Composition, film, and electroluminescent device

Abstract

A composition including a polymer having a structural unit (A) represented by Chemical Formula 1 and a compound represented by Chemical Formula 10 can be cured at a low temperature, and the cured hole transport layer has a high film retention rate, such that an electroluminescent device including the hole transport layer has excellent light emission characteristics and high light emission efficiency. Ar, Ar1, Ar2, Ar5 to Ar8, Ar11, Ar12, L1, X1 and Y1 are each independently as described in the specification. The electroluminescent device includes a first electrode, a second electrode, and at least one layer of organic film between the first electrode and the second electrode, the at least one layer of organic film including a thin film.

Description

[0001] This application claims priority and all rights to Korean Patent Application No. 10-2024-0116281, filed on August 28, 2024, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0002] Compositions, thin films made from the compositions, and electroluminescent devices comprising the thin films. Background Technology

[0003] Research and development of electroluminescent devices (EL devices) are actively underway. Specifically, EL devices are envisioned for use as solid-state (solid-state) light-emitting large-area full-color display devices or as write-in light source arrays. An EL device is a light-emitting device comprising a thin film with a thickness of several nanometers to several hundred nanometers between the anode and cathode. EL devices typically include a hole transport layer, a light-emitting layer, an electron transport layer, etc.

[0004] The light-emitting layer comprises fluorescent and / or phosphorescent materials. Phosphorescent materials are expected to have higher luminous efficiency than fluorescent materials. Furthermore, to cover a wide color gamut, RGB light sources require emission spectra with narrow full width at half maximum (FWHM). For example, while deep blue is particularly advantageous for blue, no device has yet been found that offers both long lifetime and satisfactory color purity.

[0005] As a solution to this problem, there exists a light-emitting device that uses "quantum dots," which are inorganic light-emitting materials, as the light-emitting material (see Patent Document 1). Quantum dots (QDs) are semiconductor materials with a crystal structure of a few nanometers in size and composed of hundreds to thousands of atoms. Because quantum dots are extremely small in size, they have a large surface area per unit volume. Therefore, most atoms reside on the surface of the nanocrystals and exhibit a quantum confinement effect. Due to this effect, the emission wavelength of quantum dots can be tuned by adjusting their size. Quantum dots have gained widespread attention because properties such as improved color purity and high photoluminescence (PL) efficiency can be achieved. A quantum dot electroluminescent device (QD LED) is a three-layer device comprising a hole transport layer, a quantum dot light-emitting layer, and an electron transport layer.

[0006] To improve the characteristics of such quantum dot electroluminescent devices, techniques have been proposed to improve the hole transport and hole injection properties of hole transport materials. For example, Patent Document 2 proposes an arylamine-fluorene alternating copolymer (polymer compound) with hydrocarbon groups in its side chain as a hole transport material.

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

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

[0009] An embodiment provides a composition for forming a hole transport layer (e.g., a hole transport material) that has high tolerance to solvents used in the manufacture of the light-emitting layer of an electroluminescent device (e.g., a quantum dot electroluminescent device) and therefore has high film retention and excellent hole transport properties.

[0010] Another embodiment provides a film manufactured using a composition.

[0011] Another embodiment provides an electroluminescent device including a thin film.

[0012] Therefore, the embodiments provide polymers and compounds, the polymer comprising a structural unit (A) represented by chemical formula 1 (also referred to as a first structural unit), and the compound represented by chemical formula 10:

[0013] Chemical Formula 1

[0014]

[0015] In chemical formula 1,

[0016] Ar 11 and Ar 12 Each is independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms.

[0017] Ar 11 with Ar 12 They can optionally be connected to each other to form a loop.

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

[0019] Ar 1 It is an aromatic hydrocarbon group, substituted or unsubstituted, having 6 to 25 cyclic atoms.

[0020] Ar 2 It is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms, and Ar 2 Can be used with Ar 1 Forming a ring,

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

[0022] Y 1 It is a group selected from an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with an alkyl group containing a thiol group having 1 to 14 carbon atoms, an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with an alkoxyalkyl group containing a thiol group having 2 to 14 carbon atoms, and an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with an alkyl group containing a thiol group having 1 to 14 carbon atoms and an alkoxyalkyl group containing a thiol group having 2 to 14 carbon atoms;

[0023] Chemical Formula 10

[0024]

[0025] In chemical formula 10,

[0026] Ar and Ar 5 To Ar 8 Each is independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, a substituted or unsubstituted heteroaromatic cyclic group having 5 to 25 cyclic atoms, or a combination thereof, wherein the aromatic hydrocarbon group and the heteroaromatic cyclic group include (e.g., each independently includes) a monocyclic ring, a fused ring of two or more rings, or a cyclic combination wherein the monocyclic ring and / or the fused rings are connected by a single bond.

[0027] Ar 5 with Ar 6 and / or Ar 7 with Ar 8 Each can be independently and optionally connected to each other to form a loop.

[0028] Ar and Ar 5 To Ar 8 At least two of them are independently replaced by C2 to C10 aliphatic hydrocarbon groups containing carbon-carbon double bonds or carbon-carbon triple bonds, or C3 to C10 alicyclic hydrocarbon groups containing carbon-carbon double bonds or carbon-carbon triple bonds.

[0029] The structural unit (A) represented by chemical formula 1 can be represented by chemical formula 1-1:

[0030] Chemical Formula 1-1

[0031]

[0032] In chemical formula 1-1,

[0033] R 11 To R14 and R 21 To R 24 Each of these can 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 With R 21 They can be connected to form a ring.

[0034] L 1 It can be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms.

[0035] Ar 1 It can be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms.

[0036] Ar 2 It can be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms, and Ar 2 Can be used with Ar 1 Forming a ring,

[0037] X 1 It can be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms, and

[0038] Y 1 It may be a group selected from an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with an alkyl group containing a thiol group having 1 to 14 carbon atoms, an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with an alkoxyalkyl group containing a thiol group having 2 to 14 carbon atoms, and an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with an alkyl group containing a thiol group having 1 to 14 carbon atoms and an alkoxyalkyl group containing a thiol group having 2 to 14 carbon atoms.

[0039] The polymer may also include a structural unit (B) represented by chemical formula 2 (also known as a second structural unit):

[0040] Chemical formula 2

[0041]

[0042] In chemical formula 2,

[0043] Ar 21 and Ar 22Each is independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms.

[0044] Ar 21 with Ar 22 They can optionally combine with each other to form a ring.

[0045] L 2 It is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms.

[0046] Ar 3 It is an aromatic hydrocarbon group, substituted or unsubstituted, having 6 to 25 cyclic atoms.

[0047] Ar 4 It is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms, and Ar 4 Can be used with Ar 3 Forming a ring,

[0048] X 2 It is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms.

[0049] Y 2 It is an aromatic hydrocarbon group having 6 to 25 cyclic atoms, substituted or unsubstituted with an alkyl group having 1 to 14 carbon atoms, and

[0050] Ar 21 Ar 22 L 2 Ar 3 Ar 4 and X 2 It does not have an alkyl group containing a thiol group having 1 to 14 carbon atoms, nor does it have an alkoxyalkyl group containing a thiol group having 2 to 14 carbon atoms.

[0051] The structural unit (B) represented by chemical formula 2 can be represented by chemical formula 2-1:

[0052] Chemical formula 2-1

[0053]

[0054] In chemical formula 2-1,

[0055] R 31 To R 34 and R 41 To R 44Each of these can 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 With R 41 They can combine to form a ring.

[0056] L 2 It can be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms.

[0057] Ar 3 It can be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms.

[0058] Ar 4 It can be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms, and Ar 4 Can be used with Ar 3 Forming a ring,

[0059] X 2 It can be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms.

[0060] Y 2 It can be an aromatic hydrocarbon group having 6 to 25 cyclic atoms, substituted with or unsubstituted with an alkyl group having 1 to 14 carbon atoms, and

[0061] R 31 To R 34 R 41 To R 44 L 2 Ar 3 Ar 4 and X 2 It does not have an alkyl group containing a thiol group having 1 to 14 carbon atoms, nor does it have an alkoxyalkyl group containing a thiol group having 2 to 14 carbon atoms.

[0062] In a polymer, structural unit (A) may be included in an amount greater than or equal to 1 mol% and less than or equal to 30 mol% based on the total number of moles of structural unit (A) and structural unit (B).

[0063] Y of chemical formula 1 1 The thiol-containing alkoxyalkyl group can be represented by chemical formula i-1, and Y of chemical formula 1 1The alkyl group containing a thiol group can be represented by the chemical formula i-2:

[0064] Chemical formula i-1,

[0065]

[0066] Chemical formula i-2

[0067]

[0068] In chemical formulas i-1 and i-2,

[0069] Z 1 It is an alkylene group having 1 to 14 carbon atoms, which may be substituted with or unsubstituted with a thiol group.

[0070] Z 2 It is an alkylene group having 1 to 13 carbon atoms, which may be substituted with or unsubstituted with a thiol group.

[0071] In chemical formula i-1, Z 1 The carbon number of the alkylene group and the Z 2 The sum of the carbon numbers of the alkylene groups is an integer of 14 or less, and

[0072] It combines with 6 to 25 cyclic atoms to form Y 1 Aromatic hydrocarbon groups.

[0073] In chemical formula 1, Y 1 It can be an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with an alkoxyalkyl group containing a thiol group having 2 to 14 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with an alkyl group containing a thiol group having 1 to 10 carbon atoms.

[0074] Alkoxyalkyl groups containing thiol groups may have two or more thiol groups.

[0075] In chemical formula 1, Y 1 It can be represented by chemical formulas (3-1) to (3-6):

[0076]

[0077] In chemical formulas (3-1) to (3-6),

[0078] R 301 R 302 R 305 R 307 and R 308 Each is independently a substituted or unsubstituted alkylene group having 1 to 14 carbon atoms.

[0079] 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

[0080] Indicates the binding site.

[0081] In chemical formula 1, L 1 It can be represented by any of the groups represented by chemical formulas (4-1) to (4-24):

[0082] In chemical formulas (4-1) to (4-24),

[0083] It can bind to nitrogen atoms, and Can be combined with Ar 1 .

[0084] In chemical formula 1, -L 1 -Ar 1 -N(Ar 2 (X) 1 It can be one of the groups represented by chemical formulas (5-1) to (5-3):

[0085]

[0086] In chemical formulas (5-1) to (4-3),

[0087] R 501 To R 506 Each of these can 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.

[0088] X 1 Same as defined in Chemical Formula 1, and

[0089] It binds to a nitrogen atom.

[0090] In chemical formula 10,

[0091] Ar and Ar 5 To Ar 8Each is independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 15 cyclic atoms, a substituted or unsubstituted heteroaromatic cyclic group having 5 to 15 cyclic atoms, or a combination thereof, wherein the aromatic hydrocarbon group and the heteroaromatic cyclic group include (e.g., each independently includes) a monocyclic ring, a fused ring of two or more rings, or a cyclic combination wherein the monocyclic ring and / or the fused rings are connected by a single bond.

[0092] Ar 5 with Ar 6 and / or Ar 7 with Ar 8 Each can be independently and optionally connected to each other to form a loop.

[0093] Ar 5 To Ar 8 At least two of them are independently replaced by C2 to C5 aliphatic hydrocarbon groups containing carbon-carbon double bonds or carbon-carbon triple bonds, or C3 to C6 alicyclic hydrocarbon groups containing carbon-carbon double bonds or carbon-carbon triple bonds.

[0094] In chemical formula 10,

[0095] Ar is a substituted or unsubstituted phenylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted pyrimidinylene, a substituted or unsubstituted pyrazinylene, a substituted or unsubstituted triazine group, a substituted or unsubstituted biphenylene, or a combination thereof.

[0096] Ar 5 To Ar 8 Each of these elements independently is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted acridineyl, a substituted or unsubstituted pyridyl, or a combination thereof.

[0097] Ar 5 with Ar 6 and / or Ar 7 with Ar 8 Each can be independently and optionally linked to each other to form a substituted or unsubstituted carbazole ring, or a fused ring of substituted or unsubstituted indole and pyridine, and

[0098] Ar 5 and Ar 6 One of them and Ar 7 and Ar 8 Each of the groups is independently replaced by a C2 to C4 aliphatic hydrocarbon group, including a carbon-carbon double bond or a carbon-carbon triple bond.

[0099] Compounds represented by chemical formula 10 can be represented by chemical formula 10-1:

[0100] Chemical formula 10-1

[0101]

[0102] In chemical formula 10-1,

[0103] It is a heteroaromatic cyclic group, substituted or unsubstituted, having 5 to 15 cyclic atoms.

[0104] Ar 5 To Ar 8 Each is independently identical to that defined in chemical formula 10.

[0105] R a and R b Each of these elements independently comprises deuterium, C1 to C10 alkyl, C2 to C10 alkenyl, C1 to C10 haloalkyl, halogen atom, cyano, nitro, or a combination thereof.

[0106] x and y are each independent integers from 0 to 4, and

[0107] m and n are each an independent integer from 0 to 3.

[0108] The polymer represented by chemical formula 1 and the compound represented by chemical formula 10 each independently have a value greater than or equal to 10. -5 cm 2 V -1 S -1 The hole transmission coefficient.

[0109] The film according to another embodiment can be manufactured by curing the composition according to the embodiment.

[0110] An electroluminescent device according to another embodiment includes a first electrode and a second electrode facing each other, a light-emitting layer disposed between the first electrode and the second electrode, and at least one organic film disposed between the first electrode and the light-emitting layer, wherein the at least one organic film includes a thin film according to an embodiment.

[0111] The thin film can be a hole transport layer.

[0112] The at least one organic membrane comprises two or more organic membranes, and the two or more organic membranes include a hole injection layer between the first electrode and the thin film.

[0113] The light-emitting layer may include semiconductor nanocrystal particles, perovskite compounds, or combinations thereof.

[0114] The compositions according to the embodiments can have excellent hole transport properties and can be used as compositions for forming hole transport layers in electroluminescent devices (e.g., quantum dot electroluminescent devices). When manufacturing electroluminescent devices (e.g., quantum dot electroluminescent devices), the film comprising the cured product of the composition can have excellent resistance to organic solvents in the composition used to form the light-emitting layer (e.g., a light-emitting layer comprising quantum dots), and therefore can have high film retention after the light-emitting layer is formed. Therefore, the film can be advantageously used as a hole transport layer in electroluminescent devices (e.g., quantum dot electroluminescent devices). Furthermore, since the film can be manufactured by heat-treating the composition at low temperatures, the film can be easily disposed on another organic layer without damaging the organic layer present beneath the film. Therefore, the compositions according to the embodiments can be advantageously applied as hole transport layers in electroluminescent devices (e.g., quantum dot electroluminescent devices), and electroluminescent devices comprising hole transport layers can exhibit low driving voltage, high brightness, and high external quantum efficiency due to their excellent hole transport characteristics. Attached Figure Description

[0115] Figure 1 This is a schematic view illustrating an electroluminescent device according to an embodiment.

[0116] Figure 2 This is a graph showing the extinction coefficient versus wavelength of a film prepared by heat treatment at 150°C according to the composition of Comparative Example 1, obtained by measuring the film using an ellipsometry before and after treatment with cyclohexylbenzene.

[0117] Figure 3 This is a graph showing the extinction coefficient versus wavelength of a film prepared by heat treatment at 190°C according to the composition of Comparative Example 1, obtained by measuring the film using an ellipsometry before and after treatment with cyclohexylbenzene.

[0118] Figure 4 This is a graph showing the extinction coefficient versus wavelength of a film prepared by heat treatment at 150°C according to the composition of Comparative Example 2. The graph was obtained by measuring the film using an ellipsometry before and after treatment with cyclohexylbenzene.

[0119] Figure 5 This is a graph showing the extinction coefficient versus wavelength of a film prepared by heat treatment at 190°C according to the composition of Comparative Example 2. The graph was obtained by measuring the film using an ellipsometry before and after treatment with cyclohexylbenzene.

[0120] Figure 6This is a graph showing the extinction coefficient versus wavelength of a film prepared by heat treatment at 150°C according to the composition of Comparative Example 3. The graph was obtained by measuring the film using an ellipsometry before and after treatment with cyclohexylbenzene.

[0121] Figure 7 This is a graph showing the extinction coefficient versus wavelength of a film prepared by heat treatment at 190°C according to the composition of Comparative Example 3. The graph was obtained by measuring the film using an ellipsometry before and after treatment with cyclohexylbenzene.

[0122] Figure 8 This is a graph showing the extinction coefficient versus wavelength of a film prepared by heat treatment at 150°C according to the composition of Example 1, obtained by measuring the film using an ellipsometry before and after treatment with cyclohexylbenzene.

[0123] Figure 9 This is a graph showing the extinction coefficient versus wavelength of a film prepared by heat treatment at 190°C according to the composition of Example 1, obtained by measuring the film using an ellipsometry before and after treatment with cyclohexylbenzene.

[0124] Figure 10 This is a graph showing the extinction coefficient versus wavelength of a film prepared by heat treatment at 150°C according to the composition of Example 2, obtained by measuring with an ellipsometry before and after treatment with cyclohexylbenzene.

[0125] Figure 11 This is a graph showing the extinction coefficient versus wavelength of a film prepared by heat treatment at 190°C according to the composition of Example 2, obtained by measuring the film using an ellipsometry before and after treatment with cyclohexylbenzene.

[0126] Figure 12 The graphs showing the external quantum efficiency (EQE) versus brightness for comparative quantum dot electroluminescent devices 1 and 2 according to comparative manufacturing examples 1 and 2, respectively, and the graphs showing the external quantum efficiency (EQE) versus brightness for quantum dot electroluminescent devices 3 and 4 according to manufacturing examples 2-3 and 2-4, respectively.

[0127] Figure 13The graphs showing the brightness versus time (in hours (h) of comparative quantum dot electroluminescent devices 1 and 2 according to comparative manufacturing examples 1 and 2, respectively, and the brightness versus time (in hours (h) of quantum dot electroluminescent devices 3 and 4 according to manufacturing examples 2-3 and 2-4, respectively, are shown. Detailed Implementation

[0128] Examples provide compositions comprising a polymer containing a structural unit (A) represented by Chemical Formula 1 and a compound represented by Chemical Formula 10:

[0129] Chemical Formula 1

[0130]

[0131] In chemical formula 1,

[0132] Ar 11 and Ar 12 Each is independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms.

[0133] Ar 11 and Ar 12 They can optionally be connected to each other to form a loop.

[0134] L 1 It is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms.

[0135] Ar 1 It is an aromatic hydrocarbon group, substituted or unsubstituted, having 6 to 25 cyclic atoms.

[0136] Ar 2 It is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms, and Ar 2 Can be used with Ar 1 Forming a ring,

[0137] X 1 It is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 5 to 25 cyclic atoms, and

[0138] Y 1It is a group selected from an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with an alkyl group containing a thiol group having 1 to 14 carbon atoms, an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with an alkoxyalkyl group containing a thiol group having 2 to 14 carbon atoms, and an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with an alkyl group containing a thiol group having 1 to 14 carbon atoms and an alkoxyalkyl group containing a thiol group having 2 to 14 carbon atoms;

[0139] Chemical Formula 10

[0140]

[0141] In chemical formula 10,

[0142] Ar and Ar 5 To Ar 8 Each is independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, a substituted or unsubstituted heteroaromatic cyclic group having 5 to 25 cyclic atoms, or a combination thereof, wherein the aromatic hydrocarbon group and the heteroaromatic cyclic group include (e.g., each independently includes) a monocyclic ring, a fused ring of two or more rings, or a cyclic combination of monocyclic and / or fused rings connected by a single bond.

[0143] Ar 5 and Ar 6 and / or Ar 7 and Ar 8 Each can be independently and optionally connected to each other to form a loop.

[0144] Ar and Ar 5 To Ar 8 At least two of them are independently replaced by C2 to C10 aliphatic hydrocarbon groups containing carbon-carbon double bonds or carbon-carbon triple bonds, or C3 to C10 alicyclic hydrocarbon groups containing carbon-carbon double bonds or carbon-carbon triple bonds.

[0145] In this specification, the structural unit (A) represented by chemical formula 1 is sometimes referred to as "structural unit (A)" or "structural unit (A) according to the embodiment".

[0146] The structural unit (A) represented by chemical formula 1 includes a unit part X represented by the following structure:

[0147]

[0148] The structural unit (A) represented by chemical formula 1 also includes unit part Y, which corresponds to the structure "-Y" in chemical formula 1. 1 -".

[0149] Polymers having structural units (A) represented by chemical formula 1 are sometimes referred to as “polymers” or “polymers according to the embodiments”.

[0150] According to another embodiment, a film prepared by curing the composition according to the embodiment is provided.

[0151] According to another embodiment, an electroluminescent device comprising a thin film according to the embodiment is provided.

[0152] The electroluminescent device includes a first electrode and a second electrode facing each other, a light-emitting layer disposed between the first electrode and the second electrode, and at least one organic film disposed between the first electrode and the light-emitting layer, wherein the at least one organic film includes a thin film according to an embodiment.

[0153] As used herein, electroluminescent devices are sometimes referred to as “LEDs”.

[0154] Quantum dot electroluminescent devices are sometimes simply referred to as "QLED".

[0155] Perovskite electroluminescent devices are sometimes referred to as "PeLEDs".

[0156] Various low-molecular-weight materials and polymeric materials are used as materials constituting the light-emitting layer or carrier transport layer of an electroluminescent device. Among them, low-molecular-weight materials can be better in terms of device efficiency and lifetime. 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. For example, polymeric materials (TFB in Patent Document 1 (e.g., paragraph "0037") and alternating arylamine-fluorene copolymer in Patent Document 2) are known as hole transport materials. However, TFB in Patent Document 1 cannot be considered to have a sufficiently long durability (luminescence lifetime), and while the alternating arylamine-fluorene copolymer in Patent Document 2 does exhibit excellent durability, it cannot be considered to have sufficient luminescence efficiency, and there are no technological options for improvement.

[0157] On the other hand, the organic polymers or monomers used in the hole transport layer during QLED manufacturing have low tolerance to the organic solvents included in the compositions used to prepare the light-emitting layer (such as QD inkjet compositions), and therefore, the residual film properties after the light-emitting layer is prepared can be poor. Therefore, when a QD-including light-emitting layer is formed on top of the hole transport layer using solution processes (such as spin coating or inkjet coating), the types of solvents that can be used are very limited. For example, in the case of inkjet coating, aromatic organic solvents with high boiling points are typically used, and in such cases, the hole transport layer including conventional hole-transporting organic polymers can exhibit very low film retention after the formation of the light-emitting layer. If the hole transport layer is not thick enough to achieve the desired thickness, it is difficult to achieve the desired hole transport characteristics, and therefore, it is difficult to anticipate the desired luminescent characteristics or excellent luminescent efficiency from the electroluminescent device.

[0158] On the other hand, it has been reported that film retention can be increased by heat-treating hole-transporting organic polymers at temperatures above approximately 200°C. However, it is known that when heat-treated at temperatures above 200°C, the hole injection properties of the hole injection material (such as PEDOT:PSS) included in the hole injection layer disposed below the hole transport layer deteriorate. Therefore, it is difficult to improve the film retention of the hole transport layer by high-temperature heat treatment. In other words, if the composition used to prepare the hole transport layer is cured at a low temperature of 200°C or lower, thereby maintaining the stability of the hole injection layer disposed below the hole transport layer, and further, if the cured hole transport layer has high resistance to the organic solvents included in the composition used to prepare the light-emitting layer disposed on the hole transport layer, resulting in a high film retention, then it is expected that the electroluminescent device including this hole transport layer can guarantee excellent hole injection and hole transport characteristics, and thus exhibit excellent light-emitting characteristics and high luminous efficiency at low driving voltages.

[0159] The composition according to the embodiments comprises a polymer having a structural unit (A) represented by Chemical Formula 1 and a compound represented by Chemical Formula 10, such that when heat-treated at a low temperature (e.g., a temperature less than or equal to 200°C), crosslinking bonds are formed between the polymer and the compound via a thiol-ene bonding reaction (or thiol-ene bonding reaction) between unsaturated bonds of carbon-carbon double or triple bonds included in the polymer and thiol-ene groups included in the compound, as shown in the following reaction scheme:

[0160] (Thiol-alkene bonding reaction)

[0161]

[0162] Therefore, the composition can be formed into a film comprising a crosslinking product between the polymer and the compound through low-temperature heat treatment, and this film, by including the crosslinking product between the polymer and the compound, exhibits significantly increased resistance to organic solvents compared to films comprising only organic polymers and / or low molecular weight compounds. Thus, when a composition comprising aromatic organic solvents (such as an inkjet composition comprising quantum dots) is applied to form a light-emitting layer on the resulting film, the problem of the film dissolving in the organic solvent and the reduction in film retention can be prevented. Furthermore, since the thiol-olefin bonding reaction is carried out at a low temperature of less than or equal to 200°C, the degradation of the layer disposed beneath the layer to which the composition is applied (e.g., a hole injection layer) can be prevented.

[0163] Therefore, the composition according to the embodiments can be advantageously applied to the hole transport layer of an electroluminescent device, and the electroluminescent device including the hole transport layer prepared from the composition can maintain excellent hole transport characteristics due to the high film retention rate of the hole transport layer, and can also maintain excellent hole injection characteristics by preventing the degradation of the hole injection layer disposed below the hole transport layer. Thus, the electroluminescent device including the hole transport layer prepared by applying the composition can achieve excellent luminescent characteristics and high luminescent efficiency while maintaining a low driving voltage.

[0164] Furthermore, since the compositions according to the embodiments possess excellent film-forming properties and solvent solubility, the compositions can be formed into films by wet (coating) methods. Therefore, by using the compositions according to the embodiments, the area of ​​the electroluminescent device can be increased accordingly, and high productivity can be achieved. The effects are also advantageously manifested when the compositions according to the embodiments are applied to the hole transport layer of an electroluminescent (EL) device (e.g., the hole transport layer of a quantum dot electroluminescent device (QLED)).

[0165] This disclosure is not limited to the following embodiments. The accompanying drawings are exaggerated for better understanding and ease of description, and the size ratio of each component element in the drawings may differ from reality. It will be understood that when an element is referred to as "on" another element, the element may be directly on said other element, or there may be an intermediate element between them. Conversely, when an element is referred to as "directly on" another element, there is no intermediate element.

[0166] The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. Unless the content clearly indicates otherwise, as used herein, the singular forms “a,” “an,” and “the” are intended to include (including the plural forms “at least one”). Thus, a reference to an element “a” followed by a reference to “the” in a claim includes one element and a plurality of said elements.

[0167] "At least one (species / man)" should not be construed as limiting "one" or "a (species / man)". "Or" means "and / or". As used herein, the term "and / or" includes any and all combinations of one or more of the relevant listed items.

[0168] It will be further understood that the terms “comprising” and / or “encompassing” or “including” and / or “containing” are used in this specification to indicate the presence of stated features, regions, integers (whole), steps, operations, elements and / or components, but do not exclude the presence or addition of one or more other features, regions, integers (whole), steps, operations, elements, components and / or groups thereof.

[0169] As used herein, “about” or “approximately” includes the stated value and means within an acceptable deviation of the specific value as determined by a person of ordinary skill in the art, taking into account the measurement in question and the errors associated with the measurement of the specific quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations of the stated value, or within ±10% or ±5% of the stated value.

[0170] Unless otherwise defined, all terms used herein (including technical and scientific terms) shall have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. It will be further understood that terms (such as those defined in common dictionaries) shall be interpreted as having a meaning consistent with their meaning in the relevant field and in the context of this disclosure, and shall not be interpreted in an idealized or overly formal sense unless expressly defined herein.

[0171] In this specification, unless otherwise stated, the operating and physical properties are measured at room temperature (e.g., 20°C or above and 25°C or below) and relative humidity (RH) of 40% or above and 50% or below.

[0172] In this specification, the number of cyclic atoms (ring atom count) refers to the number of atoms of the corresponding ring itself in a compound having a structure in which atoms are bonded together to form a ring (e.g., monocyclic, fused-ring, ring complex, etc.). Atoms that do not form a ring (e.g., hydrogen atoms terminating the bonds of the ring-forming atoms) or atoms included in substituents (e.g., where the cyclic atom has substituents) are not included in the number of cyclic atoms. Unless otherwise stated, the number of cyclic atoms described below is assumed to have the same meaning as described herein.

[0173] For example, the benzene ring has 6 cyclic atoms, the naphthalene ring has 10 cyclic atoms, the pyridine ring has 6 cyclic atoms, and the furan ring has 5 cyclic atoms.

[0174] When a benzene ring is substituted with a substituent (e.g., an alkyl group), the number of carbon atoms in the alkyl group is not included in the number of cyclic atoms of the benzene ring. Therefore, the number of cyclic atoms in a benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, the number of atoms in the alkyl group is not included in the number of cyclic atoms of the naphthalene ring. Therefore, the number of cyclic atoms in a naphthalene ring substituted with an alkyl group is 10.

[0175] For example, the number of hydrogen atoms bonded to the pyridine ring or the number of atoms constituting substituents is not included in the number of cyclic atoms of the pyridine ring. Therefore, the number of cyclic atoms of a pyridine ring bonded with hydrogen atoms or substituents is 6.

[0176] In this specification, "substituent represents a hydrogen atom" indicates that the structure in which a substituent is present is unsubstituted. For example, in chemical formula 1-1, when R 11 To R 14 When all atoms are hydrogen, it indicates that it has R 11 To R 14 The benzene ring is a phenylene ring.

[0177] In this specification, unless specifically defined, the term "substituted" refers to an alkyl, cycloalkyl, hydroxyalkyl, alkoxy, alkoxyalkyl, cycloalkoxy, alkenyl, alkynyl, primary amino (-NH2), secondary amino (-NH(R)) group. 1 ):R 1 It is an alkyl or aryl group, a tertiary amino group (-N(R)). 1 (R) 2 ):R 1 and R 2 Each is independently alkyl or aryl, and in such a case, R 1 and R 2 Substitution can be achieved by forming rings, aryl groups, aryloxy groups, alkylthio groups, cycloalkylthio groups, arylthio groups, alkoxycarbonyl groups, aryloxycarbonyl groups, hydroxyl groups (-OH), carboxyl groups (-COOH), thiols (-SH), cyano groups (-CN), halogen atoms (fluorine, chlorine, bromine, or iodine), or combinations thereof. On the other hand, when a group is substituted, the form of the group included in the definition of a substituent does not include forms in which the group already being substituted has been further substituted. For example, when the substituent is an alkyl group, the alkyl group being substituted is not further substituted by the alkyl group.

[0178] Here, the alkyl group used as a substituent can be a straight-chain alkyl group or a branched alkyl group (e.g., a straight-chain alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms). Specifically, the alkyl group can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, neopentyl, 1,2-dimethylpropyl, n-hexyl, isohexyl, 1,3-dimethylbutyl, 1-isopropylpropyl, 1,2-dimethylbutyl, n-heptyl, 1,4-dimethylpentyl, 3-ethylpentyl, 2-methyl-1-isopropylpropyl, 1-ethyl-3-methylbutyl, n-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-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, nonadecanyl, eicosyl, etc.

[0179] As substituents, cycloalkyl groups may include, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0180] Hydroxyalkyl can be, for example, an alkyl group substituted with one to three (e.g., one or two, and for example one) hydroxyl groups (e.g., hydroxymethyl, hydroxyethyl).

[0181] The alkoxy group used as a substituent can be a straight-chain alkoxy or a branched-chain alkoxy, but preferably a straight-chain alkoxy having 1 to 20 carbon atoms or a branched-chain alkoxy having 3 to 20 carbon atoms. For example, the alkoxy group can be, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, undecoxy, dodecoxy, tridecoxy, tetradecoxy, pentadecoxy, hexadecoxy, heptadecanoxy, octadecoxy, 2-ethylhexoxy, 3-ethylpentoxy, etc.

[0182] Hydroxyalkyl can be, for example, an alkyl group substituted with one to three (e.g., one or two, and for example one) hydroxyl groups (e.g., hydroxymethyl, hydroxyethyl).

[0183] The cycloalkoxy group used as a substituent can be, for example, cyclopropoxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, etc.

[0184] Alkenyl groups that can be used as substituents 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.

[0185] Alkynyl groups that can be used 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-hepynyl, 2-hepynyl, 5-hepynyl, 1-octyynyl, 3-octyynyl, 5-octyynyl, etc.

[0186] Secondary amino groups that are substituents may include, for example, alkylamino groups having 1 to 10 carbon atoms (such as methylamino, ethylamino, n-propylamino, n-butylamino, isobutylamino, etc.) and monoarylamino groups (such as monophenylamino, mononaphthylamino, etc.).

[0187] Tertiary amino groups that are substituents may include, for example, dialkylamino groups (such as dimethylamino, diethylamino, di-n-propylamino, di-n-butylamino, methylethylamino) and diarylamino groups (such as diphenylamino, dinaphthylamino) having 2 to 20 carbon atoms.

[0188] The aryl group used as a substituent can be an aryl group having 6 to 30 cyclic atoms (carbon atoms). Examples of aryl groups include phenyl, naphthyl, biphenyl, fluorenyl, anthraceneyl, pyrene, azulel, acenaphthene, diphenyl, and phenanthrene.

[0189] Examples of aryloxy groups as substituents may include phenoxy and naphthoxy.

[0190] Examples of alkylthio groups as substituents may include methylthio, ethylthio, propanethio, pentylthio, hexylthio, octylthio, and dodecylthio.

[0191] Examples of cycloalkylthio groups as substituents include cyclopentylthio, cyclohexylthio, etc.

[0192] Examples of arylthio groups as substituents may include phenylthio and naphthio.

[0193] Examples of alkoxycarbonyl groups as substituents may include methoxycarbonyl, ethoxycarbonyl, butoxycarbonyl, octoxycarbonyl, and dodecyloxycarbonyl.

[0194] Examples of aryloxycarbonyl groups as substituents may include phenoxycarbonyl and naphthoxycarbonyl.

[0195] The term "aromatic hydrocarbon group" refers to a hydrocarbon having an aromatic ring, and includes monocyclic hydrocarbons and polycyclic hydrocarbons, wherein the additional ring of a polycyclic hydrocarbon may be aromatic or non-aromatic.

[0196] The term "heteroaromatic group" refers to an aromatic ring, and includes monocyclic and polycyclic systems (where one to three aromatic ring atoms are selected from N, O, S, Si and P), and the additional rings of polycyclic systems can be aromatic or non-aromatic.

[0197] The polymers and compounds included in the compositions according to the embodiments are described in detail below.

[0198] polymer

[0199] Structural unit (A)

[0200] The polymer included in the composition according to the embodiments comprises a structural unit (A) represented by Chemical Formula 1. Two or more structural units (A) are present in the polymer; that is, the structural unit (A) represented by Chemical Formula 1 may be a repeating unit. Polymers having structural units (A) exhibit excellent properties such as the ability to inject holes into quantum dots, and can improve the durability (luminescence lifetime) of electroluminescent devices. Furthermore, high current efficiency and low driving voltage can be achieved, and / or luminescence efficiency can be improved. The polymer may include only one type of structural unit (A) or may include two or more different types of structural units (A). Multiple structural units (A) may exist in block, random, alternating, or periodic forms.

[0201] Chemical Formula 1

[0202]

[0203] Structural unit A of chemical formula 1 includes unit part X and unit part Y. Unit part X is sandwiched between two aromatic hydrocarbon groups Ar by a nitrogen atom. 11 and Ar 12 Formed between, the unit part Y is composed of Y 1 In other words, a polymer can be referred to as a copolymer comprising partial units X and partial units Y.

[0204] In chemical formula 1, Y 1 It may be a group selected from the following: an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with an alkyl group containing a thiol group having 1 to 14 carbon atoms; an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with an alkoxyalkyl group containing a thiol group having 2 to 14 carbon atoms; and an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with an alkyl group containing a thiol group having 1 to 14 carbon atoms and an alkoxyalkyl group containing a thiol group having 2 to 14 carbon atoms.

[0205] In structural unit (A), Y 1It may have an alkyl group containing a thiol group having 1 to 14 carbon atoms (an alkyl group having 1 to 14 carbon atoms with a thiol group) or an alkoxyalkyl group containing a thiol group having 2 to 14 carbon atoms (an alkoxyalkyl group having 2 to 14 carbon atoms with a thiol group). Furthermore, Y 1 It may have both an alkyl group containing a thiol group having 1 to 14 carbon atoms and an alkoxyalkyl group containing a thiol group having 2 to 14 carbon atoms.

[0206] Alkyl groups containing thiol groups having 1 to 14 carbon atoms are sometimes referred to as "thiol-containing alkyl groups" or simply "substituents (a)".

[0207] Alkoxyalkyl groups having 2 to 14 carbon atoms are sometimes referred to as "thiol-containing alkoxyalkyl groups" or simply "substituents (b)".

[0208] Y 1 It may have at least one of a thiol-containing alkyl group (substituent (a)) and a thiol-containing alkoxyalkyl group (substituent (b)), or it may have at least two of them. 1 It may have both alkyl groups containing thiol groups (substituent (a)) and alkoxyalkyl groups containing thiol groups (substituent (b)). 1 It may have two or more substituents (a), or it may have two or more substituents (b). If in a Y 1 It includes only substituents (a) and if in a Y 1 If only substituent (b) is included, then a Y 1 There is no particular upper limit to the number of substituents (a) or (b) included, but it can be, for example, six or fewer, and, for example, four or fewer. If in a Y 1 If a Y contains both substituent (a) and substituent (b), then a Y 1 The sum of the number of substituents (a) and substituents (b) included can be two or more. In addition, there is no particular upper limit to the sum of the number of substituents (a) and substituents (b), but it can be, for example, six or fewer, and for example, four or fewer.

[0209] If Y 1 If Y has two or more substituents (a), the structures of the substituents (a) can be the same or different. Similarly, if Y... 1 If there are two or more substituents (b), the structures of the substituents (b) may be the same or different.

[0210] According to embodiments, the alkyl group having 1 to 14 carbon atoms included in the thiol-containing alkyl group (substituent (a)) can be a straight-chain alkyl group or a branched-chain alkyl group, and examples 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, Heptylbutyl, 1,4-dimethylpentyl, 3-ethylpentyl, 2-methyl-1-isopropylpropyl, 1-ethyl-3-methylbutyl, octyl, 2-ethylhexyl, 3-methyl-1-isopropylbutyl, 2-methyl-1-isopropylbutyl, 1-tert-butyl-2-methylpropyl, nonyl, 3,5,5-trimethylhexyl, decyl, isodecyl, undecyl, 1-methyldecyl, dodecyl, tridecyl, tetradecyl, etc.

[0211] The alkoxyalkyl group having 2 to 14 carbon atoms included in the thiol-containing alkoxyalkyl group (substituent (b)) is a straight-chain alkoxyalkyl group or a branched-chain alkoxyalkyl group. Substituent (b) can be a group in which an alkyl group having 1 to 13 carbon atoms is replaced by 1 to 3 (e.g., 1 to 2, e.g., 1) alkoxy groups having 1 to 13 carbon atoms (in which case the sum of the carbon number of the alkyl group and the carbon number of the alkoxy group is 2 to 14). Specific examples of alkyl groups include those in substituent (a) having 13 or fewer carbon atoms. Specific examples of alkoxy groups include those in the specific examples of alkoxy groups having 1 to 13 carbon atoms.

[0212] Therefore, examples of alkoxyalkyl groups having 2 to 14 carbon atoms included in 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, etc.

[0213] Furthermore, in order to further improve the durability of electroluminescent devices (e.g., luminescence lifetime), Y in chemical formula 1 1 It may include substituents (b).

[0214] For example, Y in chemical formula 1 1 It can be an aromatic hydrocarbon group having 6 to 25 cyclic atoms, substituted with an alkoxyalkyl group containing a thiol group comprising 2 to 14 carbon atoms. 1It can be an aromatic hydrocarbon group having 6 to 25 cyclic atoms, substituted with a thiol-containing alkoxyalkyl group comprising 2 to 10 carbon atoms. The number of carbon atoms in the thiol-containing alkoxyalkyl group represents the sum of the number of carbon atoms constituting "the alkoxy and alkyl groups that make up the group". In Y 1 In the form including substituent (b), the number of thiol groups included in substituent (b) can be one or more (e.g., two or more). Therefore, in the embodiments, substituent (b) (an alkoxyalkyl group containing a thiol group) can have one or more thiol groups. For example, substituent (b) can have two or more thiol groups. There is no particular upper limit to the number of thiol groups included in substituent (b), and it can be four or fewer.

[0215] To further improve luminescence efficiency, Y in chemical formula 1... 1 It may include substituents (a). Therefore, Y in chemical formula 1 1 It can be an aromatic hydrocarbon group having 6 to 25 cyclic atoms, substituted with an alkyl group containing a thiol group having 1 to 14 carbon atoms. 1 It can be an aromatic hydrocarbon group having 6 to 25 cyclic atoms, substituted with an alkyl group containing a thiol group having 1 to 10 carbon atoms. In Y 1 In the form including substituent (a), the number of thiol groups included in substituent (a) can be one or more (e.g., two or more). Therefore, in an embodiment, substituent (a) (an alkyl group containing a thiol group) may have one thiol group. In another embodiment, substituent (a) may have two or more thiol groups. There is no particular upper limit to the number of thiol groups included in substituent (a), and it can be four or fewer.

[0216] To further improve the balance between device durability and luminous efficiency, or to ensure that the glass transition temperature (Tg) of the polymer is within an appropriate range, or to ensure that good thermal stability is maintained, the alkyl group included in each of substituents (a) or (b) (in the case of substituent (b), the alkyl moiety bonded to the aromatic hydrocarbon group other than the alkoxy group (-OR)) may have one or more and 12 or fewer carbon atoms (e.g., one or more and 10 or fewer carbon atoms, e.g., two or more and eight or fewer carbon atoms, or four or more and eight or fewer carbon atoms; e.g., six carbon atoms). By setting the number of carbon atoms of the alkyl group constituting substituent (a) or the alkyl group constituting substituent (b) within the above-mentioned range, solvent solubility can be excellent and film-forming properties can be improved when forming a film using a wet (coating) method.

[0217] The alkoxy group included in substituent (b) may have 1 to 10 carbon atoms (e.g., 1 to 8 carbon atoms, 1 to 6 carbon atoms, or 2 to 4 carbon atoms; e.g., 3 carbon atoms).

[0218] From the viewpoint of improving durability and luminous efficiency in a better balance, the alkyl group (constituting the alkyl group of substituent (a) or substituent (b)) included in substituent (a) or substituent (b) may be straight-chain. In addition, the alkoxy group (constituting the alkoxy group of substituent (b)) included in substituent (b) may be straight-chain.

[0219] The substitution position of the thiol group in substituent (a) or substituent (b) is not particularly limited; however, for example, substituent (a) or substituent (b) may have a thiol group at the end of the substituent. In such a case, the polymer may more readily form thiol-ene crosslinks with the carbon-carbon unsaturated bond groups of the compound represented by Formula 10 in the composition according to the examples.

[0220] The thiol-containing alkyl group (substituent (a)) or the thiol-containing alkoxyalkyl group (substituent (b)) may have a structure represented by chemical formula i:

[0221] Chemical formula i

[0222]

[0223] In chemical formula i, Z 1 Z represents an unsubstituted or thiol-substituted alkylene group having 1 to 14 carbon atoms, where n is 0 or 1, and when n is 1, Z 2 This indicates an unsubstituted or thiol-substituted alkylene group having 1 to 13 carbon atoms, and is represented by Z. 1 The carbon number of the alkylene group and the Z 2 The sum of the carbon numbers of the alkylene groups represented is an integer of 14 or less (in other words, n is 0 or 1, and when n is 0, Z...). 1 Z represents an alkylene group having 1 to 14 carbon atoms, whether substituted with a thiol group or not; and when n is 1, Z 1 Z represents an alkylene group having 1 to 13 carbon atoms, substituted or unsubstituted with a thiol group. 2 This indicates an alkylene group having 1 to 13 carbon atoms, substituted or unsubstituted with a thiol group, and is composed of Z... 1 The carbon number of the alkylene group is represented by Z. 2 The sum of the carbon numbers of the alkylene groups is an integer of 14 or less, and It is incorporated into an aromatic hydrocarbon group having 6 to 25 cyclic atoms. In some cases, a group having a structure represented by the chemical formula i is simply referred to as "substituent (i)".

[0224] To facilitate the formation of thiol-ene crosslinks between the polymer and the compound represented by formula 10, as Z 1 The alkylene group having 1 to 14 carbon atoms is either a straight-chain alkylene group or a branched alkylene group, and may be substituted with a thiol group. As Z 1 Examples of alkylene compounds include methylene, ethylene, n-propylene (trimethylene), isopropylene (1,1-dimethylmethylene), n-butylene, isobutylene, secondary 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-Dimethylpentane, 3-ethylpentane, 2-methyl-1-isopropylpropane, 1-ethyl-3-methylbutylene, n-octane, 2-ethylhexane, 3-methyl-1-isopropylbutylene, 2-methyl-1-isopropylbutylene, 1-tert-butyl-2-methylpropane, n-nonane, 3,5,5-trimethylhexane, n-decane, isodene, n-undecanyl, 1-methyldecane. n-Dodecane, n-tridecane, and n-tetradecane.

[0225] As Z 1 The number of carbon atoms in the alkylene group can be 1 or more and 12 or less (e.g., 1 or more and 10 or less, 2 or more and 8 or less, 4 or more and 8 or less; e.g., 6).

[0226] As Z 1 The alkylene groups can be straight-chain, and therefore, the polymer can more easily form thiol-ene crosslinks with compounds represented by chemical formula 10.

[0227] As described in detail below, the compositions according to the embodiments can be formed into films by coating methods. However, "in order to further improve film-forming properties and form a uniform (consistent) film, thereby improving the durability (e.g., luminescence lifetime) of the electroluminescent device," the composition Z... 1 The alkylene group may be unsubstituted.

[0228] Furthermore, to further improve durability (e.g., luminescence lifetime), in chemical formula i, n can be 1, i.e., [OZ] is present. 2 Therefore, in the embodiments, the thiol-containing alkoxyalkyl group may have a structure represented by chemical formula i-1:

[0229] Chemical formula i-1

[0230]

[0231] In chemical formula i-1, Z 1Z represents an alkylene group having 1 to 13 carbon atoms, substituted or unsubstituted with a thiol group. 2 Represents an unsubstituted or thiol-substituted alkylene group having 1 to 13 carbon atoms, represented by Z. 1 The carbon number of the alkylene group and the Z 2 The sum of the carbon numbers of the alkylene groups is an integer of 14 or less, and It is incorporated into an aromatic hydrocarbon group having 6 to 25 cyclic atoms. A group having a structure represented by the chemical formula i-1 can be simply referred to as a "substituent (i-1)".

[0232] In chemical formula i, when n is 1 (substituent (b) has a structure represented by chemical formula i-1), it is considered as Z. 2 The alkylene group having 1 to 13 carbon atoms can be a straight-chain alkylene group or a branched alkylene group, and can be substituted with a thiol group. As Z 2 Examples of alkylene groups as Z 1 Among specific examples of alkylene groups, those having 1 to 13 carbon atoms may be cited.

[0233] As Z 2 The number of carbon atoms in the alkylene group can be 1 or more and 10 or less (e.g., 1 or more and 8 or less, e.g., 1 or more and 6 or less, 2 or more and 4 or less; e.g., 3).

[0234] By Z 1 The carbon number of the alkylene group and the Z 2 The sum of the carbon numbers of the represented alkylene groups can be 2 or greater and 12 or less (e.g., 2 or greater and 10 or less, 4 or greater and 10 or less, e.g., 6 or greater and 9 or less).

[0235] From the viewpoint that it forms a better thiol-ene crosslink with the compound represented by chemical formula 10, as Z 2 The alkylene groups can be straight-chain.

[0236] Furthermore, to facilitate the formation of thiol-ene crosslinks between the polymer and the compound represented by Formula 10, as Z 2 The alkylene group can be replaced by a thiol group, that is, in formula i, when n is 1 (substituent (b) has the structure represented by formula i-1), the substituent (i-1) can have two or more thiol groups. There is no particular upper limit to the number of thiol groups included in the above substituent (i-1), but it can be 4 or less.

[0237] In chemical formula i-1, Z 1 An exemplary form can be referenced to Z in chemical formula i. 1 The description.

[0238] To further improve luminescence efficiency, n in chemical formula i can be 0, i.e., [OZ 2 [This may not exist.] That is, in the embodiments, the alkyl group containing the thiol group may have a structure represented by chemical formula i-2:

[0239] Chemical formula i-2

[0240]

[0241] In chemical formula i-2, Z 1 This refers to an unsubstituted or thiol-substituted alkylene group having 1 to 14 carbon atoms, and Combined with the composition of Y 1 Aromatic hydrocarbon groups having 6 to 25 cyclic atoms. Groups with a structure represented by the chemical formula i-2 can be simply referred to as "substituents (i-2)".

[0242] In chemical formula i-2, Z 1 An exemplary form can be referenced to Z in chemical formula i. 1 The description.

[0243] According to the embodiments, the thiol-containing alkyl group (substituent (a)) or the thiol-containing alkoxyalkyl group (substituent (b)), i.e., the substituent (i), can be in the following form: In chemical formula i-1, Z 1 Z represents an unsubstituted or thiol-substituted alkylene group having 1 to 10 carbon atoms. 2 This indicates an unsubstituted or thiol-substituted alkylene group having 1 to 8 carbon atoms, and is composed of Z... 1 The carbon number of the alkylene group is represented by Z. 2 The sum of the carbon numbers of the alkylene groups is an integer from 2 to 12, or in the chemical formula i-2, Z 1 It is an unsubstituted or thiol-substituted alkylene group having 1 to 10 carbon atoms;

[0244] In another embodiment, in chemical formula i-1, Z 1 Z represents an unsubstituted or thiol-substituted alkylene group having 2 to 8 carbon atoms. 2 This indicates an unsubstituted or thiol-substituted alkylene group having 1 to 6 carbon atoms, and is composed of Z. 1 The carbon number of the alkylene group and the Z 2 The sum of the carbon numbers of the alkylene groups is an integer from 3 to 10, or in chemical formula i-2, Z 1 This refers to unsubstituted or thiol-substituted alkylene groups having 2 to 8 carbon atoms; and

[0245] In another embodiment, in chemical formula i-1, Z 1 Z represents an unsubstituted or thiol-substituted alkylene group having 4 to 8 carbon atoms. 2 This indicates an unsubstituted or thiol-substituted alkylene group having 2 to 4 carbon atoms, and is represented by Z. 1 The carbon number of the alkylene group and the Z 2 The sum of the carbon numbers of the alkylene groups is an integer from 6 to 10, or in chemical formula i-2, Z 1 This refers to an unsubstituted or thiol-substituted alkylene group having 4 to 8 carbon atoms.

[0246] In the above embodiments, by Z 1 The alkylene group and the Z 2 The alkylene groups represented can both be straight-chain.

[0247] One or more (or two or more) substituents (i) may be included in Y 1 In, and Y 1 There is no particular upper limit to the number of substituents (i) included, but it can be, for example, six or fewer, such as four or fewer. If there are two or more substituents (i), the structures of the substituents (i) can be the same or different. Therefore, in the embodiments, Y 1 It has two or more, and six or fewer (e.g., four or fewer) substituents (i-1), and the structures of the substituents (i-1) may be identical to each other. In another embodiment, Y 1 It has two or more and six or fewer (e.g., four or fewer) substituents (i-2), and the structures of the substituents (i-2) may be identical to each other.

[0248] In chemical formula 1, Y 1 The group is selected from the following: an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted by a substituent (a), an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted by a substituent (b), and an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted by both substituent (a) and substituent (b).

[0249] Here, as an aromatic hydrocarbon group having 6 to 25 cyclic atoms, examples may include groups derived from aromatic hydrocarbons such as benzene, naphthalene, anthracene, pyrene, cyclopentadiene, indene, azulene, heptaene, acenaphthene, phenanthene, biphenyl, terphenyl, tetraphenyl, fluorene, or 9,9'-spirodifluorene.

[0250] Among them, Y 1 The aromatic hydrocarbon groups included may be groups derived from benzene or fluorene (e.g., phenylene or fluoreneyl).

[0251] In the embodiments, in chemical formula 1, Y 1 It can be any of the groups represented by chemical formulas (Y-1) to (Y-3).

[0252]

[0253] In chemical formulas (Y-1) to (Y-3), R 311 To R 315 Each is independently a group having a structure represented by chemical formula i (substituent (i)), and Indicates the binding site. Exemplary forms of substituents (i) included in chemical formulas (Y-1) to (Y-3) refer to the description of substituents (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 They can be the same or different, but R 311 and R 312 and R 314 and R 315 They can be the same as each other. For example, Y 1 It can be a group represented by the chemical formula (Y-1).

[0254] In another embodiment, from the viewpoint of better balancing the improvement of electroluminescent device durability (e.g., luminous lifetime) and luminous efficiency when applied to an electroluminescent device, in chemical formula 1, Y 1 It can be any of the groups represented by chemical formulas (3-1) to (3-6):

[0255] In chemical formulas (3-1) to (3-6), R 301 R 302 R 305 R 307 and R 308 Each is 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 Indicates the binding site.

[0256] Furthermore, in chemical formulas (3-1), (3-2), (3-5), and (3-6), R 301 and R 302 R 303 and R304 R 307 and R 308 Or R 309 and R 310 They can be the same or different. R 301 and R 302 R 303 and R 304 R 307 and R 308 and R 309 and R 310 They can be the same as each other.

[0257] As R 301 To R 310 There are no particular limitations on the alkylene groups having 1 to 14 carbon atoms (or 1 to 11 carbon atoms), but they can be straight-chain or branched alkylene groups, and specific examples include those with Z in formula i. 1 The same alkylene group having 1 to 14 carbon atoms (e.g., 11 or fewer carbon atoms).

[0258] From the perspective of achieving a better balance between improving durability (e.g., luminescent lifetime) and luminescent efficiency, as R 301 To R 310 The alkylene group may have 1 to 10 carbon atoms, for example 1 to 8 carbon atoms, for example 2 to 8 carbon atoms, for example 4 to 8 carbon atoms, for example 6 carbon atoms.

[0259] Furthermore, from the same perspective as above, as R 301 To R 310 The alkylene groups can be straight-chain.

[0260] In chemical formula 1, Y 1 It can be a group represented by chemical formula (3-1) or chemical formula (3-2). To further improve durability (e.g., luminescence lifetime), Y... 1 It can be a group represented by chemical formula (3-2). To further improve luminescence efficiency, Y... 1 It can be a group represented by chemical formula (3-1).

[0261] In chemical formula 1, Ar 11 and Ar 12 Each can independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms. Ar 11 and Ar 12They may be the same or different. Examples include groups derived from aromatic hydrocarbons such as benzene, naphthalene, anthracene, pyrene, cyclopentadiene, indene, azulene, heptaene, acenaphthene, phenanthene, biphenyl, terphenyl, tetraphenyl, fluorene, or 9,9'-spirodifluorene.

[0262] Aromatic hydrocarbon group Ar 11 and Ar 12 It can be a group derived from compounds selected from benzene, biphenyl, terphenyl and fluorene (e.g., a group selected from phenylene, biphenylene, terphenylene and fluorene), a group derived from compounds selected from benzene and fluorene (e.g., a group selected from phenylene and fluorene), or a group derived from benzene (e.g., phenylene).

[0263] In the composition according to the embodiments, the structural unit (A) may be represented by chemical formula 1-1:

[0264] Chemical Formula 1-1

[0265]

[0266] In chemical formula 1-1,

[0267] R 11 To R 14 and R 21 To R 24 Each of these can 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 can be connected to form a ring.

[0268] L 1 It can be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms.

[0269] Ar 1 It can be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms.

[0270] Ar 2 It can be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms, and Ar 2 Can be used with Ar 1 Forming a ring,

[0271] X 1It can be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms, and

[0272] Y 1 It may be a group selected from the following: an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with an alkyl group containing a thiol group having 1 to 14 carbon atoms; an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with an alkoxyalkyl group containing a thiol group having 2 to 14 carbon atoms; and an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with an alkyl group containing a thiol group having 1 to 14 carbon atoms and an alkoxyalkyl group containing a thiol group having 2 to 14 carbon atoms.

[0273] In chemical formula 1-1, Y 1 It can be the same as that defined in Chemical Formula 1, and Y in Chemical Formula 1-1 1 The exemplary form can also be referred to in the example of Y in chemical formula 1. 1 The description. In chemical formula 1-1, Y 1 It can have the same properties as Y in chemical formula 1. 1 The same meaning, and can be its exemplary form or a combination of these forms.

[0274] In chemical formula 1 (or chemical formula 1-1), X 1 It can represent an aromatic hydrocarbon group having 6 to 25 cyclic atoms, substituted or unsubstituted, or a heteroaromatic group having 5 to 25 cyclic atoms, substituted or unsubstituted.

[0275] "Substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms" means any of the following: (I) an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted by substituent (a), an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted by substituent (b), and an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted by both substituent (a) and substituent (b); (II) an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted by substituents other than substituent (a) and substituent (b); and (III) an unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms.

[0276] In (I) and (II) above, substituents other than substituent (a) and substituent (b) may be further included. Furthermore, "substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms" may represent any of the following: (I') a heteroaromatic group having 5 to 25 cyclic atoms substituted by substituent (a), a heteroaromatic group having 5 to 25 cyclic atoms substituted by substituent (b), and a heteroaromatic group having 5 to 25 cyclic atoms substituted by both substituent (a) and substituent (b); (II') a heteroaromatic group having 5 to 25 cyclic atoms substituted by substituents other than substituent (a) and substituent (b); and (III') an unsubstituted heteroaromatic group having 5 to 25 cyclic atoms. In (I') and (II') above, substituents other than substituent (a) and substituent (b) may be further included. In the specification of this application, "substituents other than substituents (a) and (b)" refers to substituents other than alkyl groups substituted with thiol groups (-SH) and alkoxyalkyl groups substituted with thiol groups (-SH) among the substituents described above as "substituted".

[0277] Examples of aromatic hydrocarbon groups having 6 to 25 cyclic atoms include, for example, benzene, naphthalene, anthracene, pyrene, cyclopentadiene, indene, azulene, heptaene, acenaphthene, phenanthene, biphenyl, terphenyl, tetraphenyl, fluorene, or 9,9'-spirodifluorene.

[0278] In addition, the heteroaromatic group having 5 to 25 cyclic atoms can be, for example, acridine, phenazine, benzoquinoline, benzoisoquinoline, phenanthridine, phenanthroxolin, anthraquinone, fluorenone, dibenzofuran, dibenzothiophene, carbazole, imidazophenanthridine, benzimizophenanthridine, azadibenzofuran, azacarbazole, azadibenzothiophene, diazadibenzofuran, diazacarbazole, diazadibenzothiophene, xanthonone, thioxanthonone, pyridine, quinoline, or anthraquinoline.

[0279] X 1 It can be a group derived from a compound selected from benzene, biphenyl, terphenyl, fluorene, and carbazole (e.g., a group selected from phenyl, biphenyl, terphenyl, fluorenyl, and carbazole), such as a group derived from a compound selected from benzene, biphenyl, terphenyl, and fluorene (e.g., a group selected from phenyl, biphenyl, terphenyl, and fluorenyl), or such as a group derived from benzene (e.g., phenyl).

[0280] In addition, X 1 It may not be substituted by either substituent (a) or substituent (b). X 1 This can be a group derived from compounds selected from benzene, biphenyl, terphenyl, fluorene, and carbazole, which is either unsubstituted or substituted with substituents other than substituents (a) and (b). For example, X 1It can be a group derived from compounds selected from benzene, biphenyl, terphenyl, and fluorene, which is either unsubstituted or substituted with substituents other than substituent (a) and substituent (b). For example, X 1 It can be an unsubstituted benzene-derived group or one substituted with a group other than substituents (a) and (b) (e.g., phenyl). For example, X 1 It can be a benzene-derived group (e.g., phenyl) that is substituted with or unsubstituted with an alkyl group having 1 to 14 carbon atoms.

[0281] Furthermore, from the viewpoint of improving durability, in chemical formula 1 (or chemical formula 1-1), X 1 It can be a group represented by chemical formula 6-1.

[0282] Chemical formula 6-1

[0283]

[0284] In chemical formula 6-1,

[0285] R 601 To R 605 Each is independently a hydrogen atom, or an alkyl group having 1 to 14 carbon atoms, either unsubstituted or substituted with a substituent other than a thiol group (-SH), and With nitrogen atoms (bound to Ar) 1 (Nitrogen atoms) are combined.

[0286] In R 601 To R 605 Of these, at least one is an unsubstituted or substituted alkyl group having 1 to 14 carbon atoms, except for a thiol group (-SH), and the remainder may be hydrogen atoms. In R 601 To R 605 Of these, at least one is an unsubstituted alkyl group having 1 to 14 carbon atoms, and the remainder may be hydrogen atoms. In R 601 To R 605 Of these, one can be an unsubstituted alkyl group having 1 to 14 carbon atoms, and the remaining four can be hydrogen atoms. 603 It can 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, an alkyl group can be relative to a nitrogen atom (bonded to Ar). 1 The bond of the nitrogen atom ) is in the correct position (p bit or 4 bits).

[0287] As R 601 To R 605There are no particular limitations on the alkyl group having 1 to 14 carbon atoms, but it can be a straight-chain alkyl group or a branched alkyl group, and examples of such alkyl groups include the same alkyl groups having 1 to 14 carbon atoms as described for substituent (a).

[0288] From the perspective of achieving a better balance between improving the durability (e.g., luminous lifetime) and luminous efficiency of electroluminescent devices, as R 601 To R 605 The alkyl group may have 1 to 12 carbon atoms (e.g., 2 to 10 carbon atoms, 4 to 8 carbon atoms), such as n-hexyl. Furthermore, R 603 It can be an alkyl group having a number of carbons within the above range.

[0289] From the perspective of improving the durability of electroluminescent devices, as R 601 To R 605 The alkyl group can be straight-chain.

[0290] In another embodiment, in chemical formula 1 (or chemical formula 1-1), X 1 It can be any of the groups represented by chemical formulas (8-1) to (8-3):

[0291]

[0292] In chemical formulas (8-1), (8-2), and (8-3),

[0293] L 11 and L 12 Each can independently represent an aromatic hydrocarbon group having 6 to 12 cyclic atoms, whether substituted or unsubstituted.

[0294] 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 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms, and

[0295] With nitrogen atoms (bound to Ar) 1 (Nitrogen atoms) are combined.

[0296] R exists in or is incorporated into a benzene ring 801 To R 807 They can be the same or different. R exists in different benzene rings or is bound to different benzene rings. 801 To R 807 They can be the same or different.

[0297] As L 11 and L 12 Examples of aromatic hydrocarbon groups include those targeting X. 1 The aromatic hydrocarbon groups described are those of the aromatic hydrocarbon groups listed, which have 6 to 12 cyclic atoms.

[0298] As R 801 To R 807 Examples of halogen atoms may include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.

[0299] As R 801 To R 807 The alkyl group can be straight-chain or branched, and examples include straight-chain 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 above for "substituted", the same specific examples as those given for alkyl groups can be exemplified.

[0300] As R 801 To R 807 Cycloalkyl groups, such as those having 3 to 16 carbon atoms, may be involved. As specific examples, among the substituents described above for "substituted," the same specific examples given for cycloalkyl groups may be exemplified.

[0301] As R 801 To R 807 The alkoxy group can be straight-chain or branched, and examples include straight-chain alkoxy groups having 1 to 20 carbon atoms or branched alkoxy groups having 3 to 20 carbon atoms. As a specific example, among the substituents described above for "substituted", the same specific examples as those given for alkoxy groups can be exemplified.

[0302] As R 801 To R 807 Cycloalkoxy groups, for example, those having 3 to 16 carbon atoms, can be exemplified. As specific examples, the same specific examples given for cycloalkoxy groups among the substituents described above as "substituted" can be exemplified.

[0303] As R 801 To R 807 The aromatic hydrocarbon group, examples of which may include an aromatic hydrocarbon group having 6 to 30 cyclic atoms. As a specific example, among the substituents described above for "substituted", the same specific examples as those given for aryl groups can be cited.

[0304] As R 801 To R 807The heteroaromatic group, examples of which may include heteroaromatic groups having 5 to 25 cyclic atoms. As a specific example, examples related to X can be cited. 1 The specific examples given are the same as those for the heteroaromatic groups described.

[0305] In Formula 1 (or Formula 1-1), a thiol-containing alkyl group (substituent (a)) or a thiol-containing alkoxyalkyl group (substituent (b)) may be included in X. 1 and Y 1 The form of either one or only includes Y 1 The form in the middle. For example, substituent (a) or substituent (b) can be only included in Y. 1 In the form of [formula 1]. That is, in chemical formula 1 (or chemical formula 1-1), X 1 It can be an aromatic hydrocarbon group having 6 to 25 cyclic atoms, either unsubstituted or substituted with substituents other than substituent (a) and substituent (b), or a heteroaromatic group having 5 to 25 cyclic atoms, either unsubstituted or substituted with substituents other than substituent (a) and substituent (b), and Y 1 It can be a group selected from an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted by substituent (a), an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted by substituent (b), or an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted by both substituent (a) and substituent (b). In Formula 1 (or Formula 1-1), X 1 It can be an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted with substituents other than substituents (a) and (b), or an unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, and Y 1 It can be a group selected from an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted by substituent (a), an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted by substituent (b), and an aromatic hydrocarbon group having 6 to 25 cyclic atoms substituted by both substituent (a) and substituent (b). Furthermore, Ar in Formula 1 11 Ar 12 L 1 Ar 1 Ar2 may not have substituents (a) and (b). Furthermore, R in chemical formula 1-1... 11 To R 14 R 21 To R 24 L 1 Ar 1 and Ar 2 It may not have substituents (a) and substituents (b).

[0306] In chemical formula 1 (or chemical formula 1-1), L 1 It can represent an aromatic hydrocarbon group having 6 to 25 cyclic atoms, substituted or unsubstituted, or a heteroaromatic group having 5 to 25 cyclic atoms, substituted or unsubstituted.

[0307] Examples of aromatic hydrocarbon groups may include groups derived from aromatic hydrocarbons such as benzene (e.g., phenylene), naphthalene, anthracene, pyrene, cyclopentadiene, indene, azulene, hepta-benzone, acenaphthene, phenanthrene, biphenyl, terphenyl, tetraphenyl, fluorene, or 9,9'-spirodifluorene. Furthermore, heteroaromatic groups may include groups derived, for example, from heteroaromatic compounds such as acridine, phenazine, benzoquinone, benzoisoquinone, phenanthridine, phenanthroline, anthraquinone, fluorenone, dibenzofuran, dibenzothiophene, carbazole, imidazophenanthridine, benzimizophenanthridine, azadibenzofuran, azacarbazole, azadibenzothiophene, diazadibenzofuran, diazacarbazole, diazadibenzothiophene, xanthonone, thioxanthonone, pyridine, quinoline, or anthraquinoline.

[0308] Among them, L 1 It can be a group derived from a compound of the choice of substituted or unsubstituted benzene, biphenyl, terphenyl, tetraphenyl and fluorene, and can be a group derived from a substituted or unsubstituted benzene or biphenyl (substituted or unsubstituted phenylene or biphenylene).

[0309] In addition, when L 1 In the case where the aromatic hydrocarbon group can be substituted, the substituent can be alkyl or phenyl, such as alkyl (methyl, ethyl, n-propyl, isopropyl, or methyl or ethyl), for example, methyl. That is, L 1 It can be a group derived from unsubstituted or substituted benzene or biphenyl groups, either methyl, ethyl, n-propyl, or isopropyl. For example, L 1 It can be derived from a group of benzene or biphenyl that is substituted with or unsubstituted with methyl or ethyl groups. For example, L 1 It can be a group derived from unsubstituted benzene or substituted with one or two methyl groups, or a group derived from unsubstituted biphenyl or substituted with one or two methyl groups. For example, L 1 It can be an unsubstituted benzene-derived group or one substituted with one or two methyl groups. For example, L 1 It can be an unsubstituted benzene-derived group (o-phenylene, m-phenylene, or p-phenylene). For example, L 1 It can be paraphenylene. Having such an L 1 This can improve the durability (e.g., luminous lifetime) and luminous efficiency of LEDs (e.g., QLEDs) in a better balance.

[0310] In chemical formula 1 (chemical formula 1-1), L 1It can be any of the groups represented by chemical formulas (4-1) to (4-24):

[0311] In chemical formulas (4-1) to (4-24), It binds to the nitrogen atom, and Combined with Ar 1 .

[0312] L 1 It can be any of the groups represented by chemical formulas (4-1) to (4-3) and (4-13) to (4-16) (i.e., substituted or unsubstituted phenylene), or L 1 It can be any of the groups represented by chemical formulas (4-1) and (4-13) through (4-16) (i.e., substituted or unsubstituted p-phenylene). For example, L 1 It can be a group represented by chemical formula (4-1) (i.e., unsubstituted p-phenylene). Such an L 1 This can achieve higher hole injection properties (and thus higher durability) or better luminous efficiency.

[0313] In chemical formula 1 (or chemical formula 1-1), Ar 1 Ar can represent an aromatic hydrocarbon group with 6 to 25 cyclic atoms, whether substituted or unsubstituted. 1 It can also be used with Ar 2 A ring is formed.

[0314] Here, as Ar 1 There are no particular restrictions on the aromatic hydrocarbon groups. Ar 1 Specific examples include those related to the L mentioned above. 1 The description is the same as the specific examples derived from aromatic hydrocarbons having 6 to 25 cyclic atoms.

[0315] Ar 1 It can be a group derived from a compound of the choice of substituted or unsubstituted benzene, biphenyl, and fluorene; it can be a group derived from benzene or biphenyl, substituted or unsubstituted; or it can be a group derived from benzene, substituted or unsubstituted (e.g., when Ar...). 1 and Ar 2 When no ring is formed, Ar 1 It can be, for example, o-phenylene, m-phenylene, or p-phenylene, and when Ar 1 and Ar 2 When forming a ring, Ar 1 It can be, for example, 1,3,4-phenylene). Furthermore, Ar 1 Can be used with Ar 2It forms a ring and can be a substituted or unsubstituted 1,3,4-phenylene. Having such an Ar... 1 This can improve durability and luminous efficiency in a better balance.

[0316] When Ar 1 There are no particular restrictions on the substituents that can exist when any of the hydrogen atoms is substituted, and the same substituents as those described for "substituted" above can be applied. In the examples, Ar 1 It can be unreplaced.

[0317] In chemical formula 1 (or chemical formula 1-1), Ar 2 Ar can represent an aromatic hydrocarbon group having 6 to 25 cyclic atoms, either substituted or unsubstituted, or a heteroaromatic group having 5 to 25 cyclic atoms, either substituted or unsubstituted. 2 It can also be used with Ar 1 A ring is formed.

[0318] As Ar 2 There are no particular restrictions on the aromatic hydrocarbon groups and heteroaromatic groups. As Ar... 2 Specific examples of aromatic hydrocarbon groups may include, for example, those for L 1 The described group is derived from aromatic hydrocarbons having 6 to 25 cyclic atoms. Similarly, as Ar 2 Specific examples of heteroaromatic groups may include, for example, those for L 1 The described group is derived from heteroaromatic compounds having 5 to 25 cyclic atoms.

[0319] Ar 2 It can be a group derived from a compound of selected benzene, biphenyl, and fluorene, whether substituted or unsubstituted; it can be a group derived from benzene or biphenyl, whether substituted or unsubstituted (e.g., when Ar...). 1 and Ar 2 When no ring is formed, Ar 2 It can be, for example, phenyl, and when Ar 1 and Ar 2 When forming a ring, Ar 2 It can be, for example, o-phenylene, m-phenylene, or p-phenylene, or it can be, for example, substituted or unsubstituted o-phenylene. 2 Can be used with Ar 1 Forming a ring. Having such an Ar 2 This can improve durability and luminous efficiency in a better balance.

[0320] When Ar 2There are no particular restrictions on the substituents that can exist when any of the hydrogen atoms is substituted, and the same substituents as those described for the "substituted" substituents above can be applied. As an example, Ar 2 It can be unreplaced.

[0321] As mentioned above, Ar 1 and Ar 2 They can be connected to form a ring. In this way, through Ar... 1 with Ar 2 The formation of rings between them can achieve higher hole injection properties, further improve durability (e.g., luminescence lifetime), and enable good film-forming properties.

[0322] When Ar 1 with Ar 2 When a ring is formed, it is produced by Ar 1 with Ar 2 There are no particular restrictions on the ring structure that can be formed, but Ar 1 with Ar 2 They can combine with each other to form a carbazole ring. Furthermore, in the examples, -Ar in Formula 1 (or Formula 1-1) 1 -N(Ar 2 (X) 1 It can have a structure represented by any of the 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 It can have a structure represented by chemical formula (7-2).

[0323]

[0324] In chemical formulas (7-1) to (7-3),

[0325] R 701 To R 706 Each of these can 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.

[0326] X 1 It is the same as that defined in Chemical Formula 1 (Chemical Formula 1-1), and Combined with L 1 .

[0327] R exists in a benzene ring or is bonded to a benzene ring 701 To R 706 They can be the same or different. R exists in different benzene rings or is bound to different benzene rings.701 To R 706 They can be the same or different.

[0328] As R 701 To R 706 The alkyl group can be straight-chain or branched, and examples include straight-chain alkyl groups having 1 to 20 carbon atoms or branched alkyl groups having 3 to 20 carbon atoms. As a specific example, among the substituents described above for "substituted", the same specific examples as those given for alkyl groups can be exemplified.

[0329] As R 701 To R 706 Cycloalkyl groups, for example, those having 3 to 16 carbon atoms, can be exemplified. As specific examples, among the substituents described above for "substituted," the same specific examples given for cycloalkyl groups can be exemplified.

[0330] As R 701 To R 706 The alkoxy group can be straight-chain or branched, and examples may include straight-chain alkoxy groups having 1 to 20 carbon atoms or branched alkoxy groups having 3 to 20 carbon atoms. As a specific example, the same specific examples as those given for the alkoxy groups in the substituents described above as "substituted" can be exemplified.

[0331] As R 701 To R 706 Cycloalkoxy groups, for example, those having 3 to 16 carbon atoms, can be exemplified. As specific examples, the same specific examples given for cycloalkoxy groups among the substituents described above as "substituted" can be exemplified.

[0332] As R 701 To R 706 Aryl groups, for example, those having 6 to 30 cyclic atoms (carbon atoms), can be exemplified. As specific examples, among the substituents described above for "substituted," the same specific examples given for aryl groups can be exemplified.

[0333] As R 701 To R 706 Examples of halogen atoms may include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.

[0334] In chemical formulas (7-1) to (7-3), R 701 To R 706 Each can be an independent hydrogen atom, or a substituted or unsubstituted alkyl group, such as a hydrogen atom. In chemical formulas (7-1) to (7-3), X 1Exemplary formal reference to X 1 The description.

[0335] From the perspective of achieving a better balance between improving durability (e.g., luminescence lifetime) and luminescence efficiency, in formula 1 (or formula 1-1), Ar 1 Can be used with Ar 2 Forming a ring, and -L 1 -Ar 1 -N(Ar 2 (X) 1 The group can be any of the groups represented by chemical formulas (5-1) to (5-3). In the examples, the -L group in chemical formula 1 (or chemical formula 1-1) 1 -Ar 1 -N(Ar 2 (X) 1 It can have a structure represented by chemical formula (5-2).

[0336]

[0337] In chemical formulas (5-1) to (5-3),

[0338] R 501 To R 506 Each of these can 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.

[0339] X 1 Same as defined in Chemical Formula 1 (or Chemical Formula 1-1), and

[0340] It binds to a nitrogen atom.

[0341] R exists in a benzene ring or is bonded to a benzene ring 501 To R 506 They can be the same or different. R exists in different benzene rings or is bound to different benzene rings. 501 To R 506 They can be the same or different.

[0342] As R 501 To R 506 Each substituent may be adopted with respect to R in chemical formulas (7-1) to (7-3). 701 Up to R7 06 The examples given use the same substituents. R 501 To R 506Each can be an independent hydrogen atom, or a substituted or unsubstituted alkyl group, such as a hydrogen atom. In chemical formulas (5-1) to (5-3), X 1 An exemplary form can be referenced to X 1 The description.

[0343] In chemical formula 1-1, R 11 To R 14 and R 21 To R 24 Each of these can 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 They can combine to form a ring.

[0344] R 11 To R 14 and R 21 To R 24 They can be the same or different.

[0345] As R 11 To R 14 and R 21 To R 24 The alkyl group can be straight-chain or branched, and examples may include straight-chain alkyl groups having 1 to 20 carbon atoms or branched alkyl groups having 3 to 20 carbon atoms. As a specific example, among the substituents described above for "substituted", the same specific examples as those given for alkyl groups can be exemplified.

[0346] As R 11 To R 14 and R 21 To R 24 Cycloalkyl groups, for example, those having 3 to 16 carbon atoms, can be exemplified. As specific examples, among the substituents described above for "substituted," the same specific examples given for cycloalkyl groups can be exemplified.

[0347] As R 11 To R 14 and R 21 To R 24 The alkoxy group can be straight-chain or branched, and examples may include straight-chain alkoxy groups having 1 to 20 carbon atoms or branched alkoxy groups having 3 to 20 carbon atoms. As a specific example, the same specific examples as those given for the alkoxy groups in the substituents described above as "substituted" can be exemplified.

[0348] As R 11 To R14 R 21 To R 24 Cycloalkoxy groups, for example, those having 3 to 16 carbon atoms, can be exemplified. As specific examples, the same specific examples given for cycloalkoxy groups among the substituents described above as "substituted" can be exemplified.

[0349] As R 11 To R 14 and R 21 To R 24 Aryl groups, for example, aryl groups having 6 to 30 cyclic atoms, can be exemplified. As specific examples, among the substituents described above for "substituted," the same specific examples as those given for aryl groups can be exemplified.

[0350] As R 11 To R 14 and R 21 To R 24 Examples of halogen atoms may include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.

[0351] In addition, R 11 and R 21 They can combine to form a ring. (By R) 11 With R 21 There are no particular restrictions on the formed ring structure, but for example, there exist ring structures where R... 11 With R 21 They combine to form a carbazole ring.

[0352] From the perspective of achieving higher durability (e.g., luminescent lifetime) or better luminescent efficiency, R 11 To R 14 and R 21 To R 24 Each can be an independent hydrogen atom or a straight-chain alkyl or branched alkyl group having one to five carbon atoms. Furthermore, R... 11 To R 14 and R 21 To R 24 Each can be an independent hydrogen atom or a straight-chain alkyl or branched alkyl group having one to three carbon atoms. 11 To R 14 and R 21 To R 24 It can consist entirely of, for example, hydrogen atoms.

[0353] According to the embodiments, the structural unit (A) can be selected from chemical formula (A-1) to chemical formula (A-3).

[0354] In chemical formulas (A-1) to (A-3), R 57 R 58 R 67 R 68 R 77 and R 78 Each can 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 Each can independently represent a hydrogen atom or a straight-chain alkyl or branched alkyl group having 1 to 12 carbon atoms;

[0355] For example, in chemical formulas (A-1) to (A-3), R 57 R 58 R 67 R 68 R 77 and R 78 Each can 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 Each can independently represent a hydrogen atom or a straight-chain alkyl or branched alkyl group having 2 to 10 carbon atoms;

[0356] For example, in chemical formulas (A-1) to (A-3), R 57 R 58 R 67 R 68 R 77 and R 78 Each can independently represent a substituent (a) or a substituent (b), R 51 To R 55 R 61 To R 65 and R 71 To R 75 Each can independently represent a hydrogen atom, and R 56 R 66 and R 76 Each can independently represent a straight-chain alkyl or branched alkyl with 4 to 8 carbon atoms.

[0357] R exists in or is incorporated into a benzene ring 51 To R 56 R 61 To R 66 and R 71 To R76 They can be the same or different. R exists in different benzene rings or is bound to different benzene rings. 51 To R 56 R 61 To R 66 and R 71 To R 76 They can be the same or different.

[0358] For each of the above forms, exemplary forms of substituents (a) and (b) can be found in the description of substituents (a) and (b). As an example, in each of the above forms, the substituents (a) and (b) included in chemical formulas (A-1) to (A-3) can be substituent (i) (substituent (i-1) or substituent (i-2)).

[0359] The structural unit (A) may be one of the structural units represented by the chemical formula (A-2) described above, and each substituent in the structural unit may be in an exemplary form as described above.

[0360] Structural Unit (B)

[0361] According to the embodiments, in addition to the structural unit (A) represented by chemical formula 1, the polymer in the composition according to the embodiments may also include a structural unit (B) represented by chemical formula 2:

[0362] Chemical formula 2

[0363]

[0364] In chemical formula 2,

[0365] Ar 21 and Ar 22 Each is independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms.

[0366] Ar 21 with Ar 22 They can optionally combine with each other to form a ring.

[0367] L 2 It is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms.

[0368] Ar 3 It is an aromatic hydrocarbon group, substituted or unsubstituted, having 6 to 25 cyclic atoms.

[0369] Ar 4It is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms, and Ar 4 Can be used with Ar 3 Forming a ring,

[0370] X 2 It is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms.

[0371] Y 2 It is an aromatic hydrocarbon group having 6 to 25 cyclic atoms, substituted or unsubstituted with an alkyl group having 1 to 14 carbon atoms, and

[0372] Ar 21 Ar 22 L 2 Ar 3 Ar 4 and X 2 It does not have an alkyl group containing a thiol group having 1 to 14 carbon atoms, nor does it have an alkoxyalkyl group containing a thiol group having 2 to 14 carbon atoms.

[0373] Structural unit (B) may exist in the polymer as two or more units, that is, structural unit (B) represented by chemical formula 2 may be a repeating unit. Therefore, the polymer may have repeating units (repeating unit (A)) represented by chemical formula 1 (e.g., chemical formula 1-1) and repeating units (repeating unit (B)) represented by chemical formula 2.

[0374] The structural unit (B) represented by chemical formula 2 is sometimes simply referred to as "structural unit (B)". Similar to structural unit A, structural unit (B) represented by chemical formula 2 includes a portion of unit X' ( ) and some units Y 2 .

[0375] In addition to the structural unit (A) represented by Chemical Formula 1, by further including structural units (B) represented by Chemical Formula 2, the polymer can possess excellent hole injection properties for quantum dots, and can further improve the durability (luminescence lifetime) and luminescence efficiency of the electroluminescent device. Furthermore, high current efficiency and low driving voltage can be achieved. If the polymer does include structural units (B), then structural units (B) may include only one type of structural unit (B), or may include two or more different types of structural units (B). Multiple structural units (B) can exist in block, random, alternating, or periodic forms.

[0376] In chemical formula 2, Y 2With Y in chemical formula 1 1 The difference is that Y 2 It does not contain alkyl groups (substituents (a)) with 1 to 14 carbon atoms containing a thiol group, or alkoxyalkyl groups (substituents (b)) with 2 to 14 carbon atoms containing a thiol group. In Formula 2, except for L... 2 Ar 3 Ar 4 Ar 21 and Ar 22 In addition to each of the substituents (a) and (b) not having substituents (a) and (b) (or not having substituents (a) and (b)) in L, 2 Ar 3 Ar 4 Ar 21 and Ar 22 The definitions are respectively related to L in chemical formula 1 1 Ar 1 Ar 2 Ar 21 and Ar 22 The definition is the same. Therefore, for L 2 Ar 3 Ar 4 Ar 21 and Ar 22 The term “substituted” unless otherwise specified means a form in which the substituent is replaced by a substituent other than substituent (a) and substituent (b).

[0377] In chemical formula 2, Ar 21 and Ar 22 Each can independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms. Ar 21 and Ar 22 They may be the same or different. Here, as an aromatic hydrocarbon group having 6 to 25 cyclic atoms, specifically, examples can be given of those corresponding to Ar in chemical formula 1. 11 and Ar 12 The aromatic hydrocarbon group described is the same as the aromatic hydrocarbon group.

[0378] As Ar 21 and Ar 22 The aromatic hydrocarbon group may be a group derived from compounds selected from benzene, biphenyl, terphenyl and fluorene (e.g., a group selected from phenylene, biphenylene, terphenylene and fluorene), a group derived from compounds selected from benzene and fluorene (e.g., a group selected from phenylene and fluorene), or a group derived from benzene (e.g., phenylene).

[0379] Structural unit (B) can be represented by chemical formula 2-1:

[0380] Chemical formula 2-1

[0381]

[0382] In chemical formula 2-1,

[0383] R 31 To R 34 and R 41 To R 44 Each of these can 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 With R 41 They can combine to form a ring.

[0384] L 2 It can be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms.

[0385] Ar 3 It can be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms.

[0386] Ar 4 It can be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms, and Ar 4 Can be used with Ar 3 A ring is formed.

[0387] X 2 It can be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 cyclic atoms.

[0388] Y 2 It can be an aromatic hydrocarbon group having 6 to 25 cyclic atoms, substituted with or unsubstituted with an alkyl group having 1 to 14 carbon atoms, and

[0389] R 31 To R 34 R 41 To R 44 L 2 Ar 3 Ar 4 and X 2 It does not have an alkyl group containing a thiol group having 1 to 14 carbon atoms, nor does it have an alkoxyalkyl group containing a thiol group having 2 to 14 carbon atoms.

[0390] In chemical formula 2 (chemical formula 2-1), Y 2 This can refer to an aromatic hydrocarbon group having 6 to 25 cyclic atoms, substituted or unsubstituted with an alkyl group having 1 to 14 carbon atoms. Specifically, examples of aromatic hydrocarbon groups having 6 to 25 cyclic atoms include those relating to the above-mentioned Y. 1 The same aromatic hydrocarbon groups with 6 to 25 cyclic atoms are described.

[0391] Among them, Y 2 The aromatic hydrocarbon groups included may be groups derived from benzene or fluorene (e.g., phenylene or fluoreneyl groups).

[0392] In the embodiments, in order to better balance improving durability (e.g., luminescence lifetime) and luminescence efficiency, in chemical formula 2 (chemical formula 2-1), Y 2 It can be any of the groups represented by chemical formulas (3'-1) to (3'-3):

[0393]

[0394] In chemical formulas (3'-1) to (3'-3), R 301' To R 305' Each can be an alkyl group having 1 to 14 carbon atoms, either independently unsubstituted or substituted with groups other than thiol groups (-SH), and Indicates the binding site.

[0395] In chemical formulas (3'-1) and (3'-3), R 301' and R 301' With R 302' R 304' and R 305' They can be the same or different. For example, R 301' and R 302' R 304' and R 305' They can be the same as each other.

[0396] As R 301' To R 305' There are no particular limitations on the alkyl group having 1 to 14 carbon atoms, but it can be a straight-chain alkyl group or a branched alkyl group, and specific examples include the same alkyl groups having 1 to 14 carbon atoms as those described with respect to substituent (a).

[0397] From the perspective of better balancing durability (e.g., luminescent lifetime) and luminescent efficiency, as R 301' To R 305'The alkyl group may have 1 to 12 carbon atoms (e.g., 2 to 12 carbon atoms, 2 to 10 carbon atoms, or 4 to 10 carbon atoms), and may be, for example, n-decyl. For example, R 301' and R 302' Each can be an alkyl group having a carbon number within the above range, independently.

[0398] As R 301' To R 305' The alkyl group can be straight-chain. As R 301' To R 304' The alkyl group may be unsubstituted.

[0399] Based on considerations such as film-forming properties, in chemical formula 2 (chemical formula 2-1), Y 2 It can be a group represented by the chemical formula (3'-1) (i.e., fluorene group).

[0400] In chemical formula 2 (chemical formula 2-1), X 2 It can represent an aromatic hydrocarbon group having 6 to 25 cyclic atoms, substituted or unsubstituted, or a heteroaromatic group having 5 to 25 cyclic atoms, substituted or unsubstituted.

[0401] As an aromatic hydrocarbon group having 6 to 25 cyclic atoms, specifically, examples can be given related to the above-mentioned X. 1 The same aromatic hydrocarbon group having 6 to 25 cyclic atoms as described. Specifically, examples of heteroaromatic groups having 5 to 25 cyclic atoms, as described above, include those related to X. 1 The same heteroaromatic groups with 5 to 25 cyclic atoms described.

[0402] Among them, X 2 It can be a group derived from compounds selected from benzene, biphenyl, terphenyl, fluorene, and carbazole (e.g., a group selected from phenyl, biphenyl, terphenyl, fluorene, and carbazole), such as a group derived from compounds selected from benzene, biphenyl, terphenyl, and fluorene (e.g., a group selected from phenyl, biphenyl, terphenyl, and fluorene), or such as a group derived from benzene (e.g., phenyl). X 2 It can be a substituted (substituted by substituents other than substituent (a) and substituent (b)) or unsubstituted group derived from compounds selected from benzene, biphenyl, terphenyl, fluorene and carbazole; a substituted (substituted by substituents other than substituent (a) and substituent (b)) or unsubstituted group derived from compounds selected from benzene, biphenyl, terphenyl and fluorene; an unsubstituted group or a group derived from compounds selected from benzene, biphenyl, terphenyl and fluorene substituted with an alkyl group having 1 to 14 carbon atoms; or an unsubstituted group or a group derived from benzene substituted with an alkyl group having 1 to 14 carbon atoms (e.g., phenyl).

[0403] To improve durability, in the embodiments, X in chemical formula 2 (or chemical formula 2-1) 2 It can be a group represented by the chemical formula (6'-1).

[0404] Chemical formula 6'-1

[0405]

[0406] In chemical formula 6'-1,

[0407] R 601' To R 605' Each can be an independent hydrogen atom or an alkyl group having 1 to 14 carbon atoms, and

[0408] With nitrogen atoms (bound to Ar) 3 (Nitrogen atoms) are combined.

[0409] In R 601' To R 605' Of these, at least one is an unsubstituted alkyl group having 1 to 14 carbon atoms, and the remainder may be hydrogen atoms. In R 601' To R 605' One of them can be an (unsubstituted) alkyl group having 1 to 14 carbon atoms, and the remaining four can be hydrogen atoms. R 603' It can 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 relative to a nitrogen atom (bonded to Ar). 3 The bond of the nitrogen atom ) is in the correct position (p bit or 4 bits).

[0410] As R 601' To R 605' There are no particular limitations on the alkyl group having 1 to 14 carbon atoms, but it can be a straight-chain alkyl group or a branched alkyl group, and specific examples may include the same alkyl groups having 1 to 14 carbon atoms as those described with respect to substituent (a).

[0411] From the perspective of achieving a better balance between improving durability (e.g., luminescent lifetime) and luminescent efficiency, as R 601' To R 605' The alkyl group may have 1 to 12 carbon atoms (e.g., 2 to 10 carbon atoms, 4 to 8 carbon atoms), for example, n-hexyl. Furthermore, R... 603' It can be an alkyl group having a number of carbons within the above range.

[0412] From the perspective of improving durability, as R 601' To R 605' The alkyl group can be straight-chain.

[0413] In another embodiment, in chemical formula 2 (or chemical formula 2-1), X 2 It can be any of the groups represented by chemical formulas (8'-1) to (8'-3):

[0414]

[0415] In chemical formulas (8'-1) to (8'-3),

[0416] L 11' and L 12' Each can independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 cyclic atoms.

[0417] R 801' To R 807' Each of these can 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 cyclic atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 12 cyclic atoms.

[0418] With nitrogen atoms (bound to Ar) 3 (Nitrogen atoms) are combined.

[0419] R exists in or is incorporated into a benzene ring 801' To R 807' They can be the same or different. R exists in different benzene rings or is bound to different benzene rings. 801' To R 807' They can be the same or different.

[0420] As L 11' and L 12' Specific examples of aromatic hydrocarbon groups may include those with L 11 and L 12 The same specific example. As R 801' To R 807' Specific examples of each substituent may include those with R 801 To R 807 The same specific example.

[0421] As mentioned above, in chemical formula 2, L 2 Ar 3 Ar4 Ar 21 and Ar 22 The definitions of L in chemical formula 1 are respectively 1 Ar 1 Ar 2 Ar 11 and Ar 12 The definition is the same. Furthermore, in chemical formula 2-1, L... 2 Ar 3 Ar 4 R 31 To R 34 and R 41 To R 44 The definitions of L in chemical formula 1-1 are respectively 1 Ar 1 Ar 2 R 11 To R 14 and R 21 To R 24 The definitions are the same. Furthermore, the exemplary forms are each the same.

[0422] In chemical formula 2 (or chemical formula 2-1), L 2 It can represent an aromatic hydrocarbon group having 6 to 25 cyclic atoms, substituted or unsubstituted, or a heteroaromatic group having 5 to 25 cyclic atoms, substituted or unsubstituted.

[0423] As L 2 Aromatic hydrocarbon groups, examples of which may include those targeting L 1 The same aromatic hydrocarbon group with 6 to 25 cyclic atoms is described, and as L 2 Examples of heteroaromatic groups, such as those targeting L, may include those specific to L 1 The same heteroaromatic groups with 5 to 25 cyclic atoms are described.

[0424] Among them, L 2 It can be a group derived from a compound selected from substituted or unsubstituted benzene, biphenyl, terphenyl, tetraphenyl and fluorene, such as a group derived from substituted or unsubstituted benzene or biphenyl (substituted or unsubstituted phenylene or biphenylene).

[0425] If L 2 If it is a substituted aromatic hydrocarbon group, then the substituent can be alkyl or phenyl (e.g., alkyl), or methyl, ethyl, n-propyl, or isopropyl (e.g., methyl or ethyl; for example, methyl), that is, L 2 It can be an unsubstituted group or a group derived from benzene or biphenyl that has been substituted with methyl, ethyl, n-propyl, or isopropyl groups. For example, L 2It can be a group derived from benzene or biphenyl, either substituted with or unsubstituted with methyl or ethyl groups. For example, L 2 It can be a group derived from benzene that is substituted or unsubstituted with one or two methyl groups, or a group derived from biphenyl that is substituted or unsubstituted with one or two methyl groups. For example, L 2 It can be a benzene-derived group that is substituted with one or two methyl groups or is unsubstituted. For example, L 2 It can be an unsubstituted benzene-derived group (o-phenylene, m-phenylene, or p-phenylene), such as p-phenylene. Thus, L 2 It can improve the durability (e.g., luminous lifetime) and luminous efficiency of LEDs (e.g., QLEDs) in a better balance.

[0426] In chemical formula 2 (or chemical formula 2-1), L 2 It can be any of the groups represented by chemical formulas (4'-1) to (4'-24):

[0427] In chemical formulas (4'-1) to (4'-24), It binds to the nitrogen atom, and Combined with Ar 3 .

[0428] L 2 It can be any of the groups represented by chemical formulas (4'-1) to (4'-3) and (4'-13) to (4'-16) (i.e., substituted or unsubstituted phenylene). L 2 It can be any of the groups represented by chemical formulas (4'-1) and (4'-13) to (4'-16) (i.e., substituted or unsubstituted p-phenylene), for example, it can be a group represented by chemical formula (4'-1) (i.e., unsubstituted p-phenylene). Thus, L 2 This can achieve higher hole injection properties (and thus higher durability) or better luminous efficiency.

[0429] In chemical formula 2 (or chemical formula 2-1), Ar 3 It can represent an aromatic hydrocarbon group with 6 to 25 cyclic atoms, whether substituted or unsubstituted. In this case, Ar... 3 It can also be used with Ar 4 A ring is formed.

[0430] As Ar 3 There are no particular restrictions on the aromatic hydrocarbon groups. Ar 3 Specific examples may include those related to the L mentioned above. 1 The description is the same as the specific examples derived from aromatic hydrocarbons having 6 to 25 cyclic atoms.

[0431] Among them, Ar 3 It can be a group selected from compounds derived from substituted or unsubstituted benzene, biphenyl, and fluorene; it can be a substituted or unsubstituted group derived from benzene or biphenyl; or it can be a substituted or unsubstituted group derived from benzene (e.g., when Ar...). 3 and Ar 4 When no ring is formed, Ar 3 It can be, for example, o-phenylene, m-phenylene, or p-phenylene, and when Ar 3 and Ar 4 When forming a ring, Ar 3 It can be, for example, 1,3,4-phenylene). Ar 3 Can be used with Ar 4 Forming a ring, and can be substituted or unsubstituted 1,3,4-phenylene, thus, Ar 3 It enables improved hole injection properties (and thus better durability) and good film-forming properties. Furthermore, it can improve durability and luminescence efficiency in a good balance.

[0432] When Ar 3 There are no particular restrictions on the substituents that can exist when any of the hydrogen atoms is substituted, and the same substituents as those described for "substituted" above can be applied. In the examples, Ar 3 It can be unreplaced.

[0433] In chemical formula 2 (or chemical formula 2-1), Ar 4 Ar can represent an aromatic hydrocarbon group having 6 to 25 cyclic atoms, either substituted or unsubstituted, or a heteroaromatic group having 5 to 25 cyclic atoms, either substituted or unsubstituted. 4 It can also be used with Ar 3 A ring is formed.

[0434] As Ar 4 There are no particular restrictions on the aromatic hydrocarbon groups and heteroaromatic groups. As Ar... 4 Specific examples of aromatic hydrocarbon groups may include, for example, those for L 1 The described group is derived from aromatic hydrocarbons having 6 to 25 cyclic atoms. Similarly, as Ar 4 Examples of heteroaromatic groups can be given for the L mentioned above. 1 The described group is derived from heteroaromatic compounds having 5 to 25 cyclic atoms.

[0435] Ar 4It can be a group derived from a compound of selected benzene, biphenyl, and fluorene, whether substituted or unsubstituted; it can be a group derived from benzene or biphenyl, whether substituted or unsubstituted (e.g., when Ar...). 3 and Ar 4 When no ring is formed, Ar 4 It can be, for example, phenyl, and when Ar 3 and Ar 4 When forming a ring, Ar 4 It can be, for example, o-phenylene, m-phenylene, or p-phenylene), or it can be, for example, substituted or unsubstituted o-phenylene. If Ar 4 with Ar 3 Forming rings can improve durability and luminous efficiency in a better balance.

[0436] When Ar 4 There are no particular restrictions on the substituents that can exist when any of the hydrogen atoms is substituted, and the same substituents as those described for "substituted" above can be applied. 4 It can be unreplaced.

[0437] As mentioned above, Ar 3 and Ar 4 They can be connected to form a ring. In this way, by utilizing Ar... 3 and Ar 4 Forming rings allows for improved hole injection properties, which further enhances durability (e.g., luminescence lifetime) and enables good film-forming properties.

[0438] If Ar 3 with Ar 4 To form a ring, it is through Ar 3 with Ar 4 There are no particular restrictions on the ring structure that can be formed, but Ar 3 with Ar 4 They can combine with each other to form a carbazole ring. In the examples, -Ar in Formula 2 (or Formula 2-1) 3 -N(Ar 4 (X) 2 It may have a structure represented by any of the chemical formulas (7'-1) to (7'-3). In the embodiments, -Ar in chemical formula 2 (or chemical formula 2-1) 3 -N(Ar 4 (X) 2 It can have a structure represented by the chemical formula (7'-2):

[0439]

[0440] In chemical formulas (7'-1) to (7'-3),

[0441] R 701' To R 706' Each of these can 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.

[0442] X 2 It can be the same as that defined in Chemical Formula 2 (Chemical Formula 2-1), and Combined with L 2 .

[0443] R exists in or is incorporated into a benzene ring 701' To R 706' They can be the same or different. R exists in different benzene rings or is bound to different benzene rings. 701' To R 706' They can be the same or different.

[0444] As R 701' To R 706' The alkyl group can be straight-chain or branched, and examples may include straight-chain alkyl groups having 1 to 20 carbon atoms or branched alkyl groups having 3 to 20 carbon atoms. As a specific example, among the substituents described above for "substituted", the same specific examples as those given for alkyl groups can be exemplified.

[0445] As R 701' To R 706' Cycloalkyl groups, for example, those having 3 to 16 carbon atoms, can be exemplified. As specific examples, among the substituents described above for "substituted," the same specific examples given for cycloalkyl groups can be exemplified.

[0446] As R 701' To R 706' The alkoxy group can be straight-chain or branched, and examples may include straight-chain alkoxy groups having 1 to 20 carbon atoms or branched alkoxy groups having 3 to 20 carbon atoms. As a specific example, the same specific examples as those given for the alkoxy groups in the substituents described above as "substituted" can be exemplified.

[0447] As R 701' To R 706' Cycloalkoxy groups, for example, those having 3 to 16 carbon atoms, can be exemplified. As specific examples, the same specific examples given for cycloalkoxy groups among the substituents described above as "substituted" can be exemplified.

[0448] As R 701' To R 706' Aryl groups, for example, aryl groups having 6 to 30 cyclic atoms, can be exemplified. As specific examples, among the substituents described above for "substituted," the same specific examples as those given for aryl groups can be exemplified.

[0449] As R 701' To R 706' Halogen atoms can be exemplified by fluorine, chlorine, bromine, or iodine atoms.

[0450] In chemical formulas (7'-1) to (7'-3), R 701' To R 706' Each can be an independent hydrogen atom, or a substituted or unsubstituted alkyl group, or, for example, a hydrogen atom. In chemical formulas (7'-1) to (7'-3), X 2 An exemplary form can be referenced to X 2 The description.

[0451] From the perspective of achieving a better balance between improving durability (e.g., luminescence lifetime) and luminescence efficiency, in formula 2 (or formula 2-1), Ar 3 Can be used with Ar 4 Forming a ring, and -L 2 -Ar 3 -N(Ar 4 (X) 2 The group can be any of the groups represented by chemical formulas (5'-1) to (5'-3). In the examples, the -L group in chemical formula 2 (or chemical formula 2-1) 2 -Ar 3 -N(Ar 4 (X) 2 It can have a structure represented by the chemical formula (5'-2):

[0452]

[0453] In chemical formulas (5'-1) to (5'-3),

[0454] R 501' To R 506' Each of these can 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.

[0455] X 2 It can be the same as that defined in Chemical Formula 2 (Chemical Formula 2-1), and It binds to a nitrogen atom.

[0456] R exists in or is incorporated into a benzene ring 501' To R 506' They can be the same or different. R exists in different benzene rings or is bound to different benzene rings. 501' To R 506' They can be the same or different.

[0457] As R 501' To R 506' Each substituent may be adopted with respect to R in chemical formulas (7'-1) to (7'-3). 701' To R 706' The examples given use the same substituents. R 501' To R 506' Each can be an independent hydrogen atom, or a substituted or unsubstituted alkyl group, or, for example, a hydrogen atom. In chemical formulas (5'-1) to (5'-3), X 2 An exemplary form can be found in X. 2 The description.

[0458] In chemical formula 2-1, R 31 To R 34 and R 41 To R 44 Each of these can 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 They can combine to form a ring.

[0459] R 31 To R 34 and R 41 To R 44 They can be the same or different.

[0460] As R 31 To R 34 and R 41 To R 44 The alkyl group can be straight-chain or branched, and examples may include straight-chain alkyl groups having 1 to 20 carbon atoms or branched alkyl groups having 3 to 20 carbon atoms. As a specific example, among the substituents described above for "substituted", the same specific examples as those given for alkyl groups can be exemplified.

[0461] As R 31 To R 34 and R 41 To R 44Cycloalkyl groups, for example, those having 3 to 16 carbon atoms, can be exemplified. As specific examples, among the substituents described above for "substituted," the same specific examples given for cycloalkyl groups can be exemplified.

[0462] As R 31 To R 34 and R 41 To R 44 The alkoxy group can be straight-chain or branched, and examples may include straight-chain alkoxy groups having 1 to 20 carbon atoms or branched alkoxy groups having 3 to 20 carbon atoms. As a specific example, the same specific examples as those given for the alkoxy groups in the substituents described above as "substituted" can be exemplified.

[0463] As R 31 To R 34 and R 41 To R 44 Cycloalkoxy groups, for example, those having 3 to 16 carbon atoms, can be exemplified. As specific examples, the same specific examples given for cycloalkoxy groups among the substituents described above as "substituted" can be exemplified.

[0464] As R 31 To R 34 and R 41 To R 44 Aryl groups, for example, aryl groups having 6 to 30 cyclic atoms, can be exemplified. As specific examples, among the substituents described above for "substituted," the same specific examples as those given for aryl groups can be exemplified.

[0465] As R 31 To R 34 and R 41 To R 44 Halogen atoms can be exemplified by fluorine, chlorine, bromine, and iodine atoms.

[0466] In addition, R 31 and R 41 They can combine to form a loop. At this point, through R... 31 and R 41 There are no particular restrictions on the formed ring structure, but for example, there exist ring structures where R... 31 and R 41 They combine to form a carbazole ring.

[0467] R 31 To R 34 and R 41 To R 44Each of these atoms can be a hydrogen atom or a straight-chain alkyl or branched alkyl group having one to five carbon atoms. Therefore, higher durability (e.g., luminescent lifetime) or better luminescent efficiency can be achieved. 31 To R 34 and R 41 To R 44 Each can be an independent hydrogen atom or a straight-chain alkyl or branched alkyl group having one to three carbon atoms. R 31 To R 34 and R 41 To R 44 It can consist entirely of, for example, hydrogen atoms.

[0468] The structural unit (B) represented by the above chemical formula 2 can be combined with the structural unit (A) represented by chemical formula 1 (except for the portion including substituent (a) or substituent (B) (i.e., Y)). 1 (Except for) it has the same structure and substituents. Therefore, Ar in chemical formula 2 21 With Ar in chemical formula 1 11 Similarly, Ar in chemical formula 2 22 With Ar in chemical formula 1 12 Similarly, L in chemical formula 2 2 With L in chemical formula 1 1 Similarly, Ar in chemical formula 2 3 With Ar in chemical formula 1 1 Similarly, 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 same.

[0469] Similarly, R in chemical formula 1-1 11 It can be combined with R in chemical formula 2-1 31 Similarly, R in chemical formula 1-1 12 It can be combined with R in chemical formula 2-1 32 Similarly, R in chemical formula 1-1 13 It can be combined with R in chemical formula 2-1 33 Similarly, R in chemical formula 1-1 14 It can be combined with R in chemical formula 2-1 34 Similarly, R in chemical formula 1-1 21 It can be combined with R in chemical formula 2-1 41 Similarly, R in chemical formula 1-1 22 It can be combined with R in chemical formula 2-1 42 Similarly, R in chemical formula 1-1 23 It can be combined with R in chemical formula 2-1 43 Similarly, R in chemical formula 1-124 It can be combined with R in chemical formula 2-1 44 Similarly, L in chemical formula 1-1 1 It can be combined with L in chemical formula 2-1 2 Similarly, Ar in chemical formula 1-1 1 It can react with Ar in chemical formula 2-1 3 Similarly, Ar in chemical formula 1-1 2 It can react with Ar in chemical formula 2-1 4 The same, and X in chemical formula 1-1 1 It can be combined with X in chemical formula 2-1 2 same.

[0470] Furthermore, in the above text, for example, "Ar in chemical formula 1" 11 With Ar in chemical formula 2 21 "Same" means Ar 11 and Ar 21 They have the same structure. For example, if Ar 11 If it is an unsubstituted phenylene, then it represents Ar. 21 It is also an unsubstituted phenylene.

[0471] According to the embodiment, the structural unit (B) may be selected from the following groups:

[0472] In chemical formulas (B-1) to (B-3), R 57' R 58' R 67' R 68' R 77' and R 78' Each can independently represent a straight-chain alkyl 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' Each can independently represent a hydrogen atom or a straight-chain alkyl or branched alkyl group having 1 to 12 carbon atoms; for example, in chemical formulas (B-1) to (B-3), R 57' R 58' R 67' R 68' R 77' and R 78' Each can independently represent a straight-chain alkyl or branched alkyl group having 2 to 12 carbon atoms, and R 51' To R 56' R 61' To R 66' and R71' To R 76' Each can independently represent a hydrogen atom or a straight-chain alkyl or branched alkyl group having 2 to 10 carbon atoms; and, for example, in chemical formulas (B-1) to (B-3), R 57' R 58' R 67' R 68' R 77' and R 78' Each can independently represent a straight-chain alkyl 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' Each can independently represent a hydrogen atom, and R 56' R 66' and R 76' Each can independently represent a straight-chain alkyl or branched alkyl with 4 to 8 carbon atoms.

[0473] R exists in or is incorporated into a benzene ring 51' To R 56' R 61' To R 66' and R 71' To R 76' They can be the same or different. R exists in different benzene rings or is bound to different benzene rings. 51' To R 56' R 61' To R 66' and R 71' To R 76' They can be the same or different.

[0474] The structural unit (B) can be one of the structural units represented by the chemical formula (B-2) mentioned above, and the specific form of each substituent in the structural unit is as described above.

[0475] Other structural units

[0476] The polymers included in the compositions of the embodiments may also include structural units other than structural unit (A) and optional structural unit (B). Where another structural unit is included, it is not particularly limited, as long as it does not inhibit the effects of the polymer. Other structural units may include structural units derived from compounds such as azurite, naphthalene, anthracene, phenanthrene, pyrene, etc. Hereinafter, other structural units are referred to as "structural unit (C)".

[0477] Polymer composition

[0478] The composition of structural units (A) to (C) in the polymer according to the embodiments is not particularly limited. Considering a further good balance between durability (luminescence lifetime) and luminescence efficiency of the layer (e.g., hole injection layer, hole transport layer) formed by the obtained polymer and the thiol-olefin crosslinking of the compound represented by Formula 10, structural unit (A) may be included in an amount based on the total molar number of structural units constituting the polymer, 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. When the polymer includes two or more types of structural units (A), the amount of structural unit (A) represents the total amount of structural units (A).

[0479] In an embodiment, structural unit (A) is included in the polymer at a rate of less than about 100 mol% based on the total molar number of structural units. Considering an objective of achieving a good balance between the durability (luminescence lifetime) and luminescence efficiency of the layer (e.g., hole injection layer, hole transport layer) formed by the obtained polymer and the thiol-olefin crosslinking of the compound represented by Formula 10, structural unit (B) may be included in an amount, 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%. When the polymer contains two or more types of structural units (B), the amount of structural unit (B) refers to the total amount of structural units (B).

[0480] As described above, the polymer may also include additional structural units (structural units (C)). The composition of these additional structural units (structural units (C)) is not particularly limited. Taking into account the crosslinking ratio resulting from the thiol-ene crosslinking between the polymer and the compound represented by Formula 10, and the effect of improved film strength obtained through the thiol-ene crosslinking between the polymer and the compound, structural units (C) may be included in an amount, for example, greater than 0 mol% and less than or equal to about 10 mol%, based on the total molar number of structural units constituting the polymer. If the polymer includes two or more types of structural units (C), the amount of structural units (C) represents the total amount of structural units (C).

[0481] Based on the total number of moles of structural unit (A) and structural unit (B), the molar ratio of structural unit (A) can 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 ratio of structural unit (B) can be greater than 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 number of moles of structural unit (A) and structural unit (B).

[0482] The molar ratios among structural units (A), (B), and (C) can be appropriately controlled by adjusting the molar ratios of the monomers used as raw materials. Furthermore, the molar ratios of each structural unit (A), (B), and (C) in the polymer can be adjusted by using… 1 H-NMR, 13 Measurements can be performed using C-NMR, mass spectrometry, liquid chromatography-mass spectrometry (LC-MS), Fourier transform infrared spectroscopy (FTIR), or a combination of these methods.

[0483] When considering a good balance between durability (e.g., luminescence lifetime) and luminescence efficiency of a film (e.g., hole transport layer) prepared from the product of a thiol-ene crosslinking reaction between a polymer and a compound represented by Formula 10, the polymer may consist only of structural units (A) and structural units (B) (i.e., the total ratio of structural units (A) and structural units (B) to the total structural units of the polymer is 100 mol%) due to heat treatment of the composition comprising the polymer and the compound at a temperature of less than or equal to 200 °C (e.g., less than or equal to 190 °C).

[0484] There are no particular limitations on the weight-average molecular weight (Mw) of the polymer. This weight-average molecular weight (Mw) can be, for example, greater than or equal to about 5,000 Da and less than or equal to about 1,000,000 Da, for example, greater than or equal to about 8,000 Da and less than or equal to about 1,000,000 Da, greater than or equal to about 10,000 Da and less than or equal to about 800,000 Da, or for example, greater than or equal to about 50,000 Da and less than or equal to about 500,000 Da. With such a weight-average molecular weight, a layer with a uniform (consistent) film thickness can be formed by appropriately controlling the viscosity of the coating solution used to form a thin film (e.g., a hole transport layer), the thin film comprising products prepared via a thiol-olefin crosslinking reaction using the composition according to the embodiments.

[0485] Furthermore, there are no particular limitations on the number-average molecular weight (Mn) of the polymer. This number-average molecular weight (Mn) can, for example, be greater than or equal to about 4,000 Da and less than or equal to about 300,000 Da, for example, greater than or equal to about 6,000 Da and less than or equal to about 250,000 Da, greater than or equal to about 10,000 Da and less than or equal to about 200,000 Da, or for example, greater than or equal to about 20,000 Da and less than or equal to about 150,000 Da. With such a number-average molecular weight, a layer with a uniform (consistent) film thickness can be formed by appropriately controlling the viscosity of the coating solution used to form a film (e.g., a hole transport layer), the film comprising products prepared via a thiol-olefin crosslinking reaction using the composition according to the embodiments. In addition, the polydispersity (weight-average molecular weight / number-average molecular weight) of the polymer may, for example, be greater than or equal to about 1.1 and less than or equal to about 5.0, 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.

[0486] There are no particular limitations on the measurement of number-average molecular weight (Mn) and weight-average molecular weight (Mw), and they can be measured using known methods or by appropriately modifying known methods. In this specification, number-average molecular weight (Mn) and weight-average molecular weight (Mw) are values ​​measured by the following method. The polydispersity of the polymer (Mw / Mn) is calculated by dividing the weight-average molecular weight (Mw) measured by the following method by the number-average molecular weight (Mn).

[0487] Measurement of number-average molecular weight (Mn) and weight-average molecular weight (Mw)

[0488] The number-average molecular weight (Mn) and weight-average molecular weight (Mw) of the polymeric material were measured by SEC (size exclusion chromatography) using polystyrene as a standard material under the following conditions:

[0489] SEC measurement conditions

[0490] Analytical Equipment (SEC): Shimadzu Corporation, Prominence (registered trademark)

[0491] Column: Polymer Laboratories, PLgel MIXED-B

[0492] Column temperature: 40℃

[0493] Flow rate: 1.0 mL / min

[0494] Sample solution injection volume: 20 μL (polymer concentration: approximately 0.05% by mass)

[0495] Eluent: Tetrahydrofuran (THF)

[0496] Detector (UV-VIS detector): Shimadzu Corporation, SPD-10AV

[0497] Standard sample: polystyrene.

[0498] The ends of the polymer backbone included in the compositions according to the embodiments are not particularly limited and are appropriately defined according to the type of raw materials used, but are generally hydrogen atoms.

[0499] The glass transition temperature (T) of the polymer according to the embodiment g There are no particular limitations, but it can be, for example, 75°C or higher, 90°C or higher, or 100°C or higher. On the other hand, the glass transition temperature (T...) g There is no particular limit to the upper limit of ), but it can be, for example, 180°C or lower, or, for example, 150°C or lower.

[0500] When the glass transition temperature of the polymer (T) g When the temperature is within the above range, it is advantageous to manufacture the device, and a device with improved characteristics can also be obtained. The glass transition temperature (T) of the polymer... g This can be measured using a differential scanning calorimeter (DSC) (manufactured by Seiko Instruments, Inc., product name: DSC6000). Details of the measurement method are described in the examples.

[0501] Even if the polymer does not form a crosslinked product with the compound represented by Formula 10 through a thiol-olefin crosslinking reaction, the polymer is still a material with inherent hole transport properties, and according to the embodiments, even if the polymer forms a crosslinked product with the compound represented by Formula 10 through a thiol-olefin crosslinking reaction, the hole transport properties remain unchanged. For example, the hole mobility of a film manufactured by curing a composition containing only the polymer and without the compound represented by Formula 10 can be greater than or equal to about 10. -5 cm 2 V -1 S -1 Furthermore, when a composition comprising a polymer and a compound represented by chemical formula 10 (i.e., the composition according to the embodiments) is cured to produce a film, the hole mobility of the film may also be greater than or equal to about 10. -5 cm 2 V -1 S -1 In other words, the composition according to the embodiments can almost completely retain the hole transport properties of the polymer containing the structural unit (A) represented by chemical formula 1.

[0502] U.S. Patent Publication US2022 / 0320453A1, published prior to the priority date of this application, discloses that crosslinked products formed by a thiol-olefin binding reaction between a hole-transporting polymer comprising unsaturated bonds (such as carbon-carbon double bonds) and an additive comprising thiol groups can be applied to hole-transporting layers, etc. However, the crosslinked products according to the prior art actually exhibit very little hole-transporting property. However, unlike the crosslinked products disclosed in the U.S. Patent Publication, the compositions according to the embodiments can be advantageously used as hole-transporting materials for electroluminescent devices because the hole-transporting properties of the polymer itself remain substantially the same even after the formation of the crosslinked product through a thiol-olefin binding reaction between the polymer and a compound represented by Formula 10. The polymer can be synthesized using known organic synthesis methods. The specific methods of polymer synthesis will be understood by those skilled in the art by referring to the examples described later.

[0503] For example, the polymer can be prepared by copolymerization using at least one monomer (Ix) represented by chemical formula IX and at least one monomer (Iy) represented by chemical formula IY. If desired, monomers of structural unit (B) can be added. Specifically, the polymer can be prepared by copolymerization using 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., the monomer constituting structural unit (B) according to the embodiment) and at least one monomer (Ix) represented by chemical formula IX and at least one monomer (Iy) represented by chemical formula IY (i.e., the monomer constituting structural unit (A) according to the embodiment). In the polymer, when X in structural unit (A) has the same structure as X' in structural unit (B), the polymer according to the embodiment can also be prepared by copolymerization using 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. If desired, other monomers corresponding to structural unit (C) can be added. The molar ratios of structural units (A), (B), and (C) in the polymer can be controlled by appropriately controlling the molar ratios of each monomer.

[0504] Chemical formula IX

[0505]

[0506] Chemical formula IY

[0507]

[0508] Chemical formula II-X

[0509]

[0510] Chemical formula II-Y

[0511]

[0512] Alternatively, the polymer can be manufactured by polymerization using one or more monomers represented by chemical formula 1'. If desired, a monomer corresponding to structural unit (B) may also be added. Specifically, when the polymer comprises structural unit (A) and structural unit (B), the polymer can be manufactured by copolymerization using at least one monomer represented by chemical formula 1' and at least one monomer represented by chemical formula 2'. If desired, an additional monomer corresponding to structural unit (C) may be added.

[0513] Chemical formula 1'

[0514]

[0515] Chemical formula 2'

[0516]

[0517] In the embodiments, monomers used for polymer polymerization can be synthesized by appropriately combining known synthetic reactions, and their structures can also be confirmed by known methods (e.g., NMR, LC-MS, etc.).

[0518] In chemical formulas IX, IY, II-X, II-Y, 1', and 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 Same as defined in Chemical Formula 1 or Chemical Formula 2, and W 1 To W 12 Each is independently a halogen atom (fluorine, chlorine, bromine, iodine, or bromine) or a group having the following structure. In the following structure, R A To R D Each is an alkyl group having one to three carbon atoms. R A To R D It can be methyl.

[0519]

[0520] W in chemical 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 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 They can be the same or different. However, in order to suppress the self-polymerization of monomers (Ix), W in chemical formula IX... 1 and W 2 These can be atoms or groups that do not react with each other. Similarly, to suppress the self-polymerization of monomers (Iy), W in the chemical formula IY... 3 and W 4 These can be atoms or groups that do not react with each other. Similarly, to suppress self-polymerization between monomers (II-x) or monomers (II-y), W in formula II-X... 5 and W 6 And W in chemical formula II-Y 7 and W 8 These can be atoms or groups that do not react with each other. Similarly, to suppress self-polymerization between monomers represented by Formula 1' or between monomers represented by Formula 2', W in Formula 1'... 9 and W 10 And W in chemical formula 2' 11 and W 12 These can be atoms or groups that do not react with each other. For example, W in chemical 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 Each can be the same. For example, W in chemical formula 1' 9 and W 10 They can be different. Similarly, for example, W in chemical formula 2' 11 and W 12 They can be different.

[0521] compound

[0522] The compounds included in the compositions according to the embodiments can be represented by chemical formula 10:

[0523] Chemical Formula 10

[0524]

[0525] In chemical formula 10,

[0526] Ar and Ar 5 To Ar 8 Each is independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 cyclic atoms, a substituted or unsubstituted heteroaromatic cyclic group having 5 to 25 cyclic atoms, or a combination thereof, wherein the aromatic hydrocarbon group and the heteroaromatic cyclic group include (e.g., each independently includes) a monocyclic ring, a fused ring of two or more rings, or a cyclic combination wherein the monocyclic ring and / or the fused rings are connected by a single bond.

[0527] Ar 5 with Ar 6 and / or Ar 7 with Ar 8 Each can be independently and optionally connected to each other to form a loop.

[0528] Ar and Ar 5 To Ar 8 At least two of them are independently replaced by C2 to C10 aliphatic hydrocarbon groups containing carbon-carbon double bonds or carbon-carbon triple bonds, or C3 to C10 alicyclic hydrocarbon groups containing carbon-carbon double bonds or carbon-carbon triple bonds.

[0529] In the compounds represented by chemical formula 10, Ar and Ar 5 To Ar 8 At least two of the groups in the compound represented by Formula 10 are replaced by aliphatic or alicyclic hydrocarbon groups containing carbon-carbon double or triple bonds. Therefore, the unsaturated bond groups containing at least two carbon-carbon double or triple bonds in the compound represented by Formula 10 can be substituted with thiol groups in the structural unit (A) of the polymer represented by Formula 1. 1 A thiol-alkene bonding reaction is formed. For example, two or more unsaturated bond groups in a compound represented by Formula 10 react with two or more thiol groups in the structural unit (A) of a polymer represented by Formula 1. 1 A thiol-olefin bonding reaction is formed, such that the composition according to the embodiments can be made into a film comprising a crosslinked product between a polymer represented by chemical formula 1 and a compound represented by chemical formula 10.

[0530] Here, the compound represented by Formula 10 can be a compound that exhibits hole transport properties. That is, when a composition containing only the compound represented by Formula 10 and not the polymer containing the structural unit (A) represented by Formula 1 is cured to manufacture a thin film, the hole mobility of the thin film can be greater than or equal to about 10. -5 cm 2 V -1 S -1 Furthermore, when the compound is cured together with a polymer comprising a structural unit (A) represented by chemical formula 1 to fabricate a thin film, the hole mobility of the thin film can also be greater than or equal to about 10. -5 cm 2 V -1 S -1 In other words, the polymer comprising the structural unit (A) represented by chemical formula 1 and the compound represented by chemical formula 10 included in the composition according to the embodiments both exhibit a value greater than or equal to about 10. -5 cm 2 V -1 S -1 The hole mobility, and the hole mobility of the film manufactured by curing the composition comprising the polymer and the compound according to the embodiment can also be greater than or equal to about 10. -5 cm 2 V -1 S -1 Therefore, the compositions according to the embodiments retain the hole transport properties of the polymer and the compound without degradation even after crosslinking of the polymer comprising the structural unit (A) represented by Chemical Formula 1 with the compound represented by Chemical Formula 10. Therefore, the compositions according to the embodiments can be advantageously applied to the hole transport layer of an electroluminescent device.

[0531] In chemical formula 10, Ar and Ar 5 To Ar 8 Each may independently be a substituted or unsubstituted aromatic hydrocarbon group having 6 to 15 cyclic atoms, a substituted or unsubstituted heteroaromatic cyclic group having 5 to 15 cyclic atoms, or a combination thereof, wherein the aromatic hydrocarbon group and the heteroaromatic cyclic group include (e.g., each independently includes) a monocyclic ring, a fused ring of two or more rings, or a cyclic combination wherein the monocyclic ring and / or the fused rings are connected by a single bond, Ar 5 with Ar 6 and / or Ar 7 with Ar 8 They can be independently and optionally connected to each other to form a ring, and Ar and Ar 5 To Ar 8At least two of them can be independently replaced by C2 to C5 aliphatic hydrocarbon groups containing carbon-carbon double bonds or carbon-carbon triple bonds, or C3 to C6 alicyclic hydrocarbon groups containing carbon-carbon double bonds or carbon-carbon triple bonds.

[0532] In Formula 10, Ar can be a substituted or unsubstituted phenylene, a substituted or unsubstituted pyridinium group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted pyrazine group, a substituted or unsubstituted triazine group, a substituted or unsubstituted biphenylene, or a combination thereof, such as a substituted or unsubstituted phenylene or a substituted or unsubstituted biphenylene, or for example, a substituted or unsubstituted biphenylene.

[0533] In chemical formula 10, Ar 5 To Ar 8 Each of these can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted acridine, a substituted or unsubstituted pyridyl, or a combination thereof. 5 with Ar 6 and / or Ar 7 with Ar 8 They can be independently and optionally linked together to form a substituted or unsubstituted carbazole ring, or a fused ring of substituted or unsubstituted indole and pyridine, and Ar 5 and Ar 6 One of them and Ar 7 and Ar 8 Each of the groups is independently replaced by a C2 to C4 aliphatic hydrocarbon group, including a carbon-carbon double bond or a carbon-carbon triple bond.

[0534] In the embodiments, the compound represented by chemical formula 10 may be represented by chemical formula 10-1:

[0535] Chemical formula 10-1

[0536]

[0537] In chemical formula 10-1,

[0538] It can be a heteroaromatic cyclic group with 5 to 15 cyclic atoms, either substituted or unsubstituted.

[0539] Ar 5 To Ar 8 Each can be independently identical to the one defined in chemical formula 10.

[0540] R a and R bEach of these can be independently a deuterium, a C1 to C10 alkyl group, a C2 to C10 alkenyl group, a C1 to C10 haloalkyl group, a halogen atom, a cyano group, a nitro group, or a combination thereof.

[0541] x and y can each be an independent integer from 0 to 4, and

[0542] m and n can each be an integer from 0 to 3 independently.

[0543] In chemical formula 10-1, It can be a substituted or unsubstituted pyridinium group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted pyrazine group, a substituted or unsubstituted triazine group, or a combination thereof.

[0544] In chemical formula 10-1, R a and R b Each of these can be independently a C1 to C4 alkyl, C1 to C2 haloalkyl, halogen atom, cyano group, or combination thereof, and for example, R a and R b Each of them can be trifluoromethyl, fluoro, cyano, or a combination thereof, but is not limited thereto. In chemical formula 10⁻¹, x and y can each be an integer of 0 or 4.

[0545] In chemical formula 10⁻¹, m and n can each be an independent integer of 0 or 1. Both m and n can be 0, both m and n can be 1, or one of m and n can be 0 while the other can be 1.

[0546] Compounds represented by chemical formula 10 may include, but are not limited to, compounds represented by groups 1, 2, 3 and 4.

[0547] Group 1

[0548] Group 2

[0549] Group 3

[0550] Group 4

[0551] In the embodiments, the compounds represented by chemical formula 10 may include, but are not limited to, compounds represented by chemical formula 10-2, compounds represented by chemical formula 10-3, or combinations thereof:

[0552] Chemical formula 10-2

[0553]

[0554] Chemical formula 10-3

[0555]

[0556] Since the two or more carbon-carbon unsaturated bond groups included in the compound represented by Formula 10 undergo a thiol-olefin bonding reaction with the thiol groups in the polymer including the structural unit (A) represented by Formula 1 in a 1:1 molar ratio, the amount of the compound represented by Formula 10 in the composition according to the embodiment can be taken into account, but is appropriate, the amount of the polymer including the structural unit (A) represented by Formula 1 and the amount of the thiol groups in the polymer.

[0557] For example, when the amount of structural unit (A) including thiol groups in the polymer is about 20 mol% based on the total number of moles of the structural units forming the polymer, the compound represented by Formula 10 may be included in an amount corresponding to about 20 mol% based on the total number of moles of the structural units forming the polymer. Furthermore, for example, when the amount of structural unit (A) in the polymer is about 10 mol% based on the total number of moles of the structural units forming the polymer, the compound represented by Formula 10 may be included in an amount corresponding to about 10 mol%.

[0558] Compounds represented by Formula 10 can be obtained by reacting Ar with compounds that satisfy the basic structure of Formula 10 among any conventional low molecular weight organic compounds known to have hole transport properties. 5 To Ar 8 It is readily prepared by substituting two or more C2-C10 aliphatic hydrocarbon groups or C3-C10 alicyclic hydrocarbon groups containing carbon-carbon double or triple bonds at corresponding positions. That is, hole-transferring of small molecular weight organic compounds satisfying the basic structure of Formula 10 is known, and the substitution of aliphatic hydrocarbon groups or alicyclic hydrocarbon groups containing carbon-carbon double or triple bonds with Ar in these small molecular weight organic compounds is readily achieved. 5 To Ar 8 The introduction of two or more of the corresponding positions can be readily performed by those skilled in the art using known organic chemical synthesis methods with reference to the examples described below.

[0559] Materials for electroluminescent devices

[0560] The compositions according to the embodiments can be advantageously used as materials for electroluminescent devices. By using the compositions according to the embodiments, a hole transport layer with a high film retention rate can be formed, and at this time, the deterioration of the hole injection layer disposed below the hole transport layer can be prevented, thereby providing an electroluminescent device with excellent hole injection and hole transport characteristics, low driving voltage, excellent light emission characteristics, and high luminous efficiency. Therefore, in another embodiment, an electroluminescent device manufactured using the compositions according to the embodiments is provided. Optionally, the use of the compositions as materials for electroluminescent devices (e.g., materials for forming hole transport layers) is provided.

[0561] Electroluminescent devices

[0562] As described above, the compositions according to the embodiments can be advantageously used in electroluminescent devices. An electroluminescent device may include a pair of electrodes facing each other, a light-emitting layer between the pair of electrodes, and at least one organic film between the light-emitting layer and one of the pair of electrodes, said at least one organic film comprising the composition or a material for forming the electroluminescent device. The electroluminescent device according to the embodiments exhibits excellent luminescent characteristics and luminescent efficiency at low driving voltages. The electroluminescent device includes a first electrode and a second electrode facing each other, a light-emitting layer between the first electrode and the second electrode, and at least one organic film between the first electrode and the light-emitting layer, wherein said at least one organic film comprises a thin film of a cured material of the composition according to the embodiments. The electroluminescent device may also include a light-emitting layer between the electrodes, wherein the light-emitting layer comprises a light-emitting material capable of emitting light from triplet excitons.

[0563] The embodiments include a method for manufacturing an electroluminescent device comprising a pair of electrodes, a light-emitting layer between the pair of electrodes, and at least one organic film between the light-emitting layer and one of the pair of electrodes, said at least one organic film being prepared from a composition according to the embodiments, wherein said at least one organic film is formed by a coating method. Therefore, the embodiments provide an electroluminescent device wherein at least one layer of the organic film is formed by a coating method.

[0564] The compositions according to the embodiments and the materials used to prepare electroluminescent devices (i.e., EL device materials) (hereinafter collectively referred to as "polymeric compounds / EL device materials" or "compositions / EL device materials") exhibit excellent solubility in organic solvents. Therefore, the compositions / EL device materials according to the embodiments can be advantageously used in the manufacture of devices (e.g., thin films) by coating methods (wet processes). Thus, liquid compositions comprising the compositions according to the embodiments and a solvent or dispersion medium are provided. The liquid compositions may also contain known dispersants.

[0565] As described above, the material for electroluminescent devices according to the embodiments can be advantageously used in the manufacture of EL devices (e.g., thin films) by a coating method (wet process). In view of the above, this embodiment provides a thin film comprising the composition according to the embodiments. Such a thin film is an example of a thin film according to the embodiments.

[0566] The material for the EL device according to this embodiment can have excellent hole injection properties and hole mobility. Therefore, the material can be advantageously used in the formation of any organic film (such as a hole injection material, a hole transport material, or a light-emitting material (body)). In particular, the material can be advantageously used as a hole injection material or a hole transport material, or for example, it can be advantageously used as a hole transport material.

[0567] In the embodiments, the luminescent material is not particularly limited, but may include at least one of semiconductor nanocrystal particles (semiconductor inorganic nanoparticles) and perovskite compounds (perovskite halides).

[0568] Reference Figure 1 A detailed description of the electroluminescent device according to an embodiment is provided. As shown in the figure, the EL device 100 according to an 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.

[0569] The composition according to the embodiments may be included in an organic film (organic layer) between, for example, the first electrode 120 and the second electrode 180. Specifically, the composition may be included as a hole transport material in the hole transport layer 140. That is, in the embodiments, the organic film including the composition according to the embodiments may be a hole transport layer.

[0570] Organic films, including those of the compositions / EL device materials according to the embodiments, can be formed by coating methods (solution coating methods). For example, organic films can be formed using solution coating methods (such as spin coating, casting, microgravure coating, gravure coating, bar coating, roller coating, wire bar coating, dip coating, spraying, screen printing, flexographic printing, offset printing, or inkjet printing).

[0571] Solvents capable of dissolving the composition / EL device material according to the embodiments can be used to provide solutions for the coating method and can be appropriately selected depending on the type of polymeric compound used. Examples may include toluene, xylene, ethylbenzene, diethylbenzene, mesitylene, propylbenzene, cyclohexylbenzene, dimethoxybenzene, anisole, ethoxytoluene, phenoxytoluene, isopropyl biphenyl, dimethyl anisole, phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, or cyclohexane, etc. The amount of solvent used is not particularly limited, but considering ease of application, the amount is such that the concentration of the composition can be, for example, greater than or equal to about 0.1% by mass and less than or equal to about 10% by mass or less, or, for example, greater than or equal to about 0.5% by mass and less than or equal to about 5% by mass.

[0572] There are no particular limitations on the method used to form a membrane other than an organic membrane comprising the composition / EL device material according to the embodiments. Layers other than an organic membrane comprising the composition / EL device material according to the embodiments can be formed by, for example, vacuum deposition or solution coating.

[0573] The substrate 110 can be a substrate used in general EL devices. For example, the substrate 110 can be a semiconductor substrate (such as a glass substrate or a silicon substrate) or a transparent plastic substrate.

[0574] A first electrode 120 is formed on a 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 with 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. The first electrode 120 can also be formed as a reflective electrode by laminating magnesium (Mg), aluminum (Al), or the like onto a transparent conductive film. After the first electrode 120 is formed on the substrate 110, cleaning and UV-ozone treatment can be performed if necessary.

[0575] Hole injection layer 130 may be formed on first electrode 120. Hole injection layer 130 may be a layer that promotes the injection of holes from first electrode 120, and specifically, may be formed to have a thickness of, for example, about 10 nm to about 1000 nm, or for example, about 20 nm to about 50 nm (dry film thickness; also applied hereinafter).

[0576] The hole injection layer 130 can be formed using known hole injection materials. Known hole injection materials for forming the hole injection layer 130 may include, for example, triphenylamine containing polyetherketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetra(pentafluorophenyl)borate (PPBI), N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), copper phthalocyanine, and 4,4',4''-tris(3-methylphenylphenylamino)triphenylamine (m-M TDATA), 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.

[0577] A hole transport layer 140 may be formed on the hole injection layer 130. The hole transport layer 140 may be a layer with the function of transporting holes and may be formed to have a thickness of, for example, about 10 nm to about 150 nm (e.g., about 20 nm to about 50 nm). The hole transport layer 140 may be formed using a composition according to the embodiments via solution coating. As demonstrated, the durability (luminescence lifetime) of the EL device 100 may be extended by the presence of the polymeric compound in the hole transport layer. Furthermore, it has also been demonstrated that improvements in the current efficiency of the EL device 100 and / or reductions in the driving voltage are also achieved. Moreover, because the hole transport layer can be formed via solution coating, large-area films can be formed efficiently.

[0578] The light-emitting layer 150 can be formed on the hole transport layer 140. The light-emitting layer 150 can be a layer that emits light through fluorescence, phosphorescence, or the like, and can be formed using vacuum deposition, spin coating, inkjet printing, or similar methods. The light-emitting layer 150 can be formed with a thickness, 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. Any known light-emitting material can be used as the light-emitting material for the light-emitting layer 150. The light-emitting material included in the light-emitting layer 150 can be a light-emitting material capable of emitting light from triplet excitons (i.e., phosphorescence). In such cases, the lifetime and luminous efficiency of the EL device 100 can be further improved.

[0579] 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 perovskite-type compounds. That is, in embodiments, the electroluminescent device may have a light-emitting layer including at least one of semiconductor nanocrystal particles and perovskite-type compounds. When the 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. Furthermore, when the emitting layer includes a perovskite compound (perovskite halide), the EL device is a perovskite electroluminescent device (PeLED) or a perovskite light-emitting device.

[0580] In the form of a light-emitting layer comprising semiconductor nanocrystal particles (QLED), the light-emitting layer is a single layer or multiple layers of semiconductor nanocrystal particles (quantum dots). Semiconductor nanocrystal particles (quantum dots) are particles of a specific size that have a quantum confinement effect. The diameter of the semiconductor nanocrystal particles (quantum dots) is not particularly limited, but can range from approximately 1 nm to approximately 20 nm.

[0581] Semiconductor nanocrystal particles (quantum dots) arranged in the light-emitting layer can be synthesized through wet chemical processes, organometallic chemical vapor deposition, molecular beam epitaxy, or other similar processes. Among them, the wet chemical process is a method of growing particles by adding precursor materials to an organic solvent.

[0582] In wet chemical processes, organic solvents naturally distribute onto the surface of quantum dot crystals and act as dispersants during crystal growth, thereby controlling the crystal growth. Therefore, compared to vapor deposition methods such as metal-organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE), the growth of semiconductor nanocrystal particles can be easily and cost-effectively controlled in wet chemical processes.

[0583] Semiconductor nanocrystal particles (quantum dots) can have their band gaps controlled by manipulating their size, allowing light of various wavelengths to be emitted from the light-emitting layer (quantum dot light-emitting layer). By using multiple quantum dots of different sizes, displays that emit light (or emit light) of multiple wavelengths can be fabricated. The size of the quantum dots can be selected to emit red, green, or blue light, enabling the construction of color displays. Furthermore, the sizes of the quantum dots can be combined to emit white light of various colors.

[0584] Semiconductor nanocrystal particles (quantum dots) can be semiconductor materials selected from group II-VI semiconductor compounds, group III-V semiconductor compounds, group IV-VI semiconductor compounds, group IV elements or compounds, or combinations thereof.

[0585] There are no particular limitations on group II-VI semiconductor compounds, and examples 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 or mixtures thereof; and quaternary compounds selected from CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe or mixtures thereof.

[0586] There are no particular limitations on III-V semiconductor compounds, and examples may include: binary compounds selected from GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb or mixtures thereof; ternary compounds selected from GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb or mixtures thereof; and quaternary compounds selected from GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb or mixtures thereof.

[0587] There are no particular limitations on group IV-VI semiconductor compounds, and examples may include: binary compounds selected from SnS, SnSe, SnTe, PbS, PbSe, PbTe or mixtures thereof; ternary compounds selected from SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe or mixtures thereof; and quaternary compounds selected from SnPbSSe, SnPbSeTe, SnPbSTe or mixtures thereof.

[0588] There are no particular limitations on Group IV elements or compounds, and examples may include: single-element materials selected from Si, Ge, or mixtures thereof; or binary compounds selected from SiC, SiGe, or mixtures thereof.

[0589] Semiconductor nanocrystal particles (quantum dots) can have a homogeneous single structure or a core-shell dual structure. The core and shell can be made of different materials. Each of the materials constituting the core and shell can be composed of different semiconductor compounds. The band gap of the shell material can be larger than that of the core material. For example, the core-shell structure can be ZnTeSe / ZnSe / ZnS, InP / ZnSe / ZnS, CdSe / ZnS, InP / ZnS, etc.

[0590] This paper describes a process for preparing quantum dots with a core (CdSe) / shell (ZnS) structure. First, a core (CdSe) precursor material, such as (CH3)2Cd (dimethylcadmium) and TOPSe (trioctylphosphine selenide), is implanted into an organic solvent using TOPO (trioctylphosphine oxide) as a surfactant to form crystals. Then, after the crystals are held at high temperature for a specific period to grow to a specific size, a ZnS precursor material is implanted to form a shell on the surface of the formed core. This allows for the fabrication of TOPO-coated CdSe / ZnS quantum dots.

[0591] In the form of a perovskite-type compound (perovskite halide) comprising the light-emitting layer (PeLED), the light-emitting layer 150 may include a compound having a perovskite-type crystal structure. The perovskite-type compound may include, for example, a compound having the general formula (A... p M q X r ) represents organic-inorganic hybrid materials or inorganic materials with a perovskite-type crystal structure.

[0592] In the above general formula, A can be at least one cation selected from alkali metal cations and organic cations, M can be at least one metal cation selected from group 14 elements (such as Ge, Sn or Pb), group 15 elements (such as Sb or Bi) or transition metals (such as Cu, Ni, Co, Fe, Mn, Cr, Pd, Cd or Ag), X can be at least one anion selected from halide ions (such as Cl, Br or I), cyanide, thiocyanate, isothiocyanate or sulfide, p can represent an integer of 1 or greater and 4 or less, q can represent 1 or 2, and r can represent an integer of 3 or greater and 9 or greater.

[0593] For example, A may include: alkali metal ions, such as Li, Na, K, Rb or Cs; or organic cations, such as ammonium ions, methylammonium ions, formamidinium ions, guanidinium ions, imidazolium ions, pyridinium ions or pyridinium ions.

[0594] Specific examples of perovskite compounds may include, for example, the following compounds: CsPbI3, CsSnI3, CsPbBr3, CsSnBr3, CsPbCl3, CsSnCl3, RbPbI3, RbSnI3, RbPbBr3, RbSnBr3, RbPbCl3, or RbSnCl3, etc.

[0595] Perovskite compounds can be obtained by known methods. Perovskite compounds can be obtained by any of the following methods: wet synthesis, dry synthesis by grinding, and in-situ synthesis.

[0596] There is no particular limitation on the average particle diameter of the perovskite compound, and it can 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, for example, greater than or equal to about 1 nm and less than or equal to about 30 nm.

[0597] Perovskite compounds may have ligands on their surface. By coordinating appropriate ligands to perovskite compounds, the photoluminescence or electroluminescence quantum yield can be improved. Examples of such ligands may include, but are not particularly limited to, cross-linked ligand compounds (such as organic ammonium ions, organic acid compounds having two or more unsaturated bonds, or organic base compounds).

[0598] There are no particular limitations on the method used to form the light-emitting layer. The light-emitting layer can be formed by coating a coating solution comprising at least one of semiconductor nanocrystal particles and perovskite-type compounds (solution coating method). As a solvent constituting the coating solution, a solvent that does not dissolve the material in the hole transport layer (e.g., hole transport material, such as a polymeric compound) can be selected. However, the hole transport layer formed using the composition according to the embodiments includes a crosslinking product formed by a thiol-olefin bonding reaction between a polymer comprising a structural unit (A) represented by Chemical Formula 1 and a compound represented by Chemical Formula 10, and this crosslinking product increases the solvent resistance of the hole transport layer, thereby significantly increasing its durability against the solvent used to form the light-emitting layer. Therefore, even for solvents such as those used to form quantum dot inkjet compositions, the hole transport layer formed using the composition according to the embodiments can exhibit a high film retention rate.

[0599] An electron transport layer 160 may be formed on the light-emitting layer 150. The electron transport layer 160 may be a layer that functions to transport electrons, and may be formed using methods such as vacuum deposition, spin coating, and inkjet printing. 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.

[0600] The electron transport layer 160 may be formed of a known electron transport material. Examples of known electron transport materials may include lithium (8-hydroxyquinoline) (lithium quinoline, Liq), tris(8-hydroxyquinoline)aluminum (Alq3), or compounds having a nitrogen-containing aromatic ring. Examples of compounds having a nitrogen-containing aromatic ring may include: compounds comprising a pyridine ring, such as 1,3,5-tris[(3-pyridyl)-benzyl-3-yl]benzene; compounds comprising a triazine ring, such as 2,4,6-tris(3'-(pyridyl-3-yl)biphenyl-3-yl)-1,3,5-triazine; compounds comprising an imidazole ring, such as 2-(4-(N-phenyl-benzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene or 1,3,5-tris(N-phenyl-benzimidazol-2-yl)benzene (TPBI). The electron transport material may be used alone or in mixtures of two or more types.

[0601] An electron injection layer 170 may be formed on the electron transport layer 160. The electron injection layer 170 may be a layer that facilitates the injection of electrons from the second electrode 180. The electron injection layer 170 may be formed using a vacuum deposition method or the like. The electron injection layer 170 may be formed to have a thickness, 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 the material for forming the electron injection layer 170. For example, the electron injection layer 170 may be formed from lithium compounds (such as lithium (8-hydroxyquinoline) (quinoline lithium, Liq)), lithium fluoride (LiF), sodium chloride (NaCl), cesium fluoride (CsF), lithium oxide (Li2O), or barium oxide (BaO).

[0602] 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 from 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), or calcium (Ca)) or an alloy (such as aluminum-lithium (Al-Li), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag)). The second electrode 180 may be formed to have a thickness of, for example, from about 10 nm to about 200 nm (e.g., from 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 metallic material having a thickness of 20 nm or less (such as a transparent conductive film, for example, indium tin oxide (In2O3-SnO2) or indium zinc oxide (In2O3-ZnO)).

[0603] As described above, the EL device 100 according to this embodiment has been described as an example of an electroluminescent device according to an embodiment. The EL device 100 according to this embodiment can exhibit increased film retention when the light-emitting layer is prepared by curing a film of the composition according to the embodiment at a low temperature of less than or equal to 200°C, and exhibits excellent hole injection or hole transport properties by preventing the degradation of another organic film (e.g., a hole injection layer) present beneath the film through heat treatment at low temperature, thereby exhibiting excellent light-emitting characteristics and high luminous efficiency (current efficiency) at low driving voltage.

[0604] The stacking structure of the EL device 100 according to the embodiment is not limited to the example described above. The EL device 100 according to the embodiment can be formed with another known stacking structure. For example, the EL device 100 may omit one or more of the hole injection layer 130, electron transport layer 160 and electron injection layer 170, and may additionally include another layer. Furthermore, each layer of the EL device 100 may be formed as a single layer or as multiple layers.

[0605] 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. Furthermore, the hole blocking layer may be formed, for example, by an oxadiazole derivative, a triazole derivative, or a phenanthroline derivative.

[0606] Furthermore, the polymeric compound according to the embodiments can be applied to electroluminescent devices other than QLEDs or PeLEDs. Other electroluminescent devices to which the polymeric compound according to the embodiments can be applied include, but are not particularly limited to, organic electroluminescent devices.

[0607] Example

[0608] 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, each operation is performed at room temperature (25°C) unless specifically stated otherwise. Furthermore, unless specifically stated otherwise, “%” and “parts” represent “mass %” and “parts by mass”, respectively. Additionally, in the following chemical formulas, unless specifically limited otherwise, the “C” indicating an alkyl group is… m H 2m+1 The description “(m is an integer)” indicates a straight-chain alkyl group.

[0609] Synthesis Example 1: Synthesis of Compound M-1

[0610] Compound M-1 was synthesized according to reaction scheme 1.

[0611] (Reaction Scheme 1)

[0612] Specifically, 2,7-dibromofluorene (26.4 g) and tetrahydrofuran (THF) (400 mL) were added to a 1 L four-necked (reaction) flask and stirred at 0 °C under a nitrogen atmosphere. Then, potassium tert-butoxy (t-BuOK, 27.0 g) was added, and the mixture was stirred at 0 °C for 10 minutes. A solution prepared by dissolving 1,5-dibromohexane (414 g) in THF (180 mL) was slowly added dropwise to the reaction flask, and the mixture was stirred at 0 °C for 30 minutes. After adding 200 mL of water to the reaction flask and subsequently removing the solvent under reduced pressure, the product was extracted with ethyl acetate. After separating the aqueous layer, the organic layer was dried with magnesium sulfate. After removing volatile organic compounds and unreacted 1,6-dibromohexane under reduced pressure, the solid was washed with hexane to obtain 2,7-dibromo-9,9-bis(5-bromopentyl)-9H-fluorene (40.9 g).

[0613] In a 200 mL four-necked (reaction) flask, 2,3-dimercapto-1-propanol (25.0 g) and acetone (100 mL) were added, followed by one drop of 10 N HCl. The mixture was stirred at room temperature for 12 hours. 25 g of magnesium sulfate was then added, and the mixture was stirred for 1 hour. The magnesium sulfate was filtered off, and the acetone was removed under reduced pressure to obtain (2,2-dimethyl-1,3-dithiacyclopentan-4-yl)methanol (31.6 g).

[0614] (2,2-Dimethyl-1,3-dithiacyclopentan-4-yl)methanol (3.10 g), 2,7-dibromo-9,9-bis(5-bromopentyl)-9H-fluorene (5.83 g), and THF (38 mL) were placed in a 50 mL four-necked (reaction) flask and stirred at 0 °C under a nitrogen atmosphere. 64% NaH (1.05 g) was added and stirred for 30 min, followed by further stirring at room temperature for 3 days. Then, additional NaH (0.3 g) was added to the reaction flask, and the reaction mixture was stirred for an additional 1 h. Subsequently, the temperature of the reaction mixture was lowered to 0 °C, and stirring was applied during the addition of methanol to quench the reaction. After removing volatile organic compounds under reduced pressure, the product residue was extracted with ethyl acetate. The collected organic layer was washed with water, separated, and dried over magnesium sulfate. After solvent removal under reduced pressure, the product residue was purified by column chromatography (silicon gel, hexane / dichloromethane) to obtain compound M-1 (1.07 g).

[0615] Synthesis Example 2: Synthesis of Compound M-2

[0616] Compound M-2 was synthesized according to reaction scheme 2.

[0617] (Reaction Scheme 2)

[0618] Specifically, 10.6 g of 2,7-dibromo-9,9-bis(6-bromohexyl)-9H-fluorene, obtained in the same manner as in Synthesis Example 1, potassium thioacetate (5.28 g), and THF (154 mL) were placed into a 300 mL four-necked flask and stirred at 60 °C for 3 hours under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, and 100 mL of deionized water was added to the mixture to separate the organic layer. The aqueous layer was extracted with dichloromethane (100 mL × 3), combined with the organic layer, washed with saturated brine (100 mL × 3), separated from the aqueous layer, and dried over magnesium sulfate. After removing volatile organic compounds under reduced pressure, the product residue was purified by column chromatography (silicon gel, hexane / toluene) to obtain compound M-2 (7.84 g).

[0619] Synthesis Example 3: Synthesis of Compound C-1

[0620] Compound C-1 was synthesized according to reaction scheme 3.

[0621] (Reaction Scheme 3)

[0622] Specifically, 2-bromocarbazole (20.0 g), 4-chloro-N-(4-chlorophenyl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxoron-2-yl)phenyl)aniline (10.0 g), sodium carbonate (4.84 g), tetra(triphenylphosphine)palladium(O) (Pd(PPh3)4, 1.31 g), toluene (80 mL), ethanol (30 mL), and water (30 mL) were placed in a 100 mL four-necked (reaction) flask and stirred at 100 °C (bath temperature) for 3 hours. After cooling to room temperature, the aqueous layer was separated and removed, and the organic layer was washed with water (100 mL × 2), separated, and dried with magnesium sulfate. After removing the volatile organic compounds under reduced pressure, toluene (200 mL) was added to the residue, refluxed at 60 °C for 1 hour, and the solid was filtered, collected and dried to obtain N-(4-(9-carbazole-2-yl)phenyl)-4-chloro-N-(4-chlorophenyl)aniline (6.08 g).

[0623] Subsequently, the obtained N-(4-(9-carbazole-2-yl)phenyl)-4-chloro-N-(4-chlorophenyl)aniline (6.00 g), 1-bromo-4-hexylbenzene (3.00 g), tris(dibenzylacetone)palladium (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 purged with argon and heated at 110 °C for 7 hours. After cooling to room temperature, impurities were removed by diatomaceous earth filtration. After distilling the solvent under reduced pressure, the product residue was purified by column chromatography to obtain 4-chloro-N-(4-chlorophenyl)-N-(4-(9-(4-hexylphenyl)-9-carbazole-2-yl)phenyl)aniline (1.60 g).

[0624] The obtained 4-chloro-N-(4-chlorophenyl)-N-(4-(9-(4-hexylphenyl)-9-carbazole-2-yl)phenyl)aniline (1.60 g), dipiconol diboronate (1.90 g), potassium acetate (KOAc, 1.47 g), tris(dibenzylacetone)dipalladium (Pd2(dba)3, 0.114 g), XPhos (0.177 g), and 1,4-dioxane (16 mL) were placed in 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 using diatomaceous earth as a filter. After removing the solvent under reduced pressure, the product residue was combined with a mixed solvent of toluene (20 mL) and hexane (40 mL), and activated carbon (2.0 g) was added, followed by reflux for 30 minutes. After removing insoluble matter by using diatomaceous earth as a filter and distilling the solvent under reduced pressure, the residue was recrystallized with toluene / acetonitrile to obtain compound C-1 (1.85 g).

[0625] Synthesis Example 4: Synthesis of Polymer P-1

[0626] 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 a 20% by weight aqueous solution of tetraethylammonium hydroxide (9.01 g) were added to a four-necked flask and stirred at 85°C for 2 hours. Subsequently, phenylboronic acid (211 mg), bis(triphenylphosphine)palladium(II) dichloride (73.6 mg), and a 20% by weight aqueous solution of tetraethylammonium hydroxide (9.01 g) were added to the flask 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 to the flask and stirred at 85 °C for 6 hours. Under a nitrogen atmosphere, after separating the organic and aqueous layers, the organic layer was washed sequentially with ion-exchanged water (50 mL × 2), saturated NH4Cl aqueous solution (50 mL × 5), and ion-exchanged water (50 mL × 2).

[0627] The solid obtained was washed with methanol while being added to the washing organic layer, filtered, and then dried under vacuum. The dried solid was dissolved in toluene (20 mL), and activated alumina (9.0 g) and diatomaceous earth (4.5 g) were added to the toluene solution. The mixture was stirred at 90 °C for 1 hour, and the solid was filtered off. The solid precipitated when methanol was added to the filtrate. The solid was filtered off and then dried under vacuum. The obtained solid was dissolved in toluene (50 mL), and 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, 10 g) was added to the toluene solution. The mixture was stirred at room temperature for 12 hours. The ion exchange resin was filtered off, and the solid was reprecipitated with methanol and then dried under vacuum to obtain the P-1 precursor (0.747 g).

[0628] Subsequently, the P-1 precursor (0.730 g), Dess-Martin reagent (648 mg), toluene (28 mL), and deionized water (7 mL) were placed in a double-necked flask and stirred at room temperature for 12 hours under a nitrogen atmosphere. The organic layer was separated and added dropwise to methanol to precipitate a solid, which was then dried under vacuum. The obtained solid was dissolved in toluene (50 mL), and anion exchange resin (10 g) was added and stirred for 12 hours. The deion exchange resin was filtered off, and the filtrate was added dropwise to methanol to precipitate a solid. The solid was filtered, dissolved in toluene, and this solution was added dropwise to methanol to precipitate the solid. The solid was filtered and dried to obtain polymer P-1 (0.634 g). The weight-average molecular weight (Mw) and polydispersity (Mw / Mn) of polymer P-1 were measured by SEC. The results showed that Mw was 202,000 Da and Mw / Mn was 3.34.

[0629] The following structural units of polymer P-1 were determined by the monomer input ratio.

[0630] (Polymer P-1)

[0631]

[0632] Synthesis Example 5: Synthesis of Polymer P-2

[0633] 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 weight aqueous solution of tetraethylammonium hydroxide (8.99 g) were added to a four-necked flask and stirred at 85°C for 2 hours. Subsequently, phenylboronic acid (211 mg), bis(triphenylphosphine)palladium(II) dichloride (73.6 mg), and a 20% by weight aqueous solution of tetraethylammonium hydroxide (9.01 g) were added to the flask 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 to the flask and stirred at 85 °C for 6 hours. Under a nitrogen atmosphere, after separating the organic layer from the aqueous layer, the organic layer was washed sequentially with ion-exchanged water (50 mL × 2), saturated NH4Cl aqueous solution (50 mL × 5), and ion-exchanged water (50 mL × 2).

[0634] The solid obtained by washing, filtering, and vacuum drying with methanol was added to the washed organic layer. The dried solid was dissolved in toluene (20 mL), and activated alumina (9.0 g) and diatomaceous earth (4.5 g) were added. The mixture was stirred at 90 °C for 1 hour and filtered. A solid was formed by adding methanol to the filtrate, which was then filtered and vacuum dried. The obtained solid was dissolved in toluene (50 mL), and 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, 10 g) was added. The mixture was stirred at room temperature for 12 hours. The ion exchange resin was filtered off, and a solid reprecipitated with methanol was obtained and vacuum dried to obtain the P-2 precursor (0.785 g).

[0635] Subsequently, the P-2 precursor (0.730 g), Desmond reagent (365 mg), toluene (20 mL), and deionized water (20 mL) were placed in a two-necked flask and stirred at room temperature for 12 hours under a nitrogen atmosphere. The resulting organic layer was added dropwise to methanol to precipitate a solid, which was then filtered and dried under vacuum. The obtained solid was dissolved in toluene (50 mL), and 10 g of anion exchange resin was added, followed by stirring for 12 hours. The ion exchange resin was filtered off, and the filtrate was added dropwise to methanol to precipitate a solid, which was then dissolved in toluene. This solution was added dropwise to methanol to precipitate a solid, which was then filtered and dried to obtain polymer P-2 (0.491 g). The weight-average molecular weight (Mw) and polydispersity (Mw / Mn) of polymer P-2 were measured by SEC. The results showed that Mw was 277,000 Da and Mw / Mn was 2.56.

[0636] The following structural units of polymer P-2 were determined by the monomer input ratio.

[0637] (Polymer P-2)

[0638] Synthesis Example 6: Preparation of Low Molecular Weight Compounds

[0639] The compounds represented by the following chemical formulas were purchased from Alfa Chemistry and used in the following synthesis.

[0640]

[0641] Example 1: Preparation of Composition 1

[0642] The polymer P-2 prepared in Synthesis Example 5 and the compound prepared in Synthesis Example 6 were mixed in a weight ratio of 2:1 and dissolved in o-xylene solvent at a concentration of 1 wt%, and 0.1 wt% (based on the weight of polymer P-2) of Irgacure 369 (photoinitiator) was added to prepare composition 1 according to Example 1.

[0643] Example 2: Preparation of Composition 2

[0644] The polymer P-1 prepared in Synthesis Example 4 and the compound prepared in Synthesis Example 6 were mixed in a weight ratio of 2:1 and dissolved in o-xylene solvent at a concentration of 1 wt%. 0.1 wt% (based on the weight of polymer P-2) of Irgacure 369 (photoinitiator) was added to prepare composition 2 according to Example 2.

[0645] Comparative Examples 1 to 3: Preparation of Comparative Compositions 1 to 3

[0646] Comparative composition 1 was prepared by dissolving polymer P-2 prepared in Synthesis Example 5 alone in o-xylene solvent at a concentration of 0.1 wt%, without adding the compound prepared in Synthesis Example 6.

[0647] Comparative composition 2 was prepared by dissolving polymer P-1 prepared in Synthesis Example 4 alone in o-xylene solvent at a concentration of 0.1 wt%, without adding the compound prepared in Synthesis Example 6.

[0648] Furthermore, comparative composition 3 was prepared by dissolving the compound prepared in synthesis example 6 alone in o-xylene solvent at a concentration of 0.1 wt% without adding any polymers prepared in synthesis examples 4 and 5.

[0649] Manufacturing Example 1: Thin Film Fabrication and Evaluation

[0650] Compositions according to Examples 1 and 2, and Comparative Examples 1 to 3, were each coated onto glass substrates using spin coating. These compositions were then heated to 150°C and 190°C respectively to produce films, and the thickness of the produced films was measured. Subsequently, each glass substrate on which the films were formed was immersed in cyclohexylbenzene, and each substrate was removed to remove the cyclohexylbenzene, and the thickness of the remaining film was measured. The thickness of each film before immersion in cyclohexylbenzene and the thickness of each film after immersion in cyclohexylbenzene are shown in Table 1 below, and the ratio of the thickness after immersion in cyclohexylbenzene to the thickness before immersion in cyclohexylbenzene is described in Table 1 below as film retention rate.

[0651] Furthermore, the absorption coefficient (or extinction coefficient) of each film prepared by curing each composition according to the comparative example and the example at 150°C and 190°C, respectively, was measured using an ellipsometer for wavelengths from approximately 300 nm to approximately 700 nm before and after immersing the film in cyclohexylbenzene, and the results are shown in... Figures 2 to 11 middle.

[0652] Reference Figure 2 and Figure 4 When the compositions according to Comparative Example 1 and Comparative Example 2 were cured at 150°C and then immersed in cyclohexylbenzene, the absorption coefficient between about 300 nm and about 450 nm was almost non-existent compared with that before immersion in cyclohexylbenzene. This indicates that the film was almost dissolved by cyclohexylbenzene, resulting in a very low film retention rate.

[0653] Conversely, refer to Figure 3 and Figure 5 It can be seen that when the compositions according to Comparative Example 1 and Comparative Example 2 are cured at 190°C, the absorption coefficient between approximately 300 nm and approximately 450 nm decreases after immersion in cyclohexylbenzene compared to before immersion, but a relatively high film retention rate is observed compared to curing at 150°C. In other words, it can be seen that curing at a higher temperature can improve the film retention rate of the polymer.

[0654] On the other hand, in the case of a film manufactured from the composition according to Comparative Example 3, when cured at 150°C ( Figure 6 ) and when cured at 190°C ( Figure 7 Both showed significantly lower absorption coefficients for wavelengths between 300 nm and 400 nm after immersion in cyclohexylbenzene than before, indicating that solvent tolerance is significantly lower in the case of low molecular weight compounds rather than high molecular weight compounds, even when cured at relatively high temperatures.

[0655] On the other hand, when the films manufactured by heat-treating the compositions of Examples 1 and 2 at 150°C and 190°C respectively were measured for absorption coefficients before and after immersion in cyclohexylbenzene, as shown from... Figures 8 to 11 It can be seen that the film prepared by curing at 150°C exhibits a slightly lower absorption coefficient after immersion in cyclohexylbenzene compared to before immersion in cyclohexylbenzene. However, the decrease in absorption coefficient is minimal compared to the film according to the comparative example, and it can be seen that when cured at 190°C, the absorption coefficient does not decrease at all compared to before cyclohexylbenzene treatment (see [link to comparative example]). Figure 9 and Figure 11 ).

[0656] In other words, by heat-treating the composition according to the embodiment, comprising both a polymer containing thiol groups and a low molecular weight compound containing vinyl groups, at a low temperature of 190°C or lower, a crosslinking product is formed between the polymer and the low molecular weight compound through a thiol-ene bonding reaction between the thiol groups and the vinyl groups. This significantly increases the solvent resistance of the film comprising the composition, and thus significantly improves the film retention even after cyclohexylbenzene treatment. The results are shown in Table 1 below.

[0657] Table 1

[0658] Manufacturing Example 2-1: Manufacturing and Evaluation of Quantum Dot Electroluminescent Device 1

[0659] As the first electrode (anode), an ITO-attached glass substrate was patterned with indium tin oxide (ITO) to form a film thickness of 150 nm. The ITO-attached glass substrate was sequentially washed with a neutral detergent, deionized water, water, and isopropanol, and then treated with UV-ozone. Subsequently, poly(3,4-ethylenedioxythiophene) / poly(4-styrene sulfonate) (PEDOT / PSS) (Sigma-Aldrich Co., Ltd.) was spin-coated onto the ITO-attached glass substrate to a dry film thickness of 30 nm and dried. As a result, a hole injection layer with a thickness of 30 nm (dry film thickness) was formed on the ITO-attached glass substrate.

[0660] On the hole injection layer, a toluene solution comprising a composition containing polymer P-2 according to synthesis example 5 and a compound according to synthesis example 6 (e.g., the composition of example 1) is spin-coated onto a dried film thickness of 30 nm and heat-treated at 150 °C for 60 minutes to form a hole transport layer. As a result, a hole transport layer with a thickness of 30 nm (dried film thickness) is formed on the hole injection layer.

[0661] A quantum dot dispersion was prepared by dispersing blue quantum dots of ZnTeSe / ZnSe / ZnS (core / shell / shell; average diameter approximately 10 nm) at 1.0% by mass in cyclohexylbenzene. The quantum dot dispersion was spin-coated onto a hole transport layer to a dry film thickness of 30 nm and then dried. As a result, a quantum dot emitting layer with a thickness of 30 nm (dry film thickness) was formed on the hole transport layer. The light emitted by the quantum dot dispersion under ultraviolet irradiation had a center wavelength of 462 nm and a full width at half maximum (FWHM) of 30 nm.

[0662] The quantum dot emitting layer was completely dried. On this quantum dot emitting layer, lithium (8-hydroxyquinoline) (quinoline lithium, Liq) and 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI) (Sigma-Aldrich Co., Ltd.) were co-deposited as electron transport materials using a vacuum deposition apparatus. As a result, an electron transport layer with a thickness of 36 nm was formed on the quantum dot emitting layer.

[0663] On the electron transport layer, lithium (8-hydroxyquinoline) (lithium quinoline, Liq) was deposited using a vacuum deposition apparatus. As a result, a 0.5 nm thick electron injection layer was formed on the electron transport layer.

[0664] Aluminum (Al) was deposited on the electron injection layer using a vacuum deposition apparatus. As a result, a second electrode (cathode) with a thickness of 100 nm was formed on the electron injection layer. In this way, a quantum dot electroluminescent device 1 was obtained.

[0665] Manufacturing Example 2-2: Manufacturing of Quantum Dot Electroluminescent Device 2

[0666] The quantum dot electroluminescent device 2 is manufactured in the same manner as in manufacturing Example 2-1, except that a hole transport layer is formed by heat-treating the composition according to Example 2 at 150°C for 60 minutes.

[0667] Manufacturing Example 2-3: Manufacturing of Quantum Dot Electroluminescent Device 3

[0668] The quantum dot electroluminescent device 3 is manufactured in the same manner as in manufacturing Example 2-1, except that a hole transport layer is formed by heat-treating the composition according to Example 1 at 190°C for 60 minutes.

[0669] Manufacturing Example 2-4: Manufacturing of Quantum Dot Electroluminescent Device 4

[0670] The quantum dot electroluminescent device 4 is manufactured in the same manner as in manufacturing Example 2-1, except that a hole transport layer is formed by heat-treating the composition according to Example 2 at 190°C for 60 minutes.

[0671] Comparative Manufacturing Example 1: Comparative Manufacturing of Quantum Dot Electroluminescent Device 1

[0672] The comparative quantum dot electroluminescent device 1 is manufactured in the same manner as in manufacturing examples 2-1, except that a hole transport layer is formed by using a composition according to comparative example 1 containing only polymer P-2 according to synthesis example 5 instead of the composition according to example 1.

[0673] Comparative Manufacturing Example 2: Comparative Manufacturing of Quantum Dot Electroluminescent Device 2

[0674] The comparative quantum dot electroluminescent device 2 is manufactured in the same manner as in manufacturing example 2-1, except that a hole transport layer is formed by using a composition of comparative example 2 containing only polymer P-1 according to synthesis example 4 instead of the composition according to example 1.

[0675] Comparative Manufacturing Example 3: Comparative Manufacturing of Quantum Dot Electroluminescent Device 3

[0676] The comparative quantum dot electroluminescent device 3 is manufactured in the same manner as in manufacturing examples 2-1, except that the hole transport layer is formed by using the composition of comparative example 3, which contains only the low molecular weight compound of synthetic example 6, instead of the composition of example 1.

[0677] Evaluation of electroluminescent devices

[0678] The following method is used to target the maximum external quantum efficiency (EQE). Max ), maximum luminance (Lum. Max.), luminous efficacy at 20,000 nits (EQE@20000nit), voltage at 5mA (V@5mA), luminance at 5mA (Cd / m²) 2 (Cd / m) 2 The quantum dot electroluminescent devices 1 to 4 of Manufacturing Examples 2-1 to 2-4 and comparative quantum dot electroluminescent devices 1 to 3 of Comparative Manufacturing Examples 1 to 3 were evaluated for durability (@5mA) and performance (Max. T90, T90, T50). The results are shown in Table 2 below.

[0679] Here, external quantum efficiency (EQE) refers to the ratio of the number of photons emitted from a given light-emitting device to the number of electrons passing through that device. EQE can be a measure of how efficiently a light-emitting device converts electrons into photons and allows photons to escape. Here, maximum external quantum efficiency (EQE) is... Max () refers to the maximum value of external quantum efficiency.

[0680] Luminous efficiency (external quantum efficiency (EQE))

[0681] When a voltage is applied to each of the quantum dot electroluminescent devices, the device emits light as current begins to flow at the predetermined voltage. The current at each device is measured by slowly increasing the voltage using a DC constant voltage power supply (Keithley 2200), and the brightness of the device at the moment of light emission is measured using a luminance meter (Minolta CS200). Brightness measurements are stopped at the moment the brightness begins to decay.

[0682] Furthermore, the spectral radiance spectrum measured by a luminance meter under the assumption of Lambertian radiation is used to calculate the maximum external quantum efficiency (EQE). Max (%), with the maximum external quantum efficiency used to evaluate luminescence efficiency.

[0683] T90, T50, and Max. T90

[0684] A predetermined voltage was applied to each of the quantum dot electroluminescent devices using a DC constant voltage power supply (Keithley 2200), causing light emission. The brightness of each device was measured by slowly increasing the applied current using a luminance meter (Minolta CS200). Then, when the brightness reached 650 nits (cd / m²), the measurement was completed. 2 When the current is kept constant, the device is operated. As time passes, the brightness of the device decreases. The amount of time taken to reach 90% of the initial brightness (100%) of the device is measured as "T90" (h), and the amount of time taken to reach 50% of the initial brightness (100%) of the device is measured as "T50" (h).

[0685] Here, Max. T90 refers to the time required for the brightness of a given device to decrease from its maximum brightness (100%) to 90% when the device is driven at a given brightness level. Here, maximum brightness (Lum. Max.) refers to the maximum brightness that the device can achieve.

[0686] Table 2

[0687] Referring to the results in Table 2, compared with comparative quantum dot electroluminescent devices 1 and 2, which included a hole transport layer prepared by replacing the composition according to the examples with a composition containing only polymers, and comparative quantum dot electroluminescent devices 3, which included a hole transport layer prepared by replacing the composition according to the examples with a composition containing only low molecular weights, quantum dot electroluminescent devices 1 to 4, which included manufacturing examples 2-1 to 2-4, confirmed that the maximum external quantum efficiency (EQE) was higher than that of comparative quantum dot electroluminescent devices 3. MaxThe luminance is at least about 1.5 times higher and no more than about 3.5 times higher, the maximum luminance is also at least about 1.1 times higher and no more than nearly 3 times higher, and the external quantum efficiency (EQE@20,000 nits) at a high luminance of 20,000 nits, as well as the voltage and luminance at 5 mA, are also significantly higher. In other words, it can be seen that the quantum dot electroluminescent device to which the composition according to the embodiments is applied to the hole transport layer exhibits better luminescent characteristics and luminescent efficiency than the comparative quantum dot electroluminescent devices. Furthermore, the maximum T90, T90, and T50 of the quantum dot electroluminescent devices manufactured in Examples 2-1 to 2-4 are much higher than the maximum T90, T90, and T50 of the comparative quantum dot electroluminescent devices, indicating that the quantum dot electroluminescent device including the hole transport layer prepared by using the composition according to the embodiments also has excellent durability (significantly long luminescent lifetime).

[0688] In particular, it can be seen that, compared with the quantum dot electroluminescent devices 1 and 2 of Manufacturing Examples 2-1 and 2-2 formed by curing the compositions according to Examples 1 and 2 at 150°C to form a hole transport layer, the quantum dot electroluminescent devices 3 and 4 of Manufacturing Examples 2-3 and 2-4, in which the hole transport layer is formed by curing the compositions at 190°C, exhibit significantly superior luminescent properties, as well as superior luminescent efficiency and lifetime compared with comparative quantum dot electroluminescent devices 1 to 3. That is, by curing at 190°C, which is above 150°C, the thiol-olefin binding reaction of the compositions according to the examples proceeds better, and as a result, a denser cross-linked structure is formed, which further improves the film retention rate of the hole transport layer, and as a result, exhibits better hole transport properties, thus enabling the electroluminescent device including it to exhibit superior physical properties.

[0689] Figure 12 This is a graph showing the external quantum efficiency versus brightness for comparative quantum dot electroluminescent devices 1 and 2 according to comparative manufacturing examples 1 and 2, and quantum dot electroluminescent devices 3 and 4 according to manufacturing examples 2-3 and 2-4. Figure 12 It can be seen that the comparative quantum dot electroluminescent devices 1 and 2, which include hole transport layers made only of polymers containing thiol groups, have significantly lower external quantum efficiencies when cured at about 150°C to form hole transport layers than the quantum dot electroluminescent devices 3 and 4, in which hole transport layers are formed by curing the compositions according to Examples 1 and 2 at 190°C, and are difficult to use as electroluminescent devices.

[0690] Figure 13This is a graph showing the decrease in brightness over time for quantum dot electroluminescent devices 3 and 4 according to manufacturing examples 2-3 and 2-4, compared to comparative quantum dot electroluminescent devices 1 and 2 according to comparative manufacturing examples 1 and 2. Figure 13 It can be seen that comparative quantum dot electroluminescent devices 1 and 2, which form a hole transport layer by curing a composition consisting only of polymers including thiol groups at 150°C, exhibit a brightness reduction to half of the initial brightness after approximately 20 hours. In contrast, quantum dot electroluminescent devices 3 and 4, which form a hole transport layer by curing the compositions according to Examples 1 and 2 at 190°C, take more than 90 hours or approximately 100 hours to exhibit a brightness reduction to 50% of the initial brightness. In other words, it can be seen that the quantum dot electroluminescent devices formed by curing the compositions according to the embodiments at 190°C to form a hole transport layer also exhibit significantly superior durability compared to the electroluminescent devices according to the comparative manufacturing examples.

[0691] In summary, it can be seen that, according to the embodiments, by curing a composition comprising a polymer containing thiol groups and a low molecular weight compound containing unsaturated bonds (such as vinyl groups) together at a low temperature of 200°C or lower (e.g., about 190°C), excellent crosslinking can be formed without the damage to the hole injection layer caused by curing at high temperatures in the prior art. As a result, the manufactured crosslinked product can exhibit excellent hole transport characteristics and thus high luminous efficiency and luminous properties due to a high film retention rate, without any deterioration of the individual hole transport characteristics.

[0692] While the foregoing has been described with reference to embodiments, this disclosure is not limited to the specific embodiments, and various modifications and alterations are possible within the scope of the invention described in the claims.

[0693] <Description of Symbols>

[0694] 100… Electroluminescent devices (EL devices)

[0695] 110…base

[0696] 120…First Electrode

[0697] 130…hole injection layer

[0698] 140…Hole transport layer

[0699] 150…Emitting layer

[0700] 160… Electron transport layer

[0701] 170… Electron Injection Layer

[0702] 180…Second electrode

Claims

1. A composition comprising a polymer and a compound, the polymer comprising a first structural unit represented by Chemical Formula 1, the compound represented by Chemical Formula 10: Chemical Formula 1 Chemical Formula 1 wherein In Chemical Formula 1, Ar 11 and Ar 12 each independently is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, Ar 11 with Ar 12 optionally connected to each other to form a ring, L 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring-forming atoms, Ar 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, Ar 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring-forming atoms, Ar 1 with Ar 2 optionally connected to each other to form a ring, X 1 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring-forming atoms, and Y 1 is a group selected from a group of aromatic hydrocarbon groups having 6 to 25 ring-forming atoms substituted with an alkyl group having a sulfur-containing mercapto group having 1 to 14 carbon atoms, an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted with an alkoxyalkyl group having a sulfur-containing mercapto group having 2 to 14 carbon atoms, and an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted with an alkyl group having a sulfur-containing mercapto group having 1 to 14 carbon atoms and an alkoxyalkyl group having a sulfur-containing mercapto group having 2 to 14 carbon atoms; Chemical Formula 10 wherein, in Chemical Formula 10, Ar and Ar 5 to Ar 8 each independently is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, a substituted or unsubstituted heteroaromatic ring group having 5 to 25 ring-forming atoms, or a combination thereof, wherein the aromatic hydrocarbon group and the heteroaromatic ring group include a monocyclic ring, a fused ring of two or more rings, or a combination of rings in which the monocyclic ring and / or the fused ring are connected by a single bond, Ar 5 with Ar 6 and / or Ar 7 with Ar 8 each independently optionally linked to each other to form a ring, Ar and Ar 5 to Ar 8 at least two of Ar and Ar are each independently substituted with a C2 to C10 aliphatic hydrocarbon group comprising a carbon-carbon double bond or a carbon-carbon triple bond, or a C3 to C10 cycloaliphatic hydrocarbon group comprising a carbon-carbon double bond or a carbon-carbon triple bond.

2. The composition of claim 1, wherein, the first structural unit is represented by Chemical Formula 1-1: Chemical Formula 1-1 wherein, in Chemical Formula 1-1, R 11 to R 14 and R 21 to R 24 each independently is 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 combined with each other to form a ring, and L 1 、Ar 1 、Ar 2 、X 1 and Y 1 are the same as L 1 , Ar 1 , Ar 2 , X 1 and Y 1 defined in Chemical Formula 1, respectively.

3. The composition of claim 1, wherein, the polymer further comprises a second structural unit represented by Chemical Formula 2: Chemical Formula 2 wherein, in Chemical Formula 2, Ar 21 and Ar 22 each independently is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, Ar 21 with Ar 22 optionally connected to each other to form a ring, L 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring-forming atoms, Ar 3 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, Ar 4 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring-forming atoms, Ar 3 with Ar 4 optionally connected to each other to form a ring, X 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 ring-forming atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring-forming atoms, Y 2 is an aromatic hydrocarbon group having 6 to 25 ring-forming atoms which is unsubstituted or substituted by alkyl having 1 to 14 carbon atoms, and Ar 21 , Ar 22 , L 2 , Ar 3 , Ar 4 and X 2 does not have an alkyl group having a thiol group having 1 to 14 carbon atoms, and does not have an alkoxyalkyl group having a thiol group having 2 to 14 carbon atoms.

4. The composition of claim 3, wherein, the second structural unit is represented by Chemical Formula 2-1: Chemical Formula 2-1 wherein, in Chemical Formula 2-1, R 31 to R 34 and R 41 to R 44 each independently is 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 combined with each other to form a ring, L 2 , Ar 3 , Ar 4 , X 2 , and Y 2 are the same as L 2 , Ar 3 , Ar 4 , X 2 , and Y 2 defined in Chemical Formula 2, respectively, and R 31 to R 34 , R 41 to R 44 , L 2 , Ar 3 , Ar 4 and X 2 do not have an alkyl group having a thiol group having from 1 to 14 carbon atoms, and do not have an alkoxyalkyl group having a thiol group having from 2 to 14 carbon atoms.

5. The composition of claim 3, wherein, in the polymer, the first structural unit is included in an amount greater than or equal to 1 mol% and less than 30 mol% based on the total moles of the first structural unit and the second structural unit.

6. The composition of claim 1, wherein, Y of Chemical Formula 1 1 The thiol group-containing alkoxyalkyl of Formula i-1, and Y of Chemical Formula 1 1 The thiol group-containing alkyl of Formula i-2: Chemical Formula i-1 Chemical Formula i-2 wherein, in Chemical Formula i-1 and Chemical Formula i-2, Z 1 represents an alkylene group having 1 to 14 carbon atoms which is substituted or unsubstituted by a thiol group, Z 2 represents an alkylene group having 1 to 13 carbon atoms which is substituted or unsubstituted by a thiol group, the sum of the carbon number of the alkylene group represented by Z 1 in Chemical Formula I-1 and the carbon number of the alkylene group represented by Z 2 is an integer of 14 or less, and Ring carbon that is bound to an aromatic hydrocarbon group having from 6 to 25 ring-forming atoms.

7. The composition of claim 1, wherein, Y in Chemical Formula 1 1 is an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted with a sulfur-containing mercapto group-containing alkoxyalkyl group having 2 to 14 carbon atoms, or an aromatic hydrocarbon group having 6 to 25 ring-forming atoms substituted with a sulfur-containing mercapto group-containing alkyl group having 1 to 10 carbon atoms.

8. The composition of claim 7, wherein, the thiol group-containing alkoxyalkyl group has two or more thiol groups.

9. The composition of claim 1, wherein, In Chemical Formula 1, Y 1 is one of groups represented by Chemical Formulae 3-1 to 3-6: wherein, in Chemical Formula 3-1 to Chemical Formula 3-6, R 301 , R 302 , R 305 , R 307 , and R 308 are each independently substituted or unsubstituted alkylene having from 1 to 14 carbon atoms, R 303 , R 304 , R 306 , R 309 , and R 310 are each independently substituted or unsubstituted alkylene having from 1 to 11 carbon atoms, and represents a binding site.

10. The composition of claim 1, wherein, L 1 is any one of the groups represented by Chemical Formula 4-1 to Chemical Formula 4-24: wherein, in Chemical Formula 4-1 to Chemical Formula 4-24, represents the position of bonding to the nitrogen atom, and represents the position of binding to Ar 1 of the formula (I) 11. The composition of claim 1, wherein, In Chemical Formula 1, -L 1 -Ar 1 -N(Ar 2 )(X 1 ) is any one of groups represented by Chemical Formula 5-1 to Chemical Formula 5-3: wherein, in Chemical Formula 5-1 to Chemical Formula 5-3, R 501 to R 506 each independently is 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 X is the same as defined in Chemical Formula 1 1 and represents the position of bonding to the nitrogen atom.

12. The composition of claim 1, wherein, in Chemical Formula 10, Ar and Ar 5 to Ar 8 each independently is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 15 ring-forming atoms, a substituted or unsubstituted heteroaromatic ring group having 5 to 15 ring-forming atoms, or a combination thereof, wherein the aromatic hydrocarbon group and the heteroaromatic ring group each independently comprises a monocyclic ring, a fused ring of two or more rings, or a combination of rings in which the monocyclic ring and / or the fused ring are connected by a single bond, Ar 5 with Ar 6 and / or Ar 7 with Ar 8 each independently optionally linked to each other to form a ring, Ar 5 to at least two of Ar 8 each independently are substituted with a C2to C5aliphatic hydrocarbon group comprising a carbon-carbon double or triple bond, or a C3to C6cycloaliphatic hydrocarbon group comprising a carbon-carbon double or triple bond.

13. The composition of claim 1, wherein, in Chemical Formula 10, Ar is a substituted or unsubstituted phenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted biphenylene group, or a combination thereof, Ar 5 to Ar 8 each independently is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted acridinyl, substituted or unsubstituted pyridinyl, or a combination thereof, Ar 5 with Ar 6 and / or Ar 7 with Ar 8 each independently optionally linked to each other to form a substituted or unsubstituted carbazole ring, or a fused ring of substituted or unsubstituted indole and pyridine, and Ar 5 and Ar 6 One of them and Ar 7 and Ar 8 Each of the groups is independently replaced by a C2 to C4 aliphatic hydrocarbon group, including a carbon-carbon double bond or a carbon-carbon triple bond.

14. The composition of claim 1, wherein, the compound represented by Chemical Formula 10 is represented by Chemical Formula 10-1: Chemical Formula 10-1 wherein, in Chemical Formula 10-1, is a substituted or unsubstituted heteroaromatic ring group having 5 to 15 ring-forming atoms, Ar 5 to Ar 8 respectively, Ar 5 to Ar 8 the same, R a and R b each independently is deuterium, a C1to C10alkyl group, a C2to C10alkenyl group, a C1to C10haloalkyl group, a halogen atom, a cyano group, a nitro group, or a combination thereof, x and y are each independently an integer of 0 to 4, and m and n are each independently an integer of 0 to 3.

15. The composition of claim 1, wherein, The polymer represented by Chemical Formula 1 and the compound represented by Chemical Formula 10 each independently have a hole transport coefficient greater than or equal to 10 -5 cm 2 V -1 s -1 of the hole transport coefficient.

16. A thin film manufactured by curing the composition according to any one of claims 1 to 15.

17. The thin film according to claim 16, comprising a crosslinked polymer in which a compound of Chemical Formula 10 forms a crosslink within the polymer between adjacent first structural units by a thiol-ene coupling reaction.

18. An electroluminescent device comprising: a first electrode and a second electrode facing each other, a light-emitting layer disposed between the first electrode and the second electrode, and at least one organic film between the first electrode and the light-emitting layer, wherein the at least one organic film comprises the thin film according to claim 16, wherein the thin film is a hole-transporting layer.

19. The electroluminescent device of claim 18, wherein, The at least one organic film further comprises a hole-injection layer between the first electrode and the thin film.

20. The electroluminescent device according to claim 18 or claim 19, wherein, The light-emitting layer comprises semiconductor nanocrystal particles, a perovskite compound, or a combination thereof.

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