Organic electroluminescent element, display device, and lighting device

Abstract

To provide an organic electroluminescent element having high luminous efficiency and long operating life.SOLUTION: An organic electroluminescent element includes an anode, a cathode, a first organic layer, and a second organic layer, and the first organic layer is provided between the anode and the cathode, and the second organic layer is in contact with the anode side of the first organic layer, the first organic layer containing a compound represented by the formula (2), and the second organic layer containing a specific polymer.SELECTED DRAWING: Figure 1

Description

[Technical Field]

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

[0002] Various electronic devices that use organic EL elements, such as organic EL lighting and organic EL displays Organic electroluminescent devices have low power consumption due to the low applied voltage, It is also possible to emit colored light, so it can be used not only for large display monitors but also for mobile phones and smartphones. Applications are beginning to be seen in small and medium-sized displays, such as smartphones. Organic electroluminescent devices are made 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 evaporating organic materials under vacuum. However, the vacuum deposition method requires a complicated deposition process, resulting in poor productivity. In organic electroluminescent devices manufactured by vacuum deposition, the size of lighting and display panels has increased. Extremely difficult.

[0003] In recent years, it has become possible to efficiently produce organic electroluminescent devices that can be used for large displays and lighting. Wet film formation (coating) is being researched as a process for producing a thin film. Compared to deposition methods, this method has the advantage of being able to easily form a stable layer, making it suitable for use in displays and lighting devices. It is expected to be applied to mass production and large devices. Patent Document 1 discloses a method for forming a light-emitting layer containing a compound having a biscarbazole skeleton as follows in a vacuum. An organic electroluminescent device formed by a vapor deposition method has been disclosed, and attempts have been made to improve the driving voltage and efficiency. It is being done.

[0004] [ka]

[0005] Patent Document 2 discloses a method for producing a light-emitting layer containing a compound having a biscarbazole skeleton as follows: The organic electroluminescent device formed by the film formation method is disclosed, and the organic electroluminescent device has excellent solubility in organic solvents. Attempts have been made to provide compositions for forming light-emitting layers for optical devices.

[0006] [ka] [Prior art documents] [Patent documents]

[0007] [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]

[0008] However, in the above-mentioned prior art, the properties of the organic electroluminescent device for display applications are Therefore, the luminous efficiency of the organic electroluminescent device formed by the wet film formation method is still insufficient. There was a demand for improved performance and operating life. The present invention has been made in view of the above-mentioned conventional circumstances, and provides a light emitting diode (LED) having high luminous efficiency and long operating life. The object of the present invention is to provide an organic electroluminescent device having a long wavelength. [Means for solving the problem]

[0009] As a result of extensive research, the present inventors have found that a repeating unit of the acrylic resin has a twisted structure and a crosslinking group. By using an organic layer containing a polymer having a triarylamine structure, the above-mentioned problems can be solved. The present invention has been completed based on the findings that the above problems can be solved. 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. An optical element, 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 (2): The second organic layer contains a polymer that satisfies at least one of the following (i) and (ii): , an organic electroluminescent device.

[0010] (i) A repeating unit represented by the following formula (54), a repeating unit represented by the following formula (55) position, a repeating unit represented by the following formula (56) and a repeating unit represented by the following formula (57) It has two or more repeating units of the above. (ii) 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) It consists of only one or more repeating units.

[0011] [ka]

[0012] [In formula (2), Ar 1 is a structure represented by formula (2a). Ar 2 each independently represents a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent; Ar 2If there are multiple, they may be the same or different. Good too.

[0013] Each R is independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a heterocyclic group having 7 to 40 carbon atoms, or a cyclic group having 1 to 20 carbon atoms. b) Aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aryl groups having 3 to 20 carbon atoms an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms; These groups, excluding hydrogen atoms, may have a substituent. The other pair has a structure represented by formula (2b). m and n each independently represents an integer of 1 to 3.

[0014] [ka]

[0015] [In formula (2a), R 1 are each independently a hydrogen atom, a (hetero)alkyl group having 3 to 20 carbon atoms which may have a substituent, ) an aryl group, or Ar 2 It is a combination with .]

[0016] [ka]

[0017] [In formula (2b), Ar 3 represents a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent. R 2 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a (hexyl) group having 7 to 40 carbon atoms, (hetero)aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aralkyl groups having 3 to 20 carbon atoms alkylsilyl groups having 1 to 20 carbon atoms, and arylsilyl groups having 6 to 20 carbon atoms. an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms. These groups, except for the hydrogen atom, may have a substituent. "★" indicates the bonding position with formula (2).

[0018] [ka]

[0019] (In formula (54), Ar 51 represents an aromatic hydrocarbon group which may have a substituent other than a bridging group, an aromatic heterocyclic group which may have a substituent, or a bridging group which may have a substituent other than Aromatic hydrocarbon groups and aromatic heterocyclic groups which may have a substituent other than a bridging group are selected from the group consisting of: a group in which a plurality of groups 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 has a substituent other than a crosslinking group is an alkyl group which may be R 207 ~R 209 and R 211 ~R 214 are each independently a hydrogen atom or a group other than a bridging group. an alkyl group which may have a substituent, an aralkyl group which may have a substituent other than a bridging group; an aromatic hydrocarbon group which may have a substituent other than a cyclic group or a crosslinking group, a, b, and d each independently represent an integer of 0 to 4; c is an integer from 0 to 3, a+b is greater than or equal to 1, 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 each independently represent an integer of 0 to 3.

[0020] [ka]

[0021] (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; is a methyl group, R 304 and R 305 each independently represents an alkyl group which may have a substituent other than a crosslinking group; an alkyl group, an alkoxy group which may have a substituent other than a crosslinking group, or an alkoxy group which may have a substituent other than a crosslinking group an aralkyl group which may be present, l, n, p, and q each independently represent 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.)

[0022] [ka]

[0023] (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 bridging group a divalent aromatic heterocyclic group which may have a substituent other than and the divalent aromatic heterocyclic group, is a divalent group linked via a group, R 441 and R 442 each independently represents an alkyl group which may have a substituent other than a crosslinking group; is a methyl group, t is 1 or 2; u is 0 or 1; r and s each independently represent an integer of 0 to 4, r+s is greater than or equal to 1, However, if s is 1 or greater, then u is 1.)

[0024] [ka]

[0025] (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 bridging group; a group, an alkoxy 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 bridging group, an aromatic hydrocarbon group which may have a substituent other than a bridging group, represents an aromatic heterocyclic group which may have a substituent other than a bridging group, f, g, and h each independently represent an integer of 0 to 4, f+g+h is greater than or equal to 1, e is an integer from 0 to 3, However, if g is 1 or greater, e is 1 or greater.) A second aspect of the present invention is the organic electroluminescent device of the first aspect, R in the formula (2), formula (2a), and formula (2b) 1 , R 2 , Ar 2 and Ar 3 has The optional substituents are each independently an alkyl group, an aralkyl group, a heteroaralkyl group, an alkoxy group, an aryl group, an aryloxy ... oxy group, aryloxy group, heteroaryloxy group, alkylsilyl group, arylsilyl group alkyl group, alkylcarbonyl group, arylcarbonyl group, alkylamino group, aryl The organic electroluminescent device is an organic group, an aryl group, or a heteroaryl group.

[0026] A third aspect of the present invention is the organic electroluminescent device of the first aspect, The organic electroluminescent device is one in which the formula (2) is represented by the following formula (2-1).

[0027] [ka]

[0028] [In formula (2-1), Ar 4 is a structure represented by the formula (2a), and Ar 5 is Ar in the formula (2). 2 and is a group selected from the same groups, and Ar 6 is Ar in the formula (2b). 3 Selected from the same group as is a group selected from R 3 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a carbon atom, (Hetero)aralkyl groups having 7 to 40 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, and alkoxy groups having 3 to 20 carbon atoms. (hetero)aryloxy groups, alkylsilyl groups having 1 to 20 carbon atoms, and alkylsilyl groups having 6 to 20 carbon atoms. an arylsilyl group, an arylamino group having 6 to 20 carbon atoms, or a (hetero)silyl group having 3 to 30 carbon atoms; ) an aryl group. These groups, except for hydrogen atoms, may have a substituent. Ar 5 and Ar 6 When there are multiple j and k, they may be the same or different. are values ​​selected from the same ranges as m and n in formula (2).

[0029] A fourth aspect of the present invention is the organic electroluminescent device of the third aspect, Ar in the formula (2-1) 5 each independently represents a 1,3-phenylene group or a 1,4- The organic electroluminescent device is a phenylene group.

[0030] A fifth aspect of the present invention relates to the organic electroluminescent device of the third or fourth aspect, R in the formula (2-1) 3 , Ar 5 , and Ar 6 The substituents which may be possessed by each of In particular, alkyl groups, aralkyl groups, heteroaralkyl groups, alkoxy groups, aryloxy groups, group, heteroaryloxy group, alkylsilyl group, arylsilyl group, alkylcarbonyl group an alkyl group, an arylcarbonyl group, an alkylamino group, an arylamino group, an aryl group, or , a heteroaryl group is an organic electroluminescent device.

[0031] A sixth aspect of the present invention is the organic electroluminescent device according to any one of the first to fifth aspects, The polymer is an organic electrolytic compound having a partial structure represented by the following formula (61) or the following formula (61'): It is a field light emitting element.

[0032] [ka]

[0033] (In formula (61) and formula (61'), R 601 is R in Eq. (54) 201 or R 202 , R in Eq. (55) 303 , R 304 , R 305 , or R 306 , R in Eq. (56) 441 or R 442 , formula (5 7) R in 517 , R 518 , or R 519 and -* represents a bond with the adjacent atom. .

[0034] Formula (61) and Formula (61') are a partial structure of Formula (54) or a partial structure of Formula (56) In this case, Ring B may be part of a fused ring. The partial structures represented by formula (61) and formula (61') are R 601 In addition to Ring A and and Ring B, when it is a partial structure of formula (54), R 201 or R 202 , formula (5 If it is a partial structure of 5), R 303 , R 304 , R 305 , or R 306 , equation (56) If it is a partial structure of 441 or R 442 , if it is a partial structure of formula (57), R 5 17 , R 518 or R 519 It may have.)

[0035] A seventh aspect of the present invention is the organic electroluminescent device according to any one of the first to sixth aspects, The organic electroluminescent device wherein the first organic layer further contains a compound represented by the following formula (7): be.

[0036] [ka]

[0037] [In the formula (7), ring A701 represents an aromatic hydrocarbon ring structure which may have a substituent or a substituent represents an aromatic heterocyclic structure which may have the following structure: Ring A702 represents an aromatic heterocyclic structure which may have a substituent. When there are multiple rings A701 and multiple rings A702, they may be the same or different. That's fine.

[0038] R 701 , R 702 are each independently a structure represented by formula (b), and "*" indicates ring A701 or represents the bonding position with ring A702. 701 , R 702 are the same but different Also, R 701 , R 702 If there are multiple of each, they may be the same but different. It may be possible. Ar 701 , Ar 703 each independently represents an aromatic hydrocarbon ring which may have a substituent; structure, or an aromatic heterocyclic structure which may have a substituent.

[0039] Ar 702 is an aromatic hydrocarbon ring structure which may have a substituent, It represents an aromatic heterocyclic structure which may have a substituent, or an aliphatic hydrocarbon structure which may have a substituent. Ar701 , Ar 702 , and Ar 703 If there are multiple of each, they are the same But it may be different. The substituents bonded to ring A701, the substituents bonded to ring A702, or the substituents bonded to ring A701 The substituents bonded to ring A702 and the substituents bonded to ring A703 are bonded to each other to form a ring. That's fine.

[0040] B 701 -L 700 -B 702 represents an anionic bidentate ligand. 701 and B 7 02 each independently represents a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms form a ring. It may be an atom that 700 is a single bond or B 701 and B 702 With 2 Represents the atomic group that constitutes the dentate ligand. B 701 -L 700 -B 702 If there are multiple They may be the same or different.

[0041] 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 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 greater, with the upper limit being the number of substitutions that can be made on ring A701 and ring A702. Represents the integer above. m is an integer from 1 to 3.

[0042] Aspect 8 of the present invention is an organic electroluminescent device according to any one of aspects 1 to 7, wherein The first organic layer further contains a compound represented by the following formula (250) and a compound represented by the following formula (260): The organic electroluminescent device contains at least one compound selected from the group consisting of compounds represented by the formula:

[0043] [ka]

[0044] (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 group having 6 to 3 carbon atoms which may have a substituent a divalent aromatic hydrocarbon group having 3 to 30 carbon atoms which may have a substituent; represents an aromatic heterocyclic group, Xa 2 , Ya 2 and Za 2 each independently represents a hydrogen atom, a carbon atom which may have a substituent, a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, or a monovalent aromatic hydrocarbon group having 3 to 30 carbon atoms which may have a substituent; represents a monovalent aromatic heterocyclic group, 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 Ku, However, if g11, h11, or j11 is 0, the corresponding Xa 2 , Ya 2 , Z a 2 is not a hydrogen atom.)

[0045] [ka]

[0046] (In formula (260), Ar 61 ~Ar 65 each independently represents a hydrogen atom or a monovalent group which may have a substituent; an aromatic hydrocarbon group having 6 to 60 carbon atoms, L 1 ~L 5 each independently represents a divalent group having 6 to 60 carbon atoms which may have a substituent; is an aromatic hydrocarbon group of the formula 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 when n is 1 or more Another Ar 65 At least one of them is not a hydrogen atom.) A ninth aspect of the present invention is the organic electroluminescent device of the eighth aspect, The first organic layer is an organic electroluminescent layer containing at least a compound represented by formula (250). Optical element.

[0047] A tenth aspect of the present invention is a display device comprising the organic electroluminescent device according to any one of the first to ninth aspects. It is a location. An eleventh aspect of the present invention is a lighting device comprising the organic electroluminescent device according to any one of the first to ninth aspects. It is a location. [Effects of the Invention]

[0048] According to the present invention, an organic electroluminescent device having higher luminous efficiency and longer operating life than conventional devices is provided. It is possible. [Brief explanation of the drawings]

[0049] [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

[0050] The embodiments of the present invention will be described in detail below, but the present invention is not limited to the following embodiments. The present invention is not limited to the above and can be practiced in various modifications within the scope of its essence. When the expression "~" is used in the specification, it is considered to be an expression including the numerical values ​​or physical properties before and after it. It is used as such. In the present invention, the term "optionally have a substituent" means that the group may have one or more substituents. This means that

[0051] In this specification, (hetero)aralkyl groups, (hetero)aryloxy groups, ( The heteroaryl group is an aralkyl group which may contain a heteroatom, a heteroaryl group which may contain a heteroatom, an aryloxy group which may contain an atom; an aryl group which may contain a hetero atom; The term "may contain a heteroatom" means an aralkyl group, an aryloxy group, or Among the carbon atoms forming the aryl skeleton in the main skeleton of the aryl group, one or more carbon atoms The heteroatom is a nitrogen atom, an oxygen atom, Examples include sulfur atoms, phosphorus atoms, and silicon atoms, and among these, nitrogen atoms are preferred from the viewpoint of durability. I wish.

[0052] In addition, in this specification, the (hetero)aryl group refers to a monocyclic group, a 2- to 4-ring condensed ring group, a monocyclic group, a fused ring group, a heterocyclic ... The term "a" is used to mean a group in which a plurality of rings and / or 2- to 4-fused ring groups are linked together. The (hetero)aryl group is an aryl group that may contain a heteroatom, i.e., The aryl group is an aromatic hydrocarbon group, and the heteroaryl group is an aromatic hydrocarbon group. An aryl group is an aromatic heterocyclic group.

[0053] <Organic electroluminescent device> The organic electroluminescent device according to the embodiment of the present invention comprises an anode, a cathode, a first organic layer, and a second organic layer. An organic electroluminescent device having an 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 (2): The second organic layer contains a polymer that satisfies at least one of the following (i) and (ii): .

[0054] (i) 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) Among them, it has two or more repeating units. (ii) A repeating unit represented by the following formula (54), a repeating unit represented by the following formula (55) position, a repeating unit represented by the following formula (56) and a repeating unit represented by the following formula (57) It consists of only one or more repeating units of the above.

[0055] The reason why the organic electroluminescent device according to the embodiment of the present invention exhibits the effect is not clear, but the following reasons may be considered. It is speculated that: The benzene ring in the carbazole skeleton has high electron density, and the 3rd and 6th positions are particularly reactive. It is thought that it easily reacts with electron-donating substances. As a result of the reaction, oxides of the electron-donating substances are produced. This oxide may cause further deterioration reactions during operation of the device. When a crosslinked polymer is used as a constituent material of the second organic layer, the unreacted polymer remains after the crosslinking process. Therefore, the remaining crosslinking groups are not intended to be crosslinked during the driving of the organic electroluminescent device. In the case of a device in which the first organic layer and the second organic layer are adjacent to each other, It is thought that the 3- or 6-position of the carbazole skeleton contained in the first organic layer is reacted with the 3- or 6-position of the carbazole skeleton contained in the first organic layer. As a result, it is presumed that the operating life of such organic electroluminescent devices is shortened. On the other hand, the compound represented by formula (2) contained in the first organic layer is indolocarbazole. It is believed that the compound has a skeleton and can suppress deterioration. The polymer to be used is composed of repeating units that do not have crosslinking groups, and the repeating units derived from the crosslinking groups described above are not included. Therefore, the reaction between the reactive species and the carbazole compound does not occur. This is thought to make the compounds that make up the organic electroluminescent device less susceptible to deterioration, thereby extending the operating life of the device. can be done.

[0056] When a crosslinked polymer is used as a constituent material of the second organic layer, the second organic layer is crosslinked. After the process, a crosslinked polymer having a crosslinking group is formed, but the crosslinking reaction It is thought that chain distortion occurs, reducing charge transport, especially near the interface. On the other hand, the polymer having a triarylamine structure used in the present invention has a crosslinking group. The crosslinking reaction described above causes a decrease in charge transport properties. It is believed that the charge transport property is improved because the charge transport property is not increased. The compound represented by formula (2) has the highest occupied molecular orbital (HOMO) in the indolocarbazole skeleton. The localization brings the energy levels of the adjacent second organic layer closer together. Therefore, it is considered that the second organic layer is composed of a repeating unit having no crosslinking group. The organic electroluminescence device of the present invention uses a polymer having the formula (2) and contains a compound represented by the formula (2) in the first organic layer. In the device, charge balancing is achieved by effectively transferring charges from the second organic layer to the first organic layer. It is expected that this will improve the performance and result in low-voltage, highly efficient organic electroluminescent devices.

[0057] The compound represented by formula (2) is a material whose energy level is close to that of the second organic layer. , recombination may occur near the interface with the second organic layer. When recombination occurs in the second organic layer, the excitation energy is easily transferred to the second organic layer, resulting in a decrease in luminous efficiency. The polymer used in the present invention has a twisted structure in the repeating unit, The larger energy gap contributes to the emission generated in the adjacent first organic layer. It is believed that the excitation energy is prevented from transferring to the second organic layer. By including a twisted structure in the repeating unit, the HOMO becomes deeper, and is expressed by equation (2). This is closer to the HOMO of the compound being used, allowing for more efficient charge transfer. Therefore, the organic electroluminescent device of the present invention is a highly efficient organic electroluminescent device. It is possible to have a child.

[0058] [First organic layer and second organic layer] The first organic layer may include a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. However, the first organic layer is preferably an emitting layer. The second organic layer is preferably a hole injection layer or a hole transport layer, and is preferably a hole transport layer. is more preferable.

[0059] In particular, the present invention relates to a semiconductor device in which the first organic layer is an emitting layer, the second organic layer is a hole transporting layer, and the first In an organic electroluminescent device in which the organic layer is formed on the second organic layer by a wet film-forming method, , are preferably used. The first organic layer and the second organic layer can be formed by dry film formation such as vacuum deposition. In the present invention, the wet film-forming method is a film-forming method, i.e., a coating method. Examples of coating methods include spin coating, dip coating, die coating, and bar coating. method, blade coating method, roll coating method, spray coating method, capillary coating method, Ink jet method, nozzle printing method, screen printing method, gravure printing method, flexible A method of forming a film by a wet method such as printing, and then drying the applied film to form a film is called a film formation method. Among these film forming methods, the spin coating method, the spray coating method, and the inkjet method are , nozzle printing method, etc. are preferred.

[0060] When the first organic layer is formed by a wet film-forming method, the first composition described below may be used. preferable. When the second organic layer is formed by a wet film-forming method, the second composition described below may be used. After applying the second composition, the polymer is insolubilized by heating. The organic layer 2 can be suitably used for laminating organic electroluminescent devices. The "first organic layer" and the "second organic layer" will be described in detail below.

[0061] <First organic layer> [Compound represented by formula (2)] The first organic layer contains a compound represented by the following formula (2).

[0062] [ka]

[0063] [In formula (2), Ar 1 is a structure represented by formula (2a). Ar 2 are each independently a (hetero)aryl having 6 to 60 carbon atoms which may have a substituent. It is a group. Ar 2 If there are multiple, they may be the same or different. good. Each R is independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a heterocyclic group having 7 to 40 carbon atoms, or a cyclic group having 1 to 20 carbon atoms. b) Aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aryl groups having 3 to 20 carbon atoms an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms; These groups, excluding hydrogen atoms, may have a substituent. The other pair has a structure represented by formula (2b). m and n each independently represents an integer of 1 to 3.

[0064] [ka]

[0065] [In formula (2a), R 1 are each independently a hydrogen atom, a (hetero)alkyl group having 3 to 20 carbon atoms which may have a substituent, ) aryl group, Ar 2 It is a combination with .]

[0066] [ka]

[0067] [In formula (2b), Ar 3 represents a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent. R 2 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a (hexyl) group having 7 to 40 carbon atoms, (hetero)aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aralkyl groups having 3 to 20 carbon atoms alkylsilyl groups having 1 to 20 carbon atoms, and arylsilyl groups having 6 to 20 carbon atoms. an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms. These groups, except for the hydrogen atom, may have a substituent. "★" indicates the bonding position with formula (2).

[0068] Ar 2 is a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent. and more preferably an aryl group having 6 to 60 carbon atoms. Ar 2 Specific examples of the ring include a benzene ring, a naphthalene ring, a dibenzofuran ring, and a thiophene ring. It is a divalent group derived from a ring, a dibenzothiophene ring, or a carbazole ring, and these are bonded A divalent group formed by bonding a benzene ring and a thiophene ring, for example, a phenylthio group formed by bonding a benzene ring and a thiophene ring From the viewpoint of device stability, a divalent group derived from phen is preferably used. benzene ring, naphthalene ring, and dibenzofuran ring, and more preferably benzene ring and naphthalene ring. It is a divalent group derived from an olefin ring, particularly preferably a benzene ring.

[0069] Ar 2 The substituent that may be possessed by the group is a substituent selected from the group Z of substituents described below. It is preferable that: Each R is independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a heterocyclic group having 7 to 40 carbon atoms, or a cyclic group having 1 to 20 carbon atoms. b) Aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aryl groups having 3 to 20 carbon atoms an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms or a (hetero)aryl group having 3 to 30 carbon atoms; From the viewpoint of device life, hydrogen atoms, alkyl groups having 1 to 20 carbon atoms, and heterocyclic groups having 7 to 40 carbon atoms are preferred. b) aralkyl groups, (hetero)aryloxy groups having 3 to 20 carbon atoms, aryloxy groups having 6 to 20 carbon atoms An arylamino group or a (hetero)aryl group having 3 to 30 carbon atoms is preferred, and a more preferred It is preferably a hydrogen atom or an aryl group having 3 to 30 carbon atoms.

[0070] At least one pair of adjacent Rs has a structure represented by formula (2b). The substituent that R may have is a substituent selected from the substituent group Z described below. preferable. Examples of alkyl groups having 1 to 20 carbon atoms include methyl, ethyl, propyl, and hexyl. From the viewpoint of device stability, a methyl group is preferred. , an ethyl group, or a hexyl group, and more preferably a methyl group.

[0071] Specific examples of the (hetero)aralkyl group having 7 to 40 carbon atoms include a phenylmethyl group, a phenylmethyl group, and a phenylmethyl group. phenylethyl group, phenylpropyl group, phenylhexyl group, phenyloctyl group, phenyl From the viewpoint of device stability, phenylpropyl is preferred. A propyl group and a phenylhexyl group are preferred. Examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, and a butyloxy group. From the viewpoint of device stability, methoxy and ethoxy groups are preferred. I wish.

[0072] Examples of the (hetero)aryloxy group having 3 to 20 carbon atoms include a phenoxy group and a naphthyl group. The examples include an oxy group and a carbazolyloxy group, and from the viewpoint of device stability, a phenoxy group is preferred. I wish. Examples of alkylsilyl groups having 1 to 20 carbon atoms include trimethylsilyl and triethylsilyl. From the viewpoint of device stability, trimethylsilyl is preferred. It is a methylsilyl group.

[0073] Examples of the arylsilyl group having 6 to 20 carbon atoms include a dimethylphenylsilyl group, a triphenylsilyl group, and a phenylsilyl group. It is a phenylsilyl group. Specific examples of the arylamino group having 6 to 20 carbon atoms include a diphenylamino group, a biphenylamino group, and a phenylamino group. From the viewpoint of device stability, diphenylamino groups and naphthylphenyl groups are preferred. The amino group is preferred.

[0074] Specific examples of the (hetero)aryl group having 3 to 30 carbon atoms include a phenyl group, a naphthyl group, Anthranyl group, biphenyl group, terphenyl group, carbazolyl group, thienyl group, benzo furyl group, benzothienyl group, dibenzofuryl group, dibenzothienyl group, phenylthienyl group From the viewpoint of extending the life of the element, phenyl, naphthyl, biphenyl, thiazolinone ... -phenyl group, carbazolyl group, dibenzofuryl group, more preferably phenyl group , a biphenyl group, and a terphenyl group.

[0075] R 1 are each independently a hydrogen atom, a (hetero)alkyl group having 3 to 20 carbon atoms which may have a substituent, ) aryl group, Ar 2 At least one bond is to Ar 2 It is a combination of. Ar 2 R other than the bond with 1 is a hydrogen atom, a group having 3 to 20 carbon atoms which may have a substituent It is preferable that the aryl group is an aryl group represented by the formula: Specific examples of the (hetero)aryl group having 3 to 20 carbon atoms which may have a substituent include: Phenyl group, naphthyl group, anthranyl group, biphenyl group, terphenyl group, carbazole group benzothienyl group, dibenzofuryl group, dibenzothienyl group, From the viewpoint of extending the life of the element, phenyl groups, naphthienyl groups, etc. are preferred. The examples of the alkyl group include phenyl, biphenyl, terphenyl, carbazolyl, and dibenzofuryl groups. More preferred are a phenyl group, a biphenyl group and a terphenyl group.

[0076] R 1 The substituent that may be possessed by the group is a substituent selected from the group Z of substituents described below. is preferred. Ar 3 represents a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent. Specific examples of the (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent include: Phenyl group, naphthyl group, anthranyl group, biphenyl group, terphenyl group, carbazole group benzothienyl group, dibenzofuryl group, dibenzothienyl group, From the viewpoint of extending the life of the element, phenyl groups, naphthienyl groups, etc. are preferred. The examples of the alkyl group include phenyl, biphenyl, terphenyl, carbazolyl, and dibenzofuryl groups. More preferred are a phenyl group, a biphenyl group and a terphenyl group.

[0077] Ar 3 The substituent that may be possessed by the group is a substituent selected from the group Z of substituents described below. It is preferable that: R 2 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a heterocyclic group having 7 to 40 carbon atoms, or a b) Aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aryl groups having 3 to 20 carbon atoms an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms or a (hetero)aryl group having 3 to 30 carbon atoms; It is preferably a hydrogen atom or an aryl group having 3 to 30 carbon atoms which may have a substituent. These groups, except for the hydrogen atom, may have a substituent.

[0078] R 2 The substituent that may be possessed by the group is a substituent selected from the group Z of substituents described below. is preferred. Examples of alkyl groups having 1 to 20 carbon atoms include methyl, ethyl, propyl, and hexyl. From the viewpoint of device stability, a methyl group is preferred. , an ethyl group, or a hexyl group, and more preferably a methyl group.

[0079] Specific examples of the (hetero)aralkyl group having 7 to 40 carbon atoms include a phenylmethyl group, a phenylmethyl group, and a phenylmethyl group. phenylethyl group, phenylpropyl group, phenylhexyl group, phenyloctyl group, phenyl From the viewpoint of device stability, phenylpropyl is preferred. A propyl group and a phenylhexyl group are preferred. Examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, and a butyloxy group. From the viewpoint of device stability, methoxy and ethoxy groups are preferred. I wish.

[0080] Examples of the (hetero)aryloxy group having 3 to 20 carbon atoms include a phenoxy group and a naphthyl group. The examples include an oxy group and a carbazolyloxy group, and from the viewpoint of device stability, a phenoxy group is preferred. I wish. Examples of alkylsilyl groups having 1 to 20 carbon atoms include trimethylsilyl and triethylsilyl. From the viewpoint of device stability, trimethylsilyl is preferred. It is a methylsilyl group.

[0081] Examples of the arylsilyl group having 6 to 20 carbon atoms include a dimethylphenylsilyl group, a triphenylsilyl group, and a phenylsilyl group. It is a phenylsilyl group. Specific examples of the arylamino group having 6 to 20 carbon atoms include a diphenylamino group, a biphenylamino group, and a phenylamino group. From the viewpoint of device stability, diphenylamino groups and naphthylphenyl groups are preferred. The amino group is preferred.

[0082] Specific examples of the (hetero)aryl group having 3 to 30 carbon atoms include a phenyl group, a naphthyl group, Anthranyl group, biphenyl group, terphenyl group, carbazolyl group, thienyl group, benzo furyl group, benzothienyl group, dibenzofuryl group, dibenzothienyl group, phenylthienyl group From the viewpoint of extending the life of the element, phenyl, naphthyl, biphenyl, thiazolinone ... -phenyl group, carbazolyl group, dibenzofuryl group, more preferably phenyl group , a biphenyl group, and a terphenyl group.

[0083] R 1 , R 2 , Ar 2 and Ar 3 The substituent that may be possessed by the group is selected from the group Z of substituents described below. It is preferable that the substituents are selected from the group consisting of aryl, ... m and n each independently represent an integer of 1 to 3. m is preferably 1 to 2, and more preferably 2. From the viewpoint of adjustment, n is preferably 1, and from the viewpoint of improving charge transportability, It is preferable that n is 2 or 3.

[0084] The compound represented by formula (2) is preferably a charge transport compound, i.e., a charge transport host. Preferably, it is a material. The first organic layer may contain only one compound represented by the formula (2). Two or more of these may be included.

[0085] [Compound represented by formula (2-1)] The formula (2) is preferably represented by the following formula (2-1).

[0086] [ka]

[0087] [In formula (2-1), Ar 4 is the structure represented by the above formula (2a). 5 is the Ar in the above formula (2). 2 is a group selected from the same groups as Ar 6 is the Ar in the above formula (2b). 3 Similar groups and R 3are each independently a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. , (hetero)aralkyl groups having 7 to 40 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, and (Hetero)aryloxy groups having up to 20 carbon atoms, alkylsilyl groups having 1 to 20 carbon atoms, and alkylsilyl groups having 6 to 10 carbon atoms. an arylsilyl group having 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or an arylsilyl group having 3 to 30 carbon atoms; These groups, excluding hydrogen atoms, may have a substituent. Ar 5 and Ar 6 When there are a plurality of each of the groups, they may be the same or different. j and k are values ​​selected from the same ranges as m and n in the above formula (2).

[0088] Ar 5 is a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent. and more preferably an aryl group having 6 to 60 carbon atoms. Ar 5 Specific examples of the ring include a benzene ring, a naphthalene ring, a dibenzofuran ring, and a thiophene ring. It is a divalent group derived from a ring, a dibenzothiophene ring, or a carbazole ring, and these are bonded A divalent group formed by bonding a benzene ring and a thiophene ring, for example, a phenylthio group formed by bonding a benzene ring and a thiophene ring From the viewpoint of device stability, a divalent group derived from phen is preferably used. benzene ring, naphthalene ring, and dibenzofuran ring, and more preferably benzene ring and naphthalene ring. It is a divalent group derived from an olefin ring, particularly preferably a benzene ring.

[0089] Ar 5 are each independently a 1,3-phenylene group or a 1,4-phenylene group. It is even more preferable that: Ar 6 represents a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent. Specific examples of the (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent include: Phenyl group, naphthyl group, anthranyl group, biphenyl group, terphenyl group, carbazole group benzothienyl group, dibenzofuryl group, dibenzothienyl group, From the viewpoint of extending the life of the element, phenyl groups, naphthienyl groups, etc. are preferred. The examples of the alkyl group include phenyl, biphenyl, terphenyl, carbazolyl, and dibenzofuryl groups. More preferred are a phenyl group, a biphenyl group and a terphenyl group.

[0090] R 3 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a (hexyl) group having 7 to 40 carbon atoms, (hetero)aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aralkyl groups having 3 to 20 carbon atoms alkylsilyl groups having 1 to 20 carbon atoms, and arylsilyl groups having 6 to 20 carbon atoms. an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms. From the viewpoint of device life, hydrogen atoms, alkyl groups with 1 to 20 carbon atoms, and alkyl groups with 7 to 40 carbon atoms are preferred. (hetero)aralkyl groups, (hetero)aryloxy groups having 3 to 20 carbon atoms, An arylamino group or a (hetero)aryl group having 3 to 30 carbon atoms is preferred, and a more preferred or a hydrogen atom, or an aryl group having 3 to 30 carbon atoms.

[0091] Examples of alkyl groups having 1 to 20 carbon atoms include methyl, ethyl, propyl, and hexyl. From the viewpoint of device stability, a methyl group is preferred. , an ethyl group, or a hexyl group, and more preferably a methyl group. Specific examples of the (hetero)aralkyl group having 7 to 40 carbon atoms include a phenylmethyl group, a phenylmethyl group, and a phenylmethyl group. phenylethyl group, phenylpropyl group, phenylhexyl group, phenyloctyl group, phenyl From the viewpoint of device stability, phenylpropyl is preferred. A propyl group and a phenylhexyl group are preferred.

[0092] Examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, and a butyloxy group. From the viewpoint of device stability, methoxy and ethoxy groups are preferred. I wish. Examples of the (hetero)aryloxy group having 3 to 20 carbon atoms include a phenoxy group and a naphthyl group. The examples include an oxy group and a carbazolyloxy group, and from the viewpoint of device stability, a phenoxy group is preferred. I wish.

[0093] Examples of alkylsilyl groups having 1 to 20 carbon atoms include trimethylsilyl and triethylsilyl. From the viewpoint of device stability, trimethylsilyl is preferred. It is a methylsilyl group. Examples of the arylsilyl group having 6 to 20 carbon atoms include a dimethylphenylsilyl group, a triphenylsilyl group, and a phenylsilyl group. It is a phenylsilyl group.

[0094] Specific examples of the arylamino group having 6 to 20 carbon atoms include a diphenylamino group, a biphenylamino group, and a phenylamino group. From the viewpoint of device stability, diphenylamino groups and naphthylphenyl groups are preferred. The amino group is preferred. Specific examples of the (hetero)aryl group having 3 to 30 carbon atoms include a phenyl group, a naphthyl group, Anthranyl group, biphenyl group, terphenyl group, carbazolyl group, thienyl group, benzo furyl group, benzothienyl group, dibenzofuryl group, dibenzothienyl group, phenylthienyl group From the viewpoint of extending the life of the element, phenyl, naphthyl, biphenyl, thiazolinone ... -phenyl group, carbazolyl group, dibenzofuryl group, more preferably phenyl group , a biphenyl group, and a terphenyl group.

[0095] R 3 , Ar 5 , and Ar 6 The substituents which may be possessed by the group are selected from the group Z of substituents described below. It is preferable that the substituent be a group that can be easily substituted. The compound represented by the above formula (2-1) (hereinafter also referred to as compound (2-1)) is preferably Preferably, the compound is a charge transport compound, i.e., a charge transport host material. The first organic layer may contain only one compound represented by the formula (2-1). Preferably, two or more types may be included.

[0096] (substituent) The substituents that the compounds represented by formula (2) and formula (2-1) may have are the following substituent groups: Substituents selected from Z are preferred.

[0097] <Substituent group Z> The substituent group Z is an alkyl group, an aralkyl group, a heteroaralkyl group, an alkoxy group, an aryl ... aryloxy group, heteroaryloxy group, alkylsilyl group, arylsilyl group, alkyl alkylcarbonyl group, arylcarbonyl group, alkylamino group, arylamino group, aryl It is a aryl group or a heteroaryl group.

[0098] Preferably, the alkyl group has 1 to 20 carbon atoms, the aralkyl group has 7 to 40 carbon atoms, and the alkyl group has 7 to 40 carbon atoms. heteroaralkyl groups having up to 40 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms alkyloxy group, heteroaryloxy group having 3 to 20 carbon atoms, alkylsilyl group having 1 to 20 carbon atoms arylsilyl groups having 6 to 20 carbon atoms, alkylcarbonyl groups having 2 to 20 carbon atoms, Arylcarbonyl groups with 7 to 20 carbon atoms, alkylamino groups with 1 to 20 carbon atoms, and alkylamino groups with 6 to 10 carbon atoms. an arylamino group having 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a hetero group having 3 to 30 carbon atoms; It is an aryl group, and more specifically, it is a substituent described in [Specific examples of substituents] below.

[0099] More preferably, the alkyl group has 1 to 20 carbon atoms, the aralkyl group has 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 aryloxy group having 6 to 30 carbon atoms is an aryl group of the formula: The alkyl group having 1 to 20 carbon atoms may be any of a linear, branched, or cyclic alkyl group. More specifically, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n- Pentyl group, n-hexyl group, n-octyl group, isopropyl group, isobutyl group, isopentyl group Examples include butyl, tert-butyl, and cyclohexyl groups. Among these, methyl groups are , ethyl group, n-butyl group, n-hexyl group, n-octyl group, etc. Alkyl groups are preferred.

[0100] The (hetero)aralkyl group having 7 to 40 carbon atoms may be a straight-chain alkyl group, a branched alkyl group, or a A part of the hydrogen atoms constituting the alkyl group or cyclic group is an aryl group or a heteroaryl group More specifically, it refers to a group substituted with a 2-phenyl-1-ethyl group, a cumyl group, , 5-phenyl-1-pentyl group, 6-phenyl-1-hexyl group, 7-phenyl-1- Examples include 5-phenyl-1-heptyl and tetrahydronaphthyl groups. Preferred are a phenyl-1-hexyl group, a 6-phenyl-1-pentyl group, and a 7-phenyl-1-heptyl group.

[0101] Specific examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, and a propoxy group. Pyroxy group, isopropyloxy group, hexyloxy group, cyclohexyloxy group, octyloxy group Among them, a hexyloxy group is preferred. Specific examples of the (hetero)aryloxy group having 3 to 20 carbon atoms include a phenoxy group, 4-methylphenyloxy group, etc. Among these, a phenoxy group is preferred.

[0102] The alkylsilyl group having 1 to 20 carbon atoms has a structure in which a part of the alkyl group is substituted with an aryl group. Specific examples thereof include a trimethylsilyl group, a triethylsilyl group, and a methylsilyl group. silyl group, triisopropylsilyl group, dimethylphenylsilyl group, tert-butyldimethylsilyl group methylsilyl group, tert-butyldiphenylsilyl group, etc. Propylsilyl group, tert-butyldimethylsilyl group, tert-butyldiphenylsilyl group The aryl group is preferred.

[0103] Specific examples of the arylsilyl group having 6 to 20 carbon atoms include diphenylpyridylsilyl. Among them, the triphenylsilyl group is preferred. stomach. Specific examples of the alkylcarbonyl group having 2 to 20 carbon atoms include an acetyl group, a propionyl group, and a methyl group. cyclohexyl group, pivaloyl group, caproyl group, decanoyl group, cyclohexylcarbonyl group, etc. Among these, an acetyl group and a pivaloyl group are preferred.

[0104] Specific examples of the arylcarbonyl group having 7 to 20 carbon atoms include a benzoyl group, a naphthyl group, and a benzoyl group. Among them, a benzoyl group is preferred. Specific examples of the alkylamino group having 1 to 20 carbon atoms include a methylamino group, a dimethylamino group, and a methylamino group. Amino group, diethylamino group, ethylmethylamino group, dihexylamino group, dioctyl Among these, dimethylamino group, dicyclohexylamino group, etc. are particularly preferred. The cyclohexylamino group is preferred.

[0105] Specific examples of the arylamino group having 6 to 20 carbon atoms include a phenylamino group, a diphenylamino group, and a phenylamino group. di(4-tolyl)amino group, di(2,6-dimethylphenyl)amino group, etc. Among these, a diphenylamino group and a di(4-tolyl)amino group are preferred. The (hetero)aryl group having 3 to 30 carbon atoms is an aromatic group having one free valence. Hydrocarbon groups, aromatic heterocyclic groups, linked aromatic hydrocarbon groups in which multiple aromatic hydrocarbons are linked together, A linked aromatic heterocyclic group in which multiple aromatic heterocyclic groups are linked together, or a combination of an aromatic hydrocarbon and an aromatic It means a group in which at least one heterocycle is arbitrarily linked.

[0106] Specific examples include benzene rings, naphthalene rings, anthracene rings, and the like, which have one free valence. ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, phenylene ring, triphenylene ring, fluoranthene ring, furan ring, benzofuran ring, dibenzofuran Ran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, pyrrole ring, pyrrole ring azole ring, imidazole ring, oxadiazole ring, indole ring, carbazole ring, pyrrole ring Roimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thieno Thiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, benzisoxazo ring, benzisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, pyridine ring, a quinolone ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, Examples include a quinoxaline ring, a perimidine ring, a quinazoline ring, a quinazolinone ring, and an azulene ring. Examples of linked aromatic hydrocarbon groups in which multiple aromatic hydrocarbons are linked include biphenyl. groups, terphenyl groups, etc.

[0107] Among (hetero)aryl groups, from the viewpoint of durability, benzophenone having one free valence is preferred. Zene ring, naphthalene ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, A lysine ring, a pyrimidine ring, or a triazine ring is preferred, and among these, a ring having one free valence and A benzene ring, a naphthalene ring or a phenyl ring which may be substituted with an alkyl group having 1 to 8 carbon atoms. An aryl group having 6 to 18 carbon atoms, such as a nanthrene ring, or a A pyridine ring optionally substituted with 1 to 4 alkyl groups is more preferred, and one free a benzene ring, a naphtha ring, or a benzene ring having a valence and optionally substituted with an alkyl group having 1 to 8 carbon atoms; It is more preferably an aryl group having 6 to 18 carbon atoms, such as an aryl ring or a phenanthrene ring. It's nice.

[0108] When a group in a compound has multiple substituents, the combination of these substituents is is, for example, a combination of an aryl group and an alkyl group, a combination of an aryl group and an aralkyl group, A combination of an aryl group, an alkyl group, and an aralkyl group can be used. Examples of the combination of an aryl group and an aralkyl group include, but are not limited to, For example, a phenyl group, a biphenyl group, or a terphenyl group and a 5-phenyl-1-pentyl group Or a combination with a 6-phenyl-1-hexyl group can be used.

[0109] (molecular weight) The molecular weight of the compound (2-1) is usually 5,000 or less, preferably 3,000 or less, and more preferably Preferably, it is 2500 or less, particularly preferably 2000 or less, and most preferably 1 The lower limit of the molecular weight of the compound (2-1) is preferably 350 or more. It is more preferably 400 or more, and particularly preferably 500 or more.

[0110] (Example) The specific structure of the compound (2-1) is not particularly limited, but examples thereof include the following compounds: It can be obtained.

[0111] [ka]

[0112] [ka]

[0113] [First composition] The first composition forming the first organic layer will now be described. The first composition contains the compound represented by the above formula (2) and an organic solvent. The composition is usually used to form a layer or film by a wet film-forming method, and is particularly useful for forming an organic electroluminescent device. It is preferably used to form the first organic layer. The first organic layer is particularly an emitting layer. That is, the first composition is preferably a composition for forming a light-emitting layer. It's nice.

[0114] [Luminescent materials] The first composition may further include a light-emitting material. The light-emitting material may be any of the publicly available light-emitting materials that are generally used as light-emitting materials in organic electroluminescent devices. Any known material can be used, and there are no particular limitations on the material, as long as it emits light at a desired emission wavelength and has a high luminous efficiency. The light-emitting material may be a fluorescent compound, or a phosphorescent compound. Although the compound may be a light-emitting compound, it is preferable that the compound be a phosphorescent compound from the viewpoint of internal quantum efficiency. From the viewpoint of achieving a wider color gamut and higher brightness, it is preferable that the compound is a fluorescent compound. In addition, when a fluorescent compound is used as a light-emitting material, a phosphorescent compound may be used as a sensitizer. It may also contain a mixture.

[0115] (fluorescent compounds) Examples of the fluorescent compound (hereinafter also referred to as a fluorescent material) include the following materials: Examples include: Examples of fluorescent materials that emit blue light (blue fluorescent materials) include naphthalene, Perylene, pyrene, anthracene, coumarin, chrysene, p-bis(2-phenylethenyl) (iii) benzene and its derivatives.

[0116] Examples of fluorescent materials that emit green light (green fluorescent materials) include quinacridone. derivatives, coumarin derivatives, and aluminum complexes such as Al(C9H6NO)3. do. Examples of fluorescent materials that emit yellow light (yellow fluorescent materials) include rubrene, pentaerythritol, and benzophenone. Rimidone derivatives and the like.

[0117] Examples of fluorescent materials that emit red light (red fluorescent materials) include DCM(4- (dicyanomethylene)-2-methyl-6-(p-dimethy laminostyryl-4H-pyran compounds, benzopyran derivatives, benzothioxanthene derivatives, benzothioxanthene derivatives, azabenzothioxanthene, etc. .

[0118] (Phosphorescent compounds) A phosphorescent compound is a compound that emits light from an excited triplet state. For example, Ir Typical examples are metal complex compounds containing Pt, Eu, etc. Those containing complexes are preferred. Among metal complexes, phosphorescent organometallic complexes that emit light via triplet states have been popular for a long time. Periodic Table (Hereinafter, unless otherwise specified, when we say "periodic table", we mean the long-period periodic table) (This refers to the table below.) Werner compounds containing a metal selected from Groups 7 to 11 as the central metal As such phosphorescent compounds, there may be mentioned: For example, International Publication No. 2014 / 024889, International Publication No. 2015 / 087961, Described in International Publication No. 2016 / 194784 and Japanese Patent Application Laid-Open No. 2014-074000 The phosphorescent compound is preferably a compound represented by the following formula (7): A compound represented by the following formula (205) is preferred, and a compound represented by the following formula (7) is more preferred. It is a compound.

[0119] [ka]

[0120] In formula (7), ring A701 is an aromatic hydrocarbon ring structure which may have a substituent or a substituent represents an aromatic heterocyclic structure which may have the following structure: Ring A702 represents an aromatic heterocyclic structure which may have a substituent. When there are multiple rings A701 and multiple rings A702, they may be the same or different. That's fine.

[0121] R 701 , R 702 are each independently a structure represented by formula (b), and "*" indicates ring A701 or represents the bonding position with ring A702. 701 , R 702 are the same but different Also, R 701 , R 702 If there are multiple of each, they may be the same but different. It may be possible. Ar 701 , Ar 703 each independently represents an aromatic hydrocarbon ring which may have a substituent; structure, or an aromatic heterocyclic structure which may have a substituent.

[0122] Ar 702 is an aromatic hydrocarbon ring structure which may have a substituent, It represents 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 If there are multiple of each, they are the same But it may be different. The substituents bonded to ring A701, the substituents bonded to ring A702, or the substituents bonded to ring A701 The substituents bonded to ring A702 may be bonded to each other to form a ring. good.

[0123] B 701 -L 700 -B 702 represents an anionic bidentate ligand. 701 and B 7 02 each independently represents a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms form a ring. It may be an atom that constitutes L 700 is a single bond or B701 and B 702 Together represents the atomic group that constitutes the bidentate ligand. 701 -L 700 -B 702 If there are multiple If so, they may be the same or different.

[0124] 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 the upper limit of the number of substitutions that can be made on ring A701 and ring A702. represents an integer greater than or equal to 0, m represents an integer of 1 to 3.

[0125] 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. alkyl groups having 1 to 8 carbon atoms, more preferably alkyl groups having 1 to 8 carbon atoms, and particularly preferably alkyl groups having 1 to 8 carbon atoms. 6 alkyl groups.

[0126] An alkoxy group, preferably an alkoxy group having 1 to 20 carbon atoms, more preferably an alkoxy group having 1 to 20 carbon atoms 12 alkoxy groups, more preferably alkoxy groups 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 20 carbon atoms An aryloxy group having 6 to 14 carbon atoms, more preferably an aryloxy group having 6 to 12 carbon atoms. An aryloxy group having 6 carbon atoms is particularly preferred.

[0127] Heteroaryloxy groups, preferably heteroaryloxy groups having 3 to 20 carbon atoms, more preferably Preferably, it is 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 20 carbon atoms Alkylamino groups with prime numbers 1 to 12. An arylamino group, preferably an arylamino group having 6 to 36 carbon atoms, more preferably an arylamino group having 6 to 36 carbon atoms Arylamino groups with prime numbers 6 to 24.

[0128] An aralkyl group, preferably an aralkyl group having 7 to 40 carbon atoms, more preferably an aralkyl group having 7 to 40 carbon atoms 18 aralkyl groups, more preferably aralkyl groups having 7 to 12 carbon atoms. Heteroaralkyl groups, preferably heteroaralkyl groups having 7 to 40 carbon atoms, more preferably is a heteroaralkyl group having 7 to 18 carbon atoms. An alkenyl group, preferably an alkenyl group having 2 to 20 carbon atoms, more preferably an alkenyl group having 2 to 20 carbon atoms Alkenyl groups having 12 carbon atoms, more preferably alkenyl groups having 2 to 8 carbon atoms, particularly preferably alkenyl groups having 1 to 8 carbon atoms. Alkenyl groups with prime numbers 2 to 6.

[0129] An alkynyl group, preferably an alkynyl group having 2 to 20 carbon atoms, more preferably an alkynyl group having 2 to 20 carbon atoms 12 alkynyl groups. An aryl group, preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 24 carbon atoms an aryl group having 6 to 18 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms, and particularly preferably an aryl group having 6 ~14 aryl groups.

[0130] Heteroaryl groups, preferably heteroaryl groups having 3 to 30 carbon atoms, more preferably Heteroaryl groups having 3 to 24 carbon atoms, more preferably heteroaryl groups having 3 to 18 carbon atoms Particularly preferred is a heteroaryl group having 3 to 14 carbon atoms. Alkylsilyl groups, preferably alkylsilyl groups in which the alkyl group has 1 to 20 carbon atoms More preferably, it is an alkylsilyl group in which the alkyl group has 1 to 12 carbon atoms.

[0131] Arylsilyl groups, preferably arylsilyl groups having 6 to 20 carbon atoms in the aryl group More preferably, it is 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.

[0132] The above groups have one or more hydrogen atoms replaced by fluorine atoms or one or more The hydrogen atoms above may be replaced with deuterium atoms. Unless otherwise specified, aryl is an aromatic hydrocarbon ring and heteroaryl is an aromatic heterocyclic ring. It is an elementary ring. Hydrogen atom, deuterium atom, fluorine atom, cyano group, or -SF 5。

[0133] Among the above-mentioned substituent group S, alkyl groups, alkoxy groups, aryloxy groups, Arylamino group, aralkyl group, alkenyl group, aryl group, heteroaryl group, alkoxy group, alkylsilyl groups, arylsilyl groups, and groups in which one or more hydrogen atoms are replaced by fluorine atoms. a substituted group, 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, or an arylamino group. and heteroaryl groups, and one or more hydrogen atoms of these groups are replaced with fluorine atoms. a substituted group, a fluorine atom, a cyano group, or -SF5; More preferably, an alkyl group, an alkoxy group, an aryloxy group, or an arylamino group. , aralkyl groups, alkenyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, is a arylsilyl group, Particularly preferred are alkyl groups, arylamino groups, aralkyl groups, alkenyl groups, and aryl groups. a aryl group, a heteroaryl group, Most preferably, it is an alkyl group, an arylamino group, an aralkyl group, an aryl group, a heteroaromatic group, or a It is a aryl group.

[0134] These substituent groups S further have a substituent selected from the substituent group S as a substituent. The preferred groups, more preferred groups, further more preferred groups, and particularly preferred groups of the substituents that may be present are The preferred groups and most preferred groups for the substituent group S are the same as the preferred groups for the substituent group S. Ring A701 has an aromatic hydrocarbon ring structure or a substituent which may be substituted. It also represents an aromatic heterocyclic structure.

[0135] The aromatic hydrocarbon ring is preferably an aromatic hydrocarbon ring having 6 to 30 carbon atoms. Specifically, benzene ring, naphthalene ring, anthracene ring, triphenylyl ring, acenaphthene ring, A fluoranthene ring, a fluorenone ring, and a fluorene ring are preferred. The aromatic heterocycle may contain any one of a nitrogen atom, an oxygen atom, and a sulfur atom as a heteroatom. Aromatic heterocycles having 3 to 30 carbon atoms, including benzophenone, ... These are benzofuran ring, thiophene ring, and benzothiophene ring.

[0136] Ring A701 is more preferably a benzene ring, a naphthalene ring, or a fluorene ring. Particularly preferred is a benzene ring or a fluorene ring, and most preferred is a benzene ring. Ring A702 represents an aromatic heterocyclic structure which may have a substituent. The aromatic heterocycle preferably contains a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom. Specifically, it is an aromatic heterocycle having 3 to 30 carbon atoms, which contains one of the following rings: a pyridine ring, Pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, oxazole ring, thiazo ring, benzothiazole ring, benzoxazole ring, benzimidazole ring, quinoline ring , isoquinoline ring, quinoxaline ring, quinazoline ring, naphthyridine ring, phenanthridine rings, preferably a pyridine ring, a pyrazine ring, a pyrimidine ring, an imidazole ring, Benzothiazole ring, benzoxazole ring, quinoline ring, isoquinoline ring, quinoxazole ring A pyridine ring, an imidazole ring, a benzothiazoline ring, and the like are more preferred. The most preferred rings are azole ring, quinoline ring, isoquinoline ring, quinoxaline ring and quinazoline ring. Preferably, the ring is a pyridine ring, an imidazole ring, a benzothiazole ring, a quinoline ring, or a quinoxalyl ring. The rings are quinazoline and quinazoline rings.

[0137] Preferred combinations of ring A701 and ring A702 include (ring A701-ring A702) and The notation is (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).

[0138] The substituents that the ring A701 and the ring A702 may have can be selected arbitrarily, but are preferably The substituent is one or more kinds of substituents selected from the above-mentioned group S of substituents. Ar 701 , Ar 703each independently represents an aromatic hydrocarbon ring which may have a substituent; structure, or an aromatic heterocyclic structure which may have a substituent. Ar 702 is an aromatic hydrocarbon ring structure which may have a substituent, It represents an aromatic heterocyclic structure which may have a substituent, or an aliphatic hydrocarbon structure which may have a substituent.

[0139] Ar 701 , Ar 702 , Ar 703 any one of which may have a substituent In the case of an aromatic hydrocarbon ring structure, the aromatic hydrocarbon ring structure preferably has 6 to 30 carbon atoms. Specifically, the aromatic hydrocarbon ring is a benzene ring, a naphthalene ring, an anthracene ring, A triphenylyl ring, an acenaphthene ring, a fluoranthene ring, or a fluorene ring is preferred, and more preferred is a A benzene ring, a naphthalene ring, or a fluorene ring is preferred, and a benzene ring is most preferred. It is a ring.

[0140] Ar 701 , Ar 702 When either of the following is an optionally substituted benzene ring: At least one benzene ring is bonded to an adjacent structure at the ortho or meta position. Preferably, at least one benzene ring is bonded to an adjacent structure at a meta position. More preferable. Ar 701 , Ar 702 , Ar 703 any one of which may have a substituent When the fluorene ring is a fluorene ring, the 9- and 9'-positions of the fluorene ring may have a substituent or an adjacent structure. It is preferred that the compound is bonded to

[0141] Ar 701 , Ar 702 , Ar 703any one of which may have a substituent In the case of an aromatic heterocyclic structure, the heteroatom is preferably a nitrogen atom. an aromatic heterocycle having 3 to 30 carbon atoms containing either an oxygen atom or a sulfur atom, Specifically, pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, o-ring, thiazole ring, benzothiazole ring, benzoxazole ring, benzimidazole ring dazole ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, naphthyridin phenanthridine ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring and preferably a pyridine ring, a pyrimidine ring, a triazine ring, a carbazole ring, Dibenzofuran ring and dibenzothiophene ring.

[0142] Ar 701 , Ar 702 , Ar 703 any one of which may have a substituent When the carbazole ring is a carbazole ring, the N-position of the carbazole ring has a substituent or is bonded to an adjacent structure. It is preferable that Ar 702 When the aliphatic hydrocarbon structure may have a substituent, or an aliphatic hydrocarbon structure having a cyclic structure, preferably having 1 to 24 carbon atoms. and more preferably, the number of carbon atoms is 1 or more and 12 or less, and still more preferably, the number of carbon atoms is 1 or more. Top 8 or below.

[0143] i1 and i2 each independently represent an integer of 0 to 12, preferably 1 to 12, more preferably The number is preferably 1 to 8, and more preferably 1 to 6. By keeping the number in this range, the solubility is improved. and improved charge transport properties are expected. i3 preferably represents an integer of 0 to 5, more preferably 0 to 2, and even more preferably 0 or is 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. It is 3, more preferably 1 or 2, and particularly preferably 1.

[0144] Ar 701 , Ar 702 , Ar 703 The substituents that may be possessed by may be selected arbitrarily. Preferably, it is one or more substituents selected from the above-mentioned substituent group S. Preferred groups are also As in the above-mentioned substituent group S, more preferably, it is unsubstituted (hydrogen atom), alkyl group, aryl group, or the like. A alkyl group is particularly preferred, and an unsubstituted (hydrogen atom) alkyl group is particularly preferred, and the most preferred Unsubstituted (hydrogen atom) or tertiary butyl group, and the tertiary butyl group is Ar 7 03 If Ar exists, 703 To, Ar 703 If Ar does not exist, 702 To, Ar 702 and Ar 703 If Ar does not exist, 701 It is preferred that the substituent is The compound represented by the formula (7) satisfies any one or more of the following (I) to (IV): It is preferable that the compound is a compound having the above structure.

[0145] (I) Phenylene-linked The structure represented by formula (b) is a structure having a group connected to a benzene ring, i.e., a benzene ring structure, i1 is 1 to 6, and at least one of the benzene rings is adjacent at the ortho or meta position It is preferred that the hydroxyl group is bonded to a structure that binds the hydroxyl group. Such a structure improves solubility and charge transport properties. is expected.

[0146] (II) (phenylene)-aralkyl(alkyl) Aromatic carbon atoms having an alkyl or aralkyl group bonded to ring A701 or ring A702 A structure having a hydrogen group or an aromatic heterocyclic group, i.e., Ar 701 is an aromatic hydrocarbon structure or aromatic heterocyclic structure, i1 is 1 to 6, Ar 702 is an aliphatic hydrocarbon structure, and 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, and more preferably, a benzene ring is It is a structure in which 1 to 5 rings are linked together, and more preferably one benzene ring. Such a structure improves solubility and charge transport properties. is expected.

[0147] (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 1~6, i3 is 2, j is 2. Such a structure improves solubility and charge transport properties. is expected.

[0148] (IV)B 701 -L 700 -B 702 B 701 -L 700 -B 702 The structure represented by the following formula (203) or the following formula (204) ) is preferable.

[0149] [ka]

[0150] In formula (203), R 211 , R 212 , R 213 each independently represents a substituent. In formula (204), ring B3 is an aromatic heterocycle containing a nitrogen atom which may have a substituent. The ring B3 is preferably a pyridine ring. The compound represented by the formula (7) is not particularly limited, but the following are preferred: The following are some examples:

[0151] [ka]

[0152] [ka]

[0153] [ka]

[0154] The molecular weight of the phosphorescent compound is preferably 5,000 or less, more preferably 4,000 or less. 0 or less, particularly preferably 3,000 or less. Preferably 1,200 or more, more preferably 1,400 or more, and even more preferably 1,600 That's all. By keeping the molecular weight within this range, the phosphorescent compounds do not aggregate together, and the charge transport material It is believed that this allows the compound to be uniformly mixed with the compound to obtain a light-emitting layer with high light-emitting efficiency.

[0155] The molecular weight of phosphorescent compounds is high, and the Tg, melting point, decomposition temperature, etc. and the light-emitting layer formed has excellent heat resistance, and gas generation, recrystallization, and molecular migration are prevented. The film quality is less likely to deteriorate due to oxidation, and the impurity concentration is less likely to increase due to thermal decomposition of the material. On the other hand, the molecular weight of the phosphorescent compound is determined by the purity of the organic compound. A small size is preferable in terms of ease of manufacturing.

[0156] The first composition further comprises a compound represented by the following formula (250) and a compound represented by the following formula (260): In view of charge balance, the compound may contain at least one selected from the compounds represented by Therefore, it is preferable that the compound contains at least a compound represented by the following formula (250). [Compound represented by formula (250)]

[0157] [ka]

[0158] (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 group having 6 to 3 carbon atoms which may have a substituent a divalent aromatic hydrocarbon group having 3 to 30 carbon atoms which may have a substituent; represents an aromatic heterocyclic group, Xa 2 , Ya 2 and Za 2 each independently represents a hydrogen atom, a carbon atom which may have a substituent, a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, or a monovalent aromatic hydrocarbon group having 3 to 30 carbon atoms which may have a substituent; represents a monovalent aromatic heterocyclic group, 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 Ku, However, if g11, h11, or j11 is 0, the corresponding Xa 2 , Ya 2 , Z a 2 is not a hydrogen atom.) The compound represented by the above formula (250) is preferably a charge transporting compound, i.e., a charge transporting compound. It is preferably a host material.

[0159] <w> In the formula (250), W represents CH or N, and at least one of them is N. However, from the viewpoint of electron transport property and electron durability, it is preferable that at least two of them are N. It is more preferable that all of the atoms are N.

[0160] <Xa 1 , Ya 1 , Za 1 , Xa 2 , Ya 2 , Za 2 > In the formula (250), Xa 1 , Ya 1 , Za 1 A carbon atom which may have a substituent When Xa is a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms, 2 , Ya 2 , Za 2 is replaced In the case of an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a group, The aromatic hydrocarbon ring of the aromatic hydrocarbon group is preferably a 6-membered monocyclic ring or 2 to 5 condensed rings. Specific examples thereof include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, Fluorene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, thiazolinone ring Examples of the ring include a phenylene ring, a fluoranthene ring, and an indenofluorene ring. or a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, or a fluorene ring ring, more preferably a benzene ring, a naphthalene ring, a phenanthrene ring or a fluorene ring. ring, and more preferably a benzene ring, a naphthalene ring, or a fluorene ring. -Xa, which is a terminal partial structure when g11 is 2 or more 1 -Xa 2 , h11 is 2 or more -Ya 1 -Ya 2 , and j11 is 2 or more The terminal partial structure of -Za 1 -Za 2 may be a spirofluorene structure. The compound represented by formula (250) is a terminal partial structure when g11 is 2 or more. -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 Less Preferably, one of them has a spirofluorene structure.

[0161] In the formula (250), Xa 1 , Ya 1 , Za 1 A carbon atom which may have a substituent When Xa is a divalent aromatic heterocyclic group having 3 to 30 carbon atoms, 2 , Ya 2 , Za 2 is a substituent In the case of an aromatic heterocyclic group having 3 to 30 carbon atoms, The aromatic heterocyclic ring of the aromatic heterocyclic group is preferably a 5- or 6-membered monocyclic ring or 2 to 5 condensed rings. Specifically, furan ring, benzofuran ring, dibenzofuran ring, thiophene ring, benzo Thiophene ring, dibenzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, o Diazolidinyl ring, indole ring, carbazole ring, indolocarbazole ring, indeno Carbazole ring, pyrroloimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thieno a thienopyrrole ring, a thienothiophene ring, a furopyrrole ring, a furofuran ring, a thienofuran ring, Benzisoxazole ring, benzisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring, quinoline ring, isoquinolin ring ring, cinnoline ring, quinoxaline ring, perimidine ring, quinazoline ring, quinazolinone ring, etc. Among these, a thiophene ring, a pyrrole ring, an imidazole ring, and a pyridine ring are preferred. , pyrimidine ring, triazine ring, quinoline ring, quinazoline ring, carbazole ring, dibenzo a furan ring, a dibenzothiophene ring, an indolocarbazole ring, a phenanthroline ring, or An indenocarbazole ring is preferable, and a pyridine ring, a pyrimidine ring, or a triazine ring is more preferable. ring, quinoline ring, quinazoline ring, carbazole ring, indolocarbazole ring, indenocarbazole ring a benzol ring, a dibenzofuran ring, or a dibenzothiophene ring, and more preferably a carboxyl ring. a carbazole ring, an indolocarbazole ring, a dibenzofuran ring, or a dibenzothiophene ring be.

[0162] Xa in the formula (250) 1 , Ya 1 , Za 1 , Xa 2 , Ya 2 , and Za 2 To Particularly preferred aromatic hydrocarbon rings are benzene ring, naphthalene ring, and phenanthrene ring. Particularly preferred aromatic heterocycles are carbazole rings, indolocarbazole rings, diphenyl benzoate rings, and phenyl benzoate rings. It is a benzofuran ring or a dibenzothiophene ring. Xa in the formula (250) 1 , Ya 1 , Za 1 , Xa 2 , Ya 2 and Za 2 Inoke the substituent that the aromatic hydrocarbon group having 6 to 30 carbon atoms may have, and The substituents that the aromatic heterocyclic groups of 1 to 30 may have are each independently selected from the following substituent group Z2: The substituents selected from the following substituent group Z2 preferably have a further substituent. It is more preferable that the substituent selected from the substituent group Z2 does not have a further substituent. It is believed that the absence of such a layer can maintain high charge transport properties and durability, which is preferable. Among the substituent groups Z2, aromatic hydrocarbon groups and and aromatic heterocyclic groups are preferred, and aromatic hydrocarbon groups are particularly preferred.

[0163] <g11、h11、j11> g11, h11, and j11 each independently represent an integer of 0 to 6; At least one of g11 is an integer of 1 or more. From the viewpoint of charge transport property and durability, It is preferable that h11 and j11 are 2 or more, or that at least one of h11 and j11 is 3 or more. In addition, the compound represented by the formula (250) includes a ring having three central Ws. The presence of a total of 8 to 18 such rings contributes to the improvement of charge transport properties, durability, and solubility in organic solvents. It is preferable from the viewpoint.

[0164] <(Xa 1 ) g11 , (Ya 1 ) h11、 (Za 1 ) j11 > (Xa 1 ) g11 , (Ya 1 ) h11、 and (Za 1 ) j11 At least one selected from From the viewpoint of the solubility and durability of the compound, the other group is independently 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): It is preferable that the partial structure is selected from the following structures: a 1 ) g11 , when h11 is 1 or more (Ya 1 ) h11、 and j11 is 1 or more In this case (Za 1 ) j11 each independently represents a partial structure represented by the following formula (11), 12) and a portion selected from the partial structure represented by the following formula (13): It is more preferable that the structure is:

[0165] [ka]

[0166] 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 is a hydrogen atom, At least one of the two * marks represents the bond position with the adjacent structure. In the description, the definition of * is the same unless otherwise specified. More preferably, when g11 is 1 or more, (Xa 1 ) g11 , h11 is 1 or more In this case (Ya 1 ) h11 , and when j11 is 1 or more (Za 1 ) j11 Each is unique Specifically, it has a partial structure represented by formula (11) or a partial structure represented by formula (12).

[0167] More preferably, when g11 is 1 or more, (Xa 1 ) g11 , h11 is 1 or more In some cases (Ya 1 ) h11 , and when j11 is 1 or more (Za 1 ) j11 are each It independently has a partial structure represented by formula (11) and a partial structure represented by formula (12). The partial structure represented by formula (12) is preferably a portion represented by the following formula (12-2): It is a structure.

[0168] [ka]

[0169] The partial structure represented by formula (12) is more preferably a partial structure represented by the following formula (12-3): It is a partial structure that is

[0170] [ka]

[0171] A partial structure having a partial structure represented by formula (11) and a partial structure represented by formula (12) From the viewpoint of solubility, the partial structure represented by formula (11) and the partial structure represented by formula (12) are The structure includes a plurality of structures selected from the following formulas (14) to (17): The selected partial structure is preferred. That is, when g11 is 1 or more, (Xa 1 ) g1 1, when h11 is 1 or more (Ya 1 ) h11、 and when j11 is 1 or greater ( Za 1 ) j11 are each independently represented by the formula (11) to the formula (13) and the following formula (14) to the following formula (15): It is preferable that the compound has a partial structure selected from the formula (17). From the viewpoint of (Xa 1 ) g11 , when h11 is 1 or more (Ya 1 ) h11 , and when j11 is 1 or more (Za 1 ) j11 are each independently a formula It is preferable that the compound has a partial structure selected from the formulas (11) to (17).

[0172] [ka]

[0173] A structure selected from the partial structure represented by formula (11) and the partial structure represented by formula (12) The structure containing a plurality of the following is, for example, a partial structure represented by formula (14) as shown in the following formula (14a): , having one partial structure represented by formula (11) and two partial structures represented by formula (12) It is a partial structure that can be considered as follows.

[0174] [ka]

[0175] More preferably, (Xa 1 ) g11 , (Ya 1 ) h11、 and (Za 1 ) j11 few At least one of the partial structures is represented by formula (14) or formula (15). More preferably, when g11 is 1 or more, (Xa 1 ) g11 , h1 (Ya when 1 is 1 or more 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) . The partial structure represented by formula (14) is preferably a part represented by the following formula (14-2): It is a structure.

[0176] [ka]

[0177] The partial structure represented by formula (14) is more preferably represented by the following formula (14-3): It is a partial structure.

[0178] [ka]

[0179] The partial structure represented by formula (15) is preferably a portion represented by the following formula (15-2): It is a structure.

[0180] [ka]

[0181] The partial structure represented by formula (15) is more preferably represented by the following formula (15-3): It is a partial structure.

[0182] [ka]

[0183] The partial structure represented by formula (17) is preferably a part represented by the following formula (17-2): It is a structure.

[0184] [ka]

[0185] (Xa 1 ) g11 , (Ya 1 ) h11、 and (Za 1 ) j11 At least one of the formula As a partial structure containing the partial structure represented by formula (13), a partial structure represented by the following formula (19) Alternatively, it is more preferable that the compound has a partial structure represented by the following formula (20):

[0186] [ka]

[0187] 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 when there are two At least one of the * marks represents the bonding position with the adjacent structure. Among the partial structures represented by formulas (14) to (20), the partial structure represented by formula (14-3) The partial structure represented by formula (15-3) is preferred, and formula (14-3) is more preferred. .

[0188] -(Xa 1 ) g11 -(Xa 2 ), -(Ya 1 ) h11 -(Ya 2 ), and -(Za 1 ) j11 -(Za 2 ) each independently represent 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) It is preferable that the compound has a partial structure. Also, -(Xa 1 ) g11 -(Xa 2 ), -(Ya 1 ) h11 -(Ya 2 ), and -( Za 1 ) j11 -(Za 2 ) is at least one of the following formula (250-1) to the following formula (25 0-10) or a terminal structure.

[0189] [ka]

[0190] In formulas (250-1) to (250-10), * represents a bonding position. 250 is the number of carbon atoms R represents an aromatic hydrocarbon group of 6 to 20 carbon atoms. 32 represents a substituent, and the formulas (250-1) to (2 The structure represented by 50-10) may further have a substituent.] The substituents that these structures may have are R 32 is the same as: Ar 250 is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably Preferably, the alkyl group is a phenyl group or a biphenyl group, and more preferably a phenyl group.

[0191] R 32 In a structure having two R 32 may be the same or different. It's okay to have it. 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 aryloxy group having 1 to 20 carbon atoms, an alkylsilyl group, an arylsilyl group having 6 to 20 carbon atoms, or an alkyl group having 1 to 8 carbon atoms; substituted with an optionally substituted aryl group having 6 to 30 carbon atoms or an alkyl group having 1 to 8 carbon atoms; and more preferably, a heteroaryl group having 1 to 30 carbon atoms. an alkyl group having 7 to 20 carbon atoms, an aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, It may be substituted with an aryloxy group having 6 to 20 carbon atoms or an alkyl group having 1 to 8 carbon atoms. An aryl group having 6 to 30 carbon atoms is preferable, and an alkyl group having 1 to 8 carbon atoms is more preferable. Aralkyl groups with 7 to 20 prime numbers, alkoxy groups with 1 to 8 carbon atoms, aryl groups with 6 to 14 carbon atoms Aryl having 6 to 14 carbon atoms which may be substituted with an oxy group or an alkyl group having 1 to 8 carbon atoms It is the base.

[0192] <R 31 > In formula (250), R when it is a substituent 31 Preferably, the group has a substituent. an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 3 to 30 carbon atoms which may have a substituent From the viewpoint of improving durability and charge transport properties, it is preferable that the aromatic heterocyclic group has a substituent. It is more preferable that R is an aromatic hydrocarbon group which may be a substituent. 31 There are multiple If present, they may be different from each other.

[0193] The substituents which the aromatic hydrocarbon group having 6 to 30 carbon atoms may have are The substituents that the aromatic heterocyclic group of R 31 may have The substituent can be selected from the following substituent group Z2. From the viewpoint of charge transport properties, R 31 is preferably a hydrogen atom. 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.

[0194] <Molecular weight> The compound represented by the formula (250) is a low molecular weight material, and the molecular weight is preferably 3,000 or less. It is preferably 2,500 or less, more preferably 2,000 or less, and particularly preferably 2,500 or less. The lower limit of the molecular weight of the compound is usually 400 or more, and most preferably 1,500 or less. , preferably 500 or more, more preferably 600 or more.

[0195] <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: It can be obtained.

[0196] [ka]

[0197] [ka]

[0198] [ka]

[0199] [ka]

[0200] [ka]

[0201] [ka]

[0202] The first composition contains only one compound represented by formula (250). It may also contain two or more types. [Compound represented by formula (260)]

[0203] [ka]

[0204] (In formula (260), Ar 61 ~Ar 65 each independently represents a hydrogen atom or a monovalent group which may have a substituent; an aromatic hydrocarbon group having 6 to 60 carbon atoms, L 1 ~L 5 each independently represents a divalent group having 6 to 60 carbon atoms which may have a substituent; is an aromatic hydrocarbon group of the formula 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 when n is 1 or more Another Ar 65 At least one of them is not a hydrogen atom.)

[0205] (Ar 61 , Ar 62 , Ar 65 ) Ar in formula (260) 61 , Ar 62 and Ar 65 are each independently a hydrogen atom or is a monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent. Ar in formula (260) 61 , Ar 62 and Ar 65 is the solubility and durability of the compound. From this viewpoint, a hydrogen atom, a monovalent group of a benzene ring, a monovalent group of a naphthalene ring, a monovalent group of the following formula (261 ) or a structure represented by the following formula (262), which is preferably a hydrogen atom, a monovalent group of a benzene ring, The structure represented by the following formula (261) or (262) is more preferred, and The monovalent group of the Zene ring is more preferably a structure represented by the following formula (262), and the following formula (262) ) is particularly preferred.

[0206] From the viewpoint of durability and charge transport property, Ar 61 , Ar 62 and at least one Ar 6 5 Among them, one or more and three or less are the following formula (261) or the following formula (262). Preferably, Ar 61 , Ar 62 and at least one of and Ar 65 One or more of the following: It is more preferable that three or less of them are represented by 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).

[0207] From the viewpoint of durability, Ar 61 , Ar 62 and at least one Ar 65 2 of them It is preferable that at least one of them is represented by the following formula (262), and three of them are represented by the following formula (262). It is even more preferable that (Equation (261), Equation (262))

[0208] [ka]

[0209] (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. Ar 61 is formula (261) or formula (262), m1 is preferably 0 or 1, and 0 More preferred is Ar 62 is formula (261) or formula (262), m2 is 0 or 1 is preferred, and 0 is more preferred. 65 is the formula (261) or the formula (262), m5 is preferably 0 or 1, and more preferably 0.

[0210] (Ar 63 , Ar 64 ) Ar in formula (260) 63 and Ar 64 each independently represents a hydrogen atom or a substituent represents an optionally present monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms. Examples of monovalent aromatic hydrocarbon groups having 6 to 60 carbon atoms include benzene rings, naphthyl groups, and the like. phenylene ring, anthracene ring, phenanthrene ring, tetraphenylene ring, chrysene ring, pyrene a monovalent group of a ring, a benzanthracene ring, a perylene ring, a biphenyl ring, or a terphenyl ring Examples include:

[0211] Ar in formula (260) 63 , Ar 64 From the viewpoint of compound solubility and durability, Independently, a hydrogen atom, a monovalent group of a benzene ring, or a monovalent group of a naphthalene ring is preferred, and hydrogen A monovalent group of an atom or a benzene ring is more preferred. In formula (260), Ar 61 , Ar 62 , Ar 63 , Ar 64 , and n is 1 or more At least one Ar in the case 65 At least one of them is not a hydrogen atom.

[0212] (L 1 ~L 5 ) L in equation (260) 1 ~L 5 each independently represents a divalent carbon atom which may have a substituent; It represents an aromatic hydrocarbon group having a prime number of 6 or more and 60 or less. Examples of divalent aromatic hydrocarbon groups having 6 to 60 carbon atoms include benzene rings, naphthyl groups, and the like. phenylene ring, anthracene ring, tetraphenylene ring, phenanthrene ring, chrysene ring, pyrene Examples of the divalent ring include a divalent group of a benzanthracene ring, a divalent group of a perylene ring, and a divalent group of a benzoanthracene ring.

[0213] L 1 ~L 5 each independently represents an optionally substituted phenylene group or a phenylene A divalent group having two or more groups, for example, 2 to 5 groups, connected by direct bonds is preferred, and the group may have a substituent. A 1,3-phenylene group is more preferred from the viewpoint of solubility. (R 60 ) R in equation (260) 60 Each of the groups independently represents a substituent. Examples of the substituent include the following substituents: Substituent groups selected from the group Z2 can be used. Among them, alkyl groups, alkenyl group, alkynyl group, alkoxy group, aryloxy group, alkoxycarbonyl group , acyl group, halogen atom, haloalkyl group, alkylthio group, arylthio group, silyl A group, a siloxy group, an aralkyl group, or an aromatic hydrocarbon group is preferred. From the viewpoint of alkyl groups, alkenyl groups, alkoxy groups, aryloxy groups, alkoxy groups, Carbonyl group, acyl group, halogen atom, haloalkyl group, silyl group, siloxy group, ara alkyl groups, alkoxy groups, aralkyl groups, aromatic hydrocarbon groups are preferred, and alkyl groups, alkoxy groups, aralkyl groups, aromatic hydrocarbon groups are preferred. Aromatic hydrocarbon groups are more preferred, alkyl groups having 10 or less carbon atoms, and aromatic hydrocarbon groups having 30 or less carbon atoms. alkyl groups, and aromatic hydrocarbon groups having 30 or less carbon atoms are more preferred. A group in which 2 to 5 alkyl rings are linked together is particularly preferred.

[0214] (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 determined from the viewpoint of the solubility and durability of the compound. Preferably, it is 4 or less, more preferably 3 or less, even more preferably 2 or less, and particularly preferably 1 or less. Preferably, 0 is the most preferable.

[0215] Also, Ar 61 is the formula (261) or the formula (262), m1, Ar 62 is the formula (2 61) or formula (262), m2, and Ar 65 is the formula (261) or the formula (26 In the case of 2), m5 is preferably 0. In the formula (260), m3 and m4 are each 1 or more from the viewpoint of the solubility and durability of the compound. is preferred, 4 or less is preferred, 3 or less is more preferred, and 2 or less is particularly preferred.

[0216] When m1 in formula (260) is 2 or more, multiple L 1 may be the same or different If m2 in formula (260) is 2 or more, multiple L 2 are the same or different If m3 in equation (260) is 2 or more, multiple L 3 are the same but different If m4 in formula (260) is 2 or more, multiple L 4 are the same but different If m5 in formula (260) is 2 or more, multiple L 5 are the same but different It is also possible.

[0217] ((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 and at least one (L 5 ) m5 At least one of the groups is responsible for the solubility and resistance of the compound. From the viewpoint of durability, the partial structure represented by the following formula (11) and the partial structure represented by the following formula (12) and a partial structure selected from the partial structures represented by the following formula (13): When m1 is 1 or more, 1 ) m1 , when m2 is 1 or more (L 2 ) m2 and n is 1 or more and m5 is 1 or more (L 5 ) m5 , and when m3 is 1 or more, (L 3 ) m 3 and m4 are 1 or more (L 4 ) m4 is a partial structure represented by the following formula (11), A partial structure selected from a partial structure represented by formula (12) and a partial structure represented by formula (13) below: It is more preferable that the compound has a partial structure.

[0218] [ka]

[0219] In each of the above formulas (11) to (13), * indicates the bonding position with the adjacent structure or A r 61 , Ar 62 , Ar 63 , Ar 64 or Ar 65 is a hydrogen atom At least one of the two * marks represents the bonding position with the adjacent structure. Unless otherwise specified, the definition of * is the same in the rest of this document. 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 following must be satisfied: ) or a partial structure represented by formula (12).

[0220] More preferably, in formula (260), when m1 is 1 or more, (L 1 ) m1 , m2 When is 1 or more, (L 2 ) m2 , when m3 is 1 or more (L 3 ) m3 , if m4 is 1 or more Combined (L 4 ) m4 , and when n is 1 or more and m5 is 1 or more, (L 5 ) m5 are respectively, It 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 , m2 is 1 or more (L 2 ) m2 , when m3 is 1 or more (L 3 ) m3 , if m4 is 1 or more (L 4 ) m4 , and when n is 1 or more and m5 is 1 or more, (L 5 ) m5 are the formulas It has a partial structure represented by formula (11) and a partial structure represented by formula (12). In formula (260), formula (12) is preferably the following formula (12-2).

[0221] [ka]

[0222] In formula (260), formula (12) is more preferably the following formula (12-3): is.

[0223] [ka]

[0224] 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 and (L 5 ) m5 Of these, The partial structure that is preferably contained in at least one of the compounds is a partial structure represented by formula (11) and It is a partial structure having a partial structure represented by formula (12). In formula (260), the partial structure represented by formula (11) and the partial structure represented by formula (12) The partial structure having the structure includes a partial structure represented by formula (11) and a partial structure represented by formula (12). The following formula (14) to the following formula (17) are structures including a plurality of structures selected from the partial structures In other words, when m1 is 1 or more, (L 1 ) m1 , m When 2 is 1 or more (L 2 ) m2 , when m3 is 1 or more (L 3 ) m3 , m4 is 1 or more In the case of (L 4 ) m4 , and when n is 1 or more and m5 is 1 or more, (L 5 ) m5 are independent and a compound selected from the formulas (11) to (13) and the following formulas (14) to (17): It is preferable that the compound has a partial structure.

[0225] [ka]

[0226] In formula (260), the partial structure represented by formula (11) and the part represented by formula (12) The structure including a plurality of structures selected from the structures of, for example, formula (14) is a structure of the following formula (14a): Similarly, there is one partial structure represented by formula (11) and two partial structures represented by formula (12). This is a partial structure that can be considered as such.

[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 It has a partial structure represented by formula (14) or a partial structure represented by formula (15). For example, when m1 is 1 or more, 1 ) m1 , when m2 is 1 or more (L 2 ) m2 , m3 1 or more (L 3 ) m3 , when m4 is 1 or more (L 4 ) m4 , and n is 1 or more and When m5 is 1 or more, (L 5 ) m5 is a partial structure represented by formula (14) or formula (15) It has a partial structure represented by the following formula: In formula (260), formula (14) is preferably the following formula (14-2).

[0229] [ka]

[0230] In formula (260), formula (14) is more preferably the following formula (14-3): do.

[0231] [ka]

[0232] In formula (260), formula (15) is preferably the following formula (15-2).

[0233] [ka]

[0234] In formula (260), formula (15) is more preferably the following formula (15-3): do.

[0235] [ka]

[0236] In formula (260), formula (17) is preferably the following formula (17-2).

[0237] [ka]

[0238] Also, (L 1 ) m1 , (L 2 ) m2 , (L 3 ) m3 , (L 4 ) m 4, and at least one (L 5 ) m5 At least one of the parts is represented by formula (13). As a partial structure containing the structure, a partial structure represented by the following formula (19) or a partial structure represented by the following formula (20) It is more preferable that the compound has a partial structure such that

[0239] [ka]

[0240] In each of the above formulas (14) to (20), * indicates a bonding position with an adjacent structure or a water bond. It represents an elementary atom, and at least one of the two * marks represents the bonding position with the adjacent structure. In the formula (260), among the formulas (14) to (20), the formulas (14-3) and (15) -3) is preferred, and formula (14-3) is more preferred. (L 1 ~L 5 (preferred substructure of In formula (260), L 1 ~L 5 is a partial structure represented by formula (11), a partial structure represented by formula (14-3) or a part represented by formula (15-3) It is preferable to have a structure.

[0241] (n) In the formula (260), n represents an integer of 0 to 10. In the formula (260), n is preferably 1 or more from the viewpoint of the solubility and durability of the compound. Preferably, the number is 2 or more, more preferably 6 or less, even more preferably 5 or less, and especially 4 or less. Preferred.

[0242] (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.

[0243] (R 101 ~R 126 ) In equation (260), R 101 ~R 126 each independently represents a hydrogen atom or a substituent. The substituent may be selected from the following group Z2 of substituents. Among these, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, aryloxy groups, group, alkoxycarbonyl group, acyl group, halogen atom, haloalkyl group, alkylthio A group, an arylthio group, a silyl group, a siloxy group, an aralkyl group, or an aromatic hydrocarbon group is preferred. From the viewpoint of durability, alkyl groups, alkenyl groups, alkoxy groups, aryloxy groups, and the like are preferred. a silyl group, an alkoxycarbonyl group, an acyl group, a halogen atom, a haloalkyl group, a silyl group, Siloxy groups, aralkyl groups, and aromatic hydrocarbon groups are preferred, and hydrogen atoms and aromatic hydrocarbon groups are also preferred. is more preferred, and a hydrogen atom is particularly preferred.

[0244] (substituent) In formula (260), Ar 61 ~Ar 65 Monovalent carbon atoms of 6 or more and 60 or less Aromatic hydrocarbon groups and L 1 ~L 5 Aromatic carbon with a divalent carbon number of 6 or more and 60 or less The substituents that the hydrogen fluoride group may have are each independently selected from the following substituent group Z2: Among these, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups , aryloxy group, alkoxycarbonyl group, acyl group, halogen atom, haloalkyl group, alkylthio group, arylthio group, silyl group, siloxy group, aralkyl group, or aromatic Aromatic hydrocarbon groups are preferred, and alkyl groups, alkenyl groups, alkoxy groups, and aryloxy groups are also preferred. , alkoxycarbonyl group, acyl group, halogen atom, haloalkyl group, silyl group, silyl An oxy group, an aralkyl group, or an aromatic hydrocarbon group is more preferred.

[0245] (molecular weight) The molecular weight of the compound represented by formula (260) is preferably 3,000 or less, more preferably is 2,500 or less, more preferably 2,000 or less, and particularly preferably 1, 500 or less, and usually 400 or more, preferably 500 or more, more preferably 60 Greater than or equal to 0.

[0246] (Example) Specific examples of the compound represented by formula (260) are shown below, but the compound is not limited to these. There is no.

[0247] [ka]

[0248] [ka]

[0249] [ka]

[0250] The first composition contains only one compound represented by the formula (260). It may also contain two or more types. [Organic solvents] The organic solvent contained in the first composition is a compound represented by formula (2) formed by wet film formation. It is a volatile liquid component used to form a layer containing

[0251] The organic solvent contains the compound represented by formula (2) as a solute, the light-emitting material, and the charge-transporting There are no particular limitations on the organic solvent as long as it dissolves the compound well. Preferred organic solvents include, for example, n-decane, cyclohexane, and ethylcyclohexane. Alkanes such as toluene, xylene, mesitylene, Phenylcyclohexane (cyclohexylbenzene), tetralin, methylnaphthalene, etc. aromatic hydrocarbons; halocarbons such as chlorobenzene, dichlorobenzene, trichlorobenzene, etc. Genated aromatic hydrocarbons; 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, Anisole, phenetole, 2-methoxytoluene, 3-methoxytoluene, 4-methoxy Dimethylanisole, 2,3-dimethylanisole, 2,4-dimethylanisole, diphenyl aromatic ethers such as phenyl acetate, phenyl propionate, methyl benzoate, Aromatic esters such as ethyl benzoate, propyl benzoate, and n-butyl benzoate; cyclo Alicyclic ketones such as hexanone, cyclooctanone, and fenchone; cyclohexanol, Alicyclic alcohols such as cyclooctanol; methyl ethyl ketone, dibutyl ketone, etc. Aliphatic ketones; aliphatic alcohols such as butanol and hexanol; ethylene glycol Dimethyl Ether, Ethylene Glycol Diethyl Ether, Propylene Glycol-1 Aliphatic ethers such as monomethyl ether acetate (PGMEA); .

[0252] Among these, from the viewpoint of viscosity and boiling point, alkanes, aromatic hydrocarbons, and aromatic ethers are the most popular. Preferred are aromatic hydrocarbons, aromatic ethers and aromatic esters, and 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. and ratios may be used.

[0253] The boiling point of the organic solvent used is usually 80°C or higher, preferably 100°C or higher, more preferably 1 20°C or higher, and usually 380°C or lower, preferably 350°C or lower, more preferably 33 If the boiling point of the organic solvent is below this range, the composition may be dissolved in water during wet film formation. The evaporation of the solvent from the solvent may reduce the stability of the film formation. If it exceeds this value, the stability of the film formation may be reduced due to residual solvent after film formation during wet film formation. There is.

[0254] In particular, two or more of the above organic solvents having a boiling point of 150°C or higher are combined. By doing so, a uniform coating film can be produced. If the temperature is less than this, it is thought that a uniform film may not be formed during application. 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, and particularly preferably 99.00% by mass or less.

[0255] Usually, the thickness of the light-emitting layer is about 3 to 200 nm, but the content of the organic solvent is below this lower limit. If the first composition rotates, the viscosity of the first composition may become too high, which may reduce the film formation workability. If the content of the organic solvent exceeds this upper limit, the thickness of the film obtained by removing the solvent after film formation becomes As a result, film formation tends to become difficult.

[0256] <Second organic layer> The polymer contained in the second organic layer is a polymer that satisfies at least one of the following (i) and (ii): Contains the body. (i) 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) Among them, it has two or more repeating units. (ii) A repeating unit represented by the following formula (54), a repeating unit represented by the following formula (55) position, a repeating unit represented by the following formula (56) and a repeating unit represented by the following formula (57) It consists of only one or more repeating units of the above.

[0257] Hereinafter, "repeating unit represented by formula (54)" and "repeating unit represented by formula (55)" will be referred to as "repeating unit represented by formula (54)" and "repeating unit represented by formula (55)". ", "Repeating unit represented by formula (56)", "Repeating unit represented by formula (57)" This section will explain the details. In addition, the polymer used in the second organic layer preferably does not have a crosslinking group. The crosslinking group in the formula (I) is as described below. <Repeating unit represented by formula (54)>

[0258] [ka]

[0259] (In formula (54), Ar 51 represents an aromatic hydrocarbon group which may have a substituent other than a bridging group, an aromatic heterocyclic group which may have a substituent, or a bridging group which may have a substituent other than Aromatic hydrocarbon groups and aromatic heterocyclic groups which may have a substituent other than a bridging group are selected from the group consisting of: a group in which a plurality of groups 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 has a substituent other than a crosslinking group is an alkyl group which may be R 207 ~R 209 and R 211 ~R 214 are each independently a hydrogen atom or a group other than a bridging group. an alkyl group which may have a substituent, an aralkyl group which may have a substituent other than a bridging group; an aromatic hydrocarbon group which may have a substituent other than a cyclic group or a crosslinking group, a, b, and d each independently represent an integer of 0 to 4; c is an integer from 0 to 3, a+b is greater than or equal to 1, 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 each independently represent an integer of 0 to 3.

[0260] (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 22 2 are each independently an alkyl group which may have a substituent other than a crosslinking group. The alkyl group may be a straight-chain, branched, or cyclic alkyl group. There is no particular limitation on the number of carbon atoms in the alkyl group. However, in order to maintain the solubility of the polymer, it is preferably 1 or more and 8 or less. The alkyl group is preferably a methyl group or an ethylene group, more preferably 6 or less, and even more preferably 3 or less. A ethyl group is more preferred.

[0261] 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. They can be uniformly distributed around the nitrogen atom and are easy to synthesize. R 201 and R 202 are preferably the same groups. 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. They can be uniformly distributed around the nitrogen atom and are easy to synthesize. R 221 and R 222 are preferably the same groups.

[0262] (R 207 ~R 209 and R 211 ~R 214 ) R 207 ~R 209 and R 211 ~R 214 are each independently a hydrogen atom or a bridging group. an alkyl group which may have a substituent other than a bridging group; It is an aromatic hydrocarbon group which may have a substituent other than a ralkyl group or a bridging group.

[0263] The alkyl group is not particularly limited, but is preferably a carbon-containing alkyl group since it tends to improve the solubility of the polymer. The number is preferably 1 or more, and is preferably 24 or less, more preferably 8 or less, and most preferably 6 or less. The alkyl group may have a linear, branched or cyclic structure. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an ethyl group. butyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n -hexyl group, n-octyl group, cyclohexyl group, dodecyl group, etc.

[0264] The aralkyl group is not particularly limited, but carbon is preferred because it tends to improve the solubility of the polymer. The prime number is preferably 5 or more, and is preferably 60 or less, and more preferably 40 or less. Specific examples of the aralkyl group include a 1,1-dimethyl-1-phenylmethyl group, a 1,1 -di(n-butyl)-1-phenylmethyl group, 1,1-di(n-hexyl)-1-phenyl phenylmethyl group, 1,1-di(n-octyl)-1-phenylmethyl group, phenylmethyl group, Phenylethyl group, 3-phenyl-1-propyl group, 4-phenyl-1-n-butyl group, 1-methyl-1-phenylethyl group, 5-phenyl-1-n-propyl group, 6-phenyl -1-n-hexyl group, 6-naphthyl-1-n-hexyl group, 7-phenyl-1-n-hexyl group butyl group, 8-phenyl-1-n-octyl group, 4-phenylcyclohexyl group, etc. can be done.

[0265] The aromatic hydrocarbon group is not particularly limited, but tends to improve the solubility of the polymer. Therefore, the number of carbon atoms is preferably 6 or more, and is preferably 60 or less, and more preferably 30 or less. stomach. Specific examples of the aromatic hydrocarbon group include a benzene ring, a naphthalene ring, an anthracene ring, Phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring 6-membered rings such as triphenylene ring, acenaphthene ring, fluoranthene ring, and fluorene ring Examples include monovalent groups of a single ring or 2 to 5 condensed rings, and groups in which a plurality of these are linked together.

[0266] From the viewpoint of improving charge transport properties and durability, R 207 and R 208 is a methyl group or aromatic carbon A hydride group is preferred, and R 207 and R 208 is more preferably a methyl group, and R 2 09 is more preferably a phenyl group. R 201 , R 202 , R 221 , R 222 alkyl group, R 207 ~R 209 and R 2 11 ~R 214 The alkyl group, aralkyl group and aromatic hydrocarbon group are substituted groups other than bridging groups. The substituents other than the bridging group may be the same as those described above for R 207 ~R 209 and R 211 ~ R 214 The groups listed as preferred alkyl groups, aralkyl groups and aromatic hydrocarbon groups are Examples include:

[0267] R 201 , R 202 , R 221 , R 222 alkyl group, R 207 ~R 209 and R 2 11 ~R 214 The alkyl group, aralkyl group and aromatic hydrocarbon group are preferred from the viewpoint of lowering voltage. Most preferably, they have no substituents.

[0268] (a, b, c and d) In the repeating unit represented by the above formula (54), a and b each independently represent 0. a is an integer of 1 to 4, and a+b is 1 or more. It is preferable that a and b are each 2 or less. It is more preferable that both a and b are 1. Here, a being 1 or more means that c is When b is 1 or more, b is 1 or more when d is 1 or more. When b is 1 or more, d is also preferably 1 or more. When c is 2 or more, The number of a's may be the same or different, and if d is 2 or more, the number of b's may be the same. They may be different.

[0269] When a+b is 1 or more, the aromatic rings in the main chain are twisted due to steric hindrance, making it difficult for the polymer to dissolve in a solvent. The coating film formed by the wet film-forming method and heat-treated has excellent insolubility in solvents. Therefore, if a+b is 1 or more, it is possible to form another organic film on this coating film by a wet film formation method. When forming a layer (for example, a light-emitting layer), the light-emitting layer forming solvent used in the present invention contains an organic solvent. As a result, the influence on the formed light-emitting layer is reduced. This is expected to further extend the operating life of the organic electroluminescent device.

[0270] In the repeating unit represented by the above formula (54), c is an integer of 0 to 3, and d is 0. It is preferable that c and d are each an integer of 2 or less, and that c and d are equal. It is more preferred that both c and d are 1 or both c and d are 2. preferable. In the repeating unit represented by the above formula (54), both c and d are 1 or both c and d are 1. If a is 2 and both a and b are 2 or 1, then R 201 and R 202 are mutual It is most preferred that the bond is symmetrical to the .

[0271] where R 201 and R 202 and bond to positions symmetric to each other means that in equation (54) The fluorene ring, carbazole ring, or 9,10-dihydrophenanthrene derivative structure Then, R 201 and R 202 In this case, the bond positions are symmetrical. A 180 degree rotation is considered to be the same structure. R 221 and R 222 are, if present, independently the carbon atom of the benzene ring to which X is attached. It is preferably present at the 1st, 3rd, 6th or 8th position relative to the atom. to R 221 and / or R 222 The existence of R 221 and / or R 222 is combined The fused ring and the adjacent benzene ring on the main chain are twisted due to steric hindrance, and the polymer is In addition to its excellent solubility, the coating film formed by the wet film-forming method and heat-treated has excellent insolubility in solvents. This tends to be preferable.

[0272] (i and j) In the repeating unit represented by the above formula (54), i and j each independently represent 0. i and j are integers of 1 to 3. Preferably, i and j are each 2 or less, and both i and j are 0 or is more preferably 1.

[0273] (Ar 51 ) In the repeating unit represented by the above formula (54), Ar 51 represents a substituent other than a bridging group. an aromatic hydrocarbon group which may have a substituent other than a crosslinking group; Aromatic hydrocarbon groups which may have a substituent other than a cyclic group or a bridging group, and aromatic hydrocarbon groups other than a bridging group It represents a group in which a plurality of groups selected from aromatic heterocyclic groups which may have a substituent are linked together.

[0274] The aromatic hydrocarbon group preferably has 6 to 60 carbon atoms. Zene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring , pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring, acenaphthene ring, fluorine ring A monovalent group of a 6-membered ring such as a lanthene ring or a fluorene ring, or a group of 2 to 5 condensed rings thereof For example, a "monovalent group of a benzene ring" refers to a "monovalent "a benzene ring having a free valence of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31,

[0275] The aromatic heterocyclic group preferably has 3 or more and 60 or less carbon atoms, and specifically, furan ring, benzofuran ring, thiophene ring, benzothiophene ring, pyrrole ring, pyrazole ring, Imidazole ring, oxadiazole ring, indole ring, carbazole ring, pyrrolyl imidazoline pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, benzisoxazole ring, benzo a diisothiazole ring, a benzimidazole ring, a pyridine ring, a pyrazine ring, a pyridazine ring, Pyrimidine ring, triazine ring, quinoline ring, isoquinoline ring, cinnoline ring, quinoxalin quinazoline ring, quinanthridine ring, phenanthridine ring, benzimidazole ring, perimidine ring, quinazoline ring, quinazoline ring a monovalent group of a 5- or 6-membered monocyclic ring or 2- to 4-condensed ring such as a zolinone ring or an azulene ring, or Examples include groups in which a plurality of these are linked together.

[0276] Ar 51 The polymer has a substituent other than a crosslinking group because of its excellent charge transport property and durability. Among them, aromatic hydrocarbon groups which may have a substituent other than a crosslinking group are preferred. The monovalent group of the benzene ring or fluorene ring, i.e., the group having a substituent other than the bridging group, 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 more preferred. Fluorenyl groups are particularly preferred.

[0277] Ar 51 and the substituents other than the bridging group that the aromatic hydrocarbon group and aromatic heterocyclic group may have. There are no particular restrictions on the substituents, so long as they do not significantly impair the properties of the present polymer. The group is preferably a group selected from the following substituent group Z2, and examples thereof include an alkyl group, ... A koxy group, an aromatic hydrocarbon group, or an aromatic heterocyclic group is more preferred, and an alkyl group is even more preferred. It's nice.

[0278] Ar 51 In terms of solubility in coating solvents, the A fluorenyl group is preferred, and in particular, a 2-fluoro group substituted with an alkyl group having 4 to 12 carbon atoms is preferred. Further, a 9-fluorenyl group in which the 9-position of a 2-fluorenyl group is substituted with an alkyl group is preferred. Alkyl-2-fluorenyl groups are preferred, and in particular 9,9-disubstituted alkyl groups. Alkyl-2-fluorenyl groups are preferred.

[0279] A fluorenyl group substituted with an alkyl group at least at the 9-position or the 9'-position This tends to improve the solubility in a solvent and the durability of the fluorene ring. The fluorenyl group substituted with an alkyl group at both the 9- and 9'-positions allows for solvent The solubility in water and the durability of the fluorene ring tend to be further improved. Also, Ar 51 is a spirobifluorenyl group from the viewpoint of solubility in the coating solvent. is also preferred.

[0280] (Other preferred Ar 51 ) The polymer may include a repeating unit represented by the formula (54) 51 At least The other one contains a monovalent or divalent group in which 2 to 5 optionally substituted benzene rings are linked together. a group containing 1-methyl-2-(2-methyl-1-propanol), a fluorenyl group which may have a substituent, a group represented by the following formula (51), a group represented by the following formula (52), A group represented by formula (52) or a group represented by formula (53) below is preferred. (Group represented by formula (51))

[0281] [ka]

[0282] In formula (51), * represents a bond to the nitrogen atom of the main chain of formula (54), Ar 53 , Ar 54 each independently represents a divalent group which may have a substituent other than a crosslinking group. an aromatic hydrocarbon group, an aromatic heterocyclic group which may have a substituent other than a bridging group, or a bridging group an aromatic hydrocarbon group which may have a substituent other than a group or a bridging group; a divalent group in which a plurality of optionally substituted aromatic heterocyclic groups are linked together directly or via a linking group; death, Ar 55 represents an aromatic hydrocarbon group which may have a substituent other than a bridging group; an aromatic heterocyclic group which may have a substituent, or an aromatic heterocyclic group which may have a substituent other than a bridging group; A compound in which a plurality of aromatic hydrocarbon groups or aromatic heterocyclic groups are linked together directly or via a linking group represents the base of valence, Ar 56 represents a hydrogen atom or a substituent.

[0283] (Ar 53 , Ar 54 ) In the repeating unit represented by the formula (51), Ar 53 , Ar 54 are respectively Independently, 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, or a bridging group, an aromatic hydrocarbon group or an aromatic heterocyclic group which may have a substituent other than a bridging group; represents a divalent group in which a plurality of groups are linked together directly or via a linking group. and has a substituent other than a divalent aromatic hydrocarbon group or a crosslinking group which may have a substituent. It is a group in which a plurality of divalent aromatic hydrocarbon groups are linked together. The substituents which the aromatic heterocyclic group may have are preferably the same as those in the following group Z2 of substituents. .

[0284] Ar 53 and Ar 54 The aromatic hydrocarbon group and aromatic heterocyclic group are 52 Similar to Aromatic hydrocarbon groups and aromatic heterocyclic groups such as those listed above can be used. An aromatic hydrocarbon group which may have a substituent or an aromatic hydrocarbon group which may have a substituent The divalent group in which a plurality of heterocyclic groups are linked directly or via a linking group is a group in which a plurality of the same groups are linked. It may be a group in which two or more groups are linked together, or a group in which two or more different groups are linked together.

[0285] When a plurality of the above divalent groups are linked together, examples include divalent groups in which 2 to 10 groups are linked together. It is preferably a divalent group with up to 5 bonds. Ar 53 is a group consisting of 1 to 6 optionally substituted divalent aromatic hydrocarbon groups linked together. A group in which 2 to 4 optionally substituted divalent aromatic hydrocarbon groups are linked is preferred. Among them, a group in which 1 to 4 phenylene rings which may have a substituent are linked is more preferable. A group having two phenylene rings linked together, which may have a substituent, is more preferred. is particularly preferred.

[0286] In addition, when a plurality of these divalent aromatic hydrocarbon groups or divalent aromatic heterocyclic groups are linked together, Preferably, the divalent aromatic hydrocarbon groups are linked together in such a way that they do not conjugate. Specifically, the 1,3-phenylene group or the substituted group have a twist due to the steric effect of the substituent. It is preferred that the compound contains a group that forms the structure. Ar 53 The substituents which may be possessed by are preferably the same as those in the following group of substituents Z2. For more details, see Ar 53 has no substituents.

[0287] Ar 54 are excellent in charge transport properties and durability, so they are A group in which one or more optionally divalent aromatic hydrocarbon groups are linked is preferred, and the divalent aromatic The hydrocarbon group may have a substituent. When a plurality of hydrocarbon groups are linked, the number of the linked hydrocarbon groups is preferably 2 to 10. A value of 6 or less is more preferable, and a value of 3 or less is particularly preferable from the viewpoint of film stability. Aromatic hydrocarbon structures include benzene ring, naphthalene ring, anthracene ring, and fluorene ring. and more preferably a benzene ring or a fluorene ring. a group in which 1 to 4 phenylene rings which may have a substituent are linked together, or a group in which A group in which an optionally substituted phenylene ring and an optionally substituted fluorene ring are linked is preferred. In view of broadening the LUMO, it is preferable that two phenylene rings which may have a substituent are linked. Biphenylene is particularly preferred.

[0288] Ar 54 The substituents which may be possessed by the group Z2 include any one of the following substituents group Z2, A combination of these groups can be used. N-carbazolyl group, indolocarbazolyl group The substituent is preferably other than an indenocarbazolyl group, and more preferably, It is also preferred that the alkyl group has no substituent. .

[0289] (Ar 55 ) Ar 55 represents an aromatic hydrocarbon group which may have a substituent, an aromatic hydrocarbon group which may have a substituent, Aromatic heterocyclic groups, or aromatic hydrocarbon groups which may have a substituent, and A plurality of groups selected from the aromatic heterocyclic groups which may be optionally substituted are linked directly or via a linking group. Preferably, it is a monovalent aromatic hydrocarbon group which may have a substituent, or It is a group in which a plurality of monovalent aromatic hydrocarbon groups, which may have a substituent, are linked together.

[0290] Here, the substituents that the aromatic hydrocarbon group and the aromatic heterocyclic group may have are the following substituents: The same groups as those in the group Z2 are preferred. When multiple groups are linked together, they are divalent groups with 2 to 10 groups linked together, and monovalent groups with 2 to 5 groups linked together. As the aromatic hydrocarbon and aromatic heterocycle, the Ar 51 The same fragrance Aromatic hydrocarbon groups and aromatic heterocyclic groups can be used.

[0291] 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 molecules, a-1 to a-4, b-1 to b-9, c- A structure selected from the group consisting of 1 to c-4, d-1 to d-16, and e1 to e4 is preferred. From the viewpoint of promoting the broadening of the LUMO of the molecule by having an electron-withdrawing group, a-1 A structure selected from a-1 to a-4, b-1 to b-9, d-1 to d-12, and e1 to e4 is preferred. Furthermore, from the viewpoint of the effect of confining excitons formed in the light-emitting layer, which has a high triplet level, it is preferable. , a-1 to a-4, d-1 to d-12, and e1 to e4 are preferred. In addition, d-1 and d-10 are more preferable from the viewpoint of easy synthesis and excellent stability. The benzene ring structures of d-1 and d-2 are particularly preferred. These structures may further have a substituent. In the figure, "-*" indicates Ar 54 If there are multiple "-*", One of them is Ar 54 represents the bonding position with

[0292] [ka]

[0293] [ka]

[0294] [ka]

[0295] <R 31 and R 32 > R in Scheme 2 31 and R 32 each independently represents a linear or branched 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 6 or less, and more preferably 3 or less. A methyl group or an ethyl group is more preferred.

[0296] R 31 and R 32 may be the same or different, but the charge is uniformly distributed between the nitrogen atoms. Since it can be distributed around and is easy to synthesize, all R 31 and R 32 teeth It is preferred that they are the same groups. Ar 55 The substituents which may be possessed by the group include any one of the following substituent group Z2 or From the viewpoint of durability and charge transportability, the above-mentioned A r 54 It is preferable that the substituents are selected from the same substituents that may be possessed by the group.

[0297] (Ar 56 ) Ar 56 represents a hydrogen atom or a substituent. 56 When is a substituent, the specific limitation is Preferably, the aromatic hydrocarbon group may have a substituent, but is not limited to a substituted aromatic hydrocarbon group. A preferred structure is an aromatic heterocyclic group such as the Ar 53 ~Ar 54 Listed in It is a monovalent structure similar to the aromatic hydrocarbon structure and aromatic heterocyclic structure mentioned above.

[0298] Ar 56 When is a substituent, bonding to the 3-position of carbazole improves durability. It is preferable from the viewpoint of Ar 56 From the viewpoint of ease of synthesis and charge transport properties, It is preferable that Ar 56 From the viewpoint of improving durability and charge transportability, an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent; It is preferable that the alkyl group is an aromatic hydrocarbon group which may have a substituent. stomach.

[0299] Ar 56 is preferably a hydrogen atom from the viewpoint of ease of synthesis and charge transport properties. stomach. Ar 56 is an aromatic hydrocarbon group which may have a substituent or an aromatic hydrocarbon group which may have a substituent In the case of an aromatic heterocyclic group, the substituents are the same as those listed in the following substituent group Z2. The same applies to the preferred substituents, and the substituents that these substituents may further have are also The same is true.

[0300] (Group represented by formula (52)) In addition, the polymer may contain Ar in the repeating unit represented by the above formula (54). 51 few At least one of them is preferably a group represented by the following formula (52): In the two carbazole structures in formula (52), an aromatic hydrocarbon group is Alternatively, the LUMO distribution in the aromatic heterocyclic group may affect the main chain amine in formula (54). This is thought to be because the effect of the main chain amine is improved by suppressing the noise and improving the durability of the main chain amine against electrons and excitons.

[0301] [ka]

[0302] (In formula (52), Ar 61 and Ar 62 each independently has a substituent other than a crosslinking group. a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group which may have a substituent other than a bridging group; and Ar 63 ~Ar 65 are each independently a hydrogen atom or a substituent. * indicates the bonding position to the nitrogen atom in formula (54).

[0303] (Ar 63 ~Ar 65 ) Ar 63 ~Ar 65 Each of Ar independently represents a hydrogen atom or a substituent. 63 ~A r 65 When is a substituent, the substituent is not particularly limited, but is preferably a substituent other than a crosslinking group. an aromatic hydrocarbon group which may have a substituent or an aromatic hydrocarbon group which may have a substituent other than a bridging group; The aromatic hydrocarbon group and the aromatic heterocyclic group are preferably is the Ar 51 The groups are the same as those listed above.

[0304] Ar 63 ~Ar 65 is a substituent, Ar 63 ~Ar 65 is the structure of each carbazole From the viewpoint of improving durability, it is preferable that the bond be at the 3-position or the 6-position. Ar 63 ~Ar 65 From the viewpoint of ease of synthesis and charge transport properties, it is preferable that the It is preferable that: Ar 63 ~Ar 65 From the viewpoint of improving durability and charge transportability, It is preferably an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent. It is more preferable that the alkyl group is an aromatic hydrocarbon group which may have a substituent.

[0305] Ar 63 ~Ar 65 an aromatic hydrocarbon group which may have a substituent or In the case of an aromatic heterocyclic group, the substituents which may be present include those exemplified in the following substituent group Z2. The same applies to the substituents, and the same applies to the preferred substituents. The same is true for good substituents.

[0306] (Ar 62 ) Ar 62 is a divalent aromatic hydrocarbon group which may have a substituent or a divalent aromatic hydrocarbon group which has a substituent. It is a divalent aromatic heterocyclic group which may be The aromatic hydrocarbon group preferably has 6 to 60 carbon atoms, more preferably 1 to 20 carbon atoms. The carbon number is preferably from 10 to 50, and more preferably from 12 to 40. Specific examples of the hydrogen hydride group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthane ring, and the like. Thylene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triflate ring six-membered monocyclic or monocyclic rings such as phenylene ring, acenaphthene ring, fluoranthene ring, and fluorene ring; Examples of such groups include divalent groups having 2 to 5 condensed rings and groups in which multiple such groups are linked together. In the case of conjugation, the group is preferably a group in which a plurality of linked divalent aromatic hydrocarbon groups are conjugated.

[0307] The aromatic heterocyclic group preferably has 3 to 60 carbon atoms, and specifically, a furan ring , benzofuran ring, thiophene ring, benzothiophene ring, pyrrole ring, pyrazole ring, Midazole ring, oxadiazole ring, indole ring, carbazole ring, pyrrolyl midazo pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring , furopyrrole ring, furofuran ring, thienofuran ring, benzisoxazole ring, benzo Isothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, pyridazine ring, Imidine ring, triazine ring, quinoline ring, isoquinoline ring, cinnoline ring, quinoxaline ring, phenanthridine ring, benzimidazole ring, perimidine ring, quinazoline ring, quinazo a divalent group of a 5- or 6-membered monocyclic ring or 2- to 4-condensed ring such as a linone ring or an azulene ring, or and groups in which a plurality of these are linked together.

[0308] The substituents that these aromatic hydrocarbon groups or aromatic heterocyclic groups may have are as follows: Examples of the alkyl group, aralkyl group and aromatic hydrocarbon group of group Z2 are as follows. By the results Ar 62 In the case where the structure of the compound is twisted, it is preferable that the compound has no substituents. Due to the steric effect of Ar 62 If the structure of the compound does not become distorted, it is preferable that the compound has a substituent. I wish.

[0309] Ar 62 Preferred groups are a benzene ring, a naphthalene ring, an anthracene ring, and a fluorene ring. or a group in which a plurality of these are linked together, and more preferably a divalent group of a benzene ring Or a group in which a plurality of such rings are linked, and particularly preferably a group in which the benzene rings are linked divalently at the 1- and 4-positions 1,4-phenylene group connected by divalent bonds at the 2- and 7-positions of the fluorene ring; 2,7-fluorene group connected by divalent bonds at the 2- and 7-positions of the fluorene ring; A phenylene group or a group in which a plurality of such groups are linked together is most preferred, and "1,4-phenylene" is the most preferred. It is a group containing the group -2,7-fluorenylene group-1,4-phenylene group-”.

[0310] In these preferred structures, the phenylene group does not have a substituent other than at the linking position. , Ar due to the steric effect of the substituents 62 In addition, the fluorenylene group is preferably In terms of improving the solubility and durability of the fluorene structure, it is preferable to have substituents at the 9 and 9' positions. It is preferable from this point of view.

[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 represents a divalent aromatic hydrocarbon group or a bridging group which may have a substituent other than a bridging group. is a divalent aromatic heterocyclic group which may have a substituent other than Ar 61 The aromatic hydrocarbon group preferably has 6 or more and 60 or less carbon atoms, and more preferably Preferably, the number of carbon atoms is 10 or more and 50 or less, and particularly preferably 12 or more and 40 or less. Specific examples of the aromatic hydrocarbon group include a benzene ring, a naphthalene ring, an anthracene ring, and ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring six-membered rings such as phenylene ring, triphenylene ring, acenaphthene ring, fluoranthene ring, and fluorene ring; Examples thereof include a divalent group of a single ring or 2 to 5 condensed rings, or a group in which a plurality of these are linked together.

[0312] Ar 61 The aromatic heterocyclic group preferably has 3 to 60 carbon atoms. Furan ring, benzofuran ring, thiophene ring, benzothiophene ring, pyrrole ring, pyrazo ring, imidazole ring, oxadiazole ring, indole ring, carbazole ring, pyrrolidine ring, Midazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienthio Phen 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, quinoline ring Xaline ring, phenanthridine ring, benzimidazole ring, perimidine ring, quinazoline ring a divalent ring having a 5- or 6-membered monocyclic ring or 2 to 4 condensed rings, such as a quinazolinone ring or an azulene ring; groups or groups in which a plurality of such groups are linked together.

[0313] The substituents that these aromatic hydrocarbon groups or aromatic heterocyclic groups may have are as follows: Examples of the group Z2 include alkyl groups, aralkyl groups and aromatic hydrocarbon groups. When a plurality of these divalent aromatic hydrocarbon groups or divalent aromatic heterocyclic groups are linked together, it is preferable that Or, it is a group in which multiple linked divalent aromatic hydrocarbon groups are bonded so as not to conjugate. The 1,3-phenylene group or the substituent group have a twisted structure due to the steric effect of the substituent. It is preferred that the group contains:

[0314] (Group represented by formula (53)) Ar in the repeating unit represented by the formula (54) 51 At least one of the following formula A group represented by (53) is also preferred.

[0315] [ka]

[0316] (In formula (53), * represents a bond to the nitrogen atom of the main chain of formula (54), Ar 71 represents a divalent aromatic hydrocarbon group which may have a substituent, Ar 72 and Ar 73 each independently represents an aromatic hydrocarbon which may have a substituent. group, an aromatic heterocyclic group which may have a substituent, or an aromatic and two or more groups selected from an aromatic hydrocarbon group and an aromatic heterocyclic group which may have a substituent are directly bonded to each other. represents a monovalent group in which a plurality of groups are linked together via a bond or 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 Less When either of them is a carbon atom, the carbon atom may have a substituent.

[0317] <Ar 71 > Ar 71 is the Ar 53 is a group similar to Ar 71 is one divalent aromatic hydrocarbon group which may have a substituent, or A group in which 2 to 10 divalent aromatic hydrocarbon groups are linked together, which may have the following substituents, is preferred. one divalent aromatic hydrocarbon group optionally having one substituent, or A group in which 2 to 8 aromatic hydrocarbon groups are linked is more preferred, and among these, a group in which 2 It is preferable that the aromatic hydrocarbon group is a group in which two or more aromatic hydrocarbon groups are linked together.

[0318] Ar 71 As the group, particularly, a group in which 2 to 6 benzene rings which may have a substituent are linked is is preferred, and a quaterphenylene group in which four benzene rings which may have substituents are linked together. is most preferred. Also, Ar 71 contains at least one benzene ring linked at the 1- and 3-positions, which is a non-conjugated moiety. It is preferable that the number of the hydroxyl groups included in the total number of the hydroxyl groups is 1 or more, and more preferable that the number of the hydroxyl groups included in the total number of the hydroxyl groups is 2 or more.

[0319] Ar 71 is a group in which a plurality of optionally substituted divalent aromatic hydrocarbon groups are linked together. From the viewpoint of charge transportability or durability, it is preferable that all of the groups are directly bonded to each other. For this reason, Ar 71 as the nitrogen atom of the main chain of the polymer and the ring HA in the formula (53) Preferred structures for connecting the two are shown in Scheme 2-1 and Scheme 2-2 below. "-*" indicates the bonding site with the nitrogen atom of the main chain of the polymer or the ring HA of the formula (53). Whichever of the two "-*" is bonded to the nitrogen atom of the polymer main chain, the ring H It may be bonded to A.

[0320] [ka]

[0321] [ka]

[0322] Ar 71 The substituents which may be possessed by the group Z2 below or A combination of Ar 71 Preferred range of substituents that may be possessed by is the same as the substituent that may be possessed when G is an aromatic hydrocarbon group.

[0323] <X 2 and Y 2 > X 2 and Y 2 each independently represents a C (carbon) atom or an N (nitrogen) atom. 2 Reach BiY 2 When at least one of them is a C atom, it may have a substituent. X is chosen to localize the LUMO more easily around the HA ring. 2 and Y 2 All of them are Nhara Preferably a child. X 2 and Y 2 When at least one of the groups is a C atom, the following substituents may be present: Any one of the above substituent groups Z2 or a combination thereof can be used. From the perspective of X 2 and Y 2 More preferably, has no substituent.

[0324] <Ar 72 and Ar 73 > Ar 72 and Ar 73 each independently represents an aromatic hydrocarbon which may have a substituent. group, an aromatic heterocyclic group which may have a substituent, or an aromatic and two or more groups selected from an aromatic hydrocarbon group and an aromatic heterocyclic group which may have a substituent are directly bonded to each other. It is a monovalent group in which multiple groups are linked together via a bond or linking group.

[0325] From the viewpoint of distributing the LUMO of the molecule, Ar 72 and Ar 73 are each independently a-1 to a-4, b-1 to b-9, c-1 to c-4, d-1 to d-1 shown in Scheme 2 It is preferable that the structure has a structure selected from e-6, and e-1 to e-4. Furthermore, the presence of electron-withdrawing groups promotes the broadening of the LUMO of the molecule. , a-1~a-4, b-1~b-9, c-1~c-5, d-1~d-12, and e-1~ The structure selected from e-4 is preferred.

[0326] Furthermore, from the viewpoint of the effect of trapping excitons formed in the light-emitting layer, which has a high triplet level, A structure selected from -1 to a-4, d-1 to d-12, and e-1 to e-4 is preferred. In order to prevent aggregation of molecules, a structure selected from d-1 to d-12 and e-1 to e-4 is Ar is more preferred from the viewpoint of easy synthesis and excellent stability. 72 =Ar 73 =d-1 again is preferably d-10, and the benzene ring structure of d-1 is particularly preferred.

[0327] These structures may also have a substituent. "-*" indicates the binding site to the ring HA. When there are multiple "-*", any one of them represents the site that binds to the ring HA. Ar 72 and Ar 73 The substituent that may be possessed by the group Z2 is any one of the following substituent groups: From the viewpoint of durability and charge transportability, It is a substituent, and the same groups as those in the following substituent group Z2 are preferred.

[0328] (X) X in the above formula (54) is -C(R 207 ) (R 208 )- or -N(R 209 )-, and -C(R 207 )(R 2 08 )- is more preferred. In addition, in the polymer containing the repeating unit represented by the above formula (54), Ar 51 , R 2 01 , R 202 , R 221 , R 222 If there are multiple Xs, they may be the same or different. Preferably, the repeating units of the polymer represented by formula (54) have the same structure. In this case, the polymer contains multiple repeating units of the same structure. By including multiple repeating units, the HOMO and LUMO of the repeating units become the same, so that a specific shallow quasi- It is believed that charges do not concentrate at the positions to form traps, and that the charge transport properties are excellent.

[0329] (Preferred repeating unit) The repeating unit represented by the above formula (54) is any one of the following formulae (54-1) to (54-4): The repeating unit represented by any one of the following is particularly preferred.

[0330] [ka]

[0331] In the above formula, R 201 and R 202 are identical and R 201 and R 202 Mutually The bonds are symmetrical.

[0332] [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 may be, for example, the following: Examples of such structures include:

[0333] [ka]

[0334] [ka]

[0335] [ka]

[0336] [ka]

[0337] [ka]

[0338] [ka]

[0339] [ka]

[0340] [ka]

[0341] [Content of repeating unit represented by formula (54)] The polymer contained in the second organic layer has a repeating unit represented by formula (54): In this case, the content of the repeating unit represented by formula (54) is not particularly limited. The repeating unit represented by the formula (I) is usually contained in the polymer at 10 mol % or more, and more preferably at 30 mol % or more. It is preferable that the content is 40 mol % or more, more preferably 50 mol % or more. It is even more preferable that:

[0342] When the polymer contained in the second organic layer has a repeating unit represented by formula (54), The repeating unit may be composed only of the repeating unit represented by formula (54), but In order to balance the various performances of the electroluminescent device, the repeating In this case, the polymer may have a repeating unit other than the repeating unit of formula (54) The content of the repeating unit represented by the formula (I) is usually 99 mol % or less, preferably 95 mol % or less. is.

[0343] [Terminal group] In this specification, the term "terminal group" refers to a group formed by an end-capping agent used at the end of polymerization of the polymer. In the second organic layer, the structure of the polymer terminal formed by the formula (54) The terminal group of the polymer containing the repeating unit represented by the formula (I) is preferably a hydrocarbon group. From the viewpoint of charge transportability, the hydrogen group preferably has 1 to 60 carbon atoms, and more preferably has 1 to 40 carbon atoms. More preferably, it is 1 or more and 30 or less.

[0344] Examples of the hydrocarbon group include: Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, iso- Butyl group, sec-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group , dodecyl group, etc., usually have 1 or more carbon atoms, preferably 4 or more carbon atoms, and usually 24 or less carbon atoms. a linear, branched, or cyclic alkyl group, preferably having 12 or less alkyl groups; The number of carbon atoms of the vinyl group or the like is usually 2 or more and usually 24 or less, preferably 12 or less. a linear, branched, or cyclic alkenyl group, The number of carbon atoms, such as an ethynyl group, is usually 2 or more and usually 24 or less, preferably 12 or less. a straight or branched alkynyl group; The carbon number of a phenyl group, a naphthyl group, etc. is usually 6 or more and usually 36 or less, and is preferably and aromatic hydrocarbon groups having 24 or less carbon atoms.

[0345] These hydrocarbon groups may further have a substituent. is preferably an alkyl group or an aromatic hydrocarbon group. When there are a plurality of such groups, they may be bonded to each other to form a ring. The terminal group is preferably an alkyl group or an aromatic carbon group from the viewpoint of charge transportability and durability. It is preferably a hydrogen group, and more preferably an aromatic hydrocarbon group. <Repeating unit represented by formula (55)>

[0346] [ka]

[0347] (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; is a methyl group, R 304 and R 305 each independently represents an alkyl group which may have a substituent other than a crosslinking group; an alkyl group, an alkoxy group which may have a substituent other than a crosslinking group, or an alkoxy group which may have a substituent other than a crosslinking group an aralkyl group which may be present, l, n, p, and q each independently represent 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.) (R 303 , R 306 ) R in the repeating unit represented by the above formula (55) 303 and R 306 are independent of each other. and is an alkyl group which may have a substituent other than a crosslinking group.

[0348] The alkyl group is R in the formula (54). 201 and R 202 Similar things are listed The substituents that may be present and the preferred structures are also shown in R 201 and R 202 and similar Examples include: 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.

[0349] (R 304 , R 305 ) R in the repeating unit represented by the above formula (55) 304 and R 305 are independent of each other. alkyl groups which may have a substituent other than a crosslinking group; and an aralkyl group which may have a substituent other than an alkoxy group which may have a substituent or a bridging group. Preferably, it is an alkyl group which may have a substituent other than the crosslinking group.

[0350] R 304 and R 304 are preferably the same. The alkyl group may be a straight-chain, branched, or cyclic alkyl group. There is no particular limitation on the number of carbon atoms in the alkyl group. However, it is preferable that the number is 1 or more because the solubility of the polymer tends to be improved. 24 or less is preferable, 8 or less is more preferable, and 6 or less is even more preferable. Specifically, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group group, iso-butyl group, sec-butyl group, tert-butyl group, n-hexyl group, n- Examples include an octyl group, a cyclohexyl group, and a dodecyl group.

[0351] The alkoxy group is not particularly limited, and may be an alkoxy group (-OR 10 )R 10 The group may be linear or branched. or cyclic structure, which tends to improve the solubility of the polymer, The number of carbon atoms is preferably 1 or more, and is preferably 24 or less, and more preferably 12 or less. Specifically, methoxy, ethoxy, n-propoxy, n-butoxy, hexyl Examples of the alkoxy group include an oxy group, a 1-methylpentyloxy group, and a cyclohexyloxy group.

[0352] The aralkyl group is not particularly limited, but carbon is preferred because it tends to improve the solubility of the polymer. A prime number of 5 or greater is preferable, and a prime number of 60 or less is preferable, and a prime number of 40 or less is more preferable. Specifically, 1,1-dimethyl-1-phenylmethyl group, 1,1-di(n-butyl)- 1-phenylmethyl group, 1,1-di(n-hexyl)-1-phenylmethyl group, 1,1- Di(n-octyl)-1-phenylmethyl group, phenylmethyl group, phenylethyl group, 3 -phenyl-1-propyl group, 4-phenyl-1-n-butyl group, 1-methyl-1-phenyl phenylethyl group, 5-phenyl-1-n-propyl group, 6-phenyl-1-n-hexyl group , 6-naphthyl-1-n-hexyl group, 7-phenyl-1-n-heptyl group, 8-phenyl Examples include a phenyl-1-n-octyl group and a 4-phenylcyclohexyl group.

[0353] (l, m and n) l represents 0 or 1, and n represents 0 or 1. l and n are each independent, and l+n is preferably 1 or more, more preferably 1 or 2, and 2 When l+n is in the above range, the solubility of the polymer contained in the second organic layer is improved. The polymer has a tendency to have high solubility and to suppress deposition from a composition for organic electroluminescent devices containing the polymer. It's in the direction. m represents 1 or 2, and the organic electroluminescent device of the present invention can be driven at a low voltage and has hole injection and transport properties. It is preferable that the ratio is 1 because this tends to improve the performance and durability.

[0354] (p and q) p represents 0 or 1, and q represents 0 or 1. When l=n=1, p and q are both 0. When p and q are not 0 at the same time, the solubility of the polymer contained in the second organic layer is improved. This tends to increase the decomposition property of the polymer, and also tends to suppress precipitation from the second composition containing the polymer. In addition, if p+q is 1 or more, the aromatic rings in the main chain are twisted due to steric hindrance, making it difficult for the polymer to dissolve in a solvent. The coating film formed by the wet film-forming method and heat-treated has excellent insolubility in solvents. Therefore, if p+q is 1 or more, it is possible to form another organic film on this coating film by a wet film forming method. When forming a layer (for example, a light-emitting layer), the organic layer is formed by the organic solvent-containing composition for forming the other organic layer. The elution of the polymer is suppressed.

[0355] (Ar 51 ) In the repeating unit represented by the above formula (55), Ar 51 is the value in the above equation (54). RuAr 51 and the aromatic hydrocarbon group, which may have a substituent other than the crosslinking group, Aromatic heterocyclic groups which may have a substituent other than a bridging group, or aromatic heterocyclic groups which have a substituent other than a bridging group 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; is a group in which a plurality of groups selected from the following are linked together.

[0356] Aromatic hydrocarbon groups which may have a substituent other than a crosslinking group, an aromatic heterocyclic group which may have a substituent other than a bridging group, or an aromatic hydrocarbon which may have a substituent other than a bridging group; a plurality of groups selected from aromatic heterocyclic groups which may have a substituent other than a bridging group and a bridging group; The group to which is linked includes Ar in the formula (54). 51 The same as in the case of The substituents other than the bridging group and the preferred structure are also defined in the Ar 51 As in the case of Examples include:

[0357] [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 For example, the following structure can be given:

[0358] [ka]

[0359] [ka]

[0360] [ka]

[0361] [ka]

[0362] [ka]

[0363] [ka]

[0364] [ka]

[0365] [ka]

[0366] [Content of repeating unit represented by formula (55)] The polymer contained in the second organic layer has a repeating unit represented by formula (55): In this case, the content of the repeating unit represented by formula (55) is not particularly limited. The repeating unit represented by the formula (I) is usually contained in the polymer at 10 mol % or more, and more preferably at 30 mol % or more. It is preferable that the content is 40 mol % or more, more preferably 50 mol % or more. It is particularly preferred that the

[0367] When the polymer contained in the second organic layer has a repeating unit represented by formula (55), The repeating unit may be composed only of the repeating unit represented by formula (55), In order to balance the various performances when used as an organic electroluminescent device, In this case, the repeating unit of the formula (55) in the polymer may be different from the repeating unit of the formula (55) The content of the repeating unit represented by the formula (I) is usually 99 mol % or less, preferably 95 mol % or less. Below.

[0368] [Terminal group] The polymer contained in the second organic layer is a polymer containing a repeating unit represented by formula (55): The terminal group of the polymer is the same as the terminal group of the polymer containing the repeating unit represented by the above formula (54). The preferred hydrocarbon groups and the substituents they may have are also described above. It is the same as the terminal group of the polymer containing the repeating unit represented by formula (54). <Repeating unit represented by formula (56)>

[0369] [ka]

[0370] (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 bridging group a divalent aromatic heterocyclic group which may have a substituent other than and the divalent aromatic heterocyclic group, is a divalent group linked via a group, R 441 and R 442 each independently represents an alkyl group which may have a substituent other than a crosslinking group; is a methyl group, t is 1 or 2; u is 0 or 1; r and s each independently represent an integer of 0 to 4, r+s is greater than or equal to 1, However, if s is 1 or greater, then u is 1.)

[0371] (R 441 , R 442 ) R in the repeating unit represented by the above formula (56) 441 , R 442 are each independently and an alkyl group which may have a substituent other than a crosslinking group. 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 alkyl group should have 1 or more carbon atoms. Preferably, the number is 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. 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.

[0372] (r, s, t and u) In the repeating unit represented by formula (56), r and s each independently represent 0 to 4. and r+s is 1 or more. If t is 2 or more, multiple r's can be the same but different. When u is 2 or more, the plural s's may be the same or different. It is preferable that each of r+s is 2 or less. When r+s is 1 or more, the driving The dynamic life is expected to be even longer. 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.

[0373] (Ar 51 ) In the repeating unit represented by the above formula (56), Ar 51 is the above formula (54) or the above Ar in formula (55) 51 and the aromatic group may have a substituent other than the crosslinking group. aromatic hydrocarbon group, aromatic heterocyclic group which may have a substituent other than a bridging group, or The aromatic hydrocarbon group may have other substituents than the bridging group. It is a group in which a plurality of groups selected from aromatic heterocyclic groups are linked together. Aromatic hydrocarbon groups which may have a substituent other than a bridging group or aromatic hydrocarbon groups which have a substituent other than a bridging group The aromatic heterocyclic group which may be present is Ar in the formula (54). 51 As in the case of The substituents other than the bridging group and the preferred structure are also the same as those of Ar 51 The same as in the case of

[0374] (Ar 41 ) Ar 41 represents a divalent aromatic hydrocarbon group which may have a substituent other than a bridging group, a bridging group a divalent aromatic heterocyclic group which may have a substituent other than and at least one group selected from the group consisting of the divalent aromatic heterocyclic group Alternatively, it is a divalent group in which a plurality of groups are linked via a linking group.

[0375] Ar 41 The aromatic hydrocarbon group and the aromatic hydrocarbon group in the formula (54) are Ar 52 In addition, aromatic hydrocarbon groups and aromatic hydrocarbon groups The substituents which may be possessed by the group Z2 are preferably the same as those in the group Z2 of substituents below. The substituents that may be used are preferably the same as those in the following group Z2 of substituents.

[0376] [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.

[0377] [ka]

[0378] [Content of repeating unit represented by formula (56)] The polymer contained in the second organic layer has a repeating unit represented by formula (56): In this case, the content of the repeating unit represented by formula (56) is not particularly limited. The repeating unit represented by the formula (I) is usually contained in the polymer at 10 mol % or more, and more preferably at 30 mol % or more. It is preferable that the content is 40 mol % or more, more preferably 50 mol % or more. It is particularly preferred that the

[0379] When the polymer contained in the second organic layer has a repeating unit represented by formula (56), The repeating unit may be composed only of the repeating unit represented by formula (56), In order to balance the various performances when used as an organic electroluminescent device, In this case, the repeating unit of the formula (56) in the polymer may be different from the repeating unit of the formula (56) The content of the repeating unit represented by the formula (I) is usually 99 mol % or less, preferably 95 mol % or less. Below.

[0380] [Terminal group] The polymer contained in the second organic layer is a polymer containing a repeating unit represented by formula (56): The terminal group of the polymer is the same as the terminal group of the polymer containing the repeating unit represented by the above formula (54). The preferred hydrocarbon groups and the substituents they may have are also described above. It is the same as the terminal group of the polymer containing the repeating unit represented by formula (54). <Repeating unit represented by formula (57)>

[0381] [ka]

[0382] (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 bridging group; a group, an alkoxy 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 bridging group, an aromatic hydrocarbon group which may have a substituent other than a bridging group, represents an aromatic heterocyclic group which may have a substituent other than a bridging group, f, g, and h each independently represent an integer of 0 to 4, f+g+h is greater than or equal to 1, e is an integer from 0 to 3, However, if g is 1 or greater, e is 1 or greater.)

[0383] (R 517 ~R 519 ) R 517 ~R 519 The aromatic hydrocarbon group and aromatic heterocyclic group in Ar 51 The substituents which these groups may have are the same as those listed in The same groups as those in the following substituent group Z2 are preferred. R 517 ~R 519 The alkyl group and aralkyl group in the R 207 The ones mentioned in The same groups as those in R are preferred, and the substituents that may be further substituted are also the same as those in R 207 A group similar to I wish. R 517 ~R 519 The alkoxy group in the formula (I) is an alkoxy group listed in the following substituent group Z2. The substituents which may further be possessed are the same as those in the following group Z2 of substituents.

[0384] (f, g, h) f, g, and h each independently represent an integer of 0 to 4, and f+g+h is 1 or more. When e is 2 or more, multiple g's may be the same or different.

[0385] (e) e represents an integer of 0 to 3, and when g is 1 or more, e is 1 or more. e=2 is preferred, and it is also preferred that e=1 or 3, but more preferred that e=2.

[0386] The repeating unit represented by the formula (57) may be a repeating unit represented by the following formula (58): It is preferable that the unit is a unit. <Repeating unit represented by formula (58)>

[0387] [ka]

[0388] (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 are the same. .) 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.

[0389] In addition, in the repeating unit represented by the formula (58), e=2 and g=1. When e=2 and g=1, there are two R 518 are located symmetrically to each other Preferably, they are bonded. Also, there are two R 518 are preferably the same. Here, there are two R 518 are bonded at symmetric positions to each other, the following bond positions However, for the purposes of notation, a 180-degree rotation around the main chain is considered to be the same structure.

[0390] [ka]

[0391] (In the above formula, Ar 51 is Ar in the formula (54). 51 is similar to R 517 ~R 519 ,f, h is R in the formula (57) 517 ~R 519 , f, h.) In the repeating unit represented by the formula (58), when e=1 or 3, 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. When f and h are both 1, R 517 and R 519 are bonded at symmetric positions to each other It is preferable that Also, R 517 and R 519 are preferably the same as where R 517 and R 519 are bonded at positions symmetric to each other, the following bond positions are However, for the purposes of notation, a 180-degree rotation around the main chain is considered to be the same structure.

[0392] [ka]

[0393] (In the above formula, Ar 51 is Ar in the formula (54). 51 is similar to R 517 ~R 519 ,e, g is R in the formula (57) 517 ~R 519 , e, g.) 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 the para position. , If g is 2, then two R 518 It is more preferred that are the same.

[0394] In addition, in the repeating unit represented by the formula (58), e=1 or 3, and g Preferably, g is 0 or 2. When g=2, the bonding positions are the 2nd and 5th positions. In the case of R 518 If there is no steric hindrance due to g=2, the bond position is 2-position. and 5-position, i.e., steric hindrance occurs between the two R 518 Diagonal position of the benzene ring to which If so, R 517 and R 519 and can be bonded at positions symmetrical to each other.

[0395] <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 For example, the following structure can be given:

[0396] [ka]

[0397] [Content of repeating unit represented by formula (57)] The polymer contained in the second organic layer has a repeating unit represented by formula (57): In this case, the content of the repeating unit represented by formula (57) is not particularly limited. The repeating unit represented by the formula (I) is usually contained in the polymer at 10 mol % or more, and more preferably at 30 mol % or more. It is preferable that the content is 40 mol % or more, more preferably 50 mol % or more. It is particularly preferred that the

[0398] When the polymer contained in the second organic layer has a repeating unit represented by formula (57), The repeating unit may be composed only of the repeating unit represented by formula (57), In order to balance the various performances when used as an organic electroluminescent device, In this case, the repeating unit of the formula (57) in the polymer may be different from the repeating unit of the formula (57). The content of the repeating unit represented by the formula (I) is usually 99 mol % or less, preferably 95 mol % or less. Below.

[0399] [Terminal group] The polymer contained in the second organic layer is a polymer containing a repeating unit represented by formula (57): The terminal group of the polymer is the same as the terminal group of the polymer containing the repeating unit represented by the above formula (54). The preferred hydrocarbon groups and the substituents they may have are also described above. It is the same as the terminal group of the polymer containing the repeating unit represented by formula (54).

[0400] <Substituent group Z2> The substituent group Z2 is an alkyl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, a silyl group, an alkoxycarbonyl group, a dialkylamino group, a diarylamino group, an arylamino group, alkylamino group, acyl group, halogen atom, haloalkyl group, alkylthio group, aryl Thio group, silyl group, siloxy group, cyano group, aromatic hydrocarbon group, and aromatic heterocyclic group These substituents may include any of straight-chain, branched, and cyclic structures. .

[0401] More specifically, the substituent group Z2 includes the following structures. For example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group The carbon number of the hydroxyl group, dodecyl group, etc. is 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 or a linear, branched, or cyclic alkyl group having 6 or less carbon atoms;

[0402] For example, the number of carbon atoms of a methoxy group, an ethoxy group, etc. is usually 1 or more and usually 24 or less. alkoxy groups, preferably 12 or less; For example, phenoxy group, naphthoxy group, pyridyloxy group, etc., which usually have 4 or more carbon atoms, Preferably, the number is 5 or more, usually 36 or less, preferably 24 or less. an aryloxy group or a heteroaryloxy group;

[0403] For example, a methoxycarbonyl group, an ethoxycarbonyl group, or the like, usually has two or more carbon atoms. alkoxycarbonyl groups, typically 24 or less, preferably 12 or less; For example, a dimethylamino group, a diethylamino group, etc., usually has two or more carbon atoms, dialkylamino groups having 24 or less, preferably 12 or less; For example, the number of carbon atoms is usually 10 or more, such as a diphenylamino group or a ditolylamino group, Preferably, it is 12 or more, usually 36 or less, preferably 24 or less diaryl amines. Noki;

[0404] For example, the number of carbon atoms is usually 7 or more and usually 36 or less, such as a phenylmethylamino group. an arylalkylamino group, preferably having a molecular weight of 24 or less; For example, acetyl groups, benzoyl groups, etc., usually have 2 or more carbon atoms and usually have 24 or less carbon atoms. acyl groups, preferably 12 or less; For example, halogen atoms such as fluorine atoms and chlorine atoms;

[0405] For example, the number of carbon atoms is usually 1 or more and usually 12 or less, such as a trifluoromethyl group. haloalkyl groups, preferably 6 or less; For example, a methylthio group, an ethylthio group, etc., usually has 1 or more carbon atoms and usually has 24 or less carbon atoms. an alkylthio group, preferably having 12 or less carbon atoms; For example, a phenylthio group, a naphthylthio group, a pyridylthio group, etc., which usually have 4 or more carbon atoms and preferably 5 or more, usually 36 or less, preferably 24 or less. thio group;

[0406] For example, a trimethylsilyl group, a triphenylsilyl group, etc., which usually has two or more carbon atoms silyl groups, preferably 3 or more and usually 36 or less, preferably 24 or less; For example, trimethylsiloxy groups, triphenylsiloxy groups, and other groups usually having two or more carbon atoms Preferably, the number of silyl groups is 3 or more, and usually 36 or less, preferably 24 or less. Si group;

[0407] cyano group; For example, the number of carbon atoms is usually 6 or more and usually 36 or less, such as a phenyl group and a naphthyl group. an aromatic hydrocarbon group, preferably having 24 or less aromatic hydrocarbon groups; For example, a thienyl group, a pyridyl group, etc., usually have 3 or more carbon atoms, preferably 4 or more carbon atoms. and the aromatic heterocyclic group has a ring structure of usually 36 or less, preferably 24 or less.

[0408] Among the above-mentioned substituent group Z2, alkyl groups, alkoxy groups, diaryla groups, From the viewpoint of charge transport properties, the substituted group is an amino group, an aromatic hydrocarbon group, or an aromatic heterocyclic group. The group is preferably an aromatic hydrocarbon group or an aromatic heterocyclic group, more preferably an aromatic hydrocarbon group. It is more preferable that the group is a hydrogen group and has no substituents. The group is preferably an alkyl group or an alkoxy group.

[0409] Each of the substituents in the above-mentioned substituent group Z2 may further have a substituent. The substituents include the same as those in the above-mentioned substituent group Z2. Each of the substituents that may be possessed is preferably an alkyl group having 8 or less carbon atoms, ... or an alkyl group having 8 or less carbon atoms. a koxy group or a phenyl group, more preferably an alkyl group having 6 or less carbon atoms, The substituents in the above-mentioned substituent group Z2 are an alkoxy group or a phenyl group, and each of the substituents in the above-mentioned substituent group Z2 is selected from the viewpoint of charge transport properties. From this point of view, it is more preferable that the aryl group has no further substituents.

[0410] [Bridging group] The repeating units represented by any of formulas (54) to (58) do not contain a crosslinking group. If the polymer does not contain a crosslinking group, it can be easily decomposed by drying or baking after wet film formation. This is preferable because it is difficult for the chain to become distorted. When the crosslinking group reacts, a change in volume may occur. This is because the distortion of the polymer chain occurs. This is because:

[0411] Here, the crosslinking group in this embodiment is a group that can be crosslinked by heat and / or irradiation with active energy rays. A group that reacts with another crosslinking group located in the vicinity of the crosslinking group to form a new chemical bond. In this case, the reactive group may be the same as or different from the crosslinking group. The crosslinking group may be a group containing an alkenyl group, a group containing a conjugated diene structure, or a group containing an alkynyl group. a group containing an oxirane structure, a group containing an oxetane structure, a group containing an aziridine structure, a group containing a maleic anhydride structure; a group containing an alkenyl group bonded to an aromatic ring; Specific examples of the bridging group include the following: Examples thereof include groups selected from the group T of bridging groups. (Bridging group T)

[0412] [ka]

[0413] [ka]

[0414] In the above-mentioned bridging group T, R XL represents a methylene group, an oxygen atom, or a sulfur atom; n X L represents an integer from 0 to 5. XL If there are multiple, they may be the same or different. Well, n XL If there are multiple, they may be the same or different. *1 is a bond These bridging groups may have a substituent.

[0415] [Preferred repeating units] The polymer contained in the second organic layer satisfies at least one of the following (i) and (ii). (i) A repeating unit represented by the formula (54) and a repeating unit represented by the formula (55) The repeating unit represented by the formula (56) and the repeating unit represented by the formula (57) Among them, it has two or more repeating units. (ii) a repeating unit represented by the formula (54) and a repeating unit represented by the formula (55) Position, repeating unit represented by the formula (56) and repeating unit represented by the formula (57) It consists of only one or more repeating units of the above.

[0416] The polymer contained in the second organic layer contains at least a repeating unit represented by the formula (54) It is preferable that the repeating unit represented by the formula (54) and the repeating unit represented by the formula (57) It is more preferable that the repeating unit has a repeating unit represented by the formula (54). It is more preferable that the repeating unit consists of only the repeating unit represented by the formula (57). The polymer contains a repeating unit represented by the following formula (54) and 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): When the compound has a repeating unit, it contains a partial structure represented by the following formula (61) or the following formula (61'): It is preferable that Among them, A compound represented by the formula (54) containing a partial structure represented by the following formula (61) or the following formula (61'): repeating units, A compound represented by the formula (55) containing a partial structure represented by the following formula (61) or the following formula (61'): repeating units, A compound represented by the formula (56) containing a partial structure represented by the following formula (61) or the following formula (61'): repeating units, or the formula (57) containing a partial structure represented by the following formula (61) or the following formula (61'): It is preferred that the repeating unit has the following structure:

[0417] [ka]

[0418] (In formula (61) and formula (61'), R 601 is R in Eq. (54) 201 or R 202 , R in Eq. (55) 303 , R 304 , R 305 , or R 406 , R in Eq. (56) 441 or R 442 ,formula( 57) in R 517 , R 518 or R 519 and -* represents a bond with the adjacent atom. .

[0419] Formula (61) and formula (61') are partial structures of formula (54) or formula (56), In this case, Ring B may be part of a fused ring. The partial structures represented by formula (61) and formula (61') are R 601 In addition to Ring A and and Ring B, when it is a partial structure of formula (54), R 201 or R 202 , formula (5 If it is a partial structure of 5), R 303 , R 304 , R 305 , or R 406 , equation (56) If it is a partial structure of 441 or R 442 , if it is a partial structure of formula (57), R 5 17 , R 518 or R 519 It may have.) The partial structure represented by the formula (61) or the formula (61') is formed by π conjugation. The approximately planar structure of Ring A and Ring B is called R 601 Distortion due to steric hindrance This results in a structure in which the main chain is more twisted than in the case of a normal π-conjugated bond.

[0420] (Repeating unit represented by formula (62)) The repeating unit contained in the polymer is particularly a repeating unit represented by formula (54): The repeating unit represented by the formula (54) is preferably a repeating unit represented by the following formula (62): Preferably, the unit is .

[0421] [ka]

[0422] (In formula (62), Ar 51 , X, R 201 , R 202 , R 221 , R 222 , a, b, c, and d are the same as those in the formula Ar in (54) 51 , X, R 201 , R 202 , R 221 , R 222 , a, b, c , d, and a 1 , a 2 , b 1 , b 2 , i 1 , i 2 , j 1 , j 2 are each independently 0 or 1.

[0423] 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.

[0424] (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 When c=1, it refers to a single bond, 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 However, when d=1, it refers to a single bond, Ring B5 is R 202 It refers to a divalent benzene ring which may have Here, a in formula (54) being 1 or more means that a 1 , a 2 and at least one of a is 1 or more, and b in formula (54) is 1 or more. The above means that in equation (62), b 1 , b 2 and at least one of b is 1 or greater This is synonymous with

[0425] As shown below, the formula (62) is a compound represented by the formula (61) or the formula (61') as a partial structure. include. 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, If a is 1 or more, in this case c is 2 or more, then Ring B2 and Ring B1 Or, Ring B2 and Ring B3 are represented by the formula (61) or the formula (61 ') as a substructure, Alternatively, when c is 3 or more and a is 1 or more, the ring B2 has the formula (61) or may contain the above formula (61') as a partial structure.

[0426] Similarly, b 1 , b 2 and b are each 1 or more. It can be seen that the formula (61') is included as a partial structure. 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 The ring to which and the benzene ring of Ring B2 or Ring B1, the partial structure is represented by the formula (61') formed, j 1 and j 2 If either or both of these are 1, then R in Ring B3 222 The ring to which and the benzene ring of Ring B4 or Ring B5, the partial structure of formula (61) is formed. It is clear that this will be achieved.

[0427] That is, Ring B3 and Ring B2 or Ring B1, or Ri It was found that Ring B3 and Ring B4 or Ring B5 have a twisted structure. do. Therefore, since formula (62) contains a twisted structure of the aromatic ring of the main chain, for the reasons mentioned above, This is preferable because it is easier to obtain a flatter film.

[0428] [Molecular weight of polymer] The molecular weight of the polymer contained in the second organic layer will be described below. The weight average molecular weight (M w) is usually 3,000,000 or less, preferably 1,000,000 or less, more preferably Preferably, the molecular weight is 500,000 or less, more preferably 200,000 or less, and particularly preferably 100 The weight average molecular weight is usually 2,500 or more, preferably 5,000 or less. ,000 or more, more preferably 10,000 or more, and even more preferably 15,000 or more, Particularly preferably, it is 17,000 or more.

[0429] When the weight average molecular weight of the polymer is equal to or less than the upper limit, solubility in a solvent is obtained. In addition, when the weight average molecular weight of the polymer is equal to or greater than the above lower limit, the film-forming property tends to be excellent. This prevents the polymer's glass transition temperature, melting point, and vaporization temperature from decreasing, improving heat resistance. There are cases where this happens. In addition, the number average in the polymer containing the repeating unit represented by formula (54) or formula (57) The molecular weight (Mn) is usually 2,500,000 or less, preferably 750,000 or less, more preferably It is 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. 000 or more, and more preferably 8,000 or more.

[0430] Furthermore, the dispersion in a polymer containing a repeating unit represented by formula (54) or formula (57) The molecular weight (Mw / Mn) is preferably 3.5 or less, more preferably 2.5 or less, and particularly preferably The lower the dispersity value, the better, so the lower limit is ideally 1. When the dispersity of the polymer is equal to or less than the upper limit, purification is easy and the polymer has good resistance to solvents. It has good solubility and charge transport ability.

[0431] The weight average molecular weight (M w) is preferably 10,000 or more, more preferably 15,000 or more, More preferably, the weight average molecular weight is 17,000 or more. ,000,000 or less, more preferably 1,000,000 or less, and particularly preferably Or less than 100,000.

[0432] By making the weight average molecular weight of the polymer equal to or less than the upper limit, the impurities are prevented from becoming high molecular weight. In addition, when the weight average molecular weight of the polymer is equal to or greater than the above lower limit, the polymer tends to be easily purified. This prevents the glass transition temperature, melting point, vaporization temperature, etc. from decreasing, improving heat resistance. This is a trend. Furthermore, the number average molecular weight of a polymer containing a repeating unit represented by formula (55) or formula (56) (Mn) is preferably 1,000,000 or less, more preferably 800,000 It is preferably 4,000 or less, and more preferably 500,000 or less. or more, more preferably 8,000 or more, and even more preferably 10,000 or more is.

[0433] Furthermore, the dispersity (M w / Mn) is preferably 3.5 or less, more preferably 3.0 or less, and Preferably it is 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 The dispersity of the polymer is the above upper limit or less, and more preferably 1.2 or more. This makes it easy to purify, and prevents the decrease in solubility in solvents and the decrease in charge transport ability. It tends to be suppressed.

[0434] Usually, the weight average molecular weight and number average molecular weight of a polymer are measured by SEC (size exclusion chromatography). In SEC measurements, the elution time is shorter for high molecular weight components, and The elution time is longer for the more abundant components, but it is the same as the elution time of polystyrene (standard sample) with known molecular weight. The weights were calculated by converting the elution time of the sample into molecular weight using a calibration curve calculated from the above. The weight average molecular weight and number average molecular weight are calculated.

[0435] [Specific example] Specific examples of the polymer containing the repeating unit represented by formula (54) are shown below. The polymers used are not limited to these. The numbers in the chemical formulas indicate the molar ratio of the repeating units. The ratio of the repeats is expressed as n. These polymers may be random copolymers, alternating copolymers, block copolymers, or graphene copolymers. The sequence of the monomers is not limited.

[0436] [ka]

[0437] [ka]

[0438] A polymer containing a repeating unit represented by formula (55) and a repeating unit represented by formula (55) Units of Ar 51 Specific examples of polymers having a structure represented by formula (52) are shown below. The polymers used in the present invention are not limited to these. represents the molar ratio of the unit, and n represents the number of repeating units. These polymers may be random copolymers, alternating copolymers, block copolymers, or graphene copolymers. The sequence of the monomers is not limited.

[0439] [ka]

[0440] [ka]

[0441] [ka]

[0442] [ka]

[0443] [ka]

[0444] [ka]

[0445] [ka]

[0446] Specific examples of the polymer containing the repeating unit represented by formula (56) are shown below. The polymers used are not limited to these. The numbers in the chemical formulas indicate the molar ratio of the repeating units. The ratio of the repeats is expressed as n. These polymers may be random copolymers, alternating copolymers, block copolymers, or graphene copolymers. The sequence of the monomers is not limited.

[0447] [ka]

[0448] [ka]

[0449] [ka]

[0450] [ka]

[0451] [Second Composition] The second composition that forms the second organic layer will now be described. The second composition contains the polymer and a solvent. This second composition is usually formed into a film by a wet process. It is used to form layers and films by the method, particularly for forming organic layers of organic electroluminescent devices. It is particularly preferable that the organic layer is a hole transport layer. The second composition may contain one of the above polymers, or may contain two or more of them. The above may be contained in any combination and in any ratio.

[0452] [Organic solvents] The second composition usually contains an organic solvent that dissolves the polymer. Specifically, the polymer is preferably added to the second composition at room temperature in an amount of usually 0.05% by mass. A solvent that dissolves 0.5% by mass or more, preferably 0.5% by mass or more, and more preferably 1% by mass or more is preferred. It is suitable.

[0453] Specific examples of organic solvents include toluene, xylene, mesitylene, and cyclohexylbenzene. Aromatic solvents such as methylnaphthalene, 1,2-dichloroethane, chlorobenzene, -Halogen-containing solvents such as dichlorobenzene; ethylene glycol dimethyl ether, ethylene Propylene glycol diethyl ether, propylene glycol-1-monomethyl ether acetate aliphatic ethers such as 1,2-dimethoxybenzene, 1,3-dimethacrylate (PGMEA); methoxybenzene, anisole, phenetole, 2-methoxytoluene, 3-methoxytoluene 4-Methoxytoluene, 2,3-Dimethylanisole, 2,4-Dimethylanisole Ether solvents such as aromatic ethers; ethyl acetate, n-butyl acetate, ethyl lactate, Aliphatic ester solvents such as n-butyl acetate; phenyl acetate, phenyl propionate, benzoin Methyl benzoate, Ethyl benzoate, Isopropyl benzoate, Propyl benzoate, n-Butyl benzoate organic solvents such as aromatic esters such as ethyl acetate; and other organic solvents, such as those for the hole injection layer described below. Examples of organic solvents include those used in the hole transport layer forming composition and the hole transport layer forming composition.

[0454] The solvent may be used alone or in any combination of two or more solvents in any ratio. may be used in combination. The content of the solvent in the second composition is usually 10% by mass or more, preferably 30% by mass or more, The content of the solvent is more preferably 50% by mass or more, and particularly preferably 80% by mass or more. By ensuring that the content is equal to or greater than the lower limit, the flatness and uniformity of the layer to be formed can be improved. Cut.

[0455] [Electron-accepting compounds] The second composition preferably further contains an electron-accepting compound in order to reduce the resistance. In particular, when the second composition is used to form a hole injection layer, the second composition Preferably, the photosensitive layer contains an electron-accepting compound. The electron-accepting compound has an oxidizing power and can accept one electron from the polymer contained in the second organic layer. Compounds having an electron affinity of 4 eV or more are preferred. Compounds having an electron affinity of 5 eV or more are preferred.

[0456] The second composition may contain only one of the electron-accepting compounds described above, or Any combination and ratio of two or more of these may be included. When the second composition contains an electron-accepting compound, the content of the electron-accepting compound in the second composition The content is usually 0.0005% by mass or more, preferably 0.001% by mass or more, and It is usually 20% by mass or less, preferably 10% by mass or less.

[0457] The ratio of the electron-accepting compound to the polymer in the second composition is usually 0.5% by mass. It is preferably 1% by mass or more, more preferably 3% by mass or more, and is usually 80% by mass or more. % by mass or less, preferably 60% by mass or less, and more preferably 40% by mass or less. When the content of the electron-accepting compound in the second composition is equal to or greater than the lower limit, electrons are released from the polymer. This is preferable because the acceptor accepts electrons and the resistance of the formed organic layer is reduced. When the content of the electron-accepting compound is equal to or less than the upper limit, defects are unlikely to occur in the formed organic layer, In addition, it is preferable because unevenness in the film thickness is unlikely to occur.

[0458] [Cation radical compounds] The second composition may further contain a cation radical compound. The cation radical compound is a chemical species obtained by removing one electron from a hole transport compound. Ionic compounds consisting of a cation radical and a counter anion are preferred. When the radical is derived from a hole-transporting polymer compound, the cation radical is The structure is one in which one electron is removed from the repeating unit.

[0459] In addition, the cation radical is a chemical compound obtained by removing one electron from a hole transport compound described later. It is preferable that the compound is a species obtained by removing one electron from a compound preferable as a hole transporting compound. The chemical species are preferable in terms of amorphousness, visible light transmittance, heat resistance, solubility, etc. be. Here, the cation radical compound is a compound containing a hole transporting compound described later and an electron accepting compound described above. It can be produced by mixing a hole transporting compound and an electron accepting compound. By mixing the compound, electrons are transferred from the hole transporting compound to the electron accepting compound. This occurs when the cation radical of the hole transport compound and the counter anion are ionized. A compound is produced.

[0460] When the second composition contains a cation radical compound, the cation radical of the composition for organic electroluminescent devices The content of the on-radical compound is usually 0.0005 mass % or more, preferably 0.001 mass % or more. % by mass or more, and is usually 40% by mass or less, preferably 20% by mass or less. When the content of the hydroxyl radical compound is equal to or greater than the lower limit, the resistance of the formed organic layer is reduced, which is preferable. Preferably, when the content is equal to or less than the upper limit, defects are unlikely to occur in the formed organic layer, and film thickness unevenness is unlikely to occur. It is preferable because it is spicy. In addition to the above components, the second composition may contain a composition for forming a hole injection layer and a hole transport layer, which will be described later. The components contained in the layer-forming composition may be contained in the amounts described below.

[0461] [Polymer manufacturing method] The method for producing the polymer contained in the second organic layer is not particularly limited and may be any method. For example, Polymerization method by Uzuki reaction, polymerization method by Grignard reaction, Yamamot Polymerization by the o reaction, polymerization by the Ullmann reaction, polymerization by the Buchwald-Harris reaction Examples include polymerization methods using the Twig reaction.

[0462] Polymerization by Ullmann reaction and Buchwald-Hartwig reaction In the case of the polymerization method, for example, an aryl dihalide represented by the following formula (2a) (Z is I, B represents a halogen atom such as r, Cl, or F, and a primary aminoaryl group represented by the following formula (2b): By reacting the compound with the repeating unit represented by formula (2), a polymer containing the repeating unit represented by formula (2) is synthesized. do.

[0463] [ka]

[0464] (In the above reaction scheme, Ar 1 , R 1 , R 2 , X and a to d are the same as in the formula (2). .) Also, polymerization methods using the Ullmann reaction and the Buchwald-Hartwig reaction In the case of the polymerization method according to the formula (3a), for example, an aryl dihalide represented by the formula (3a) (Z is I, represents a halogen atom such as Br, Cl, or F.) and a primary aminoaryl represented by formula (2b) By reacting with the above, a polymer containing a repeating unit represented by formula (3) is synthesized. .

[0465] [ka]

[0466] (In the above reaction scheme, Ar 2 , R 3 ~R 6 , l to n, p, and q are the same as in the formula (3). be.) In the above polymerization method, the reaction for forming an N-aryl bond is usually carried out by, for example, This is carried out in the presence of a base such as potassium tert-butoxide, 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.

[0467] [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. In 1, 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, 5 is a light emitting layer, and 6 is 7 represents an electron transport layer, and 7 represents a cathode. The compound of formula (2) is preferably contained in the light-emitting layer 5, and the compound of formula (2) is preferably a charge-transporting compound of the light-emitting layer 5. It is more preferable to use it as such.

[0468] <Structure of organic electroluminescent device> As an example of the structure of the organic electroluminescent device of the present invention, an example of the structure of the organic electroluminescent device 8 is shown in FIG. In Fig. 1, 1 is a substrate, 2 is an anode, 3 is a hole injection layer, and 4 is a hole 5 represents a light-emitting layer, 6 represents an electron-transporting layer, and 7 represents a cathode.

[0469] [substrate] The substrate 1 serves as a support for the organic electroluminescent device, and is usually made of a quartz or glass plate, a gold plate, or a metal plate. Metal plates, metal foils, plastic films and sheets, etc. are used. Among these, glass plates and transparent composites such as polyester, polymethacrylate, polycarbonate, and polysulfone. A resin plate is preferable. The substrate is less likely to cause deterioration of the organic electroluminescent element due to the outside air. Therefore, it is preferable to use a material with high gas barrier properties. When using a material with low gas barrier properties, such as It is preferable to provide a protective film or the like to improve the gas barrier properties.

[0470] [anode] The anode 2 has the function of injecting holes into the layer on the light-emitting layer 5 side. The anode 2 is usually made of a metal such as aluminum, gold, silver, nickel, palladium, or platinum; Metal oxides such as zinc and / or tin oxide; metal halides such as copper iodide; carbon Black and highly conductive materials such as poly(3-methylthiophene), polypyrrole, and polyaniline It is composed of molecules, etc.

[0471] The anode 2 is usually formed by a dry method such as sputtering or vacuum deposition. In addition, there are many metal particles such as silver, copper iodide particles, carbon black, conductive gold When forming the anode using metal oxide fine particles, conductive polymer fine powder, etc., a suitable binder is required. Alternatively, the layer can be formed by dispersing the layer in a dye resin solution and applying it onto a substrate. In the case of conductive polymers, a thin film can be formed directly on the substrate by electrolytic polymerization, or a conductive film can be formed on the substrate. The anode can also be formed by coating a polymer (Appl. Phys. Lett. ,Vol. 60, p. 2711, 1992).

[0472] The anode 2 usually has a single-layer structure, but may have a laminated structure as appropriate. In this case, a different conductive material may be laminated on the first anode layer. The thickness of the anode 2 may be determined depending on the required transparency and material. When this is required, the thickness is preferably such that the transmittance of visible light is 60% or more. The thickness of the anode 2 is preferably 5 nm or more, more preferably 80% or more. It is usually 10 nm or more, and is 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 can be arbitrarily determined depending on the required strength, etc. In this case, the anode 2 may have the same thickness as the substrate. When forming another layer on the surface of the anode 2, ultraviolet light / ozone, oxygen plasma, By applying argon plasma treatment or the like, impurities on the anode 2 are removed and the It is preferable to adjust the ionization potential to improve the hole injection property.

[0473] [Hole injection layer] The layer that transports holes from the anode 2 side to the light-emitting layer 5 side is usually a hole injection transport layer or This layer is called a hole transport layer. It transports holes from the anode 2 side to the light-emitting layer 5 side. When there are two or more layers, the layer closer to the anode side is sometimes called the hole injection layer 3. The injection layer 3 is formed to enhance the function of transporting holes from the anode 2 to the light-emitting layer 5. When the hole injection layer 3 is formed, the hole injection layer 3 is usually formed on the anode 2. can be.

[0474] The thickness of the hole injection layer 3 is usually 1 nm or more, preferably 5 nm or more, and is usually 1000 nm or less, preferably 500 nm or less. The hole injection layer may be formed by a vacuum deposition method or a wet film formation method. is preferably formed by a wet film forming method. A general method for forming a hole injection layer will be described below. In the device, the hole injection layer is formed by a wet film formation method using a composition for forming a hole injection layer. It is preferable that

[0475] [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 composition for forming a hole injection layer usually further contains a solvent. The hole injection layer-forming composition has high hole transport properties and can efficiently transport injected holes. Therefore, the hole mobility is large, and impurities that become traps are easily removed during manufacturing and use. It is preferable that the generation of the ionized gas is difficult. It is preferable that the transparency to light is high. In particular, when the hole injection layer is in contact with the light emitting layer, it is preferable that the light emitting layer is transparent. The luminescence efficiency is improved by forming an exciplex with the luminescent layer, which does not quench the luminescence from the luminescent layer. Preferably, it does not reduce the

[0476] As the hole transporting compound, from the viewpoint of the charge injection barrier from the anode to the hole injection layer, 4.5 A compound having an ionization potential of 6.0 eV to 6.0 eV is preferred. Examples of the compounds include aromatic amine compounds, phthalocyanine compounds, and porphyrin compounds. , oligothiophene compounds, polythiophene compounds, benzylphenyl compounds, Compounds in which tertiary amines are linked via fluorene groups, hydrazone compounds, silazane compounds, Examples thereof include nacridone compounds.

[0477] Among the above-mentioned exemplary compounds, aromatic amine compounds are preferred in terms of amorphousness and visible light transmittance. An aromatic tertiary amine compound is particularly preferred. is a compound having an aromatic tertiary amine structure, and having a group derived from an aromatic tertiary amine Also includes compounds. The type of aromatic tertiary amine compound is not particularly limited, but it is preferable to use a compound having a uniform surface smoothing effect. Polymerization with a weight average molecular weight of 1,000 or more and 1,000,000 or less is preferred because it is easy to obtain light emission. It is preferable to use a polymer compound (a polymer compound having a series of repeating units).

[0478] [Formation of hole injection layer by wet film formation method] When the hole injection layer 3 is formed by a wet film formation method, the material for the hole injection layer is usually a soluble material. Mix with a solvent (solvent for hole injection layer) to prepare a film-forming composition (composition for forming hole injection layer) Then, this hole injection layer-forming composition is applied to a layer corresponding to the layer below the hole injection layer (usually, The hole injection layer 3 is formed by applying the solution onto the anode (electrode) to form a film and drying it.

[0479] The concentration of the hole transporting compound in the composition for forming the hole injection layer significantly improves the effect of the present invention. However, in terms of uniformity of the film thickness, a lower value is preferable. A higher content is preferable in that defects are less likely to occur in the hole injection layer. It is preferably 0.1% by mass or more, more preferably 0.5% by mass or more. It is particularly preferable that the content is 70% by mass or less, and more preferably 60% by mass or less. It is more preferable that the content is less than 50% by mass, and particularly preferable that the content is 50% by mass or less.

[0480] Examples of the solvent include ether solvents, ester solvents, aromatic hydrocarbon solvents, and Examples include mide-based solvents. Examples of ether solvents include ethylene glycol dimethyl ether, ethylene glycol Licorice diethyl ether, propylene glycol-1-monomethyl ether acetate Aliphatic ethers such as (PGMEA) and 1,2-dimethoxybenzene, 1,3-dimethoxybenzene Dibenzoylbenzene, Anisole, Phenetole, 2-Methoxytoluene, 3-Methoxytoluene , 4-methoxytoluene, 2,3-dimethylanisole, 2,4-dimethylanisole, etc. Examples of aromatic ethers include the following.

[0481] Examples of ester solvents include phenyl acetate, phenyl propionate, and methyl benzoate. aromatic esters such as benzoic acid ethyl, benzoic acid ethyl, benzoic acid propyl, benzoic acid n-butyl, etc. Examples include: Examples of aromatic hydrocarbon solvents include toluene, xylene, and cyclohexylbenzene. benzene, 3-isopropylbiphenyl, 1,2,3,4-tetramethylbenzene, 1,4-diphenyl Examples include isopropylbenzene, cyclohexylbenzene, and methylnaphthalene.

[0482] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethyla cetoamide and the like. In addition to these, dimethyl sulfoxide and the like can also be used. 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, followed by: This is applied to the layer below the hole injection layer 3 (usually the anode 2) to form a film, and then dried. This is done by: After the hole injection layer 3 is formed, the coated film is usually dried by heating, drying under reduced pressure, or the like.

[0483] [Formation of hole injection layer by vacuum deposition method] When the hole injection layer 3 is formed by vacuum deposition, the material of the hole injection layer 3 is usually One or more types of materials are placed in a crucible installed in a vacuum chamber (using two or more types of materials) In this case, each is usually placed in a separate crucible), and the vacuum chamber is evacuated to 1.0 × 10 -4 P After that, the crucible is heated (usually when using two or more materials). Each crucible is heated to evaporate the material in the crucible while controlling the amount of evaporation (two or more types of When using materials, they are usually evaporated while controlling the evaporation rate independently, and then poured into a crucible. A hole injection layer is formed on the anode on the substrate placed opposite to the substrate. If so, place the mixture in a crucible, heat and evaporate it to form the hole injection layer. It is also possible.

[0484] The degree of vacuum during deposition is not limited as long as it does not significantly impair the effects of the present invention. x10 -6 Torr (0.13 × 10 -4 Pa) or more, 9.0×10 -6 Torr(12 .0×10 -4 The deposition rate is not more than 100 Pa. The deposition rate is not limited as long as it does not significantly impair the effects of the present invention. The deposition rate is not fixed, but is usually between 0.1 Å / sec and 5.0 Å / sec. There are no particular limitations as long as the effect of the present invention is not significantly impaired, but the temperature is preferably 10°C or higher, 50°C or higher. It is done below. The hole injection layer 3 may be crosslinked.

[0485] [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 transport layer 4 has a function of transporting holes from the anode 2 to the light-emitting layer 5. In order to enhance the hole transporting property, it is preferable to form this layer. The hole transport layer 4 is usually formed between the anode 2 and the light emitting layer 5. In some cases, it is formed between the hole injection layer 3 and the light emitting layer 5 .

[0486] The thickness of the hole transport layer 4 is usually 5 nm or more, preferably 10 nm or more. , usually 300 nm or less, preferably 100 nm or less. The hole transport layer 4 may be formed by vacuum deposition or wet film formation. In this case, it is preferable to form the film by a wet film forming method. A general method for forming a hole transport layer will be described below. In the method, the hole transport layer is formed by a wet film formation method using the second composition. preferable.

[0487] The hole transport layer 4 usually contains a hole transporting compound. The transport compound is preferably a polymer contained in the second organic layer. In addition to the polymer contained in the second organic layer, the hole transporting compound, 4,4'-bis(4,4'-biphenyl)-2-(4-methyl-2-propanol), two or more substituted bis[N-(1-naphthyl)-N-phenylamino]biphenyl Aromatic diamines containing tertiary amines and having two or more condensed aromatic rings substituted on the nitrogen atom (Japan JP-A-5-234681), 4,4',4''-tris(1-naphthylphenyl) Aromatic amine compounds with starburst structure such as (JL)triphenylamine umin., vol. 72-74, p. 985, 1997), from the tetramer of triphenylamine Aromatic amine compounds (Chem. Commun., p. 2175, 1996), 2, 2',7,7'-tetrakis-(diphenylamino)-9,9'-spirobifluorene, etc. Spiro compounds (Synth. Metals, Vol. 91, p. 209, 1997), 4,4 Carbazole derivatives such as '-N,N'-dicarbazolebiphenyl are preferred. In addition, for example, polyvinylcarbazole, polyvinyltriphenylamine ( (JP Patent Publication No. 7-53953) Polyaryl containing tetraphenylbenzidine Polyethylene ether sulfone (Polym. Adv. Tech., Vol. 7, p. 33, 1996) etc. may be included.

[0488] [Formation of hole transport layer by wet film formation method] When forming a hole transport layer by a wet film formation method, the hole injection layer is usually formed by a wet film formation method. In the same manner as in the case of forming a hole transport layer, the hole transport layer forming composition is used instead of the hole injection layer forming composition. It is formed using. When the hole transport layer is formed by a wet film formation method, the composition for forming the hole transport layer is usually further dissolved. The solvent used in the composition for forming a hole transport layer is the same as that used in the composition for forming a hole injection layer. The same solvent as used in the step (1) can be used. The concentration of the hole transport compound in the composition for forming the hole transport layer is The concentration of the hole transporting compound in the material can be in the same range as that of the hole transporting compound in the material. The hole transport layer can be formed by a wet film formation method in the same manner as the hole injection layer formation method described above. Cut.

[0489] [Formation of hole transport layer by vacuum deposition method] When forming a hole transport layer by vacuum deposition, the hole injection layer is usually formed by vacuum deposition. In the same manner as in the case of forming the hole injection layer by the deposition method, a hole transport layer forming composition is used instead of the hole injection layer forming composition. The film can be formed using a composition. The film formation conditions, such as the degree of vacuum during deposition, deposition rate, and temperature, can be adjusted. The film can be formed under the same conditions as those for the vacuum deposition of the hole injection layer.

[0490] [Emitting layer] When an electric field is applied between the pair of electrodes, the light-emitting layer 5 converts holes injected from the anode 2 and electrons injected from the cathode This layer is excited by the recombination of electrons injected from 7 and emits light. The light-emitting layer 5 is a layer formed between the anode 2 and the cathode 7, and the light-emitting layer is formed on the anode by a hole-injecting If there is a layer, it is formed between the hole injection layer and the cathode, and if there is a hole transport layer on the anode, , formed between the hole transport layer and the cathode.

[0491] The organic electroluminescent device of the present invention has a first organic layer, and the first organic layer is a light-emitting layer. It is preferable that the compound represented by formula (2) is contained, and preferably further contains the light-emitting material and The charge transport compound is included. The thickness of the light-emitting layer 5 is arbitrary as long as it does not significantly impair the effects of the present invention. On the other hand, a thinner film is preferable because it is easier to achieve a low driving voltage. Therefore, it is preferable that the thickness is 3 nm or more, and more preferably 5 nm or more. On the other hand, it is usually preferably 200 nm or less, more preferably 100 nm or less. It's nice. The light-emitting layer 5 contains at least a material having a light-emitting property as a light-emitting material, and Preferably, the host material contains one or more charge transporting compounds.

[0492] (Charge transport material) The charge transport material is a material that has the ability to transport positive charges (holes) or negative charges (electrons). There are no particular limitations, and known materials can be used as long as they do not impair the effects of the invention. The charge transport material may be a compound that has been used in the light emitting layer 5 of an organic electroluminescent device. In particular, the compounds used as the host material of the light-emitting layer 5 are preferred.

[0493] Specific examples of the charge transport material include aromatic amine compounds and phthalocyanine compounds. compounds, porphyrin compounds, oligothiophene compounds, polythiophene compounds, benzophenone compounds, Dylphenyl compounds, compounds with tertiary amines linked via fluorene groups, hydrazone compounds Silazane compounds, silanamine compounds, phosphamine compounds, quinacridone compounds In addition to the compounds exemplified as the hole transporting compound of the hole injection layer 3, Thracene compounds, pyrene compounds, carbazole compounds, pyridine compounds, phenanthracene compounds, Electron transporting compounds such as thoroline compounds, oxadiazole compounds, and silole compounds Examples include:

[0494] Also, for example, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenanthrin Contains two or more tertiary amines, typically phenyl, and two or more fused aromatic rings substituted on the nitrogen atom Aromatic diamines (JP Patent Publication No. 5-234681), 4,4',4''-triamine Starburst structure such as bis(1-naphthylphenylamino)triphenylamine Aromatic amine compounds (J. Lumin., vol. 72-74, p. 985, 1997), Aromatic amine compounds consisting of tetramers of phenylamine (Chem. Commun., 2175, 1996), 2,2',7,7'-tetrakis-(diphenylamino)- Fluorene-based compounds such as 9,9'-spirobifluorene (Synth.Metals,9 1, p. 209, 1997), 4,4'-N,N'-dicarbazole biphenyl, etc. Compounds exemplified as hole transporting compounds for the hole transport layer 4, such as rubazoline compounds, are also preferred. In addition, 2-(4-biphenylyl)-5-(p-tert-butyl) (tBu-PBD), 2,5-bis(2,5-dimethylphenyl)-1,3,4-oxadiazole (tBu-PBD), Oxadiazoles such as bis(1-naphthyl)-1,3,4-oxadiazole (BND) The compound, 2,5-bis(6'-(2',2"-bipyridyl))-1,1-dimethyl-3, Silole compounds such as 4-diphenylsilole (PyPySPyPy), bathophenanthrene Lorin (BPhen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthate Phenanthroline compounds such as bathocuproine (BCP) are also included.

[0495] [Formation of light-emitting layer by wet film formation method] The light-emitting layer may be formed by vacuum deposition or wet film formation. From these viewpoints, wet film-forming methods are preferred, and spin coating and ink-jet methods are more preferred. The above composition for organic electroluminescent devices is used to form a hole injection layer or a hole transport layer which is a layer below the light emitting layer. When a transfer layer is formed, lamination by a wet film forming method is easy, so the wet film forming method is adopted. When the light-emitting layer is formed by a wet film-forming method, the hole-injecting layer is usually formed by a wet film-forming method. In the same manner as in the case of forming the layer by the film-forming method, a layer to be used as the light-emitting layer is used instead of the hole-injection layer-forming composition. The light-emitting layer is formed using a composition for forming a light-emitting layer prepared by mixing the material to be formed with a soluble solvent (solvent for the light-emitting layer). Complete.

[0496] Examples of the solvent include the ether-based solvents and ester-based solvents mentioned for forming the hole injection layer. Solvents, aromatic hydrocarbon solvents, amide solvents, alkane solvents, halogenated aromatic hydrocarbons Hydrogen hydride solvents, aliphatic alcohol solvents, alicyclic alcohol solvents, aliphatic ketone solvents Specific examples of the solvent are listed below, but the effects of the present invention can be achieved by The present invention is not limited to these examples, provided that they do not impair the rights of the applicant.

[0497] For example, ethylene glycol dimethyl ether, ethylene glycol diethyl ether , aliphatic alcohols such as propylene glycol-1-monomethyl ether acetate (PGMEA) Ether solvents; 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole phenetole, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene 2,3-dimethylanisole, 2,4-dimethylanisole, diphenyl ether, etc. Aromatic ether solvents; phenyl acetate, phenyl propionate, methyl benzoate, benzoic acid Aromatic ester solvents such as ethyl benzoate, propyl benzoate, and n-butyl benzoate; toluene benzene, xylene, mesitylene, cyclohexylbenzene, tetralin, 3-isopropylbenzene Phenyl, 1,2,3,4-tetramethylbenzene, 1,4-diisopropylbenzene, Aromatic hydrocarbon solvents such as cyclohexylbenzene and methylnaphthalene; N,N-dimethyl Amide solvents such as methylformamide and N,N-dimethylacetamide; n-decane, cyclohexane Alkane solvents such as hexane, ethylcyclohexane, decalin, and bicyclohexane; Halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, and trichlorobenzene Solvents: Aliphatic alcohol solvents such as butanol, hexanol, etc.; cyclohexanol, cyclohexanol, etc. Alicyclic alcohol solvents such as cyclooctanol; methyl ethyl ketone, dibutyl ketone, etc. Aliphatic ketone solvents such as cyclohexanone, cyclooctanone, and fenchone; Among these, alkane solvents and aromatic hydrocarbon solvents are Particularly preferred.

[0498] [Hole blocking layer] A hole-blocking layer may be provided between the light-emitting layer 5 and the electron-injecting layer described below. This layer is laminated on the optical layer 5 so as to be in contact with the interface of the light-emitting layer 5 on the cathode 7 side. This hole blocking layer has the role of preventing holes migrating from the anode 2 from reaching the cathode 7. and efficiently transports electrons injected from the cathode 7 toward the light-emitting layer 5. The properties required for the material that constitutes the hole blocking layer are high electron mobility and low hole mobility. The energy gap (difference between HOMO and LUMO) is large, and the excited triplet level ( T1) is high.

[0499] Examples of materials for the hole blocking layer that satisfy these conditions include bis(2-methyl-8- Quinolinolato) (phenolato) aluminum, bis(2-methyl-8-quinolinolato) ( Mixed ligand complexes such as triphenylsilanolate)aluminum, bis(2-methyl-8-oxo) (2-methyl-8-quinolinolato)aluminum-μ-oxo-bis-(2-methyl-8-quinolinolato)aluminum metal complexes such as dinuclear metal complexes, styryl compounds such as distyrylbiphenyl derivatives (Japan) JP-A-11-242996), 3-(4-biphenylyl)-4-phenyl-5- Triazole derivatives such as (4-tert-butylphenyl)-1,2,4-triazole (Japanese Patent Application Laid-Open No. 7-41759), phenanthroline derivatives such as bathocuproine ( Japanese Patent Application Laid-Open No. 10-79297 and the like. Compounds having at least one pyridine ring substituted at the 2-, 4-, and 6-positions described in No. 22962 The material is also preferred as the hole blocking layer material.

[0500] There is no limitation on the method for forming the hole blocking layer. Therefore, the hole blocking layer may be formed by a wet film forming method, a vapor deposition method, or other methods. It can be formed. The thickness of the hole blocking layer is arbitrary as long as it does not significantly impair the effect of the present invention. nm or more, preferably 0.5 nm or more, and is usually 100 nm or less, preferably 5 0nm or less.

[0501] [Electron transport layer] The electron transport layer 6 is formed between the light-emitting layer 5 and the cathode in order to further improve the current efficiency of the device. It is located between 7. The electron transport layer 6 efficiently transports electrons injected from the cathode 7 between the electrodes to which an electric field is applied. The electron transport layer 6 is made of a compound that can transport electrons in the direction of the light-emitting layer 5. The electron transporting compound to be used is one having high electron injection efficiency from the cathode 7 and high electron mobility. It is necessary that the compound has a high conductivity and can efficiently transport injected electrons. do.

[0502] Specific examples of the electron transporting compound used in the electron transport layer include 8-hydroxybenzophenone-1, ...2, 8-hydroxybenzophenone-3, 8-hydroxybenzophenone-4, 8-hydroxybenzophenone-5, 8-hydroxybenzophenone-6, 8-hydroxybenzophenone-7, 8-hydroxybenzophenone-8, 8-hydroxybenzophenone-9, 8-hydroxybenzophenone-10, Metal complexes such as aluminum complexes of quinoline (Japanese Patent Publication No. 59-194393), Metal complexes of 10-hydroxybenzo[h]quinoline, oxadiazole derivatives, distyriazoles Iridium biphenyl derivatives, silole derivatives, 3-hydroxyflavone metal complexes, 5-hydroxyflavone Ciflavonoid metal complexes, benzoxazole metal complexes, benzothiazole metal complexes, tris Benzimidazolylbenzene (U.S. Pat. No. 5,645,948), quinoxaline compounds (Japanese Unexamined Patent Publication No. 6-207169), phenanthroline derivative (Japanese Unexamined Patent Publication No. 5-207169), -331459), 2-tert-butyl-9,10-N,N'-dicyanoanthracene Laquinone diimine, n-type hydrogenated amorphous silicon carbide, n-type zinc sulfide, n-type zinc selenide, etc. Examples include: The thickness of the electron transport layer 6 is usually 1 nm or more, preferably 5 nm or more. 00 nm or less, preferably 100 nm or less. The electron transport layer 6 is formed by the wet film formation method or the vacuum deposition method in the same manner as described above. It is formed by laminating it on the hole blocking layer, usually by vacuum deposition.

[0503] [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 . 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 barium and calcium. The thickness of the film is preferably 0.1 nm or more and 5 nm or less. It's nice.

[0504] Furthermore, nitrogen-containing heterocyclic compounds such as bathophenanthroline and 8-hydroxyquinoline Organic electron transport materials, such as metal complexes, are often used in combination with sodium, potassium, and cerium. Doping with alkali metals such as sodium, lithium, rubidium, etc. (Japanese Patent Application Laid-Open No. 2008-27 Publication No. 0171, Japanese Patent Application Publication No. 2002-100478, Japanese Patent Application Publication No. 2002-10 0482, etc.), it is possible to improve electron injection and transport properties and achieve excellent film quality. This is preferable because it is possible to

[0505] The thickness of the electron injection layer is usually 5 nm or more, preferably 10 nm or more, and is usually 20 The thickness is in the range of 0 nm or less, preferably 100 nm or less. The electron injection layer is formed by a wet film formation method or a vacuum deposition method on the light-emitting layer 5 or the hole-blocking layer thereon. The insulating layer 10 is formed by laminating it on the electron transport layer 6 . The details of the wet film formation method are the same as those of the light-emitting layer described above. The hole blocking layer, electron transport layer, and electron injection layer are formed by co-doping the electron transport material with a lithium complex. It may also be made into one layer.

[0506] [cathode] The cathode 7 serves to inject electrons into the layer (electron injection layer or light-emitting layer, etc.) on the light-emitting layer 5 side. vinegar. The cathode 7 may be made of the same material as the anode 2. For efficient electron injection, it is preferable to use a metal with a low work function, for example, , tin, magnesium, indium, calcium, aluminum, silver, or other metals or Specific examples include magnesium-silver alloys, magnesium -Indium alloy, aluminum-lithium alloy, and other low work function alloy electrodes. do.

[0507] In terms of the stability of the organic electroluminescent device, a material with a high work function and stability against the atmosphere is placed on the cathode. It is preferable to laminate a metal layer having a low work function to protect the cathode. Examples of metals that can be used include aluminum, silver, copper, nickel, chromium, gold, and platinum. Examples include: The thickness of the cathode is usually the same as that of the anode.

[0508] [Other layers] The organic electroluminescent device of the present invention may further comprise other layers as long as the effects of the present invention are not significantly impaired. That is, any of the other layers described above may be present between the anode and the cathode. stomach.

[0509] [Other element configurations] The organic electroluminescent device of the present invention has a structure opposite to that described above, i.e., a cathode on a substrate. , electron injection layer, electron transport layer, hole blocking layer, light emitting layer, hole transport layer, hole injection layer, and anode in this order. Stacking is also possible. When the organic electroluminescent element of the present invention is applied to an organic electroluminescent device, a single organic electroluminescent element When used as an element, a plurality of organic electroluminescent elements are arranged in an array. Alternatively, the anodes and cathodes may be arranged in an XY matrix.

[0510] <Organic EL display device> The organic EL display device (organic electroluminescent device display device, also simply referred to as "display device") of the present invention ) is equipped with the organic electroluminescent device of the present invention. There are no particular restrictions on the method, and the organic electroluminescent device of the present invention can be assembled in accordance with a conventional method. This can be done. For example, "Organic EL Display" (Ohmsha, August 20, 2004, Shizuo Tokito) The organic EL display device of the present invention can be manufactured by a method such as that described in the publications by Adachi Chihaya and Murata Hideyuki. can be formed.

[0511] <Organic EL lighting> The organic EL lighting (organic electroluminescent element lighting, also simply referred to as "lighting device") of the present invention is The organic electroluminescent device of the present invention is provided. The type and structure of the organic EL lighting device of the present invention are not particularly limited. There is no limitation, and the organic electroluminescent device of the present invention can be assembled in accordance with a conventional method. [Example]

[0512] The present invention will be described in more detail below with reference to the following examples. The present invention is not limited to the above, and can be implemented by any modification without departing from the spirit of the invention. do.

[0513] [Example 1] An organic electroluminescent device was fabricated in the following manner. A transparent conductive film of indium tin oxide (ITO) was deposited to a thickness of 50 nm on a glass substrate. The product (manufactured by Geomatec, sputtered film) was then processed using ordinary photolithography technology. The anode was formed by patterning into stripes of 2 mm width using hydrochloric acid etching. The substrate on which the ITO pattern was formed was then subjected to ultrasonic cleaning with a surfactant solution and ultrapure water. After washing in the order of water washing with ultrasonic cleaning using ultrapure water and water washing with ultrapure water, it was dried with compressed air. Finally, UV ozone cleaning was performed.

[0514] The composition for forming a hole injection layer is a compound having a repeating structure represented by the following formula (P-1): 3.0% by mass of a hole transporting polymer compound and an electron accepting compound represented by the following formula (HI-1): 0.6% by mass of the compound was dissolved in ethyl benzoate to prepare a composition. This solution was spin-coated onto the substrate in the atmosphere, and then heated on a hot plate in the atmosphere for 24 The coating was dried at 0° C. for 30 minutes to form a uniform thin film with a thickness of 40 nm, which served as a hole injection layer.

[0515] [ka]

[0516] Next, 100 mass % of a charge transport polymer compound having a structure represented by the following formula (HT-1) was added. The resulting part was dissolved in mesitylene to prepare a 2.5% by mass solution. This solution was spin-coated on the substrate on which the hole injection layer had been formed in a nitrogen glove box. The coated film was dried at 240°C for 30 minutes on a hot plate in a nitrogen glove box. A uniform thin film with a thickness of 60 nm was formed as a hole transport layer.

[0517] [ka]

[0518] Subsequently, as a material for the light-emitting layer, 75 parts by mass of a compound represented by the following formula (H-1) 25 parts by mass of the compound represented by the formula (H-2) and 2 parts by mass of the compound represented by the formula (D-1) 0 parts by mass, 2 parts by mass of a compound represented by the following formula (D-2) were weighed, and cyclohexylbenzene The resulting solution was dissolved in ethanol to prepare a 5% by mass solution as a composition for forming a light-emitting layer.

[0519] [ka]

[0520] [ka]

[0521] [ka]

[0522] [ka]

[0523] This composition for forming a light-emitting layer was applied to the substrate on which the hole transport layer had been formed by coating in a nitrogen globe box. The film was spin-coated in a nitrogen glove box at 120°C for 2 min. The coating was dried for 10 minutes to form a uniform thin film with a thickness of 50 nm, which was used as the light-emitting 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 Pa or less It was vented until

[0524] 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 that the film thickness ratio was 2:3. A hole blocking layer having a thickness of 30 nm was formed.

[0525] [ka]

[0526] Next, a 2mm wide striped shadow mask was used as a mask for cathode evaporation, and the anode The ITO stripes were then placed in a vacuum deposition chamber. Then, aluminum was heated in a molybdenum boat and evaporated at a rate of 1 to 8.6 Å / s. An aluminum layer having a thickness of 80 nm was formed as a cathode. In this way, an organic electroluminescent device having a light-emitting area of ​​2 mm x 2 mm was obtained. Obtained.

[0527] [Comparative Example 1] Instead of the charge transport polymer compound having the structure represented by formula (HT-1), A hole transport layer was formed using 100 parts by mass of a charge transport compound having a structure represented by T-2). An organic electroluminescent device was produced in the same manner as in Example 1, except that the above-mentioned organic electroluminescent element was formed.

[0528] [ka]

[0529] [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 Lights up with External quantum efficiency (EQE) (%) at 15 mA / cm 2 The current density of The time it took for the luminance to decrease to 95% of the initial luminance (LT95) was measured. The ratio of the EQE of Example 1 to the EQE of Comparative Example 1, which was taken as 1, was calculated as the relative EQE. The ratio of the LT95 of Example 1 to the LT95 of Comparative Example 1, which was set to 1, was calculated to obtain the relative driving life. did. 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.

[0530] [Table 1] [Industrial Applicability]

[0531] The organic electroluminescent device of the present invention is suitably used for, for example, organic EL display devices and organic EL lighting. You can be there. [Explanation of symbols]

[0532] 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 (2): The second organic layer contains a polymer that satisfies at least one of the following (i) and (ii): , organic electroluminescent devices. (i) 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) Among them, it has two or more repeating units. (ii) 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) It consists of only one or more repeating units of the above. 【Chemical 1】 [In formula (2), Ar １ is a structure represented by formula (2a). Ar ２ each independently represents a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent; Ar is a aryl group. ２ If there are multiple, they may be the same or different. Good too. Each R is independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a hetero group having 7 to 40 carbon atoms, or b) an aralkyl group, an alkoxy group having 1 to 20 carbon atoms, a (hetero)aryl group having 3 to 20 carbon atoms; an alkylsilyl group having 1 to 20 carbon atoms; an arylsilyl group having 6 to 20 carbon atoms; an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms; These groups, except for hydrogen atoms, may have a substituent. The other group has a structure represented by formula (2b). m and n each independently represent an integer of 1 to 3. 【Chemistry 2】 [In formula (2a), R １ each independently represents a hydrogen atom, a heterocyclic group having 3 to 20 carbon atoms which may have a substituent, ) an aryl group, or Ar ２ It is a combination with 【Chemistry 3】 [In formula (2b), Ar ３ represents a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent. R ２ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a hydroxy group having 7 to 40 carbon atoms, (hetero)aralkyl groups, alkoxy groups having 1 to 20 carbon atoms, (hetero)aralkyl groups having 3 to 20 carbon atoms an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms. These groups, except for the hydrogen atom, may have a substituent. "★" indicates the bonding position with formula (2). 【Chemistry 4】 (In formula (54), Ar ５１ represents an aromatic hydrocarbon group which may have a substituent other than a bridging group, an aromatic heterocyclic group which may have a substituent, or a bridging group which may have a substituent other than Aromatic hydrocarbon groups and aromatic heterocyclic groups which may have a substituent other than a bridging group are selected from the group consisting of: a group in which a plurality of groups 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 has a substituent other than a crosslinking group is an alkyl group which may be R ２０７ ~R ２０９ and R ２１１ ~R ２１４ are each independently a hydrogen atom or a group other than a bridging group. an alkyl group which may have a substituent, an aralkyl group which may have a substituent other than a bridging group; an aromatic hydrocarbon group which may have a substituent other than a cyclic group or a crosslinking group, a, b, and d each independently represent an integer from 0 to 4; c is an integer from 0 to 3; a+b is 1 or greater; 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 each independently represent an integer from 0 to 3. 【Chemistry 5】 (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; is a methyl group, R ３０４ and R ３０５ each independently represents an alkyl group which may have a substituent other than a crosslinking group; an alkyl group, an alkoxy group which may have a substituent other than a crosslinking group, or an alkoxy group which may have a substituent other than a crosslinking group an aralkyl group which may be present, l, n, p, and q each independently represent 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 6】 (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 bridging group a divalent aromatic heterocyclic group optionally having a substituent other than and the divalent aromatic heterocyclic group, is a divalent group linked via a group, R ４４１ and R ４４２ each independently represents an alkyl group which may have a substituent other than a crosslinking group; is a methyl group, t is 1 or 2; u is 0 or 1; r and s each independently represent an integer from 0 to 4; r+s is 1 or greater; However, if s is 1 or greater, u is 1.) 【Chemistry 7】 (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 bridging group; a group, an alkoxy 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 bridging group, an aromatic hydrocarbon group which may have a substituent other than a bridging group, represents an aromatic heterocyclic group which may have a substituent other than a bridging group, f, g, and h each independently represent an integer from 0 to 4; f+g+h is 1 or greater; e is an integer from 0 to 3; However, when g is 1 or more, e is 1 or more.)

2. R in the formula (2), formula (2a), and formula (2b) １ , R ２ , Ar ２ and Ar ３ has The optional substituents are each independently an alkyl group, an aralkyl group, a heteroaralkyl group, an alkoxy group, an aryl group, an aryloxy ... oxy group, aryloxy group, heteroaryloxy group, alkylsilyl group, arylsilyl group alkyl group, alkylcarbonyl group, arylcarbonyl group, alkylamino group, aryl 2. The organic electroluminescent device according to claim 1, wherein the aryl group is an amino group, an aryl group, or a heteroaryl group. child.

3. 2. The organic electroluminescent device according to claim 1, wherein the formula (2) is represented by the following formula (2-1): 【Chemistry 8】 [In formula (2-1), Ar ４ is a structure represented by the formula (2a), and Ar ５ is Ar in the formula (2). ２ and is a group selected from the same groups, and Ar ６ is Ar in the formula (2b). ３ Selected from the same group as is a group selected from ３ are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a carbon atom (Hetero)aralkyl groups having 7 to 40 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, and (hetero)aryloxy groups, alkylsilyl groups having 1 to 20 carbon atoms, and (hetero)aryl groups having 6 to 20 carbon atoms. an arylsilyl group, an arylamino group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms; ) an aryl group. These groups, except for the hydrogen atom, may have a substituent. Ar ５ and Ar ６ When there are a plurality of j and k, they may be the same or different. are values ​​selected from the same ranges as m and n in formula (2).

4. Ar in the formula (2-1) ５ each independently represents a 1,3-phenylene group or a 1,4- The organic electroluminescent device according to claim 3 , wherein the group is a phenylene group.

5. R in the formula (2-1) ３ , Ar ５ , and Ar ６ The substituents which may be possessed by each of In particular, alkyl groups, aralkyl groups, heteroaralkyl groups, alkoxy groups, aryloxy groups, group, heteroaryloxy group, alkylsilyl group, arylsilyl group, alkylcarbonyl group an alkyl group, an arylcarbonyl group, an alkylamino group, an arylamino group, an aryl group, or 4. The organic electroluminescent device according to claim 3, wherein the aryl group is a heteroaryl group.

6. The polymer contains a partial structure represented by the following formula (61) or the following formula (61'): Item 2. The organic electroluminescent device according to item 1. 【Chemistry 9】 (In formula (61) and formula (61′), R ６０１ is R in formula (54) ２０１ or R ２０２ , R in formula (55) ３０３ , R ３０４ , R ３０５ , or R ３０６ , R in formula (56) ４４１ or R ４４２ , formula (5 7) R in ５１７ , R ５１８ , or R ５１９ represents a bond with the adjacent atom, and -* represents a bond with the adjacent atom. 。 Formula (61) and Formula (61') are a partial structure of Formula (54) or a partial structure of Formula (56) In this case, Ring B may be part of a fused ring. The partial structures represented by formula (61) and formula (61′) are R ６０１ In addition to Ring A and and Ring B, when it is a partial structure of formula (54), R ２０１ or R ２０２ , formula (5 5) is a partial structure of R ３０３ , R ３０４ , R ３０５ , or R ３０６ , formula (56) In the case of a partial structure of ４４１ or R ４４２ , when it is a partial structure of formula (57), R ５ １７ , R ５１８ or R ５１９ It may have.)

7. The compound according to claim 1 , wherein the first organic layer further contains a compound represented by the following formula (7): Organic electroluminescent device. 【Chemistry 10】 [In formula (7), ring A701 represents an aromatic hydrocarbon ring structure which may have a substituent or a substituent represents an aromatic heterocyclic structure which may have the following structure: Ring A702 represents an aromatic heterocyclic structure which may have a substituent. When there are a plurality of rings A701 and A702, they may be the same or different. That's fine. R ７０１ , R ７０２ are each independently a structure represented by formula (b), and "*" represents ring A701. or represents the bonding position with ring A702. ７０１ , R ７０２ are the same but different Also, R ７０１ , R ７０２ If there are multiple of each, they may be the same but different. It may be possible. Ar ７０１ , Ar ７０３ each independently represents an aromatic hydrocarbon ring which may have a substituent; structure, or an aromatic heterocyclic structure which may have a substituent. Ar ７０２ is an aromatic hydrocarbon ring structure which may have a substituent, It represents 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 If there are multiple of each, they are the same But it may be different. The substituents bonded to ring A701, the substituents bonded to ring A702, or the substituents bonded to ring A701 The substituents bonded to ring A702 and the substituents bonded to ring A703 are bonded to each other to form a ring. That's fine. B ７０１ -L ７００ -B ７０２ represents an anionic bidentate ligand. ７０１ and B ７ ０２ each independently represents a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms form a ring. It may be an atom that ７００ is a single bond, or B ７０１ and B ７０２ Together 2 represents the atomic group constituting the dentate ligand. ７０１ -L ７００ -B ７０２ If there are multiple They may be the same or different. In addition, in the formulas (7) and (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 greater, with the upper limit being the number of groups that can be substituted on ring A701 and ring A702. Represents the integer above. and m is an integer of 1 to 3.

8. The first organic layer further comprises a compound represented by the following formula (250) and a compound represented by the following formula (260): The organic electroluminescence according to claim 1, comprising at least one compound selected from the group consisting of compounds represented by the formula: element. 【Chemistry 11】 (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 group having 6 to 3 carbon atoms which may have a substituent a divalent aromatic hydrocarbon group having 3 to 30 carbon atoms which may have a substituent; represents an aromatic heterocyclic group, Xa ２ , Ya ２ and Za ２ each independently represents a hydrogen atom, a carbon atom which may have a substituent, a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, or a monovalent aromatic hydrocarbon group having 3 to 30 carbon atoms, which may have a substituent; represents a monovalent aromatic heterocyclic group, 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 Ku, However, when g11, h11, or j11 is 0, the corresponding Xa ２ , Ya ２ , Z a ２ is not a hydrogen atom.) 【Chemistry 12】 (In formula (260), Ar ６１ ~Ar ６５ each independently represents a hydrogen atom or a monovalent group which may have a substituent; an aromatic hydrocarbon group having 6 to 60 carbon atoms, L １ ~L ５ each independently represents a divalent group having 6 to 60 carbon atoms which may have a substituent; is an aromatic hydrocarbon group of the formula 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 when n is 1 or more Another Ar ６５ At least one of them is not a hydrogen atom.)

9. 9. The method of claim 8, wherein the first organic layer comprises at least a compound represented by formula (250). The organic electroluminescent device according to claim 1.

10. A display device comprising the organic electroluminescent device according to any one of claims 1 to 9.

11. A lighting device comprising the organic electroluminescent device according to any one of claims 1 to 9.

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