned conventional circumstances, and an object to be achieved is to provide an organic electroluminescent device that has a low driving voltage, high luminous efficiency, and a long driving life. [Means for solving the problem]

[0012] As a result of extensive investigations, the present inventors have found that the above-mentioned problems can be solved by using an organic layer containing a polymer having a triarylamine structure and no crosslinking group, and have thus completed the present invention.

[0013] That is, the gist of the present invention is as follows. A first aspect of the present invention is an organic electroluminescent device having an anode, a cathode, a first organic layer, and a second organic layer, the first organic layer is provided between the anode and the cathode; the second organic layer is in contact with the anode side of the first organic layer, The first organic layer contains a compound represented by the following formula (240) or the following formula (241): The second organic layer is an organic electroluminescent device containing a polymer having a triarylamine structure and no crosslinking group.

[0014] [ka]

[0015] (In formula (240), Ar 611 , Ar 612 each independently represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. R 611 , R 612 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, or a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent; R 611 and R 612 At least one of these represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms. G represents a single bond or a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. n 611 , n 612 are each independently an integer of 1 to 4.

[0016] [ka]

[0017] (In formula (241), Ar 613 ~Ar 615 each independently represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. R 613 , R 614 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, or a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent; R 613 and R 614 At least one of these represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms. G 612 , G 613 each independently represents a single bond or a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. n 613 , n 614 are each independently an integer of 1 to 4.

[0018] A second aspect of the present invention is the organic electroluminescent device of the first aspect, Ar in the formula (240) 611 and Ar 612 are each independently a monovalent group in which a plurality of benzene rings, which may have a substituent, are bonded in a linear or branched manner.

[0019] A third aspect of the present invention is the organic electroluminescent device of the first or second aspect, Ar in the formula (241) 613 ~Ar 615 are each independently a monovalent group in which a plurality of benzene rings, which may have a substituent, are bonded in a linear or branched manner.

[0020] A fourth aspect of the present invention is the organic electroluminescent device according to any one of the first to third aspects, R in the formula (240) and the formula (241) 611 ~R 614 are each independently a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent.

[0021] A fifth aspect of the present invention is the organic electroluminescent device according to any one of the first to fourth aspects, The organic electroluminescent device is one in which the polymer in the second organic layer has one or more repeating units selected from the group consisting of a repeating unit represented by the following formula (54), a repeating unit represented by the following formula (55), a repeating unit represented by the following formula (56), and a repeating unit represented by the following formula (57).

[0022] [ka]

[0023] (In formula (54), Ar 51 is a monovalent group in which a plurality of groups selected from an aromatic hydrocarbon group which may have a substituent other than a crosslinking group, an aromatic heterocyclic group which may have a substituent other than a crosslinking group, and an aromatic hydrocarbon group which may have a substituent other than a crosslinking group and an aromatic heterocyclic group which may have a substituent other than a crosslinking group are linked directly or via a linking group, 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 other than a crosslinking group, R 207 ~R 209 and R 211 ~R 214 each independently represents a hydrogen atom, an alkyl group which may have a substituent other than a bridging group, an aralkyl group which may have a substituent other than a bridging group, or a monovalent aromatic hydrocarbon group which may have a substituent other than a bridging group; a, b, and d each independently represent an integer of 0 to 4; c is an integer from 0 to 3, However, if a is 1 or more, c is 1 or more, and if b is 1 or more, d is 1 or more, R 201If 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, 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, i and j are each independently an integer of 0 to 3.

[0024] [ka]

[0025] (In formula (55), Ar 51 is Ar in the formula (54). 51 is the same as R 303 and R 306 each independently represents an alkyl group which may have a substituent other than a crosslinking group, R 304 and R 305 each independently represents an alkyl group which may have a substituent other than a crosslinking group, an alkoxy group which may have a substituent other than a crosslinking group, or an aralkyl group which may have a substituent other than a crosslinking group, l, n, p, and q are each independently 0 or 1; m is 1 or 2; However, if p is 1, then l is 1, and if q is 1, then n is 1.)

[0026] [ka]

[0027] (In formula (56), Ar 51 is Ar in the formula (54).51 is the same as Ar 41 represents a divalent aromatic hydrocarbon group which may have a substituent other than a bridging group, a divalent aromatic heterocyclic group which may have a substituent other than a bridging group, or a divalent group in which a plurality of groups selected from the group consisting of the divalent aromatic hydrocarbon groups and the divalent aromatic heterocyclic groups are linked together directly or via a linking group, R 441 and R 442 each independently represents an alkyl group which may have a substituent other than a crosslinking group, t is 1 or 2; u is 0 or 1; r and s each independently represent an integer of 0 to 4, However, if s is 1 or greater, then u is 1.)

[0028] [ka]

[0029] (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 other than a crosslinking group, an alkoxy group which may have a substituent other than a crosslinking group, an aralkyl group which may have a substituent other than a crosslinking group, a monovalent aromatic hydrocarbon group which may have a substituent other than a crosslinking group, or a monovalent aromatic heterocyclic group which may have a substituent other than a crosslinking group; f, g, and h each independently represent an integer of 0 to 4; e is an integer from 0 to 3, However, if g is 1 or greater, e is 1 or greater.)

[0030] A sixth aspect of the present invention is the organic electroluminescent device of the fifth aspect, the polymer in the second organic layer has one or more repeating units selected from the repeating units represented by formula (54), the repeating units represented by formula (55), the repeating units represented by formula (56), and the repeating units represented by formula (57), In the formula (54), a+b is 1 or more, In the formula (56), r+s is 1 or more, In the organic electroluminescent device, f+g+h in the formula (57) is 1 or more.

[0031] A seventh aspect of the present invention is the organic electroluminescent device of the sixth aspect, The polymer in the second organic layer has two or more repeating units selected from the repeating unit represented by formula (54), the repeating unit represented by formula (55), the repeating unit represented by formula (56), and the repeating unit represented by formula (57).

[0032] Aspect 8 of the present invention relates to the organic electroluminescent device of aspect 6 or aspect 7, The organic electroluminescent device is one in which the polymer in the second organic layer is composed of only one or more repeating units selected from the repeating units represented by formula (54), the repeating units represented by formula (55), the repeating units represented by formula (56), and the repeating units represented by formula (57).

[0033] A ninth aspect of the present invention is the organic electroluminescent device according to any one of the fifth to eighth aspects, The organic electroluminescent device is one in which the polymer in the second organic layer contains a partial structure represented by the following formula (61) or (61'):

[0034] [ka]

[0035] (In formula (61) and formula (61'), R 601 is R in the formula (54)201 or R 202 , R in the formula (55) 303 , R 304 , R 305 , or R 306 , R in the formula (56) 441 or R 442 , R in the formula (57) 517 , R 518 , or R 519 and -* represents a bond to the adjacent atom. When formula (61) and formula (61') are 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 R 601 In addition, when Ring A and Ring B are a partial structure of the formula (54), R 201 or R 202 When the partial structure of the formula (55) is R 303 , R 304 , R 305 , or R 306 If it is a partial structure of formula (56), R 441 or R 442 If it is a partial structure of formula (57), R 517 , R 518 or R 519 )

[0036] A tenth aspect of the present invention is the organic electroluminescent device according to any one of the first to ninth aspects, In the organic electroluminescent device, the first organic layer further contains a compound represented by the following formula (7):

[0037] [ka]

[0038] [In formula (7), ring A701 represents an aromatic hydrocarbon ring structure which may have a substituent or an aromatic heterocyclic structure which may have a substituent.] Ring A702 represents an aromatic heterocyclic structure which may have a substituent. When a plurality of rings A701 and a plurality of rings A702 are present, they may be the same or different. R 701 , R 702 are each independently a structure represented by formula (b), and "*" indicates the bonding position to ring A701 or ring A702. 701 , R 702 may be the same or different, and R 701 , R 702 When there are a plurality of each of the groups, they may be the same or different. In formula (b), Ar 701 , Ar 703 each independently represents an aromatic hydrocarbon ring structure which may have a substituent, or an aromatic heterocyclic structure which may have a substituent. Ar 702 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. Ar 701 , Ar 702 , and Ar 703 When there are a plurality of each of the groups, they may be the same or different. The substituents bonded to ring A701 may be bonded to each other, the substituents bonded to ring A702 may be bonded to each other, or the substituents bonded to ring A701 and the substituents bonded to ring A702 may be bonded to each other to form a ring. In equation (7), B 701 -L 700 -B 702 represents an anionic bidentate ligand. 701 and B 702 each independently represents a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms may be atoms constituting a ring. 700 is a single bond or B 701 and B 702 represents the atomic group that together with B constitutes a bidentate ligand. 701 -L 700 -B 702 When there are multiple groups, they may be the same or different. In addition, in formula (7) and formula (b), i1 and i2 each independently represent an integer of 0 to 12, i3 is Ar 702 represents an integer greater than or equal to 0, with the upper limit being the number that can be replaced by j is Ar 701 represents an integer greater than or equal to 0, with the upper limit being the number that can be replaced by k1 and k2 each independently represent an integer of 0 or more, the upper limit of which is the number of groups that can be substituted on ring A701 and ring A702. m is an integer from 1 to 3.

[0039] Aspect 11 of the present invention is the organic electroluminescent device according to any one of aspects 1 to 10, In the organic electroluminescent device, the first organic layer further contains at least one compound selected from the group consisting of a compound represented by the following formula (250) and a compound represented by the following formula (260).

[0040] [ka]

[0041] (In formula (250), each W independently represents CH or N, and at least one W is N; Xa 1 , Ya 1 , and Za 1 each independently represents a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a divalent aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent, Xa 2 , Ya 2 and Za 2 each independently represents a hydrogen atom, an optionally substituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted monovalent aromatic heterocyclic group having 3 to 30 carbon atoms, g11, h11, and j11 each independently represent an integer of 0 to 6; At least one of g11, h11, and j11 is an integer of 1 or greater, If g11 is 2 or more, multiple Xa 1may be the same or different, If h11 is 2 or more, multiple Ya 1 may be the same or different, If j11 is 2 or more, multiple Za 1 may be the same or different, R 31 represents a hydrogen atom or a substituent, and four R 31 may be the same or different, However, if g11, h11, or j11 is 0, the corresponding Xa 2 , Ya 2 , Za 2 is not a hydrogen atom.)

[0042] [ka]

[0043] (In formula (260), Ar 61 ~Ar 65 each independently represents a hydrogen atom or an optionally substituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, L 1 ~L 5 each independently represents a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, R 60 each independently represents a substituent, m1 to m5 each independently represent an integer of 0 to 5; n represents an integer of 0 to 10, a1 to a3 each independently represent an integer of 0 to 3; However, Ar 61 , Ar 62 , Ar 63 , Ar 64 and at least one Ar when n is 1 or more. 65 At least one of them is not a hydrogen atom.)

[0044] A twelfth aspect of the present invention is the organic electroluminescent device according to any one of the first to eleventh aspects, The organic electroluminescent device is one in which the first organic layer contains at least the compound represented by formula (250).

[0045] A thirteenth aspect of the present invention is a display device comprising the organic electroluminescent device according to any one of the first to twelfth aspects.

[0046] A fourteenth aspect of the present invention is a lighting device including the organic electroluminescent device according to any one of the first to twelfth aspects. [Effects of the Invention]

[0047] According to the present invention, it is possible to provide an organic electroluminescent device which has a lower driving voltage, a higher luminous efficiency, and a longer driving life than conventional devices. [Brief explanation of the drawings]

[0048] [Figure 1] FIG. 1 is a cross-sectional view showing a structural example of an organic electroluminescent device of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0049] The following describes in detail the embodiments of the present invention, but the present invention is not limited to the following embodiments and can be practiced in various modifications within the scope of the gist. In addition, when the expression "to" is used in this specification, it is used as an expression including the numerical values ​​or physical property values ​​before and after it.

[0050] In the present invention, the phrase "may have a substituent" means that it may have one or more substituents.

[0051] In this specification, the terms "(hetero)aralkyl group," "(hetero)aryloxy group," and "(hetero)aryl group" refer to an aralkyl group that may contain a heteroatom, an aryloxy group that may contain a heteroatom, and an aryl group that may contain a heteroatom, respectively. "May contain a heteroatom" means that one or more carbon atoms forming the aryl skeleton in the main skeleton of the aralkyl group, aryloxy group, or aryl group are substituted with heteroatoms. Examples of heteroatoms include nitrogen atoms, oxygen atoms, sulfur atoms, phosphorus atoms, and silicon atoms. Among these, nitrogen atoms are preferred from the viewpoint of durability. In addition, in this specification, the term "(hetero)aryl group" is used to mean a monocyclic group, a 2- to 4-fused ring group, and a group in which a plurality of monocyclic and / or 2- to 4-fused ring groups are linked together. The (hetero)aryl group represents an aryl group which may contain a heteroatom, that is, an aryl group or a heteroaryl group, where an aryl group is an aromatic hydrocarbon group and a heteroaryl group is an aromatic heterocyclic group.

[0052] <Organic electroluminescent device> An organic electroluminescent device according to an embodiment of the present invention is an organic electroluminescent device having an anode, a cathode, a first organic layer, and a second organic layer, the first organic layer is provided between the anode and the cathode; the second organic layer is in contact with the anode side of the first organic layer, The first organic layer contains a compound represented by the formula (240) described later or the following formula (241), The second organic layer contains a polymer having a triarylamine structure and no crosslinking group.

[0053] [ka]

[0054] (In formula (240), Ar 611 , Ar 612each independently represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. R 611 , R 612 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, or a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent; R 611 and R 612 At least one of these represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms. G represents a single bond or a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. n 611 , n 612 are each independently an integer of 1 to 4.

[0055] [ka]

[0056] (In formula (241), Ar 613 ~Ar 615 each independently represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. R 613 , R 614 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, or a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent; R 613 and R 614 At least one of these represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms. G 612 , G 613 each independently represents a single bond or a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. n 613 , n 614 are each independently an integer of 1 to 4.

[0057] The reason why the organic electroluminescent device according to the embodiment of the present invention exhibits such effects is not clear, but is presumed to be as follows. The benzene ring in the carbazole skeleton has a high electron density, and the 3- or 6-position is particularly reactive and likely to react with electron-donating substances. As a result of this reaction, an oxide of the electron-donating substance is formed, which may further degrade the device during operation. Furthermore, when a crosslinked polymer is used as a constituent material of the second organic layer, unreacted crosslinking groups remain after the crosslinking process. Therefore, the remaining crosslinking groups may generate unintended reactive species during operation of the organic electroluminescent device. In devices where the first and second organic layers are adjacent, these may react with the 3- or 6-position of the carbazole skeleton contained in the first organic layer. This is thought to result in a shortened operating life of such organic electroluminescent devices. On the other hand, the compound represented by formula (240) or formula (241) contained in the first organic layer caps the highly reactive site of the carbazole skeleton, thereby suppressing compound degradation. Furthermore, the polymer having a triarylamine structure contained in the second organic layer does not have a crosslinking group, and therefore the reactive species derived from the crosslinking group do not react with the carbazole compound, which is thought to prevent deterioration of the compounds constituting the organic electroluminescent device and extend the operating life of the organic electroluminescent device. When a crosslinked polymer is used as a constituent material of the second organic layer, the second organic layer forms a crosslinked polymer having a crosslinking group after the crosslinking process. However, the crosslinking reaction causes distortion of the polymer molecular chain, which is thought to reduce the charge transport property, especially near the interface. On the other hand, the polymer having a triarylamine structure used in the present invention does not have a crosslinking group, and is therefore thought to be free from the reduction in charge transport property caused by the crosslinking reaction, thereby improving the charge transport property. Furthermore, the compound represented by formula (240) or formula (241) contained in the first organic layer of the present invention has a structure in which aromatic rings are connected longer in the para-position of the nitrogen atom of the carbazole skeleton, and the highest occupied molecular orbital (HOMO) is wider, which is thought to improve the charge transport property. Therefore, in the organic electroluminescent device of the present invention, in which a polymer not containing a crosslinked body is used in the second organic layer and a compound represented by formula (240) or formula (241) is contained in the first organic layer, it is considered that the charge balance is improved by the effective transfer of charges from the second organic layer to the first organic layer, and an organic electroluminescent device with low voltage and high efficiency can be obtained.

[0058] [First organic layer and second organic layer] The first organic layer may be a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like, but the first organic layer is preferably a light emitting layer. The second organic layer is preferably a hole injection layer or a hole transport layer, more preferably a hole transport layer. The present invention is particularly suitable for use in an organic electroluminescent device in which a first organic layer is an emitting layer, a second organic layer is a hole transport layer, and the first organic layer is formed on the second organic layer by a wet film formation method. Examples of methods for forming the first organic layer and the second organic layer include dry film-forming methods such as vacuum deposition, and wet film-forming methods. In the present invention, the wet film-forming method refers to a film-forming method, i.e., a coating method, such as spin coating, dip coating, die coating, bar coating, blade coating, roll coating, spray coating, capillary coating, inkjet printing, nozzle printing, screen printing, gravure printing, or flexographic printing, which is used to form a wet film, and then drying the coated film to form a film. Among these film-forming methods, spin coating, spray coating, inkjet printing, nozzle printing, and the like are preferred.

[0059] When the first organic layer is formed by a wet film-forming method, it is preferable to use the first composition described below. When the second organic layer is formed by a wet film-forming method, it is preferable to use the second composition described below. After applying the second composition, the polymer is insolubilized by heating. Therefore, the second organic layer can be suitably used for laminating organic electroluminescent devices.

[0060] The "first organic layer" and the "second organic layer" will be described in detail below.

[0061] <First organic layer> [Compound represented by formula (240) or (241)] The first organic layer contains a compound represented by the above formula (240) or (241).

[0062] (Ar 611 ~Ar 615 ) Ar in formula (240) and formula (241) 611 ~Ar 615 each independently represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. The aromatic hydrocarbon group typically has 6 to 50 carbon atoms, preferably 6 to 30 carbon atoms, and more preferably 6 to 18 carbon atoms. Specific examples of the aromatic hydrocarbon group include monovalent groups of aromatic hydrocarbon structures, such as benzene rings, naphthalene rings, anthracene rings, tetraphenylene rings, phenanthrene rings, chrysene rings, pyrene rings, benzanthracene rings, and perylene rings, each having a carbon number of typically 6 or more and typically 30 or less, preferably 18 or less, and more preferably 14 or less, or monovalent groups of structures in which multiple structures selected from these structures are linked in a chain or branched manner. When multiple aromatic hydrocarbon rings are linked, typically, a structure in which 2 to 8 rings are linked is used, and a structure in which 2 to 5 rings are linked is preferred. When multiple aromatic hydrocarbon rings are linked, the linked rings may be the same structure or different structures.

[0063] Ar 611 ~Ar 615 are preferably each independently phenyl group, a monovalent group in which multiple benzene rings are bonded in a chain or branched manner, a monovalent group in which one or more benzene rings and at least one naphthalene ring are bonded in a linear or branched manner, a monovalent group in which one or more benzene rings and at least one phenanthrene ring are bonded in a linear or branched manner, or a monovalent group in which one or more benzene rings and at least one tetraphenylene ring are bonded in a linear or branched manner; and more preferably a monovalent group in which a plurality of benzene rings are bonded in a linear or branched manner. In either case, the order of bonding does not matter. Ar 611 ~Ar 615 is particularly preferably each independently a monovalent group in which a plurality of benzene rings, which may have a substituent, are bonded in a linear or branched manner, and is most preferably each independently a monovalent group in which a plurality of benzene rings, which may have a substituent, are bonded in a linear or branched manner.

[0064] As described above, the number of linked benzene rings, naphthalene rings, phenanthrene rings, and tetraphenylene rings is usually 2 to 8, and preferably 2 to 5. Among these, preferred are monovalent groups in which 1 to 4 benzene rings are linked together, monovalent groups in which 1 to 4 benzene rings and a naphthalene ring are linked together, monovalent groups in which 1 to 4 benzene rings and a phenanthrene ring are linked together, and monovalent groups in which 1 to 4 benzene rings and a tetraphenylene ring are linked together.

[0065] These aromatic hydrocarbon groups may have a substituent. The substituent that the aromatic hydrocarbon group may have can be selected from the following substituent group Z2. Preferred substituents are the preferred substituents in the following substituent group Z2.

[0066] Ar 611 ~Ar 615 From the viewpoint of the solubility and durability of the compound, it is preferable that at least one of the above has at least one partial structure selected from the following formulae (72-1) to (72-7).

[0067] [ka]

[0068] In each of the above formulas (72-1) to (72-7), * represents a bond to an adjacent structure or a hydrogen atom, and at least one of the two * represents the bonding position to the adjacent structure. In the following description, * has the same definition unless otherwise specified.

[0069] More preferably, Ar 611 , Ar 612 At least one of the above has at least one partial structure selected from the formulae (72-1) to (72-4) and (72-7). More preferably, Ar 611 , Ar 612 Each of these has at least one partial structure selected from the formulae (72-1) to (72-3) and (72-7). Particularly preferably, Ar 611 , Ar 612Each of these has at least one partial structure selected from the formula (72-1), the formula (72-2), and the formula (72-7).

[0070] Formula (72-2) is preferably the following formula (72-2-2).

[0071] [ka]

[0072] Formula (72-2) is more preferably the following formula (72-2-3).

[0073] [ka]

[0074] In addition, from the viewpoint of the solubility and durability of the compound, Ar 611 , Ar 612 The partial structure that at least one of the above preferably has includes a partial structure represented by formula (72-1) and a partial structure represented by formula (72-2).

[0075] (R 611 ~R 614 ) R in equations (240) and (241) 611 ~R 614 R are each independently a hydrogen atom, a deuterium atom, a halogen atom such as a fluorine atom, or a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. 611 and R 612 At least one of R represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms. 613 and R 614 At least one of these represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms. Preferably, R 611 ~R 614 are each independently a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms, more preferably 6 to 30 carbon atoms, still more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 10 carbon atoms, which may have a substituent. Specific examples of the monovalent aromatic hydrocarbon group include the above-mentioned Ar 611 The same applies to the preferred aromatic hydrocarbon groups, with a phenyl group being particularly preferred. These aromatic hydrocarbon groups may have a substituent. The substituent that the aromatic hydrocarbon group may have is as described above, and specifically, can be selected from the following substituent group Z2. Preferred substituents are the preferred substituents in the following substituent group Z2.

[0076] (n 611 ~n 614 ) n in equations (240) and (241) 611 ~n 614 are each independently an integer of 1 to 4. 611 ~n 614 are each independently preferably an integer of 1 to 2, and more preferably 1. In addition, n 611 ~n 614 If is an integer between 1 and 3, R 611 ~R 614 R in a benzene ring having 611 ~R 614 There are hydrogen atoms at bonding positions other than the above.

[0077] (substituent) Ar 611 ~Ar 615 , R 611 ~R 614 When is a monovalent aromatic hydrocarbon group, the substituent that may be possessed is preferably a substituent selected from the following substituent group Z2.

[0078] <Substituent group Z2> The substituent group Z2 is a group consisting of an alkyl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkoxycarbonyl group, a dialkylamino group, a diarylamino group, an arylalkylamino group, an acyl group, a halogen atom, a haloalkyl group, an alkylthio group, an arylthio group, a silyl group, a siloxy group, a cyano group, an aromatic hydrocarbon group, and an aromatic heterocyclic group. These substituents may have any of a linear, branched, and cyclic structure.

[0079] More specifically, the substituent group Z2 includes the following structures. For example, linear, branched, or cyclic alkyl groups having a carbon number of usually 1 or more, preferably 4 or more, and usually 24 or less, preferably 12 or less, more preferably 8 or less, and even more preferably 6 or less, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-hexyl group, a cyclohexyl group, or a dodecyl group; For example, alkoxy groups such as a methoxy group and an ethoxy group, each of which usually has 1 or more carbon atoms and usually has 24 or less carbon atoms, preferably 12 or less carbon atoms; For example, an aryloxy group or heteroaryloxy group, such as a phenoxy group, a naphthoxy group, or a pyridyloxy group, which usually has 4 or more, preferably 5 or more, and usually has 36 or less, preferably 24 or less carbon atoms; For example, alkoxycarbonyl groups having usually 2 or more carbon atoms and usually 24 or less, preferably 12 or less carbon atoms, such as a methoxycarbonyl group or an ethoxycarbonyl group; For example, dialkylamino groups having usually 2 or more carbon atoms and usually 24 or less, preferably 12 or less, such as a dimethylamino group or a diethylamino group; For example, diarylamino groups, such as diphenylamino groups and ditolylamino groups, which usually have 10 or more, preferably 12 or more, and usually have 36 or less, preferably 24 or less carbon atoms; For example, an arylalkylamino group having usually 7 or more carbon atoms and usually 36 or less, preferably 24 or less, such as a phenylmethylamino group; For example, acyl groups such as an acetyl group and a benzoyl group, each of which usually has 2 or more carbon atoms and usually has 24 or less carbon atoms, preferably 12 or less carbon atoms; For example, halogen atoms such as fluorine atoms and chlorine atoms; For example, haloalkyl groups having usually 1 or more carbon atoms and usually 12 or less, preferably 6 or less, such as a trifluoromethyl group; For example, alkylthio groups having usually 1 or more carbon atoms and usually 24 or less, preferably 12 or less, such as a methylthio group or an ethylthio group; For example, an arylthio group having usually 4 or more, preferably 5 or more, and usually 36 or less, preferably 24 or less, carbon atoms, such as a phenylthio group, a naphthylthio group, or a pyridylthio group; For example, a silyl group having a carbon number of usually 2 or more, preferably 3 or more, and usually 36 or less, preferably 24 or less, such as a trimethylsilyl group or a triphenylsilyl group; For example, siloxy groups such as trimethylsiloxy groups and triphenylsiloxy groups, each having a carbon number of usually 2 or more, preferably 3 or more, and usually 36 or less, preferably 24 or less; cyano group; For example, aromatic hydrocarbon groups such as phenyl and naphthyl groups, each having a carbon number of usually 6 or more and usually 36 or less, preferably 24 or less; For example, aromatic heterocyclic groups such as thienyl and pyridyl groups, each having a carbon number of usually 3 or more, preferably 4 or more, and usually 36 or less, preferably 24 or less.

[0080] Among the above-mentioned substituent group Z2, alkyl groups, alkoxy groups, diarylamino groups, aromatic hydrocarbon groups, and aromatic heterocyclic groups are preferred. From the viewpoint of charge transportability, aromatic hydrocarbon groups or aromatic heterocyclic groups are preferred as the substituent, more preferably aromatic hydrocarbon groups, and even more preferably no substituent. From the viewpoint of improving solubility, alkyl groups or alkoxy groups are preferred as the substituent.

[0081] Each of the substituents in the substituent group Z2 may further have a substituent. Examples of such a substituent include the same as those in the substituent group Z2. Each of the substituents that may be contained in the substituent group Z2 is preferably 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 each of the substituents in the substituent group Z2 does not have any further substituent.

[0082] (G, G 612 , G 613 ) G in equation (240), G in equation (241) 612 , G 613 each independently represents a single bond or a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent.

[0083] G, G 612 , G 613 The number of carbon atoms in the aromatic hydrocarbon group is usually 6 to 50, preferably 6 to 30, and more preferably 6 to 18. Specific examples of the aromatic hydrocarbon group include divalent groups of aromatic hydrocarbon structures such as benzene rings, naphthalene rings, anthracene rings, tetraphenylene rings, phenanthrene rings, chrysene rings, pyrene rings, benzanthracene rings, and perylene rings, each of which has a carbon number of usually 6 or more and usually 30 or less, preferably 18 or less, and more preferably 14 or less, or divalent groups of structures in which multiple structures selected from these structures are linked in a chain or branched manner. When multiple aromatic hydrocarbon rings are linked, usually 2 to 8 rings are linked, and preferably 2 to 5 rings are linked. When multiple aromatic hydrocarbon rings are linked, the linked rings may have the same structure or different structures.

[0084] G, G 612 , G 613 is preferably single bond, a phenylene group, a divalent group in which multiple 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 linear or branched manner, a divalent group in which one or more benzene rings and at least one phenanthrene ring are bonded in a linear or branched manner, or a divalent group in which one or more benzene rings and at least one tetraphenylene ring are bonded in a linear or branched manner, and more preferably a divalent group in which a plurality of benzene rings are bonded in a linear or branched manner. In either case, the order of bonding is not important.

[0085] As described above, the number of linked benzene rings, naphthalene rings, phenanthrene rings, and tetraphenylene rings is usually 2 to 8, and preferably 2 to 5. Among these, more preferred are divalent groups in which 1 to 4 benzene rings are linked together, divalent groups in which 1 to 4 benzene rings and a naphthalene ring are linked together, divalent groups in which 1 to 4 benzene rings and a phenanthrene ring are linked together, and divalent groups in which 1 to 4 benzene rings and a tetraphenylene ring are linked together.

[0086] These aromatic hydrocarbon groups may have a substituent. The substituent that the aromatic hydrocarbon group may have can be selected from the aforementioned substituent group Z2. Preferred substituents are the preferred substituents in the aforementioned substituent group Z2.

[0087] The compound represented by the formula (240) or (241) is preferably a compound represented by the following formula (240-1) or (241-1).

[0088] [ka]

[0089] (In formula (240-1), Ar 611 , Ar 612 each independently represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. R 611 , R 612each independently represents a hydrogen atom, a deuterium atom, a halogen atom, or a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent, provided that R 611 and R 612 At least one of these represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms.)

[0090] [ka]

[0091] (In formula (241-1), Ar 613 ~Ar 615 each independently represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. R 613 , R 614 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, or a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent, provided that R 613 and R 614 At least one of these represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms.)

[0092] Ar in formula (240-1) and formula (241-1) 611 ~Ar 615 , R 611 ~R 614 Preferred examples of the substituents that may be present include Ar in formula (240) and formula (241). 611 ~Ar 615 , R 611 ~R 614 is the same as:

[0093] (molecular weight) The compound represented by the formula (240), the formula (241), the formula (240-1), or the formula (241-1) is a low-molecular-weight material, and its molecular weight is preferably 3,000 or less, more preferably 2,500 or less, even more preferably 2,000 or less, particularly preferably 1,500 or less, and is usually 300 or more, preferably 350 or more, more preferably 400 or more.

[0094] (Specific examples of the compounds represented by the formula (240), the formula (241), the formula (240-1) or the formula (241-1)) Preferred specific examples of the compound represented by the formula (240), the formula (241), the formula (240-1) or the formula (241-1) are shown below, but the present invention is not limited to these.

[0095] [ka]

[0096] The light-emitting layer according to the embodiment of the present invention may contain only one kind of compound represented by the formula (240), the formula (241), the formula (240-1), or the formula (241-1), or may contain two or more kinds of compounds.

[0097] [First composition] The first composition forming the first organic layer will now be described. The first composition contains the compounds represented by the above formulas (240) and (241) and an organic solvent. This first composition is usually used to form a layer or film by a wet film-forming method, and is particularly preferably used to form the first organic layer of an organic electroluminescent device. The first organic layer is particularly preferably an emitting layer. That is, the first composition is preferably a composition for forming an emitting layer.

[0098] [Luminescent materials] The first composition may further include a light-emitting material. The light-emitting material may be any known material that is normally used as a light-emitting material for organic electroluminescent devices, and is not particularly limited as long as it emits light at a desired emission wavelength and has good luminous efficiency. The light-emitting material may be a fluorescent compound or a phosphorescent compound, but from the viewpoint of internal quantum efficiency, a phosphorescent compound is preferred, and from the viewpoints of widening the color gamut and increasing the brightness, a fluorescent compound is preferred. Furthermore, when a fluorescent compound is used as the light-emitting material, it may contain a phosphorescent compound as a sensitizer.

[0099] (fluorescent compounds) Examples of the fluorescent compound (hereinafter also referred to as fluorescent material) include the following materials. Examples of fluorescent light-emitting materials that emit blue light (blue fluorescent light-emitting materials) include naphthalene, perylene, pyrene, anthracene, coumarin, chrysene, p-bis(2-phenylethenyl)benzene, and derivatives thereof. Examples of fluorescent materials that emit green light (green fluorescent materials) include quinacridone derivatives, coumarin derivatives, and aluminum complexes such as Al(C9H6NO)3. Examples of fluorescent materials that emit yellow light (yellow fluorescent materials) include rubrene and perimidon derivatives. Examples of fluorescent materials that emit red light (red fluorescent materials) include DCM (4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran) compounds, benzopyran derivatives, rhodamine derivatives, benzothioxanthene derivatives, and azabenzothioxanthene.

[0100] (Phosphorescent compounds) A phosphorescent compound is a compound 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. Among metal complexes, phosphorescent organometallic complexes that emit light via a triplet state include Werner complexes or organometallic complex compounds containing a central metal selected from Groups 7 to 11 of the long-form periodic table (hereinafter, unless otherwise specified, the term "periodic table" refers to the long-form periodic table). Examples of such phosphorescent compounds include the phosphorescent compounds described in WO 2014 / 024889, WO 2015 / 087961, WO 2016 / 194784, and JP 2014-074000 A. Preferably, the compound represented by the following formula (7) or the compound represented by the following formula (205) is preferred, and more preferably, the compound represented by the following formula (7).

[0101] [ka]

[0102] In formula (7), ring A701 represents an aromatic hydrocarbon ring structure which may have a substituent or an aromatic heterocyclic structure which may have a substituent. Ring A702 represents an aromatic heterocyclic structure which may have a substituent. When a plurality of rings A701 and a plurality of rings A702 are present, they may be the same or different.

[0103] R 701 , R 702 are each independently a structure represented by formula (b), and "*" indicates the bonding position to ring A701 or ring A702. 701 , R 702 may be the same or different, and R 701 , R 702 When there are a plurality of each of the groups, they may be the same or different. Ar 701 , Ar 703 each independently represents an aromatic hydrocarbon ring structure which may have a substituent, or an aromatic heterocyclic structure which may have a substituent. Ar 702represents 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. Ar 701 , Ar 702 , and Ar 703 When there are a plurality of each of the groups, they may be the same or different.

[0104] The substituents bonded to ring A701 may be bonded to each other, the substituents bonded to ring A702 may be bonded to each other, or the substituents bonded to ring A701 and the substituents bonded to ring A702 may be bonded to each other to form a ring.

[0105] B 701 -L 700 -B 702 represents an anionic bidentate ligand. 701 and B 702 each independently represents a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms may be atoms constituting a ring. 700 is a single bond or B 701 and B 702 represents the atomic group that together with B constitutes a bidentate ligand. 701 -L 700 -B 702 When there are multiple groups, they may be the same or different.

[0106] In addition, in equations (7) and (b), i1 and i2 each independently represent an integer of 0 to 12, i3 is Ar 702 represents an integer greater than or equal to 0, with the upper limit being the number that can be replaced by i4 is Ar 701 represents an integer greater than or equal to 0, with the upper limit being the number that can be replaced by k1 and k2 each independently represent an integer of 0 or more, the upper limit of which is the number of groups that can be substituted on ring A701 and ring A702; m represents an integer of 1 to 3.

[0107] Unless otherwise specified, the substituent is preferably a group selected from the following substituent group S. Substituent group S: An alkyl group, preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 8 carbon atoms, and particularly preferably an alkyl group having 1 to 6 carbon atoms. An alkoxy group, preferably an alkoxy group having 1 to 20 carbon atoms, more preferably an alkoxy group having 1 to 12 carbon atoms, and even more preferably an alkoxy group having 1 to 6 carbon atoms. An aryloxy group, preferably an aryloxy group having 6 to 20 carbon atoms, more preferably an aryloxy group having 6 to 14 carbon atoms, even more preferably an aryloxy group having 6 to 12 carbon atoms, and particularly preferably an aryloxy group having 6 carbon atoms. A heteroaryloxy group, preferably a heteroaryloxy group having 3 to 20 carbon atoms, more preferably a heteroaryloxy group having 3 to 12 carbon atoms. An alkylamino group, preferably an alkylamino group having 1 to 20 carbon atoms, more preferably an alkylamino group having 1 to 12 carbon atoms.

[0108] An arylamino group, preferably an arylamino group having 6 to 36 carbon atoms, more preferably an arylamino group 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. Heteroaralkyl groups, preferably heteroaralkyl groups having 7 to 40 carbon atoms, more preferably heteroaralkyl groups 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, more preferably an alkynyl group having 2 to 12 carbon atoms.

[0109] 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 6 to 20 carbon atoms in the aryl group, more preferably an arylsilyl group having 6 to 14 carbon atoms in the aryl group. 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. In the above groups, one or more hydrogen atoms may be replaced by fluorine atoms, or one or more hydrogen atoms may be replaced by deuterium atoms. Unless otherwise specified, aryl is an aromatic hydrocarbon ring and heteroaryl is an aromatic heterocyclic ring.

[0110] -Hydrogen atom, deuterium atom, fluorine atom, cyano group, or -SF5.

[0111] Among the substituent group S, preferred are 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, an arylsilyl group, and groups in which one or more hydrogen atoms of these groups are replaced by fluorine atoms, a fluorine atom, a cyano group, or -SF5; More preferably, it is 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 are replaced with fluorine atoms, a fluorine atom, a cyano group, or -SF5; More preferred are alkyl groups, alkoxy groups, aryloxy groups, arylamino groups, aralkyl groups, alkenyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, and arylsilyl groups. Particularly preferred are alkyl groups, arylamino groups, aralkyl groups, alkenyl groups, aryl groups, and heteroaryl groups. Most preferred are alkyl groups, arylamino groups, aralkyl groups, aryl groups and heteroaryl groups.

[0112] These substituents in the substituent group S may further have a substituent selected from the substituent group S as a substituent. The preferred groups, more preferred groups, even 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.

[0113] Ring A701 represents an aromatic hydrocarbon ring structure which may have a substituent or an aromatic heterocyclic structure which may have a substituent. 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, or a fluorene ring is preferred. 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, more preferably a furan ring, a benzofuran ring, a thiophene ring, or a benzothiophene ring.

[0114] Ring A701 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.

[0115] Ring A702 represents an aromatic heterocyclic structure which may have a substituent. 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. 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.

[0116] Preferred combinations of ring A701 and ring A702, when expressed as (ring A701-ring A702), 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). The substituents that may be possessed by ring A701 and ring A702 can be selected arbitrarily, but are preferably one or more types of substituents selected from the above-mentioned group S of substituents.

[0117] Ar 701 , Ar 703 each independently represents an aromatic hydrocarbon ring structure which may have a substituent, or an aromatic heterocyclic structure which may have a substituent. Ar 702 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.

[0118] Ar 701 , Ar702 , Ar 703 When any one of the above is an aromatic hydrocarbon ring structure which may have a substituent, the aromatic hydrocarbon ring structure 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, 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.

[0119] Ar 701 , Ar 702 When any of the above is a benzene ring which may have a substituent, it is preferable that at least one benzene ring is bonded to an adjacent structure at an ortho-position or a meta-position, and it is more preferable that at least one benzene ring is bonded to an adjacent structure at a meta-position.

[0120] Ar 701 , Ar 702 , Ar 703 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.

[0121] Ar 701 , Ar 702 , Ar 703 is an aromatic heterocyclic structure which may have 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. Ar 701 , Ar702 , Ar 703 When either of the groups 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.

[0122] Ar 702 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.

[0123] i1 and i2 each independently represent an integer of 0 to 12, preferably 1 to 12, further preferably 1 to 8, and even more preferably 1 to 6. Within this range, improvements in solubility and 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 more preferably 0 or 1. k1 and k2 each independently represent an integer of preferably 0 to 3, more preferably 1 to 3, even more preferably 1 or 2, and particularly preferably 1.

[0124] Ar 701 , Ar 702 , Ar 703 The substituents that may be possessed by may be arbitrarily selected, but are preferably one or more substituents selected from the above-mentioned substituent group S. The 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 preferably Ar 703 If Ar exists, 703 To, Ar 703 If Ar does not exist, 702 To, Ar 702 and Ar 703 If Ar does not exist, 701It is preferred that the substituent is

[0125] The compound represented by the formula (7) is preferably a compound that satisfies one or more of the following (I) to (IV):

[0126] (I) Phenylene-linked The structure represented by formula (b) is preferably a structure having a group linked to benzene rings, i.e., a benzene ring structure, i1 being 1 to 6, and 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.

[0127] (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 A701 or the ring A702, i.e., Ar 701 is an aromatic hydrocarbon structure or an aromatic heterocyclic structure, i1 is 1 to 6, Ar 702 is an aliphatic hydrocarbon structure, i2 is 1 to 12, preferably 3 to 8, Ar 703 is a benzene ring structure, i3 is 0 or 1, preferably Ar 701 is 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.

[0128] (III) Dendron A structure in which a dendron is bonded to the ring A701 or the ring A702, for example, Ar 701 , Ar 702 is a benzene ring structure, Ar 703 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.

[0129] (IV)B 701 -L 700 -B 702 B 701 -L 700 -B 702 The structure represented by the formula (203) is preferably a structure represented by the formula (204) below.

[0130] [ka]

[0131] 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, and ring B3 is preferably a pyridine ring.

[0132] The phosphorescent compound represented by the formula (7) is not particularly limited, but preferred examples include the following.

[0133] [ka]

[0134] [ka]

[0135] [ka]

[0136] The molecular weight of the phosphorescent compound is preferably 5,000 or less, more preferably 4,000 or less, and particularly preferably 3,000 or less. The molecular weight of the phosphorescent compound is preferably 1,200 or more, more preferably 1,400 or more, and even more preferably 1,600 or more. It is believed that within this molecular weight range, the phosphorescent compounds do not aggregate with each other and can be uniformly mixed with the charge transport material, thereby making it possible to obtain a light-emitting layer with high luminous efficiency.

[0137] The molecular weight of the phosphorescent compound is preferably large in that it has a high Tg, melting point, decomposition temperature, etc., and the heat resistance of the phosphorescent compound and the formed light-emitting layer is excellent, and it is less likely to cause deterioration in film quality due to gas generation, recrystallization, molecular migration, etc., or an increase in impurity concentration due to thermal decomposition of the material. On the other hand, the molecular weight of the phosphorescent compound is preferably small in that it makes it easier to purify the organic compound.

[0138] The first composition may further contain at least one selected from the group consisting of a compound represented by the following formula (250) and a compound represented by the following formula (260), and from the viewpoint of charge balance, it preferably contains at least a compound represented by the following formula (250).

[0139] [Compound represented by formula (250)]

[0140] [ka]

[0141] (In formula (250), each W independently represents CH or N, and at least one W is N; Xa 1 , Ya 1 , and Za 1 each independently represents a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a divalent aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent, Xa 2 , Ya 2 and Za 2 each independently represents a hydrogen atom, an optionally substituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted monovalent aromatic heterocyclic group having 3 to 30 carbon atoms, g11, h11, and j11 each independently represent an integer of 0 to 6; At least one of g11, h11, and j11 is an integer of 1 or greater, If g11 is 2 or more, multiple Xa 1 may be the same or different, If h11 is 2 or more, multiple Ya 1 may be the same or different, If j11 is 2 or more, multiple Za 1 may be the same or different, R 31 represents a hydrogen atom or a substituent, and four R 31 may be the same or different, However, if g11, h11, or j11 is 0, the corresponding Xa 2 , Ya 2 , Za 2 is not a hydrogen atom.)

[0142] The compound represented by the above formula (250) is preferably a charge transporting compound, that is, a charge transporting host material.

[0143] <w> In the formula (250), W represents CH or N, and at least one of them is N. From the viewpoint of electron transport properties and electron durability, it is preferable that at least two of them are N, and it is more preferable that all of them are N.

[0144] <Xa 1 , Ya 1 , Za 1 , Xa 2 , Ya 2 , Za 2 > In the formula (250), Xa 1 , Ya 1 , Za 1 is a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, and Xa 2 , Ya 2 , Za 2 When the aromatic hydrocarbon group having 6 to 30 carbon atoms is an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, the aromatic hydrocarbon ring of the aromatic hydrocarbon group having 6 to 30 carbon atoms is preferably a 6-membered monocyclic ring or 2 to 5 condensed rings. Specific examples include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring, a triphenylene ring, a fluoranthene ring, and an indenofluorene ring. Among these, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, or a fluorene ring is preferred, a benzene ring, a naphthalene ring, a phenanthrene ring, or a fluorene ring is more preferred, and a benzene ring, a naphthalene ring, or a fluorene ring is even more preferred. In addition, when g11 is 2 or more, the terminal partial structure -Xa 1 -Xa 2 , -Ya is a terminal partial structure when h11 is 2 or more. 1 -Ya 2 and a terminal partial structure when j11 is 2 or more, -Za 1 -Za 2 The compound represented by formula (250) may have a spirofluorene structure. 1 -Xa 2 , -Ya is a terminal partial structure when h11 is 2 or more. 1 -Ya 2 and a terminal partial structure when j11 is 2 or more, -Za 1 -Za 2 At least one of these preferably has a spirofluorene structure.

[0145] In the formula (250), Xa 1 , Ya 1 , Za 1 is a divalent aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent, and Xa 2 , Ya 2 , Za 2 When is an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent, the aromatic heterocyclic ring of the aromatic heterocyclic group having 3 to 30 carbon atoms is preferably a 5- or 6-membered monocyclic ring or 2 to 5 condensed rings. Specific examples thereof include a furan ring, a benzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, an oxadiazole ring, an indole ring, a carbazole ring, an indolocarbazole ring, an indenocarbazole 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 perimidine ring, a quinazoline ring, and a quinazolinone ring. Among these, a thiophene ring, a pyrrole ring, an imidazole ring, a pyridine ring, a pyrimidine ring, a triazine ring, a quinoline ring, a quinazoline ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, an indolocarbazole ring, a phenanthroline ring, or an indenocarbazole ring is preferred, a pyridine ring, a pyrimidine ring, a triazine ring, a quinoline ring, a quinazoline ring, a carbazole ring, an indolocarbazole ring, an indenocarbazole ring, a dibenzofuran ring, or a dibenzothiophene ring is more preferred, and a carbazole ring, an indolocarbazole ring, a dibenzofuran ring, or a dibenzothiophene ring is even more preferred.

[0146] Xa in the formula (250) 1 , Ya 1 , Za 1 , Xa 2 , Ya 2 , and Za 2 In the above, particularly preferred aromatic hydrocarbon rings are a benzene ring, a naphthalene ring, or a phenanthrene ring, and particularly preferred aromatic heterocycles are a carbazole ring, an indolocarbazole ring, a dibenzofuran ring, or a dibenzothiophene ring.

[0147] Xa in the formula (250) 1 , Ya 1 , Za 1 , Xa 2 , Ya 2 and Za 2 In the above, the substituent that the aromatic hydrocarbon group having 6 to 30 carbon atoms may have and the substituent that the aromatic heterocyclic group having 3 to 30 carbon atoms may have are preferably each independently selected from the substituent group Z2, and it is more preferable that the substituent selected from the substituent group Z2 does not have an additional substituent. It is believed that the absence of an additional substituent in the substituent selected from the substituent group Z2 makes it possible to maintain high charge transport properties and durability, which is preferable. Among the substituent group Z2, aromatic hydrocarbon groups and aromatic heterocyclic groups are preferred, and aromatic hydrocarbon groups are particularly preferred, from the viewpoint of charge transport properties and durability.

[0148] <g11、h11、j11> g11, h11, and j11 each independently represent an integer of 0 to 6, and at least one of g11, h11, and j11 is an integer of 1 or greater. From the viewpoint of charge transport properties and durability, it is preferred that g11 is 2 or greater, or at least one of h11 and j11 is 3 or greater.

[0149] Furthermore, it is preferable that the compound represented by the formula (250) has a total of 8 to 18 of these rings, including the ring having three central Ws, from the viewpoints of charge transport properties, durability, and solubility in organic solvents.

[0150] <(Xa 1 ) g11 , (Ya 1 ) h11 , (Za 1 ) j11 > (Xa 1 ) g11 , (Ya 1 ) h11 , and (Za 1 ) j11 From the viewpoint of the solubility and durability of the compound, it is preferable that at least one group selected from each of the following formulas (11), (12), and (13) has a partial structure independently selected from the partial structure represented by the following formula (14): 1 ) g11 , when h11 is 1 or more (Ya 1 ) h11 , and when j11 is 1 or more (Za 1 ) j11 It is more preferable that each independently have a partial structure selected from a partial structure represented by the following formula (11), a partial structure represented by the following formula (12), and a partial structure represented by the following formula (13).

[0151] [ka]

[0152] In each of the above formulas (11) to (13), * indicates the bonding position with the adjacent structure, or Xa in formula (250). 2 , Ya 2 , or Za 2 represents the hydrogen atom when * is a hydrogen atom. At least one of the two * marks represents the bonding position to the adjacent structure. In the following description, * has the same definition unless otherwise specified.

[0153] More preferably, when g11 is 1 or more, (Xa 1 ) g11 , when h11 is 1 or more (Ya 1 ) h11 , and when j11 is 1 or more (Za 1 ) j11 each independently has a partial structure represented by formula (11) or a partial structure represented by formula (12). More preferably, when g11 is 1 or more, (Xa 1 ) g11 , when h11 is 1 or more (Ya 1 ) h11 , and when j11 is 1 or more (Za 1 ) j11 each independently has a partial structure represented by formula (11) and a partial structure represented by formula (12).

[0154] The partial structure represented by formula (12) is preferably a partial structure represented by the following formula (12-2).

[0155] [ka]

[0156] The partial structure represented by formula (12) is more preferably a partial structure represented by the following formula (12-3).

[0157] [ka]

[0158] As the partial structure having the partial structure represented by formula (11) and the partial structure represented by formula (12), from the viewpoint of solubility, a partial structure selected from the following formulas (14) to (17), which is a structure containing a plurality of structures selected from the partial structure represented by formula (11) and the partial structure represented by formula (12), is preferred. That is, when g11 is 1 or more, (Xa 1 ) g11 , when h11 is 1 or more (Ya 1 ) h11あ , and when j11 is 1 or more (Za 1 ) j11 Each of the formulas (11) to (13) preferably has a partial structure selected from the following formulas (14) to (17). In other words, from the viewpoint of solubility, when g11 is 1 or more, (Xa 1 ) g11 , when h11 is 1 or more (Ya 1 ) h11 , and when j11 is 1 or more (Za 1 ) j11 each independently preferably has a partial structure selected from formulas (11) to (17).

[0159] [ka]

[0160] A structure containing a plurality of structures selected from the partial structure represented by formula (11) and the partial structure represented by formula (12) means, for example, a partial structure represented by formula (14) that can be considered to have one partial structure represented by formula (11) and two partial structures represented by formula (12), as in the following formula (14a):

[0161] [ka]

[0162] More preferably, (Xa 1 ) g11 , (Ya 1 ) h11 , and (Za 1 ) j11 At least one of the groups has at least a partial structure represented by formula (14) or a partial structure represented by formula (15). More preferably, when g11 is 1 or more, (Xa 1 ) g11 , when h11 is 1 or more (Ya 1 ) h11 , and when j11 is 1 or more (Za 1 ) j11 has a partial structure represented by formula (14) or a partial structure represented by formula (15).

[0163] The partial structure represented by formula (14) is preferably a partial structure represented by the following formula (14-2).

[0164] [ka]

[0165] The partial structure represented by formula (14) is more preferably a partial structure represented by the following formula (14-3).

[0166] [ka]

[0167] The partial structure represented by formula (15) is preferably a partial structure represented by the following formula (15-2).

[0168] [ka]

[0169] The partial structure represented by formula (15) is more preferably a partial structure represented by the following formula (15-3).

[0170] [ka]

[0171] The partial structure represented by formula (17) is preferably a partial structure represented by the following formula (17-2).

[0172] [ka]

[0173] (Xa 1 ) g11 , (Ya 1 ) h11、 and (Za 1 ) j11 It is more preferable that at least one of the above has a partial structure represented by the following formula (19) or a partial structure represented by the following formula (20) as a partial structure containing a partial structure represented by formula (13).

[0174] [ka]

[0175] In each of the above formulas (14) to (20), * indicates the bonding position with the adjacent structure, or Xa 2 , Ya 2 , or Za 2 represents the hydrogen atom. At least one of the two * marks represents the bonding position to the adjacent structure.

[0176] Among the partial structures represented by formulas (14) to (20), the partial structure represented by formula (14-3) and the partial structure represented by formula (15-3) are preferred, with formula (14-3) being more preferred.

[0177] -(Xa 1 ) g11 -(Xa 2 ), -(Ya 1 ) h11 -(Ya 2 ), and -(Za 1 ) j11 -(Za 2 ) each independently preferably has a partial structure represented by formula (11), a partial structure represented by formula (12-3), a partial structure represented by formula (14-3), or a partial structure represented by formula (15-3).

[0178] Also, -(Xa 1 ) g11 -(Xa 2 ), -(Ya 1 ) h11 -(Ya 2 ), and -(Za 1 ) j11 -(Za 2 ) preferably has any one of partial structures or terminal structures represented by the following formulae (250-1) to (250-10).

[0179] [ka]

[0180] In formulas (250-1) to (250-10), * represents a bonding position. 250 represents an aromatic hydrocarbon group having 6 to 20 carbon atoms. 32 represents a substituent, and the structures represented by formulae (250-1) to (250-10) may further have a substituent.]

[0181] The substituents that these structures may have are R 32 is the same as:

[0182] Ar 250 is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably a phenyl group or a biphenyl group, and even more preferably a phenyl group.

[0183] R 32 In a structure having two R 32 may be the same or different. R 32 is preferably an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms which may be substituted with an alkyl group having 1 to 8 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms which may be substituted with an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may be substituted with an alkyl group having 1 to 8 carbon atoms, and even more preferably an alkyl group having 1 to 8 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an aryloxy group having 6 to 14 carbon atoms, or an aryl group having 6 to 14 carbon atoms which may be substituted with an alkyl group having 1 to 8 carbon atoms.

[0184] <R 31 > In formula (250), R when it is a substituent 31 is preferably an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent. From the viewpoint of improving durability and charge transportability, an aromatic hydrocarbon group which may have a substituent is more preferred. When R is a substituent, 31 When there are a plurality of groups, they may be different from each other.

[0185] The substituents that the aromatic hydrocarbon group having 6 to 30 carbon atoms may have, the substituents that the aromatic heterocyclic group having 3 to 30 carbon atoms may have, and the substituent R 31 The substituent that may be possessed by can be selected from the above-mentioned substituent group Z2.

[0186] From the viewpoint of charge transport properties, R 31 is preferably a hydrogen atom.

[0187] In addition, from the viewpoint of solubility, -(Ya 1 ) h11 -(Ya 2 ), and -(Za 1 ) j11 -(Za 2 ) is preferably not also an unsubstituted phenyl group.

[0188] <Molecular weight> The compound represented by the formula (250) is a low molecular weight material, and its molecular weight is preferably 3,000 or less, more preferably 2,500 or less, particularly preferably 2,000 or less, and most preferably 1,500 or less. The lower limit of the molecular weight of the compound is usually 400 or more, preferably 500 or more, and more preferably 600 or more.

[0189] <Specific examples of the compound represented by formula (250)> The compound represented by formula (250) is not particularly limited, but examples thereof include the following compounds.

[0190] [ka]

[0191] [ka]

[0192] [ka]

[0193] [ka]

[0194] [ka]

[0195] [ka]

[0196] The first composition may contain only one type of compound represented by the formula (250), or may contain two or more types.

[0197] [Compound represented by formula (260)]

[0198] [ka]

[0199] (In formula (260), Ar 61 ~Ar 65 each independently represents a hydrogen atom or an optionally substituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, L 1 ~L 5 each independently represents a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, R 60 each independently represents a substituent, m1 to m5 each independently represent an integer of 0 to 5; n represents an integer of 0 to 10, a1 to a3 each independently represent an integer of 0 to 3; However, Ar 61 , Ar 62 , Ar 63 , Ar 64 and at least one Ar when n is 1 or more. 65 At least one of them is not a hydrogen atom.)

[0200] (Ar 61 , Ar 62 , Ar 65 ) Ar in formula (260) 61 , Ar 62 and Ar 65 are each independently a hydrogen atom or an optionally substituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0201] Ar in formula (260) 61 , Ar 62 and Ar 65 From the viewpoint of the solubility and durability of the compound, is preferably a hydrogen atom, a monovalent group of a benzene ring, a monovalent group of a naphthalene ring, or a structure represented by the following formula (261) or the following formula (262), more preferably a hydrogen atom, a monovalent group of a benzene ring, or a structure represented by the following formula (261) or the following formula (262), still more preferably a hydrogen atom, a monovalent group of a benzene ring, or a structure represented by the following formula (262), and particularly preferably a structure represented by the following formula (262).

[0202] From the viewpoint of durability and charge transport property, Ar 61 , Ar 62 and at least one Ar 65 Among these, it is preferable that one or more and three or less are represented by the following formula (261) or the following formula (262), and Ar 61 , Ar 62 and at least one of and Ar 65 It is more preferable that one or more and three or less of the above be the following formula (262). From the viewpoint of charge transport property and solubility, Ar 61 , Ar 62 and at least one Ar 65 Among these, it is preferable that one of them is represented by the following formula (262). From the viewpoint of durability, Ar 61 , Ar 62 and at least one Ar 65 Among them, it is preferable that two or more are represented by the following formula (262), and it is more preferable that three are represented by the following formula (262).

[0203] (Equation (261), Equation (262))

[0204] [ka]

[0205] (In formula (261) or formula (262), The asterisk (*) indicates the bond position with the adjacent structure. R 101 ~R 126 each independently represents a hydrogen atom or a substituent.

[0206] Ar 61 When Ar is formula (261) or formula (262), m1 is preferably 0 or 1, and more preferably 0. 62 When Ar is formula (261) or formula (262), m2 is preferably 0 or 1, and more preferably 0. 65 When is formula (261) or formula (262), m5 is preferably 0 or 1, and 0 is more preferred.

[0207] (Ar 63 , Ar 64 ) Ar in formula (260) 63 and Ar 64 each independently represents a hydrogen atom or an optionally substituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms. Examples of the monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms include monovalent groups of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a tetraphenylene ring, a chrysene ring, a pyrene ring, a benzanthracene ring, a perylene ring, a biphenyl ring, or a terphenyl ring.

[0208] Ar in formula (260) 63 , Ar 64 are each independently preferably a hydrogen atom, a monovalent group of a benzene ring, or a monovalent group of a naphthalene ring, and more preferably a hydrogen atom or a monovalent group of a benzene ring, from the viewpoint of the solubility and durability of the compound.

[0209] In formula (260), Ar 61 , Ar 62 , Ar 63 , Ar 64 and at least one Ar when n is 1 or more. 65 At least one of them is not a hydrogen atom.

[0210] (L 1 ~L 5 ) L in equation (260) 1 ~L 5 each independently represents a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent. Examples of divalent aromatic hydrocarbon groups having 6 to 60 carbon atoms include divalent groups of a benzene ring, a naphthalene ring, an anthracene ring, a tetraphenylene ring, a phenanthrene ring, a chrysene ring, a pyrene ring, a benzanthracene ring, or a perylene ring. L 1 ~L 5 are each independently preferably a phenylene group or a divalent group in which two or more, for example, 2 to 5, phenylene groups are linked by direct bonds, which may have a substituent, and are more preferably a 1,3-phenylene group which may have a substituent from the viewpoint of solubility.

[0211] (R 60 ) R in equation (260) 60 each independently represents a substituent. The substituent may be one selected from the substituent group Z2. Among these, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, aryloxy groups, alkoxycarbonyl groups, acyl groups, halogen atoms, haloalkyl groups, alkylthio groups, arylthio groups, silyl groups, siloxy groups, aralkyl groups, and aromatic hydrocarbon groups are preferred. From the viewpoint of heat resistance and durability, alkyl groups, alkenyl groups, alkoxy groups, aryloxy groups, alkoxycarbonyl groups, acyl groups, halogen atoms, haloalkyl groups, silyl groups, siloxy groups, aralkyl groups, and aromatic hydrocarbon groups are preferred, alkyl groups, alkoxy groups, aralkyl groups, and aromatic hydrocarbon groups are more preferred, alkyl groups having 10 or less carbon atoms, aralkyl groups having 30 or less carbon atoms, and aromatic hydrocarbon groups having 30 or less carbon atoms are more preferred, and a benzene ring or a group in which 2 to 5 benzene rings are linked is particularly preferred.

[0212] (m1~m5) In formula (260), m1, m2, and m5 each independently represent an integer of 0 to 5, m3 and m4 each independently represent an integer of 0 to 5. In formula (260), m1, m2, and m5 are preferably 4 or less, more preferably 3 or less, even more preferably 2 or less, particularly preferably 1 or less, and most preferably 0, from the viewpoint of the solubility and durability of the compound.

[0213] Also, Ar 61 is the formula (261) or the formula (262), m1, Ar 62 is the formula (261) or the formula (262), and m2, and Ar 65 When is formula (261) or formula (262), m5 is preferably 0.

[0214] In terms of the solubility and durability of the compound, m3 and m4 in formula (260) are preferably 1 or more, preferably 4 or less, more preferably 3 or less, and particularly preferably 2 or less. When m1 in formula (260) is 2 or more, multiple L 1 may be the same or different. When m2 in formula (260) is 2 or more, multiple L 2 may be the same or different. When m3 in formula (260) is 2 or more, multiple L 3 may be the same or different. When m4 in formula (260) is 2 or more, multiple L 4 may be the same or different. When m5 in formula (260) is 2 or more, multiple L 5 may be the same or different.

[0215] ((L 1 ) m1 , (L 2 ) m2 , (L 3 ) m3 , (L 4 ) m4 , (L 5 ) m5 ) (L 1 ) m1 , (L 2 ) m2 , (L 3 ) m3 , (L 4 ) m4 , and at least one (L 5 ) m5 Among these, at least one group preferably has a partial structure selected from the partial structure represented by the following formula (11), the partial structure represented by the following formula (12), and the partial structure represented by the following formula (13) from the viewpoint of the solubility and durability of the compound, and when m1 is 1 or more, (L 1 ) m1 , when m2 is 1 or more (L 2 ) m2 And when n is 1 or more and m5 is 1 or more, (L 5 ) m5 , and when m3 is 1 or more, (L 3 ) m3 and m4 is 1 or more (L 4 ) m4 It is more preferable that the compound has a partial structure selected from the group consisting of a partial structure represented by the following formula (11), a partial structure represented by the following formula (12), and a partial structure represented by the following formula (13).

[0216] [ka]

[0217] In each of the above formulas (11) to (13), * indicates the bonding position with the adjacent structure or Ar 61 , Ar 62 , Ar 63 , Ar 64 or Ar 65 represents a hydrogen atom when * is a hydrogen atom, and at least one of the two * represents the bonding position with the adjacent structure. In the following description, * has the same definition unless otherwise specified.

[0218] More preferably, (L 1 ) m1 , (L 2 ) m2 , (L 3 ) m3 , (L 4 ) m4 , and at least one (L 5 ) m5 At least one of the above has a partial structure represented by formula (11) or a partial structure represented by formula (12). More preferably, in formula (260), when m1 is 1 or more, (L 1 ) m1 , when m2 is 1 or more (L 2 ) m2 , when m3 is 1 or more (L 3 ) m3 , when m4 is 1 or more (L 4 ) m4 , and when n is 1 or more and m5 is 1 or more, (L 5 ) m5 Each of them has a partial structure represented by formula (11) or a partial structure represented by formula (12). Particularly preferably, in formula (260), when m1 is 1 or more, (L 1 ) m1 , when m2 is 1 or more (L 2 ) m2 , when m3 is 1 or more (L 3 ) m3 , when m4 is 1 or more (L 4 ) m4 , and when n is 1 or more and m5 is 1 or more, (L 5 ) m5 have a partial structure represented by formula (11) and a partial structure represented by formula (12), respectively.

[0219] In formula (260), formula (12) is preferably the following formula (12-2).

[0220] [ka]

[0221] In formula (260), formula (12) is more preferably the following formula (12-3).

[0222] [ka]

[0223] In addition, from the viewpoint of the solubility and durability of the compound, (L 1 ) m1 , (L 2 ) m2 , (L 3 ) m3 , (L 4 ) m4 , at least one of and (L 5 ) m5 Among these, at least one of the partial structures preferably has a partial structure represented by formula (11) and a partial structure represented by formula (12).

[0224] In formula (260), the partial structure having the partial structure represented by formula (11) and the partial structure represented by formula (12) is preferably a partial structure selected from the following formulas (14) to (17), which is a structure containing a plurality of structures selected from the partial structure represented by formula (11) and the partial structure represented by formula (12). That is, when m1 is 1 or more, (L 1 ) m1 , when m2 is 1 or more (L 2 ) m2 , when m3 is 1 or more (L 3 ) m3 , when m4 is 1 or more (L 4 ) m4 , and when n is 1 or more and m5 is 1 or more, (L 5 ) m5 each independently has a partial structure selected from the formulas (11) to (13) and the following formulas (14) to (17):

[0225] [ka]

[0226] In formula (260), the structure containing a plurality of structures selected from the partial structure represented by formula (11) and the partial structure represented by formula (12) means, for example, a partial structure in formula (14) that can be regarded as having one partial structure represented by formula (11) and two partial structures represented by formula (12), as in the following formula (14a):

[0227] [ka]

[0228] More preferably, (L 1 ) m1 , (L 2 ) m2 , (L 3 ) m3 , (L 4 ) m4 , and at least one (L 5 ) m5 At least one of the groups has a partial structure represented by formula (14) or a partial structure represented by formula (15). More preferably, when m1 is 1 or more, (L 1 ) m1 , when m2 is 1 or more (L 2 ) m2 , when m3 is 1 or more (L 3 ) m3 , when m4 is 1 or more (L 4 ) m4 , and when n is 1 or more and m5 is 1 or more, (L 5 ) m5 has a partial structure represented by formula (14) or a partial structure represented by formula (15).

[0229] In formula (260), formula (14) is preferably the following formula (14-2).

[0230] [ka]

[0231] In formula (260), formula (14) is more preferably the following formula (14-3).

[0232] [ka]

[0233] In formula (260), formula (15) is preferably the following formula (15-2).

[0234] [ka]

[0235] In formula (260), formula (15) is more preferably the following formula (15-3).

[0236] [ka]

[0237] In formula (260), formula (17) is preferably the following formula (17-2).

[0238] [ka]

[0239] Also, (L 1 ) m1 , (L 2 ) m2 , (L 3 ) m3 , (L 4 ) m4 , and at least one (L 5 ) m5 It is more preferable that at least one of the above has a partial structure represented by the following formula (19) or a partial structure represented by the following formula (20) as a partial structure containing a partial structure represented by formula (13).

[0240] [ka]

[0241] In each of the above formulas (14) to (20), * represents a bonding position to an adjacent structure or a hydrogen atom, and at least one of the two * represents a bonding position to an adjacent structure. In formula (260), among formulas (14) to (20), formulas (14-3) and (15-3) are preferred, and formula (14-3) is more preferred.

[0242] (L 1 ~L 5 (preferred substructure of In formula (260), L 1 ~L 5 preferably has a partial structure represented by formula (11), a partial structure represented by formula (12-3), a partial structure represented by formula (14-3), or a partial structure represented by formula (15-3).

[0243] (n) In the formula (260), n represents an integer of 0 to 10. In the formula (260), n is preferably 1 or more, more preferably 2 or more, and is preferably 6 or less, more preferably 5 or less, and particularly preferably 4 or less, from the viewpoint of the solubility and durability of the compound.

[0244] (a1~a3) a1 to a3 each independently represent an integer of 0 to 3. a1 to a3 are selected from the viewpoints of the solubility and durability of the compound. It is preferable that a1 to a3 each independently represent 0 or 1. It is most preferable that a1=a2=a3=0.

[0245] (R 101 ~R 126 ) In equation (260), R 101 ~R 126 each independently represents a hydrogen atom or a substituent. The substituent may be one selected from the substituent group Z2. Among these, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, aryloxy groups, alkoxycarbonyl groups, acyl groups, halogen atoms, haloalkyl groups, alkylthio groups, arylthio groups, silyl groups, siloxy groups, aralkyl groups, or aromatic hydrocarbon groups are preferred. From the viewpoint of durability, alkyl groups, alkenyl groups, alkoxy groups, aryloxy groups, alkoxycarbonyl groups, acyl groups, halogen atoms, haloalkyl groups, silyl groups, siloxy groups, aralkyl groups, and aromatic hydrocarbon groups are preferred, with hydrogen atoms and aromatic hydrocarbon groups being more preferred, and hydrogen atoms being particularly preferred.

[0246] (substituent) In formula (260), Ar 61 ~Ar 65 and L 1 ~L 5 The substituents that the divalent aromatic hydrocarbon group having 6 to 60 carbon atoms in the formula (I) may have can be independently selected from the substituent group Z2. Among these, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an acyl group, a halogen atom, a haloalkyl group, an alkylthio group, an arylthio group, a silyl group, a siloxy group, an aralkyl group, or an aromatic hydrocarbon group is preferred, and an alkyl group, an alkenyl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an acyl group, a halogen atom, a haloalkyl group, a silyl group, a siloxy group, an aralkyl group, or an aromatic hydrocarbon group is more preferred.

[0247] (molecular weight) The molecular weight of the compound represented by formula (260) is preferably 3,000 or less, more preferably 2,500 or less, even more preferably 2,000 or less, particularly preferably 1,500 or less, and is usually 400 or more, preferably 500 or more, more preferably 600 or more.

[0248] (Example) Specific examples of the compound represented by formula (260) are shown below, but the invention is not limited to these.

[0249] [ka]

[0250] [ka]

[0251] [ka]

[0252] The first composition may contain only one type of compound represented by the formula (260), or may contain two or more types.

[0253] [Organic solvents] The organic solvent contained in the first composition is a volatile liquid component used to form a layer containing the compound represented by formula (240) or formula (241) by wet film formation. The organic solvent is not particularly limited as long as it is an organic solvent in which the compound represented by formula (240) or formula (241), the light-emitting material, and the charge-transporting compound, which are solutes, can be well dissolved.

[0254] Preferred organic solvents include, for example, alkanes such as n-decane, cyclohexane, ethylcyclohexane, decalin, and bicyclohexane; aromatic hydrocarbons such as toluene, xylene, mesitylene, phenylcyclohexane (cyclohexylbenzene), tetralin, and methylnaphthalene; halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, and trichlorobenzene; 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole, phenetole, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3-dimethylanisole, 2,4-dimethylanisole, and diphenyl ether. aromatic esters such as phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, propyl benzoate, and n-butyl benzoate; alicyclic ketones such as cyclohexanone, cyclooctanone, and fenchone; alicyclic alcohols such as cyclohexanol and cyclooctanol; aliphatic ketones such as methyl ethyl ketone and dibutyl ketone; aliphatic alcohols such as butanol and hexanol; and aliphatic ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and propylene glycol-1-monomethyl ether acetate (PGMEA).

[0255] Among these, from the viewpoints of viscosity and boiling point, alkanes, aromatic hydrocarbons, aromatic ethers, and aromatic esters are preferred, aromatic hydrocarbons, aromatic ethers, and aromatic esters are more preferred, and aromatic hydrocarbons and aromatic esters are particularly preferred. These organic solvents may be used alone or in any combination of two or more in any ratio.

[0256] The boiling point of the organic solvent used is usually 80°C or higher, preferably 100°C or higher, more preferably 120°C or higher, and usually 380°C or lower, preferably 350°C or lower, more preferably 330°C or lower. If the boiling point of the organic solvent is below this range, the film formation stability may decrease during wet film formation due to solvent evaporation from the composition. If the boiling point of the organic solvent is above this range, the film formation stability may decrease during wet film formation due to solvent residue after film formation.

[0257] In particular, a uniform coating film can be produced by combining two or more of the above organic solvents having a boiling point of 150° C. or higher. If there is only one or more organic solvents having a boiling point of 150° C. or higher, it is thought that a uniform film may not be formed during coating.

[0258] The content of the organic solvent in the first composition is preferably 1% by mass or more, more preferably 10% by mass or more, particularly preferably 50% by mass or more, and preferably 99.99% by mass or less, more preferably 99.90% by mass or less, particularly preferably 99.00% by mass or less. The thickness of the light-emitting layer is usually about 3 to 200 nm, but if the content of the organic solvent is below this lower limit, the viscosity of the first composition becomes too high, which may reduce the workability of film formation. On the other hand, if the content of the organic solvent is above this upper limit, the thickness of the film obtained by removing the solvent after film formation will be insufficient, which tends to make film formation difficult.

[0259] <Second organic layer> The polymer contained in the second organic layer has a triarylamine structure as a repeating unit and does not have a crosslinking group, and the triarylamine structure is preferably contained in the main chain of the polymer. The repeating unit of the triarylamine structure is represented by the following formula (50).

[0260] [ka]

[0261] (In formula (50), Ar 51 represents an aromatic hydrocarbon group which may have a substituent other than a crosslinking group, an aromatic heterocyclic group which may have a substituent other than a crosslinking group, or a group in which a plurality of groups selected from an aromatic hydrocarbon group which may have a substituent other than a crosslinking group and an aromatic heterocyclic group which may have a substituent other than a crosslinking group are linked together; Ar 52 represents a divalent aromatic hydrocarbon group which may have a substituent other than a bridging group, a divalent aromatic heterocyclic group which may have a substituent other than a bridging group, or a divalent group in which a plurality of at least one group selected from the group consisting of the divalent aromatic hydrocarbon groups and the divalent aromatic heterocyclic groups 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.

[0262] (Ar 51 ) In the repeating unit represented by the above formula (50), Ar 51 represents an aromatic hydrocarbon group which may have a substituent other than a crosslinking group, an aromatic heterocyclic group which may have a substituent other than a crosslinking group, or a group in which a plurality of groups selected from an aromatic hydrocarbon group which may have a substituent other than a crosslinking group and an aromatic heterocyclic group which may have a substituent other than a crosslinking group are linked together.

[0263] The aromatic hydrocarbon group preferably has 6 to 60 carbon atoms, and specific examples thereof include monovalent groups of 6-membered monocyclic rings or 2 to 5 condensed rings, such as a 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, or groups in which multiple of these are linked together. Note that, for example, a "monovalent group of a benzene ring" means a "benzene ring having a single free valence," i.e., a phenyl group.

[0264] The aromatic heterocyclic group preferably has 3 or more and 60 or less carbon atoms, and specific examples thereof include 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 benzoyl ... Examples of the 5- or 6-membered ring include a monovalent group of a 5- or 6-membered monocyclic ring or a monovalent group of 2- to 4-fused rings, such as an isoxazole 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, and an azulene ring, or a group in which a plurality of these rings are linked together.

[0265] Ar 51 is preferably an aromatic hydrocarbon group which may have a substituent other than a crosslinking group, from the viewpoints of excellent charge transport properties and excellent durability, and among these, a monovalent group of a benzene ring or a fluorene ring which may have a substituent other than a crosslinking group, i.e., a phenyl group or a fluorenyl group which may have a substituent other than a crosslinking group, is more preferred, a fluorenyl group which may have a substituent other than a crosslinking group is even more preferred, and a 2-fluorenyl group which may have a substituent other than a crosslinking group is particularly preferred.

[0266] Ar 51 The substituents other than the crosslinking group that the aromatic hydrocarbon group and aromatic heterocyclic group may have are not particularly limited as long as they do not significantly impair the properties of the present polymer. The substituents are preferably groups selected from the above-mentioned substituent group Z2, more preferably alkyl groups, alkoxy groups, aromatic hydrocarbon groups, and aromatic heterocyclic groups, and even more preferably alkyl groups.

[0267] Ar 51 In terms of solubility in a coating 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.

[0268] 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.

[0269] Also, Ar 51 is also preferably a spirobifluorenyl group from the viewpoint of solubility in a coating solvent.

[0270] (Other preferred Ar 51 ) The polymer may include a repeating unit represented by the formula (50) 51 At least one of the above is preferably a group containing a monovalent or divalent group in which 2 to 5 optionally substituted benzene rings are linked together, a fluorenyl group which may have a substituent, 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).

[0271] (Group represented by formula (51))

[0272] [ka]

[0273] In formula (51), * represents a bond to the nitrogen atom of the main chain of formula (50), Ar 53 , Ar 54 each independently represent a divalent aromatic hydrocarbon group which may have a substituent other than a crosslinking group, an aromatic heterocyclic group which may have a substituent other than a crosslinking group, or a divalent group in which a plurality of aromatic hydrocarbon groups which may have a substituent other than a crosslinking group or aromatic heterocyclic groups which may have a substituent other than a crosslinking group are linked together directly or via a linking group; Ar 55 represents an aromatic hydrocarbon group which may have a substituent other than a crosslinking group, an aromatic heterocyclic group which may have a substituent other than a crosslinking group, or a monovalent group in which a plurality of aromatic hydrocarbon groups or aromatic heterocyclic groups which may have a substituent other than a crosslinking group are linked together directly or via a linking group, Ar 56 represents a hydrogen atom or a substituent.

[0274] (Ar 53 , Ar 54 ) In the repeating unit represented by the formula (51), Ar 53 , Ar 54 each independently represent a divalent aromatic hydrocarbon group which may have a substituent other than a crosslinking group, a divalent aromatic heterocyclic group which may have a substituent other than a crosslinking group, or a divalent group in which a plurality of aromatic hydrocarbon groups which may have a substituent other than a crosslinking group or aromatic heterocyclic groups which may have a substituent other than a crosslinking group are linked together directly or via a linking group. A preferred group is a divalent aromatic hydrocarbon group which may have a substituent other than a crosslinking group or a group in which a plurality of divalent aromatic hydrocarbon groups which may have a substituent other than a crosslinking group are linked together. Here, the substituents which the aromatic hydrocarbon group and the aromatic heterocyclic group may have are preferably the same as those in the above-mentioned substituent group Z2.

[0275] Ar 53 and Ar 54 The aromatic hydrocarbon group and aromatic heterocyclic group are 52 The same aromatic hydrocarbon groups and aromatic heterocyclic groups as those mentioned above can be used.

[0276] The divalent group in which a plurality of optionally substituted aromatic hydrocarbon groups or optionally substituted aromatic heterocyclic groups are linked directly or via a linking group may be a group in which a plurality of the same groups are linked, or a group in which a plurality of different groups are linked.

[0277] When a plurality of the above divalent groups are linked together, examples include divalent groups with 2 to 10 linked groups, and divalent groups with 2 to 5 linked groups are preferred.

[0278] Ar 53 is preferably a group in which 1 to 6 optionally substituted divalent aromatic hydrocarbon groups are linked together, more preferably a group in which 2 to 4 optionally substituted divalent aromatic hydrocarbon groups are linked together, and among these, a group in which 1 to 4 optionally substituted phenylene rings are linked together is more preferred, and biphenylene in which 2 optionally substituted phenylene rings are linked together is particularly preferred.

[0279] When a plurality of such 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 be conjugated. Specifically, it is preferable that the group 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.

[0280] Ar 53 The substituents that Ar may have are preferably the same as those in the substituent group Z2. 53 has no substituents.

[0281] Ar 54 From the viewpoints 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 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 one to four phenylene rings, which may have a substituent, are linked together, or groups in which a phenylene ring, which may have a substituent, and a fluorene ring, which may have a substituent, are linked together. From the viewpoint of a wider LUMO, biphenylene, in which two phenylene rings, which may have a substituent, are linked together, is particularly preferred.

[0282] Ar 54 The substituents that may be possessed by may be any of the substituents in the above-mentioned group Z2, or a combination thereof. The substituents are preferably other than an N-carbazolyl group, an indolocarbazolyl group, and an indenocarbazolyl group, and more preferably, a phenyl group, a naphthyl group, or a fluorenyl group. It is also preferable that the group has no substituent.

[0283] (Ar 55 ) Ar 55 is a monovalent group in which a plurality of groups selected from an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, and an aromatic hydrocarbon group which may have a substituent and the aromatic heterocyclic group which may have a substituent are linked directly or via a linking group. Preferably, it is a group in which a plurality of monovalent aromatic hydrocarbon groups which may have a substituent or monovalent aromatic hydrocarbon groups which may have a substituent are linked.

[0284] Here, the substituents which the aromatic hydrocarbon group and the aromatic heterocyclic group may have are preferably the same groups as those in the above-mentioned substituent group Z2.

[0285] When a plurality of aromatic hydrocarbons are linked, they are preferably divalent groups of 2 to 10 linked rings, and more preferably monovalent groups of 2 to 5 linked rings. 51 The same aromatic hydrocarbon groups and aromatic heterocyclic groups as those mentioned above can be used.

[0286] Ar 55 It is preferable that the compound has a structure represented by any one of the following schemes 2. Furthermore, from the viewpoint of distributing the LUMO of the molecule, 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 e1 to e4 is preferable. 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, and e1 to e4 is preferable. Furthermore, from the viewpoint of a high triplet level and the effect of confining excitons formed in the light-emitting layer, a structure selected from a-1 to a-4, d-1 to d-12, and e1 to e4 is preferable. Furthermore, from the viewpoint of easy synthesis and excellent stability, d-1 and d-10 are more preferable, and the benzene ring structure of d-1 is particularly preferable. Furthermore, these structures may have a substituent. In the figure, "-*" represents Ar 54 If there are multiple "-*", one of them must be Ar 54 represents the bonding position with

[0287] [ka]

[0288] [ka]

[0289] [ka]

[0290] <R 31 and R 32 > R in Scheme 2 31 and R 32 are each independently preferably 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.

[0291] R 31 and R 32 may be the same or different, but all R 31 and R 32 are preferably the same group.

[0292] Ar 55 As the substituent that may be possessed by Ar, any one of the substituents in the above-mentioned group Z2 or a combination thereof can be used. 54 It is preferable that the substituents are selected from the same substituents that may be possessed by the group.

[0293] (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 which may have a substituent or an aromatic heterocyclic group which may have a substituent. 53 ~Ar 54 It is a monovalent structure similar to the aromatic hydrocarbon structure and aromatic heterocyclic structure mentioned above.

[0294] Ar 56 When Ar is a substituent, it is preferably bonded to the 3-position of carbazole from the viewpoint of improving durability. 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 transportability, 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.

[0295] Ar 56 is preferably a hydrogen atom from the viewpoint of ease of synthesis and charge transport properties.

[0296] Ar 56 When is an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent, the substituents are the same as those exemplified in the substituent group Z2, the preferred substituents are also the same, and the substituents that these substituents may further have are also the same.

[0297] (Group represented by formula (52)) In addition, the polymer may contain Ar in the repeating unit represented by the above formula (50). 51 At least one of the groups is preferably a group represented by the following formula (52): The reason for this is thought to be that in the two carbazole structures in the following formula (52), the LUMOs are distributed in the aromatic hydrocarbon group or aromatic heterocyclic group between the nitrogen atoms, thereby suppressing the influence on the main chain amine in formula (50) and improving the durability of the main chain amine against electrons and excitons.

[0298] [ka]

[0299] (In formula (52), Ar 61 and Ar 62 each independently represents a divalent aromatic hydrocarbon group which may have a substituent other than a crosslinking group or a divalent aromatic heterocyclic group which may have a substituent other than a crosslinking group, Ar 63 ~Ar 65 are each independently a hydrogen atom or a substituent. * indicates the bonding position to the nitrogen atom in formula (50).

[0300] (Ar 63 ~Ar 65 ) Ar 63 ~Ar 65 Each of Ar independently represents a hydrogen atom or a substituent. 63 ~Ar 65 When is a substituent, the substituent is not particularly limited, but is preferably an aromatic hydrocarbon group which may have a substituent other than a bridging group, or an aromatic heterocyclic group which may have a substituent other than a bridging group. Preferred structures of the aromatic hydrocarbon group and aromatic heterocyclic group include the above-mentioned Ar 51 The groups are the same as those listed above.

[0301] Ar 63 ~Ar 65 is a substituent, Ar 63 ~Ar 65 is preferably bonded to the 3- or 6-position of each carbazole structure from the viewpoint of improving durability.

[0302] Ar 63 ~Ar 65 is preferably a hydrogen atom from the viewpoint of ease of synthesis and charge transport properties.

[0303] Ar 63 ~Ar 65 From the viewpoint of improving durability and charge transportability, 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.

[0304] Ar 63 ~Ar 65 When is an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent, the substituents are the same as those exemplified in the substituent group Z2, the preferred substituents are also the same, and the substituents that these substituents may further have are also the same.

[0305] (Ar 62 ) Ar 62 is a divalent aromatic hydrocarbon group which may have a substituent or a divalent aromatic heterocyclic group which may have a substituent.

[0306] The aromatic hydrocarbon group preferably has 6 to 60 carbon atoms, more preferably 10 to 50 carbon atoms, and particularly preferably 12 to 40 carbon atoms. Specific examples of the aromatic hydrocarbon group include divalent groups of 6-membered monocyclic 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 multiple such groups are linked together. When multiple such groups are linked together, the multiple linked divalent aromatic hydrocarbon groups are preferably conjugated.

[0307] The aromatic heterocyclic group preferably has 3 to 60 carbon atoms, and specific examples thereof include 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, and a benzoiso Examples thereof include a divalent group of a 5- or 6-membered monocyclic ring or a 2- to 4-condensed ring such as an oxazole 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 a group in which a plurality of these rings are linked together.

[0308] The substituents that these aromatic hydrocarbon groups or aromatic heterocyclic groups may have include the alkyl groups, aralkyl groups, and aromatic hydrocarbon groups of the above-mentioned substituent group Z2. 62 In the case where the structure of Ar is twisted, it is preferable to have no substituents. 62 In the case where the structure does not become distorted, it is preferable that the group has a substituent.

[0309] Ar 62 Preferred groups are divalent groups of a benzene ring, a naphthalene ring, an anthracene ring, or a fluorene ring, or groups in which multiple such groups are linked together, more preferably divalent groups of benzene rings or groups in which multiple such groups are linked together, particularly preferably 1,4-phenylene groups in which benzene rings are linked together at the divalent positions 1 and 4, 2,7-fluorenylene groups in which fluorene rings are linked together at the divalent positions 2 and 7, or groups 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-".

[0310] In these preferred structures, the phenylene group does not have a substituent other than the linking position, which is due to the steric effect of the substituent. 62 In addition, it is preferable that the fluorenylene group has substituents at the 9- and 9'-positions from the viewpoint of improving the solubility and durability of the fluorene structure.

[0311] (Ar 61 ) Ar 61 is a divalent group that connects to the nitrogen atom of the main chain amine in formula (52). Ar 61 is a divalent aromatic hydrocarbon group which may have a substituent other than a bridging group, or a divalent aromatic heterocyclic group which may have a substituent other than a bridging group.

[0312] Ar 61 The aromatic hydrocarbon group preferably has 6 to 60 carbon atoms, more preferably 10 to 50 carbon atoms, and particularly preferably 12 to 40 carbon atoms. Specific examples of the aromatic hydrocarbon group include divalent groups of a 6-membered monocyclic ring 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 multiple of these are linked together.

[0313] Ar 61 The aromatic heterocyclic group preferably has 3 to 60 carbon atoms. Specific examples thereof include a 5- or 6-membered monocyclic or 2- to 4-fused ring divalent group, such as a furan ring, benzofuran ring, thiophene ring, benzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, oxadiazole ring, indole ring, carbazole ring, pyrroloimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, benzisoxazole ring, benzisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring, quinoline ring, isoquinoline ring, cinnoline ring, quinoxaline ring, phenanthridine ring, benzimidazole ring, perimidine ring, quinazoline ring, quinazolinone ring, and azulene ring, or a group in which a plurality of these are linked together.

[0314] The substituents which these aromatic hydrocarbon groups or aromatic heterocyclic groups may have include the alkyl groups, aralkyl groups and aromatic hydrocarbon groups of the above-mentioned substituent group Z2.

[0315] When a plurality of such divalent aromatic hydrocarbon groups or divalent aromatic heterocyclic groups are linked, the plurality of linked divalent aromatic hydrocarbon groups are preferably linked so as not to be conjugated. Specifically, it is preferable that the group 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.

[0316] (Group represented by formula (53)) Ar in the repeating unit represented by the formula (50) 51 At least one of the above is preferably a group represented by the following formula (53):

[0317] [ka]

[0318] 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 which may have a substituent, Ar 72 and Ar 73 each independently represent an optionally substituted aromatic hydrocarbon group, an optionally substituted aromatic heterocyclic group, or a monovalent group in which two or more groups selected from optionally substituted aromatic hydrocarbon groups and optionally substituted aromatic heterocyclic groups are linked together directly or via a linking group; 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 the groups is a carbon atom, the carbon atom may have a substituent.

[0319] <Ar 71 > Ar 71 is the Ar 53 is a group similar to Ar 71 As the alkyl group, one optionally substituted divalent aromatic hydrocarbon group or a group in which 2 to 10 optionally substituted divalent aromatic hydrocarbon groups are linked together is preferred, one optionally substituted divalent aromatic hydrocarbon group or a group in which 2 to 8 optionally substituted divalent aromatic hydrocarbon groups are linked together is more preferred, and a group in which two or more optionally substituted divalent aromatic hydrocarbon groups are linked together is particularly preferred.

[0320] 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.

[0321] Also, Ar 71 preferably contains at least one benzene ring linked at the 1- and 3-positions, which is a non-conjugated moiety, and more preferably contains two or more.

[0322] Ar 71 In the case of a group in which 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.

[0323] For this reason, Ar 71 Preferred structures linking the nitrogen atom in the main chain of the polymer and the ring HA in the 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 the 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.

[0324] [ka]

[0325] [ka]

[0326] Ar 71 The substituents that Ar may have include any one of the substituents in the above-mentioned group Z2 or a combination thereof. 71 The preferred range of the substituent that may be possessed by G is the same as the substituent that may be possessed by G when it is an aromatic hydrocarbon group.

[0327] <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 them is a C atom, it may have a substituent.

[0328] X is chosen to localize the LUMO more easily around the HA ring. 2 and Y 2 are preferably all N atoms.

[0329] X 2 and Y 2 When at least one of X is a C atom, the substituent may be any one of the substituents in the group Z2 or a combination thereof. 2 and Y 2 More preferably, has no substituent.

[0330] <Ar 72 and Ar 73 > Ar 72 and Ar 73 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 two or more groups selected from an aromatic hydrocarbon group which may have a substituent and an aromatic heterocyclic group which may have a substituent are linked together directly or via a linking group.

[0331] From the viewpoint of distributing the LUMO of the molecule, Ar 72 and Ar 73 each independently have 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 Scheme 2 above.

[0332] Furthermore, from the viewpoint of promoting the broadening of the LUMO of the molecule by having an electron-withdrawing group, structures selected from a-1 to a-4, b-1 to b-9, c-1 to c-5, d-1 to d-12, and e-1 to e-4 are preferred.

[0333] Furthermore, from the viewpoint of a high triplet level and the effect of confining excitons formed in the light-emitting layer, structures selected from a-1 to a-4, d-1 to d-12, and e-1 to e-4 are preferred.

[0334] In order to prevent aggregation of molecules, structures selected from d-1 to d-12 and e-1 to e-4 are more preferred. 72 =Ar 73 = d-1 or d-10 is preferred, and the benzene ring structure of d-1 is particularly preferred.

[0335] These structures may also have a substituent. "-*" represents the binding site to the cyclic HA. When there are multiple "-*", any one of them represents the binding site to the cyclic HA.

[0336] Ar 72 and Ar 73 As the substituent that may be possessed by the compound, any one of the substituents in the substituent group Z2 described above or a combination thereof can be used. From the viewpoint of durability and charge transport properties, the substituent is preferably the same group as that in the substituent group Z2 described above.

[0337] (Ar 52 ) Ar 52 The aromatic hydrocarbon group in the formula (50) is Ar 51 In addition, Ar 52 The aromatic hydrocarbon group and the substituent that the aromatic hydrocarbon group may have in the above formula are preferably the same groups as those in the above group of substituents Z2.

[0338] [Bridging group] The polymer used in the second organic layer does not have a crosslinking group. Here, the crosslinking group in this embodiment refers to a group that reacts with another crosslinking group located in the vicinity of the crosslinking group 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.

[0339] Examples of the crosslinking group include 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 examples of the crosslinking group include groups selected from the following group T of crosslinking groups.

[0340] (Bridging group T)

[0341] [ka]

[0342] [ka]

[0343] In the above-mentioned bridging group T, R XL represents a methylene group, an oxygen atom, or a sulfur atom; n XL represents an integer from 0 to 5. R XL When there are multiple, they may be the same or different, and n XL When there are multiple groups, they may be the same or different. *1 indicates the bonding position. These bridging groups may have a substituent.

[0344] Hereinafter, the repeating unit represented by formula (54), the repeating unit represented by formula (55), the repeating unit represented by formula (56), and the repeating unit represented by formula (57) will be described in detail as more preferred repeating units of formula (50).

[0345] It is also preferable that the polymer having a triarylamine structure as a repeating unit contains a plurality of repeating units of different structures in each of the repeating units represented by these formulas.

[0346] <Repeating unit represented by formula (54)>

[0347] [ka]

[0348] (In formula (54), Ar 51 is Ar in the formula (50). 51 is the same as 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 other than a crosslinking group, R 207 ~R 209 and R 211 ~R 214 each independently represents a hydrogen atom, an alkyl group which may have a substituent other than a bridging group, an aralkyl group which may have a substituent other than a bridging group, or an aromatic hydrocarbon group which may have a substituent other than a bridging group, a, b, and d each independently represent an integer of 0 to 4; c is an integer from 0 to 3, However, if a is 1 or more, c is 1 or more, and if b is 1 or more, d is 1 or more, 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, 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, i and j are each independently an integer of 0 to 3.

[0349] (R 201 , R 202 , R 221 , R 222 ) R in the repeating unit represented by the above formula (54) 201 , R 202 , R 221 and R 222 are each independently an alkyl group which may have a substituent other than a crosslinking group.

[0350] 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.

[0351] R 201 If there are multiple R 201 may be the same or different, and 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 R 201 and R 202 are preferably the same group.

[0352] R 221 If there are multiple R 221 may be the same or different, and R 222 If there are multiple R 222 may be the same or different. Since the charge can be uniformly distributed around the nitrogen atom and synthesis is easy, all R 221 and R 222 are preferably the same group.

[0353] (R 207 ~R 209 and R 211 ~R 214 ) R 207 ~R 209 and R 211 ~R 214 are each independently a hydrogen atom, an alkyl group which may have a substituent other than a crosslinking group, an aralkyl group which may have a substituent other than a crosslinking group, or an aromatic hydrocarbon group which may have a substituent other than a crosslinking group.

[0354] 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.

[0355] Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-hexyl group, an n-octyl group, a cyclohexyl group, and a dodecyl group.

[0356] 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.

[0357] 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.

[0358] 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.

[0359] 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 are linked together.

[0360] From the viewpoint of improving charge transport properties 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.

[0361] R 201 , R 202 , R 221 , R 222 alkyl group, R 207 ~R 209 and R 211 ~R 214 The alkyl group, aralkyl group, and aromatic hydrocarbon group may have a substituent other than a bridging group. The substituent other than a bridging group may be any of the substituents described above in R 207 ~R 209 and R 211 ~R 214 Examples of the alkyl group, aralkyl group and aromatic hydrocarbon group include those mentioned above as preferred groups.

[0362] R 201 , R 202 , R 221 , R 222 alkyl group, 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.

[0363] (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. Preferably, a+b is 1 or greater, and each of a and b is preferably 2 or less, with both a and b being 1 being more preferred. Here, a being 1 or greater means that c is 1 or greater, and b being 1 or greater means that d is 1 or greater. When b is 1 or greater, d is also preferably 1 or greater. 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.

[0364] When a+b is 1 or more, the aromatic rings in the main chain are twisted due to steric hindrance, resulting in excellent solubility of the polymer in solvents, and the coating film formed by a wet film-forming method and heat-treated tends to be excellent insolubility in solvents. 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, elution of the polymer into the organic solvent-containing composition for forming the light-emitting layer used in the present invention is suppressed. As a result, it is thought that the formed light-emitting layer is less affected, and the operating life of the organic electroluminescent device is further extended.

[0365] 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.

[0366] 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.

[0367] where R 201 and R 202 and are bonded at positions symmetric to each other means that R 201 and R 202 In this case, a 180-degree rotation around the main chain is considered to be the same structure.

[0368] 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.

[0369] (i and j) In the repeating unit represented by the above formula (54), i and j each independently represent an integer of 0 to 3. Preferably, i and j are each 2 or less, and more preferably, both i and j are 0 or 1.

[0370] (Ar 51 ) In the repeating unit represented by the above formula (54), Ar 51 is Ar in the formula (50). 51 and is a group in which a plurality of groups selected from an aromatic hydrocarbon group which may have a substituent other than a crosslinking group, an aromatic heterocyclic group which may have a substituent other than a crosslinking group, and an aromatic hydrocarbon group which may have a substituent other than a crosslinking group and an aromatic heterocyclic group which may have a substituent other than a crosslinking group are linked together.

[0371] Examples of the group in which a plurality of groups selected from an aromatic hydrocarbon group which may have a substituent other than a bridging group, an aromatic heterocyclic group which may have a substituent other than a bridging group, and an aromatic hydrocarbon group which may have a substituent other than a bridging group and an aromatic heterocyclic group which may have a substituent other than a bridging group are linked include Ar 51 The same as in the case of Ar in the formula (50) can be mentioned, and the substituents other than the bridging group and the preferred structure are also the same as in the case of Ar 51 The same as in the case of

[0372] (Other preferred Ar 51 ) Ar in the repeating unit represented by the above formula (54) 51 It is more preferable that at least one of the groups is a group represented by the formula (51), the formula (52), or the formula (53). In the two carbazole structures in the formula (52), the LUMOs are distributed in the aromatic hydrocarbon group or aromatic heterocyclic group between the nitrogen atoms, which is thought to tend to improve durability against electrons and excitons.

[0373] (X) X in the above formula (54) is -C(R 207 )(R 208 )- or -N(R 209 )-, and -C(R 207 )(R 208 )- is more preferred.

[0374] In addition, in the polymer containing the repeating unit represented by the above formula (54), Ar 51 , R 201 , R 202 , R 221 , R 222 When there are a plurality of X's, they may be the same or different. Preferably, the polymer contains a plurality of repeating units represented by formula (54) having the same structure. In this case, when the polymer contains a plurality of repeating units having the same structure, the HOMO and LUMO of the repeating units are the same, so that charges are not concentrated at a specific shallow level to form traps, and it is thought that this results in excellent charge transport properties.

[0375] (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).

[0376] [ka]

[0377] [ka]

[0378] 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.

[0379] [Specific 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 examples include the following structures.

[0380] [ka]

[0381] [ka]

[0382] [ka]

[0383] [ka]

[0384] [ka]

[0385] [ka]

[0386] [ka]

[0387] [ka]

[0388] [Content of repeating unit represented by formula (54)] When the polymer contained in the second organic layer has a repeating unit represented by formula (54), the content of the repeating unit represented by formula (54) is not particularly limited, but the repeating unit represented by formula (54) is usually contained in the polymer at 10 mol % or more, preferably 30 mol % or more, more preferably 40 mol % or more, and even more preferably 50 mol % or more.

[0389] When the polymer contained in the second organic layer has a repeating unit represented by formula (54), the repeating unit may consist solely of the repeating unit represented by formula (54), but for the purpose of balancing various performances when formed into an organic electroluminescent device, the polymer may contain a repeating unit other than the repeating unit represented by formula (54). In this case, the content of the repeating unit represented by formula (54) in the polymer is usually 99 mol % or less, preferably 95 mol % or less.

[0390] [Terminal group] In this specification, the term "terminal group" refers to the structure of the terminal portion of the polymer formed by an endcapping agent used at the end of polymerization of the polymer. In the second organic layer, the terminal group of the polymer containing the repeating unit represented by formula (54) is preferably a hydrocarbon group. From the viewpoint of charge transportability, the hydrocarbon group preferably has 1 to 60 carbon atoms, more preferably 1 to 40 carbon atoms, and even more preferably 1 to 30 carbon atoms.

[0391] 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, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-hexyl group, a cyclohexyl group, or a dodecyl group; a linear, branched, or cyclic alkenyl group, such as a vinyl group, which usually has 2 or more carbon atoms and usually has 24 or less carbon atoms, preferably 12 or less carbon atoms; a linear or branched alkynyl group, such as an ethynyl group, having typically 2 or more carbon atoms and typically 24 or less, and preferably 12 or less, carbon atoms; Examples include aromatic hydrocarbon groups having usually 6 or more carbon atoms and usually 36 or less, and preferably 24 or less, such as a phenyl group and a naphthyl group.

[0392] 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 a plurality of these optional optional substituents, they may be bonded to each other to form a ring.

[0393] From the viewpoint of charge transportability and durability, the terminal group is preferably an alkyl group or an aromatic hydrocarbon group, and more preferably an aromatic hydrocarbon group.

[0394] <Repeating unit represented by formula (55)>

[0395] [ka]

[0396] (In formula (55), Ar 51 is Ar in the formula (50) or the formula (54). 51 is the same as R 303 and R 306 each independently represents an alkyl group which may have a substituent other than a crosslinking group, R 304 and R 305 each independently represents an alkyl group which may have a substituent other than a crosslinking group, an alkoxy group which may have a substituent other than a crosslinking group, or an aralkyl group which may have a substituent other than a crosslinking group, l, n, p, and q are each independently 0 or 1; m is 1 or 2; However, if p is 1, then l is 1, and if q is 1, then n is 1.)

[0397] (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 other than a crosslinking group. The alkyl group is R in the formula (54). 201 and R 202 The substituents that may be possessed and the preferred structures are the same as those of R 201 and R 202 The same can be mentioned. R 303 If there are multiple R 303 may be the same or different, and R 306 If there are multiple R 306 may be the same or different.

[0398] (R 304 , R 305 ) R in the repeating unit represented by the above formula (55) 304 and R 305 are each independently an alkyl group which may have a substituent other than a crosslinking group, an alkoxy group which may have a substituent other than a crosslinking group, or an aralkyl group which may have a substituent other than a crosslinking group, preferably an alkyl group which may have a substituent other than a crosslinking group. R 304 and R 304 are preferably the same.

[0399] 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.

[0400] Specific examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-hexyl group, an n-octyl group, a cyclohexyl group, and a dodecyl group.

[0401] The alkoxy group is not particularly limited, and may be an alkoxy group (-OR 10 )R 10 The group may have a linear, branched, or cyclic structure, and preferably has 1 or more carbon atoms, preferably 24 or less, and more preferably 12 or less, since this tends to improve the solubility of the polymer.

[0402] Specific examples 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.

[0403] The aralkyl group is not particularly limited, but preferably has 5 or more carbon atoms, and preferably has 60 or less, and more preferably has 40 or less carbon atoms, since this tends to improve the solubility of the polymer.

[0404] Specific examples 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.

[0405] (l, m and n) l represents 0 or 1, and n represents 0 or 1.

[0406] 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 contained in the second organic layer tends to be increased, and precipitation from the composition for organic electroluminescent elements containing the polymer tends to be suppressed.

[0407] m represents 1 or 2, and is preferably 1, since the organic electroluminescent device of the present invention can be driven at a low voltage and hole injection ability, transport ability, and durability tend to be improved.

[0408] (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 contained in the second organic layer is increased, and precipitation from the second composition containing the polymer tends to be suppressed. Furthermore, when p + q is 1 or more, the aromatic rings in 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, which contains an organic solvent, is suppressed.

[0409] (Ar 51 ) In the repeating unit represented by the above formula (55), Ar 51 is Ar in the formula (50) or the formula (54). 51 and is a group in which a plurality of groups selected from an aromatic hydrocarbon group which may have a substituent other than a crosslinking group, an aromatic heterocyclic group which may have a substituent other than a crosslinking group, and an aromatic hydrocarbon group which may have a substituent other than a crosslinking group and an aromatic heterocyclic group which may have a substituent other than a crosslinking group are linked together.

[0410] Examples of the group in which a plurality of groups selected from an aromatic hydrocarbon group which may have a substituent other than a bridging group, an aromatic heterocyclic group which may have a substituent other than a bridging group, and an aromatic hydrocarbon group which may have a substituent other than a bridging group and an aromatic heterocyclic group which may have a substituent other than a bridging group are linked include Ar 51 The same as in the case of Ar in the formula (50) can be mentioned, and the substituents other than the bridging group and the preferred structure are also the same as in the case of Ar 51 The same as in the case of

[0411] [Specific examples of the main chain of the repeating unit represented by formula (55)] The main chain structure excluding the N atom of the repeating unit represented by formula (55) is not particularly limited, but examples thereof include the following structures.

[0412] [ka]

[0413] [ka]

[0414] [ka]

[0415] [ka]

[0416] [ka]

[0417] [ka]

[0418] [ka]

[0419] [ka]

[0420] [Content of repeating unit represented by formula (55)] When the polymer contained in the second organic layer has a repeating unit represented by formula (55), the content of the repeating unit represented by formula (55) is not particularly limited, but the repeating unit represented by formula (55) is usually contained in the polymer at 10 mol % or more, preferably 30 mol % or more, more preferably 40 mol % or more, and particularly preferably 50 mol % or more.

[0421] When the polymer contained in the second organic layer has a repeating unit represented by formula (55), the repeating unit may consist solely of the repeating unit represented by formula (55), but for the purpose of balancing various performances when formed into an organic electroluminescent device, the polymer may contain a repeating unit other than the repeating unit represented by formula (55). In this case, the content of the repeating unit represented by formula (55) in the polymer is usually 99 mol % or less, preferably 95 mol % or less.

[0422] [Terminal group] In the polymer contained in the second organic layer, the end group of the polymer containing the repeating unit represented by formula (55) is preferably a hydrocarbon group, similar to the end group of the polymer containing the repeating unit represented by formula (54). Preferred hydrocarbon groups and the substituents that may be possessed are also similar to those of the end group of the polymer containing the repeating unit represented by formula (54).

[0423] <Repeating unit represented by formula (56)>

[0424] [ka]

[0425] (In formula (56), Ar 51 is Ar in the formula (50), the formula (54) or the formula (55). 51 is the same as Ar 41 represents a divalent aromatic hydrocarbon group which may have a substituent other than a bridging group, a divalent aromatic heterocyclic group which may have a substituent other than a bridging group, or a divalent group in which a plurality of groups selected from the group consisting of the divalent aromatic hydrocarbon groups and the divalent aromatic heterocyclic groups are linked together directly or via a linking group, R 441 and R 442 each independently represents an alkyl group which may have a substituent other than a crosslinking group, t is 1 or 2; u is 0 or 1; r and s each independently represent an integer of 0 to 4, However, if s is 1 or greater, then u is 1.)

[0426] (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 other than a crosslinking group.

[0427] The alkyl group is 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 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.

[0428] R 441 and R 442 When there are a plurality of repeating units represented by the above formula (56), R 441 and R 442 may be the same or different.

[0429] (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 or greater, multiple r's may be the same or different, and when u is 2 or greater, multiple s's may be the same or different. r+s is preferably 1 or greater, and each of r and s is preferably 2 or less. When r+s is 1 or greater, the operating life of the organic electroluminescent device is thought to be further extended.

[0430] 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.

[0431] (Ar 51 ) In the repeating unit represented by the above formula (56), Ar 51 is Ar in the formula (50), the formula (54) or the formula (55). 51 and is a group in which a plurality of groups selected from an aromatic hydrocarbon group which may have a substituent other than a crosslinking group, an aromatic heterocyclic group which may have a substituent other than a crosslinking group, and an aromatic hydrocarbon group which may have a substituent other than a crosslinking group and an aromatic heterocyclic group which may have a substituent other than a crosslinking group are linked together.

[0432] The aromatic hydrocarbon group which may have a substituent other than a bridging group or the aromatic heterocyclic group which may have a substituent other than a bridging group includes Ar 51 The same as in the case of Ar in the formula (50) can be mentioned, and the substituents other than the bridging group and the preferred structure are also the same as in the case of Ar 51 The same as in the case of

[0433] (Ar 41 ) Ar 41 is a divalent aromatic hydrocarbon group which may have a substituent other than a bridging group, a divalent aromatic heterocyclic group which may have a substituent other than a bridging group, or a divalent group in which a plurality of at least one group selected from the group consisting of the divalent aromatic hydrocarbon groups and the divalent aromatic heterocyclic groups are linked together directly or via a linking group.

[0434] Ar 41 The aromatic hydrocarbon group in the formula (50) is preferably Ar 52 The aromatic hydrocarbon group and the substituents that the aromatic hydrocarbon group may have are preferably the same as those in the substituent group Z2, and the substituents that the aromatic hydrocarbon group may further have are also preferably the same as those in the substituent group Z2.

[0435] [Specific examples of repeating units represented by formula (56)] Specific examples of the main chain of the repeating unit represented by formula (56) are shown below.

[0436] [ka]

[0437] [Content of repeating unit represented by formula (56)] When the polymer contained in the second organic layer has a repeating unit represented by formula (56), the content of the repeating unit represented by formula (56) is not particularly limited, but the repeating unit represented by formula (56) is usually contained in the polymer at 10 mol % or more, preferably 30 mol % or more, more preferably 40 mol % or more, and particularly preferably 50 mol % or more.

[0438] When the polymer contained in the second organic layer has a repeating unit represented by formula (56), the repeating unit may consist solely of the repeating unit represented by formula (56), but for the purpose of balancing various performances when formed into an organic electroluminescent device, the polymer may contain a repeating unit other than the repeating unit represented by formula (56). In this case, the content of the repeating unit represented by formula (56) in the polymer is usually 99 mol % or less, preferably 95 mol % or less.

[0439] [Terminal group] In the polymer contained in the second organic layer, the end group of the polymer containing the repeating unit represented by formula (56) is preferably a hydrocarbon group, similar to the end group of the polymer containing the repeating unit represented by formula (54). Preferred hydrocarbon groups and the substituents that may be possessed are also similar to those of the end group of the polymer containing the repeating unit represented by formula (54).

[0440] <Repeating unit represented by formula (57)>

[0441] [ka]

[0442] (In formula (57), Ar 51 is Ar in the formula (50), the formula (54), the formula (55) or the formula (56). 51 is the same as R 517 ~R 519 each independently represents an alkyl group which may have a substituent other than a crosslinking group, an alkoxy group which may have a substituent other than a crosslinking group, an aralkyl group which may have a substituent other than a crosslinking group, an aromatic hydrocarbon group which may have a substituent other than a crosslinking group, or an aromatic heterocyclic group which may have a substituent other than a crosslinking group; f, g, and h each independently represent an integer of 0 to 4; e is an integer from 0 to 3, However, if g is 1 or greater, e is 1 or greater.)

[0443] (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 same as those in the above-mentioned group Z2 or the substituents in the above-mentioned group Z3 or the substituents in the above-mentioned group Z4 or the substituents in the above-mentioned group Z5 or the substituents in the above-mentioned group Z6 or the substituents in the above-mentioned group Z7 or the substituents in the above-mentioned group Z8 or the substituents in the above-mentioned group Z9 or the substituents in the above-mentioned group Z10 or the substituents in the above-

[0444] R 517 ~R 519 The alkyl group and aralkyl group in the R 207 The same groups as those listed in R are preferred, and the substituents that may be further substituted are also the same as those listed in R 207 Groups similar to the following are preferred.

[0445] R 517 ~R 519 The alkoxy group in the formula (I) is preferably the alkoxy group exemplified in the above-mentioned group Z2 of substituents, and the substituents that may be further substituted are also the same as those in the above-mentioned group Z2 of substituents.

[0446] (f, g, h) f, g, and h each independently represent an integer of 0 to 4. When e is 2 or more, multiple g's may be the same or different.

[0447] (e) e represents an integer of 0 to 3, and when g is 1 or greater, e is 1 or greater. It is preferable that e=2, and it is also preferable that e=1 or 3, but it is more preferable that e=2.

[0448] The repeating unit represented by the formula (57) is preferably a repeating unit represented by the following formula (58).

[0449] <Repeating unit represented by formula (58)>

[0450] [ka]

[0451] (In formula (58), Ar 51 is Ar in the formula (54). 51 is similar to R 517 ~R 519 , f, g, h, and e are R in the formula (57) 517 ~R 519 , f, g, h, e.)

[0452] In the repeating unit represented by the formula (58), when e=2, It is preferable that g is 1 or more, It is more preferable that g is 1 or more, and f and h are 2 or less. It is more preferable that g is 1 or more, and f and h are 1 or less. It is particularly preferred that g is 1 or more and f and h are 0. In addition, in the repeating unit represented by the formula (58), it is preferable that e = 2 and g = 1. When e = 2 and g = 1, the two R 518 are preferably bonded at positions symmetrical to each other. Also, there are two R 518 are preferably the same. Here, there are two R 518 are bonded at positions symmetrical to each other, the bond positions shown below are used. However, for the purposes of notation, structures rotated 180 degrees around the main chain are considered to be the same structure.

[0453] [ka]

[0454] (In the above formula, Ar 51 is Ar in the formula (54). 51 is similar to R 517 ~R 519 , f, h are R in the formula (57) 517 ~R 519 , f, h.)

[0455] In the repeating unit represented by the formula (58), when e=1 or 3, It is preferable that f+g+h is 1 or more. f+h is preferably 1 or greater, It is more preferable that f+h is 1 or more, and f, g, and h are 2 or less. It is more preferable that f+h is 1 or more, and f and h are 1 or less, Most preferably, f and h are both 1.

[0456] When f and h are both 1, R 517 and R 519 are preferably bonded at positions symmetrical to each other. Also, R 517 and R 519 are preferably the same as

[0457] where R 517 and R 519 are bonded at positions symmetrical to each other, the bond positions shown below are used. However, for the purposes of notation, structures rotated 180 degrees around the main chain are considered to be the same structure.

[0458] [ka]

[0459] (In the above formula, Ar 51 is Ar in the formula (54). 51 is similar to R 517 ~R 519 , e, g are R in the formula (57) 517 ~R 519 , e, g.)

[0460] It is also preferable that g is 2 in the repeating unit represented by the formula (58). If g is 2, then two R 518 are more preferably bonded to each other at para positions, If g is 2, then two R 518 It is more preferred that are the same.

[0461] In the repeating unit represented by the formula (58), it is preferable that e=1 or 3 and g=0 or 2. When g=2, the bonding positions are the 2nd and 5th positions. When g=0, that is, R 518 When there is no steric hindrance due to the presence of two R 518 When the bond is diagonal to the benzene ring, R 517 and R 519 and can be bonded at positions symmetrical to each other.

[0462] <Specific examples of the main chain of the repeating unit represented by formula (57)> The main chain structure excluding the N atom of the repeating unit represented by formula (57) is not particularly limited, but examples thereof include the following structures.

[0463] [ka]

[0464] [Content of repeating unit represented by formula (57)] When the polymer contained in the second organic layer has a repeating unit represented by formula (57), the content of the repeating unit represented by formula (57) is not particularly limited, but the repeating unit represented by formula (57) is usually contained in an amount of 10 mol % or more in the polymer, preferably 30 mol % or more, more preferably 40 mol % or more, and particularly preferably 50 mol % or more.

[0465] When the polymer contained in the second organic layer has a repeating unit represented by formula (57), the repeating unit may consist solely of the repeating unit represented by formula (57), but for the purpose of balancing various performances when formed into an organic electroluminescent device, the polymer may contain a repeating unit other than the repeating unit represented by formula (57). In this case, the content of the repeating unit represented by formula (57) in the polymer is usually 99 mol % or less, preferably 95 mol % or less.

[0466] [Terminal group] In the polymer contained in the second organic layer, the end group of the polymer containing the repeating unit represented by formula (57) is preferably a hydrocarbon group, similar to the end group of the polymer containing the repeating unit represented by formula (54). Preferred hydrocarbon groups and the substituents that may be possessed are also similar to those of the end group of the polymer containing the repeating unit represented by formula (54).

[0467] The repeating units represented by any of formulas (50) to (58) do not contain a crosslinking group. When a crosslinking group is not contained, the polymer chain is less likely to be distorted by 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.

[0468] [Preferred repeating units] When the polymer contained in the second organic layer 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). Furthermore, it is preferable that the polymer has one or more repeating units selected from the repeating units represented by the formula (54), the repeating units represented by the formula (55), the repeating units represented by the formula (56), and the repeating units represented by the formula (57), and that a+b in the formula (54) is 1 or more, r+s in the formula (56) is 1 or more, and f+g+h in the formula (57) is 1 or more, in terms of increasing the energy gap and suppressing a decrease in luminous efficiency. Furthermore, it is also preferable to have two or more repeating units selected from the repeating units represented by the formula (54), the repeating units represented by the formula (55), the repeating units represented by the formula (56), and the repeating units represented by the formula (57), or to consist of only one or more repeating units, since this contains many structures with a large energy gap. The polymer contained in the second organic layer preferably has at least a repeating unit represented by the formula (54), more preferably has a repeating unit represented by the formula (54) and a repeating unit represented by the formula (57), and further preferably consists of only a repeating unit represented by the formula (54) and a repeating unit represented by the formula (57).

[0469] When the polymer has a repeating unit represented by the following formula (54), a repeating unit represented by the following formula (55), a repeating unit represented by the following formula (56), or a repeating unit represented by the following formula (57), it preferably contains a partial structure represented by the following formula (61) or the following formula (61′), and among these, A repeating unit represented by formula (54) containing a partial structure represented by formula (61) or formula (61′): A repeating unit represented by formula (55) containing a partial structure represented by formula (61) or formula (61′): A repeating unit represented by formula (56) containing a partial structure represented by formula (61) or formula (61′): Alternatively, it is preferable that the repeating unit has the repeating unit represented by the formula (57) above, which contains a partial structure represented by the following formula (61) or formula (61').

[0470] [ka]

[0471] (In formula (61) and formula (61'), R 601 is R in equation (54) 201 or R 202 , R in Eq. (55) 303 , R 304 , R 305 , or R 406 , R in Eq. (56) 441 or R+, R in formula (57) 517 , R 518 or R 519 and -* represents a bond to the adjacent atom. When formula (61) and formula (61') are partial structures of formula (54) or formula (56), Ring B may be part of a fused ring. The partial structures represented by formula (61) and formula (61') are R 601 In addition, when Ring A and Ring B are a partial structure of formula (54), R 201 or R 202 , if it is a partial structure of formula (55), R 303 , R 304 , R 305 , or R 406 , if it is a partial structure of formula (56), R 441 or R 442 , if it is a partial structure of formula (57), R 517 , R 518 or R 519 )

[0472] The partial structure represented by the formula (61) or (61′) is a substantially planar structure of Ring A and Ring B formed by π conjugation, which is represented by R 601 The main chain is distorted by the steric hindrance of the π-conjugated bond, resulting in a structure in which the main chain is twisted more than in the normal case.

[0473] (Formula (62)) The repeating unit contained in the polymer is particularly preferably a repeating unit represented by formula (54). The repeating unit represented by formula (54) is preferably a repeating unit represented by the following formula (62).

[0474] [ka]

[0475] (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, a 1 , a 2 , b 1 , b 2 , i 1 , i 2 , j 1 , j 2 are each independently 0 or 1. However, either of the following conditions (1) or (2) must be met. (1)a 1 , a 2 and at least one of a is 1 or greater; b 1 , b 2 and at least one of b is 1 or greater; c is 1 or greater and d is 1 or greater; If c is 1, then a 1 or a 2 At least one of is 1, If d is 1, then b 1 or b 2 At least one of them is 1. (2)i 1 , i 2 , j 1 and j 2 At least one of is 1. Ring B1 is R 201 and Ring B2 is R 201 a divalent group having c-1 benzene rings linked together, which may have the formula: Ring B3 refers to a divalent fused ring in which a biphenyl structure is further bonded with X. Ring B4 is R 202 a divalent group having d-1 benzene rings linked together, which may have the formula: Ring B5 is R 202 It refers to a divalent benzene ring which may have

[0476] Here, a in formula (54) being 1 or more means that a 1 , a 2 and a are equal to or greater than 1, and b being equal to or greater than 1 in formula (54) means that b 1 , b 2 and at least one of b is 1 or greater.

[0477] As shown below, the formula (62) contains the formula (61) or the formula (61') as a partial structure. a 1 , a 2 and at least one of a is 1 or greater, a 1 or a 2 If at least one of is 1, When c is 2 or more, Ring B1 and Ring B2, or When c is 1, Ring B1 and Ring B3 are containing the formula (61) or the formula (61') as a partial structure, When a is 1 or more, in this case c is 2 or more, Ring B2 and Ring B1, or Ring B2 and Ring B3 contain the formula (61) or the formula (61') as a partial structure, Alternatively, when c is 3 or more and a is 1 or more, the formula (61) or (61') may be contained in Ring B2 as a partial structure.

[0478] Similarly, b 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.

[0479] Also, i 1 , i 2 , j 1 and j 2 If at least one of is 1, i 1 and i 2 If either or both of these are 1, then R in Ring B3 221 and the benzene ring of Ring B2 or Ring B1 form a partial structure represented by formula (61'), j 1 and j 2 If either or both of these are 1, then R in Ring B3 222 It can be seen that the ring to which is bonded and the benzene ring of Ring B4 or Ring B5 form the partial structure of formula (61).

[0480] That is, it is clear that Ring B3 and Ring B2 or Ring B1, or Ring B3 and Ring B4 or Ring B5 have a twisted structure. Therefore, since the formula (62) contains a structure in which the aromatic ring of the main chain is twisted, it is preferable because a flat film can be easily obtained for the reasons described above.

[0481] [Molecular weight of polymer] The molecular weight of the polymer contained in the second organic layer will be described below.

[0482] The weight-average molecular weight (Mw) of the polymer containing the repeating unit represented by formula (54) or formula (57) is usually 3,000,000 or less, preferably 1,000,000 or less, more preferably 500,000 or less, even more preferably 200,000 or less, and particularly preferably 100,000 or less. The weight-average molecular weight is usually 2,500 or more, preferably 5,000 or more, more preferably 10,000 or more, even more preferably 15,000 or more, and particularly preferably 17,000 or more.

[0483] When the weight-average molecular weight of the polymer is equal to or less than the upper limit, the polymer tends to have good solubility in a solvent and excellent film-forming properties. When the weight-average molecular weight of the polymer is equal to or greater than the lower limit, the polymer may have improved heat resistance because the glass transition temperature, melting point, and vaporization temperature are prevented from decreasing.

[0484] The number average molecular weight (Mn) of the polymer containing the repeating unit represented by formula (54) or formula (57) is usually 2,500,000 or less, preferably 750,000 or less, more preferably 400,000 or less, and particularly preferably 100,000 or less. The number average molecular weight 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.

[0485] Furthermore, the dispersity (Mw / Mn) of the polymer containing the repeating unit represented by formula (54) or formula (57) is preferably 3.5 or less, more preferably 2.5 or less, and particularly preferably 2.0 or less. Since the smaller the dispersity, the better, the lower limit is ideally 1. When the dispersity of the polymer is the above upper limit or less, purification is easy and the solubility in solvents and charge transport ability are good.

[0486] The weight average molecular weight (Mw) of the polymer containing the repeating unit represented by formula (55) or formula (56) is preferably 10,000 or more, more preferably 15,000 or more, and even more preferably 17,000 or more. The weight average molecular weight is preferably 2,000,000 or less, more preferably 1,000,000 or less, and particularly preferably 100,000 or less.

[0487] When the weight-average molecular weight of the polymer is equal to or less than the upper limit, the increase in molecular weight of impurities is suppressed, and purification tends to be easy. On the other hand, when the weight-average molecular weight of the polymer is equal to or more than the lower limit, the decrease in the glass transition temperature, melting point, vaporization temperature, etc. is suppressed, and heat resistance tends to be improved.

[0488] The number average molecular weight (Mn) of the polymer containing the repeating unit represented by formula (55) or formula (56) is preferably 1,000,000 or less, more preferably 800,000 or less, and even more preferably 500,000 or less, and is preferably 4,000 or more, more preferably 8,000 or more, and even more preferably 10,000 or more.

[0489] Furthermore, the dispersity (Mw / Mn) of the polymer containing the repeating unit represented by formula (55) or formula (56) is preferably 3.5 or less, more preferably 3.0 or less, even more preferably 2.4 or less, particularly preferably 2.1 or less, and most preferably 2 or less. The dispersity of the polymer is preferably 1 or more, more preferably 1.1 or more, and even more preferably 1.2 or more. When the dispersity of the polymer is the above upper limit or less, purification becomes easy, and a decrease in solubility in solvents and a decrease in charge transport ability tend to be suppressed.

[0490] 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 higher the molecular weight component, the shorter the elution time, and the lower the molecular weight component, the longer the elution time. 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.

[0491] [Specific example] Specific examples of polymers containing the repeating unit represented by formula (54) are shown below, but the polymers used in the present invention are not limited to these. The numbers in the chemical formulas represent the molar ratios of the repeating units, and n represents the number of repeats.

[0492] These polymers may be any of random copolymers, alternating copolymers, block copolymers, graft copolymers, etc., and there are no limitations on the sequence of the monomers.

[0493] [ka]

[0494] [ka]

[0495] A polymer containing a repeating unit represented by formula (55) and Ar of the repeating unit represented by formula (55) 51 Specific examples of polymers having a structure represented by formula (52) are shown below, but the polymers used in the present invention are not limited to these. The numbers in the chemical formula represent the molar ratio of repeating units, and n represents the number of repeats.

[0496] These polymers may be any of random copolymers, alternating copolymers, block copolymers, graft copolymers, etc., and the sequence of the monomers is not limited.

[0497] [ka]

[0498] [ka]

[0499] [ka]

[0500] [ka]

[0501] [ka]

[0502] [ka]

[0503] [ka]

[0504] Specific examples of polymers containing the repeating unit represented by formula (56) are shown below, but the polymers used in the present invention are not limited to these. The numbers in the chemical formula represent the molar ratio of the repeating unit. n represents the number of repeats.

[0505] These polymers may be any of random copolymers, alternating copolymers, block copolymers, graft copolymers, etc., and there are no limitations on the sequence of the monomers.

[0506] [ka]

[0507] [ka]

[0508] [ka]

[0509] [ka]

[0510] [Second Composition] The second composition that forms the second organic layer will now be described. The second composition contains the above-mentioned polymer and a solvent. This second composition is usually used to form a layer or film by a wet film-forming method, and is preferably used to form an organic layer of an organic electroluminescent device. The organic layer is preferably a hole transport layer. The second composition may contain one type of the above-mentioned polymer, or two or more types in any combination and in any ratio.

[0511] [Organic solvents] The second composition usually contains an organic solvent. The organic solvent is preferably one that dissolves the polymer. Specifically, a suitable solvent is one that dissolves the polymer in the second composition at room temperature in a concentration of usually 0.05% by mass or more, preferably 0.5% by mass or more, and more preferably 1% by mass or more. Specific examples of organic solvents include aromatic solvents such as toluene, xylene, mesitylene, cyclohexylbenzene, and methylnaphthalene; halogen-containing solvents such as 1,2-dichloroethane, chlorobenzene, and o-dichlorobenzene; aliphatic ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and propylene glycol-1-monomethyl ether acetate (PGMEA); 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole, phenetole, 2-methoxytoluene, and 3-methoxytoluene. Examples of organic solvents include ether-based solvents such as aromatic ethers such as toluene, 4-methoxytoluene, 2,3-dimethylanisole, and 2,4-dimethylanisole; aliphatic ester-based solvents such as ethyl acetate, n-butyl acetate, ethyl lactate, and n-butyl lactate; and ester-based solvents such as aromatic esters such as phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, isopropyl benzoate, propyl benzoate, and n-butyl benzoate; as well as other organic solvents used in the composition for forming a hole injection layer and the composition for forming a hole transport layer, which will be described later.

[0512] The solvent may be used alone or in any combination of two or more in any ratio. The content of the solvent in the second composition is usually 10% by mass or more, preferably 30% by mass or more, more preferably 50% by mass or more, and particularly preferably 80% by mass or more. By ensuring that the solvent content is equal to or greater than the lower limit, the flatness and uniformity of the formed layer can be improved.

[0513] [Electron-accepting compounds] In order to reduce the resistance, the second composition preferably further contains an electron-accepting compound. In particular, when the second composition is used to form a hole injection layer, the second composition preferably contains an electron-accepting compound.

[0514] The electron-accepting compound is preferably a compound having oxidizing power and the ability to accept one electron from the polymer contained in the second organic layer. Specifically, a compound having an electron affinity of 4 eV or more is preferred, and a compound having an electron affinity of 5 eV or more is more preferred.

[0515] The second composition may contain one type of electron-accepting compound as described above, or may contain two or more types in any combination and ratio.

[0516] When the second composition contains an electron-accepting compound, the content of the electron-accepting compound in the second composition is usually 0.0005% by mass or more, preferably 0.001% by mass or more, and usually 20% by mass or less, preferably 10% by mass or less.

[0517] Furthermore, the ratio of the electron accepting compound to the polymer in the second composition is usually 0.5% by mass or more, preferably 1% by mass or more, more preferably 3% by mass or more, and is usually 80% by mass or less, preferably 60% by mass or less, and even more preferably 40% by mass or less.

[0518] When the content of the electron-accepting compound in the second composition is equal to or greater than the lower limit, the electron acceptor accepts electrons from the polymer, thereby reducing the resistance of the formed organic layer. When the content of the electron-accepting compound in the second composition is equal to or less than the upper limit, the formed organic layer is less likely to have defects and less likely to have uneven thickness.

[0519] [Cation radical compounds] The second composition may further contain a cation radical compound. The cation radical compound is preferably an ionic compound consisting of a cation radical, which is a chemical species obtained by removing one electron from a hole-transporting compound, and a counter anion. However, when the cation radical is derived from a hole-transporting polymer compound, the cation radical has a structure in which one electron is removed from the repeating unit of the polymer compound.

[0520] The cation radical is preferably a chemical species obtained by removing one electron from a hole transport compound described below, which is preferable in terms of amorphousness, visible light transmittance, heat resistance, solubility, etc.

[0521] The cation radical compound can be produced by mixing a hole transport compound (described later) with the electron acceptor compound described above. That is, by mixing the hole transport compound with the electron acceptor compound, electrons are transferred from the hole transport compound to the electron acceptor compound, and a cation ion compound consisting of a cation radical of the hole transport compound and a counter anion is produced.

[0522] When the second composition contains a cation radical compound, the content of the cation radical compound in the composition for organic electroluminescent elements is usually 0.0005% by mass or more, preferably 0.001% by mass or more, and usually 40% by mass or less, preferably 20% by mass or less. A content of the cation radical compound of at least the lower limit is preferred because the resistance of the formed organic layer is low, while a content of the cation radical compound of at most the upper limit is preferred because defects are less likely to occur in the formed organic layer and film thickness unevenness is less likely to occur.

[0523] In addition to the above components, the second composition may contain components contained in the composition for forming a hole injection layer or the composition for forming a hole transport layer, which will be described later, in the amounts described later.

[0524] [Polymer manufacturing method] The method for producing the polymer contained in the second organic layer is not particularly limited and may be any method, such as a polymerization method based on the Suzuki reaction, a polymerization method based on the Grignard reaction, a polymerization method based on the Yamamoto reaction, a polymerization method based on the Ullmann reaction, or a polymerization method based on the Buchwald-Hartwig reaction.

[0525] In 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 (2) 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).

[0526] [ka]

[0527] (In the above reaction scheme, Ar 1 , R 1 , R 2 , X, and a to d have the same meanings as in the formula (2).

[0528] 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 (3) 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 aminoaryl represented by formula (2b).

[0529] [ka]

[0530] (In the above reaction scheme, Ar 2 , R 3 ~R 6 , l to n, p, and q have the same meanings as in the formula (3).

[0531] 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, or triethylamine. It can also be carried out in the presence of a transition metal catalyst such as a copper or palladium complex.

[0532] [Organic electroluminescent device] An example of the structure of the organic electroluminescent device of the present invention is an organic electroluminescent device 8 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.

[0533] The compound represented by the formula (240) or (241) is preferably contained in the light-emitting layer 5, and more preferably used as a charge-transporting compound in the light-emitting layer 5.

[0534] <Structure of organic electroluminescent device> As an example of the structure of the organic electroluminescent device of the present invention, Fig. 1 shows a schematic diagram (cross section) of an example of the structure of an organic electroluminescent device 8. 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.

[0535] [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 exposure to the outside air. Therefore, when using a material with low gas barrier properties, such as a synthetic resin substrate, 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.

[0536] [anode] The anode 2 has the function of injecting holes into the layer on the light-emitting layer 5 side.

[0537] 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; carbon black, or a conductive polymer such as poly(3-methylthiophene), polypyrrole, or polyaniline.

[0538] The anode 2 is usually formed by a dry method such as sputtering or vacuum deposition. When forming the anode using metal particles such as silver, copper iodide, carbon black, conductive metal oxide particles, or conductive polymer fine powder, the anode can be formed by dispersing the particles in an appropriate binder resin solution and applying it to the substrate. In the case of a conductive polymer, the anode can be formed by forming a thin film directly on the substrate by electrolytic polymerization or by applying the conductive polymer to the substrate (Appl. Phys. Lett., Vol. 60, p. 2711, 1992).

[0539] 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.

[0540] 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 even 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.

[0541] 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 its ionization potential to improve hole injection properties.

[0542] [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 is sometimes 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.

[0543] The thickness of the hole injection layer 3 is usually 1 nm or more, preferably 5 nm or more, and usually 1000 nm or less, preferably 500 nm or less.

[0544] The hole injection layer may be formed by vacuum deposition or wet film formation, but is preferably formed by wet film formation in terms of excellent film formability.

[0545] A general method for forming a hole injection layer will be described below. In the organic electroluminescent device of the present invention, the hole injection layer is preferably formed by a wet film formation method using a composition for forming a hole injection layer.

[0546] [Hole transport compounds] The composition for forming a hole injection layer usually contains a hole transporting compound that will become the hole injection layer 3 . In addition, in the case of a wet film formation method, the hole injection layer-forming composition usually further contains a solvent. It is preferable that the hole injection layer-forming composition has high hole transport properties and can efficiently transport injected holes. Therefore, it is preferable that the hole injection layer-forming composition has high hole mobility and is less likely to generate impurities that become traps during production, use, etc. It is also preferable that the composition has excellent stability, a small ionization potential, and high transparency to visible light. In particular, when the hole injection layer is in contact with the light-emitting layer, it is preferable that the composition does not quench the light emission from the light-emitting layer or that does not form exciplexes with the light-emitting layer to reduce the light-emitting efficiency.

[0547] From the viewpoint of the charge injection barrier from the anode to the hole injection layer, the hole transport compound is preferably a compound having an ionization potential of 4.5 eV to 6.0 eV. Examples of the hole transport compound include aromatic amine compounds, phthalocyanine compounds, porphyrin compounds, oligothiophene compounds, polythiophene compounds, benzylphenyl compounds, compounds in which a tertiary amine is linked via a fluorene group, hydrazone compounds, silazane compounds, and quinacridone compounds.

[0548] Among the above-mentioned exemplary compounds, aromatic amine compounds are preferred, and aromatic tertiary amine compounds are particularly preferred, from the viewpoints of amorphousness and visible light transmittance. Here, the aromatic tertiary amine compounds are compounds having an aromatic tertiary amine structure and also include compounds having a group derived from an aromatic tertiary amine.

[0549] The type of aromatic tertiary amine compound is not particularly limited, but it is preferable to use a polymer compound (polymerizable compound having a series of repeating units) having a weight-average molecular weight of 1,000 or more and 1,000,000 or less, since uniform light emission is easily obtained due to the surface smoothing effect.

[0550] [Formation of hole injection layer by wet film formation method] When forming the hole injection layer 3 by a wet film formation method, a composition for film formation (hole injection layer composition) is usually prepared by mixing the material for the hole injection layer with a soluble solvent (hole injection layer solvent). Then, the hole injection layer 3 is formed by applying the hole injection layer composition onto a layer (usually an anode) corresponding to the layer below the hole injection layer to form a film and drying it.

[0551] The concentration of the hole transport compound in the composition for forming a hole injection layer may be any concentration as long as it does not significantly impair the effects of the present invention, but a lower concentration is preferable in terms of uniformity of the film thickness, and a higher concentration is preferable in terms of preventing defects from occurring in the hole injection layer. Specifically, the concentration is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and particularly preferably 0.5% by mass or more, and is preferably 70% by mass or less, more preferably 60% by mass or less, and particularly preferably 50% by mass or less.

[0552] Examples of the solvent include ether solvents, ester solvents, aromatic hydrocarbon solvents, and amide solvents.

[0553] 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.

[0554] Examples of ester solvents include aromatic esters such as phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, propyl benzoate, and n-butyl benzoate.

[0555] Examples of aromatic hydrocarbon solvents include toluene, xylene, cyclohexylbenzene, 3-isopropylbiphenyl, 1,2,3,4-tetramethylbenzene, 1,4-diisopropylbenzene, cyclohexylbenzene, and methylnaphthalene.

[0556] Examples of amide solvents include N,N-dimethylformamide and N,N-dimethylacetamide.

[0557] In addition to these, dimethyl sulfoxide and the like can also be used.

[0558] The formation of the hole injection layer 3 by a wet film formation method is usually carried out by preparing a composition for forming the 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.

[0559] After the hole injection layer 3 is formed, the coated film is usually dried by heating, drying under reduced pressure, or the like.

[0560] [Formation of hole injection layer by vacuum deposition method] When forming the hole injection layer 3 by vacuum deposition, one or more types of materials constituting the hole injection layer 3 are usually placed in a crucible installed in a vacuum chamber (when two or more types of materials are used, each is usually placed in a separate crucible), and the inside of the vacuum chamber is vacuumed by a vacuum pump for 10 -4 The chamber is evacuated to approximately 100 Pa. The crucible is then heated (when two or more materials are used, each crucible is usually heated) and the materials in the crucible are evaporated while controlling their evaporation rates (when two or more materials are used, each material is usually evaporated while controlling its evaporation rate independently), forming a hole injection layer on the anode on the substrate placed opposite the crucible. When two or more materials are used, a mixture of the materials can also be placed in the crucible and heated to evaporate to form the hole injection layer.

[0561] The degree of vacuum during deposition is not limited as long as it does not significantly impair the effects of the present invention. -6 Torr (0.13 × 10 -4 Pa) or above, 9.0×10 -6 Torr (12.0 × 10 -4 The deposition rate is not limited as long as it does not significantly impair the effects of the present invention, but is usually 0.1 Å / sec or more and 5.0 Å / sec or less. The deposition temperature during deposition is not limited as long as it does not significantly impair the effects of the present invention, but is preferably 10°C or more and 50°C or less.

[0562] The hole injection layer 3 may be crosslinked.

[0563] [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. In the organic electroluminescent device of the present invention, the hole transport layer 4 is preferably formed 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.

[0564] The thickness of the hole transport layer 4 is usually 5 nm or more, preferably 10 nm or more, and on the other hand, is usually 300 nm or less, preferably 100 nm or less.

[0565] The hole transport layer 4 may be formed by vacuum deposition or wet film formation, but is preferably formed by wet film formation in terms of excellent film formability.

[0566] A general method for forming a hole transport layer will be described below, but in the organic electroluminescent device of the present invention, the hole transport layer is preferably formed by a wet film formation method using the second composition.

[0567] The hole transport layer 4 usually contains a hole transport compound. The hole transport compound contained in the hole transport layer 4 is preferably a polymer contained in the second organic layer.

[0568] In addition to the polymer contained in the second organic layer, the hole transporting compound, aromatic diamines containing two or more tertiary amines and having two or more condensed aromatic rings substituted with nitrogen atoms, such as 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (JP-A-5-234681), and aromatic amine compounds having a starburst structure, such as 4,4',4''-tris(1-naphthylphenylamino)triphenylamine (J. Lumin Preferred examples include aromatic amine compounds consisting of triphenylamine tetramers (Chem. Commun., vol. 72-74, p. 985, 1997), spiro compounds such as 2,2',7,7'-tetrakis-(diphenylamino)-9,9'-spirobifluorene (Synth. Metals, vol. 91, p. 209, 1997), and carbazole derivatives such as 4,4'-N,N'-dicarbazolebiphenyl. Other examples include polyvinylcarbazole, polyvinyltriphenylamine (JP-A-7-53953), and polyarylene ether sulfones containing tetraphenylbenzidine (Polym. Adv. Tech., vol. 7, p. 33, 1996).

[0569] [Formation of hole transport layer by wet film formation method] When the hole transport layer is formed by a wet film formation method, it is usually formed using a composition for forming a hole transport layer instead of the composition for forming a hole injection layer, in the same manner as when the hole injection layer described above is formed by a wet film formation method.

[0570] When the hole transport layer is formed by a wet film formation method, the composition for forming the hole transport layer usually further contains a solvent. The solvent used in the composition for forming the hole transport layer can be the same as the solvent used in the composition for forming the hole injection layer described above.

[0571] The concentration of the hole transporting compound in the composition for forming a hole transport layer can be set to the same range as the concentration of the hole transporting compound in the composition for forming a hole injection layer.

[0572] The hole transport layer can be formed by a wet film formation method in the same manner as the above-mentioned hole injection layer formation method.

[0573] [Formation of hole transport layer by vacuum deposition method] When forming the hole transport layer by vacuum deposition, it can be formed in the same manner as when forming the hole injection layer by vacuum deposition, except that the hole transport layer-forming composition is used instead of the hole injection layer-forming composition. The film formation conditions, such as the degree of vacuum, deposition rate, and temperature during deposition, can be the same as those for the vacuum deposition of the hole injection layer.

[0574] [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. When a hole transport layer is present on the anode, the light-emitting layer is formed between the hole transport layer and the cathode.

[0575] The organic electroluminescent device of the present invention has a first organic layer, and the first organic layer is preferably an emitting layer, and contains a compound represented by formula (240) or formula (241), and preferably further contains the emitting material and the charge transport compound.

[0576] 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 preferably 200 nm or less, more preferably 100 nm or less.

[0577] The light-emitting layer 5 contains at least a material having light-emitting properties as a light-emitting material, and preferably contains one or more charge-transporting compounds as a host material.

[0578] (Charge transport material) The charge transporting material is a material that has the ability to transport positive charges (holes) or negative charges (electrons), and is not particularly limited as long as it does not impair the effects of the present invention, and known materials can be used.

[0579] As the charge transporting material, compounds that have been used in the light-emitting layer 5 of organic electroluminescent devices can be used, and compounds that have been used as host materials for the light-emitting layer 5 are particularly preferred.

[0580] Specific examples of the charge transporting material include the compounds exemplified as the hole transporting compound for the hole injection layer 3, such as aromatic amine compounds, phthalocyanine compounds, porphyrin compounds, oligothiophene compounds, polythiophene compounds, benzylphenyl compounds, compounds in which a tertiary amine is linked via a fluorene group, hydrazone compounds, silazane compounds, silanamine compounds, phosphamine compounds, and quinacridone compounds, as well as electron transporting compounds such as anthracene compounds, pyrene compounds, carbazole compounds, pyridine compounds, phenanthroline compounds, oxadiazole compounds, and silole compounds.

[0581] Further, for example, aromatic diamines containing two or more tertiary amines, such as 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl, in which two or more condensed aromatic rings are substituted on the nitrogen atom (Japanese Patent Application Laid-Open No. 5-234681), aromatic amine compounds having a starburst structure, such as 4,4',4''-tris(1-naphthylphenylamino)triphenylamine (J. Lumin., vol. 72-74, p. 985, 1997), triphenylamines, etc. Compounds exemplified as hole-transporting compounds for the hole-transport layer 4, such as aromatic amine compounds consisting of a tetramer of amine (Chem. Commun., p. 2175, 1996), fluorene compounds such as 2,2',7,7'-tetrakis-(diphenylamino)-9,9'-spirobifluorene (Synth. Metals, Vol. 91, p. 209, 1997), and carbazole compounds such as 4,4'-N,N'-dicarbazolebiphenyl, can also be preferably used. Other examples include oxadiazole compounds such as 2-(4-biphenylyl)-5-(p-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD) and 2,5-bis(1-naphthyl)-1,3,4-oxadiazole (BND); silole compounds such as 2,5-bis(6'-(2',2"-bipyridyl))-1,1-dimethyl-3,4-diphenylsilole (PyPySPyPy); and phenanthroline compounds such as bathophenanthroline (BPhen) and 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP, bathocuproine).

[0582] [Formation of light-emitting layer by wet film formation method] The method for forming the light-emitting layer may be a vacuum deposition method or a wet film-forming method, but a wet film-forming method is preferred due to its excellent film-forming properties, and a spin coating method and an ink-jet method are more preferred. In particular, when the hole injection layer or hole transport layer underlying the light-emitting layer is formed using the above-mentioned composition for organic electroluminescent elements, lamination by the wet film-forming method is easy, so that a wet film-forming method is preferably employed. When the light-emitting layer is formed by the wet film-forming method, it is usually formed using a light-emitting layer-forming composition prepared by mixing the material to be the light-emitting layer with a soluble solvent (light-emitting layer solvent) instead of the hole injection layer-forming composition, as in the case of forming the hole injection layer by the above-mentioned wet film-forming method.

[0583] Examples of the solvent include the ether solvents, ester solvents, aromatic hydrocarbon solvents, and amide solvents mentioned for forming the hole injection layer, as well as alkane solvents, halogenated aromatic hydrocarbon solvents, aliphatic alcohol solvents, alicyclic alcohol solvents, aliphatic ketone solvents, and alicyclic ketone solvents. Specific examples of the solvent are listed below, but are not limited to these as long as the effects of the present invention are not impaired.

[0584] For example, aliphatic ether solvents such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and propylene glycol-1-monomethyl ether acetate (PGMEA); aromatic ether solvents such as 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole, phenetole, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3-dimethylanisole, 2,4-dimethylanisole, and diphenyl ether; aromatic ester solvents such as phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, propyl benzoate, and n-butyl benzoate; toluene, xylene, mesitylene, cyclohexylbenzene, tetralin, 3-isopropylbiphenyl, 1, Examples of suitable solvents include aromatic hydrocarbon solvents such as 2,3,4-tetramethylbenzene, 1,4-diisopropylbenzene, cyclohexylbenzene, and methylnaphthalene; amide solvents such as N,N-dimethylformamide and N,N-dimethylacetamide; alkane solvents such as n-decane, cyclohexane, ethylcyclohexane, decalin, and bicyclohexane; halogenated aromatic hydrocarbon solvents such as chlorobenzene, dichlorobenzene, and trichlorobenzene; aliphatic alcohol solvents such as butanol and hexanol; alicyclic alcohol solvents such as cyclohexanol and cyclooctanol; aliphatic ketone solvents such as methyl ethyl ketone and dibutyl ketone; and alicyclic ketone solvents such as cyclohexanone, cyclooctanone, and fenchone. Among these, alkane solvents and aromatic hydrocarbon solvents are particularly preferred.

[0585] [Hole blocking layer] A hole-blocking layer may be provided between the light-emitting layer 5 and the electron-injecting 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.

[0586] This hole-blocking layer has the roles of preventing holes migrating from the anode 2 from reaching the cathode 7 and efficiently transporting electrons injected from the cathode 7 toward the light-emitting layer 5. Required physical properties of the material constituting the hole-blocking layer include high electron mobility and low hole mobility, a large energy gap (difference between HOMO and LUMO), and a high excited triplet level (T1).

[0587] Examples of materials for hole-blocking layers 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.

[0588] 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.

[0589] 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.

[0590] [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.

[0591] 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.

[0592] 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.

[0593] 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.

[0594] The electron transport layer 6 is formed by laminating it on the light-emitting layer or the hole-blocking layer by the wet film-forming method or the vacuum deposition method in the same manner as described above. Usually, the vacuum deposition method is used.

[0595] [Electron injection layer] In order to efficiently inject electrons injected from the cathode 7 into the electron transport layer 6 or the light emitting layer 5, an electron injection layer may be provided between the electron transport layer 6 and the cathode 7.

[0596] 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 usually preferably 0.1 nm or more and 5 nm or less.

[0597] Furthermore, it is also preferable to dope an organic electron transport 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), since this improves both the electron injection and transport properties and enables excellent film quality to be achieved.

[0598] 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.

[0599] 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. The details of the wet film formation method are the same as those of the light-emitting layer described above.

[0600] 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.

[0601] [cathode] The cathode 7 serves to inject electrons into the layer on the light-emitting layer 5 side (such as the electron injection layer or the light-emitting layer).

[0602] 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.

[0603] 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.

[0604] The thickness of the cathode is usually the same as that of the anode.

[0605] [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-mentioned layers between the anode and the cathode.

[0606] [Other element 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 laminated on a substrate in this order.

[0607] 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.

[0608] <Organic EL display device> The organic EL display device (organic electroluminescent element display device) of the present invention includes the organic electroluminescent element of the present invention. The type and structure of the organic EL display 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.

[0609] For example, the organic EL display device of the present invention can be formed by the method described in "Organic EL Display" (Ohmsha, published August 20, 2004, by Tokito Shizuo, Adachi Chinaya, and Murata Hideyuki).

[0610] <Organic EL lighting> The organic EL lighting (organic electroluminescent element lighting) of the present invention comprises the organic electroluminescent element of the present invention. There are no particular limitations on the type or structure of the organic EL lighting of the present invention, and it can be assembled using the organic electroluminescent element of the present invention according to a conventional method. [Example]

[0611] The present invention will be described in more detail below with reference to examples. 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.

[0612] [Example 1] An organic electroluminescent device was fabricated in the following manner. A 50-nm-thick transparent conductive film of indium tin oxide (ITO) (Geomatec, sputter-deposited) was deposited on a glass substrate and patterned into 2-mm-wide stripes using standard photolithography and hydrochloric acid etching to form the anode. The substrate with the ITO pattern formed was then ultrasonically cleaned with a surfactant solution, rinsed with ultrapure water, ultrasonically cleaned with ultrapure water, and rinsed with ultrapure water again, followed by drying with compressed air and finally cleaning with ultraviolet ozone. A composition for forming a hole injection layer was prepared by dissolving 3.0 mass % of a hole transporting polymer compound having a repeating structure represented by the following formula (P-1) and 0.6 mass % of an electron accepting compound represented by the following formula (HI-1) in ethyl benzoate.

[0613] This solution was spin-coated onto the substrate in the atmosphere and dried on a hot plate in the atmosphere at 240° C. for 30 minutes to form a uniform thin film with a thickness of 40 nm, which was used as a hole injection layer.

[0614] [ka]

[0615] Next, 100 parts by mass of a charge transporting polymer compound having a structure represented by the following formula (HT-1) was dissolved in mesitylene to prepare a 2.0% by mass solution. This solution was spin-coated in a nitrogen glove box onto the substrate on which the hole injection layer had been coated, and dried at 230°C for 30 minutes on a hot plate in the nitrogen glove box to form a uniform thin film with a thickness of 40 nm, which served as a hole transport layer.

[0616] [ka]

[0617] Subsequently, as materials for the light-emitting layer, 25 parts by mass of a compound represented by the following formula (H-1), 25 parts by mass of a compound represented by the following formula (H-2), 50 parts by mass of a compound represented by the following formula (H-3), and 20 parts by mass of a compound represented by the following formula (D-1) were weighed out and dissolved in cyclohexylbenzene to prepare a 6% by mass solution as a composition for forming a light-emitting layer.

[0618] [ka]

[0619] [ka]

[0620] [ka]

[0621] [ka]

[0622] This composition for forming an emissive layer was spin-coated in a nitrogen glove box onto the substrate on which the hole transport layer had been coated, and dried at 120°C for 20 minutes on a hot plate in the nitrogen glove box to form a uniform thin film with a thickness of 60 nm, which was used as the emissive layer. The substrate on which the light-emitting layer had been formed was placed in a vacuum deposition device, and the inside of the device was heated to 2 × 10 -4 The pressure was evacuated until it reached a pressure of 0.1 Pa or less.

[0623] Next, a compound represented by the following formula (HB-1) and 8-hydroxyquinolinolatolithium were co-deposited on the light-emitting layer at a rate of 1 Å / sec by vacuum deposition so as to give a thickness ratio of 2:3, thereby forming a hole-blocking layer with a thickness of 30 nm.

[0624] [ka]

[0625] Next, a 2 mm striped shadow mask was attached to the substrate so that it was perpendicular to the ITO stripes of the anode, and the substrate was placed in another vacuum deposition apparatus. Aluminum was then heated using a molybdenum boat, and an 80 nm thick aluminum layer was formed at a deposition rate of 1 to 8.6 Å / s to form the cathode.

[0626] In this manner, an organic electroluminescent device having a light-emitting area measuring 2 mm×2 mm was obtained.

[0627] [Comparative Example 1] An organic electroluminescent device was produced in the same manner as in Example 1, except that a hole transport layer was formed using 100 parts by mass of a charge transport compound having a structure represented by the following formula (HT-2) instead of the charge transport polymer compound having a structure represented by formula (HT-1).

[0628] [ka]

[0629] [Element evaluation] The organic electroluminescent devices obtained in Example 1 and Comparative Example 1 were tested at a luminance of 1,000 cd / m 2 Voltage (V) and external quantum efficiency (EQE) (%) when emitting light at 15 mA / cm 2 The time (LT95) until the luminance decreased to 95% of the initial luminance was measured when the device was continuously energized at a current density of 1000 kJ / s. The value obtained by subtracting the voltage of Comparative Example 1 from the voltage of Example 1 was taken as the relative voltage (V) of Example 1, and the ratio of the EQE of Example 1 when the EQE of Comparative Example 1 was taken as 1 was calculated to obtain the relative EQE, and the ratio of the LT95 of Example 1 when the LT95 of Comparative Example 1 was taken as 1 was calculated to obtain the relative driving life. The measurement results are shown in Table 1. The results in Table 1 show that the organic electroluminescent device of the present invention has improved performance.

[0630] [Table 1]

[0631] [Example 2] In the same manner as in Example 1, an anode and a hole injection layer were formed on a glass substrate. Next, 100 parts by mass of a charge transporting polymer compound having a structure represented by formula (HT-1) was dissolved in mesitylene to prepare a 2.5% by mass solution. This solution was spin-coated in a nitrogen glove box onto the substrate on which the hole injection layer had been coated, and dried at 230°C for 30 minutes on a hot plate in the nitrogen glove box to form a uniform thin film with a thickness of 60 nm, which served as a hole transport layer. Subsequently, as materials for the light-emitting layer, 70 parts by mass of a compound represented by the following formula (H-4), 30 parts by mass of a compound represented by the following formula (H-3), and 10 parts by mass of a compound represented by the following formula (D-2) were weighed out and dissolved in cyclohexylbenzene to prepare a 6% by mass solution as a composition for forming a light-emitting layer.

[0632] [ka]

[0633] [ka]

[0634] This composition for forming an emissive layer was spin-coated in a nitrogen glove box onto the substrate on which the hole transport layer had been coated, and dried at 120°C for 20 minutes on a hot plate in the nitrogen glove box to form a uniform thin film with a thickness of 60 nm, which was used as the emissive layer. A hole blocking layer and a cathode were formed in the same manner as in Example 1, and an organic electroluminescent device having a light-emitting area of ​​2 mm x 2 mm was fabricated.

[0635] Comparative Example 2 An organic electroluminescent device was produced in the same manner as in Example 2, except that a compound represented by the following formula (H-5) was used instead of the compound represented by formula (H-3), and the composition for forming an emitting layer was such that the mass ratio of the compounds represented by each formula was (H-4):(H-5):(D-2)=70:30:10.

[0636] [ka]

[0637] [Element evaluation] The organic electroluminescent devices obtained in Example 2 and Comparative Example 2 were tested at a luminance of 5,000 cd / m 2 The voltage (V) and external quantum efficiency (EQE) (%) were measured when the device was lit. The value obtained by subtracting the voltage of Comparative Example 2 from the voltage of Example 2 was taken as the relative voltage (V) of Example 2, and the ratio of the EQE of Example 2 when the EQE of Comparative Example 2 was taken as 1 was calculated to obtain the relative EQE. The measurement results are shown in Table 2. The results in Table 2 show that the organic electroluminescent device of the present invention has improved performance.

[0638] [Table 2] [Industrial Applicability]

[0639] The organic electroluminescent device of the present invention can be suitably used in, for example, organic EL display devices and organic EL lighting. [Explanation of symbols]

[0640] 1 board 2 Anode 3. Hole injection layer 4. Hole transport layer 5. Light-emitting layer 6 Electron transport layer 7 Cathode 8. Organic electroluminescent device< / w>

Claims

1. An organic electroluminescent device having an anode, a cathode, a first organic layer, and a second organic layer, the first organic layer is provided between the anode and the cathode; the second organic layer is in contact with the anode side of the first organic layer, The first organic layer contains a compound represented by the following formula (240) or (241): The organic electroluminescent device, wherein the second organic layer contains a polymer having a triarylamine structure and having no crosslinking group. 【Chemical 1】 (In formula (240), Ar ６１１ , Ar ６１２ each independently represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. R ６１１ , R ６１２ each independently represents a hydrogen atom, a deuterium atom, a halogen atom, or a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent; R ６１１ and R ６１２ At least one of the groups represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms. G represents a single bond or a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. n ６１１ , n ６１２ are each independently an integer of 1 to 4. 【Chemistry 2】 (In formula (241), Ar ６１３ ~Ar ６１５ each independently represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. R ６１３ , R ６１４ each independently represents a hydrogen atom, a deuterium atom, a halogen atom, or a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent; R ６１３ and R ６１４ At least one of the groups represents a monovalent aromatic hydrocarbon group having 6 to 50 carbon atoms. G ６１２ , G ６１３ each independently represents a single bond or a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent. n ６１３ , n ６１４ are each independently an integer of 1 to 4.

2. Ar in the formula (240) ６１１ and Ar ６１２ 2. The organic electroluminescent device according to claim 1, wherein each of the groups independently represents a monovalent group in which a plurality of benzene rings, which may have a substituent, are bonded in a linear or branched manner.

3. Ar in the formula (241) ６１３ ~Ar ６１５ 2. The organic electroluminescent device according to claim 1, wherein each of the groups independently represents a monovalent group in which a plurality of benzene rings, which may have a substituent, are bonded in a linear or branched manner.

4. R in the formula (240) and the formula (241) ６１１ ~R ６１４ 2. The organic electroluminescent device according to claim 1, wherein each of the groups independently represents a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent.

5. 2. The organic electroluminescent device according to claim 1, wherein the polymer in the second organic layer has one or more repeating units selected from the group consisting of a repeating unit represented by the following formula (54), a repeating unit represented by the following formula (55), a repeating unit represented by the following formula (56), and a repeating unit represented by the following formula (57): 【Chemistry 3】 (In formula (54), Ar ５1 is a monovalent group in which a plurality of groups selected from an aromatic hydrocarbon group which may have a substituent other than a crosslinking group, an aromatic heterocyclic group which may have a substituent other than a crosslinking group, and an aromatic hydrocarbon group which may have a substituent other than a crosslinking group and an aromatic heterocyclic group which may have a substituent other than a crosslinking group are linked directly or via a linking group, 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 other than a crosslinking group, R ２０７ ~R ２０９ and R ２１１ ~R ２１４ each independently represents a hydrogen atom, an alkyl group which may have a substituent other than a bridging group, an aralkyl group which may have a substituent other than a bridging group, or a monovalent aromatic hydrocarbon group which may have a substituent other than a bridging group, a, b, and d are each independently an integer from 0 to 4; c is an integer from 0 to 3; However, when a is 1 or more, c is 1 or more, and when b is 1 or more, d is 1 or more; 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, 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, i and j are each independently an integer of 0 to 3. 【Chemistry 4】 (In formula (55), Ar ５1 is Ar in the formula (54). ５１ is the same as R ３０３ and R ３０６ each independently represents an alkyl group which may have a substituent other than a crosslinking group, R ３０４ and R ３０５ each independently represents an alkyl group which may have a substituent other than a crosslinking group, an alkoxy group which may have a substituent other than a crosslinking group, or an aralkyl group which may have a substituent other than a crosslinking group, l, n, p, and q are each independently 0 or 1; m is 1 or 2; However, when p is 1, l is 1, and when q is 1, n is 1.) 【Chemistry 5】 (In formula (56), Ar ５１ is Ar in the formula (54). ５１ is the same as Ar ４１ represents a divalent aromatic hydrocarbon group which may have a substituent other than a bridging group, a divalent aromatic heterocyclic group which may have a substituent other than a bridging group, or a divalent group in which a plurality of groups selected from the group consisting of the divalent aromatic hydrocarbon groups and the divalent aromatic heterocyclic groups are linked together directly or via a linking group, R ４４１ and R ４４２ each independently represents an alkyl group which may have a substituent other than a crosslinking group, t is 1 or 2; u is 0 or 1; r and s are each independently an integer from 0 to 4; However, if s is 1 or greater, u is 1.) 【Chemistry 6】 (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 other than a crosslinking group, an alkoxy group which may have a substituent other than a crosslinking group, an aralkyl group which may have a substituent other than a crosslinking group, a monovalent aromatic hydrocarbon group which may have a substituent other than a crosslinking group, or a monovalent aromatic heterocyclic group which may have a substituent other than a crosslinking group; f, g, and h each independently represent an integer from 0 to 4; e is an integer from 0 to 3; However, when g is 1 or more, e is 1 or more.)

6. the polymer in the second organic layer has one or more repeating units selected from the repeating units represented by formula (54), the repeating units represented by formula (55), the repeating units represented by formula (56), and the repeating units represented by formula (57), In the formula (54), a+b is 1 or more, In the formula (56), r+s is 1 or more, The organic electroluminescent device according to claim 5 , wherein f+g+h in the formula (57) is 1 or more.

7. 7. The organic electroluminescent device according to claim 6, wherein the polymer in the second organic layer has two or more repeating units selected from the repeating unit represented by formula (54), the repeating unit represented by formula (55), the repeating unit represented by formula (56), and the repeating unit represented by formula (57).

8. 7. The organic electroluminescent device according to claim 6, wherein the polymer in the second organic layer is composed of only one or more repeating units selected from the repeating unit represented by formula (54), the repeating unit represented by formula (55), the repeating unit represented by formula (56), and the repeating unit represented by formula (57).

9. 6. The organic electroluminescent device according to claim 5, wherein the polymer in the second organic layer contains a partial structure represented by the following formula (61) or the following formula (61'): 【Chemistry 7】 (In formula (61) and formula (61′), R ６０１ is R in the formula (54) ２０１ or R ２０２ , R in the formula (55) ３０３ , R ３０４ , R ３０５ , or R ３０６ , R in the formula (56) ４４１ or R ４４２ , R in the formula (57) ５１７ , R ５１８ , or R ５１９ represents a bond with the adjacent atom, and -* represents a bond with the adjacent atom. When formula (61) and formula (61') are 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 R ６０１ In addition, when Ring A and Ring B are a partial structure of the formula (54), R ２０１ or R ２０２ When it is a partial structure of the 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.)

10. The organic electroluminescent device according to claim 1 , wherein the first organic layer further contains a compound represented by the following formula (7): 【Chemistry 8】 In formula (7), ring A701 represents an aromatic hydrocarbon ring structure which may have a substituent or an aromatic heterocyclic structure which may have a substituent. Ring A702 represents an aromatic heterocyclic structure which may have a substituent. When a plurality of rings A701 and a plurality of rings A702 are present, they may be the same or different. R ７０１ , R ７０２ are each independently a structure represented by formula (b), and "*" represents the bonding position with ring A701 or ring A702. ７０１ , R ７０２ may be the same or different, R ７０１ , R ７０２ When there are a plurality of each of the groups, they may be the same or different. In formula (b), Ar ７０１ , Ar ７０３ each independently represents an aromatic hydrocarbon ring structure which may have a substituent, or an aromatic heterocyclic structure which may have a substituent. Ar ７０２ 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. Ar ７０１ , Ar ７０２ , and Ar ７０３ When there are a plurality of each of the groups, they may be the same or different. The substituents bonded to ring A701 may be bonded to each other, the substituents bonded to ring A702 may be bonded to each other, or the substituents bonded to ring A701 and the substituents bonded to ring A702 may be bonded to each other to form a ring. In formula (7), B ７０１ -L ７００ -B ７０２ represents an anionic bidentate ligand. ７０１ and B ７０２ each independently represents a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms may be atoms constituting a ring. ７００ is a single bond, or B ７０１ and B ７０２ represents an atomic group that together with B constitutes a bidentate ligand. ７０１ -L ７００ -B ７０２ When there are multiple groups, they may be the same or different. In the formula (7) and the formula (b), i1 and i2 each independently represent an integer of 0 to 12, i3 is Ar ７０２ represents an integer of 0 or more, with the upper limit being the number that can be replaced by j is Ar ７０１ represents an integer of 0 or more, with the upper limit being the number that can be replaced by k1 and k2 each independently represent an integer of 0 or more, the upper limit of which is the number of groups that can be substituted on ring A701 and ring A702. m is an integer of 1 to 3.

11. The organic electroluminescent device according to claim 1, wherein the first organic layer further comprises at least one compound selected from the group consisting of a compound represented by the following formula (250) and a compound represented by the following formula (260): 【Chemistry 9】 (In formula (250), Each W independently represents CH or N, and at least one W is N; Xa １ , Ya １ , and Za １ each independently represents a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a divalent aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent, Xa ２ , Ya ２ and Za ２ each independently represents a hydrogen atom, an optionally substituted monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted monovalent aromatic heterocyclic group having 3 to 30 carbon atoms, g11, h11, and j11 each independently represent an integer of 0 to 6; At least one of g11, h11, and j11 is an integer of 1 or more, When g11 is 2 or more, a plurality of Xa １ may be the same or different, When h11 is 2 or more, multiple Ya １ may be the same or different, If j11 is 2 or more, multiple Za １ may be the same or different, R ３１ represents a hydrogen atom or a substituent, and four R ３１ may be the same or different, However, when g11, h11, or j11 is 0, the corresponding Xa ２ , Ya ２ , Za ２ is not a hydrogen atom.) 【Chemistry 10】 (In formula (260), Ar ６１ ~Ar ６５ each independently represents a hydrogen atom or an optionally substituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, L １ ~L ５ each independently represents a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms, which may have a substituent; R ６０ each independently represents a substituent, m1 to m5 each independently represent an integer of 0 to 5; n represents an integer of 0 to 10; a1 to a3 each independently represent an integer of 0 to 3; However, Ar ６１ , Ar ６２ , Ar ６３ , Ar ６４ and at least one Ar when n is 1 or more. ６５ At least one of them is not a hydrogen atom.)

12. The organic electroluminescent device according to claim 11, wherein the first organic layer contains at least the compound represented by formula (250).

13. A display device comprising the organic electroluminescent device according to any one of claims 1 to 12.

14. A lighting device comprising the organic electroluminescent device according to any one of claims 1 to 12.

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