Organic light emitting device, crosslinker compound for organic light emitting device, and method for manufacturing organic light emitting device

Abstract

An organic light emitting device of embodiments of the present disclosure includes a first electrode, a hole transport zone, an emission layer, an electron transport zone, and a second electrode stacked one by one, wherein the hole transport zone is obtained from a hole transport material including a crosslinker compound represented by Formula 1. The organic light emitting device can be manufactured by a wet process, and emission efficiency and driving voltage properties of the organic light emitting device can be improved. Formula 1

Description

[0001] Cross-reference to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2020-0054089, filed on May 6, 2020, the entire contents of which are incorporated herein by reference. Technical Field

[0003] One or more aspects of embodiments of this disclosure relate to organic light-emitting devices and crosslinking agent compounds used therein, and for example, to crosslinking agent compounds used as materials for forming hole transport regions and organic light-emitting devices comprising said crosslinking agent compounds. Background Technology

[0004] Organic light-emitting displays (OLEDs) are being actively developed as image displays. Unlike liquid crystal displays (LCDs), OLEDs are so-called self-emissive displays, in which holes and electrons injected from the first and second electrodes recombine in the emitting layer, and the organic light-emitting material in the emitting layer can emit light to achieve the display.

[0005] In display applications, there is a desire for lower driving voltages and increased emission efficiency and / or lifespan of organic light-emitting devices, and there is a continuous expectation for the development of materials for organic light-emitting devices that can reliably meet these requirements.

[0006] To achieve highly efficient organic light-emitting devices, improved hole transport layer materials are being developed. Summary of the Invention

[0007] One or more aspects of the embodiments of this disclosure relate to organic light-emitting devices having improved emission efficiency and / or driving voltage properties.

[0008] One or more aspects of the embodiments of this disclosure relate to organic light-emitting devices that can be manufactured using wet processes and the crosslinking agent compounds described herein.

[0009] One or more exemplary embodiments of this disclosure provide an organic light-emitting device including a first electrode, a hole transport region disposed on the first electrode, an emission layer disposed on the hole transport region, an electron transport region disposed on the emission layer, and a second electrode disposed on the electron transport region, wherein at least a portion of the hole transport region is formed (e.g., formed) of a hole transport material comprising a crosslinking agent compound represented by Formula 1:

[0010] Formula 1

[0011]

[0012] In Formula 1, A can be a hydrogen atom or a deuterium atom, L1and L2may each independently be a direct bond or a substituted or unsubstituted methylene group, "m" can be an integer of 1 to 100, and "n1" and "n2" can each independently be 1 or 2. "N3" refers to an azido group.

[0013] In an embodiment, the hole transport zone can include a hole injection layer disposed on the first electrode and a hole transport layer disposed on the hole injection layer, and the hole transport layer can be derived from the hole transport material including the crosslinker compound represented by Formula 1.

[0014] In an embodiment, the hole transport zone can include a plurality of organic layers, and an organic layer of the plurality of organic layers adjacent (e.g., closest or directly adjacent) to the emission layer can be derived from the hole transport material including the crosslinker compound represented by Formula 1.

[0015] In an embodiment, the crosslinker compound represented by Formula 1 can be represented by Formula 1-1 or Formula 1-2:

[0016] Formula 1-1

[0017]

[0018] Formula 1-2

[0019]

[0020] In Formula 1-1 and Formula 1-2, A can be the same as defined in Formula 1.

[0021] In an embodiment, the hole transport material can further include a polymer compound including a substituted or unsubstituted triarylamine group.

[0022] In an embodiment, the polymer compound can be represented by Formula 2-1 or Formula 2-2:

[0023] Formula 2-1

[0024]

[0025] Formula 2-2

[0026]

[0027] In Formula 2-1 and Formula 2-2, R1 to R7 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, "a1" can be an integer of 0 to 5, "a2" and "a3" can each independently be an integer of 0 to 4, "a4" and "a5" can each independently be an integer of 0 to 3, and "p1" and "p2" can each independently be an integer of 1 to 100.

[0028] In an embodiment, the polymer compound can be represented by any one of Formula 2-1-1, Formula 2-1-2, and Formula 2-2-1:

[0029] Formula 2-1-1

[0030]

[0031] Formula 2-1-2

[0032]

[0033] Formula 2-2-1

[0034]

[0035] In Formula 2-1-1, Formula 2-1-2, and Formula 2-2-1, "p1" and "p2" can be the same as defined in Formula 2-1 and Formula 2-2.

[0036] In an embodiment, a weight ratio of the polymer compound and the crosslinker compound included in the hole transport material can be about 4:1 to about 19:1.

[0037] In an embodiment, in the hole transport zone, the polymer compound can be thermally or photo-crosslinked with the crosslinker compound.

[0038] In an embodiment of the present disclosure, the crosslinker compound according to the embodiment can be represented by Formula 1.

[0039] One or more exemplary embodiments of the present disclosure provide a method of manufacturing an organic light emitting device, including: preparing a first electrode, supplying a hole transport material onto the first electrode to form a hole transport zone, forming an emission layer on the hole transport zone, and forming a second electrode on the emission layer, wherein the hole transport material includes a crosslinker compound represented by Formula 1.

[0040] In the method of manufacturing an organic light emitting device according to an embodiment of the disclosure, the hole transport layer can be formed by the hole transport material.

[0041] In an embodiment, the method can further include preparing the hole transport material by mixing the polymer compound, the crosslinker compound, and a solvent, before the hole transport material is supplied onto the first electrode.

[0042] In an embodiment, the forming of the hole transport zone can further include, after the hole transport material is supplied, applying heat or photo-curing the supplied hole transport material.

[0043] In an embodiment, the supplying of the hole transport material can be performed by a wet process such as spin coating, inkjet printing, nozzle printing, and spray printing. BRIEF DESCRIPTION OF DRAWINGS

[0044] The accompanying drawings are included to provide a further understanding of the disclosure and are incorporated in and constitute a part of this specification, illustrate exemplary embodiments of the disclosure, and together with the description serve to explain the principles of the disclosure. In the drawings:

[0045] Figure 1 FIG. 1 is schematically illustrates a cross-sectional view of an organic light emitting device according to an embodiment of the disclosure;

[0046] Figure 2 FIG. 2 is schematically illustrates a cross-sectional view of an organic light emitting device according to an embodiment of the disclosure;

[0047] Figure 3 FIG. 3 is schematically illustrates a cross-sectional view of an organic light emitting device according to an embodiment of the disclosure; and

[0048] Figures 4A to 4C FIG. 4 is schematically illustrates a cross-sectional view of a part of steps in a method for manufacturing an organic light emitting device according to an embodiment of the disclosure. DETAILED DESCRIPTION

[0049] The present disclosure can have various modifications and can be implemented in different forms, and exemplary embodiments will be explained in more detail with reference to the accompanying drawings. The present disclosure should not be construed as being limited to the embodiments set forth herein. Rather, all modifications, equivalents, and alternatives falling within the spirit and technical scope of the inventive concept should be included in the present disclosure.

[0050] It will be understood that when an element is referred to as being "on" another element, "connected to" another element, or "coupled to" another element, it can be directly on, directly connected to, or directly coupled to, the other element or intervening elements can be present. In contrast, when an element is referred to as being "directly on," "directly connected to," or "directly coupled to" another element, there are no intervening elements present.

[0051] The same reference numerals are used throughout the drawings and description to refer to the same or like elements and no repeated description is provided for them. In addition, the thickness, proportions and dimensions of the constituent elements in the drawings can be exaggerated for effective explanation of the technology.

[0052] The term "and / or" includes one or more of the associated listed items. As used herein, the singular forms "a," "an," and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.

[0053] As used herein, expressions such as "at least one of," "one or more of," and "selected from the group consisting of," when preceding the list of elements, modify the entire list of elements and do not modify the individual elements of the list.

[0054] It will be understood that, although the terms first, second, etc. can be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another. Thus, a first element could be termed a second element without departing from the teachings of the present disclosure. Similarly, a second element could be termed a first element without departing from the teachings of the present disclosure.

[0055] In addition, the terms "below," "under," "above," and "on" are used to explain the relationships of elements shown in the drawings. The terms are relative concepts and are explained based on the directions shown in the drawings.

[0056] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

[0057] It will be further understood that the terms "includes", "including", "comprises" and / or "comprising", when used in this specification, specify the presence of stated features, integers, steps, operations, elements, components and / or combinations thereof, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components and / or combinations thereof.

[0058] Hereinafter, an organic light emitting device according to an embodiment will be explained with reference to the accompanying drawings.

[0059] Figures 1 to 3 is a cross-sectional view schematically showing an organic light emitting device according to an exemplary embodiment of the present disclosure. Referring to Figures 1 to 3 In the organic light emitting device 10 according to the embodiment, the first electrode EL1 and the second electrode EL2 are disposed opposite to each other, and a plurality of organic layers can be disposed between the first electrode EL1 and the second electrode EL2. The plurality of organic layers can include a hole transport region HTR, an emission layer EML, and an electron transport region ETR. For example, the organic light emitting device 10 according to the embodiment can include the first electrode EL1, the hole transport region HTR, the emission layer EML, the electron transport region ETR, and the second electrode EL2, which are stacked one by one. In some embodiments, a capping layer can be further disposed on the second electrode EL2.

[0060] The organic light emitting device 10 of the embodiment can include the crosslinker compound of the embodiment in at least one layer of the plurality of organic layers disposed between the first electrode EL1 and the second electrode EL2, which will be explained later. For example, the organic light emitting device 10 of the embodiment can include the crosslinker compound of the embodiment in the hole transport region HTR disposed between the first electrode EL1 and the second electrode EL2. However, the embodiment of the present disclosure is not limited thereto. The organic light emitting device 10 of the embodiment can include the crosslinker compound of the embodiment in at least one layer included in the emission layer EML and the electron transport region ETR, which are among the plurality of organic layers disposed between the first electrode EL1 and the second electrode EL2, or can include the crosslinker compound of the embodiment in a functional layer, for example, a capping layer disposed on the second electrode EL2.

[0061] In comparison with Figure 1 In comparison with Figure 2 A cross-sectional view showing the organic light emitting device 10 of the embodiment is shown, in which the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. In comparison with Figure 1 In comparison with Figure 3The diagram shows a cross-sectional view of an organic light-emitting device 10 according to an embodiment, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL.

[0062] The first electrode EL1 is conductive. It can be formed using a metal alloy or a conductive compound. The first electrode EL1 can be an anode. Alternatively, it can be a pixel electrode. The first electrode EL1 can be a transmissive electrode, a semi-transmissive reflective electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, it can be formed using a transparent metal oxide (e.g., indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO)). When the first electrode EL1 is a semi-transparent reflective electrode or a reflective electrode, the first electrode EL1 may comprise silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), LiF / Ca, LiF / Al, molybdenum (Mo), titanium (Ti), tungsten (W), indium (In), tin (Sn), zinc (Zn), their compounds, mixtures thereof (e.g., a mixture of Ag and Mg), or oxides of one or more of these. In some embodiments, the first electrode EL1 may have a structure comprising multiple layers, including a reflective or semi-transparent reflective layer formed using the above materials, and a transmissive conductive layer formed using ITO, IZO, ZnO, or ITZO. For example, the first electrode EL1 may comprise a three-layer structure of ITO / Ag / ITO. However, embodiments of this disclosure are not limited thereto. The thickness of the first electrode EL1 may be approximately to approximately For example, about to approximately

[0063] A hole transport region (HTR) can be provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a hole buffer layer, and an electron blocking layer EBL. The thickness of the hole transport region HTR may be approximately to approximately

[0064] The hole transport region (HTR) can have (including) a single layer formed using a single material, a single layer formed using multiple different materials, or a multilayer structure including multiple layers formed using multiple different materials.

[0065] For example, the hole transport region HTR can have a structure of a single layer of a hole injection layer HIL or a hole transport layer HTL, or can have a structure of a single layer formed using a hole injection material and a hole transport material. In some embodiments, the hole transport region HTR can have a structure of a single layer formed using a plurality of different materials, or a structure of a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / hole buffer layer, a hole injection layer HIL / hole buffer layer, a hole transport layer HTL / hole buffer layer, or a hole injection layer HIL / hole transport layer HTL / electron blocking layer stacked from the first electrode EL1, but embodiments of the present disclosure are not limited thereto.

[0066] The hole transport region HTR can be formed using any suitable method, for example, a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and / or a laser-induced thermal imaging (LITI) method.

[0067] The hole transport region HTR in the organic light emitting device 10 of embodiments can include the crosslinker compound of embodiments. In the organic light emitting device 10 of embodiments, the hole transport region HTR can be obtained (e.g., formed) from a hole transport material (HTM, see Figure 4A ) including the crosslinker compound of embodiments.

[0068] In the description, the term "substituted or unsubstituted" means a state of being unsubstituted or substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, an oxyl group, a sulfoxy group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkoxy group, an aliphatic hydrocarbon ring group, an aryl group, and a heterocyclic group. Further, each of the above substituents can be further substituted or unsubstituted. For example, a biphenyl group can be interpreted as a so-called aryl group, or as a phenyl group substituted with a phenyl group.

[0069] In the description, the term "form a ring via bonding with an adjacent group" can mean to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring via bonding with an adjacent group. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocyclic ring can be an aliphatic heterocyclic ring or an aromatic heterocyclic ring. The ring formed by bonding with an adjacent group can be a monocyclic ring or a polycyclic ring. Further, the ring formed by bonding with an adjacent group can be combined with another ring to form a spiro structure.

[0070] In the description, the term "adjacent groups" can mean substituents on the same atom or point, substituents on atoms directly connected to the base atom or point, or substituents spatially positioned (e.g., within bonding distance within a molecule) to the corresponding substituents. For example, in 1,2-dimethylbenzene, the two methyl groups can be interpreted as "adjacent groups" to each other, and in 1,1-diethylcyclopentane, the two ethyl groups can be interpreted as "adjacent groups" to each other.

[0071] In the description, the term "direct bond" can mean a single bond.

[0072] In the description, a halogen atom can be a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0073] In the description, the term "alkyl group" can mean a straight-chain, branched, or cyclic alkyl group. The number of carbons of the alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butyihexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyileicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-uneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, and the like, but are not limited thereto.

[0074] In the description, the hydrocarbon ring and the heterocyclic ring can be a monocyclic ring or a polycyclic ring.

[0075] In the description, the hydrocarbon ring group can be a functional group or a substituent derived from an aliphatic hydrocarbon ring, or a functional group or a substituent derived from an aromatic hydrocarbon ring. The hydrocarbon ring group can have 5 to 60 carbon atoms for forming a ring.

[0076] In this description, the term "aryl group" refers to a functional group or substituent derived from an aromatic hydrocarbon ring. An aryl group can be a monocyclic or polycyclic aryl group. The number of carbons in the aryl group used to form the ring can be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, hexaphenyl, benzo[a]phenanthryl, pyrene, benzo[a]fluoranyl, and so on. Basic, but not restricted.

[0077] In the description, the fluorenyl group may be substituted (e.g., at the 9H position), and two substituents may combine with each other to form a spirostructure. Examples of substituted fluorenyl groups are given below. However, embodiments of this disclosure are not limited thereto.

[0078]

[0079] In the description, a heteroaryl group may contain one or more of B, O, N, P, Si, and S as a heteroatom. When a heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different. A heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of carbon atoms in the heteroaryl group for forming the ring may be 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups include groups derived from the following compounds: thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridine, bipyridine, pyrimidine, triazine, triazole, acridine, pyridazine, pyrazine, quinoline, quinazoline, quinoxaline, phenoxazine, phthalazine, pyridopyrimidine, pyridopyrazine, pyrazinopyrazine, isoquinoline, indole, carbazole, N-arylcarbazole, N-heteroarylcarbazole, N-alkylcarbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, thienothiophene, benzofuran, phenanthroline, isoxazole, thiadiazole, phenthiazine, dibenzothiophene, dibenzofuran, etc., but are not limited thereto.

[0080] In the description, the interpretation of aryl groups can be applied to arylene groups, but arylene groups are divalent groups. The interpretation of heteroaryl groups can be applied to heteroarylene groups, but heteroarylene groups are divalent groups.

[0081] In the description, the term "alkenyl group" can refer to a straight-chain or branched alkenyl group. The number of carbon atoms in the alkenyl group is not particularly limited, but can be 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl groups, 1-butenyl groups, 1-pentenyl groups, 1,3-butadienylaryl groups, styryl groups, styrylvinyl groups, etc.

[0082] In the description, the term "silyl group" can refer to an alkylsilyl group or an arylsilyl group. Examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but are not limited thereto.

[0083] In the description, the term "boron group" can refer to an alkylboron group or an arylboron group. Examples of the boron group include a trimethylboron group, a triethylboron group, a tert-butyldimethylboron group, a triphenylboron group, a diphenylboron group, a phenylboron group, and the like, but are not limited thereto.

[0084] In the description, the number of carbons of the amine group is not particularly limited, but can be 1 to 30. The amine group can be an alkylamine group or an arylamine group. Examples of the amine group include a methylamine group, a dimethylamine group, a phenylamine group, a diphenylamine group, a naphthylamine group, a 9-methyl-anthrylamine group, a triphenylamine group, and the like, but are not limited thereto.

[0085] In the description, the term "hydrocarbon ring group" refers to a functional group or a substituent derived from an aliphatic hydrocarbon ring. The hydrocarbon ring group can be a saturated hydrocarbon ring group having 5 to 20 carbon atoms for forming a ring.

[0086] In the description, the heterocyclic group can contain one or more than one of B, O, N, P, Si, and S as a heteroatom. When the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms can be the same or different. The heterocyclic group can be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and in some embodiments, it can be a heteroaryl group. The number of carbons for forming a ring of the heterocyclic group can be 2 to 30, 2 to 20, or 2 to 10.

[0087] In the description, represents a connecting position.

[0088] The crosslinker compound includes a bis-azido structure (e.g., containing two azido groups) and a polyacetylene (PA) group as a main chain. The crosslinker compound of embodiments can include a connecting structure of two azido groups at both sides (e.g., both ends) of a polyacetylene main chain.

[0089] The crosslinker compound of embodiments can be represented by Formula 1:

[0090] Formula 1

[0091]

[0092] In Formula 1, A can be a hydrogen atom or a deuterium atom. In Formula 1, a plurality of A can be the same or different. In some embodiments, all of A can be a hydrogen atom. In some embodiments, at least one of a plurality of A can be a deuterium atom, and the rest can be a hydrogen atom. The crosslinker compound represented by Formula 1 can include a polyacetylene group as a main chain, which can be unsubstituted (e.g., can not include any substituents other than a hydrogen atom or a deuterium atom).

[0093] In Formula 1, L1and L2may each independently be a direct bond or a substituted or unsubstituted methylene group. In embodiments, L1and L2may be the same or different. For example, both L1and L2may be a direct bond or an unsubstituted methylene group.

[0094] In Formula 1, "m" can be an integer of 1 to 100. When "m" is an integer of 2 or more, the main chain of the compound includes a plurality of repetitions of the acetylene group. For example, when "m" is an integer of 2 or more, a plurality of acetylene groups can be repeatedly connected (e.g., in a row). In embodiments, "m" can be an integer of 3 to 20.

[0095] In Formula 1, "n1" and "n2" can each independently be 1 or 2. When "n1" and "n2" are each 1, two azido groups are present, and one azido group is present on each side of the main chain. In embodiments, "n1" and "n2" can be the same or different. For example, "n1" and "n2" can each be 1 or 2.

[0096] The crosslinker compound of embodiments has a structure in which one or two pairs of azido groups are connected (present) at both sides (ends) of a polyacetylene chain, which is a main chain of the compound. The crosslinker compound of embodiments can have a structure in which a bis-azido group is connected at both sides of a central polyacetylene main chain substituted only with hydrogen atoms or deuterium atoms, and can improve crosslinking efficiency without reducing the hole transport capability of a polymer compound included in a hole transport region. Accordingly, when a hole transport region is formed by a wet process such as inkjet printing, an organic light emitting device including the crosslinker compound of embodiments can have improved resolution, high emission efficiency, and low driving voltage.

[0097] The crosslinker compound according to embodiments of the present disclosure can be represented by Formula 1-a:

[0098] Formula 1-a

[0099]

[0100] In Formula 1-a, A and "m" can be the same as described with respect to Formula 1.

[0101] In Formula 1-a, B can be represented by Formula 1-b or Formula 1-c:

[0102] Formula 1-b

[0103]

[0104] Formula 1-c

[0105]

[0106] In Formula 1-b and Formula 1-c, represents a linking moiety to the acetylene backbone represented in Formula 1-a.

[0107] In Formula 1-a, the two B groups attached at both sides of the acetylene backbone can be the same or different. In embodiments, the two B groups can be represented by Formula 1-b. In embodiments, the two B groups can be represented by Formula 1-c.

[0108] The crosslinker compound according to embodiments of the present disclosure can be represented by Formula 1-1 or Formula 1-2:

[0109] Formula 1-1

[0110]

[0111] Formula 1-2

[0112]

[0113] Formula 1-1 corresponds to an embodiment of Formula 1, where “m” is 3, L1 and L2 are both direct bonds, and n1 and n2 are both 1. Formula 1-2 corresponds to an embodiment of Formula 1, where “m” is 3, L1 and L2 are both unsubstituted methylene groups, and n1 and n2 are both 2.

[0114] In Formula 1-1 and Formula 1-2, A can be the same as described with respect to Formula 1.

[0115] In the organic light emitting device 10 of embodiments, in addition to the crosslinker compound of embodiments, the hole transport region HTR can further comprise a polymer compound having hole transporting properties (e.g., ability). The polymer compound can comprise a substituted or unsubstituted triarylamine group. The polymer compound can comprise or be formed from a monomer comprising a substituted or unsubstituted triarylamine group as a repeating unit.

[0116] The polymer compound according to embodiments can be represented by Formula 2-1 or Formula 2-2. For example, the polymer compound according to embodiments can be a polymer comprising the monomer in Formula 2-1 or Formula 2-2 as a repeating unit.

[0117] Formula 2-1

[0118]

[0119] Formula 2-2

[0120]

[0121] In Formula 2-1 and Formula 2-2, R1 to R7 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring. In an embodiment, R1 to R7 can each independently be a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms. For example, R1 can be a hydrogen atom, a substituted or unsubstituted methyl group, or a substituted or unsubstituted butyl group. For example, R6 and R7 can each independently be a substituted or unsubstituted octyl group.

[0122] In Formula 2-1 and Formula 2-2, "a1" can be an integer of 0 to 5. "a2" and "a3" can each independently be an integer of 0 to 4. "a4" and "a5" can each independently be an integer of 0 to 3. When each of "a1" to "a5" is 0, in the polymer compound according to an embodiment, each of R1 to R5 can be a hydrogen atom. When each of "a1" to "a5" is an integer of 2 or more, a plurality of R1 to R5 can be the same or different.

[0123] In Formula 2-1 and Formula 2-2, "p1" and "p2" can each independently be an integer of 1 to 100. In an embodiment, a case in which each of "p1" and "p2" is an integer of 2 or more corresponds to a case in which a plurality of monomers represented by Formula 2-1 and Formula 2-2 are provided. For example, a case in which each of "p1" and "p2" is an integer of 2 or more corresponds to a case in which a plurality of monomers represented in Formula 2-1 and Formula 2-2 are repeatedly connected. In an embodiment, each of "p1" and "p2" can be an integer of 3 to 20.

[0124] The polymer compound according to an embodiment can be represented by Formula 2-1-1, Formula 2-1-2, or Formula 2-2-1:

[0125] Formula 2-1-1

[0126]

[0127] Formula 2-1-2

[0128]

[0129] Formula 2-2-1

[0130]

[0131] Formula 2-1-1, Formula 2-1-2, and Formula 2-2-1 are exemplary embodiments of Formula 2-1 and Formula 2-2, in which substituents represented by R1to R7are specified.

[0132] In Formula 2-1-1, Formula 2-1-2, and Formula 2-2-1, “p1” and “p2” can be the same as described with respect to Formula 1.

[0133] The crosslinker compound and the polymer compound according to embodiments can each independently be included in a hole transport layer HTL in the hole transport zone HTR. The weight ratio of the polymer compound and the crosslinker compound included in the hole transport layer HTL can be about 4:1 to about 19:1. In some embodiments, the weight ratio of the polymer compound and the crosslinker compound included in the hole transport layer HTL can be about 9:1. The polymer compound included in the hole transport layer HTL can be thermally crosslinked or photo-crosslinked by the crosslinker compound.

[0134] In the organic light emitting device 10 of embodiments, the hole transport zone HTR can further include any suitable material.

[0135] The hole injection layer HIL can include, for example, a phthalocyanine compound (e.g., copper phthalocyanine), N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris{N-2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphor sulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-bis(naphthalen-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyl diphenyl iodonium [tetrakis(pentafluorophenyl)borate], and dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).

[0136] In some embodiments, the hole transport layer HTL can further include, in addition to the crosslinker compound and the polymer compound, a carbazole derivative (e.g., N-phenylcarbazole and / or polyvinylcarbazole), a fluorene-based derivative, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), a triphenylamine-based derivative (e.g., 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA)), N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), 4,4'-bis[N,N'-(3-methylphenyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-bis(N-carbazolyl)benzene (mCP), or the like.

[0137] The thickness of the hole transport region HTR can be, for example, about 1 nm to about 100 nm. to about 100 nm. For example, the thickness of the hole transport region HTR can be about 1 nm to about 50 nm. to about 100 nm. The thickness of the hole injection layer HIL can be, for example, about 1 nm to about 100 nm. to about 100 nm. The thickness of the hole transport layer HTL can be, for example, about 1 nm to about 100 nm. to about 100 nm. For example, the thickness of the hole transport layer HTL can be about 1 nm to about 50 nm. to about 100 nm. When the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the ranges described above, satisfactory hole transport properties can be achieved without a significant increase in driving voltage.

[0138] In addition to the materials described above, the hole transport region HTR can further include a charge generating material to increase conductivity. The charge generating material can be dispersed substantially uniformly or non-uniformly in the hole transport region HTR. The charge generating material can be, for example, a p-dopant. The p-dopant can be selected from quinone derivatives, metal oxides, and compounds containing a cyano group, but is not limited thereto. For example, the p-dopant can include quinone derivatives (e.g., tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane (F4-TCNQ)), metal oxides (e.g., tungsten oxide and / or molybdenum oxide), but is not limited thereto.

[0139] As described above, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR can further include at least one of a hole buffer layer and an electron blocking layer EBL. The hole buffer layer can compensate for an optical resonance distance of a wavelength of light emitted from the emission layer EML, and can thereby increase light emission efficiency of the device. Materials that can be included in the hole transport region HTR can be included in the hole buffer layer. The electron blocking layer EBL can prevent or reduce electron injection from the electron transport region ETR to the hole transport region HTR. When the hole transport region HTR includes at least one selected from the hole buffer layer and the electron blocking layer EBL adjacent to the emission layer EML, the crosslinker compound according to the embodiments can be included in the hole buffer layer and / or the electron blocking layer EBL adjacent to the emission layer EML. Further, the polymer compound according to the embodiments (included in the hole buffer layer and / or the electron blocking layer EBL adjacent to the emission layer EML) can be thermally crosslinked or photo-crosslinked by the crosslinker compound.

[0140] The emission layer EML is provided on the hole transport region HTR. The emission layer EML can have, for example, a thickness of about 1 nm to about 50 nm, about 1 nm to about 30 nm, about 1 nm to about 20 nm, about 1 nm to about 10 nm, about 1 nm to about 5 nm, about 5 nm to about 50 nm, about 5 nm to about 30 nm, about 5 nm to about 20 nm, about 5 nm to about 10 nm, about 10 nm to about 50 nm, about 10 nm to about 30 nm, about 10 nm to about 20 nm, about 20 nm to about 50 nm, about 20 nm to about 30 nm, about 30 nm to about 50 nm, or about 50 nm or greater. about 10 nm to about 50 nm, about 10 nm to about 30 nm, about 10 nm to about 20 nm, about 20 nm to about 50 nm, about 20 nm to about 30 nm, about 30 nm to about 50 nm, or about 50 nm or greater. about 10 nm to about 50 nm, about 10 nm to about 30 nm, about 10 nm to about 20 nm, about 20 nm to about 50 nm, about 20 nm to about 30 nm, about 30 nm to about 50 nm, or about 50 nm or greater. about 10 nm to about 50 nm, about 10 nm to about 30 nm, about 10 nm to about 20 nm, about 20 nm to about 50 nm, about 20 nm to about 30 nm, about 30 nm to about 50 nm, or about 50 nm or greater. The emission layer EML can have a single layer formed using a single material, a single layer formed using a plurality of different materials, or a multi-layer structure having a plurality of layers formed using a plurality of different materials.

[0141] Further, the emission layer EML of the organic light emitting device 10 can be intended to emit blue light. For example, the emission layer EML of the organic light emitting device 10 according to the embodiments can emit blue light in a region of about 490 nm or greater than 490 nm. However, embodiments of the present disclosure are not limited thereto, but can be intended to emit green light or red light.

[0142] In some embodiments, the organic light emitting device 10 according to the embodiments can include a plurality of emission layers. The plurality of emission layers can be stacked one by one, and for example, the organic light emitting device 10 including a plurality of emission layers can be intended to emit white light. The organic light emitting device including a plurality of emission layers can be an organic light emitting device having a tandem structure.

[0143] In embodiments, the emission layer EML can be a delayed fluorescence emission layer, a fluorescent emission layer, a phosphorescent emission layer, etc., and the emission layer EML can include any suitable host material and dopant. For example, the emission layer EML can be intended to emit thermally activated delayed fluorescence (TADF).

[0144] As a host material of the emission layer EML, any suitable material can be used, and can be selected from a fluoranthene derivative, a pyrene derivative, an aryl acetylene derivative, an anthracene derivative, a fluorene derivative, a perylene derivative, Derivatives, etc., but are not particularly limited. In some embodiments, pyrene derivatives, perylene derivatives, and anthracene derivatives can be used. For example, as a host material of the emission layer EML, an anthracene derivative represented by Formula 3 can be used:

[0145] Formula 3

[0146]

[0147] In Formula 3, R 31 to R 40 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, or be combined with an adjacent group to form a ring. In some embodiments, R 31 to R 40 may be combined with an adjacent group to form a ring.

[0148] In Formula 3, "c" and "d" can each independently be an integer of 0 to 5.

[0149] Formula 3 can be represented by any one of compounds 3-1 to 3-16:

[0150]

[0151]

[0152] In embodiments, the emission layer EML can include, as a host material, tris(8-hydroxyquinolinolato)aluminum (Alq3), 4,4'-bis(carbazolyl)-1,1 '-biphenyl (CBP), poly(N-vinylcarbazole) (PVK), 9,10-di(naphthalen-2-yl)anthracene (ADN), 4,4',4"-tris(carbazol-9-yl)-triphenylamine (TCTA), 1,3,5-tris(1 -phenyl-1 H-benzo[d]imidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-di(naphthalen-2-yl)anthracene (TBADN), diphenylstyrylarylidene (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-di(naphthalen-2-yl)anthracene (MADN), bis[2-(diphenylphosphinyl)phenyl]ether oxide (DPEPO), hexaphenylcyclotriphosphazene (CP1 ), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), 2,8-bis(diphenylphosphoryl)dibenzo-furan (PPF), 3,3'-bis(N-carbazolyl)-1,1 '-biphenyl (mCBP), 1,3-bis(N-carbazolyl)benzene (mCP), 9,10-di(naphthalen-2-yl)anthracene (DNA), and the like. However, embodiments of the present disclosure are not limited thereto, and can include any suitable host material that emits delayed fluorescence in addition to the suggested host materials.

[0153] In embodiments, the emission layer EML can include, as a dopant, a styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), and / or N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N- phenylaniline (N-BDAVBi)), perylene and its derivatives (e.g., 2,5,8,1 1 -tetra-tert- butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1 '-dipyrene, 1,4-dipyrenylbenzene, and / or 1,4-bis(N,N-diphenylamino)pyrene), and the like.

[0154] In some embodiments, the emission layer EML can include two dopant materials having different lowest triplet excitation energy levels (T1 energy levels). In the organic light emitting device 10 of embodiments, the emission layer EML can include a host having a first lowest triplet excitation energy level, a first dopant having a second lowest triplet excitation energy level lower than the first lowest triplet excitation energy level, and a second dopant having a third lowest triplet excitation energy level lower than the second lowest triplet excitation energy level.

[0155] In the organic light emitting device 10 of the embodiment including the host, the first dopant, and the second dopant in the emission layer EML, the first dopant can be a delayed fluorescence dopant, and the second dopant can be a fluorescent dopant.

[0156] For example, when the emission layer EML of the organic light emitting device 10 of the embodiment includes a plurality of dopants, the emission layer EML can include the first dopant and the second dopant different from each other. For example, when the emission layer EML is intended to emit blue light, the emission layer EML can further include any one selected from the group consisting of spiro-DPVBi, spiro-6P, diphenylstyryl-benzene (DSB), diphenylstyryl-arylidene (DSA), a polyfluorene (PFO)-based polymer, and a poly(p-phenylenevinylene) (PPV)-based polymer. In addition, as the second dopant, a metal or organometallic complex such as (4,6-F2ppy)2Irpic or perylene and derivatives thereof can be used.

[0157] In the organic light emitting device 10 of the embodiment as shown in Figures 1 to 3 In the organic light emitting device 10 of the embodiment as shown in

[0158] The electron transport zone ETR can have a single layer formed using a single material, a single layer formed using a plurality of different materials, or a multi-layer structure having a plurality of layers formed using a plurality of different materials.

[0159] For example, the electron transport zone ETR can have a single layer structure of the electron injection layer EIL or the electron transport layer ETL, or a single layer structure formed using an electron injection material and an electron transport material. In some embodiments, the electron transport zone ETR can have a single layer structure containing a plurality of different materials, or a structure of the electron transport layer ETL / electron injection layer EIL, or the hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL stacked from the emission layer EML, but is not limited thereto. The thickness of the electron transport zone ETR can be, for example, about 1 nm to about 200 nm. to about 200 nm.

[0160] The electron transport zone ETR can be formed using any suitable method such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and / or a laser induced thermal imaging (LITI) method.

[0161] When the electron transport region (ETR) includes an electron transport layer (ETL), the ETR can contain anthracene-based compounds. The ETR can contain, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridyl)-benzene-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), and 4,7-diphenyl-1,10-phenanthroline (Bphe). n), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-quinoline-N1,O8)-(1,1'-biphenyl-4-oxoline)aluminum (BAlq), bis(benzoquinoline-10-oxoline)beryllium (Bebq2), 9,10-bis(naphthyl-2-yl)anthracene (ADN), or any mixture thereof, but not limited thereto. The thickness of the electron transport layer ETL can be approximately to approximately For example, about to approximately When the thickness of the electron transport layer (ETL) meets the range described above, satisfactory electron transport properties can be obtained without a significant increase in driving voltage.

[0162] When the electron transport region (ETR) includes an electron injection layer (EIL), the ETR may comprise a metal halide (e.g., LiF, NaCl, CsF, RbCl, RbI, and / or CuI), a lanthanide (e.g., ytterbium (Yb)), a metal oxide (e.g., Li₂O and / or BaO), or lithium hydroxyquinoline (LiQ). However, embodiments of this disclosure are not limited thereto. A mixture of an electron injection material and an insulating organometallic salt can also be used to form the electron injection layer (EIL). The insulating organometallic salt can be a material having a band gap of about 4 eV or greater. For example, the insulating organometallic salt may include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and / or metal stearates. The thickness of the electron injection layer (EIL) can be about... to approximately Or about to approximately When the thickness of the electron injection layer EIL satisfies the range described above, satisfactory electron injection properties can be obtained without a significant increase in driving voltage.

[0163] The electron transport zone ETR can include the hole blocking layer HBL as described above. The hole blocking layer HBL can include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 4,7-diphenyl-1,10-phenanthroline (Bphen). However, embodiments of the present disclosure are not limited thereto.

[0164] A second electrode EL2 is provided on the electron transport zone ETR. The second electrode EL2 can be a common electrode or a cathode. The second electrode EL2 can be a transmissive electrode, a semi-transmissive and reflective electrode, or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 can include a transparent metal oxide, for example, ITO, IZO, ZnO, ITZO, or the like.

[0165] When the second electrode EL2 is a semi-transmissive and reflective electrode or a reflective electrode, the second electrode EL2 can include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, Yb, W, In, Sn, Zn, a compound thereof, a mixture thereof (for example, a mixture of Ag and Mg), or an oxide thereof. The second electrode EL2 can have a multi-layer structure including a reflective layer or a semi-transmissive and reflective layer formed using the materials described above, and a transparent conductive layer formed using ITO, IZO, ZnO, ITZO, or the like.

[0166] In some embodiments, the second electrode EL2 can be connected with an auxiliary electrode. When the second electrode EL2 is connected with the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.

[0167] In some embodiments, the organic light emitting device 10 of the embodiments can further include a buffer layer between the emission layer EML and the electron transport zone ETR. The buffer layer can control the concentration of excitons generated in the emission layer EML. For example, the buffer layer can include a portion of the material of the emission layer EML. The buffer layer can include a host material among the materials of the emission layer EML. Depending on the combination of the host and dopant materials, the material of the buffer layer can be selected to have a lowest triplet excitation energy level that is greater than or equal to the lowest triplet excitation energy level of the second dopant and less than or equal to the lowest triplet excitation energy level of the first dopant.

[0168] The organic light emitting device 10 according to the embodiments of the disclosure can include the crosslinker compound of the embodiments in a hole transport region HTR disposed between the first electrode EL1 and the second electrode EL2, and can provide an organic light emitting device having high emission efficiency and low driving voltage by an increase in a residual layer ratio of the hole transport region HTR through a wet process such as inkjet printing to form the hole transport region.

[0169] Figures 4A to 4C is a cross-sectional view schematically illustrating partial steps of a manufacturing method of an organic light emitting device according to the embodiments of the disclosure. In Figures 4A to 4C , a step of forming a hole transport layer HTL on a hole injection layer HIL in the manufacturing method of the organic light emitting device according to the embodiments of the disclosure is shown step by step. Hereinafter, a method of manufacturing an organic light emitting device according to the embodiments of the disclosure will be explained with reference to Figures 4A to 4C

[0170] The method of manufacturing an organic light emitting device according to the embodiments includes a step of preparing a first electrode, a step of forming a hole transport region by providing a hole transport material on the first electrode, a step of forming an emission layer on the hole transport region, and a step of forming a second electrode on the emission layer.

[0171] Referring to Figures 4A to 4C , the hole transport region HTR (see Figure 1 ) includes a hole injection layer HIL formed on the first electrode EL1 and a hole transport layer HTL formed on the hole injection layer HIL, and the hole transport layer HTL can be formed by a hole transport material HTM. The hole transport material HTM can include the crosslinker compound of the embodiments. The hole transport material HTM can include the crosslinker compound represented by Formula 1. The hole transport material HTM can further include a polymer compound including a substituted or unsubstituted triarylamine group, and the polymer compound can be represented by Formula 2-1 or Formula 2-2. In the hole transport material HTM, the weight ratio of the polymer compound and the crosslinker compound can be about 4:1 to about 19:1. For example, the weight ratio of the polymer compound and the crosslinker compound in the hole transport material HTM can be about 9:1. The hole transport material HTM can be prepared by mixing the polymer compound and the crosslinker compound in a solvent. In embodiments, the solvent can include any one of toluene, xylene, o-xylene, m-xylene, and anisole, or any combination thereof (e.g., as a mixed solvent).

[0172] The hole transport material HTM can be deposited on the hole injection layer HIL by a wet process. Figure 4A ​An exemplary embodiment illustrating that a hole transport material HTM is supplied onto a hole injection layer HIL through a nozzle NZ is illustrated. However, the hole transport material HTM can be deposited using any suitable solution processing technique, including spin coating, inkjet printing, nozzle printing, and spray printing, but is not limited thereto.

[0173] The method of manufacturing an organic light emitting device according to the embodiments can include, after the hole transport material HTM is supplied onto the hole injection layer HIL to form a preliminary hole transport layer P-HTL, a step of forming the hole transport layer HTL by applying heat or light to the preliminary hole transport layer P-HTL. Figure 4B An exemplary embodiment illustrating that the hole transport layer HTL is formed by thermally cross-linking a polymer compound and a cross-linker compound included in the preliminary hole transport layer P-HTL is illustrated, but the embodiments of the present disclosure are not limited thereto, or the hole transport layer HTL can be formed by photo-crosslinking a polymer compound and a cross-linker compound included in the preliminary hole transport layer P-HTL.

[0174] Hereinafter, the cross-linker compound, the polymer compound, and the organic light emitting device of the embodiments according to the present disclosure will be specifically explained with reference to the embodiments and comparative embodiments. The following embodiments are merely examples to help understanding of the present disclosure, and the scope of the present disclosure is not limited thereto.

[0175] Embodiments

[0176] 1. Synthesis of a cross-linker compound

[0177] First, the method of synthesizing the cross-linker compound according to the embodiments will be explained in more detail with reference to the synthesis method of Example Compound 1 and Example Compound 2. The synthesis method of the cross-linker compound explained herein below is an embodiment, and the synthesis method of the cross-linker compound according to the embodiments of the present disclosure is not limited thereto. The structures of Example Compound 1 and Example Compound 2 are as follows:

[0178] Example Compound 1

[0179]

[0180] Example Compound 2

[0181]

[0182] 1) Synthesis of Example Compound 1

[0183] Example Compound 1 according to the embodiments was synthesized by the following method.

[0184] Example Compound 1 was synthesized by replacing the chlorine atoms of 1,6-dichlorohexa-1,3,5-triene with azido groups through a nucleophilic substitution reaction. 1,6-Dichlorohexa-1,3,5-triene (10.0 g, 0.067 mol) and sodium azide (10.5 g, 0.161 mol, 2.4 eq) were dissolved in DMF solvent in a flask under a nitrogen atmosphere, and stirred at room temperature for about 12 hours to synthesize Example Compound 1 at a yield of 95%.

[0185] 2) Synthesis of Example Compound 2

[0186] Example Compound 2 according to the embodiment was synthesized by the following method.

[0187] Example Compound 2 was synthesized by replacing the chlorine atoms of 1,1,8,8-tetrachlorohexa-2,4,6-triene with azido groups through a nucleophilic substitution reaction. 1,1,8,8-Tetrachlorohexa-2,4,6-triene (10 g, 0.040 mol) and sodium azide (12.5 g, 0.192 mol, 4.8 eq) were dissolved in DMF solvent in a flask under a nitrogen atmosphere, and stirred at room temperature for about 12 hours to synthesize Example Compound 2 at a yield of 89%.

[0188] 2. Preparation of a polymer compound

[0189] In the crosslinker compounds according to the embodiment, commercially available materials were used as the polymer compounds A to C. The structures of the polymer compounds A to C are as follows. In the following compounds, q1 and q2 are each independently an integer of 10 to 50.

[0190] Polymer Compound A

[0191]

[0192] Polymer Compound B

[0193]

[0194] Polymer Compound C

[0195]

[0196] 3. Evaluation of residual layer properties

[0197] Each of the crosslinker compounds and each of the polymer compounds of the examples and comparative examples were mixed to form inks, a single layer was formed by the inks, and the residual layer ratio of the single layer was measured. The combination of the crosslinker compounds and the polymer compounds used in each of the inks and the method of preparing the inks are as follows.

[0198] Example Ink 1

[0199] Example Ink 1 was prepared via the same preparation method of Example Ink 1, but using Polymer Compound B as the polymer compound.

[0200] Example Ink 2

[0201] Example Ink 2 was prepared via the same preparation method of Example Ink 1, but using Example Compound 2 as the crosslinker compound.

[0202] Example Ink 3

[0203] Example Ink 3 was prepared via the same preparation method of Example Ink 1, but using Polymer Compound B as the polymer compound.

[0204] Example Ink 4

[0205] Example Ink 4 was prepared via the same preparation method of Example Ink 3, but using Example Compound 2 as the crosslinker compound.

[0206] Example Ink 5

[0207] Example Ink 5 was prepared via the same preparation method of Example Ink 1, but using Polymer Compound C as the polymer compound.

[0208] Example Ink 6

[0209] Example Ink 6 was prepared via the same preparation method of Example Ink 5, but using Example Compound 2 as the crosslinker compound.

[0210] Comparative Ink 1

[0211] Comparative Ink 1 was prepared via the same preparation method of Example Ink 1, but using Comparative Compound 1 as the crosslinker compound.

[0212] Comparative Ink 2

[0213] Comparative Ink 2 was prepared via the same preparation method of Comparative Ink 1, but using Polymer Compound B as the polymer compound.

[0214] Example Compound 1

[0215]

[0216] Example compound 2

[0217]

[0218] Polymer compound A

[0219]

[0220] Polymer compound B

[0221]

[0222] Polymer compound C

[0223]

[0224] Compare compound 1

[0225]

[0226] Evaluation of the formation of individual layers and the ratio of residual layers

[0227] Supply each of the inks prepared in the above-described examples and comparative examples to form an ink having approximately A layer of thickness was formed and dried at approximately 200°C for approximately 30 minutes to complete the formation of a single layer. First, the UV of the corresponding single layer was measured. Then, 50 μL of methyl benzoate was dropped onto the top of the corresponding single layer and allowed to stand for approximately 30 minutes. The solvent was then absorbed by a wiping agent, and the film was dried at approximately 100°C for approximately 1 minute, followed by UV measurement. The residual layer ratio (e.g., the area ratio of the remaining layer) of the single layer was calculated using Equation 1:

[0228] Equation 1

[0229] Residual layer ratio (%) = Second UV measurement area / First UV measurement area

[0230] The residual layer ratios of individual layers formed using Example Ink 1 to Example Ink 6, as well as Comparative Ink 1 and Comparative Ink 2, were evaluated and are shown in Table 1.

[0231] Table 1

[0232] Ink composition Crosslinker compound Polymer compound Residual layer ratio (%) Example Ink 1 Example Compound 1 Polymer compound A 100 Example Ink 2 Example Compound 2 Polymer compound A 100 Example Ink 3 Example Compound 1 Polymer compound B 100 Example Ink 4 Example Compound 2 Polymer compound B 100 Example Ink 5 Example Compound 1 Polymer compound C 100 Example Ink 6 Example Compound 2 Polymer compound C 100 Comparative Ink 1 Comparative Compound 1 Polymer compound A 20 Comparative Ink 2 Comparative Compound 1 Polymer compound B Comparative Ink 3 Comparative Compound 1 Polymer compound B 10

[0233] Referring to the results of Table 1, it can be confirmed that the individual layers formed by including the crosslinker compound according to the embodiments of the disclosure each have a higher residual layer ratio than the individual layers formed by including the crosslinker compound of the comparative example. The individual layer including the crosslinker compound according to the embodiments has improved layering properties due to the crosslinking efficiency of the crosslinker compound, and since the conjugation property of the polymer compound having a hole transport ability should not be deteriorated by the crosslinker compound, an organic light emitting device having high emission efficiency and low driving voltage can be manufactured.

[0234] The organic light emitting device of the embodiments can exhibit low driving voltage and improved device characteristics with high efficiency.

[0235] The crosslinker compound of the embodiments can be used in the process of forming a hole transport zone of an organic light emitting device, and can contribute to improved resolution and efficiency of the organic light emitting device.

[0236] As used herein, the terms "substantially," "about," and similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art.

[0237] Any numerical range recited herein is intended to include all sub-ranges of the same numerical precision, within the recited range. For example, a range of "1.0 to 10.0" is intended to include all sub-ranges, e.g., 2.4 to 7.6, within the same precision used in the recited range, e.g., 2.5. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, the applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited in this specification.

[0238] While exemplary embodiments of the disclosure have been described, it is to be understood that the disclosure is not limited to those precise embodiments, and that various changes and modifications can be made by those skilled in the art without departing from the scope and spirit of the disclosure as set forth in the claims and equivalents thereof.

Claims

1. An organic light emitting device comprising: a first electrode; a hole transport zone on the first electrode; an emission layer on the hole transport zone; an electron transport zone on the emission layer; and a second electrode on the electron transport zone, wherein the hole transport zone is obtained from a hole transport material including a crosslinker compound represented by Formula 1 and a polymer compound including a substituted or unsubstituted triarylamine group: Formula 1 wherein in Formula 1, A is a hydrogen atom or a deuterium atom, and a plurality of A is the same or different, and L1 and L2 are each independently a direct bond or a substituted or unsubstituted methylene group, m is an integer of 1 to 100, and n1 and n2 are each independently 1 or 2. 2.The organic light emitting device of claim 1, wherein the hole transport zone comprises: a hole injection layer on the first electrode; a hole transport layer on the hole injection layer, and wherein the hole transport layer is obtained from the hole transport material including the crosslinker compound represented by Formula 1 and the polymer compound. 3.The organic light emitting device of claim 1, wherein the hole transport zone comprises a plurality of organic layers, and wherein an organic layer of the plurality of organic layers adjacent to the emission layer is obtained from the hole transport material including the crosslinker compound represented by Formula 1 and the polymer compound. 4.The organic light emitting device of claim 1, wherein the crosslinker compound represented by Formula 1 is represented by Formula 1-1 or Formula 1-2: Formula 1-1 Formula 1-2 wherein in Formula 1-1 and Formula 1-2, A is the same as defined in Formula 1. and 5.The organic light emitting device of claim 1, wherein the polymer compound is represented by Formula 2-1 or Formula 2-2: Formula 2-1 Formula 2-2 wherein in Formula 2-1 and Formula 2-2, and R1 to R7 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a1 is an integer of 0 to 5, a2 and a3 are each independently an integer of 0 to 4, a4 and a5 are each independently an integer of 0 to 3, and p1 and p2 are each independently an integer of 1 to 100. 6.The organic light emitting device of claim 5, wherein the polymer compound is represented by any one selected from Formula 2-1-1, Formula 2-1-2, and Formula 2-2-1: Formula 2-1-1 Formula 2-1-2 Formula 2-2-1 wherein in Formula 2-1-1, Formula 2-1-2, and Formula 2-2-1, and p1 and p2 are the same as defined in Formula 2-1 and Formula 2-2. 7.The organic light emitting device of claim 1, wherein a weight ratio of the polymer compound and the crosslinker compound included in the hole transport material is 4:1 to 19:

1. in the hole transport zone, the polymer compound and the crosslinker compound are thermally or photo-crosslinked.

8. The organic light emitting device as claimed in claim 1, wherein, 9.A method of manufacturing an organic light emitting device, the method comprising: ​ manufacturing a first electrode; supplying a hole-transporting material onto the first electrode to form a hole-transporting region; forming an emission layer on the hole-transporting region; and forming a second electrode on the emission layer, wherein the hole-transporting material includes a crosslinking agent compound represented by Formula 1 and a polymer compound including a substituted or unsubstituted triarylamine group: Formula 1 and wherein in Formula 1, A is a hydrogen atom or a deuterium atom, and a plurality of A is the same or different, m is an integer of 1 to 100, L1and L2are each independently a direct bond or a substituted or unsubstituted methylene group, and n1and n2are each independently 1 or 2.

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