Polymers having overlap indices within a specific range, polymers with a specific structure, compositions, and electroluminescent elements.

Abstract

To provide means for providing an electroluminescent device capable of achieving high luminance, high efficiency, and a long device life.SOLUTION: The present invention relates to a polymer having an overlap index of 0.00001 or more and 1.8 or less. The present invention also relates to a polymer including a structural unit represented by the formula (1).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to polymers having a specific overlap index, polymers with a specific structure, compositions, and electroluminescent elements. [Background technology]

[0002] Electroluminescent devices (EL devices) are undergoing active research and development. In particular, EL devices are considered promising for use as inexpensive, large-area full-color display elements and writing light source arrays of the solid-state type. An EL device is a light-emitting element that has a thin film of several nanometers to several hundred nanometers between the anode and cathode. In addition, EL devices typically have a hole transport layer, an emissive layer, an electron transport layer, etc.

[0003] From the perspective of realizing EL elements with long lifespan and excellent color purity, light-emitting devices using "quantum dots," which are inorganic light-emitting materials, are being considered (Patent Document 1). Quantum dots (QDs) are semiconductor materials with a crystalline structure of several nanometers in size, and are composed of several hundred to several thousand atoms. Because the size of a quantum dot corresponds to the de Broglie wavelength of an atom, quantum dots exhibit quantum confinement effects. Due to this quantum confinement effect, the emission wavelength of quantum dots can be adjusted simply by adjusting their size, and they have characteristics such as excellent color purity and high PL (photoluminescence) luminescence efficiency, attracting much attention. Quantum dot electroluminescence devices (QD LEDs, QLEDs) are known to have a basic three-layer structure with a quantum dot light-emitting layer in between, and hole transport layers and electron transport layers at both ends.

[0004] Furthermore, as an example of charge transport materials, polymers containing nitrogen atoms that form a triarylamine structure in the main chain, such as poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine)](TFB), are known (Patent Documents 2-7). It is known that in organic electroluminescent devices (organic EL devices), using polymers with specific structures as hole transport materials in the hole transport layer can yield excellent device characteristics (Patent Documents 3, 4, 6, and 7). [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] Japanese Patent Publication No. 2010-199067 [Patent Document 2] Chinese Patent Application Publication No. 108559066 Specification [Patent Document 3] International Publication No. 2020 / 009069 [Patent Document 4] Japanese Patent Publication No. 2009-263665 [Patent Document 5] Japanese Patent Publication No. 2005-306998 [Patent Document 6] International Publication No. 2009 / 110360 [Patent Document 7] International Publication No. 2019 / 177175 [Overview of the project] [Problems that the invention aims to solve]

[0006] However, the electroluminescent device using the hole transport material described in Patent Document 1 could not achieve a sufficient device lifetime.

[0007] Furthermore, the present inventors have found that even with electroluminescent elements using TFB or polymer compounds described in Patent Documents 2 to 7 as hole transport materials, it may not be possible to achieve a sufficient element lifetime.

[0008] Therefore, the present invention aims to provide a means for achieving high brightness, high efficiency, and excellent device life in an electroluminescent element. [Means for solving the problem]

[0009] The inventors diligently conducted research to solve the above problems. As a result, the inventors discovered that the above problems can be solved by using a polymer having an overlap index within a specific range, and thus completed the present invention.

[0010] In other words, the above problem can be solved by the following means.

[0011] Polymers whose overlap index, expressed by the following formula, is between 0.00001 and 1.8:

[0012]

number

[0013] In the above formula, k is the sequential number assigned to the atom in the chemical formula of the constituent unit of the polymer, and d k HOMO This shows the distribution density of the HOMO in the atom with serial number k, and d k LUMO This shows the distribution density of LUMOs in the atom with serial number k.

[0014] d k HOMO and d k LUMOThese are values calculated using density functional theory (DFT) with quantum chemistry software, using the B3LYP functional and the 6-31G(d,p) basis function. As the quantum chemistry software, Gaussian 16 (Gaussian Inc.) can be used.

[0015] The inventors of the present invention conducted intensive studies to solve the above problems. As a result, the inventors of the present invention found that the above problems can be solved by using a polymer having a specific structure, and completed the present invention.

[0016] That is, the above problems can be achieved by the following means.

[0017] A polymer comprising a structural unit represented by the following formula (1):

[0018] [[ID===15]]

Chemical formula

[0019] In the above formula (1), Ar 1 and Ar 2 each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 carbon atoms, Ar 3 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 120 carbon atoms, Ar 4 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 carbon atoms, or a substituted or unsubstituted divalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, Ar 5 represents a single bond, or a substituted or unsubstituted divalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, Each R 1Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), and a cyano group (-CN). Each R 2 Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), and a cyano group (-CN). A is a structure represented by the following formula (2) or formula (3):

[0020] [ka]

[0021] In the above equation (2), Each Ar 6 Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. Each Ar 7Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. 2 or more Ar 7 The two or more Ar 7 A fused ring may be formed between the bonded benzene ring and the bonded ring. * indicates the bond position with an adjacent atom; In the above equation (3), Each Ar 8 Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. Each Ar 9Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. X represents S, O, or C substituted with two linear or branched hydrocarbon groups having 1 to 16 carbon atoms, either substituted or unsubstituted. 2 or more Ar 9 The two or more Ar 9 A fused ring may be formed between the bonded benzene ring and the bonded ring. * indicates the bond position with an adjacent atom. [Effects of the Invention]

[0022] According to the present invention, it is possible to provide a means for achieving high brightness, high efficiency, and excellent device life in an electroluminescent element. [Brief explanation of the drawing]

[0023] [Figure 1] This is a schematic diagram showing an electroluminescent element according to one embodiment of the present invention. [Figure 2] This diagram illustrates the method for calculating the overlap index of TFB, a comparative compound, as well as the overlap in the distribution densities of the HOMO and LUMO. [Figure 3] This diagram illustrates the method for calculating the overlap index of TFB, a comparative compound, as well as the overlap in the distribution densities of the HOMO and LUMO. [Figure 4]This is an explanatory diagram illustrating a method for calculating the overlap index of polymer A-7 according to one embodiment of the present invention, as well as the overlap of the distribution densities of HOMO and LUMO. [Figure 5] This is an explanatory diagram illustrating a method for calculating the overlap index of polymer A-7 according to one embodiment of the present invention, as well as the overlap of the distribution densities of HOMO and LUMO. [Figure 6] This is an explanatory diagram illustrating a method for calculating the overlap index of polymer A-1 according to one embodiment of the present invention, as well as the overlap of the distribution densities of HOMO and LUMO. [Figure 7] This is an explanatory diagram illustrating a method for calculating the overlap index of polymer A-1 according to one embodiment of the present invention, as well as the overlap of the distribution densities of HOMO and LUMO. [Figure 8] This is an explanatory diagram illustrating a method for calculating the overlap index of polymer A-2 according to one embodiment of the present invention, as well as the overlap of the distribution densities of HOMO and LUMO. [Figure 9] This is an explanatory diagram illustrating a method for calculating the overlap index of polymer A-2 according to one embodiment of the present invention, as well as the overlap of the distribution densities of HOMO and LUMO. [Figure 10] This is an explanatory diagram illustrating a method for calculating the overlap index of polymer A-3 according to one embodiment of the present invention, as well as the overlap of the distribution densities of HOMO and LUMO. [Figure 11] This is an explanatory diagram illustrating a method for calculating the overlap index of polymer A-3 according to one embodiment of the present invention, as well as the overlap of the distribution densities of HOMO and LUMO. [Modes for carrying out the invention]

[0024] Embodiments of the present invention will be described below. However, the present invention is not limited to the embodiments described below. Unless otherwise specified, operations and measurements of physical properties, etc., will be performed under conditions of room temperature (20°C to 25°C) and relative humidity of 40%RH to 50%RH.

[0025] In this specification, "X and Y are independent of each other" means that X and Y may be the same or different.

[0026] In this specification, "ring-derived group" refers to a group obtained by removing hydrogen atoms directly bonded to the ring constituent elements from a ring structure, in proportion to their valence.

[0027] In this specification, "ring assembly" refers to two or more rings linked by single bonds. Furthermore, "ring assembly group" and "group derived from a ring assembly" refer to a group obtained by removing hydrogen atoms directly bonded to the ring constituent elements by the amount of their valence from a ring assembly structure.

[0028] <polymer> One aspect of the present invention relates to a polymer having an overlap index represented by the following formula of 0.00001 or more and 1.8 or less:

[0029]

number

[0030] In the above formula, k is the sequential number assigned to the atom in the chemical formula of the constituent unit of the polymer, and d k HOMO This shows the distribution density of the HOMO in the atom with serial number k, and d k LUMO This shows the distribution density of LUMOs in the atom with serial number k.

[0031] d k HOMO and d k LUMO These values ​​were calculated using density functional theory (DFT) with quantum chemistry calculation software, employing the functional B3LYP and basis set 6-31G(d,p). Gaussian 16 (Gaussian Inc.) can be used as the quantum chemistry calculation software.

[0032] The polymer may be a homopolymer or a copolymer.

[0033] The inventors hypothesize the following mechanism by which the above configuration solves the problem.

[0034] The overlap index, described in detail below, is a parameter that indicates the degree of overlap between the HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital) within a molecular structure of interest. A larger overlap index value indicates greater overlap between the HOMO and LUMO within the molecular structure of interest. Conversely, a smaller overlap index value (closer to 0) indicates less overlap between the HOMO and LUMO within the molecular structure of interest.

[0035] Within the molecules of charge-transporting materials, there is a region primarily responsible for charge transport. For example, within the molecules of hole-transporting materials, there is a region primarily responsible for hole transport. This region, primarily responsible for hole transport, corresponds to the HOMO within the molecule of the hole-transporting material. This region is vulnerable to electrons, and the injection of electrons into this region causes irreversible changes, leading to the degradation of the compound. Furthermore, when electrons are injected into a hole-transporting material, the region to which these electrons are injected corresponds to the LUMO within the molecule of the hole-transporting material. Now, consider the case where the region primarily responsible for hole transport and the region to which electrons are injected overlap in the hole-transporting material, that is, the region corresponding to the HOMO and the region corresponding to the LUMO overlap. In this case, the greater the overlap between the HOMO and LUMO regions, the higher the probability that electrons will be injected into these overlapping regions. And the greater the overlap between the HOMO and LUMO regions, the higher the probability that irreversible changes will occur in the hole-transporting material due to electron injection originating from these overlapping regions. Therefore, the greater the overlap between the portion corresponding to the HOMO and the portion corresponding to the LUMO, the higher the likelihood of degradation of the hole transport material. Thus, the device lifetime of electroluminescent elements using charge transport materials is shortened by the degradation of the charge transport material.

[0036] However, in the polymer according to one aspect of the present invention, the overlap index is below a certain value, and the overlap between the HOMO and LUMO within the molecular structure of interest is extremely small. As a result, the smaller the overlap between the portion corresponding to the HOMO and the portion corresponding to the LUMO, the lower the possibility of irreversible changes occurring in the polymer due to electron injection in these overlapping portions. Therefore, the smaller the overlap between the portion corresponding to the HOMO and the portion corresponding to the LUMO, the lower the possibility of polymer degradation. Consequently, the device life of an electroluminescent device using the polymer according to one aspect of the present invention is significantly improved.

[0037] It should be noted that the above mechanism is based on speculation, and its accuracy does not affect the technical scope of the present invention. Similarly, the accuracy of other speculations in this specification does not affect the technical scope of the present invention.

[0038] From the viewpoint of improving the device lifetime of electroluminescent elements, a smaller overlap index is preferable. The overlap index is preferably 1.8 or less, more preferably 1.2 or less, even more preferably 1.0 or less, and even more preferably 0.6 or less. Furthermore, the overlap index is preferably 0.00001 or more, more preferably 0.00005 or more, and even more preferably 0.0001 or more. Within these ranges, the effect of improving the device lifetime, particularly in quantum dot electroluminescent elements, is significant. Examples of preferred overlap index ranges include 0.00001 to 1.8, 0.00001 to 1.2, 0.00005 to 1.0, and 0.0001 to 0.6, but the overlap index range is not limited to these.

[0039] The overlap index can be calculated as follows: First, for the constituent units (repeating units) of the polymer, the HOMO, LUMO, and their distribution densities are calculated using Density Functional Theory (DFT) with Gaussian 16 (Gaussian Inc.) as the calculation software, using the functional B3LYP and basis set 6-31G(d,p). Next, using the distribution densities of the HOMO and LUMO on each atom of the constituent units of the polymer calculated above, the overlap index is calculated as the overlap between the HOMO and LUMO according to the overlap index calculation formula described above.

[0040] The overlap index is calculated for the ground state of the polymer's constituent units, with the highest orbital where electrons are distributed being defined as the HOMO and the lowest orbital where electrons are not distributed being defined as the LUMO.

[0041] If a polymer has only one type of constituent unit (repeating unit), the overlap index is calculated based on that single constituent unit. If a polymer has two or more constituent units (repeating units), the overlap index for each constituent unit is calculated separately. The product of this overlap index and the content ratio of each constituent unit (the ratio of each constituent unit to the total number of constituent units in the polymer) is then calculated, and the sum of these values ​​is used as the polymer's overlap index. Further details are provided in the examples.

[0042] A polymer according to one embodiment of the present invention is preferably a polymer that includes a structural unit represented by the following formula (1):

[0043] [ka]

[0044] In the above formula (1), Ar 1 and Ar 2 Each of these independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 carbon atoms. Ar 3 This represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 120 carbon atoms. Ar 4 This represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 carbon atoms, or a substituted or unsubstituted divalent aromatic heterocyclic group having 3 to 60 ring-forming atoms. Ar 5 This represents a divalent aromatic heterocyclic group with a single bond, or a substituted or unsubstituted ring-forming group with 3 to 60 ring-forming atoms. Each R 1Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), and a cyano group (-CN). Each R 2 Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), and a cyano group (-CN). A is a structure represented by the following formula (2) or formula (3):

[0045] [ka]

[0046] In the above equation (2), Each Ar 6 Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. Each Ar 7Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. 2 or more Ar 7 The two or more Ar 7 A fused ring may be formed between the bonded benzene ring and the bonded ring. * indicates the bond position with an adjacent atom; In the above equation (3), Each Ar 8 Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. Each Ar 9Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. X represents S, O, or C substituted with two linear or branched hydrocarbon groups having 1 to 16 carbon atoms, either substituted or unsubstituted. 2 or more Ar 9 The two or more Ar 9 A fused ring may be formed between the bonded benzene ring and the bonded ring. * indicates the bond position with an adjacent atom.

[0047] The inventors hypothesize the following mechanism by which the problem is solved by a polymer containing the constituent unit represented by the above formula (1).

[0048] Within the molecules of charge-transporting materials, there is a region primarily responsible for charge transport. For example, within the molecules of hole-transporting materials, there is a region primarily responsible for hole transport. This region, primarily responsible for hole transport, corresponds to the HOMO within the molecule of the hole-transporting material. This region is vulnerable to electrons, and the injection of electrons into this region causes irreversible changes, leading to the degradation of the compound. Furthermore, when electrons are injected into a hole-transporting material, the region to which these electrons are injected corresponds to the LUMO within the molecule of the hole-transporting material. Now, consider the case where the region primarily responsible for hole transport and the region to which electrons are injected overlap in the hole-transporting material, that is, the region corresponding to the HOMO and the region corresponding to the LUMO overlap. In this case, the greater the overlap between the HOMO and LUMO regions, the higher the probability that electrons will be injected into these overlapping regions. And the greater the overlap between the HOMO and LUMO regions, the higher the probability that irreversible changes will occur in the hole-transporting material due to electron injection originating from these overlapping regions. Therefore, the greater the overlap between the portion corresponding to the HOMO and the portion corresponding to the LUMO, the higher the likelihood of degradation of the hole transport material. Thus, the device lifetime of electroluminescent elements using charge transport materials is shortened by the degradation of the charge transport material.

[0049] However, in polymers containing the structural units represented by formula (1) above, the portion corresponding to the HOMO in these structural units is located around the triarylamine structure containing the nitrogen atom that constitutes the main chain. The portion corresponding to the LUMO is located around an aromatic hydrocarbon group bonded to the nitrogen atom of the carbazole ring in the side chain, an aromatic heterocyclic group, or a ring aggregate group having a structure in which one or more aromatic hydrocarbon rings and one or more aromatic heterocyclic rings are bonded via single bonds. Therefore, the overlap between the HOMO and LUMO within these structural units is extremely small. As a result, the smaller the overlap between the portion corresponding to the HOMO and the portion corresponding to the LUMO, the lower the possibility of irreversible changes occurring in these overlapping portions due to electron injection. Therefore, the smaller the overlap between the portion corresponding to the HOMO and the portion corresponding to the LUMO, the lower the possibility of compound degradation. Consequently, the device lifetime of electroluminescent devices using polymers containing these structural units is significantly improved.

[0050] It should be noted that the above mechanism is based on speculation, and its accuracy does not affect the technical scope of the present invention. Similarly, the accuracy of other speculations in this specification does not affect the technical scope of the present invention.

[0051] Therefore, another embodiment of the present invention can be said to be a polymer containing the constituent unit represented by formula (1) above.

[0052] In the above equation (1), Ar 1 and Ar 2 Each of these independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 carbon atoms. In formula (1) above, Ar 3 represents a substituted or unsubstituted divalent aromatic hydrocarbon group with 6 to 120 carbon atoms. 1 ~Ar 3 They may be the same or different. From the viewpoint of improving the lifespan of the element, Ar 1 ~Ar 3 It is preferable that they are the same. In the above formula (1), Ar 4represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 carbon atoms, or a substituted or unsubstituted divalent aromatic heterocyclic group having 3 to 60 ring-forming atoms. In formula (1) above, Ar 5 This represents a divalent aromatic heterocyclic group with a single bond, or substituted or unsubstituted ring-forming atoms numbering between 3 and 60.

[0053] Ar 1 Ar 2 and Ar 4 There are no particular limitations on the divalent aromatic hydrocarbon groups having 6 to 60 carbon atoms that can constitute each of these. 3 The divalent aromatic hydrocarbon group having 6 to 120 carbon atoms (preferably a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms) that can constitute the Ar is not particularly limited. 1 ~Ar 4 Examples of aromatic hydrocarbon groups that can constitute each of these include divalent groups derived from aromatic hydrocarbon rings such as benzene (phenylene group), indene, naphthalene, anthracene, azulene, heptalene, acenaphthene, phenalene, fluorene, phenanthrine, and pyrene, and divalent groups derived from ring aggregates of two or more aromatic hydrocarbon rings linked by single bonds, such as biphenyl (biphenylene group), terphenyl (terphenylene group), quaterphenyl (quaterphenylene group), quinquiphenyl (quinquiphenylene group), and sexiphenyl (sexiphenylene group). In this specification, hydrocarbon rings containing an aromatic hydrocarbon ring portion, such as fluorene, are also treated as aromatic heterocycles.

[0054] Ar 4 and Ar 5 There are no particular restrictions on the divalent aromatic heterocyclic groups with 3 to 60 ring-forming atoms that can constitute each of these groups. 4 and Ar 5Examples of aromatic heterocyclic groups that can constitute each of these include, for example, divalent groups derived from aromatic heterocyclic rings such as acridine, phenazine, benzoquinoline, benzoisoquinoline, phenanthridine, phenanthroline, anthraquinone, fluorenone, dibenzofuran, dibenzothiophene, carbazole, imidazophenantholidine, benzimidazophenantholidine, azadibenzofuran, azacarbazole, azadibenzothiophene, diazadibenzofuran, diazacarbazole, diazadibenzothiophene, xanthone, thioxanthone, pyridine, quinoline, and anthraquinoline, as well as divalent groups derived from ring assemblies of two or more aromatic heterocyclic rings linked by single bonds, such as bipyridine, bipyrimidine, and bipyrazine. In this specification, heterocyclic rings containing aromatic ring portions, such as dibenzofuran, dibenzothiophene, and carbazole, are also treated as aromatic heterocyclic rings. In this specification, aromatic heterocycles also include rings having a structure in which a heteroatom is bonded via a double bond to an atom that directly forms a cyclic portion.

[0055] Ar 1 ~Ar 5 If the group is substituted with substituents, the number of substituents introduced is not particularly limited. 1 ~Ar 5 The number of substituents introduced in each is preferably 1 to 3, more preferably 1 to 2, and even more preferably 1. 1 ~Ar 5 If the group is substituted with a substituent, the type of substituent is not particularly limited. 1 ~Ar 5 When the group is substituted with a substituent, examples of the substituents include alkyl groups, hydroxyalkyl groups, alkoxy groups, alkoxyalkyl groups, alkenyl groups, alkynyl groups, alkylthio groups, alkoxycarbonyl groups, hydroxyl groups (-OH), carboxyl groups (-COOH), thiol groups (-SH), cyano groups (-CN), halogen groups, etc. 1 ~Ar 5 If is a group substituted with substituents, the substituents may be the same or different.1 ~Ar 5 If each of these is a group substituted with a substituent, and each has two or more such substituents, then Ar 1 ~Ar 5 In each of these, the two or more substituents may be the same or different.

[0056] The alkyl group is not particularly limited. The number of carbon atoms in the alkyl group is not particularly limited, but it is preferably between 1 and 20.

[0057] The alkyl group is not particularly limited and may be linear, branched, or cyclic. Specifically, it may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, neopentyl, 1,2-dimethylpropyl, n-hexyl, isohexyl, 1,3-dimethylbutyl, 1-isopropylpropyl, 1,2-dimethylbutyl, n-heptyl, 1,4-dimethylpentyl, 3-ethylpentyl, 2-methyl-1-isopropylpropyl, 1-ethyl-3-methylbutyl, n Examples include 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, n-octadecyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group.

[0058] The hydroxyalkyl group is not particularly limited, but examples include those in which the alkyl group is substituted with 1 to 3 (preferably 1 to 2, particularly preferably 1) hydroxyl groups (e.g., hydroxymethyl group, hydroxyethyl group).

[0059] The alkoxy group is not particularly limited, but examples include methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, 2-ethylhexyloxy, 3-ethylpentyloxy, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups.

[0060] The alkoxyalkyl group is not particularly limited, but examples include those in which the alkyl group is substituted with 1 to 3 (preferably 1 to 2, particularly preferably 1) of the above alkoxy groups.

[0061] The alkenyl group is not particularly limited, but examples include vinyl group, allyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 1-heptenyl group, 2-heptenyl group, 5-heptenyl group, 1-octenyl group, 3-octenyl group, 5-octenyl group, and 1,3-butadienyl group.

[0062] The alkynyl group is not particularly limited, but examples include acetylenyl group (ethynyl group), 1-propynyl group, 2-propynyl group (propargyl group), 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentetyl group, 2-pentetyl group, 3-pentetyl group, 1-hexynyl group, 2-hexynyl group, 3-hexynyl group, 1-heptynyl group, 2-heptynyl group, 5-heptynyl group, 1-octinyl group, 3-octinyl group, and 5-octinyl group.

[0063] The alkylthio group is not particularly limited, but examples include methylthio group, ethylthio group, propylthio group, pentylthio group, hexylthio group, octylthio group, dodecylthio group, cyclopentylthio group, and cyclohexylthio group.

[0064] The alkoxycarbonyl group is not particularly limited, but examples include methyloxycarbonyl group, ethyloxycarbonyl group, butyloxycarbonyl group, octyloxycarbonyl group, and dodecyloxycarbonyl group.

[0065] The halogen group is not particularly limited, but examples include fluoro groups, chloro groups, bromo groups, and iodo groups.

[0066] Ar 1 ~Ar 5 If the group is substituted with a substituent, the substituent is preferably an alkyl group, more preferably a linear or branched alkyl group having 1 to 18 carbon atoms. A linear alkyl group having 1 to 8 carbon atoms is even more preferred, and an n-octyl group is particularly preferred.

[0067] Ar 1 ~Ar 3 The groups that can constitute each of these are preferably substituted or unsubstituted phenylene groups, substituted or unsubstituted naphthylene groups, substituted or unsubstituted divalent groups derived from anthracene (divalent groups derived from substituted or unsubstituted anthracene rings), substituted or unsubstituted divalent groups derived from fluorene (divalent groups derived from substituted or unsubstituted fluorene rings), or substituted or unsubstituted biphenylene groups. 1 ~Ar 3 The groups that can constitute each of these are more preferably substituted or unsubstituted phenylene groups, even more preferably phenylene groups, and particularly preferably p-phenylene groups.

[0068] Ar 4The group that can form it is preferably a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a divalent group derived from a substituted or unsubstituted anthracene (a divalent group derived from a substituted or unsubstituted anthracene ring), a divalent group derived from a substituted or unsubstituted fluorene (a divalent group derived from a substituted or unsubstituted fluorene ring), or a substituted or unsubstituted biphenylene group. Ar 4 The group that can form it is more preferably a divalent group derived from a substituted or unsubstituted fluorene, and even more preferably a divalent group derived from a fluorene substituted with two alkyl groups, and particularly preferably a divalent group derived from a fluorene substituted with two n-hexyl groups, n-octyl groups, n-decyl groups, or n-dodecyl groups.

[0069] Ar 5 is preferably a single bond.

[0070] In the polymer according to one embodiment of the present invention, in the above formula (1), Ar 3 is preferably a group selected from the following group (I) In the above formula (1), Ar 3 is a group selected from the following group (I ), and it is more preferable that Ar 5 is a single bond. In the above formula (1), Ar 3 is the following I-1 or the following I-4, and it is even more preferable that Ar 5 is a single bond. In the above formula (1), Ar 3 is a phenylene group, and it is even more preferable that Ar 5 is a single bond. In the above formula (1), Ar 3 is a p-phenylene group, and it is particularly preferable that Ar 5 is a single bond. According to these structures, the effect of improving the device lifetime in an electroluminescence device using the polymer, particularly in a quantum dot electroluminescence device, becomes large.

[0071]

Chemical formula

[0072] Here, R 111 ~R 123 Each of these independently represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 16 carbon atoms. * indicates the bond position with an adjacent atom.

[0073] In other words, in group (I) below, * represents the adjacent nitrogen atom and the adjacent Ar 5 This is the bonding position with the atom. 5 If it is a single bond, * represents the bond position with the adjacent nitrogen atom and the adjacent carbon atom of the benzene ring in the carbazole ring of formula (1) above.

[0074] A polymer according to one embodiment of the present invention is, in formula (1) above, Ar 1 Ar 2 and Ar 4 Preferably, at least one selected from the group consisting of is independently selected from the group (II) below. In formula (1) above, Ar 1 Ar 2 and Ar 4 It is more preferable that each of these groups is independently selected from group (II) above. In formula (1) above, Ar 1 and Ar 2 These are, independently, II-1 or II-4 below, and Ar 4 It is even more preferable that the following II-5 applies. In the above formula (1), Ar 1 and Ar 2 It is a phenylene group, and Ar 4 In section II-5 below, R 216 and R 217 Each of these is independently an alkyl group having 1 to 20 carbon atoms (preferably an n-hexyl group, an n-octyl group, an n-decyl group, or an n-dodecyl group), and R 218 and R 219 It is even more preferable that is a hydrogen atom. In formula (1) above, Ar 1 and Ar2 This is a p-phenylene group, and Ar 4 In section II-5 below, R 216 and R 217 Each of these is independently an alkyl group having 1 to 20 carbon atoms (preferably an n-hexyl group, an n-octyl group, an n-decyl group, or an n-dodecyl group), and R 218 and R 219 It is particularly preferable that the atom is a hydrogen atom. These structures greatly improve the device lifetime of electroluminescent devices using polymers, especially quantum dot electroluminescent devices.

[0075] Alternatively, the polymer according to one embodiment of the present invention is, in formula (1) above, Ar 1 and Ar 2 These are, independently, II-6 or II-7 below, and Ar 4 It is even more preferable that the following II-5 applies. In the above formula (1), Ar 1 and Ar 2 It is a biphenylene group, and Ar 4 In section II-5 below, R 216 and R 217 Each of these is independently an alkyl group having 1 to 20 carbon atoms (preferably an n-hexyl group, an n-octyl group, an n-decyl group, or an n-dodecyl group), and R 218 and R 219 It is even more preferable that is a hydrogen atom. In formula (1) above, Ar 1 and Ar 2 This is a p-biphenylene group, and Ar 4 In section II-5 below, R 216 and R 217 Each of these is independently an alkyl group having 1 to 20 carbon atoms (preferably an n-hexyl group, an n-octyl group, an n-decyl group, or an n-dodecyl group), and R 218 and R 219 It is particularly preferable that the atom is a hydrogen atom. These structures greatly improve the device lifetime of electroluminescent devices using polymers, especially quantum dot electroluminescent devices.

[0076] Alternatively, the polymer according to one embodiment of the present invention is, in formula (1) above, Ar 1 and Ar 2 These are, independently, II-6 or II-7 below, and Ar 4 It is even more preferable that the following II-4 applies. In formula (1) above, Ar 1 and Ar 2 It is a pyrenylene group, and Ar 4 In section II-4 below, R 214 and R 215 It is even more particularly preferred that each of them independently is an alkyl group having 1 to 20 carbon atoms (preferably an n-hexyl group, an n-octyl group, an n-decyl group, or an n-dodecyl group). In the above formula (1), Ar 1 and Ar 2 This is a p-pyrenylene group, and Ar 4 In section II-4 below, R 214 and R 215 It is even more particularly preferable that each of these groups is an alkyl group having 1 to 20 carbon atoms (preferably an n-hexyl group, an n-octyl group, an n-decyl group, or an n-dodecyl group). These structures greatly improve the device lifetime of electroluminescent devices using polymers, especially quantum dot electroluminescent devices.

[0077] [ka]

[0078] Here, R 211 ~R 225 Each of these independently represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 16 carbon atoms. * indicates the bond position with an adjacent atom.

[0079] In the above equation (1), "(R 1 )3" indicates that there are 3 R1s. 1Each R independently represents a hydrogen atom, alkyl group, hydroxyalkyl group, alkoxy group, alkoxyalkyl group, alkenyl group, alkynyl group, alkylthio group, alkoxycarbonyl group, hydroxyl group (-OH), carboxyl group (-COOH), thiol group (-SH), and cyano group (-CN). 1 They may be the same or different. In the above equation (1), "(R 2 )4" indicates that there are 4 R2s. 2 Each R independently represents a hydrogen atom, alkyl group, hydroxyalkyl group, alkoxy group, alkoxyalkyl group, alkenyl group, alkynyl group, alkylthio group, alkoxycarbonyl group, hydroxyl group (-OH), carboxyl group (-COOH), thiol group (-SH), and cyano group (-CN). 2 These may be the same or different. Each R 1 and each R 2 They may be the same or different.

[0080] R 1 and R 2 The above groups that can constitute each of them are not particularly limited, but for example, Ar 1 ~Ar 5 Examples of substituents in cases where the group is substituted with a substituent include those listed above.

[0081] In the above equation (2), "(Ar 6 )4" means 4 Ar 6 This indicates that each Ar 6Each is independently represented by a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. 6 They may be the same or different. In the above equation (2), "(Ar 7 )5" means 5 Ar 7 This indicates that each Ar 7 Each is independently represented by a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. 7 They may be the same or different. 2 or more Ar 7 The two or more Ar 7 A fused ring may be formed between the bonded benzene ring and the bonded ring.

[0082] In the above equation (3), "(Ar 8 )3" means 3 Ar 8 This indicates the existence of Ar. 8Each is independently represented by a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. 8 They may be the same or different. In the above equation (3), "(Ar 9 )4" means 4 Ar 9 This indicates the existence of Ar. 9 Each is independently represented by a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. 9 They may be the same or different. 2 or more Ar 9 The two or more Ar 9 A fused ring may be formed between the bonded benzene ring and the bonded ring.

[0083] Each Ar 6 and each Ar 7 They may be the same or different. Each Ar 8 and each Ar 9 They may be the same or different.

[0084] Ar 6 Ar 7 Ar 8 and Ar 9 The alkyl group, hydroxyalkyl group, alkoxy group, alkoxyalkyl group, alkenyl group, alkynyl group, alkylthio group, and alkoxycarbonyl group that can constitute each of these are not particularly limited. These groups are not particularly limited, but for example, Ar 1 ~Ar 5 Examples of substituents in cases where the group is substituted with a substituent include those listed above.

[0085] Ar 6 Ar 7 Ar 8 and Ar 9 There are no particular limitations on the monovalent aromatic hydrocarbon groups having 6 to 60 carbon atoms that can constitute each of them. 6 Ar 7 Ar 8 and Ar 9 Aromatic hydrocarbon groups that can constitute each of these include monovalent groups derived from aromatic hydrocarbon rings such as benzene (phenylene group), indene, naphthalene, anthracene, azulene, heptalene, acenaphthene, phenalene, fluorene, phenanthrine, and pyrene, and monovalent groups derived from ring aggregates of two or more aromatic hydrocarbon rings linked by single bonds, such as biphenyl (biphenylene group), terphenyl (terphenylene group), quaterphenyl (quaterphenylene group), quinquiphenyl (quinquiphenylene group), and sexiphenyl (sexiphenylene group).

[0086] Ar 6 Ar 7 Ar 8 and Ar 9 There are no particular restrictions on monovalent aromatic heterocyclic groups having 3 to 60 ring-forming atoms that can constitute each of these groups. 6 Ar 7 Ar 8 and Ar 9Examples of aromatic heterocyclic groups that can constitute each of these include monovalent groups derived from aromatic heterocyclic rings such as acridine, phenazine, benzoquinoline, benzoisoquinoline, phenanthridine, phenanthroline, anthraquinone, fluorenone, dibenzofuran, dibenzothiophene, carbazole, imidazophenanthidine, benzimidazophenanthidine, azadibenzofuran, azacarbazole, azadibenzothiophene, diazadibenzofuran, diazacarbazole, diazadibenzothiophene, xanthone, thioxanthone, pyridine, quinoline, and anthraquinoline, as well as monovalent groups derived from ring assemblies of two or more aromatic heterocyclic rings linked by single bonds, such as bipyridine, bipyrimidine, and bipyrazine.

[0087] Ar 6 Ar 7 Ar 8 and Ar 9 There are no particular limitations on substituted or unsubstituted monovalent ring aggregates having a structure in which one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocycles having 3 to 60 ring-forming atoms are linked via single bonds, which can each constitute the respective. 6 Ar 7 Ar 8 and Ar 9 In the monovalent ring aggregate groups that can constitute each of these, examples of aromatic hydrocarbon rings having 6 to 60 carbon atoms include the rings exemplified above as aromatic hydrocarbon rings constituting the monovalent aromatic hydrocarbon groups having 6 to 60 carbon atoms. 6 Ar 7 Ar 8 and Ar 9 In the monovalent ring aggregate groups that can constitute each of these, examples of aromatic heterocycles with 3 to 60 ring-forming atoms include the rings exemplified as aromatic heterocycles constituting the above-mentioned monovalent aromatic heterocycle groups with 3 to 60 ring-forming atoms. 6 Ar 7 Ar 8 and Ar 9In the monovalent ring aggregate group that can constitute each of the above, the number of aromatic hydrocarbon rings having 6 to 60 carbon atoms is not particularly limited as long as it is 1 or more, but is preferably 1 to 5, more preferably 1 to 3, even more preferably 1 to 2, and particularly preferably 1. In the ring aggregate group, the number of aromatic heterocycles having 3 to 60 ring-forming atoms is not particularly limited as long as it is 1 or more, but is preferably 1 to 5, more preferably 1 to 3, even more preferably 1 to 2, and particularly preferably 1.

[0088] Ar 6 Ar 7 Ar 8 and Ar 9 If the group is substituted with substituents, the number of substituents introduced is not particularly limited. 6 Ar 7 Ar 8 and Ar 9 The number of substituents introduced in each is preferably 1 to 3, more preferably 1 to 2, and even more preferably 2. 6 Ar 7 Ar 8 and Ar 9 If the group is substituted with a substituent, the type of substituent is not particularly limited. 6 Ar 7 Ar 8 and Ar 9 When the group is substituted with a substituent, examples of the substituents include alkyl groups, hydroxyalkyl groups, alkoxy groups, alkoxyalkyl groups, alkenyl groups, alkynyl groups, alkylthio groups, alkoxycarbonyl groups, hydroxyl groups (-OH), carboxyl groups (-COOH), thiol groups (-SH), cyano groups (-CN), halogen groups, etc. 6 Ar 7 Ar 8 and Ar 9When the group is substituted with a substituent, the substituents are not particularly limited and include alkyl groups, hydroxyalkyl groups, alkoxy groups, alkoxyalkyl groups, alkenyl groups, alkynyl groups, alkylthio groups, alkoxycarbonyl groups, and halogen groups. Examples of these groups include, for example, Ar 1 ~Ar 5 The following are examples of substituents when the group is substituted with a substituent. 6 and Ar 7 If is a group substituted with substituents, the substituents may be the same or different. 6 and Ar 7 If each of the following exists in 2 or more cases, and there are 2 or more Ar 6 and 2 or more Ar 7 If is a group substituted with a substituent, each Ar 6 and each Ar 7 The substituents may be the same or different. 6 and Ar 7 If each of these is a group substituted with a substituent, and each has two or more such substituents, then Ar 6 and Ar 7 In each of these, the two or more substituents may be the same or different. 8 and Ar 9 If is a group substituted with substituents, the substituents may be the same or different. 8 and Ar 9 If each of the following exists in 2 or more cases, and there are 2 or more Ar 8 and 2 or more Ar 9 If is a group substituted with a substituent, each Ar 8 and each Ar 9 The substituents may be the same or different. 8 and Ar 9 If each of these is a group substituted with a substituent, and each has two or more such substituents, then Ar 8 and Ar 9 In each of these, the two or more substituents may be the same or different.

[0089] Ar 6 Ar 7 Ar 8 and Ar 9 The groups that can constitute each of these are preferably a hydrogen atom, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. More preferably a hydrogen atom or a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms. More preferably a hydrogen atom or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 carbon atoms. Even more preferably a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted biphenyl group. Furthermore, a hydrogen atom, a phenyl group, a fluorenyl group, or a biphenyl group is particularly preferred.

[0090] 4 Ar 6 Preferably, three or four of them are hydrogen atoms. Five Ar 7 Preferably, three, four, or five of them are hydrogen atoms. 8 Preferably, three of them are hydrogen atoms. 9 Preferably, four of them are hydrogen atoms.

[0091] 2 or more Ar 7 When these bonded benzene rings form a fused ring, and two or more Ar 9When these elements form a fused ring with the bonded benzene ring, the fused ring is not particularly limited as long as it contains a benzene ring. The fused ring containing a benzene ring may be an aromatic hydrocarbon ring or an aromatic heterocycle, but it is preferably an aromatic hydrocarbon ring, more preferably an aromatic hydrocarbon ring having 9 to 60 carbon atoms, and particularly preferably an aromatic hydrocarbon ring having 10 to 22 carbon atoms. The aromatic hydrocarbon ring having 9 to 60 carbon atoms is not particularly limited, but examples include indene, naphthalene, anthracene, acenaphthene, phenalene, fluorene, phenanthrine, pyrene, etc. Among these, naphthalene is more preferred.

[0092] In the above formula (2), X represents C substituted with S, O, or two linear or branched hydrocarbon groups having 1 to 16 carbon atoms, either substituted or unsubstituted. Here, "C substituted with two linear or branched hydrocarbon groups having 1 to 16 carbon atoms" means that C is substituted with two linear or branched hydrocarbon groups having 1 to 16 carbon atoms, and that each of these hydrocarbon groups may be substituted or unsubstituted. In a C that can constitute X and is substituted with two linear or branched hydrocarbon groups having 1 to 16 carbon atoms, the two linear or branched hydrocarbon groups having 1 to 16 carbon atoms may be the same or different, but from the viewpoint of improving the lifespan of the element, it is preferable that they be the same.

[0093] In C, which is substituted with two linear or branched hydrocarbon groups having 1 to 16 carbon atoms that can constitute X, the linear or branched hydrocarbon groups having 1 to 16 carbon atoms are not particularly limited. The linear or branched hydrocarbon groups having 1 to 16 carbon atoms may be alkyl groups, alkenyl groups, or alkynyl groups. The linear or branched alkyl group having 1 to 16 carbon atoms is not particularly limited, but examples include linear alkyl groups such as methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, isopentyl group, tert-pentyl group, neopentyl group, 1,2-dimethylpropyl group, isohexyl group, 1, Examples of branched alkyl groups include 3-dimethylbutyl group, 1-isopropylpropyl group, 1,2-dimethylbutyl group, 1,4-dimethylpentyl group, 3-ethylpentyl group, 2-methyl-1-isopropylpropyl group, 1-ethyl-3-methylbutyl group, 2-ethylhexyl group, 3-methyl-1-isopropylbutyl group, 2-methyl-1-isopropyl group, 1-tert-butyl-2-methylpropyl group, 3,5,5-trimethylhexyl group, isodecyl group, 1-methyldecyl group, vinyl group, allyl group, 1-propenyl group, 2-butenyl group, 1,3-butadienyl group, and 2-pentenyl group. The linear or branched alkenyl group having 2 to 16 carbon atoms is not particularly limited, but examples include vinyl group, allyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 1-heptenyl group, 2-heptenyl group, 5-heptenyl group, 1-octenyl group, 3-octenyl group, 5-octenyl group, 1,3-butadienyl group, etc.There are no particular limitations on the linear or branched alkynyl group having 2 to 16 carbon atoms, but examples include acetylenyl group (ethynyl group), 1-propynyl group, 2-propynyl group (propargyl group), 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentetyl group, 2-pentetyl group, 3-pentetyl group, 1-hexynyl group, 2-hexynyl group, 3-hexynyl group, 1-heptynyl group, 2-heptynyl group, 5-heptynyl group, 1-octinyl group, 3-octinyl group, and 5-octinyl group.

[0094] When a linear or branched hydrocarbon group having 1 to 16 carbon atoms is substituted with a substituent to replace a carbon atom that can constitute X, the number of substituents introduced is not particularly limited. When a linear or branched hydrocarbon group having 1 to 16 carbon atoms is substituted with a substituent to replace a carbon atom that can constitute X, the type of substituent is not particularly limited. Examples of substituents when a linear or branched hydrocarbon group having 1 to 16 carbon atoms is substituted with a substituent to replace a carbon atom that can constitute X include hydroxyl groups (-OH), carboxyl groups (-COOH), thiol groups (-SH), cyano groups (-CN), halogen groups, etc. There are no particular limitations on halogen groups, but for example, Ar 1 ~Ar 5 Examples of substituents when the group is substituted with substituents include those listed above. In two linear or branched hydrocarbon groups having 1 to 16 carbon atoms, the substituents substituting them may be the same or different. In a linear or branched hydrocarbon group having 1 to 16 carbon atoms, where each group has two or more substituents, the two or more substituents may be the same or different.

[0095] In C, which can constitute X, two substituted or unsubstituted linear or branched hydrocarbon groups having 1 to 16 carbon atoms are not particularly limited. The two substituted or unsubstituted linear or branched hydrocarbon groups having 1 to 16 carbon atoms are preferably alkyl groups, more preferably linear or branched alkyl groups having 1 to 18 carbon atoms. Furthermore, linear alkyl groups having 1 to 8 carbon atoms are even more preferred, and methyl groups are particularly preferred.

[0096] In formula (2) and general formula (3) above, * represents the bond position with an adjacent atom, that is, * represents the bond position with the adjacent nitrogen atom of the carbazole ring in general formula (1) above.

[0097] In a polymer according to one embodiment of the present invention, the constituent unit represented by the above formula (1) is Each R 1 These all represent hydrogen atoms. Each R 2 These all represent hydrogen atoms. Each Ar 6 Each of these independently represents a hydrogen atom, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. Each Ar 7 Each of these independently represents a hydrogen atom, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. 2 or more Ar 7 The two or more Ar 7A fused ring may be formed between the bonded benzene ring and the bonded ring. Each Ar 8 Each of these independently represents a hydrogen atom, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. Each Ar 9 Each of these independently represents a hydrogen atom, a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. X represents carbon (C) substituted with sulfur (S), oxygen (O), or two unsubstituted straight-chain or branched hydrocarbon groups having 1 to 16 carbon atoms. 2 or more Ar 9 The two or more Ar 9 A fused ring may be formed between the bonded benzene ring and the bonded ring. It is preferable that the following conditions are met. According to this structure, the effect of improving the device lifetime in electroluminescent elements using polymers, in particular quantum dot electroluminescent elements, is greatly enhanced.

[0098] A polymer according to one embodiment of the present invention preferably contains at least one constituent unit selected from the following group (A). In one embodiment of the present invention, it is more preferable that the constituent unit represented by the above formula (1) contained in the polymer is at least one constituent unit selected from the following group (A).

[0099] [ka]

[0100] [Chemical]

[0101] [Chemical]

[0102] [Chemical]

[0103] [Chemical]

[0104] In the above formula, n represents an integer, and each is independently preferably an integer of 1 or more and 20 or less, more preferably an integer of 6 or more and 12 or less, and even more preferably 6, 8, 10, or 12. When the compound represented by the above formula has two or more groups represented by "C n H 2n+1 -", the n in each "C n H 2n+1 -" may be the same or different from each other. When the compound represented by the above formula has two or more groups represented by "C n H 2n+1 -", the groups represented by each "C n H 2n+1 -" may be the same or different from each other. The group represented by "C n H 2n+1 -" may be linear or branched, but is preferably a linear group.

[0105] A polymer according to one embodiment of the present invention preferably contains at least one constituent unit selected from the following group (B). In one embodiment of the present invention, it is more preferable that the constituent unit represented by the above formula (1) contained in the polymer is at least one constituent unit selected from the following group (B). Among these, polymers A-1 to A-21 used in the examples described later are preferred. Polymers A-1 to A-6 and A8 to A21 are more preferred, and A-1 to A-3 and A-8 to A-17 are even more preferred. Polymers A-1, A-2, A-3, A-15 and A-17 are even more preferred, polymers A-3, A-15 and A-17 are particularly preferred, and polymer A-17 is even more particularly preferred. With these structures, the effect of improving the device lifetime in electroluminescent elements using polymers, in particular quantum dot electroluminescent elements, is greatly increased.

[0106] [ka]

[0107] [ka]

[0108] [ka]

[0109] In the above formula, "C 12 H 25 The group represented by "-" preferably represents an n-dodecyl group. In the above formula, "C 10 H 21 The group represented by "-" preferably represents an n-decyl group. In the above formula, "C8H 17 The group represented by "-" preferably represents an n-octyl group. In the above formula, "C6H 13 The group represented by "-" preferably represents an n-hexyl group.

[0110] The polymer according to an embodiment of the present invention is not particularly limited, and examples thereof include a polymer containing at least one structural unit selected from the following group (B'). In one embodiment of the present invention, the structural unit represented by the above formula (1) contained in the polymer may be, for example, at least one structural unit selected from the following group (B)'. Among the following group (B'), polymers A-1 to A-7 used in the examples described later are preferable. Further, polymers A-1 to A-6 are more preferable, A-1 to A-3 are even more preferable, polymer A-1 or A-3 is even more preferable, and polymer A-3 is particularly preferable. According to these structures, the effect of improving the element lifetime in an electroluminescence element using the polymer, particularly in a quantum dot electroluminescence element, becomes greater.

[0111]

Chemical formula

[0112] In the above formula, the group represented by "C8H 17 -" represents an n-octyl group.

[0113] The compositional ratio of the structural unit represented by the above formula (1) in the polymer is not particularly limited. Considering the further improvement effect of the element lifetime and hole transport ability of the electroluminescence element using the polymer, the polymer according to an embodiment of the present invention preferably contains the structural unit represented by the above formula (1) at 10 mol% or more and 100 mol% or less with respect to all the structural units constituting the polymer. The polymer according to an embodiment of the present invention preferably contains the structural unit represented by the above formula (1) at more than 50 mol% and 100 mol% or less with respect to all the structural units constituting the polymer, and more preferably contains it at 100 mol%. That is, the polymer according to an embodiment of the present invention is preferably composed only of the structural unit represented by the above formula (1) and the end group. When the polymer contains two or more structural units represented by the above formula (1), the above compositional ratio means the ratio of the total amount of the structural units represented by the above formula (1).

[0114] As described above, the polymer according to one embodiment of the present invention may contain only the constituent unit represented by formula (1) as a constituent unit. The polymer according to one embodiment of the present invention may further contain, in addition to the constituent unit represented by formula (1), other constituent units other than the constituent unit represented by formula (1) as a constituent unit.

[0115] If other constituent units are included, the other constituent units are not particularly limited as long as they do not hinder the effects of the present invention. For example, Ar, which constitutes the main chain of formula (1) above. 1 Ar 2 and Ar 4 If the group does not include a group selected from group (III) below, other constituent units include, for example, at least one constituent unit selected from group (III) below.

[0116] [ka]

[0117] The proportion of the constituent units selected from group (III) above in the polymer is not particularly limited. Considering the ease of film formation and the effect of further improving the strength of the film by the composition containing the polymer, it is preferable that the polymer according to one embodiment of the present invention contains the constituent units selected from group (III) below in an amount of 1 mol% to 10 mol% of the total constituent units of the polymer. If the polymer contains two or more constituent units selected from group (III) above, the above proportion refers to the proportion of the total amount of constituent units selected from group (III) above.

[0118] The ends (end groups) of the main chain of the polymer according to one embodiment of the present invention are not particularly limited and are appropriately determined depending on the type of raw material used, but for example, they are hydrogen atoms.

[0119] The weight-average molecular weight (Mw) of the polymer according to one embodiment of the present invention is not particularly limited as long as the desired effects of the present invention are obtained. The weight-average molecular weight (Mw) is preferably, for example, 12,000 or more and 1,000,000 or less, and more preferably 50,000 or more and 500,000 or less. With such a weight-average molecular weight, it is possible to appropriately adjust the viscosity of the coating solution used to form layers (e.g., hole injection layers, hole transport layers) using the polymer to form layers with uniform film thickness.

[0120] The number-average molecular weight (Mn) of the polymer according to one embodiment of the present invention is not particularly limited as long as the desired effects of the present invention are obtained. The number-average molecular weight (Mn) is preferably, for example, 10,000 to 250,000, and more preferably 30,000 to 100,000. With such a number-average molecular weight, it is possible to appropriately adjust the viscosity of the coating solution used to form layers (e.g., hole injection layers, hole transport layers) using the polymer to form layers with uniform film thickness.

[0121] The polydispersity (weight-average molecular weight / number-average molecular weight) of the polymer according to one embodiment of the present invention is, for example, 1.2 or more and 4.0 or less, preferably 1.5 or more and 3.5 or less.

[0122] The measurement of number-average molecular weight (Mn) and weight-average molecular weight (Mw) is not particularly limited and can be performed using known methods or by appropriately modifying known methods. In this specification, the values ​​of number-average molecular weight (Mn) and weight-average molecular weight (Mw) obtained by the following methods are adopted. The polydispersity (Mw / Mn) is calculated by dividing the weight-average molecular weight (Mw) by the number-average molecular weight (Mn) obtained by the following methods.

[0123] (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 polymer according to one embodiment of the present invention can be measured by size exclusion chromatography (SEC) using polystyrene as a standard substance under the following conditions.

[0124] [ka]

[0125] The glass transition temperature (Tg) of the polymer according to one embodiment of the present invention is not particularly limited, but is preferably 70°C or higher, more preferably 80°C or higher, and even more preferably 100°C or higher. The glass transition temperature (Tg) of the polymer according to one embodiment of the present invention is not particularly limited, but is preferably 200°C or lower, more preferably 180°C or lower, and even more preferably 150°C or lower. Within these ranges, the device is suitable for device fabrication and a device with improved characteristics can be obtained. The glass transition temperature can be measured using a differential scanning calorimeter (DSC) (Seiko Instruments Ltd., product name: DSC6000). Details of the measurement method are described in the examples.

[0126] The HOMO level of the polymer according to one embodiment of the present invention is not particularly limited, but is preferably -5.75 eV or higher, more preferably -5.7 eV or higher, and even more preferably -5.65 eV or higher. The HOMO level of the polymer according to one embodiment of the present invention is not particularly limited, but is preferably -4.5 eV or lower, more preferably -5.0 eV or lower, and even more preferably -5.3 V or lower. Within these ranges, the hole injection efficiency into the light-emitting layer is further improved, and a device with improved characteristics can be obtained. The HOMO level can be measured using an air-in-air photoelectron spectrometer (AC-3, manufactured by Riken Keiki Co., Ltd.). Details of the measurement method are described in the examples.

[0127] The LUMO level of the polymer according to one embodiment of the present invention is not particularly limited, but is preferably -3.0 eV or higher, more preferably -2.8 eV or higher, and even more preferably -2.7 eV or higher. The LUMO level of the polymer according to one embodiment of the present invention is not particularly limited, but is preferably -2.0 eV or lower, more preferably -2.2 eV or lower, and even more preferably -2.4 eV or lower. Within these ranges, electrons are efficiently confined in the light-emitting layer, and a device with improved characteristics can be obtained. The LUMO level can be calculated by photoluminescence (PL) spectroscopy. Details of the measurement method are described in the examples.

[0128] A polymer according to one embodiment of the present invention is preferably highly solvent resistant. In this specification, solvent resistantness is defined as the ratio of the intensity at the reference wavelength of the absorption spectrum after immersion in the solvent to the intensity at the reference wavelength of the absorption spectrum before immersion in the solvent ("intensity at the reference wavelength of the absorption spectrum after immersion in the solvent" / "intensity at the reference wavelength of the absorption spectrum after immersion in the solvent" × 100 (%)), and can be determined from this value. Details of the method for determining the reference wavelength and the method for evaluating the solvent resistantness are described in the examples. The solvent resistantness of a polymer according to one embodiment of the present invention is not particularly limited, but is preferably 75% or more, and more preferably 90% or more. By using a polymer that satisfies these ranges, film mixing between the polymer-containing layer and the other layer can be further suppressed even when other layers are formed by a wet method. For example, when an electroluminescent element, which will be described later, is manufactured using a wet method (e.g., an inkjet method), using a polymer that satisfies these ranges can further suppress film mixing between the polymer-containing layer and the other layer.

[0129] A polymer according to one embodiment of the present invention can be synthesized using a known organic synthesis method. A specific synthesis method for the polymer according to one embodiment of the present invention can be easily understood by those skilled in the art by referring to the examples described later.

[0130] Specifically, a polymer according to one embodiment of the present invention can be produced, for example, by a polymerization reaction using one or more monomers represented by the following formula (1'), or by a copolymerization reaction using one or more monomers represented by the following formula (1') and other monomers corresponding to the other constituent units mentioned above.

[0131] [ka]

[0132] Alternatively, a polymer according to one embodiment of the present invention can be produced, for example, by a copolymerization reaction using one or more monomers represented by the following formula (1-1') and one or more monomers represented by the following formula (1-2'), or by a copolymerization reaction using one or more monomers represented by the following formula (1-1'), one or more monomers represented by the following formula (1-2'), and other monomers corresponding to the other constituent units mentioned above.

[0133] [ka]

[0134] [ka]

[0135] In equations (1'), (1-1'), and (1-2') above, A and Ar 1 Ar 2 Ar 3 Ar 4 Ar 5 , R 1 , R 2 The definition is the same as in formula (1) above. Z1, Z2, Z1', Z2', Z1'' and Z2'' are each independently a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom, especially bromine atom) or a base of a structure represented by the following formula (Z-1). Note that in the structure represented by the following formula (Z-1), R A ~R DEach of these is an alkyl group having 1 to 3 carbon atoms. Preferably, R A ~R D is a methyl group. Note that Z1 and Z2 in formula (1') above may be the same or different. Similarly, Z1' and Z2' in formula (1-1') above may be the same or different. Z1'' and Z2'' in formula (1-2') above may be the same or different. Preferably, Z1 and Z2 are different in formula (1'). Preferably, Z1' and Z2' are the same in formula (1-1'); Z1'' and Z2' are the same in formula (1-2'); and Z1' and Z2' in formula (1-1') are different from Z1'' and Z2' in formula (1-2').

[0136] [ka]

[0137] The monomer represented by formula (1'), the monomer represented by formula (1-1'), and the monomer represented by formula (1-2'), which can be used in the polymerization of the polymer according to one embodiment of the present invention, can each be synthesized by appropriately combining known synthesis reactions, and their structures can be confirmed by known methods (e.g., NMR, LC-MS, etc.). Furthermore, other monomers corresponding to the other constituent units, which can be used in the polymerization of the polymer according to one embodiment of the present invention, can also be synthesized by appropriately combining known synthesis reactions, and their structures can also be confirmed by known methods (e.g., NMR, LC-MS, etc.).

[0138] <Electroluminescent element materials> As described above, the polymer according to the above embodiment is suitably used in electroluminescent elements. The polymer according to the above embodiment provides an electroluminescent element with excellent element lifespan. Therefore, another embodiment of the present invention can be said to relate to an electroluminescent element material (EL element material) including the polymer according to the above embodiment. Alternatively, it can be said to relate to the use of the polymer according to the above embodiment as an EL element material. In particular, in the case of a polymer containing the constituent unit represented by formula (1) above, the main chain has appropriate flexibility. For this reason, the polymer according to the above embodiment exhibits high solubility in solvents and high heat resistance. Thus, it can be easily formed into a film (thin film) by a wet (coating) method.

[0139] <Composition> Another aspect of the present invention can be said to relate to a composition comprising a polymer according to the above aspect. Furthermore, as an embodiment of the present invention, a composition comprising an EL element material according to the above aspect can be cited. The polymer according to the above aspect may be used alone or as a mixture of two or more types. The composition according to this aspect further comprises other compounds in addition to the polymer according to the above aspect. The other compounds are not particularly limited, but are preferably at least one material selected from the group consisting of hole transport materials, electron transport materials and light-emitting materials. Here, the light-emitting material included in the composition is not particularly limited, but examples include organometallic complexes (luminescent organometallic complex compounds) or semiconductor nanoparticles (e.g., semiconductor inorganic nanoparticles). As described above, the polymer according to the above aspect is suitably used in electroluminescent elements. Thus, the composition according to this aspect also provides an electroluminescent element with excellent element lifetime.

[0140] <Electroluminescent element> As described above, the polymer according to the above embodiment is suitably used in electroluminescent elements. The polymer according to the above embodiment may be used alone or as a mixture of two or more types. Such an electroluminescent element can achieve excellent element life. Thus, another embodiment of the present invention can also be said to relate to an electroluminescent element comprising a pair of electrodes and at least one layer of organic film containing the polymer according to the above embodiment, disposed between the pair of electrodes. One embodiment of the present invention can also be said to relate to an electroluminescent element comprising a pair of electrodes and at least one layer of organic film containing the EL element material according to the above embodiment, disposed between the pair of electrodes. One embodiment of the present invention can also be said to relate to an electroluminescent element comprising a pair of electrodes and at least one layer of organic film containing the composition according to the above embodiment, disposed between the pair of electrodes. The object (or effect) of the present invention can also be achieved by the electroluminescent element according to this embodiment.

[0141] The electroluminescent element according to this embodiment preferably further comprises a layer containing quantum dots. An electroluminescent element according to a preferred embodiment of the present invention further comprises a layer containing quantum dots in addition to at least one organic film containing the polymer according to the above embodiment. The polymer according to the above embodiment may be used alone or as a mixture of two or more types. In one embodiment of the present invention, the polymer according to the above embodiment may be included in the organic layer as an EL element material according to the above embodiment, or as a composition according to the above embodiment. The layer containing quantum dots in the electroluminescent element according to a preferred embodiment of the present invention is not particularly limited, but for example, those listed in the description of the case in which quantum dots are included in the light-emitting layer of the electroluminescent element described later can be applied. The layer containing quantum dots may contain other materials other than quantum dots. Examples of other materials include organic compounds. The layers other than the layer containing quantum dots are not particularly limited, but for example, those listed in the description of an example of an electroluminescent element described later can be applied.

[0142] The method for manufacturing an electroluminescent element is not particularly limited, and known methods can be used. The method for forming an organic film containing a polymer according to the above embodiment, and the method for forming an organic film containing a composition according to the above embodiment, are not particularly limited, but a coating method is preferred. Therefore, another embodiment of the present invention can be said to be a method for manufacturing an electroluminescent element containing an organic film containing a polymer according to the above embodiment, wherein at least one layer of the organic film containing the polymer is formed by a coating method. Furthermore, it can be said that one embodiment of the present invention is a method for manufacturing an electroluminescent element containing an organic film containing an EL element material according to the above embodiment, wherein at least one layer of the organic film containing the EL element material is formed by a coating method. Another embodiment of the present invention can be said to be a method for manufacturing an electroluminescent element containing an organic film containing a composition according to the above embodiment, wherein at least one layer of the organic film containing the composition is formed by a coating method.

[0143] The polymer according to one embodiment of the present invention exhibits excellent solubility in organic solvents. Therefore, the polymer according to one embodiment of the present invention, the EL element material according to one embodiment of the present invention, and the composition according to one embodiment of the present invention are particularly suitable for use in the manufacture of devices (especially thin films) by a coating method (wet process). For this reason, another aspect of the present invention can also be said to relate to a liquid composition containing any of the polymer, the EL element material, and the composition according to the above embodiment, and a solvent or dispersion medium. The liquid composition according to one embodiment of the present invention may further contain other compounds in addition to the polymer and the solvent or dispersion medium. The other compounds are not particularly limited, but examples include materials that constitute each layer of the electroluminescent device described later. Furthermore, for these reasons, another aspect of the present invention can also be said to relate to a thin film containing any of the polymer, the EL element material, and the composition according to the above embodiment.

[0144] Furthermore, the polymer according to one embodiment of the present invention exhibits excellent hole implantation and hole mobility. For this reason, the polymer according to one embodiment of the present invention, the EL element material according to one embodiment of the present invention, and the composition according to one embodiment of the present invention can be suitably used in the formation of any organic film such as a hole injection material, a hole transport material, or a light-emitting material (host). Of these, from the viewpoint of hole transportability, they are suitably used as a hole injection material or a hole transport material, and are particularly suitably used as a hole transport material.

[0145] [An example of an electroluminescent element] In the following, an electroluminescent element according to one embodiment of the present invention will be described in detail with reference to Figure 1. Figure 1 is a schematic diagram showing an electroluminescent element according to one embodiment of the present invention. In this specification, "electroluminescent element" may be abbreviated as "EL element". In the description of the drawings, the same elements are denoted by the same reference numerals, and redundant explanations are omitted. Also, the dimensional ratios in the drawings are exaggerated for illustrative purposes and may differ from the actual ratios.

[0146] As shown in Figure 1, an EL element 100 according to one embodiment of the present invention comprises 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, a light-emitting layer 150 disposed on the hole transport layer 140, an electron transport layer 160 disposed on the light-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.

[0147] Here, the polymer according to the above embodiment is included, for example, in an organic film (organic layer) disposed between the first electrode 120 and the second electrode 180. In this specification, a film containing an organic compound is referred to as an organic film (organic layer), and the organic film (organic layer) may further contain an inorganic compound. Specifically, it is preferable that the polymer according to the above embodiment satisfies at least one selected from the group consisting of being included in the hole injection layer 130 as a hole injection material, being included in the hole transport layer 140 as a hole transport material, and being included in the light-emitting layer 150 as a light-emitting material (host). It is more preferable that the polymer according to the above embodiment is included in the hole injection layer 130 as a hole injection material or in the hole transport layer 140 as a hole transport material. It is even more preferable that the polymer according to the above embodiment is included 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 according to the above embodiment 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 according to the above embodiment is a hole transport layer or a hole injection layer. In a further preferred embodiment of the present invention, the organic film containing the polymer according to the above embodiment is a hole transport layer. In these embodiments, the polymer according to the above embodiment may be included in the organic layer as an EL element material according to the above embodiment, or as a composition according to the above embodiment.

[0148] Furthermore, the method for forming the organic film containing the polymer according to the above embodiment, the organic film containing the EL element material according to the above embodiment, and the organic film containing the composition according to the above embodiment is not particularly limited. However, these organic films are preferably formed by a coating method (solution coating method). Specifically, the organic film can be formed by spin coating, casting, microgravure coating, gravure coating, bar coating, roll coating, or wire bar coating. The film is formed using solution coating methods such as the coat method, dip coat method, spray coat method, screen printing method, flexographic printing method, offset printing method, and inkjet printing method.

[0149] The solvent used in the solution coating method is not particularly limited, as long as it can dissolve the polymer according to the above embodiment, the EL element material according to the above embodiment, and the composition according to the above embodiment. The solvent used in the solution coating method can be appropriately selected depending on the type of solute. Examples include toluene, xylene, ethylbenzene, diethylbenzene, methylene, propylbenzene, cyclohexylbenzene, dimethoxybenzene, anisole, ethoxytoluene, phenoxytoluene, isopropyl biphenyl, dimethylanisole, phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, cyclohexane, etc. The solvent may be used alone or as a mixture of two or more. The amount of solvent used is not particularly limited, but considering ease of coating, the amount should preferably be such that the concentration of the polymer according to the above embodiment is 0.1% by mass or more and more than 0.5% by mass or less.

[0150] The method for forming the organic film containing the polymer according to the above embodiment, the organic film containing the EL element material according to the above embodiment, and layers other than the organic film containing the composition according to the above embodiment are not particularly limited. The organic film containing the polymer according to the above embodiment, the organic film containing the EL element material according to the above embodiment, and layers other than the organic film containing the composition according to the above embodiment may be formed, for example, by vacuum deposition or by solution coating.

[0151] The substrate 110 can be a substrate commonly used in EL elements. For example, the substrate 110 may be a glass substrate, a semiconductor substrate such as a silicon substrate, or a transparent plastic substrate.

[0152] 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 high work function. For example, the first electrode 120 may be formed as a transmissive electrode using indium tin oxide (In2O3-SnO2:ITO), indium zinc oxide (In2O3-ZnO), tin oxide (SnO2), zinc oxide (ZnO), etc., which have excellent transparency and conductivity. Alternatively, the first electrode 120 may be formed as a reflective electrode by laminating magnesium (Mg), aluminum (Al), etc., onto the transparent conductive film. Furthermore, after forming the first electrode 120 on the substrate 110, cleaning and UV-ozone treatment may be performed if necessary.

[0153] 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 with a thickness of, for example, 10 nm to 1000 nm, preferably 20 nm to 50 nm (dry film thickness; the same applies hereinafter).

[0154] The hole injection layer 130 can be formed using known hole injection materials. 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), and copper phthalocyanine. phthalocyanine), 4,4',4”-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), N,N'-di(1-naphthyl)-N,N'-diphenyl Nylbenzidine (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine: NPB), 4,4',4”-tris(diphenylamino)triphenylamine (4,4',4”-tris(diphenylamino)triphenylamine: TDATA), 4,4',4”-tris(N,N-2-naphthylphenylamino)triphenylamine (4,4',4”-tris(N,N-2-naphthylphenylamino)triphenylamine: 2-TNATA), polyaniline / dodecylbenzenesulfonic acid Examples include poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate):PEDOT / PSS, and polyaniline / 10-camphorsulfonic acid. The hole implantation material may be used individually or as a mixture of two or more.

[0155] A hole transport layer 140 is formed on the hole injection layer 130. The hole transport layer 140 is a layer that has the function of transporting holes, and may be formed with a thickness of, for example, 10 nm to 150 nm, preferably 20 nm to 50 nm.

[0156] In one embodiment of the present invention, the hole transport layer 140 is preferably formed by a solution coating method using the polymer according to the above embodiment. In one embodiment of the present invention, the polymer according to the above embodiment may be used as an EL element material according to the above embodiment, or as a composition according to the above embodiment. The polymer according to the above embodiment may be used alone or as a mixture of two or more types. These methods make it possible to extend the device life of the EL element 100, in particular the device life of the quantum dot electroluminescent element. Furthermore, since the hole transport layer can be formed by a solution coating method, it is possible to efficiently form a film over a large area.

[0157] In one embodiment of the present invention, the hole transport layer 140 may include the polymer according to the above embodiment and other low molecular weight materials.

[0158] (Low molecule material) The hole transport layer preferably comprises a polymer according to the above embodiment and a low-molecular-weight material. The low-molecular-weight material is present in the hole transport layer so as to fill the gaps in the polymer material (for example, the polymer according to the above embodiment). This allows for the formation of a dense hole transport layer, improving the hole transport capacity of the hole transport layer. A quantum dot electroluminescent element equipped with such a hole transport layer exhibits excellent luminescence efficiency and luminescence lifetime.

[0159] The low molecular weight material is preferably a hole transport material or a wide-gap material. The hole transport material may have a wide gap, and the wide-gap material may have hole transport properties. Furthermore, it is preferable that one or more types of the low molecular weight material are included in the hole transport layer.

[0160] Here, a wide-gap material refers to a material having a HOMO-LUMO energy gap of 3.3 eV or more. It is preferable that the wide-gap material has a HOMO-LUMO energy gap larger than the HOMO-LUMO energy gap of at least one of the polymers according to the above embodiment used in combination. Furthermore, although the HOMO-LUMO energy gap is not particularly limited, it is preferable to be 4 eV or less. Within this range, the luminescence efficiency and luminescence lifetime of the quantum dot electroluminescent element are further improved.

[0161] The molecular weight of the low molecular weight material is preferably between 100 and 1,500. Within this range, the film can be solidified, and sublimation purification is easy, making it easier to obtain a high-purity product. Furthermore, because the molecular size is appropriate, the effect of filling gaps in polymer materials (for example, polymers according to the above embodiment) is further improved. The molecular weight of the low molecular weight material is more preferably between 500 and 1,500, and even more preferably between 600 and 1,300. Note that the molecular weight of the low molecular weight material is the sum of the atomic weights of each atom.

[0162] The low molecular weight material preferably satisfies condition (a) below, and also satisfies condition (b), condition (c), or both of these conditions. That is, preferred low molecular weight materials include compounds that satisfy condition (a) and condition (b), compounds that satisfy condition (a) and condition (c), and compounds that satisfy condition (a), condition (b), and condition (c): (a) The band gap of the low molecular weight material is larger than that of the polymer according to the above embodiment to be mixed. (b) With respect to the polymer according to the above embodiment to be mixed, the LUMO of the low molecular weight material is shallower. (c) The HOMO of the low molecular weight material is deeper than the polymer according to the above embodiment that is mixed.

[0163] By including a low-molecular-weight material that satisfies condition (a) and also satisfies condition (b), condition (c), or both, together with the polymer according to the above embodiment, the electroluminescent device achieves enhanced charge injection, improved electron resistance, or both.

[0164] Condition (a) above indicates that the value calculated using "LUMO(eV)-HOMO(eV)" for the low molecular weight material is greater than the value calculated using "LUMO(eV)-HOMO(eV)" for the polymer relating to the above embodiment of mixing.

[0165] Condition (b) above indicates that the LUMO(eV) value of the low molecular weight material is greater than the LUMO(eV) value of the polymer according to the above embodiment that is mixed.

[0166] Condition (c) above indicates that the HOMO(eV) value of the low molecular weight material is smaller than the HOMO(eV) value of the low molecular weight material related to the above embodiment of mixing.

[0167] Furthermore, the HOMO and LUMO levels of low-molecular-weight materials are typically negative values.

[0168] In addition to condition (a) above, satisfying condition (b) above improves the electron resistance of the light-emitting layer. Furthermore, in addition to condition (a) above, satisfying condition (c) above promotes hole injection.

[0169] The following describes low-molecular-weight compounds 1 to 6, which are preferred embodiments of low-molecular-weight materials.

[0170] Low molecular weight compounds 1 to 6 can be synthesized using known organic synthesis methods. The specific synthesis methods for the low molecular weight materials in this embodiment can be easily understood by those skilled in the art. The structure of the low molecular weight materials can also be confirmed by known methods (e.g., NMR, LC-MS, etc.).

[0171] (Low molecular compounds 1, 2) Examples of low molecular weight materials according to a preferred embodiment of the present invention include a low molecular weight compound represented by the following formula (L1) (hereinafter also referred to as "low molecular weight compound 1") and a low molecular weight compound represented by the following formula (L2) (hereinafter also referred to as "low molecular weight compound 2"). Low molecular weight compounds 1 and 2 are hole transport materials, and when used in combination with the polymer according to the above embodiment, low molecular weight compounds 1 and 2 exist in such a way that they fit into the gaps of the polymer according to the above embodiment. As a result, a denser hole transport layer is formed, and the hole transport ability of the hole transport layer is improved. Furthermore, since the hole transport ability of the low molecular weight compounds 1 and 2 themselves, which are the added hole transport materials, is imparted to the hole transport layer, an effect of further improving hole transportability is obtained. According to a more preferred embodiment, the low molecular weight material includes low molecular weight compound 1, low molecular weight compound 2, or a combination thereof.

[0172] The following describes low-molecular-weight compound 1 and low-molecular-weight compound 2.

[0173] (Low molecular compound 1) Low molecular weight compound 1 is a compound represented by the following formula (L1).

[0174] [ka]

[0175] In the above formula (L1), each R is independently a hydrogen atom, a deuterium atom, or a monovalent organic group. In the above formula (L1), multiple Rs may form a ring. In the above formula (L1), multiple Ar a They may form a ring. In the above formula (L1), one or more Ar a And, Ar b The and may form a ring. In the above formula (L1), one or more Ar a And, one or more Rs may form a ring. In the above formula (L1), one or more Rs and Ar b The two atoms may form a ring. From the viewpoint of further improving the advantageous effects of adding low molecular weight materials, in the above formula (L1), R is preferably a hydrogen atom.

[0176] Specific examples of monovalent organic groups include alkyl groups, cycloalkyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, acyl groups, alkoxycarbonyl groups, amino groups, alkoxy groups, cycloalkyloxy groups, aryloxy groups, aryloxycarbonyl groups, acyloxy groups, acylamino groups, alkoxycarbonylamino groups, aryloxycarbonylamino groups, sulfonylamino groups, sulfamoyl groups, carbamoyl groups, alkylthio groups, arylthio groups, silyl groups, sulfonyl groups, sulfinyl groups, ureido groups, phosphate amide groups, halogen atoms, hydroxyl groups, mercapto groups, cyano groups, sulfo groups, carboxyl groups, nitro groups, hydroxamic acid groups, sulfino groups, hydrazino groups, imino groups, and the like.

[0177] In the above formula (L1), if multiple Rs form a ring, the multiple Rs may bond to each other to form a ring. a When a ring is formed, the multiple Ar that form the ring a They may bond to each other to form a ring. In the above formula (L1), one or more Ar a And, Ar b When and form a ring, one or more Ar forms the ring. a And, Ar b These may be bonded to each other to form a ring. In the above formula (L1), one or more Ar a When one or more Rs form a ring, one or more Ars form the ring. a And, one or more Rs may bond with each other to form a ring. In the above formula (L1), one or more Rs and Ar b When and form a ring, the ring consists of multiple R and Ar b These elements may be joined together to form a ring.

[0178] In the above formula (L1), when multiple R groups form a ring, it is preferable that the multiple R groups forming the ring share one aryl group or heteroaryl group to form the ring. a When a ring is formed, the multiple Ar that form the ringa However, it is preferable to share one aryl group or heteroaryl group to form a ring. In the above formula (L1), one or more Ar a And, Ar b When and form a ring, one or more Ar forms the ring. a And, Ar b It is preferable that the two groups share one aryl group or heteroaryl group to form a ring. In the above formula (L1), one or more Ar a When one or more Rs form a ring, one or more Ars form the ring. a Preferably, one or more Rs share one aryl group or heteroaryl group to form a ring. In the above formula (L1), one or more Rs and Ar b When and form a ring, the ring consists of multiple R and Ar b It is preferable that the two groups share one aryl group or heteroaryl group to form a ring.

[0179] The number of carbon atoms in the above alkyl group is more preferably in the following forms.

[0180] For example, if the ligand of the quantum dot is a long-chain alkyl-containing compound such as oleic acid, oleylamine, or trioctylphosphine, it is desirable that the compound contained in the hole transport layer also contains a long-chain alkyl group. This is because the interaction between the ligand of the quantum dot and the alkyl group present in the hole transport layer may result in effects such as improved hole injection.

[0181] Furthermore, when the solvent used to disperse the quantum dots is a long-chain hydrocarbon solvent, it is desirable that the number of carbon atoms in the alkyl group contained in the polymer according to the above embodiment be small, from the viewpoint of ensuring solvent resistance of the hole transport layer.

[0182] Therefore, linear or branched alkyl groups having 1 to 18 carbon atoms are more preferable as the alkyl group. The alkyl group can be selected appropriately depending on the quantum dots used or the solvent in which the quantum dots are dispersed.

[0183] The number of carbon atoms in the above-mentioned alkoxy group is more preferably in the following configurations.

[0184] For example, if the ligand of the quantum dot is a long-chain alkyl-containing compound such as oleic acid, oleylamine, or trioctylphosphine, it is desirable that the compound contained in the hole transport layer also contains a long-chain acoxy group. This is because the interaction between the ligand of the quantum dot and the alkoxy group present in the hole transport layer may result in effects such as improved hole injection.

[0185] Furthermore, when the solvent used to disperse the quantum dots is a long-chain hydrocarbon solvent, it is desirable that the number of carbon atoms in the alkoxy groups contained in the polymer according to the above embodiment be small, from the viewpoint of ensuring solvent resistance of the hole transport layer.

[0186] Therefore, linear or branched alkoxy groups having 1 to 18 carbon atoms are more preferable as the alkoxy group. These alkoxy groups can be selected appropriately depending on the quantum dots used or the solvent in which the quantum dots are dispersed.

[0187] In the above formula (L1), Ar a This is a group represented by the following formula (L1-a). In the above formula (L1), multiple Ar a They may be the same or different, but it is preferable that they be different. In the above formula (L1), multiple Ar a They may be joined together to form a ring.

[0188] [ka]

[0189] In the above formula (L1-a), R is independently a hydrogen atom, a deuterium atom, or a monovalent organic group. In the above formula (L1-a), multiple Rs may form a ring with each other. Here, the monovalent organic group is not particularly limited, but preferably a linear or branched alkyl group having 1 to 24 carbon atoms. Also, in the above formula (L1-a), n is an integer between 0 and 3, preferably an integer between 0 and 2, and more preferably 0 or 1. Also, in the above formula (L1-a), * represents a bonding site with an adjacent atom.

[0190] In the above formula (L1-a), if multiple Rs form a ring, the multiple Rs may also bond to each other to form a ring.

[0191] In the above formula (L1-a), when multiple R groups form a ring, it is preferable that the multiple R groups forming the ring share one aryl group or heteroaryl group to form the ring.

[0192] Specific examples of linear or branched alkyl groups having 1 to 24 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, tert-pentyl group, neopentyl group, 1,2-dimethylpropyl group, n-hexyl group, isohexyl group, 1,3-dimethylbutyl group, 1-isopropylpropyl group, 1,2-dimethylbutyl group, n-heptyl group, 1,4-dimethylpentyl group, 3-ethylpentyl group, 2-methyl-1-isopropylpropyl group, and 1-ethyl-3-methylbutyl group. Examples include 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, n-octadecyl group, n-nonadecyl group, n-eicosyl group, n-heneicosyl group, n-docosyl group, n-tricosyl group, and n-tetracosyl group.

[0193] The number of carbon atoms in the above alkyl group is more preferably in the following forms.

[0194] For example, if the ligand of the quantum dot is a long-chain alkyl-containing compound such as oleic acid, oleylamine, or trioctylphosphine, it is desirable that the compound contained in the hole transport layer also contains a long-chain alkyl group. This is because the interaction between the ligand of the quantum dot and the alkyl group present in the hole transport layer may result in effects such as improved hole injection.

[0195] Furthermore, when the solvent used to disperse the quantum dots is a long-chain hydrocarbon solvent, it is desirable that the number of carbon atoms in the alkyl group contained in the polymer according to the above embodiment be small, from the viewpoint of ensuring the residual film rate of the hole transport layer.

[0196] Therefore, linear or branched alkyl groups having 1 to 18 carbon atoms are more preferable as the alkyl group. The alkyl group can be selected appropriately depending on the quantum dots used or the solvent in which the quantum dots are dispersed.

[0197] From the perspective of further improving the advantageous effects of adding low molecular weight materials, Ar a It is preferable that the group is selected from the following group L1-A. In the following group L1-A, R' is a linear or branched alkyl group having 1 to 24 carbon atoms, preferably a linear alkyl group having 1 to 16 carbon atoms. In the following group L1-A, * represents a bonding site with an adjacent atom.

[0198] [ka]

[0199] From the perspective of further improving the advantageous effects of adding low molecular weight materials, Ar a It is particularly preferable that the group is selected from the following group L1-A'. In group L1-A', dodecyl represents an n-dodecyl group. Also, * represents a bonding site with an adjacent atom.

[0200] [ka]

[0201] In the above formula (L1), Ar b This is a group represented by the following formula (L1-b).

[0202] [ka]

[0203] In the above formula (L1-b), R is independently a hydrogen atom, a deuterium atom, or a monovalent organic group. In the above formula (L1-b), multiple Rs may form a ring. From the viewpoint of further improving the advantageous effects of using low molecular weight materials, in the above formula (L1-b), R is preferably a hydrogen atom.

[0204] In the above formula (L1-b), if multiple Rs form a ring, the multiple Rs may also bond to each other to form a ring.

[0205] In the above formula (L1-b), when multiple R groups form a ring, it is preferable that the multiple R groups forming the ring share one aryl group or heteroaryl group to form the ring.

[0206] In the above formula (L1-b), m is an integer between 0 and 2, preferably 1 or 2, and more preferably 1. In the above formula (L1-b), * represents a bonding site with an adjacent atom.

[0207] In the above formula (L1), Ar b It is preferable that the group is selected from the following groups L1-B. In the following groups L1-B, each R' is independently a linear or branched alkyl group having 1 to 24 carbon atoms. In the following groups L1-B, multiple R's may bond to each other to form a ring. Also, in the following groups L1-B, * represents a bonding site with an adjacent atom. In particular, from the viewpoint of further improving the advantageous effects of adding low molecular weight materials, Ar b It is particularly preferable that the group is a paraphenylene group.

[0208] The number of carbon atoms in the above alkyl group is more preferably in the following forms.

[0209] For example, if the ligand of the quantum dot is a long-chain alkyl-containing compound such as oleic acid, oleylamine, or trioctylphosphine, it is desirable that the compound contained in the hole transport layer also contains a long-chain alkyl group. This is because the interaction between the ligand of the quantum dot and the alkyl group present in the hole transport layer may result in effects such as improved hole injection.

[0210] Furthermore, when the solvent used to disperse the quantum dots is a long-chain hydrocarbon solvent, it is desirable that the number of carbon atoms in the alkyl group contained in the polymer according to the above embodiment be small, from the viewpoint of ensuring solvent resistance of the hole transport layer.

[0211] Therefore, linear or branched alkyl groups having 1 to 18 carbon atoms are more preferable as the alkyl group. The alkyl group can be selected appropriately depending on the quantum dots used or the solvent in which the quantum dots are dispersed.

[0212] [ka]

[0213] Low molecular weight compound 1 is a compound represented by one of the following chemical formulas (L1-1) to (L1-3) It is preferable that it be a physical object.

[0214] [ka]

[0215] In the above equations (L1-1) to (L1-3), R and Ar a and Ar b The definition is given by the above formula (L This is the same definition as in 1).

[0216] A specific example of low molecular weight compound 1 is the compound represented by the following chemical formula. Compound 1 may be used alone or in combination of two or more compounds.

[0217] [ka]

[0218] Low molecular weight compound 1 can be synthesized using known organic synthesis methods.

[0219] (Low molecular compound 2) Low molecular weight compound 2 is a compound represented by the following formula (L2).

[0220] [ka]

[0221] In the above formula (L2), Ar a This is a group represented by the following formula (L2-a).

[0222] [ka]

[0223] In the above formula (L2-a), R is independently a hydrogen atom, a deuterium atom, or a monovalent organic group. In the above formula (L2-a), multiple Rs may bond to each other to form a ring. In the above formula (L2-a), Z is a linear or branched alkyl group having 1 to 12 carbon atoms, preferably a linear alkyl group having 4 to 12 carbon atoms. In the above formula (L2-a), * represents a bonding site with an adjacent atom.

[0224] From the viewpoint of further improving the advantageous effects of adding low molecular weight materials, in the above formula (L2), Ar a It is preferable that the group is represented by the following formula (L2-a').

[0225] [ka]

[0226] In formula (L2-a') above, Z has the same definition as in formula (L2-a) above. In formula (L2-a') above, R' is a hydrogen atom or a methyl group. In formula (L2-a') above, * represents a bond site with an adjacent atom.

[0227] From the viewpoint of further improving the effects of the present invention, Ar a It is more preferable that the group is selected from the following group L2-A. In the following group L2-A, * represents a bonding site with an adjacent atom.

[0228] [ka]

[0229] In the above formula (L2), X is a group represented by the following formula (L2-b). In the above formula (L2), the multiple Xs may be the same or different. In the above formula (L2), the multiple Xs may be bonded to each other to form a ring.

[0230] [ka]

[0231] In the above formula (L2-b), R is independently a hydrogen atom, a deuterium atom, or a monovalent organic group. In the above formula (L2-b), multiple Rs may bond to each other to form a ring. Also, in the above formula (L2-b), n is an integer between 0 and 3, preferably between 0 and 2. Also, in the above formula (L2-b), * represents a bonding site with an adjacent atom.

[0232] From the viewpoint of further enhancing the advantageous effects of adding low molecular weight materials, X is preferably a group selected from the following group L2-B. In the following group L2-B, each R' is independently a linear or branched alkyl group having 1 to 24 carbon atoms. In the following group L2-B, multiple R's may bond to each other to form a ring. Also, in the following group L2-B, * represents a bonding site with an adjacent atom.

[0233] The number of carbon atoms in the above alkyl group is more preferably in the following forms.

[0234] For example, if the ligand of the quantum dot is a long-chain alkyl-containing compound such as oleic acid, oleylamine, or trioctylphosphine, it is desirable that the compound contained in the hole transport layer also contains a long-chain alkyl group. This is because the interaction between the ligand of the quantum dot and the alkyl group present in the hole transport layer may result in effects such as improved hole injection.

[0235] Furthermore, when the solvent used to disperse the quantum dots is a long-chain hydrocarbon solvent, it is desirable that the number of carbon atoms in the alkyl group contained in the polymer according to the above embodiment be small, from the viewpoint of ensuring solvent resistance of the hole transport layer.

[0236] Therefore, linear or branched alkyl groups having 1 to 18 carbon atoms are more preferable as the alkyl group. The alkyl group can be selected appropriately depending on the quantum dots used or the solvent in which the quantum dots are dispersed.

[0237] [ka]

[0238] From the viewpoint of further improving the advantageous effects of adding low molecular weight materials, in the above formula (L2), Ar a The group (-NX2) to be linked is preferably a group selected from the following group L2-B'. In the above formula (L2), multiple Ar a The base (-NX2) connected to it may be the same but different. It is also acceptable. In the group L2-B' below, * represents Ar in the above formula (L2). a The joint It indicates rank.

[0239] [ka]

[0240] A specific example of low molecular weight compound 2 is the compound represented by the following chemical formula. Compound 2 may be used alone or in combination of two or more compounds.

[0241] [ka]

[0242] Low molecular weight compound 2 can be synthesized using known organic synthesis methods.

[0243] (Low molecular compound 3) A low molecular weight material according to a preferred embodiment of the present invention may also include, for example, a low molecular weight compound represented by the following formula (L3) (hereinafter also referred to as "low molecular weight compound 3"). Low molecular weight compound 3 is a hole transport material, and when used in combination with the polymer according to the above embodiment, low molecular weight compound 3 exists in such a way that it fits into the gaps of the polymer according to the above embodiment. As a result, a denser hole transport layer is formed, and the hole transport ability of the hole transport layer is improved. Furthermore, since the hole transport ability of the low molecular weight compound 3 itself, which is the added hole transport material, is imparted to the hole transport layer, an effect of further improving hole transportability is obtained. According to a more preferred embodiment, the low molecular weight material includes low molecular weight compound 3.

[0244] The following describes low-molecular-weight compound 3.

[0245] (Low molecular compound 3) Low molecular weight compound 3 is a compound represented by the following formula (L3).

[0246] [ka]

[0247] In the above formula (L3), R1 to R3 are each independently a hydrogen atom, a monovalent hydrocarbon group, or a monovalent aromatic hydrocarbon group. R1 to R3 may be the same or different. In addition, in the above formula (L3), two R1s may be bonded to each other to form a ring. Here, the monovalent hydrocarbon group is not particularly limited, but linear or branched alkyl groups, alkenyl groups and alkynyl groups, and cyclic alkyl groups (cycloalkyl groups) are preferred. The alkyl group is preferably a linear or branched alkyl group having 1 to 20 carbon atoms. Such alkyl groups are not limited to the following, but include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, tert-pentyl group, neopentyl group, 1,2-dimethylpropyl group, n-hexyl group, isohexyl group, 1,3-dimethylbutyl group, 1-isopropylpropyl group, 1,2-dimethylbutyl group, n-heptyl group, 1,4-dimethylpentyl group, 3-ethylpentyl group, 2-methyl-1- Examples include 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, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, and n-octadecyl group.

[0248] The number of carbon atoms in the above alkyl group is more preferably in the following forms.

[0249] For example, if the ligand of the quantum dot is a long-chain alkyl-containing compound such as oleic acid, oleylamine, or trioctylphosphine, it is desirable that the compound contained in the hole transport layer also contains a long-chain alkyl group. This is because the interaction between the ligand of the quantum dot and the alkyl group present in the hole transport layer may result in effects such as improved hole injection.

[0250] Furthermore, when the solvent used to disperse the quantum dots is a long-chain hydrocarbon solvent, it is desirable that the number of carbon atoms in the alkyl group contained in the polymer according to the above embodiment be small, from the viewpoint of ensuring solvent resistance of the hole transport layer.

[0251] Therefore, linear or branched alkyl groups having 1 to 18 carbon atoms are more preferable as the alkyl group. The alkyl group can be selected appropriately depending on the quantum dots used or the solvent in which the quantum dots are dispersed.

[0252] The alkenyl group is preferably a linear or branched alkenyl group having 2 to 12 carbon atoms. Examples of such alkenyl groups, but not limited to the following, include vinyl, allyl, 1-propenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, and isopropenyl groups. The alkynyl group is preferably a linear or branched alkynyl group having 2 to 12 carbon atoms. Examples of such alkynyl groups, but not limited to the following, include ethynyl and propargyl groups. The cycloalkyl group is preferably a cycloalkyl group having 3 to 12 carbon atoms. Examples of such cycloalkyl groups, but not limited to the following, include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups. The monovalent aromatic hydrocarbon group is not particularly limited, but aromatic hydrocarbon groups having 6 to 25 carbon atoms are preferred. Aromatic hydrocarbon groups having 6 to 25 carbon atoms are not limited to the following, but examples include monovalent groups derived from aromatic hydrocarbons such as benzene (phenyl group), indene, naphthalene, anthracene, azulene, heptalene, acenaphthene, phenalene, fluorene, anthraquinoline, phenanthrine, biphenyl, terphenyl, quaterphenyl, quinkiphenyl, sexiphenyl, pyrene, 9,9-diphenylfluorene, and 9,9'-spirobi[fluorene]. From the viewpoint of further improving the advantageous effects of adding low molecular weight materials, R1 is preferably independently a hydrogen atom or a linear or branched alkyl group, phenyl group, or biphenyl group having 1 to 12 carbon atoms, more preferably a linear or branched alkyl group, phenyl group, or biphenyl group having 3 to 10 carbon atoms, and particularly preferably a linear alkyl group or phenyl group having 5 to 8 carbon atoms. Furthermore, from the viewpoint of further enhancing the advantageous effects of adding low molecular weight materials, R2 to R3 are each preferably independently a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms, preferably a hydrogen atom or a linear alkyl group having 1 to 3 carbon atoms, and particularly preferably a hydrogen atom.

[0253] In other words, from the viewpoint of further improving the advantageous effects of adding low molecular weight materials, the structure of formula (L3) excluding X1 and X2 (i.e., as shown below):

[0254] [ka]

[0255] The structure of the following is preferably selected from the following group. In the following, "Alkyl" means "unsubstituted (i.e., Alkyl = hydrogen atom) or substituted with an alkyl group". Preferably, "Alkyl" means substituted with a linear or branched alkyl group having 1 to 12 carbon atoms. More preferably, "Alkyl" means substituted with a linear alkyl group having 5 to 8 carbon atoms. Also, "Alkyl" may be the same alkyl group or different alkyl groups. In the following structure, * represents a bonding site with an adjacent atom.

[0256] [ka]

[0257] In the above formula (L3), X1 is a hydrogen atom or a group represented by the following formula (L3-a). Also, X2 is a group represented by the following formula (L3-a). That is, low molecular weight compound 3 has one or two groups represented by the following formula (L3-a). In the following formula (L3-a), "*" represents the site where X1 or X2 is attached to the fluorene ring in formula (L3).

[0258] [ka]

[0259] In the above formula (L3-a), each R is independently a hydrogen atom or a monovalent hydrocarbon group. Note that multiple Rs may be the same or different. Furthermore, in the above formula (L3-a), Rs may be bonded to each other to form a ring. Here, there are no particular limitations on specific examples of monovalent hydrocarbon groups, but the definition is the same as that for R1 to R3 in the above formula (L3). Of these, from the viewpoint of further improving the advantageous effects of adding low molecular weight materials, each R is preferably independently a hydrogen atom or a linear or branched alkyl group having 1 to 12 carbon atoms, and more preferably a hydrogen atom or a linear or branched alkyl group having 3 to 10 carbon atoms.

[0260] Furthermore, in the above formula (L3-a), l, m, and n are each independent integers between 0 and 3. From the viewpoint of further improving the advantageous effects of adding low molecular weight materials, l is preferably an integer between 0 and 2, more preferably 0 or 1. Furthermore, from the viewpoint of further improving the advantageous effects of adding low molecular weight materials, n and m are preferably integers between 0 and 2, more preferably 0 or 2.

[0261] In the above formula (L3-a), the two terminal phenyl groups may be bonded together to form a carbazole ring, as in the low molecular weight compound (L3-2) below.

[0262] In other words, from the viewpoint of further improving the advantageous effects of adding low molecular weight materials, it is preferable that the group represented by the above formula (L3-a) has one of the structures selected from the following group L3-A. In the following group L3-A, * represents a bonding site with an adjacent atom.

[0263] [ka]

[0264] [ka]

[0265] [ka]

[0266] The low molecular weight compound 3 is preferably a compound represented by any of the following chemical formulas (L3-1) to (L3-10).

[0267] [ka]

[0268] [ka]

[0269] Low molecular weight compound 3 can be synthesized using known organic synthesis methods.

[0270] (Low molecular compound 4) A low molecular weight material according to a preferred embodiment of the present invention may also include, for example, a low molecular weight compound represented by the following formula (L4) (hereinafter also referred to as "low molecular weight compound 4"). When low molecular weight compound 4 is used in combination with the polymer according to the above embodiment, low molecular weight compound 4 exists in such a way that it fits into the gaps of the polymer according to the above embodiment. As a result, a denser hole transport layer is formed, and the hole transport capacity of the hole transport layer is improved. According to a more preferred embodiment, the low molecular weight material includes low molecular weight compound 4.

[0271] The following describes low-molecular-weight compound 4.

[0272] Low molecular weight compound 4 is a compound represented by the following formula (L4). When the low molecular weight material includes a wide-gap material, it is preferable that the wide-gap material includes at least one low molecular weight compound 4 represented by the following formula (L4). Low molecular weight compound 4 may have hole transport properties.

[0273] [ka]

[0274] In the above formula (L4), Ar a This is a group represented by the following formula (L4-a).

[0275] [ka]

[0276] In the above formula (L4-a), R is independently a hydrogen atom, a deuterium atom, or a monovalent organic group. In the above formula (L4-a), multiple Rs may be bonded to each other to form a ring. In the above formula (L4-a), Z is a linear or branched alkyl group having 1 to 12 carbon atoms, preferably a linear alkyl group having 4 to 12 carbon atoms. In the above formula (L4-a), * represents a bonding site with an adjacent atom.

[0277] From the viewpoint of further improving the advantageous effects of adding low molecular weight materials, in the above formula (L4), Ar a It is preferable that the group is represented by the following formula (L4-a').

[0278] [ka]

[0279] In formula (L4-a') above, Z has the same definition as in formula (L4-a). In formula (L4-a') above, R' is a hydrogen atom or a methyl group. In formula (L4-a') above, * represents a bond site with an adjacent atom.

[0280] From the viewpoint of further improving the effects of the present invention, Ar a It is more preferable that the group is selected from the following group L4-A. In the following group L4-A, * represents a bonding site with an adjacent atom.

[0281] [ka]

[0282] In the above formula (L4), X is a group represented by the following formula (L4-b). In the above formula (L4), the multiple Xs may be the same or different. In the above formula (L4), the multiple Xs may be bonded to each other to form a ring.

[0283] [ka]

[0284] In the above formula (L4-b), R is independently a hydrogen atom, a deuterium atom, or a monovalent organic group. In the above formula (L4-b), multiple Rs may bond to each other to form a ring. Also, in the above formula (L4-b), n is an integer between 0 and 3, preferably between 0 and 2. Also, in the above formula (L4-b), * represents a bonding site with an adjacent atom.

[0285] From the viewpoint of further enhancing the advantageous effects of adding low molecular weight materials, X is preferably a group selected from the following group L4-B. In the following group L4-B, each R' is independently a linear or branched alkyl group having 1 to 24 carbon atoms. In the following group L4-B, multiple R's may bond to each other to form a ring. Also, in the following group L4-B, * represents a bonding site with an adjacent atom.

[0286] The number of carbon atoms in the above alkyl group is more preferably in the following forms.

[0287] For example, if the ligand of the quantum dot is a long-chain alkyl-containing compound such as oleic acid, oleylamine, or trioctylphosphine, it is desirable that the compound contained in the hole transport layer also contains a long-chain alkyl group. This is because the interaction between the ligand of the quantum dot and the alkyl group present in the hole transport layer may result in effects such as improved hole injection.

[0288] Furthermore, when the solvent used to disperse the quantum dots is a long-chain hydrocarbon solvent, it is desirable that the number of carbon atoms in the alkyl group contained in the polymer according to the above embodiment be small, from the viewpoint of ensuring solvent resistance of the hole transport layer.

[0289] Therefore, linear or branched alkyl groups having 1 to 18 carbon atoms are more preferable as the alkyl group. The alkyl group can be selected appropriately depending on the quantum dots used or the solvent in which the quantum dots are dispersed.

[0290] [ka]

[0291] A specific example of low molecular weight compound 4 is the compound represented by the following chemical formula. Compound 4 may be used alone or in combination of two or more compounds.

[0292] [ka]

[0293] Low molecular weight compound 4 can be synthesized using known organic synthesis methods.

[0294] (Low molecular compounds 5, 6) Examples of low molecular weight materials according to one preferred embodiment of the present invention include a low molecular weight compound represented by the following formula (L5) (hereinafter also referred to as "low molecular weight compound 5") and a low molecular weight compound represented by the following formula (L6) (hereinafter also referred to as "low molecular weight compound 6"). When low molecular weight compounds 5 and 6 are used in combination with the polymer according to the above embodiment, the low molecular weight compounds 5 and 6 are present in such a way that they fit into the gaps of the polymer according to the above embodiment, resulting in a denser hole transport layer and improving the hole transport capacity of the hole transport layer. According to a more preferred embodiment, the low molecular weight material includes low molecular weight compound 5, low molecular weight compound 6, or a combination thereof.

[0295] The following describes low-molecular-weight compounds 5 and 6.

[0296] (Low molecular compound 5) Low molecular weight compound 5 is a compound represented by the following formula (L5). When the low molecular weight material includes a wide-gap material, it is preferable that the wide-gap material includes at least one low molecular weight compound 5 represented by the following formula (L5). Low molecular weight compound 5 may also have hole transport properties.

[0297] [ka]

[0298] In the above equation (L5), m and n each independently represent integers between 0 and 3 (inclusive). Each R independently represents a hydrogen atom or a monovalent organic group, and two or more Rs may condense or bond to form a ring. X represents O, S, NR', C(R")2, or a divalent organic group other than NR' and C(R")2. R' and R'' each independently represent a hydrogen atom or a monovalent organic group.

[0299] In the above formula (L5), the monovalent organic group that can constitute R is not particularly limited. Examples include a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, an alkylamino group having a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group having 6 to 30 carbon atoms, or a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 30 ring-forming atoms.

[0300] Aromatic hydrocarbon ring groups having 6 to 30 carbon atoms that can constitute R are groups derived from hydrocarbon (aromatic hydrocarbon) rings having a carbon ring containing one or more aromatic rings having 6 to 30 carbon atoms. Furthermore, if an aromatic hydrocarbon ring group contains two or more rings, the two or more rings may be fused to each other. In addition, one or more hydrogen atoms present in these aromatic hydrocarbon ring groups may be substituted with substituents.

[0301] The aromatic hydrocarbon rings constituting the aromatic hydrocarbon ring group are not particularly limited, but specific examples include benzene, indene, naphthalene, anthracene, azulene, heptalene, acenaphthalene, phenalene, fluorene, phenanthrene, biphenyl, triphenylene, pyrene, chrysene, picene, perylene, pentaphene, pentacene, tetrafen, hexaphene, hexacene, rubicene, trinaphthylene, heptafen, pyranthrene, and the like.

[0302] A monovalent aromatic heterocyclic group with 3 to 30 ring-forming atoms that can constitute R is a group derived from a ring (aromatic heterocycle) with 3 to 30 ring-forming atoms, containing one or more aromatic rings having one or more heteroatoms (e.g., nitrogen (N), oxygen (O), phosphorus (P), sulfur (S)) and the remaining ring atoms being carbon atoms (C). Furthermore, if the aromatic heterocyclic group contains two or more rings, the two or more rings may be fused to each other. In addition, one or more hydrogen atoms present in these aromatic heterocyclic groups may be substituted with substituents.

[0303] Here, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself in a compound having a structure in which atoms are bonded in a ring (e.g., a monocycle, a fused ring, or a ring assembly). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of atoms that constitute a ring) and atoms included in substituents when the ring is substituted are not included in the number of ring-forming atoms. For example, the carbazolyl group (a substituent composed of carbazoline) has a number of ring-forming atoms of 13.

[0304] The aromatic heterocycles constituting the aromatic heterocyclic group are not particularly limited, but examples include π-electron-deficient aromatic heterocycles, π-electron-excess aromatic heterocycles, and π-electron-deficient-π-electron-excess mixed aromatic heterocycles obtained by mixing π-electron-deficient aromatic heterocycles and π-electron-excess aromatic heterocycles.

[0305] Specific examples of π-electron-deficient aromatic heterocycles include pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, naphthyridine, acridine, phenazine, benzoquinoline, benzoisoquinoline, phenanthridine, phenanthroline, benzoquinone, coumarin, anthraquinone, and fluorenone.

[0306] Specific examples of π-electron-rich aromatic heterocycles include furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, pyrrole, indole, and carbazole.

[0307] Specific examples of π-electron-deficient-π-electron-excess mixed aromatic heterocycles include imidazole, benzimidazole, pyrazole, indazole, oxazole, isoxazole, benzoxazole, benzoisoxazole, thiazole, isothiazole, benzothiazole, benzoisothiazole, imidazolinone, benzimidazolinone, imidazopyridine, imidazopyrimidine, imidazophenanthlysine, benzimidazphenanthlysine, azadibenzofuran, azacarbazole, azadibenzothiophene, diazadibenzofuran, diazacarbazole, diazadibenzothiophene, xanthone, thioxanthone, and the like.

[0308] The alkyl groups having 1 to 30 carbon atoms that can constitute R are not particularly limited. For example, linear or branched alkyl groups having 1 to 30 carbon atoms. Specifically, these include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, tert-pentyl group, neopentyl group, 1,2-dimethylpropyl group, n-hexyl group, isohexyl group, 1,3-dimethylbutyl group, 1-isopropylpropyl group, 1,2-dimethylbutyl group, n-heptyl group, 1,4-dimethylpentyl group, 3-ethylpentyl group, 2-methyl-1-isopropylpropyl group, 1-ethyl-3-methylbutyl group, n-octyl group, 2-ethylpentyl group. Examples include the hexyl 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, n-octadecyl group, n-nonadecyl group, n-eicosyl group, n-heneicosyl group, n-docosyl group, n-tricosyl group, and n-tetracosyl group.

[0309] The number of carbon atoms in the above alkyl group is more preferably in the following forms.

[0310] For example, if the ligand of the quantum dot is a long-chain alkyl-containing compound such as oleic acid, oleylamine, or trioctylphosphine, it is desirable that the compound contained in the hole transport layer also contains a long-chain alkyl group. This is because the interaction between the ligand of the quantum dot and the alkyl group present in the hole transport layer may result in effects such as improved hole injection.

[0311] Furthermore, when the solvent used to disperse the quantum dots is a long-chain hydrocarbon solvent, it is desirable that the number of carbon atoms in the alkyl group contained in the polymer according to the above embodiment be small, from the viewpoint of ensuring solvent resistance of the hole transport layer.

[0312] Therefore, linear or branched alkyl groups having 1 to 18 carbon atoms are more preferable as the alkyl group. The alkyl group can be selected appropriately depending on the quantum dots used or the solvent in which the quantum dots are dispersed.

[0313] The alkoxy groups having 1 to 30 carbon atoms that can constitute R are not particularly limited. For example, linear or branched alkoxy groups having 1 to 30 carbon atoms. Specifically, examples 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.

[0314] The number of carbon atoms in the above-mentioned alkoxy group is more preferably in the following configurations.

[0315] For example, if the ligand of the quantum dot is a long-chain alkyl-containing compound such as oleic acid, oleylamine, or trioctylphosphine, it is desirable that the compound contained in the hole transport layer also contains a long-chain acoxy group. This is because the interaction between the ligand of the quantum dot and the alkoxy group present in the hole transport layer may result in effects such as improved hole injection.

[0316] Furthermore, when the solvent used to disperse the quantum dots is a long-chain hydrocarbon solvent, it is desirable that the number of carbon atoms in the alkoxy groups contained in the polymer according to the above embodiment be small, from the viewpoint of ensuring solvent resistance of the hole transport layer.

[0317] Therefore, linear or branched alkoxy groups having 1 to 18 carbon atoms are more preferable as the alkoxy group. These alkoxy groups can be selected appropriately depending on the quantum dots used or the solvent in which the quantum dots are dispersed.

[0318] The aryloxy group having 6 to 30 carbon atoms that can constitute R is not particularly limited. For example, it may be a monocyclic or condensed polycyclic aryloxy group having 6 to 30 carbon atoms that may contain a heteroatom. Specifically, examples include phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 2-azlenyloxy group, 2-furanyloxy group, 2-thienyloxy group, 2-indolyloxy group, 3-indolyloxy group, 2-benzofuryloxy group, 2-benzothienyloxy group, and the like.

[0319] The alkylamino group having an alkyl group with 1 to 30 carbon atoms that can constitute R is not particularly limited. For example, it is an alkylamino group having a linear or branched alkyl group with 1 to 30 carbon atoms. Specifically, examples include N-alkylamino groups such as N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, N-pentylamino group, and N-hexylamino group, and N,N-dialkylamino groups such as N,N,N-dimethylamino group, N-methyl-N-ethylamino group, N,N-diethylamino group, N,N-dipropylamino group, N,N-diisopropylamino group, N,N-dibutylamino group, N,N-diisobutylamino group, N,N-dipentylamino group, and N,N-dihexylamino group.

[0320] Furthermore, there are no particular restrictions on other substituents that further substitute R with alkyl groups having 1 to 30 carbon atoms, alkoxy groups having 1 to 30 carbon atoms, aryloxy groups having 6 to 30 carbon atoms, alkylamino groups having 1 to 30 carbon atoms, cyano groups, monovalent aromatic hydrocarbon ring groups having 6 to 30 carbon atoms, or monovalent aromatic heterocyclic ring groups having 3 to 30 ring-forming atoms. Other substituents are, for example, the same as substituents that can constitute R. That is, hydrogen atoms, cyano groups, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, alkoxy groups having 1 to 30 carbon atoms, aryloxy groups having 6 to 30 carbon atoms, alkylamino groups having 1 to 30 carbon atoms, monovalent aromatic hydrocarbon ring groups having 6 to 30 carbon atoms, monovalent aromatic heterocyclic ring groups having 3 to 30 ring-forming atoms, etc. The description of other substituents is the same as the description of R above, so the description is omitted.

[0321] Furthermore, other substituents that further substitute for other substituents, and even more substituents that further substitute for other substituents, are treated the same as these other substituents.

[0322] In the above formula (L5), R' and R'' in NR', C(R''2), which can constitute X, are not particularly limited. Examples include hydrogen atoms, cyano groups, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted amino groups having 1 to 30 carbon atoms, substituted or unsubstituted monovalent aromatic hydrocarbon ring groups having 6 to 30 carbon atoms, or substituted or unsubstituted monovalent aromatic heterocyclic groups having 3 to 30 ring-forming atoms.

[0323] The explanation of the monovalent organic groups that can constitute R' and R'' is the same as the explanation for R above, so the explanation is omitted.

[0324] There are no particular restrictions on the divalent organic groups that can constitute X or other than NR' and C(R)2.

[0325] Here, in the compound represented by the above formula (L5), it is preferable that m and n are each independent integers between 1 and 3. Furthermore, it is more preferable that m and n are each independent integers between 2 and 3, and even more preferable that they are 3.

[0326] Furthermore, the compound represented by the above formula (L5) is the compound represented by the following chemical formula (L5-A) It is preferable that it be a physical object.

[0327] [ka]

[0328] In equation (L5-A) above, R and X are the same as in equation (L5) above.

[0329] In the above formulas (L5) and (L5-A), R is preferably independently a hydrogen atom, a cyano group, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an alkylamino group having an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted monovalent aromatic hydrocarbon ring group having 6 to 30 carbon atoms, or an unsubstituted monovalent aromatic heterocyclic group having 3 to 30 ring-forming atoms. Furthermore, it is even more preferable that R is independently a hydrogen atom, a cyano group, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, or an alkylamino group having an unsubstituted alkyl group having 1 to 30 carbon atoms. And it is even more preferable that R is entirely a hydrogen atom.

[0330] In the above formulas (L5) and (L5-A), R' is preferably a hydrogen atom, a cyano group, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted amino group having 1 to 30 carbon atoms, an unsubstituted monovalent aromatic hydrocarbon ring group having 6 to 30 carbon atoms, or an unsubstituted monovalent aromatic heterocyclic group having 3 to 30 ring-forming atoms. Furthermore, it is even more preferable that each of R' independently consists of a hydrogen atom, a cyano group, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, or an alkylamino group having an unsubstituted alkyl group having 1 to 30 carbon atoms. And it is even more preferable that all of R' are hydrogen atoms.

[0331] In the above formulas (L5) and (L5-A), R'' is preferably independently a hydrogen atom, a cyano group, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an alkylamino group having an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted monovalent aromatic hydrocarbon ring group having 6 to 30 carbon atoms, or an unsubstituted monovalent aromatic heterocyclic group having 3 to 30 ring-forming atoms. Furthermore, it is even more preferable that R'' is independently a hydrogen atom, a cyano group, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, or an unsubstituted amino group having 1 to 30 carbon atoms. And it is even more preferable that R'' is entirely a hydrogen atom.

[0332] The number of carbon atoms in the above alkyl group is more preferably in the following forms.

[0333] For example, if the ligand of the quantum dot is a long-chain alkyl-containing compound such as oleic acid, oleylamine, or trioctylphosphine, it is desirable that the compound contained in the hole transport layer also contains a long-chain alkyl group. This is because the interaction between the ligand of the quantum dot and the alkyl group present in the hole transport layer may result in effects such as improved hole injection.

[0334] Furthermore, when the solvent used to disperse the quantum dots is a long-chain hydrocarbon solvent, it is desirable that the number of carbon atoms in the alkyl group contained in the polymer according to the above embodiment be small, from the viewpoint of ensuring solvent resistance of the hole transport layer.

[0335] Therefore, linear or branched alkyl groups having 1 to 18 carbon atoms are more preferable as the alkyl group. The alkyl group can be selected appropriately depending on the quantum dots used or the solvent in which the quantum dots are dispersed.

[0336] The number of carbon atoms in the above-mentioned alkoxy group is more preferably in the following configurations.

[0337] For example, if the ligand of the quantum dot is a long-chain alkyl-containing compound such as oleic acid, oleylamine, or trioctylphosphine, it is desirable that the compound contained in the hole transport layer also contains a long-chain acoxy group. This is because the interaction between the ligand of the quantum dot and the alkoxy group present in the hole transport layer may result in effects such as improved hole injection.

[0338] Furthermore, when the solvent used to disperse the quantum dots is a long-chain hydrocarbon solvent, it is desirable that the number of carbon atoms in the alkoxy groups contained in the polymer according to the above embodiment be small, from the viewpoint of ensuring the solvent resistance rate of the hole transport layer.

[0339] Therefore, linear or branched alkoxy groups having 1 to 18 carbon atoms are more preferable as the alkoxy group. These alkoxy groups can be selected appropriately depending on the quantum dots used or the solvent in which the quantum dots are dispersed.

[0340] In the above formulas (L5) and (L5-A), X is preferably O, S, NR', or C(R")2. More preferably, X is O or S, and even more preferably S.

[0341] The following are specific examples of low-molecular-weight compound 5. However, low-molecular-weight compound 5 is not limited to these specific examples.

[0342] [ka]

[0343] [ka]

[0344] The method for producing the low molecular weight compound 5 is not particularly limited and includes various known synthesis methods. A manufacturing method can be used.

[0345] (Low molecular compound 6) The low molecular weight compound 6 is a compound represented by the following formula (L6). When the low molecular weight material includes a wide-gap material, it is preferable that the wide-gap material includes at least one of the low molecular weight compounds 6 represented by the following formula (L6). The low molecular weight compound 6 may also have hole transport properties.

[0346] [ka]

[0347] In the above equation (L6), m and n each independently represent integers between 0 and 3 (inclusive). Each R independently represents either a hydrogen atom or a monovalent organic group.

[0348] In the above formula (L6), two or more R atoms may condense or bond to form a ring.

[0349] In the above formula (L6), the monovalent organic group that can constitute R is not particularly limited. Examples include a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, an alkylamino group having a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monovalent aromatic hydrocarbon ring group having 6 to 30 carbon atoms, or a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 30 ring-forming atoms.

[0350] Aromatic hydrocarbon ring groups having 6 to 30 carbon atoms that can constitute R are groups derived from hydrocarbon (aromatic hydrocarbon) rings having a carbon ring containing one or more aromatic rings having 6 to 30 carbon atoms. Furthermore, if an aromatic hydrocarbon ring group contains two or more rings, the two or more rings may be fused to each other. In addition, one or more hydrogen atoms present in these aromatic hydrocarbon ring groups may be substituted with substituents.

[0351] The aromatic hydrocarbon rings constituting the aromatic hydrocarbon ring group are not particularly limited, but specific examples include benzene, indene, naphthalene, anthracene, azulene, heptalene, acenaphthalene, phenalene, fluorene, phenanthrene, biphenyl, triphenylene, pyrene, chrysene, picene, perylene, pentaphene, pentacene, tetrafen, hexaphene, hexacene, rubicene, trinaphthylene, heptafen, pyranthrene, and the like.

[0352] A monovalent aromatic heterocyclic group with 3 to 30 ring-forming atoms that can constitute R is a group derived from a ring (aromatic heterocycle) with 3 to 30 ring-forming atoms, containing one or more aromatic rings having one or more heteroatoms (e.g., nitrogen (N), oxygen (O), phosphorus (P), sulfur (S)) and the remaining ring atoms being carbon atoms (C). Furthermore, if the aromatic heterocyclic group contains two or more rings, the two or more rings may be fused to each other. In addition, one or more hydrogen atoms present in these aromatic heterocyclic groups may be substituted with substituents.

[0353] Here, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself in a compound having a structure in which atoms are bonded in a ring (e.g., a monocycle, a fused ring, or a ring assembly). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of atoms that constitute a ring) and atoms included in substituents when the ring is substituted are not included in the number of ring-forming atoms. For example, the carbazolyl group (a substituent composed of carbazoline) has a number of ring-forming atoms of 13.

[0354] The aromatic heterocycles constituting the aromatic heterocyclic group are not particularly limited, but examples include π-electron-deficient aromatic heterocycles, π-electron-excess aromatic heterocycles, and π-electron-deficient-π-electron-excess mixed aromatic heterocycles obtained by mixing π-electron-deficient aromatic heterocycles and π-electron-excess aromatic heterocycles.

[0355] Specific examples of π-electron-deficient aromatic heterocycles include pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, naphthyridine, acridine, phenazine, benzoquinoline, benzoisoquinoline, phenanthridine, phenanthroline, benzoquinone, coumarin, anthraquinone, and fluorenone.

[0356] Specific examples of π-electron-rich aromatic heterocycles include furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, pyrrole, indole, and carbazole.

[0357] Specific examples of π-electron-deficient-π-electron-excess mixed aromatic heterocycles include imidazole, benzimidazole, pyrazole, indazole, oxazole, isoxazole, benzoxazole, benzoisoxazole, thiazole, isothiazole, benzothiazole, benzoisothiazole, imidazolinone, benzimidazolinone, imidazopyridine, imidazopyrimidine, imidazophenanthlysine, benzimidazphenanthlysine, azadibenzofuran, azacarbazole, azadibenzothiophene, diazadibenzofuran, diazacarbazole, diazadibenzothiophene, xanthone, thioxanthone, and the like.

[0358] In a group where two or more monovalent aromatic hydrocarbon ring groups having 6 to 30 carbon atoms or monovalent aromatic heterocyclic ring groups having 3 to 30 ring-forming atoms are bonded together via single bonds, the monovalent aromatic hydrocarbon ring groups having 6 to 30 carbon atoms and the monovalent aromatic heterocyclic ring groups having 3 to 30 ring-forming atoms are as described above, and therefore the explanation is omitted.

[0359] The alkyl groups having 1 to 30 carbon atoms that can constitute R are not particularly limited. For example, linear or branched alkyl groups having 1 to 30 carbon atoms. Specifically, these include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, tert-pentyl group, neopentyl group, 1,2-dimethylpropyl group, n-hexyl group, isohexyl group, 1,3-dimethylbutyl group, 1-isopropylpropyl group, 1,2-dimethylbutyl group, n-heptyl group, 1,4-dimethylpentyl group, 3-ethylpentyl group, 2-methyl-1-isopropylpropyl group, 1-ethyl-3-methylbutyl group, n-octyl group, 2-ethylpentyl group. Examples include the hexyl 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, n-octadecyl group, n-nonadecyl group, n-eicosyl group, n-heneicosyl group, n-docosyl group, n-tricosyl group, and n-tetracosyl group.

[0360] The number of carbon atoms in the above alkyl group is more preferably in the following forms.

[0361] For example, if the ligand of the quantum dot is a long-chain alkyl-containing compound such as oleic acid, oleylamine, or trioctylphosphine, it is desirable that the compound contained in the hole transport layer also contains a long-chain alkyl group. This is because the interaction between the ligand of the quantum dot and the alkyl group present in the hole transport layer may result in effects such as improved hole injection.

[0362] Furthermore, when the solvent used to disperse the quantum dots is a long-chain hydrocarbon solvent, it is desirable that the number of carbon atoms in the alkyl group contained in the polymer according to the above embodiment be small, from the viewpoint of ensuring solvent resistance of the hole transport layer.

[0363] Therefore, linear or branched alkyl groups having 1 to 18 carbon atoms are more preferable as the alkyl group. The alkyl group can be selected appropriately depending on the quantum dots used or the solvent in which the quantum dots are dispersed.

[0364] The alkoxy groups having 1 to 30 carbon atoms that can constitute R are not particularly limited. For example, linear or branched alkoxy groups having 1 to 30 carbon atoms. Specifically, examples 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.

[0365] The number of carbon atoms in the above-mentioned alkoxy group is more preferably in the following configurations.

[0366] For example, if the ligand of the quantum dot is a long-chain alkyl-containing compound such as oleic acid, oleylamine, or trioctylphosphine, it is desirable that the compound contained in the hole transport layer also contains a long-chain alkoxy group. This is because the interaction between the ligand of the quantum dot and the alkoxy group present in the hole transport layer may result in effects such as improved hole injection.

[0367] Furthermore, when the solvent used to disperse the quantum dots is a long-chain hydrocarbon solvent, it is desirable that the number of carbon atoms in the alkoxy groups contained in the polymer according to the above embodiment be small, from the viewpoint of ensuring solvent resistance of the hole transport layer.

[0368] Therefore, linear or branched alkoxy groups having 1 to 18 carbon atoms are more preferable as the alkoxy group. These alkoxy groups can be selected appropriately depending on the quantum dots used or the solvent in which the quantum dots are dispersed.

[0369] The aryloxy group having 6 to 30 carbon atoms that can constitute R is not particularly limited. For example, it may be a monocyclic or condensed polycyclic aryloxy group having 6 to 30 carbon atoms that may contain a heteroatom. Specifically, examples include phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 2-azlenyloxy group, 2-furanyloxy group, 2-thienyloxy group, 2-indolyloxy group, 3-indolyloxy group, 2-benzofuryloxy group, 2-benzothienyloxy group, and the like.

[0370] The alkylamino group having an alkyl group with 1 to 30 carbon atoms that can constitute R is not particularly limited. For example, it is an alkylamino group having a linear or branched alkyl group with 1 to 30 carbon atoms. Specifically, examples include N-alkylamino groups such as N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, N-pentylamino group, and N-hexylamino group, and N,N-dialkylamino groups such as N,N,N-dimethylamino group, N-methyl-N-ethylamino group, N,N-diethylamino group, N,N-dipropylamino group, N,N-diisopropylamino group, N,N-dibutylamino group, N,N-diisobutylamino group, N,N-dipentylamino group, and N,N-dihexylamino group.

[0371] Furthermore, there are no particular restrictions on other substituents that further substitute R, such as alkyl groups having 1 to 30 carbon atoms, alkoxy groups having 1 to 30 carbon atoms, aryloxy groups having 6 to 30 carbon atoms, alkylamino groups having 1 to 30 carbon atoms, monovalent aromatic hydrocarbon ring groups having 6 to 30 carbon atoms, or monovalent aromatic heterocyclic groups having 3 to 30 ring-forming atoms. Other substituents are, for example, the same as substituents that can constitute R. That is, hydrogen atoms, cyano groups, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, alkoxy groups having 1 to 30 carbon atoms, aryloxy groups having 6 to 30 carbon atoms, amino groups having 1 to 30 carbon atoms, monovalent aromatic hydrocarbon ring groups having 6 to 30 carbon atoms, and monovalent aromatic heterocyclic groups having 3 to 30 ring-forming atoms. The explanation of other substituents is the same as the explanation for R above, so the explanation is omitted.

[0372] Furthermore, subsequent substituents that substitute groups present in other substituents, such as further substituents that substitute other substituents, and even further substituents that substitute even more substituents, are treated similarly to these other substituents.

[0373] Furthermore, the compound represented by the above formula (L6) is preferably a compound represented by the following formulas (L6-A), (L6-B), (L6-C), or (L6-D).

[0374] [ka]

[0375] In the above equations (L6-A), (L6-B), (L6-C), and (L6-D), R is the same as in equation (L6) above, Each R' independently represents a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, or an alkylamino group having a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0376] In the above formulas (L6), (L6-A), (L6-B), (L6-C), and (L6-D), R is preferably independently a hydrogen atom, a cyano group, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted amino group having 1 to 30 carbon atoms, an unsubstituted monovalent aromatic hydrocarbon ring group having 6 to 30 carbon atoms, or an unsubstituted monovalent aromatic heterocyclic group having 3 to 30 ring-forming atoms. Furthermore, it is even more preferable that all R are hydrogen atoms.

[0377] In the above formulas (L6-A), (L6-B), (L6-C), and (L6-D), R' is preferably independently a cyano group, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, or an alkylamino group having an unsubstituted alkyl group having 1 to 30 carbon atoms. Furthermore, it is even more preferable that R' consists entirely of hydrogen atoms.

[0378] The number of carbon atoms in the above alkyl group is more preferably in the following forms.

[0379] For example, if the ligand of the quantum dot is a long-chain alkyl-containing compound such as oleic acid, oleylamine, or trioctylphosphine, it is desirable that the compound contained in the hole transport layer also contains a long-chain alkyl group. This is because the interaction between the ligand of the quantum dot and the alkyl group present in the hole transport layer may result in effects such as improved hole injection.

[0380] Furthermore, when the solvent used to disperse the quantum dots is a long-chain hydrocarbon solvent, it is desirable that the number of carbon atoms in the alkyl group contained in the polymer according to the above embodiment be small, from the viewpoint of ensuring solvent resistance of the hole transport layer.

[0381] Therefore, linear or branched alkyl groups having 1 to 18 carbon atoms are more preferable as the alkyl group. The alkyl group can be selected appropriately depending on the quantum dots used or the solvent in which the quantum dots are dispersed.

[0382] The number of carbon atoms in the above-mentioned alkoxy group is more preferably in the following configurations.

[0383] For example, if the ligand of the quantum dot is a long-chain alkyl-containing compound such as oleic acid, oleylamine, or trioctylphosphine, it is desirable that the compound contained in the hole transport layer also contains a long-chain acoxy group. This is because the interaction between the ligand of the quantum dot and the alkoxy group present in the hole transport layer may result in effects such as improved hole injection.

[0384] Furthermore, when the solvent used to disperse the quantum dots is a long-chain hydrocarbon solvent, it is desirable that the number of carbon atoms in the alkoxy groups contained in the polymer according to the above embodiment be small, from the viewpoint of ensuring solvent resistance of the hole transport layer.

[0385] Therefore, linear or branched alkoxy groups having 1 to 18 carbon atoms are more preferable as the alkoxy group. These alkoxy groups can be selected appropriately depending on the quantum dots used or the solvent in which the quantum dots are dispersed.

[0386] Among the compounds represented by the above formulas (L6-A), (L6-B), (L6-C), and (L6-D), the compound represented by formula (L6-C) is more preferred.

[0387] The following are specific examples of low-molecular-weight compounds 6. However, low-molecular-weight compounds 6 are not limited to these specific examples.

[0388] [ka]

[0389] [ka]

[0390] The method for producing the low molecular weight compound 6 is not particularly limited, and various production methods, including known synthesis methods, can be used.

[0391] In a preferred embodiment of the present invention, the low molecular weight material comprises at least one low molecular weight compound selected from the group consisting of low molecular weight compound 1, low molecular weight compound 2, low molecular weight compound 3, low molecular weight compound 4, low molecular weight compound 5, and low molecular weight compound 6. In a more preferred embodiment of the present invention, the low molecular weight material comprises at least one or more low molecular weight compounds selected from the following group (C).

[0392] [ka]

[0393] In an electroluminescent element according to another preferred embodiment of the present invention, the organic layer (preferably a hole transport layer) comprises at least one polymer selected from group (A) above and at least one low-molecular-weight compound selected from the group consisting of low-molecular-weight compound 1, low-molecular-weight compound 2, low-molecular-weight compound 3, low-molecular-weight compound 4, low-molecular-weight compound 5 and low-molecular-weight compound 6. In an electroluminescent element according to another preferred embodiment of the present invention, the organic layer (preferably a hole transport layer) comprises at least one polymer selected from group (B) above and at least one low-molecular-weight compound selected from the group consisting of low-molecular-weight compound 1, low-molecular-weight compound 2, low-molecular-weight compound 3, low-molecular-weight compound 4, low-molecular-weight compound 5 and low-molecular-weight compound 6. In an electroluminescent element according to another preferred embodiment of the present invention, the organic layer (preferably a hole transport layer) comprises at least one polymer selected from group (A) above and at least one low-molecular-weight compound selected from group (C) above. In an electroluminescent element according to another preferred embodiment of the present invention, the organic layer (preferably a hole transport layer) comprises at least one polymer selected from group (B) and at least one low-molecular-weight compound selected from group (C).

[0394] When using low molecular weight materials, the content of the low molecular weight material in the composition according to the above embodiment is not particularly limited. However, when the total of the polymer and the low molecular weight material according to the above embodiment is taken as 100% by mass, the content of the low molecular weight material is preferably greater than 0% by mass and 50% by mass or less, more preferably 10% by mass or more and 30% by mass or less, and even more preferably 15% by mass or more and 25% by mass or less. According to these methods, the device life of the EL element, in particular the device life of the quantum dot electroluminescent element, is further improved. The preferred content of the low molecular weight material in the electroluminescent element material according to the above embodiment is also the same as the range of the preferred content of the low molecular weight material in the composition according to the above embodiment. The preferred content of the low molecular weight material in the organic layer (preferably the hole transport layer) of the electroluminescent element according to the above embodiment is also the same as the range of the preferred content of the low molecular weight material in the composition according to the above embodiment.

[0395] In one embodiment of the present invention, the hole transport layer 140 may include the polymer according to the above embodiment and a known hole transport material.

[0396] If any other organic film of the EL element 100 contains a polymer according to the above embodiment, the hole transport layer 140 may be formed of a known hole transport material.

[0397] Known hole transport materials include, for example, carbazole derivatives such as 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), N-phenylcarbazole, and polyvinylcarbazole, and N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (N Examples include 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). The hole transport material may be used individually or as a mixture of two or more.

[0398] A 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, etc., and is preferably formed using a vacuum deposition method, spin coating method, inkjet printing method, etc. The light-emitting layer 150 may be formed with a thickness of, for example, 10 nm to 60 nm, preferably 20 nm to 50 nm.

[0399] The light-emitting material for the light-emitting layer 150 is not particularly limited, and known light-emitting materials can be used. Preferably, the light-emitting material included in the light-emitting layer 150 is a light-emitting material capable of emitting light from triplet excitons (i.e., phosphorescence). In such a case, the operating life of the EL element 100 can be further improved. The light-emitting material may be used alone or as a mixture of two or more types.

[0400] The light-emitting layer 150 is not particularly limited and can have a known configuration. Preferably, the light-emitting layer contains quantum dots or an organometallic complex, and more preferably, it contains quantum dots. That is, in a preferred embodiment of the present invention, the organic film has a light-emitting layer containing quantum dots or an organometallic complex, and in a more preferred embodiment of the present invention, the organic film has a light-emitting layer containing quantum dots. When the light-emitting layer contains quantum dots, the EL element is a quantum dot electroluminescent element (QLED), a quantum dot light-emitting element, or a quantum point light-emitting element. When the light-emitting layer contains an organometallic complex, the EL element is an organic electroluminescent element (OLED).

[0401] In a configuration where the light-emitting layer includes quantum dots (QLED), the light-emitting layer consists of a large number of quantum dots arranged in a single or multiple layer. Here, the quantum dots are semiconductor nanoparticles of a predetermined size that exhibit quantum constraint effects. The diameter of the semiconductor nanoparticles (quantum dots) is not particularly limited, but is preferably between 1 nm and 15 nm, and more preferably between 1 nm and 10 nm.

[0402] Semiconductor nanoparticles (quantum dots) arranged in the light-emitting layer can be synthesized by wet chemical processes, organometallic chemical vapor deposition processes, molecular beam epitaxy processes, or other similar processes. Among these, wet chemical processes are methods in which precursor substances are added to an organic solvent to grow particles.

[0403] In wet chemical processes, as crystals grow, organic solvents naturally coordinate to the surface of quantum dot crystals, acting as dispersants and regulating crystal growth. Therefore, wet chemical processes are used for vapor-phase deposition such as metal-organic chemical vapor deposition (MOCVD) and molecular beam epitaxy (MBE). Compared to conventional methods, this allows for easier and lower-cost control of semiconductor nanoparticle growth.

[0404] Semiconductor nanoparticles (quantum dots) can have their energy bandgap adjusted by controlling their size, allowing for the generation of light across diverse wavelengths in the light-emitting layer (quantum dot light-emitting layer). Therefore, using multiple 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, enabling the creation of color displays. Alternatively, the sizes of the quantum dots can be combined to emit white light from various colored light sources.

[0405] As semiconductor nanoparticles (quantum dots), semiconductor materials selected from the group consisting of group II-VI semiconductor compounds; group III-V semiconductor compounds; group IV-VI semiconductor compounds; group IV elements or compounds; and combinations thereof can be used.

[0406] The group II-VI semiconductor compounds are not particularly limited, but include, for example, two-element compounds selected from the group consisting of CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, and mixtures thereof; three-element 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 four-element compounds selected from the group consisting of CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and mixtures thereof.

[0407] III-V semiconductor compounds are not particularly limited, but include, for example, two-element compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; three-element 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 four-element compounds selected from the group consisting of GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof.

[0408] The IV-VI semiconductor compounds are not particularly limited, but can be selected from, for example, two-element compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; three-element compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and four-element compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof.

[0409] The Group IV elements or compounds are not particularly limited, but include, for example, mono-element compounds selected from the group consisting of Si, Ge, and mixtures thereof; and di-element compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0410] 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 constituting the core and shell can consist of different semiconductor compounds. However, the energy band gap of the shell material is greater than the energy band gap of the core material. Specifically, structures such as ZnTeSe / ZnSe / ZnS, InP / ZnSe / ZnS, CdSe / ZnS, and InP / ZnS are preferred.

[0411] For example, let's explain the process of creating quantum dots with a core (CdSe) and shell (ZnS) structure. First, a precursor material for the core (CdSe), such as (CH3)2Cd (dimethylcadmium) or TOPSe (trioctylphosphine selenide), is injected into an organic solvent using TOPO (trioctylphosphine oxide) as a surfactant to generate crystals. At this time, the crystals are maintained at a high temperature for a certain period of time to grow to a certain size, and then a precursor material for the shell (ZnS) is injected to form a shell on the surface of the already formed core. In this way, a CdSe / ZnS quantum dot capped with TOPO can be created.

[0412] Semiconductor nanoparticles (quantum dots) may be modified with organic compounds.

[0413] Quantum dots may be used individually or as a mixture of two or more types.

[0414] If the light-emitting layer contains quantum dots, the light-emitting layer may also contain other materials in addition to the quantum dots. These other materials are not particularly limited, but examples include organic compounds.

[0415] In an OLED (Organometallic Light-Emitting Layer) configuration, the light-emitting layer 150 may include, 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,-triazine-2-yl)phenyl)-9H-carbazole, 9,9'-diphenyl-3,3'-bi[9H-carbazole], tris(8-quinolinato)aluminium (Alq3), 4,4'-bis(carbazol-9-yl)biphenyl (CBP), poly(n-vinyl carbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (1,3,5- The host material may also contain benzene (yl:TPBI), 3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), distyrylarylene (DSA), 4,4'-bis(9-carbazole)2,2'-dimethyl-biphenyl (dmCBP), etc. The host material may be used individually or as a mixture of two or more.

[0416] The light-emitting layer 150 contains, as dopant materials, for example, perylene and its derivatives, rubrene and its derivatives, coumarin and its derivatives, 4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DCM) and its derivatives, and bis[2-(4,6-difluorophenyl)pyridinate]picolinate iridium(III) The dopant material may also contain iridium (Ir) complexes such as 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-xyl)phenyl)pyridineiridium(III), as well as osmium (Os) complexes, platinum complexes, etc. Of these, it is preferable that the luminescent material is a luminescent organometallic complex compound. The dopant material may be used individually or as a mixture of two or more.

[0417] The method for forming the light-emitting layer is not particularly limited. It can be formed by applying a coating solution containing quantum dots or organometallic complexes (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 the polymer according to the above embodiment) as the solvent constituting the coating solution.

[0418] 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 and is formed using methods such as vacuum deposition, spin coating, or inkjet. The electron transport layer 160 may be formed with a thickness of, for example, 15 nm to 50 nm.

[0419] The electron transport layer 160 may be formed from a known electron transport material. Examples of known electron transport materials include (8-quinolinato)lithium (also known as lithium quinolate) ((8-quinolinato)lithium: Liq), tris(8-quinolinato)aluminium (tris(8-quinolinato)aluminium: Alq3), and compounds having a nitrogen-containing aromatic ring. Specific examples of compounds containing nitrogen-containing aromatic rings include, for example, compounds containing a pyridine ring such as 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, compounds containing a triazine ring such as 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, and 2-(4-(N-phenylbenzo Examples of compounds containing an imidazole ring include inidazolyl-1-ylphenyl)-9,10-dinaphthylanthracene and 1,3,5-tris(N-phenyl-benzimidazol-2-yl)benzene (TPBI). Electron transport materials may be used individually or as a mixture of two or more.

[0420] An electron injection layer 170 is formed on the electron transport layer 160. The electron injection layer 170 is a layer that facilitates the injection of electrons from the second electrode 180. The electron injection layer 170 is formed using a method such as vacuum deposition. The electron injection layer 170 may be formed with a thickness of, for example, 0.1 nm to 5 nm, preferably 0.3 nm to 2 nm. Any known material can be used to form the electron injection layer 170. For example, the electron injection layer 170 may be formed from lithium compounds such as (8-quinolinato)lithium (also known as lithium quinolate) ((8-quinolinato)lithium: Liq), lithium fluoride (LiF), sodium chloride (NaCl), cesium fluoride (CsF), lithium oxide (Li2O), or barium oxide (BaO). The electron injection material may be used alone or as a mixture of two or more materials.

[0421] A second electrode 180 is formed on the electron injection layer 170. The second electrode 180 is formed using a method such as vacuum deposition. Specifically, the second electrode 180 is a cathode and is formed from a metal, alloy, or conductive compound with a small work function. For example, the second electrode 180 may be formed as a reflective electrode from a metal such as lithium (Li), magnesium (Mg), aluminum (Al), or calcium (Ca), or from an alloy such as aluminum-lithium (Al-Li), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag). The second electrode 180 may be formed with a thickness of, for example, 10 nm to 200 nm, preferably 50 nm to 150 nm. Alternatively, the second electrode 180 may be formed as a transmissive electrode from a thin film of the above-mentioned metal material with a thickness of 20 nm or less, or from a transparent conductive film such as indium tin oxide (In2O3-SnO2) or indium zinc oxide (In2O3-ZnO).

[0422] The above describes an EL element 100 according to one embodiment of the present invention as an example of an electroluminescent element according to one aspect of the present invention. The EL element 100 according to one embodiment of the present invention can have its element life, in particular the element life of a quantum dot electroluminescent element, extended by installing an organic film (particularly a hole transport layer or a hole injection layer) containing the polymer according to the above embodiment. In one embodiment of the present invention, the polymer according to the above embodiment may be included in the organic layer as an EL element material according to the above embodiment, or it may be included as a composition according to the above embodiment.

[0423] An EL element 100 according to one embodiment of the present invention may be formed in other known stacked structures. For example, the EL element 100 may omit one or more layers selected from the group consisting of a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, and an electron injection layer 170, or it may have additional layers. Furthermore, each layer of the EL element 100 may be formed as a single layer or as multiple layers. For example, the EL element 100 may further include a hole blocking layer between the electron transport layer 160 and the light-emitting layer 150 to prevent excitons or holes from diffusing into the electron transport layer 160. The hole blocking layer can be formed from, for example, an oxadiazole derivative, a triazole derivative, or a phenanthroline derivative. For example, the EL element 100 may further include an electron blocking layer between the hole transport layer 140 and the light-emitting layer 150 to prevent excitons or electrons from diffusing into the hole transport layer 140.

[0424] Furthermore, the polymer according to the above embodiment, the EL element material according to the above embodiment, and the composition according to the above embodiment can be applied to electroluminescent elements other than the QLED or OLED described above. Other electroluminescent elements are not particularly limited, but examples include organic-inorganic perovskite light-emitting elements.

[0425] Another preferred embodiment of the composition according to the above embodiment is, for example, a composition comprising the polymer according to the above embodiment, satisfying condition (a) above, and further comprising a low molecular weight material satisfying condition (b), condition (c) or both above. The composition is more preferably a hole transport layer forming composition.

[0426] Another preferred embodiment of the electroluminescent element according to this embodiment is, for example, an electroluminescent element comprising a pair of electrodes and one or more organic layers disposed between the pair of electrodes, wherein at least one of the organic layers comprises a polymer according to the above embodiment and a low molecular weight material that satisfies condition (a) and condition (b), condition (c), or both thereof. A more preferred embodiment is an electroluminescent element comprising a pair of electrodes and a hole transport layer disposed between the pair of electrodes, wherein the hole transport layer comprises a polymer according to the above embodiment and a low molecular weight material that satisfies condition (a) and condition (b), condition (c), or both thereof. These electroluminescent elements preferably further comprise a layer containing quantum dots.

[0427] While embodiments of the present invention have been described in detail, these are descriptive and illustrative, and not limiting, and it is clear that the scope of the present invention should be interpreted by the appended claims.

[0428] The present invention encompasses the following aspects and embodiments: [1] Polymers whose overlap index, expressed by the following formula, is between 0.00001 and 1.8:

[0429]

number

[0430] In the above formula, k is the sequential number assigned to the atom in the chemical formula of the constituent unit of the polymer, and d kHOMO This shows the distribution density of the HOMO in the atom with serial number k, and d k LUMO This shows the distribution density of LUMOs in the atom with serial number k; [2] The polymer according to [1], wherein the overlap index represented by the above formula is 0.00001 or more and 1.2 or less; [3] A polymer according to [1] or [2], comprising a constituent unit represented by formula (1) above; [4] A polymer comprising the constituent unit represented by the above formula (1); [5] In the above formula (1), Ar 3 The polymer described in [3] or [4] is a group selected from the above group (I); [6] In the above formula (1), Ar 1 Ar 2 and Ar 4 The polymer according to any one of [3] to [5], wherein at least one selected from the group consisting of is independently a group selected from group (II) above; [7] In the above formula (1), Ar 1 Ar 2 and Ar 4 Each of these groups is independently selected from group (II) above, and is the polymer described in [6]; [8] The polymer according to any one of [3] to [7], wherein the constituent unit represented by formula (1) is at least one constituent unit selected from group (A) above; [9] The polymer according to any one of [3] to [7], wherein the constituent unit represented by formula (1) is at least one constituent unit selected from group (B) above;

[10] The polymer according to [9], wherein the constituent unit represented by formula (1) is at least one constituent unit selected from the group (B') above; A composition comprising the polymer described in any of

[11] [1] to

[10] ;

[12] The composition according to

[11] , further comprising a low molecular weight material that satisfies condition (a) above and also satisfies condition (b), condition (c), or both of the above;

[13] An electroluminescent element comprising a pair of electrodes and at least one layer of organic film comprising a polymer according to any one of [1] to

[10] , disposed between the pair of electrodes;

[14] An electroluminescent element comprising a pair of electrodes and one or more organic layers disposed between the pair of electrodes, wherein at least one of the organic layers comprises a polymer according to any one of [1] to

[10] and a low molecular weight material that satisfies condition (a) and condition (b), condition (c), or both;

[15] An electroluminescent element comprising a pair of electrodes and at least one layer of organic film comprising the composition described in

[11] or

[12] , disposed between the pair of electrodes;

[16] An electroluminescent element according to any one of

[13] to

[15] , further comprising a layer containing quantum dots. [Examples]

[0431] 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, the operations were carried out at room temperature (25°C). Unless otherwise specified, "%" and "parts" mean "mass%" and "parts by mass," respectively.

[0432] <Synthesis of polymers> (Synthesis of Intermediate 1) Intermediate 1 was synthesized according to the following reaction.

[0433] [ka]

[0434] In a 3L four-necked flask, 4-chloroaniline (510 mmol, 65.0 g), 1-bromo-4-chlorobenzene (535 mmol, 102.4 g), t-butoxysodium (t-BuONa) (764 mmol, 73.4 g), toluene (1020 ml), and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (PdCl2(dppf)·CH2Cl2) (15.3 mmol, 12.5 g) were added, and the mixture was heated and stirred under a nitrogen atmosphere at 110°C to start the reaction. Subsequently, the reaction mixture was heated and stirred at 110°C for 6 hours while monitoring the progress of the reaction. After the reaction was complete, the resulting solution was cooled to room temperature and filtered through Celite. The obtained solution was concentrated and purified by silica gel chromatography (hexane:toluene = 7:3). The obtained solution was concentrated and purified by recrystallization using toluene (toluene) and hexane (hexane). The obtained solid was vacuum dried (50°C, 16 hours) to obtain intermediate 1a (yield 100g, yield 83%).

[0435] In a 1L four-necked flask, intermediate 1a (168 mmol, 40.0 g), p-bromoiodobenzene (252 mmol, 71.3 g), t-BuONa (336 mmol, 32.3 g), toluene (336 ml), and PdCl2 (dppf)·CH2Cl2 (0.50 mmol, 4.12 g) were added, and the mixture was heated and stirred at 110°C under a nitrogen atmosphere to initiate the reaction. The reaction mixture was then heated and stirred at 110°C for 6 hours while monitoring the progress of the reaction. After the reaction was complete, the resulting solution was cooled to room temperature and filtered through Celite. The resulting solution was concentrated and purified by silica gel chromatography (hexane:toluene = 7:3). The resulting solution was concentrated and purified by two recrystallizations using tetrahydrofuran (THF) and methanol. The obtained solid was vacuum-dried (50°C, 16 hours) and then vacuum-dried again (50°C, 12 hours) to obtain intermediate 1b (yield 34g, yield 50%).

[0436] In a 2L three-necked flask, intermediate 1b (178 mmol, 70.0 g), bis(pinacolate)diboron (267 mmol, 67.8 g), potassium acetate (356 mmol, 34.2 g), and 1,4-dioxane (650 ml) were added and stirred to disperse. Bis(triphenylphosphine)palladium(II) dichloride (PdCl2(PPh3)2)) (5.34 mmol, 4.36 g) was added and refluxed under an argon atmosphere for 20 hours. The resulting solution was cooled to room temperature and filtered through Celite to remove insoluble matter. The resulting solution was concentrated and filtered through a silica gel pad to remove the origin component. The resulting solution was concentrated and purified by recrystallization using toluene and hexane. The obtained solid was vacuum-dried (50°C, 12 hours) to obtain intermediate 1 (yield 53.5g, yield 68%).

[0437] (Synthesis of Intermediate 2) Intermediate 2 was synthesized according to the following reaction.

[0438] [ka]

[0439] In a 500 mL three-necked flask, intermediate 1 (73.1 mmol, 9.0 g), 3-bromo-9H-carbazole (73.1 mmol, 16.1 g), and toluene (180 ml) were dissolved. Na2CO3 aqueous solution (109.7 mmol, 5.82 g, 90 mL of pure water) and ethanol (90 mL) were added and dispersed, and the mixture was bubbling under nitrogen for 30 minutes. Then, tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (3.66 mol, 2.11 g) was added and the mixture was refluxed under a nitrogen atmosphere for 5 hours. After the reaction was complete, the resulting solution was cooled to room temperature, diluted with toluene, and washed three times with pure water. The resulting solution was dried using MgSO4 and then filtered through a silica gel pad. The obtained filtrate was purified by removing the solvent under reduced pressure, followed by two recrystallizations using toluene and methanol. The resulting solid was vacuum-dried (50°C, 16 hours) to obtain intermediate 2 (yield 13.8 g, yield 79%).

[0440] (Synthesis of Intermediate 3) Intermediate 3 was synthesized according to the following reaction.

[0441] [ka]

[0442] Intermediate 3 was synthesized in the same manner as intermediate 2, except that 3-bromo-9H-carbazole was replaced with 2-bromo-9H-carbazole (yield). 14.5g, yield 89%.

[0443] (Synthesis of Intermediate 4) Intermediate 4 was synthesized according to the following reaction.

[0444] [ka]

[0445] Intermediate 4 was synthesized in the same manner as intermediate 2, except that 3-bromo-9H-carbazole was replaced with 4-bromo-9H-carbazole (yield 32.1 g, yield 64%).

[0446] (Synthesis of monomer M-1) Monomer M-1 was synthesized according to the following reaction.

[0447] [ka]

[0448] In a 300 mL four-necked flask, intermediate 2 (28.8 mmol, 13.8 g), 3-bromo-1,1':3',1”-terphenyl (31.7 mmol, 9.79 g), t-BuONa (43.2 mmol, 4.15 g), and toluene (toluene) (160 ml) were dispersed. Trisdibenzylideneacetone dipalladium (0.58 mmol, 0.53 g) and tri-tert-butylphosphine tetrafluoroborate (1.15 mmol, 0.33 g) were added, and the mixture was heated and stirred at 110 °C under a nitrogen atmosphere for 4 hours. After the reaction was complete, the resulting solution was cooled to room temperature, and insoluble matter was filtered off using Celite. The solvent was removed from the filtrate under reduced pressure, and the residue was purified by column chromatography (silica gel, hexane / toluene) to obtain precursor M-1a (yield 11.0 g, yield 54%).

[0449] In a 2 L three-necked flask, precursor M-1a (15.5 mmol, 11.0 g), bis(pinacolate)diboron (62.2 mmol, 15.8 g), potassium acetate (93.3 mmol, 9.0 g), and 1,4-dioxane (155 ml) were added and stirred to disperse. Palladium acetate (1.55 mmol, 0.35 g) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1.55 mmol, 0.74 g) were added and refluxed under an argon atmosphere for 5 hours. The resulting solution was cooled to room temperature and filtered through Celite to remove insoluble matter. The solvent was removed from the filtrate under reduced pressure and filtered through a silica gel pad to remove the origin component. The resulting solution was concentrated and purified by recrystallization using toluene and acetonitrile. The obtained solid was vacuum-dried (50°C, 12 hours) to obtain monomer M-1 (yield 5.3g, yield 38%.

[0450] (Synthesis of monomer M-2) Monomer M-2 was synthesized using the same procedure as monomer M-1, except that 3-bromo-1,1':3',1”-terphenyl was replaced with 2-(3-bromophenyl)naphthalene in monomer M-1, according to the reaction described below (yield 5.1g, yield 57%).

[0451] [ka]

[0452] (Synthesis of monomer M-3) Monomer M-3 was synthesized using the same procedure as monomer M-1, except that 3-bromo-1,1':3',1”-terphenyl was replaced with 2-bromodibenzofuran in monomer M-1, according to the reaction described below (yield 6.5g, yield 60%).

[0453] [ka]

[0454] (Synthesis of monomer M-4) Monomer M-4 was synthesized using the same procedure as for monomer M-1, except that intermediate 2 in monomer M-1 was replaced with intermediate 3, and 3-bromo-1,1':3',1”-terphenyl was replaced with 2-bromodibenzothiophene (yield 3.8g, yield 40%).

[0455] [ka]

[0456] (Synthesis of monomer M-5) Monomer M-5 was synthesized using the same procedure as for monomer M-1, except that 3-bromo-1,1':3',1”-terphenyl was replaced with 3-bromo-9,9-dimethylfluorene in monomer M-1, according to the reaction described below (yield 3.0 g, yield 17%).

[0457] [ka]

[0458] (Synthesis of monomer M-6) Monomer M-6 was synthesized using the same procedure as for monomer M-1, except that intermediate 2 in monomer M-1 was replaced with intermediate 4, and 3-bromo-1,1':3',1”-terphenyl was replaced with 3-bromo-9,9-dimethylfluorene (yield 9.3g, yield 73%).

[0459] [ka]

[0460] (Example 1: Synthesis of polymer A-1) Under an argon atmosphere, monomer M-1 (1.978 g), 9,9-dioctyl-3,6-dibromofluorene (1.212 g), palladium acetate (5.0 mg), tris(2-methoxyphenyl)phosphine (47.0 g), toluene (64 mL), and 11.5 g of 20% by mass aqueous solution of tetraethylammonium hydroxide were mixed and stirred under reflux for 6 hours. Next, phenylboronic acid (268.8 mg), bis(triphenylsphine)palladium(II) dichloride (93.5 mg), and 11.5 g of 20% by mass aqueous solution of tetraethylammonium hydroxide were added to the reaction solution and heated under reflux for 6 hours. After that, the aqueous layer was removed from the resulting solution, and sodium N,N-diethyldithiocarbamate trihydrate (7.51 g) and deionized water (70 mL) were added and stirred at 85°C for 6 hours. After separating the organic layer from the aqueous layer of the obtained solution, the organic layer was washed with water, 3% by mass aqueous acetic acid 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 silica gel / alumina-packed column chromatography, and the solvent was removed by vacuum distillation. The resulting liquid was added dropwise to methanol, and the precipitated solid was filtered off and dried to obtain polymer A-1 (yield 0.35 g).

[0461] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-1 were measured using SEC. As a result, the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-1 were 213,000 and 1.85, respectively.

[0462] The polymer A-1 obtained in this way is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0463] [ka]

[0464] (Example 2: Synthesis of Polymer A-2) Polymer A-2 was synthesized using the same procedure as polymer A-1, except that monomer M-1 was replaced with monomer M-2 (yield: 0.77g).

[0465] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-2 were measured using SEC. As a result, the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-2 were 217,000 and 1.83, respectively.

[0466] The polymer A-2 obtained in this way is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0467] [ka]

[0468] (Example 3: Synthesis of Polymer A-3) Polymer A-3 was synthesized using the same procedure as polymer A-1, except that monomer M-1 was replaced with monomer M-3 (yield: 0.70 g).

[0469] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-3 were measured using SEC. As a result, the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-3 were 220,000 and 1.58, respectively.

[0470] The polymer A-3 obtained in this way is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0471] [ka]

[0472] (Example 4: Synthesis of Polymer A-4) Polymer A-4 was synthesized using the same procedure as polymer A-1, except that monomer M-1 was replaced with monomer M-4 (yield: 0.43 g).

[0473] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-4 were measured using SEC. As a result, the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-4 were 140,000 and 2.90, respectively.

[0474] The polymer A-4 obtained in this way is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0475] [ka]

[0476] (Example 5: Synthesis of Polymer A-5) Polymer A-5 was synthesized using the same procedure as polymer A-1, except that monomer M-1 was replaced with monomer M-5 (yield: 0.15 g).

[0477] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-5 were measured using SEC. As a result, the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-5 were 74,000 and 1.58, respectively.

[0478] The polymer A-5 obtained in this way is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0479] [ka]

[0480] (Example 6: Synthesis of Polymer A-6) Polymer A-6 was synthesized using the same procedure as polymer A-1, except that monomer M-1 was replaced with monomer M-6 (yield: 0.92 g).

[0481] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-6 were measured using SEC. As a result, the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-6 were 114,000 and 2.56, respectively.

[0482] The polymer A-6 obtained in this way is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0483] [ka]

[0484] In the above polymers A-1 to A-6, "C8H 17 The group represented by "-" represents an n-octyl group.

[0485] (Example 7: Polymer A-7) Polymer A-7 will be discussed later.

[0486] (Examples 8-21: Polymer A-8 to Polymer A-21) (Synthesis of Intermediate 5) Intermediate 5 was synthesized according to the following reaction.

[0487] [ka]

[0488] In a 1L four-necked flask, 1-bromo-4-hexylbenzene (207.3 mmol, 50.0 g), bis(pinacolato)diborone (248.8 mmol, 63.2 g), potassium acetate (310.1 mmol, 29.9 g), and 1,4-dioxane (691 ml) were dispersed. [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), dichloromethane adduct (20.7 mmol, 16.9 g) was added, and the mixture was heated and stirred at 90°C under a nitrogen atmosphere for 4 hours. After the reaction was complete, the resulting solution was cooled to room temperature, and insoluble matter was filtered off using Celite. The solvent was removed from the filtrate under reduced pressure, and the residue was purified by column chromatography (silica gel, hexane / toluene) to obtain intermediate 5 (yield 48.0 g, yield 80%).

[0489] In 1-bromo-4-hexylbenzene and intermediate 5, "C6H 13 The group represented by "-" represents an n-hexyl group.

[0490] (Synthesis of monomer M-7) Monomer M-7 was synthesized according to the following reaction.

[0491] [ka]

[0492] The monomer M-7 was synthesized using the same procedure as monomer M-1, except that intermediate 1 was replaced with intermediate 2. The yields of precursor M-7a and monomer M-7 were as follows: Precursor M-7a (yield 7.0g, yield 73%) Monomer M-7 (Yield 6.0g, yield 68%) That was the case.

[0493] (Synthesis of monomer M-8) Monomer M-8 was synthesized according to the following reaction.

[0494] [ka]

[0495] In precursor M-8b and monomer M-8, "C6H 13 The group represented by "-" represents an n-hexyl group.

[0496] In a 200 mL four-necked flask, intermediate 2 (31.3 mmol, 15.0 g), 4-bromo-4'-iodo-1,1'-biphenyl (31.3 mmol, 11.2 g), t-BuONa (46.9 mmol, 4.51 g), and 1,4-dioxane (31 mL) were dispersed. Copper iodide (1.56 mmol, 0.30 g) and trans-cyclohexanediamine (6.26 mmol, 0.75 g) were added, and the mixture was heated and stirred at 90°C under a nitrogen atmosphere for 20 hours. After the reaction was complete, the resulting solution was cooled to room temperature, and insoluble materials were filtered off using Celite. The solvent was removed from the filtrate under reduced pressure, and the residue was purified by column chromatography (silica gel, hexane / toluene). The resulting solid was recrystallized and purified using tetrahydrofuran and methanol to obtain precursor M-8a (yield 19.3 g, yield 87%).

[0497] In a 500 mL three-necked flask, precursor M-8a (27.2 mmol, 19.3 g), intermediate 5 (27.2 mmol, 7.83 g), sodium carbonate (40.8 mmol, 4.32 g), toluene (136 mL), ethanol (68 mL), and distilled water (68 mL) were added and stirred to disperse the mixture. Tetrakis(triphenylphosphine)palladium (0.81 mmol, 0.94 g) was added and the mixture was refluxed under an argon atmosphere for 14 hours. The resulting solution was cooled to room temperature, the precipitate was filtered off, and washed with methanol. The precipitate was purified by recrystallization using tetrahydrofuran and methanol. The resulting solid was vacuum-dried (50°C, 12 hours) to obtain precursor M-8b (yield 17.4 g, yield 80%).

[0498] In a 500 mL three-necked flask, precursor M-8b (22.0 mmol, 17.4 g), bis(pinacolate)diboron (87.9 mmol, 22.3 g), potassium acetate (131.9 mmol, 12.7 g), and 1,4-dioxane (220 mL) were added and stirred to disperse. Palladium acetate (2.20 mmol, 0.50 g) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (2.20 mmol, 1.05 g) were added and refluxed under an argon atmosphere for 3 hours. The resulting solution was cooled to room temperature and filtered through Celite to remove insoluble matter. The solvent was removed from the filtrate under reduced pressure and filtered through a silica gel pad to remove the origin component. The resulting solution was concentrated and purified by recrystallization using toluene and acetonitrile. The obtained solid was vacuum-dried (50°C, 12 hours) to obtain monomer M-8 (yield 9.6g, yield 44%).

[0499] (Synthesis of monomer M-9) Monomer M-9 was synthesized according to the following reaction.

[0500] [ka]

[0501] In precursor M-9b and monomer M-9, "C6H 13 The group represented by "-" represents an n-hexyl group.

[0502] Monomer M-9 was synthesized using the same procedure as monomer M-8, except that 4-bromo-4'-iodo-1,1'-biphenyl was replaced with 4-bromo-3'-iodo-1,1'-biphenyl. The yields of precursor M-9a, precursor M-9b, and monomer M-9 were respectively: Precursor M-9a (yield 14.5g, yield 65%) Precursor M-9b (yield 4.4g, yield 44%) Monomer M-9 (yield 3.4g, yield 62%) That was the case.

[0503] (Synthesis of monomer M-10) Monomer M-10 was synthesized according to the following reaction.

[0504] [ka]

[0505] In precursor M-10b and monomer M-10, "C6H 13 The group represented by "-" represents an n-hexyl group.

[0506] Monomer M-10 was synthesized using the same procedure as monomer M-8, except that intermediate 2 was replaced with intermediate 3. The yields of precursor M-10a, precursor M-10b, and monomer M-10 were as follows: Precursor M-10a (yield 12.9g, yield 58%) Precursor M-10b (yield 10.8g, yield 75%) Monomer M-10 (yield 7.8g, yield 57%) That was the case.

[0507] (Synthesis of monomer M-11) Monomer M-11 was synthesized according to the following reaction.

[0508] [ka]

[0509] In precursor M-11b and monomer M-11, "C6H 13 The group represented by "-" represents an n-hexyl group.

[0510] Monomer M-11 was synthesized using the same procedure as monomer M-8, except that intermediate 2 was replaced with intermediate 3 in monomer M-8, and 4-bromo-4'-iodo-1,1'-biphenyl was replaced with 4-bromo-3'-iodo-1,1'-biphenyl. The yields of precursor M-11a, precursor M-11b, and monomer M-11 were as follows: Precursor M-11a (yield 14.5g, yield 65%) Precursor M-11b (yield 14.4g, yield 89%) Monomer M-11 (yield 9.1g, yield 53%) That was the case.

[0511] (Monomer M-12) Monomer M-12 was synthesized according to the following reaction.

[0512] [ka]

[0513] In a 500 mL three-necked flask, precursor M-7 (11.2 mmol, 10.0 g), 1-bromo-4-chlorobenzene (28.1 mmol, 5.37 g), sodium carbonate (16.8 mmol, 1.79 g), toluene (56 mL), ethanol (28 mL), and distilled water (28 mL) were added and stirred to disperse the mixture. Tetrakis(triphenylphosphine)palladium (0.34 mmol, 0.389 g) was added and the mixture was refluxed under an argon atmosphere for 7 hours. The resulting solution was cooled to room temperature, the precipitate was filtered off, and washed with methanol. The precipitate was purified by recrystallization using tetrahydrofuran and methanol. The resulting solid was vacuum-dried (50°C, 12 hours) to obtain precursor M-12a (yield 7.8 g, yield 81%).

[0514] Monomer M-12 was synthesized using the same procedure as monomer M-1, except that the precursor M-1a in monomer M-1 was replaced with the precursor M-12a (yield 5.6g, yield 59%).

[0515] Each monomer obtained above is used in a nuclear magnetic resonance apparatus ( 1 Its structure was identified by 1H-NMR.

[0516] (Example 8: Synthesis of Polymer A-8) (Synthesis of polymer A-8) Polymer A-8 was synthesized using the same procedure as polymer A-1, except that 9,9-dioctyl-3,6-dibromofluorene was replaced with 9,9-didodecyl-3,6-dibromofluorene (yield 1.1g).

[0517] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-8 were measured using SEC. The results showed that the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-8 were 89,000 and 2.2, respectively.

[0518] The polymer A-8 obtained in this way is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0519] [ka]

[0520] In the above polymer A-8, "C 12 H 25 The group represented by "-" represents an n-dodecyl group.

[0521] (Example 9: Synthesis of Polymer A-9) (Synthesis of polymer A-9) Polymer A-9 was synthesized using the same procedure as polymer A-1, except that monomer M-1 was replaced with monomer M-7 (yield: 1.1g).

[0522] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-9 were measured using SEC. As a result, the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-9 were 196,000 and 2.7, respectively.

[0523] The polymer A-9 obtained in this manner is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0524] [ka]

[0525] In polymer A-9 described above, "C8H 17 The group represented by "-" represents an n-octyl group.

[0526] (Example 10: Synthesis of polymer A-10) Polymer A-10 was synthesized using the same procedure as polymer A-9, except that 9,9-dioctyl-3,6-dibromofluorene was replaced with 9,9-didecyl-3,6-dibromofluorene (yield 0.90g).

[0527] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-10 were measured using SEC. As a result, the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-10 were 115,000 and 1.48, respectively.

[0528] The polymer A-10 obtained in this way is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0529] [ka]

[0530] In the above polymer A-10, "C 10 H 21 The group represented by "-" represents an n-decyl group.

[0531] (Example 11: Synthesis of polymer A-11) Polymer A-11 was synthesized using the same procedure as polymer A-9, except that 9,9-dioctyl-3,6-dibromofluorene was replaced with 9,9-didodecyl-3,6-dibromofluorene (yield 2.0g).

[0532] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-11 were measured using SEC. As a result, the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-11 were 227,000 and 1.7, respectively.

[0533] The polymer A-11 obtained in this way is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0534] [ka]

[0535] In the above-mentioned Polymer A-11, "C 12 H 25 The group represented by "-" represents an n-dodecyl group.

[0536] (Example 12: Synthesis of Polymer A-12) Polymer A-12 was synthesized using the same procedure as polymer A-1, except that monomer M-1 was replaced with monomer M-4 and 9,9-dioctyl-3,6-dibromofluorene was replaced with 9,9-didecyl-3,6-dibromofluorene (yield 1.17g).

[0537] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-12 were measured using SEC. As a result, the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-12 were 63,000 and 2.3, respectively.

[0538] The polymer A-12 obtained in this way is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0539] [ka]

[0540] In the above-mentioned Polymer A-12, "C 10 H 21 The group represented by "-" represents an n-decyl group.

[0541] (Example 13: Synthesis of polymer A-13) Polymer A-13 was synthesized using the same procedure as polymer A-1, except that monomer M-1 was replaced with monomer M-8 (yield: 0.8g).

[0542] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-13 were measured using SEC. As a result, the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-13 were 145,000 and 2.3, respectively.

[0543] The polymer A-13 obtained in this way is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0544] [ka]

[0545] In polymer A-13 described above, "C8H 17 The group represented by "-" represents an n-octyl group, and "C6H 13 The group represented by "-" represents an n-hexyl group.

[0546] (Example 14: Synthesis of Polymer A-14) Polymer A-14 was synthesized using the same procedure as polymer A-1, except that monomer M-1 was replaced with monomer M-9 (yield: 0.9g).

[0547] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-14 were measured using SEC. As a result, the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-2 were 303,000 and 2.0, respectively.

[0548] The polymer A-14 obtained in this way is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0549] [ka]

[0550] In the above polymer A-14, "C8H 17 The group represented by "-" represents an n-octyl group, and "C6H 13 The group represented by "-" represents an n-hexyl group.

[0551] (Example 15: Synthesis of Polymer A-15) Polymer A-15 was synthesized using the same procedure as polymer A-14, except that 9,9-dioctyl-3,6-dibromofluorene was replaced with 9,9-didodecyl-3,6-dibromofluorene (yield 1.0g).

[0552] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-15 were measured using SEC. As a result, the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-15 were 123,000 and 1.8, respectively.

[0553] The polymer A-15 obtained in this manner is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0554] [ka]

[0555] In the above polymer A-15, "C 12 H 25 The group represented by "-" represents an n-dodecyl group, and "C6H 13 The group represented by "-" represents an n-hexyl group.

[0556] (Example 16: Synthesis of Polymer A-16) Polymer A-16 was synthesized using the same procedure as polymer A-1, except that monomer M-1 was replaced with monomer M-10 and 9,9-dioctyl-3,6-dibromofluorene was replaced with 9,9-didecyl-3,6-dibromofluorene (yield 0.7g).

[0557] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-16 were measured using SEC. The results showed that the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-16 were 114,000 and 1.6, respectively.

[0558] The polymer A-16 obtained in this way is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0559] [ka]

[0560] In the above-mentioned polymerization A-16, "C 10 H 21 The group represented by "-" represents an n-decyl group, and "C6H 13 The group represented by "-" represents an n-hexyl group.

[0561] (Example 17: Synthesis of polymer A-17) Polymer A-17 was synthesized using the same procedure as polymer A-16, except that 9,9-didecyl-3,6-dibromofluorene was replaced with 9,9-didodecyl-3,6-dibromofluorene (yield 0.7g).

[0562] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-17 were measured using SEC. As a result, the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-17 were 140,000 and 1.6, respectively.

[0563] The polymer A-17 obtained in this way is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0564] [ka]

[0565] In the above Polymer A-17, "C 12 H 25 The group represented by "-" represents an n-dodecyl group, and "C6H 13 The group represented by "-" represents an n-hexyl group.

[0566] (Example 18: Synthesis of polymer A-18) Polymer A-18 was synthesized using the same procedure as polymer A-1, except that monomer M-1 in polymer A-1 was replaced with monomer M-11 (yield 1.0g).

[0567] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-18 were measured using SEC. As a result, the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-18 were 100,000 and 2.0, respectively.

[0568] The polymer A-18 obtained in this way is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0569] [ka]

[0570] In the above polymer A-18, "C8H 17 The group represented by "-" represents an n-octyl group, and "C6H 13 The group represented by "-" represents an n-hexyl group.

[0571] (Example 19: Synthesis of polymer A-19) Polymer A-19 was synthesized using the same procedure as polymer A-1, except that monomer M-1 in polymer A-1 was replaced with monomer M-12 (yield: 1.3g).

[0572] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-19 were measured using SEC. The results showed that the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-19 were 12,000 and 1.7, respectively.

[0573] The polymer A-19 obtained in this way is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0574] [ka]

[0575] In polymer A-19 above, "C8H 17 The group represented by "-" represents an n-octyl group.

[0576] (Example 20: Synthesis of polymer A-20) Polymer A-20 was synthesized using the same procedure as polymer A-19, except that 9,9-dioctyl-3,6-dibromofluorene was replaced with 9,9-didodecyl-3,6-dibromofluorene (yield 1.1g).

[0577] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-20 were measured using SEC. As a result, the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-20 were 196,000 and 2.7, respectively.

[0578] The polymer A-20 obtained in this manner is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0579] [ka]

[0580] In the above polymer A-20, "C 12 H 25 The group represented by "-" represents an n-dodecyl group.

[0581] (Example 21: Synthesis of polymer A-21) Polymer A-21 was synthesized using the same procedure as polymer A-19, except that 9,9-dioctyl-3,6-dibromofluorene was replaced with 1,4-dibromo-2,5-dihexylbenzene (yield 1.1g).

[0582] The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of the obtained polymer A-21 were measured using SEC. As a result, the weight-average molecular weight (Mw) and dispersion (Mw / Mn) of polymer A-21 were 196,000 and 2.7, respectively.

[0583] The polymer A-21 obtained in this way is estimated to have the following repeating units (constituent units) based on the monomer input ratio.

[0584] [ka]

[0585] In the above polymerA-21, "C6H 13The group represented by "-" represents an n-hexyl group.

[0586] <Evaluation of each polymer> [Simulation Evaluation] The overlap index was calculated for the polymers of Examples 1 to 6 (polymers A-1 to A-6), the polymer of Example 7 (polymer A-7), the polymers of Examples 8 to 21 (polymers A-8 to A-21), and poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine)] (TFB) having the following structural units, using the method described below.

[0587] Furthermore, the polymer of Example 7 (polymer A-7) can be synthesized by changing the raw materials in the synthesis of polymer A-1 of Example 1.

[0588] [ka]

[0589] [ka]

[0590] In polymer A-7 described above, "C8H 17 The group represented by "-" represents an n-octyl group.

[0591] For the constituent units of the polymer, the HOMO, LUMO, and their distribution densities were calculated using Density Functional Theory (DFT) with Gaussian 16 (Gaussian Inc.) as the computational software, using the functional B3LYP and the basis set 6-31G(d,p).

[0592] Using the distribution densities of HOMO and LUMO on each atom of the constituent units of the polymer, calculated in the above calculation, the overlap index was calculated as the overlap between HOMO and LUMO according to the following formula.

[0593]

number

[0594] In the above formula, k is the sequential number assigned to the atom in the chemical formula of the constituent unit of the polymer, and d k HOMO This shows the distribution density of the HOMO in the atom with serial number k, and d k LUMO This shows the distribution density of LUMO in the atom with serial number k. d k HOMO and d k LUMO These values ​​were calculated using Density Functional Theory (DFT), with Gaussian 16 (Gaussian Inc.) as the computational software, using the functional B3LYP and the basis set 6-31G(d,p).

[0595] The overlap index was calculated for the ground state of the polymer's constituent units, with the highest orbital where electrons are distributed being defined as the HOMO and the lowest orbital where electrons are not distributed being defined as the LUMO.

[0596] If the polymer has only one type of constituent unit, the overlap index is calculated based on that single unit. If the polymer has two or more constituent units, the overlap index for each constituent unit is calculated separately. The product of the overlap index for each constituent unit and the content ratio of each constituent unit (the ratio of each constituent unit to the total number of constituent units constituting the polymer) is then calculated, and the sum of these values ​​is used as the polymer's overlap index.

[0597] More specifically, the overlap index was calculated using the following procedure: First, each atom contained in the polymer's constituent units was assigned a sequential number.

[0598] Next, for each atom assigned these sequential numbers, the distribution density of the HOMO and LUMO on the atoms of the constituent units constituting the polymer was determined using the method described above. As an example, for the comparative example poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine)](TFB), the distribution density of the HOMO at each sequentially numbered atom d was determined by simulation. k HOMO and the distribution density of LUMO d k LUMO The graph shows the distribution density d of the HOMO in each atom with serial number k. k HOMO And the distribution density of LUMO d k LUMO Figures 2 and 3 show the graph of the product and the molecular orbital diagram obtained by simulation. Furthermore, for polymer A-7 according to Example 7 of the present invention, the distribution density d of the HOMO at each sequentially numbered atom, obtained by simulation, is shown. k HOMO and the distribution density of LUMO d k LUMO The graph shows the distribution density d of the HOMO in each atom with serial number k. k HOMO And the distribution density of LUMO d k LUMO Figures 4 and 5 show the graph illustrating the product of the two, and the molecular orbital diagram obtained by the simula rayon.

[0599] Then, the overlap index was calculated according to the above formula based on the distribution density of HOMO and LUMO on each atom of the constituent units of the polymer. As a result, as shown in Figures 2 to 5, it was confirmed that polymer A-7 in Example 7 had less overlap between the HOMO portion and the LUMO portion within the constituent unit compared to TFB in the comparative example, and that the overlap index was also smaller, as shown in Table 1 below.

[0600] Furthermore, as other examples, polymers A-1 to A-6 from Examples 1 to 6 and polymers A-8 to A-21 from Examples 8 to 21 were similarly found to have less overlap between the HOMO and LUMO portions within the constituent unit compared to the TFB of the comparative examples, and the overlap index was also smaller, as shown in Table 1 below. Of these, the distribution density d of the HOMO at each atom with serial number k, obtained by simulation, is as follows: k HOMO and the distribution density of LUMO d k LUMO The graph shows the distribution density d of the HOMO in each atom with serial number k. k HOMO And the distribution density of LUMO d k LUMO Figures 6 to 11 show graphs illustrating the product of the two orbitals, and molecular orbital diagrams obtained through simulation. The overlap index values ​​are shown in Table 1 below.

[0601] [Table 1]

[0602] Table 1 shows that the overlap index of the polymer in the example was in the range of 0.00001 to 1.8, while the overlap index of the TFB in the comparative example was outside this range.

[0603] Figures 2-11 show that the polymers of the examples having overlap indices within the scope of the present invention have less overlap between the HOMO and LUMO compared to the TFB of the comparative examples having overlap indices outside the scope of the present invention.

[0604] [Characteristic evaluation] Polymers A-1 to A-6 from Examples 1 to 6, polymers A-8 to A-21 from Examples 8 to 21, and poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine)] (TFB) (manufactured by Luminescence Technology Corp.) having the above constituent units were measured for HOMO level (eV), LUMO level (eV), glass transition temperature (Tg) (°C), and solvent resistance by the following method. The weight-average molecular weight (Mw) and dispersion (Mw / Mn) of TFB were measured using SEC. As a result, the weight-average molecular weight and Mw / Mn of TFB were 359,000 and 3.4, respectively. The results are shown in Tables 2 and 3 below.

[0605] (Measurement of HOMO level) A polymer was dissolved in xylene to a concentration of 1% by mass to prepare a coating solution. The prepared coating solution was applied to a UV-cleaned ITO-coated glass substrate and coated by spin coating at a rotation speed of 2000 rpm. The film was then dried on a hot plate at 150°C for 30 minutes to prepare a sample for measurement. The HOMO level of the sample was measured using an air-in-air photoelectron spectrometer (AC-3, RIKEN KEKI Co., Ltd.). The tangent intersection point of the rising edge was calculated from the measurement results and defined as the HOMO level (eV). Note that the HOMO level is usually a negative value.

[0606] (Measurement of LUMO level) A polymer was dissolved in toluene to a concentration of 3.2% by mass to prepare a coating solution. The prepared coating solution was used to deposit a film on a UV-cleaned ITO-coated glass substrate by spin coating at a rotation speed of 1600 rpm. The film was then dried on a hot plate at 250°C for 60 minutes to prepare a sample for measurement (film thickness: approximately 70 nm). The obtained sample was cooled to 77 K (-196°C), and the photoluminescence (PL) spectrum was measured. The LUMO level (eV) was calculated from the shortest wavelength peak value of the PL spectrum.

[0607] (Glass transition temperature (Tg)) Using a differential scanning calorimeter (DSC) (Seiko Instruments, product name: DSC6000), a sample (polymer) was heated to 300°C at a heating rate of 10°C / min and held for 10 minutes. Then, it was cooled to 25°C at a cooling rate of 10°C / min and held for 10 minutes. Finally, it was heated back up to 300°C at a heating rate of 10°C / min for measurement. After the measurement, it was cooled to room temperature (25°C) at 10°C / min.

[0608] (solvent resistance) The solvent resistance of the polymer was evaluated by the following method. Specifically, a polymer coating solution was prepared by dissolving the polymer in xylene, a solvent, at a concentration of 1% by mass. Next, the polymer coating solution was applied to a quartz substrate by spin coating, and then dried at 140°C for 30 minutes to form a film with a dry thickness of 25 nm. The absorption spectrum of the formed film (film before solvent immersion) was measured using a UV-Vis spectrophotometer (Shimadzu Corporation, UV-1800). The wavelength of the longest wavelength peak in the absorption spectrum was measured and used as the reference wavelength.

[0609] Next, the same film on the quartz substrate (the film before solvent immersion) was immersed for 20 minutes in solvents of the type and temperature listed in Table 3 below. After removal from the solvent, it was dried at 140°C for 30 minutes. The absorption spectrum of the dried film (the film after solvent immersion) was measured using a UV-Vis spectrophotometer in the same manner as above. For this absorption spectrum, the ratio of the intensity of the absorption spectrum after solvent immersion at the reference wavelength to the intensity of the absorption spectrum before solvent immersion at the reference wavelength ("intensity of absorption spectrum after solvent immersion at the reference wavelength" / "intensity of absorption spectrum after solvent immersion at the reference wavelength" × 100 (%)) was defined as the solvent resistance value (%). Solvent resistance was evaluated according to the following criteria: A: Solvent resistance value is 90% or higher. B: Solvent resistance value is 75% or more but less than 90%. C: Solvent resistance value is less than 75%.

[0610] Solvent resistance is preferably rated A or B, with A being more preferable. With these ratings, even if another layer is formed on the polymer-containing layer by a wet process, film mixing between the polymer-containing layer and the other layer is further suppressed.

[0611] [Table 2]

[0612] [Table 3]

[0613] <Fabrication and Evaluation of Quantum Dot Electroluminescent Devices 1> [Fabrication of quantum dot electroluminescent devices using blue quantum dots] (Example 101: Quantum dot electroluminescent element 1B) As the first electrode (anode), an ITO-coated glass substrate patterned with indium tin oxide (ITO) to a thickness of 150 nm was used. This ITO-coated glass substrate was sequentially washed with a neutral detergent, deionized water, water, and isopropyl alcohol, and then subjected to UV-ozone treatment. Next, poly(3,4-ethylenedioxythiophene) / poly(4-styrene sulfonate) (PEDOT / PSS) (manufactured by Sigma-Aldrich) was applied to this ITO-coated glass substrate by spin coating to a dry film thickness of 30 nm, and then dried. As a result, a hole injection layer with a thickness (dry film thickness) of 30 nm was formed on the ITO-coated glass substrate.

[0614] A 1.0% by mass toluene solution of polymer A-3 (hole transport material) from Example 3 was applied to this hole injection layer by spin coating to a dry film thickness of 30 nm, and then heat-treated 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.

[0615] The following structure is contained in cyclohexane:

[0616] [ka]

[0617] A quantum dot dispersion was prepared by dispersing blue quantum dots of ZnTeSe / ZnSe / ZnS (core / shell / shell; average diameter = approximately 10 nm) at a concentration of 1.0 mass%. The hole transport layer is almost insoluble in cyclohexane. 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 emitting layer with a thickness (dry film thickness) of 30 nm was formed on the hole transport layer. The light emitted when the quantum dot dispersion was irradiated with ultraviolet light had a center wavelength of 462 nm and a full width at half maximum of 30 nm.

[0618] The quantum dot light-emitting layer was completely dried. On this quantum dot light-emitting layer, lithium quinolate (Liq) and 1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI) (manufactured by Sigma-Aldrich) as an electron transport material were co-deposited using a vacuum deposition apparatus. As a result, an electron transport layer with a thickness of 36 nm was formed on the quantum dot light-emitting layer.

[0619] Using a vacuum deposition apparatus, (8-quinolinolate)lithium (lithium quinolate) (Liq) was deposited onto this electron transport layer. As a result, an electron injection layer with a thickness of 0.5 nm was formed on the electron transport layer.

[0620] Using a vacuum deposition apparatus, aluminum (Al) was deposited onto this electron injection layer. As a result, a second electrode (cathode) with a thickness of 100 nm was formed on the electron injection layer. This yielded quantum dot electroluminescent device 1B.

[0621] (Example 102: Quantum dot electroluminescent device 2B) Quantum dot electroluminescent element 2B was fabricated using the same procedure as for the quantum dot electroluminescent element 1B in Example 101, except that polymer A-2 from Example 2 was used instead of polymer A-3 from Example 3. Note that the hole transport layer is hardly soluble in cyclohexane.

[0622] (Example 103: Quantum dot electroluminescent element 3B) Quantum dot electroluminescent element 3B was fabricated using the same procedure as for the quantum dot electroluminescent element 1B in Example 101, except that polymer A-1 from Example 1 was used instead of polymer A-3 from Example 3. Note that the hole transport layer is hardly soluble in cyclohexane.

[0623] (Comparative Example 2: Quantum Dot Electroluminescent Element 4B) Quantum dot electroluminescent element 4B was fabricated using the same procedure as for the quantum dot electroluminescent element 1B in Example 101, except that poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine)] (TFB) (manufactured by Luminescence Technology Corp.) was used instead of polymer A-3 in Example 3. Note that the hole transport layer is hardly soluble in cyclohexane.

[0624] (Example 104: Quantum dot electroluminescent element 5B) Quantum dot electroluminescent element 5B was fabricated using the same procedure as for the fabrication of quantum dot electroluminescent element 1B in Example 101, except that polymer A-8 from Example 8 was used instead of polymer A-3 from Example 3. Note that the hole transport layer is hardly soluble in cyclohexane.

[0625] (Example 105: Quantum dot electroluminescent element 6B) Quantum dot electroluminescent element 6B was fabricated using the same procedure as for the quantum dot electroluminescent element 1B in Example 101, except that polymer A-10 from Example 10 was used instead of polymer A-3 from Example 3. Note that the hole transport layer is hardly soluble in cyclohexane.

[0626] (Example 106: Quantum dot electroluminescent element 7B) Quantum dot electroluminescent element 7B was fabricated using the same procedure as for the quantum dot electroluminescent element 1B in Example 101, except that polymer A-11 from Example 11 was used instead of polymer A-3 from Example 3. Note that the hole transport layer is hardly soluble in cyclohexane.

[0627] (Example 107: Quantum dot electroluminescent element 8B) Quantum dot electroluminescent element 8B was fabricated using the same procedure as for the quantum dot electroluminescent element 1B in Example 101, except that polymer A-12 from Example 12 was used instead of polymer A-3 from Example 3. Note that the hole transport layer is hardly soluble in cyclohexane.

[0628] (Example 108: Quantum dot electroluminescent element 9B) Quantum dot electroluminescent element 9B was fabricated using the same procedure as for the quantum dot electroluminescent element 1B in Example 101, except that polymer A-14 from Example 14 was used instead of polymer A-3 from Example 3. Note that the hole transport layer is hardly soluble in cyclohexane.

[0629] (Example 109: Quantum dot electroluminescent element 10B) Quantum dot electroluminescent element 10B was fabricated using the same procedure as for the quantum dot electroluminescent element 1B in Example 101, except that polymer A-15 from Example 15 was used instead of polymer A-3 from Example 3. Note that the hole transport layer is hardly soluble in cyclohexane.

[0630] (Example 110: Quantum dot electroluminescent element 11B) Quantum dot electroluminescent element 11B was fabricated using the same procedure as for the quantum dot electroluminescent element 1B in Example 101, except that polymer A-16 from Example 16 was used instead of polymer A-3 from Example 3. Note that the hole transport layer is hardly soluble in cyclohexane.

[0631] (Example 111: Quantum dot electroluminescent element 12B) Quantum dot electroluminescent element 12B was fabricated using the same procedure as for the quantum dot electroluminescent element 1B in Example 101, except that polymer A-17 from Example 17 was used instead of polymer A-3 from Example 3. Note that the hole transport layer is hardly soluble in cyclohexane.

[0632] (Example 201: Quantum dot electroluminescent element 13B) In forming the hole transport layer, a toluene solution containing 0.8% by mass of polymer A-1 (hole transport material) from Example 1 and 0.2% by mass of compound AD-1 (described below) was used instead of a 1.0% by mass toluene solution of polymer A-3 (hole transport material) from Example 3. The same procedure as for fabricating quantum dot electroluminescent element 1B in Example 101 was followed to fabricate quantum dot electroluminescent element 13B. Note that the hole transport layer is almost insoluble in cyclohexane.

[0633] (Example 202: Quantum dot electroluminescent element 14B) Quantum dot electroluminescent element 14B was fabricated using the same procedure as for the quantum dot electroluminescent element 13B in Example 201, except that polymer A-10 from Example 10 was used instead of polymer A-1 from Example 1. Note that the hole transport layer is hardly soluble in cyclohexane.

[0634] (Example 203: Quantum dot electroluminescent element 15B) Quantum dot electroluminescent element 15B was fabricated using the same procedure as for the fabrication of quantum dot electroluminescent element 14B in Example 202, except that compound AD-2 was used instead of compound AD-1. Note that the hole transport layer is hardly soluble in cyclohexane.

[0635] (Example 204: Quantum dot electroluminescent element 16B) Quantum dot electroluminescent element 16B was fabricated using the same procedure as for the fabrication of quantum dot electroluminescent element 14B in Example 202, except that compound AD-3 was used instead of compound AD-1. Note that the hole transport layer is hardly soluble in cyclohexane.

[0636] (Example 205: Quantum dot electroluminescent element 17B) Quantum dot electroluminescent element 17B was fabricated using the same procedure as for the fabrication of quantum dot electroluminescent element 14B in Example 202, except that compound AD-4 was used instead of compound AD-1. Note that the hole transport layer is hardly soluble in cyclohexane.

[0637] (Example 206: Quantum dot electroluminescent element 18B) Quantum dot electroluminescent element 18B was fabricated using the same procedure as for the fabrication of quantum dot electroluminescent element 14B in Example 202, except that compound AD-5 was used instead of compound AD-1. Note that the hole transport layer is hardly soluble in cyclohexane.

[0638] (Example 207: Quantum dot electroluminescent element 19B) Quantum dot electroluminescent element 19B was fabricated using the same procedure as for the fabrication of quantum dot electroluminescent element 14B in Example 202, except that compound AD-6 was used instead of compound AD-1. Note that the hole transport layer is hardly soluble in cyclohexane.

[0639] (Example 208: Quantum dot electroluminescent element 20B) Quantum dot electroluminescent element 20B was fabricated using the same procedure as for the fabrication of quantum dot electroluminescent element 14B in Example 202, except that compound AD-7 was used instead of compound AD-1. Note that the hole transport layer is hardly soluble in cyclohexane.

[0640] [ka]

[0641] (HOMO and LUMO of compounds AD-1 to AD-7) The HOMO and LUMO of compounds AD-1 to AD-7 were measured using the same method as the evaluation method for the polymers in the above examples. The HOMO and LUMO of compounds AD-1 to AD-7 are shown below.

[0642] Compound AD-1: HOMO=-6.56eV, LUMO=-2.73eV, Compound AD-2: HOMO=-6.24eV, LUMO=-2.80eV, Compound AD-3: HOMO=-5.98eV, LUMO=-2.65eV, Compound AD-4: HOMO=-5.80eV, LUMO=-2.48eV, Compound AD-5: HOMO=-5.67eV, LUMO=-2.24eV, Compound AD-6: HOMO=-5.57eV, LUMO=-2.50eV, Compound AD-7: HOMO=-5.38eV, LUMO=-2.34eV.

[0643] [Evaluation of Quantum Dot Electroluminescent Devices 1] The quantum dot electroluminescent elements 1B-3B of Examples 101-103, quantum dot electroluminescent element 4B of Comparative Example 2, quantum dot electroluminescent elements 5B-12B of Examples 104-111, and quantum dot electroluminescent elements 13B-20B of Examples 201-208 were evaluated for their lifetime using the method described below. The emission of light from these elements was confirmed to be blue, with a maximum emission wavelength of approximately 480 nm. The results are shown in Tables 4 and 5 below.

[0644] (This element's lifespan) Using a DC constant voltage power supply (Source Meter, manufactured by Keyence Corporation), a predetermined voltage was applied to each quantum dot electroluminescent element, causing each element to emit light. While measuring the light emitted by the quantum dot electroluminescent elements with a luminance measuring device (SR-3, manufactured by Topcom Corporation), the current was gradually increased until the luminance reached 650 nits (cd / m²). 2 The current was kept constant once the reading reached 50%, and the device was left undisturbed. The time it took for the brightness value measured by the brightness measuring device to gradually decrease to 50% of the initial brightness was defined as "LT50 (hr)".

[0645] [Table 4]

[0646] [Table 5]

[0647] The results in Tables 4 and 5 show that the quantum dot electroluminescent elements 1B-3B and 5B-20B of the examples exhibit significantly longer device lifetimes compared to the comparative example quantum dot electroluminescent element 4B, which does not use the polymer according to the present invention.

[0648] <Fabrication and Evaluation of Quantum Dot Electroluminescent Devices 2> [Fabrication of quantum dot electroluminescent devices using red quantum dots] (Example 112: Electroluminescent element 3R) The blue quantum dot used in Example 103 has the following structure:

[0649] [ka]

[0650] Quantum dot electroluminescent element 3R was fabricated in the same manner as the electroluminescent element 3B of Example 103, except that the red quantum dots were changed to InP / ZnSe / ZnS (core / shell / shell; average diameter = approximately 10 nm). The light emitted when ultraviolet light was irradiated onto the quantum dot dispersion had a center wavelength of 627 nm and a full width at half maximum of 35 nm.

[0651] (Comparative Example 3: Electroluminescent element 4R) Quantum dot electroluminescent element 4R was fabricated in the same manner as the electroluminescent element 4B in Comparative Example 2, except that the blue quantum dots used in Comparative Example 2 were replaced with the red quantum dots used in the fabrication of electroluminescent element 3R in Example 112.

[0652] [Fabrication of quantum dot electroluminescent devices using green quantum dots] (Example 113: Electroluminescent element 3G) The blue quantum dot used in Example 103 has the following structure:

[0653] [ka]

[0654] Quantum dot electroluminescent element 3G was fabricated in the same manner as the electroluminescent element 3B of Example 103, except that the green quantum dots were changed to InP / ZnSe / ZnS (core / shell / shell; average diameter = approximately 15 nm). The light emitted when ultraviolet light was irradiated onto the quantum dot dispersion had a center wavelength of 550 nm and a full width at half maximum of 45 nm.

[0655] (Comparative Example 4: Electroluminescent element 4G) Quantum dot electroluminescent element 4G was fabricated in the same manner as the electroluminescent element 4B in Comparative Example 2, except that the blue quantum dots used in Comparative Example 2 were replaced with green quantum dots used in the fabrication of electroluminescent element 3G in Example 113.

[0656] [Evaluation of Quantum Dot Electroluminescent Devices 2] The quantum dot electroluminescent elements 3R, 3G, and 3B of Examples 112, 113, and 103, and quantum dot electroluminescent elements 4R, 4G, and 4B of Comparative Examples 3, 4, and 2, were evaluated for their lifetimes using the method described below. Regarding the light emission of these elements, quantum dot electroluminescent elements 3R and 4R were confirmed to emit red light with a maximum emission wavelength of approximately 640 nm. Quantum dot electroluminescent elements 3G and 4G were confirmed to emit green light with a maximum emission wavelength of approximately 550 nm. Quantum dot electroluminescent elements 3B and 4B were confirmed to emit blue light with a maximum emission wavelength of approximately 480 nm. The results are shown in Tables 6-8 below.

[0657] (This element's lifespan) Using a DC constant voltage power supply (Source Meter, manufactured by Keyence Corporation), a predetermined voltage was applied to each quantum dot electroluminescent element, causing each element to emit light. While measuring the light emitted by the quantum dot electroluminescent elements with a luminance meter (SR-3, manufactured by Topcom Corporation), the current was gradually increased until the luminance for red light reached 9000 nits (cd / m²). 2 ), in green it is 5400 nits (cd / m²). 2 ), in blue, 650 nits (cd / m²) 2 The current was kept constant once the luminance reached 90%, and the device was left undisturbed. The time it took for the luminance value measured by the luminance measuring device to gradually decrease and reach 90% of the initial luminance was defined as "LT90 (hr)".

[0658] [Table 6]

[0659] [Table 7]

[0660] [Table 8]

[0661] From the results in Tables 6-8, it can be seen that the quantum dot electroluminescent element 3R of the example exhibits a significantly longer device lifetime compared to the comparative example quantum dot electroluminescent element 4R, which does not use the polymer according to the present invention. It can be seen that the quantum dot electroluminescent element 3G of the example exhibits a significantly longer device lifetime compared to the comparative example quantum dot electroluminescent element 4G, which does not use the polymer according to the present invention. It can be seen that the quantum dot electroluminescent element 3B of the example exhibits a significantly longer device lifetime compared to the comparative example quantum dot electroluminescent element 4B, which does not use the polymer according to the present invention. From these results, it can be seen that the quantum dot electroluminescent elements using the polymer according to the present invention exhibit a significantly longer device lifetime for all RGB emission colors compared to the quantum dot electroluminescent elements that do not use the polymer according to the present invention.

[0662] Although the present invention has been described above with reference to embodiments and examples, the present invention is not limited to specific embodiments or examples, and various modifications and changes are possible within the scope of the invention as described in the claims. [Explanation of Symbols]

[0663] 100... Electroluminescent element (EL element), 110... Circuit board, 120...first electrode, 130... Hole injection layer, 140... Hole transport layer, 150...Luminescent layer, 160...electron transport layer, 170...electron injection layer, 180...Second electrode.

Claims

1. A polymer having an overlap index of 0.00001 or more and 1.8 or less, and containing a constituent unit represented by the following formula (1): [Math 1] In the above formula, k is the sequential number assigned to the atom in the chemical formula of the constituent unit of the polymer, and d ｋ ＨＯＭＯ This shows the distribution density of HOMO in the atom with serial number k, and d ｋ ＬＵＭＯ This shows the distribution density of LUMO in the atom with serial number k; 【number】 In the above formula (1), Ar1 and Ar2 each independently represent a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 carbon atoms. Ar3 represents a group selected from the following group (I): 【number】 In the above sections I-1 to I-7, R111 to R123 each independently represent a hydrogen atom or a linear or branched hydrocarbon group having 1 to 16 carbon atoms. * indicates the bond position with an adjacent atom. Ar 4 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 carbon atoms, or a substituted or unsubstituted divalent aromatic heterocyclic group having 3 to 60 ring-forming atoms. Ar 5 represents a divalent aromatic heterocyclic group with a single bond, or substituted or unsubstituted ring-forming atoms numbering between 3 and 60. Each R1 independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), or a cyano group (-CN). Each R2 independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), or a cyano group (-CN). A is a structure represented by the following formula (2) or formula (3), 【number】 In the above formula (2), Each Ar6 independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. Each Ar7 independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. Two or more Ar7 atoms may form fused rings with the benzene ring to which they are bonded. * indicates the bond position with an adjacent atom; In the above formula (3), Each Ar8 independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. Each Ar9 independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. X represents S, O, or C substituted with two linear or branched hydrocarbon groups having 1 to 16 carbon atoms, either substituted or unsubstituted. Two or more Ar9 atoms may form fused rings with the benzene ring to which they are bonded. * indicates the bond position with an adjacent atom.

2. The polymer according to claim 1, wherein the overlap index represented by the above formula is 0.00001 or more and 1.2 or less.

3. A polymer containing the constituent units represented by the following formula (1): 【Chemistry 4】 In the above formula (1), Ar １ and Ar ２ Each of these independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 carbon atoms. Ar ３ This represents a group selected from the following group (I): 【Transformation 5】 In the above sections I-1 to I-7, R111 to R123 each independently represent a hydrogen atom or a linear or branched hydrocarbon group having 1 to 16 carbon atoms. * indicates the bond position with an adjacent atom. Ar ４ This represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 60 carbon atoms, or a substituted or unsubstituted divalent aromatic heterocyclic group having 3 to 60 ring-forming atoms. Ar ５ represents a single bond or a divalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, which may be substituted or unsubstituted. Each R １ Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), and a cyano group (-CN). Each R ２ Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), and a cyano group (-CN). A is a structure represented by the following formula (2) or formula (3), 【Transformation 6】 In the above formula (2), Each Ar ６ Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. Each Ar ７ Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. 2 or more Ar ７ The two or more Ar ７ A fused ring may be formed between the bonded benzene ring and the bonded ring. * indicates the bond position with an adjacent atom; In the above formula (3), Each Ar ８ Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. Each Ar ９ Each of these independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylthio group, an alkoxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms, a substituted or unsubstituted monovalent aromatic heterocyclic group having 3 to 60 ring-forming atoms, or a substituted or unsubstituted monovalent ring aggregate group having one or more aromatic hydrocarbon rings having 6 to 60 carbon atoms and one or more aromatic heterocyclic rings having 3 to 60 ring-forming atoms linked by a single bond. X represents S, O, or C substituted with two linear or branched hydrocarbon groups having 1 to 16 carbon atoms, either substituted or unsubstituted. 2 or more Ar ９ The two or more Ar ９ A fused ring may be formed between the bonded benzene ring and the bonded ring. * indicates the bond position with an adjacent atom.

4. In formula (1) above, Ar １ Ar ２ and Ar ４ The polymer according to any one of claims 1 to 3, wherein at least one selected from the group consisting of is independently a group selected from the following group (II): 【Transformation 7】 In the above sections II-1 to II-7, R ２１１ ~R ２２５ Each of these independently represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 16 carbon atoms. * indicates the bond position with an adjacent atom.

5. In formula (1) above, Ar １ Ar ２ and Ar ４ The polymer according to claim 4, wherein each of the groups is independently selected from group (II) above.

6. The polymer according to any one of claims 1 to 3, wherein the aforementioned structural unit is at least one structural unit selected from the following group (A): 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 In the above formula, n represents an integer between 1 and 20, The compound represented by the above formula contains two or more "C" ｎ H ２ｎ＋１ If it has a group represented by "-", each "C ｎ H ２ｎ＋１ The n in the "-" can be the same or different from each other, and each "C ｎ H ２ｎ＋１ The bases represented by "-" may be the same or different from each other.

7. The polymer according to any one of claims 1 to 3, wherein the aforementioned structural unit is at least one structural unit selected from the following group (B): 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 In the above formula, "C １２ H ２５ The group represented by "-" represents an n-dodecyl group. "C １０ H ２１ The group represented by "-" represents an n-decyl group. "C ８ H １７ The group represented by "-" represents an n-octyl group. "C ６ H １３ The group represented by "-" represents an n-hexyl group.

8. The polymer according to any one of claims 1 to 3, wherein the aforementioned structural unit is at least one structural unit selected from the following group (B'): 【Chemistry 16】 In the above formula, "C ８ H １７ The group represented by "-" represents an n-octyl group.

9. A composition comprising the polymer described in any one of claims 1 to 3.

10. The composition according to claim 9, further comprising a low molecular weight material that satisfies condition (a) below, and also satisfies condition (b), condition (c), or both: (a) The band gap of the polymer is larger than that of the polymer. (b) The LUMO is shallower than that of the polymer. (c) The HOMO is deeper than that of the polymer.

11. An electroluminescent element comprising a pair of electrodes and at least one layer of organic film containing the polymer described in any one of claims 1 to 3, disposed between the pair of electrodes.

12. An electroluminescent element comprising a pair of electrodes and one or more organic layers disposed between the pair of electrodes, wherein at least one of the organic layers comprises a polymer according to any one of claims 1 to 3 and a low molecular weight material satisfying the following condition (a) and the following condition (b), the following condition (c), or both: (a) The band gap of the low molecular weight material is larger than that of the polymer. (b) The LUMO of the low molecular weight material is shallower than that of the polymer. (c) The HOMO of the low molecular weight material is deeper than that of the polymer.

13. An electroluminescent element comprising a pair of electrodes and at least one layer of organic film containing the composition described in claim 9, disposed between the pair of electrodes.

14. The electroluminescent element according to claim 11, further comprising a layer containing quantum dots.

15. The electroluminescent element according to claim 12, further comprising a layer containing quantum dots.

16. The electroluminescent element according to claim 13, further comprising a layer containing quantum dots.

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