Polymer compound, and electroluminescent device material and electroluminescent device using said polymer compound

Abstract

To provide a technique that can improve the durability of an electroluminescence element (particularly emission lifetime).SOLUTION: A polymer compound contains a constitutional unit represented by the formula (1), or the constitutional unit represented by the formula (1) and a constitutional unit represented by the formula (2).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a polymer compound, and an electroluminescent device material and an electroluminescent device using the polymer compound. [Background technology]

[0002] Research and development of electroluminescent elements (EL elements) is currently underway. EL elements are particularly promising for use as inexpensive, solid-state, large-area full-color display elements and writing light source arrays. EL elements are light-emitting elements that have a thin film between an anode and a cathode, with a thickness of several nanometers to several hundred nanometers. EL elements also typically have a hole transport layer, a light-emitting layer, an electron transport layer, and the like.

[0003] Among these, the light-emitting layer can be made of fluorescent or phosphorescent materials. Phosphorescent materials are expected to have higher luminous efficiency than fluorescent materials. Furthermore, to cover a wide color gamut, RGB light sources are required to have a narrow emission spectrum with a half-width. In particular, a deep blue is required, but currently, no element has been found that satisfies the requirements for long life and color purity.

[0004] One approach to solving these problems is the development of light-emitting devices that use "quantum dots," an inorganic light-emitting material, as the light-emitting material (Patent Document 1). Quantum dots (QDs) are semiconductor materials with a crystalline structure measuring several nanometers in size and composed of hundreds to thousands of atoms. Because of their extremely small size, quantum dots have a large surface area per unit volume. Therefore, most of the atoms reside on the surface of the nanocrystals, exhibiting quantum confinement effects. Due to this quantum confinement effect, quantum dots can adjust the emission wavelength simply by adjusting their size. They have also attracted considerable attention for their excellent color purity and high photoluminescence (PL) efficiency. A quantum dot electroluminescence device (QD LED) is known to have a three-layer structure consisting of a quantum dot light-emitting layer sandwiched between a hole transport layer (HTL) and an electron transport layer (ETL).

[0005] Furthermore, for the purpose of improving the durability (particularly the luminescence lifetime) of the electroluminescence element (particularly the quantum dot electroluminescence element) described in Patent Document 1, an electroluminescence element using an arylamine-fluorene alternating copolymer having a structural unit (A) with a specific structure has been reported (Patent Document 2). [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Laid-Open No. 2010-199067 [Patent Document 2] Patent Publication No. 2021-138915 Summary of the Invention [Problem to be solved by the invention]

[0007] An electroluminescent element using the arylamine-fluorene alternating copolymer described in Patent Document 2 as a hole transport material has excellent durability. As the performance of sensing elements improves, there is a demand for improved durability.

[0008] Therefore, the present invention has been made in view of the above circumstances, and has an object to provide a technique capable of improving the durability (particularly the luminescence life) of electroluminescence elements (particularly quantum dot electroluminescence elements). [Means for solving the problem]

[0009] The present inventors have conducted extensive research to solve the above problems, and as a result have found that the above problems can be solved by using a polymer compound having a specific structure, thereby completing the present invention.

[0010] That is, the above object can be achieved by a polymer compound containing a constitutional unit represented by the following formula (1), or a constitutional unit represented by the following formula (1) and a constitutional unit represented by the following formula (2):

[0011] [ka]

[0012] In the above formula (1), R 11 ~R 14 , R 21 , R 22 , R 31 and R 32 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms, L 1 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having from 6 to 25 ring atoms, or a substituted or unsubstituted divalent aromatic heterocyclic group having from 5 to 14 ring atoms, x is 0, 1 or 2, and when x is 2, L 1 may be the same or different, L 2 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms or a substituted or unsubstituted aromatic heterocyclic group having 5 to 14 ring atoms, 2 Ar 1 may form a ring with Ar 1 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 ring atoms or a substituted or unsubstituted divalent aromatic heterocyclic group having 5 to 14 ring atoms, and Ar 2 or L 2 and form a ring, Ar 2 represents a linear or branched hydrocarbon group having 1 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring atoms, which may be substituted with a divalent aromatic heterocyclic group having 5 to 14 ring atoms, or an aromatic heterocyclic group having 5 to 14 ring atoms, which may be substituted with a linear or branched hydrocarbon group having 1 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring atoms, or an aromatic heterocyclic group having 5 to 14 ring atoms, which may be substituted with a divalent aromatic heterocyclic group having 5 to 14 ring atoms, 2 Ar 1 may form a ring with;

[0013] [ka]

[0014] In the above formula (2), R 41 ~R 44 , R 23 , R 24 , R 33 and R 34 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms, and in this case, R 41 ~R 44is R in the above formula (1). 11 ~R 14 and differ from each other, L 3 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having from 6 to 25 ring atoms, or a substituted or unsubstituted divalent aromatic heterocyclic group having from 5 to 14 ring atoms, y is 0, 1 or 2, and when y is 2, L 3 may be the same or different, L 4 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms or a substituted or unsubstituted aromatic heterocyclic group having 5 to 14 ring atoms, 4 Ar 3 may form a ring with Ar 3 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 ring atoms or a substituted or unsubstituted divalent aromatic heterocyclic group having 5 to 14 ring atoms, and Ar 4 or L 4 and form a ring, Ar 4 represents a linear or branched hydrocarbon group having 1 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring atoms, which may be substituted with a divalent aromatic heterocyclic group having 5 to 14 ring atoms, or an aromatic heterocyclic group having 5 to 14 ring atoms, which may be substituted with a linear or branched hydrocarbon group having 1 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring atoms, or an aromatic heterocyclic group having 5 to 14 ring atoms, which may be substituted with a divalent aromatic heterocyclic group having 5 to 14 ring atoms, 4 Ar 3 may form a ring with [Effects of the Invention]

[0015] According to the present invention, the durability (particularly the luminescence life) of an electroluminescence element (particularly a quantum dot electroluminescence element) can be improved. [Brief explanation of the drawings]

[0016] [Figure 1] 1 is a schematic diagram illustrating an electroluminescence element according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0017] In a first aspect, the present invention provides a polymer compound comprising a constitutional unit represented by the following formula (1), or a constitutional unit represented by the following formula (1) and a constitutional unit represented by the following formula (2):

[0018] [ka]

[0019] In the above formula (1), R 11 ~R 14 , R 21 , R 22 , R 31 and R 32 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms, L 1 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having from 6 to 25 ring atoms, or a substituted or unsubstituted divalent aromatic heterocyclic group having from 5 to 14 ring atoms, x is 0, 1 or 2, and when x is 2, L 1 may be the same or different, L 2 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms or a substituted or unsubstituted aromatic heterocyclic group having 5 to 14 ring atoms, 2 Ar 1 may form a ring with Ar 1represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 ring atoms or a substituted or unsubstituted divalent aromatic heterocyclic group having 5 to 14 ring atoms, and Ar 2 or L 2 and form a ring, Ar 2 represents a linear or branched hydrocarbon group having 1 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring atoms, which may be substituted with a divalent aromatic heterocyclic group having 5 to 14 ring atoms, or an aromatic heterocyclic group having 5 to 14 ring atoms, which may be substituted with a linear or branched hydrocarbon group having 1 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring atoms, or an aromatic heterocyclic group having 5 to 14 ring atoms, which may be substituted with a divalent aromatic heterocyclic group having 5 to 14 ring atoms, 2 Ar 1 may form a ring with;

[0020] [ka]

[0021] In the above formula (2), R 41 ~R 44 , R 23 , R 24 , R 33 and R 34 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms, and in this case, R 41 ~R 44 is R in the above formula (1). 11 ~R 14 and differ from each other, L 3 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having from 6 to 25 ring atoms, or a substituted or unsubstituted divalent aromatic heterocyclic group having from 5 to 14 ring atoms, y is 0, 1 or 2, and when y is 2, L 3 may be the same or different, L 4 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms or a substituted or unsubstituted aromatic heterocyclic group having 5 to 14 ring atoms, 4 Ar 3 may form a ring with Ar 3 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 ring atoms or a substituted or unsubstituted divalent aromatic heterocyclic group having 5 to 14 ring atoms, and Ar 4 or L 4 and form a ring, Ar 4 represents a linear or branched hydrocarbon group having 1 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring atoms, which may be substituted with a divalent aromatic heterocyclic group having 5 to 14 ring atoms, or an aromatic heterocyclic group having 5 to 14 ring atoms, which may be substituted with a linear or branched hydrocarbon group having 1 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring atoms, or an aromatic heterocyclic group having 5 to 14 ring atoms, which may be substituted with a divalent aromatic heterocyclic group having 5 to 14 ring atoms, 4 Ar 3 may form a ring with

[0022] In a second aspect, the present invention provides an electroluminescent device material comprising the polymer compound of the present invention.

[0023] In a third aspect, the present invention provides an electroluminescent device comprising a first electrode, a second electrode, and one or more organic films disposed between the first electrode and the second electrode, wherein at least one layer of the organic films contains a polymer compound according to the present invention. In this specification, the electroluminescent device is also referred to simply as an "LED." A quantum dot electroluminescent device is also referred to simply as a "QLED." An organic electroluminescent device is also referred to simply as an "OLED."

[0024] In this specification, the indenofluorene-derived structural unit of a polymer compound is referred to as "structural unit A," and the structural unit of a polymer compound other than the indenofluorene-derived structural unit is referred to as "structural unit B." A structural unit consisting of structural units A and B is also referred to as "structural unit C." For example, the structural units A, B, and C in the structural unit of formula (1) above are as follows. In this specification, when a polymer compound contains a structural unit of formula (1) above and a structural unit of formula (2) above, the structural unit of formula (1) above and the structural unit of formula (2) above are collectively referred to as "structural unit C" unless otherwise specified.

[0025] [ka]

[0026] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic compound, a fused ring compound, and a ring assembly). The number of ring atoms does not include atoms that do not constitute the ring (e.g., a hydrogen atom terminating the bond of an atom constituting the ring) or atoms contained in the substituent when the ring is substituted with a substituent. The number of ring atoms described below is the same unless otherwise specified.

[0027] For example, a benzene ring has 6 ring atoms, a naphthalene ring has 10 ring atoms, a pyridine ring has 6 ring atoms, and a furan ring has 5 ring atoms.

[0028] When a benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring atoms of the benzene ring. Therefore, the number of ring atoms of a benzene ring substituted with an alkyl group is 6. Furthermore, when a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of atoms of the alkyl group is not included in the number of ring atoms of the naphthalene ring. Therefore, the number of ring atoms of a naphthalene ring substituted with an alkyl group is 10.

[0029] For example, the number of hydrogen atoms or atoms constituting a substituent bonded to a pyridine ring is not included in the number of ring atoms of the pyridine ring. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6.

[0030] Various low molecular weight materials and polymeric materials are used as materials for composing the light-emitting layer and carrier transport layer of electroluminescent devices. For example, Patent Document 1 reports TFB (e.g., paragraph "0037") as a polymeric material, and Patent Document 2 reports an alternating copolymer of fluorene and an arylamine of a specific structure (claimed). The present inventors have conducted extensive research into means for further improving durability (device life, luminescence life) compared to these polymeric materials (particularly the arylamine-fluorene alternating copolymer of Patent Document 2). As a result, they have found that durability (device life, luminescence life) can be further improved by replacing fluorene-derived structural units with indenofluorene-derived structural units. The mechanism by which the above-mentioned effects of the present invention are exhibited is presumed to be as follows: structural unit A and structural unit B [particularly the arylamine structure in structural unit B (-L in the above formula (1))] 2 -N(Ar 1 )(Ar 2 ) or -L in the above formula (2) 4 -N(Ar 3 )(Ar 4))] has a large number of resonance structures such as fused rings. Therefore, the structural unit C has a stable skeleton with high resonance energy. Therefore, the bond dissociation energy (BDE) of the C-N bond in the exciton state and anion state is high (strong against excitons and electrons). In particular, by using an indenofluorene-derived structural unit as the structural unit A, the bond dissociation energy of the C-N bond in the exciton state can be made higher than in the case of a fluorene-derived structural unit as described in Patent Document 2. A hole transport layer or hole injection layer using the polymer compound according to the present invention is likely to maintain its structure even in the presence of electrons leaked from the electron transport layer or excitons generated by the recombination of these electrons and holes. Therefore, an electroluminescent device (particularly a quantum dot electroluminescent device) using the polymer compound according to the present invention can further improve its durability (device life, light-emitting life).

[0031] Furthermore, in the structural unit (structural unit C) of formula (1) or (2), the nitrogen atom cleaves the conjugation of the main chain. This increases the triplet energy level of the polymer compound, increasing the hole mobility (bulk mobility) along the main chain and achieving high current efficiency. Therefore, electroluminescent devices (particularly quantum dot electroluminescent devices) using the polymer compound (main chain) of the present invention can achieve excellent luminous efficiency. Furthermore, because the main chain is cleaved by the nitrogen atom in structural unit C, the polymer compound of the present invention, even when polymerized, exhibits properties similar to those of low-molecular-weight compounds, with energy levels close to those of quantum dots. Therefore, electroluminescent devices (particularly quantum dot electroluminescent devices) using the polymer compound of the present invention can suppress increases in driving voltage and enable lower driving voltages.

[0032] In addition, the polymer compound according to the present invention has excellent film-forming properties and solvent solubility, and therefore can be used to form a film by a wet (coating) method. Therefore, it is possible to increase the area of ​​electroluminescence elements and increase productivity. The above-mentioned effects can be effectively exhibited when the polymer compound according to the present invention is applied to an EL element, particularly a hole transport layer or a hole injection layer of a QLED.

[0033] The above mechanism is based on speculation, and the present invention is not limited to the above mechanism.

[0034] Hereinafter, embodiments for carrying out the present invention will be described in detail. Note that the present invention is not limited to the following embodiments, and various modifications can be made within the scope of the claims. Furthermore, unless otherwise specified, operations and measurements of physical properties are performed at room temperature (20°C to 25°C) and a relative humidity of 40% RH to 50% RH. Furthermore, the dimensional proportions in the drawings are exaggerated for the sake of explanation and may differ from the actual proportions.

[0035] As used herein, "X and Y are each independently" means that X and Y may be the same or different. Furthermore, as used herein, "X and / or Y" means that at least one of X and Y is included, and encompasses "X alone," "Y alone," and "a combination of X and Y."

[0036] [High molecular compound] The polymer compound according to the present invention includes a structural unit represented by the following formula (1). Alternatively, the polymer compound according to the present invention includes a structural unit represented by the following formula (1) and a structural unit represented by the following formula (2). A polymer compound having such a structural unit has a stable skeleton with high resonance energy and high C-N bond dissociation energy. In addition, the polymer compound has high hole injection and transport properties to quantum dots. Therefore, durability (device life, luminescence life) can be further improved. In addition, high current efficiency and low driving voltage can be achieved.

[0037] [ka]

[0038] The constitutional unit represented by the above formula (1) and the constitutional unit represented by the above formula (2) are at least R 11 ~R 14 R 41 ~R 44 In this specification, "a polymer compound comprising a structural unit represented by formula (1)" means that the structural unit C present in the polymer compound is at least one type. Also, "a polymer compound comprising a structural unit represented by formula (1) and a structural unit represented by the following formula (2)" means that the structural unit C present in the polymer compound is at least two types. That is, The polymer compound according to the present invention may contain one type of structural unit C or two or more types of structural unit C. From the viewpoint of further improving the effects of the present invention, the polymer compound according to the present invention preferably contains one or two types of structural unit C, and more preferably two types. In particular, by having two different types of structural unit C, desired properties (e.g., durability, glass transition temperature) can be more appropriately and easily adjusted.

[0039] In the above formula (1), R 11 ~R 14 , R 21 , R 22 , R 31 and R 32 are each independently a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms. 11 ~R 14 , R 21 , R 22 , R 31 and R 32 may be the same or different. From the viewpoint of further improving the effects of the present invention, R 11 and R 12 and R 13 and R 14 Preferably, at least one of R 11 ~R 14 It is more preferable that all of R 21 and R22 may be the same or different. 21 and R 22 are preferably the same. 31 and R 32 may be the same or different. 31 and R 32 are preferably the same.

[0040] In the above formula (2), R 41 ~R 44 , R 23 , R 24 , R 33 and R 34 Each of R in the formula (2) represents independently a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms. 41 ~R 44 is R in the above formula (1). 11 ~R 14 are mutually different. R 41 ~R 44 , R 23 , R 24 , R 33 and R 34 may be the same or different. From the viewpoint of further improving the effects of the present invention, R 41 and R 42 and R 43 and R 44 Preferably, at least one of R 41 ~R 44 It is more preferable that all of R 23 and R 24 may be the same or different. 23 and R 24 are preferably the same. 33 and R 34 may be the same or different. 33 and R 34 are preferably the same.

[0041] The hydrocarbon group having 1 to 18 carbon atoms is not particularly limited, and examples thereof include linear or branched alkyl groups, linear or branched alkenyl groups, linear or branched alkynyl groups, and cycloalkyl groups. When the hydrocarbon group is an alkenyl or alkynyl group, the hydrocarbon group has 2 to 18 carbon atoms. Similarly, when the hydrocarbon group is a cycloalkyl group, the hydrocarbon group has 3 to 18 carbon atoms.

[0042] Examples of the alkyl group having 1 to 18 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a tert-pentyl group, a neopentyl group, a 1,2-dimethylpropyl group, an n-hexyl group, an isohexyl group, a 1,3-dimethylbutyl group, a 1-isopropylpropyl group, a 1,2-dimethylbutyl group, an n-heptyl group, a 1,4-dimethylpentyl group, a 3-ethylpentyl group, a 2-methyl-1-isopropyl Examples of such groups include a propylpropyl group, a 1-ethyl-3-methylbutyl group, an n-octyl group, a 2-ethylhexyl group, a 3-methyl-1-isopropylbutyl group, a 2-methyl-1-isopropyl group, a 1-tert-butyl-2-methylpropyl group, an n-nonyl group, a 3,5,5-trimethylhexyl group, an n-decyl group, an isodecyl group, an n-undecyl group, a 1-methyldecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, and an n-octadecyl group.

[0043] Examples of the alkenyl group having 2 to 18 carbon atoms include a vinyl group, an allyl group, a 1-propenyl group, a 2-butenyl group, a 1,3-butadienyl group, a 2-pentenyl group, and an isopropenyl group.

[0044] Examples of the alkynyl group having 2 to 18 carbon atoms include an ethynyl group and a propargyl group.

[0045] Examples of the cycloalkyl group having 3 or more and 18 or less carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0046] R 11 ~R 14 At least two of and / or R 41 ~R 44 At least two of R are preferably hydrocarbon groups having 1 to 18 carbon atoms, 11 ~R 14 At least three of and / or R 41 ~R 44 It is more preferable that at least three of the groups R are hydrocarbon groups having 1 to 18 carbon atoms. 11 ~R 14 All of and R 41 ~R 44 It is particularly preferred that all of are hydrocarbon groups having 1 to 18 carbon atoms. Increasing the number of hydrocarbon groups present in the indenofluorene ring in this way improves hole injection and transport properties, thereby further improving durability (device life).

[0047] Also, R 11 ~R 14 or R 41 ~R 44 The hydrocarbon group as R may be a linear alkyl group having 1 to 18 carbon atoms or a branched alkyl group having 3 to 18 carbon atoms. 11 ~R 14 or R 41 ~R 44 The hydrocarbon group as the alkyl group is preferably a linear alkyl group having 3 to 14 carbon atoms or a branched alkyl group having 3 to 14 carbon atoms.

[0048] In particular, when the polymer compound contains only one type of structural unit C (the polymer compound contains the structural unit of the above formula (1)), R 11 ~R 14 The hydrocarbon group as is more preferably a linear alkyl group having 6 to 12 carbon atoms, even more preferably a linear alkyl group having 7 to 9 carbon atoms, and particularly preferably an n-octyl group.

[0049] When the number of carbon atoms of the hydrocarbon group present in the indenofluorene ring is within the above range, in a quantum dot electroluminescence device having a hole transport layer containing a polymer compound and a light-emitting layer containing quantum dots, the hydrocarbon group present in the indenofluorene ring of the polymer compound in the hole transport layer and the quantum dots contained in the light-emitting layer are closer to each other (the hydrocarbon group and the quantum dots interact closely).Therefore, the hole injection and transport properties can be further improved, and the durability (device life, light-emitting life) can be further improved.

[0050] In addition, when there are two types of structural units C present in the polymer compound (the polymer compound contains the structural unit of the above formula (1) and the structural unit of the above formula (2)), R 11 ~R 14 and R in the above formula (2) 41 ~R 44 In one embodiment of the present invention, the polymer compound contains a constitutional unit represented by the above formula (1) and a constitutional unit represented by the above formula (2), and in this case, R 11 ~R 14 represents a hydrocarbon group having 1 to 9 carbon atoms, and R in the above formula (2) 41 ~R 44 represents a hydrocarbon group having 10 to 18 carbon atoms. In a preferred embodiment of the present invention, the polymer compound contains a constitutional unit represented by the above formula (1) and a constitutional unit represented by the above formula (2), and in this case, R 11 ~R 14 each independently represents a hydrocarbon group having 3 to 9 carbon atoms, and R 41 ~R 44 each independently represents a hydrocarbon group having 10 to 14 carbon atoms. In a more preferred embodiment of the present invention, the polymer compound contains a constitutional unit represented by the above formula (1) and a constitutional unit represented by the above formula (2), and in this case, R 11 ~R 14each independently represents a linear or branched alkyl group having 5 to 7 carbon atoms, and R 41 ~R 44 each independently represents a linear or branched alkyl group having from 11 to 13 carbon atoms. In a particularly preferred embodiment of the present invention, the polymer compound contains a structural unit represented by the above formula (1) and a structural unit represented by the above formula (2), and in this case, R 11 ~R 14 represents an n-hexyl group, and R in the above formula (2) 41 ~R 44 is n-dode In the above preferred embodiment, R 11 ~R 14 may be the same or different, but preferably all are the same. 41 ~R 44 may be the same or different, but it is preferable that they are all the same. 11 ~R 14 All things being equal and R 41 ~R 44 It is particularly preferred that they are all the same.

[0051] R in two types of structural units C present in polymer compounds 11 ~R 14 and R 41 ~R 44 By combining these materials as described above, it is possible to adjust the hole injection and transport properties (hence durability) and film forming properties (for example, glass transition temperature) in an appropriate balance.

[0052] Also, R 21 , R 22 , R 31 , R 32 , R 23 , R 24 , R 33 and R 34are each independently preferably a hydrogen atom (unsubstituted) or a linear alkyl group having from 1 to 8 carbon atoms or a branched alkyl group having from 3 to 8 carbon atoms, more preferably a hydrogen atom (unsubstituted) or a linear alkyl group having from 3 to 6 carbon atoms, and particularly preferably a hydrogen atom (unsubstituted).

[0053] In the above formula (1), L 1 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 ring atoms or a substituted or unsubstituted divalent aromatic heterocyclic group having 5 to 14 ring atoms. 3 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted divalent aromatic heterocyclic group having 5 to 14 ring atoms. When the polymer compound contains a structural unit of the above formula (1) and a structural unit of the above formula (2), L in the above formula (1) 1 and L in the above formula (2) 3 may be the same or different, but are preferably the same.

[0054] Examples of the aromatic hydrocarbon group include divalent groups derived from aromatic hydrocarbons such as benzene (phenylene group), pentalene, indene, naphthalene, anthracene, azulene, acenaphthene, phenalene, fluorene, phenanthroline, biphenyl, terphenyl, quaterphenyl, pyrene, 9,9-diphenylfluorene, 9,9'-spirobi[fluorene], and 9,9-dialkylfluorene. Examples of the aromatic heterocyclic group include pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, naphthyridine, acridine, phenazine, benzoquinoline, benzoisoquinoline, phenanthridine, phenanthroline, benzoquinone, coumarin, fluorenone, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, pyrrole, indole, carbazole, imidazole, benzimidazole, pyrazoline, and the like. Examples of divalent groups include divalent groups derived from heterocyclic aromatic compounds such as benzoyl, indazole, oxazole, isoxazole, benzoxazole, benzisoxazole, thiazole, isothiazole, benzothiazole, benzisothiazole, imidazolinone, benzimidazolinone, imidazopyridine, imidazopyrimidine, azadibenzofuran, azacarbazole, azadibenzothiophene, diazadibenzofuran, diazacarbazole, diazadibenzothiophene, xanthone, and thioxanthone. 1 and L 3 are preferably each independently a divalent group derived from a compound selected from benzene, fluorene, dibenzofuran, dibenzothiophene, and biphenyl. 1 and L 3 are each independently a divalent group derived from a compound selected from benzene (o-, m-, or p-phenylene), dibenzofuran, and fluorene. 1 and L 3 are each independently more preferably a phenylene group, even more preferably an m-phenylene group or a p-phenylene group, and particularly preferably a p-phenylene group. 1 or L 3In addition, a higher bond dissociation energy can be achieved from the viewpoints of higher hole injection transport property and triplet energy level, lower driving voltage and film formability, and a balance of any two or more of these (especially In the above preferred embodiment, the balance between hole injection and transport properties and film-forming properties can be achieved. 1 or L 3 Each of these may be unsubstituted or any of the hydrogen atoms may be substituted with a substituent.

[0055] where L 1 or L 3 When any hydrogen atom of L is substituted, the number of substituents to be introduced is not particularly limited, but is preferably 1 or more and 3 or less, more preferably 1 or more and 2 or less, and particularly preferably 1. In one embodiment of the present invention, 1 and L 3 In one embodiment of the present invention, L 1 or L 3 has one substituent. 1 or L 3 When the group has a substituent, the bonding position of the substituent is not particularly limited. 1 or L 3 is preferably located as far away as possible from the nitrogen atom of the main chain to which it is linked. 1 or L 3 When is a p-phenylene group, the substituent is preferably located at a meta position relative to the bond connected to the nitrogen atom of the main chain. The presence of the substituent at such a position can achieve a higher bond dissociation energy. It can also achieve higher hole injection / transport properties and triplet energy levels, lower driving voltages, and film-forming properties, as well as a balance of any two or more of these (particularly a balance between hole injection / transport properties and film-forming properties).

[0056] Also, L 1 or L 3The substituent that can be present when any hydrogen atom of the above is substituted is not particularly limited, and examples thereof include an alkyl group, a cycloalkyl group, a hydroxyalkyl group, an alkoxyalkyl group, an alkoxy group, a cycloalkoxy group, an alkenyl group, an alkynyl group, an amino group, an aryl group, an aryloxy group, an alkylthio group, a cycloalkylthio group, an arylthio group, an alkoxycarbonyl group, an aryloxycarbonyl group, a hydroxy group (-OH), a carboxy group (-COOH), a thiol group (-SH), and a cyano group (-CN).

[0057] Here, the alkyl group may be either linear or branched, and preferably includes a linear alkyl group having from 1 to 18 carbon atoms or a branched alkyl group having from 3 to 18 carbon atoms. Specific examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a tert-pentyl group, a neopentyl group, a 1,2-dimethylpropyl group, an n-hexyl group, an isohexyl group, a 1,3-dimethylbutyl group, a 1-isopropylpropyl group, a 1,2-dimethylbutyl group, an n-heptyl group, a 1,4-dimethylpentyl group, a 3-ethylpentyl group, a 2-methyl-1-isopropylpropyl group, Examples of such alkyl groups include 1-ethyl-3-methylbutyl group, n-octyl group, 2-ethylhexyl group, 3-methyl-1-isopropylbutyl group, 2-methyl-1-isopropyl group, 1-tert-butyl-2-methylpropyl group, n-nonyl group, 3,5,5-trimethylhexyl group, n-decyl group, isodecyl group, n-undecyl group, 1-methyldecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, and n-octadecyl group.

[0058] Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0059] Examples of hydroxyalkyl groups include the above alkyl groups substituted with 1 to 3 (preferably 1 to 2, particularly preferably 1) hydroxy groups (for example, hydroxymethyl group, hydroxyethyl group).

[0060] Examples of the alkoxyalkyl group include the above alkyl groups substituted with 1 to 3 (preferably 1 to 2, particularly preferably 1) alkoxy groups below.

[0061] Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, 2-ethylhexyloxy, and 3-ethylpentyloxy groups.

[0062] Examples of the cycloalkoxy group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0063] Examples of alkenyl groups include vinyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 1-heptenyl, 2-heptenyl, 5-heptenyl, 1-octenyl, 3-octenyl, and 5-octenyl groups.

[0064] Examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 1-hexynyl group, a 2-hexynyl group, a 3-hexynyl group, a 1-heptynyl group, a 2-heptynyl group, a 5-heptynyl group, a 1-octynyl group, a 3-octynyl group, and a 5-octynyl group.

[0065] Examples of the aryl group include a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, anthryl group, a pyrenyl group, an azulenyl group, an acenaphthylenyl group, a terphenyl group, and a phenanthryl group.

[0066] Examples of the aryloxy group include a phenoxy group and a naphthyloxy group.

[0067] Examples of the alkylthio group include a methylthio group, an ethylthio group, a propylthio group, a pentylthio group, a hexylthio group, an octylthio group, and a dodecylthio group.

[0068] Examples of the cycloalkylthio group include a cyclopentylthio group and a cyclohexylthio group.

[0069] Examples of the arylthio group include a phenylthio group and a naphthylthio group.

[0070] Examples of the alkoxycarbonyl group include a methyloxycarbonyl group, an ethyloxycarbonyl group, a butyloxycarbonyl group, an octyloxycarbonyl group, and a dodecyloxycarbonyl group.

[0071] Examples of the aryloxycarbonyl group include a phenyloxycarbonyl group and a naphthyloxycarbonyl group.

[0072] Of these, L 1 or L 3The substituent that may be present when any hydrogen atom of the above is substituted is preferably a linear or branched alkyl group having 1 to 8 carbon atoms, more preferably a linear or branched alkyl group having 1 to 3 carbon atoms, and particularly preferably a methyl group.

[0073] Of the above, L 1 and L 3 are each independently a divalent group selected from the following group: That is, in a preferred embodiment of the present invention, in the above formula (1), x is 1 or 2 (particularly preferably 1), and L 1 are each independently a divalent group selected from the following group: In a preferred embodiment of the present invention, in the above formula (2), y is 1 or 2 (particularly preferably 1), and L 3 are each independently a divalent group selected from the following group: 111 ~R 125 each independently represents a hydrogen atom or a linear hydrocarbon group having 1 to 18 carbon atoms or a branched hydrocarbon group having 3 to 18 carbon atoms (preferably, R 111 ~R 125 is a hydrogen atom or a methyl group, and particularly preferably, R 111 ~R 125 is a hydrogen atom).

[0074] [ka]

[0075] In the above formula (1), x is 0, 1 or 2. When x is 2, L 1 may be the same or different. When x is 0, L 1 is a single bond, and the nitrogen atom in the main chain is L 2 From the viewpoint of further improving the effects of the present invention, x is preferably 0 or 1, and more preferably 1. In the above formula (2), y is 0, 1, or 2. When y is 2, L 3may be the same or different. When y is 0, L 3 is a single bond, and the nitrogen atom in the main chain is L 4 From the viewpoint of further improving the effects of the present invention, y is preferably 0 or 1, and more preferably 1. x in the above formula (1) and y in the above formula (2) may be the same or different, but are preferably the same.

[0076] In the above formula (1), L 2 represents a substituted or unsubstituted divalent or trivalent aromatic hydrocarbon group having 6 to 25 carbon atoms or a substituted or unsubstituted divalent or trivalent aromatic heterocyclic group having 5 to 14 ring atoms. 2 Ar 1 may form a ring with L 2 Ar 1 When forming a ring with L 2 is a trivalent group. 2 Ar 1 When it does not form a ring with L 2 is a divalent group. In the above formula (2), L 4 represents a substituted or unsubstituted divalent or trivalent aromatic hydrocarbon group having 6 to 25 carbon atoms or a substituted or unsubstituted divalent or trivalent aromatic heterocyclic group having 5 to 14 ring atoms. 4 Ar 3 may form a ring with L 4 Ar 3 When forming a ring with L 4 is a trivalent group. 4 Ar 3 When it does not form a ring with L 4 is a divalent group.

[0077] When the polymer compound contains the structural unit of the above formula (1) and the structural unit of the above formula (2), L in the above formula (1) 2 and L in the above formula (2) 4 may be the same or different, but are preferably the same.

[0078] where L 2 or L 4 The aromatic hydrocarbon group and aromatic heterocyclic group as L are not particularly limited. 2 Ar 1 When a ring is not formed with L 4 Ar 3 When a ring is not formed with the above L 1 and L 3 Examples of the divalent group include a divalent group derived from an aromatic hydrocarbon having 6 to 25 ring atoms as defined in the above. 2 or L 4 The aromatic heterocyclic group as L is not particularly limited, but may be any of the above-mentioned 1 and L 3 Examples of the divalent group derived from a heterocyclic aromatic compound are those defined in the above. 2 Ar 1 Form a ring with or L 4 Ar 3 When forming a ring with the above L 1 and L 3 In the same manner, in the above case, a divalent group derived from an aromatic hydrocarbon having 6 to 25 ring atoms as defined in 2 or L 4 The aromatic heterocyclic group as L is not particularly limited, but may be any of the above-mentioned 1 and L 3 Examples of the heterocyclic aromatic compounds include those derived from the heterocyclic aromatic compounds defined in the above, which are converted into trivalent groups. 2 and L 4 are preferably each independently a divalent or trivalent group derived from a compound selected from benzene, fluorene, dibenzofuran, dibenzothiophene, and biphenyl. 2 and L 4 are each independently a divalent group (e.g., o-, m-, or p-phenylene group) or a trivalent group (e.g., 1,3,4-phenylylene group) derived from a compound selected from benzene, fluorene, and dibenzofuran. Particularly preferably, L 2 and L 4are each independently a divalent (phenylene group) (particularly a p-phenylene group) or trivalent (particularly a 1,3,4-phenylene group) group derived from benzene. 2 or L 4 If L is 1, a higher bond dissociation energy can be achieved. In addition, it is possible to achieve higher hole injection transport properties and triplet energy levels, lower driving voltages, film formability, and a balance of any two or more of these (particularly a balance between hole injection transport properties and film formability). 2 or L 4 may be unsubstituted or any hydrogen atom may be substituted with a substituent. 2 or L 4 The substituent that may be present when any hydrogen atom of the above is substituted is not particularly limited, and may be any of the substituents 1 and L 3 The same examples as in the above can be applied. Preferably, L 2 or L 4 is unsubstituted.

[0079] In the above formula (1), Ar 1 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 ring atoms or a substituted or unsubstituted divalent aromatic heterocyclic group having 5 to 14 ring atoms. 3 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having from 6 to 25 ring atoms or a substituted or unsubstituted divalent aromatic heterocyclic group having from 5 to 14 ring atoms.

[0080] When the polymer compound contains the structural unit of the above formula (1) and the structural unit of the above formula (2), Ar 1 and Ar in the above formula (2) 3 may be the same or different, but are preferably the same.

[0081] where Ar 1 or Ar 3The aromatic hydrocarbon group having 6 to 25 ring atoms as the aromatic hydrocarbon group is not particularly limited, but may be any of the above-mentioned L 1 and L 3 Examples of divalent groups include those derived from aromatic hydrocarbons having 6 to 25 ring atoms as defined in the above. 1 or Ar 3 The aromatic heterocyclic group as L is not particularly limited, but may be any of the above-mentioned 1 and L 3 Examples of the divalent groups are those derived from heterocyclic aromatic compounds defined in the above. 1 and Ar 3 are each preferably independently selected from a phenylene group, a biphenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, and a fluorenylene group. 1 and Ar 3 are each independently a phenylene group (o-, m-, or p-phenylene group). 1 and Ar 3 is an o-phenylene group. 1 or Ar 3 In this case, a higher bond dissociation energy can be achieved. In addition, higher hole injection transport properties and triplet energy levels, lower driving voltages, film formability, and a balance of any two or more of these (particularly the balance between hole injection transport properties and film formability) can be achieved. 1 or Ar 3 may be unsubstituted or any hydrogen atom may be substituted with a substituent. 1 or Ar 3 Any hydrogen atom of When substituted, the substituents that can be present are not particularly limited, and include those described above for L 1 and L 3 The same examples as above can be applied. Preferably, Ar 1 and Ar 3are each independently a divalent group derived from a compound selected from benzene which is unsubstituted or substituted with a linear or branched alkyl group having 3 to 10 carbon atoms, biphenyl which is unsubstituted or substituted with a linear or branched alkyl group having 3 to 10 carbon atoms, and fluorene which is unsubstituted or substituted with a linear or branched alkyl group having 3 to 10 carbon atoms. More preferably, Ar 1 and Ar 3 are each independently an o-, m-, or p-phenylene group that is unsubstituted or substituted with a linear or branched alkyl group having from 3 to 10 carbon atoms. Even more preferably, Ar 1 and Ar 3 are each independently an unsubstituted o-phenylene group or an o-phenylene group substituted with a linear alkyl group having 5 to 8 carbon atoms. 1 and Ar 3 is an unsubstituted o-phenylene group. 1 or Ar 3 has a substituent (i.e., is a substituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms or a substituted divalent aromatic heterocyclic group), the position of the substituent is not particularly limited, but 1 or Ar 3 It is preferable that the nitrogen atom bonded to the Ar group is located as far away as possible from the nitrogen atom bonded to the Ar group. 1 or Ar 3 When is an o-phenylene group, the substituent is preferably present at the para-position relative to the nitrogen atom. This arrangement reduces the distance between the polymer compound and the quantum dots, strengthening the interaction between the polymer compound in the hole transport layer and the quantum dots in the light-emitting layer, thereby further improving the hole injection and transport properties (and therefore durability (device life, light-emitting life)).

[0082] In the above formula (1), Ar 1 Ar 2 or L 2 In the above formula (2), Ar 3 Ar4 or L 4 Thus, Ar 1 Ar 2 or L 2 Forms a ring with and Ar 3 Ar 4 or L 4 Among these, from the viewpoint of further improving the effects of the present invention, Ar 1 L 2 Forms a ring with, and Ar 3 L 4 and Ar 1 L 2 and Ar 3 L 4 More preferably, a ring is formed with Ar 1 L 2 Forms a ring with or Ar 3 L 4 In a more preferred embodiment of the present invention, Ar 1 L 2 Forms a ring with Ar 3 L 4 It forms a ring with Ar 1 L 2 Ar when forming a ring with 1 and L 2 and a ring structure formed by Ar 3 L 4 Ar when forming a ring with 3 and L 4 The ring structure formed by Ar is not particularly limited. 1 and L 2 and Ar 3 and L 4 It is preferable that at least one of Ar 1 and L 2 and Ar 3 and L 4 In other words, in a preferred embodiment of the present invention, -L in the above formula (1) 2 -N(Ar 1 )(Ar2 ) has a structure selected from the following group. In a preferred embodiment of the present invention, -L in the above formula (2) 4 -N(Ar 3 )(Ar 4 ) has a structure selected from the following group. In the following structure, R 211 ~R 214 are each independently a hydrogen atom or a linear or branched alkyl group having 3 to 10 carbon atoms. 211 ~R 214 is a hydrogen atom. In the following structures, "*1" indicates L 1 or L 3 The *2 is the binding site for Ar 2 or Ar 4 This is the binding site for

[0083] [ka]

[0084] More preferably, Ar 1 and L 2 and Ar 3 and L 4 At least one of Ar and Ar forms a carbazole ring having the following structure. 1 and L 2 and Ar 3 and L 4 and form a carbazole ring of the following structure. In the following structure, R 211 ~R 214 are each independently a hydrogen atom or a linear or branched alkyl group having 3 to 10 carbon atoms. 211 ~R 214 is a hydrogen atom. In the following structures, "*1" indicates L 1 or L 3 The *2 is the binding site for Ar 2 or Ar 4 This is the binding site for

[0085] [ka]

[0086] In a preferred embodiment of the present invention, in the above formula (1), Ar 1 L 2 and forms a ring with -(L 1 ) x -L 2 -N(Ar 1 )(Ar 2 In a preferred embodiment of the present invention, in the above formula (2), Ar 3 L 4 and forms a ring with -(L 3 ) y -L 4 -N(Ar 3 )(Ar 4 ) has a structure selected from the following group. In the following structure, "*1" is the bonding site with the nitrogen atom of the main chain, and "*2" is Ar 2 or Ar 4 This is the binding site for

[0087] [ka]

[0088] However, R 211 ~R 214 are each independently a hydrogen atom or a linear or branched alkyl group having 3 to 10 carbon atoms. 211 and R 213 is a hydrogen atom, and R 212 and R 214 is a hydrogen atom or a straight-chain alkyl group having 5 to 8 carbon atoms.

[0089] In the above formula (1), Ar 2represents a linear or branched hydrocarbon group having 1 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring atoms, which may be substituted with a divalent aromatic heterocyclic group having 5 to 14 ring atoms, or an aromatic heterocyclic group having 5 to 14 ring atoms, which may be substituted with a linear or branched hydrocarbon group having 1 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring atoms, or an aromatic heterocyclic group having 5 to 14 ring atoms, which may be substituted with a divalent aromatic heterocyclic group having 5 to 14 ring atoms, or an aromatic heterocyclic group having 1 to 12 carbon atoms, or an aromatic heterocyclic group having 5 to 14 ring atoms, which may be substituted with a linear or branched hydrocarbon group having 1 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring atoms, or an aromatic heterocyclic group having 5 to 14 ring atoms, 2 Ar 1 It may form a ring with Ar 2 Ar 1 When forming a ring with Ar 2 is a divalent group. Ar 2 Ar 1 When the ring does not form with Ar 2 is a monovalent group. , Ar 4 represents a linear or branched hydrocarbon group having 1 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring atoms, which may be substituted with a divalent aromatic heterocyclic group having 5 to 14 ring atoms, or an aromatic heterocyclic group having 5 to 14 ring atoms, which may be substituted with a linear or branched hydrocarbon group having 1 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring atoms, or an aromatic heterocyclic group having 5 to 14 ring atoms, which may be substituted with a divalent aromatic heterocyclic group having 5 to 14 ring atoms, or an aromatic heterocyclic group having 1 to 12 carbon atoms, or an aromatic heterocyclic group having 5 to 14 ring atoms, which may be substituted with a linear or branched hydrocarbon group having 1 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring atoms, or an aromatic heterocyclic group having 5 to 14 ring atoms, 4 Ar 3 It may form a ring with Ar 4 Ar 3 When forming a ring with Ar 4 is a divalent group. Ar 4 Ar 3 When the ring does not form with Ar 4 is a monovalent group. 2 and Ar in the above formula (2) 4 may be the same or different, but are preferably the same.

[0090] In a preferred embodiment of the present invention, when the polymer compound according to the present invention contains a structural unit of the above formula (1) and a structural unit of the above formula (2), R 21 , R 22 , R 31 , R 32 , L 1 , x, L 2 , Ar 1 and Ar 2 are R in the above formula (2), respectively. 23 , R 24 , R 33 , R 34 , L 3 ,y,L 4 , Ar 3 and Ar 4 is the same as

[0091] where Ar 2 or Ar 4 The aromatic hydrocarbon group having 6 to 25 ring atoms and the divalent aromatic heterocyclic group having 5 to 14 ring atoms as Ar are not particularly limited. 2 or Ar 4 Ar 1 or Ar 3 When a ring is not formed with the above L 1 or L 3 In the same manner, in the above case, a divalent group derived from an aromatic hydrocarbon having 6 to 25 ring atoms as defined in the above formula can be converted into a monovalent group. 2 or Ar 4 The aromatic heterocyclic group as L is not particularly limited, but may be any of the above-mentioned 1 or L 3 Examples of such heterocyclic aromatic compounds include those derived from the heterocyclic aromatic compounds defined in the above, which are converted into monovalent groups. 2 or Ar 4 Ar 1 or Ar 3 When forming a ring with the above L 1 or L 3 Examples of such a divalent group include a divalent group derived from an aromatic hydrocarbon having 6 to 25 ring atoms as defined in the above. 2 or Ar4 The aromatic heterocyclic group as L is not particularly limited, but may be any of the above-mentioned 1 or L 3 Examples of the divalent groups are those derived from heterocyclic aromatic compounds defined in the above. 2 and Ar 4 are preferably each independently a group derived from a compound selected from benzene, biphenyl, dibenzofuran, dibenzothiophene, and fluorene. 2 and Ar 4 are each independently a group derived from benzene (phenyl group or o-, m-, or p-phenylene group). Particularly preferably, Ar 2 or Ar 4 Ar 2 or Ar 4 Ar 1 or Ar 3 When it does not form a ring with Ar, it is a phenyl group, or Ar 2 or Ar 4 Ar 1 or Ar 3 When a ring is formed with Ar, it is an o-phenylene group. 2 or Ar 4 In the case of the unsubstituted form, a higher bond dissociation energy can be achieved. In addition, higher hole injection / transport properties and triplet energy levels, lower driving voltages, film-forming properties, and a balance of any two or more of these (particularly, a balance between hole injection / transport properties and film-forming properties) can be achieved.

[0092] In one embodiment of the present invention, Ar 2 or Ar 4has as a substituent a linear hydrocarbon group having from 1 to 12 carbon atoms or a branched hydrocarbon group having from 3 to 12 carbon atoms, an aromatic hydrocarbon group having from 6 to 25 ring atoms, or a divalent aromatic heterocyclic group having from 5 to 14 ring atoms. By locating such a substituent at the end of the polymer compound, the polymer compound in the hole transport layer can closely interact with the quantum dots in the light-emitting layer, thereby improving the hole injection and transport properties. Therefore, the durability (device life, light-emitting life) of an electroluminescent device (particularly a quantum dot electroluminescent device) using the polymer compound of the present invention can be further effectively improved.

[0093] Here, the hydrocarbon group having 1 to 12 carbon atoms is not particularly limited, but may be a linear or branched alkyl group, a linear or branched alkenyl group, a linear or branched aryl group, a linear or branched alkyl ... Examples of the Ar group include alkynyl and cycloalkyl groups. 2 or Ar 4 When is an alkenyl or alkynyl group, Ar 2 or Ar 4 The number of carbon atoms in Ar is 2 or more and 12 or less. 2 or Ar 4 When is a cycloalkyl group, Ar 2 or Ar 4 The number of carbon atoms is 3 or more and 12 or less.

[0094] Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a tert-pentyl group, a neopentyl group, a 1,2-dimethylpropyl group, an n-hexyl group, an isohexyl group, a 1,3-dimethylbutyl group, a 1-isopropylpropyl group, a 1,2-dimethylbutyl group, an n-heptyl group, a 1,4-dimethylbutyl group, an 1,5-dimethylbutyl group, an 1,6-dimethylbutyl group, an 1,7-dimethylbutyl group, an 1,8-dimethylbutyl group, an 1,9-dimethylbutyl group, an 1,10-dimethylbutyl group, an 1,11-dimethylbutyl group, an 1,12-dimethylbutyl group, an 1,13-dimethylbutyl group, an 1,14-dimethylbutyl group, an 1,15-dimethylbutyl group, an 1,16-dimethylbutyl group, an 1,17-dimethylbutyl group, an 1,18-dimethylbutyl group, an 1,19-dimethylbutyl group, an 1,20-dimethylbutyl group, an 1,21-dimethylbutyl group, an 1,22-dimethylbutyl group, an 1,23-dimethylbutyl group, an 1,24-dimethylbutyl group, an 1,25-dimethylbutyl group, an 1,26-dimethylbutyl group, an 1,27-dimethylbutyl group, an 1,28-dimethylbutyl group, an 1,29 ...9-dimethylbutyl group, an 1,29-dimethylbutyl group, an 1,29-dimethylbutyl group, Examples of such alkyl groups include ethylpentyl group, 3-ethylpentyl group, 2-methyl-1-isopropylpropyl group, 1-ethyl-3-methylbutyl group, n-octyl group, 2-ethylhexyl group, 3-methyl-1-isopropylbutyl group, 2-methyl-1-isopropyl group, 1-tert-butyl-2-methylpropyl group, n-nonyl group, 3,5,5-trimethylhexyl group, n-decyl group, isodecyl group, n-undecyl group, 1-methyldecyl group, and n-dodecyl group.

[0095] Examples of the alkenyl group having 2 to 12 carbon atoms include a vinyl group, an allyl group, a 1-propenyl group, a 2-butenyl group, a 1,3-butadienyl group, a 2-pentenyl group, and an isopropenyl group.

[0096] Examples of the alkynyl group having 2 to 12 carbon atoms include an ethynyl group and a propargyl group.

[0097] Examples of the cycloalkyl group having 3 or more and 12 or less carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0098] Also, Ar 2 or Ar 4 The aromatic hydrocarbon group having 6 to 25 ring atoms present in the above L is not particularly limited, but 1 or L 3 The divalent group derived from an aromatic hydrocarbon having 6 to 25 ring atoms as defined in the above formula can be converted into a monovalent group. 2 or Ar 4The aromatic hydrocarbon group having 6 to 25 ring atoms present in the formula (I) is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a 9,9-dimethylfluorenyl group, or any combination thereof (for example, a 9,9-dimethyl-2-phenylfluorenyl group).

[0099] Also, Ar 2 or Ar 4 The divalent aromatic heterocyclic group having 5 to 14 ring atoms present in is not particularly limited, but may be any of the above-mentioned L 1 or L 3 The divalent group derived from a heterocyclic aromatic compound having 5 to 14 ring atoms as defined in the above formula can be converted into a monovalent group. 2 or Ar 4 The divalent aromatic heterocyclic group having 5 to 14 ring atoms present in is a group derived from pyridine.

[0100] In addition, aromatic hydrocarbon groups having 6 to 25 ring atoms and divalent aromatic heterocyclic groups having 5 to 14 ring atoms can be combined to form Ar 2 or Ar 4 may be present in

[0101] Of these, Ar 2 or Ar 4 The substituents present in the hole transport layer are preferably selected from the group consisting of a linear alkyl group having 4 to 10 carbon atoms or a branched alkyl group having 4 to 10 carbon atoms, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a 9,9-dimethylfluorenyl group, a pyridinyl group, and any combination thereof (for example, a 9,9-dimethyl-2-phenylfluorenyl group). This allows the polymer compound in the hole transport layer to be present in closer proximity to (and interact more closely with) the quantum dots in the light-emitting layer. Therefore, the hole injection and transport properties can be further improved. Therefore, the durability (device life, light emission life) of an electroluminescent device (particularly a quantum dot electroluminescent device) using the polymer compound according to the present invention can be further effectively improved. That is, in a preferred embodiment of the present invention,2 and Ar 4 are each independently a group derived from a compound selected from the group consisting of benzene, biphenyl, dibenzofuran, dibenzothiophene, and fluorene, and are substituted with a linear or branched alkyl group having from 4 to 10 carbon atoms, or a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a 9,9-dimethylfluorenyl group, a 9,9-dimethyl-2-phenylfluorenyl group, a pyridinyl group, a 3-pyridinylphenyl group, a 4-pyridinylphenyl group, or a biphenyl group substituted with a pyridinyl group. More preferably, Ar 2 or Ar 4 The hydrocarbon group present in Ar is a linear alkyl group having 5 to 8 carbon atoms. 2 or Ar 4 is a group derived from benzene (phenyl group, o-, m-, or p-phenylene group) substituted with a linear alkyl group having 5 to 8 carbon atoms. 2 or Ar 4 The hydrocarbon group present in Ar is a linear alkyl group having 6 to 8 carbon atoms. 2 or Ar 4 is a phenyl group (Ar 2 or Ar 4 Ar 1 or Ar 3 o-phenylene group (Ar 2 or Ar 4 Ar 1 or Ar 3 (When a ring is formed with

[0102] In addition, Ar 2 or Ar 4 The position of the substituent in -L is not particularly limited. 2 -N(Ar 1 )(Ar 2 ) or -L 4 -N(Ar 3)(Ar 4 It is preferable that the nitrogen atom of Ar is located as far away as possible from the nitrogen atom of Ar. 1 L 2 forms a ring with Ar 2 When is a phenyl group, the hydrocarbon group is preferably present at the para-position relative to the nitrogen atom. This arrangement allows the polymer compound in the hole transport layer to be closer to the quantum dots in the light-emitting layer (allowing for closer interaction), thereby further improving hole injection and transport properties. Therefore, electroluminescent devices (particularly quantum dot electroluminescent devices) using the polymer compound of the present invention can be more effectively improved in durability (device life, light-emitting life).

[0103] Ar 2 or Ar 4 Ar 1 or Ar 3 It may form a ring with Ar 2 or Ar 4 Ar 1 or Ar 3 When forming a ring with Ar 2 or Ar 4 and Ar 1 or Ar 3 The ring structure formed by Ar is not particularly limited. 2 or Ar 4 and Ar 1 or Ar 3 In other words, in a more preferred embodiment of the present invention, in the above formula (1), Ar 1 Ar 2 Forms a ring with -N(Ar 1 )(Ar 2 In a more preferred embodiment of the present invention, in the above formula (2), Ar 3 Ar 4 Forms a ring with -N(Ar 3 )(Ar 3 ) is a group selected from the following group:

[0104] [ka]

[0105] However, R 311 ~R 323 Each of R independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms. 311 ~R 312 At least one of R 313 ~R 315 At least one of R 316 ~R 319 At least one of R 320 ~R 321 At least one of or R 322 ~R 323 At least one of the groups represents a linear or branched alkyl group having 1 to 12 carbon atoms (more preferably a linear or branched alkyl group having 4 to 10 carbon atoms, even more preferably a linear alkyl group having 5 to 8 carbon atoms, and particularly preferably a linear alkyl group having 6 to 8 carbon atoms).

[0106] More preferably, Ar 2 or Ar 4 and Ar 1 or Ar 3 In other words, in a more preferred embodiment of the present invention, -L in the above formula (1) 2 -N(Ar 1 )(Ar 2 In a more preferred embodiment of the present invention, -L in the above formula (2) has the following structure: 4 -N(Ar 3 )(Ar 4 ) has the following structure:

[0107] [ka]

[0108] However, R 311represents a hydrogen atom or a linear or branched alkyl group having from 4 to 10 carbon atoms (more preferably a hydrogen atom or a linear alkyl group having from 5 to 8 carbon atoms), and R 312 represents a linear or branched alkyl group having from 4 to 10 carbon atoms (more preferably a linear alkyl group having from 5 to 8 carbon atoms, particularly preferably a linear alkyl group having from 6 to 8 carbon atoms).

[0109] Therefore, the structural unit B preferably has the following structure: That is, in a preferred embodiment of the present invention, the structural unit B has the following structure in the formula (1):

[0110] [ka]

[0111] Or the following structure in the formula (2):

[0112] [ka]

[0113] each independently has a structure selected from the following group:

[0114] [ka]

[0115] In the above structure, R 51 ~R 54 each independently represents a hydrogen atom, a linear alkyl group having from 1 to 12 carbon atoms or a branched alkyl group having from 3 to 12 carbon atoms, or a group selected from the following group:

[0116] [ka]

[0117] Ar 411 ~Ar417 each independently represents a group selected from the following group:

[0118] [ka]

[0119] In this case, R 55 ~R 57 each independently represents a hydrogen atom, a linear alkyl group having from 1 to 12 carbon atoms or a branched alkyl group having from 3 to 12 carbon atoms, or a group selected from the following group:

[0120] [ka]

[0121] R 58 and R 59 are each independently a hydrogen atom or a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms.

[0122] The structural unit B more preferably has the following structure: That is, in a more preferred embodiment of the present invention, the structural unit B has the following structure in the formula (1):

[0123] [ka]

[0124] Or the following structure in the formula (2):

[0125] [ka]

[0126] each independently has a structure selected from the following group:

[0127] [ka]

[0128] In the above structure, Ar 412 ~Ar 416 each independently represents a group selected from the following group:

[0129] [ka]

[0130] In the above structure, R 55 ~R 57 each independently represents a linear or branched alkyl group having 4 to 10 carbon atoms.

[0131] Therefore, it is more preferable that the structural unit of formula (1) or formula (2) according to the present invention is selected from the following group.

[0132] [ka]

[0133] [ka]

[0134] [ka]

[0135] The structural unit of formula (1) or formula (2) according to the present invention is even more preferably selected from the following group:

[0136] [ka]

[0137] [ka]

[0138] In the above structure, R 11 ~R 14 , R 21 and R 22 is defined as in the above formula (1), R 41 ~R 44 , R 23 and R 24 is defined as in the above formula (2), Ar 412 ~Ar 416 each independently represents a group selected from the following group:

[0139] [ka]

[0140] In the above structure, R 55 ~R 57 each independently represents a linear or branched alkyl group having 4 to 10 carbon atoms.

[0141] The composition of the structural unit C in the polymer compound of the present invention is not particularly limited. Considering the durability (device life, luminescence life) of a layer (e.g., hole injection layer, hole transport layer) formed using the obtained polymer compound and the effect of further improving the hole injection and transport ability, the structural unit C preferably accounts for 10 mol % or more and 100 mol % or less, more preferably more than 50 mol % and 100 mol % or less, and particularly preferably 100 mol % of all structural units constituting the polymer compound (i.e., the polymer compound is composed only of structural unit C). Note that when the polymer compound contains two or more types of structural unit C, the content of the structural unit C refers to the total amount of the structural units C.

[0142] When the polymer compound according to the present invention contains the structural unit of the above formula (1) and the structural unit of the above formula (2), the structural unit represented by the following formula (1) and the structural unit represented by the following formula (2) The composition is such that the constitutional unit represented by the above formula (2) is, for example, a constitutional unit represented by the above formula (1) Preferably, the structural unit represented by formula (2) is present in a ratio of 1 to 20 moles per mole of the structural unit represented by formula (1), and more preferably, the structural unit represented by formula (2) is present in a ratio of 1 to 3 moles per mole of the structural unit represented by formula (1). The presence of two types of structural unit C in such a composition allows for more appropriate adjustment of desired properties (e.g., durability, film-forming ability).

[0143] As described above, the polymer compound of the present invention may be composed solely of structural unit C. Alternatively, the polymer compound of the present invention may further contain other structural units in addition to structural unit C. When other structural units are contained, the other structural units are not particularly limited as long as they do not impair the effects of the polymer compound (particularly durability, film-forming ability, high triplet energy level, and low driving voltage). Specific examples include structural units selected from the following group. Note that, hereinafter, the structural units shown in the following group will also be referred to as "structural unit D".

[0144] [ka]

[0145] The composition of the structural unit D in the polymer compound of this embodiment is not particularly limited. Considering the ease of film formation using the resulting polymer compound and the effect of further improving coating strength, the structural unit D is preferably 1 mol % or more and 10 mol % or less of all structural units constituting the polymer compound. Note that when the polymer compound contains two or more types of structural unit D, the content of the structural unit D refers to the total amount of the structural units D.

[0146] The weight-average molecular weight (Mw) of the polymer compound is not particularly limited as long as the intended effect of the present invention is obtained. The weight-average molecular weight (Mw) is, for example, preferably 8,000 to 1,000,000, more preferably 12,000 to 1,000,000, even more preferably 20,000 to 800,000, and particularly preferably 50,000 to 500,000. With such a weight-average molecular weight, it is possible to appropriately adjust the viscosity of a coating solution for forming a layer (e.g., a hole injection layer, a hole transport layer) using the polymer compound, thereby forming a layer with a uniform thickness.

[0147] The number-average molecular weight (Mn) of the polymer compound is not particularly limited as long as the intended effects of the present invention are achieved. The number-average molecular weight (Mn) is, for example, preferably 4,000 to 250,000, more preferably 10,000 to 250,000, even more preferably 20,000 to 150,000, and particularly preferably 25,000 to 100,000. With such a number-average molecular weight, it is possible to appropriately adjust the viscosity of a coating solution for forming a layer (e.g., a hole injection layer or a hole transport layer) using the polymer compound to form a layer with a uniform thickness. Furthermore, the polydispersity (weight-average molecular weight / number-average molecular weight) of the polymer compound of this embodiment is, for example, 1.2 to 6.0, preferably 1.2 to 4.0, and preferably 1.5 to 3.5. Below.

[0148] In this specification, the number average molecular weight (Mn) and weight average molecular weight (Mw) can be measured using any known method, or by appropriately modifying a known method. In this specification, the number average molecular weight (Mn) and weight average molecular weight (Mw) are values ​​measured by the following method. The polydispersity (Mw / Mn) of a polymer is calculated by dividing the weight average molecular weight (Mw) by the number average molecular weight (Mn) measured by the following method.

[0149] (Measurement of number average molecular weight (Mn) and weight average molecular weight (Mw)) The number average molecular weight (Mn) and weight average molecular weight (Mw) of a polymeric material are measured by SEC (Size Exclusion Chromatography) using polystyrene as a standard substance under the following conditions: (SEC measurement conditions) Analytical equipment (SEC): Shimadzu Corporation, Prominence Column: Polymer Laboratories, PLgel MIXED-B Column temperature: 40℃ Flow rate: 1.0mL / min Injection volume of sample solution: 20 μL (polymer concentration: approximately 0.05% by mass) Eluent: tetrahydrofuran (THF) Detector (UV-VIS detector): Shimadzu Corporation, SPD-10AV Standard sample: polystyrene.

[0150] The terminal of the main chain of the polymer compound of this embodiment is not particularly limited and is determined appropriately depending on the type of raw material used, but is usually a hydrogen atom.

[0151] The polymer compound of this embodiment can be synthesized using a known organic synthesis method. Specific synthesis methods for the polymer compound of this embodiment can be easily understood by those skilled in the art by referring to the examples described below. Specifically, the polymer compound of this embodiment can be produced by a polymerization reaction using a monomer represented by the following formula (1'), or a monomer represented by the following formula (1') and a monomer represented by the following formula (2'), or by a copolymerization reaction using a monomer represented by the following formula (1'), or a monomer represented by the following formula (1') and a monomer represented by the following formula (2'), and other monomers corresponding to the other structural units described above.

[0152] [ka]

[0153] [ka]

[0154] In the present invention, the above-mentioned monomers used in the polymerization of the polymer compound can be synthesized by appropriately combining known synthesis reactions, and their structures can be confirmed by known methods (e.g., NMR, LC-MS, etc.). For example, the monomer represented by the above formula (1') can be obtained by reacting a compound represented by the following formula (3') with a compound represented by the following formula (4'). Similarly, the monomer represented by the above formula (2') can be obtained by reacting a compound represented by the following formula (5') with a compound represented by the following formula (6').

[0155] [ka]

[0156] In the above formulas (1') to (6'), R 11 ~R 14 , R 21 , R 22 , R 31 , R 32 , L 1 , x, L 2 , Ar 1 and Ar 2 has the same definition as in the above formula (1). In the above formulas (1') to (6'), R 41 ~R 44 , R 23 , R 24 , R 33 , R 34 , L 3 ,y,L 4 , Ar 3 and Ar 4 is defined as in the above formula (2). 1 and Z 2 , Z 3 and Z 4 , Z 1’ and Z 2’ , Z 3’ and Z 4’ , Z 1” and Z2” , and Z 3” and Z 3” are each independently a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, in particular a bromine atom) or a group having the following structure: In the following structure, R A ~R D are each independently an alkyl group having 1 to 3 carbon atoms. A ~R D is a methyl group.

[0157] [ka]

[0158] In addition, Z in the above formulas (1') to (6') 1 and Z 2 , Z 3 and Z 4 , Z 1’ and Z 2’ , Z 3’ and Z 4’ , Z 1” and Z 2” , and Z 3” and Z 3” may be the same or different. Preferably, in the above formula (1′), Z 1 and Z 2 Preferably, in the above formula (2'), Z 3 and Z 4 In addition, Z in the above formula (1') 1 and Z 2 are different and Z in the above formula (2') 3 and Z 4 are different and Z in the above formula (1') 1 and Z 3 are the same and Z in the above formula (1') 2 and Z 4 It is more preferable that Z in the above formula (3') are the same. 1’ and Z 2’ are the same. Preferably, in the above formula (4'), Z 1” and Z2” In addition, Z in the above formula (3') is the same. 1’ and Z 2’ is the same and Z in the above formula (4') 1” and Z 2” is the same and Z in the above formula (3') 1’ and Z 2’ is Z in the above formula (4') 1” and Z 2” Preferably, in the above formula (5'), Z 3’ and Z 4’ are the same. Preferably, in the above formula (6'), Z 3” and Z 4” In addition, Z in the above formula (5') is the same. 3’ and Z 4’ is the same and Z in the above formula (6') 3” and Z 4” is the same and Z in the above formula (3') 3’ and Z 4’ is Z in the above formula (6') 3” and Z 4” It is more preferable that it is different from

[0159] The polymer compound of this embodiment has a structural unit C. Therefore, the polymer compound has a large C-N bond dissociation energy and high hole injection and transport properties. Therefore, when the polymer compound of this embodiment is used as a hole injection material or hole transport material (particularly a hole transport material), high durability (device life, luminescence life) can be achieved. Furthermore, the polymer compound of this embodiment has a high triplet energy level and a low driving voltage. Therefore, when the polymer compound of this embodiment is used as a hole injection material or hole transport material (particularly a hole transport material), high hole mobility can be achieved at a low driving voltage. Therefore, an electroluminescence device using the polymer compound of this embodiment has excellent durability (device life, luminescence life) and luminous efficiency.

[0160] [Electroluminescent element materials] The polymer compound according to this embodiment is suitable for use as an electroluminescence device material. The polymer compound according to this embodiment provides an electroluminescence device material with excellent durability (device life, luminescence life). The polymer compound according to this embodiment also provides an electroluminescence device material with a high triplet energy level (current efficiency) and a low driving voltage. Furthermore, the main chain (structural unit C) of the polymer compound has appropriate flexibility. Therefore, the polymer compound according to this embodiment exhibits high solubility in solvents and high heat resistance. Therefore, it can be easily formed into a film (thin film) by a wet (coating) method. Therefore, in a second aspect, an electroluminescence device material containing the polymer compound of the present invention is provided. Alternatively, the use of the polymer compound as an electroluminescence device material is provided.

[0161] Furthermore, the polymer compound according to this embodiment has a refractive index exceeding 5.20 eV, particularly 5.47 eV. Therefore, the polymer compound according to this embodiment can be suitably used in quantum dot electroluminescence devices (particularly in hole transport layers).

[0162] [Electroluminescent element] As described above, the polymer compound according to this embodiment is suitable for use in electroluminescence devices. Specifically, an electroluminescence device is provided, which includes a pair of electrodes and one or more organic films disposed between the electrodes and containing the polymer compound or electroluminescence device material according to this embodiment. Such electroluminescence devices have excellent durability (device life, luminescence life). Furthermore, such electroluminescence devices can exhibit excellent luminous efficiency at low driving voltages. Therefore, in a third aspect, the present invention provides an electroluminescence device comprising a first electrode, a second electrode, and one or more organic films disposed between the first and second electrodes, wherein at least one layer of the organic films contains the polymer compound according to this embodiment. The object (or effect) of the present invention can also be achieved by such an electroluminescence device according to this embodiment. In a preferred embodiment of the above aspect, the electroluminescence device further includes an emitting layer disposed between the electrodes and containing a luminescent material capable of emitting light from triplet excitons. The electroluminescent element of this embodiment is an example of the electroluminescent element according to the present invention.

[0163] Furthermore, the present embodiment provides a method for manufacturing an electroluminescent device comprising a pair of electrodes and one or more organic films disposed between the electrodes and containing the polymer compound of the present embodiment, wherein at least one of the organic films is formed by a coating method. The present embodiment also provides an electroluminescent device in which at least one of the organic films is formed by a coating method using such a method.

[0164] The polymer compound of this embodiment and the electroluminescence device material (EL device material) of this embodiment (hereinafter collectively referred to as "polymer compound / EL device material") have excellent solubility in organic solvents. Therefore, the polymer compound / EL device material of this embodiment is particularly suitable for use in producing devices (particularly thin films) by a coating method (wet process). For this reason, this embodiment provides a liquid composition containing the polymer compound of this embodiment and a solvent or dispersion medium. Such a liquid composition is an example of the liquid composition according to the present invention.

[0165] Furthermore, the electroluminescent device material according to the embodiment as described above is suitably used in the production of devices (particularly thin films) by a coating method (wet process). From the above viewpoint, the present embodiment provides a thin film containing the polymer compound of the present embodiment. Such a thin film is an example of the thin film according to the present invention.

[0166] Furthermore, the EL device material according to this embodiment has excellent hole injection and transport properties. Therefore, it can be suitably used in forming any organic film of a hole injection material, a hole transport material, a light-emitting material (host), etc. Among these, from the viewpoint of hole transport properties, it is suitably used as a hole injection material or a hole transport material, and is particularly suitably used as a hole transport material.

[0167] That is, the present embodiment provides a composition containing a polymer compound and at least one material selected from the group consisting of a hole transport material, an electron transport material, and a light-emitting material. The light-emitting material contained in the composition is not particularly limited, but may contain an organometallic complex (a light-emitting organometallic complex compound) or semiconductor nanoparticles (semiconductor inorganic nanoparticles).

[0168] [Electroluminescent element] The electroluminescent element according to this embodiment will be described below with reference to FIG. 1 is a schematic diagram showing an electroluminescent element according to this embodiment. In this specification, "electroluminescent element" may be abbreviated to "EL element."

[0169] As shown in FIG. 1, the EL device 100 according to this embodiment includes a substrate 110, a first electrode 120 disposed on the substrate 110, a hole injection layer 130 disposed on the first electrode 120, a hole transport layer 140 disposed on the hole injection layer 130, an emitting layer 150 disposed on the hole transport layer 140, an electron transport layer 160 disposed on the emitting layer 150, an electron injection layer 170 disposed on the electron transport layer 160, and a second electrode 180 disposed on the electron injection layer 170.

[0170] Here, the polymer compound of this embodiment is contained, for example, in any organic film (organic layer) disposed between the first electrode 120 and the second electrode 180. Specifically, the polymer compound is preferably contained in the hole injection layer 130 as a hole injection material, the hole transport layer 140 as a hole transport material, or the light-emitting layer 150 as a light-emitting material (host). The polymer compound is more preferably contained in the hole injection layer 130 as a hole injection material or the hole transport layer 140 as a hole transport material. The polymer compound is particularly preferably contained in the hole transport layer 140 as a hole transport material. That is, in a preferred embodiment of the present invention, the organic film containing the polymer compound is a hole transport layer, a hole injection layer, or a light-emitting layer. In a more preferred embodiment of the present invention, the organic film containing the polymer compound is a hole transport layer or a hole injection layer. In a particularly preferred embodiment of the present invention, the organic film containing the polymer compound is a hole transport layer.

[0171] The organic film containing the polymer compound / EL element material of this embodiment is formed by a coating method (solution coating method). Specifically, the organic film is formed by a solution coating method such as spin coating, casting, microgravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing, offset printing, or ink jet printing.

[0172] The solvent used in the solution coating method can be any solvent capable of dissolving the polymer compound / EL device material, and can be appropriately selected depending on the type of polymer compound used. Examples include toluene, xylene, ethylbenzene, diethylbenzene, methylene, propylbenzene, cyclohexylbenzene, dimethoxybenzene, anisole, ethoxytoluene, phenoxytoluene, isopropylbiphenyl, dimethylanisole, phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, and cyclohexane. The amount of solvent used is not particularly limited, but considering ease of coating, it is preferably an amount such that the polymer compound concentration is approximately 0.1% by mass to 10% by mass, more preferably 0.5% by mass to 5% by mass.

[0173] The method for forming the layers other than the organic film containing the polymer compound / EL element material is not particularly limited. The layers other than the organic film containing the polymer compound / EL element material of this embodiment may be formed by, for example, a vacuum deposition method or a solution coating method.

[0174] A substrate used in a general EL device can be used as the substrate 110. For example, the substrate 110 may be a glass substrate, a semiconductor substrate such as a silicon substrate, or a transparent plastic substrate.

[0175] A first electrode 120 is formed on the substrate 110. Specifically, the first electrode 120 is an anode and is formed from a metal, alloy, or conductive compound with a large work function. For example, the first electrode 120 may be formed as a transmissive electrode from indium tin oxide (In2O3-SnO2:ITO), indium zinc oxide (In2O3-ZnO), tin oxide (SnO2), zinc oxide (ZnO), or the like, which have excellent transparency and conductivity. The first electrode 120 may also be formed as a reflective electrode by laminating magnesium (Mg), aluminum (Al), or the like on the transparent conductive film. After the first electrode 120 is formed on the substrate 110, cleaning and UV-ozone treatment may be performed, if necessary.

[0176] A hole injection layer 130 is formed on the first electrode 120. The hole injection layer 130 is a layer that facilitates the injection of holes from the first electrode 120, and may be formed to a thickness of, specifically, about 10 nm to about 1000 nm, more specifically, about 20 nm to about 50 nm (dry film thickness; the same applies below).

[0177] The hole injection layer 130 can be formed of a known hole injection material. Examples of known hole injection materials for forming the hole injection layer 130 include poly(ether ketone)-containing triphenylamine (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate (PPBI), N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), copper capping layer, and the like. Copper phthalocyanine, 4,4',4"-tris(3-methylphenyl) N,N'-di(1-naphthyl)-N,N'-diphenylamine (4,4',4"-tris(3-methylphenylphenylamino)triphenylamine: m-MTDATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), 4,4',4"-tris(diphenylamino)triphenylamine (TDATA), 4,4',4"-tris(N,N-2-naphthyl)triphenylamine 4,4',4"-tris(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA), polyaniline / dodecylbenzenesulphonic acid, poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate) (poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate): PEDOT / PSS) and polyaniline / 10-camphorsulfone Examples of suitable amines include polyaniline / 10-camphorsulfonic acid.

[0178] A hole transport layer 140 is formed on the hole injection layer 130. The hole transport layer 140 is a layer having the function of transporting holes and may be formed to a thickness of, for example, about 10 nm to about 150 nm, more specifically, about 20 nm to about 50 nm. The hole transport layer 140 is preferably formed by a solution coating method using the polymer compound of this embodiment. This method can further improve the durability (device life, luminescence life) of the EL device 100. It can also improve the current efficiency of the EL device 100 and reduce the driving voltage. Furthermore, since the hole transport layer can be formed by a solution coating method, it can be efficiently formed over a large area.

[0179] However, when any other organic film of the EL device 100 contains the polymer compound of this embodiment, the hole transport layer 140 may be formed of a known hole transport material. Examples of known hole transport materials include 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), N-phenylcarbamoyl methyl ether, and the like. N-phenylcarbazole and polyvinylcarbazole Carbazole derivatives, such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), 4,4' ,4"-tris(N-carbazolyl)triphenylamine (TCTA), and N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB).

[0180] The light-emitting layer 150 is formed on the hole transport layer 140. The light-emitting layer 150 is a layer that emits light by fluorescence, phosphorescence, or the like, and is formed using a method such as vacuum deposition, spin coating, or inkjet printing. The light-emitting layer 150 may be formed to a thickness of, for example, about 10 nm to about 60 nm, more specifically, about 20 nm to about 50 nm. Known light-emitting materials can be used as the light-emitting material of the light-emitting layer 150. However, it is preferable that the light-emitting material contained in the light-emitting layer 150 be a light-emitting material that can emit light from triplet excitons (i.e., phosphorescence). In such a case, the operating life of the EL device 100 can be further improved.

[0181] The light-emitting layer 150 is not particularly limited and can have a known configuration. Preferably, the light-emitting layer contains semiconductor nanoparticles or an organometallic complex. That is, in a preferred embodiment of the present invention, the organic film has a light-emitting layer containing semiconductor nanoparticles or an organometallic complex. When the light-emitting layer contains semiconductor nanoparticles, the EL device is a quantum dot electroluminescent device (QLED), a quantum dot light-emitting device, or a quantum dot light-emitting device. When the light-emitting layer contains an organometallic complex, the EL device is an organic electroluminescent device (OLED).

[0182] In a configuration (QLED) in which the light-emitting layer contains semiconductor nanoparticles, the light-emitting layer is composed of a large number of semiconductor nanoparticles (quantum dots) arranged in a single layer or multiple layers. Here, the semiconductor nanoparticles (quantum dots) are particles of a predetermined size that exhibit a quantum confinement effect. The diameter (average diameter) of the semiconductor nanoparticles (quantum dots) is not particularly limited, but is approximately 1 nm or more and 10 nm or less.

[0183] The semiconductor nanoparticles (quantum dots) arranged in the light-emitting layer can be synthesized by wet chemical processes, metalorganic chemical vapor deposition processes, molecular beam epitaxy processes, or other similar processes, etc. Among these, wet chemical processes are methods in which precursor materials are added to an organic solvent to grow particles.

[0184] In the wet chemical process, the organic solvent naturally coordinates with the surface of the quantum dot crystals as they grow, acting as a dispersant and regulating the growth of the crystals. Therefore, wet chemical processes include vapor deposition such as metal organic chemical vapor deposition (MOCVD) and molecular beam epitaxy (MBE). Compared to conventional methods, the growth of semiconductor nanoparticles can be controlled easily and at low cost.

[0185] By adjusting the size of semiconductor nanoparticles (quantum dots), the energy band gap can be adjusted, allowing light of various wavelengths to be obtained in the light-emitting layer (quantum dot light-emitting layer). Therefore, using quantum dots of different sizes enables displays that emit (or emit) light of multiple wavelengths. The size of the quantum dots can be selected to emit red, green, and blue light, allowing the construction of a color display. In addition, the size of the quantum dots can be combined to emit various color lights to emit white light.

[0186] As the semiconductor nanoparticles (quantum dots), semiconductor materials selected from the group consisting of II-VI group semiconductor compounds; III-V group semiconductor compounds; IV-VI group semiconductor compounds; IV group elements or compounds; and combinations thereof can be used.

[0187] The II-VI semiconductor compound is not particularly limited, but may be selected from the group consisting of binary compounds selected from the group consisting of CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, and mixtures thereof; ternary compounds selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnTeSe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, and mixtures thereof; and quaternary compounds selected from the group consisting of CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and mixtures thereof.

[0188] The III-V semiconductor compound is not particularly limited, but may be selected from the group consisting of binary compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, and mixtures thereof; and quaternary compounds selected from the group consisting of GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof.

[0189] The IV-VI semiconductor compound is not particularly limited, and may be selected from the group consisting of binary compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof.

[0190] The Group IV element or compound is not particularly limited, but may be selected from the group consisting of mono-element compounds selected from the group consisting of Si, Ge, and mixtures thereof; and bi-element compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0191] Semiconductor nanoparticles (quantum dots) can have a homogeneous single structure or a core-shell dual structure. The core and shell can contain different materials. The materials composing each core and shell can be made of different semiconductor compounds. However, the energy band gap of the shell material is larger than that of the core material. Specifically, structures such as ZnTeSe / ZnSe / ZnS, InP / ZnSe / ZnS, CdSe / ZnS, and InP / ZnS are preferred.

[0192] For example, we will explain how to fabricate quantum dots with a core (CdSe)-shell (ZnS) structure. First, we used TOPO (trioctylphosphine oxide) as a surfactant. Precursors of the core (CdSe), such as (CH3)2Cd (dimethylcadmium) and TOPSe (trioctylphosphine selenide), are injected into an organic solvent to generate crystals. After maintaining the crystal at a high temperature for a certain time so that it grows to a certain size, a shell (ZnS) precursor material is injected to form a shell on the surface of the already formed core. TOPO-capped CdSe / ZnS quantum dots can be fabricated.

[0193] In addition, in the form (OLED) in which the light-emitting layer includes an organic metal complex, the light-emitting layer 150 includes, as a host material, for example, 6,9-diphenyl-9'-(5'-phenyl-[1,1':3',1"-terphenyl]-3-yl)3,3'-bi[9H-carbazole], 3,9-diphenyl-5-(3-(4-phenyl-6-(5'-phenyl-[1,1':3',1"-terphenyl]-3-yl)-1,3,5,-triazin-2-yl) )phenyl)-9H-carbazole, 9,9'-diphenyl-3,3'-bi[9H-carbazole], tris(8-quinolinato)aluminum (Alq3), 4,4'-bis(carbazol-9-yl)biphenyl (CBP), poly(n-vinyl carbazole) (PVK) ), 9,10-di(naphthalene)anthracene (ADN), 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), 1,3,5-tris(N-phenyl-benzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di(naphth-2-yl) Anthracene (3-tert-butyl-9,10-di(naphth-2-yl)anthracene:TBADN), distir Distyrylarylene (DSA), 4,4'-bis(9-carbazole)- It may also contain 2,2'-dimethyl-biphenyl (4,4'-bis(9-carbazole)2,2'-dimethyl-biphenyl: dmCBP).

[0194] The light-emitting layer 150 may contain, as a dopant material, for example, perylene and its derivatives, rubrene and its derivatives, coumarin and its derivatives, Derivative, 4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DC) The light-emitting material may include iridium (Ir) complexes such as bis[2-(4,6-difluorophenyl)pyridinate]picolinate iridium(III):FIrpic, bis(1-phenylisoquinoline)(acetylacetonate)iridium(III):Ir(piq)2(acac), tris(2-phenylpyridine)iridium(III):Ir(ppy)3, and tris(2-(3-p-oxyyl)phenyl)pyridineiridium(III), as well as osmium (Os) complexes and platinum complexes. Among these, the light-emitting material is preferably a light-emitting organometallic complex compound.

[0195] The method for forming the light-emitting layer is not particularly limited. The light-emitting layer can be formed by applying a coating solution containing semiconductor nanoparticles or an organometallic complex (solution coating method). In this case, it is preferable to select a solvent that does not dissolve the material in the hole transport layer (hole transport material, particularly a polymer compound) as the solvent constituting the coating solution.

[0196] An electron transport layer 160 is formed on the light-emitting layer 150. The electron transport layer 160 is a layer that has the function of transporting electrons. The electron transport layer is formed using a vacuum deposition method, a spin coating method, an inkjet method, or the like. The electron transport layer 160 may be formed to a thickness of, for example, about 15 nm or more and about 50 nm or less.

[0197] The electron transport layer 160 may be formed of a known electron transport material. Examples of electron transport materials include ZnCl, ZnMgO, (8-quinolinolato)lithium (lithium quinolate) (Liq), tris(8-quinolinolato)aluminum (Alq3), and compounds having a nitrogen-containing aromatic ring. Specific examples of compounds having an aromatic ring include 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene. Compounds containing a pyridine ring, compounds containing a triazine ring such as 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, imidazoles such as 2-(4-(N-phenylbenzoimidazolyl-1-yl-phenyl)-9,10-dinaphthylanthracene and 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI), The electron transport material may be a compound containing only one type of compound. They may be used alone or as a mixture of two or more.

[0198] An electron injection layer 170 is formed on the electron transport layer 160. The electron injection layer 170 is a layer that has the function of facilitating the injection of electrons from the second electrode 180. The electron injection layer 170 is formed using a vacuum deposition method or the like. The electron injection layer 170 may be formed to a thickness of about 0.1 nm or more and about 5 nm or less, more specifically about 0.3 nm or more and about 2 nm or less. Any known material can be used to form the electron injection layer 170. For example, the electron injection layer 170 can be formed using a lithium compound such as (8-quinolinato)lithium (lithium quinolate) ((8-quinolinato)lithium:Liq) and lithium fluoride (LiF), sodium chloride (NaCl), cesium fluoride (CsF), lithium oxide ( It may be formed of Li2O, barium oxide (BaO), or the like.

[0199] The second electrode 180 is formed on the electron injection layer 170. The second electrode 180 is formed by vacuum deposition or the like. Specifically, the second electrode 180 is a cathode and is formed of a metal, alloy, or conductive compound with a low work function. For example, the second electrode 180 may be formed as a reflective electrode using a metal such as lithium (Li), magnesium (Mg), aluminum (Al), or calcium (Ca), or an alloy such as aluminum-lithium (Al-Li), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag). The second electrode 180 may be formed to a thickness of about 10 nm to about 200 nm, more specifically, about 50 nm to about 150 nm. Alternatively, the second electrode 180 may be formed as a transmissive electrode using a thin film of the above metal materials, such as a transparent conductive film of indium tin oxide (In2O3-SnO2) or indium zinc oxide (In2O3-ZnO), with a thickness of 20 nm or less.

[0200] The EL element 100 according to this embodiment has been described above as an example of an electroluminescent element according to the present invention. The EL element 100 according to this embodiment can further improve durability (element life, luminous life) by providing an organic film (particularly a hole transport layer or a hole injection layer) containing a polymer compound. In addition, the luminous efficiency (current efficiency) can be further improved and the driving voltage can be reduced.

[0201] The layered structure of the EL element 100 according to this embodiment is not limited to the above example. The EL element 100 according to this embodiment may be formed with other known layered structures. For example, the EL element 100 may omit one or more of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, and the electron injection layer 170, or may include other layers in addition. Each layer of the EL element 100 may be formed as a single layer or as multiple layers.

[0202] For example, the EL device 100 may further include a hole-blocking layer between the hole-transporting layer 140 and the light-emitting layer 150 to prevent excitons or holes from diffusing into the electron-transporting layer 160. The hole-blocking layer may be formed of, for example, an oxadiazole derivative, a triazole derivative, or a tetraazolone derivative. It can be formed by a triazole derivative, a phenanthroline derivative, or the like.

[0203] Furthermore, the polymer compound according to this embodiment can be applied to electroluminescence devices other than the QLED or OLED. Examples of other electroluminescence devices to which the polymer compound according to this embodiment can be applied include, but are not limited to, organic-inorganic perovskite light-emitting devices. [Example]

[0204] The effects of the present invention will be explained using the following examples and comparative examples. However, the technical scope of the present invention is not limited to the following examples. In the following examples, unless otherwise specified, operations were performed at room temperature (25°C). Furthermore, unless otherwise specified, "%" and "parts" mean "% by mass" and "parts by mass", respectively.

[0205] Synthesis Example 1 (Synthesis of Compound M-1) Compound M-1 was synthesized according to the following reaction.

[0206] [ka]

[0207] (Synthesis of Compound 1a) In a four-neck flask, 6,12-dihydroindeno[1,2-b]fluorene (39.3 mmol, 10.0 g) and DMSO (65 ml) were added. Sodium t-butoxide (NaOtBu) (235 mmol, 22.7 g) was added and stirred for 10 minutes at room temperature (25°C) under a nitrogen atmosphere. 1-Bromohexane (235 mmol, 38.9 g) was then added dropwise, and the mixture was heated and stirred at 80°C for 3 hours. After the reaction was completed, the resulting solution was cooled to room temperature and extracted with hexane. The resulting organic layer was concentrated and recrystallized from hexane and ethanol to obtain compound 1a (yield: 19.7 g, 85%).

[0208] (Synthesis of Compound M-1) Compound 1a (16.9 mmol, 10.0 g), iron(III) chloride (FeCl3) (0.25 mmol, 15 mg), and chloroform (150 ml) were placed in a four-neck flask and stirred at 0°C for 5 minutes under a nitrogen atmosphere. Bromine (33.8 mmol, 1.7 ml) was then added dropwise, and the mixture was stirred at room temperature for 3 hours. After the reaction was completed, an aqueous solution of sodium thiosulfate was added to the reaction system, followed by extraction with hexane. The resulting organic layer was concentrated and recrystallized from hexane and ethanol to obtain compound M-1 (yield 6.1 g, 72%).

[0209] Synthesis Example 2 (Synthesis of Compound M-2) Compound M-2 was synthesized according to the following reaction.

[0210] [ka]

[0211] Compound M-2 was obtained in the same manner as in Synthesis Example 1, except that 1-bromooctane was used instead of 1-bromohexane (yield: 5.9 g, 70%).

[0212] Synthesis Example 3 (Synthesis of Compound M-3) Compound M-3 was synthesized according to the following reaction.

[0213] [ka]

[0214] Compound M-3 was obtained in the same manner as in Synthesis Example 1, except that 1-bromododecane was used instead of 1-bromohexane (yield: 5.4 g, 74%).

[0215] Synthesis Example 4 (Synthesis of M-A1) Compound M-A1 was synthesized according to the following reaction.

[0216] [ka]

[0217] A 1 L four-neck flask was charged with 9-(4-hexylphenyl)-3-iodo-9-carbazole (20.0 g), 4-(diphenylamino)phenylboronic acid (15.3 g), sodium carbonate (9.51 g), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (2.49 g), toluene (221 mL), ethanol (110 mL), and water (110 mL) and stirred at 120 °C (bath temperature) for 3 hours. After cooling to room temperature, the aqueous layer was separated, and the organic layer was washed with water (100 L × 2) and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by column chromatography to give 4-(9-(4-hexylphenyl)-9-carbazol-3-yl)-N,N-diphenyl)aniline (17.7 g).

[0218] The resulting 4-(9-(4-hexylphenyl)-9-carbazol-3-yl)-N,N-diphenyl)aniline (17.7 g) and N,N-dimethylformamide (DMF) (310 mL) were added to a 500 mL four-neck flask and cooled on ice. Under a nitrogen atmosphere, N-bromosuccinimide (NBS) (11.7 g) dissolved in DMF (30 mL) was added dropwise and stirred for 6 hours. The insoluble material was filtered off, washed with methanol (800 mL) and water (800 mL), and dried under vacuum to give 4-bromo-N-(4-bromophenyl)-N-(4-(9-(4-hexylphenyl)-9-carbazol-3-yl)phenyl)aniline (14.0 g).

[0219] The 4-bromo-N-(4-bromophenyl)-N-(4-(9-(4-hexylphenyl)-9-carbazol-3-yl)phenyl)aniline (14.0 g) obtained above, bispinacol diborate (14.8 g), potassium acetate (KOAc) (11.4 g), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (PdCl2(dppf)CH2Cl2) (0.477 g), and 1,4-dioxane (160 mL) were placed in a 500 mL four-neck flask and refluxed at 100°C for 4 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature, and the solid was filtered off using Celite as a filter aid. The residue was filtered off, and the filtrate was passed through silica gel. The solvent was removed by distillation under reduced pressure, and the residue was dissolved in toluene (200 mL). Activated carbon (14.2 g) was added and refluxed for 30 minutes. The activated carbon was removed by filtration, and the solvent was removed by distillation under reduced pressure. The residue was recrystallized using a mixed solvent of toluene and acetonitrile to obtain compound M-A1 (11.9 g).

[0220] Example 1 (Synthesis of polymer compound P-1) Compound M-A1 (1.777 g) synthesized in Synthesis Example 4 above, compound M-1 (1.617 g) synthesized in Synthesis Example 1 above, palladium acetate (4.8 mg), tris(2-methoxyphenyl)phosphine (45.7 g), toluene (64 mL), and 20% by weight aqueous tetraethylammonium hydroxide solution (11.1 g) were mixed under an argon atmosphere and refluxed for 6 hours. Next, phenylboronic acid (261.4 mg), bis(triphenylsphine)palladium(II) dichloride (91.0 mg), and 20% by weight aqueous tetraethylammonium hydroxide solution (11.1 g) were added to the reaction solution and refluxed for 6 hours. The aqueous layer was then removed from the resulting solution, and sodium N,N-diethyldithiocarbamate trihydrate (6.5 g) and ion-exchanged water (60 mL) were added and stirred at 85°C for 6 hours. The organic layer of the resulting solution was separated from the aqueous layer, and then the organic layer was washed with water, a 3% by mass aqueous solution of acetic acid, and water. The organic layer was added dropwise to methanol to precipitate the polymer, which was then filtered and dried to obtain a solid. This solid was dissolved in toluene and passed through a column chromatography packed with silica gel / alumina, and the solvent was distilled off under reduced pressure. The resulting liquid was added dropwise to methanol, and the precipitated solid was filtered and dried to obtain polymer compound P-1 (yield: 1.56 g). The weight-average molecular weight (Mw) and dispersity (Mw / Mn) of the resulting polymer compound P-1 were measured by SEC. As a result, the weight-average molecular weight (Mw) and dispersity (Mw / Mn) of polymer compound P-1 were 150,600 and 2.35, respectively.

[0221] The polymer compound P-1 thus obtained is presumed to be a polymer compound having the following structural units based on the monomer charging ratio.

[0222] [ka]

[0223] Example 2 (Synthesis of polymer compound P-2) Polymer compound P-2 was obtained in the same manner as in Example 1, except that compound M-2 (1.296 g) synthesized in the above Synthesis Example 2 was used instead of compound M-1. The weight-average molecular weight (Mw) and dispersity (Mw / Mn) of the obtained polymer compound P-2 were measured by SEC. As a result, the weight-average molecular weight (Mw) and dispersity (Mw / Mn) of the polymer compound P-2 were 149,000 and 2.24, respectively.

[0224] The polymer compound P-2 thus obtained is presumed to be a polymer compound having the following structural units based on the monomer charging ratio.

[0225] [ka]

[0226] Example 3 (Synthesis of polymer compound P-3) Polymer compound P-3 was obtained in the same manner as in Example 1, except that compound M-3 (1.673 g) synthesized in Synthesis Example 3 above was used instead of compound M-1. The weight-average molecular weight (Mw) and dispersity (Mw / Mn) of the obtained polymer compound P-3 were measured by SEC. As a result, the weight-average molecular weight (Mw) and dispersity (Mw / Mn) of polymer compound P-2 were 134,400 and 2.23, respectively.

[0227] The polymer compound P-3 thus obtained is presumed to be a polymer compound having the following structural units based on the monomer charging ratio.

[0228] [ka]

[0229] Example 4 (Synthesis of polymer compound P-4) Under an argon atmosphere, the compound M-A1 (0.592 g, 1.0 mol equivalent) synthesized in Synthesis Example 4 above, the compound M-1 (0.270 g, 0.5 mol equivalent) synthesized in Synthesis Example 1 above, the compound M-3 (0.391 g, 0.5 mol equivalent) synthesized in Synthesis Example 3 above, palladium acetate (1.6 mg), tris(2-methoxyphenyl)phosphine (15.7 g), toluene (20 mL), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (4.1 g) were mixed and refluxed for 6 hours. Next, phenylboronic acid (261 0.4 mg), bis(triphenylsphine)palladium(II) dichloride (30.1 mg), and 20% by mass tetraethylammonium hydroxide aqueous solution (11.1 g) were added and heated to reflux for 6 hours. The aqueous layer was then removed from the resulting solution, and sodium N,N-diethyldithiocarbamate trihydrate (6.5 g) and ion-exchanged water (60 mL) were added and stirred at 85°C for 6 hours. The organic layer of the resulting solution was separated from the aqueous layer, and then the organic layer was washed with water, a 3% by mass acetic acid aqueous solution, and water. The organic layer was added dropwise to methanol to precipitate the polymer, which was then filtered and dried to obtain a solid. This solid was dissolved in toluene and passed through a column filled with silica gel / alumina, and the solvent was distilled off under reduced pressure. The resulting liquid was added dropwise to methanol, and the precipitated solid was filtered and dried to obtain polymer compound P-4 (yield 0.56 g). The weight-average molecular weight (Mw) and dispersity (Mw / Mn) of the polymer compound P-4 were measured by SEC, and the weight-average molecular weight (Mw) and dispersity (Mw / Mn) of the polymer compound P-4 were found to be 185,000 and 2.56, respectively.

[0230] The polymer compound P-4 thus obtained is presumed to be a polymer compound having the following structural units based on the monomer charging ratio.

[0231] [ka]

[0232] Example 5 (Synthesis of polymer compound P-5) Polymer compound P-5 was obtained in the same manner as in Example 4, except that compound M-A1 (0.790 g, 1.0 mol equivalent) synthesized in Synthesis Example 4 above, compound M-1 (0.270 g, 0.375 mol equivalent) synthesized in Synthesis Example 1 above, and compound M-3 (0.651 g, 0.625 mol equivalent) synthesized in Synthesis Example 3 above were used instead. The weight-average molecular weight (Mw) and polydispersity (Mw / Mn) of the obtained polymer compound P-5 were measured by SEC. As a result, the weight-average molecular weight (Mw) and polydispersity (Mw / Mn) of polymer compound P-5 were 102,000 and 2.12, respectively.

[0233] The polymer compound P-5 thus obtained is presumed to be a polymer compound having the following structural units based on the monomer charging ratio.

[0234] [ka]

[0235] Example 6 (Synthesis of polymer compound P-6) Polymer compound P-6 was obtained in the same manner as in Example 4, except that compound M-A1 (0.592 g, 1.0 mol equivalent) synthesized in Synthesis Example 4 above, compound M-1 (0.135 g, 0.25 mol equivalent) synthesized in Synthesis Example 1 above, and compound M-3 (0.586 g, 0.75 mol equivalent) synthesized in Synthesis Example 3 above were used instead. The weight-average molecular weight (Mw) and polydispersity (Mw / Mn) of the obtained polymer compound P-6 were measured by SEC. As a result, the weight-average molecular weight (Mw) and polydispersity (Mw / Mn) of polymer compound P-6 were 55,000 and 2.20, respectively.

[0236] The polymer compound P-6 thus obtained is presumed to be a polymer compound having the following structural units based on the monomer charging ratio.

[0237] [ka]

[0238] Comparative Example 1 (Synthesis of polymer compound P-7) Under an argon atmosphere, compound M-A1 (1.64 g) synthesized in Synthesis Example 4 above, 2,7-dibromo-9,9-di-n-hexylfluorene (0.983 g), palladium acetate (9.0 mg), tris(2-methoxyphenyl)phosphine (42.2 mg), toluene (53 mL), and 20% by mass tetraethylammonium hydroxide aqueous solution (10.3 g) were added to a four-neck flask and stirred at 85° C. for 6 hours. Next, phenylboronic acid (241 mg), tetrakis(triphenylphosphino)palladium (140 mg), and 20% by mass tetraethylammonium hydroxide aqueous solution (10.3 g) were added and stirred for 3 hours. Next, sodium N,N-diethyldithiocarbamate trihydrate (13.5 g) dissolved in ion-exchanged water (50 mL) was added and stirred at 85°C for 2 hours. After separating the organic layer from the aqueous layer, the organic layer was washed with water, a 3% by mass aqueous acetic acid solution, and water. The organic layer was passed through a column chromatograph packed with silica gel / alumina, and the solvent was distilled off under reduced pressure. The resulting liquid was added dropwise to methanol, and the precipitated solid was dissolved in toluene. Next, this solution was added dropwise to methanol to precipitate, and the precipitated solid was filtered and dried to obtain polymer compound P-7 (1.35 g). The weight-average molecular weight (Mw) and polydispersity (Mw / Mn) of the resulting polymer compound P-7 were measured by SEC. As a result, the weight-average molecular weight (Mw) and polydispersity (Mw / Mn) of polymer compound P-7 were 86,000 and 2.56, respectively.

[0239] The polymer compound P-7 thus obtained is presumed to be a polymer compound having the following structural units based on the monomer charging ratio.

[0240] [ka]

[0241] Example 7 A glass substrate with an indium tin oxide (ITO) patterned to a thickness of 150 nm was used as the first electrode (anode). This ITO-coated glass substrate was sequentially cleaned with a neutral detergent, deionized water, water, and isopropyl alcohol, followed by UV-ozone treatment. Next, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS) (Sigma-Aldrich) was spin-coated onto the ITO-coated glass substrate to a dry thickness of 30 nm, and then dried. As a result, a hole injection layer with a dry thickness of 30 nm was formed on the ITO-coated glass substrate.

[0242] A 1.0% by mass toluene solution of polymer compound P-1 (hole transport material) of Example 1 was applied onto the hole injection layer by spin coating to a dry film thickness of 30 nm, followed by heat treatment at 230° C. for 60 minutes to form a hole transport layer. As a result, a hole transport layer with a thickness (dry film thickness) of 30 nm was formed on the hole injection layer.

[0243] In octane, the following structure:

[0244] [ka]

[0245] A quantum dot dispersion was prepared by dispersing blue quantum dots of ZnTeSe / ZnSe / ZnS (core / shell / shell; average diameter = approximately 10 nm) having the above structure at a concentration of 2.0 mass %. The hole transport layer (particularly polymer compound P-1) is insoluble in octane. This quantum dot dispersion was applied to the hole transport layer by spin coating to a dry film thickness of 30 nm, and then dried. As a result, a quantum dot light-emitting layer with a thickness (dry film thickness) of 30 nm was formed on the hole transport layer. The light emitted by irradiating the quantum dot dispersion with ultraviolet light had a center wavelength of 462 nm and a half-width of 30 nm.

[0246] Next, ZnCl was dissolved in ethanol as a solvent at a concentration of 0.7 mol / L to prepare a ZnCl coating solution. The ZnCl coating solution prepared above was slowly dripped onto the light-emitting surface formed above, left for 60 seconds, then spin-coated at 1000 rpm for 40 seconds, and dried by heating at 80°C for 20 minutes. Next, ethanol was slowly dripped onto the light-emitting surface formed above, and the spin-coated process at 1000 rpm was repeated twice, followed by drying by heating at 80°C for 20 minutes.

[0247] ZnMgO was dispersed in ethanol to a concentration of 1% by mass to prepare a ZnMgO dispersion. The ZnMgO dispersion was applied to the quantum dot light-emitting layer by spin coating to a dry film thickness of 20 nm, and then heated and dried at 80°C for 30 minutes. As a result, an electron transport layer with a dry film thickness of 20 nm was formed on the quantum dot light-emitting layer.

[0248] Aluminum (Al) was evaporated onto the electron transport layer using a vacuum evaporation system, resulting in a 100 nm thick second electrode (cathode) on the electron transport layer, thereby obtaining the quantum dot electroluminescence device 1.

[0249] Example 8 A quantum dot electroluminescence device 2 was produced in the same manner as in Example 7, except that the polymer compound P-2 of Example 2 was used instead of the polymer compound P-1.

[0250] Example 9 A quantum dot electroluminescence device 3 was produced in the same manner as in Example 7, except that the polymer compound P-3 of Example 3 was used instead of the polymer compound P-1.

[0251] Example 10 A quantum dot electroluminescent element was prepared in the same manner as in Example 7, except that the polymer compound P-4 of Example 4 was used instead of the polymer compound P-1. Four offspring were produced.

[0252] Example 11 Quantum dot electroluminescence device 5 was produced in the same manner as in Example 7, except that polymer compound P-5 of Example 5 was used instead of polymer compound P-1.

[0253] Example 12 A quantum dot electroluminescence device 6 was produced in the same manner as in Example 7, except that the polymer compound P-6 of Example 2 was used instead of the polymer compound P-1.

[0254] Comparative Example 2 Comparative quantum dot electrodes were prepared in the same manner as in Example 7, except that the polymer compound P-1 in Example 7 was replaced with poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine)] (TFB) (manufactured by Luminescence Technology Corp.) having the following structural unit. Luminescence device 1 was fabricated. The weight-average molecular weight (Mw) and dispersity (Mw / Mn) of TFB were measured by SEC. The weight-average molecular weight and Mw / Mn of TFB were found to be 359,000 and 3.4, respectively.

[0255] [ka]

[0256] Comparative Example 3 Comparative quantum dot electroluminescence device 2 was produced in the same manner as in Example 7, except that polymer compound P-7 of Comparative Example 1 was used instead of polymer compound P-1.

[0257] [Evaluation of quantum dot electroluminescence devices 1] The quantum dot electroluminescent devices 1 to 6 prepared in Examples 7 to 12 and the comparative quantum dot electroluminescent devices 1 and 2 prepared in Comparative Examples 2 and 3 were evaluated for luminescence characteristics (V@5mA (V), ΔV (V)) and luminescence lifetime by the following method. The results are shown in Table 1 below.

[0258] (V@5mA(V)) When a voltage is applied to each quantum dot electroluminescence element using a DC constant voltage power supply (Keyence, source meter), a current begins to flow at a certain voltage, and the quantum dot electroluminescence element emits light. 2 The voltage (V) at this point was defined as the driving voltage "V@5mA (V)".

[0259] (ΔV(V) and luminescence lifetime) A predetermined voltage was applied to each quantum dot electroluminescent element using a DC constant voltage power supply (Keyence Corporation, source meter), causing each quantum dot electroluminescent element to emit light. While measuring the light emission of the quantum dot electroluminescent element with a brightness measuring device (Topcon Corporation, SR-3), the current was gradually increased until the brightness reached 650 nit (cd / m 2 ), the current is made constant and left as is. The brightness measured by the brightness measuring device gradually decreases, and the time it takes for the brightness to reach 90% of the initial brightness is called "LT90 (hr)." Also, when the brightness reaches 650 nit (cd / m 2 The difference between the initial voltage (V) at which the luminance reached 50% of the initial value and the voltage (V) at which the luminance reached 50% of the initial value is defined as ΔV (V). In Table 1 below, the LT90 (hr) of each element is calculated as a relative value when the LT90 (hr) of comparative quantum dot electroluminescent element 2 in Comparative Example 2 is set to 1.0, and is shown in the column "LT90 TFB=1."

[0260] [Table 1]

[0261] The results in Table 1 above show that the quantum dot electroluminescent devices 1 to 6 of the examples can exhibit significantly higher durability (significantly longer luminescence life) than the comparative quantum dot electroluminescent devices 1 and 2.

[0262] [Evaluation of the properties of each polymer compound] The HOMO levels (eV) and glass transition temperatures (Tg) (°C) of the polymer compounds P-1 to P-6 and TFB of Examples 1 to 6 and the polymer compound P-7 of Comparative Example 1 were measured by the following method. The results are shown in Table 2 below.

[0263] Furthermore, the characteristics of model devices were evaluated by the following method for the polymer compounds P-1 to P-6 and TFB of Examples 1 to 6 and the polymer compound P-7 of Comparative Example 1. The results are shown in Table 2 below.

[0264] (HOMO level measurement) Each polymer compound is dissolved in xylene to a concentration of 1% by mass to prepare a coating solution. The coating solution prepared above is used to form a film on a UV-cleaned ITO-coated glass substrate by spin coating at a rotation speed of 2000 rpm, and then dried on a hot plate at 150°C for 30 minutes to prepare a sample for measurement. The HOMO level of the sample is measured using an atmospheric photoelectron spectrometer (AC-3, manufactured by Riken Keiki Co., Ltd.). From the measurement results, the tangent intersection point of the rising edge is calculated and taken as the HOMO level (eV). Note that the HOMO level is usually a negative value.

[0265] (glass transition temperature (Tg)) Each polymer compound is measured using a differential scanning calorimeter (DSC) (Seiko Instruments Inc., trade name: DSC6000) by heating the sample to 300°C at a heating rate of 10°C / min and holding for 10 minutes, then cooling to 25°C at a cooling rate of 10°C / min and holding for 10 minutes, and then heating to 300°C at a heating rate of 10°C / min. After measurement, the sample is cooled to room temperature (25°C) at a rate of 10°C / min.

[0266] (Reference experiment: Evaluation of the characteristics of a model element) (Reference example 1) A glass substrate with a 150 nm thick stripe of indium tin oxide (ITO) was prepared as the first electrode (anode). PEDOT-PSS (Sigma-Aldrich) was spin-coated onto the glass substrate to a dry thickness of 30 nm, and then dried to form a hole injection layer with a dry thickness of 30 nm.

[0267] Next, the polymer compound P-1 (hole transport material) of Example 1 was dissolved in a xylene solvent at a concentration of 1% by mass to prepare a polymer coating solution. The polymer coating solution prepared above was applied to the hole injection layer formed above by spin coating so that the dry film thickness would be 30 nm, and then heated and dried at 150°C for 30 minutes. This formed a hole transport layer with a dry film thickness of 30 nm.

[0268] Separately, a quantum dot dispersion was prepared in the same manner as in Example 7. This quantum dot dispersion was applied by spin coating onto the hole transport layer formed above so that the dry film thickness would be 20 nm, and then heated and dried at 80° C. for 30 minutes. This formed a quantum dot emitting layer with a dry film thickness of 20 nm.

[0269] Next, ZnCl was dissolved in ethanol as a solvent at a concentration of 0.7 mol / L to prepare a ZnCl coating solution. The ZnCl coating solution prepared above was slowly dripped onto the quantum dot light-emitting layer formed above, left for 60 seconds, then spin-coated at 1000 rpm for 40 seconds, and dried by heating at 80°C for 20 minutes. Next, ethanol was slowly dripped onto the light-emitting layer formed above, and this spin-coating at 1000 rpm operation was repeated twice, followed by drying by heating at 80°C for 20 minutes.

[0270] α-NPD (N,N'-di-1-naphthyl-N,N'-diphenylbenzidine) and HAT-CN (dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile) were successively deposited by vacuum deposition onto the hole transport layer formed above to form electron blocking layers with thicknesses of 36 nm and 10 nm, respectively, to fabricate hole-only device 1.

[0271] (Reference example 2) A hole-only device 2 was prepared in the same manner as in Reference Example 1, except that the polymer compound P-2 of Example 2 was used instead of the polymer compound P-1.

[0272] (Reference example 3) A hole-only device 3 was prepared in the same manner as in Reference Example 1, except that the polymer compound P-3 of Example 3 was used instead of the polymer compound P-1.

[0273] (Reference example 4) A hole-only device 4 was prepared in the same manner as in Reference Example 1, except that the polymer compound P-4 of Example 4 was used instead of the polymer compound P-1.

[0274] (Reference example 5) A hole-only device 5 was prepared in the same manner as in Reference Example 1, except that the polymer compound P-5 of Example 5 was used instead of the polymer compound P-1.

[0275] (Reference example 6) A hole-only device 6 was prepared in the same manner as in Reference Example 1, except that the polymer compound P-6 of Example 6 was used instead of the polymer compound P-1.

[0276] (Comparative Reference Example 1) A comparative hole-only device 1 was prepared in the same manner as in Reference Example 1, except that TFB of Comparative Example 2 was used instead of polymer compound P-1.

[0277] (Comparative Reference Example 2) A comparative hole-only device 2 was prepared in the same manner as in Reference Example 1, except that polymer compound P-7 of Comparative Example 1 was used instead of polymer compound P-1.

[0278] The hole current density @ 8 V of the hole-only devices 1 to 6 and comparative hole-only devices 1 and 2 obtained above was evaluated by the following method.

[0279] (Hole Current Density @ 8V) Each hole-only device was subjected to a DC constant voltage power supply (Keyence Corporation, source meter) while gradually increasing the voltage. The current value at 8 V was measured, and the current value per unit area (current density (A / m)) was calculated from the area of ​​each device. 2 ) was calculated and this was designated as "Hole Current Density @ 8V." The results are shown in Table 2 below. In Table 2 below, the current density of each hole-only device is expressed as a relative value when the current density of Comparative Hole-Only Device 1 of Reference Comparative Example 1 is set to 1.00, and is shown in Table 2 below as "HOD@8V TFB=1."

[0280] [Table 2]

[0281] As is clear from Table 2 above, the elements of Reference Examples 1 to 6 are superior in hole injection and transport properties compared to the elements of Comparative Reference Examples 1 and 2. From this, it is considered that the elements according to the present invention have a long life effect. [Explanation of symbols]

[0282] 100...Electroluminescence element (EL element), 110...substrate, 120...first electrode, 130...hole injection layer, 140...hole transport layer, 150...light-emitting layer, 160...electron transport layer, 170...electron injection layer, 180...Second electrode.

Claims

1. A polymer compound containing a constitutional unit represented by the following formula (1), or a constitutional unit represented by the following formula (1) and a constitutional unit represented by the following formula (2): 【Chemical 1】 In the above formula (1), R １１ R14 to R14 each independently represent a hydrocarbon group having 6 to 12 carbon atoms; R 21 , R 22 , R 31 and R 32 each represent a hydrogen atom; L １ represents an unsubstituted divalent aromatic hydrocarbon group having 6 ring atoms, x is 1, L ２ represents an unsubstituted aromatic hydrocarbon group having 6 ring atoms, ２ is Ar １ and form a ring, Ar １ represents an unsubstituted divalent aromatic hydrocarbon group having 6 ring atoms, and L ２ and form a ring, Ar ２ represents an aromatic hydrocarbon group having 6 ring atoms which may be substituted with a linear hydrocarbon group having 1 to 6 carbon atoms, in which case Ar ２ is Ar １ does not form a ring with 【Chemistry 2】 In the above formula (2), R ４１ R to R44 each independently represent a hydrocarbon group having 6 to 12 carbon atoms, ４１ ~R ４４ is R in the above formula (1). １１ ~R １４ and differ from each other, R 23 , R 24 , R 33 and R 34 each represent a hydrogen atom; L ３ represents an unsubstituted divalent aromatic hydrocarbon group having 6 ring atoms, y is 1, L ４ represents an unsubstituted aromatic hydrocarbon group having 6 ring atoms, ４ is Ar ３ and form a ring, Ar ３ represents an unsubstituted divalent aromatic hydrocarbon group having 6 ring atoms, and L ４ and form a ring, Ar ４ represents an aromatic hydrocarbon group having 6 ring atoms which may be substituted with a linear hydrocarbon group having 1 to 12 carbon atoms, in which case Ar ４ is Ar ３ does not form a ring.

2. The structural unit represented by the formula (1) and the structural unit represented by the formula (2) are contained, and in this case, R １１ ~R １４ each independently represents a hydrocarbon group having 6 to 9 carbon atoms, and R ４１ ~R ４４ and each independently represent a hydrocarbon group having 10 to 12 carbon atoms.

3. The structural unit represented by the formula (1) and the structural unit represented by the formula (2) are contained, and in this case, R ２１ , R ２２ , R ３１ , R ３２ , L １ , x, L ２ , Ar １ and Ar ２ are R in the formula (2), respectively. ２３ , R ２４ , R ３３ , R ３４ , L ３ , y, L ４ , Ar ３ and Ar ４ The polymer compound according to claim 1 or 2, wherein

4. The polymer compound according to claim 2 or 3, wherein the constitutional unit represented by formula (2) is present in a ratio of 1 mole to 20 moles per mole of the constitutional unit represented by formula (1).

5. The following structure in the formula (1): 【Chemistry 3】 Or the following structure in the formula (2): 【Chemistry 4】 The polymer compound according to any one of claims 1 to 4, wherein each of the groups independently has a structure selected from the following group: 【Chemistry 5】 Ar 412 , Ar 413 , Ar 416 , and Ar ４１７ each independently represents a group selected from the following group: 【Chemistry 6】 At this time, R 55 to R 57 in the formula (1) each independently represent a hydrogen atom or a linear alkyl group having 1 to 6 carbon atoms; R in the formula (2) ５５ ~R ５７ each independently represents a hydrogen atom or a linear alkyl group having 1 to 12 carbon atoms.

6. The following structure in the formula (1): 【Chemistry 7】 Or the following structure in the formula (2): 【Chemistry 8】 each independently have a structure selected from the following group: 【Chemistry 9】 In the above structure, Ar ４１２ , Ar 413 , and Ar ４１６ each independently represents a group selected from the following group: 【Chemistry 10】 In the above structure, R 55 to R 57 in the formula (1) each independently represent a linear alkyl group having 4 to 6 carbon atoms; R in the formula (2) ５５ ~R ５７ each independently represents a linear alkyl group having 4 to 10 carbon atoms.

7. A polymeric compound comprising at least one structural unit selected from the group consisting of a structural unit represented by the following formula (i), a structural unit represented by the following formula (ii), and a structural unit represented by the following formula (iii): 【Chemistry 11】 8. The polymer compound according to claim 7, comprising a structural unit represented by formula (i) and a structural unit represented by formula (iii).

9. The polymer compound described in claim 8, wherein the constitutional unit represented by formula (iii) is present in a ratio of 1 mole to 20 moles per mole of the constitutional unit represented by formula (i).

10. An electroluminescence device material comprising the polymer compound according to any one of claims 1 to 9.

11. An electroluminescent element comprising a first electrode, a second electrode, and one or more organic films disposed between the first electrode and the second electrode, 10. An electroluminescence device, wherein at least one layer of the organic film comprises the polymer compound according to claim 1.

12. 12. The electroluminescence device according to claim 11, wherein the organic film containing the polymer compound is a hole transport layer or a hole injection layer.

13. 13. The electroluminescence device according to claim 11, wherein the organic film has a light-emitting layer containing semiconductor nanoparticles or an organometallic complex.

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