Polymer compound, and electroluminescent device material, liquid composition, and electroluminescent device including same

Abstract

Disclosed are a polymer compound, and an electroluminescent device material, a liquid composition, and an electroluminescent device including the polymer compound. Embodiments provide a technique capable of achieving a good balance between durability (e.g., light emission lifetime) and light emission efficiency of an electroluminescent device, and in order to solve the above problem, provide a polymer compound including a structural unit (A) represented by Chemical Formula 1. In Chemical Formula 1, Ar1, Ar2, Ar11, Ar12, X1, Y1, and L1 are each independently as described in the specification. (Chemical Formula 1)

Description

[0001] This application claims priority to and the benefit of Japanese Patent Application No. 2024-49468 filed in the Japan Patent Office on March 26, 2024, and Korean Patent Application No. 10-2025-0001767 filed in the Korean Intellectual Property Office on January 6, 2025, the entire contents of which are incorporated herein by reference. Technical Field

[0002] Disclosed are a polymer compound, and an electroluminescent device material, a liquid composition, and an electroluminescent device comprising the polymer compound. Background Art

[0003] The research and development of electroluminescent devices (EL devices) are actively progressing. In particular, EL devices are expected to be used as solid-state light-emitting, inexpensive, and large-area full-color display devices or write light source arrays. EL devices are light-emitting devices that include a thin film with a thickness of several nanometers to several hundred nanometers between an anode and a cathode. In addition, EL elements often further include a hole transport layer, a light-emitting layer, an electron transport layer, etc.

[0004] Among these, the light-emitting layer includes a fluorescent light-emitting material and / or a phosphorescent light-emitting material. Phosphorescent light-emitting materials are materials that are expected to have a higher luminous efficiency than fluorescent light-emitting materials. In addition, in order to cover a wide color gamut, RGB light sources need to have an emission spectrum with a narrow half-width (FWHM). For example, although deep blue is particularly desired for blue, no device has been found to have a long lifespan and meet the requirements of color purity.

[0005] As a solution to the problem, there is a light-emitting device using "quantum dots" (which are inorganic light-emitting materials) as light-emitting materials (see patent document 1). Quantum dots (QD) are semiconductor materials with a crystal structure with a size of several nanometers and are composed of hundreds to thousands of atoms. Because quantum dots are very small in size, the surface area per unit volume is large. For this reason, most of the atoms are present on the surface of the nanocrystals and exhibit a quantum confinement effect. Due to the quantum confinement effect, quantum dots can adjust the emission wavelength by adjusting their size, and have received much attention due to their characteristics such as improved color purity and high photoluminescence (PL) luminous efficiency. A quantum dot electroluminescent device (QD LED) is a three-layer device including a hole transport layer and an electron transport layer at both sides of the quantum dot light-emitting layer, which is referred to as a basic device.

[0006] In order to improve the characteristics of such quantum dot electroluminescent devices, technologies for improving the hole transport and hole injection properties of hole transport materials have been proposed. For example, Patent Document 2 proposes an arylamine-fluorene alternating copolymer (polymer compound) having a hydrocarbon group in the side chain as a hole transport material.

[0007] [Patent Document 1] Japanese Patent Laid-Open Publication No. 2010-199067

[0008] [Patent Document 2] Japanese Patent Publication No. 2021-138915 Summary of the Invention

[0009] According to the arylamine-fluorene alternating copolymer disclosed in Patent Document 2, the hole injection properties of the hole transport material are improved, the durability (especially the luminescence lifetime) is improved, and sufficient luminescence efficiency is achieved. However, there is a need for a technology that can further improve the durability (especially the luminescence lifetime) and luminescence efficiency in a good balance compared to electroluminescent devices (especially quantum dot electroluminescent devices) using the hole transport material disclosed in Patent Document 2.

[0010] Therefore, the embodiments provide a technology capable of achieving a good balance between durability (eg, luminescence lifetime) and luminous efficiency of an electroluminescent device (eg, a quantum dot electroluminescent device).

[0011] The present inventors have found that the above problems can be solved by using a polymer compound having a specific structure.

[0012] Therefore, the embodiment provides a polymer compound including a structural unit (A) represented by Chemical Formula 1:

[0013] Chemical formula 1

[0014]

[0015] In Chemical Formula 1,

[0016] Ar 11 and Ar 12 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms,

[0017] Ar 11 and Ar 12 are optionally linked to each other to form a ring,

[0018] L 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms,

[0019] Ar 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms,

[0020] Ar 2is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms, and Ar 2 Optionally with Ar 1 Form a ring,

[0021] X 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms, and

[0022] Y 1 is a group selected from the following: an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by a thiol group-containing alkyl group having 1 to 14 carbon atoms, an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by a thiol group-containing alkoxyalkyl group having 2 to 14 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by a thiol group-containing alkyl group having 1 to 14 carbon atoms and a thiol group-containing alkoxyalkyl group having 2 to 14 carbon atoms.

[0023] The electroluminescent device according to the embodiment (eg, quantum dot electroluminescent device) may have a good balance of durability (eg, luminescence lifetime) and luminous efficiency. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] Figure 1 is a schematic diagram showing an electroluminescent device according to an embodiment. DETAILED DESCRIPTION

[0025] One embodiment provides a polymer compound including a structural unit (A) represented by Chemical Formula 1:

[0026] Chemical formula 1

[0027]

[0028] In Chemical Formula 1,

[0029] Ar 11 and Ar 12 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms,

[0030] Ar 11 and Ar 12 are optionally linked to each other to form a ring,

[0031] L 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms,

[0032] Ar 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms,

[0033] Ar 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms, and Ar 2 Optionally with Ar 1 Form a ring,

[0034] X 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms,

[0035] Y 1 is a group selected from the following: an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by a thiol group-containing alkyl group having 1 to 14 carbon atoms, an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by a thiol group-containing alkoxyalkyl group having 2 to 14 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by a thiol group-containing alkyl group having 1 to 14 carbon atoms and a thiol group-containing alkoxyalkyl group having 2 to 14 carbon atoms.

[0036] In this specification, the structural unit (A) represented by Chemical Formula 1 is also simply referred to as “structural unit (A)” or “structural unit (A) according to an embodiment”.

[0037] In addition, the structural unit having the following structure in the “structural unit (A) represented by Chemical Formula 1” is also simply referred to as “structural unit X” or “structural unit X according to an embodiment”.

[0038]

[0039] Likewise, the structural unit "-Y" in the "structural unit (A) represented by Chemical Formula 1" 1 -" is also referred to as "structural unit Y" or "structural unit Y according to an embodiment".

[0040] In addition, the polymer compound having the structural unit (A) represented by Chemical Formula 1 is also simply referred to as a “polymer compound” or a “polymer compound according to an embodiment”.

[0041] According to another embodiment, provided is an electroluminescent device material including the polymer compound according to the embodiment.

[0042] According to another embodiment, a liquid composition including the polymer compound according to the embodiment and at least one solvent is provided.

[0043] According to another embodiment, an electroluminescent device includes a first electrode, a second electrode, and at least one organic film between the first electrode and the second electrode, wherein the at least one organic film includes the polymer compound according to the embodiment.

[0044] As used herein, an electroluminescent device is simply referred to as an "LED" or an "EL device."

[0045] Quantum dot electroluminescent devices are also referred to as "QLEDs".

[0046] Perovskite electroluminescent devices are also referred to as "PeLEDs".

[0047] By such a configuration, it is possible to provide a device that can achieve durability such as luminous lifetime (e.g., LT 50 ) and luminous efficiency such as maximum external quantum efficiency (EQE max ) are electroluminescent devices such as quantum dot electroluminescent devices.

[0048] As materials constituting the light-emitting layer or carrier transport layer of an electroluminescent device, a variety of low-molecular-weight materials and polymer materials are used. Among these, low-molecular-weight materials are superior in terms of device efficiency and lifespan. However, when using low-molecular-weight materials, there is a problem of high manufacturing cost because the device needs to be manufactured using a vacuum process. Meanwhile, as polymeric materials, TFB of Patent Document 1 (e.g., paragraph "0037") and arylamine-fluorene alternating copolymer of Patent Document 2 are known as hole transport materials. However, in terms of recent high performance, TFB of Patent Document 1 cannot be said to have sufficiently long durability (luminescence lifetime), and arylamine-fluorene alternating copolymer of Patent Document 2, although it certainly has excellent durability, cannot be said to have sufficient luminescence efficiency, and there is room for improvement. Therefore, the present inventors have carefully studied means for solving the above-mentioned problem, i.e., achieving a good balance between durability (luminescence lifetime) and luminescence efficiency.

[0049] As a result, it has been found that by applying a polymer compound having the structural unit (A) represented by Chemical Formula 1 to an electroluminescent device, durability (luminescence lifetime) and luminous efficiency can be well balanced, compared to the case where a known material (e.g., the polymer material disclosed in Patent Document 2) is used. In addition, by applying the polymer compound to an electroluminescent device, it was found that sufficient luminous efficiency and luminous lifetime can be achieved while maintaining a certain level of low driving voltage.

[0050] The mechanism by which the above-mentioned effects are achieved by the embodiment is presumed to be as follows.

[0051] According to an embodiment, the polymer compound has a thiol group in the structural unit Y constituting the main chain. When the polymer compound according to the embodiment is included in the hole transport layer, the thiol group is firmly coordinated (bound (bonded)) to the light-emitting material included in the light-emitting layer adjacent to the hole transport layer, for example, the metal atom included in the quantum dot or perovskite compound. As a result, the arrangement of the light-emitting material such as the quantum dot or perovskite compound included in the light-emitting layer, for example, at the interface adjacent to the hole transport layer, is improved, and by arranging the light-emitting material at a high density, the hole injection property is improved. Therefore, an electroluminescent device such as a quantum dot electroluminescent device using the polymer compound according to the embodiment can exhibit high durability (luminescence lifetime) and also achieve excellent luminous efficiency.

[0052] In addition, since the polymer compound according to the embodiment has excellent film-forming properties and solvent solubility, it can be formed into a film using a wet (coating) method. Therefore, by using the polymer compound according to the embodiment, it becomes possible to expand the area of ​​the electroluminescent device and achieve high productivity. When the polymer compound is applied to the hole transport layer or hole injection layer of an EL device, particularly a QLED, the above effects can be effectively exhibited.

[0053] Additionally, the mechanism is speculation, and the present disclosure is not limited by the mechanism at all.

[0054] Hereinafter, embodiments are described. On the other hand, the present disclosure is not limited to the following embodiments. In addition, for better understanding and ease of description, the drawings are enlarged, and the size ratios of the components in the drawings may be different from those in reality. In addition, when describing the embodiments of the present disclosure with reference to the drawings, the same reference numerals are given to the same elements in the description of the drawings, and redundant descriptions may be omitted.

[0055] In this specification, unless otherwise specified, operations and measurements of physical properties are performed under the conditions of room temperature, for example, 20° C. or higher and 25° C. or lower and a relative humidity (RH) of 40% or higher and 50% or lower.

[0056] In the present specification, “x and y are each independently (are)” means that x and y may be the same or different.

[0057] In the present specification, "a group derived from compound z" or "a group derived from compound z" refers to a group in which, when "compound z" is a cyclic compound, as many hydrogen atoms directly bonded to ring atoms as the valences are removed from the cyclic structure to express free valences.

[0058] In this specification, the number of ring-forming atoms refers to the number of atoms constituting the corresponding ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a condensed ring, a ring set, etc.). Atoms that do not form a ring (e.g., a hydrogen atom that terminates a bond to an atom that forms a ring) or atoms included in a substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms. The number of ring-forming atoms described below is considered to be the same unless otherwise stated.

[0059] For example, a benzene ring has 6 ring-forming atoms, a naphthalene ring has 10 ring-forming atoms, a pyridine ring has 6 ring-forming atoms, and a furan ring has 5 ring-forming atoms.

[0060] When a benzene ring is substituted with a substituent such as an alkyl group, the number of carbon atoms in the alkyl group is not included in the number of ring atoms in the benzene ring. Therefore, the number of ring atoms in a benzene ring substituted with an alkyl group is 6. Furthermore, when a naphthalene ring is substituted with an alkyl group as a substituent, the number of carbon atoms in the alkyl group is not included in the number of ring atoms in the naphthalene ring. Therefore, the number of ring atoms in a naphthalene ring substituted with an alkyl group is 10.

[0061] For example, the number of hydrogen atoms or atoms constituting a substituent bonded to a pyridine ring is not included in the number of ring atoms of the pyridine ring. Therefore, the number of ring atoms of the pyridine ring bonded to hydrogen atoms or substituents is 6.

[0062] In this specification, "a substituent represents a hydrogen atom" means that the structure in which the substituent exists is unsubstituted. For example, in Chemical Formula 1-1, when R 11 to R 14 When all are hydrogen atoms, it means that R 11 to R 14 The benzene ring is p-phenylene.

[0063] In this specification, unless specifically defined, "substituted" refers to substituted by: alkyl, cycloalkyl, hydroxyalkyl, alkoxy, alkoxyalkyl, cycloalkoxy, alkenyl, alkynyl, primary amino (-NH2), secondary amino (-NH(R 1 ):R 1 is an alkyl or aryl group), a tertiary amino group (-N(R 1 )(R 2 ):R 1 and R 2 are each independently alkyl or aryl, and in this case, R 1 and R 2(optionally forming a ring), an aryl group, an aryloxy group, an alkylthio group, a cycloalkylthio group, an arylthio group, an alkoxycarbonyl group, an aryloxycarbonyl group, a hydroxyl group (-OH), a carboxyl group (-COOH), a thiol group (-SH), a cyano group (-CN), a halogen atom (fluorine atom, chlorine atom, bromine atom or iodine atom), or a combination thereof. On the other hand, when a group is substituted, the form of the group included in the definition of the substituent does not include a form further substituted by the group as a substituent. For example, when the substituent is an alkyl group, the alkyl group as a substituent is not further substituted by an alkyl group.

[0064] Herein, the alkyl group as a substituent may be a linear or branched alkyl group, for example, a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms. In particular, the alkyl group may be a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a tert-pentyl group, a neopentyl group, a 1,2-dimethylpropyl group, an n-hexyl group, an isohexyl group, a 1,3-dimethylbutyl group, a 1-isopropylpropyl group, a 1,2-dimethylbutyl group, an n-heptyl group, a 1,4-dimethylpentyl group, a 3-ethylpentyl group, a 2-methyl-1-isopropylpropyl group, a 1-ethyl-3-methyl Butyl, n-octyl, 2-ethylhexyl, 3-methyl-1-isopropylbutyl, 2-methyl-1-isopropylbutyl, 1-tert-butyl-2-methylpropyl, n-nonyl, 3,5,5-trimethylhexyl, n-decyl, isodecyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, nonadecyl, eicosyl, etc.

[0065] As a substituent, the cycloalkyl group may include, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0066] The hydroxyalkyl group may be, for example, an alkyl group (eg, hydroxymethyl, hydroxyethyl) substituted with 1 to 3 (eg, 1 or 2, and for example, 1) hydroxy groups.

[0067] The alkoxy group as a substituent may be a linear or branched alkoxy group, but is desirably a linear alkoxy group having 1 to 20 carbon atoms or a branched alkoxy group having 3 to 20 carbon atoms. For example, the alkoxy group may be, for example, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, a dodecyloxy group, a tridecyloxy group, a tetradecyloxy group, a pentadecyloxy group, a hexadecyloxy group, a heptadecyloxy group, an octadecyloxy group, a 2-ethylhexyloxy group, a 3-ethylpentyloxy group, and the like.

[0068] Examples of the cycloalkoxy group as a substituent include cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, and cyclohexyloxy.

[0069] The alkenyl group as a substituent may include, for example, vinyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 1-heptenyl, 2-heptenyl, 5-heptenyl, 1-octenyl, 3-octenyl, 5-octenyl, etc.

[0070] Alkyl groups as substituents may include, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 1-heptynyl, 2-heptynyl, 5-heptynyl, 1-octynyl, 3-octynyl, 5-octynyl, and the like.

[0071] The secondary amino group as a substituent may include, for example, an alkylamino group having 1 to 10 carbon atoms such as methylamino, ethylamino, n-propylamino, n-butylamino, isobutylamino, etc., and a monoarylamino group such as monophenylamino, mononaphthylamino, etc.

[0072] The tertiary amino group as a substituent may include, for example, a dialkylamino group having 2 to 20 carbon atoms such as dimethylamino, diethylamino, di-n-propylamino, di-n-butylamino and methylethylamino, and a diarylamino group such as diphenylamino and dinaphthylamino.

[0073] The aryl group as a substituent may be an aryl group having 6 to 30 (e.g., 6 to 25, 6 to 20, or 6 to 12) ring atoms (carbon atoms). Examples may include phenyl, naphthyl, biphenyl, fluorenyl, anthracenyl, pyrenyl, azulenyl, acenaphthenyl, biphenyl, and phenanthrenyl.

[0074] Examples of the aryloxy group as a substituent may include a phenoxy group and a naphthoxy group.

[0075] Examples of the alkylthio group as a substituent may include a methylthio group, an ethylthio group, a propylthio group, a pentylthio group, a hexylthio group, an octylthio group, and a dodecylthio group.

[0076] Examples of the cycloalkylthio group as a substituent may include a cyclopentylthio group, a cyclohexylthio group, and the like.

[0077] Examples of the arylthio group as a substituent may include a phenylthio group and a naphthylthio group.

[0078] Examples of the alkoxycarbonyl group as a substituent may include a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group, an octyloxycarbonyl group, and a dodecyloxycarbonyl group.

[0079] Examples of the aryloxycarbonyl group as a substituent may include a phenoxycarbonyl group and a naphthoxycarbonyl group.

[0080] The term "aromatic hydrocarbon group" refers to a hydrocarbon having an aromatic ring and includes monocyclic and polycyclic hydrocarbons, wherein the additional ring(s) of the polycyclic hydrocarbon may be aromatic or non-aromatic.

[0081] The term "heteroaromatic group" refers to an aromatic ring and includes monocyclic and polycyclic ring systems in which one to three aromatic ring atoms are selected from N, O, S, Si and P, and the additional ring(s) of the polycyclic ring system may be aromatic or non-aromatic.

[0082] [Polymer compound]

[0083] Structural Unit (A)

[0084] The polymer compound according to the embodiment has the structural unit (A) represented by Chemical Formula 1. There are two or more structural units (A) in the polymer compound. That is, the structural unit (A) represented by Chemical Formula 1 may be a repeating unit. Therefore, the polymer compound according to the embodiment may have a repeating unit (repeating unit A) represented by Chemical Formula 1. The polymer compound with structural unit (A) has excellent hole injection properties into quantum dots, etc., and can improve the durability (luminescence life) of the electroluminescent device. In addition, high current efficiency and low driving voltage can be achieved, and luminous efficiency can be improved. The polymer compound according to the embodiment may include only one type of structural unit (A), or may include two or more types of structural units (A). Furthermore, a plurality of structural units (A) may exist in block form, random form, alternating form, or periodic form.

[0085] Chemical formula 1

[0086]

[0087] In Chemical Formula 1, the structural unit X (the structural unit on the left side of Chemical Formula 1, i.e., the structural unit formed by two aromatic hydrocarbon groups and a nitrogen atom sandwiched therebetween) is a structural unit of the polymer compound according to an embodiment. Similarly, the structural unit Y of Chemical Formula 1 (the structural unit on the right side of Chemical Formula 1, i.e., the structural unit formed by “Y 1 ”) is a constituent unit of the polymer compound according to an embodiment. That is, the polymer compound according to an embodiment may be referred to as a copolymer including the structural unit X and the structural unit Y.

[0088] In Chemical Formula 1, Y 1The aromatic hydrocarbon group may be a group selected from the following: an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by an alkyl group having 1 to 14 carbon atoms containing a thiol group, an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by an alkoxyalkyl group having 2 to 14 carbon atoms containing a thiol group, or an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by an alkyl group having 1 to 14 carbon atoms containing a thiol group and an alkoxyalkyl group having 2 to 14 carbon atoms containing a thiol group.

[0089] Therefore, in the structural unit (A) according to the embodiment, Y 1 It may have an alkyl group having 1 to 14 carbon atoms containing a thiol group (an alkyl group having 1 to 14 carbon atoms having a thiol group), or an alkoxyalkyl group having 2 to 14 carbon atoms containing a thiol group (an alkoxyalkyl group having 2 to 14 carbon atoms having a thiol group). 1 It may have both an alkyl group having 1 to 14 carbon atoms containing a thiol group and an alkoxyalkyl group having 2 to 14 carbon atoms containing a thiol group. Therefore, when the polymer compound according to the embodiment is used as a hole transport material of an electroluminescent device, it can be firmly coordinated (bound) to a light-emitting material such as a quantum dot or a perovskite compound in the light-emitting layer, and improve (enhance) the arrangement of the light-emitting material included in the light-emitting layer. As a result, since the light-emitting material can be present in the light-emitting layer at a high density, for example, at the interface adjacent to the hole transport layer, durability (luminescence lifetime) and luminous efficiency can be well balanced.

[0090] In the present specification, the thiol group-containing alkyl group having 1 to 14 carbon atoms is sometimes simply referred to as a "thiol group-containing alkyl group" or simply as a "substituent (a)".

[0091] In addition, the thiol group-containing alkoxyalkyl group having 2 to 14 carbon atoms is sometimes simply referred to as a "thiol group-containing alkoxyalkyl group" or simply as a "substituent (b)".

[0092] Y 1 The substituent (a) may contain at least one of a thiol group-containing alkyl group and a thiol group-containing alkoxyalkyl group. For example, the substituent (b) may contain at least two of them. 1 It may have both a thiol group-containing alkyl group (substituent (a)) and a thiol group-containing alkoxyalkyl group (substituent (b)). 1 It may have two or more substituents (a), or may have two or more substituents (b). 1 When only substituent (a) is included in the 1 When only substituent (b) is included, one Y 1The number of the substituent (a) or the substituent (b) included in may be 1 or more, for example 2 or more, and one Y 1 The upper limit of the number of substituents (a) or substituents (b) included in is not particularly limited, but may be, for example, 6 or less, and, for example, 4 or less. 1 When both substituent (a) and substituent (b) are included, one Y 1 The sum of the number of substituents (a) and substituents (b) included in the formula (I) may be 2 or more. Meanwhile, the upper limit of the sum of the number of substituents (a) and substituents (b) is not particularly limited, but may be, for example, 6 or less, and, for example, 4 or less.

[0093] When Y 1 When there are two or more substituents (a), the structures of the substituents (a) may be the same or different. 1 When there are two or more substituents (b), the structures of the substituents (b) may be the same or different.

[0094] According to an embodiment, the alkyl group having 1 to 14 carbon atoms included in the thiol group-containing alkyl group (substituent (a)) may be a linear or branched alkyl group, and examples thereof may include 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-octyl-2-methylbutyl, 1-octyl-3-methylbutyl, 1-octyl-4-methylbutyl, 1-octyl-5-methylbutyl, 1-octyl-6-methylbutyl, 1-octyl-7-methylbutyl, 1-octyl-8-methylbutyl, 1-octyl-10-methylbutyl, 1-octyl-20-methylbutyl, 1-octyl-1 ... butyl, 1,4-dimethylpentyl, 3-ethylpentyl, 2-methyl-1-isopropylpropyl, 1-ethyl-3-methylbutyl, n-octyl, 2-ethylhexyl, 3-methyl-1-isopropylbutyl, 2-methyl-1-isopropylbutyl, 1-tert-butyl-2-methylpropyl, n-nonyl, 3,5,5-trimethylhexyl, n-decyl, isodecyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, n-tetradecyl, etc.

[0095] According to an embodiment, the alkoxyalkyl group having 2 to 14 carbon atoms included in the thiol group-containing alkoxyalkyl group (substituent (b)) is a linear or branched alkoxyalkyl group. The substituent (b) may be a group obtained by substituting an alkyl group having 1 to 13 carbon atoms with 1 to 3 (e.g., 1 to 2, for example, 1) alkoxy groups having 1 to 13 carbon atoms (in this case, the sum of the carbon numbers of the alkyl group and the alkoxy group is 2 to 14). Here, specific examples of the alkyl group include those of the substituent (a) having 13 or fewer carbon atoms. In addition, specific examples of the alkoxy group include those having 1 to 13 carbon atoms among the specific examples of the alkoxy group as a substituent.

[0096] Therefore, examples of the alkoxyalkyl group having 2 to 14 carbon atoms included in the substituent (b) may include methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, methoxypropyl, ethoxypropyl, propoxypropyl, butoxypropyl, methoxybutyl, ethoxybutyl, propoxybutyl, butoxybutyl, methoxypentyl, ethoxypentyl, propoxypentyl, butoxypentyl, methoxyhexyl, ethoxyhexyl, propoxyhexyl, butoxyhexyl, methoxyheptyl, ethoxyheptyl, propoxyheptyl, butoxyheptyl, and the like.

[0097] From the viewpoint of further improving durability (eg, luminescence lifetime), Y in Chemical Formula 1 1 Substituent (b) may be included. For example, Y in Chemical Formula 1 1 It may be an aromatic hydrocarbon group having 6 to 25 ring atoms substituted with an alkoxyalkyl group containing 2 to 14 carbon atoms and containing a thiol group. 1 It may be an aromatic hydrocarbon group having 6 to 25 ring atoms substituted with an alkoxyalkyl group containing 2 to 10 carbon atoms containing a thiol group. Also, the number of carbon atoms in the alkoxyalkyl group containing a thiol group means the sum of the number of carbon atoms constituting the alkoxy group and the alkyl group constituting the group. 1 In the form including the substituent (b), the number of thiol groups included in the substituent (b) may be 1 or more, or may be 2 or more. That is, in an embodiment, the substituent (b) (thiol group-containing alkoxyalkyl) may have one or more thiol groups. For example, the substituent (b) may have two or more thiol groups. At the same time, the upper limit of the number of thiol groups included in the substituent (b) is not particularly limited, and may be 4 or less.

[0098] From the viewpoint of further improving the luminous efficiency, Y in Chemical Formula 1 1 Substituent (a) may be included. That is, Y in Chemical Formula 1 1 It may be an aromatic hydrocarbon group having 6 to 25 ring atoms substituted with an alkyl group having 1 to 14 carbon atoms containing a thiol group. 1 It may be an aromatic hydrocarbon group having 6 to 25 ring atoms substituted with an alkyl group having 1 to 10 carbon atoms containing a thiol group. 1In the form including substituent (a), the number of thiol groups included in substituent (a) may be 1 or more, or may be 2 or more. That is, in one embodiment, substituent (a) (thiol group-containing alkyl) may have one thiol group. In another embodiment, substituent (a) may have two or more thiol groups. Meanwhile, the upper limit of the number of thiol groups included in substituent (a) is not particularly limited, but may be 4 or less.

[0099] From the viewpoint of further improving the balance between durability and luminous efficiency, or from the viewpoint of ensuring that the glass transition temperature (Tg) of the polymer compound is within an appropriate range and good thermal stability can be maintained, the alkyl group included in each of the substituent (a) or the substituent (b) (in the case of the substituent (b), excluding the alkyl portion of the alkoxy group (-OR) bonded to the aromatic hydrocarbon group) may have 1 or more and 12 or less carbon atoms, for example, 1 or more and 10 or less, for example, 2 or more and 8 or less, or 4 or more and 8 or less, for example, 6 carbon atoms. In addition, by setting the carbon number of the alkyl group constituting the substituent (a) or the alkyl group constituting the substituent (b) within the above range, when a film is formed using a wet (coating) method, solvent solubility can be excellent and film-forming properties can be improved.

[0100] The alkoxy group included in the substituent (b) may have 1 to 10 carbon atoms, for example, 1 to 8 carbon atoms, 1 to 6 carbon atoms, 2 to 4 carbon atoms, for example, 3 carbon atoms. According to the above form, durability and luminous efficiency can be improved with a better balance.

[0101] From the viewpoint of improving durability and luminous efficiency with a better balance, the alkyl group included in the substituent (a) or the substituent (b) (the alkyl group constituting the substituent (a) or the substituent (b)) may be a linear group. In addition, from the same viewpoint, the alkoxy group included in the substituent (b) (the alkoxy group constituting the substituent (b)) may be a linear group.

[0102] In substituent (a) or substituent (b), the substitution position of the thiol group is not particularly limited, but for example, substituent (a) or substituent (b) may have a thiol group at least at the end. According to this form, when the polymer compound according to the embodiment is used as a hole transport material, the thiol group is likely to be located on the surface of the hole transport layer, and therefore it is likely to interact with the light-emitting material (such as quantum dots or perovskite compounds) in the light-emitting layer. As a result, the arrangement of the light-emitting material included in the light-emitting layer can be improved, so that the durability (light-emitting lifetime) and light-emitting efficiency can be improved in a better balance.

[0103] That is, the thiol group-containing alkyl group (substituent (a)) or the thiol group-containing alkoxyalkyl group (substituent (b)) according to the embodiment may have a structure represented by Chemical Formula i:

[0104] Chemical formula i

[0105] *-Z 1 -(OZ 2 )n-SH

[0106] In chemical formula i, Z 1 represents an unsubstituted or thiol-substituted alkylene group having 1 to 14 carbon atoms, n is 0 or 1, and when n is 1, Z 2 represents an unsubstituted or thiol-substituted alkylene group having 1 to 13 carbon atoms, and Z 1 The carbon number of the alkylene represented by Z 2 The sum of the carbon numbers of the alkylene groups represented by Z is an integer of 14 or less (in other words, n is 0 or 1, and when n is 0, Z 1 represents an alkylene group having 1 to 14 carbon atoms which is unsubstituted or substituted with a thiol group; and when n is 1, Z 1 represents an unsubstituted or thiol-substituted alkylene group having 1 to 13 carbon atoms, Z 2 represents an unsubstituted or thiol-substituted alkylene group having 1 to 13 carbon atoms, and Z 1 The carbon number of the alkylene represented by Z 2 The sum of the carbon numbers of the alkylene groups represented by is an integer of 14 or less), and * is bonded to 1 An aromatic hydrocarbon group having 6 to 25 ring-constituting atoms. In addition, there is a case where the group having the structure represented by Chemical Formula i is simply referred to as "substituent (i)".

[0107] In order to improve durability (such as luminous lifetime) and luminous efficiency with better balance, as Z 1 The alkylene group having 1 to 14 carbon atoms is a linear or branched alkylene group and may be substituted with a thiol group. 1Examples of the alkylene group include methylene, ethylene, n-propylene (trimethylene), isopropylene (1,1-dimethylmethylene), n-butylene, isobutylene, sec-butylene, tert-butylene, n-pentylene, isopentylene, tert-pentylene, neopentylene, 1,2-dimethylpropylene, n-hexylene, isohexylene, 1,3-dimethylbutylene, 1-isopropylpropylene, 1,2-dimethylbutylene, n-heptylene, 1,4-dimethylpentylene, 3-ethylpentylene, 2-methyl-1-isopropylpropylene, 1-ethyl-3-methylbutylene, n-octylene, 2-ethylhexylene, 3-methyl-1-isopropylbutylene, 2-methyl-1-isopropylbutylene, 1-tert-butyl-2-methylpropylene, n-nonylene, 3,5,5-trimethylhexylene, n-decylene, isodecylene, n-undecylene, 1-methyldecylene, n-dodecylene, n-tridecylene and n-tetradecylene.

[0108] As Z 1 The carbon number of the alkylene group may be 1 or more and 12 or less, for example, 1 or more and 10 or less, 2 or more and 8 or less, 4 or more and 8 or less, for example, 6.

[0109] In addition, from the perspective of improving durability and luminous efficiency with a better balance, as Z 1 The alkylene group may be linear.

[0110] As described in detail below, the polymer compound according to the embodiment can be formed into a film by a coating method. However, in this case, in order to improve the film-forming properties and form a uniform film, thereby improving durability (such as luminous lifetime), the Z 1 The alkylene group may be unsubstituted.

[0111] In addition, from the viewpoint of further improving durability (for example, luminescence lifetime), in the chemical formula i, n may be 1, that is, [OZ 2 ] exists. That is, in an embodiment, the thiol group-containing alkoxyalkyl group may have a structure represented by Chemical Formula i-1:

[0112] Chemical formula i-1

[0113] *-Z 1 -OZ 2 -SH

[0114] In chemical formula i-1, Z 1 represents an unsubstituted or thiol-substituted alkylene group having 1 to 13 carbon atoms, Z 2 represents an alkylene group which is unsubstituted or substituted with a thiol group and has 1 to 13 carbon atoms, wherein Z 1 The carbon number of the alkylene represented by Z 2The sum of the carbon numbers of the alkylene groups represented by is an integer of 14 or less, and * is bonded to the 1 An aromatic hydrocarbon group having 6 to 25 ring atoms. Also, the group having the structure represented by Chemical Formula i-1 may be simply referred to as a "substituent (i-1)".

[0115] In Chemical Formula i, when n is 1 (when the substituent (b) has a structure represented by Chemical Formula i-1), as Z 2 The alkylene group having 1 to 13 carbon atoms may be a linear or branched alkylene group and may be substituted with a thiol group. 2 Examples of alkylene groups, where Z 1 Among specific examples of the alkylene group, those having 1 to 13 carbon atoms can be cited.

[0116] As Z 2 The carbon number of the alkylene group may be 1 or more and 10 or less, for example, 1 or more and 8 or less, for example, 1 or more and 6 or less, 2 or more and 4 or less, for example, 3.

[0117] In addition, by Z 1 The carbon number of the alkylene represented by Z 2 The sum of the carbon numbers of the alkylene groups represented may be 2 or more and 12 or less, for example, 2 or more and 10 or less, 4 or more and 10 or less, for example, 6 or more and 9 or less.

[0118] In addition, from the perspective of improving durability and luminous efficiency with a better balance, as Z 2 The alkylene group may be linear.

[0119] In addition, from the viewpoint of further improving durability, as Z 2 The alkylene group may be substituted with a thiol group. That is, in Chemical Formula i, when n is 1 (when the substituent (b) has a structure represented by Chemical Formula i-1), the substituent (i-1) may have two or more thiol groups. Meanwhile, the upper limit of the number of thiol groups included in the above substituent (i-1) is not particularly limited, but may be 4 or less.

[0120] In chemical formula i-1, Z 1 The exemplary form can refer to Z in chemical formula i 1 Description.

[0121] Meanwhile, from the viewpoint of further improving the luminous efficiency, n in the chemical formula i may be 0, that is, [OZ 2 ] may not exist. That is, in an embodiment, the alkyl group containing a thiol group may have a structure represented by Chemical Formula i-2:

[0122] Chemical formula i-2

[0123] *-Z 1 -SH

[0124] In chemical formula i-2, Z 1 represents an unsubstituted or thiol-substituted alkylene group having 1 to 14 carbon atoms, and * is bonded to 1 An aromatic hydrocarbon group having 6 to 25 ring atoms. Also, the group having the structure represented by Chemical Formula i-2 may be simply referred to as a "substituent (i-2)".

[0125] In chemical formula i-2, Z 1 The exemplary form can refer to Z in chemical formula i 1 Description.

[0126] From the above, the thiol group-containing alkyl group (substituent (a)) or the thiol group-containing alkoxyalkyl group (substituent (b)) (ie, substituent (i)) according to the embodiment may be in the following form: That is, in one embodiment, in Chemical Formula i-1, Z 1 represents an alkylene group which is unsubstituted or substituted with a thiol group and has 1 to 10 carbon atoms, Z 2 represents an alkylene group which is unsubstituted or substituted with a thiol group and has 1 to 8 carbon atoms, and is represented by Z 1 The carbon number of the alkylene represented by Z 2 The sum of the carbon numbers of the alkylene groups represented by is an integer from 2 to 12, or in the chemical formula i-2, Z 1 represents an alkylene group which is unsubstituted or substituted with a thiol group and has 1 to 10 carbon atoms;

[0127] In another embodiment, in Chemical Formula i-1, Z 1 represents an unsubstituted or thiol-substituted alkylene group having 2 to 8 carbon atoms, Z 2 represents an unsubstituted or thiol-substituted alkylene group having 1 to 6 carbon atoms, and Z 1 The carbon number of the alkylene represented by Z 2 The sum of the carbon numbers of the alkylene groups represented by is an integer from 3 to 10, or in the chemical formula i-2, Z 1 represents an unsubstituted or thiol-substituted alkylene group having 2 to 8 carbon atoms; and

[0128] In another embodiment, in Chemical Formula i-1, Z 1 represents an unsubstituted or thiol-substituted alkylene group having 4 to 8 carbon atoms, Z 2 represents an unsubstituted or thiol-substituted alkylene group having 2 to 4 carbon atoms, and Z 1The carbon number of the alkylene represented by Z 2 The sum of the carbon numbers of the alkylene groups represented by is an integer from 6 to 10, or in the chemical formula i-2, Z 1 represents an unsubstituted or thiol-substituted alkylene group having 4 to 8 carbon atoms.

[0129] In addition, in each of the above embodiments, Z 1 The alkylene represented by Z 2 The alkylene groups represented may both be straight-chain.

[0130] Substituent (i) may be one or more and may be included in Y 1 and, for example, two or more may be included. And, Y 1 The upper limit of the number of substituents (i) included in is not particularly limited, but may be, for example, 6 or less, for example, 4 or less. When there are two or more substituents (i), the structures of the substituents (i) may be the same or different, but may be, for example, the same. Therefore, in one embodiment, Y 1 There are 2 or more and 6 or less (for example, 4 or less) substituents (i-1), and the structures of the substituents (i-1) may be the same as each other. In another embodiment, Y 1 There are 2 or more and 6 or less (eg, 4 or less) substituents (i-2), and the structures of the substituents (i-2) may be the same as each other.

[0131] In Chemical Formula 1, Y 1 represents a group selected from the following: an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by the substituent (a), an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by the substituent (b), and an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by the substituent (a) and the substituent (b).

[0132] Here, as the aromatic hydrocarbon group having 6 to 25 ring-forming atoms, examples thereof may include a group derived from an aromatic hydrocarbon such as benzene, naphthalene, anthracene, pyrene, pentalene, indene, azulene, heptalene, acenaphthene, phenalene, phenanthrene, biphenyl, terphenyl, quaterphenyl, fluorene, or 9,9′-spirobi[fluorene].

[0133] Among these, Y 1 The aromatic hydrocarbon group included in may be a group derived from benzene or fluorene (for example, a phenylene group or a fluorenylene group).

[0134] In an embodiment, in Formula 1, Y 1 Any one of the groups represented by Chemical Formulae (Y-1) to (Y-3) may be used.

[0135]

[0136] In the chemical formulas (Y-1) to (Y-3), R 311 to R 315 Each is independently a group (substituent (i)) having a structure represented by Chemical Formula i, and ** represents a bonding site. Also, exemplary forms of substituent (i) included in Chemical Formulas (Y-1) to (Y-3) refer to the description of substituent (i), and for example, substituent (i) may be substituent (i-1) or substituent (i-2). In Chemical Formulas (Y-1) and (Y-3), R 311 and R 312 , or R 314 and R 315 can be the same or different, but R 311 and R 312 and R 314 and R 315 can be the same as each other. For example, Y 1 It may be a group represented by Chemical Formula (Y-1).

[0137] In another embodiment, from the viewpoint of improving durability (eg, luminescence lifetime) and luminescence efficiency with better balance, in Chemical Formula 1, Y 1 It may be any one of the groups represented by chemical formulas (3-1) to (3-6):

[0138]

[0139] In the chemical formulas (3-1) to (3-6), R 301 、R 302 、R 305 、R 307 and R 308 are each independently a substituted or unsubstituted alkylene group having 1 to 14 carbon atoms, R 303 、R 304 、R 306 、R 309 and R 310 Each is independently a substituted or unsubstituted alkylene group having 1 to 11 carbon atoms, and ** represents a bonding site.

[0140] In addition, in the chemical formulas (3-1), (3-2), (3-5) and (3-6), R 301 and R 302 、R 303 and R 304 、R 307 and R 308 , or R 309 and R 310 They may be the same or different. 301 and R 302、R 303 and R 304 、R 307 and R 308 , and R 309 and R 310 Can be the same as each other.

[0141] As R 301 to R 310 The alkylene group having 1 to 14 carbon atoms (or 1 to 11 carbon atoms) is not particularly limited but is a linear or branched alkylene group, and specific examples thereof include the same as for Z in Chemical Formula i. 1 The same alkylene groups described have 1 to 14 carbon atoms, for example, 11 or fewer carbon atoms.

[0142] From the perspective of improving durability (such as luminous lifetime) and luminous efficiency with better balance, as R 301 to R 310 The alkylene group can have 1 to 10 carbon atoms, such as 1 to 8 carbon atoms, such as 2 to 8 carbon atoms, such as 4 to 8 carbon atoms, such as 6 carbon atoms.

[0143] In addition, from the same point of view as above, as R 301 to R 310 The alkylene group may be linear.

[0144] In Chemical Formula 1, Y 1 It may be a group represented by Chemical Formula (3-1) or (3-2). From the viewpoint of further improving durability (eg, luminescence lifetime), Y 1 It can be a group represented by chemical formula (3-2). At the same time, from the perspective of improving luminous efficiency, Y 1 It may be a group represented by Chemical Formula (3-1).

[0145] In Chemical Formula 1, Ar 11 and Ar 12 Each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms. 11 and Ar 12 Here, as the aromatic hydrocarbon group having 6 to 25 ring atoms, examples thereof include groups derived from aromatic hydrocarbons such as benzene, naphthalene, anthracene, pyrene, pentalene, indene, azulene, heptalene, acenaphthene, phenalene, phenanthrene, biphenyl, terphenyl, quaterphenyl, fluorene, or 9,9'-spirobi[fluorene].

[0146] As Ar 11 and Ar 12The aromatic hydrocarbon group may be a group derived from a compound selected from benzene, biphenyl, terphenyl and fluorene (for example, a group selected from phenylene, biphenylene, terphenylene and fluorenylene), a group derived from a compound selected from benzene and fluorene (for example, a group selected from phenylene and fluorenylene), or a group derived from benzene (for example, phenylene).

[0147] That is, in the polymer compound according to the embodiment, the structural unit (A) may be represented by Chemical Formula 1-1:

[0148] Chemical formula 1-1

[0149]

[0150] In Chemical Formula 1-1,

[0151] R 11 to R 14 and R 21 to R 24 can each independently be a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aryl group, or a halogen atom, wherein R 11 and R 21 They may be optionally bonded to each other to form a ring.

[0152] L 1 may be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms,

[0153] Ar 1 may be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms,

[0154] Ar 2 It may be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms, and Ar 2 Optionally with Ar 1 Form a ring.

[0155] X 1 may be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms, and

[0156] Y 1The aromatic hydrocarbon group may be a group selected from the following: an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by an alkyl group having 1 to 14 carbon atoms containing a thiol group, an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by an alkoxyalkyl group having 2 to 14 carbon atoms containing a thiol group, or an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by an alkyl group having 1 to 14 carbon atoms containing a thiol group and an alkoxyalkyl group having 2 to 14 carbon atoms containing a thiol group.

[0157] In Chemical Formula 1-1, Y 1 The same as defined in Chemical Formula 1, and Y in Chemical Formula 1-1 1 The exemplary form of can also refer to Y in Chemical Formula 1 1 That is, in Chemical Formula 1-1, Y 1 It may have the same Y as in Chemical Formula 1 1 The same meanings may be given in their exemplary forms or in combinations of these forms.

[0158] In Chemical Formula 1 (Chemical Formula 1-1), X 1 It may represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms; or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms.

[0159] Here, the “substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms” refers to any of the following: (I) an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by substituent (a), an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by substituent (b), and an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by substituent (a) and substituent (b); (II) an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by a substituent other than substituent (a) and substituent (b); or (III) an unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms.

[0160] Furthermore, in the above (I) and (II), substituents other than substituent (a) and substituent (b) may be further included. In addition, similarly, “substituted or unsubstituted heteroaromatic group having 5 to 25 ring-forming atoms” may represent any of the following: (I') a heteroaromatic group having 5 to 25 ring-forming atoms substituted by substituent (a), a heteroaromatic group having 5 to 25 ring-forming atoms substituted by substituent (b), and a heteroaromatic group having 5 to 25 ring-forming atoms substituted by substituent (a) and substituent (b); (II') a heteroaromatic group having 5 to 25 ring-forming atoms substituted by substituents other than substituent (a) and substituent (b); or (III') an unsubstituted heteroaromatic group having 5 to 25 ring-forming atoms. Furthermore, in the above (I') and (II'), substituents other than substituent (a) and substituent (b) may be further included. Furthermore, in the specification of the present application, “substituents other than substituent (a) and substituent (b)” refer to substituents other than alkyl groups substituted with a thiol group (—SH) and alkoxyalkyl groups substituted with a thiol group (—SH) among the substituents described for “substituted” above.

[0161] Here, as the aromatic hydrocarbon group having 6 to 25 ring-forming atoms, examples thereof may include a group derived from an aromatic hydrocarbon such as benzene, naphthalene, anthracene, pyrene, pentalene, indene, azulene, heptalene, acenaphthene, phenalene, phenanthrene, biphenyl, terphenyl, quaterphenyl, fluorene, or 9,9′-spirobi[fluorene].

[0162] In addition, the heteroaromatic group having 5 to 25 ring atoms may be, for example, a group derived from a heteroaromatic compound such as acridine, phenazine, benzoquinoline, benzisoquinoline, phenanthridine, phenanthroline, anthraquinone, fluorenone, dibenzofuran, dibenzothiophene, carbazole, imidazophenanthridine, benzimidazolophenanthridine, azadibenzofuran, azacarbazole, azadibenzothiophene, diazadibenzofuran, diazacarbazole, diazadibenzothiophene, xanthone, thioxanthone, pyridine, quinoline, or anthraquinone.

[0163] X 1 It may be a group derived from a compound selected from benzene, biphenyl, terphenyl, fluorene and carbazole (for example, a group selected from phenyl, biphenyl, terphenyl, fluorenyl, and carbazole), for example, a group derived from a compound selected from benzene, biphenyl, terphenyl, or fluorene (for example, a group selected from phenyl, biphenyl, terphenyl, and fluorenyl), or for example, a group derived from benzene (for example, phenyl).

[0164] In addition, X 1 It may not be substituted by substituent (a) or substituent (b). 1A group derived from a compound selected from benzene, biphenyl, terphenyl, fluorene, or carbazole, which may be unsubstituted or substituted with a substituent other than substituent (a) and substituent (b). 1 A group derived from a compound selected from benzene, biphenyl, terphenyl, or fluorene, which may be unsubstituted or substituted with a substituent other than substituent (a) and substituent (b). 1 A group derived from benzene (e.g., phenyl) may be unsubstituted or substituted with a substituent other than the substituent (a) and the substituent (b). 1 The benzene-derived group (eg, phenyl) may be unsubstituted or substituted with an alkyl group having 1 to 14 carbon atoms.

[0165] In addition, from the viewpoint of improving durability, in one embodiment, in Chemical Formula 1 (or Chemical Formula 1-1), X 1 It may be a group represented by Chemical Formula 6-1.

[0166] Chemical formula 6-1

[0167]

[0168] In Chemical Formula 6-1,

[0169] R 601 to R 605 are each independently a hydrogen atom or an alkyl group having 1 to 14 carbon atoms which is unsubstituted or substituted with a substituent other than a thiol group (-SH), and is bonded to a nitrogen atom (bonded to Ar 1 of nitrogen atoms).

[0170] Here, in R 601 to R 605 Among them, at least one is an alkyl group having 1 to 14 carbon atoms which is unsubstituted or substituted with a substituent other than a thiol group (-SH), and the rest may be hydrogen atoms. 601 to R 605 Among them, at least one is an unsubstituted alkyl group having 1 to 14 carbon atoms, and the rest may be hydrogen atoms. 601 to R 605 Among them, one may be an unsubstituted alkyl group having 1 to 14 carbon atoms, and the remaining four may be hydrogen atoms. 603 may be an unsubstituted alkyl group having 1 to 14 carbon atoms, and R 601 、R 602 、R 604 and R 605 That is, the alkyl group may be in the position relative to the nitrogen atom (bonded to Ar 1 The nitrogen atom of the nitrogen atom is located in the para position (p position or 4 position) of the bond (*).

[0171] As R 601 to R 605 The alkyl group having 1 to 14 carbon atoms is not particularly limited but is a linear or branched alkyl group, and examples thereof include the same alkyl groups having 1 to 14 carbon atoms as described for the substituent (a).

[0172] Here, from the viewpoint of improving durability (eg, luminous lifetime) and luminous efficiency with better balance, as R 601 to R 605 The alkyl group of R may have 1 to 12 carbon atoms, such as 2 to 10 carbon atoms, or 4 to 8 carbon atoms, for example, n-hexyl. 603 It may be an alkyl group having a carbon number within the above range.

[0173] In addition, from the perspective of improving durability, as R 601 to R 605 The alkyl group may be linear.

[0174] In addition, in another embodiment, in Chemical Formula 1 (Chemical Formula 1-1), X 1 It may be any one of the groups represented by chemical formulas (8-1) to (8-3):

[0175]

[0176] In chemical formulas (8-1) to (8-3),

[0177] L 11 and L 12 each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 ring atoms,

[0178] R 801 to R 807 each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms, and

[0179] * with nitrogen atoms (bonded to Ar 1 nitrogen atoms) combined.

[0180] Here, R present in a benzene ring 801 to R 807 They may be the same or different. In addition, R 801 to R 807 Can be the same or different.

[0181] As L 11 and L 12 Examples of aromatic hydrocarbon groups include those in the case of X 1 The aromatic hydrocarbon group described is exemplified by those having 6 to 12 ring-constituting atoms.

[0182] As R 801 to R 807 Examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0183] As R 801 to R 807 The alkyl group may be linear or branched, and examples thereof include linear alkyl groups having 1 to 20 carbon atoms and branched alkyl groups having 3 to 20 carbon atoms. As specific examples, among the substituents described for the above “substituted”, the same specific examples as those given for the alkyl group can be exemplified.

[0184] As R 801 to R 807 As the cycloalkyl group, for example, there can be mentioned a cycloalkyl group having 3 to 16 carbon atoms. As specific examples, among the substituents described for the above “substituted”, the same specific examples as those given for the cycloalkyl group can be exemplified.

[0185] As R 801 to R 807 The alkoxy group may be linear or branched, and examples thereof include linear alkoxy groups having 1 to 20 carbon atoms or branched alkoxy groups having 3 to 20 carbon atoms. As specific examples, among the substituents described for the above “substituted”, the same specific examples as those given for the alkoxy group can be exemplified.

[0186] As R 801 to R 807 The cycloalkoxy group may be, for example, a cycloalkoxy group having 3 to 16 carbon atoms. As specific examples, the same specific examples as those given for the cycloalkoxy group among the substituents described for the above “substituted” can be exemplified.

[0187] As R 801 to R 807 The aromatic hydrocarbon group of the present invention includes an aromatic hydrocarbon group having 6 to 30 ring atoms. As specific examples, among the substituents described for the above “substituted”, the same specific examples as those given for the aryl group can be exemplified.

[0188] As R 801 to R 807The heteroaromatic group of X includes, for example, a heteroaromatic group having 5 to 25 ring atoms. 1 The specific examples given for the described heteroaromatic groups are the same as the specific examples.

[0189] In Chemical Formula 1 (or Chemical Formula 1-1), the thiol group-containing alkyl group (substituent (a)) or the thiol group-containing alkoxyalkyl group (substituent (b)) may be included in X 1 and Y 1 Either of the two or only Y 1 From the viewpoint of improving durability (eg, luminescence lifetime) and luminescence efficiency with better balance, the substituent (a) or the substituent (b) may be a substituent including only Y 1 That is, in Chemical Formula 1 (or Chemical Formula 1-1), X 1 may be an aromatic hydrocarbon group having 6 to 25 ring atoms which is unsubstituted or substituted with a substituent other than the substituent (a) and the substituent (b), or a heteroaromatic group having 5 to 25 ring atoms which is unsubstituted or substituted with a substituent other than the substituent (a) and the substituent (b), and Y 1 It may be a group selected from the following: an aromatic hydrocarbon group having 6 to 25 ring atoms substituted by a substituent (a), an aromatic hydrocarbon group having 6 to 25 ring atoms substituted by a substituent (b), or an aromatic hydrocarbon group having 6 to 25 ring atoms substituted by a substituent (a) and a substituent (b). In addition, in Chemical Formula 1 (or Chemical Formula 1-1), X 1 may be an aromatic hydrocarbon group having 6 to 25 ring atoms substituted with a substituent other than the substituent (a) and the substituent (b), or an unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, and Y 1 It may be a group selected from the following: an aromatic hydrocarbon group having 6 to 25 ring atoms substituted by a substituent (a), an aromatic hydrocarbon group having 6 to 25 ring atoms substituted by a substituent (b), or an aromatic hydrocarbon group having 6 to 25 ring atoms substituted by a substituent (a) and a substituent (b). In addition, in this case, Ar in Chemical Formula 1 11 、Ar 12 , L 1 、Ar 1 and Ar 2 It may not have substituent (a) and substituent (b). 11 to R 14 、R 21 to R 24 , L 1 、Ar 1 and Ar 2The substituent (a) and the substituent (b) may not be present.

[0190] In Chemical Formula 1 (or Chemical Formula 1-1), L 1 It may represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms; or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms.

[0191] Here, examples of the aromatic hydrocarbon group include groups derived from aromatic hydrocarbons such as benzene (e.g., phenylene), naphthalene, anthracene, pyrene, pentalene, indene, azulene, heptalene, acenaphthene, phenalene, phenanthrene, biphenyl, terphenyl, quaterphenyl, fluorene, or 9,9'-spirobi[fluorene]. In addition, the heteroaromatic group may include, for example, groups derived from heteroaromatic compounds such as acridine, phenazine, benzoquinoline, benzisoquinoline, phenanthridine, phenanthroline, anthraquinone, fluorenone, dibenzofuran, dibenzothiophene, carbazole, imidazophenanthridine, benzimidazophenanthridine, azadibenzofuran, azacarbazole, azadibenzothiophene, diazadibenzofuran, diazacarbazole, diazadibenzothiophene, xanthone, thioxanthone, pyridine, quinoline, or anthraquinone.

[0192] Among these, L 1 It may be a group derived from a compound selected from substituted or unsubstituted benzene, biphenyl, terphenyl, quaterphenyl, and fluorene, and may be a group derived from substituted or unsubstituted benzene or biphenyl (substituted or unsubstituted phenylene or biphenylene).

[0193] In addition, when L 1 When the aromatic hydrocarbon group may be substituted, the substituent may be an alkyl group or a phenyl group, for example, an alkyl group such as methyl, ethyl, n-propyl, isopropyl, or a methyl or ethyl group, for example, a methyl group. 1 It may be a group derived from benzene or biphenyl which may be unsubstituted or substituted by methyl, ethyl, n-propyl or isopropyl. 1 It may be a group derived from benzene or biphenyl which may be unsubstituted or substituted by methyl or ethyl. 1 It may be a group derived from benzene which is unsubstituted or substituted by one or two methyl groups, or a group derived from biphenyl which is unsubstituted or substituted by one or two methyl groups. 1 It may be a benzene-derived group which is unsubstituted or substituted with one or two methyl groups. 1 It may be an unsubstituted benzene-derived group (o-, m-, or p-phenylene). For example, L 1 It can be p-phenylene. 1 , which can better balance and improve the durability (e.g., luminous lifetime) and luminous efficiency of LEDs (e.g., QLEDs).

[0194] In addition, in Chemical Formula 1 (Chemical Formula 1-1), L 1It may be any one of the groups represented by Chemical Formula (4-1) to Chemical Formula (4-24):

[0195]

[0196] In the chemical formulae (4-1) to (4-24), *** is bonded to the nitrogen atom, and **** is bonded to Ar 1 .

[0197] In addition, L 1 It may be any one of the groups represented by Chemical Formulas (4-1) to (4-3) and (4-13) to (4-16) (ie, substituted or unsubstituted phenylene groups), or L 1 It may be any of the groups represented by chemical formulae (4-1) and (4-13) to (4-16) (ie, substituted or unsubstituted p-phenylene groups). For example, L 1 It may be a group represented by the chemical formula (4-1) (ie, unsubstituted p-phenylene). 1 Higher (better) hole injection properties (and thus higher durability) or better luminous efficiency can be achieved.

[0198] In Chemical Formula 1 (or Chemical Formula 1-1), Ar 1 It may represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms. 1 Can also be used with Ar 2 Form a ring.

[0199] Here, as Ar 1 There is no particular limitation on the aromatic hydrocarbon group. 1 Specific examples include the same as for the above L 1 The same ones as those described as being derived from aromatic hydrocarbons having 6 to 25 ring-forming atoms.

[0200] Among these, Ar 1 may be a group derived from a compound selected from substituted or unsubstituted benzene, biphenyl and fluorene, may be a substituted or unsubstituted group derived from benzene or biphenyl, or may be a substituted or unsubstituted group derived from benzene (for example, when Ar 1 and Ar 2 When no ring is formed, Ar 1 can be, for example, o-, m- or p-phenylene, and when Ar 1 and Ar 2 When forming a ring, Ar 1 It may be, for example, 1,3,4-phenylene. 1 Can be used with Ar 2 Form a ring, and may be a substituted or unsubstituted 1,3,4-phenylene group. 1, which can better balance the improvement of durability and luminous efficiency.

[0201] In addition, when Ar 1 The substituents that may be present when any one of the hydrogen atoms of is replaced are not particularly limited, and the same substituents as those described for the above “substituted” are applicable. 1 It may be unsubstituted.

[0202] In Chemical Formula 1 (or Chemical Formula 1-1), Ar 2 It may represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms; or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms. 2 Can also be used with Ar 1 Form a ring.

[0203] Here, as Ar 2 There is no particular limitation on the aromatic hydrocarbon group and heteroaromatic group. 2 Specific examples of the aromatic hydrocarbon group may include, for example, 1 The described radicals are derived from aromatic hydrocarbons having 6 to 25 ring atoms. 2 Specific examples of the heteroaromatic group may include, for example, 1 The groups described are those derived from heteroaromatic compounds having 5 to 25 ring atoms.

[0204] Among these, Ar 2 It may be a group derived from a compound of substituted or unsubstituted benzene, biphenyl or fluorene, it may be a group derived from benzene or biphenyl, it may be a group derived from benzene (for example, when Ar 1 and Ar 2 When no ring is formed, Ar 2 can be, for example, phenyl, and when Ar 1 and Ar 2 When forming a ring, Ar 2 may be, for example, o-, m-, or p-phenylene), or may be, for example, substituted or unsubstituted o-phenylene. 2 Can be used with Ar 1 Using such Ar 2 , which can better balance the improvement of durability and luminous efficiency.

[0205] In addition, when Ar 2 The substituents that may be present when any one of the hydrogen atoms of is replaced are not particularly limited, and the same substituents as those described for the above "substituted" are applicable. As an example, Ar 2 It may be unsubstituted.

[0206] As mentioned above, Ar 1 and Ar 2 Can be bonded to each other to form a ring. In this way, by 1 and Ar 2 By forming a ring therebetween, higher hole injection properties can be obtained, durability (eg, luminescence lifetime) can be further improved, and good film-forming properties can be achieved.

[0207] When Ar 1 and Ar 2 When forming a ring, Ar 1 and Ar 2 The ring structure formed is not particularly limited, but Ar 1 and Ar 2 may be bonded to each other to form a carbazole ring. In addition, in an embodiment, -Ar in Chemical Formula 1 (or Chemical Formula 1-1) 1 -N(Ar 2 )(X 1 ) may have a structure represented by any one of Chemical Formulas (7-1) to (7-3). For example, -Ar in Chemical Formula 1 (or Chemical Formula 1-1) 1 -N(Ar 2 )(X 1 ) may have a structure represented by Chemical Formula (7-2).

[0208]

[0209] In chemical formulas (7-1) to (7-3),

[0210] R 701 to R 706 Each of them independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aryl group, or a halogen atom.

[0211] X 1 Same as defined in Chemical Formula 1 (Chemical Formula 1-1), and * with L 1 combination.

[0212] Here, R present in a benzene ring 701 to R 706 Can be the same or different. In addition, R present in different benzene rings 701 to R 706 Can be the same or different.

[0213] As R 701 to R 706The alkyl group may be linear or branched, and examples thereof include linear alkyl groups having 1 to 20 carbon atoms or branched alkyl groups having 3 to 20 carbon atoms. As specific examples, among the substituents described for the above “substituted”, the same specific examples as those given for the alkyl group can be exemplified.

[0214] As R 701 to R 706 The cycloalkyl group of the present invention can be exemplified by, for example, a cycloalkyl group having 3 to 16 carbon atoms. As specific examples, among the substituents described for the above “substituted”, the same specific examples as those given for the cycloalkyl group can be exemplified.

[0215] As R 701 to R 706 The alkoxy group may be linear or branched, and examples thereof may include a linear alkoxy group having 1 to 20 carbon atoms or a branched alkoxy group having 3 to 20 carbon atoms. As specific examples, the same specific examples as those given for the alkoxy group among the substituents described for the above “substituted” can be exemplified.

[0216] As R 701 to R 706 The cycloalkoxy group may be, for example, a cycloalkyl group having 3 to 16 carbon atoms. As specific examples, the same specific examples as those given for the cycloalkoxy group among the substituents described for the above “substituted” can be exemplified.

[0217] As R 701 to R 706 The aryl group of the present invention may be, for example, an aryl group having 6 to 30 ring atoms (carbon atoms). As specific examples, among the substituents described for the above “substituted”, the same specific examples as those given for the aryl group may be exemplified.

[0218] As R 701 to R 706 Examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0219] In the chemical formulas (7-1) to (7-3), R 701 to R 706 Each of X and X is independently a hydrogen atom or a substituted or unsubstituted alkyl group, for example, a hydrogen atom. 1 Exemplary form of reference X 1 Description.

[0220] From the viewpoint of improving durability (eg, luminescence lifetime) and luminescence efficiency with better balance, in Chemical Formula 1 (Chemical Formula 1-1), Ar1 Can be used with Ar 2 Form a ring, and -L 1 -Ar 1 -N(Ar 2 )(X 1 ) may be any one of the groups represented by Chemical Formulas (5-1) to (5-3). In addition, in an embodiment, -L in Chemical Formula 1 (or Chemical Formula 1-1) 1 -Ar 1 -N(Ar 2 )(X 1 ) may have a structure represented by Chemical Formula (5-2).

[0221]

[0222] In chemical formulas (5-1) to (5-3),

[0223] R 501 to R 506 Each of them independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aryl group, or a halogen atom.

[0224] X 1 The same as defined in Chemical Formula 1 (or Chemical Formula 1-1), and

[0225] *****Bound to nitrogen atom.

[0226] Here, R present in a benzene ring 501 to R 506 Can be the same or different. In addition, R present in different benzene rings 501 to R 506 Can be the same or different.

[0227] As R 501 to R 506 Each substituent of can be applied to R in chemical formula (7-1) to (7-3) 701 to R 706 The same substituents as given in the examples. 501 to R 506 Each of X and X is independently a hydrogen atom or a substituted or unsubstituted alkyl group, for example, a hydrogen atom. 1 The exemplary form can be referred to as X 1 Description.

[0228] In Chemical Formula 1-1, R 11 to R 14 and R 21 to R24 may each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aryl group, or a halogen atom, wherein R 11 and R 21 may be bonded to each other to form a ring.

[0229] Here, R 11 to R 14 and R 21 to R 24 Can be the same or different.

[0230] As R 11 to R 14 and R 21 to R 24 The alkyl group may be linear or branched, and examples thereof may include a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms. As specific examples, among the substituents described for the above “substituted”, the same specific examples as those given for the alkyl group can be exemplified.

[0231] As R 11 to R 14 and R 21 to R 24 The cycloalkyl group of the present invention can be exemplified by, for example, a cycloalkyl group having 3 to 16 carbon atoms. As specific examples, among the substituents described for the above “substituted”, the same specific examples as those given for the cycloalkyl group can be exemplified.

[0232] As R 11 to R 14 and R 21 to R 24 The alkoxy group may be linear or branched, and examples thereof include linear alkoxy groups having 1 to 20 carbon atoms or branched alkoxy groups having 3 to 20 carbon atoms. As specific examples, the same specific examples as those given for the alkoxy group among the substituents described for the above “substituted” can be exemplified.

[0233] As R 11 to R 14 and R 21 to R 24 The cycloalkoxy group may be, for example, a cycloalkyl group having 3 to 16 carbon atoms. As specific examples, the same specific examples as those given for the cycloalkoxy group among the substituents described for the above “substituted” can be exemplified.

[0234] As R 11 to R 14 and R21 to R 24 The aryl group of the present invention may be, for example, an aryl group having 6 to 30 ring-constituting atoms. As specific examples, among the substituents described for the above “substituted”, the same specific examples as those given for the aryl group may be exemplified.

[0235] As R 11 to R 14 and R 21 to R 24 Examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0236] In addition, R 11 and R 21 Can be bonded to each other to form a ring. In this case, R 11 and R 21 The ring structure formed is not particularly limited, but for example, there is one in which R 11 and R 21 They are bonded to each other to form a carbazole ring.

[0237] From the perspective of obtaining higher durability (such as luminous lifetime) or better luminous efficiency, R 11 to R 14 and R 21 to R 24 Each of R and R is independently a hydrogen atom or a linear or branched alkyl group having 1 to 5 carbon atoms. 11 to R 14 and R 21 to R 24 Each of R and R is independently a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms. 11 to R 14 and R 21 to R 24 For example, all of them may be hydrogen atoms.

[0238] The structural unit (A) according to an embodiment may be selected from Chemical Formulae (A-1) to (A-3).

[0239]

[0240] In the chemical formulas (A-1) to (A-3), R 57 、R 58 、R 67 、R 68 、R 77 and R 78 may each independently represent a substituent (a) or a substituent (b), and R 51 to R 56 、R 61 to R 66and R 71 to R 76 may each independently represent a hydrogen atom or a straight-chain or branched-chain alkyl group having 1 to 12 carbon atoms;

[0241] For example, in the chemical formulas (A-1) to (A-3), R 57 、R 58 、R 67 、R 68 、R 77 and R 78 may each independently represent a substituent (a) or a substituent (b), and R 51 to R 56 、R 61 to R 66 and R 71 to R 76 may each independently represent a hydrogen atom or a straight-chain or branched-chain alkyl group having 2 to 10 carbon atoms;

[0242] For example, in the chemical formulas (A-1) to (A-3), R 57 、R 58 、R 67 、R 68 、R 77 and R 78 Each independently represents a substituent (a) or a substituent (b), R 51 to R 55 、R 61 to R 65 and R 71 to R 75 may each independently represent a hydrogen atom, and R 56 、R 66 and R 76 Each independently may represent a straight-chain or branched-chain alkyl group having 4 to 8 carbon atoms.

[0243] R present in a benzene ring 51 to R 56 、R 61 to R 66 and R 71 to R 76 Can be the same or different. 51 to R 56 、R 61 to R 66 and R 71 to R 76 Can be the same or different.

[0244] In addition, for each of the above forms, exemplary forms of substituent (a) and substituent (b) can refer to the description of substituent (a) and substituent (b). As an example, in each of the above forms, substituent (a) and substituent (b) included in chemical formulas (A-1) to (A-3) may be substituent (i) (substituent (i-1) or substituent (i-2)).

[0245] In addition, the structural unit (A) may be a structural unit represented by the chemical formula (A-2) among the above, and exemplary forms of each substituent in the structural unit are as described above.

[0246] Structural Unit (B)

[0247] According to an embodiment, the polymer compound may further include a structural unit (B) represented by Chemical Formula 2 in addition to the structural unit (A) represented by Chemical Formula 1:

[0248] Chemical formula 2

[0249]

[0250] In Chemical Formula 2,

[0251] Ar 21 and Ar 22 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms,

[0252] Ar 21 and Ar 22 are optionally bonded to each other to form a ring,

[0253] L 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms,

[0254] Ar 3 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms,

[0255] Ar 4 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms, and Ar 4 Optionally with Ar 3 Form a ring,

[0256] X 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms,

[0257] Y 2 is an aromatic hydrocarbon group having 6 to 25 ring atoms which is unsubstituted or substituted with an alkyl group having 1 to 14 carbon atoms, and

[0258] Ar 21 、Ar 22 , L 2 、Ar 3 、Ar 4 and X 2 An alkyl group having 1 to 14 carbon atoms does not have a thiol group-containing group, and an alkoxyalkyl group having 2 to 14 carbon atoms does not have a thiol group-containing group.

[0259] The structural unit (B) may be present in two or more units in the polymer compound. That is, the structural unit (B) represented by Chemical Formula 2 may be a repeating unit. Therefore, the polymer compound according to the embodiment may have a repeating unit (repeating unit (A)) represented by Chemical Formula 1 (e.g., Chemical Formula 1-1) and a repeating unit (repeating unit (B)) represented by Chemical Formula 2.

[0260] In this specification, the structural unit (B) represented by Chemical Formula 2 is also simply referred to as “structural unit (B)” or “structural unit (B) according to an embodiment”.

[0261] In addition, among the structural units (B) represented by Chemical Formula 2, the structural unit having the following structure is also simply referred to as “structural unit X′” or “structural unit X′ according to an embodiment”:

[0262]

[0263] Similarly, the structural unit "-Y" in the "structural unit (B) represented by Chemical Formula 2" 2 -" is also referred to as "structural unit Y'" or "structural unit Y' according to an embodiment".

[0264] In addition to the structural unit (A) represented by Chemical Formula 1, by further including the structural unit (B) represented by Chemical Formula 2, the polymer compound according to the embodiment may have excellent hole injection properties for quantum dots, and the durability (luminescence life) and luminous efficiency of the electroluminescent device may be further improved. In addition, high current efficiency and low driving voltage can be achieved. In the case where the polymer compound according to the embodiment may further include a structural unit (B), the structural unit (B) may include only one type, or may include two or more types. Furthermore, a plurality of structural units (B) may exist in block form, random form, alternating form or periodic form.

[0265] As described above, in an embodiment, the polymer compound may include the structural unit (B) represented by Chemical Formula 2. That is, the structural unit X' in Chemical Formula 2 (the structural unit on the left side of Chemical Formula 2; that is, the structural unit formed by connecting the nitrogen atom between two aromatic hydrocarbon groups) constitutes the polymer compound according to the embodiment. In addition, similarly, the structural unit Y' in Chemical Formula 2 (the structural unit on the right side of Chemical Formula 2; that is, the structural unit formed by "Y 2 ") constitutes the polymer compound according to the embodiment. That is, the polymer compound according to the embodiment may be a copolymer further including structural units X' and Y' in addition to the structural unit X and the structural unit Y.

[0266] In Chemical Formula 2, Y 2 With Y in chemical formula 1 1 The difference is that it does not have an alkyl group having 1 to 14 carbon atoms (substituent (a)) containing a thiol group and an alkoxyalkyl group having 2 to 14 carbon atoms (substituent (b)) containing a thiol group. In addition, in Chemical Formula 2, L 2 、Ar 3 、Ar 4 、Ar 21 and Ar 22 The definitions of L are the same as those of Chemical Formula 1 1 、Ar 1 、Ar 2 、Ar 21 and Ar 22 are the same as defined above, except that each of them does not have substituent (a) and substituent (b) (or is not substituent (a) and substituent (b)). 2 、Ar 3 、Ar 4 、Ar 21 and Ar 22 , unless specifically defined otherwise, the term "substituted" means a form substituted with a substituent other than the substituent (a) and the substituent (b).

[0267] In Chemical Formula 2, Ar 21 and Ar 22 Each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms. 21 and Ar 22 Here, as the aromatic hydrocarbon group having 6 to 25 ring atoms, specifically, the same as for Ar in Chemical Formula 1 can be exemplified. 11 and Ar 12 The same aromatic hydrocarbon groups as those described.

[0268] As Ar21 and Ar 22 The aromatic hydrocarbon group may be a group derived from a compound selected from benzene, biphenyl, terphenyl and fluorene (for example, a group selected from phenylene, biphenylene, terphenylene and fluorenylene), a group derived from a compound selected from benzene and fluorene (for example, a group selected from phenylene and fluorenylene), or a group derived from benzene (for example, phenylene).

[0269] That is, in the polymer compound according to the embodiment, the structural unit (B) may be represented by Chemical Formula 2-1:

[0270] Chemical formula 2-1

[0271]

[0272] In Chemical Formula 2-1,

[0273] R 31 to R 34 and R 41 to R 44 can each independently be a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aryl group, or a halogen atom, wherein R 31 and R 41 may bond to each other to form a ring,

[0274] L 2 may be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms,

[0275] Ar 3 may be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms,

[0276] Ar 4 It may be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms, and Ar 4 Optionally with Ar 3 Form a ring.

[0277] X 2 may be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms,

[0278] Y 2 An aromatic hydrocarbon group having 6 to 25 ring atoms which may be unsubstituted or substituted with an alkyl group having 1 to 14 carbon atoms, and

[0279] R31 to R 34 、R 41 to R 44 , L 2 、Ar 3 、Ar 4 and X 2 An alkyl group having 1 to 14 carbon atoms does not have a thiol group-containing group, and an alkoxyalkyl group having 2 to 14 carbon atoms does not have a thiol group-containing group.

[0280] In Chemical Formula 2 (Chemical Formula 2-1), Y 2 It may represent an aromatic hydrocarbon group having 6 to 25 ring atoms which is unsubstituted or substituted by an alkyl group having 1 to 14 carbon atoms. Here, as the aromatic hydrocarbon group having 6 to 25 ring atoms, specifically, the same as those mentioned above for Y 1 The same aromatic hydrocarbon groups having 6 to 25 ring atoms are described.

[0281] Among these, Y 2 The aromatic hydrocarbon group included in may be a group derived from benzene or fluorene (for example, a phenylene group or a fluorenylene group).

[0282] In an embodiment, from the viewpoint of improving durability (eg, luminescence lifetime) and luminescence efficiency with good balance, in Chemical Formula 2 (Chemical Formula 2-1), Y 2 It may be any one of the groups represented by chemical formulae (3'-1) to (3'-3):

[0283]

[0284] In the chemical formulas (3'-1) to (3'-3), R 301' to R 305' Each may independently be an alkyl group having 1 to 14 carbon atoms which is unsubstituted or substituted with a substituent other than a thiol group (—SH), and ** represents a bonding site.

[0285] In the chemical formulas (3'-1) and (3'-3), R301' and R 301' and R 302' 、R 304' and R 305' Can be the same or different. For example, R 301' and R 302' 、R 304' and R 305' Can be the same as each other.

[0286] As R 301' to R 305'The alkyl group having 1 to 14 carbon atoms is not particularly limited but is a linear or branched alkyl group, and specific examples thereof include the same alkyl groups having 1 to 14 carbon atoms as those described for the substituent (a).

[0287] Here, from the viewpoint of better balancing durability (eg, luminous lifetime) and luminous efficiency, as R 301' to R 305' The alkyl group of can have 1 to 12 carbon atoms, for example, 2 to 12 carbon atoms, 2 to 10 carbon atoms, or 4 to 10 carbon atoms, and can be, for example, n-decyl. 301' and R 302' The groups may each independently be an alkyl group having a carbon number within the above range.

[0288] In addition, from the same point of view as above, as R 301' to R 305' The alkyl group of R may be straight chain. 301' to R 304' The alkyl group may be unsubstituted.

[0289] In addition, considering the film forming properties and the like, in Chemical Formula 2 (Chemical Formula 2-1), Y 2 It may be a group represented by Chemical Formula (3′-1) (ie, a fluorenylene group).

[0290] In Chemical Formula 2 (Chemical Formula 2-1), X 2 It may represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms; or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms.

[0291] Here, as the aromatic hydrocarbon group having 6 to 25 ring-forming atoms, specifically, the same as those mentioned above for X can be exemplified. 1 The same aromatic hydrocarbon groups having 6 to 25 ring atoms as described above. In addition, as the heteroaromatic groups having 5 to 25 ring atoms, specifically, the same as those for X can be exemplified. 1 The same heteroaromatic groups having 5 to 25 ring-forming atoms are described.

[0292] Among these, X 2 It may be a group derived from a compound selected from benzene, biphenyl, terphenyl, fluorene, or carbazole (e.g., a group selected from phenyl, biphenyl, terphenyl, fluorenyl, or carbazole), for example, a group derived from a compound selected from benzene, biphenyl, terphenyl, or fluorene (e.g., a group selected from phenyl, biphenyl, terphenyl, or fluorenyl), or for example, a group derived from benzene (e.g., phenyl). That is, X 2It may be a substituted (substituted by a substituent other than substituent (a) and substituent (b)) or unsubstituted group derived from a compound selected from benzene, biphenyl, terphenyl, fluorene or carbazole, a substituted (substituted by a substituent other than substituent (a) and substituent (b)) or unsubstituted group derived from a compound selected from benzene, biphenyl, terphenyl or fluorene, an unsubstituted or substituted group derived from a compound selected from benzene, biphenyl, terphenyl or fluorene, or an unsubstituted or substituted group derived from benzene (e.g., phenyl).

[0293] In addition, from the viewpoint of improving durability, in one embodiment, in Chemical Formula 2 (or Chemical Formula 2-1), X 2 It may be a group represented by Chemical Formula (6'-1).

[0294] Chemical formula 6'-1

[0295]

[0296] In Chemical Formula 6'-1,

[0297] R 601' to R 605' may each independently be a hydrogen atom or an alkyl group having 1 to 14 carbon atoms, and

[0298] * with nitrogen atoms (bonded to Ar 3 nitrogen atoms) combined.

[0299] Here, in R 601' to R 605' Among them, at least one is an (unsubstituted) alkyl group having 1 to 14 carbon atoms, and the rest may be hydrogen atoms. 601' to R 605' Among them, one may be an (unsubstituted) alkyl group having 1 to 14 carbon atoms, and the remaining four may be hydrogen atoms. 603' may be an (unsubstituted) alkyl group having 1 to 14 carbon atoms, and R 601' 、R 602' 、R 604' and R 605' It can be a hydrogen atom. That is, the alkyl group can be in the position relative to the nitrogen atom (bonded to Ar 3 The nitrogen atom of the nitrogen atom is located in the para position (p position or 4 position) of the bond (*).

[0300] As R 601' to R 605'The alkyl group having 1 to 14 carbon atoms is not particularly limited but may be a linear or branched alkyl group, and specific examples thereof may include the same alkyl groups having 1 to 14 carbon atoms as those described for the substituent (a).

[0301] Here, from the viewpoint of improving durability (eg, luminous lifetime) and luminous efficiency with better balance, as R 601' to R 605' The alkyl group of may have 1 to 12 carbon atoms, such as 2 to 10 carbon atoms, or 4 to 8 carbon atoms, for example, is n-hexyl. 603' It may be an alkyl group having a carbon number within the above range.

[0302] In addition, from the perspective of improving durability, as R 601' to R 605' The alkyl group may be linear.

[0303] In addition, in another embodiment, in Chemical Formula 2 (or Chemical Formula 2-1), X 2 It may be any one of the groups represented by chemical formulas (8'-1) to (8'-3):

[0304]

[0305] In chemical formulas (8'-1) to (8'-3),

[0306] L 11' and L 12' may each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 ring atoms,

[0307] R 801' to R 807' may each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 12 ring atoms, and

[0308] * with nitrogen atoms (bonded to Ar 3 nitrogen atoms) combined.

[0309] Here, R present in a benzene ring 801' to R 807' Can be the same or different. In addition, R present in different benzene rings 801' to R 807' Can be the same or different.

[0310] As L 11' and L 12'Specific examples of the aromatic hydrocarbon group may include L 11 and L 12 The same ones. In addition, as R 801' to R 807' Specific examples of each substituent may include 801 to R 807 The same ones.

[0311] As described above, in Chemical Formula 2, L 2 、Ar 3 、Ar 4 、Ar 21 and Ar 22 The definitions of L in Chemical Formula 1 are respectively the same as 1 、Ar 1 、Ar 2 、Ar 11 and Ar 12 The same definition as in Chemical Formula 2-1. 2 、Ar 3 、Ar 4 、R 31 to R 34 and R 41 to R 44 The definitions of L are the same as those of L in Chemical Formula 1-1. 1 、Ar 1 、Ar 2 、R 11 to R 14 and R 21 to R 24 The definitions of are the same. In addition, the exemplary forms are the same. Hereinafter, they are described in detail.

[0312] In Chemical Formula 2 (or Chemical Formula 2-1), L 2 It may represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms; or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms.

[0313] Here, as the aromatic hydrocarbon group, examples thereof may include 1 The same aromatic hydrocarbon groups having 6 to 25 ring-forming atoms and heteroaromatic groups having 5 to 25 ring-forming atoms are described.

[0314] Among these, L 2 It may be a group derived from a compound selected from substituted or unsubstituted benzene, biphenyl, terphenyl, quaterphenyl or fluorene, for example, a group derived from substituted or unsubstituted benzene or biphenyl (substituted or unsubstituted phenylene or phenylene group).

[0315] In addition, when L 2When L is a substituted aromatic hydrocarbon group, the substituent may be an alkyl group or a phenyl group, for example, an alkyl group such as methyl, ethyl, n-propyl or isopropyl, for example, methyl or ethyl, for example, methyl. 2 It may be a group derived from benzene or biphenyl which may be unsubstituted or substituted by methyl, ethyl, n-propyl or isopropyl. 2 It may be a group derived from benzene or biphenyl which may be unsubstituted or substituted by methyl or ethyl. 2 It may be a group derived from benzene which is unsubstituted or substituted by one or two methyl groups, or a group derived from biphenyl which is unsubstituted or substituted by one or two methyl groups. 2 It may be a benzene-derived group which is unsubstituted or substituted with one or two methyl groups. 2 It may be an unsubstituted benzene-derived group (o-, m- or p-phenylene), for example p-phenylene. 2 The durability (eg, luminous lifetime) and luminous efficiency of LEDs (eg, QLEDs) can be improved with better balance.

[0316] In addition, in Chemical Formula 2 (or Chemical Formula 2-1), L 2 It may be any one of the groups represented by chemical formulae (4'-1) to (4'-24):

[0317]

[0318] In the chemical formulae (4'-1) to (4'-24), *** is bonded to a nitrogen atom, and **** is bonded to Ar 3 .

[0319] In addition, L 2 It may be any one of the groups represented by chemical formulae (4'-1) to (4'-3) and (4'-13) to (4'-16) (ie, substituted or unsubstituted phenylene groups). 2 It may be any of the groups represented by chemical formulae (4'-1) and (4'-13) to (4'-16) (i.e., substituted or unsubstituted p-phenylene groups), for example, it may be a group represented by chemical formula (4'-1) (i.e., unsubstituted p-phenylene groups). 2 Higher hole injection properties (and thus higher durability) or better luminous efficiency can be achieved.

[0320] In Chemical Formula 2 (or Chemical Formula 2-1), Ar 3 It may represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms. 3 Optionally, Ar 4 Form a ring.

[0321] Here, as Ar 3There is no particular limitation on the aromatic hydrocarbon group. 3 Specific examples may include the same as for the above L 1 The same ones as those described as being derived from aromatic hydrocarbons having 6 to 25 ring-forming atoms.

[0322] Among these, Ar 3 may be a group derived from a compound selected from substituted or unsubstituted benzene, biphenyl or fluorene, may be a substituted or unsubstituted group derived from benzene or biphenyl, or may be a substituted or unsubstituted group derived from benzene (for example, when Ar 3 and Ar 4 When no ring is formed, Ar 3 can be, for example, o-, m- or p-phenylene, and when Ar 3 and Ar 4 When forming a ring, Ar 3 It may be, for example, 1,3,4-phenylene. 3 Can be used with Ar 4 Form a ring, and may be a substituted or unsubstituted 1,3,4-phenylene group. Such Ar 3 Higher hole injection properties (and thus higher durability) and good film-forming properties can be achieved. In addition, durability and luminous efficiency can be improved with a good balance.

[0323] In addition, when Ar 3 The substituents that may be present when any one of the hydrogen atoms of is replaced are not particularly limited, and the same substituents as those described for the above “substituted” are applicable. 3 It may be unsubstituted.

[0324] In Chemical Formula 2 (or Chemical Formula 2-1), Ar 4 It may represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms; or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms. 4 Optionally, Ar 3 Form a ring.

[0325] Here, as Ar 4 There is no particular limitation on the aromatic hydrocarbon group and heteroaromatic group. 4 Specific examples of the aromatic hydrocarbon group may include, for example, 1 The described radicals are derived from aromatic hydrocarbons having 6 to 25 ring atoms. 4 The heteroaromatic group can be obtained by 1 The described groups are exemplified by groups derived from heteroaromatic compounds having 5 to 25 ring-forming atoms.

[0326] Among these, Ar4 may be a group derived from a compound selected from substituted or unsubstituted benzene, biphenyl or fluorene, may be a substituted or unsubstituted group derived from benzene or biphenyl, may be a substituted or unsubstituted group derived from benzene (for example, when Ar 3 and Ar 4 When no ring is formed, Ar 4 can be, for example, phenyl, and when Ar 3 and Ar 4 When forming a ring, Ar 4 may be, for example, o-, m-, or p-phenylene), or may be, for example, substituted or unsubstituted o-phenylene. 4 Can be used with Ar 3 Form a ring. Such Ar 4 It can better balance and improve durability and luminous efficiency.

[0327] In addition, when Ar 4 The substituents that may be present when any one of the hydrogen atoms of is replaced are not particularly limited, and the same substituents as those described for the above “substituted” are applicable. 4 It may be unsubstituted.

[0328] As mentioned above, Ar 3 and Ar 4 can be bonded to each other to form a ring. In this way, by using Ar 3 and Ar 4 By forming the ring, higher hole injection properties can be obtained, durability (for example, luminescence lifetime) can be further improved, and good film-forming properties can be achieved.

[0329] When Ar 3 and Ar 4 When forming a ring, Ar 3 and Ar 4 The ring structure formed is not particularly limited, but Ar 3 and Ar 4 may be bonded to each other to form a carbazole ring. In addition, in an embodiment, -Ar in Chemical Formula 2 (or Chemical Formula 2-1) 3 -N(Ar 4 )(X 2 ) may have a structure represented by any one of Chemical Formulas (7'-1) to (7'-3). In addition, in an embodiment, -Ar in Chemical Formula 2 (or Chemical Formula 2-1) 3 -N(Ar 4 )(X 2 ) may have a structure represented by chemical formula (7'-2):

[0330]

[0331] In chemical formulas (7'-1) to (7'-3),

[0332] R 701' to R 706' Each of them independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aryl group, or a halogen atom.

[0333] X 2 It may be the same as defined in Chemical Formula 2 (Chemical Formula 2-1), and * and L 2 combination.

[0334] Here, R present in a benzene ring 701' to R 706' Can be the same or different. In addition, R present in different benzene rings 701' to R 706' Can be the same or different.

[0335] As R 701' to R 706' The alkyl group may be linear or branched, and examples thereof may include a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms. As specific examples, among the substituents described for the above “substituted”, the same specific examples as those given for the alkyl group can be exemplified.

[0336] As R 701' to R 706' The cycloalkyl group of the present invention can be exemplified by, for example, a cycloalkyl group having 3 to 16 carbon atoms. As specific examples, among the substituents described for the above “substituted”, the same specific examples as those given for the cycloalkyl group can be exemplified.

[0337] As R 701' to R 706' The alkoxy group may be linear or branched, and examples thereof may include a linear alkoxy group having 1 to 20 carbon atoms or a branched alkoxy group having 3 to 20 carbon atoms. As specific examples, the same specific examples as those given for the alkoxy group among the substituents described for the above “substituted” can be exemplified.

[0338] As R 701' to R 706' The cycloalkoxy group may be, for example, a cycloalkyl group having 3 to 16 carbon atoms. As specific examples, the same specific examples as those given for the cycloalkoxy group among the substituents described for the above “substituted” can be exemplified.

[0339] As R 701'to R 706' The aryl group of the present invention may be, for example, an aryl group having 6 to 30 ring-constituting atoms. As specific examples, among the substituents described for the above “substituted”, the same specific examples as those given for the aryl group may be exemplified.

[0340] As R 701' to R 706' The halogen atom may be, for example, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0341] In the chemical formulas (7'-1) to (7'-3), R 701' to R 706' Each of X and X is independently a hydrogen atom, a substituted or unsubstituted alkyl group, or a hydrogen atom. 2 The exemplary form can be referred to as X 2 Description.

[0342] From the viewpoint of improving durability (eg, luminescence lifetime) and luminescence efficiency with better balance, in Chemical Formula 2 (or Chemical Formula 2-1), Ar 3 Can be used with Ar 4 Form a ring, and -L 2 -Ar 3 -N(Ar 4 )(X 2 ) may be any one of the groups represented by Chemical Formulas (5'-1) to (5'-3). In addition, in an embodiment, -L in Chemical Formula 2 (or Chemical Formula 2-1) 2 -Ar 3 -N(Ar 4 )(X 2 ) may have a structure represented by chemical formula (5'-2):

[0343]

[0344] In chemical formulas (5'-1) to (5'-3),

[0345] R 501' to R 506' Each of them independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aryl group, or a halogen atom.

[0346] X 2 It may be the same as defined in Chemical Formula 2 (Chemical Formula 2-1), and ***** is bonded to the nitrogen atom.

[0347] Here, R present in a benzene ring 501' to R506' Can be the same or different. In addition, R present in different benzene rings 501' to R 506' Can be the same or different.

[0348] As R 501' to R 506' Each substituent of can be applied to R in chemical formula (7'-1) to (7'-3) 701' to R 706' The same substituents as given in the examples. 501' to R 506' Each of X and X is independently a hydrogen atom, a substituted or unsubstituted alkyl group, or a hydrogen atom. 2 The exemplary form can be referred to as X 2 Description.

[0349] In Chemical Formula 2-1, R 31 to R 34 and R 41 to R 44 may each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aryl group, or a halogen atom, wherein R 31 and R 41 may be bonded to each other to form a ring.

[0350] Here, R 31 to R 34 and R 41 to R 44 Can be the same or different.

[0351] As R 31 to R 34 and R 41 to R 44 The alkyl group may be linear or branched, and examples thereof include linear alkyl groups having 1 to 20 carbon atoms or branched alkyl groups having 3 to 20 carbon atoms. As specific examples, among the substituents described for the above “substituted”, the same specific examples as those given for the alkyl group can be exemplified.

[0352] As R 31 to R 34 and R 41 to R 44 The cycloalkyl group of the present invention can be exemplified by, for example, a cycloalkyl group having 3 to 16 carbon atoms. As specific examples, among the substituents described for the above “substituted”, the same specific examples as those given for the cycloalkyl group can be exemplified.

[0353] As R 31 to R 34 and R 41 to R 44 The alkoxy group may be linear or branched, and examples thereof include linear alkoxy groups having 1 to 20 carbon atoms or branched alkoxy groups having 3 to 20 carbon atoms. As specific examples, the same specific examples as those given for the alkoxy group among the substituents described for the above “substituted” can be exemplified.

[0354] As R 31 to R 34 and R 41 to R 44 The cycloalkoxy group may be, for example, a cycloalkyl group having 3 to 16 carbon atoms. As specific examples, the same specific examples as those given for the cycloalkoxy group among the substituents described for the above “substituted” can be exemplified.

[0355] As R 31 to R 34 and R 41 to R 44 The aryl group of the present invention may be, for example, an aryl group having 6 to 30 ring-constituting atoms. As specific examples, among the substituents described for the above “substituted”, the same specific examples as those given for the aryl group may be exemplified.

[0356] As R 31 to R 34 and R 41 to R 44 Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0357] In addition, R 31 and R 41 Can be bonded to each other to form a ring. In this case, R 31 and R 41 The ring structure formed is not particularly limited, but for example, there is one in which R 31 and R 41 They are bonded to each other to form a carbazole ring.

[0358] From the perspective of obtaining higher durability (such as luminous lifetime) or better luminous efficiency, R 31 to R 34 and R 41 to R 44 Each of R and R is independently a hydrogen atom or a linear or branched alkyl group having 1 to 5 carbon atoms. 31 to R 34 and R 41 to R 44Each of R and R is independently a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms. 31 to R 34 and R 41 to R 44 For example, all of them may be hydrogen atoms.

[0359] In addition to the moiety comprising substituent (a) or substituent (b) (ie, Y 1 ), the structural unit (B) represented by the above-described Chemical Formula 2 may have the same structure and substituent as the structural unit (A) represented by Chemical Formula 1. That is, Ar in Chemical Formula 2 21 With Ar in chemical formula 1 11 Same as Ar in Chemical Formula 2 22 With Ar in chemical formula 1 12 Same, L in Chemical Formula 2 2 With L in chemical formula 1 1 Same as Ar in Chemical Formula 2 3 With Ar in chemical formula 1 1 Same as Ar in Chemical Formula 2 4 With Ar in chemical formula 1 2 The same, and X in Chemical Formula 2 2 With X in chemical formula 1 1 Similarly, R in Chemical Formula 1-1 11 Can be combined with R in Chemical Formula 2-1 31 Same, R in Chemical Formula 1-1 12 Can be combined with R in Chemical Formula 2-1 32 Same, R in Chemical Formula 1-1 13 Can be combined with R in Chemical Formula 2-1 33 Same, R in Chemical Formula 1-1 14 Can be combined with R in Chemical Formula 2-1 34 Same, R in Chemical Formula 1-1 21 Can be combined with R in Chemical Formula 2-1 41 Same, R in Chemical Formula 1-1 22 Can be combined with R in Chemical Formula 2-1 42 Same, R in Chemical Formula 1-1 23 Can be combined with R in Chemical Formula 2-1 43 Same, R in Chemical Formula 1-1 24 Can be combined with R in Chemical Formula 2-1 44 Same, L in Chemical Formula 1-1 1 Can be used with L in Chemical Formula 2-1 2 The same, Ar in chemical formula 1-1 1 Can be combined with Ar in chemical formula 2-1 3 The same, Ar in chemical formula 1-12 Can be combined with Ar in chemical formula 2-1 4 are the same, and X in Chemical Formula 1-1 1 Can be used with X in chemical formula 2-1 2 same.

[0360] Also, in the above, for example, "Ar in Chemical Formula 1 11 With Ar in chemical formula 2 21 Same means Ar 11 and Ar 21 have the same structure. For example, if Ar 11 is an unsubstituted phenylene group, then it represents Ar 21 It is also an unsubstituted phenylene group.

[0361] The structural unit (B) according to an embodiment may be selected from the following groups:

[0362]

[0363] In the chemical formulas (B-1) to (B-3), R 57' 、R 58' 、R 67' 、R 68' 、R 77' and R 78' may each independently represent a linear or branched alkyl group having 1 to 14 carbon atoms, and R 51' to R 56' 、R 61' to R 66' and R 71' to R 76' may each independently represent a hydrogen atom or a straight-chain or branched-chain alkyl group having 1 to 12 carbon atoms;

[0364] For example, in the chemical formulas (B-1) to (B-3), R 57' 、R 58' 、R 67' 、R 68' 、R 77' and R 78' may each independently represent a linear or branched alkyl group having 2 to 12 carbon atoms, and R 51' to R 56' 、R 61' to R 66' and R 71' to R 76' may each independently represent a hydrogen atom or a straight-chain or branched-chain alkyl group having 2 to 10 carbon atoms; and

[0365] For example, in the chemical formulas (B-1) to (B-3), R 57' 、R 58'、R 67' 、R 68' 、R 77' and R 78' may each independently represent a linear or branched alkyl group having 4 to 10 carbon atoms, R 51' to R 55' 、R 61' to R 65' and R 71' to R 75 ' may each independently represent a hydrogen atom, and R 56' 、R 66' and R 76' Each independently may represent a straight-chain or branched-chain alkyl group having 4 to 8 carbon atoms.

[0366] R present in a benzene ring 51' to R 56' 、R 61' to R 66' and R 71' to R 76' R in different benzene rings 51' to R 56' 、R 61' to R 66' and R 71' to R 76' Can be the same or different.

[0367] The structural unit (B) may be a structural unit represented by the chemical formula (B-2) among the above, and the specific form of each substituent in the structural unit is as described above.

[0368] Other structural units

[0369] The polymer compound of the embodiment may further include a structural unit other than the structural unit (A) and optionally the structural unit (B). In the case of including another structural unit, the structural unit is not particularly limited as long as it does not inhibit the effect of the polymer compound. The other structural unit may include a structural unit derived from a compound such as azulene, naphthalene, anthracene, phenanthrene, pyrene, etc. Hereinafter, the other structural unit is referred to as "structural unit (C)".

[0370] Composition of polymer compounds

[0371] The composition of the structural unit (A) to (C) in the polymer compound of the embodiment is not particularly limited. Considering the further good balance of durability (luminescence lifetime) and luminous efficiency of the layer (for example, hole injection layer, hole transport layer) formed using the obtained polymer compound, based on the total molar number of the structural unit constituting the polymer compound, it can be, for example, about 1 mol % or more and less than about 100 mol %, for example, about 1 mol % or more and about 30 mol % or less, for example, about 5 mol % or more and about 20 mol % or less, or for example, about 8 mol % or more and about 15 mol % or less including structural unit (A). When the polymer compound includes two or more types of structural unit (A), the amount of structural unit (A) means the total amount of structural unit (A).

[0372] That is, in an embodiment, based on the total molar number of the structural units constituting the polymer compound, structural unit (A) is included in the polymer compound at a ratio of less than about 100 mol %. At this point, structural unit (B) may be further included. Taking into account the further good balance of durability (luminescence lifetime) and luminous efficiency of the layer (e.g., hole injection layer, hole transport layer) formed using the obtained polymer compound, based on the total molar number of the structural units constituting the polymer compound, it can be, for example, greater than about 0 mol % and less than or equal to about 99 mol %, for example, greater than about 70 mol % and less than or equal to about 99 mol %, for example, greater than about 80 mol % and less than or equal to about 95 mol %, or for example, greater than about 85 mol % and less than or equal to about 92 mol % including structural unit (B). When a polymer compound contains two or more types of structural units (B), the amount of structural unit (B) means the total amount of structural unit (B).

[0373] In addition, as described above, the polymer compound according to the embodiment may further include another structural unit (structural unit (C)). In this case, the composition of the other structural unit (structural unit (C)) is not particularly limited. In view of the effect of further improving the ease of film formation and film strength by the obtained polymer compound, based on the total molar number of the structural units constituting the polymer compound, the structural unit (C) can be included in an amount greater than 0 mol% and less than or equal to about 10 mol%. When the polymer compound includes two or more types of structural units (C), the amount of the structural unit (C) means the total amount of the structural unit (C).

[0374] As an example, the structural unit (C) may be a structural unit having a cross-linking group. Here, "cross-linking group" means a group that reacts (cross-links) with the same or different groups in a nearby structural unit by heating or irradiation with active energy rays to produce a new bond. By including a structural unit having a cross-linking group, a cross-linking reaction can occur by heating or irradiation with active energy rays, making the polymer compound insoluble in a solvent and forming a more solid film. As a result, the productivity and durability of the electroluminescent device can be further improved.

[0375] The crosslinking group is not particularly limited as long as it is a group that can induce a crosslinking reaction by heat or active energy rays, but examples may include bicyclo[4.2.0]octa-1,3,5-trienyl, vinyl, hexenyl, styryl, (3-ethoxyeth-3-yl)methoxy, and the like.

[0376] Based on the total (sum) moles of the structural unit (A) and the structural unit (B), the molar ratio (proportion) of the structural unit (A) may be greater than or equal to about 1 mol% and less than about 30 mol%, or greater than or equal to about 5 mol% and less than or equal to about 20 mol%, or, for example, greater than or equal to about 8 mol% and less than or equal to about 15 mol%. Similarly, the molar proportion of the structural unit (B) may be greater than or equal to about 70 mol% and less than or equal to about 99 mol%, greater than or equal to about 80 mol% and less than or equal to about 95 mol%, or greater than or equal to about 85 mol% and less than or equal to about 92 mol% (based on the total moles of the structural unit (A) and the structural unit (B)).

[0377] The molar ratio of the structural unit (A), the structural unit (B) and the structural unit (C) can be appropriately controlled by adjusting the molar ratio of the monomers used as raw materials. 1 H-NMR, 13 The molar ratio of each structural unit (A), structural unit (B) and structural unit (C) in the polymer compound can be measured by C-NMR, mass spectrometry, liquid chromatography-mass spectrometry (LC-MS), Fourier transform infrared spectroscopy (FTIR), or the like, or by combining these methods.

[0378] In consideration of a further good balance between the durability (e.g., luminescence lifetime) and luminescence efficiency of a layer (e.g., a hole injection layer, a hole transport layer) formed by using the obtained polymer compound, in an embodiment, the polymer compound may be composed only of the structural unit (A) and the structural unit (B) (i.e., the total ratio of the structural unit (A) and the structural unit (B) to all the structural units of the polymer compound is 100 mol %).

[0379] The weight average molecular weight (Mw) of the polymer compound according to the embodiment is not particularly limited, as long as the desired effect of the embodiment is obtained. The weight average molecular weight (Mw) may be, for example, greater than or equal to about 5,000Da and less than or equal to about 1,000,000Da, for example, greater than or equal to about 8,000Da and less than or equal to about 1,000,000Da, greater than or equal to about 10,000Da and less than or equal to about 800,000Da, or for example, greater than or equal to about 50,000Da and less than or equal to about 500,000Da. Utilizing such a weight average molecular weight, a polymer compound can be used to form a layer having a uniform film thickness by appropriately controlling the viscosity of the coating solution for forming a layer (e.g., hole injection layer, hole transport layer).

[0380] In addition, the number average molecular weight (Mn) of the polymer compound is not particularly limited, as long as the desired effect of the embodiment is obtained. The number average molecular weight (Mn) may be, for example, greater than or equal to about 4,000Da and less than or equal to about 300,000Da, for example, greater than or equal to about 6,000Da and less than or equal to about 250,000Da, greater than or equal to about 10,000Da and less than or equal to about 200,000Da, or for example, greater than or equal to about 20,000Da and less than or equal to about 150,000Da. Utilizing such a number average molecular weight, a polymer compound can be used to form a layer having a uniform film thickness by appropriately controlling the viscosity of the coating solution for forming a layer (e.g., a hole injection layer, a hole transport layer). In addition, the polydispersity (weight average molecular weight / number average molecular weight) of the polymer compound according to the embodiment may be, for example, greater than or equal to about 1.1 and less than or equal to about 50, for example, greater than or equal to about 1.5 and less than or equal to about 4.0, or for example, greater than or equal to about 2.0 and less than or equal to about 3.5.

[0381] In this specification, the measurement of the number average molecular weight (Mn) and the weight average molecular weight (Mw) is not particularly limited, and can be measured by using a known method or by appropriately adjusting a known method. In this specification, the number average molecular weight (Mn) and the weight average molecular weight (Mw) adopt the values ​​measured by the following method. The polydispersity (Mw / Mn) of the polymer is calculated by dividing the weight average molecular weight (Mw) measured by the following method by the number average molecular weight (Mn).

[0382] (Measurement of Number Average Molecular Weight (Mn) and Weight Average Molecular Weight (Mw))

[0383] The number average molecular weight (Mn) and weight average molecular weight (Mw) of the polymer material were measured by SEC (size exclusion chromatography) using polystyrene as a standard material under the following conditions:

[0384] (SEC measurement conditions)

[0385] Analytical equipment (SEC): Shimadzu Corporation, Prominence (registered trademark)

[0386] Column: Polymer Laboratories, PLgel MIXED-B

[0387] Column temperature: 40°C

[0388] Flow rate: 1.0 mL / min

[0389] Injection volume of sample solution: 20 μL (polymer concentration: approximately 0.05 mass %)

[0390] Eluent: tetrahydrofuran (THF)

[0391] Detector (UV-VIS detector): Shimadzu Corporation, SPD-10AV

[0392] Standard sample: polystyrene.

[0393] The terminal of the main chain of the polymer compound according to the present embodiment is not particularly limited and is appropriately defined depending on the type of raw material used, but is usually a hydrogen atom.

[0394] The polymer compound of this embodiment can be synthesized by using a known organic synthesis method. A specific synthesis method of the polymer compound of this embodiment can be easily understood by those skilled in the art with reference to Examples described later.

[0395] For example, the polymer compound according to the embodiment can be prepared by using at least one monomer (Ix) represented by chemical formula IX and at least one monomer (Iy) represented by chemical formula IY through copolymerization. In addition, at this time, if necessary, a monomer constituting the structural unit (B) according to the embodiment can be further added. In particular, the polymer compound according to the embodiment can be prepared by using at least one monomer (Ix) represented by chemical formula IX and at least one monomer (Iy) represented by chemical formula IY (i.e., monomers constituting the structural unit (A) according to the embodiment) through copolymerization of at least one monomer (II-x) represented by chemical formula II-X and at least one monomer (II-y) represented by chemical formula II-Y (i.e., monomers constituting the structural unit (B) according to the embodiment) in addition to the monomer (Ix) represented by chemical formula IX and at least one monomer (Iy) represented by chemical formula IY (i.e., monomers constituting the structural unit (A) according to the embodiment). Herein, in the polymer compound, when X in the structural unit (A) and X' in the structural unit (B) have the same structure, the polymer compound according to the embodiment can also be prepared by copolymerization of at least one monomer (Ix) represented by chemical formula IX, at least one monomer (Iy) represented by chemical formula IY, and at least one monomer (II-y) represented by chemical formula II-Y. In addition, in any of the above cases, if necessary, other monomers corresponding to other structural units (structural units (C)) can be further added. By appropriately controlling the molar ratio of each monomer, the molar ratio of the structural units (A) to (C) in the polymer compound can be controlled.

[0396] Chemical formula IX

[0397]

[0398] Chemical formula IY

[0399] W 3 -Y 1 -W 4

[0400] Chemical formula II-X

[0401]

[0402] Chemical formula II-Y

[0403] W 7 -Y 2 -W 8

[0404] Alternatively, the polymer compound according to the embodiment can be prepared by the polymerization reaction using one or more monomers represented by Chemical Formula 1 '. In addition, at this time, if necessary, a monomer corresponding to the structural unit (B) according to the embodiment can be further added. In particular, when the polymer compound according to the embodiment includes structural unit (A) and structural unit (B), it can be prepared by the copolymerization reaction using at least one monomer represented by Chemical Formula 1 ' and at least one monomer represented by Chemical Formula 2 '. In addition, at this time, if necessary, another monomer corresponding to another structural unit (structural unit (C)) can be further added.

[0405] Chemical formula 1'

[0406]

[0407] Chemical formula 2'

[0408]

[0409] In an embodiment, monomers used for polymerization of a polymer compound can be synthesized by appropriately combining known synthetic reactions, and their structures can also be confirmed by known methods (eg, NMR, LC-MS, etc.).

[0410] In Formula IX, Formula IY, Formula II-X, Formula II-Y, Formula 1' and Formula 2', Ar 11 、Ar 12 、Ar 21 、Ar 22 , L 1 , L 2 、Ar 1 、Ar 2 、Ar 3 、Ar 4 、X 1 、X 2 、Y 1 and Y 2 The same as defined in Chemical Formula 1 or Chemical Formula 2, and W 1 To W 12 Each independently represents a halogen atom (fluorine atom, chlorine atom, bromine atom, or iodine atom, such as bromine atom) or a group having the following structure. A to R D Each is independently an alkyl group having 1 to 3 carbon atoms. A to R D It may be methyl.

[0411]

[0412] W in Formula IX 1and W 2 , W in chemical formula IY 3 and W 4 , W in chemical formula II-X 5 and W 6 , W in chemical formula II-Y 7 and W 8 , W in Chemical Formula 1' 9 and W 10 , and W in Chemical Formula 2' 11 and W 12 However, in order to suppress the self-polymerization of monomer (Ix), W in chemical formula IX 1 and W 2 Similarly, in order to suppress the self-polymerization of monomer (Iy), W in chemical formula IY 3 and W 4 Can be atoms or groups that do not react with each other. In addition, similarly, in order to suppress the self-polymerization between monomers (II-x) or monomers (II-y), W in chemical formula II-X 5 and W 6 and W in the chemical formula II-Y 7 and W 8 In addition, similarly, in order to suppress the self-polymerization between the monomers represented by Chemical Formula 1' or between the monomers represented by Chemical Formula 2', W in Chemical Formula 1' 9 and W 10 and W in Chemical Formula 2' 11 and W 12 can be atoms or groups that do not react with each other. For example, W in Formula IX 1 and W 2 , W in chemical formula IY 3 and W 4 , W in chemical formula II-X 5 and W 6 , and W in Chemical Formula II-Y 7 and W 8 In addition, for example, W in Chemical Formula 1' 9 and W 10 Similarly, for example, W in Chemical Formula 2' 11 and W 12 But it's different.

[0413] [Materials for electroluminescent devices]

[0414] The polymer compound according to the embodiment can be advantageously used as a material for an electroluminescent device. The polymer compound according to the embodiment can provide a material for an electroluminescent device (organic layer such as a hole transport layer) having excellent durability (luminescence lifetime) and high luminous efficiency. Therefore, according to another embodiment, a material for an electroluminescent device including the polymer compound according to the embodiment is provided. Alternatively, the use of the polymer compound as a material for an electroluminescent device is provided.

[0415] In addition, the polymer compound according to the embodiment may have a HOMO energy level exceeding about 5.20 eV. Therefore, the polymer compound according to the embodiment may also be advantageously used in a quantum dot electroluminescent device (eg, a hole transport layer thereof).

[0416] The glass transition temperature (Tg) of the polymer compound according to the embodiment is not particularly limited, but may be about 75° C. or higher, about 90° C. or higher, or about 100° C. or higher. Meanwhile, the upper limit is not particularly limited, but may be about 200° C. or lower, for example, about 180° C. or lower, for example, about 150° C. or lower.

[0417] When the glass transition temperature (Tg) of the polymer is within the above range, it is desirable for device manufacturing, and further, a device with improved properties can be obtained. The glass transition temperature (Tg) of the polymer can be measured using a differential scanning calorimeter (DSC) (manufactured by Seiko Instruments, Inc., product name: DSC6000). The details of the measurement method are described in the Examples.

[0418] [Electroluminescent device]

[0419] As described above, the polymer compound according to the embodiment can be advantageously used in an electroluminescent device. That is, the electroluminescent device may include an electrode pair, and at least one layer of organic film between the electrode pair, the at least one layer of organic film including the polymer compound according to the embodiment or a material for an electroluminescent device. Such an electroluminescent device can exhibit excellent luminous efficiency at a low driving voltage. Therefore, according to another embodiment, there is provided an electroluminescent device comprising a first electrode, a second electrode, and at least one layer of organic film between the first electrode and the second electrode, wherein the at least one layer of organic film includes the polymer compound according to the embodiment. The purpose (or effect) of the embodiment can also be achieved by the electroluminescent device according to the embodiment. In a preferred form of the above embodiment, the electroluminescent device may further include a light-emitting layer between the electrodes, wherein the light-emitting layer includes a light-emitting material capable of emitting light from triplet excitons. Furthermore, the electroluminescent element of the embodiment is an example of an electroluminescent element according to the embodiment.

[0420] In addition, an embodiment provides a method for manufacturing an electroluminescent device, the electroluminescent device including an electrode pair and an organic film disposed between the electrodes and including at least one layer of the polymer compound according to the embodiment, wherein the at least one organic film is formed by a coating method. In addition, through this method, the present embodiment provides an electroluminescent device, wherein the at least one organic film is formed by a coating method.

[0421] The polymer compound according to the embodiment and the electroluminescent device material (EL device material) according to the present embodiment (hereinafter collectively referred to as "polymer compound / EL device material") may have excellent solubility in organic solvents. Therefore, the polymer compound / EL device material according to the embodiment can be advantageously used in the manufacture of devices (e.g., thin films) by a coating method (wet process). Therefore, according to another embodiment, a liquid composition comprising a polymer compound according to the embodiment and a solvent or a dispersion medium is provided. That is, a liquid composition comprising a polymer compound according to the embodiment and at least one solvent is also provided. A liquid composition like this is an example of a liquid composition according to an embodiment. In addition, the liquid composition may further contain a known dispersant.

[0422] In addition, as described above, the material for an electroluminescent device according to the embodiment can be advantageously used in the manufacture of a device (e.g., a thin film) by a coating method (wet process). In view of the above, this embodiment provides a thin film including the polymer compound according to the embodiment. Such a thin film is an example of a thin film according to the embodiment.

[0423] In addition, the material for EL element according to the present embodiment can have excellent hole injection properties and hole mobility. Therefore, the material can be advantageously used in the formation of any layer of the organic film, for example, as a hole injection material, a hole transport material, or a luminescent material (host). Among these, from the viewpoint of hole transport performance, it can be advantageously used as a hole injection material or a hole transport material, or can be advantageously used as a hole transport material.

[0424] That is, the present embodiment provides a composition comprising a polymer compound and at least one material selected from a hole transport material, an electron transport material, and a luminescent material (host). Here, the luminescent material included in the composition is not particularly limited, but may include at least one of semiconductor nanocrystal particles (semiconductor inorganic nanoparticles) and a perovskite compound (perovskite halide).

[0425] In the following, reference will be made to Figure 1 An electroluminescent device according to an embodiment is described in detail. Figure 1Schematic diagram showing an electroluminescent device according to an embodiment. In this specification, "electroluminescent device" may be abbreviated as "EL device".

[0426] like Figure 1 As shown in , the EL device 100 according to the embodiment includes a substrate 110, a first electrode 120 on the substrate 110, a hole injection layer 130 on the first electrode 120, a hole transport layer 140 on the hole injection layer 130, a light-emitting layer 150 on the hole transport layer 140, an electron transport layer 160 on the light-emitting layer 150, an electron injection layer 170 on the electron transport layer 160, and a second electrode 180 on the electron injection layer 170.

[0427] Here, the polymer compound according to the embodiment may be included in an organic film (organic layer) of a layer, for example, between the first electrode 120 and the second electrode 180. In particular, the polymer compound may be included in the hole injection layer 130 as a hole injection material, in the hole transport layer 140 as a hole transport material, or in the light emitting layer 150 as a light emitting material (host). The polymer compound may be included in the hole injection layer 130 as a hole injection material or in the hole transport layer 140 as a hole transport material. For example, the polymer compound may be included in the hole transport layer 140 as a hole transport material. That is, in an embodiment, the organic film including the at least one layer of the polymer compound may be a hole transport layer, a hole injection layer, or a light emitting layer. In an embodiment, the organic film including the at least one layer of the polymer compound may be a hole transport layer or a hole injection layer. In another embodiment, the organic film including the at least one layer of the polymer compound may be a hole transport layer.

[0428] In addition, the organic film including the at least one layer of the polymer compound / EL device material according to the embodiment can be formed by a coating method (solution coating method). For example, the at least one layer of the organic film can be formed using a solution coating method such as a spin coating method, a casting method, a micro-gravure coating method, a gravure coating method, a rod coating method, a roller coating method, a wire bar coating method, a dip coating method, a spray coating method, a screen printing method, a flexographic printing method, an offset printing method, or an inkjet printing method.

[0429] Any solvent that can dissolve the polymer compound / EL device material can be used as the solvent used in solution coating method, and can be appropriately selected depending on the type of the polymer compound used. Its example can include toluene, dimethylbenzene, ethylbenzene, diethylbenzene, mesitylene, propylbenzene, cyclohexylbenzene, dimethoxybenzene, anisole, ethoxytoluene, phenoxytoluene, isopropylbiphenyl, dimethylanisole, phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate or cyclohexane etc.In addition, the amount of the solvent used is not particularly limited, but in view of the ease of application etc., the amount makes the concentration of the polymer compound can be such as being greater than or equal to about 0.1 mass % and less than or equal to about 10 mass % or such as being greater than or equal to about 0.5 mass % and less than or equal to about 5 mass %.

[0430] Furthermore, there is no particular limitation on the method for forming the organic film layer other than the at least one layer of organic film including the polymer compound / EL device material. The organic film layer other than the at least one layer of organic film including the polymer compound / EL device material according to the embodiment can be formed by, for example, a vacuum deposition method or a solution coating method.

[0431] The substrate 110 may be a substrate used in a general EL device. For example, the substrate 110 may be a semiconductor substrate, such as a glass substrate, a silicon substrate, or a transparent plastic substrate.

[0432] The first electrode 120 is formed on the substrate 110. The first electrode 120 can be, for example, an anode and can be formed from a metal, alloy, conductive compound, or the like having a large work function. For example, the first electrode 120 can be formed as a transparent electrode using indium tin oxide (In2O3-SnO2: ITO), indium zinc oxide (In2O3-ZnO), tin oxide (SnO2), or zinc oxide (ZnO), which have excellent transparency and conductivity. Alternatively, the first electrode 120 can be formed as a reflective electrode by laminating magnesium (Mg), aluminum (Al), or the like on a transparent conductive film. After forming the first electrode 120 on the substrate 110, cleaning and UV-ozone treatment may be performed, if necessary.

[0433] The hole injection layer 130 may be formed on the first electrode 120. The hole injection layer 130 may be a layer that facilitates injection of holes from the first electrode 120, and in particular, may be formed to have a thickness (dry film thickness; the same applies hereinafter) of, for example, about 10 nm to about 1000 nm, or, for example, about 20 nm to about 50 nm.

[0434] The hole injection layer 130 may be formed using a known hole injection material. Known hole injection materials for forming the hole injection layer 130 may include, for example, triphenylamine containing poly(ether ketone) (TPAPEK), 4-isopropyl-4'-methyldiphenyl iodide tetrakis(pentafluorophenyl)borate, (PPBI), N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), copper phthalocyanine, 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), 4,4',4"-tris(diphenylamino)triphenylamine (TDATA), 4,4',4"-tris(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA), polyaniline / dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate): PEDOT / PSS, or polyaniline / 10-camphorsulfonic acid.

[0435] The hole transport layer 140 may be formed on the hole injection layer 130. The hole transport layer 140 may be a layer having a function of transporting holes, and may be formed to have a thickness of, for example, about 10 nm to about 150 nm, for example, about 20 nm to about 50 nm. The hole transport layer 140 may be formed by a solution coating method using a polymer compound according to an embodiment. According to this method, the durability (luminescence lifetime) of the EL device 100 may be extended. In addition, the current efficiency of the EL device 100 may be improved and the driving voltage may be reduced. In addition, since the hole transport layer may be formed by a solution coating method, a large-area film may be effectively formed.

[0436] However, when another organic film of the EL device 100 includes a polymer compound according to an embodiment, the hole transport layer 140 may be formed of a known hole transport material. The known hole transport material may include, for example, carbazole derivatives such as 1,1-bis[(di-4-methylphenylamino)phenyl]cyclohexane (TAPC), N-phenylcarbazole and polyvinylcarbazole, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), or N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), etc.

[0437] The light-emitting layer 150 may be formed on the hole transport layer 140. The light-emitting layer 150 may be a layer that emits light by fluorescence, phosphorescence, or the like, and may be formed using a vacuum deposition method, a spin coating method, an inkjet printing method, or the like. The light-emitting layer 150 may be formed to have a thickness of, for example, greater than or equal to about 10 nm and less than or equal to about 60 nm, or, for example, greater than or equal to about 20 nm and less than or equal to about 50 nm. As the light-emitting material of the light-emitting layer 150, any known light-emitting material may be used. However, the light-emitting material included in the light-emitting layer 150 may be a light-emitting material that can emit light from triplet excitons (i.e., phosphorescence). In this case, the lifespan and luminous efficiency of the EL device 100 may be further improved.

[0438] The light-emitting layer 150 is not particularly limited and may have a known structure. For example, the light-emitting layer includes at least one of semiconductor nanocrystal particles and a perovskite compound. That is, in an embodiment, the electroluminescent device may have a light-emitting layer including at least one of semiconductor nanocrystal particles and a perovskite compound. When the light-emitting layer includes semiconductor nanocrystal particles, the EL device may be a quantum dot electroluminescent device (QLED), a quantum dot light-emitting device, or a quantum dot light-emitting diode. In addition, when the light-emitting layer includes a perovskite compound (perovskite halide), the EL device is a perovskite electroluminescent device (PeLED) or a perovskite light-emitting device.

[0439] In the form of a light-emitting layer including semiconductor nanocrystal particles (QLED), the light-emitting layer is a single layer or multiple layers of a plurality of semiconductor nanocrystal particles (quantum dots). Here, the semiconductor nanocrystal particles (quantum dots) are particles of a certain size that have a quantum confinement effect. The diameter of the semiconductor nanocrystal particles (quantum dots) is not particularly limited, but can be approximately about 1 nm to about 20 nm.

[0440] The semiconductor nanocrystal particles (quantum dots) arranged in the light emitting layer can be synthesized by wet chemical process, metal organic chemical vapor deposition process, molecular beam epitaxy process or other similar processes. Among these, the wet chemical process is a method of growing particles by adding precursor materials to an organic solvent.

[0441] In the wet chemical process, as the crystal grows, the organic solvent naturally distributes to the surface of the quantum dot crystal and acts as a dispersant, thereby controlling the growth of the crystal. Therefore, in the wet chemical process, the growth of semiconductor nanocrystal particles can be easily controlled and at a low cost compared to vapor deposition methods such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).

[0442] Semiconductor nanocrystal particles (quantum dots) can control the band gap by controlling their size, thereby obtaining light of various wavelengths from the light-emitting layer (quantum dot light-emitting layer). Therefore, by using multiple quantum dots of different sizes, it is possible to create a display that emits light of multiple wavelengths. The size of the quantum dots can be selected to emit red, green, or blue light, making it possible to construct a color display. In addition, the sizes of the quantum dots can be combined to emit white light with a variety of colors.

[0443] As semiconductor nanocrystal particles (quantum dots), semiconductor materials selected from the group consisting of: II-VI semiconductor compounds; III-V semiconductor compounds; IV-VI semiconductor compounds; Group IV elements or compounds; or combinations thereof may be used.

[0444] The II-VI semiconductor compounds are not particularly limited, and examples thereof may include: binary compounds selected from CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, and mixtures thereof; ternary compounds selected from CdSeS, CdSeTe, CdSTe, ZnSeS, ZnTeSe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, and mixtures thereof; and quaternary compounds selected from CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and mixtures thereof.

[0445] The III-V semiconductor compounds are not particularly limited, and examples thereof may include binary compounds selected from GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds selected from GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof; and quaternary compounds selected from GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof.

[0446] The IV-VI semiconductor compounds are not particularly limited, and examples thereof may include binary compounds selected from SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof.

[0447] The Group IV element or compound is not particularly limited, and examples thereof may include a single element (simple substance) selected from Si, Ge, and a mixture thereof; or a binary compound selected from SiC, SiGe, or a mixture thereof.

[0448] Semiconductor nanocrystal particles (quantum dots) can have a uniform single structure or a core-shell dual structure. The core and shell can comprise different materials. The materials constituting the core and shell can each be composed of different semiconductor compounds. However, the energy band gap of the shell material can be greater than the energy band gap of the core material. For example, the core-shell structure can be ZnTeSe / ZnSe / ZnS, InP / ZnSe / ZnS, CdSe / ZnS, InP / ZnS, etc.

[0449] For example, the manufacturing process of quantum dots with a core (CdSe) / shell (ZnS) structure is described. First, a core (CdSe) precursor material, such as (CH3)2Cd (dimethyl cadmium) and TOPSe (trioctylphosphine selenide), is injected into an organic solvent using TOPO (trioctylphosphine oxide) as a surfactant to form crystals. At this time, after the crystals are kept at a high temperature for a certain period of time so that they grow to a certain size, a precursor material for the shell (ZnS) is injected to form a shell on the surface of the core that has been formed. This allows the manufacture of TOPO-terminated CdSe / ZnS quantum dots.

[0450] In addition, in a form (PeLED) in which the light-emitting layer includes a perovskite compound (perovskite halide), the light-emitting layer 150 may include a compound having a perovskite crystal structure (perovskite compound). The perovskite compound may include, for example, an organic-inorganic hybrid material or an inorganic material having a perovskite crystal structure represented by the following general formula: ApMqXr.

[0451] In the above general formula, A may be at least one cation selected from cations of alkali metal elements and organic cations; M may be a cation of at least one metal element selected from the following: 14 Group elements such as Ge, Sn or Pb, 15 Group elements such as Sb or Bi, or transition metals such as Cu, Ni, Co, Fe, Mn, Cr, Pd, Cd or Ag; X may be at least one anion selected from the following: halide ions such as Cl, Br or I, cyanide, thiocyanate, isothiocyanate or sulfide; p may represent an integer of 1 or greater and 4 or less; q may represent 1 or 2; and r may represent an integer of 3 or greater and 9 or less.

[0452] A may include, for example, an alkali metal ion such as Li, Na, K, Rb, or Cs; or an organic cation such as ammonium ion, methylammonium ion, formamidine ion Ions, guanidine Ion, imidazole ions, pyridine ions or pyrimidines ion.

[0453] Specific examples of the perovskite compound may include, for example, the following compounds: CsPbI3, CsSnI3, CsPbBr3, CsSnBr3, CsPbCl3, CsSnCl3, RbPbI3, RbSnI3, RbPbBr3, RbSnBr3, RbPbCl3, or RbSnCl3, etc.

[0454] The perovskite compound can be obtained by a known method. The perovskite compound can be obtained by any of the following methods: wet synthesis, dry synthesis by grinding, and in situ synthesis.

[0455] The average particle diameter of the perovskite compound is not particularly limited and may be, for example, greater than or equal to about 1 nm and less than or equal to about 100 nm, greater than or equal to about 1 nm and less than or equal to about 50 nm, or greater than or equal to about 1 nm and less than or equal to about 30 nm.

[0456] The perovskite compound may have a ligand on its surface. By coordinating a suitable ligand to the perovskite compound, the photoluminescence quantum yield can be improved. Examples of such ligands include, but are not particularly limited to, cross-linking ligand compounds such as organic ammonium ions, organic acid compounds having two or more unsaturated bonds, or organic base compounds.

[0457] The method for forming the light-emitting layer is not particularly limited. The light-emitting layer can be formed by applying a coating solution containing at least one of semiconductor nanocrystal particles and a perovskite compound (solution coating method). In this case, the solvent constituting the coating solution can be selected from a solvent that does not dissolve the materials in the hole transport layer, such as the hole transport material, for example, a polymer compound.

[0458] The electron transport layer 160 may be formed on the light emitting layer 150. The electron transport layer 160 may be a layer having a function of transporting electrons and may be formed by using a vacuum deposition method, a spin coating method, an inkjet method, etc. The electron transport layer 160 may be formed to have a thickness of, for example, greater than or equal to about 15 nm and less than or equal to about 50 nm.

[0459] The electron transport layer 160 may be formed of a known electron transport material. Examples of known electron transport materials may include (8-hydroxyquinoline) lithium (hydroxyquinoline lithium, Liq), tris (8-hydroxyquinoline) aluminum (Alq3), or a compound having a nitrogen-containing aromatic ring. Examples of compounds having nitrogen-containing aromatic rings may include: compounds including pyridine rings such as 1,3,5-tris [(3-pyridyl)-phenyl-3-yl] benzene, compounds including triazine rings such as 2,4,6-tris (3'-(pyridin-3-yl) biphenyl-3-yl) -1,3,5-triazine, compounds including imidazole rings such as 2- (4- (N-phenylbenzimidazole-1-yl-phenyl) -9,10-dinaphthyl anthracene or 1,3,5-tris (N-phenyl-benzimidazole-2-yl) benzene (TPBI). The electron transport material may be used alone or as a mixture of two or more types.

[0460] The electron injection layer 170 may be formed on the electron transport layer 160. The electron injection layer 170 may be a layer having a function of promoting the injection of electrons from the second electrode 180. The electron injection layer 170 may be formed by using a vacuum deposition method or the like. The electron injection layer 170 may be formed to have a thickness of, for example, greater than or equal to about 0.1 nm and less than or equal to about 5 nm, or, for example, greater than or equal to about 0.3 nm and less than or equal to about 2 nm. Any known material may be used as a material for forming the electron injection layer 170. For example, the electron injection layer 170 may be formed of a lithium compound such as (8-hydroxyquinoline) lithium (hydroxyquinoline lithium, Liq), lithium fluoride (LiF), sodium chloride (NaCl), cesium fluoride (CsF), lithium oxide (Li2O) or barium oxide (BaO).

[0461] The second electrode 180 may be formed on the electron injection layer 170. The second electrode 180 may be formed using a vacuum deposition method or the like. The second electrode 180 may be, for example, a cathode and may be formed of a metal, alloy, or conductive compound having a small work function. For example, the second electrode 180 may be formed as a reflective electrode using a metal such as lithium (Li), magnesium (Mg), aluminum (Al), calcium (Ca), or an alloy such as aluminum-lithium (Al-Li), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag). The second electrode 180 may be formed to have a thickness of, for example, about 10 nm to about 200 nm, for example, about 50 nm to about 150 nm. Alternatively, the second electrode 180 may be formed as a transparent electrode using a thin film of a metal material having a thickness of 20 nm or less, a transparent conductive film such as indium tin oxide (In2O3-SnO2) or indium zinc oxide (In2O3-ZnO).

[0462] As described above, the EL device 100 according to the present embodiment has been described as an example of the electroluminescent device according to the embodiment. The EL device 100 according to the present embodiment can improve durability (luminescence lifetime) and luminous efficiency (current efficiency) with good balance by including an organic film (e.g., a hole transport layer or a hole injection layer) including the polymer compound according to the embodiment.

[0463] The stacked structure of the EL device 100 according to the embodiment is not limited to the above example. The EL device 100 according to the embodiment may be formed in another known stacked structure. For example, the EL device 100 may omit one or more of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, or the electron injection layer 170, and may further include another layer. In addition, each layer of the EL device 100 may be formed as a single layer or a plurality of layers.

[0464] For example, the EL device 100 may further include a hole blocking layer between the hole transport layer 140 and the light emitting layer 150 to prevent electrons or holes from diffusing into the electron transport layer 160. Also, the hole blocking layer may be formed of, for example, oxadiazole derivatives, triazole derivatives, or phenanthroline derivatives.

[0465] In addition, the polymer compound according to the embodiment may be applied to an electroluminescent device other than QLED or PeLED. Other electroluminescent devices to which the polymer compound according to the embodiment may be applied include, but are not particularly limited to, organic electroluminescent devices.

[0466] Implementations may include the following aspects and forms.

[0467] 1. A polymer compound comprising a structural unit (A) represented by Chemical Formula 1:

[0468] Chemical formula 1

[0469]

[0470] In Chemical Formula 1,

[0471] Ar 11 and Ar 12 may each independently be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms,

[0472] Ar 11 and Ar 12 may optionally be linked to each other to form a ring,

[0473] L 1 may be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms,

[0474] Ar 1 may be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms,

[0475] Ar 2 It may be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms, and Ar 2 Optionally with Ar 1 Form a ring,

[0476] X 1 may be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms, and

[0477] Y 1 The aromatic hydrocarbon group may be a group selected from the following: an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by an alkyl group having 1 to 14 carbon atoms containing a thiol group, an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by an alkoxyalkyl group having 2 to 14 carbon atoms containing a thiol group, or an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by an alkyl group having 1 to 14 carbon atoms containing a thiol group and an alkoxyalkyl group having 2 to 14 carbon atoms containing a thiol group.

[0478] 2. The polymer compound described in 1 above, wherein the structural unit (A) can be represented by Chemical Formula 1-1:

[0479] Chemical formula 1-1

[0480]

[0481] In Chemical Formula 1-1,

[0482] R 11 to R 14 and R 21 to R 24 can each independently be a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aryl group, or a halogen atom, wherein R 11 and R 21 may bond to each other to form a ring, and

[0483] L 1 、Ar 1 、Ar 2 、X 1 and Y 1 Same as defined in Chemical Formula 1.

[0484] 3. The polymer compound described in 1 or 2 above, further comprising a structural unit (B) represented by Chemical Formula 2:

[0485] Chemical formula 2

[0486]

[0487] In Chemical Formula 2,

[0488] Ar 21 and Ar 22 may each independently be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms,

[0489] Ar 21 and Ar 22 may be optionally bonded to each other to form a ring,

[0490] L 2 may be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms,

[0491] Ar 3 may be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms,

[0492] Ar 4 It may be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms, and Ar 4 Optionally with Ar 3 Form a ring,

[0493] X 2may be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms,

[0494] Y 2 An aromatic hydrocarbon group having 6 to 25 ring atoms which may be unsubstituted or substituted with an alkyl group having 1 to 14 carbon atoms, and

[0495] Ar 21 、Ar 22 , L 2 、Ar 3 、Ar 4 and X 2 An alkyl group having 1 to 14 carbon atoms does not have a thiol group-containing group, and an alkoxyalkyl group having 2 to 14 carbon atoms does not have a thiol group-containing group.

[0496] 4. The polymer compound described in 3 above, wherein the structural unit (B) can be represented by Chemical Formula 2-1:

[0497] Chemical formula 2-1

[0498]

[0499] In Chemical Formula 2-1,

[0500] R 31 to R 34 and R 41 to R 44 can each independently be a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aryl group, or a halogen atom, wherein R 31 and R 41 may be optionally bonded to each other to form a ring,

[0501] L 2 、Ar 3 、Ar 4 、X 2 and Y 2 may be the same as defined in Chemical Formula 2, and

[0502] R 31 to R 34 、R 41 to R 44 , L 2 、Ar 3 、Ar 4 and X 2 An alkyl group having 1 to 14 carbon atoms does not have a thiol group-containing group, and an alkoxyalkyl group having 2 to 14 carbon atoms does not have a thiol group-containing group.

[0503] 5. The polymer compound described in 3 or 4 above, wherein the molar ratio of structural unit (A) may be greater than or equal to about 1 mol% and less than about 30 mol% (when the total molar ratio of structural unit (A) and structural unit (B) is 100 mol%).

[0504] 6. The polymer compound described in any one of 3 to 5 above, wherein Ar in Chemical Formula 1 11 Can be combined with Ar in chemical formula 2 21 same,

[0505] Ar in Chemical Formula 1 12 Can be combined with Ar in chemical formula 2 22 same,

[0506] L in Chemical Formula 1 1 Can be used with L in chemical formula 2 2 same,

[0507] Ar in Chemical Formula 1 1 Can be combined with Ar in chemical formula 2 3 same,

[0508] Ar in Chemical Formula 1 2 Can be combined with Ar in chemical formula 2 4 Same, and

[0509] X in Chemical Formula 1 1 Can be combined with X in chemical formula 2 2 same.

[0510] 7. The polymer compound described in any one of 4 to 6 above, wherein R in Chemical Formula 1-1 11 Can be combined with R in Chemical Formula 2-1 31 Same, R in Chemical Formula 1-1 12 Can be combined with R in Chemical Formula 2-1 32 Same, R in Chemical Formula 1-1 13 Can be combined with R in Chemical Formula 2-1 33 Same, R in Chemical Formula 1-1 14 Can be combined with R in Chemical Formula 2-1 34 Same, R in Chemical Formula 1-1 21 Can be combined with R in Chemical Formula 2-1 41 Same, R in Chemical Formula 1-1 22 Can be combined with R in Chemical Formula 2-1 42 Same, R in Chemical Formula 1-1 23 Can be combined with R in Chemical Formula 2-1 43 Same, R in Chemical Formula 1-1 24 Can be combined with R in Chemical Formula 2-1 44Same, L in Chemical Formula 1-1 1 With L in chemical formula 2-1 2 The same, Ar in chemical formula 1-1 1 Can be combined with Ar in chemical formula 2-1 3 The same, Ar in chemical formula 1-1 2 Can be combined with Ar in chemical formula 2-1 4 Same as X in Chemical Formula 1-1 1 Can be used with X in chemical formula 2-1 2 same.

[0511] 8. The polymer compound described in any one of 1 to 7 above, wherein the thiol group-containing alkoxyalkyl group may have a structure represented by Chemical Formula i-1:

[0512] Chemical formula i-1

[0513] *-Z 1 -OZ 2 -SH

[0514] In chemical formula i-1,

[0515] Z 1 may represent an alkylene group having 1 to 14 carbon atoms which is unsubstituted or substituted with a thiol group,

[0516] Z 2 may represent an alkylene group having 1 to 13 carbon atoms which is unsubstituted or substituted with a thiol group,

[0517] By Z 1 The carbon number of the alkylene represented by Z 2 The sum of the carbon numbers of the alkylene groups represented by may be an integer of 14 or less, and

[0518] *bonded to constituent Y 1 An aromatic hydrocarbon group having 6 to 25 ring atoms.

[0519] 9. The polymer compound described in any one of 1 to 8 above, wherein the thiol group-containing alkyl group may have a structure represented by Chemical Formula i-2:

[0520] Chemical formula i-2

[0521] *-Z 1 -SH

[0522] In chemical formula i-2,

[0523] Z 1 may represent an alkylene group having 1 to 14 carbon atoms which is unsubstituted or substituted with a thiol group, and

[0524] *bonded to constituent Y1 An aromatic hydrocarbon group having 6 to 25 ring atoms.

[0525] 10. The polymer compound described in any one of 1 to 8 above, wherein Y in Chemical Formula 1 1 The aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted with an alkoxyalkyl group having 2 to 14 carbon atoms and containing a thiol group may be used.

[0526] 11. The polymer compound described in any one of 1 to 10 above, wherein the thiol group-containing alkoxyalkyl group may have two or more thiol groups.

[0527] 12. The polymer compound described in any one of 1 to 9 above, wherein Y in Chemical Formula 1 1 The aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted with an alkyl group having 1 to 10 carbon atoms and containing a thiol group may be used.

[0528] 13. The polymer compound described in any one of 1 to 12 above, wherein in Chemical Formula 1, Y 1 It may be one of the groups represented by chemical formulas (3-1) to (3-6):

[0529]

[0530] In chemical formulas (3-1) to (3-6),

[0531] R 301 、R 302 、R 305 、R 307 and R 308 may each independently be a substituted or unsubstituted alkylene group having 1 to 14 carbon atoms,

[0532] R 303 、R 304 、R 306 、R 309 and R 310 may each independently be a substituted or unsubstituted alkylene group having 1 to 11 carbon atoms, and

[0533] ** indicates binding sites.

[0534] 14. The polymer compound described in 13 above, wherein Y in Chemical Formula 1 1 It may be a group represented by Chemical Formula (3-1) or (3-2).

[0535] 15. The polymer compound described in any one of 1 to 14 above, wherein in Chemical Formula 1, L 1 It may be any one of the groups represented by chemical formulas (4-1) to (4-24):

[0536]

[0537] In chemical formulas (4-1) to (4-24),

[0538] *** is bound to nitrogen, and **** is bound to Ar 1 .

[0539] 16. The polymer compound described in any one of 1 to 15 above, wherein in Chemical Formula 1, -L 1 -Ar 1 -N(Ar 2 )(X 1 ) may be any one of the groups represented by chemical formulas (5-1) to (5-3):

[0540]

[0541] In chemical formulas (5-1) to (5-3),

[0542] R 501 to R 506 Each of them independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aryl group, or a halogen atom.

[0543] X 1 may be the same as defined in Chemical Formula 1, and

[0544] *****Bound to nitrogen atom.

[0545] 17. An electroluminescent device material comprising the polymer compound described in any one of 1 to 16 above.

[0546] 18. A liquid composition comprising the polymer compound as described in any one of 1 to 16 above and at least one solvent.

[0547] 19. An electroluminescent device comprising a first electrode, a second electrode, and at least one organic film between the first electrode and the second electrode.

[0548] The at least one organic film may include the polymer compound described in any one of 1 to 16.

[0549] 20. The electroluminescent device described in 19 above, wherein the at least one layer of the organic film including the polymer compound may be a hole transport layer or a hole injection layer.

[0550] 21. The electroluminescent device described in 19 or 20 above, wherein the electroluminescent device may further have a light-emitting layer comprising at least one of semiconductor nanoparticles and a perovskite compound.

[0551] Example

[0552] The present disclosure is described in more detail using the following examples and comparative examples. However, the technical scope of the present disclosure is not limited to the following examples. In the following examples, unless otherwise specified, each operation is performed at room temperature (25°C). In addition, unless otherwise specified, "%" and "parts" represent "mass %" and "mass parts", respectively. In addition, in the following chemical formulas, unless otherwise specified, "C" representing an alkyl group is m H 2m+1 (m is an integer)" means a straight-chain alkyl group.

[0553] Synthesis Example 1: Synthesis of Compound M-1

[0554] Compound M-1 was synthesized according to Reaction Scheme 1.

[0555] (Reaction Scheme 1)

[0556]

[0557] Specifically, 2,7-dibromofluorene (26.4g) and tetrahydrofuran (THF) (400mL) are added to a 1L four-necked flask and stirred at 0°C under a nitrogen atmosphere. Subsequently, potassium tert-butoxide (t-BuOK) (27.0g) is added thereto and stirred at 0°C for 10 minutes. A solution prepared by dissolving 1,6-dibromohexane (414g) in THF (180mL) is slowly added dropwise thereto and stirred at 0°C for 30 minutes. After adding 200mL of water thereto and evaporating the solvent under reduced pressure, extraction is performed by using ethyl acetate. After separating the aqueous layer, the organic layer therefrom is washed with water and dried over magnesium sulfate. After evaporating the solvent and unreacted 1,6-dibromohexane under reduced pressure, the solid obtained therefrom is washed with hexane to obtain 2,7-dibromo-9,9-bis(6-bromohexyl)-9H-fluorene (40.9g).

[0558] In a 200 mL four-necked flask, 2,3-dimercapto-1-propanol (25.0 g) and acetone (100 mL) were added, 1 drop of 10 N HCl was added thereto, and the mixture was stirred at room temperature for 12 hours. 25 g of magnesium sulfate was added thereto, and the mixture was stirred for 1 hour. After filtering the magnesium sulfate, acetone was evaporated under reduced pressure to obtain (2,2-dimethyl-1,3-dithiolan-4-yl)methanol (31.6 g).

[0559] (2,2-dimethyl-1,3-dithiolane-4-yl)methanol (3.10g), 2,7-dibromo-9,9-bis(6-bromohexyl)-9H-fluorene (5.83g) and THF (38mL) are loaded into a 50mL four-necked flask and stirred at 0°C under a nitrogen atmosphere. 64% NaH (1.05g) is added thereto, and 30 minutes, and then further stirred at room temperature for 3 days. NaH (0.3g) is added thereto, and stirred for another hour. Subsequently, the mixture is stirred at 0°C, and methanol is added thereto to quench the reaction. After the solvent is evaporated under reduced pressure, extraction is performed by using ethyl acetate. The organic layer therefrom is washed with water and dried over magnesium sulfate. After the solvent is evaporated under reduced pressure, the residue is purified by column chromatography (chromatography) (silica gel, hexane / dichloromethane) to obtain compound M-1 (1.07g).

[0560] Synthesis Example 2: Synthesis of Compound M-2

[0561] Compound M-2 was synthesized according to Reaction Scheme 2.

[0562] (Reaction Scheme 2)

[0563]

[0564] Specifically, 2,7-dibromo-9,9-bis(6-bromohexyl)-9H-fluorene (10.6 g), potassium thioacetate (5.28 g) and THF (154 mL) obtained in the same manner as in Synthesis Example 1 were charged into a 300 mL four-necked flask and stirred for 3 hours at 60 ° C under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, and ion exchange water (100 mL) was added thereto to separate the organic layer. The aqueous layer therefrom was extracted with dichloromethane (100 mL × 3) to obtain another organic layer, which was combined with the organic layer obtained previously, washed with saturated brine (100 mL × 3), and dried over magnesium sulfate. After removing the solvent under reduced pressure, the residue was purified by column chromatography (silica gel, hexane / toluene) to obtain compound M-2 (7.84 g).

[0565] Synthesis Example 3: Synthesis of Compound C-1

[0566] Compound C-1 was synthesized according to Reaction Scheme 3.

[0567] (Reaction Scheme 3)

[0568]

[0569] Specifically, 2-bromocarbazole (20.0 g), 4-chloro-N-(4-chlorophenyl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline (10.0 g), sodium carbonate (4.84 g), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh 3 ) 4 , 1.31 g), toluene (80 mL), ethanol (30 mL) and water (30 mL) were placed in a 100 mL four-necked flask and stirred at 100° C. (bath temperature) for 3 hours. After cooling to room temperature, the aqueous layer was removed, and the organic layer therefrom was washed with water (100 mL×2) and dried over magnesium sulfate. After evaporating the solvent under reduced pressure, toluene (200 mL) was added to the residue, refluxed at 60° C. for 1 hour, and a solid was filtered therefrom and dried to obtain N-(4-(9-carbazol-2-yl)phenyl)-4-chloro-N-(4-chlorophenyl)aniline (6.08 g).

[0570] Subsequently, the obtained N-(4-(9-carbazol-2-yl)phenyl)-4-chloro-N-(4-chlorophenyl)aniline (6.00 g), 1-bromo-4-hexylbenzene (3.00 g), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.580 g), tri-tert-butylphosphonium tetrafluoroborate (t-Bu3PH·BF4, 0.276 g), sodium tert-butoxide (t-BuONa, 2.43 g) and toluene (60 mL) were placed in a four-necked flask replaced with argon and heated at 110°C for 7 hours. After cooling to room temperature, impurities were filtered out using celite. After evaporating the solvent under reduced pressure, the residue was purified by column chromatography to obtain 4-chloro-N-(4-chlorophenyl)-N-(4-(9-(4-hexylphenyl)-9-carbazol-2-yl)phenyl)aniline (1.60 g).

[0571] Then, the obtained 4-chloro-N-(4-chlorophenyl)-N-(4-(9-(4-hexylphenyl)-9-carbazol-2-yl)phenyl)aniline (1.60 g), diboronic acid pinacol ester (1.90 g), potassium acetate (KOAc, 1.47 g), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.114 g), Xphos (0.177 g) and 1,4-dioxane (16 mL) were charged into a 50 mL three-necked flask and stirred at a bath temperature of 100°C for 3 hours under a nitrogen atmosphere. After cooling to room temperature, insoluble matter was removed by using diatomaceous earth as a filter agent. After removing the solvent under reduced pressure, the residue was added to a mixed solvent of toluene (20 mL) and hexane (40 mL), and activated carbon (2.0 g) was added thereto, and refluxed for 30 minutes. After removing insoluble matter by using celite as a filtering agent and evaporating the solvent under reduced pressure, the residue was recrystallized with toluene / acetonitrile to obtain Compound C-1 (1.85 g).

[0572] Example 1-1: Synthesis of polymer compound P-1

[0573] Under a nitrogen atmosphere, compound M-1 (0.141 g) according to Synthesis Example 1, compound C-1 (1.438 g) according to Synthesis Example 3, 2,7-dibromo-9,9-di-n-decylfluorene (hereinafter, also described as “Compound D-1”, 0.941 g), dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphine]palladium(II) (12.1 mg), toluene (50 mL), and 20% by mass tetraethylammonium hydroxide aqueous solution (9.01 g) were added to a four-necked flask and stirred at 85° C. for 2 hours. Subsequently, phenylboric acid (211 mg), bis(triphenylphosphine)palladium(II) dichloride (73.6 mg), and 20% by mass tetraethylammonium hydroxide aqueous solution (9.01 g) were added thereto, and stirred at 85° C. for 6 hours. Then, sodium N,N-diethyldithiocarbamate trihydrate (5.91 g) dissolved in ion-exchanged water (50 mL) was added thereto, and stirred at 85° C. for 6 hours. Under a nitrogen atmosphere, after separation of the organic layer and the aqueous layer, the organic layer was sequentially washed with ion-exchanged water (50 mL×2), a saturated NH4Cl aqueous solution (50 mL×5), and ion-exchanged water (50 mL×2).

[0574] After being reprecipitated by using methanol, the solid obtained by it is washed with methanol, filtered and vacuum dried.The dry solid is dissolved in toluene (20mL), activated alumina (9.0g) and diatomaceous earth (4.5g) are added thereto, and stirred at 90 ℃ for 1 hour, and solid is filtered.The filtrate from it is reprecipitated by using methanol, solid is filtered and vacuum dried from it.The solid obtained is dissolved in toluene (50mL), ion exchange resin (a mixture of 0.5 weight parts of cationic exchange resins and 0.5 weight parts of anionic exchange resins, 10g) is added thereto, and at room temperature stirred for 12 hours.Ion exchange resin is filtered, and the filtrate from it is reprecipitated with methanol, and vacuum dried to obtain P-1 precursor (0.747g).

[0575] Subsequently, P-1 precursor (0.730g), Dess-Martin reagent (648mg), toluene (28mL) and ion exchange water (7mL) are loaded into 2-necked flasks, and stirred at room temperature for 12 hours under a nitrogen atmosphere. Organic layer is added dropwise to methanol to precipitate solid, and the solid is vacuum dried. Gained solid is dissolved in toluene (50mL), and anion exchange resin (10g) is added thereto, and stirred for 12 hours. Ion exchange resin is filtered, the filtrate therefrom is added dropwise to methanol to precipitate solid, the solid is dissolved in toluene, and the solution is added dropwise to methanol to precipitate solid, the solid is filtered and dried to obtain polymer compound P-1 (0.634g). Weight average molecular weight (Mw) and polydispersity (Mw / Mn) of polymer compound P-1 are measured by SEC. As a result, Mw is 202,000Da (dalton), and Mw / Mn is 3.34.

[0576] The polymer compound P-1 had the following structural units as determined from the charging ratio of the monomers.

[0577] (Polymer Compound P-1)

[0578]

[0579] Example 1-2: Synthesis of polymer compound P-2

[0580] Under a nitrogen atmosphere, monomer M-2 (0.111 g) according to Synthesis Example 2, compound C-1 (1.434 g) according to Synthesis Example 3, 2,7-dibromo-9,9-di-n-decylfluorene (compound D-1, 0.939 g), dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphine]palladium(II) (12.3 mg), toluene (54 mL), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (8.99 g) were placed in a four-necked flask and stirred at 85° C. for 2 hours. Subsequently, phenylboric acid (211 mg), bis(triphenylphosphine)palladium(II) dichloride (73.6 mg), and a 20% by mass aqueous solution of tetraethylammonium hydroxide (9.01 g) were added thereto, and stirred at 85° C. for 6 hours. Then, a solution prepared by dissolving sodium N,N-diethyldithiocarbamate trihydrate (5.89 g) in ion-exchanged water (50 mL) was added thereto, and stirred for 6 hours at 85° C. Under a nitrogen atmosphere, after separation of the organic layer and the aqueous layer, the organic layer was sequentially washed with ion-exchanged water (50 mL×2), a saturated NH4Cl aqueous solution (50 mL×5), and ion-exchanged water (50 mL×2).

[0581] After the reprecipitation by using methanol, the solid obtained by it is washed with methanol, filtered and vacuum dried.Dry solid is dissolved in toluene (20mL), activated alumina (9.0g) and diatomaceous earth (4.5g) are added to it, stirred 1 hour at 90 DEG C, and filtered solid from it.The filtrate from it is reprecipitated by using methanol, and filtered solid and vacuum dried from it.The solid obtained is dissolved in toluene (50mL), ion exchange resin (a mixture of 0.5 parts by mass of cation exchange resin and 0.5 parts by mass of anion exchange resin, 10g) is added thereto, and at room temperature stirred 12 hours.Ion exchange resin is filtered, and the filtrate from it is reprecipitated with methanol, and vacuum dried to obtain P-2 precursor (0.785g).

[0582] Subsequently, P-2 precursor (0.730g), Dess-Martin reagent (365mg), toluene (20mL) and ion exchange water (20mL) are loaded into 2-necked flasks, and stirred at room temperature for 12 hours under a nitrogen atmosphere. The organic layer from it is dropwise added to methanol to precipitate solid, and the solid is vacuum dried. The solid obtained is dissolved in toluene (50mL), 10g anion exchange resins are added thereto, and stirred for 12 hours. Ion exchange resin is filtered, the filtrate from it is dropwise added to methanol to precipitate solid, the solid is dissolved in toluene, the solution is dropwise added to methanol to precipitate solid, the solid is filtered and dried to obtain polymer compound P-2 (0.491g). Weight average molecular weight (Mw) and polydispersity (Mw / Mn) of polymer compound P-2 are measured by SEC. As a result, Mw is 277,000Da, and Mw / Mn is 2.56.

[0583] The polymer compound P-2 had the following structural units as determined from the charging ratio of the monomers.

[0584] (Polymer Compound P-2)

[0585]

[0586] Comparative Example 1-1: Synthesis of polymer compound CP-1

[0587] As polymer compound CP-1, poly[(9,9-dioctylfluorene-2,7-diyl)-co-(4,4′-(N-(4-sec-butylphenyl)diphenylamine)] (TFB, Luminescence Technology Corp.) having the following structural units was prepared. The weight average molecular weight (Mw) and polydispersity (Mw / Mn) of TFB (polymer compound CP-1) were measured by SCE. As a result, Mw was 320,000 Da and Mw / Mn was 3.70.

[0588] (Polymer compound CP-1)

[0589]

[0590] Comparative Example 1-2: Synthesis of polymer compound CP-2

[0591] Under an argon atmosphere, compound C-1 (1.64 g) according to Synthesis Example 3, 2,7-dibromo-9,9-di-n-hexylfluorene (hereinafter, also described as “Compound D-2”) (0.983 g), palladium acetate (4.5 mg), tris(2-methoxyphenyl)phosphine (42.2 mg), toluene (54 mL) and 20% by mass tetraethylammonium hydroxide aqueous solution (10.2 g) were placed in a four-necked flask and stirred at 85° C. for 6 hours. Subsequently, phenylboric acid (241 mg), tetrakis(triphenylphosphino)palladium (84.1 mg) and 20% by mass tetraethylammonium hydroxide aqueous solution (10.2 g) were added thereto and stirred for 3 hours. Then, sodium N,N-diethyldithiocarbamate trihydrate (6.75 g) dissolved in 50 mL of ion-exchanged water was added thereto and stirred at 85° C. for 2 hours. The organic layer is separated from the aqueous layer and washed sequentially with water, 3% by mass acetic acid aqueous solution and water. The organic layer is added to a column chromatography filled with silica gel / alumina for purification and a portion of the solvent is evaporated under reduced pressure. The obtained liquid is added dropwise to methanol to precipitate a solid, and the solid is dissolved in toluene. Subsequently, the solution is added dropwise to methanol to precipitate a solid, the solid is filtered and dried to obtain polymer compound CP-2 (0.930g). The weight average molecular weight (Mw) and polydispersity (Mw / Mn) of polymer compound CP-2 are measured by SCE. As a result, Mw is 104,000Da, and Mw / Mn is 2.04.

[0592] The polymer compound CP-2 has the following structural units as determined from the charging ratio of the monomers.

[0593] (Polymer compound CP-2)

[0594]

[0595] Comparative Example 1-3: Synthesis of polymer compound CP-3

[0596] Under a nitrogen atmosphere, compound C-1 (1.49 g) according to Synthesis Example 3, 2,7-dibromo-9,9-di-n-decylfluorene (compound D-1, 0.97 g), palladium acetate (3.6 mg), tri(2-methoxyphenyl)phosphine (33.9 mg), toluene (54 mL) and 20% by mass tetraethylammonium hydroxide aqueous solution (8.27 g) were placed in a four-necked flask and stirred at 85° C. for 6 hours. Subsequently, phenylboric acid (194 mg), bis(triphenylphosphine)palladium(II) dichloride (67.6 mg), 20% by mass tetraethylammonium hydroxide aqueous solution (8.27 g) and sodium carbamate trihydrate (5.42 g) were added thereto and stirred at 85° C. for 2 hours. The organic layer was separated from the aqueous layer and washed with water. The washed organic layer was purified by column chromatography (filler: silica gel / alumina, eluent: toluene), reprecipitated with toluene / methanol, and vacuum dried to obtain polymer compound CP-3 (1.17 g). The weight average molecular weight (Mw) and polydispersity (Mw / Mn) of polymer compound CP-3 were measured by SEC. As a result, Mw was 73,000 Da and Mw / Mn was 1.40.

[0597] The polymer compound CP-3 obtained in this manner has the following structural units as determined from the charging ratio of the monomers.

[0598] Polymer compound CP-3

[0599]

[0600] [Evaluation of Properties of Each Polymer Compound]

[0601] The glass transition temperatures (Tg) (° C.) of polymer compounds P-1 and P-2 according to Examples 1-1 and 1-2 and polymer compounds CP-1 to CP-3 according to Comparative Examples 1-1 to 1-3 were measured as follows.

[0602] (Glass transition temperature (Tg))

[0603] The glass transition temperature (Tg) of each sample of the polymer compound was measured using differential scanning calorimetry (DSC) (Tradename: DSC6000, Seiko Instrument Inc.) by increasing the temperature to 300° C. at an increasing rate of 10° C. / min and holding the temperature for 10 minutes, decreasing the temperature to 25° C. at a decreasing rate of 10° C. / min and holding the temperature for 10 minutes, and increasing the temperature to 300° C. over 10 minutes and measuring. After the measurement, the sample was cooled to room temperature (25° C.) at a rate of 10° C. / min.

[0604] Table 1

[0605]

[0606] Example 2-1: Fabrication of a quantum dot electroluminescent device 1

[0607] As the first electrode (anode), an ITO-attached glass substrate was used, on which indium tin oxide (ITO) was patterned to have a film thickness of 150 nm. The ITO-attached glass substrate was washed sequentially with a neutral detergent, deionized water, water, and isopropyl alcohol, and treated with UV-ozone. Subsequently, poly (3,4-ethylenedioxythiophene) / poly (4-styrene sulfonate) (PEDOT / PSS) (Sigma-Aldrich Co., Ltd.) was spin-coated on the ITO-attached glass substrate to have a dry film thickness of 30 nm and dried. As a result, a hole injection layer with a thickness (dry film thickness) of 30 nm was formed on the ITO-attached glass substrate.

[0608] On the hole injection layer, a toluene solution containing 1.0% by mass of the polymer compound P-1 (hole transport material) according to Example 1-1 was spin-coated to have a dry film thickness of 30 nm, and heat-treated at 230° C. for 60 minutes to form a hole transport layer. As a result, a hole transport layer having a thickness (dry film thickness) of 30 nm was formed on the hole injection layer.

[0609] A quantum dot dispersion was prepared by dispersing blue quantum dots ZnTeSe / ZnSe / ZnS (core / shell / shell; average diameter of about 10 nm) in cyclohexane to 1.0% by mass. The hole transport layer, particularly polymer compound P-1, was insoluble in cyclohexane. The quantum dot dispersion was spin-coated on the hole transport layer to a dry film thickness of 30 nm and dried. As a result, a quantum dot light-emitting layer having a thickness (dry film thickness) of 30 nm was formed on the hole transport layer. Light emitted by the quantum dot dispersion upon irradiation with ultraviolet light had a central wavelength of 462 nm and a full width at half maximum (FWHM) of 30 nm.

[0610] The quantum dot light-emitting layer was completely dried. (8-Hydroxyquinolinate) lithium (Liq) and 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI) (Sigma-Aldrich Co., Ltd.) were co-deposited as electron transport materials on the quantum dot light-emitting layer using a vacuum deposition apparatus. As a result, an electron transport layer having a thickness of 36 nm was formed on the quantum dot light-emitting layer.

[0611] On the electron transport layer, (8-hydroxyquinoline)lithium (Liq) was deposited by using a vacuum deposition apparatus. As a result, a 0.5 nm thick electron injection layer was formed on the electron transport layer.

[0612] Aluminum (Al) was deposited on the electron injection layer using a vacuum deposition apparatus. As a result, a 100 nm thick second electrode (cathode) was formed on the electron injection layer. In this way, a quantum dot electroluminescent device 1 was obtained.

[0613] Example 2-2: Fabrication of quantum dot electroluminescent device 2

[0614] A quantum dot electroluminescent device 2 was manufactured in the same manner as in Example 2-1, except that the polymer compound P-2 of Example 1-2 was used instead of the polymer compound P-1 of Example 2-1.

[0615] Comparative Example 2-1: Preparation of Comparative Quantum Dot Electroluminescent Device 1

[0616] A comparative quantum dot electroluminescent device 1 was manufactured in the same manner as in Example 2-1, except that the polymer compound CP-1 of Comparative Example 1-1 was used instead of the polymer compound P-1 of Example 2-1.

[0617] Comparative Example 2-2: Comparative Preparation of Quantum Dot Electroluminescent Device 2

[0618] A comparative quantum dot electroluminescent device 2 was manufactured in the same manner as in Example 2-1, except that the polymer compound CP-2 of Comparative Example 1-2 was used instead of the polymer compound P-1 of Example 2-1.

[0619] Comparative Example 2-3: Comparative Preparation of Quantum Dot Electroluminescent Device 3

[0620] A comparative quantum dot electroluminescent device 3 was manufactured in the same manner as in Example 2-1, except that the polymer compound CP-3 of Comparative Example 1-3 was used instead of the polymer compound P-1 of Example 2-1.

[0621] [Evaluation of electroluminescent devices]

[0622] The luminous efficiency (EQE) and durability (LT50) of the electroluminescent devices 1 and 2 of Examples 2-1 and 2-2 and the comparative electroluminescent devices 1 to 3 of Comparative Examples 2-1 to 2-3 were evaluated as follows.

[0623] <Luminous Efficiency (External Quantum Efficiency (EQE))>

[0624] When voltage is applied to each of the quantum dot electroluminescent devices, the quantum dot electroluminescent device emits light as current begins to flow at a predetermined voltage. A DC constant voltage power supply (source meter, Keyence Corp.) was used to slowly increase the voltage for each device to measure the current at that point, and a luminance meter (SR-3, Topcom Technology Cp., Ltd.) was used to measure the luminance of the device during light emission. Luminance measurement was stopped at the point where the luminance began to decrease.

[0625] In addition, the maximum external quantum efficiency (EQE) was calculated using the spectral radiance spectrum measured by a luminance meter assuming Lambertian radiation. max (%), which was used to evaluate the luminous efficiency.

[0626] <lt50>

[0627] A DC constant voltage power supply (source meter, Keyence Corp.) was used to apply a predetermined voltage to each of the quantum dot electroluminescent devices to cause each of the quantum dot electroluminescent devices to emit light. When the brightness reached 650 nits (cd / m 2 ), while measuring the luminance by slowly increasing the current using a luminance meter (SR-3, Topcom), the quantum dot electroluminescent devices were each allowed to stand by keeping the current constant. The time when the luminance measured by the luminance meter gradually decreased and reached 50% of the initial luminance was measured as "LT50 (hr)".

[0628] Table 2-1

[0629]

[0630] Table 2-2 (continued)

[0631]

[0632] Referring to the results of Tables 2-1 and 2-2, compared with the comparative quantum dot electroluminescent devices 1 to 3 that do not use the polymer compound according to the embodiment, the quantum dot electroluminescent devices 1 and 2 of the examples were confirmed to have good balance and compatibility in durability (significantly long luminescence lifetime) and luminescence efficiency.

[0633] In particular, compared to the comparative quantum dot electroluminescent device 3 (Comparative Example 2-3) using a polymer compound composed only of a structural unit (B) not including a thiol group, the quantum dot electroluminescent devices 1 and 2 (Examples 2-1 and 2-2) using a polymer compound further having a structural unit (A) including a thiol group in addition to the same structural unit (B) showed improved luminous efficiency (EQE max ) and a satisfactory luminescence lifetime (LT50). In this way, the quantum dot electroluminescent device according to the embodiment exhibits a sufficiently long luminescence lifetime (LT50) and excellent luminescence efficiency (EQE max ), thereby achieving satisfactory luminous performance (balance between luminous efficiency and luminous lifetime) in practical use.

[0634] The comparative quantum dot electroluminescent devices 2 and 3 according to Comparative Examples 2-2 and 2-3 exhibit relatively excellent luminescence lifetime (LT50), but slightly deteriorated luminescence efficiency (EQE max ). Therefore, the quantum dot electroluminescent device according to the embodiment exhibits very excellent effects in terms of luminous performance (balance between luminous efficiency and luminous lifetime) in actual use.

[0635] Although the above has been described with reference to the embodiment, the present disclosure is not limited to the specific embodiment, and various variations and modifications are possible within the scope of the present invention described in the claims.

[0636] <Description of symbols>

[0637] 100 Electroluminescent Devices (EL Devices)

[0638] 110 substrate

[0639] 120 first electrode

[0640] 130 hole injection layer

[0641] 140 hole transport layer

[0642] 150 Luminous Layer

[0643] 160 Electron Transport Layer

[0644] 170 Electron injection layer

[0645] 180 Second Electrode

Claims

1. A polymer compound comprising a structural unit (A) represented by Chemical Formula 1: Chemical formula 1 in, In Chemical Formula 1, Ar 11 and Ar 12 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, Ar 11 and Ar 12 are optionally linked to each other to form a ring, L 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms, Ar 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, Ar 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms, Ar 1 and Ar 2 are optionally linked to each other to form a ring, X 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms, Y 1 is a group selected from the following: an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by a thiol group-containing alkyl group having 1 to 14 carbon atoms, an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by a thiol group-containing alkoxyalkyl group having 2 to 14 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted by a thiol group-containing alkyl group having 1 to 14 carbon atoms and a thiol group-containing alkoxyalkyl group having 2 to 14 carbon atoms.

2. The polymer compound according to claim 1, wherein the structural unit (A) is represented by Chemical Formula 1-1: Chemical formula 1-1 in, In Chemical Formula 1-1, R 11 to R 14 and R 21 to R 24 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aryl group, or a halogen atom, wherein R 11 and R 21 are optionally bonded to each other to form a ring, and L 1 、Ar 1 、Ar 2 、X 1 and Y 1 Same as defined in Chemical Formula 1.

3. The polymer compound according to claim 1, further comprising a structural unit (B) represented by Chemical Formula 2: Chemical formula 2 in, In Chemical Formula 2, Ar 21 and Ar 22 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, Ar 21 and Ar 22 are optionally bonded to each other to form a ring, L 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms, Ar 3 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, Ar 4 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms, Ar 3 and Ar 4 are optionally linked to each other to form a ring, X 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms, Y 2 is an aromatic hydrocarbon group having 6 to 25 ring atoms which is unsubstituted or substituted with an alkyl group having 1 to 14 carbon atoms, and Ar 21 、Ar 22 , L 2 、Ar 3 、Ar 4 and X 2 An alkyl group having 1 to 14 carbon atoms does not have a thiol group-containing group, and an alkoxyalkyl group having 2 to 14 carbon atoms does not have a thiol group-containing group.

4. The polymer compound according to claim 3, wherein the structural unit (B) is represented by Chemical Formula 2-1: Chemical formula 2-1 in, In Chemical Formula 2-1, R 31 to R 34 and R 41 to R 44 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aryl group, or a halogen atom, wherein R 31 and R 41 are optionally bonded to each other to form a ring, L 2 、Ar 3 、Ar 4 、X 2 and Y 2 is the same as defined in Chemical Formula 2, and R 31 to R 34 、R 41 to R 44 , L 2 、Ar 3 、Ar 4 and X 2 An alkyl group having 1 to 14 carbon atoms does not have a thiol group-containing group, and an alkoxyalkyl group having 2 to 14 carbon atoms does not have a thiol group-containing group. 5 . The polymer compound according to claim 3 , wherein the structural unit (A) is included in an amount of greater than or equal to 1 mol % and less than 30 mol % based on the total moles of the structural unit (A) and the structural unit (B) in the polymer compound. The polymer compound according to claim 3 , wherein Ar in Chemical Formula 2 21 With Ar in chemical formula 1 11 same, Ar in Chemical Formula 2 22 With Ar in chemical formula 1 12 same, L in Chemical Formula 2 2 With L in chemical formula 1 1 same, Ar in Chemical Formula 2 3 With Ar in chemical formula 1 1 same, Ar in Chemical Formula 2 4 With Ar in chemical formula 1 2 Same, and X in Chemical Formula 2 2 With X in chemical formula 1 1 same.

7. The polymer compound according to claim 1, wherein the thiol group-containing alkoxyalkyl group has a structure represented by Chemical Formula i-1: Chemical formula i-1 *-WITH 1 -OZ 2 -SH in, In chemical formula i-1, Z 1 represents an unsubstituted or thiol-substituted alkylene group having 1 to 13 carbon atoms, Z 2 represents an unsubstituted or thiol-substituted alkylene group having 1 to 13 carbon atoms, By Z 1 The carbon number of the alkylene represented by Z 2 The sum of the carbon numbers of the alkylene groups represented by is an integer of 14 or less, and *bonded to constituent Y 1 An aromatic hydrocarbon group having 6 to 25 ring atoms.

8. The polymer compound according to claim 1, wherein the alkyl group containing a thiol group has a structure represented by Chemical Formula i-2: Chemical formula i-2 *-WITH 1 -SH in, In chemical formula i-2, Z 1 represents an unsubstituted or thiol-substituted alkylene group having 1 to 14 carbon atoms, and *bonded to constituent Y 1 An aromatic hydrocarbon group having 6 to 25 ring atoms.

9. The polymer compound according to claim 1, wherein Y in Chemical Formula 1 1 It is an aromatic hydrocarbon group having 6 to 25 ring atoms substituted with an alkoxyalkyl group having 2 to 14 carbon atoms and containing a thiol group. 10 . The polymer compound according to claim 9 , wherein the thiol group-containing alkoxyalkyl group has two or more thiol groups.

11. The polymer compound according to claim 1, wherein Y in Chemical Formula 1 1 It is an aromatic hydrocarbon group having 6 to 25 ring atoms substituted with an alkyl group having 1 to 10 carbon atoms containing a thiol group.

12. The polymer compound according to claim 1, wherein in Chemical Formula 1, Y 1 is one of the groups represented by chemical formulas (3-1) to (3-6): in, In Chemical Formulas 3-1 to 3-6, R 301 、R 302 、R 305 、R 307 and R 308 are each independently a substituted or unsubstituted alkylene group having 1 to 14 carbon atoms, R 303 、R 304 、R 306 、R 309 and R 310 are each independently a substituted or unsubstituted alkylene group having 1 to 11 carbon atoms, and ** indicates binding sites.

13. The polymer compound according to claim 12, wherein Y in Chemical Formula 1 1 It is a group represented by Chemical Formula (3-1) or (3-2).

14. The polymer compound according to claim 1, wherein L 1 is any one of the groups represented by chemical formulas (4-1) to (4-24): in, In Chemical Formulas 4-1 to 4-24, *** indicates the position where it is bonded to the nitrogen atom, and **** indicates that it is 1 Bonding location.

15. The polymer compound according to claim 1, wherein in Chemical Formula 1, -L 1 -Ar 1 -N(Ar 2 )(X 1 ) is any one of the groups represented by chemical formulas (5-1) to (5-3): in, In chemical formulas (5-1) to (5-3), R 501 to R 506 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aryl group, or a halogen atom, X 1 is the same as defined in Chemical Formula 1, and ***** indicates the position where it is bonded to the nitrogen atom.

16. An electroluminescent device material comprising the polymer compound according to any one of claims 1 to 15.

17. A liquid composition comprising the polymer compound according to any one of claims 1 to 15 and at least one solvent.

18. An electroluminescent device comprising: a first electrode, a second electrode, and at least one organic film between the first electrode and the second electrode, The at least one organic film comprises the polymer compound according to any one of claims 1 to 15. 19 . The electroluminescent device according to claim 18 , wherein the at least one organic film comprising the polymer compound is a hole transport layer or a hole injection layer.

20. The electroluminescent device of claim 18, wherein the electroluminescent device further comprises a light-emitting layer comprising semiconductor nanocrystal particles, a perovskite compound, or a combination thereof.

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