Polymer, composition for forming organic film, method for producing organic film, organic electroluminescent element, display device, and illumination device

Abstract

This polymer satisfies formulae (1) and (2), satisfies at least one of conditions (i) and (ii), and includes a repeating unit represented by formula (59).　Formula (1): Abs500nm ≤ 0.004　Formula (2): Abs460nm ≤ 0.010　Abs500nm and Abs460nm each represent the absorbance of a 1 mass% tetrahydrofuran solution of the polymer. (i) The polymer has two or more repeating units among the repeating unit represented by formula (54), the repeating unit represented by formula (55), the repeating unit represented by formula (56), and the repeating unit represented by formula (57). (ii) The polymer consists of one or more repeating units among the repeating unit represented by formula (54), the repeating unit represented by formula (55), the repeating unit represented by formula (56), and the repeating unit represented by formula (57).

Description

Polymer, composition for forming organic films, method for producing organic films, organic field light-emitting device, display device, and lighting device

[0001] The present invention relates to a polymer, an organic film-forming composition, a method for producing an organic film, an organic electroluminescent element, a display device and a lighting device equipped with an organic electroluminescent element.

[0002] In recent years, the development of organic electroluminescent devices using organic thin films has shifted from those using inorganic materials to organic electroluminescent devices. Organic electroluminescent devices (OLEDs) typically have a hole injection layer, a hole transport layer, an organic light-emitting layer, and an electron transport layer between the anode and cathode. Materials suitable for each of these layers are being developed, and development is progressing on the emission colors, including red, green, and blue.

[0003] Methods for forming the organic layer of an organic electroluminescent device include vacuum deposition and wet deposition (coating). Vacuum deposition has the advantage of easy stacking, improving charge injection from the anode and / or cathode, and facilitating exciton containment in the light-emitting layer. On the other hand, wet deposition does not require a vacuum process, is easy to scale up to large areas, and allows for the easy formation of layers containing multiple materials with various functions by using a coating solution that mixes multiple materials with various functions. For this reason, research and development of organic electroluminescent devices using wet deposition has been actively pursued in recent years.

[0004] For example, Patent Documents 1 to 5 disclose organic electroluminescent devices comprising an organic layer fabricated by a wet film deposition method, the hole transport layer containing the following polymer.

[0005]

[0006] Patent Document 6 discloses an organic electroluminescent device comprising an organic layer fabricated by a wet film deposition method, the hole transport layer containing the following polymer.

[0007]

[0008] Patent Document 7 discloses an organic electroluminescent device comprising a hole transport layer containing a polymer having the following repeating units, which is an organic layer fabricated by a wet film deposition method.

[0009]

[0010] However, the organic electroluminescent devices described in Patent Documents 1 to 7, which consist of organic layers, are not sufficient in terms of performance for display applications, and there is a need for further improvements in luminous efficiency and operating life of organic electroluminescent devices formed by wet film deposition methods.

[0011] International Publication No. 2019 / 198699, International Publication No. 2019 / 235452, International Publication No. 2020 / 040298, International Publication No. 2020 / 045681, International Publication No. 2020 / 080528, International Publication No. 2022 / 092046, International Publication No. 2015 / 179037

[0012] The present invention has been made in view of the above-mentioned conventional circumstances, and aims to provide a polymer that, when used in an organic layer constituting an organic electroluminescent element, yields an organic electroluminescent element that is superior in at least one of luminous efficiency and driving life.

[0013] As a result of diligent research by the inventors, it has been found that the above problems can be solved by using a polymer that satisfies a specific formula and has a specific structure. The gist of the embodiments of the present invention is as follows.

[0014] [1] A polymer that satisfies the following formulas (1) and (2), and satisfies at least one of the following (i) and (ii), and contains repeating units represented by the following formula (59). Abs 500 nm ≤ 0.004 ... (1) Abs 460 nm ≤ 0.010 ... (2) Abs 500 nm and Abs 460 nm each represent the absorbance of a 1 mass% tetrohydrofuran solution of the polymer. (i) Having two or more repeating units from among the following repeating units represented by formula (54), formula (55), formula (56), and formula (57). (ii) Consisting of only one or more repeating units from among the following repeating units represented by formula (54), formula (55), formula (56), and formula (57). (In formula (54), Ar ５1is a group in which a plurality of groups selected from the group consisting of an aromatic hydrocarbon group which may have a substituent other than a crosslinking group, an aromatic heterocyclic group which may have a substituent other than a crosslinking group, or an aromatic hydrocarbon group which may have a substituent other than a crosslinking group and an aromatic heterocyclic group which may have a substituent other than a crosslinking group are directly or indirectly connected 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 )-; R ２０１ , R ２０２ , R ２２１ and R ２２２ are each independently an alkyl group which may have a substituent other than a crosslinking group; R ２０７ to R ２０９ and R ２１１ to R ２１４ ] are each independently a hydrogen atom, an alkyl group which may have a substituent other than a crosslinking group, an aralkyl group which may have a substituent other than a crosslinking group, or an aromatic hydrocarbon group which may have a substituent other than a crosslinking group; a, b and d are each independently an integer of 0 to 4; c is an integer of 0 to 3; provided that when a is 1 or more, c is 1 or more, and when b is 1 or more, d is 1 or more; when there are a plurality of R[[ID=??]] ２０１ , the plurality of R ２０１ may be the same or different; when there are a plurality of R ２０２ , the plurality of R ２０２ may be the same or different; when there are a plurality of R ２２１ , the plurality of R ２２１ may be the same or different; when there are a plurality of R ２２２ , the plurality of R ２２２ may be the same or different; i and j are each independently an integer of 0 to 3.) (In Formula (55), Ar ５１ is the same as Ar ５１ in the above Formula (54), and R ３０３ and R ３０６ It should be noted that there seems to be an unclear tag "[[ID=??]]" in the original text which needs to be further clarified for a more accurate translation.Each of these is an alkyl group which may have substituents other than a crosslinking group, and R ３０４ and R ３０５ Each of these is independently an alkyl group which may have substituents other than a crosslinking group, an alkoxy group which may have substituents other than a crosslinking group, or an aralkyl group which may have substituents other than a crosslinking group; l, n, p, and q are each independently 0 or 1; m is 1 or 2, however, if p is 1, l is 1, and if q is 1, n is 1. (In formula (56), Ar ５１ Ar in formula (54) ５１ It is similar to Ar ４１ R is a divalent group in which multiple groups selected from the group consisting of a divalent aromatic hydrocarbon group which may have substituents other than a crosslinking group, a divalent aromatic heterocyclic group which may have substituents other than a crosslinking group, or an aromatic hydrocarbon group which may have substituents other than a crosslinking group and an aromatic heterocyclic group which may have substituents other than a crosslinking group are directly or via a linking group, ４４１ and R ４４２ Each of these is an alkyl group which may have substituents other than a crosslinking group, t is 1 or 2, u is 0 or 1, and r and s are each an integer from 0 to 4, provided that if s is 1 or greater, u is 1. (In formula (57), Ar ５１ Ar in formula (54) ５１ It is similar to R ５１７ ~R ５１９ Each of these independently represents an alkyl group which may have substituents other than a crosslinking group, an alkoxy group which may have substituents other than a crosslinking group, an aralkyl group which may have substituents other than a crosslinking group, an aromatic hydrocarbon group which may have substituents other than a crosslinking group, or an aromatic heterocyclic group which may have substituents other than a crosslinking group; f, g, and h are each independently integers from 0 to 4, and e is an integer from 0 to 3, provided that if g is 1 or greater, then e is 1 or greater. (In formula (59), Ar ５１ X, R ２０１ , R ２０２This is Ar in formula (54) above. ５１ X, R ２０１ , R ２０２ It is similar to R ５１８ R in formula (57) is ５１８ It is similar to the two Ar ５１ They may be the same or different, and the two R's ５１８ (These may be the same or different.) [2] A polymer that satisfies the following formulas (1) and (2), and also satisfies the following (i), wherein the total number of carbon atoms of alkyl groups contained in the main chain of the repeating units constituting the polymer is C Ａ The total number of carbon atoms in the alkyl groups contained in the side chains of the repeating units that make up the polymer is C Ｂ A polymer that satisfies the following formula (TI): Abs500nm ≤ 0.004 ... (1) Abs460nm ≤ 0.010 ... (2) Abs500nm and Abs460nm represent the absorbance of a 1% by mass tetrohydrofuran solution of the polymer, respectively. 1.5 ≤ C Ｂ / C Ａ ≤2.2 ... (TI) (i) Having two or more repeating units from among the repeating units represented by the following formula (54), the repeating unit represented by the following formula (55), the repeating unit represented by the following formula (56), and the repeating unit represented by the following formula (57). (In formula (54), Ar ５１ This is a group in which multiple groups selected from the group consisting of an aromatic hydrocarbon group which may have substituents other than a crosslinking group, an aromatic heterocyclic group which may have substituents other than a crosslinking group, or an aromatic hydrocarbon group which may have substituents other than a crosslinking group and an aromatic heterocyclic group which may have substituents other than a crosslinking group are linked directly or via a linking group, provided that N-Ar ５1 In this, the nitrogen atom is not directly bonded to a fused ring, and X is -C(R ２０７ ) (Caution ２０８ )-,-N(R ２０９ )-, or-C(R ２１１ ) (Caution ２１２ )-C(R ２１３ ) (Caution ２１４ ) - and R ２０１ , R ２０２ , R２２１ and R ２２２ Each of these is an alkyl group which may have substituents other than a crosslinking group, and R ２０７ ~R ２０９ and R ２１１ ~R ２１４ Each of these is independently a hydrogen atom, an alkyl group which may have substituents other than a crosslinking group, an aralkyl group which may have substituents other than a crosslinking group, or an aromatic hydrocarbon group which may have substituents other than a crosslinking group, and each of a, b and d is independently an integer from 0 to 4, and c is an integer from 0 to 3, provided that if a is 1 or more, then c is 1 or more, and if b is 1 or more, then d is 1 or more, R ２０１ If there are multiple R's, ２０１ They may be the same or different, R ２０２ If there are multiple R's, ２０２ They may be the same or different, R ２２１ If there are multiple R's, ２２１ They may be the same or different, R ２２２ If there are multiple R's, ２２２ (i and j may be the same or different, and each of them is an independent integer between 0 and 3.) (In formula (55), Ar ５1 Ar in formula (54) ５１ It is similar to N-Ar ５1 In this case, the nitrogen atom is not directly bonded to the fused ring, R ３０３ and R ３０６ Each of these is an alkyl group which may have substituents other than a crosslinking group, and R ３０４ and R ３０５ Each of these is independently an alkyl group which may have substituents other than a crosslinking group, an alkoxy group which may have substituents other than a crosslinking group, or an aralkyl group which may have substituents other than a crosslinking group; l, n, p, and q are each independently 0 or 1; m is 1 or 2, however, if p is 1, l is 1, and if q is 1, n is 1. (In formula (56), Ar ５１ Ar in formula (54)５１ is the same as above, provided that N-Ar ５1 in which the nitrogen atom is not directly bonded to a condensed ring, and Ar ４１ is a divalent aromatic hydrocarbon group which may have a substituent other than a crosslinking group, a divalent aromatic heterocyclic group which may have a substituent other than a crosslinking group, or a plurality of groups selected from the group consisting of a divalent group in which a divalent aromatic hydrocarbon group which may have a substituent other than a crosslinking group and a divalent aromatic heterocyclic group which may have a substituent other than a crosslinking group are directly or via a linking group linked, and R ４４１ and R ４４２ are each independently an alkyl group which may have a substituent other than a crosslinking group, t is 1 or 2, u is 0 or 1, r and s are each independently an integer of 0 to 4, provided that when s is 1 or more, u is 1. ) (In formula (57), Ar ５１ is the same as Ar in the above formula (54) ５１ provided that N-Ar ５1 in which the nitrogen atom is not directly bonded to a condensed ring, and R ５１７ to R ５１９ are each independently an alkyl group which may have a substituent other than a crosslinking group, an alkoxy group which may have a substituent other than a crosslinking group, an aralkyl group which may have a substituent other than a crosslinking group, an aromatic hydrocarbon group which may have a substituent other than a crosslinking group, or an aromatic heterocyclic group which may have a substituent other than a crosslinking group, f, g and h are each independently an integer of 0 to 4, e is an integer of 0 to 3, provided that when g is 1 or more, e is 1 or more. ) [3] A polymer according to [1] or [2] above, containing a partial structure represented by the following formula (61) or the following formula (61'). (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 , R in formula (57)５１７ , R ５１８ , or R ５１９ This represents at least one of the following, where -* indicates the bond position with an adjacent atom. If formulas (61) and (61') are substructures of formula (54) or formula (56), Ring B may be part of a fused ring. The substructures represented by formulas (61) and (61') are R ６０１ In addition, if the structural parts of Ring A and Ring B are substructures of formula (54), then R ２０１ or R ２０２ However, if it is a substructure of equation (55), then R ３０３ , R ３０４ , R ３０５ , or R ３０６ However, if it is a substructure of equation (56), then R ４４１ or R ４４２ However, if it is a substructure of equation (57), then R ５１７ , R ５１８ or R ５１９ (These may be bonded together.) [4] The polymer according to [2] or [3] above, comprising a repeating unit represented by the following formula (59). (In formula (59), Ar ５１ X, R ２０１ , R ２０２ This is Ar in formula (54) above. ５１ X, R ２０１ , R ２０２ It is similar to N-Ar ５1 In this case, the nitrogen atom is not directly bonded to the fused ring, R ５１８ R in formula (57) is ５１８ It is similar to the two Ar ５１ They may be the same or different, and the two R's ５１８ They may be the same or different.) [5] In the above formula (59), if X is -C(R ２０７ ) (Caution ２０８ ) - and R ２０１ , R ２０２ , R ５１８ , R ２０７ , R ２０８ A polymer according to any one of [1] to [4] above, wherein each of is an alkyl group. [6] In formula (59), Ar５１ The polymer according to any one of [1] to [5] above, wherein at least one of is a biphenyl group substituted with an alkyl group. [7] The Ar in the repeating unit represented by formulas (54), (55), (56), (57), and (59) ５１ A polymer according to any one of [1], [3] to [6], wherein at least one of the is represented by the following formula (81). (In formula (81), Fu is a monovalent aromatic hydrocarbon condensed ring group which may have substituents, or a carbazolyl group which may have substituents, and ab is an integer from 0 to 1.) [8] The Ar in the repeating units represented by formulas (54), (55), (56), and (57) ５１ A polymer according to any one of [2] to [6] above, wherein at least one of is represented by the following formula (81). (In formula (81), Fu is a monovalent aromatic hydrocarbon condensed ring group which may have substituents, or a carbazolyl group which may have substituents, and ab is an integer from 0 to 1.) [9] The polymer according to [7] or [8] above, wherein Fu in formula (81) is a fluorenyl group which may have substituents.

[10] The polymer according to any one of [7] to [9] above, wherein formula (81) is the following formula (82). (In formula (82), Fu is a monovalent aromatic hydrocarbon condensed ring group which may have substituents, or a carbazolyl group which may have substituents, and ab is an integer from 0 to 1.)

[11] A composition for forming an organic film, comprising the polymer according to any one of [1] to

[10] above and a solvent.

[12] A method for producing an organic film, formed by a wet film formation method using the organic film-forming composition according to

[11] above.

[13] An organic electroluminescent element having an organic layer comprising the polymer according to any one of [1] to

[10] above.

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

[13] above.

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

[13] above.

[0015] According to the present invention, when used in the organic layer constituting an organic electroluminescent element, a polymer can be provided that yields an organic electroluminescent element with higher luminous efficiency than conventional ones. Furthermore, according to the present invention, a polymer can be provided that yields an organic electroluminescent element with an even longer operating life. According to the present invention, an organic film-forming composition containing the above polymer, a method for producing an organic film using the organic film-forming composition, an organic electroluminescent element having an organic layer containing the polymer according to an embodiment of the present invention, a display device equipped with the organic electroluminescent element, and a lighting device.

[0016] Figure 1 is a schematic cross-sectional view showing an example of the structure of an organic electroluminescent element according to an embodiment of the present invention.

[0017] The following describes in detail embodiments of the present invention. The present invention is not limited to the following embodiments, and can be implemented in various ways within the scope of its gist.

[0018] In this invention, "may have substituents" means that it may have one or more substituents. When the expression "~" is used in this specification, it is used to include the numerical value or physical property value before and after it.

[0019] In this specification, (hetero)aralkyl group, (hetero)aryloxy group, and (hetero)aryl group refer to an aralkyl group that may contain a heteroatom, an aryloxy group that may contain a heteroatom, and an aryl group that may contain a heteroatom, respectively. "May contain a heteroatom" means that one or more carbon atoms among the carbon atoms forming the aryl skeleton in the main skeleton of the aralkyl group, aryloxy group, or aryl group are substituted with heteroatoms. Examples of heteroatoms include nitrogen atoms, oxygen atoms, sulfur atoms, phosphorus atoms, silicon atoms, etc., and among these, nitrogen atoms are preferred from the viewpoint of durability.

[0020] In this specification, the term (hetero)aryl group is used to mean a group that includes a monocyclic group, a 2- to 4-cyclic fused ring group, or a group in which multiple monocyclic and / or 2- to 4-cyclic fused ring groups are linked together. The term (hetero)aryl group refers to an aryl group that may contain a heteroatom, i.e., an aryl group or a heteroaryl group, where an aryl group is an aromatic hydrocarbon group and a heteroaryl group is an aromatic heterocyclic group.

[0021] [Polymers] The polymer according to the first embodiment of the present invention is a polymer that satisfies the following formulas (1) and (2), and at least one of the following (i) and (ii). Abs 500 nm ≤ 0.004 ... (1) Abs 460 nm ≤ 0.010 ... (2) Abs 500 nm and Abs 460 nm each represent the absorbance of a 1 mass% tetrohydrofuran solution of the polymer. (i) Having two or more repeating units from among the repeating units represented by the following formula (54), the repeating units represented by the following formula (55), the repeating units represented by the following formula (56), and the repeating units represented by the following formula (57). (ii) Consisting of only one or more repeating units from among the repeating units represented by the following formula (54), the repeating units represented by the following formula (55), the repeating units represented by the following formula (56), and the repeating units represented by the following formula (57).

[0022]

[0023] In formula (54), Ar ５1 X is a group in which multiple groups selected from the group consisting of an aromatic hydrocarbon group which may have substituents other than a crosslinking group, an aromatic heterocyclic group which may have substituents other than a crosslinking group, or an aromatic hydrocarbon group which may have substituents other than a crosslinking group and an aromatic heterocyclic group which may have substituents other than a crosslinking group are linked directly or via a linking group, and X is -C(R ２０７ ) (Caution ２０８ )-,-N(R ２０９ )-, or-C(R ２１１ ) (Caution ２１２ )-C(R ２１３ ) (Caution ２１４ ) - and R ２０１ , R ２０２ , R ２２１ and R２２２ Each of these is an alkyl group which may have substituents other than a crosslinking group, and R ２０７ ~R ２０９ and R ２１１ ~R ２１４ Each is independently a hydrogen atom, an alkyl group which may have substituents other than a crosslinking group, an aralkyl group which may have substituents other than a crosslinking group, or an aromatic hydrocarbon group which may have substituents other than a crosslinking group, and a, b and d are each independently integers from 0 to 4, and c is an integer from 0 to 3, provided that if a is 1 or more, then c is 1 or more, and if b is 1 or more, then d is 1 or more, R ２０１ If there are multiple R's, ２０１ They may be the same or different, R ２０２ If there are multiple R's, ２０２ They may be the same or different, R ２２１ If there are multiple R's, ２２１ They may be the same or different, R ２２２ If there are multiple R's, ２２２ i and j are integers between 0 and 3, and they may be the same or different.

[0024]

[0025] In formula (55), Ar ５1 Ar in formula (54) ５１ It is similar to R ３０３ and R ３０６ Each of these is an alkyl group which may have substituents other than a crosslinking group, and R ３０４ and R ３０５ Each is independently an alkyl group which may have substituents other than a crosslinking group, an alkoxy group which may have substituents other than a crosslinking group, or an aralkyl group which may have substituents other than a crosslinking group, l, n, p and q are each independently 0 or 1, and m is 1 or 2, provided that when p is 1, l is 1, and when q is 1, n is 1.

[0026]

[0027] In formula (56), Ar ５１ Ar in formula (54) ５１ It is similar to Ar ４１ R is a divalent aromatic hydrocarbon group which may have substituents other than a crosslinking group, a divalent aromatic heterocyclic group which may have substituents other than a crosslinking group, or a divalent group in which a plurality of groups selected from the group consisting of the divalent aromatic hydrocarbon group and the divalent aromatic heterocyclic group are linked directly or via a linking group, ４４１ and R ４４２ Each is independently an alkyl group which may have substituents other than a crosslinking group, t is 1 or 2, u is 0 or 1, and r and s are each independently integers from 0 to 4, provided that if s is 1 or greater, u is 1.

[0028]

[0029] In formula (57), Ar ５１ This is Ar in formula (54) above. ５１ It is similar to R ５１７ ~R ５１９ Each independently represents an alkyl group which may have substituents other than a crosslinking group, an alkoxy group which may have substituents other than a crosslinking group, an aralkyl group which may have substituents other than a crosslinking group, an aromatic hydrocarbon group which may have substituents other than a crosslinking group, or an aromatic heterocyclic group which may have substituents other than a crosslinking group, and each independently is an integer from 0 to 4, and e is an integer from 0 to 3, provided that if g is 1 or more, then e is 1 or more.

[0030] The polymer according to the first embodiment of the present invention also includes a repeating unit represented by the following formula (59).

[0031]

[0032] In formula (59), Ar ５１ X, R ２０１ , R ２０２ This is Ar in the above formula (54). ５１ X, R ２０１ , R ２０２ It is similar to R ５１８is the same as R in the above formula (57). ５１８ is the same, and the two Ars ５１ may be the same or different, and the two Rs ５１８ may be the same or different.

[0033] The polymer according to the first embodiment of the present invention satisfies the above formulas (1) and (2), so that there are few secondary amine compounds and oxidized products of amine structures contained in trace amounts in the polymer. When the polymer receives holes, it tends to be stable in a radical cation state and is less likely to deteriorate. In addition, there are few organic halogen compounds and metal impurities contained in trace amounts in the polymer, there are few charge trap sites, and it tends to be possible to efficiently transport charges. Further, the polymer according to the first embodiment of the present invention satisfies at least one of the following (i) and (ii), so that it has high solubility in an organic solvent and tends to have excellent stability in a solution state. Furthermore, since the energy gap is wide and it tends to have excellent electron blocking properties, when this polymer is used for an organic layer constituting an organic electroluminescent device, particularly a hole transport layer, it is considered that hole injection into a material having a deep HOMO in an adjacent light emitting layer is promoted. From the above, it is considered that an organic electroluminescent device with high efficiency and long life can be obtained by using the polymer according to the first embodiment of the present invention.

[0034] <Formulas (1), Formula (2)> The polymer according to the first embodiment of the present invention satisfies the following formulas (1) and (2). Abs500nm ≤ 0.004 ··· (1) Abs460nm ≤ 0.010 ··· (2) Abs500nm and Abs460nm each represent the absorbance of a 1% by mass tetrahydrofuran solution of the polymer at wavelengths of 500 nm and 460 nm, respectively.

[0035] When the Abs500nm of the polymer is 0.004 or less as in formula (1), there are few secondary amine compounds and oxidized products of amine structures contained in trace amounts in the polymer. When the polymer receives holes, it becomes stable in the radical cation state and is less likely to deteriorate. When such a polymer is used in an organic layer constituting an organic electroluminescent device, particularly in a hole transport layer, the driving life of the organic electroluminescent device tends to be long. From such a viewpoint, the Abs500nm of the polymer is preferably 0.0038 or less, more preferably 0.0035 or less, still more preferably 0.0030 or less, and even more preferably less than 0.003. The lower limit is not particularly limited, but is usually 0.001 or more.

[0036] On the other hand, when the Abs460nm of the polymer is 0.010 or less as in formula (2), there are few organic halogen compounds and metal impurities contained in trace amounts in the polymer, there are few charge trap sites, and it becomes possible to efficiently transport charges. When such a polymer is used in an organic layer constituting an organic electroluminescent device, particularly in a hole transport layer, the luminous efficiency of the organic electroluminescent device tends to be high. From such a viewpoint, the Abs460nm of the polymer is preferably 0.008 or less, preferably 0.007 or less, more preferably 0.006 or less, and even more preferably less than 0.006. The lower limit is not particularly limited, but is usually 0.001 or more.

[0037] Abs500nm and Abs460nm are obtained by using a 1% by mass tetrahydrofuran solution of the polymer, irradiating light with wavelengths of 460 nm and 500 nm respectively with a spectrophotometer, and calculating the absorbance Abs (= log ０ (I １０ / I)) from the incident light intensity I ０ and the transmitted light intensity I.

[0038] The tetrahydrofuran used for preparing the 1% by mass tetrahydrofuran solution of the polymer is not particularly limited, but is preferably one that does not contain a stabilizer.

[0039] The polymer according to the second embodiment of the present invention is a polymer that satisfies the following (i). The total number of carbon atoms C of the alkyl groups contained in the main chain of all repeating units constituting the polymer ＡThe total number of carbon atoms in the alkyl groups contained in the side chains of the repeating units that make up the polymer is C Ｂ It is a polymer that satisfies the following formula (TI): 1.5 ≤ C Ｂ / C Ａ ≤2.2 ... (TI) (i) Having two or more repeating units from among the repeating units represented by the following formula (54), the repeating unit represented by the following formula (55), the repeating unit represented by the following formula (56), and the repeating unit represented by the following formula (57). (In formula (54), Ar ５1 This is a group in which multiple groups selected from the group consisting of an aromatic hydrocarbon group which may have substituents other than a crosslinking group, an aromatic heterocyclic group which may have substituents other than a crosslinking group, or an aromatic hydrocarbon group which may have substituents other than a crosslinking group and an aromatic heterocyclic group which may have substituents other than a crosslinking group are linked directly or via a linking group, provided that N-Ar ５1 In this, the nitrogen atom is not directly bonded to a fused ring, and X is -C(R ２０７ ) (Caution ２０８ )-,-N(R ２０９ )-, or-C(R ２１１ ) (Caution ２１２ )-C(R ２１３ ) (Caution ２１４ ) - and R ２０１ , R ２０２ , R ２２１ and R ２２２ Each of these is an alkyl group which may have substituents other than a crosslinking group, and R ２０７ ~R ２０９ and R ２１１ ~R ２１４ Each is independently a hydrogen atom, an alkyl group which may have substituents other than a crosslinking group, an aralkyl group which may have substituents other than a crosslinking group, or an aromatic hydrocarbon group which may have substituents other than a crosslinking group, and a, b and d are each independently integers from 0 to 4, and c is an integer from 0 to 3, provided that if a is 1 or more, then c is 1 or more, and if b is 1 or more, then d is 1 or more, R ２０１ If there are multiple R's, ２０１ They may be the same or different, R ２０２If there are multiple R's, ２０２ They may be the same or different, R ２２１ If there are multiple R's, ２２１ They may be the same or different, R ２２２ If there are multiple R's, ２２２ (i and j may be the same or different, and each of them is an independent integer between 0 and 3.) (In formula (55), Ar ５1 Ar in formula (54) ５１ It is similar to N-Ar ５1 In this case, the nitrogen atom is not directly bonded to the fused ring, R ３０３ and R ３０６ Each of these is an alkyl group which may have substituents other than a crosslinking group, and R ３０４ and R ３０５ Each of these is independently an alkyl group which may have substituents other than a crosslinking group, an alkoxy group which may have substituents other than a crosslinking group, or an aralkyl group which may have substituents other than a crosslinking group; l, n, p, and q are each independently 0 or 1; m is 1 or 2, however, if p is 1, l is 1, and if q is 1, n is 1. (In formula (56), Ar ５１ Ar in formula (54) ５１ It is similar to N-Ar ５1 In this, the nitrogen atom is not directly bonded to the fused ring, Ar ４１ R is a divalent group in which multiple groups selected from the group consisting of a divalent aromatic hydrocarbon group which may have substituents other than a crosslinking group, a divalent aromatic heterocyclic group which may have substituents other than a crosslinking group, or an aromatic hydrocarbon group which may have substituents other than a crosslinking group and an aromatic heterocyclic group which may have substituents other than a crosslinking group are directly or via a linking group, ４４１ and R ４４２Each of these is an alkyl group which may have substituents other than a crosslinking group, t is 1 or 2, u is 0 or 1, and r and s are each an integer from 0 to 4, provided that if s is 1 or greater, u is 1. (In formula (57), Ar ５１ Ar in formula (54) ５１ It is similar to N-Ar ５1 In this case, the nitrogen atom is not directly bonded to the fused ring, R ５１７ ~R ５１９ Each of these independently represents an alkyl group which may have substituents other than a crosslinking group, an alkoxy group which may have substituents other than a crosslinking group, an aralkyl group which may have substituents other than a crosslinking group, an aromatic hydrocarbon group which may have substituents other than a crosslinking group, or an aromatic heterocyclic group which may have substituents other than a crosslinking group; f, g, and h are each independently integers from 0 to 4, and e is an integer from 0 to 3, provided that if g is 1 or greater, then e is 1 or greater.

[0040] In a second embodiment of the present invention, formulas (1) and (2), and (i) and (ii) are the same as those described in the first embodiment.

[0041] The polymer in another aspect of the second embodiment of the present invention preferably satisfies formulas (1) and (2) above, and satisfies at least one of (i) and (ii) below, wherein the total number of carbon atoms of the alkyl groups contained in the main chain of the repeating units constituting the polymer is C Ａ The total number of carbon atoms in the alkyl groups contained in the side chains of the repeating units that make up the polymer is C Ｂ It is a polymer that satisfies the following formula (TI): 1.5 ≤ C Ｂ / C Ａ≤2.2 ... (TI) (i) Having two or more repeating units from among the repeating units represented by formula (54), formula (55), formula (56), and formula (57). (ii) Consisting of only one or more repeating units from among the repeating units represented by formula (54), formula (55), formula (56), and formula (57). In this embodiment of the second embodiment, formulas (1) and (2), and (i) and (ii) above are the same as those described in the first embodiment.

[0042] <Formula (TI)> The polymer according to the second embodiment of the present invention satisfies the following formula (TI): 1.5 ≤ C Ｂ / C Ａ ≦2.2...(TI)

[0043] In formula (TI), C Ａ This represents the total number of carbon atoms in the alkyl groups contained in the main chain of the repeating units that make up the polymer, C Ｂ This represents the total number of carbon atoms in the alkyl groups contained in the side chains of the repeating units that make up the polymer.

[0044] Alkyl groups include linear or branched alkyl groups. The main chain refers to the continuous chain that forms the primary structure of the polymer; for example, in the following formula, N-Ar ｍ This is the structure represented by -. On the other hand, a side chain is a branch that is bonded to the main chain of a polymer, for example, in the following formula, Ar ｓ This is a structure represented by [this].

[0045]

[0046] C Ａ and C Ｂ The calculation method is shown below using polymers P-C1 and P-C2 as examples.

[0047]

[0048] In the case of the polymer P-C1 described above, C Ａ =1+6×2+1=14,C Ｂ=3 + 3 = 6, and C Ｂ / C Ａ = 6 / 14 = 0.429.

[0049]

[0050] In the polymer P-C2 described above, the number in the lower right of the structure represents the molar ratio of the repeating units. In the case of polymer P-C2 described above, C Ａ =16×0.9+16×0.1=16,C Ｂ = (3 + 3) × 0.9 = 5.4, and C Ｂ / C Ａ = 5.4 / 16 = 0.338.

[0051] C Ｂ / C Ａ If the value is less than 1.5, it is possible that (a) the proportion of alkyl groups in the main chain of the repeating units constituting the polymer is large, or (b) the total number of carbon atoms in the alkyl groups in the side chains of the repeating units constituting the polymer is small. In case (a), the packing of the main chain in the film is suppressed due to the influence of alkyl groups that are abundant in the main chain, which reduces charge transport performance and is undesirable. In case (b), it is undesirable because solubility suitable for the coating process cannot be ensured.

[0052] On the other hand, C Ｂ / C Ａ If the ratio is greater than 2.2, it is possible that (c) the proportion of alkyl groups in the main chain of the repeating units constituting the polymer is small, or (d) the total number of carbon atoms in the alkyl groups in the side chains of the repeating units constituting the polymer is large. In case (c), it is undesirable because suitable solubility for the coating process cannot be ensured. In case (d), the solubility of the polymer is high, which suppresses polymer packing in the film, making it undesirable for forming a laminated structure in the coating process. Ｂ / C Ａ The fact that is within the range of formula (TI) results in a polymer that has solubility applicable to the coating process, good charge transport properties without inhibiting packing in the film, and solvent resistance that allows for the formation of a laminated structure in the coating process.

[0053] From the above, it is considered that a highly efficient, long-life organic electroluminescent device can be obtained by using the polymer according to the second embodiment. Ｂ / C Ａ From the above viewpoint, it is more preferable that the value is 2.0 or more and 2.2 or less, even more preferable that it is 2.1 or more and 2.2 or less, even more preferable that it is 2.15 or more and 2.2 or less, and particularly preferable that it is 2.18 or more and 2.2 or less.

[0054] The polymer according to the third embodiment of the present invention is a polymer comprising repeating units represented by the following formula (50), wherein each repeating unit represented by the following formula (50) comprises a main chain (N-Ar ５２ The ratio of the number of nitrogen atoms to the total number of carbon atoms that make up the carbon atom N / C (main) and the side chain (Ar ５１ The ratio of nitrogen atoms to the total number of carbon atoms constituting the main chain, N / C(side), satisfies the following formula (a), and the ratio of nitrogen atoms to carbon atoms per repeating unit represented by the following formula (50) is N-Ar ５２ The molecular weight Mw (main) and the side chain (Ar ５１ The polymer is such that its molecular weight Mw(side) satisfies the following formula (b): 0 ≤ [N / C(side)] / [N / C(main)] < 0.25 ... (a) 0 < Mw(side) / Mw(main) ≤ 0.85 ... (b)

[0055]

[0056] In formula (50), Ar ５１ This represents a monovalent group formed by linking multiple groups selected from substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted aromatic hydrocarbon groups and substituted or unsubstituted aromatic heterocyclic groups, and multiple Ar ５１ If they exist, they may be the same or different, Ar ５２ This represents a divalent group in which multiple groups selected from the group consisting of substituted or unsubstituted divalent aromatic hydrocarbon groups, substituted or unsubstituted divalent aromatic heterocyclic groups, or substituted or unsubstituted aromatic hydrocarbon groups and substituted or unsubstituted aromatic heterocyclic groups are directly or via linking groups, and multiple Ar ５２If they exist, they may be identical or different.

[0057] The reason why the polymer of the third embodiment exhibits the above effects is not entirely clear, but the following is a possible explanation. In an organic electroluminescent device having an organic layer containing the polymer of the third embodiment, not only the main chain structure of the polymer but also the side chain structure plays a significant role at the interface between the organic layer and the cathode-side adjacent layer. For example, when the side chains of the polymer contain heteroaryl structures such as carbazole rings, they have relatively low-energy occupied orbitals, thus playing a certain role in the injection of holes into the adjacent layer, while also having relatively low-energy empty orbitals, making them more likely to accept electrons from the adjacent layer. When the side chains of the polymer contain many heteroaryl structures, in an organic electroluminescent device having an organic layer containing the polymer, the side chain structure may accept electrons at the interface between the organic layer and the cathode-side adjacent layer, generating a reduced state, which may cause a degradation reaction in the side chain or main chain structure of the polymer. Furthermore, if the ratio of the molecular weight of the side chains to the main chain is large, the spread of empty orbitals may become too large, or the proportion occupied by the side chain structure at the interface may become too large, which can easily accelerate the above degradation reaction. From the above, it is believed that by controlling the ratio of nitrogen atoms to carbon atoms constituting the main chain, the ratio of nitrogen atoms to carbon atoms constituting the side chain, and the ratio of molecular weight of the main chain to molecular weight of the side chain within a predetermined range, degradation of the polymer contained in the organic layer due to electrons received from the cathode-side adjacent layer can be suppressed, resulting in an organic electroluminescent element with a low driving voltage, high luminous efficiency, and long driving life.

[0058] [N / C(side) / N / C(main)] The polymer of the third embodiment has a main chain (N-Ar) per repeating unit represented by formula (50). ５２ The ratio of nitrogen atoms to carbon atoms in the main chain (N / C) and the side chain (Ar ５１ The ratio of nitrogen atoms to carbon atoms in a given carbon atom, N / C(side), satisfies the following equation (a): 0 ≤ [N / C(side)] / [N / C(main)] < 0.25 ... (a)

[0059] When the polymer of the third embodiment has repeating units represented by two or more formulas (50), N / C(main) is the ratio of the sum of the values obtained by multiplying the number of carbon atoms constituting each repeating unit by the mole fraction of each repeating unit with respect to the total repeating units represented by the formula (50), to the sum of the values obtained by multiplying the number of nitrogen atoms constituting each repeating unit by the mole fraction of each repeating unit with respect to the total repeating units represented by the formula (50).

[0060] When the polymer of the third embodiment has two or more side chain structures in the repeating unit represented by the formula (50), N / C(side) is the ratio of the sum of the values obtained by multiplying the number of carbon atoms constituting each side chain by the mole fraction of each side chain with respect to the total side chains, to the sum of the values obtained by multiplying the number of nitrogen atoms constituting each side chain by the mole fraction of each side chain with respect to the total side chains.

[0061] Taking the following polymer as an example, N / C(side) is calculated as (2×0.1 + 0×0.35 + 0×0.55) / (73×0.1 + 25×0.35 + 15×0.55), N / C(main) is calculated as (1×0.5 + 1×0.5) / (26×0.5 + 29×0.5), and N / C(side) / N / C(main) ≒ 0.23 is calculated. In the following polymer, each dotted frame corresponds to the repeating unit represented by the formula (50). That is, in the following formula, it means that there are two kinds of repeating units represented by the formula (50).

[0062] I [[ID=]]

[0063] [Mw(side) / Mw(main)] The polymer of the third embodiment satisfies the following formula (b) for the molecular weight Mw(main) of the main chain (N-Ar ５２ ) and the molecular weight Mw(side) of the side chain (Ar ５１ ) per repeating unit represented by the formula (50). 0 < Mw(side) / Mw(main) ≦ 0.85...(b)

[0064] If the polymer of the third embodiment has two or more repeating units represented by formula (50), Mw (main) is the sum of the values ​​obtained by multiplying the molecular weight of the main chain of each repeating unit by the mole fraction of each repeating unit relative to the total repeating units represented by formula (50).

[0065] In the case where the polymer of the third embodiment has two or more side chain structures in the repeating unit represented by formula (50), Mw(side) is the sum of the values ​​obtained by multiplying the molecular weight of each side chain by the mole fraction of each side chain relative to the total side chain.

[0066] Mw(s) / Mw(m) is greater than 0, preferably greater than 0.4, more preferably greater than 0.6, and even more preferably greater than 0.7. The upper limit is 0.85 or less. It is preferable that Mw(s) / Mw(m) is greater than or equal to the lower limit above, as this allows for greater exposure of the side chain structure at the adjacent layer interface, protecting the reduction-sensitive main chain from reduction by electrons in the adjacent layer. Furthermore, the spread of empty orbitals distributed in the side chains and the distance between the main chains of the polymer are optimized, which is expected to improve the performance of the organic electroluminescent device. It is also preferable that the value is less than or equal to the upper limit above, as this tends to prevent the side chain structure from becoming too large and thus not hindering charge transport in the main chain.

[0067] The first to third embodiments of the present invention described above will now be explained in more detail. The first to third embodiments may be collectively referred to simply as "embodiments of the present invention," and terms used in common in each embodiment (for example, "repeating unit represented by formula (54)") have the same meaning and will be described collectively below.

[0068] As described above, the polymer according to the embodiment of the present invention is a polymer containing repeating units represented by the following formula (50).

[0069]

[0070] (Ar ５１) In the repeating unit represented by the above formula (50), a monovalent group is formed by linking multiple groups selected from substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted aromatic hydrocarbon groups and substituted or unsubstituted aromatic heterocyclic groups, and multiple Ar ５１ If they exist, they may be identical or different.

[0071] The aromatic hydrocarbon group is preferably one having 6 to 60 carbon atoms. Specifically, examples include monovalent groups of 6-membered rings or 2- to 5-fused rings, such as benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, perylene rings, tetracene rings, pyrene rings, benzpyrene rings, chrysene rings, triphenylene rings, acenaphthene rings, fluorantene rings, and fluorene rings, or groups formed by linking multiple such rings. Of the above, for example, "monovalent group of a benzene ring" means "a benzene ring with a monovalent free valence," that is, a phenyl group.

[0072] The aromatic heterocyclic group is preferably a monovalent group of a 5-6 membered ring or a 2-4 fused ring, such as a furan ring, benzofuran ring, thiophene ring, benzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, oxadiazole ring, indole ring, carbazole ring, pyrroloimidazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring, phlopyrrole ring, phlofuran ring, thienofuran ring, benzoisoxazole ring, benzoisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring, quinoline ring, isoquinoline ring, sinnoline ring, quinoxaline ring, phenantholidine ring, benzimidazole ring, perimidine ring, quinazoline ring, quinazolinone ring, azulene ring, etc., or a group in which multiple such groups are linked. Similarly, for aromatic heterocyclic groups, for example, "a monovalent group of a furan ring" means "a furan ring with a monovalent free valence," that is, a furyl group.

[0073] Ar ５１From the standpoint of excellent charge transport properties and durability, substituted or unsubstituted aromatic hydrocarbon groups are preferred, and among them, monovalent groups of substituted or unsubstituted benzene rings or fluorene rings, i.e., substituted or unsubstituted phenyl groups or fluorenyl groups are more preferred. In one embodiment of the present invention (for example, the first and second embodiments), Ar ５１ From the standpoint of excellent charge transport properties and durability, aromatic hydrocarbon groups which may have substituents other than the crosslinking group are preferred, among which monovalent groups of benzene rings or fluorene rings which may have substituents other than the crosslinking group are more preferred, phenyl groups or biphenyl groups which may have substituents other than the crosslinking group are even more preferred, biphenyl groups which may have substituents other than the crosslinking group are even more preferred, and para-bonded biphenyl groups which may have substituents other than the crosslinking group are particularly preferred.

[0074] Ar ５１ The substituents that the aromatic hydrocarbon group and aromatic heterocyclic group may have are not particularly limited, as long as they do not significantly reduce the properties of the polymer. Preferably, the substituents are groups selected from the substituent group Z2 below, with alkyl groups, alkoxy groups, aromatic hydrocarbon groups, or aromatic heterocyclic groups being more preferred, and alkyl groups being even more preferred.

[0075] In a third embodiment of the present invention, Ar ５１ From the viewpoint of solubility in the coating solvent, a fluorenyl group substituted with an alkyl group having 1 to 24 carbon atoms is preferred, and a 2-fluorenyl group substituted with an alkyl group having 4 to 12 carbon atoms is particularly preferred. Furthermore, a 9-alkyl-2-fluorenyl group in which the 9th position of the 2-fluorenyl group is substituted with an alkyl group is preferred, and a 9,9-dialkyl-2-fluorenyl group substituted with two alkyl groups is particularly preferred. When at least one of the 9th position of the fluorenyl group is substituted with an alkyl group, the solubility in the solvent and the durability of the fluorene ring tend to improve. Furthermore, when both positions of the 9th position are substituted with alkyl groups, the solubility in the solvent and the durability of the fluorene ring tend to improve even further. ５１From the viewpoint of solubility in the coating solvent, it is also preferable that it be a spirobifluorenyl group, and more preferably a biphenyl group substituted with an alkyl group having 1 to 24 carbon atoms, or a biphenylfluorenyl group.

[0076] Ar ５１ It is preferable that it has at least two different structures. Also, N-Ar ５１ In this case, it is preferable that the nitrogen atom is not directly bonded to a fused ring.

[0077] <Substituent Group Z2> Substituent group Z2 consists of alkyl groups, alkoxy groups, aryloxy groups, heteroaryloxy groups, alkoxycarbonyl groups, dialkylamino groups, diarylamino groups, arylalkylamino groups, acyl groups, halogen atoms, haloalkyl groups, alkylthio groups, arylthio groups, silyl groups, siloxy groups, cyano groups, aromatic hydrocarbon groups, and aromatic heterocyclic groups. These substituents may include linear, branched, or cyclic structures.

[0078] More specifically, the substituent group Z2 may include the following structures: linear, branched, or cyclic alkyl groups, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-hexyl, cyclohexyl, and dodecyl groups, which typically have 1 or more carbon atoms, preferably 3 or more, more preferably 4 or more, and typically 24 or fewer, preferably 12 or fewer, more preferably 8 or fewer, and even more preferably 6 or fewer; alkoxy groups, such as methoxy and ethoxy groups, which typically have 1 or more carbon atoms, and typically 24 or fewer, and preferably 12 or fewer; aryloxy or heteroaryloxy groups, such as phenoxy, naphthoxy, and pyridyloxy groups, which typically have 4 or more carbon atoms, preferably 5 or more, more preferably 6 or more, and typically 36 or fewer, and preferably 24 or fewer; For example, alkoxycarbonyl groups such as methoxycarbonyl groups and ethoxycarbonyl groups, which typically have 2 or more carbon atoms, and usually 24 or fewer, preferably 12 or fewer; dialkylamino groups such as dimethylamino groups and diethylamino groups, which typically have 1 or more carbon atoms, preferably 2 or more, and usually 24 or fewer, preferably 12 or fewer; diarylamino groups such as diphenylamino groups and ditolylamino groups, which typically have 10 or more carbon atoms, preferably 12 or more, more preferably 14 or more, and usually 36 or fewer, preferably 24 or fewer; arylalkylamino groups such as phenylmethylamino groups, which typically have 7 or more carbon atoms, and usually 36 or fewer, preferably 24 or fewer; acyl groups such as acetyl groups and benzoyl groups, which typically have 2 or more carbon atoms, and usually 24 or fewer, preferably 12 or fewer; halogen atoms such as fluorine atoms and chlorine atoms; haloalkyl groups such as trifluoromethyl groups, which typically have 1 or more carbon atoms, and usually 12 or fewer, preferably 6 or fewer; For example, alkylthio groups such as methylthio groups and ethylthio groups, which typically have one or more carbon atoms, and typically 24 or fewer carbon atoms, preferably 12 or fewer carbon atoms;Examples include: arylthio groups such as phenylthio groups, naphthylthio groups, and pyridylthio groups, which typically have 4 or more carbon atoms, preferably 5 or more, more preferably 6 or more, and typically 36 or less, preferably 24 or less; silyl groups such as trimethylsilyl groups and triphenylsilyl groups, which typically have 2 or more carbon atoms, preferably 3 or more, and typically 36 or less, preferably 24 or less; siloxy groups such as trimethylsiloxy groups and triphenylsiloxy groups, which typically have 2 or more carbon atoms, preferably 3 or more, and typically 36 or less, preferably 24 or less; cyano groups; aromatic hydrocarbon groups such as phenyl groups and naphthyl groups, which typically have 6 or more carbon atoms, and typically 36 or less, preferably 24 or less; and aromatic heterocyclic groups such as thienyl groups and pyridyl groups, which typically have 3 or more carbon atoms, preferably 4 or more, more preferably 5 or more, and typically 36 or less, preferably 24 or less; and these may be unsubstituted or further substituted. ;

[0079] Among the substituent group Z2 described above, the substituents are preferably alkyl groups, alkoxy groups, diarylamino groups, aromatic hydrocarbon groups, or aromatic heterocyclic groups. From the viewpoint of charge transport, aromatic hydrocarbon groups or aromatic heterocyclic groups are preferred as substituents, more preferably aromatic hydrocarbon groups, and even more preferably no substituents. From the viewpoint of improving solubility, alkyl groups or alkoxy groups are preferred as substituents.

[0080] Each substituent in the substituent group Z2 may have further substituents. Examples of these substituents are the same as those in the substituent group Z2. The substituents that the substituent group Z2 may have are preferably alkyl groups having 8 or fewer carbon atoms, alkoxy groups having 8 or fewer carbon atoms, or phenyl groups, more preferably alkyl groups having 6 or fewer carbon atoms, alkoxy groups having 6 or fewer carbon atoms, or phenyl groups. From the viewpoint of charge transport, it is more preferable that each substituent in the substituent group Z2 does not have further substituents.

[0081] (Other preferred Ar ５１) Ar in the repeating unit represented by the above formula (50) ５１ It is also preferable that the group comprises a monovalent or divalent group consisting of 2 to 5 linked substituted or unsubstituted benzene rings, a substituted or unsubstituted fluorenyl group, a group represented by the following formula (51), a group represented by the following formula (52), a group represented by the following formula (53), a group represented by the following formula (81), or a group consisting of multiple linked groups thereof. In one embodiment of the present invention, in the first embodiment, Ar ５１ The nitrogen atom to which it is bonded (N-Ar ５１ It is preferable that the fused ring is not directly bonded to the nitrogen atom (represented by ). If the fused ring is directly bonded to the nitrogen atom, the HOMO orbital expands around the nitrogen atom and the fused ring, the HOMO level becomes shallower and the energy gap narrows. Therefore, when this polymer is used as the hole transport layer of an organic light-emitting device, it is thought that the luminous efficiency and operating life may decrease.

[0082] (The base represented by formula (51))

[0083] In formula (51), * represents the bonding position with the nitrogen atom of the main chain in formula (50), Ar ５３ and Ar ５４ Each independently represents a divalent group in which multiple groups selected from the group consisting of substituted or unsubstituted divalent aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted aromatic hydrocarbon groups and substituted or unsubstituted aromatic heterocyclic groups are directly or via linking groups. ５５ Ar represents a monovalent group in which multiple groups selected from the group consisting of substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or aromatic hydrocarbon groups and optionally substituted aromatic heterocyclic groups are directly linked or via linking groups. ５６ represents a hydrogen atom or substituent. In one embodiment of the present invention, in the first and second embodiments described above, Ar ５３ Ar ５４ and Ar ５５ and Ar ５６ The substituents that may be present are substituents other than crosslinking groups. In the detailed description below, Ar ５３ Ar５４ and Ar ５５ and Ar ５６ Examples of substituents that may be present should be read as "substituents other than crosslinking groups." ５３ Ar ５４ and Ar ５５ and Ar ５６ The same interpretation shall apply to examples of specific forms, etc.

[0084] (Ar ５３ Ar ５４ ) In the repeating unit represented by the above formula (51), Ar ５３ and Ar ５４ Each of these independently represents a divalent group in which multiple groups selected from the group consisting of substituted or unsubstituted divalent aromatic hydrocarbon groups, substituted or unsubstituted divalent aromatic heterocyclic groups, or substituted or unsubstituted aromatic hydrocarbon groups and substituted or unsubstituted aromatic heterocyclic groups are linked directly or via linking groups. Preferably, it is a group in which multiple groups selected from the group consisting of substituted or unsubstituted divalent aromatic hydrocarbon groups or substituted or unsubstituted divalent aromatic hydrocarbon groups are linked directly or via linking groups. Here, the substituents that the aromatic hydrocarbon group and the aromatic heterocyclic group may have are those listed in substituent group Z2, and the preferred substituents are the same as those in substituent group Z2.

[0085] Ar ５３ and Ar ５４ The aromatic hydrocarbon group and aromatic heterocyclic group are Ar, as described later. ５２ Similar aromatic hydrocarbon groups and aromatic heterocyclic groups can be used.

[0086] A divalent group formed by the direct linking or via linking groups of multiple groups selected from the group consisting of substituted or unsubstituted aromatic hydrocarbon groups and substituted or unsubstituted aromatic heterocyclic groups may be a group in which multiple identical groups are directly linked, or a group in which multiple different groups are directly linked.

[0087] When multiple divalent groups are linked together, examples include 2 to 10 linked divalent groups, and preferably 2 to 5 linked divalent groups.

[0088] Ar５３ The group is preferably a group consisting of one to six substituted or unsubstituted divalent aromatic hydrocarbon groups linked together, more preferably a group consisting of two to four substituted or unsubstituted divalent aromatic hydrocarbon groups linked together, more preferably a group consisting of one to four substituted or unsubstituted phenylene rings linked together, and particularly preferably a biphenylene group consisting of two substituted or unsubstituted phenylene rings linked together.

[0089] When multiple divalent aromatic hydrocarbon groups or divalent aromatic heterocyclic groups are linked together, it is preferable that the linked divalent aromatic hydrocarbon groups are bonded in such a way that they are not conjugated. Specifically, it is preferable that the group includes a 1,3-phenylene group or a group having substituents that form a twisted structure due to the steric effect of the substituents.

[0090] Ar ５３ Examples of substituents that may be present include the groups listed in substituent group Z2, and preferred substituents are the same as those in substituent group Z2. Preferably, Ar ５３ It has no substituents.

[0091] Ar ５４ From the viewpoint of excellent charge transport and durability, a group consisting of one or more linked divalent aromatic hydrocarbon groups, which may be the same or different, is preferred, and the divalent aromatic hydrocarbon groups may have substituents. When multiple divalent aromatic hydrocarbon groups are linked, the number of linked aromatic hydrocarbon groups is preferably 2 to 10, more preferably 6 or less, and particularly preferred if it is 3 or less from the viewpoint of film stability. Preferred aromatic hydrocarbon structures are benzene rings, naphthalene rings, anthracene rings, and fluorene rings, and more preferably benzene rings and fluorene rings. As for the group consisting of multiple linked groups, a group consisting of one to four linked substituted or unsubstituted phenylene rings, or a group consisting of a substituted or unsubstituted phenylene ring and a substituted or unsubstituted fluorene ring is preferred. From the viewpoint of expanding LUMO, a biphenylene group consisting of two linked substituted or unsubstituted phenylene rings is particularly preferred.

[0092] Ar ５４The substituents that may be present are any of the substituents listed in the substituent group Z2, or a combination thereof, and are preferably other than the N-carbazolyl group, indrocarbazolyl group, and indenocarbazolyl group, and more preferably the phenyl group, naphthyl group, and fluorenyl group. ５４ It is also preferable that it does not have substituents.

[0093] In one embodiment of the present invention, in the first and second embodiments described above, Ar ５３ and Ar ５４ The divalent aromatic hydrocarbon group is preferably one with 6 to 60 carbon atoms, and specifically includes a 6-membered monocyclic or 2- to 5-fused divalent group, such as a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring, acenaphthene ring, fluorantene ring, or fluorene ring, or a group in which these are directly or in multiple linked groups. For example, "divalent group of a benzene ring" means "a benzene ring having a divalent free valence," that is, a phenylene group. The divalent aromatic heterocyclic group is preferably one having 3 to 60 carbon atoms, specifically a furan ring, benzofuran ring, thiophene ring, benzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, oxadiazole ring, indole ring, carbazole ring, pyrroloimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring, phlopyrrole ring, phlofuran ring, thienofuran ring, benzo Examples include divalent groups of 5-6 membered monocyclic or 2-4 fused rings, such as soxazole rings, benzoisothiazole rings, benzimidazole rings, pyridine rings, pyrazine rings, pyridazine rings, pyrimidine rings, triazine rings, quinoline rings, isoquinoline rings, sinnoline rings, quinoxaline rings, phenanthridine rings, benzimidazole rings, perimidine rings, quinazoline rings, quinazolinone rings, and azulene rings, or groups formed by linking multiple such rings. Similarly, for aromatic heterocyclic groups, for example, "divalent group of a furan ring" means "a furan ring with a divalent free valency," i.e., a furanylidene group.

[0094] (Ar５５ ) Ar ５５ This is a monovalent group in which multiple groups selected from the group consisting of substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted aromatic hydrocarbon groups and substituted or unsubstituted aromatic heterocyclic groups are directly linked or via linking groups. Preferably, it is a monovalent group in which multiple groups selected from the group consisting of substituted or unsubstituted aromatic hydrocarbon groups and substituted or unsubstituted aromatic heterocyclic groups are linked.

[0095] Here, examples of substituents that the aromatic hydrocarbon group and the aromatic heterocyclic group may have are the groups listed in substituent group Z2, and preferred substituents are the same as those in substituent group Z2.

[0096] When multiple units are linked together, it is preferable that 2 to 10 units are linked together, and more preferably 2 to 5 units are linked together.

[0097] Ar ５５ The aromatic hydrocarbon group and aromatic heterocyclic group are the Ar ５１ Similar aromatic hydrocarbon groups and aromatic heterocyclic groups can be used.

[0098] Ar ５５ From the viewpoint of distributing the LUMO of the polymer, structures selected from a-1 to a-4, b-1 to b-9, c-1 to c-4, d-1 to d-16, and e-1 to e-4 shown in schemes 1-1 to 1-3 below are preferred. From the viewpoint of promoting the spreading of the polymer's LUMO by having electron-withdrawing groups, structures selected from a-1 to a-4, b-1 to b-9, d-1 to d-12, and e-1 to e-4 are more preferred. Furthermore, from the viewpoint of having a high triplet level and the effect of confining excitons formed in the luminescent layer, structures selected from a-1 to a-4, d-1 to d-12, and e-1 to e-4 are even more preferred. Furthermore, from the viewpoint of being easy to synthesize and having excellent stability, d-1 and d-10 are preferred, and the benzene ring structure of d-1 is particularly preferred. These structures may also have substituents. In schemes 1-1 to 1-3 below, "-*" represents Ar ５４ This indicates the connection position with Ar. If there are multiple "-*" symbols, then one of them is Ar. ５４ This indicates the connection point with [the other element].

[0099]

[0100]

[0101]

[0102] (R ３１ and R ３２ ) R in schemes 1-1 to 1-2 ３１ and R ３２ Each of these is preferably a substituted or unsubstituted linear, branched, or cyclic alkyl group. The number of carbon atoms in the alkyl group is not particularly limited, but in order to maintain the solubility of the polymer in organic solvents, it is preferably 1 or more and 6 or less, more preferably 3 or less, and even more preferably a methyl group or an ethyl group.

[0103] R ３１ and R ３２ They may be the same or different, but since they can uniformly distribute the charge around the nitrogen atom and are also easy to synthesize, all R ３１ and R ３２ It is preferable that they are the same group.

[0104] Ar ５５ The substituents that may be present in Ar are as follows: ５４ Similar substituents can be mentioned, and preferred substituents are also the above Ar ５４ It is similar to that.

[0105] (Ar ５６ ) Ar ５６ Ar represents a hydrogen atom or substituent. ５６ When is a substituent, it is not particularly limited, but is preferably a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group. ５６ The aromatic hydrocarbon group and aromatic heterocyclic group are the Ar ５１ Similar aromatic hydrocarbon groups and aromatic heterocyclic groups can be used.

[0106] Ar ５６ If Ar is a substituent, it is preferable from the viewpoint of improving durability that it is bonded to the 3-position of the carbazole skeleton in formula (51).５６ From the viewpoint of ease of synthesis and charge transport properties, it is preferable that it be a hydrogen atom. ５６ From the viewpoint of improving durability and charge transport, it is preferable that the group is a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, and more preferably a substituted or unsubstituted aromatic hydrocarbon group. Examples of substituents that may be present are those listed in substituent group Z2, and the preferred substituents are the same as those in substituent group Z2.

[0107] (The group represented by formula (52)) Furthermore, as a polymer, from the viewpoint of improving durability, Ar in the repeating unit represented by formula (50) above ５１ It is also preferable that the group is represented by the following formula (52). This is because, in the two carbazole structures in formula (52), the LUMO is distributed between the nitrogen atoms of each other in the aromatic hydrocarbon group or aromatic heterocyclic group, which suppresses the influence on the main chain amine in formula (50) and improves the durability of the main chain amine against electrons and excitons.

[0108]

[0109] In formula (52), Ar ６１ and Ar ６２ Each is independently a substituted or unsubstituted divalent aromatic hydrocarbon group or a substituted or unsubstituted divalent aromatic heterocyclic group, Ar ６３ ~Ar ６５ Each of these is independently a hydrogen atom or a substituent. * indicates the bond position to the nitrogen atom in formula (50).

[0110] (Ar ６３ ~Ar ６５ ) Ar ６３ ~Ar ６５ Each of these independently represents a hydrogen atom or a substituent. ６３ ~Ar ６５ When is a substituent, the substituent is not particularly limited, but is preferably a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group. The aromatic hydrocarbon group and aromatic heterocyclic group are the aforementioned Ar ５１Similar aromatic hydrocarbon groups and aromatic heterocyclic groups can be used.

[0111] Ar ６３ ~Ar ６５ If Ar is a substituent, ６３ ~Ar ６５ It is preferable from the viewpoint of improving durability that Ar is bonded to the 3rd or 6th position of each carbazole structure. ６３ ~Ar ６５ From the viewpoint of ease of synthesis and charge transport properties, it is preferable that the atom be a hydrogen atom.

[0112] Ar ６３ ~Ar ６５ From the viewpoint of improving durability and charge transport, it is preferable that the group be a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, and more preferably a substituted or unsubstituted aromatic hydrocarbon group.

[0113] Ar ６３ ~Ar ６５ When is a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, examples of substituents include the groups listed in substituent group Z2, and preferred substituents are the same as those in substituent group Z2.

[0114] (Ar ６２ ) Ar ６２ This is a substituted or unsubstituted divalent aromatic hydrocarbon group or a substituted or unsubstituted divalent aromatic heterocyclic group.

[0115] The aromatic hydrocarbon group preferably has 6 to 60 carbon atoms, more preferably 10 to 50 carbon atoms, and particularly preferably 12 to 40 carbon atoms. Specifically, the aromatic hydrocarbon group may be a 6-membered monocyclic or 2- to 5-condensed divalent group, such as a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring, acenaphthene ring, fluorantene ring, or fluorene ring, or a group in which multiple such groups are linked. When multiple such groups are linked, it is preferable that the multiple linked divalent aromatic hydrocarbon groups are conjugated.

[0116] The aromatic heterocyclic group preferably has 3 to 60 carbon atoms, specifically a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, an oxadiazole ring, an indole ring, a carbazole ring, a pyrroloimidazole ring, a pyrrolopyrazole ring, a pyrrolopyrrole ring, a thienopyrrole ring, a thienothiophene ring, a phlopyrrole ring, a phlofuran ring, a thienofuran ring, a benzoiso Examples include monocyclic rings with 5 or 6 members, such as xazole rings, benzoisothiazole rings, benzimidazole rings, pyridine rings, pyrazine rings, pyridazine rings, pyrimidine rings, triazine rings, quinoline rings, isoquinoline rings, sinnoline rings, quinoxaline rings, phenanthridine rings, benzimidazole rings, perimidine rings, quinazoline rings, quinazolinone rings, and azulene rings, or divalent groups of 2 to 4 fused rings, or groups formed by linking multiple such rings.

[0117] The substituents that these aromatic hydrocarbon groups or aromatic heterocyclic groups may have include alkyl groups, aralkyl groups, and aromatic hydrocarbon groups of the substituent group Z2. ６２ If a twist in the structure occurs, it is preferable to have no substituents, and the steric effect of the substituents may cause Ar ６２ If no twisting of the structure occurs, it is preferable to have substituents.

[0118] Ar ６２ The group is preferably a divalent group of a benzene ring, naphthalene ring, anthracene ring, or fluorene ring, or a group in which multiple such groups are linked; more preferably a divalent group of a benzene ring, or a group in which multiple such groups are linked; particularly preferably a 1,4-phenylene group in which a benzene ring is linked at the 1,4 positions; a 2,7-fluorenylene group in which a fluorene ring is linked at the 2,7 positions; or a group in which multiple such groups are linked; and most preferably a group containing "1,4-phenylene group-2,7-fluorenylene group-1,4-phenylene group-".

[0119] In these preferred structures, the phenylene group has no substituents other than at the linking position, which is due to the steric effect of substituents. ６２This is preferable because it prevents twisting. Furthermore, it is preferable for the fluorenylene group to have a substituent at the 9-position from the viewpoint of improving solubility in organic solvents and durability of the fluorene structure.

[0120] (Ar ６１ ) Ar ６１ Ar is a divalent group that links to the nitrogen atom of the main chain in the repeating unit represented by formula (50). ６１ This is a substituted or unsubstituted divalent aromatic hydrocarbon group, or a substituted or unsubstituted divalent aromatic heterocyclic group.

[0121] Ar ６１ The aromatic hydrocarbon group preferably has 6 to 60 carbon atoms, more preferably 10 to 50 carbon atoms, and particularly preferably 12 to 40 carbon atoms. Specifically, the aromatic hydrocarbon group may be a 6-membered monocyclic or 2- to 5-fused divalent group, or a group formed by linking multiple such rings, such as a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring, acenaphthene ring, fluorantene ring, or fluorene ring.

[0122] Ar ６１ The aromatic heterocyclic group preferably has 3 to 60 carbon atoms. Specifically, examples include furan rings, benzofuran rings, thiophene rings, benzothiophene rings, pyrrole rings, pyrazole rings, imidazole rings, oxadiazole rings, indole rings, carbazole rings, pyrroloimidazole rings, pyrrolopyrrole rings, thienopyrrole rings, thienothiophene rings, phlopyrrole rings, phlofuran rings, thienofuran rings, benzoisoxazole rings, benzoisothiazole rings, benzimidazole rings, pyridine rings, pyrazine rings, pyridazine rings, pyrimidine rings, triazine rings, quinoline rings, isoquinoline rings, sinnoline rings, quinoxaline rings, phenantholidine rings, benzimidazole rings, perimidine rings, quinazoline rings, quinazolinone rings, azulene rings, and other groups consisting of a 5- or 6-membered monocyclic ring or a 2- to 4-fused ring, or a group in which multiple such rings are linked.

[0123] The substituents that these aromatic hydrocarbon groups or aromatic heterocyclic groups may have include alkyl groups, aralkyl groups, and aromatic hydrocarbon groups of the substituent group Z2.

[0124] When multiple divalent aromatic hydrocarbon groups or divalent aromatic heterocyclic groups are linked together, it is preferable that the linked divalent aromatic hydrocarbon groups are bonded in such a way that they are not conjugated. Specifically, it is preferable that the group includes a 1,3-phenylene group or a group having a substituent that forms a twisted structure due to the steric effect of the substituent.

[0125] (Base represented by formula (53)) Ar in the repeating unit represented by formula (50) ５１ It is also preferable that the group is represented by the following formula (53).

[0126]

[0127] In formula (53), * represents the bond position with the nitrogen atom of the main chain in formula (50), Ar ７１ Ar represents a substituted or unsubstituted divalent aromatic hydrocarbon group, or a divalent group consisting of multiple substituted or unsubstituted aromatic hydrocarbon groups linked together. ７２ and Ar ７３ Each independently represents a monovalent group consisting of two or more groups directly or via linking groups, selected from the group consisting of substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted aromatic hydrocarbon groups and substituted or unsubstituted aromatic heterocyclic groups, where ring HA is an aromatic heterocyclic ring containing a nitrogen atom, and X ２ , Y ２ Each of these independently represents a carbon atom or a nitrogen atom, and X ２ and Y ２ If at least one of them is a carbon atom, that carbon atom may have substituents.

[0128] (Ar ７１ ) Ar ７１ Ar is a substituted or unsubstituted divalent aromatic hydrocarbon group, or a divalent group consisting of multiple substituted or unsubstituted aromatic hydrocarbon groups linked together. ７１Preferably, the group consists of one substituted or unsubstituted divalent aromatic hydrocarbon group, or two to ten substituted or unsubstituted divalent aromatic hydrocarbon groups linked together. More preferably, the group consists of one substituted or unsubstituted divalent aromatic hydrocarbon group, or two to eight substituted or unsubstituted divalent aromatic hydrocarbon groups linked together. In particular, a group consisting of two or more substituted or unsubstituted divalent aromatic hydrocarbon groups linked together is preferred.

[0129] Ar ７１ In particular, groups consisting of 2 to 6 linked substituted or unsubstituted benzene rings are preferred, groups consisting of 3 to 6 linked substituted or unsubstituted benzene rings are more preferred, and quaterphenylene groups consisting of 4 linked substituted or unsubstituted benzene rings are most preferred.

[0130] Ar ７１ It is preferable that it contains at least one benzene ring linked at the 1,3 positions, which are non-conjugated sites, and more preferably two or more.

[0131] Ar ７１ In the case of a group consisting of multiple linked divalent aromatic hydrocarbon groups, which may have substituents, it is preferable from the viewpoint of charge transportability or durability that all of the aromatic hydrocarbon groups are directly bonded together.

[0132] Therefore, Ar ７１ The preferred structures connecting the nitrogen atom of the polymer's main chain to the ring HA in formula (53) are shown in schemes 2-1 and 2-2 below. "-*" represents the bonding position with the nitrogen atom of the polymer's main chain or the ring HA in formula (53). Either of the two "-*"s may be bonded to the nitrogen atom of the polymer's main chain or to the ring HA.

[0133]

[0134]

[0135] Ar ７１ Examples of substituents that may be present include the groups described in substituent group Z2, and preferred substituents are the same as those in substituent group Z2.

[0136] (X ２ and Y ２) X ２ and Y ２ Each of these independently represents either a carbon (C) atom or a nitrogen (N) atom. ２ and Y ２ If at least one of them is a carbon atom, it may have substituents.

[0137] From the perspective of making it easier to localize LUMO around the ring HA, X ２ and Y ２ Preferably, all of these are N atoms.

[0138] X ２ and Y ２ If at least one of them is a C atom, the substituents that may be present are the groups listed in substituent group Z2. From the viewpoint of charge transport, X ２ and Y ２ It is even more preferable that it does not have substituents.

[0139] (Ar ７２ and Ar ７３ ) Ar ７２ and Ar ７３ Each of these is a monovalent group in which two or more groups selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted aromatic hydrocarbon group and a substituted or unsubstituted aromatic heterocyclic group are linked directly or via linking groups.

[0140] From the perspective of distributing the LUMO of molecules, Ar ７２ and Ar ７３ Preferably, each of them independently has a structure selected from a-1 to a-4, b-1 to b-9, c-1 to c-4, d-1 to d-16, and e-1 to e-4 shown in schemes 1-1 to 1-3.

[0141] Furthermore, from the viewpoint of promoting the expansion of the molecular LUMO by having electron-withdrawing groups, structures selected from a-1 to a-4, b-1 to b-9, c-1 to c-4, d-1 to d-12, and e-1 to e-4 are preferred.

[0142] Furthermore, from the viewpoint of achieving a higher triplet level and confining excitons formed in the light-emitting layer, structures selected from a-1 to a-4, d-1 to d-12, and e-1 to e-4 are preferred.

[0143] To prevent molecular aggregation, structures selected from d-1 to d-12 and e-1 to e-4 are even more preferred. From the viewpoint of being easy to synthesize and having excellent stability, Ar ７２ =Ar ７３ = d-1 or d-10 is preferred, and the benzene ring structure of d-1 is particularly preferred.

[0144] These structures may have substituents. Here, the "-*" in each structure shown in schemes 1-1 to 1-3 represents the bond position with ring HA. If there are multiple "-*" symbols, each one represents a site that bonds with ring HA.

[0145] Ar ７２ and Ar ７３ Examples of substituents that may be present include the groups described in substituent group Z2. From the viewpoint of durability and charge transport, Ar ７２ and Ar ７３ It is preferable that it has substituents, and the preferred substituents are the same as those in substituent group Z2.

[0146] (Base represented by formula (81)) Ar in the repeating unit represented by formula (50) ５１ It is also preferable that the group is represented by the following formula (81).

[0147]

[0148] In formula (81), Fu is a substituted or unsubstituted monovalent aromatic hydrocarbon condensed ring group, or a substituted or unsubstituted carbazolyl group, and ab is an integer from 0 to 1.

[0149] (Fu) In formula (81), Fu represents a substituted or unsubstituted monovalent aromatic hydrocarbon condensed ring group, or a substituted or unsubstituted carbazolyl group. The monovalent aromatic hydrocarbon condensed ring group preferably has 6 to 60 carbon atoms, more preferably 10 to 50 carbon atoms, and particularly preferably 12 to 40 carbon atoms. Specifically, the monovalent aromatic hydrocarbon condensed ring group includes monovalent groups of 2 to 5 condensed rings such as naphthalene rings, anthracene rings, phenanthrene rings, perylene rings, tetracene rings, pyrene rings, benzpyrene rings, chrysene rings, triphenylene rings, acenaphthene rings, fluorantene rings, and fluorene rings, or groups in which multiple such groups are linked. When multiple such groups are linked, it is preferable that the multiple linked monovalent aromatic hydrocarbon groups are conjugated.

[0150] The substituents that these monovalent aromatic hydrocarbon condensed ring groups may have include alkyl groups, aralkyl groups, and aromatic hydrocarbon groups of the substituent group Z2. From the viewpoint of charge transport, it is preferable that the substituents that Fu may have are alkyl groups or aromatic hydrocarbon groups.

[0151] In formula (81), Fu is preferably a fluorenyl group which may have substituents, due to its high stability during charge transport.

[0152] (ab) In formula (81) above, ab is an integer between 0 and 1. From the viewpoint of charge transport, it is preferable that ab is 1.

[0153] From the viewpoint of charge transport, the above formula (81) is preferably the following formula (82).

[0154]

[0155] In formula (82), Fu is a substituted or unsubstituted monovalent aromatic hydrocarbon condensed ring group, or a substituted or unsubstituted carbazolyl group, and ab is an integer from 0 to 1.

[0156] In formula (82), Fu and ab are the same as in formula (81), and the preferred structure is the same as in the case of Fu in formula (81).

[0157] The following are some specific examples of equation (81), but are not limited to these.

[0158]

[0159] (Ar ５２ ) Ar in equation (50) ５２ The aromatic hydrocarbon group and the aromatic hydrocarbon group are Ar of formula (51) above. ５３ Examples include aromatic hydrocarbon groups and groups similar to aromatic hydrocarbon groups. Also, Ar ５２ Examples of aromatic hydrocarbon groups and substituents that the aromatic hydrocarbon group may have include the groups described in substituent group Z2, and preferred substituents are the same as those in substituent group Z2.

[0160] [Crosslinking Groups] It is preferable that the polymer according to the embodiment of the present invention does not have crosslinking groups. In one embodiment of the present invention, in the first and second embodiments, the repeating units represented by any of the following formulas (54) to (58) do not contain crosslinking groups. When crosslinking groups are not present, distortion of the polymer chain is less likely to occur due to heat drying or baking (heat firing) after wet film formation, which is preferable. When crosslinking groups are present, distortion of the polymer chain tends to occur when the crosslinking groups react. In the first and second embodiments, Ar ５３ Ar ５４ and Ar ５５ and Ar ５６ As mentioned above, the substituents that can be present are substituents other than crosslinking groups.

[0161] In this embodiment, a crosslinking group refers to a group that reacts with other crosslinking groups located in its vicinity upon irradiation with heat and / or active energy rays to form a new chemical bond. In this case, the reacting group may be the same as the crosslinking group or a different group.

[0162] Examples of crosslinking groups include groups containing alkenyl groups, groups containing conjugated diene structures, groups containing alkynyl groups, groups containing oxirane structures, groups containing oxetane structures, groups containing aziridine structures, azide groups, groups containing maleic anhydride structures, groups containing alkenyl groups bonded to aromatic rings, and cyclobutene rings fused to aromatic rings. Specific examples of crosslinking groups include, for example, groups selected from the following crosslinking group group T (XL-1 to XL-18).

[0163] (Bridging group group T)

[0164]

[0165] In the above crosslinking group T (XL-1 to XL-18), R ＸＬ n represents a methylene group, an oxygen atom, or a sulfur atom. ＸＬ This represents an integer between 0 and 5. ＸＬ If there are multiple instances, they may be the same or different, n ＸＬ If multiple such groups exist, they may be identical or different. *1 indicates the bonding position. These bridging groups may have substituents.

[0166] When the polymer according to the embodiment of the present invention is used, for example, in an organic layer constituting an organic electroluminescent element, it can achieve both the promotion of hole injection from the organic layer containing the polymer to the cathode-side adjacent layer and the suppression of degradation by the polymer receiving electrons from the cathode-side adjacent layer, thus enabling the use of at least two different structures of the Ar ５１ It is preferable that it has

[0167] The repeating unit represented by formula (50) is preferably the repeating unit represented by formula (54), formula (55), formula (56), or formula (57). As described above, the polymer in the first embodiment of the present invention satisfies at least one of the following (i) and (ii), and the polymer in the second embodiment satisfies the following (i). (i) It has two or more repeating units from among the repeating units represented by formula (54), formula (55), formula (56), and formula (57). (ii) It consists of only one or more repeating units from among the repeating units represented by formula (54), formula (55), formula (56), and formula (57). Each repeating unit will be described in detail.

[0168] Polymers having repeating units represented by the following formulas (54) to (57) may preferably include multiple repeating units, each of which has a different structure.

[0169] <Repeating unit represented by formula (54)>

[0170]

[0171] In formula (54), Ar ５1 This is Ar in formula (50) above. ５１ Similarly, X is -C(R ２０７ ) (Caution ２０８ )-,-N(R ２０９ )-, or-C(R ２１１ ) (Caution ２１２ )-C(R ２１３ ) (Caution ２１４ ) - and R ２０１ , R ２０２ , R ２２１ and R ２２２ Each of these is independently a substituted or unsubstituted alkyl group, R ２０７ ~R ２０９ and R ２１１ ~R ２１４Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted monovalent aromatic hydrocarbon group, and each of a, b and d is independently an integer from 0 to 4, and c is an integer from 0 to 3, provided that if a is 1 or greater, then c is 1 or greater, and if b is 1 or greater, then d is 1 or greater, R ２０１ If there are multiple R's, ２０１ They may be the same or different, R ２０２ If there are multiple R's, ２０２ They may be the same or different, R ２２１ If there are multiple R's, ２２１ They may be the same or different, R ２２２ If there are multiple R's, ２２２ i and j may be the same or different, and each is an independent integer between 0 and 3.

[0172] (R ２０１ , R ２０２ , R ２２１ , R ２２２ ) R in the repeating unit represented by the above formula (54) ２０１ , R ２０２ , R ２２１ and R ２２２ Each of these is independently a substituted or unsubstituted alkyl group.

[0173] The alkyl group is a linear, branched, or cyclic alkyl group. The number of carbon atoms in the alkyl group is not particularly limited, but in order to maintain the solubility of the polymer in organic solvents, it is preferably 1 or more, preferably 8 or less, more preferably 6 or less, and more preferably 3 or less. The alkyl group is more preferably a methyl group or an ethyl group. Optional substituents are those listed in substituent group Z2, and preferred substituents are the same as those in substituent group Z2. Optional substituents are preferably substituents other than crosslinking groups.

[0174] R ２０１ If there are multiple R's, ２０１ They may be the same or different, R ２０２ If there are multiple R's,２０２ They may be the same or different. Since the charge can be uniformly distributed around the nitrogen atom and it is also easy to synthesize, all R ２０1 and R ２０２ It is preferable that they are the same group.

[0175] R ２２１ If there are multiple R's, ２２１ They may be the same or different, R ２２２ If there are multiple R's, ２２２ They may be the same or different. Since the charge can be uniformly distributed around the nitrogen atom and it is also easy to synthesize, all R ２２1 and R ２２２ It is preferable that they are the same group.

[0176] (R ２０７ ~R ２０９ and R ２１１ ~R ２１４ ) R ２０７ ~R ２０９ and R ２１１ ~R ２１４ Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aromatic hydrocarbon group.

[0177] The alkyl group is not particularly limited, but it is preferable that the alkyl group has 1 or more carbon atoms, preferably 24 or fewer, more preferably 8 or fewer, and even more preferably 6 or fewer, as this tends to improve the solubility of the polymer in organic solvents. The alkyl group may have a linear, branched, or cyclic structure.

[0178] Examples of alkyl groups include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n-hexyl group, n-octyl group, cyclohexyl group, and dodecyl group.

[0179] The aralkyl group is not particularly limited, but it tends to improve the solubility of the polymer in organic solvents, so it is preferable that it has 5 or more carbon atoms, preferably 60 or fewer, and more preferably 40 or fewer.

[0180] Examples of aralkyl groups include 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-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-1-n-octyl group, and 4-phenylcyclohexyl group.

[0181] While there are no particular limitations on the aromatic hydrocarbon group, it is preferable that the number of carbon atoms be 6 or more, preferably 60 or less, and more preferably 30 or less, as this tends to improve the solubility of the polymer in organic solvents.

[0182] Examples of aromatic hydrocarbon groups include monovalent groups of six-membered rings or 2- to 5-fused rings, such as benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, perylene rings, tetracene rings, pyrene rings, benzpyrene rings, chrysene rings, triphenylene rings, acenaphthene rings, fluorantene rings, and fluorene rings, or groups formed by linking multiple such rings.

[0183] From the viewpoint of improving charge transport and durability, R ２０７ and R ２０８ R is preferably a methyl group or an aromatic hydrocarbon group. ２０７ and R ２０８ It is more preferable that R is a methyl group. ２０９ It is more preferable that it be a phenyl group.

[0184] R ２０１ , R ２０２ , R ２２１ , R ２２２ alkyl group, R ２０７ ~R ２０９ and R ２１１ ~R ２１４The alkyl group, aralkyl group, and aromatic hydrocarbon group may have substituents. Examples of substituents that may be present are the groups listed in substituent group Z2, and preferred substituents are the same as those in substituent group Z2.

[0185] R ２０１ , R ２０２ , R ２２１ , R ２２２ alkyl group, R ２０７ ~R ２０９ and R ２１１ ~R ２１４ From the viewpoint of lowering the voltage, it is most preferable that the alkyl, aralkyl, and aromatic hydrocarbon groups do not have substituents.

[0186] (X) X is -C(R ２０７ ) (Caution ２０８ )-,-N(R ２０９ )-, or-C(R ２１１ ) (Caution ２１２ )-C(R ２１３ ) (Caution ２１４ ) - is.

[0187] Due to its high stability during charge transport, X is -C(R ２０７ ) (Caution ２０８ )-, or -N(R ２０９ ) - is preferable, -C(R ２０７ ) (Caution ２０８ ) - is more preferable, -C(R ２０７ ) (Caution ２０８ ) - and R ２０７ , R ２０８ It is particularly preferable that each of these groups is independently a substituted or unsubstituted alkyl group. Optional substituents include the groups listed in substituent group Z2, and preferred substituents are the same as those in substituent group Z2. Optional substituents are preferably substituents other than crosslinking groups.

[0188] (a, b, c, and d) In the repeating unit represented by the above formula (54), a and b are each independent integers from 0 to 4. It is preferable that a + b is 1 or greater. Furthermore, it is preferable that a and b are each 2 or less, and it is more preferable that both a and b are 1. Here, a being 1 or greater means that c is 1 or greater, and b being 1 or greater means that d is 1 or greater. Also, if b is 1 or greater, it is preferable that d is also 1 or greater. Furthermore, if c is 2 or greater, the multiple as may be the same or different, and if d is 2 or greater, the multiple bs may be the same or different.

[0189] When a+b is 1 or greater, the aromatic rings of the main chain are twisted due to steric hindrance, resulting in excellent solubility of the polymer in organic solvents. Furthermore, coatings formed by wet deposition and heat-treated tend to exhibit excellent insolubility in organic solvents. Therefore, when a+b is 1 or greater, if another organic layer (e.g., a light-emitting layer) is formed on this coating by wet deposition, the elution of the polymer into the light-emitting layer-forming composition used in the embodiments of the present invention, which contains an organic solvent, is suppressed. As a result, the impact on the formed light-emitting layer is reduced, and the driving life and luminous efficiency of the organic electroluminescent device are expected to be further extended.

[0190] In the repeating unit represented by the above formula (54), c is an integer from 0 to 3, and d is an integer from 0 to 4. Preferably, c and d are each 2 or less, more preferably c and d are equal, and particularly preferably both c and d are 1, or both c and d are 2.

[0191] When both c and d in the repeating unit represented by the above formula (54) are 1, or both c and d are 2, and both a and b are 2 or 1, R ２０１ and R ２０２ It is most preferable that they are joined in positions symmetrical to each other.

[0192] Here, R ２０１ and R ２０２ The bond between them in symmetrical positions means that, in formula (54), R is attached to the fluorene ring, carbazole ring, or 9,10-dihydrophenanthrene derivative structure. ２０１ and R ２０２This refers to the symmetrical positioning of the bonds. In this case, a 180-degree rotation around the main chain axis is considered to result in the same structure.

[0193] R ２２１ and R ２２２ If present, it is preferable that each is independently located at the 1st, 3rd, 6th, or 8th position relative to the carbon atom of the benzene ring to which X is bonded. ２２１ and / or R ２２２ The existence of R ２２１ and / or R ２２２ The condensed ring to which the polymer is bonded and the adjacent benzene ring on the main chain are twisted due to steric hindrance, resulting in excellent solubility of the polymer in organic solvents. Furthermore, the coating film formed by the wet film formation method and heat-treated tends to have excellent insolubility in organic solvents, which is preferable.

[0194] (i and j) In the repeating unit represented by the above formula (54), i and j are each independent integers from 0 to 3. It is preferable that i and j are each 2 or less, and it is more preferable that both i and j are 0 or 1.

[0195] (Ar ５１ ) In the repeating unit represented by the above formula (54), Ar ５１ Ar in formula (50) ５１ Similar to the above, it is a monovalent group formed by linking multiple groups selected from substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted aromatic hydrocarbon groups and substituted or unsubstituted aromatic heterocyclic groups. ５１ If present, they may be the same or different. Preferably, the substituents are other than crosslinking groups.

[0196] As a group formed by linking multiple groups selected from the group consisting of substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted aromatic hydrocarbon groups and substituted or unsubstituted aromatic heterocyclic groups, the Ar in formula (50) ５１ Examples similar to those in the case of formula (50) include substituents that may be present and preferred structures, as in Ar ５１The same examples as in the case of [this case] can be cited.

[0197] In the second embodiment, in the repeating unit represented by formula (54) above, Ar ５１ Ar represents a group formed by linking multiple groups selected from the group consisting of an aromatic hydrocarbon group which may have substituents other than a crosslinking group, an aromatic heterocyclic group which may have substituents other than a crosslinking group, or an aromatic hydrocarbon group which may have substituents other than a crosslinking group and an aromatic heterocyclic group which may have substituents other than a crosslinking group. ５１ The nitrogen atom to which it is bonded (N-Ar ５１ It is preferable that the fused ring is not directly bonded to the nitrogen atom (represented by ). If the fused ring is directly bonded to the nitrogen atom, the HOMO orbital expands around the nitrogen atom and the fused ring, causing the HOMO level to become shallower and the energy gap to narrow. Therefore, when this polymer is used as the hole transport layer of an organic light-emitting device, it is thought that the luminous efficiency and operating life may decrease. ５１ The nitrogen atom to which it is bonded (N-Ar ５１ It is preferable that the nitrogen atom represented by does not form a fused ring with adjacent aromatic hydrocarbon rings or aromatic heterocycles. When the nitrogen atom forms a fused ring with adjacent aromatic hydrocarbon rings or aromatic heterocycles, the HOMO orbital expands around that portion, causing the HOMO level to become shallower and the energy gap to narrow. Therefore, when used as a hole transport layer in an organic light-emitting device, it is thought that the luminous efficiency and operating life will decrease. The aromatic hydrocarbon group preferably has 6 to 60 carbon atoms, and specifically, examples include monovalent groups of 6-membered rings or 2 to 5-fused rings such as benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, perylene rings, tetracene rings, pyrene rings, benzpyrene rings, chrysene rings, triphenylene rings, acenaphthene rings, fluorantene rings, and fluorene rings, or groups in which multiple such groups are linked. Among the above, for example, "monovalent group of a benzene ring" means "a benzene ring having a monovalent free valency," that is, a phenyl group.

[0198] (Other preferred Ar ５１ ) Ar in the repeating unit represented by the above formula (54) ５１However, it is also preferable that the group be represented by formula (51), formula (52), or formula (53). In the two carbazole structures in formula (52), it is thought that the distribution of LUMOs between the nitrogen atoms of each other in the aromatic hydrocarbon group or aromatic heterocyclic group tends to improve the durability against electrons and excitons.

[0199] In one embodiment of the present invention, in the second embodiment, Ar in the repeating unit represented by formula (54) ５１ However, it is preferable that the group includes a monovalent or divalent group in which 2 to 5 benzene rings, which may have substituents other than the crosslinking group, are linked together, the group represented by formula (51), the group represented by formula (52), the group represented by formula (53), the group represented by formula (81), or a group in which a plurality of these are linked together, and it is more preferable that the group is a monovalent group in which 2 to 5 benzene rings, which may have substituents other than the crosslinking group, are linked together, or the group represented by formula (81).

[0200] In a polymer containing repeating units represented by the above formula (54), Ar ５１ , R ２０１ , R ２０２ , R ２２１ , R ２２２ If there are multiple X values, they may be the same or different. Preferably, the polymer contains multiple repeating units, each having the same structure as the repeating unit represented by formula (54). In this case, because the polymer contains multiple repeating units with the same structure, the HOMO and LUMO of the repeating units are the same, so charge does not concentrate at specific shallow levels and become a trap, and thus the polymer is considered to have excellent charge transport properties.

[0201] (Preferred repeating unit) The repeating unit represented by formula (54) above is particularly preferably a repeating unit represented by any of the following formulas (54-1) to (54-8).

[0202]

[0203]

[0204] Ar in the above formulas (54-1) to (54-8) ５１ , R ２０１ , R２０２ , R ２２１ , R ２２２ And X are, respectively, Ar in equation (54). ５１ , R ２０１ , R ２０２ , R ２２１ , R ２２２ And the same as X. However, in the above equations (54-1) to (54-4), R ２０１ and R ２０２ They are identical, and R ２０１ and R ２０２ They are joined in positions symmetrical to each other. Also, in the above equations (54-5) to (54-8), R ２２１ and R ２２２ They are identical, and R ２２１ and R ２２２ They are joined in positions symmetrical to each other.

[0205] [Specific examples of the main chain in the repeating unit represented by formula (54)] The main chain structure excluding the nitrogen atom in the repeating unit represented by formula (54) is not particularly limited, but the following structure is an example.

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214] [Content of repeating units represented by formula (54)] In the polymer according to the embodiments of the present invention, if it has repeating units represented by formula (54), the content thereof is not particularly limited, but the repeating units represented by formula (54) are usually contained in 10 mol% or more of the total repeating units of the polymer, preferably 30 mol% or more, more preferably 40 mol% or more, and even more preferably 50 mol% or more.

[0215] In embodiments of the present invention, if the polymer has repeating units represented by formula (54), the repeating units may consist only of repeating units represented by formula (54). However, for the purpose of balancing the various performance characteristics when used as an organic electroluminescent element, it may also have repeating units other than those represented by formula (54). In that case, the content of repeating units represented by formula (54) in the total repeating units of the polymer is usually 99 mol% or less, preferably 95 mol% or less.

[0216] [End Groups] In this specification, end groups refer to the structures of the end portions of a polymer formed by an end capping agent used at the end of polymerization. The end groups of a polymer containing repeating units represented by formula (54) are preferably hydrocarbon groups. From the viewpoint of charge transport properties, hydrocarbon groups with 1 to 60 carbon atoms are preferred, 1 to 40 carbon atoms are more preferred, and 1 to 30 carbon atoms are even more preferred.

[0217] Examples of hydrocarbon groups include linear, branched, or cyclic alkyl groups having typically 1 or more carbon atoms, preferably 4 or more, and usually 24 or less, and preferably 12 or less, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-hexyl, cyclohexyl, and dodecyl groups; linear, branched, or cyclic alkenyl groups having typically 2 or more carbon atoms, usually 24 or less, and preferably 12 or less, such as vinyl groups; linear or branched alkynyl groups having typically 2 or more carbon atoms, usually 24 or less, and preferably 12 or less, such as ethynyl groups; and aromatic hydrocarbon groups having typically 6 or more carbon atoms, usually 36 or less, and preferably 24 or less, such as phenyl and naphthyl groups.

[0218] These hydrocarbon groups may have further substituents, and the substituents that may be present are preferably alkyl groups or aromatic hydrocarbon groups. If there are multiple such substituents, they may be bonded to each other to form a ring.

[0219] The terminal group is preferably an alkyl group or an aromatic hydrocarbon group, and more preferably an aromatic hydrocarbon group, from the viewpoint of charge transport and durability.

[0220] <Repeating unit represented by formula (55)>

[0221]

[0222] In formula (55), Ar ５1 Ar in formula (50) ５１ It is similar to R ３０３ and R ３０６ Each of these is independently a substituted or unsubstituted alkyl group, R ３０４ and R ３０５ Each is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aralkyl group, and l, n, p, and q are independently 0 or 1, and m is 1 or 2, provided that when p is 1, l is 1, and when q is 1, n is 1. ５１The nitrogen atom to which it is bonded (N-Ar ５１ It is preferable that the fused ring is not directly bonded to the nitrogen atom represented by .

[0223] (R ３０３ , R ３０６ ) R in the repeating unit represented by the above formula (55) ３０３ and R ３０６ Each of these is independently a substituted or unsubstituted alkyl group. As an alkyl group, R in formula (54) above is ２０１ and R ２０２ Similar examples include substituents that may be present and preferred structures of R. ２０１ and R ２０２ Similar examples include R. ３０３ If there are multiple R's, ３０３ They may be the same or different, R ３０６ If there are multiple R's, ３０６ They may be the same or different.

[0224] (R ３０４ , R ３０５ ) R in the repeating unit represented by the above formula (55) ３０４ and R ３０５ Each of these is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aralkyl group. Preferably, it is a substituted or unsubstituted alkyl group. ３０４ and R ３０５ It is preferable that they are the same.

[0225] The alkyl group is a linear, branched, or cyclic alkyl group. The number of carbon atoms in the alkyl group is not particularly limited, but it is preferable to have 1 or more carbon atoms, preferably 24 or fewer, more preferably 8 or fewer, and even more preferably 6 or fewer, as this tends to improve the solubility of the polymer in organic solvents.

[0226] Specifically, examples include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n-hexyl group, n-octyl group, cyclohexyl group, dodecyl group, and the like.

[0227] The alkoxy group is not particularly limited, and the alkoxy group (-OR １０ ) R １０ The group may have a linear, branched, or cyclic structure, and since this tends to improve the solubility of the polymer in organic solvents, the number of carbon atoms is preferably 1 or more, preferably 24 or less, and more preferably 12 or less.

[0228] Specifically, examples include methoxy groups, ethoxy groups, n-propoxy groups, n-butoxy groups, hexyloxy groups, 1-methylpentyloxy groups, and cyclohexyloxy groups.

[0229] The aralkyl group is not particularly limited, but it is preferable to have 5 or more carbon atoms, preferably 60 or fewer, and more preferably 40 or fewer, as it tends to improve the solubility of the polymer in organic solvents.

[0230] Specifically, examples include 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-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-1-n-octyl group, and 4-phenylcyclohexyl group.

[0231] (l, m, and n) l represents 0 or 1, and n represents 0 or 1. l and n are independent of each other, and l + n is preferably 1 or more, more preferably 1 or 2, and even more preferably 2. When l + n is within the above range, the solubility of the polymer in organic solvents in the embodiments of the present invention tends to be improved, and the precipitation of the polymer from the organic electroluminescent element composition containing the polymer tends to be suppressed.

[0232] m represents 1 or 2, and it is preferable that m be 1, as this allows the organic electroluminescent element in the embodiment of the present invention to be driven at a low voltage, and tends to improve hole injection ability, transport ability, and durability.

[0233] (p and q) p represents 0 or 1, and q represents 0 or 1. When l = n = 1, p and q cannot be 0 at the same time. The fact that p and q cannot be 0 at the same time tends to improve the solubility of the polymer in organic solvents in the embodiments of the present invention and suppress the precipitation of the polymer from the organic electroluminescent light-emitting composition containing the polymer. Furthermore, when p + q is 1 or greater, the aromatic ring of the main chain is twisted due to steric hindrance, resulting in excellent solubility of the polymer in organic solvents, and the coating film formed by the wet film deposition method and heat-treated tends to have excellent insolubility in organic solvents. Therefore, when p + q is 1 or greater, if another organic layer (e.g., a light-emitting layer) is formed on this coating film by the wet film deposition method, the elution of the polymer into the other organic layer-forming composition containing an organic solvent is suppressed.

[0234] (Ar ５１ ) In the repeating unit represented by the above formula (55), Ar ５１ Ar in formula (50) ５１ Similar to the above, it is a group formed by linking multiple groups selected from the group consisting of substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted aromatic hydrocarbon groups and substituted or unsubstituted aromatic heterocyclic groups.

[0235] As a group formed by linking multiple groups selected from the group consisting of substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted aromatic hydrocarbon groups and substituted or unsubstituted aromatic heterocyclic groups, the Ar in formula (50) ５１ Examples similar to those in the case of formula (50) include substituents that may be present and preferred structures, as in Ar ５１ The same examples as in the case of [this case] can be cited.

[0236] [Specific examples of the main chain in the repeating unit represented by formula (55)] The main chain structure excluding the nitrogen atom in the repeating unit represented by formula (55) is not particularly limited, but the following structures are examples.

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245] [Content of repeating units represented by formula (55)] In the polymer of the embodiment of the present invention, if it has repeating units represented by formula (55), the content thereof is not particularly limited, but the repeating units represented by formula (55) are usually contained in 10 mol% or more of the total repeating units of the polymer, preferably 30 mol% or more, more preferably 40 mol% or more, and particularly preferably 50 mol% or more.

[0246] In embodiments of the present invention, if the polymer has repeating units represented by formula (55), the repeating units may consist only of repeating units represented by formula (55). However, for the purpose of balancing the various performance characteristics when used as an organic electroluminescent element, it may also have repeating units other than those represented by formula (55). In that case, the content of repeating units represented by formula (55) in the total repeating units of the polymer is usually 99 mol% or less, preferably 95 mol% or less.

[0247] [End Groups] In the polymers of the embodiments of the present invention, the end groups of the polymer containing the repeating unit represented by formula (55) are preferably hydrocarbon groups, similar to the end groups of the polymer containing the repeating unit represented by formula (54). The preferred hydrocarbon groups and optional substituents are the same as those of the end groups of the polymer containing the repeating unit represented by formula (54).

[0248] <Repeating unit represented by formula (56)>

[0249]

[0250] In formula (56), Ar ５１ Ar in formula (50)５１ It is similar to Ar ４１ R is a divalent group in which multiple groups selected from the group consisting of substituted or unsubstituted divalent aromatic hydrocarbon groups, substituted or unsubstituted divalent aromatic heterocyclic groups, or substituted or unsubstituted aromatic hydrocarbon groups and substituted or unsubstituted aromatic heterocyclic groups are directly or via linking groups, ４４１ and R ４４２ Each of the elements is independently a substituted or unsubstituted alkyl group, t is 1 or 2, u is 0 or 1, and r and s are independently integers from 0 to 4, except when s is 1 or greater, u is 1. ５１ The nitrogen atom to which it is bonded (N-Ar ５１ It is preferable that the fused ring is not directly bonded to the nitrogen atom represented by .

[0251] (R ４４１ , R ４４２ ) R in the repeating unit represented by the above formula (56) ４４１ , R ４４２ Each of these is independently a substituted or unsubstituted alkyl group.

[0252] The alkyl group is a substituted or unsubstituted linear, branched, or cyclic alkyl group. The number of carbon atoms in the alkyl group is not particularly limited, but in order to maintain the solubility of the polymer in organic solvents, it is preferable to have 1 or more carbon atoms, preferably 10 or fewer, more preferably 8 or fewer, and even more preferably 6 or fewer. The alkyl group is more preferably a methyl group or a hexyl group. Optional substituents include the groups listed in substituent group Z2, and preferred substituents are the same as those in substituent group Z2.

[0253] R ４４１ and R ４４２ If there are multiple instances of in the repeating unit represented by the above formula (56), R ４４１ and R ４４２ They may be the same or different.

[0254] (r, s, t, and u) In the repeating unit represented by equation (56), r and s are each independent integers from 0 to 4. When t is 2 or greater, multiple r may be the same or different, and when u is 2 or greater, multiple s may be the same or different. It is preferable that r + s is 1 or greater, and furthermore, it is preferable that r and s are each 2 or less. It is believed that the driving life of the organic electroluminescent element is further extended when r + s is 1 or greater.

[0255] 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.

[0256] (Ar ５１ ) In the repeating unit represented by the above formula (56), Ar ５１ Ar in formula (50) ５１ Similar to the above, it is a group formed by linking multiple groups selected from the group consisting of substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted aromatic hydrocarbon groups and substituted or unsubstituted aromatic heterocyclic groups.

[0257] As a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, Ar in formula (50) ５１ Examples similar to those in the case above include substituents that may be present and preferred structures, such as Ar in formula (50). ５１ The same examples as in the case of [this case] can be cited.

[0258] (Ar ４１ ) Ar ４１ This refers to a divalent group in which multiple groups selected from the group consisting of substituted or unsubstituted divalent aromatic hydrocarbon groups, substituted or unsubstituted divalent aromatic heterocyclic groups, or substituted or unsubstituted aromatic hydrocarbon groups and substituted or unsubstituted aromatic heterocyclic groups are directly or via linking groups.

[0259] Ar ４１ The aromatic hydrocarbon group and aromatic hydrocarbon group in the above formula (50) are Ar ５２Similar groups can be cited. Furthermore, the aromatic hydrocarbon group and the substituents that the aromatic hydrocarbon group may have are preferably the same as those in substituent group Z2, and it is even more preferable that the substituents that may be present are the same as those in substituent group Z2.

[0260] [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.

[0261]

[0262] [Content of repeating units represented by formula (56)] In the polymer according to the embodiments of the present invention, if it has repeating units represented by formula (56), the content thereof is not particularly limited, but the repeating units represented by formula (56) are usually contained in an amount of 10 mol% or more, preferably 30 mol% or more, more preferably 40 mol% or more, and particularly preferably 50 mol% or more in the total repeating units of the polymer.

[0263] In embodiments of the present invention, if the polymer has repeating units represented by formula (56), the repeating units may consist only of repeating units represented by formula (56). However, for the purpose of balancing the various performance characteristics when used as an organic electroluminescent device, it may also have repeating units other than those represented by formula (56). In that case, the content of repeating units represented by formula (56) in the total repeating units of the polymer is usually 99 mol% or less, preferably 95 mol% or less.

[0264] [End Groups] In the polymers of the embodiments of the present invention, the end groups of the polymer containing the repeating unit represented by formula (56) are preferably hydrocarbon groups, similar to the end groups of the polymer containing the repeating unit represented by formula (54). Preferred hydrocarbon groups and optional substituents are the same as those of the end groups of the polymer containing the repeating unit represented by formula (54).

[0265] <Repeating unit represented by formula (57)>

[0266]

[0267] In formula (57), Ar５１ Ar in formula (50) ５１ It is similar to R ５１７ ~R ５１９ Each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group; f, g, and h are each independently integers from 0 to 4; and e is an integer from 0 to 3, provided that if g is 1 or greater, then e is 1 or greater. ５１ The nitrogen atom to which it is bonded (N-Ar ５１ It is preferable that the fused ring is not directly bonded to the nitrogen atom represented by .

[0268] (R ５１７ ~R ５１９ ) R ５１７ ~R ５１９ In formula (50), the aromatic hydrocarbon group and the aromatic heterocyclic group are each independently of the Ar group in formula (50). ５１ The substituents are similar to those listed above, and these groups may have substituents that are listed in substituent group Z2, and preferred substituents are the same as those in substituent group Z2.

[0269] R ５１７ ~R ５１９ The alkyl and aralkyl groups in the R ２０７ Groups similar to those listed above are preferred, and substituents that may also be present are also R ２０７ A similar base is preferred.

[0270] R ５１７ ~R ５１９ The alkoxy group in is preferably one of the alkoxy groups listed in substituent group Z2, and any other substituents that may be present are also those listed in substituent group Z2, with preferred substituents being the same as those in substituent group Z2.

[0271] (f, g, h) f, g, and h each independently represent integers from 0 to 4. If e is 2 or greater, the multiple gs may be the same or different. It is preferable that f + g + h is 1 or greater. It is preferable that g is 1 or greater.

[0272] (e) e represents an integer between 0 and 3, and if g is 1 or greater, then e is 1 or greater. e is preferably between 1 and 3, and more preferably e = 2.

[0273] The repeating unit represented by formula (57) is preferably the repeating unit represented by the following formula (58).

[0274] <Repeating unit represented by formula (58)>

[0275]

[0276] In formula (58), Ar ５１ Ar in formula (50) ５１ It is similar to R ５１７ ~R ５１９ , f, g, h, e are R in formula (57) above. ５１７ ~R ５１９ It is similar to f, g, h, and e.

[0277] In the repeating unit represented by formula (58) above, when e = 2, it is preferable that g is 1 or more, more preferably that g is 1 or more and f and h are 2 or less, even more preferably that g is 1 or more and f and h are 1 or less, and particularly preferably that g is 1 or more and f and h are 0. ５１ The nitrogen atom to which it is bonded (N-Ar ５１ It is preferable that the fused ring is not directly bonded to the nitrogen atom represented by .

[0278] In the repeating unit represented by formula (58) above, it is preferable that e = 2 and g = 1. When e = 2 and g = 1, there are two R ５１８ It is preferable that the two Rs are bonded in symmetrical positions to each other. ５１８ It is preferable that they are the same. Here, there are two R ５１８ The term "bonding in symmetrical positions" refers to the following bond positions. However, for notational purposes, a structure rotated 180 degrees around the main chain axis is considered the same structure.

[0279]

[0280] In the above formula, Ar５１ Ar in formula (54) ５１ It is similar to R ５１７ ~R ５１９ , f, h are R in equation (57) above. ５１７ ~R ５１９ It is similar to f and h.

[0281] In the repeating unit represented by formula (58), when e = 1 or 3, it is preferable that f + g + h is 1 or greater. It is preferable that f + h is 1 or greater, more preferably that f + h is 1 or greater and f, g, and h are 2 or less, even more preferably that f + h is 1 or greater and f, h are 1 or less, and most preferably that both f and h are 1.

[0282] If both f and h are 1, R ５１７ and R ５１９ It is preferable that they are bonded in positions symmetrical to each other. Also, R ５１７ and R ５１９ It is preferable that it be identical to the above.

[0283] Here, R ５１７ and R ５１９ The term "bonding in symmetrical positions" refers to the following bond positions. However, for notational purposes, a structure rotated 180 degrees around the main chain axis is considered the same structure.

[0284]

[0285] In the above formula, Ar ５１ Ar in formula (50) ５１ It is similar to R ５１７ ~R ５１９ e and g are R in formula (57) above. ５１７ ~R ５１９ It is the same as e and g.

[0286] It is also preferable that g is 2 in the repeating unit represented by formula (58) above. When g is 2, two R ５１８ It is more preferable that they are bonded to each other in the para position, and when g is 2, the two R ５１８ It is even more preferable that they be identical.

[0287] In the repeating unit represented by formula (58), it is preferable that e = 1 or 3 and g = 0 or 2. When g = 2, the bond positions are at positions 2 and 5. When g = 0, i.e., R ５１８ When there is no steric hindrance, and when g=2 and the bond positions are at positions 2 and 5, i.e., when there are two R steric hindrances ５１８ If it is at a diagonal position on the benzene ring to which it is bonded, then R ５１７ and R ５１９ It is possible for them to be joined in positions symmetrical to each other.

[0288] [Specific examples of the main chain in the repeating unit represented by formula (57)] The main chain structure excluding the nitrogen atom in the repeating unit represented by formula (57) is not particularly limited, but the following structures are examples.

[0289]

[0290] [Content of repeating units represented by formula (57)] In the polymer of the embodiment of the present invention, if it has repeating units represented by formula (57), the content thereof is not particularly limited, but the repeating units represented by formula (57) are usually contained in 10 mol% or more of the total repeating units of the polymer, preferably 30 mol% or more, more preferably 40 mol% or more, and particularly preferably 50 mol% or more.

[0291] In embodiments of the present invention, if the polymer has repeating units represented by formula (57), the repeating units may consist only of repeating units represented by formula (57). However, for the purpose of balancing the various performance characteristics when used as an organic electroluminescent device, it may also have repeating units other than those represented by formula (57). In that case, the content of repeating units represented by formula (57) in the total repeating units of the polymer is usually 99 mol% or less, preferably 95 mol% or less.

[0292] [End Groups] In the polymers of the embodiments of the present invention, the end groups of the polymer containing the repeating unit represented by formula (57) are preferably hydrocarbon groups, similar to the end groups of the polymer containing the repeating unit represented by formula (54). Preferred hydrocarbon groups and optional substituents are the same as those of the end groups of the polymer containing the repeating unit represented by formula (54).

[0293] It is preferable that the repeating units represented by formulas (50) to (58) do not have crosslinking groups. This is preferable because the absence of crosslinking groups makes it less likely for distortion of the polymer chain to occur during heating and drying or baking (heat firing) after wet film formation.

[0294] [Preferred Repeating Units] In the polymer of the embodiment of the present invention, it is preferable that the repeating unit represented by formula (50) is the repeating unit represented by formula (54), the repeating unit represented by formula (55), the repeating unit represented by formula (56), or the repeating unit represented by formula (57). Furthermore, it is preferable that in formula (54), a+b is 1 or more, in formula (56), r+s is 1 or more, and in formula (57), f+g+h is 1 or more, from the viewpoint of increasing the energy gap and suppressing a decrease in luminescence efficiency.

[0295] In one aspect of the present invention, the following embodiments are more preferred in the first and third embodiments. Furthermore, as described above, in other embodiments of the second embodiment of the present invention, which preferably satisfy formulas (1) and (2) above and at least one of (i) and (ii) below, the following embodiments are also more preferred. (i) Having two or more repeating units from among the repeating units represented by formula (54), the repeating units represented by formula (55), the repeating units represented by formula (56), and the repeating units represented by formula (57), or (ii) consisting of only one or more repeating units from among the repeating units represented by formula (54), the repeating units represented by formula (55), the repeating units represented by formula (56), and the repeating units represented by formula (57), that is, satisfying at least one of (i) and (ii) above is even more preferable because it includes many structures with a large energy gap, and satisfying (i) above is particularly preferable.

[0296] The polymer in the embodiments of the present invention preferably has at least the repeating unit represented by formula (54), more preferably the repeating unit represented by formula (54) and the repeating unit represented by formula (57), and even more preferably consists only of the repeating unit represented by formula (54) and the repeating unit represented by formula (57).

[0297] When the polymer has repeating units represented by the following formula (54), repeating units represented by the following formula (55), repeating units represented by the following formula (56), or repeating units represented by the following formula (57), it is preferable that it includes a substructure represented by the following formula (61) or the following formula (61'), and in particular, it is preferable that it has repeating units represented by the following formula (54) including a substructure represented by the following formula (61) or the following formula (61'), repeating units represented by the following formula (55) including a substructure represented by the following formula (61) or the following formula (61'), repeating units represented by the following formula (56) including a substructure represented by the following formula (61) or the following formula (61'), or repeating units represented by the following formula (57) including a substructure represented by the following formula (61) or the following formula (61').

[0298]

[0299] In equations (61) and (61'), R ６０１ R in formula (54) is ２０１ or R ２０２ , R in formula (55) ３０３ , R ３０４ , R ３０５ , or R ３０６ , R in formula (56) ４４１ or R ４４２ , R in formula (57) ５１７ , R ５１８ , or R ５１９ This represents at least one of the above, where -* indicates the bond position with an adjacent atom. If formula (61) and formula (61') are substructures of formula (54) or formula (56), Ring B may be part of a fused ring. The substructures represented by formula (61) and formula (61') are R ６０１ In addition, if the structural parts of Ring A and Ring B are the substructures of formula (54), then R ２０１ or R ２０２ However, if it is a substructure of formula (55) above, R ３０３ , R ３０４ , R ３０５ , or R ３０６ However, if it is a substructure of equation (56), then R ４４１ or R ４４２ However, if it is a substructure of equation (57), then R ５１７ , R ５１８ or R ５１９ They may be joined together.

[0300] The substructure represented by formula (61) or formula (61') is a substantially planar structure of Ring A and Ring B formed by π conjugation, R ６０１ The steric hindrance causes distortion, resulting in a more twisted main chain structure than typical π-conjugated bonds.

[0301] (Repeating unit represented by formula (62)) The repeating unit of the polymer is particularly preferably the repeating unit represented by formula (54). The repeating unit represented by formula (54) is preferably the repeating unit represented by the following formula (62).

[0302]

[0303] In formula (62), Ar ５１ X, R ２０１ , R ２０２ , R ２２１ , R ２２２ a and b are Ar in formula (54) ５１ X, R ２０１ , R ２０２ , R ２２１ , R ２２２ The same applies to a and b, where c is an integer between 1 and 3, d is an integer between 1 and 4, and a1, a2, b1, b2, i1, i2, j1, and j2 are each independently 0 or 1. Note that c-1 and d-1 represent integers obtained by subtracting 1 from c and d, respectively. However, either of the following conditions (I) or (II) must be met. (I) At least one of a1, a2, and a is 1 or greater, at least one of b1, b2, and b is 1 or greater, c is 1 or greater, d is 1 or greater, if c is 1, at least one of a1 or a2 is 1, and if d is 1, at least one of b1 or b2 is 1. (II) At least one of i1, i2, j1, and j2 is 1. Ring B1 is R ２０１ This refers to a divalent benzene ring which may have R at a specific position, and Ring B2 is R ２０１ A divalent group having c-1 linked benzene rings, where c=1 refers to a single bond; Ring B3 refers to a divalent fused ring in which the biphenyl structure is further bonded by X; Ring B4 is R ２０２ A divalent group having d-1 linked benzene rings, where d=1 refers to a single bond, and Ring B5 is R ２０２ This refers to a divalent benzene ring that may have a specific position.

[0304] Here, in equation (54), "a is 1 or greater" is equivalent to "at least one of a1, a2, and a in equation (62) is 1 or greater," and in equation (54), "b is 1 or greater" is equivalent to "at least one of b1, b2, and b in equation (62) is 1 or greater."

[0305] As described below, formula (62) includes formula (61) or formula (61') as a substructure. If at least one of a1, a2, and a is 1 or more, if at least one of a1 or a2 is 1, then Ring B1 and Ring B2, or if c is 1, then Ring B1 and Ring B3, include formula (61) or formula (61') as a substructure. 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, include formula (61) or formula (61') as a substructure, or if c is 3 or more and a is 1 or more, then Ring B2 may also include formula (61) or formula (61') as a substructure.

[0306] Similarly, it can be seen that formula (61) or formula (61') is included as a substructure when at least one of b1, b2, and b is 1 or more.

[0307] Furthermore, if at least one of i1, i2, j1, and j2 is 1, then if one or both of i1 and i2 are 1, then Ring B3's R ２２１ The ring to which is bonded and the benzene ring of Ring B2 or Ring B1 form a substructure of formula (61'), and when one or both of j1 and j2 are 1, the R of Ring B3 ２２２ It can be seen that formula (61) is formed as a substructure between the bonded ring and the benzene ring of Ring B4 or Ring B5.

[0308] In other words, it can be seen that Ring B3 and Ring B2 or Ring B1, or Ring B3 and Ring B4 or Ring B5, have a twisted structure. Therefore, formula (62) is preferable because it contains a twisted structure in the aromatic ring of the main chain, resulting in high solubility in organic solvents, cleavage of conjugation, and a wider energy gap.

[0309] [Molecular Weight of Polymer] The weight-average molecular weight (Mw) of the polymer in the embodiments of the present invention is usually 3,000,000 or less, preferably 1,000,000 or less, more preferably 500,000 or less, even more preferably 200,000 or less, and particularly preferably 100,000 or less, for example, 50,000 or less. Furthermore, the weight-average molecular weight is usually 2,500 or more, preferably 5,000 or more, more preferably 10,000 or more, even more preferably 15,000 or more, and particularly preferably 17,000 or more.

[0310] When the weight-average molecular weight of the polymer is below the upper limit, solubility in organic solvents is obtained, and the polymer tends to have excellent film-forming properties. Furthermore, when the weight-average molecular weight of the polymer is above the lower limit, the decrease in the polymer's glass transition temperature, melting point, and vaporization temperature is suppressed, and the heat resistance tends to improve.

[0311] The number-average molecular weight (Mn) of the polymer in the embodiments of the present invention is usually 2,500,000 or less, preferably 750,000 or less, more preferably 400,000 or less, particularly preferably 100,000 or less, for example, 50,000 or less. Furthermore, the number-average molecular weight is usually 2,000 or more, preferably 4,000 or more, more preferably 6,000 or more, and even more preferably 8,000 or more.

[0312] The degree of dispersion (Mw / Mn) of the polymer in the embodiments of the present invention is preferably 3.5 or less, more preferably 2.5 or less, even more preferably 2.0 or less, and even more preferably 1.5 or less. Since a smaller degree of dispersion is better, the lower limit is ideally 1. When the degree of dispersion of the polymer is below the above upper limit, it is easy to purify and has good solubility in organic solvents and charge transport ability.

[0313] In embodiments of the present invention, it is particularly preferable that the weight-average molecular weight (Mw) of the polymer is 10,000 or more, and the degree of dispersion (Mw / Mn) is 3.5 or less.

[0314] Typically, the weight-average molecular weight and number-average molecular weight of polymers are determined by SEC (size exclusion chromatography) measurement. In SEC measurement, components with higher molecular weights have shorter elution times, while components with lower molecular weights have longer elution times. However, by using a calibration curve calculated from the elution time of polystyrene (standard sample) with a known molecular weight, the weight-average molecular weight and number-average molecular weight can be calculated by converting the sample's elution time to molecular weight.

[0315] [Specific Examples] In embodiments of the present invention, specific examples of polymers containing repeating units represented by formula (54) are shown below, but the polymers according to embodiments of the present invention are not limited to these. The numbers in the chemical formulas represent the molar ratio of repeating units. n represents the number of repeats. These polymers may be random copolymers, alternating copolymers, block copolymers, or graft copolymers, and are not limited to the order of arrangement of monomers.

[0316]

[0317]

[0318] A polymer containing a repeating unit represented by formula (55), and Ar of the repeating unit represented by formula (55). ５１ Specific examples of polymers having a structure represented by formula (52) are shown below, but the polymers used in the embodiments of the present invention are not limited to these. The numbers in the chemical formulas represent the molar ratio of repeating units. n represents the number of repeats. These polymers may be random copolymers, alternating copolymers, block copolymers, or graft copolymers, and the arrangement order of the monomers is not limited.

[0319]

[0320]

[0321]

[0322]

[0323] Specific examples of polymers containing repeating units represented by formula (56) are shown below, but the polymers used in the embodiments of the present invention are not limited to these. The numbers in the chemical formulas represent the molar ratio of repeating units. n represents the number of repeats. These polymers may be random copolymers, alternating copolymers, block copolymers, or graft copolymers, and are not limited to the order of monomer arrangement.

[0324]

[0325]

[0326] <Repeating unit represented by formula (59)> The repeating unit represented by formula (59) is most preferred as the repeating unit of the polymer according to the embodiment of the present invention. The repeating unit represented by formula (59) includes the repeating unit represented by formula (54) and the repeating unit represented by formula (57).

[0327]

[0328] In formula (59), Ar ５１ X, R ２０１ , R ２０２ This is Ar in formula (54) above. ５１ X, R ２０１ , R ２０２ It is similar to Ar ５１ The nitrogen atom to which it is bonded (N-Ar ５１ It is preferable that the nitrogen atom represented by R is not directly bonded to the fused ring, ５１８ R in formula (57) is ５１８ It is similar to the two Ar ５１ They may be the same or different, and the two R's ５１８ They may be the same or different. In the second embodiment of the present invention, similar to formula (54) above, N-Ar ５1 In this case, it is preferable that the nitrogen atom is not directly bonded to the fused ring.

[0329] In equation (59) above, from the viewpoint of stability during charge transport, X is -C(R ２０７ ) (Caution２０８ ) - Preferably R ２０１ , R ２０２ , R ５１８ , R ２０７ and R ２０８ Each of these groups is preferably an alkyl group, more preferably a methyl group, ethyl group, propyl group, butyl group, pentyl group, or hexyl group, and even more preferably a methyl group.

[0330] Furthermore, in a polymer containing the repeating unit represented by formula (59) above, if there are multiple repeating units represented by formula (59), that is, Ar ５１ , R ２０１ , R ２０２ If there are multiple X's, they may be the same or different. Preferably, the polymer contains multiple repeating units, each having the same structure as the repeating unit represented by formula (59). In this case, because the polymer contains multiple repeating units with the same structure, the HOMO and LUMO of the repeating units are the same, so charge does not concentrate at specific shallow levels and become a trap, and thus the polymer is considered to have excellent charge transport properties.

[0331] In the above formula (59), from the viewpoint of charge transport characteristics and stability during charge transport, Ar ５１ Preferably, at least one of the groups is a biphenyl group substituted with an alkyl group, more preferably a biphenyl group substituted with a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or a hexyl group, and even more preferably a biphenyl group substituted with a hexyl group.

[0332] Specific examples of polymers containing repeating units represented by formula (59) are shown below, but the polymers according to the embodiments of the present invention are not limited to these. The numbers in the chemical formulas represent the molar ratio of repeating units. n represents the number of repeats. These polymers may be random copolymers, alternating copolymers, block copolymers, or graft copolymers, and are not limited to the order of arrangement of monomers.

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343] [Organic Film Forming Composition] The organic film forming composition according to the embodiment of the present invention is described below. The organic film forming composition contains the above polymer and solvent. This organic film forming composition is usually used to form layers or films by a wet film formation method, and is particularly preferably used to form the organic layer of an organic electroluminescent device. The organic layer is particularly preferably a hole transport layer, and in the third embodiment, it is preferably at least one of a hole injection layer and a hole transport layer, and is particularly preferably a hole transport layer. The organic film forming composition may contain one type of the above polymer, or it may contain two or more types in any combination and any ratio.

[0344] [Organic solvent] The organic film-forming composition usually contains an organic solvent. The organic solvent is preferably one that dissolves the polymer. Specifically, an organic solvent that dissolves the polymer in the organic film-forming composition at room temperature in an amount of 0.05% by mass or more, preferably 0.5% by mass or more, and more preferably 1% by mass or more is preferred.

[0345] Specific examples of organic solvents include aromatic solvents such as toluene, xylene, mesitylene, cyclohexylbenzene, and methylnaphthalene; halogen-containing solvents such as 1,2-dichloroethane, chlorobenzene, and o-dichlorobenzene; aliphatic ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and propylene glycol-1-monomethyl ether acetate (PGMEA); and 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole, phenethole, 2-methoxytoluene, and 3-methoxytoluene. Examples of organic solvents include ether-based solvents such as ruene, 4-methoxytoluene, 2,3-dimethylanisole, and 2,4-dimethylanisole; aliphatic ester-based solvents such as ethyl acetate, n-butyl acetate, ethyl lactate, and n-butyl lactate; ester-based solvents such as aromatic esters such as phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, isopropyl benzoate, propyl benzoate, and n-butyl benzoate; and other organic solvents used in the hole injection layer formation composition and hole transport layer formation composition described later.

[0346] The solvent may be one type, or two or more types may be used in any combination and ratio. When multiple types of solvents are used, their total amount shall satisfy the following "solvent content". The solvent content in the organic film-forming composition is usually 10% by mass or more, preferably 30% by mass or more, more preferably 50% by mass or more, and particularly preferably 80% by mass or more, based on the total mass of the organic film-forming composition. By having a solvent content above the lower limit mentioned above, the flatness and uniformity of the formed layer can be improved.

[0347] [Electron-Accepting Compounds] The organic film-forming composition may also preferably contain electron-accepting compounds in order to reduce resistance. In particular, when the organic film-forming composition is used to form a hole injection layer, it is preferable that the organic film-forming composition contains electron-accepting compounds. Preferred electron-accepting compounds are those that have oxidizing power and the ability to accept one electron from the polymer according to the embodiment of the present invention. Specifically, compounds with an electron affinity of 4 eV or more are preferred, and compounds with an electron affinity of 5 eV or more are even more preferred.

[0348] The organic film-forming composition may contain one of the above-mentioned electron-accepting compounds alone, or it may contain two or more in any combination and ratio. When the organic film-forming composition contains an electron-accepting compound, the content of the electron-accepting compound in the organic film-forming composition is usually 0.0005% by mass or more, preferably 0.001% by mass or more, and usually 20% by mass or less, preferably 10% by mass or less, based on the total mass of the organic film-forming composition.

[0349] Furthermore, the ratio of the electron-accepting compound to 100 parts by mass of the polymer according to the embodiment of the present invention is usually 0.5 parts by mass or more, preferably 1 part by mass or more, more preferably 3 parts by mass or more, and also usually 80 parts by mass or less, preferably 60 parts by mass or less, and even more preferably 40 parts by mass or less.

[0350] It is preferable that the content of electron-accepting compounds in the organic film-forming composition is above the lower limit above, because the electron acceptors accept electrons from the polymer, resulting in a low-resistance organic layer. It is also preferable that the content of electron-accepting compounds in the organic film-forming composition is below the upper limit above, because defects are less likely to occur in the formed organic layer, and uneven film thickness is less likely to occur.

[0351] [Cationic Radical Compounds] The organic film-forming composition may further contain a cationic radical compound. The cationic radical compound is preferably an ionic compound consisting of a cationic radical, which is a chemical species obtained by removing one electron from a hole-transporting compound, and a counter anion. However, if the cationic radical is derived from a hole-transporting polymer compound, the cationic radical will have a structure obtained by removing one electron from a repeating unit of the polymer compound.

[0352] The cation radical is preferably a species obtained by removing one electron from a hole-transporting compound, as described later. It is preferable that the cation radical be a species obtained by removing one electron from a preferred hole-transporting compound, given its amorphous nature, visible light transmittance, heat resistance, and solubility.

[0353] Here, a cationic radical compound can be generated by mixing a hole-transporting compound (described later) with the aforementioned electron-accepting compound. That is, by mixing the hole-transporting compound and the electron-accepting compound, electron transfer occurs from the hole-transporting compound to the electron-accepting compound, generating a cationic ion compound consisting of the cationic radical and counter anion of the hole-transporting compound.

[0354] When an organic film-forming composition contains a cationic radical compound, the content of the cationic radical compound in the organic film-forming composition is usually 0.0005% by mass or more, preferably 0.001% by mass or more, and usually 40% by mass or less, preferably 20% by mass or less, based on the total mass of the organic film-forming composition. It is preferable that the content of the cationic radical compound is above the lower limit because the formed organic layer has low resistance, and it is preferable that the content is below the upper limit because defects are less likely to occur in the formed organic layer and uneven film thickness is less likely to occur.

[0355] In addition to the components mentioned above, the organic film-forming composition may also contain components found in the hole injection layer-forming composition and hole transport layer-forming composition described later, in the amounts described later.

[0356] [Method for producing polymers] The method for producing polymers according to the embodiments of the present invention is not particularly limited and is arbitrary. Examples include polymerization by the Suzuki-Coupling reaction, polymerization by the Grignard reaction, polymerization by the Yamamoto reaction, polymerization by the Ullmann reaction, polymerization by the Butchwald-Hartwig reaction, and so on.

[0357] In polymerization methods using the Ulmann reaction and the Butchwald-Hartwig reaction, for example, a polymer containing repeating units represented by formula (2c) is synthesized by reacting an aryl dihalide represented by formula (2a) below (where Z represents a halogen atom such as I, Br, Cl, or F) with a primary aminoaryl represented by formula (2b) below.

[0358]

[0359] In the above reaction equation, Ar １ , R １ , R ２ X, a to d are respectively Ar in formula (54) ５１ , R ２０１ , R ２０２ X is synonymous with a-d.

[0360] Furthermore, in the case of polymerization by the Ulmann reaction and polymerization by the Buchwald-Hartwig reaction, for example, a polymer containing repeating units represented by formula (3) is synthesized by reacting an aryl dihalide represented by formula (3a) (where Z represents a halogen atom such as I, Br, Cl, or F) with a primary aminoaryl represented by formula (2b).

[0361]

[0362] In the above reaction equation, Ar １ , R ３ ~R ６ l to n, p, and q are respectively Ar in formula (55) above. ５１ , R ３０３ ~R ３０６ It is synonymous with l~n, p, and q.

[0363] In the polymerization method described above, the reaction to form the N-aryl bond is usually carried out in the presence of a base such as potassium carbonate, tert-butoxide sodium, or triethylamine. It can also be carried out in the presence of a transition metal catalyst such as a copper or palladium complex.

[0364] [Method for manufacturing an organic film] The method for forming an organic film using the above-mentioned organic film-forming composition is not particularly limited as long as it is a wet film deposition method. For example, the method for forming a hole transport layer by a wet film deposition method, which will be described later, can be applied.

[0365] The aforementioned wet film formation method refers to a method in which a film is formed in a wet manner, such as spin coating, dip coating, die coating, bar coating, blade coating, roll coating, spray coating, capillary coating, inkjet, nozzle printing, screen printing, gravure printing, or flexographic printing, and the film formed by these methods is dried to complete the film formation.

[0366] [Organic Electroluminescent Device] An organic electroluminescent device according to an embodiment of the present invention has an organic layer containing the polymer of the embodiment of the present invention. An example of the structure of an organic electroluminescent device according to an embodiment of the present invention is the organic electroluminescent device 8 shown in Figure 1. In Figure 1, 1 represents a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, 5 is a light-emitting layer, 6 is an electron transport layer, and 7 is a cathode. The organic layer containing the polymer of the embodiment of the present invention can be applied to an organic electroluminescent device as the hole injection layer or hole transport layer, but when used as the hole transport layer of an organic electroluminescent device in particular, it exhibits excellent hole transport characteristics and high chemical stability, so that a highly efficient and long-life organic electroluminescent device can be obtained.

[0367] <Structure of Organic Electroluminescent Device> As an example of the structure of an organic electroluminescent device according to an embodiment of the present invention, Figure 1 shows a schematic diagram (cross-section) of an example of the structure of an organic electroluminescent device 8. In Figure 1, 1 represents the substrate, 2 represents the anode, 3 represents the hole injection layer, 4 represents the hole transport layer, 5 represents the light-emitting layer, 6 represents the electron transport layer, and 7 represents the cathode.

[0368] The materials applied to these structures can be known materials and are not particularly limited, but as specific examples of typical materials and manufacturing methods for each layer, we can cite, for example, the organic electroluminescent devices disclosed in International Publication 2022 / 255403, International Publication 2022 / 092046, International Publication 2023 / 085171, etc. The organic electroluminescent device according to the embodiment of the present invention can also have a structure reversed from the above description, that is, for example, stacking cathode, electron injection layer, electron transport layer, hole blocking layer, light-emitting layer, hole transport layer, hole injection layer, and anode on a substrate in that order. When the organic electroluminescent device according to the embodiment of the present invention is applied to an organic electroluminescent device, it may be used as a single organic electroluminescent device, as a configuration in which multiple organic electroluminescent devices are arranged in an array, or as a configuration in which the anode and cathode are arranged in an X-Y matrix.

[0369] [Method for Manufacturing an Organic Electroluminescent Device] An organic electroluminescent device according to an embodiment of the present invention can be manufactured by a manufacturing method that includes the step of forming the organic layer by a wet film deposition method using an organic film-forming composition according to an embodiment of the present invention. Preferably, in a method for manufacturing an organic electroluminescent device having an anode and a cathode on a substrate, and an organic layer between the anode and the cathode, the method includes the step of forming the organic layer by a wet film deposition method using a composition according to an embodiment of the present invention. It is more preferable that the organic layer is an organic layer located between the anode and the light-emitting layer. For example, the organic layer consists of at least two layers, of which at least one layer is formed by a wet film deposition method using a composition according to an embodiment of the present invention. In one embodiment of the present invention, in a third embodiment, it is even more preferable that the layer formed by the wet film deposition method is at least one of a hole injection layer and a hole transport layer. Furthermore, it is preferable that the organic electroluminescent device according to an embodiment of the present invention includes a hole injection layer, a hole transport layer and a light-emitting layer between the anode and the cathode, and that all of the hole injection layer, hole transport layer and light-emitting layer are formed by a wet film deposition method.

[0370] In the embodiment of the present invention, the organic electroluminescent element is preferably an organic electroluminescent element manufactured by the above-described manufacturing method.

[0371] [Display Device] The display device (organic electroluminescent element display device) according to the embodiment of the present invention comprises an organic electroluminescent element according to the embodiment of the present invention. There are no particular restrictions on the type or structure of the display device according to the embodiment of the present invention, and it can be assembled according to a conventional method using the organic electroluminescent element according to the embodiment of the present invention.

[0372] For example, an organic EL display device according to an embodiment of the present invention can be formed by a method such as that described in "Organic EL Display" (Ohmsha, published August 20, 2004, authored by Shizuka Tokito, Chihaya Adachi, and Hideyuki Murata).

[0373] [Lighting device] The lighting device (organic electroluminescent light-emitting device) according to the embodiment of the present invention is equipped with an organic electroluminescent light-emitting device according to the embodiment of the present invention. There are no particular restrictions on the type or structure of the lighting device according to the embodiment of the present invention, and it can be assembled according to a conventional method using the organic electroluminescent light-emitting device according to the embodiment of the present invention.

[0374] The first embodiment of the present invention will be described in more detail below with reference to examples. The first embodiment of the present invention is not limited to the following examples, and the first embodiment of the present invention can be modified as needed without departing from its essence.

[0375] Compounds M1 and M3 were synthesized using the method described in International Publication No. 2019 / 177175. Compound M2 was also synthesized using the method described in International Publication No. 2022 / 059725.

[0376]

[0377]

[0378]

[0379] <Synthesis of compound M4>

[0380] Under a nitrogen atmosphere, 4-bromoaniline (25.1 g, 0.15 mol) and 4-hexylphenylboronic acid (33.1 g, 0.16 mol) were sequentially bubbled with nitrogen to toluene (300 mL), ethanol (150 mL), and tripotassium phosphate aqueous solution (2.0 mol / L, 183 mL). Subsequently, tetrakis(triphenylphosphine)palladium (0)(Pd(PPh) ３ ) ４ (3.37 g, 2.92 mmol) was added and the mixture was stirred at 95°C for 2.5 hours. After cooling to room temperature, saturated sodium chloride aqueous solution was added and extraction was performed using toluene. The organic layer was washed with saturated sodium chloride aqueous solution, dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was subjected to silica gel column chromatography to obtain compound M4 (yield 30.9 g, yield 83.5%).

[0381] <Synthesis of Compound M5>

[0382] Compound M5-1 was synthesized using the method described in Chem. Commun., 2002, 784-785.

[0383] Under a nitrogen stream, 4-bromoaniline (2.92 g, 17.0 mmol) and compound M5-1 (9.10 g, 17.0 mmol) were sequentially bubbled with nitrogen to toluene (42 mL), ethanol (21 mL), and tripotassium phosphate aqueous solution (2.0 mol / L, 21 mL). Subsequently, tetrakis(triphenylphosphine)palladium (0)(Pd(PPh) ３ ) ４ (0.20 g, 0.17 mmol) was added and the mixture was stirred at 90°C for 6 hours. After cooling to room temperature, saturated sodium chloride aqueous solution was added and extraction was performed using toluene. The organic layer was washed with saturated sodium chloride aqueous solution, dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was subjected to silica gel column chromatography to obtain compound M5 (yield 4.12 g, yield 48.4%).

[0384] <Synthesis of Polymer P1>

[0385] Compound M1 (2.50 g, 4.70 mmol), 2-amino-9,9-dimethylfluorene (0.85 g, 4.04 mmol), 2-amino-9,9-dihexylfluorene (1.87 g, 5.35 mmol), tert-butoxysodium (3.48 g, 36.2 mmol), and toluene (52 ml) were charged, the system was thoroughly purged with nitrogen, and heated to 60°C to obtain solution A1. To a 15 ml solution of tris(dibenzylideneacetone)dipalladium complex (0.086 g, 0.094 mmol) in toluene, [4-(N,N-dimethylamino)phenyl]di-tert-butylphosphine (Amphos) (0.20 g, 0.75 mmol) was added, and heated to 60°C to obtain solution B1.

[0386] Under a nitrogen atmosphere, solution B1 was added to solution A1 and the reaction was carried out under reflux for 1.0 hour. After confirming that compound M1 had disappeared, compound M2 (1.88 g, 3.83 mmol) was added. After 1 hour, bromobenzene (1.36 g, 8.69 mmol) was added and the reaction was carried out under reflux for 1 hour. The reaction mixture was allowed to cool, and the solution was added dropwise to an ethanol / water (350 ml / 100 ml) solution to obtain a crude polymer with end caps.

[0387] The end-capped crude polymer was dissolved in toluene, reprecipitated in acetone, and the precipitated polymer was filtered off to obtain the target polymer P1 (2.6 g). The molecular weight and other properties of the obtained polymer P1 were as follows: Weight-average molecular weight (Mw) = 27002 Number-average molecular weight (Mn) = 20456 Degree of dispersion (Mw / Mn) = 1.32

[0388] <Synthesis of Polymer P2>

[0389] Compound M1 (2.50 g, 4.70 mmol), compound M4 (2.38 g, 9.39 mmol), tert-butoxysodium (3.48 g, 36.2 mmol), and toluene (52 ml) were charged, the system was thoroughly purged with nitrogen, and heated to 60°C to obtain solution A2. To a 15 ml solution of tris(dibenzylideneacetone)dipalladium complex (0.086 g, 0.094 mmol) in toluene, [4-(N,N-dimethylamino)phenyl]di-tert-butylphosphine (Amphos) (0.20 g, 0.75 mmol) was added and heated to 60°C to obtain solution B2.

[0390] Under a nitrogen atmosphere, solution B2 was added to solution A2 and the reaction was carried out under reflux for 1.0 hour. After confirming that compound M1 had disappeared, compound M2 (1.91 g, 3.88 mmol) was added. After 1 hour, bromobenzene (1.29 g, 8.22 mmol) was added and the reaction was carried out under reflux for 1 hour. The reaction mixture was allowed to cool, and the solution was added dropwise to an ethanol / water (400 ml / 260 ml) solution to obtain a crude polymer with end caps.

[0391] The end-capped crude polymer was dissolved in toluene, reprecipitated in acetone, and the precipitated polymer was filtered off to obtain the target polymer P2 (2.9 g). The molecular weight and other properties of the obtained polymer P2 were as follows: Weight-average molecular weight (Mw) = 29950 Number-average molecular weight (Mn) = 22863 Degree of dispersion (Mw / Mn) = 1.31

[0392] <Synthesis of Polymer P3>

[0393] Compound M1 (3.00 g, 5.64 mmol), compound M3 (1.11 g, 1.13 mmol), compound M4 (2.57 g, 10.1 mmol), tert-butoxysodium (4.18 g, 43.5 mmol), and toluene (62 ml) were charged, the system was thoroughly purged with nitrogen, and heated to 60°C to obtain solution A3. To a 21 ml solution of tris(dibenzylideneacetone)dipalladium complex (0.10 g, 0.11 mmol) in toluene, [4-(N,N-dimethylamino)phenyl]di-tert-butylphosphine (Amphos) (0.24 g, 0.90 mmol) was added, and heated to 60°C to obtain solution B3.

[0394] Under a nitrogen atmosphere, solution B3 was added to solution A3 and the reaction was carried out under reflux for 1.0 hour. After confirming that compound M1 had disappeared, compound M2 (2.27 g, 4.62 mmol) was added. After 1 hour, bromobenzene (1.59 g, 10.1 mmol) was added and the reaction was carried out under reflux for 1 hour. The reaction mixture was allowed to cool, and the solution was added dropwise to an ethanol / water (367 ml / 150 ml) solution to obtain a crude polymer with end caps.

[0395] The end-capped crude polymer was dissolved in toluene, reprecipitated in acetone, and the precipitated polymer was filtered off to obtain the target polymer P3 (4.0 g). The molecular weight and other properties of the obtained polymer P3 were as follows: Weight-average molecular weight (Mw) = 31590 Number-average molecular weight (Mn) = 23752 Degree of dispersion (Mw / Mn) = 1.33

[0396] <Synthesis of Polymer P4>

[0397] Compound M1 (2.00 g, 3.76 mmol), compound M4 (1.71 g, 6.76 mmol), compound M5 (0.38 g, 0.75 mmol), tert-butoxysodium (2.78 g, 29.0 mmol), and toluene (42 ml) were charged, the system was thoroughly purged with nitrogen, and heated to 60°C to obtain solution A4. To a 15 ml solution of tris(dibenzylideneacetone)dipalladium complex (0.069 g, 0.075 mmol) in toluene, [4-(N,N-dimethylamino)phenyl]di-tert-butylphosphine (Amphos) (0.16 g, 0.60 mmol) was added and heated to 60°C to obtain solution B4.

[0398] Under a nitrogen atmosphere, solution B4 was added to solution A4 and the reaction was carried out under reflux for 1.0 hour. After confirming that compound M1 had disappeared, compound M2 (1.51 g, 3.08 mmol) was added. After 1 hour, bromobenzene (1.06 g, 6.76 mmol) was added and the reaction was carried out under reflux for 1 hour. The reaction mixture was allowed to cool, and the solution was added dropwise to an ethanol / water (230 ml / 100 ml) solution to obtain a crude polymer with end caps.

[0399] The end-capped crude polymer was dissolved in toluene, reprecipitated in acetone, and the precipitated polymer was filtered off to obtain the target polymer P4 (2.5 g). The molecular weight and other properties of the obtained polymer P4 were as follows: Weight-average molecular weight (Mw) = 30207 Number-average molecular weight (Mn) = 22712 Degree of dispersion (Mw / Mn) = 1.33

[0400] <Synthesis of Polymer P5>

[0401] Compound M1 (2.00 g, 3.76 mmol), compound M3 (0.74 g, 0.75 mmol), 2-amino-9,9-dimethylfluorene (0.86 g, 4.13 mmol), 2-amino-9,9-dihexylfluorene (0.92 g, 2.63 mmol), tert-butoxysodium (2.78 g, 29.0 mmol), and toluene (42 ml) were charged, the system was thoroughly purged with nitrogen, and heated to 60°C to obtain solution A5. To a 15 ml solution of tris(dibenzylideneacetone)dipalladium complex (0.069 g, 0.075 mmol) in toluene, [4-(N,N-dimethylamino)phenyl]di-tert-butylphosphine (Amphos) (0.16 g, 0.60 mmol) was added, and heated to 60°C to obtain solution B5.

[0402] Under a nitrogen atmosphere, solution B5 was added to solution A5 and the reaction was carried out under reflux for 1.0 hour. After confirming that compound M1 had disappeared, compound M2 (1.64 g, 3.33 mmol) was added. After 1 hour, bromobenzene (0.69 g, 4.32 mmol) was added and the reaction was carried out under reflux for 1 hour. The reaction mixture was allowed to cool, and the solution was added dropwise to an ethanol / water (442 ml / 50 ml) solution to obtain a crude polymer with end caps.

[0403] The end-capped crude polymer was dissolved in toluene, reprecipitated in acetone, and the precipitated polymer was filtered off to obtain the target polymer P5 (2.8 g). The molecular weight and other properties of the obtained polymer P5 were as follows: Weight-average molecular weight (Mw) = 40200 Number-average molecular weight (Mn) = 30454 Degree of dispersion (Mw / Mn) = 1.32

[0404] [Absorbance Evaluation] A 1% by mass tetrohydrofuran solution was prepared for each of the polymers P1 to P5. The tetrahydrofuran solvent used was stabilizer-free high-performance liquid chromatograph tetrahydrofuran manufactured by Fujifilm Wako Co., Ltd. For absorbance measurement, a Hitachi High-Tech Science Co., Ltd. U-3900H spectrophotometer was used, a 1 cm × 1 cm quartz cell was used, and measurements were taken at room temperature. The measurement results are shown in Table 1. In Table 1, if Abs 500 nm is less than 0.003, it is classified as "A", if it is between 0.003 and 0.004, it is classified as "B", and if it is greater than 0.004, it is classified as "C". If Abs 460 nm is less than 0.006, it is classified as "A", if it is between 0.006 and 0.010, it is classified as "B", and if it is greater than 0.010, it is classified as "C".

[0405] [Example 1] An organic electroluminescent device was fabricated by the following method. A transparent conductive film of indium tin oxide (ITO) to a thickness of 50 nm was deposited on a glass substrate (Geomatec Co., Ltd., sputter-deposited product). The anode was formed by patterning a 2 mm wide stripe using conventional photolithography techniques and hydrochloric acid etching. The substrate with the ITO pattern formed in this way was cleaned in the following order: ultrasonic cleaning with an aqueous surfactant solution, rinsing with ultrapure water, ultrasonic cleaning with ultrapure water, rinsing with ultrapure water, drying with compressed air, and finally, ultraviolet ozone cleaning.

[0406] As a composition for forming a hole injection layer, a composition was prepared by dissolving 3.0% by mass of a hole-transporting polymer compound having a repeating structure represented by the following formula (P-1) and 0.6% by mass of an electron-accepting compound represented by the following formula (HI-1) in ethyl benzoate. This solution was spin-coated onto the substrate in air and dried at 240°C for 30 minutes using a hot plate in air to form a uniform thin film with a thickness of 40 nm, which served as the hole injection layer.

[0407]

[0408]

[0409] Next, the polymer P1 described above was dissolved in mesitylene to prepare a 2.5% by mass solution. This solution was spin-coated onto a substrate coated with the hole injection layer in a nitrogen glove box, and dried at 230°C for 30 minutes using a hot plate in the nitrogen glove box to form a uniform thin film with a thickness of 60 nm, which served as the hole transport layer.

[0410] Next, 97 parts by mass of the compound represented by the following formula (H-1) and 3 parts by mass of the compound represented by the following formula (D-1) were weighed out as materials for the light-emitting layer, and dissolved in cyclohexylbenzene to prepare a 4.2% by mass solution as a composition for forming the light-emitting layer.

[0411]

[0412]

[0413] This light-emitting layer-forming composition was spin-coated onto a substrate coated with the hole transport layer in a nitrogen glove box, and dried at 120°C for 20 minutes on a hot plate in the nitrogen glove box to form a uniform thin film with a thickness of 40 nm, which served as the light-emitting layer. The substrate with the light-emitting layer deposited was placed in a vacuum deposition apparatus, and the inside of the apparatus was 2 × 10 －４ The exhaust was vented until the pressure dropped below Pa.

[0414] Next, the compound represented by the following formula (HB-1) and 8-hydroxyquinolinolatritium were co-deposited onto the light-emitting layer at a rate of 1 Å / second by vacuum deposition in a film thickness ratio of 2:3 to form a hole-blocking layer with a film thickness of 30 nm.

[0415]

[0416] Next, a 2 mm wide striped shadow mask was placed in close contact with the substrate, perpendicular to the anode's ITO stripe, as a mask for cathode deposition, and then placed in a separate vacuum deposition apparatus. Then, aluminum was heated using a molybdenum boat to form an aluminum layer with a thickness of 80 nm at a deposition rate of 1 to 8.6 Å / second, thereby forming the cathode. In this way, an organic electroluminescent device with an emitting area of ​​2 mm x 2 mm was obtained.

[0417] [Example 2] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that polymer P2 was used instead of polymer P1.

[0418] [Example 3] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that polymer P3 was used instead of polymer P1.

[0419] [Example 4] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that polymer P4 was used instead of polymer P1.

[0420] [Comparative Example 1] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that polymer P5 was used instead of polymer P1.

[0421] [Evaluation of Organic Electroluminescent Devices] The organic electroluminescent devices obtained in Examples 1 to 4 and Comparative Example 1 were evaluated for a brightness of 1000 cd / m². ２ The current efficiency (cd / A) and external quantum efficiency (%) were measured when light was emitted using the device. Also, 20 mA / cm² was measured. ２ The time it took for the brightness to decrease to 90% of the initial brightness (LT90, drive life) was measured when the element was continuously energized at the specified current density. These measurement results are shown in Table 1. In Table 1, the values ​​for Examples 1 to 4 are relative values ​​with the value for Comparative Example 1 set to 1.00.

[0422]

[0423] From the results in Table 1, it was found that the organic electroluminescent device using a polymer according to the embodiment of the present invention, which satisfies equations (1) and (2) and at least one of (i) and (ii), has high luminous efficiency and a long operating life.

[0424] [Example 5] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that polymer P6, represented by the following formula, was dissolved in anisole instead of polymer P1, and a hole transport layer was obtained by spin-coating the prepared 2.0% by mass solution.

[0425]

[0426] [Example 6] An organic electroluminescent device was fabricated in the same manner as in Example 5, except that polymer P7 represented by the following formula was used instead of polymer P6.

[0427]

[0428] [Example 7] An organic electroluminescent device was fabricated in the same manner as in Example 5, except that polymer P8, represented by the following formula, was used instead of polymer P6.

[0429]

[0430] [Comparative Example 2] An organic electroluminescent device was fabricated in the same manner as in Example 5, except that polymer P9 represented by the following formula was used instead of polymer P6.

[0431]

[0432] [Evaluation of Organic Electroluminescent Devices] The organic electroluminescent devices obtained in Examples 5-7 and Comparative Examples 1 and 2 were evaluated for brightness of 1000 cd / m². ２ The current efficiency (cd / A) and external quantum efficiency (%) were measured when light was emitted using the device. Also, 20 mA / cm² was measured. ２ The time it took for the brightness to decrease to 90% of the initial brightness (LT90, drive life) was measured when the element was continuously energized at the specified current density. These measurement results are shown in Table 2. In Table 2, the values ​​for Examples 5-7 and Comparative Example 2 are relative values ​​with the value for Comparative Example 1 set to 1.00.

[0433]

[0434] From the results in Table 2, it was found that the organic electroluminescent device using a polymer according to the embodiment of the present invention, which satisfies equations (1) and (2) and at least one of (i) and (ii), has high luminous efficiency and a long operating life.

[0435] The second embodiment will be described in more detail below with reference to examples. This embodiment is not limited to the following examples and can be modified as needed without departing from its essence.

[0436] Compounds M1 and M3 were synthesized using the method described in International Publication No. 2019 / 177175. Compound M2 was also synthesized using the method described in International Publication No. 2022 / 059725.

[0437]

[0438]

[0439]

[0440] <Synthesis of compound M4>

[0441] Under a nitrogen atmosphere, 4-bromoaniline (25.1 g, 0.15 mol) and 4-hexylphenylboronic acid (33.1 g, 0.16 mol) were sequentially bubbled with nitrogen to toluene (300 mL), ethanol (150 mL), and tripotassium phosphate aqueous solution (2.0 mol / L, 183 mL). Subsequently, tetrakis(triphenylphosphine)palladium (0)(Pd(PPh) ３ ) ４ (3.37 g, 2.92 mmol) was added and the mixture was stirred at 95°C for 2.5 hours. After cooling to room temperature, saturated sodium chloride aqueous solution was added and extraction was performed using toluene. The organic layer was washed with saturated sodium chloride aqueous solution, dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was subjected to silica gel column chromatography to obtain compound M4 (yield 30.9 g, yield 83.5%).

[0442] <Synthesis of Compound M5>

[0443] Compound M5-1 was synthesized using the method described in Chem. Commun., 2002, 784-785.

[0444] Under a nitrogen stream, 4-bromoaniline (2.92 g, 17.0 mmol) and compound M5-1 (9.10 g, 17.0 mmol) were sequentially bubbled with nitrogen to toluene (42 mL), ethanol (21 mL), and tripotassium phosphate aqueous solution (2.0 mol / L, 21 mL). Subsequently, tetrakis(triphenylphosphine)palladium (0)(Pd(PPh) ３ ) ４(0.20 g, 0.17 mmol) was added and the mixture was stirred at 90°C for 6 hours. After cooling to room temperature, saturated sodium chloride aqueous solution was added and extraction was performed using toluene. The organic layer was washed with saturated sodium chloride aqueous solution, dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was subjected to silica gel column chromatography to obtain compound M5 (yield 4.12 g, yield 48.4%).

[0445] <Synthesis of Polymer P1>

[0446] Compound M1 (3.00 g, 5.64 mmol), compound M3 (1.11 g, 1.13 mmol), compound M4 (2.57 g, 10.1 mmol), tert-butoxysodium (4.18 g, 43.5 mmol), and toluene (62 ml) were charged, the system was thoroughly purged with nitrogen, and heated to 60°C to obtain solution A1. To a 21 ml solution of tris(dibenzylideneacetone)dipalladium complex (0.10 g, 0.11 mmol) in toluene, [4-(N,N-dimethylamino)phenyl]di-tert-butylphosphine (Amphos) (0.24 g, 0.90 mmol) was added and heated to 60°C to obtain solution B1.

[0447] Under a nitrogen atmosphere, solution B1 was added to solution A1 and the reaction was carried out under reflux for 1.0 hour. After confirming that compound M1 had disappeared, compound M2 (2.27 g, 4.62 mmol) was added. After 1 hour, bromobenzene (1.59 g, 10.1 mmol) was added and the reaction was carried out under reflux for 1 hour. The reaction mixture was allowed to cool, and the solution was added dropwise to an ethanol / water (367 ml / 150 ml) solution to obtain a crude polymer with end caps.

[0448] The end-capped crude polymer was dissolved in toluene, reprecipitated in acetone, and the precipitated polymer was filtered off to obtain the target polymer P1 (4.0 g). The molecular weight and other properties of the obtained polymer P1 were as follows: Weight-average molecular weight (Mw) = 31590 Number-average molecular weight (Mn) = 23752 Degree of dispersion (Mw / Mn) = 1.33 C of polymer P1 Ｂ / C Ａ The calculation yielded 2.2.

[0449] <Synthesis of Polymer P2>

[0450] Compound M1 (2.00 g, 3.76 mmol), compound M4 (1.71 g, 6.76 mmol), compound M5 (0.38 g, 0.75 mmol), tert-butoxysodium (2.78 g, 29.0 mmol), and toluene (42 ml) were charged, the system was thoroughly purged with nitrogen, and heated to 60°C to obtain solution A2. To a 15 ml solution of tris(dibenzylideneacetone)dipalladium complex (0.069 g, 0.075 mmol) in toluene, [4-(N,N-dimethylamino)phenyl]di-tert-butylphosphine (Amphos) (0.16 g, 0.60 mmol) was added and heated to 60°C to obtain solution B2.

[0451] Under a nitrogen atmosphere, solution B2 was added to solution A2 and the reaction was carried out under reflux by heating for 1.0 hour. After confirming that compound M1 had disappeared, compound M2 (1.51 g, 3.08 mmol) was added. After 1 hour, bromobenzene (1.06 g, 6.76 mmol) was added and the reaction was carried out under reflux by heating for 1 hour. The reaction mixture was allowed to cool, and the solution was added dropwise to an ethanol / water (230 ml / 100 ml) solution to obtain a crude polymer with end caps.

[0452] The end-capped crude polymer was dissolved in toluene, reprecipitated in acetone, and the precipitated polymer was filtered off to obtain the target polymer P2 (2.5 g). The molecular weight and other properties of the obtained polymer P2 were as follows: Weight-average molecular weight (Mw) = 30207 Number-average molecular weight (Mn) = 22712 Degree of dispersion (Mw / Mn) = 1.33 C of polymer P2 Ｂ / C Ａ The calculation yielded 2.2.

[0453] <Synthesis of Polymer P3>

[0454] Compound M1 (2.50 g, 4.70 mmol), compound M4 (2.38 g, 9.39 mmol), tert-butoxysodium (3.48 g, 36.2 mmol), and toluene (52 ml) were charged, the system was thoroughly purged with nitrogen, and heated to 60°C to obtain solution A3.

[0455] To a 15 ml solution of tris(dibenzylideneacetone)dipalladium complex (0.086 g, 0.094 mmol) in toluene, [4-(N,N-dimethylamino)phenyl]di-tert-butylphosphine (Amphos) (0.20 g, 0.75 mmol) was added, and the mixture was heated to 60°C to obtain solution B3.

[0456] Under a nitrogen atmosphere, solution B3 was added to solution A3 and the reaction was carried out under reflux for 1.0 hour. After confirming that compound M1 had disappeared, compound M2 (1.91 g, 3.88 mmol) was added. After 1 hour, bromobenzene (1.29 g, 8.22 mmol) was added and the reaction was carried out under reflux for 1 hour. The reaction mixture was allowed to cool, and the solution was added dropwise to an ethanol / water (400 ml / 260 ml) solution to obtain a crude polymer with end caps.

[0457] The end-capped crude polymer was dissolved in toluene, reprecipitated in acetone, and the precipitated polymer was filtered off to obtain the target polymer P3 (2.9 g). The molecular weight and other properties of the obtained polymer P3 were as follows: Weight-average molecular weight (Mw) = 29950 Number-average molecular weight (Mn) = 22863 Degree of dispersion (Mw / Mn) = 1.31 C of polymer P3 Ｂ / C Ａ The calculation yielded 2.0.

[0458] [Example 2-1] An organic electroluminescent device was fabricated by the following method. A transparent conductive film of indium tin oxide (ITO) to a thickness of 50 nm was deposited on a glass substrate (Geomatec Co., Ltd., sputter-deposited product). The anode was formed by patterning the film into 2 mm wide stripes using conventional photolithography techniques and hydrochloric acid etching. The substrate with the ITO pattern formed in this way was cleaned in the following order: ultrasonic cleaning with an aqueous surfactant solution, rinsing with ultrapure water, ultrasonic cleaning with ultrapure water, rinsing with ultrapure water, drying with compressed air, and finally, ultraviolet ozone cleaning.

[0459] As a composition for forming a hole injection layer, a composition was prepared by dissolving 3.0% by mass of a hole-transporting polymer compound having a repeating structure represented by the following formula (P-1) and 0.6% by mass of an electron-accepting compound represented by the following formula (HI-1) in ethyl benzoate. This solution was spin-coated onto the substrate in air and dried at 240°C for 30 minutes using a hot plate in air to form a uniform thin film with a thickness of 40 nm, which served as the hole injection layer.

[0460]

[0461]

[0462] Next, the polymer P1 described above was dissolved in mesitylene to prepare a 2.5% by mass solution. This solution was spin-coated onto a substrate coated with the hole injection layer in a nitrogen glove box, and dried at 230°C for 30 minutes using a hot plate in the nitrogen glove box to form a uniform thin film with a thickness of 60 nm, which served as the hole transport layer.

[0463] Next, 3.13 parts by mass of the compound represented by the following formula (H-1), 1.04 parts by mass of the compound represented by the following formula (H-2), and 0.83 parts by mass of the compound represented by the following formula (D-1) were weighed out as materials for the light-emitting layer, and dissolved in cyclohexylbenzene to prepare a 5.0% by mass solution as a composition for forming the light-emitting layer.

[0464]

[0465]

[0466]

[0467] This light-emitting layer-forming composition was spin-coated onto a substrate coated with the hole transport layer in a nitrogen glove box, and dried at 120°C for 20 minutes on a hot plate in the nitrogen glove box to form a uniform thin film with a thickness of 40 nm, which served as the light-emitting layer. The substrate with the light-emitting layer deposited was placed in a vacuum deposition apparatus, and the inside of the apparatus was 2 × 10 －４ The exhaust was vented until the pressure dropped below Pa.

[0468] Next, the compound represented by the following formula (HB-1) and 8-hydroxyquinolinolatritium were co-deposited onto the light-emitting layer at a rate of 1 Å / second by vacuum deposition in a film thickness ratio of 2:3 to form a hole-blocking layer with a film thickness of 30 nm.

[0469]

[0470] Next, a 2 mm wide striped shadow mask was placed in close contact with the substrate, perpendicular to the anode's ITO stripe, as a mask for cathode deposition, and then placed in a separate vacuum deposition apparatus. Then, aluminum was heated using a molybdenum boat to form an aluminum layer with a thickness of 80 nm at a deposition rate of 1 to 8.6 Å / second, thereby forming the cathode. In this way, an organic electroluminescent device with an emitting area of ​​2 mm x 2 mm was obtained.

[0471] [Example 2-2] An organic electroluminescent device was fabricated in the same manner as in Example 2-1, except that polymer P2 was used instead of polymer P1.

[0472] [Comparative Example 2-1] An organic electroluminescent device was fabricated in the same manner as in Example 2-1, except that a hole-transporting polymer compound (HT-1) having a repeating structure represented by the following formula (HT-1) was used instead of the polymer P1.

[0473]

[0474] C of a hole-transporting polymer compound having a repeating structure represented by the above formula (HT-1) Ｂ / C Ａ The calculation yielded 2.33.

[0475] [Comparative Example 2-2] An organic electroluminescent device was fabricated in the same manner as in Example 2-1, except that a hole-transporting polymer compound (HT-2) having a repeating structure represented by the following formula (HT-2) was used instead of the polymer P1.

[0476]

[0477] C of a hole-transporting polymer compound having a repeating structure represented by the above formula (HT-2) Ｂ / C Ａ The calculation yielded 1.33.

[0478] [Evaluation of Organic Electroluminescent Devices] The organic electroluminescent devices obtained in Examples 2-1, 2-2 and Comparative Examples 2-1, 2-2 were evaluated to a brightness of 1000 cd / m². ２ The current efficiency (cd / A) and external quantum efficiency (%) when light was emitted were measured. The measurement results are shown in Table 3. In Table 3, the values ​​for Examples 2-1, 2-2 and Comparative Example 2-1 are relative values ​​with the value for Comparative Example 2-2 set to 1.00. Also, in Table 3, C Ｂ / C Ａ In the column, "A" means that the polymer used in the hole transport layer satisfies formula (TI), and "B" means that the polymer used in the hole transport layer does not satisfy formula (TI).

[0479]

[0480] [Example 2-3] Organic electroluminescent devices were fabricated by the following method. A transparent conductive film of indium tin oxide (ITO) to a thickness of 50 nm was deposited on a glass substrate (Geomatec Co., Ltd., sputter-deposited product). The anode was formed by patterning a 2 mm wide stripe using conventional photolithography techniques and hydrochloric acid etching. The substrate with the ITO pattern formed in this way was cleaned in the following order: ultrasonic cleaning with an aqueous surfactant solution, rinsing with ultrapure water, ultrasonic cleaning with ultrapure water, rinsing with ultrapure water, drying with compressed air, and finally ultraviolet ozone cleaning.

[0481] As a composition for forming a hole injection layer, a composition was prepared by dissolving 3.0% by mass of a hole-transporting polymer compound having a repeating structure represented by the following formula (P-1) and 0.6% by mass of an electron-accepting compound represented by the following formula (HI-1) in ethyl benzoate. This solution was spin-coated onto the substrate in air and dried at 240°C for 30 minutes using a hot plate in air to form a uniform thin film with a thickness of 40 nm, which served as the hole injection layer.

[0482]

[0483]

[0484] Next, 100 parts by mass of the polymer P1 was dissolved in mesitylene to prepare a 2.5% by mass solution. This solution was spin-coated onto a substrate coated with the hole injection layer in a nitrogen glove box, and dried at 230°C for 30 minutes on a hot plate in the nitrogen glove box to form a uniform thin film with a thickness of 60 nm, which served as the hole transport layer.

[0485] Next, 97 parts by mass of the compound represented by the following formula (H-3) and 3 parts by mass of the compound represented by the following formula (D-2) were weighed out as materials for the light-emitting layer, and dissolved in cyclohexylbenzene to prepare a 4.2% by mass solution as a composition for forming the light-emitting layer.

[0486]

[0487]

[0488] This light-emitting layer-forming composition was spin-coated onto a substrate coated with the hole transport layer in a nitrogen glove box, and dried at 120°C for 20 minutes on a hot plate in the nitrogen glove box to form a uniform thin film with a thickness of 40 nm, which served as the light-emitting layer. The substrate with the light-emitting layer deposited was placed in a vacuum deposition apparatus, and the inside of the apparatus was 2 × 10 －４ The exhaust was vented until the pressure dropped below Pa.

[0489] Next, the compound represented by the following formula (HB-1) and 8-hydroxyquinolinolatritium were co-deposited onto the light-emitting layer at a rate of 1 Å / second by vacuum deposition in a film thickness ratio of 2:3 to form a hole-blocking layer with a film thickness of 30 nm.

[0490]

[0491] Next, a 2 mm wide striped shadow mask was placed in close contact with the substrate, perpendicular to the anode's ITO stripe, as a mask for cathode deposition, and then placed in a separate vacuum deposition apparatus. Then, aluminum was heated using a molybdenum boat to form an aluminum layer with a thickness of 80 nm at a deposition rate of 1 to 8.6 Å / second, thereby forming the cathode. In this way, an organic electroluminescent device with an emitting area of ​​2 mm x 2 mm was obtained.

[0492] [Example 2-4] An organic electroluminescent device was fabricated in the same manner as in Example 2-3, except that polymer P2 was used instead of polymer P1.

[0493] [Comparative Example 2-3] An organic electroluminescent device was fabricated in the same manner as in Example 2-3, except that a hole-transporting polymer compound (HT-2) having a repeating structure represented by (HT-2) was used instead of the polymer P1.

[0494] [Comparative Example 2-4] An organic electroluminescent device was fabricated in the same manner as in Example 2-3, except that a hole-transporting polymer compound (HT-5) having a repeating structure represented by the following formula (HT-5) was used instead of the polymer P1.

[0495]

[0496] C of a hole-transporting polymer compound having a repeating structure represented by the above formula (HT-5) Ｂ / C Ａ The calculation yielded 3.20.

[0497] [Comparative Example 2-5] An organic electroluminescent device was fabricated in the same manner as in Example 2-3, except that a hole-transporting polymer compound (HT-1) having a repeating structure represented by the formula (HT-1) was used instead of the polymer P1.

[0498] [Comparative Example 2-6] An organic electroluminescent device was fabricated in the same manner as in Example 2-3, except that a hole-transporting polymer compound (HT-6) having a repeating structure represented by the following formula (HT-6) was used instead of the polymer P1.

[0499]

[0500] C of a hole-transporting polymer compound having a repeating structure represented by the above formula (HT-6) Ｂ / C Ａ The calculation yielded 3.18.

[0501] [Comparative Example 2-7] An organic electroluminescent device was fabricated in the same manner as in Example 2-3, except that a hole-transporting polymer compound (HT-7) having a repeating structure represented by the following formula (HT-7) was used instead of the polymer P1.

[0502]

[0503] C of a hole-transporting polymer compound having a repeating structure represented by the above formula (HT-7) Ｂ / C Ａ The calculation yielded 2.17.

[0504] [Evaluation of Organic Electroluminescent Devices] The organic electroluminescent devices obtained in Examples 2-3 to 2-4 and Comparative Examples 2-3 to 2-7 were evaluated at 1000 cd / m². ２ The current efficiency (cd / A) and external quantum efficiency (%) were measured at the brightness level of 20 mA / cm². ２ The time (LT95, drive life) (h) at which the brightness decreased to 95% of the initial brightness was measured when the element was continuously energized at the specified current density. The results are shown in Table 4. In Table 4, the values ​​for Examples 2-3 to 2-4 and Comparative Examples 2-3 to 2-6 are relative values ​​with the value for Comparative Example 2-7 set to 1.00.

[0505]

[0506] [Example 2-5] An organic electroluminescent device was fabricated in the same manner as in Example 2-3.

[0507] [Example 2-6] An organic electroluminescent device was fabricated in the same manner as in Example 2-3, except that polymer P2 was used instead of polymer P1.

[0508] [Example 2-7] An organic electroluminescent device was fabricated in the same manner as in Example 2-3, except that polymer P3 was used instead of polymer P1.

[0509] [Comparative Example 2-8] An organic electroluminescent device was fabricated in the same manner as in Example 2-3, except that HT-7 was used instead of polymer P1.

[0510] [Evaluation of Organic Electroluminescent Devices] The organic electroluminescent devices obtained in Examples 2-5 to 2-7 and Comparative Example 2-8 were evaluated at 1000 cd / m². ２ The current efficiency (cd / A) and external quantum efficiency (%) were measured at the brightness level of 20 mA / cm². ２The time (LT90, drive life) (h) at which the brightness decreased to 90% of the initial brightness was measured when the element was continuously energized at the specified current density. The results are shown in Table 5. In Table 5, the values ​​for Examples 2-5 to 2-7 are relative values ​​with the value for Comparative Example 2-8 set to 1.00.

[0511]

[0512] <Evaluation of Solvent Resistance> The formation of a film for evaluating solvent resistance using a polymer, and the evaluation of the solvent resistance of the obtained film, were carried out as follows. First, a solution was prepared by dissolving polymer P1 in mesitylene at a concentration of 2.4% by mass. This solution was dropped onto an ITO substrate in air and spin-coated, and dried on a hot plate at 100°C for 1 minute. This substrate was baked on a hot plate at 230°C for 30 minutes to form a film for evaluating solvent resistance with a thickness of 60 nm. Next, the substrate with the film for evaluating solvent resistance was set in a spin coater, 150 μL of test solvent was dropped onto the substrate, and the substrate was left to stand for 600 seconds after dropping to perform the solvent resistance test. Cyclohexylbenzene was used as the test solvent. After that, the substrate was rotated at 1500 rpm for 30 seconds, and then at 4000 rpm for 30 seconds to spin out the dropped solvent. This substrate was dried on a hot plate at 130°C for 10 minutes. Solvent resistance was estimated from the change in film reflectance in the 250–850 nm range before and after the solvent resistance test.

[0513] For polymer P2, polymer P3, hole-transporting polymer compound (HT-1), and hole-transporting polymer compound (HT-3) having a repeating structure represented by the following formula (HT-3), and hole-transporting polymer compound (HT-4) having a repeating structure represented by the following formula (HT-4), solvent resistance evaluation films were prepared using the same method as for polymer P1, and solvent resistance tests were conducted.

[0514]

[0515] C of a hole-transporting polymer compound having a repeating structure represented by the above formula (HT-3) Ｂ / C Ａ The calculation yielded 3.20.

[0516]

[0517] C of a hole-transporting polymer compound having a repeating structure represented by the above formula (HT-4) Ｂ / C Ａ The calculation yielded 1.20.

[0518] Solvent resistance was evaluated based on the following criteria: A: The mean squared root error of the film reflectance in the 250-850 nm range was less than 1.0% before and after the solvent resistance test. X: The mean squared root error of the film reflectance in the 250-850 nm range was 1.0% or more before and after the solvent resistance test.

[0519] The results of the solvent resistance tests for polymers P1-P3, HT-1, HT-3, and HT-4 are summarized in Table 6 below.

[0520]

[0521] From the results in Table 3, it was found that the organic electroluminescent device using the polymer of the second embodiment that satisfies formulas (1) and (2), (i) and satisfies (TI) exhibits high luminous efficiency. Furthermore, from the results in Tables 4 and 5, it was found that the organic electroluminescent device using the polymer of the present invention that satisfies formulas (1) and (2), (i) and satisfies (TI) exhibits high luminous efficiency and a long operating life. Furthermore, from the results in Table 6, it was found that the polymer of the present invention that satisfies formulas (1) and (2), (i) and satisfies (TI) exhibits high solvent resistance to organic solvents.

[0522] The third embodiment will be described in more detail below with reference to examples. This embodiment is not limited to the following examples and can be modified as needed without departing from its essence. [Reference Example 3-1] An organic electroluminescent element was fabricated by the following method. A transparent conductive film of indium tin oxide (ITO) deposited to a thickness of 50 nm (Geomatec Co., Ltd., sputter-deposited product) was patterned into 2 mm wide stripes using conventional photolithography and hydrochloric acid etching to form an anode. The substrate with the ITO pattern formed in this way was cleaned in the following order: ultrasonic cleaning with an aqueous surfactant solution, rinsing with ultrapure water, ultrasonic cleaning with ultrapure water, rinsing with ultrapure water, drying with compressed air, and finally ultraviolet ozone cleaning. As a composition for forming a hole injection layer, a composition was prepared by dissolving 3.0% by mass of a hole-transporting polymer compound having a repeating structure represented by the following formula (P-1) and 0.6% by mass of an electron-accepting compound represented by the following formula (HI-1) in ethyl benzoate. This solution was spin-coated onto the substrate in air and dried at 240°C for 30 minutes using a hot plate in air to form a uniform thin film with a thickness of 40 nm, which served as the hole injection layer.

[0523]

[0524] Next, 100 parts by mass of a charge-transporting polymer compound having a repeating structure represented by the following formula (HT-1) was dissolved in mesitylene to prepare a 2.5% by mass solution. This solution was spin-coated onto a substrate coated with the hole-injection layer in a nitrogen glove box, and dried at 230°C for 30 minutes using a hot plate in the nitrogen glove box to form a uniform thin film with a thickness of 60 nm, which served as the hole transport layer.

[0525]

[0526] Next, 75 parts by mass of the compound represented by the following formula (H-1), 25 parts by mass of the compound represented by the following formula (H-2), and 20 parts by mass of the compound represented by the following formula (D-1) were weighed out as materials for the light-emitting layer, and dissolved in cyclohexylbenzene to prepare a 5.0% by mass solution as a composition for forming the light-emitting layer.

[0527]

[0528]

[0529]

[0530] This light-emitting layer-forming composition was spin-coated onto a substrate coated with the hole transport layer in a nitrogen glove box, and dried at 120°C for 20 minutes on a hot plate in the nitrogen glove box to form a uniform thin film with a thickness of 50 nm, which served as the light-emitting layer. The substrate with the light-emitting layer deposited was placed in a vacuum deposition apparatus, and the inside of the apparatus was 2 × 10 －４ The system was evacuated until the pressure fell below Pa. Next, the compound represented by the following formula (HB-1) and 8-hydroxyquinolinolatritium were co-deposited onto the light-emitting layer at a rate of 1 Å / second using vacuum deposition in a film thickness ratio of 2:3 to form a hole-blocking layer with a film thickness of 30 nm.

[0531]

[0532] Next, a 2 mm wide striped shadow mask was placed in close contact with the substrate, perpendicular to the anode ITO stripe, as a mask for cathode deposition, and then set up in a separate vacuum deposition apparatus. Then, aluminum was heated using a molybdenum boat to form an aluminum layer with a thickness of 80 nm at a deposition rate of 1 to 8.6 Å / second, thereby forming the cathode. In this way, an organic electroluminescent element with an emitting area of ​​2 mm × 2 mm was obtained.

[0533] [Example 3-2] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that 100 parts by mass of a charge-transporting polymer compound having the structure represented by the following formula (HT-2) was used to form a hole transport layer, instead of the charge-transporting polymer compound having the structure represented by formula (HT-1).

[0534]

[0535] [Example 3-3] An organic electroluminescent device was fabricated in the same manner as in Example 3-1, except that 100 parts by mass of a charge-transporting polymer compound having the structure represented by the following formula (HT-3) was used to form a hole transport layer, instead of the charge-transporting polymer compound having the structure represented by formula (HT-1).

[0536]

[0537] [Comparative Example 3-1] An organic electroluminescent element was fabricated in the same manner as in Example 3-1, except that 100 parts by mass of a charge-transporting polymer compound having the structure represented by the following formula (HT-4) was used to form a hole transport layer, instead of the charge-transporting polymer compound having the structure represented by formula (HT-1).

[0538]

[0539] [Comparative Example 3-2] An organic electroluminescent element was fabricated in the same manner as in Example 3-1, except that 100 parts by mass of a charge-transporting polymer compound having the structure represented by the following formula (HT-5) was used to form a hole transport layer, instead of the charge-transporting polymer compound having the structure represented by formula (HT-1).

[0540]

[0541] [Evaluation of Organic Electroluminescent Devices] The organic electroluminescent devices obtained in Examples 3-1 to 3-3 and Comparative Examples 3-1 and 3-2 were subjected to a current of 15 mA / cm². ２ The drive life was measured by applying a current of 1,000 cd / m². ２ The equivalent lifespan was calculated. An acceleration factor of 1.5 was used, and the time it took for the brightness to decrease to 95% of the initial brightness was measured to achieve a value of 1,000 cd / m². ２ The converted lifespan (LT95) was calculated. The ratio of the LT95 of Examples 3-1 to 3-3 and Comparative Example 3-2 was calculated, with the LT95 of Comparative Example 3-1 set to 100, and this was used as the relative drive life. The measurement results and the [N / C(side)] / [N / C(main)] and Mw(side) / Mw(main) of the polymer used to form the hole transport layer are shown in Table 7.

[0542]

[0543] The results in Table 7 show that the performance of the organic electroluminescent device using the polymer of the third embodiment as the hole transport layer is improved.

[0544] [Reference Example 3-2] An organic electroluminescent device was fabricated in the same manner as in Example 3-1, except that the light-emitting layer was formed as described below. As the material for the light-emitting layer, 97 parts by mass of the compound represented by the following formula (H-3) and 3 parts by mass of the compound represented by the following formula (D-2) were weighed out and dissolved in cyclohexylbenzene to prepare a 4.0% by mass solution as the composition for forming the light-emitting layer.

[0545]

[0546] This light-emitting layer-forming composition was spin-coated onto a substrate coated with a hole transport layer in a nitrogen glove box, and dried at 120°C for 20 minutes on a hot plate in the nitrogen glove box to form a uniform thin film with a thickness of 40 nm, which served as the light-emitting layer.

[0547] [Example 3-5] An organic electroluminescent device was fabricated in the same manner as in Reference Example 3-2, except that a charge-transport polymer compound (HT-2) was used to form the hole transport layer instead of the charge-transport polymer compound (HT-1).

[0548] [Example 3-6] An organic electroluminescent device was fabricated in the same manner as in Reference Example 3-2, except that a charge-transport polymer compound (HT-3) was used to form the hole transport layer instead of the charge-transport polymer compound (HT-1).

[0549] [Example 3-7] An organic electroluminescent device was fabricated in the same manner as in Reference Example 3-2, except that the hole transport layer was formed using a charge transport polymer compound represented by the following formula (HT-6) instead of the charge transport polymer compound (HT-1).

[0550]

[0551] [Comparative Example 3-3] An organic electroluminescent device was fabricated in the same manner as in Reference Example 3-2, except that a charge-transport polymer compound (HT-4) was used to form the hole transport layer instead of the charge-transport polymer compound (HT-1).

[0552] [Comparative Example 3-4] An organic electroluminescent device was fabricated in the same manner as in Reference Example 3-2, except that a charge-transport polymer compound (HT-5) was used to form the hole transport layer instead of the charge-transport polymer compound (HT-1).

[0553] [Comparative Example 3-5] An organic electroluminescent device was fabricated in the same manner as in Reference Example 3-2, except that the hole transport layer was formed using a charge transport polymer compound represented by the following formula (HT-7) instead of the charge transport polymer compound (HT-1).

[0554]

[0555] [Evaluation of Organic Electroluminescent Devices] The organic electroluminescent devices obtained in Reference Example 3-2, Examples 3-5 to 3-7, and Comparative Examples 3-3 to 3-5 were subjected to a current of 20 mA / cm². ２ The drive life was measured by applying a current of 1,000 cd / m². ２ The equivalent lifespan was calculated. An acceleration factor of 1.5 was used, and the time it took for the brightness to decrease to 95% of the initial brightness was measured to achieve a value of 1,000 cd / m². ２ The converted lifespan (LT95) was calculated. The ratio of the LT95 of Reference Example 3-2, Examples 3-5 to 3-7, and Comparative Examples 3-4 and 3-5 was calculated, with the LT95 of Comparative Example 3-3 set to 100, and this was used as the relative drive life. The measurement results and the [N / C(side)] / [N / C(main)] and Mw(side) / Mw(main) of the polymer used to form the hole transport layer are shown in Table 8.

[0556]

[0557] The results in Table 8 show that the performance of an organic electroluminescent device using the polymer of the present invention as the hole transport layer is improved.

[0558] 1. Substrate 2. Anode 3. Hole injection layer 4. Hole transport layer 5. Light-emitting layer 6. Electron transport layer 7. Cathode 8. Organic electroluminescent element

Claims

1. A polymer that satisfies the following formulas (1) and (2), satisfies at least one of the following (i) and (ii), and contains a repeating unit represented by the following formula (59). Abs500nm ≤ 0.004...(1) Abs460nm ≤ 0.010...(2) Abs500nm and Abs460nm each represent the absorbance of a 1% by mass tetrahydrofuran solution of the polymer. (i) It has two or more repeating units among the repeating unit represented by the following formula (54), the repeating unit represented by the following formula (55), the repeating unit represented by the following formula (56), and the repeating unit represented by the following formula (57). (ii) It consists of only one or more repeating units among the repeating unit represented by the following formula (54), the repeating unit represented by the following formula (55), the repeating unit represented by the following formula (56), and the repeating unit represented by the following formula (57). (In formula (54), Ar ５1 is a group in which a plurality of groups selected from the group consisting of an aromatic hydrocarbon group which may have a substituent other than a crosslinking group, an aromatic heterocyclic group which may have a substituent other than a crosslinking group, or an aromatic hydrocarbon group which may have a substituent other than a crosslinking group and an aromatic heterocyclic group which may have a substituent other than a crosslinking group are 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 ) -, R ２０１ , R ２０２ , R [[ID=…]] ２２１ and R ２２２ are each independently an alkyl group which may have a substituent other than a crosslinking group, R ２０７ ~R ２０９ and R ２１１ ~R ２１４ Each of these is independently a hydrogen atom, an alkyl group which may have substituents other than a crosslinking group, an aralkyl group which may have substituents other than a crosslinking group, or an aromatic hydrocarbon group which may have substituents other than a crosslinking group, and each of a, b and d is independently an integer from 0 to 4, and c is an integer from 0 to 3, provided that if a is 1 or more, then c is 1 or more, and if b is 1 or more, then d is 1 or more, R ２０１ If there are multiple R's, ２０１ They may be the same or different, R ２０２ If there are multiple R's, ２０２ They may be the same or different, R ２２１ If there are multiple R's, ２２１ They may be the same or different, R ２２２ If there are multiple R's, ２２２ (i and j may be the same or different, and each of them is an independent integer between 0 and 3.) (In formula (55), Ar ５１ Ar in formula (54) ５１ It is similar to R ３０３ and R ３０６ Each of these is an alkyl group which may have substituents other than a crosslinking group, and R ３０４ and R ３０５ Each of these is independently an alkyl group which may have substituents other than a crosslinking group, an alkoxy group which may have substituents other than a crosslinking group, or an aralkyl group which may have substituents other than a crosslinking group; l, n, p, and q are each independently 0 or 1; m is 1 or 2, however, if p is 1, l is 1, and if q is 1, n is 1. (In formula (56), Ar ５１ Ar in formula (54) ５１ It is similar to Ar ４１ R is a divalent group in which multiple groups selected from the group consisting of a divalent aromatic hydrocarbon group which may have substituents other than a crosslinking group, a divalent aromatic heterocyclic group which may have substituents other than a crosslinking group, or an aromatic hydrocarbon group which may have substituents other than a crosslinking group and an aromatic heterocyclic group which may have substituents other than a crosslinking group are directly or via a linking group, ４４１ and R ４４２ Each of these is an alkyl group which may have substituents other than a crosslinking group, t is 1 or 2, u is 0 or 1, and r and s are each an integer from 0 to 4, provided that if s is 1 or greater, u is 1. (In formula (57), Ar ５１ Ar in formula (54) ５１ It is similar to R ５１７ ~R ５１９ Each of these independently represents an alkyl group which may have substituents other than a crosslinking group, an alkoxy group which may have substituents other than a crosslinking group, an aralkyl group which may have substituents other than a crosslinking group, an aromatic hydrocarbon group which may have substituents other than a crosslinking group, or an aromatic heterocyclic group which may have substituents other than a crosslinking group; f, g, and h are each independently integers from 0 to 4, and e is an integer from 0 to 3, provided that if g is 1 or greater, then e is 1 or greater. (In formula (59), Ar ５１ X, R ２０１ , R ２０２ This is Ar in formula (54) above. ５１ X, R ２０１ , R ２０２ It is similar to R ５１８ R in formula (57) is ５１８ It is similar to the two Ar ５１ They may be the same or different, and the two R's ５１８ They may be the same or different.

2. A polymer that satisfies the following formulas (1) and (2), and also satisfies (i) below, wherein the total number of carbon atoms of the alkyl groups contained in the main chain of the repeating units constituting the polymer is C Ａ The total number of carbon atoms in the alkyl groups contained in the side chains of the repeating units that make up the polymer is C Ｂ A polymer that satisfies the following formula (TI): Abs500nm ≤ 0.004 ... (1) Abs460nm ≤ 0.010 ... (2) Abs500nm and Abs460nm represent the absorbance of a 1% by mass tetrohydrofuran solution of the polymer, respectively. 1.5 ≤ C Ｂ / C Ａ ≤2.2 ... (TI) (i) Having two or more repeating units from among the repeating units represented by the following formula (54), the repeating unit represented by the following formula (55), the repeating unit represented by the following formula (56), and the repeating unit represented by the following formula (57). (In formula (54), Ar ５１ This is a group in which multiple groups selected from the group consisting of an aromatic hydrocarbon group which may have substituents other than a crosslinking group, an aromatic heterocyclic group which may have substituents other than a crosslinking group, or an aromatic hydrocarbon group which may have substituents other than a crosslinking group and an aromatic heterocyclic group which may have substituents other than a crosslinking group are linked directly or via a linking group, provided that N-Ar ５1 In this, the nitrogen atom is not directly bonded to a fused ring, and X is -C(R ２０７ ) (Caution ２０８ )-,-N(R ２０９ )-, or-C(R ２１１ ) (Caution ２１２ )-C(R ２１３ ) (Caution ２１４ ) - and R ２０１ , R ２０２ , R ２２１ and R ２２２ Each of these is an alkyl group which may have substituents other than a crosslinking group, and R ２０７ ~R ２０９ and R ２１１ ~R ２１４ Each of these is independently a hydrogen atom, an alkyl group which may have substituents other than a crosslinking group, an aralkyl group which may have substituents other than a crosslinking group, or an aromatic hydrocarbon group which may have substituents other than a crosslinking group, and each of a, b and d is independently an integer from 0 to 4, and c is an integer from 0 to 3, provided that if a is 1 or more, then c is 1 or more, and if b is 1 or more, then d is 1 or more, R ２０１ If there are multiple R's, ２０１ They may be the same or different, R ２０２ If there are multiple R's, ２０２ They may be the same or different, R ２２１ If there are multiple R's, ２２１ They may be the same or different, R ２２２ If there are multiple R's, ２２２ (i and j may be the same or different, and each of them is an independent integer between 0 and 3.) (In formula (55), Ar ５1 Ar in formula (54) ５１ It is similar to N-Ar ５1 In this case, the nitrogen atom is not directly bonded to the fused ring, R ３０３ and R ３０６ Each of these is an alkyl group which may have substituents other than a crosslinking group, and R ３０４ and R ３０５ Each of these is independently an alkyl group which may have substituents other than a crosslinking group, an alkoxy group which may have substituents other than a crosslinking group, or an aralkyl group which may have substituents other than a crosslinking group; l, n, p, and q are each independently 0 or 1; m is 1 or 2, however, if p is 1, l is 1, and if q is 1, n is 1. (In formula (56), Ar ５１ Ar in formula (54) ５１ It is similar to N-Ar ５1 In this, the nitrogen atom is not directly bonded to the fused ring, Ar ４１ is a divalent group in which a plurality of groups selected from the group consisting of a divalent aromatic hydrocarbon group which may have a substituent other than a crosslinking group, a divalent aromatic heterocyclic group which may have a substituent other than a crosslinking group, or an aromatic hydrocarbon group which may have a substituent other than a crosslinking group and an aromatic heterocyclic group which may have a substituent other than a crosslinking group are directly or via a linking group, and R ４４１ and R ４４２ are each independently an alkyl group which may have a substituent other than a crosslinking group, t is 1 or 2, u is 0 or 1, r and s are each independently an integer from 0 to 4, provided that when s is 1 or more, u is 1.) (In formula (57), Ar ５１ is the same as Ar ５１ in the above formula (54), provided that in N-Ar ５1 , a condensed ring is not directly bonded to the nitrogen atom, and R ５１７ to R ５１９ each independently represent an alkyl group which may have a substituent other than a crosslinking group, an alkoxy group which may have a substituent other than a crosslinking group, an aralkyl group which may have a substituent other than a crosslinking group, an aromatic hydrocarbon group which may have a substituent other than a crosslinking group, or an aromatic heterocyclic group which may have a substituent other than a crosslinking group, f, g and h are each independently an integer from 0 to 4, e is an integer from 0 to 3, provided that when g is 1 or more, e is 1 or more.) 3. The polymer according to claim 1 or 2, comprising a partial structure represented by the following formula (61) or the following formula (61'). (In formula (61) and formula (61'), ６０１ R represents 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 , R in formula (57) ５１７ , R ５１８ , or R ５１９ represents at least any one of them, and - * represents the bonding position with an adjacent atom. When formula (61) and formula (61') are the partial structure of formula (54) or the partial structure of formula (56), Ring B may be a part of a condensed ring., The partial structure represented by formula (61) and formula (61') has, in addition to R ６０１ , in the structural parts of Ring A and Ring B, when it is the partial structure of formula (54), R ２０１ or R ２０２ is, when it is the partial structure of formula (55), R ３０３ , R ３０４ , R ３０５ , or R ３０６ is, when it is the partial structure of formula (56), R ４４１ or R ４４２ is, when it is the partial structure of formula (57), R ５１７ , R ５１８ or R ５１９ may be bonded.) 4. The polymer according to claim 2, comprising a repeating unit represented by the following formula (59). (In formula (59), Ar ５１ X, R ２０１ , R ２０２ This is Ar in formula (54) above. ５１ X, R ２０１ , R ２０２ It is similar to N-Ar ５1 In this case, the nitrogen atom is not directly bonded to the fused ring, R ５１８ R in formula (57) is ５１８ It is similar to the two Ar ５１ They may be the same or different, and the two R's ５１８ They may be the same or different.

5. In the above formula (59), X is -C(R ２０７ ) (Caution ２０８ ) - and R ２０１ , R ２０２ , R ５１８ , R ２０７ , R ２０８ The polymer according to claim 1 or 4, wherein each of them is independently an alkyl group.

6. In the above formula (59), Ar ５１ The polymer according to claim 1 or 4, wherein at least one of the groups is a biphenyl group substituted with an alkyl group.

7. The Ar in the repeating unit represented by formulas (54), (55), (56), (57), and (59) ５１ The polymer according to claim 1, wherein at least one of the following is represented by formula (81). (In formula (81), Fu is a monovalent aromatic hydrocarbon condensed ring group which may have substituents, or a carbazolyl group which may have substituents, and ab is an integer from 0 to 1.) 8. The Ar in the repeating unit represented by formulas (54), (55), (56), and (57) above. ５１ The polymer according to claim 2, wherein at least one of the following is represented by formula (81). (In formula (81), Fu is a monovalent aromatic hydrocarbon condensed ring group which may have substituents, or a carbazolyl group which may have substituents, and ab is an integer from 0 to 1.) 9. The polymer according to claim 7 or 8, wherein Fu in formula (81) is a fluorenyl group which may have substituents.

10. The polymer according to claim 7 or 8, wherein formula (81) is formula (82) shown below. (In formula (82), Fu is a monovalent aromatic hydrocarbon condensed ring group which may have substituents, or a carbazolyl group which may have substituents, and ab is an integer from 0 to 1.) 11. A composition for forming an organic film, comprising the polymer according to claim 1 or 2 and a solvent.

12. A method for producing an organic film by a wet film formation method using the organic film-forming composition described in claim 11.

13. An organic electroluminescent element having an organic layer containing the polymer described in claim 1 or 2.

14. A display device comprising the organic electroluminescent element described in claim 13.

15. A lighting device comprising the organic electroluminescent element described in claim 13.

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